It was early December, 1998. I was a few weeks from turning 19.
It was memorable only because it was so, um, unmemorable?
My boyfriend was tiny. When I say tiny, I mean I’ve used tampons which were bigger.
I honestly wondered if I’d even, technically, lost my virginity with him.
In addition to that, he was so small, none of the condoms would stay on and we went though a 6-pack before he even finished. I did not finish. He didn’t care.
I later found out he was dating me because he was obsessed with my (then) married sister and he was hoping she’d see how great he treated me and divorce her husband for him.
Hahahahahahaha - the joke was on him. She was disgusted with how he treated me and stopped speaking to him.
Early August 1987 (I could give you the exact date if I felt like digging out the calendar from my keepsake box). It was a Sunday, the day before my senior year of high school started for me, the day before he left to go to Air Force boot camp for him. He liked me well enough. I loved him and knew I would never see him again.
Well, that depends. The first time my dick was inside a pussy was July, 1984. No idea of the date or time. I was 17. I didn’t finish. My friends and I were driving around one night at the beach and picked up a girl who had just hopped out of a cab and was walking to her front door. My friend called her over & asked if she wanted to take a ride with us. I was driving my big station wagon. Friend 1 went into the back with her and they did it while I drove around in the dark, then it was my turn. We did it for a while but I couldn’t finish- the back of the car was uncomfortable, it was a bumpy ride, I was nervous about cops seeing us, etc. Then she sat in the backseat and blew friend #2. Not sure if that counts as my first time.
I had gotten blowjobs before that, starting when I was 16. The first time I finished inside a girl was in college, I was 18 and my girlfriend and I had anal sex (she was really nervous about getting pregnant). The first time I finished in a pussy was also college, 19, the couch in her apartment. I have no idea even what month these occurred.
Early September 1997, a few days after I’d moved into university residence. I was 19, he was 21. We’d been dating for a little over a year by then.
Even though we’d done just about everything else up to that point, both of us were virgins and had no idea how to go about the whole thing, so it was more comedy of errors than X-rated porno… awkward, uncomfortable and not particularly spectacular. We managed to work out all the kinks in the process after a couple more tries, though.
September 9, 1982, at about 3 in the afternoon. It was really quite horrible. We were outside behind a brick wall near the Connetquot River on the Dowling College campus on a week day. Not only could we have been interrupted, but there was broken glass nearby. Also, I think my dad was at my dorm waiting to bring me over to visit my Grandma.
Girlfriend’s dorm room, either Spring or Fall semester 1980. It was late at night. I would have been 18. I remember we were on the floor and not the bed, I don’t know why. I remember also thinking and say something, like “wow, I see what all the fuss is about.” and she replied something like the 1980 version of “meh.” I had a bit to learn about how to please a woman, (and apparently so did she, as about two years later she became a committed lesbian). We had other, more satisfying moments.
December 29th, 2002. Day after our wedding. It was awkward and fun. I was a virgin, he was not. We spent the rest of our honeymoon enjoyably practicing.
It was September of1995. I was nineteen. In his dorm room. In those little tiny twin beds. I don’t remember much about it, not even the time. First time wasn’t memorable - not much pain, not much pleasure, just sort of meh.
My tangentially related story was that I had made a promise to myself that I would not have sex before twenty. I had only two months to spare and think I did pretty well.
At about 10 am, May 28, 1996, in my future ex-wife’s bed at her parents’ house, about a week after graduating high school (and the day before her birthday, now that I think about it). They had both left for work, and I came over to hang out. One thing led to another, and before you know it, two cherries had gone missing before lunchtime.
For me, it was a slow process that began in spring 1975 (at age 13) and ended in summer 1983 (at age 21). Her name was CarolineKathyEllenPennyBetsyMarcyPamelaRose. She was quite a girl!
