When I was in high school I was awarded the opportunity to go on a foreign exchange to a lovely tropical paradise — ah, Brazil — for senior year. As high-school girls are prone to do, I met a guy, another exchange student. We were the queen and king of virgin teenagers: I never had any dates in high school and neither did he. After the first kiss all thoughts went to sex almost immediately. We decided that as soon as humanly possible we were going to lose our virginities to each other.
We first tried at his house. We thought the shower would be a "sexy" place to do it and that the rushing water would also be a nice cover for any strange noises. In this particular tropical country, showerheads are often electric and some fool had made theirs out of metal. I touched the showerhead briefly and was shocked so severely that I fell and spun out across the floor. At that point his host mother barged in, dragged me out of the house by my feet (buck naked, mind you), called me a "whore," and kicked me to the curb.
We came up with another brilliant idea: We would borrow something similar to a rowboat from a friend, paddle out onto the local lake, and get the deed done. This boat was something like 20 feet long, about 1 foot deep, and about 4 feet wide, and made of wood. We brought the necessary items: a bottle of liquor, a joint and a condom. We paddled out and were almost instantly naked. I stuffed our clothes under the seat in the front of the boat. After one slug of the booze and one puff off the joint, we commenced to clumsily roll around in the bottom of the boat. We were about to do the deed when I told him my ass was getting wet.
"That’s supposed to happen," he said.
A little lesson in boats: They sink slowly until they’re about half full of water, then they go down like lead weights. I was a little too preoccupied with getting it on to notice that the boat was filling from the rear until the fateful moment of entry. I figured I’d better be on my back for this moment, so I let myself lay back and I’ll be damned if my hair wasn’t floating about my head. I threw him off me, jumped up hollering about the boat sinking, and grabbed a paddle to head for shore.
We didn’t make it. We sunk. Like the Titanic. A few minutes later we were standing on shore bare-naked. Yes, we had to walk home bare-naked. We decided to go to my house instead of his because we figured that the people I was staying with would be more understanding or easier to lie to. Upon arrival, the house was dark and it looked as if they weren’t home. He asked me to unlock the gate. I said, "Where, exactly, would I have put the keys?" So, he had to boost me over the gate so I could unlock it from the other side.
I landed on the other side and was about to unlock the gate when my host father and brother walked around the corner of the house. They asked what I’d been doing.
"Swimming," I said.
"Naked?" my host father asked.
"Is Andrew with you?"
I was about to say "No" when Andrew shouts from the other side of the fence, "Yeah, I’m here, can you let me in please?"
When he walked in naked, they lost it laughing at us. But they never actually said anything or asked any "real" questions. For days afterward, my girlfriends kept asking, "So … did you?" and I honestly didn’t know. In the excitement, I couldn’t remember if he ever got it in or not.
I did eventually lose my virginity. In my host family’s house, on a marble floor, while watching an AC/DC concert broadcast from São Paulo. The family graciously gave us lots of alone time and pretended that they never noticed. —Titanic Love
After a brief period of fooling around in the bedroom at a party, this girl I had just met decided that we should "take a drive." We found a dark spot off a country road and continued fooling around in the back of my car. She pulled out the condoms she bought at a gas station and we started to do the deed. As things started getting hot and heavy, my foot slipped off the center hump on the floorboard. I lost my balance and did a face plant into the side window. My nose started to bleed all over her head. I was glad that bleeding all over her did not deter her from wanting to "see" me again. —Bleeder Boy
I was 15 and my BF was 17. We were at a party and we snuck off into a bedroom and pushed a dresser against the door. After some serious dry humping it was time to get naked. I had never seen my BF’s cock before, just kinda felt it through his clothes, and suddenly there was this gigantic cock in front of me. In my mind, I think this is about the worst thing that could happen to a virgin. I was already scared it was going to hurt and then I see this trouser anaconda flop out of ol’ BF’s pants. I went on to have the single worst sexual experience of my life — let’s just say I didn’t do a lot of walking for a couple days. You may think that this huge dick was just my perception, as I hadn’t seen a lot of dick by age 15, but I am now 28 and have seen plenty of dick, and his is still by far the biggest I have ever seen.
Now I find myself thinking, "Do I still have his number?" —Now Appreciates Large Erections
I was 16, and my girlfriend and I planned on having sex — my first time, not hers — at a party where we were guaranteed a room to stay the night. I showed up to find my girlfriend pissed drunk. I was bummed, but I was so eager to lose my virginity that we had sex anyway. She passed out and I went back downstairs to hang out with friends. At that point I learned from other people there that she had gone down on some other guy in the bathroom before I showed up. The next morning she woke up and asked me if we had sex last night. I was so mortified that I lied and pretended to still be a virgin until we could have sex under more preferred conditions. I never did tell her the truth. —Anonymous
I was a freshman at a Big 10 university and had already broken up with my first college girlfriend, who told me toward the end of our monthlong endeavor that she was "a born-again virgin," and that I shouldn’t ask her to have sex with me because — here’s the kicker — she’d probably say yes. By the way, she told me all of this while we were naked and in bed.
