[MF] My first good sex started at the pool

I had some other stories I was planning to write, but this one fits with the contest theme. Not sure it is as sexy as some of my previous ones. Always appreciate feedback.

I was 21 when I had good sex for the first time. 

Up until then it was mostly quickies or clumsy and drunken.

When I was a sophomore in high school Dana really liked me. She was pretty with a long, lean body. Great ass and legs from running track. We hooked up a few times. Even though she was a grade behind me, she was far more experienced. And we did things I had never done before. 

But I had always had a crush on Mandy. Since fifth grade she just strung me along. We were really good friends, but I could never break through. 

Once Dana and I started getting together, Mandy suddenly changed and told me she wanted to be with me. I guess it was a case of wanting what you can’t have. So I bailed on Dana, without any maturity or grace, and jumped right in with Mandy. 

Mandy was far less experienced and things were not as sexual. But I thought she was the one. It lasted about a month and she was on to someone else. Broke my heart at the time, but in hindsight, it was even worse because Dana had moved on and was a bit bitter about the whole thing. And the things I could have learned from Dana. My first good sex could have been a regular thing years before it was a one-time event. 

Dana and I stayed friends through high school. Good friends. Talked on the phone several times a week, etc. A couple of times we made out at a party, but she was still hurt by me casually tossing her aside and never let me forget it. And she had boyfriends most of high school. 

I learned later from one of them that she was a nympho. He said they had sex all the time and she blew him everywhere. Damn. I really fucked up. 

We lost touch after high school. I moved away for college. But then one day she called me to say her family was going on a trip to the city where I was going to college and asked if I wanted to hang out. She was engaged at the time. Yeah, I know she was only 20, but we came from a small town and several classmates were already married with babies. 

She was engaged to a guy a year older than me who was finishig his senior year of college in another state. I assumed she just wanted to hang out platonically. 

She drove over to my apartment about 9 p.m. after dinner with her family. It was my first solo apartment. A one-bedroom with no roommates. That only lasted six months and then I was with roomates again for a decade. 

She showed up wearing a long dress with big slits up both sides. Not a formal dress. Made of cotton or something like that. The top of the dress had spaghetti straps and she wore strappy wedge heels. She is 5’7” with dirty blonde hair. It was long when were in high school, but she had recently chopped it off. She didn’t look as pretty with the shorter hair, but her body looked great. 

We talked for a bit and then I asked her if she wanted to eat, go to a touristy area, a bar, or something? She said she could do all the tourist things with her family and she had already eaten. She said she just wanted to hang out with me because it had been so long and she missed me. 

At some point we talked about our missed opportunity. I apogized and told her it was a mistake I had always regretted. She made a joke about how if we had been together in high school I never would have thrown the wild hot tub parties at my friend Shawna’s house. (Those were a lot of fun, but I can’t tell them here.)

I asked her what she knew about those as she had never gone to one. She had two long-term boyfriends in high school and dated the guy she is engaged to now through most of it. He was pretty controlling and never partied with us. Knowing what I know now, I don’t blame him. I think they were just fucking all weekend long. Why go to a party when you can just fuck?

She admitted she regretted not participating in some of the hijinks back then. I joked that the apartment complex has a hot tub. 

She said, “okay.”

What? It was November. Yes, I lived in a sunbelt state so it wasn’t  snowing or anything, but it was still not pool weather and it was about 10 p.m. 

I asked her what she would wear. She said she’d wear one of my T-shirts. I wasn’t sure if she was teasing me, or really meant it. But I went and grabbed her a T-shirt. I thought about handing her a white one, but that seemed a bit crude.

She went in to the bathroom and came out wearing my shirt. I couldn’t tell if she kept on her bra or panties. I quickly put on swim shorts and we headed to the pool. 

It was late, and definitely not swimming season. The pool was empty. Turns out it closes at 10 and the gate was locked. So we jumped the fence. The pool was at the center of the apartment complex and well lighted along the perimeter. But not many people were around. 

