My Sister Set Me Up on a Blind Date
“Son, are you trying to tell me that this is really your driver’s license?”
It was a Friday night at the end of my sophomore year at college. A cop had pulled me over as I was driving home.
“Yes it is, Officer.”
“And your last name is really Chevrolet?”
“That’s my last name. Just like it was the last name of Louis Chevrolet, the co-founder of the Chevrolet car company.”
I hated it when people wouldn’t believe that my last name was Chevrolet.
If it was Ford, they wouldn’t think twice. Now if it was “Google” or “FedEx”, I could understand them being doubtful.
“Are you any kin of his?”
“Not that I know of, Officer. He was born in Switzerland in 1878 and the Chevrolet I’m descended from came to the US from France in 1795.”
“I find it hard to believe that anyone is really named Chevrolet.”
“Can I show you an article from my high school that has my name in it?”
“That’d be nice.”
I learned long ago that seeing my name on a website somehow made it real for people. I pulled up an article from my senior year. The picture with the article showed me with short, dark blond hair and blue eyes.
“Here you go, Officer,” I said as I handed him my phone.
“Wrestler, huh? Made district semi-finals?”
“In the 170 weight class.” For a school as small as ours, it was an impressive performance.
“Have you been drinking tonight?” the cop asked as he handed me back my phone.
“No, Officer.” Fortunately, I hadn’t.
“Then why do I smell alcohol?”
I pointed my thumb to the passenger seat. “Because my stupid little sister got sloshed at a party. She called me to come get her when her date wouldn’t take no for an answer.”
“Todd!” squealed my sister Ashlynne. “Why did you tell him that?”
“Because he was going to want to know why I’m driving a drunk girl home. Isn’t that right, Officer?”
“I’m not drunk!”
“That question was going to come up,” said the officer in a slow drawl. He seemed to be enjoying our conversation. A small town cop having a little fun. I wasn’t. “Roll down her window.”
I rolled down Ashlynne’s window as the cop walked around to her side of the car. I had no idea why he had pulled me over. If he wrote me a ticket, the cost of my car insurance would explode.
“My, you are a sporty little model,” said the cop to my sister. I ground my teeth – I was sick of car jokes and puns. “Do you have any ID?”
“No,” she said in a small voice. “I was on a date and I didn’t think I would need my wallet.”
I offered, “I can show you a picture of her with her name on our school website.”
“That’d be good,” said the officer.
I pulled up a web page that had Ashlynne on it. “You’ll have to trust me that she’s not an unrelated Chevrolet.”
The cop laughed. “I don’t know if there’s another Chevrolet family in the whole state.”
I reached over and handed him my phone. He looked at the web page. “Cheerleader captain? Miss Chevrolet must be great at revving up a crowd.” The cop held his flashlight so it wasn’t shining in Ashlynne’s eyes but he could clearly see her face. Ashlynne was the quintessential cheerleader –
5’5″, blue-eyed, blond, pretty, big tits, firm body.
“How old are you?”
“Are you in this car of your own free will?”
“Do you want me to take you home instead of your brother?”
Mom and Dad would hit the roof if their little princess was driven home by a cop. As it was, it was going to be a challenge to get Ashlynne in the house without Mom and Dad noticing she was sloshed.
“Making sure you’re okay.” The cop turned off his flashlight and walked around to my window. “Now, you probably know why I pulled you over…”
“I have no idea.”
“You were doing 36 in a 35 mile per hour speed zone.”
I bit my tongue. My insurance rate was going to go through the roof because I was going one mile over the speed limit while rescuing my asshole sister from a bad party scene.
“Now, I can write you a ticket,” continued the cop. “Or you can come blow into a little tube in my car and I’ll give you just a warning.”
“Fuck!” I said.
“I’m sorry, Officer. You’re only doing your job. I have to drive back to the dorms tonight and then get up ridiculously early tomorrow for my Geology final. Losing all this sleep because of my stupid sister is killing me.” I exhaled to clear my mind. “Let’s go.”
I got out of the car and we walked back to his cruiser. He motioned me to get into the passenger seat. I sat down in the seat and then blew into a tube he held for me.
“No alcohol,” said the cop.
I started to get out of the cruiser when the cop motioned me to be still. “Let’s talk while I fill out the warning.” As he was writing, he asked, “Why didn’t your mom or dad get your sister?”
“Because they would have been furious that she had drunk alcohol and that she had gone to a party where people were drinking.”
The cop shook his head. “So she feared her parents’ anger more than possibly being raped by her date?” That pulled me up short. I hadn’t thought of it that way. “Too many parents are like that. She was lucky she could call you.”
He silently filled out the warning, letting that sink in. Ashlynne was lucky that I was home tonight. I lived in the dorms, though I’d be moving home in a few days. I came home tonight to meet with the owner of the fast food place I’ve worked at since high school about a summer job. I had been about to head back to the dorms when Ashlynne had called. The cop finished the paperwork and began typing into his computer. “Be easy on her. She needs to have someone to get her when she’s in an unsafe situation.”
I sighed. I knew the cop was right. However, I really wanted to chew my sister out when I got back into the car. “I will.”
He moved away from the computer and his voice lightened as he handed me my warning. “I put on your record that you were cooperative and had gone out of your way to help a drunk friend, so hopefully the next cop to pull you over will cut you some slack.”
“Thanks!” I said. I was surprised at the kindness.
“Now go home and good luck on your final tomorrow.”
* * * *
After dinner that next day, Ashlynne came into my room and closed the door.
“Thanks again for getting me yesterday.”
“It was no problem.”
“Thanks for taking Mom and Dad to the living room. I expected you to have left before I came in and for one of them to be in the kitchen waiting for me.”
The plan we had agreed to in the car was that I would go in first and that she would come in ten minutes later. When I came in, I told Mom and Dad that I had something important to discuss with them and that I wanted to talk in the living room.
I shrugged my shoulders. “It wasn’t a big deal. I had something to discuss with them.”
“How did the final go?”
“Well. Turned out that sleep wasn’t an issue. A bus drove us out to where our final was. I slept the whole drive and felt fresh when I got there. I identified everything I was asked about and had a good answer to every question. On last night – call me if you’re ever in a situation like that again. I won’t be thrilled, but I’d much rather you be safe.”
I felt awkward being nice to Ashlynne. She and I had fought all the time growing up. One of the things I had liked about college was that I was away from her. I had hardly seen her since last summer as my roommate’s mom had gotten me a job during Christmas break working at an amusement park and I had stayed with them for all but Christmas Eve and Christmas Day. I had changed a lot in that time.
Ashlynne asked, “Is there something I could do for you?”
“Could you set me up with a cheerleader? A smart cheerleader with a great personality?”
“Almost every cheerleader I know who isn’t a bitch is dating someone.”
“Oh well. It was worth a try.” Nothing ventured, nothing gained. “How about you tell me how you wound up in that situation?”
Ashlynne had been standing while I was sitting in my desk chair, but now she sat down on my bed.
“That’s fair.” She sighed. “I’ve been wanting for a long time to go out with a smart athlete and last night, I thought I had finally gone out with someone who was right for me. You don’t know Jeffrey as he transferred to our school this year. Offensive lineman. Shot putter. He’s also in most of my AP classes. A really nice guy I thought. I think he found me intimidating as it was a long time before he would talk with me. It wasn’t until a few weeks ago that he showed much interest in me. I finally told him that if he wanted to ask me out that he needed to do it soon as school was almost over. So he asked me out for last night.”
Ashlynne leaned forward, apparently happy to have an audience for her story. Ashlynne was a talker and always dominated our conversations the few times that we did talk.
“So we went out to dinner and had a great time. He was so different than the other football players. Instead of talking about only football, he talked about books, movies and music. We have very similar tastes. He seemed thoughtful and caring. I was thinking ‘Wow! This is great.’ We went to a movie and we held hands and kissed during the movie. When we got outside, I suggested we go someplace where we could be alone.”
“So everything was great to that point.”
“Yes. Best date I had ever been on. As we drove, I decided that I was going to let Jeffrey do whatever he wanted as long as our clothes stayed on.”
“Then everything fell apart. He drove us to a house that was hosting a football team party. I was not happy about that. He said that we would be
there for only a few minutes and then he left me to go find someone. I decided to have a daiquiri while I waited. When Jeffrey didn’t come back, I went looking for him and found him with some football players. It was awful. It was like his IQ dropped 30 points in their company. The only thing they would talk about was football games and football practices.”
Ashlynne’s face was getting flushed in anger. “I had finished my daiquiri and someone handed me another one. I drank it and fumed while he talked with his buddies instead of me. I was about to tell Jeffrey to take me home when a football player came up to Jeffrey and slapped him on the back. Jeffrey grabbed my hand and pulled me upstairs. As I was climbing the stairs, I realized I was drunk; that someone had spiked the second daiquiri.”
“Jeffrey pulled me into a bedroom and closed the door. The room reeked. The bed was a mess. Couples apparently had been taking turns in the room and Jeffrey had been waiting for our turn to come up.”
The look on Ashlynne’s face turned from anger to fear.
“I was scared. I had been dragged into a room without being asked and now I was alone with a really big guy. Jeffrey said ‘We’ve got some privacy now. Let’s lay down on the bed.’ At this point, I was completely out of the mood. I told Jeffrey that I wanted to go home. He said that I had wanted to go someplace where we could be alone and here we were. He tried to kiss me. I dodged away. He said, ‘What’s wrong? You were kissing me earlier.’ I said that I had been comfortable then but I wasn’t comfortable now. I stepped away from him and he followed me. I kept saying that I wanted to go home and he kept saying that we were alone now just like I wanted. Finally, he lunged at me and missed. I got behind him and kicked him in the back of the knee. He went down. The bedroom had a bathroom. I ran in there, locked the door and called you. Once you agreed to get me, I yelled through the door that you were on your way and that you were a champion wrestler. I recited every tournament you’ve ever won and a few more I made up. Jeffrey tried to talk me out of the bathroom, but I
refused. Once you texted me that you had arrived, I opened the bathroom door and Jeffrey let me leave the room. Then you took me home.”
I thought Ashlynne’s story over. Had Ashlynne blown it all out of proportion? Had Jeffrey realized he was being stupid when Ashlynne locked herself in the bathroom and if she had come out, would he had taken her home? Maybe. Or maybe Jeffrey would have fucked her against her will.Too many football players at my old high school thought that every girl that showed interest in them wanted to fuck them. I wished that they taught positive consent at my old high school, but anything about sex was verboten.
“You did the right thing in calling me. I’m glad that I could come get you.”
Ashlynne sprang off the bed and gave me a hug. “Thanks again.” She sat back down on the bed. “How was college?”
“Great up until the very end, where it really sucked.”
“How did it suck?”
“In a sucky way.”
I turned back to my computer and brought up a video that I had been watching before Ashlynne came in.
“That’s all you’re going to tell me? I tell you all the details of my harrowing date and all you’re going to tell me about your year in college is that at the end it sucked?”
I shrugged, grabbed my headphones and lifted them towards me head.
Ashlynne shot up. “God, you’re the biggest jerk. Why do I have to have such a loser for a big brother?”
I never told Ashlynne or my parents anything that I didn’t have to. My parents were so uptight that my doing something the least bit wrong would set them off. But Ashlynne had a point – she had told me all the details of her date when I had asked and now I was stonewalling her. As Ashlynne stormed across the room, I began regretting blowing her off. When she reached the door, I said, “Okay. I’ll tell you more but you have to promise to tell none of this to Mom and Dad.”
“I promise,” said Ashlynne as she crossed back to my bed.
“Start of the year in the dorms, I went trawling for freshmen girls. I found one named Mandy that I hit it off with. Mandy is very cute, very smart and lots of fun.”
“Is she good in bed?” Ashlynne said it kind of joking, kind of seriously.
None of your fucking business.
“She is very FUN. Anyways, after a couple of weeks we went out. We dated the whole year. It was great – she was my best girlfriend ever.”
“My plan was to visit her regularly this summer. Mandy’s family lives a little over an hour from here. Work and Mandy were the sum total of my summer plans.” I took a big breath. “Thursday, Mandy had her last final in the morning and then her family moved her out of the dorms.”
“Why didn’t you help?”
“Mandy’s sister Brooke goes to the university too – just got her degree and Brooke and I don’t get along.”
“While Mandy was having her final, I helped my roommate Zach take his stuff out to his car. The dorms were a madhouse with too many cars for not a lot of spaces, so we had to haul his stuff a major distance. We bitched about the dorms the whole time. After we loaded the last of his stuff, Zach turned to me and said, ‘What would you think about getting an apartment next year instead of going back to the dorms?’ I said I liked the idea and that I’d research it.”
“Do Mom and Dad know you’re thinking of getting an apartment?”
“It was the important discussion we had last night.” Really none of her business. “As I walked back to the dorms, I had a brilliant idea – why not live with Mandy instead of Zach? Mom and Dad would probably freak and cut me off financially, but Mandy and I still might be able to afford it.”
“Mom and Dad would freak out.”
I shrugged. “Maybe. Parents aren’t as strict on juniors in college, particularly if they don’t have a little sister in high school. Regardless, I was looking on my laptop at apartments near the university when I heard a knock. I looked up as Mandy came in. ‘Mandy! I was just thinking about you! What are you doing here?’ ‘I can only stay a minute. My parents surprised Brooke with a summer vacation touring Europe. Airfare, Eurail pass and spending money.’ ‘Great for her!’ ‘And my parents surprised me by giving me the exact same trip. Brooke and I are going to tour Europe together. As I’m not going to see you for the summer, let’s break up and get back together in the fall. Gotta go!’ And she left.” I sighed. “I was stunned. I sat there in shock for ten minutes. Finally, I decided that we needed to talk this out. I called Mandy, but it went to voicemail. She texted me back that she’s crazy busy right now, but she’ll get back to me later. Then she never got back to me.”
