Poolside: Sex With a New Mother

by Steppenwolf2814


It seemed like I had everything going for me. I'd managed to survive my first year of college with near-perfect grades. I'd gotten on the swim team; most importantly, I had managed to get an excellent deal on a car (a 1995 Chevy Cavalier).

However, despite all of these things, there was one aspect of my life that still bothered me a little. It wasn't something I brought up to a lot of people, but I was still a virgin. Sure, I had dated some girls, had been told by several that I was good-looking, with my blonde hair (dyed) and green eyes, and a decent body, but some of them either were saving themselves for marriage, or they weren't interested, or stuff like that. It was so frustrating. I was jerking off like a fucking zoo monkey on a daily basis.

After my first year of college, I was home for the summer, visiting my folks. Throughout those months, we were hit with a massive heat wave that would remain until the end of August. Around early July, on my 19th birthday, I was bored out of my mind by ten a.m. My parents and twin sister wouldn't be home until that evening, when they'd take Gwen and me out to dinner (a tradition we did every year).

With nothing else planned, I decided to head over to one of my mom's friends' houses. Mrs. Bennett was a widow who moved into the neighborhood a few years ago with her daughter, and she had a very big swimming pool, so I figured it'd help me cool off a little. Grabbing a towel, I drove on over to the Bennett's in my swim trunks.

Mrs. Bennett answered the door. She was in her early 40s, about 5'7", with shoulder-length dark red hair and the brightest blue eyes I'd ever seen. It looked like she managed to keep fit. Since she worked out of the home as a personal trainer, it didn't surprise me. It was hard to tell, though, with the baggy T-shirts and jeans I almost always saw her in. She reminded me of Julianne Moore, and I'd had an on again/off again crush on her since I was 14.

"Hey, Mrs. Bennett, is Laura home?" Laura was five years younger than I; despite this, we were quite good friends, though it was obvious nothing would ever happen between us.

"Nope, she's visiting relatives out of town until August 4th. You can go on out to the pool if you want, Jack; I know it's such a scorcher today."

Heading out back, I leapt into the pool, which was surrounded by hedges, allowing their family privacy. The chill of the water was like an instant wake-up. After swimming a few laps, I climbed onto a raft floating in the pool, just drifting and relaxing. Suddenly I heard the back door open, and Mrs. Bennett came out. When I saw her, I nearly fell off the raft.

Apparently, Mrs. Bennett had a better body than I could have possibly imagined, with plenty of jiggle factor. Her tits were huge, at least 40D, without any sag. She also had a flat stomach and narrow waist, with the greatest ass I'd ever seen. It rode really high and meaty, each cheek jouncing around independently of the other. She could have passed herself off as 10-15 years younger if she wanted. If this body wasn't natural, then she had a damn good plastic surgeon.

I was shocked to see that Mrs. Bennett had managed to find a bikini designed for a Barbie doll, with the suit consisting of two yellow triangles over her hard nipples and an impossibly tiny thong, which disappeared between her big, round butt cheeks. It was barely visible even on her hips and covered just the bare minimum to keep her decent.

I was shocked. Hell, I didn't even know any girls my age that had a body like this, let alone would dress like this. Quickly sliding off of the raft, so she wouldn't notice my hard-on, Mrs. Bennett dove into the pool, swimming as gracefully as a mermaid, before surfacing near me and splashing me.

"Y-you're a really good swimmer, Mrs. Bennett," I managed to stammer out.

She just laughed, a cheerful, friendly one accompanied by a beautiful smile. "Oh Jack, you can call me Deirdre." Deirdre then turned so her back was facing me. "Could you help me out, here? My top feels a little loose. Could you retie it?"

"Um, s-sure thing, Deirdre."

It didn't seem that difficult, just a simple tie, but I stepped forward, hoping she wouldn't feel my shaking hands. She got closer to me, her ass just centimeters away from my fully erect dick. Just as I undid the knot, Deirdre suddenly 'accidentally' lunged forward, pulling the top out of my hands and slamming that giant caboose of hers into my crotch.

"Oops, I'm such a klutz. Didn't mean to do that."

Giggling like a schoolgirl, Deirdre suddenly turned around to face me, lust in her eyes, not even bothering covering up her tits or grab her bikini top. This was the first uncovered pair of boobs I'd ever seen outside of a magazine or video. They were magnificent, with juicy nipples.

