Fun in the Pool

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Young man is tempted by much older woman.
3k words
4.26
140.7k
35

Part 1 of the 2 part series

Updated 10/18/2022
Created 07/20/2013
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What a day. Even for the Midwest in the middle of July this is too hot and humid of a day for me. Luckily, my homeowner's association has a pool for our use in the summer and today I plan on being there to cool off.

I picked this townhouse community because it's so quiet with mostly older folks and a lot of retired people in it. It's rare to see a kid or anyone under 50 years old here, so at age 26 I really stand out. Lately I've been getting the idea that a few of the older women here talk about me in their little groups, either walking or sitting around the pool. I've been out for a run and have seen a few of them looking at me, all sweaty with my shirt plastered to my chest and have turned around a couple of times and have seen them also turned around looking at my ass as I run past them. Crazy.

Since it's a mid-week holiday and most people are out of town visiting their kids or friends, it's quiet around here. I'm working in my small backyard planting a few hostas and watering the rest of the plants, etc and I'm sweating like a hog. I'm soaking wet and my t-shirt and cargo shorts are sticking to me like paint, outlining every muscle I've worked so hard to get over the last few years all through high school and college.

Since I have an end unit, I have the last house before the pool and there are three older ladies sitting at a table with an umbrella looking over at me work, they've been doing that for the last half hour. One older woman is sunning herself on a towel on the pool deck, lying on your stomach. I can't lie, when I was in my living room I was also looking out at them, fantasizing about what it would be like to have sex with much older woman than the usual 20-somethings that I run around with.

The one lying on her stomach was in such great shape that I didn't know she was "old" until she got up to put more suntan lotion on. Wow, what a great body! Full-figured with a great, full ass and those cheeks.. I could imagine putting her over my knee and spanking that beautiful, full ass. I sure love a full-figured ass on a woman. This tan, older woman had a work of art for an ass and I jerked off when I was fantasizing about her. I imagined what it would feel like to slip my cock in-between those beautiful, sweaty, oiled-up ass cheeks as she was lying on her stomach. Just pulling her swim suit to one side and slipping right in, my cock would already be lubricated and ready to go. Mmmmmmm.. I could almost feel her tight hole as my cock slithered right up it like a snake and she writhed around on her stomach there on that towel. Living here has given me an appreciation for older women and I was hoping to get to meet some of them up close and personal one of these days. This one in particular was on my mind.

As I was in the backyard sweating and working, I heard some voices and saw a couple of the women waving me over to the fence around the pool deck. They were the only ones in there. I walked up the tiny hill up to the fence and wondered what they wanted. I wondered if they were as horny as I was.

The oldest looking one, probably in her late-60's and quite attractive I thought, asked me why I was working so hard on the yard during the week and why I wasn't in the pool keeping cool on such a hot, humid day. I explained that my office was closed for the extra day after the holiday and I didn't have anywhere to go so I was just puttering around the backyard.

I could tell that they were looking at my chest and arms. I was in great shape. Not as in pumped up bodybuilder looking shape like where they stick an air hose in you and pump you up until you look like you're going to pop. But, more like Bruce Lee or some other all-around athlete with hardly any fat what so ever and well-defined muscles and abs. They were definitely checking me out through my sweaty, tight t-shirt. And, I was also checking them out. Apparently, their husbands were out of town and they had been enjoying a few cocktails I could tell, they were silly and giddy. Not to mention the drink glasses on the table.

After a few minutes of chatting I said that I could use a dip in the pool and that I was going in to change into my trunks and head back over. They all agreed that it was a good idea and that I should be relaxing rather than working so hard on such a hot day.

I went inside and changed out of my sweaty clothes and put on my swim trunks, wrapped a towel around my neck and put on my flip-flops. Before I went downstairs I looked out of the living room window at those ladies and I could see three of them were in the pool now and the hot-assed one was still lying on a towel, only this time she was face up with sunglasses on. Nice tits! I haven't really noticed them before but I sure did now. I imagined sucking on those great tits and nibbling on those nipples and sliding my cock in-between them and fucking them until I shot my cum in her mouth. Wow, what an imagination I had, there's no way they could be thinking the same things that I was. My cock was getting hard thinking about that.

I went downstairs and walked over to the pool. I couldn't believe that there weren't more people in there, just the five of us, the four women friends and myself. It was great, no kids or loud people or anything. They saw me walk through the gate in the fence and I kicked off my flip-flops, put my towel on a chair over by their table and stood on the edge of the pool testing the water temperature with my foot. They were all sort of floating around in the shallow end looking at me. Two of them were bigger ladies but not fat; just.. big. Full-figured with some extra weight but not bags of fat hanging off, they seemed to be in good shape for being in their 50's and 60's. The youngest one, I guessed, was in her mid-50's and she was the skinniest one of the bunch. She had brown eyes and brown hair and a tiny body but a tight, small ass. I've seen her out walking her dog in the past year since I've lived here and we've casually chatted about the weather or the neighborhood or whatever. I've jerked off thinking about her hot little ass quite a few times in the last few months.