“And she’s gone to Europe.”
“I think so, but I don’t know squat. What I do know is that everything I was looking forward to this summer won’t happen. Living together is out. Suckety suck suck suck.”
“Are you going to get back together with her in the fall?”
“Maybe.” I got up and started pacing. “She was a great girlfriend and it’s not her fault that her parents surprised her with a trip to Europe. She was looking forward to being with me this summer as much as I was looking forward to being with her. Her sister isn’t dating anyone and will be looking to pick up guys. I’d guess that it was her idea that Mandy break up with me so they can prowl together. Right now, I don’t want to forgive her. But will that change when I see her in the fall? It’s easy to forgive a hot girl who knows how to turn you on. There are few women in my engineering classes, I won’t be in the dorms to trawl freshman girls and I don’t know how easy it will be to meet girls at our apartment. By not getting back together with her, I could be cutting off my nose to spite my face.”
I sat back down. “So this summer is going to suck big time unless I somehow hook up with a nice girl who’s open to dating only for the summer.” I turned back to the computer and picked up my headphones. “Get out of here so I can cry in my beer.”
* * * *
After that weekend, things changed between Ashlynne and me. I rarely
saw her as I was closing every night except Friday and she had two more
weeks of school. When we did run into each other, we didn’t have any
fights and in fact were friendly. Ashlynne graduated as the valedictorian
with a perfect 4.0 grade point average. The Monday morning after
Ashlynne’s graduation, I came down the stairs to find Ashlynne in the
kitchen eating breakfast in a bikini. Mom and Dad had already left for
“Good morning,” I said.
My sister had been reading a book while eating non-fat yogurt with some
healthy, high-fiber cereal added. I pulled out a box of Cap’n Crunch and
poured myself a big bowl.
“I don’t think I’ve ever seen you eat breakfast in a bikini before.”
Ashlynne laughed. “I slept in late and as soon as I finish breakfast,
I’m going over to a friend’s to hang out at her pool all day. How was work
“Same old, same old; which is a good thing. Work is only interesting
when bad things happen.”
“I was wondering – what major was Mandy? Engineering?”
“I didn’t picture you as the type to date a women’s studies major.”
I shrugged. “She wasn’t how I pictured a women’s studies major to be
and I did picture myself dating someone as cute as Mandy, so I decided to
give it a try. It was a little rough at first because Mandy was so big
into positive consent, but it worked out. We had a lot of long,
interesting discussions that opened my eyes to what was going on around
“Have you forgiven Mandy for going to Europe?”
“Umm…No. It really pisses me off that she’d suddenly unilaterally
change our relationship. Our relationship had been all about communication
and mutual agreement. When she gets back from Europe, we’ll meet and talk
things over. I’ll decide then if I want to get back together with her.”
The more I got over the shock of our breakup, the more doubtful I was that
we’d get back together. “Regardless, I’m looking to date someone this
summer; somebody to have fun with. Speaking of that, I hope I wasn’t too
pushy when I asked you to set me up with a cheerleader.”
“It didn’t bother me, but don’t ask me again. I don’t keep track of the
love lives of other cheerleaders.”
“Anyone at your work you’re thinking of asking out?”
“There’s someone my age who has expressed interest in me.” I paused for
the punch line. “She’s a mother of two.”
Ashlynne laughed. “I’m guessing that you don’t want an insta-family.”
I shrugged. “It’s not the end of the world, but she’s not special.”
“What do you consider special?”
“Smart. Good-looking. Fun, ambitious, nice personality and fit.”
Ashlynne nodded her head. “Girls who are good-looking, fun, nice
personality and fit get snapped up pretty fast. Guys aren’t that
interested in ambitious smart girls, so most girls have learned to act not
smart. But overall, you’re not likely to date someone special here.”
I wasn’t surprised. The joys of small town life. “You said way back
that you want to go out with a smart athlete. How come? Why not just
someone smart or just an athlete?”
“He definitely has to be smart. I’m not going to play dumb for some
guy. As for being an athlete, it’s what’s attractive to me. As a
cheerleader, I was around athletes all the time and I’m used to muscular
guys. Thin, little nerds have no appeal. I’m hoping I’ll have better luck
at the university than I’ve had here.” Ashlynne and I were going to be
attending the same public university. “I’ve had lots of dates, but I
haven’t met a guy that I wanted as a boyfriend.”
“Seriously. I’ve been so busy all through high school. Cheerleading
took up a huge amount of time and classes took up most of the rest. If I
was going to make time for a guy, he had to be something special and I
didn’t met anyone that special.” Ashlynne closed her book. “Time for me to
be off. Would you please take my dish when you take yours?”
I watched as Ashlynne stood and left the room. It was hard for me to
believe that someone as hot as she was couldn’t find a boyfriend. I did
know that nobody had worked harder at cheer than her. Nobody had
outstudied her. I had worked hard at wrestling and my studies, but not as
hard as Ashlynne had. So her not having time for a boyfriend sounded
plausible. She would have time this summer for one, but then she would
have to study, study, study at college if she was going to get into med
Ashlynne had always been the one my parents had been the most proud of.
Growing up, I had played a variety of sports and had been good but not
great at all of them. Ashlynne had also played a variety of sports, but
had been great at cheer right away. When I had settled on wrestling, Mom
and Dad had been supportive but never excited. Whenever they had talked to
friends and family, they had always started with the latest news on
Ashlynne’s cheerleading and then had discussed my wrestling if they had
time. Now, they were over the moon about Ashlynne becoming a doctor while
they were merely pleased that I was going to be an engineer.
I had to admit that I had done a lot of mean things to Ashlynne over the
years. I had started most of our fights. I had loved to mock her about
not being able to spell her own name correctly. But now that we weren’t
fighting, it was hard for me to remember why I had been always so angry at
her. Was it because I was really angry at my parents for so obviously
favoring her? If so, how was that her fault?
* * * *
The next Monday, I was on my second bowl of Cap’n Crunch when Ashlynne
came into the kitchen. I nearly spewed my food – Ashlynne was wearing a
When Ashlynne had been thirteen, she realized one night that I was
checking out her then-small titties. She had freaked out and had been
furious at me. Since then, she would never let me see her in a nightshirt
if she could help it. It had been one of those things that we had fought
constantly about. Once she was in a nightshirt, I couldn’t come into her
room. If I had to talk to her, she’d crack open the door a tiny bit and
hide behind it so I’d couldn’t see any of her as we talked. If our parents
wanted her to come out of her room while she was in a nightshirt, I had to
stay in my room. If we traveled, she’d tell me every night to not be a
perv and check her out. If Mom and Dad left the room and/or looked away,
I’d check out her body. She did have a hot body and it royally pissed her
“What are you reading?” asked Ashlynne.
“Uncle Tom’s Cabin.”
“What? Why are you reading that?”
We had had breakfast together all last week. Without Mom and Dad to
rouse us out of bed, we both got up at about the same time. Ashlynne was
down later than usual and I had slowed my eating so that I was still at the
dinner table when she showed. I had come to enjoy our morning talks before
we went our separate ways for the day.
“I should have read it for History during my freshman year, but I waited
too long and had to make due reading up on it online. It was in my room
and I thought ‘What the hell?'”
“How do you like it?”
“Not bad, but I can handle it only so long.”
Once Ashlynne had her yogurt and cereal, she joined me.
“You’re wearing a nightshirt.”
Ashlynne blushed. “Yeah. I didn’t feel like getting dressed yet. I’m
going to have to get used to boys seeing me in my nightshirt when I live in
She seemed very embarrassed. Was that why she was late coming down this
morning – building up the courage to let me see her in a nightshirt?
“What are you reading?” I asked.
“It’s a book about patients with bizarre neurological disorders. It’s
interesting yet weird.”
She told me about some of the patients.
Out of left field, Ashlynne said, “You’ve changed.”
“That happens. But don’t tell Mom and Dad.”
Ashlynne smiled. “You don’t treat me like I’m a little brat anymore.
You treat me like I have a brain.”
“You treat me with respect, like I’m your equal.”
“I wouldn’t go that far,” I said slightly sarcastically.
Ashlynne chuckled. “I wish other guys would treat me that way.”
“How do they treat you?”
“It’s hard to describe. They put me on a pedestal. They’re intimidated
by me. They really want to impress me.”
“Like a celebrity?”
“Yeah,” said Ashlynne a little surprised.
“I’ve lived in the big city for two years now. Small-town celebrities
don’t impress me.”
Ashlynne laughed. “Have you been going to the gym?”
“Would you mind if I joined you?”
“Not at all.”
“I haven’t had any kind of exercise since the end of the school year and
I’m starting to feel out of shape. Could I ask a big favor?”
“If some guy keeps talking to me and won’t take the hint that I’m not
interested, would you please shoo him away?”
* * * *
The next Monday, I was the one who came into the kitchen second.
Ashlynne was in a nightshirt. She had worn a nightshirt to breakfast
through Friday, had come down dressed on the weekend when Mom and Dad were
home, and was now back to a nightshirt. By now, we were spending quite a
bit of time with each other. We were both still tentative around each
other, like we expected the fighting to start back up at any time. But as
the summer had gone on, the conversations had gotten longer and the laughs
had come more easily.
Once I was seated at the table with my bowl of cereal, Ashlynne asked,
“You have this Friday off, right?”
“Right.” Friday was my only day off.
“Well, I’ve been discretely asking around about someone who might be
interested in going out with you and I’ve set you up for a blind date
“Really? With who?”
“Someone you wouldn’t know. I met her at a cheerleading camp a couple
of summers ago. We hit it off and have stayed in touch. She’s very smart,
good-looking, fun and is very nice. She lives an hour away from here. Is
that too far?”
“No. Not for someone like that.”
“She’ll meet you at 5:30 at the outside tables at the,” and she named my
favorite upscale fast-food place. “She’ll be wearing a T-shirt with a
unicorn on it.” Ashlynne gave me a piece of paper. “Here’s the address.”
“Thanks, Ashlynne.” I got up and gave her a hug. “This is awesome. I
wasn’t expecting this. I’m so excited. Thanks again.”
* * * *
All week, I looked forward to going out. Ashlynne wouldn’t tell me
anything more about my date other than to assure me that she indeed had all
the traits I was looking for. I was getting very bored at home and was
excited about the possibility of having someone to do things with.
I arrived a few minutes early for my date, wasted some time texting
Ashlynne that I had made it safely, then walked to the outside tables. One
person was waiting there – Ashlynne.
“What are you doing here?”
“What do you think?”
Then it struck me – she was wearing a t-shirt with a unicorn on it.
“Oh come on, Ashlynne! Is this some kind of sick joke?”
“No. Sit down.” I sat down. “I did ask around about girls for you to
go out with. I also asked around about guys I could go out with. Then I
realized that you’re the type of guy I want to go out with and I’m the type
of girl you want to go out. So why don’t we go out?”
“Because we’re brother and sister.”
“And we fought like cats and dogs for years. But we’ve been getting
along great this summer. When I described me to you, weren’t you excited
about going out with me?”
“Was it an accurate description?”
“Yeah but…weren’t you going to be staying at a friend’s this weekend?”
“Yes. Her parents are divorced and her dad lives here. She stays with
him every weekend and I tagged along this time.”
This was very weird, like one of those oddball neurological cases in
Ashlynne’s book. No way was I going out with my sister.
“Please, Todd. Just for once, I want a great date. Nobody knows us
here. Show me what it’s like to go out with a nice, smart athlete.”
I opened my mouth to tell her no, that it was a stupid idea and that I
couldn’t believe she wasted my Friday. Then I closed my mouth. We had
been getting along so well this summer and I didn’t want to go back to
fighting all the time. If I embarrassed her by saying no, how would she
“We’ll pretend it’s a true blind date,” said Ashlynne. “Two strangers
having fun together. Please, Todd. Just this once. I’ll never tell a
soul. What’s the harm?”
What would be the harm? Actually, wouldn’t it be good? To show my
sister how a guy should treat her on a date? She was very assertive and
once she knew how a guy should treat her, I felt that she would be able to
steer dates that way.
But I couldn’t date my sister. That was sick. Nobody dates their
sister. Even a sister as hot as Ashlynne. How would I react to her around
the house if I had been out on a date with her? What if the date was a
flop? Wouldn’t we revert back to our cycle of constantly fighting? And
what if our date was a success? That’d be awkward as hell.
I looked at Ashlynne. She wasn’t saying anything, but she had a
pleading look on her face. This was obviously important to her.
I couldn’t date my sister. I could date anyone else in the world, but I
couldn’t date my sister. Yes, she had all the traits I was looking for in
a date, but she was still my sister.
I asked, “So, Grace, how would this date work?” Grace was Ashlynne’s
middle name. “Am I paying for everything or are we going Dutch?”
Ashlynne frowned briefly then smiled. “Well, Oliver.” Oliver was my
middle name. “As you didn’t ask me out, I was thinking we would go Dutch.”
If we were going Dutch, then it wouldn’t be a real date. This would be
a show date, where I showed Ashlynne how guys should act on a date. I
could live with that.
“Grace, do you want to have dinner here? This is my favorite fast-food
“Your sister told me that. This is fine.”
We went in, ordered, got our food and sat down to eat. We both
continued to act as if it was a true blind date and that we didn’t know
anything about each other.
“Where are you going to go college at?” I asked. Ashlynne named a
university. “That’s where I go! I’m an engineering major. What are you
going to major in?”