My mind was reeling. On the one hand, this ultra-hot woman was standing right near me, showing off her fantastic body; on the other hand, this was my friend's MOM! Apparently, Deirdre read my mind.

"Now, Jack, just because, I'm a mom doesn't mean I'm not a woman. I don't mind if you stare; I like it that you think I'm attractive."

She reached under the water and tugged on my dick through my shorts as she said this last part. It took every ounce of willpower to avoid blasting off. Letting go, she held both of her hands under the water near her bikini bottoms, evidently slipping out of them without crouching under the water.

"Besides, I need your hard dick inside of me. I've wanted it ever since Cindy described it to me."

The Cindy in question was another neighbor of ours; a 27-year-old blonde bimbo (and I mean that literally, in voice, appearance and attitude). After a party she'd thrown last summer, we both were slightly drunk (her more than me), had a long make-out/dry-hump session in her backyard. She taught me how to go down on a girl, and she jacked me off, giggling the whole time. She wanted me to take it further, but I didn't want to take advantage of her in that state.

"I need to fuck something other than one of my toys."

The lower half of her bikini floated to the surface.

"Think you can accommodate me, Jack?"

Before I could respond, Deirdre pulled me close for a deep French kiss. I decided to respond in kind, letting my tongue probe her mouth, running my hands over her body, but especially focusing my hands on her juicy ass and huge tits.

Deirdre headed over to the edge of the pool, obviously timing it so that I'd get there just as her butt was at my eye level. Shaking it in my face, she headed over to the huge beach towels set up around the pool.

"Lie back," she ordered. Instantly, I complied. Faster than I could see, Deirdre ripped my shorts off and threw them aside, her eyes lighting up at the sight of my erect dick, nearly 9 inches long by 3 inches wide.

"Jesus," she gasped softly, running a finger down the shaft. My cock jerked slightly as I looked at her huge round melons. Suddenly Deirdre's warm, soft MILF hands were wrapped firmly around my throbbing member.

"Whoa!" I gasped. "Jesus, lady!!"

"Shut the fuck up and lie back," she commanded, looking into my eyes. "It'll help you last longer."

I gulped. "Um, yeah . . . yeah ok," I stuttered. I laid back, Deirdre's hands still firmly wrapped around my shaft, and she followed me over, ending up on her knees on the ground next to me. She gave my tip a wet kiss, making me gasp.

Deirdre didn't say a word, but smiled for the first time as I reached out to touch her. She recoiled slightly and smacked my hand away. "You like my big boobies, right?" she asked, licking me once from the bottom of my shaft to the top and hefting one breast in her hand. I nodded again.

Deirdre released my cock and took both her breasts in hand, straightening up a little bit as she wrapped the soft, warm flesh around my cock and slowly began to stroke me up and down . . . up and down, the soft, smooth skin sliding over my rock-hard shaft.

"Ohhhh man," I gasped, letting my head rest back.

I gulped as I felt Deirdre's lips on my tip in addition to her tits on my shaft, and looked down to find her slowly giving me the most amazing (and first) blowjob of my life! The combination of her soft breasts and her hot mouth was driving me insane! I couldn't hold back and flooded her mouth. Caught off-guard, Deirdre's eyes grew wide as her cheeks ballooned out. Swallowing most of my cum, she let some of it drool out and splatter her tits. Suddenly, she stopped, giving my cock one last suck before releasing me and standing up.

"Don't think I'm going to make it that easy for you, boy," she taunted, rubbing my remaining cum into her tits. "You've got to give me something first."

"Anything!" I breathed. Crawling away from me, she stretched out like a cat and lay on her stomach, her legs spread, giving me a full view of her pussy, which was shaved smooth.

"I'll fuck your brains out, but first you have to eat my pussy."

Still shaky, I slid down Deirdre's body, then planted the tip of my tongue at the bottom of one of her ass cheeks, licking my way over the sensitive skin and making Deirdre moan with pure lust. I then slid my tongue backwards down her ass crack, making her shake, and reamed her asshole with my tongue. Excited by the strong scent of her cunt, I dribbled a big wad of spit onto her asshole, and then painted it all around with my tongue, with Deirdre pressing her ass into my mouth.

