This is the story about how I met the most important woman in my sexual history. If Kiki is reading this, I hope she remembers who I am, and sends me a PM.
I was a shy kid with few friends all through high school. I went to college having gone to prom without a date, and not having dated anyone all 4 years. I tried dating once I got to college, but after having my heart broken a couple of times, and being friend zoned by a woman I pined over for 2 years, I was still a virgin at 22, and frustration was setting in.
By that point, I had discovered that the Internet was a good way to kill some of the frustration I was feeling. I discovered cam models, who would pay attention to my needs, and then get naked for me. I remember accidentally spending over $70 on a session once because we got to chatting about other stuff than sex, and the minutes just kept ticking by.
Through the cam sites I used, I saw an ad for Adult Friendfinder, and signed up for a free account. I still wasn’t thinking about using it to meet in person, only to meet people for cybersex (hopefully for free this time), but soon the hormones of a young man overtook any moral question I might have had, and I soon met with a woman who took my virginity.
I don’t remember that woman’s name. We only met a couple of times, and the sex was never great. I discovered that I’m well endowed, and therefore wasn’t able to enjoy a blowjob, regular condoms didn’t fit, and while she let me in bareback, I was unable to cum. I went back to the website, and started chatting with other people, which is how I met Kiki.
Kiki isn’t her real name, but it is what she preferred to be called. We were both students at the same university, though in different programs, so we would have never met without the site. Her profile had no pictures, but at that point I was just excited to have a woman respond to my request to chat, so I didn’t care. As you’d think, men far outnumber women on sexual sites, and therefore have tons of guys to choose from. Just getting a response was a jackpot in my eyes.
We agreed to meet at a bar near campus, chat for a while, and then go to a nearby hotel. I met her outside the bar, and I admit I was a little disappointed with what I saw. She was tall for a woman, but still shorter than me. She had a round face, and long chocolate brown hair. As it was winter, she wore a long peacoat, but I could tell that her figure underneath would put her into the “heavy” category. Still, I was lonely, and she was willing.
We went to the bar, had a few drinks, and got to know each other. I don’t remember what we discussed, but she seemed to like me, so, not wanting to disturb roommates, we got a hotel room. Despite no longer being a virgin, I was still a bundle of nerves, and had a hard time getting hard. However, my previous experience taught me how to go down on a woman, and its something I enjoy to this day.
She wanted the lights off, not being happy with her body. I didnt mind. . We got naked, and into the bed, kissing each other. I am vey much a boob guy, and she had those in spades, and I enjoyed playing with them, making her moan my name.
Again my nerves and a too tight condom got the best of me, and I was unable to keep an erection. Instead, I put my head between her thighs and went to town on her with my tongue. She was shaved, clean, and delicious. I tried a trick I read about online, and started to write the letters of the alphabet over her clit with my tongue, my fingers inside her pussy providing the punctuation on her g-spot. Kiki moaned loudly in delight, and while my previous lover wasn’t silent, I found Kiki’s louder screaming to be much more erotic.
She came hard for me. Figuring it wasn’t going to happen for me that night, I climbed back up the bed, and she immediately latched onto me while she came down from the high. I didn’t mind. By that point I had found that I enjoy giving a woman an orgasm as much as I enjoyed my own. It was late, and so we cuddled up together under the hotel blankets and tried to sleep
This was the first time in my life that I had to share a bed, and I found that I could not sleep *at all*. I lay there for hours, not able to sleep, still kinda horny as I never got my own release. Sometime around 2, my body had finally calmed down enough, and realized that I had a willing woman in bed, that I was finally able to get an erection. I could tell that Kiki was having similar problems sleeping, so I got a condom, put it on, and asked if she was up to a round 2. She Enthusiastically agreed.
That goddamed condom again gave me problems. Circulation cut off, I immediately lost my hard earned hard on. It was then that she said those 4 little words that made my night: “I’m on the pill.” Permission granted, I got rid of the damn balloon, and again went down on her to keep her motor running while I worked on myself.
Finally ready to go, I worked my way back up her body. Her legs hooked over my hips as I finally pushed into her. She was wet, open and ready for me. Her pussy, while not tight, was pleasantly warm and firm. We fucked like that for what felt like an eternity, he moans and screams egging me on. I lifted her legs up higer, her ankles up by my ears, folding her nearly in half, and allowing me to plunge deeper inside her. This resulted in louder screams which encouraged me to go harder. Finally, I felt my own orgasm approach. I buried my cock as deep as possible, and came inside her. Her eyes rolled up as she felt me pulse.
Finally spent, I withdrew. This time it was both of us who wanted to cuddle. We lay together the rest of the night, sleeping fitfully, and leaving at first light. She gave me a goodbye kiss as I dropped her off at her car, and told me to call her again some time. That was the start of a friend with benefits relationship that lasted for years. We lost touch maybe 6 or 7 years ago, and sometimes I miss her. I got married last year, and my wife looks an awful lot like Kiki, same round face, long chocolate brown hair, and heavy body. I don’t doubt that my taste in women is because of her. I hope she’s doing well.
I do have other stories of adventures with KiKi, and with the other women I met on AFF. I’d be happy to share if this story is popular.