The answers that “Grace” gave were always true for Ashlynne. I could
have made up a different life story for Oliver, but I wanted to keep things
simple and kept to what was true for me.
Ashlynne asked, “Have you read any novels lately?”
“I finished Uncle Tom’s Cabin yesterday.”
We talked about how Uncle Tom’s Cabin, Twelve Years a Slave and
Huckleberry Finn compared. Somehow that led to comparing the Avenger
movies with the X-Men movies. As we headed out the door, we were onto
parallels between gay marriage and the civil rights movement.
“What do you want to do next, Grace? A movie?”
“How about mini-golf?”
“I’ll warn you that I swing a mean putter.”
“Guys always brag about what’s swinging between their legs.”
I laughed. That was not a comment I ever expected my sister to say.
She was such a goody two-shoes that she never swore or said anything
Ashlynne had already picked out a mini-golf place and it was busy when
we arrived, but not nuts busy. We’d play a hole, talk about plot holes in
movies we had seen recently, and then when the family in front of us
finished the next hole, we’d play on.
“Let’s take a break for a little bit,” said Ashlynne as she pointed to a
bench. It was a bench slightly off the course that I guessed was for
parents to sit on as they watched their kids play. We walked over and sat
“I want to drop out of Grace-and-Oliver mode for a bit,” said Ashlynne.
“This is exactly what I want on a date – having fun while having
intelligent conversation. Why is it so hard for me to find a date like
“Because you live in a patriarchal small town where men are men and
women are to admire their manliness. Dates are shows where the guy is the
star, performing feats of manliness. The girl is to be attractive, which
you’re good at, and be appreciative of their manliness, which I’m guessing
you suck at. Relationships are based around the model of earned physical
affection – the guy earns it and the girl gives him what he has earned.”
Ashlynne looked at me openmouthed for a while and then said, “You have
changed.” Ashlynne shook her head. “And here I always thought of you as a
I flinched. That had been her standard insult for me. There was
something about bringing it up after I had gone along with her stupid blind
date idea that really ticked me off.
Ashlynne put her hand on my knee. “I hope I didn’t offend you with
“No, that didn’t offend me. I hope this doesn’t offend you, but I’ve
always thought of you as an entitled princess.”
“An entitled princess?!”
“Yeah. You always got what you wanted from Mom and Dad. When I got my
driver’s license, I somehow became Ashlynne’s taxi service.”
“Mom and Dad told me to have you drive me to all my cheerleading stuff.”
“QED! And did you ever say please or ask would it be too much trouble?
Never! Instead, it was always ‘Todd, drive me here! Drive me there!’
‘Todd, don’t do anything this afternoon because you have to pick me up.'”
“Maybe I would have asked nicely if you would have talked to me. I
could never get more than a monosyllable out of you as you sulked in the
“How would you have felt if your life was controlled by a fucking
entitled princess?” Anger over so many slights came boiling out. “Do you
know why I never talked to you? Because you kept squealing on me to Mom
and Dad. Why the hell should I’ve talked with you when you constantly
plucked some little tidbit out of what I told you and presented it to Mom
and Dad in the worst possible light?”
Ashlynne said nothing.
“And what about the stuff you found out about me at school? Who told
Mom and Dad that I had two six-packs hidden away in the garage?” Guilty
silence. “Who told Mom and Dad that Emily Thompson had been sexting me.”
Emily Thompson had been a classmate who flirted with guys by sending
topless selfies. “I lost my fucking cell phone because of that and had to
use a damn flip phone that couldn’t receive texts or emails. Do you know
how embarrassing that was?”
I seethed with anger. I waited, hoping for the apology that I felt I
had deserved years ago. Finally, Ashlynne said, “You did so many mean
things to me and you were so much bigger than me. Tattling was the only
way I could get back at you.”
That was it. No fucking apology. No regrets.
“Date’s over,” I said with controlled fury. “I’m taking you to your
I took Ashlynne’s club and ball and turned all of our stuff in at the
“Did you have a good time?” asked the cashier.
“Great!” I said sarcastically.
I turned and saw that Ashlynne had joined me. She looked very small. I
was still smoldering.
We walked silently to my car. I had opened the door for Ashlynne when
we arrived, but she could fucking well open it herself now. By the time I
had the car started, Ashlynne’s phone was giving me directions. We drove
Finally, the baggage between us had been pulled out. We had fought like
cats and dogs for years for damn good reasons. We had plenty of hurts to
hold grudges for. We had danced around our baggage the whole summer,
pretending that it wasn’t there; but it always there. It was why Ashlynne
had known nothing about my life at college. It was why I had been willing
to tell her about my life at college when I did – because she had given me
plenty to retaliate with if she squealed to Mom and Dad. It was why even a
short, pleasant conversation at breakfast each morning had seemed
revolutionary. Yes, hardly speaking for nine months had allowed some
wounds to close, but they were far from healed.
I heard Ashlynne mutter, “Us going out together was a stupid idea.”
My first instinct was to agree, but the way she said it pulled me up
short. Her voice was filled with such pain. Her tone made me want to put
my arm around her and tell her that it’ll be okay.
That was when I realized why we had gotten along so well this summer –
it had started with Ashlynne asking me to protect her and I had loved it. I
had been her hero when I picked her up at the party. She had intentionally
made herself vulnerable to me when she had agreed to me going in the house
first after the party and I had risen to the occasion. Then she had asked
me to shoo guys away when we went to the gym. I had never been protective
of Ashlynne before, but now I was. Maybe it was because I had wanted to be
protective of Mandy and she had never let me.
When I stopped in front of Ashlynne’s friend’s house, I decided to try
to salvage the evening. “Ashlynne, I’m sorry that I lost my temper. I’m
sorry that I’ve been holding on to all these hurts. I did many, many
things to hurt you and I felt justified doing every single one of them.
And I’m sure it’s the same for you. But we’re adults now. It’s time to
move past all that. I promise to not intentionally hurt you and to talk to
you if you promise to not act entitled around me and to not to squeal to
Mom and Dad about me.”
I waited. To my surprise, Ashlynne didn’t quickly agree. She was bent
over in her seat, staring at the glove box. She looked miserable.
Finally, she said, “I can’t agree to that, Todd. You were right – I am an
entitled princess. I always expect to get my way. Maybe it’s because Mom
and Dad spoil me. Maybe it’s because I’m so much better than everyone else
at everything I care about. I hate that I act that way. It’s hurt many
friendships. It’s probably why I’m so lousy at dating. I wish I was some
other way, but I’m not.” Ashlynne turned to me. “Do you want to know why I
arranged this blind date for us?”
She went back to staring at the glove box. “About a week ago, I was
with a bunch of my friends and somehow kissing your brother came up. All
of my friends were grossed out at the idea. I didn’t say anything, but I
thought, ‘Hey, my brother is a good-looking hunk. What would be so bad
about kissing him? I’ve kissed lots worse.’ So I took it as a challenge to
test if kissing my brother on a date would be yucky or fun. I felt
entitled to lie to you, to pull a big switcheroo when you got here. I
didn’t care if you wanted to go on a date with me or not. And of course, I
got my way. But only for a little while because it was a stupid idea.”
Ashlynne turned to me. “Would you have kissed me at the end of the date?”
“No.” I quickly amended. “Probably not. At most, a quick kiss on the
She went back to staring at the glove box. “I was wanting a lot more
kissing than that. That wouldn’t have proved if kissing your brother is
fun or yucky. Like I said, the whole thing was a stupid idea.”
I hated seeing Ashlynne looking so miserable. I had grown over the
summer to like her a lot. I wanted to end the evening on a positive note.
“Ashlynne, I give you permission to act entitled to me.”
“You can act entitled around me. Just make it fun.”
“What are you talking about? You hate it when I act entitled. And
I stopped and pulled my thoughts together. “When Mandy first brought up
the idea of us going out, she had a big list of Do’s and Don’ts that I
would have to follow on the date. My gut response was to say, ‘No way.’
But Mandy was a wonderful person that I really enjoyed being with, so I
said I’d give it a try. It was rocky at first, but we eventually developed
a strong relationship. You’re a wonderful person that I really enjoy being
with. If acting entitled is a part of you, then I’m willing to accept that
as long you try to make it fun for me.”
“I don’t believe you.”
“Look, Ashlynne. Tonight was fun until I lost my temper. If I hadn’t
gone along with your idea, I would have had another boring, sucky Friday
night. So even though you acted entitled, I gave you the benefit of the
doubt and everything turned out okay.”
“Until we had the fight.”
“Which was a good fight to have. We needed to discuss those issues. I
was never fully comfortable around you because I knew that eventually one
of those issues would blow up.”
“I’ve felt the same way.”
“But I think we can move on from them now. And I think I can handle you
acting entitled if you make it fun for me. Any other issues we should
“I’m a perfectionist.”
“That’s not an issue.”
“It is. It makes me miserable all the time.”
I didn’t see how being a perfectionist could make Ashlynne miserable. I
decide to leave that alone.
“Wrapping up – I’m suggesting we wipe the slate clean, we act towards
each other as we act towards our friends, and I’ll let you act entitled
around me as long as you make it fun. Think it over and we’ll talk about
it Monday at breakfast.”
“Okay.” She sounded agreeable to the idea. Ashlynne took the hint and
gathered her stuff to go. “Thanks, Todd.”
I watched her walk down the driveway. A fence ran along the driveway
and Ashlynne went through a gate in it. I then drove home.
* * * *
Monday morning, Ashlynne came in wearing a nightshirt and carrying two
“Good morning, Todd.”
“Good morning, Ashlynne.”
“So how is this going to work?”
“I don’t know. Act like you want to act and we’ll talk things through.”
“Okay.” Ashlynne handed me a book. “I want you to read this.” It was a
young adult book with a female protagonist. Not my type of book. “It’s my
favorite book. I’ve always wanted to have a serious discussion of it, but
none of my friends are interested in that type of thing.” Ashlynne seemed
uneasy, like she half expected me to flat out reject the idea.
I took the book, looked at the cover and read the back. “Does it have
“Hot sex scenes?”
“No, you silly.”
I sighed in fake exasperation. “I guess I can read it anyway.”
Ashlynne gave me a big smile, set her book down on the dining table and
went to get her yogurt and cereal. “How was your date with Grace?”
I thought it a very odd question. “It was good until we had a fight.”
“She told me that she had a good time up until the fight and she was
sorry for starting it. I had a good date with a guy named Oliver, but it
Ashlynne sounded psycho to me, but I played along. “Sorry to hear
Ashlynne sat down and told me about some show she had seen at her
* * * *
The next morning I came down carrying Ashlynne’s book. A bookmark was
inserted about a quarter way down.
“How do you like the book?”
“I’m enjoying it.”
Ashlynne and I spent breakfast and a good deal longer discussing the
book. The book was so-so, but discussing it with Ashlynne was a lot of
* * * *
When I got home that night, I found a note in my room from Ashlynne.
“I’d like a big favor tomorrow. Please be ready to go out by 8”
When I came down to breakfast, I asked Ashlynne, “So what’s the big
“Mrs. Armstrong was my favorite teacher and she has to go to school
today for a half-day. I volunteered to watch her two boys and I’d like you
to help me.”
“You want me to babysit?”
“I want you to have fun playing with the boys. They’re four and six and
I think they’d enjoy playing with a big guy.”
“I’ll do the little things to make sure everyone has a great time. I
have lunches and snacks packed.”
“And I get half the pay?”
“I’ll give you three-quarters. You can split zero anyway you want to.
I’m doing it because I like Mrs. Armstrong and I know you liked her, too.”
I drove us over to Mrs. Armstrong’s house and we took the boys to a
park. I played tag, hide-and-seek, run-from-the-scary-monster and a few
other games that Ashlynne thought up. I pushed the boys on the swings. I
gave piggyback rides. I raced the boys and always lost. Ashlynne took the
mommy role and I took the big kid role. Ashlynne made sure we were all
hydrated and had sunblock on. When one of the kids acted up, I would do
the same and then Ashlynne would sternly scold me. The boys found that
hilarious. Once Mrs. Armstrong was back, we took the boys home. They
gave me big hugs and told me I was the best babysitter they had ever had.
Back at our house, I said, “I’ve had my workout for the day. I’m going
to take a nap.”
“Before you go, would you please tell me something?”
“You said Mandy was big into positive consent and that it was rough
initially. What did you mean?”
“Positive consent means that both of us had to consent to every step in
the making out process every time.”
“Every step every time?”
“Didn’t that feel stupid, particularly after a while?”
“It felt very stupid at first. On our first date, we went to dinner and
a movie. At the movie, I asked if I could hold her hand and she agreed.
Then she asked if she could kiss me and I agreed. Once the movie was over,
we got in the car and once I was out of the parking spot, I reach over and
grabbed her hand. She yanked it out of my hand and told me that I needed
to ask permission before I did something.”
“And what did you think of that?”
“I thought this was going to be our only date.”
“But you went out again?”
“I changed my mind when later, back in her room, she asked if she could
give me head.” Ashlynne chuckled. “We quickly dropped verbally asking
permission and went to using hand and body gestures.”
“If I wanted to hold Mandy’s hand, I’d stick my hand out like this.” I
held my hand down at 45 degrees from my body with my fingers spread wide.
“If she wanted to hold my hand, she’d grab it. She wasn’t obligated to do
I discussed the other gestures we used to ask and give permission.
There were a lot of them. I finished with, “If I wanted to touch her
pussy, I’d put my palm on her belly button with my fingers pointed down.
She would spread her legs to give me permission. Same for her if she
wanted to touch my dick. We’d always ask verbal permission for oral sex
and for intercourse.”
“Wow. That sounds so crazy.”
