by Wannabe Chic
Synopsis: This story is partly based on fact, partly a fantasy. It is the story of a young man on vacation with his girlfriend and the night they have sex for the first time. The girlfriend has, up to this point, been reluctant to try sex. The big night finally comes for the two of them and the young man realizes, at last, what has made her so hesitant to share herself. The story is divided into several parts - the first focusing on oral sex and the second part on anal sex. The rest . . . we'll find out when we get there!
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The hour was growing late as I looked around the cozy living room. Six of my friends were sitting in various places, in various positions, all watching some late night horror movie on the television. There was a feeling of general contentment. We had arrived at the house several hours earlier and were enjoying our visit already. It belonged the family of one of the group and her family had allowed us to use it for a week in the height of summer. Life couldn't have been sweeter.
My girlfriend Rebecca sat on my lap wearing a dark blue tank-top and tiny denim shorts. Her right arm was around my shoulders and her left hand rested on mine, which was resting on her thigh. I gently stroked the pale flesh of her thigh as I held her tightly around the waist with my other arm.
"Tired, baby?" she asked me.
"Why don't you go to bed?" she asked.
"We're all having such a good time," I answered.
"Well, if you go up, I'll join you in a few minutes," she said, "I'm pretty tired too."
"Alright," I said. I gave her a quick kiss and she climbed off my lap. I stood up, wished everyone a good night, and then trudged up the stairs to my bedroom.
"My" bedroom was actually the master bedroom of the house which had been assigned to Rebecca and me, since we were one of the only two couples on the trip. In the center of the room against the back wall was our bed, a cozy king-sized. We had our own television, our own bathroom, and a private world all to ourselves.
I suppose now would be the appropriate time to tell you about Rebecca and me.
We had gone to high school together, but had never been more than casual acquaintances. A few months earlier, however, we were re-introduced through a mutual friend. I marveled at the transformation. Either I was grossly disremembering her or she had definitely grown up while she was away. She had a really gothic way about her, wearing lots of dark clothing and dark make-up, but she lacked the annoying pretentiousness of most goth chicks I had met. We clicked instantly.
Physically, we were almost the opposite. I was tall and wide with a solid frame of muscle and bone. Rebecca was tiny and thin, with small breasts and a perfect little ass. With her dark hair and fair skin, she couldn't have been any more perfect to me.
"Are you decent?" I heard her ask from outside the room.
"Yeah," I said. "Come on in."
She stepped into the room, smiling at me as I unbuttoned my shirt, then stripped it away. Rebecca stood close to me, nuzzling her face against my plain white t-shirt, and wrapping her arms around my waist. She cooed softly.
"It's time for bed," I told her.
"I know, I know," she replied.
"How about you change in the bathroom and I'll get ready in here?" I suggested.
Rebecca agreed that sounded like a good plan and took her pajamas into the bathroom. Meanwhile, I took off my socks and my shorts, leaving only a t-shirt and boxer shorts on me. I turned the lamps beside our bed on and turned the main, overheard light out. I crawled beneath the blankets and had just settled in as Rebecca emerged from the bathroom.
She wore black, flannel pajamas pants and a matching tank top. She smiled at me sweetly and then climbed into bed beside me. She pulled the blankets over her legs and turned out her lamp. She snuggled in closely against me.
"Turn out the light," she instructed.
I reached over and turned the knob, plunging the room into warm, comforting darkness. Rebecca and I lay still for a while, each content with our own thoughts, and with one another's company.
"I love you," I told her, breaking the silence.
"I love you too," she said.
"How much do you love me?" she suddenly asked.
That caught me off guard. "Very much," I said, not knowing exactly how I should respond to a question like that. Love wasn't exactly a quantitative thing, after all.
"I think I'm ready to do it," she said, after a long, slightly nerve-wracking pause.
"Do what?" I asked.
She laughed. "You know. Have . . . sex."
It caught me completely off guard. I didn't know how to react so, like an idiot, I went silent. My grip on her relaxed slightly and she took this as a bad sigh. She slid away from me to her side of the bed.
"I'm sorry," she said.
"No, don't," I told her, moving alongside her. "I'm sorry, I was just surprised. I wasn't expecting you to say that. But I'm glad you did."