There was some flirting, but nothing had happened yet. Then she asked if the pool was heated. I told her i didn’t know. She got out of the hot tub, her back to me, pulled off the wet shirt and jumped in. She was wearing panties and no bra. 

She said the water was great and I should join her. So I jumped in. It was cold. So cold. She laughed. We splashed each other and kind of wrestled around in the pool dunking each other for a few minutes. 

At some point we were holding each other and started kissing. 

Then she said the pool is too cold and got out of the pool and went back to the hot tub. Her 20-year-old B cup tits were perky and perfect. Her tight ass in wet panties was even better than I remembered. And her toned runner’s legs looked so good.

I followed her to the hot tub. She grabbed the wet shirt and looked at it trying to figure out how to put it back on. Then tossed it aside. I was not sure if she was feeling guilty about the kissing. So I sat near her, but didn’t try to kiss her. 

She looked so sexy in the glow of the lights. Her tits hidden by the bubbles. Then she told me it was not fair that she was the only one naked. I said that we were both topless so it was equal. She immediately slipped off her panties and tossed them by the wet shirt. 

So I slipped off my shorts and tossed them to the side before going in for the kiss. 

We passionately made out. I fondled her tits. Kissed her neck. Sucked a nipple. She made a slight moan, almost a hum, as I sucked her tit. Then she reached down and stroked me. She flipped us around so she was on top, straddling me. Her tits were now out of the water, giving me full access. She was grinding against my dick as I sucked her tits. Then she just took me inside her. 

I wasn’t expecting it. I had almost always used condoms before. Growing up in a small town, I saw way too many teen pregancies. But I didn’t give a shit. 

Little did I know then that sex in water may sound hot and look sexy on TV/Movies, but it kind of sucks in real life. I still didn’t care. Like I said, I hadn’t had good sex yet anyway. 

Occassionally people would walk by the pool area going to and from an apartment, but she didn’t seem to care. She would stop riding when she noticed, but then would start again. The hot tub was off to the side and kind of surrounded by bushes and trees. If anyone looked, they would see us. But there wasn’t much reason for anyone to be looking. 

At some point we heard keys and the gate to the pool opening. It was the security guy. He was on the far side, so I don’t think he could see much. He stood just inside the gate and told us the pool was closed and we should be gone by the time he comes back. He was cool about it and even left the gate propped open for us, so we didn’t have to hop the fence to get out. 

When he left we got out. She put on her panties but just held the shirt against her chest to cover her tits. We got back to my apartment and she suggested we needed to shower. 

My first time showering with someone. It was hot. I soaped a wash cloth and made sure to get every spot. As I said, my sexual experiences were all quickies. So I enjoyed exploring her body. Spending time on her tits and ass and her incredible legs. She returned the favor and then when she was done she knelt down and took me in her mouth. We tried shower sex, but of course shower sex sucks. What did I know back then?

We got out and laid on the bed. Holding each other. Kissing. Fondling. I asked her what she wanted to do next and she asked if I had whipped cream. Of course, I didn’t. But I said there is a convenience store two blocks away and I’d be happy to get some. She said she wanted me to. 

I was very inexperienced (well, I had had sex with about 10 women in my life at this point, but clearly had no clue what I was doing). And whild she had a lot more experience, we were still so young. So we were just trying out stupid shit we saw on movies. There was no Internet back then so we didn’t even have much porn to guide us.

I can’t even imagine how we looked walking in to the convenience store. She was wearing a pair of my sweats and a shirt with soaking wet hair. It must have been around 11 by now. As we were checking out with nothing but a can of whipped cream, I saw a friend from school who gave us an odd look. 

Back at the apartment, she told me to get naked and lay on the bed. 

She sprayed the whipped cream on my dick and balls, then up my stomach, on both my nipples, up my neck, and onto my face. 