“It was, but I got used to it. Positive consent was how Mandy wanted
foreplay. And as sex with her was frequent and good, I was willing to do
it. Any more questions?”
“Was Grace’s date with you like your dates with Mandy?”
“Not really. It was somewhat like my first dates with Mandy in that I
was trying to treat Grace with respect. To not be in charge and to not say
‘we’re going to eat here’ and ‘we’re going to do this after dinner.’
Instead, I suggested dinner and went along with her suggestion of
mini-golf. My later dates with Mandy were much, much different.”
“They were. Trust me.”
“Tell me how. You brought it up. It’s not fair to dangle clues then
not tell me.”
She had a point. “Okay. You have to understand that Mandy and I saw
each other every day in the dorms. We did lots of things together, either
by ourselves or with friends. Dates were a special time that happened only
occasionally. After we had been together for a while, we decided that
dates would be a safe space where we could act differently than we normally
did. Dates for us were all about sex. Positive consent went out the
window. We’d grope each other and Mandy would flash me. I’d talk dirty to
her and tell her in graphic detail what I was going to do when I got her
back to the room. It was all about building up a sexual frenzy. Then once
we got back to the room, we were like animals. We were all over each other
and anything went. Once we were satiated, we’d cuddle and have long,
serious talks. We’d talk about how much we loved each other and our plans
for the future. During those cuddle sessions, I could see us getting
married and living the rest of our lives together.” I missed those dates.
“Do you know what’s ironic about our dates? It’s the university’s policy
that every couple do positive consent every time for every step. Mandy is
the biggest advocate of positive consent I know and even she couldn’t
handle it all the time. I’ve come to understand that positive consent is a
good thing because it makes the guy pay attention to what the girl wants,
but the university’s policy needs to be something mere mortals can follow.”
“Do you still love Mandy?”
“No. She had me believing that I was the most important thing in the
world to her and then I discovered I wasn’t. Love is all about commitment
and I’ll never believe again that she’s fully committed to me.”
“Thanks for telling me all this.” Ashlynne gave me a firm hug. Once the
hug was over, I turned to go up for a nap. Ashlynne added, “Grace wants to
go out Friday.”
“She wants to go out with you Friday. You pick the place to eat; she’ll
pick what you’ll do afterward.”
“Ashlynne…I thought the date with Grace was a one-time thing.”
“It was. But it got interrupted. And she said she has a challenge she
wants to finish with you.”
I shook my head. “No, Ashlynne.”
“She’ll make it fun.”
* * * *
Thursday morning, Ashlynne came down in a nightshirt I hadn’t seen
before. It was a light blue that nicely complimented her blue eyes and
“Is that new?” I asked.
“I was getting bored with my old nightshirts, so I traded with a friend.
Do you like this?”
“It looks great on you.”
The nightshirt was also very clingy and thin. I could see her tits
quite well. I could easily discern the dark ring of her areola.
Ashlynne’s nipples tented the fabric. Ashlynne was well-endowed and the
nightshirt clung tightly to every curve of her tits as they stood up
proudly on her chest.
I realized that I was staring at Ashlynne’s chest. When I looked back
up to Ashlynne’s face, she smiled.
“I got a game for us to play,” she said as she handed me a video game.
It was a dancing game.
“I’ll suck at this.”
“Doesn’t matter. You’ll have fun anyway.”
I hemmed and hawed, but finally agreed. I got the feeling that my
fighting her suggestions made my final submission even sweeter for her.
We played for over an hour and I did suck at the game. Ashlynne got
near perfect scores, particularly after she had done a dance once. But it
was fun. Ashlynne played braless and watching her big tits bounce up and
down as she danced had me hard the whole time.
When we were sitting on the couch after playing, Ashlynne said, “If you
went out with Grace on Friday…”
“I’m not going out with Grace on Friday.”
“If hypothetically you went out with Grace on Friday, it could be a safe
space, couldn’t it? You could let Grace act as she wants and you’d go
along, even if that’s not how you would want to act on a day-to-day basis?”
“I’m not going out with Grace on Friday.”
“But if you did, would you go along with what she wanted? And not hold
how she acted against her?”
I knew what Ashlynne was doing – I’d seen her do it so many times with
our parents. Whenever she decided to do something that they didn’t agree
to, she’d push and push and push. Most of the pushes were subtle so our
parents hadn’t been able to say to stop bringing up the subject. Ashlynne
would turn almost every topic into how great it would be if she had her
way. Eventually, she would wear them down and they’d agree. I wasn’t going
to wear down.
“If I were to go on a hypothetical date with the hypothetical Grace who
I would hypothetically never see after the date, then I wouldn’t hold any
of her actions against her when I didn’t see her again.”
Ashlynne smiled, apparently accepting my statement as agreement. “I
really like the idea of a date as a safe space where I could act how I want
to act, not how I feel I should act.”
I was very distracted at work that night. When I got home, I was eager
to jerk off but I couldn’t find any porn that was satisfying. I eventually
closed my eyes and came while envisioning Ashlynne’s naked tits bouncing in
front of me.
* * * *
Friday morning, Ashlynne came down in the light blue nightshirt again.
“What are your plans for your day off?”
“Work out, take the minivan to the dealer, then play Xbox at a friend
from work’s house.” Mom’s minivan needed some routine service and Dad had
volunteered me to take it the dealership while Mom drove my car.
“You could play with your friend on Saturday and go out with Grace
tonight. She’s picked something to do that I think you’ll really enjoy.”
“No, Ashlynne. I have other plans.”
“If you change your mind, let me know. She’ll be waiting for you.”
At the gym, a guy kept trying to talk to Ashlynne after she had put on
her earbuds and had started running on the treadmill. I had to come over
and explain to him that my sister wasn’t interested. He gave me an ugly
look, but finally moved on. Ashlynne gave me a big smile while she kept
After lunch, I took the minivan to the dealership. While I was chilling
in the waiting area, my friend from work called. “Hey, Todd. Courtney
called in sick and I’m going to work her shift. I need the hours. Sorry
about canceling on you.”
“Get together tomorrow?”
“Sure.” We set a time and I hung up.
Another Friday night and nothing to do in our podunk little town. Of
course, I had another option. I could go out on a date with “Grace”. I’d
almost certainly have fun. Lots of fun. Maybe too much fun.
If I went out with Ashlynne, I would show her how a guy should treat
her. I knew from training people at work that you could tell people how to
do something over and over again, but it never sank in until they actually
did it. After the date, we’d hopefully go back to being brother and
sister. When Ashlynne went out on a date at the university, she’d know how
to steer the relationship into the right direction and she’d never have to
call me again to come rescue her. Mission accomplished by the protective
The problem was that Ashlynne and I weren’t acting like a brother and
sister anymore. As stupid as our fights over her nightshirts had been,
they had made sense in terms of a normal brother-sister relationship. We
were acting more like Mandy and I had acted before our first date. That
made me feel queasy about going out on a date with Ashlynne.
The other choice was to stay home, lock myself in my bedroom and beat my
meat while watching some babe with fake tits that I cared nothing about get
fucked by some dude that I’d never seen before.
Having fun won.
“Hey, Ashlynne.” I said when she answered her phone. “My friend
canceled and I’m available for a date with Grace.”
“I’ll text you where to meet. I’ll see her at 5:30.”
* * * *
Ashlynne was waiting outside when I arrived. She was wearing a tank top
that had a unicorn on it which showed off her nice shoulders.
“Hello, Grace. Good to see you again.”
“Good to see you, Oliver.”
“Is that a new shirt?”
“How would you know if it is a new shirt if you’ve only met me once
Duh. I rolled me eyes and we went inside.
One problem with the blind date charade was that I couldn’t remember
what we had told each other. Ashlynne was prepared and she spent the most
of the meal recapping what we had told each other before. After that, we
talked about the novel she had given me and that I had finished at the
After dinner, Ashlynne wouldn’t tell me where we were going, but only
that it was about a half hour away. She had the address plugged into her
phone and I followed the directions. While we drove, we talked more about
the novel, compared the movie to the novel and discussed similar movies.
Our destination was a convention center not that far from the
university. They were having a car show.
“Is this okay?” asked Ashlynne.
“Should be interesting.”
In the parking lot, I got out and opened the door for Ashlynne. When
she stood up, she stuck out her hand and wiggled her fingers. It was the
gesture Mandy and I had used to request to hold hands. It was decision
time – was this going to be a show date like our first date or a real date?
I took Ashlynne’s hand in mine.
Ashlynne said, “Let’s go see what the cousins have been up to.”
“The cousins” was the term in our family for the Chevrolet division of
General Motors. As they had been nice enough to name a car brand after us,
we had always felt obligated to support them. Dad drove a Chevy, as did
Ashlynne and I. It irked Dad to no end that Mom had insisted on driving a
non-Chevy minivan. My dream job was to work for Chevrolet, preferably
designing cars. I thought it would be great to freak people out. Some
vendor giving our department problems? “We’ll have Mr. Chevrolet speak
Inside the show, we made a beeline for the Chevrolet display, where we
lovingly checked out each car they had on display. Ashlynne started acting
differently – sillier and more demanding.
“Open the door for me, Oliver.” “Now take my picture.” She batted her
lashes at me. “How do you think I look in this car?” as she posed with one
arm raised behind her head. “Does this interior color go with my
lipstick?” “Did you bring any reflective sunglasses? I need to see how I
look in this car with reflective sunglasses on.”
I didn’t know what Ashlynne was doing. She had never been this vain and
shallow. I took lots of pictures of her because she wanted me to take lots
of pictures of her.
As she was getting into a Silverado with a black interior, she stopped
and thrust her ass at me. “Does this interior make my butt look big?”
I rolled my eyes. I had no clue how to answer that. She got the rest
of the way in, sat up in the seat and closed the door. I leaned through
the window and said, “The interior makes your chest look big.”
“Oooh! I like that! Take a picture of me and my big chest!”
I did and then leaned forward again. “All the interiors make your chest
“I like that even better!” Ashlynne smiled then winked at me.
After that, I did my best to play along by constantly complimenting her
looks, showering her with attention and taking her picture whenever she
seemed close to striking a pose. I let her be the star of our date.
“Which one are you going to buy me, Oliver?”
“That one,” I said as I pointed to a massive four-by-four truck.
Ashlynne laughed. “That’s for guys with small dicks.”
“No, it’s not. It’s the vehicle of choice for someone living a
lifestyle that you don’t understand. That doesn’t mean that it’s wrong,
it’s just different. You’ll learn to respect alternative lifestyles at
Ashlynne snorted. “I’m too familiar with that lifestyle. And I still
think it’s for guys with small dicks.”
“Don’t take human sexuality at college. It sounds cool, but it’s
actually boring. The only thing I found interesting was the discussion of
dick size. Most guys think their dicks are too small, even if they’re of
“And you don’t think your dick is too small?”
“No. It’s about average and I’ve never gotten any complaints. It’s not
that important to girls.”
“What makes you think that?” she said as she batted her eyes at me.
“I’ll believe it’s important to girls when they come out with the
boxer’s equivalent of a push up bra.” Ashlynne laughed. “And what do you
think of dick size?” Ashlynne blushed and said nothing. “I think it’s
become a new curse. Before people would say,” I raised my fist and shook
it, “‘May the fleas of a thousand camels invade your armpits!’ Now, people
say, ‘May you have a microdick!'”
I said the last line too loudly and several people turned and stared.
Ashlynne giggled while holding tight to my arm.
“My, my, Oliver,” Ashlynne said in a pompous voice. “You must learn to
watch your language.”
“You’re acting crazy.”
“Go ahead. Get in my face and tell me I’m acting like a crazy, entitled
I scrunched down so that I was at her eye level and my nose was an inch
away from hers. “You’re acting like a crazy, entitled princess.”
Ashlynne kissed me.
I felt like I was stuck by lightning. I heard Ashlynne giggling as she
danced around me. I stood there like a statue. I finally gathered my wits
and moved on to the next Chevy. Ashlynne moved next to me and gave me the
“I want to hold your hand” signal. I ignored her.
“That was very bad of you.”
Ashlynne snorted and giggled, then danced away from me.
I couldn’t believe how my sister was acting. She had always been so
serious. One of my favorite ways to annoy her had been to tell her to
lighten up or to smile. Both of course had the opposite effect every time.
Ashlynne asked, “What do you think of this paint job?”
I looked at Ashlynne and she was bent way forward over the hood of a
small car. I could see all the way down her tank top. She was wearing a
lacy red bra that was dangling down enticingly.
Ashlynne cracked up and danced away again. Then she came up to me and
said, “This is so different from my other dates.” She held up her hand next
to her head and made circles with her finger. “I’ve got these thoughts
running through my head…”
“You know, you’re giving the universal crazy, entitled princess signal.”
Ashlynne exploded in laughter. “That was very bad of you.”
I shrugged. She held out her arm, wriggled her fingers and said, “I
know you’ll forgive a hot girl who knows how to turn you on.” I shook my
head then took her hand.
We finished the Chevrolet display and started wandering through the
other car brands. Ashlynne said, “I’ve never really flirted before.”
“Mom would punish me if she thought I was flirting. It wasn’t what good
“Mom wasn’t around you all the time.”
“Yes, but guys who I didn’t want to encourage were.”
“And you want to encourage me?”
“Of course! As I was saying before you rudely interrupted, I’m
constantly thinking of ideas of how to encourage you. That’s never
happened to me before. When you’re on a date with a girl, are you
constantly thinking of ideas to encourage her?”
“No. I’m trying to figure out if she has any padding in her bra.”
Ashlynne snorted. “Are you familiar with positive consent, Oliver?”
“I’ve had the term explained to me.”