"So you want to?" she asked.
"Of course!" I told her, smiling.
"There's just one thing . . ." She said that nervously, looking down at her own body. "I want to keep my breasts covered, if that's OK. It's just . . . you know . . ."
"It's fine, babe," I told her. "However you want to do it is fine by me."
I had a feeling this might happen. Although it might seem like an unusual request, it made sense, given the context. Rebecca was, for reasons I couldn't understand, very self-conscious about her breasts. I suppose a small-chested woman living in this world of d-cup porn stars, where tiny waists and giant tits are glamorized, could feel that way. I wouldn't have wanted Rebecca any way but the way she was. Despite my total and complete comfort with her body, I would grant her wish.
"So . . ." she said, "how do we . . . start?"
"I guess we just go for it," I said.
We began kissing, closing our eyes and holding one another tightly. I opened my mouth and flicked my tongue against her lips. She responded by opening her mouth and our tongues began to rub against one another. My tongue was in her mouth and her tongue was in mind. Saliva escaped both of our lips, but neither cared.
I grabbed Rebecca by the waist as I rolled on to my back, easily pulling her on top of me. She straddled my waist, leaning down over me without ever breaking the passionate French kiss. I moved my hands down to the seat of her pajama pants, feeling the firm round globes of her ass. Finally, she broke the kiss, lifting her head as a small string of drool fell from her lips into my mouth.
She grabbed the bottom of my shirt and began bunching it up. I sat up quickly and raised my arms, allowing her to pull it off over my head. She pushed me back down and began kissing my neck, licking and sucking one spot before moving to the next. My neck became my shoulder and then my chest. She dragged her tongue from my sternum to my right nipple and sucked on it for a moment before moving back across my chest to the left. She bit my nipple and my body surged slightly as the wonderful pain spread out through my body.
"Are you OK?" she asked softly.
"Keep going," I answered quickly.
She returned her face to my chest and continued biting and sucking my nipples. My body writhed and I strained not to cry out, lest I draw attention to our room or make Rebecca think she'd hurt me again. Sadly, she proceeded down my body, kissing my stomach. I took her hand and placed it over my chest, allowing her to squeeze my nipples as she kissed my torso.
By the time she reached the elastic band of my boxer shorts, I had a raging erection. My cock bulged through the fabric of my underwear and I felt a little embarrassed for a moment. But she seemed to be flattered by it. Hesitantly, she reached out, and rubbed the tip of my cock with the palm of her hand, making a concentric circle. It felt amazing, and even more amazing because I knew it was the first time she had ever touched a penis before.
She pushed my knees apart, causing me to spread my legs. On her hands and knees between my feet, she leaned down, and kissed me gently through the cloth. She then proceeded to kiss me up and down my shaft, only hinting at how wonderful this would feel without the material in between us. I could feel her frenzy building as she stopped kissing, and began licking my shift, pausing at the top each time to take my head in her mouth. My underwear was covered in spit but I didn't care. A bomb could have gone off and I wouldn't have cared.
"What?" I said. This was a bad sigh.
"You're peeking out," she said.
I felt her finger go into the gap between my thigh and the leg of my shorts. Her finger tickled my scrotum. Closing her eyes, she put her face against my leg, and buried her face in my shorts. I felt her tongue gently flick against my sack, then her lips pinch a flap of skin, tug at it, and then release it.
"You're killing me," I said.
"You want me to let him loose?" she asked with a smile.
"God yes . . ." was my response.
She grabbed the elastic band and slowly pulled my underwear off. My dick popped out, standing at its full height. Rebecca tossed the underwear on the floor and then stopped as she turned back and finally saw my cock and my balls in all their glory.
She took my long, thick shaft in her small hand. I could tell by her expression that she was marveling at the size of it and that gave me some confidence. She began to slowly stroke it up and down, getting a feel for the unfamiliar organ. A gob of precum had appeared on the very tip and she smeared it across my head with a finger.
Finally, after what seemed like an eternity of waiting, she worked up the nerve and opened her mouth wide. She lowered her head just enough so that my head was in her mouth. She waited a moment before closing her lips. Her tongue probed, getting the feel for it, and getting used to the taste.
