It wasn’t this adorable redhead by any chance, was it?
I hired a prostitute. She was a very nice girl from Jamaica who went by the name Ophelia. A pleasant experience over all, although I didn’t get a happy ending.
Afterwards, I went back to my hotel and threw up. Not sure what that was about. I think it was the jet lag.
I lost my gay cherry on my soon-to-be boyfriend’s couch while watching Dark City. Much more enjoyable, and no vomiting, which is always a plus. Kind of a wierd date movie, though.
We were 16. I was late getting home from school, because we’d been making out on the stairs to her house. I got grounded for a week. That very night, we sneaked out at 2:00 am. She lived with her grandparents in the second floor of a cinder block house. The ground floor was storage. We slipped in there, pulled the dust cover off a sofa, and quietly, hastily coupled.
The next day, I had the age-old, idiotic idea that dipping the wick somehow made her my steady girl. She went along with the gag, right into what the names of our first six children would be after we got married. She was truly, seriously disturbed. I had the mistaken impression that I was an outcast, and I couldn’t get a weekly humping anywhere else. :rolleyes: I later found out that I was liked and respected by many classmates, and several saner, prettier girls were wishing I’d ask them out.
Maybe I’ve done dumber shit than that, and maybe I haven’t. :smack:
Uneventful. She was 18, I was 15. I wasn’t very coordinated and wasn’t entirely sure of what went where. Yikes.
I was 15, she was 16. My bedroom, after school, Grandma downstairs watching her stories. Went at it for an hour, an hour and a half or so. Never did have an orgasm, neither then nor the second (and last) time with her. Sent her over the top many times with my, um, linguistic talents, however (not right then, necessarily, but over the time we were getting into each other’s pants).
Between my oral skills and my (apparent) porn-star quality stamina, she eventually came to the conclusion that I had lied about being a virgin altogether just to get her riled up to jump me. I still think it was just the lack of quality sensation through the condoms.
I was 20, she was 19. Front seat of my car (good old bench seats!). She was a redhead, and it was St. Patrick’s Day. Woot!
Aaaaaaaaand what a coincidence! I was born in 1975. 
I knew I was gay since the age of 5, but couldn’t get laid till I was a college freshman. I had an acquaintance named Fred, who was obviously gay. Though I considered him very hot, I had no idea how to let him know how I felt. (He later told me that he thought I was simply not interested in him.) Fred and I lived in different rooming houses on the same street. We both had Calculus finals on the same day, and decided to study for it the night before, in his room. Long story short, math was the furthest thing from our minds that night. It turned out, Fred had quite a sexual history, both straight and gay, since the age of 9. He refused to believe that it was my first time.
And by the way, we both aced our finals.
I met a girl in Myrtle Beach, SC on a trip with my two best friends from high school, Tim and Kevin. We were there for a week and I met her on the first day. On the last day before we left, I was lucky enough to be able to put my hand down her pants on the beach at night. My first feeling of wet pussy.
We corresponded for the next year, and my friends, along with my two brothers went back that summer. We all stayed in the same hotel, and I ended up fucking her in the hotel room with my two best friends and my two brothers in the same room.
I forgot to add, I was 21 years old at the time. I can’t believe I let the women of this world wait so long to experience the sex god that is Fiddle Peghead.
Well, I kept it in a lockbox…and then forgot what I did with the key.
Of course, I’m not sure that quite fits what you meant when you said ‘lost’…
I had a long-distance relationship with a Japanese woman. I was 21 and she was 30. We did cyber sex, phone sex, MMORPG sex, webcam sex for a long long time, and finally we met.
Penis ensued.
For a little description, we made out the whole way back home… with my parents driving. We had no shame. It was like an explosion. When we got back home, we immediately went upstairs. We stripped. I hesitated a little, thinking maybe we should slow down. No way. She sat on top of my member and proudly announced in English: “Congratulations, you are not a virgin.”