“You keep your hands to yourself unless I give you permission
beforehand. And it doesn’t apply to me.”
Ashlynne gave my ass a squeeze, then exploded in giggles and danced
away. I shook my head in mock disapproval, which made her giggle more.
“So what are you encouraging me to do?” I asked.
“I should be clear on that. When we leave here, we’re going to go to my
friend’s house and park in the driveway. It’s a very private spot and
she’s told her dad to not bother us. We’re going to make out there for a
while. Then I’m going to go into her house and I’ll never see you again.
Is that okay with you?”
I felt slightly disappointed for some reason. “Yes.”
“And I can trust you to do only what I give you permission to do?”
“Great!” And she bent forward to give me another look down her shirt.
After she had giggled some more, she sidled up to me and took my
outstretched hand. “I feel so wicked. And I’m having so much fun. I
can’t imagine acting this way all the time, but it’s a lot of fun acting
this way in a safe space.” Ashlynne hugged me. “Thanks for playing along
and giving me the safe space.” She released the hug and went back to
holding my hand. “Maybe I should go into the bathroom and take off my
bra?” She flashed me a wicked smile and then laughed some more.
I couldn’t believe how my sister was acting. The girl who spent years
not letting me see her in a nightshirt was talking about flashing me her
“Aren’t you worried that you’ll give me the wrong impression?”
“No.” Her voice was serious for once. “I’ve realized that I can’t worry
about giving the wrong impression. After my date with Jeffrey, I beat
myself up over and over for having led him on more that I intended. I
thought it was my fault that I ended up locking myself in the bathroom.
But I’ve done a lot of reading since you talked to me about Mandy and I’ve
realized that I did nothing wrong. A woman cannot act or dress in such a
way that some man doesn’t get the wrong impression. My mistake was going
on a date with someone I couldn’t trust.”
Ashlynne stopped me and gave me a hug. “Thanks for letting me go out on
a date with someone who’s worthy of my trust.” She went up on tiptoes and
gave me a kiss. It wasn’t a long kiss, but it definitely wasn’t a sisterly
kiss. She moved back to my side and took my hand. “Ready to go?”
As we walked towards the exit, Ashlynne swung our hands way high. I
laughed at her childishness.
“By the way,” said Ashlynne. “I’ve already resolved my challenge.
Kissing my brother is fun.”
* * * *
When I got into the car, Ashlynne said, “My crazy, entitled princess
phase is over.”
“You’re now merely an entitled princess.”
“Yes. And a very happy one. What’s the gesture for you want to hold
hands in the car?”
I held my hand outstretched a foot above the console. Ashlynne laced
her fingers in mine.
I felt that we were both nervous on the drive to her friend’s house. I
responded to my nerves by being quiet and Ashlynne responded by talking
more, so the drive consisted of Ashlynne prattling on with me occasionally
saying something in response.
On the drive, I thought back to something Ashlynne had said about her
date with Jeffry – because it had gone well, she was going to let him do
anything he wanted as long as the clothes stayed on. I felt like our date
had gone great so far. Would she let me do anything I wanted as long as
our clothes stayed on? No, that was crazy. I was her brother and she
wouldn’t let me go too far. But I could probably stroke a lot of her body
and that’d be okay. But not her tits. I definitely wasn’t going to touch
I parked in the driveway in front of the garage at Ashlynne’s friend’s
house. We were well away from what looked like a quiet street. Her
friend’s house and the house next to it were both one-story, so no one
could look down on us. It was a very private place to park.
“Let’s get in the back, Oliver.”
We got out of the minivan and opened the side doors. I could hear the
faint sound of a movie or TV show from her friend’s house. The neighbor’s
house was dark. As we got back into the minivan, Ashlynne slipped her
fingers in mine. I felt so nervous – I hadn’t felt so nervous since my
first few dates. I tried to think of some line of conversation to discuss,
but my mind was mush. I thought briefly about sitting in one of the middle
seats but Ashlynne pulled me towards the back.
When we were seated on the back bench facing each other, I said, “Grace,
thanks for the-”
Ashlynne kissed me. Then she broke quickly broke it off.
“I’m sorry,” she said. “I should have asked permission.”
She seemed defensive.
“It’s okay. Do what you want. Don’t worry about positive consent.
You’re not going to overpower me and make me do something I don’t want to.
I’ll do positive consent so you’ll be in charge. Can I hold your hand?”
“Yes.” She laughed nervously.
I took her hand. “Are you okay?”
“Yes.” She seemed anxious.
“We don’t have to do anything else. I’ve had a great date and I don’t
mind ending it here.”
Ashlynne seemed to be getting pissed. “I want to kiss. I want to make
out. Let’s not talk about it anymore.”
“Okay.” I leaned forward to kiss her, giving her plenty of chance to
stop me. Instead, she leaned into my kiss. It was a short, soft kiss that
was followed by another one, then a longer one. I slipped my hand across
her flat stomach and pulled her closer to me. It was like a switch turned
off in my brain and I no longer thought of Ashlynne as my sister. She was
a woman who wanted to be kissed and I wanted to kiss her.
I slipped my tongue inside her mouth and she greedily sucked it in. I
explored her mouth while my hands roamed across the top of her collarbones,
across her shoulders, down her arms and along her long smooth legs.
Ashlynne kept her hands pressed against my chest, holding me in the same
relative position to her. I withdrew tongue and Ashlynne’s followed mine
into my mouth.
We Frenched like that for a long time. Ashlynne wanted to kiss on her
blind date and I was happy to go along. It had been a long time since
Mandy left. I enjoyed kissing and it felt good to use my lips and tongue
so intimately again.
My hands kept roaming and in each circuit, they moved a little bit
closer to Ashlynne’s tits. I kept the presence of mind to not grope my
sister. I pulled back and kissed her on the lips. That triggered a series
of hot, sloppy kisses where we kissed each other all around our mouths. As
we kissed, I kept thinking about her tits. How they looked when the last
time I saw her in a bikini. How they looked in various nightshirts. I
tried to not think about them, but the harder I tried, the more images of
them leapt unrequested to my mind. I had never dated anyone with tits as
large as Ashlynne’s. And they called to me like sirens.
I decided to do something different. I broke off our kisses, dropped my
head down and nibbled lightly on Ashlynne’s neck.
“Do you like that, Grace?”
“Oh yes, Oliver.”
Ashlynne ran her fingers through my hair as I continued lightly nibbling
on her neck. I nibbled upwards until I reached her right ear. I whispered
in, “You’re so wonderful, Grace.” I nibbled here earlobe. “Do you like
“God yes, Oliver.”
Ashlynne was panting. I nibbled her ear a few more times before
swinging my face around for a kiss. As I did, Ashlynne grabbed my head and
rammed her tongue into my mouth while pulling me upwards so we were
somewhat standing with one bent knee on the bench seat and one angled leg
on the floor. Our tongues dueled frantically in my mouth as we ground our
bodies together. Any thought of asking permission was gone. Besides,
Ashlynne was initiating as much as I was. I realized I was cupping
Ashlynne’s ass with my right hand to balance myself. When I moved my hand
away, she grabbed it and pulled it back. I began running my hand up from
above the back of her knee up to her ass and then back down as we continued
to frantically kiss. On each trip up, I gave her ass a strong rub and a
I broke off the kiss and switched to nibbling on her neck. At the same
time, I grabbed Ashlynne’s ass with both hands and pulled her against me.
“Do you want this?” I asked.
I rubbed her shorts-covered pussy up and down on my cock. My brain was
filled with animal lust, a lust that didn’t care that this woman I was
madly groping was my sister. I continued dry humping Ashlynne while
squeezing her perfect ass. We were moving too much for me to nibble on her
neck so I concentrated on grinding my crotch against hers. It felt so damn
good that I was completely lost in the pleasure. The only things that
existed in the world were Ashlynne’s ass, my dick and her crotch.
Suddenly, something else existed – sperm. Lots and lots of sperm. They
were fleeing my balls in a quest for freedom. My cock exploded with a
massive cum inside my underwear. Each spurt felt huge. My knees almost
buckled from the strength of the explosion.
What the hell was I doing? Dry humping my sister? This was not what I
intended. This was crazy. And sick. And crazy sick.
“Let’s stop, Grace,” I said.
“Did I do something wrong?” Ashlynne sounded scared.
“You did nothing wrong.”
I put my hands on her hips and guided her so that I had one leg down the
bench seat and one leg on the floor and Ashlynne in front of me with her
back pressed against my chest.
“If I did nothing wrong, then why are we stopping?” The pitch of her
voice was rising.
I wrapped my arms around her.
“I got carried away and should have checked in more. Were you okay with
what we were doing?”
“Yes. Are you sure that I didn’t mess up?” Ashlynne sounded close to
“You were great! You were too good. I wanted you to be in control but
once I started kissing you, I lost control. I’m sorry. You were a great
“Yes, really. It was crazy hot kissing you. I did things that I didn’t
intend to do, so I stopped to make sure that you weren’t upset that I had
gone too far.”
“No. I wasn’t upset at all. When you stopped, I thought it was because
“Would you like to kiss some more?”
Ashlynne twisted in the seat and we kissed. With a big load blown, I
didn’t feel nearly as frantic. The kisses were softer and more caressing.
I slipped my tongue into her mouth again, but slowly this time. I was in
no hurry and broke off kissing to talk.
“You’re wonderful to kiss,” I said.
“Thanks. You’re great kisser, too. I’m sorry that I panicked there.”
“It was okay. You had nothing to be concerned about it.”
“It’s just that…” Ashlynne sighed. “I’m a perfectionist. I hate
doing anything wrong. On dates, I worry constantly that I’m screwing up;
that I’m kissing wrong; or I’m kissing when I should be doing something
else; that I’m too aggressive or I’m too passive.”
“You were wonderful. Relax and enjoy.”
I moved Ashlynne so we could kiss again and she rose to meet me. We
kissed awhile, some Frenching and some on the lips. I stopped us once
“So good,” I told Ashlynne. “You’re great to be with.”
“I know this is probably going to sound awful, but I was really enjoying
it when we were out of control.”
“And I was enjoying it to.” My nasty underwear was a testimonial to
that. “But we were doing things that you enjoyed. It could have gone on to
something that you weren’t ready for. It’s a lot better to go slow.”
Ashlynne pouted slightly. “You’re not trying to set a speed record.
You’re trying to build a strong relationship. A strong relationship takes
trust. And building trust takes time. So go slow.”
She seemed more satisfied with that. She leaned back into me and
“I never thought I’d say this,” I said as I wrapped her in my arms. “I
like being the protective big brother.”
Ashlynne laughed. “You do a great job of it. I feel safe with you.”
She put her arms on my arms and squeezed, effectively giving herself a hug.
“I don’t mean just physically safe. I feel emotionally safe with you. I
had that panic and I was afraid that I was going to ruin the date again,
but you calmed me down and made me feel good about myself.”
I gave her a hug. “You have a lot to feel good about.”
“I know. It’s that…” Ashlynne sighed. “Mom and Dad have always been
DON’T DO ANYTHING. And I’ve always been a good girl. But I feel like I
should have moved beyond that long ago. I’ve should have spread my wings
and explored. I feel like when I go out now that guys expect me to have a
certain level of experience that I don’t have. I’m afraid that I’ll do
something super stupid, then my date will laugh at me and tell everyone at
school that I’m such a noob. When something happens that I’m not
expecting, I panic.”
“Be upfront about your inexperience to your date. I’m sure that he’ll
understand. He’ll probably find it exciting that he gets to teach you.
I’d find it exciting.”
“There you go, making me feel good about myself.”
“We’ve done everything you wanted to do. Are you ready to go in?”
“Not yet. Can we kiss some more?”
“Sure. I’ll kiss you as long as you want to kiss.”
We kissed some more. As we kissed, our kisses got steamier. Soon, we
were Frenching vigorously. I was sorely tempted to slide my hands up and
cup her big tits. I was getting too excited and I stopped.
“How do you feel?” I asked.
“Happy. Sexy. A little out of control and I like that. Ready to do
I didn’t know what to make of Ashlynne’s last comment. She didn’t give
me any time to think about it – she resumed vigorously kissing me. As she
kissed me, she put her arms over mine and pressed her fingers inside of
mine. As we continued to tongue wrestle, she slowly lifted my right hand
up until it cupped her tit. I stopped kissing.
“Ashlynne, we shouldn’t do that.”
“I’m an entitled princess – we’ll do what I want.”
“Ashlynne, I don’t think-”
She cut me off with a kiss, sliding her tongue into my mouth. I lost my
train of thought and was soon ardently kissing her back. I had noticed
that we had dropped the “Grace” and “Oliver”. It was now Todd and Ashlynne
who were making out. She raised both of my hands and put them on her tits.
Fuck it – if she wanted me to grope her tits, I wasn’t going to fight it.
I broke off the kiss and then repositioned Ashlynne so that I could kiss
on the right side of her neck while she leaned against me. I cupped her
tits in both of my hands and gently massaged them.
“Do you like this?”
I went back to kissing Ashlynne’s neck while she gently moaned. I loved
the feeling of her tits in my hands. It would have been even better if she
hadn’t been wearing a bra. Still, it was far, far more than I had expected
being able to do when she first suggested that we go on a blind date
“You’re so wonderful,” I said between kisses. “And beautiful. You have
such a great body.” Ashlynne made a kind of purring sound as she pressed
her body against mine. “You’ve been great to be with tonight. You’re such
a fun person. I’ve loved talking with you.”
As I continued complimenting Ashlynne, she started arching her back to
rub her ass against my now hard dick; essentially dry humping with her ass.
