Where it happened: My house
Langauge: English
Sex: Male
Rating: 2
Category: Straight
To me, sex is a special thing. It takes more than a fleeting, one-night connection for me to really feel like doing it. That’s not to say I wasn’t a stereotypical horny teenager — far from it.
No, I’ve only ever fooled around with my girlfriends. The first girl I ever saw naked was my first girlfriend. I was 14 and she was 15 at the time. It started with lengthy make-out sessions in the back of our parents’ vans en route to our dates and escalated to marathon sessions of dry humping when we were alone. Eventually we began exploring each other’s bodies by shedding clothes. I still remember the thrill of seeing my first set of breasts, first female nipples, and first wisps of female pubic hair. While we were nothing if not physical, we never went beyond using our hands to bring each other to orgasm.
I had my first experience with oral sex with my next girlfriend. We were smitten with each other, though we didn’t get to see each other often. When we did, it was often an explosion of physicality. One of my regrets is focusing so much on that and not the other aspects of the relationship but given how life has turned out, I can’t complain. I loved playing with her smallish breasts, running my hands and tongue over her nipples until they stood erect. As I mentioned, she was the first girl I ever went down on. While that no doubt biases my thoughts, she had the best taste and loveliest quiver when I’d hit the right spot with my tongue. She also gave me my first blow job. While she was as inexperienced as I, it still felt amazing. I like to think she found her first times as enjoyable as mine.
It wasn’t until college that I completely lost my virginity. Sure, I’d brought girlfriends to orgasm before and had the same done to me, but I’d never entered a woman. I didn’t have a girlfriend until my junior year. She was very experienced sexually but felt like she always reached that stage of relationships too quickly. Since I had really hurt a girl by being too fooling around rather than romance and been hurt by a girl treating me as a “friend” with benefits in turn, we resolved to put off sex for a while. Long story short, hormones won out and we did the usual get-naked-and-grope thing often. We would trade oral sex, watch each other masturbate, and even play around with condoms (for the future, of course).
After a few months, we were alone at my house. After watching TV for a bit, we started fooling around and decided to move to my bedroom. We each stripped off our clothes and intended to play around without penetration like usual. She put on a condom on me because it was different. I laid on the bed and she knelt over me. I loved (and still love) the way her breasts hung down over me and couldn’t resist taking each nipple in my mouth. Meanwhile, I ran my hand in between her legs and felt up and down her slit. After a little bit of this, I moved my hand away and she began rubbing my penis between her legs. As she’s kind of vocal, it was obvious she was able to find a satisfactory angle to build an orgasm. As we started moving our hips back and forth, suddenly things changed. I felt a flood of warmth around my penis and her eyes got large. We both paused immediately, unsure of what to do next.
She said, “Umm…,” and I replied by asking, “I’m in, aren’t I?” That sounds contrived, but it’s really the only thing I could think to say. Obviously, I was inside her, our foreplay being more than enough to make it go smoothly. Momentarily stunned by the suddenness of it all, I enjoyed how warm it felt. I enjoyed finally feeling that raw human connection sex brings. At the same time, I recall being somewhat surprised that it wasn’t as tight as I expected. I knew she wasn’t a virgin and hadn’t been for a relatively long time, but it still caught me off-guard. Regardless, that thought soon left my mind as she, knowing I still wanted to wait, suggested we could stop and “forget” it happened. I figured the important step had already been taken, so we might as well finish it off. She began moving up and down on me, setting a rhythm I tried to match. It felt different sliding in and out of her. Not bad–actually quite good–but different. She’s a women who can reach orgasm VERY quickly just through vaginal intercourse and since giving an orgasm always sets me off, I didn’t last terribly long.
Given how physical we were before doing it, it shouldn’t be surprising that we went at it a couple more times that day alone. Since then, we’ve had sex often and tried some things that were new to both of us. It’s a cliche, but it’s also the raison d’être of this site: no matter what new things we try or how many times we do it, I’ll never forget the first time.
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