The other two ladies were much bigger but still had great bodies and great full asses. I would have loved to be fucking into those big, full asses under that water. I wondered if any of my fantasies would come true today.

I stepped down the ladder into the pool as they watched me from about twenty feet away. The water was pretty cold compared to the outside air temperature and I could feel my formerly plump cock doing the "significant shrinkage" thing. But, it wasn't long before it plumped up again as the three ladies bobbed over to me and sort of surrounded me and started talking. Just talking about whatever, a mile a minute, like they were nervous or something. I think they were a little tipsy from having a few cocktails at their poolside table.

We all floated there for a while and eventually one of the older, bigger ladies floated over and asked about my muscles. I was embarrassed because I'm not a muscle head or anything, but I said I just work out to stay in shape. She asked if she could feel my arms and I said, sure.

She ran her hand and fingers up and down my arm, holding it and now using both of her hands to squeeze it and rub it, ohhing and ahhing. I thought she was joking around but I think she was really getting turned on from rubbing my arm. The other bigger lady took my other arm and started holding it and rubbing it up and down and I didn't even notice that Leslie, the 50-something woman, disappeared until I felt something behind me and it was her wrapping her arms around my waist, hugging me and wrapping her skinny little legs around my waist.

She was running her hands over my chest and abs and sort of humping into my ass as the other two women were almost acting like they were holding onto me so Leslie could do that. Little did they know that they didn't have to force me at all, I was ready for some action and I knew I was about to get some. When Leslie's hands started going further down and finally started rubbing my crotch and cock, I tried to reach back and get my hands on her but the two other women wouldn't let go! It was like they were going to force themselves on me!

I finally got my arms free and reached around and slipped my hands under Leslie's bikini bottom and felt her sweet little ass. She really started pushing into me as I did that and as soon as I found her slippery little pussy she started humping my fingers like she was in heat! I was spreading her ass cheeks apart as far as I could and fingering her naughty little pussy.

The two other women joined in rubbing my cock and ass and one of them went down under the water and pulled my trunks down, which wasn't easy with Leslie still holding onto me from the back like that. I felt two hands on my thighs and felt a mouth engulf my cock which was now fully in a hot mouth! I didn't even know this woman's name and she had my cock in her mouth! It was a strange feeling to be there, in public, and to be groped and used by these older women like this. Luckily nobody else was around to see this or who knows what might have happened. I grabbed her head and started fucking her mouth.

It didn't take long before I shot my load in this woman's mouth under the water, this was just too exciting! She was only down there for fifteen or twenty seconds at a time working on my cock but whatever she did worked. She came up and kissed me and transferred some of my own cum into my mouth! She really was a dirty old girl, I was going to have some fun with her.

Leslie's hands were on my now somewhat soft cock and she started stroking it as my fingers slipped easily in and out of her pussy two and three at a time, stretching that tiny thing out. I even once or twice shoved my fingers into her tiny little asshole and I could feel how tight it was when it closed around my fingers.

I couldn't take any more so I grabbed her by the waist from behind me and sort of spun around and buried my cock into her cunt!

"OHHHHH!!! Gawwwwwdddd..", was all she said as I pumped in and out of her tight little pussy as fast as I could under the water.

I pulled her bikini top off and her tiny titties had tiny little nipples that were ROCK hard! My mouth was on them so fast and I was nibbling and sucking on them as I continued to fuck into her tight 50-something pussy and pull her into me, bottoming out over and over again. She was bucking with orgasm when I spun her around again so I was looking at her wet ass and back and I slid my cock into her asshole in one move.

"AHHHHHH! What are you.. ohhhh.. that feels so good, I feel so full.. ohhh.."

I held onto her slim hips and pounded into her tight little asshole as hard as I could. It was like a shark attack with the sloshing that we were doing in there. The other two women were rubbing both of us all over and I could feel their hands on my cock as it came out of Leslie's asshole. They were putting fingers in my ass and squeezing my balls and spanking my ass cheeks, which wasn't doing much being under the water like that, but it was still exciting to see how dirty these older women really were. I had no idea I'd find anyone like these women in real life, it was just a fantasy of mine I thought.

I was close to cumming again so I grabbed onto Leslie's waist and held her against the wall of the pool and rammed into her ass and let loose with a hot load of cum.

"Here it comes! I can't take any more! I'm cumming in your little ass!"

She said, "Do it! Fill my naughty asshole with your dirty sperm! Do it! Do it! I'm such a dirty girl, fill me with your hot cum!"

