This happened a while ago, so some details are fuzzy, but the jist of the story is still clear in my memory.
After my first year of college I moved back home for the summer to work and save money. In high school I was an average guy, decent looking, a little over 6’ tall, 180 pounds, but a little soft. I played baseball but wasn’t particularly outgoing or smooth with the ladies. However, during my freshman year of college I spent a lot of time in the weight room, attracted the attention of the coeds, and came back home with some swagger.
Back at home, a friend of mine (let’s call her Amy) invited me to a pool party at her house because her parents were out of town. In high school, Amy and I were in the same friend group and I got hints that she had a crush on me, but due to my shyness around girls I never pursued it. I hadn’t seen Amy since arriving back home, and when she first saw me I could tell she was impressed with how I had changed while at school. The feeling was mutual, as she was looking better than ever – about 5’6”, toned soccer player body, bigger boobs than I remembered, straight dark hair she usually wore in a ponytail, and a beaming smile.
The party was pretty tame since only six or seven people could make it, but we had fun sharing college stories, swimming and jumping off the diving board, drinking beer, and flirting a bit. After a few hours the party broke up but I told Amy I’d stick around since I lived just a few houses away and could walk home. So we had a few more beers and the flirting got more serious. It was still pretty warm and humid so we decided to take another swim. In the pool Amy started getting a bit more touchy and we started play-wrestling a bit. This turned in to a few playful kisses that mixed with real kisses. Her bouncing boobs that she had been pressing in to me were having an effect also, and I know she was well aware of my growing hard-on.
At this point we could both tell where this was headed, but I was really nervous – because I was still a virgin. I had fooled around with a few girls in college, but never gone all the way, or even gotten a girl’s panties off yet.
Anyway, we continued to wrestle around in the water, Amy got a mischievous look on her face, and she and started trying to pants me. I was able to fight her off, and started trying to grab her bikini bottom too. Somehow I got ahold of one of the strings on the side of her bikini, gave it a sharp tug, and it was off! So as I’m dancing around with a white bikini bottom in my hand, she goes underwater, takes firm hold of my trunks, and yanks them down.
So there we are, each holding the other’s swim suit. We’re both in the water, but she can see my big obvious boner, and I can see her dark brown muff ( this is the late 80s, and I learned later that her muff was carefully trimmed). We come back together and start kissing a bit more passionately, my hands are all over her firm butt and beautiful full tits, and she has a tight grip on my ass. Eventually, I’m rubbing her pussy, she’s stroking my dick, and I can feel that my head is very close to her entrance. As we continue to kiss and grope, I gradually (and awkwardly) start to ease in to her pussy, and eventually we’re full-on screwing. I’m finally getting laid!
As you might know, sex in a pool can be difficult, and I’m doing it for the first time, so we decide to get out, dry off, and continue in her bedroom.
We continue the first round in the missionary position but I’m Quick Draw McGraw, so after 10-15 strokes I pulled out and came on her belly. After a clean up and apology, we go back to kissing and cuddling and my dick is back to life. She has a bit more experience than me and wanted to take charge so she got on top and rode me, instructed me where to rub her clit, and climaxed hard. When I told her I was getting close she told to come inside her because she was on the pill. Afterward she just laid on top of me with my cock still inside her, and I stared up at the ceiling, probably with a dazed look on my face, and then I headed home.
We ended up having a bit of a fling that summer, I eventually told her I had been a virgin, and we did naughty things to each other in a variety of ways and locations.
Source: reddit.com/r/gonewildstories/comments/d05l7h/first_time_m_at_pool_party_with_friend_f_a_bit