There was a girl that lived on the floor above me who was a sophomore and attractive. She had stopped by my room a couple of times with excuses that seemed feasible as a freshman, but upon retrospect seem pretty ridiculous. Anyway, once she was in my room she proceeded to pretend to fall asleep on my shoulder while puckering her lips. All of a sudden we were nekkid and she asked me if I wanted to have sex. Hooray! So I grabbed my three-pack of Trojans (my dad had given them to me when I left for school), and slipped one on.
I followed the procedure and achieved penetration, which was supposed to be the be-all and end-all of my life as a male. However, she did absolutely nothing. She laid there completely still — no motion, movement of hands or arms, hip tilting or gyration, nor anything else that could be construed as helpful, enjoyable or cooperative. It was like fucking a girl in a coma. After about two minutes I was having zero fun and I could tell that my erection was going to fade, and so I faked my orgasm during my first time to get her out of my room. I was fucked up about it for a couple of days wondering if every time I had sex it would be like this, and I was even more confused when she came by the next day to collect a flip-flop that she had strategically left behind. I mean, here was a girl that was willing to have sex with me, but I had to say "no" because I didn’t want to have to fake an orgasm on my first two sexual encounters!
To all the ladies out there: If you think you might be breaking in some young buck on his first ride, do him a favor and move at least once. Get on top and moan if you really want to give him a treat. Otherwise he’ll end up calling you a cold fish 10 years later in some syndicated sex-advice column. —Still Life With Woodpecker
I lost my virginity at 24 — but that’s not the embarrassing part. Just a few thrusts after penetration, I felt a sharp pain at the tip of my penis — a very sharp pain — but since it lasted just a second and was replaced by rather nice sensations, neither of us bothered to stop. Shortly after, things started to get very slippery (which was also rather nice), but when I looked down, I saw that someone was bleeding. We reluctantly stopped, and she was embarrassed to be menstruating at the wrong moment. I assured her that it was OK, but before long we realized that the blood was mine. I had torn my frenulum, the sensitive "bowstring" of skin on the underside of the glans penis. In my case it had been abnormally short, a condition urologists know as frenulum breve. This is curable by creams that stretch the skin, minor surgery or full-on circumcision, but in my case it pretty much cured itself. We enjoy great sex today and still laugh that, in our case, it was the man and not the woman who had a painful, though pleasurable, deflowering. —Broken Bowstring Boy
I lost my virginity during my freshman year of high school. It was with my girlfriend, and between my sexual ignorance and my dad’s intrusion, it’s safe to say it was disastrous. My door was void of a lock and my parents were upstairs, but after multiple false alarms we started ignoring the parental noises. In accordance with any virgin girl’s dreams, I said, "Let’s hurry." I was on the brink of orgasm when we heard dad’s footsteps. Pulling the blanket off my bed, I hastened to intercept him as he walked into the room, all while coming all over the blanket and myself. He handed me a plate of cookies, and said, "Enjoy." Thanks, Dad. I turned around to see my girlfriend huddled in the fetal position naked on the bed with no blanket. I offered her some cookies. —Coitus Confections
I was a freshman in high school (14) and found myself receiving the attentions of a junior (16) — oooh, an "older man." Some months later we set up a time for me to go over to his house after school while his parents and brother were out. I put on a short skirt and cute top and rode my bike over to his place. We started to make out on his bed and then his mom came home — his brother had forgotten something for an after-school group and she drove him home to get it. My older man moved us onto the floor between his bed and the window, where his mother couldn’t see us if she came into his room. His dog, some fluffy thing named Elvis, saw me, though, and barked at me and kept sniffing at my crotch. I remember he said, "I think I’m done," and I thought, "Crap, that’s it?" He’s now gay and living in San Francisco. —I’m Bi Now
My first time was in high school. When the moment came to finally get it on, I laid her down on the couch, climbed on, and slowly slid in. After a few seconds I felt an uncomfortable friction, which I was afraid to mention. Another 10 seconds and the friction was becoming painful. I remember thinking, "I don’t see what the big deal is, this kinda hurts." Then I finished, looked down, and realized I was pumping between the cushions of the couch. The only thing that made it worse was the look on her face: a combination of frustration and pity. —I Lost It To A Couch Send letters to email@example.com