Damn – we should talk through that escalation of physical intimacy, but I
was enjoying it too much to stop it. The more I said sweet nothings while
rubbing her breasts, the more she undulated against me. I was losing
Then it struck me – I needed to end the date before I completely lost
control again. But I couldn’t end the date abruptly as Ashlynne would
think she’d done something wrong and freak out. But what if I ended the
date in a spectacular but safe manner? She had made me cum already. I
decided I should return the favor. We would keep our clothes on. I would
show her how her date could make her very happy.
I said softly into Ashlynne’s ear, “I’m going to make you feel very good
if it’s okay with you.” No response other than Ashlynne continued to
undulate against me. I moved my hands from Ashlynne’s tits down her torso.
“You can say to stop at any time and I’m fine with that.” When my hands had
moved down, Ashlynne had stopped undulating against me. Now, she lay
flopped against me, watching my hands move down her body. “You have such a
great body and I’m going to explore a little more of it.” My right hand
went to her crotch while my left hand went a bit further to grab her thigh
below her shorts. I rubbed my right hand’s middle finger in her cleft,
creating a camel toe.
“Do you want me to stop?”
“Does this feel good?”
“So far.” Ashlynne seemed a little tense, a little scared. She hadn’t
expected this escalation, but she trusted me.
“Good. I’m going to do this for you and then you’ll go inside. All
Ashlynne turned her head and kissed me while she pushed her crotch
against my hand. We kissed as I slowly pulled my hand up her camel toe
while pressing against her. She pushed her crotch against my hand in time
with my strokes. Our kisses slowed as I continued rubbing her slit. After
a bit, she stopped kissing me and laid back against me. She began taking
“You’re so wonderful,” I said softly. “I enjoy being with you. I’m so
happy being with you. I want to make you happy. I want to show you how
much I enjoy being with you. Cum for me. Let me make you happy.”
I continued rubbing my hand against her cleft. Ashlynne pressed her
crotch harder and harder against my hand. Her breath got more ragged and
then she was breathing in pants. I kissed her neck gently while I
continued rubbing hard against her crotch. Ashlynne said, “Oh!” Then
another “Oh!” Then a stream of “Oh! Oh! Oh!” Finally, her whole body
shuddered as she clamped her legs on my hand. I held her lightly as her
orgasm swept over her.
When Ashlynne recovered, she said, “God, that was great!” She gave me a
quick kiss. “Thanks for making me feel so good. I’ve never cum that hard
before.” Another quick kiss. “But I’m a mess now. My panties are soaked.”
“My underwear is a mess from when I came earlier.”
“You came earlier?”
“When we were dry humping.”
“Mom has a beach towel behind this seat. Let’s clean ourselves up.”
I reached down and opened the box of emergency supplies Mom kept. I
pulled out the beach towel. When I turned back around, Ashlynne had
slipped off her shorts and panties and was naked from the waist down. She
grabbed one end of the towel and started drying her crotch area.
“Take off your shorts and underwear.”
I felt torn. I had kept moving the goal posts, but had stopped at both
of us keeping our clothes on. I didn’t want to show my dick to my sister.
That was crossing a line that I didn’t want to cross.
“Come on. It’s not like I haven’t seen a boy’s dick before.”
That was it. It was enough to galvanize me into action. My underwear
was very uncomfortable and I did want to get cleaned up. I took off my
shorts and underwear.
“You did make a huge mess,” said Ashlynne. “Cum is everywhere.” She
took the other end of the towel and rubbed it all over my crotch, moving my
dick around when it got in the way. I stood upright with one knee on the
bench seat and one leg on the floor. Ashlynne turned on the light so she
could see better.
“Tonight’s been so crazy,” she said. “I felt so nervous about holding
your hand and now I’m cleaning your crotch like it’s the most natural thing
in the world.”
“It’s a great brother-sister bonding activity.”
Ashlynne laughed. “By the way, I lied when I said I’d seen a guy’s dick
before. I’ve seen them only in pictures and movies. Yours looks kind of
weird in person.”
“Thanks!” I said chuckling. “You feel good about tonight?”
“I do. I had a great time and I learned a lot. I’m hopeful I’ll be
comfortable and confident on my next date.”
Globs seemed to be stuck to each of my crotch hairs. Ashlynne was
drying each one with the towel.
“You’re such a perfectionist,” I said.
“I am. And it makes me miserable at times. I had to get every
cheerleading routine perfect. Any mistake and I was crushed, even if no
one noticed. You don’t know how many times I cried when I didn’t get a 100
on a test or assignment. And as I told you, it made me panic on dates.”
“Hopefully on your next date, you’ll be able to relax. When things
flowed tonight, they were great. You’re a very sexy woman.”
“I feel that way now, but I haven’t on other dates.” Ashlynne had the
area above my dick cleaned up and was working now on the area to the right
of my dick. “You know what really scares me? The idea of giving head to a
guy. It’s a valuable skill to learn. If you know how to do it well, it’ll
keep your guy satisfied without fucking. No need for birth control. No
chance of pregnancy. It’s how Mandy convinced you to go out with her on a
second date. When I was driving in the car with Jeffrey after the movie, I
thought briefly about giving him head when we got somewhere private. Then
I remembered I had no idea of how to do it.”
“It’s not that hard. You can learn.”
“No, I can’t. Normally for something like this, I’d watch videos and
practice, practice, practice by myself until I had it mastered. Only then
would I be comfortable trying it with someone else.”
“You can easily find videos where girls give head to a guy.”
“I’ve watched porn at some sleepovers. The other girls who’ve given
head hoot at the oral sex in those videos. They say nobody’s dick is that
big and they’d gag on something so huge. They say when they give head,
it’s nothing like that. So I’m not going to learn how to give head by
watching porn.” The right side was clean and Ashlynne was working on the
left side. “And I’d still need a guy’s dick to practice on.”
“Well, I could-”
I was tired; it was late and I had driven a lot. I almost made a big
mistake and fortunately caught myself in time.
“You could what?”
Ashlynne gave me a “don’t give me that shit” look.
“Okay. I could give you some instructions on what to do.” That wasn’t
what I was going to say, but it sounded reasonable.
Ashlynne went back to cleaning me up. She grabbed my dick and lifted it
up so she could run the towel over my balls. “Have you ever given head
“Then I’d be better off with instructions from one of my girlfriends.”
Ashlynne had accepted my altered line. I felt like I had dodged a
Ashlynne was apparently satisfied that my balls were clean and moved the
towel up into my ass crack. Without so many hairs, she could clean a lot
faster. Finally, Ashlynne seemed satisfied. She tossed the towel over the
seat back and turned off the light, but she kept her left hand wrapped
around my dick.
“Would you?” she asked.
“Would I what?”
“Would you teach me how to give head? That’s what you were going to
say, wasn’t it?”
She had caught me out.
“And I stopped myself because it was a very bad idea. I hope you
weren’t offended that I’d think of such a thing.”
“I wasn’t offended. I want to learn.” She slowly caressed my dick with
“Why not learn from your next boyfriend?” Should I have said first
“Because he’ll expect I already know how to give head. And I’ll panic
because I can’t do it right.” She dropped her left hand to her side and
moved her right hand down to cup my balls. In a sweet voice, she said,
“You’ve made me cum but I haven’t made you cum.”
“It’s okay. I came earlier.” She moved her hand back up to my dick. I
was very hard now and her touch was giving me tingles. I needed to bring
this date to an end. “You said you would go in after I made you cum.”
“I’ve changed my mind.”
“We’ve done enough for one night.”
“There’s no night after this. We’re both on a blind date with someone
we’ll never see again.”
Ashlynne was playing the entitled princess game, where she expected to
get what she wanted and wouldn’t take no for an answer.
Or was I playing the entitled princess game? Putting up a fight while
knowing that I’d give in because once I did, she’d make it fun.
Regardless, I could feel my will to fight crumbling. Her hand softly
exploring my dick wasn’t helping. I found Ashlynne’s combination of
assertiveness and innocence irresistible. Who didn’t want to teach a
gorgeous young woman how to give head?
“When I see you on Monday morning,” said Ashlynne, “none of this will
have happened. We’ll be as we have always been. You won’t try to kiss me
or touch me and I won’t try to kiss you or touch you. Tonight will be our
special secret that we’ll never discuss. Why not add a little bit more to
Why not? It wouldn’t hurt her and it is something that would be good
for her to know.
“If you’re sure you want to do this…”
“I feel safe doing things with you. You’ve been so patient and haven’t
pushed me. Just the opposite. I’ve liked being in control.” A little hint
of concern crossed her face. “You’ll be appreciative even if I screw up,
“I doubt that’ll you screw up and I’ll be appreciative of whatever you
decide to do.”
“Then I’m sure. I know already that I have to swallow. I’m probably
not going to like the taste, but not swallowing ruins it for the guy.”
“You learned that from your friends?”
“Yes. A few times, girls who don’t like the taste have brought up not
swallowing to my more experienced friends while I was around. The
consensus is that none of the other options will satisfy the guy.” She gave
me a wicked smile. “And don’t ask to cum on my face – that’s totally
I chuckled. “I won’t.” How does a girl give head? “I’ve not thought a
lot about giving head from a girl’s point of view before. It’s been all
about kicking back and enjoying the sensation. Receiving head is great.” I
paused to gather my thoughts. “Okay. I’d say there are two parts to
giving head. The first part is about getting the guy excited.”
“Should I take off my shirt and bra?”
I shook my head. “Excited was the wrong word. I should have said
‘stimulated’. And as much as I’d love to see your tits, we are in a car
visible from the street so I think it’s best if you keep your shirt on.”
This was crazy. The whole night was so fucking crazy. I felt like my
head as going to explode.
“The second part is about simulating intercourse with your mouth and
hand. Your hand is almost as important as your mouth. Let me show you
your go-to move for the second part. Sit down.” She sat down so that her
legs were in the aisle between the middle seats but her upper body was
twisted so that she was facing me. I had one knee on the back seat and one
foot of the floor. “Put my dick in your mouth.” Words I never thought I’d
tell my sister.
Ashlynne leaned forward and slipped a few inches of my dick into her
“Good. Now wrap you hand around my dick. Firmly but not tightly.”
Ashlynne did. “Good. Now while keeping your lips sealed around my dick,
slide your head back. At the same time, slide your hand away from you.”
Ashlynne tentatively did that and then took my dick out of her mouth.
“Yes. Then you’ll slide your lips back down while moving your hand
towards your face.”
“Let me try that.” Ashlynne took my dick into her mouth again. She slid
her mouth slowly up my dick while moving her hand down before reversing the
“Oh yeah, Ashlynne.” Her lips moved back up and back down while her hand
did the opposite. “That feels so good, Ashlynne.” Her lips and hand made a
couple more synchronized trips along my dick. “You’ve got it. Stop doing
“Was I doing it right?”
“For the most part. The area where your hand was should be slick.
It’ll get uncomfortable after a while if it’s not.” Ashlynne nodded. “So
back to the first part. It’s all about stimulating my dick. Really, that
whole area. Get the nerve endings excited. Do it in a lot of different
ways. Doing the same thing over and over again gets boring. If you gave
head by doing only the second part until I came, it would work but I’d be
bored. Variety means excitement. You want to get me so excited that when
you start the second part, I’ll cum fairly quick.”
Ashlynne nodded her head. “Got it.” She studied my dick for a moment.
“I wasn’t able to get much of you into my mouth. How do those girls in
those videos get those big dicks all the way into their mouths?”
“I don’t know. Maybe if I had a dick that big I’d know. I’d guess
they’ve learned to suppress their gag reflex. You can research it later if
you want. But don’t worry about it – I’ve loved every blow job I’ve ever
“Okay. So back to the first part. How do I stimulate you?”
“You were doing a great job while you were trying to convince me to
teach you. Go back to doing what you were doing then.”
Ashlynne smiled. She was getting a little confident in her abilities.
She put her hand so that her fingertips were evenly spaced around my dick
and slowly moved her hand up from my base to my crown. “Like that?”
“That was great. You can give little tickles.”
“Like this?” she asked as she tickled just under my crown.
“Again, that’s great. Do lots of different things. Be creative. But
don’t use only your hand – use your mouth, too. In fact, you need to get
the bottom of my dick wet during part one in preparation for part two.”
“How do I do that?”
“You can lick it.”
Ashlynne gave my dick a short lick.
“Just like that,” I said.
“Did you like that?”
“Very much. You can give it a sloppy kiss.”
Ashlynne held my dick up and give it a wet kiss near the base.
“Very good, Ashlynne. You can run your mouth up and down my dick while
drooling on it.”
Ashlynne smiled and then proceeded to give that a try.
“You’re picking this up quick, Ashlynne. I’ve seen girls in some porn
videos spit on it, but I don’t find that sexy. What I do find sexy is if
you make eye contact while you’re stimulating my dick. There’s nothing
Ashlynne licked the underside of my shaft while watching me, then ran
her mouth up and down my shaft. She stroked the top of my shaft with her
fingers while holding my dick with a gentle kiss. She continued trying
different ways of worshiping my cock while maintaining eye contact most of
“You’re great at this, Ashlynne. And you look so fucking sexy.” A
streetlight provided some light to the car and my eyes had adjusted enough
that I could see Ashlynne pretty well. “Now take me into your mouth.” She
took my dick into her mouth and looked up to me. “Swirl your tongue around
the crown like it’s an ice cream cone.” She did. “That feels so good. You
have a talented tongue, Ashlynne. You can do a couple of the second part
pumps.” She slid her lips down my shaft while sliding her hand up, then
reversed her lips and hand. After a couple of cycles of that, I said, “Now
move on to something else.”
When my dick slid out of her mouth, Ashlynne said, “I’m enjoying this. I
didn’t think giving head would be this much fun. Or exciting.” She gave me
a devilish grin before sliding her lips down my cock.