But she got used to it quickly. Her head began to bob up and down as she swallowed my meat, or at least as much as she could. Her free hand cupped my balls and played with them gently as she licked and sucked my throbbing dick.
She moved her hands again, now letting go of my shaft, and letting her mouth do all the work. She grabbed my hips and used them to support herself as she used the entire upper body to suck me deeper and harder. I added support, letting my hips rise and fall, trying to force as many inches in as possible without choking her.
I felt a familiar feeling and quickly recoiled. Rebecca was loathe to let my dick leave her mouth, but finally she let it slide out, and frowned at me.
"What's wrong?" she asked.
"Nothing," I sighed. "But I was about to cum and I don't want to finish just yet."
"Oh, OK," she said. "I thought I'd done something wrong."
"No," I said, reassuringly. "It was perfect."
"Good," she said. "Now it's your turn."
"You want me to eat you out?" I asked her.
Rebecca sighed, looking forlorn, and sat up in bed beside me. Despite the fact that she was still wearing her flannel pajamas and I was stark naked, I felt comfortable. She looked away from me and I sat up on my elbows.
"What's wrong?" I asked.
"Do you love me?" she asked.
"You know I do," was my reply. I didn't like where this was going.
"Would you love me no matter what?" she asked. I nodded.
"Of course," I told her.
"There's a reason I've been so afraid to try sex with you," she said, "and it's not just about self-consciousness or wanting to keep my virginity."
"What is it?" I asked.
Rebecca turned back to face me. Without a word, she lay on her back, pulling her legs up to her chest. She grabbed the band of her pajamas and pulled them off, revealing her shapely white legs. She wore black thong panties underneath. With her pants discarded, she knelt in front of me. I watched her, waiting to find out what she would do next, and what secret she would reveal.
"I can't do it," she said after a moment's hesitation.
"Yes you can," I told her. "I promise. This won't change anything."
Giving me a look of infinite trust, she climbed over me and stood beside the bed. Slowly, she turned her back, and slowly pulled her underwear down to her ankles, then stepped out of the thong. Her ass was inches away, so perfect in its shape and size that I wanted to caress it right there, but I knew this wasn't the time.
Rebecca was trembling, her elbows crooked with her hands on her stomach. With an unbearable slowness, she turned around to face me. My eyes met hers and then moved down her body, past her belly button, and her neatly-trimmed pubic hair. At last I understood. Nestled in her dark bush was a small, pink cock and sack.
I couldn't say anything. I just stared with my jaw slack. My girlfriend's lower lip begin to tremble and I knew she was on the verge of tears. Without thinking, just reacting to her face, I quickly sprang to a sitting position, whipping my legs over the side of the bed, and wrapped my arms around her, pulling her close to me. We held one another for a long time in the dark.
"You hate me, don't you?" she said into my shoulder.
"I don't hate you," I replied. "I just didn't expect this. I don't know how to feel about it."
Suddenly, I noticed something peculiar. My own cock was as hard as steel. I hadn't noticed it, but I'd become painfully erect since the blowjob had ended. I moved my hips slightly, feeling the tip of my dick brushing against something soft and realized instantly what it was. Rebecca was standing between my legs as I embraced her. My cock was rubbing against hers and apparently it loved the feeling.
I pulled her head away from my shoulder and kissed her passionately, forcing my tongue into her mouth. She met my kiss with equal fervor, wrapping her arms around my head as we kissed. I fell back on the bed, pulling her down on top of me, not breaking the lip lock.
Rebecca's hips were gyrating against me and I realized she was grinding her cock against mine, probably not even conscious of it. Our shafts were pressed against our stomachs and the veiny undersides were rubbing together. I gripped each of her ass cheeks in my hands and forced her crotch against mine, creating more of that sensual friction.
By this point, any thoughts of gay or straight had gone out the window. This was my beautiful girlfriend whom I loved. She had a dick, but my body didn't seem to mind, so neither did I. I gave myself fully over to this new, wonderful experience.
I broke our kiss. She lay on top of me, breathing heavily.
"I have questions," I told her.
"OK," she replied.
"But they can wait until the morning," I said. Rebecca smiled and I continued. "Can I suck it?"
