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Holiday treats: Tales of losing it 

Lest I be accused of waging a war on Christmas by the pro-Christmas lobby — oh, whatever would I do if the all-powerful puckerbutts at the American Family Association called for a boycott of Savage Love? — I’m presenting a heartwarming selection of how-I-lost-my-virginity horror stories submitted by my readers.

What do these stories have to do with Christmas? Well, wasn’t Jesus Christ responsible for the most traumatic how-I-lost-my-virginity horror story ever told? Not his deflowering, I mean his mother’s. As everyone knows, Mary was a virgin when she conceived and a virgin when she gave birth. This means, of course, that Jesus busted his own mom’s hymen, kicking it down like a door on His way into the world. And you thought your first time was traumatic!


I was an 18-year-old virgin with visions of Hollywood movie sex — perfect lighting and angles, climax together, etc. Instead, my first penetration made the same impression as a tampon, and ended so quickly that I was sure he hadn’t come. I was angry that he faked it, so I broke up with him the next day. About a month later I discovered he hadn’t faked his orgasm: I was pregnant! After the abortion, I was a tad leery about the sex thing: fucking = pregnancy. —Fucking Happily Now


I got my cherry popped when I was 15 years old, by a 22-year-old man. We were making out on a reclining plastic pool chair. When I told him I wanted to do it, he hopped right in. The initial pain gave way to a feeling of pressure “down there.” I naively thought that maybe if I let my body release this pressure, I would get my big “O.” I let go of the pressure ... and immediately started peeing. It flowed through the chair’s slats and hit the concrete beneath us in a steady stream. Try stopping your flow of urine while you are being pumped. You can’t. I died a million deaths while he finished. When it was over, I asked him how he felt about being my first. “Well, sleeping with a virgin is kind of a pain in the ass,” he said, quickly followed by, “Did you pee?” —Pool Party Girl


After the stereotypical first fumbling experience, which lasted about three minutes before I shot my wad, I laid down next to my girlfriend (failing to notice how very disappointed she looked), stroked her hair, and asked, “How many times did you come?” —MN


By 19, I was eager to lose my virginity, not yet having discovered my Sapphic proclivity. I turned down some enthusiastic offers (dear, sweet Tag!), and instead chose a cycling maniac like myself. I remember being under-impressed with the event (“Is that all there is?”) and he seemed disappointed that I didn’t bleed. After we finished, the condom came off his flaccid dick inside me. I freaked and ran to the bathroom. The whole household got involved with suggestions and solutions. Looking back, it’s pretty funny, but I was mortified at the time. —Bike Geek Love


It’s so common that it’s a cliché: A girl loses her virginity and thinks, “Is that it?” Except that I’m a boy. I had expected that it would feel amazingly better than jerking off or blow jobs, but it didn’t. So when she asked me what I thought, I wanted to say, “Is that it?” But I decided to soften the blow while telling the truth. “Um, ... I’ve, ah ... had better,” I said.

Bzzzt! Wrong! —Naked Cuddling Rocks


I lost my virginity during a one-night stand to a goofy guy I met my freshman year at Washington State University. The relationship didn’t work out, and I relayed my woes to my brother. A few weeks later, my family came to visit for “Mom’s Weekend.” While we were shopping at the mall I saw the goofy guy. I went to my brother and said, “That’s the guy I lost my virginity to.” My brother couldn’t spot him, so I kept loudly pointing the boy out until a woman next to me said, “You mean my son John?” When she looked at me with that same goofy smile I knew that she was definitely his mother. Ouch! —Still Shamed


Four years ago, I lost it in a boy-girl-boy three-way on a cruise ship. The girl was 16, the other boy was 17, and I was 15, gay and closeted. In the girl’s parents’ cabin, the other boy fucked the girl first. When it was my turn the girl noticed that I was staring at the other guy while I was fucking her. “Are you gay?” she suddenly asked. I was so shocked that I couldn’t say anything. Then she started screaming, “Oh my God, you are! You gave me AIDS!” She pushed me off, the other boy jumped up, pulled on his shorts, and then punched me in the face for looking at him. Then he made me wash my dick, which had his come on it, because he didn’t want me “tasting his sperm” after they threw me out. The best part? This happened on the first night, and I was trapped on the ship with them for another week. Oh, and I had to make up a story for my parents about how I fell and broke my nose on the Fiesta Deck. —My Crooked Nose Looks Sexy


My boyfriend and I decided to consummate our relationship. Everything started OK, until I was hit with a blinding pain. I crawled to the bathroom where the pain caused me to start puking. He asked what was wrong, and I told him to get the fuck out of my house. I called my mom at work. She explained that the first time hurts and thanked me for sharing. In between hurling, I said that this couldn’t be normal. She told me to get to a hospital. My boyfriend came back and carried me to the car. After having every resident in the ER stick his hand up me and having two orderlies hold my knees apart so they could stick what looked like a dildo in me for an ultrasound, they determined that the sex had caused a cyst on my ovary to rupture. The doctors thanked me for making them part of my first time. I was too doped up to say go fuck yourselves. Do I win? —First Time Not All That


No, FTNAT, you don’t win. Mary Mother of God wins — but I’d say you come in a damn close second, with MCNLS a close third. Readers who want more virginity horror stories can find them at Readers who want to know more about the war on Christmas can read all about it at And, as many readers wrote in to point out, by the time last week’s column came out, Ford reversed itself. Like Kraft, the car company told the gay-haters at the American Family Association where to stick their boycott, and announced that they would continue to advertise in gay publications and sponsor gay events. A very nice Christmas gift to us all.

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