I could feel another load rapidly building up. Her mouth and hand were
in constant motion while she gave me the sultriest looks I had ever seen.
She was the hottest girl I had ever been with.
“Let’s finish this, Ashlynne.”
She took my dick in her mouth and wrapped her right hand around my
shaft, then established a quick rhythm of bobbing her head up and down my
dick. I began thrusting my hips slightly in time, lightly fucking her
mouth. I started panting and in short order I was about to explode.
“Here it comes, Ashlynne.” I blasted a load down her throat. Having cum
once, it wasn’t so big that it overwhelmed her. She kept up the bobbing as
I fired spurt after spurt.
“Slow down, Ashlynne. Slower. I’m overly sensitive right now. Stop.”
I pulled her up so that we were face-to-face, then hugged her and kissed
her. “That’s was awesome, Ashlynne. Any guy in the world would have been
delighted with that blow job. You’re a tremendous learner.” Ashlynne
beamed. “How was it for you?”
“Great! I enjoyed doing it, though I almost gagged when you came. I
didn’t care for the taste, but it wasn’t awful like some girls say. I
definitely want to do it again.”
We were in a tight space in the back of the minivan. I turned Ashlynne
so that I was standing in the aisle between the two middle seats.
“Sit down, Ashlynne.”
As she sat down, I knelt. Ashlynne was still naked from the waist down
from when she had slipped off her wet panties.
“What are you going to do?” she asked.
“I’m going to show my appreciation for a great blow job.”
I knew I should have ended the date after the blow job. Ashlynne would
have accepted ending it there. We certainly didn’t need to do another act
of brother-sister sex.
I put Ashlynne’s legs on my shoulders then pulled her ass to the edge of
the bench seat. I spread her legs so that her feet were on the middle
seats. Her legs were lightly tanned, but her crotch area was lily white.
It made her seem even more virginal. Her pussy was right in front of me. I
leaned forward and separated her pussy lips with my tongue before licking
“Oh my god!” said Ashlynne.
Maybe I was doing this because of all the years where I expected my
girlfriend to suck me off and I refused to eat her out in return. I knew
now that I was an asshole then. I had always felt like a selfish bastard
when Mandy sucked me off when she wasn’t in the mood for sex and I did
nothing for her. I didn’t want my sister to learn to let the guy walk away
I dropped my tongue down to Ashlynne’s hole and she was sopping again.
Or still. I lapped up a huge amount of fluid. Moving on, I worked up and
down Ashlynne’s pussy lips while she ran her fingers through my hair and
moaned. I made my way up to her clit and then moved my tongue very gently
back and forth as I made a slow circle around her clit.
“You’re going to make me cum again, Todd.”
“That’s the point.”
Maybe I was doing this because I just wanted to eat my sister out. Once
we crossed over the oral sex line, why not explore her body with my tongue?
I knew that if I didn’t, I’d regret letting the opportunity pass. I loved
her taste. I loved holding her firm body in my hands. I loved hearing her
little pants of pleasure. I loved making her happy. I had loved
everything we had done tonight, even dealing with the crazy, entitled
princess. I wanted to make Ashlynne cum one more time.
I went back to working my tongue up and down her whole slit to get all
of nerve endings excited. I enjoyed licking up her nectar. I thought
about finger-fucking her, but I didn’t want to tear her hymeneal tissue.
Hymens were the second most interesting topic in my human sexuality class.
As she had used tampons and had apparently masturbated, she may not have a
lot of hymeneal tissue left.
“Oh, Todd.” Pant. Pant. Pant. “Feels so good!”
Based on her sighs and moans, I felt that she was ready for me to get
down to the business of making her cum. I focused on her clit, making
circles around it while making small up and down wiggles with my tongue.
“My god, Todd!”
Ashlynne wiggled slowly in the seat as I continued lashing her clit, her
arms flopping around. As she had cum once already, it was taking a lot of
work to get her to cum again. Eventually, my work was rewarded with heavy
pants. I redoubled my efforts. Again, I wished I could mix things up by
finger-fucking her. My jaw and tongue were getting a little tired, but I
never slackened my pace. I steadily pushed her towards that mountain top.
She dropped her hands by her side and laid passively as I brought her to
the brink of another orgasm.
“Oh God! Oh God! Oh! Oh! Oh!”
Ashlynne clamped her legs against me and suddenly lurched forward as she
came for the second time tonight.
I slowed my lapping. I waited for her to start breathing again before I
pulled away from her sweet pussy. I sat between the middle seats while I
waited for Ashlynne to recover.
“I thought that the first time you made me cum felt great,” said
Ashlynne. She panted a few times. “That was much more intense. It was
I smiled. “A great way to end a great night.”
Ashlynne nodded in agreement.
“Move over,” I said as I stood up. She scooted on the back seat a
little to my right. I climbed on the seat and reached over to get the
beach towel. “Time for you to go. It’s late and I’ve got a long drive
home.” I wiped my face, which was coated with her juices.
“Okay. We’ll have a goodnight talk, then I’ll give you a good-bye kiss
Ashlynne moved to one of the middle seats. Once I had finished wiping
my face, I sat down in the other middle seat. I stuck out my hand and
spread my fingers. Ashlynne took my hand.
“I like you asking for consent,” said Ashlynne. “It makes me feel more
“After dating Mandy for so long, it’s automatic for me now. She was a
control freak and got bent out of shape whenever I did anything without her
“She was a control freak?”
“Yeah. Didn’t requiring positive consent every step every time sound
like a control freak to you? It wasn’t just limited to sex. Crumbs drove
her nuts. I had to tell her every time I got an assignment or test
announcement. Then everyday she’d make a list for each of us of what we
had to do that night before we could have any fun.”
“What did you think of that?”
“I wasn’t wild about it, but when I committed to Mandy, I accepted all
of her quirks.”
“She’s going to want you back.”
“She’s not going to get me. I worked hard to make our relationship
work, and the only reason I was willing to do it was because I thought she
was totally committed to me. Now, I wouldn’t be able to put up with her
“I’m a control freak, too. It fits in well with being entitled and a
“I recommend that you don’t show it by making lists of stuff to do. It
was very frustrating on nights when one of our roommates was gone and she
refused to take advantage of the privacy because something was still on the
“I used to plan out every bit of our cheer practices and our
performances. At games, I had a general script worked out in detail and
contingencies based upon how the game went. I controlled everything as
cheer captain. But when it comes to dates, I don’t control anything.”
“I’m not surprised you’re a control freak. Do you remember when I used
to sneak into your room and move a few of your things around? Then you’d
go ballistic when you’d come into your room.”
“And you’d deny it all. You were such liar. It’d make me so angry.”
“You were such an asshole.”
“I was. And not just to you. I regret it now. Will you forgive me for
all the asshole things I did to you?”
“Yes. It’s easy to forgive you now that you aren’t an asshole.”
“A little maturity and a lot of sex goes a long way in calming a guy
Ashlynne chuckled and then shook her head. We sat comfortably for a
while. I was thinking of saying it was time for me to go when Ashlynne
said, “This isn’t how I envisioned our date going.”
“You didn’t expect it to end with me talking about my ex-girlfriend and
the mean things I used to do to you?”
Ashlynne laughed. “It’s not that at all. Do you want to hear how I
envisioned our date going?”
“You were going to reach for my hand at some point and I’d reluctantly
agree. Then later, you’d try to kiss me and I’d put you off, I’d put you
off again. Finally, I’d let you kiss me. When we got here, I’d let you
drag me to the back seat. After kissing for a while, you’d ask to touch my
tits and I’d say no. Then you’d beg to touch my tits and suck on them and
I’d say no. Then you’d grovel, I’d laugh evilly and that’s how the date
I cracked up.
“Nothing happened the way I’d planned! I kept making the first moves.
And I practically begged you to let me give you head. You probably think
I’m a slut.”
I didn’t like the last thought. “Do you care for me, Ashlynne?”
A pause, then an embarrassed, “Yes.”
“A lot”, then an embarrassed smile.
“A slut is someone who has sex with multiple guys she cares little for.
You’re not a slut.”
“Okay, I’m a basket case then. I don’t know why I’m complaining about
how the date went. I liked being the aggressor. It made me feel in
control. At the same time, a voice kept screaming in my head that this
isn’t how good girls act. When I was having fun, I was miserable at the
“It was wrong for you to kiss me first but it would have been okay if
your brother had kissed you first?”
“It was all wrong. I had so much fun and yet felt so guilty. I’m so
I hadn’t expected this roller coaster ride from Ashlynne. She had
always been so levelheaded. She didn’t have the big mood swings that most
“Let’s move to the back for a bit.”
I positioned us so that I was sitting in the middle of the back seat
with my legs down the aisle and Ashlynne was facing me, straddling my lap.
I put her head on my shoulder and then I put my arms around her and held
her tight against me. Ashlynne hugged me back the best she could. We held
that position for a while, savoring the feeling of physical intimacy.
“Are you crazy about me, Ashlynne?”
A long silence, then “Yes.”
“So when you went into crazy Grace mode, you acted out that you were
crazy about me. That’s why the date went as it did. I enjoyed it. You
enjoyed it. Everything turned out fine. You were following your heart and
that’s a good thing.”
We hugged for a while more. Ashlynne seemed more relaxed. She asked,
“Are you crazy about me?”
“I’ve been fighting it all night, but yes I am. And it’s going to be
hard Monday to not be crazy about you anymore. I’m glad we have the rest
of the weekend to reset our feelings towards each other.”
We hugged for a little more. I felt like we had reached a good stopping
point. Then Ashlynne leaned back, gave me a big smirk and pulled her
“What the hell, Ash?”
Ashlynne reached back to the clasp of her bra.
“What are you doing?”
“Following my heart.”
She unsnapped her bra and then dropped it forward to reveal her
beautiful tits. They were large, rounded cones with just a hint of sag due
to their size. They were very white except for some tanned areas on top.
It was tough to tell because of the poor lighting, but the areola seemed a
dark pink. I wanted to reach out and touch them, to feel their heft in my
I said, “Ashlynne, as it is I’m going to have a tough time forgetting
this ever happened.”
Ashlynne gave me a knowing smile. Ashlynne adjusted her length so that
her nipple was at the height of my mouth. Ashlynne grabbed my head and
guided my mouth to her right tit.
I knew I shouldn’t. I should shake her off me and go home. But we had
already done oral sex on each other, so why the hell not? I opened my
mouth and latched on to her nipple. It felt perfect in my mouth.
“Do you like that?” Ashlynne asked.
I nodded my head gently.
“I like it, too.” Ashlynne ran her fingers through my hair as I sucked.
“Jenna Peterson says her boyfriend is like a little baby because he likes
sucking on her tits so much.”
Ashlynne pulled on my head and I let the nipple go. She guided me to
her left tit. I happily sucked on it.
“And I like being back in control again. Enough talk about how I’m a
basket case. More spreading of my wings.”
I ran my tongue around Ashlynne’s nipple.
“So nice,” Ashlynne cooed.
I sucked on her tit for a bit and then switched to kissing around her
areola, holding her tit flesh in my mouth briefly during each kiss.
“I really like that,” said Ashlynne as she ran her fingers through my
hair. “But I’ve enjoyed everything I’ve done with you tonight.”
“Any particular place you like being kissed on your tit the most?”
“Along the bottom.”
I continued giving little kisses along the bottom of her areola.
“That’s making me wet again.” My dick was hard again. “There’s a lot
more I want to learn, and I don’t feel as intimidated by how little I do
know. I feel like a sexy woman now, and I like that.”
“You are a sexy woman.”
“And sexy women have tits that their dates want to suck on. Quit
talking and keep sucking.”
As Ashlynne guided my head back to one of her tits, she added “The
biggest thing I learned tonight was how emotionally needy I am. I’ve been
so focused on succeeding that I haven’t been growing as a person. I need
someone who thinks I’m wonderful when I’m not Miss Perfect. I’ve been a
bitch to you all my life. Will you forgive me?”
“I forgive you.”
“Being a bitch to you was so stupid because you can make me feel so
“Well, it doesn’t have to be me…”
“You were right that I’m crazy about you. I’m glad you’re crazy about
me. Somehow, you made it through my emotional minefield. I can be who I
want to be with you. I can do what I want to do with you.”
I didn’t like the direction this was going. “Other guys can make it
through your minefield.”
“A guy from our town? Don’t even go there.”
“You could join a dating website…”
“Entitled, perfectionist control-freak seeks man who’ll make her
personality flaws fun.”
“You’d get a lot of responses.”
“Yeah, from guys who don’t give a shit about my needs and just want to
date someone who looks like me.”
She had a point. “When you get to the university, there’ll be lots of
“I’m going to be so busy with my studies. With pre-med, I’ll be
competing with the best of the state. To get into med school, I’ll be
competing with the best of the best in the world. I’m not going to have
time to get to know guys well enough to determine if they’re a good fit for
a basket case like me. Besides, I want to have fun now. I want to have a
great summer before I start killing myself again.”
Ashlynne put her hands on the side of my head and pulled me off her tit,
then tilted my head up so she could kiss me. She then guided my hands to
her tits. She slipped her tongue into my mouth while rolling her tits in
my hands. Her tits felt great in my hands – just the perfect size and
heft. She was getting me hot again while I wanted to wind things down. My
dick was rock hard now.
Ashlynne broke off the kiss and guide my mouth to one of her tits again.
“Guys are so fascinated with my tits. When I did cheers, I could see them
staring at my chest the whole time. But you haven’t showed them much
“It was the way things worked out. I didn’t want to suddenly grope your
tits and then we moved on to other things.”
