Having sex with an ex, and it started in the pool. [M/f] | 2016

This was "that ex" — the girl who I thought was "the one" while we were dating, and who I had dated longer than anyone else prior, and with whom the breakup fucked with my head for at least a year afterwards. Her name was Rosa. (Editor's note: Fortunately, I met another girl about 2 years later who helped me get over Rosa and realize that we were never good for each other. Rosa and I eventually made our peace and went our separate ways; we haven't talked in years and that's probably for the better. The new girl and I ended up getting married and are extraordinarily happy together.)

Rosa and I had gone through a nasty break up. She essentially told me she wanted me to move out (although she later confessed that she had done it in hopes of "scaring me" in to making the changes she wanted) and that was that. Before that, though, we had been fairly sexually adventurous and she was my first for a lot of experiences — first time I came inside a girl without a condom, first time I came on a girl's face, first time having all-day marathon sex, the first girl to consistently give me head, and a bunch of others that I'm sure I'm forgetting.

After breaking up, we obviously still had a lot of lingering feelings because we stayed in contact. We would occasionally meet up at a bar or something to "talk" which usually turned in to her trying to make me feel guilty. I don't know why I kept meeting up with her, but love is a fickle mistress that plays some messed up games with your head.

One time I ended up meeting her at her place (what used to be our place). I'm not sure how that happened, but it was the middle of the day and we were both sober, so it seemed innocent enough to my desperate mind. It was a hot day and soon we had agreed that it was a good idea to go swimming in the community pool. Only problem was that I hadn't brought any swim trunks. She told me not to worry and went to her dresser, returning with a pair of her shorts. Now Rosa was a very petite girl — tall, but very skinny. I'm pretty skinny, too, but there was no way her shorts would fit around my waist. I tried them on to prove it to her. I was able to pull them all the way up, but they left very little to the imagination. Not only were they short, but also tight. I have a slightly above average dick — not a record breaker, but something that most girls I've been with have commented on. Rosa used to make the most comments about my size, as a matter of fact. I know that she was particularly fond of it. My dick was almost poking out the bottom of the shorts from how short they were, and their tightness meant a very obvious bulge. Not just a bulge — outline is probably the better word. You could see quite a few details. It was like wearing a pair of boxer briefs that were two sizes too small. As I stood in front of her to prove that they didn't fit, I noticed her gaze lingering for what seemed like a long time on my outline, before looking me in the eye, giggling, and telling me not to be so prude. She ran out of the house and towards the pool. I followed.

We swam for a while, but just swimming for swimming's sake was boring. So we started doing what any two, bored people with mutual attraction would do — we started flirting. It started really simply and subtly. Making comments, then playing tag, then grabbing each others hips instead of just tagging, then grabbing the other person from behind in a hug. Next thing we knew we were caught up in each others arms with no real idea how it happened. And of course, that became kissing, which became making out. We had made out once or twice since breaking up so I guess it didn't catch either of us too off guard.

One of those first experiences we shared was exhibitionism. It wasn't anything too crazy, but her house faced a busy street/sidewalk. There was a wall and some trees so that people couldn't look directly in, but someone who wanted to look could do so fairly easily. We had the doors and curtains open one warm day and ended up having sex on the couch. She was pretty vocal and I reminded her that people on the street could easily hear us and, if they decided to investigate, see us. Wow, she went wild when I told her that. I mean it really turned her on, and that's when I learned that she was in to light exhibitionism. So as you can imagine, us making out in the pool while I'm wearing almost nothing was having an effect on both of us, but especially her. We hadn't gone any further than kissing since breaking up because I was really trying to put space between us (and failing miserably, but hey). This time, however, I couldn't help myself. She was there wearing a tiny bikini; it was a warm, beautiful, spring day; we had been flirting for at least an hour straight; she was here in my arms right now. I never stood a chance.

She started rubbing me through my painted-on shorts while we were kissing, and I got hard very quickly. I started rubbing her ass through her bikini and was as hard as I've ever been. I directed her hand in to my shorts. She gasped in mock surprise but started stroking me directly while I slipped my hand in to the back of her swimsuit to continue feeling her ass. I brought my hand around her hips and pulled her bathing suit down just a little bit while doing so. Not much, but enough to expose her pussy while I started to finger her. She moaned my name in protest, but when I backed off, she looked at me like I had killed her. She wanted this very much, but was pretending to be a "good girl". I slid her bikini down again and rubbed my fingers against her, and her face showed immediate relief. We did this for a minute or so — me fingering her clit and eventually working a finger inside of her, and her stroking my cock underneath my (her) shorts. We both became exponentially more turned on, so I pulled my (her) shorts down enough for my dick to come free. Her eyes widened, but a small smile also flashed across her face. I pushed against her and felt myself start to enter her. We had had problems in the past with needing lube; that was not the case now.