She started kissing me on the mouth then worked her way down. She was so good. Every part of me felt like electricity was running through my skin. I had never even considered having my nipples sucked until she did it. It was incredible. She explored every part of my body. I had never had someone take the time to just give me pleasure like that. 

Then she made it down to my dick and gave me the first great blow job of my life. She licked and teased. Sucked my balls. Constantly made eye contact. Licking up and down the shaft while looking me in the eyes. Then took me in her mouth until I came. She held it in her mouth. Smiled. Then swallowed. 

She then stripped off her clothes and laid back ready for her turn. 

I just tried to copy what she had done to me as much as possible. I knew it felt great and assumed if she was doing it to me, she would probably like it done to her. I sprayed the cream on her tits, down her stomach, and between her legs. I put the can to her mouth and sprayed some in and kissed her. Then I started working my way down. Kissing. Slirping. Sucking. I got to her pussy and licked up the cream and slid my tongue inside her. 

In the coming years, I would learn to be really good at eating pussy. I now think it is my sexual super power. But back then, I was just fumbling along. 

I slid my tongue inside and tongue fucked her. I knew a clit existed and roughly where to find it. So I pushed against it with my finger while I licked her and tongue fucked her. 

I may not have known what I was doing, but it worked. She had her first orgasm of the night. I went up to kiss her and we laid next to each other for a minute. Then she told me that I had missed some whipped cream. 

Where? I don’t see any. 

She pointed down. I moved down to inspect and she lifted her legs to show me her ass. I didn’t know ass play was a thing between straight people. This was the mid-90s and I was naive. But I was having such a great time and had made me feel so good that I was up for anything. 

There was some sticky, melted cream down her ass crack. Then she grabbed the can and sprayed it right on her hole. It was clear what she wanted. Then I licked it up. FIrst around her asshole, then my tongue dove in. She rubbed her clit while I rimmed her and she had her second orgasm of the night. 

“Fuck me,” she said after she caught her breath. 

I was 21 so I was hard almost instantly after I came from her blow job. So I climbed on top of her and started fucking in missionary. I had no skills. So it was just thrust in and out as hard as possible. Couldn’t have been the best for her. But then she told me to wait for a minute. She got up and turned around. We fucked doggy style, a position that better matched my limited skill set. She came again. And the sounds she made while cumming turned me on so much I came inside her. 

I was shocked I had lasted that long. At that age, I was so happy to be getting any, that I usually came way too quickly. I couldn’t believe I had only cum once before that the whole evening. Some of it makes sense now that I know it is difficult to cum during water sex. 

God, I hoped she was on the pill. I just unloaded in her without a rubber. I started to get a little concerned about it and then she started kissing me again and I forgot all about it. 

She then got on top of me in a 69 position and started sucking my semi-erect dick back to hardness. I licked and did everything I could think to do. She seemed to like it but didn’t cum from it. She climed off and got between my legs. She licked my shaft, sucked my balls. Then licked my taint. I had never had a good blow job before. No one had licked my taint. It felt amazing. She noticed how by body responded and kept licking lower. Next thing I know she was rimming my asshole. 

Being from a small town, there were lots of weird gay hang ups I had to shed in my 20s. I wasn’t sure what to do. It felt wrong, but felt so good. She licked around my ass and tongued it. It was a feeling I had never had before. She loved teasing and toying with me. Lightly stroking my dick while licking my ass. 

Then she climbed on top of me and rode me like I had never been ridden before. Before this it was mostly just up and down. But she had this amazing hip control. The way she rolled her hips while I was inside her was incredible. That combined with the previous ass play and I exploded inside her again. 

We kissed and cuddled and fondled for a bit. But it was now 3 a.m. and she had to go. We took a quick shower to wash off the cream and the sex. Then she was gone.

Source: reddit.com/r/gonewildstories/comments/vswm3m/mf_my_first_good_sex_started_at_the_pool