Even in the darkness, I could see her blushing when I mentioned it.
"Only if you promise to make it feel good," she told me.
"I'll try," I promised.
Rebecca climbed off me and crawled on all fours to the top of the bed. I turned my head to watch her go, her cute butthole exposed as her ass wiggled, and her hanging scrotum peeking out beneath her crack as she moved into position.
She turned over, laying on her back with her legs spread. She was rubbing her cock with the open palm of her right hand as I lay down with my head between her thighs. She was harder now and I saw that she must be about six inches fully erect, not as big as me, but a respectable size. I pushed her hand away, leaving her meat fully exposed to me. She watched in anticipation of her first blowjob with a nervous eagerness.
I began kissing her inner thighs slowly and gently, working my way up. I did this to bide time more than anything. I'd never sucked another guy's dick, certainly not a girl's dick, and I needed a moment to steel my nerves.
Finally, I could go no higher. I stopped and lowered my face towards her dick, stopping when my face was inches away to breathe in the unfamiliar scent. I puckered my lips and with deliberate hesitation kissed the base of her shaft. Her body trembled at my touch. I kissed again, this time closer to the head, about halfway up. Finally, summoning all my courage, I kissed the tip of Rebecca's dick, a string of precum touching my lips.
I was surprised to find that the taste was actually rather pleasant. It was a strange, fleshy taste unlike any I'd ever experienced. I stuck out my tongue, taking a moment to wet it first, and ran it from her piss hole all the way to her bush. Rebecca was now groaning audiby.
In a move so quick I even surprised myself, I opened my mouth and swallowed her cock in its entirety, feeling my nose tickled by her pubes. The warm organ filled my mouth, hardening to its full height. I slowly pulled back, running my tongue along every inch until I reached the head, which I nursed like a baby for a few minutes before swallowing it again.
I repeated this cycle, increasing my pace each time. Rebecca was going wild, her hips were bucking, and she was raising her ass from the bed, trying to force herself deeper into me. I welcomed her aggressive face-fucking with a genuine desire to pleasure her as much as possible.
I pulled back after a few minutes of sucking, letting her cock slide out of my mouth. Now glistening with saliva, it lay back against her stomach again, twitching. I plunged down again, burying my face between her thighs and her balls, licking them fiercely. They were shaved completely bald and felt smooth and silky in my mouth.
I opened my mouth and let one of her testicles pop into my mouth where I squeezed it very gently between my lips. Rebecca cried out, cooing in sweet pain. I lapped at her sack for a little while before once again returning to her delicious dick.
"Stop," said Rebecca breathlessly. I regretfully pulled away, letting her flop out of my mouth again.
"What's wrong?" I asked.
"I want to try something," she said.
Rebecca began to move and urged me to roll on to my back. She climbed on top of my, crawling forward until she was straddling my head. Her meat was lying across my face, warm and wet. Rebecca raised her hips, pointing her dick at my mouth, and I opened to receive her.
From here on, Rebecca did the work. I kept my lips firmly locked around her as she thrust her hips forward and backward, ramming her cock into my mouth so hard it nearly made me gag. She grunted with excursion and pleasure as she pounded my eager mouth.Rebecca's hands were on the mattress above my head and her body tensed as she did push ups to face fuck me. Her dick went deep into me and I could feel her soft, warm balls bumping against my chin with each hard thrust. My nostrils were filled with the musky scent of her sweaty crotch and I was in Heaven.
I closed my eyes, rubbing her butt with my hands as she fucked my face with an intensity I didn't know she was capable of. She whimpered and squealed with delight, crying out so loudly I wondered if she even remembered we were sharing this house. Finally, I heard her breathing quicken to a pace where I thought she might pass out and she whispered raggedly, "I'm . . . going . . . to . . . cum . . ."
I seized her ass cheeks and forced her deeper into my throat. With one, final cataclysmic thrust, she forced her cock into my mouth, and I felt a hot salty spurt against the back of my throat. Rebecca cried out in ecstacy and her ass cheeks quivered with explosive delight as her entire body trembled. I swallowed down her cum with one gulp, then sucked out the last few drops from her limpening dick.
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