After that I thought I was spent for the day but after a few minutes of just floating there and rubbing each other, my cock was once again at attention. I floated on my back with my cock sticking out of the water and they took turns sucking on it making it even harder.

After telling them that they were going to make me cum again I slid it into the pussy of the older women, the one that motioned me over to the pool fence about a half hour ago and the one that had sucked on my cock under the water. She was floating on her back and I grabbed her by her beautiful feet and legs and floated her over to my waist and speared her cunt with my rock hard cock and hit bottom in one motion. She just groaned and started treading water behind her with her hands to try to stay floating as I pulled her onto my cock. I was plunging deeper and deeper into this seldom-used, slick, tight tunnel of mature love and it felt as good as any hole I've ever fucked. Her tits were out of her bathing suit and I slapped them and grabbed at them, twisting her fat, hard nipples until she was writhing in orgasm.

What a ride. She had a great, smooth pussy and I pictured myself filling it with a load of my hot sperm, but the other older woman came over and sort of pulled her friend off of my cock and backed into me. I didn't hesitate, I pulled her suit to one side and squeezed my cockhead between her sweet, fat ass cheeks and poked my cock head into her tight sphincter, sliding my dick all the way into her asshole until I was hitting my wet chest against her wet back. I started humping her like I had never humped anyone in my life; over and over, bottoming out in this cushioned fat ass and then pulling all the way out and pushing cold pool water in her asshole before my cock would squeeze it out again. I could feel her pushing out the cold pool water when my cock hit her hole again over and over. I wished that I could see this better but since she was mostly under water it was blurry. I grabbed onto her around her waist and by her tits and pulled her back into me as I rammed forward into her plump ass. My cock wasn't going to be able to do this for much longer, the feeling was too great. Sliding between her two big balloon ass cheeks under the water was too much for my sensitive cock head.

"Mmmmmm.. I always wondered what a cock would feel like in my ass.. Our husbands have lost all interest in sex and we're all in our horny prime!We've been watching you for months and were always hoping to talk you into coming over for a dip."

Hearing her say that was too much so I grabbed onto her huge tits and pulled her back into me as I squirted jet after jet of cum deep in her colon.

"Rrrrr.. mmmmmmmmmmmm.. I can't stop! I'm going to fill your beautiful fat ass with hot cum! Your beautiful, tight, fat ass!"

"Fill me! Do it, we've wanted to get you in here for so long, fill me with your young sperm! I can feel it squirting in me!"

After that I needed a rest so I suggested that we head out of the water to relax for a while. As Leslie went in front of me I pulled her bikini bottom to one side and kissed her right on her beautiful asshole as she walked up the ladder. My tongue pressed and flicked into her sweet little rosebud and it was picture-perfect. She shuddered and her knees buckled and she fell back into my arms so I carried her up to her chair, kissing her passionately on the way back to the table. I knew it wouldn't be the last time I'd have my mouth and tongue on her mouth and tongue, or on her hot asshole.

As I carried her over to the table I noticed that the mystery woman wasn't there on the towel. I wondered aloud where she went and they all sort of giggled.. hmm..

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AnonymousAnonymousalmost 4 years ago
Oh god that's so good

My god, that was amazing! I was disappointed the Mystery Woman on the Towel didn't come into play, but I'm glad to see you have written a part two! This Part 1 is amazing!!! :D

AnonymousAnonymousabout 4 years ago
Neighbor

I had an erotic experience like this with my 72 year-old downstairs neighbor when I was 40. We'd been neighbors for about 4 months, and I'd helped her with a few things in her apartment. One night I went to the jacuzzi and was delighted to find here there. She looked amazing in her one-piece bathing suit, and after a wine buzz, she became flirtatious and started feeling my cock. When her thighs touched my cock, I went instantly erect. She loved every inch of my big thick cock, and we ended up at her place, where I fucked her to 3 orgasms, then spurted all over her tits!

AnonymousAnonymousover 4 years ago
My dream set up

BUT, let's not kid ourselves. I would LOVE this but in real life i would be wondering about disease. Even if i didn't usually wonder i would in this ultra easy set up.

Sighing here, not sure what is better, open fantasy or restricted reality.

shadoblivionshadoblivionover 10 years ago
keep on going and keep up the anal theme!

Dont listen to those anonymous douches! This story is great and I hope you continue his adventures in the asses of cougars. taking a woman in the ass is one of the greatest joys a man can experience and I lord knows I wouldve done the same thing if I was this kid. keep it up, this is great stuff!

LITTLEBUM2002LITTLEBUM2002over 10 years ago
great story, love the anal

I love anal sex as well. Glad to find it in a Cougar story. And those guys are nuts: why would you want to fuck only a pussy when an ass is tighter?

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