I didn’t have a condom, so monkey sex had to wait for the next day. Mmmmmm… sex.
I was 15 and was at a party at my friend’s house while her parents were out of town. I liked a 19 year old friend who was very cute but shy. He was a virgin too so I threw myself at him.
The sex would be best described as disorganized. I think we both felt like it was our big chance to try out all kinds of ideas and some of them were a bit ambitious. It was also extremely dark and we were both kind of drunk. Later I had a lot of blood on my underwear but the dumb thing was that a month later I did it again with someone else and I bled again. All in all I remember my first time as being thrilling but mostly because of the spirit of adventure and being proud that I overcame my shyness. I had been very worried about getting the nerve to have sex. Or course I look back and think I had plenty of time but at the time it seemed like number one on the to do list so I had the feeling of accomplishment crossing that off.
It involved Robert Burns, a lot of Scotch, a kitchen table, mailboxes, and a liberal sprinkling of guilt.
High, while at a cast party, in the bathroom, at 17. With an older woman of another race.
In my red 'Vette, which was parked in the driveway of my best friend’s parents house, a couple of days after my 19th birthday. Never saw the gal before or since. 
I lost my virginity twice. Let me explain.
The first time was when I was 19 in my boyfriend’s bedroom. Only thing is, I was really nervous and he was kinda big and it just hurt too much. He got about half way in and that was it. It sucked, and he wouldn’t even try with me again. It was his first time too. I guess it counted because there was penetration, but it lacked everything else. I almost don’t want to count it.
The second time was when I was 21 in my bedroom in my apartment. I was still nervous, but a lot more turned on so things went a lot more smoothly…and my hymen broke. Different guy.
I’ve still got mine; any of you lasses want it?
I was 13 and she was 93 (but was a hot 93 years young).
I was never allowed to sell Cub Scout Peanuts at the retirement home again.
Interesting story about that, not flattering in any way, but still interesting IMO.
I dated a girl in HS when I was 16. She was 15, and had been with two guys before, only one in the biblical sense. I didn’t know this yet. I was a bit shy I guess.
I was the leader of the percussion section of the marching band by my junior year, and when we went on a trip in a tour bus, things changed. I took the very back seat in the bus, the very biggest one, and I had my minions keeping watch (the lower classmen) to make sure I had my privacy. Things got more heated than usual and I did some “digital exploration”. Eventually the call was made on the bus to separate the males and females. Haha, I was sharing the “stink finger” seconds later.
My more experienced GF was in full attack mode now. We visited a well known aquarium, all the while I had a raging boner because she would not let go of my dick the whole time. Soon I learned what blue balls were.
So, we get back from the trip and we’re doing the usual make out on her couch. Did I mention that her dad was a cop and loved to scare the shit out of us with full lights and sirens (basically everything minus guns drawn)?
So, before I know it, her pants are off and my dick is in her hand guiding it in. Her brother (younger) was anywhere between one and two blocks away with a friend, and her slightly insane father who is required to carry a gun, plus his partner, could have been outside the garage door at any moment. Fear took over and I became “unable” to accommodate her at the moment. She said “maybe you’re not ready yet”.
She may as well have said “I dare you to show up and fuck me like it’s your job.” I tried to do that, but I don’t think I got much past “satisfactory”. Until later. But that’s a whole other story. That one involves pregnancy, divorce, assault, angry parents, unprotected sex, and a few other things. (I was only responsible for two angry parents, a messy divorce issue, a false pregnancy scare, and a little bit of unprotected sex though) funny story that…
I lost mine in the traditional method, by having sex 
It was lost at what seems like a relatively un-average age of 25, to my girlfriend of 43 (why is age so important?). Better yet, less than a year later she was pregnant 
not :smack:
First time was a bit of a flop, so I suppose (as mentioned above) it wasn’t really loosing it. So I tried again a minute later and got it right. They say your first time is rubbish, but I quite enjoyed it