I switched to giving her tits little kisses as we talked.
“Do you like my tits?”
“Oh yes. They’re beautiful. I’ve secretly longed to see them for
“Do they look like you expected?”
“They look like how I hoped they’d look. They look perfect to me.”
“Do you like my ass?” Ashlynne grabbed my hands and pulled them down to
her ass. I immediately cupped her cheeks.
“Yes. You have a great ass.” I gave her ass a couple of squeezes. “So
firm. Such a great shape. I love your ass. I know you work hard to keep
in such great shape and it shows. You should be very proud of your body.”
“Which do you like better, my tits or my ass?”
“They’re both great. If I had to choose, I’d pick your tits because I
can see your beautiful face while I look at them.”
Ashlynne lunged forward and kissed me, sliding her tongue into my mouth.
She rose up and leaned my head back, so it was like she was towering over
me while we kissed.
After she broke the kiss, Ashlynne asked me, “Do you love me, Todd?”
“Yeah.” Her wild mood swings were throwing me off. “If you had asked me
a month ago, I would have said no.” I chuckled. “I would have said I hated
your guts. But I’ve really enjoyed being with you this summer. I’d say I
love you as a sister.”
“Do you love me as a girlfriend?”
“No, Ashlynne.” I sighed. “I enjoy being with you. I’ve enjoyed
kissing you and everything we’ve done tonight, but I don’t love you as a
Ashlynne laughed before aggressively kissing me again. When the kiss
was done, Ashlynne kind of slid down my body. My dick, which was standing
straight up, rubbed against her crotch.
“Well, someone wants attention!” said Ashlynne gaily. I lightly
blushed. “Let me give him some.”
She maneuvered herself so that her pussy lips spread on each side of my
dick. She then moved her body up and down some, sliding my dick inside of
her pussy lips. I moaned. I grabbed her ass so I could help her raise and
“You like that?” Ashlynne asked.
“Hell yes. It feels great, Ashlynne.”
“I’m liking it, too. I love being the assertive one. I love being in
control. I’ve enjoyed everything we’ve done, but we could do so much
Danger! Danger! Danger!
“Ashlynne, we need to wrap this up so I can go.”
Ashlynne laughed. “I meant to tell you before your friend distracted me
was that I love that you’re so honest with me. Patient and honest. Guys
will tell me all the time how great of a body I have and it means nothing
to me because I know they’re trying to get into my pants. When you told me
I had a great body, it meant a lot to me because I knew you weren’t trying
to bullshit me.”
The whole time we talked, Ashlynne kept sliding her pussy lips up and
down my shaft. Wet humping? Whatever it was, it had me panting. Despite
having cum twice this evening, I could feel another load building.
“There’s only one guy in our town that I want to be with,” said
Ashlynne. “I know it. You know it. And it’s time to spread my wings more
With that, she rose up on one side while grabbing my dick with her hand.
She started to maneuver it to her hole.
“Stop it, Ashlynne! Stop it right now!” She let go of my dick. “We’re
brother and sister and that’s one line we shouldn’t cross.”
Ashlynne lowered herself on to me. “But…”
“Are you on birth control? No way should we risk getting you pregnant.”
My dick was sideways against Ashlynne instead of between her pussy lips.
She leaned a little back so we could look each other in the face. We had
been so close to fucking that I almost didn’t stop her. But now, I could
“I’m not on birth control. Mom would freak if she found out that I was
on birth control. But I have a plan B pill in my purse.”
“Ashlynne, we’ve done way too much tonight already. It’s going to be
very awkward Monday. I’m not your boyfriend and I’ll never be your
boyfriend, as much I would love to be.”
Ashlynne smiled at me. I swear, I’ll never understand women. Then she
leaned forward, put her head on my shoulder and said, “Wrap your arms
I did. She felt wonderful in my arms. Ashlynne started humming
lightly. We stayed in that position a long time. Finally, Ashlynne pulled
back and looked me in the face again. She was still raised up, so she was
looking down at me.
“Do you love me, Todd?”
“I do, as a sister.”
She smiled. “Will you protect me?”
“Yes, Ashlynne. If you ever need me, I’ll be there for you.”
“I feel so safe with you, Todd.”
Ashlynne leaned forward and put her head on my shoulder. I wrapped my
arms around her. We held that position for a long time again.
“Am I an entitled princess?”
“Am I your entitled princess?”
“You’re my sister.”
“Todd,” Ashlynne said she pulled back to look at me. “An entitled
princess always gets what she wants.” She rose up on one side while
grasping my dick again and once again started to steer it towards her hole.
“Ashlynne, stop.” Again, she released my dick and sat back down on me,
facing me. “It’s not going to be the way you think it will be. It’s going
to hurt the first time. The mutual orgasm thing is a myth. What’s going
to happen is I’m going to cum well before you’re ready to cum, and then
we’ll stop. I’ll enjoy it, but it won’t be that great for you. Wait for
another time, another place, another guy. A guy who’s madly in love with
you. That’s what you deserve.”
Ashlynne gave me a long stare. Then she said, “What you’re saying is
that if we fuck tonight, it will be all about making you happy.”
Ashlynne rose up and kissed me aggressively again, ramming her tongue
deep into my mouth while squeezing me hard. My hands wiggled in the air
aimlessly. I had no idea what was going on.
When Ashlynne broke the kiss, she reached down and grabbed my dick. As
she guided the tip to her hole, she said defiantly, “I want to make you
happy!” Then she lowered herself down and I was in her.
It felt wonderful to be inside of her. Her pussy was warm and wet.
Sliding into her sent thrills all over my body.
When Ashlynne was about halfway down, she said, “You’re so big!” and
“It’s okay, Ashlynne. Take your time. If you want to stop now, that’s
Ashlynne gave me a withering look. “I’m going to fuck you, you
lunkhead. Give up trying to stop me.”
I laughed. What else could I do? Ashlynne slowly lowered herself down
until I was all the way in. I wrapped my arms around her and kissed her.
I was going to fuck Ashlynne. I wanted to. I had fought and fought my
attraction for her, but no more. She felt perfect to me, her body pressed
tight against mine and her pussy surrounding my dick. She was everything I
wanted in a woman. And she wanted me to have her. I couldn’t resist.
We kissed for a while. No Frenching, no sloppy kisses. Just the tender
kisses of two people who wanted to make each other happy.
I asked, “How bad was the pain?”
“Not bad. Most of the more impressive cheer moves are painful, so I’ve
learned to block out pain. I’m ready to get down to the job of fucking.”
“Okay. One thing first.” I looked around and found the beach towel,
which was forgotten on one side of the seat. I leaned over, snagged it and
stuffed it below us. “We want to minimize the mess.”
I cupped Ashlynne’s ass with my hands. “We’ll start slow so that you
can get use to me being in you. Ready?”
Ashlynne gave me a brilliant smile. “Yes.”
I lifted her up a little bit and then brought her back down. I lifted
her a little higher and brought her back down again. Soon, only the tip of
my dick was in her when she reached her peak.
“It feels so good,” moaned Ashlynne.
It did. She was so wet and slippery that it felt wonderful sliding in
and out of her.
Ashlynne cooed, “You didn’t tell me fucking would feel so good.”
“I didn’t want you to fuck me because it feels good. I agreed to make
love with you because I thought there was something special between us.”
Ashlynne rose up so high that I slipped out. She pushed my head back to
kiss me aggressively again. My hands roamed over her firm, wonderful body
as we kissed. When we broke the kiss, she lowered herself slowly back down
and I guided my dick into her again.
“This is special,” Ashlynne said. “This is the most special night of my
Lift and drop, lift and drop. Ashlynne punctuated each drop with a
gasping “Oh!” Sometimes I held Ashlynne around her small waist and other
times I held her ass. Ashlynne’s tits were bouncing right in front of me.
I brought my hands up to cup them for a little bit and let her fuck me by
herself. They were magnificent. Ashlynne smiled at me and then went back
moaning. She was so god damn sexy. I dropped my hands back to Ashlynne’s
Ashlynne surprised me by suddenly stopping. “Am I doing okay?”
“You’re doing great.” I hugged and kissed her. “Would you mind if we
“Something wrong with this one?” She sounded concerned, but not panicky.
“It’s been fine, but I’d like to fuck you harder than I can in this
As Ashlynne slid off my lap, she said, “You want to be more in charge?”
When my dick slipped out of her, it had some blood on it. “Hell, yeah.
I’m about to go all caveman on you. Can you brace yourself against the
I quickly wiped my dick clean with the towel and then tossed the towel
on the seat. Ashlynne bent over and put her hands on the window while
bending her arms to brace herself. In the meantime, I moved behind her so
we were in a modified doggie-style position.
“One more thing,” I said as I moved close enough for my dick to touch
her pussy. “Be vocal. Moan as loud as you comfortably can. Occasionally
tell me how much you are enjoying me fucking you.”
As I was sliding my dick back inside of Ashlynne, she turned her head to
face me. “You want me to cheer you on?”
“Please. And don’t worry that much about being vocal – I’ll appreciated
whatever you do.”
I grabbed her hips at where the white bikini marks narrowed the most and
buried myself as deep as I could go.
“Ready?” I asked.
I pulled back a few inches and then pushed back into her. I pulled a
little further out and then pushed harder back into her. On the third
push, Ashlynne pushed back to meet my thrust.
“Fuck me, Todd. It feels so good.”
It did feel good. I loved the feel of her firm ass in my hands. I had
let Ashlynne be in control most of the night, but I wanted be in control
when I came in her. When I came in my virgin sister. I hadn’t asked to
become lovers – I had fought it the best I could – but I was enjoying every
second of it now.
“Give it to me, Todd.”
Ashlynne went back to moaning as she met my every thrust. Her moans
were louder than before, but didn’t sound forced. She sounded like a woman
enjoying being thoroughly fucked.
I was getting close. I was also covered in sweat. The minivan reeked
of sex. It gently rocked back and forth as I pounded Ashlynne against the
window. I could see that her back too was covered in sweat. My sister had
a beautiful body and was one hot fuck.
Slam! Slam! Slam! I fucked Ashlynne hard and she fucked back just as
hard. The pleasure of fucking her was so intense. She was my woman, I was
her man and we were doing what God designed us to do.
I felt the tingling in my balls. Fucking her had been so good that I
was surprised that I had last this long. “I’m about to cum, Ashlynne.”
She kept on fucking me hard. I shot my third load of the night, this
time into her virgin cunt. As the spurts slowed, I slowed Ashlynne down
and then stopped her when I was done. We collapsed next to each other in
the back seat. I pushed the towel against her pussy to keep the cum from
getting on the seat. Ashlynne grabbed me and pulled me into a hug.
“Are you happy?” Ashlynne asked.
“Over the moon. It felt great and 100% right. How do you feel?”
“Sore, but otherwise on top of the world.”
I kissed her. We kissed tenderly for a while.
“Ashlynne, I want to talk to you about Monday.”
I interrupted her by putting my finger on her mouth.
“Look, Ashlynne. The agreement was that on Monday, this would all be a
secret that we would never discuss. I accepted that. Now, I’d like to do
something like this again, even if it means a lot of hassle like driving
out of town. I’ll fully understand if you want to keep to our original
agreement, but I’d like for you to think over the weekend about possibly
doing something like this again. Is that okay?”
Ashlynne nodded. “Okay.”
“We’ll discuss it Monday at breakfast, alright?”
“Monday at breakfast.”
“Time for us to clean up and go.”
I grabbed the loose end of the towel and used it to dry my crotch. I
then got up and moved to the middle seat, where I pulled my shorts on.
Ashlynne joined me and pulled her shorts. She said, “You need to do
something about the towel before Mom sees it.”
“When I leave here, I’m going to buy a big fruit punch drink, knock it
over then clean it up with the towel. My blind date was clumsy.”
“Perfect. I’ll take the plan B pill once I’m inside.”
Ashlynne put her wet panties in her purse and I put my nasty underwear
with the towel. I opened the door, got into the front seat and rolled down
“I’m going to air out the car.”
Ashlynne gave me a quick kiss and moved to the gate in the fence. “See you Monday morning!” she said with a wave. I waved back. Then she was through the gate and gone.
* * * *
Monday morning, I woke to the sound of my bedroom door opening. I opened my eyes to see Ashlynne striding across the room to my bed in her light blue nightshirt.
“Mom and Dad are gone,” she announced. “Grace wants to go on another date Friday.” She sat down on my bed next to me. “She wants it to be a much nicer date. You’re going to take her to a nice restaurant and pay. She’ll decide on the post-dinner entertainment and she’ll pay for that. Then after that, you’ll split the cost of a hotel room.”
Fucking Ashlynne on a bed. Sleeping with Ashlynne. Having morning sex
with Ashlynne. I felt myself harden.
Ashlynne added, “Grace probably won’t be a crazy, entitled princess on the next date.”
“Okay. What’s she going to be?”
“That’s for her to know and you to find out. By the way, she started on the pill Saturday.”
“That’s good. Is she seeing this as a regular thing?”
“She likes you a lot. It was just one date, but she’s thinking this
could be a long-term relationship.”
I smiled. Ashlynne smiled. I knew to grouse before submitting to her
“That’d be a lot more money. And I don’t know if I can handle a different Grace every week.”
Ashlynne surprised me by pulling off her nightshirt. She was naked underneath.
“Grace has authorized me to do everything to convince you.”
“Everything?” I asked as I moved my hands towards her tits.
Ashlynne grabbed my wrists and held my hands tantalizingly close to her tits. “Can you handle my quirks if I’m fully committed to this relationship?”
“I think so.”
“Then everything,” she said as she pulled my hands to her tits while leaning forward to kiss me.