"Mmm . . . I love having your tongue in my butt, Jack. It feels so goooood . . . so dirty."

Holding onto her hips, I licked down to the outer lips of her pussy, licking around the lubricant-glazed juicy lips as Deirdre pulled her hips against my restraint. Then, I took one of her inner lips between my lips and hummed on it as I sucked, making her cum and releasing her fluids on my waiting tongue.

Holding Deirdre's body down by gripping her sides, I went to work on her pussy, sucking on each of her lips and running my tongue along the edge, making her start to shudder in a continuous orgasm. After giving Deirdre's lips a long, wet goodbye lick from her clit up, I shoved my tongue inside her pussy, wiggling around and fucking her cunt in and out.

"I know you want my fucking cock!" I screamed over Deirdre's moans, raking one of my fingers over her clit.


"You'll get it soon enough, slut. You'll just have to cum some more for me."

Deirdre whimpered in lust, looking like she was having an out-of-body experience as I shoved my tongue back inside her pussy, rubbing and raking her clit with my thumb as I twisted my tongue around, stabbing her pussy as deep within those sugar walls as possible.

As I tasted the depths of this MILF's pussy, I rubbed Deirdre's slick clit between my thumb and forefinger, rendering her speechless and motionless as yet another cum racked her body. Finally, I took her clit between my teeth and lightly pressed them to it as a vice, flicking my tongue across her clit and making Deirdre shake uncontrollably. After raking my teeth back and forth over Deirdre's clit, I took her clit between my teeth and sucked on it hard, pulling it away from her body with the vacuum formed in my mouth. I flicked my tongue over Deirdre's clit a few more times, my ears ringing from her incoherent moans and yelps before I finally pulled my mouth away from her pussy, giving her jiggly ass a final slap and grab.

Deirdre rolled over on her front, glassy-eyed and gasping like a fish out of water. Watching her huge boobs rise and fall as she caught her breath, I laid down next to her, running a hand over one of her tits and giving her a kiss with plenty of tongue.

"Mmmm, slut, you taste sooo good," I said, smiling. By then my dick was slowly returning to full mast. Deirdre decided to accelerate the process (so to speak). As soon as she caught her breath, she climbed onto me, her pussy inches from my face. I thought she was going to let me eat her again, but she had other plans. Turning around, she began to smother me, grinding her luscious ass directly in my face.

"Yeah, you like my butt, don't you bitch? You want to ram your hard dick into my big ass; you like burying your dirty tongue in my little asshole, and you've wanted to butt-fuck me ever since I rammed it into you." She continued in this way (though some of this was inaudible to me), slowly cutting off my oxygen with her glorious gluteus.

I could barely breathe from this, when she suddenly reached forward and began jacking me. With Deirdre flooding the air with a huge amount of dirty talk, I was back to attention in no time. Before I could pass out, she stood up, after smacking her ass against my face one last time.

"Now, I'm gonna fuck you until you scream, 'cause you're my little bitch."

I took myself in hand and held my shaft straight up as she slowly lowered her hips down onto me. I ran my hands up one of Deirdre's thighs, loving the way her skin felt. I had barely time to finish the thought before I felt her slick, wet lips suddenly envelope my tip and slowly slide down my cock, engulfing me in her hot pussy! She didn't stop until her butt was resting on me.

"Ahhhh yessss!!" she hissed. Putting her hands on my chest for balance, Deirdre slowly began to bounce her hips up and down on my cock, my shaft sliding smoothly in and out of her hot, MILF pussy. She was so wet that it was running down over my balls and making hot little noises as we fucked like rabbits.

"Fuck! Fuck! Uh! Yes! Yes! Oh, yes give it to me!" Deirdre cried, with her head back and her eyes closed, her butt bouncing up and down on my cock with a nice rhythm. My shaft slipped easily in and out, in and out of her tight, wet pussy. I reached up to suck on one of her huge melons. This triggered another reaction from her.

"Ohhh fuck I'm coming! Yes! Yes! Uuuhhh shit yes!!" Deirdre cried, her rhythm faltering as her orgasm washed over her, her body thrashing around and her pussy squeezing my cock for all it was worth.