Getting inside her while standing and facing each other wasn't the easiest, but we were persistent and finally I had the entire length of my cock inside of her. Oh, she was tight. She sighed my name again and said, "Anyone can see us!" I told her she was right, and already knowing what her answer would be, told her I could stop right there. "No! Fuck me!" she whisper-yelled, so I kept going. I had her back against the pool wall and used it as leverage. That allowed me to push harder, but with the resistance from the water, it was hard to pick up any speed. She was one of those girls who wanted it fast and hard every time, so I knew I wouldn't be able to get her off going at that speed. I considered turning her around so that the angles would be better, but quickly decided that that would make it considerably more obvious to any passers-by. Instead I reluctantly pulled out of her, told her to follow me, and got out of the pool. My first thought was to try and adjust myself so that my erection wouldn't be obvious, but quickly remembered what I was wearing and gave up any pretenses. Her house was only a 30 second walk from the pool so I'd just risk it. I headed out the pool gate and, looking back, saw her close behind.

We got in to the house and, remembering her kink for semi-public sex, I closed the screen door but left the regular door open. The screen was dense enough that no one could see unless they got close, but sound traveled through it like it wasn't even there. I pushed her over the arm of the couch so that her ass was pointing up and pulled off my laughably small shorts. Without any more hesitation, I pushed in to her from behind with two or three strokes. Her deep moan told me it was just the angle she wanted, so I picked speed like I remembered she loved and started giving it to her as hard as I could.

I could tell that she was slowly approaching orgasm, but I didn't want it to be slow. At this time I also started having some messed up thoughts. I remembered all the games she had played with me, culminating in her "breaking up with me" in hopes that it would scare me in to doing whatever she wanted, and realized that this whole encounter was probably just a play to lure me back in. I got a little angry and figured I might as well get mine. So I pulled out of her and briefly reveled in her protest, then moved her around to the other arm of the couch so that she was facing the open door. I guess she hadn't realized that I left the door open, or maybe she had forgotten, but now she was staring at it. I watched her put the pieces together in her head, but before she could complete the puzzle, I pushed in to her again and immediately picked up the rapid pace that she loved. In all our time together, I'd never heard her moan as loudly as she did right then. It only took about another minute of this before she was cumming so hard that her legs started shaking. She went up on her tip toes, then down again, then back up, then back down. Her face contorted and she held in her breath before finally letting it out in a breathy, throaty groan of "Yesssss".

Watching a girl cum has always been a turn on for me so by the time she came down, I was just about there. In our early days of dating, she had this strange (and awesome) habit of almost always finishing me in to her mouth. I asked about it once, and she said it was what her previous boyfriends wanted, so she thought it was standard for sex to end with the guy cumming in the girl's mouth. I didn't complain. I would announce to her that I was about to cum, she would push my chest until I rocked back on to my legs, and she would almost jump to get her mouth around my dick in time to catch all my cum, then neatly swallow it. After a couple months she realized that it wasn't the norm, and she started asking me to finish inside of her instead, but it was a lot of fun while it lasted. So now, as I'm about to finish, I flashed back to that and decided I wanted to do it again. I figured it would be difficult because of our positioning — her bent over the arm of the couch, and me fucking her from behind. But I also figured it was worth a shot. So I pulled out and said "I'm gonna cum!" Fortunately she got the hint and in a blur spun herself around and dropped down to her knees. In the same, fluid motion, she dove her head forward and took me in to her mouth. The timing was perfect, as if it had been rehearsed. No sooner had her lips sealed over the head of my cock than I started to shoot. She didn't back off of me until after I had finished, and she wasn't the type to make a show by opening her mouth and showing off my cum to me, so I'll never know how much I came. But let me tell you, it felt like a lot. And through my orgasm, I was able to make out her throat move in no fewer than three swallows, so I can only assume that it was a hell of a load. As I came down she diligently cleaned my cock off with her tongue, gave a final swallow, and then I collapsed on the floor next to her with our backs against the couch.

After we'd caught our breaths, she said "Wow." I parroted her in agreement. Never one to beat around the bush, she asked, "What does this mean?" I responded that I didn't know. We eventually composed ourselves, got dressed, and I told her I had to leave for work. Afterwards, I did not allow myself to fall back in to any sort of relationship with her. She probably felt used, and that was probably a fair feeling for her, but we just were not good for each other. Our sexual compatibility was about our only compatibility, and as stupid as I was to keep meeting up with her and now have sex with her, I still knew that we had no future together. She redoubled her efforts, and I redoubled my resistance. As I said earlier, I eventually met a really great woman who helped me to realize how toxic Rosa and I were for each other, and that was that. We cut off all communication. But I'd be a liar if I said I didn't fantasize from time to time about the sex we had.