As she came, she lunged forward with a deep tongue-kiss, screaming into my mouth. But even after she came, she kept going! The insatiable bitch wasn't kidding when she said hadn't had a good fucking in a long time! Reacting on instinct, I took hold of Deirdre's hips and pounded up into her pussy on the down stroke, making her squeal with pleasure. After a few of these, she suddenly stopped, breathing hard, and took to swiveling her hips around on my shaft, sliding off of me. Mere inches away from my dick, Deirdre let it be exposed to oxygen for a few seconds, her ass at eye level.

"Harder!" she barked.

She looked back at me over her shoulder and licked her upper lip, gnashing her teeth slightly before putting on a pleading face. I reached over and ran my fingertips over her ass cheeks, letting a finger brush against her rear entry and making her scream at the contact. A soft, piteous moan escaped her lips, followed by a wavering cry. I took hold of her hips and slowly started to feed my meat into her again, letting her ride me reverse-cowgirl style.

"Uuunnnggghh! Oh! Oh! Oh! Uhhh fuck, please!" Deirdre pleaded, looking back at me. Her well-lubed cunt was eagerly accepting inch after inch of hard cock. With every passing second, the lady's whines and moans became more piteous.

"Uhhh shit!" she whined, her fingernails digging into her massive melons. I didn't stop until I felt her warm, jiggly ass on my abs, my cock firmly planted in her tight pussy. "It's so . . . so . . . unnngggh! So deep!" she whined. "Do me," she pleaded, looking back at me again. "Fuck me like I deserve to be fucked!"

With a wry grin, I followed Deirdre's orders. I withdrew my cock all the way to the tip, and then slammed it back into her snatch all the way to the balls. Deirdre squeezed her nipples and whined, my thrusts punctuated with little squeals of mixed pain and pleasure. I held her butt cheeks tight, our bodies coming together with a sharp slap as my cock plunged in and out of her, gliding smoothly back and forth in her slick snatch. Fuck, she was tight! Deirdre was wringing the life out of my cock. Had I been a day older, I might not have had the stamina to keep her from cutting it right off!

In and out, in and out, over and over I fucked Deirdre. She moaned and cried, whined and groaned, biting and clawing at her big boobs as I fucked her faster and faster, my orgasm approaching quickly. Turning back to face me, she was rubbing her clit as I fucked her, and it was beginning to have an effect! She shrieked shrilly.

"Fuck!" Deirdre cried. "Fuck I'm coming!! Uuunnngghh!!"

Her pussy rippled around my cock as her second orgasm of the ride washed over her hot body, quaking and shaking with the force of it. I couldn't hold on any longer. Grabbing her boobs, I pulled Deirdre forward and began French-kissing her, roughly manhandling her tits at the same time.

Screaming into Deirdre's mouth as loud as I could, I held onto her with both arms wrapped around her as the orgasm came. She looked directly into my eyes as I blew the biggest load of my life into her hot snatch. As Deirdre was orgasming again, it took every ounce of strength to keep her from falling off, due to the huge amount of thrashing around she was doing. Spurt after spurt of hot white cum flooded her pussy. After I finished cumming, I grayed out for a few seconds. I do remember Deirdre sliding off my dick, still on top of me, our mingled juices running down her thighs. We half-dozed, just holding each other, sleeping and cuddling (it sounds faggy, but there's no other way to say it), both of us drenched in sweat, cum and pussy juice. I was drained; it felt like I had just been hit by a tornado. My cock was sore; her cunt had been so tight, wringing every drop of cum out of me.

It had probably only been a few minutes when I felt Deirdre's tongue enter my mouth again, probing every part of it as I groped her ass. Breaking free of the kiss (except for a strand of saliva between us), she looked into my eyes almost hypnotically.

"Thanks, honey. I've always wanted to break in a virgin."

Slowly getting off of me, the two of us walked into the house, hands on each other's butts, leaving our swimsuits out at the pool. Well, 'staggered' was a more appropriate word; we both had a bit of trouble walking. We cleaned each other up in the shower, before heading into her bedroom for another lovemaking session; one that was more romantic than lust-induced.

For the rest of the summer, Deirdre continued to be my 'trainer,' enjoying marathon sessions in every room of her house. She even took my anal cherry with her favorite strap-on at one point. But those are stories for other times .

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