11 ‘How I Lost My Virginity’ Stories That Are Awkward And Then Some


Your first time having sex is almost always going to be a letdown: You’ll fumble with the condom or underestimate the need for lube. Or maybe your partner will starfish their way through the whole thing ― all 10 seconds of it.

You’re a clean slate, sexually speaking ― anything and everything can go wrong. Below, comedians, entertainers and other funny people on the web share the funniest things that happened during their first time.

An Assist from Adam Sandler

“I was 16 years old, had zero knowledge of porn, zero knowledge of sex. I was in my boyfriend’s mom’s basement and we used his mom’s strawberry scented body butter as lube (please for your genital health, do not try this at home). The radio was playing Adam Sandler’s ‘Lunch Lady Land.’ Have you ever tried to have your first non-solo orgasm while listening to the lyrics ‘Sloppy Joe. Slop-Sloppy Joe’? Not good” ― Kyra Kane, the host of the Sex Work BB podcast

Mistaken Identity

“I was in college and determined to lose my virginity so I just grabbed a guy at a party and started making out with him. We went to his dorm, I got my cherry popped, it was fine, mission accomplished. Leaving his dorm the next morning I realized I had no idea what his name was and had to try to find it using the campus directory for that building. He had a roommate so I guessed at which one it was.

I ended up telling my friends I’d banged the wrong guy. I was eventually corrected when I was confronted by the guy’s roommate’s girlfriend who’d heard through the small-liberal-arts-college grapevine that I had sex with her boyfriend. I explained and she and I laughed about it and are still Facebook acquaintances to this day.” ― Allison Mick, a comedian in Oakland, California

MacGyvering the Lube

“There are classes in school that give straight people a decent idea of how it’s supposed to go but there are some key things that differ from straight sex versus gay sex, especially when preparing yourself for what’s to come. Being the brilliant person that I am, I just chose to eat one light meal at breakfast because I definitely, totally planned to have sex that night.

When we were getting down to it, I was so frustrated because it wasn’t working (mostly due to the lack of lube which NO ONE WARNS YOU ABOUT). Once again, being the brilliant person I am and a former Boy Scout, I knew to think on my feet so spit became the next best option. Despite the hiccups along the way, it was a successful but challenging experience and it has taught me that I can conquer any feat put in front of me.” ― Miss Toto, a drag queen in Miami, Florida

The Sunglasses Stay On

“My older cousin let me use his place and left a pair of Ray-Bans on the coffee table with a note that read ‘take them if you do it, leave them if you don’t.’ Being young and stupid I thought he wanted me to wear them while having sex. I wish I could remember more about that night but I couldn’t see much.” ― Daniel Tirado, a comedian in New York City

The Slip

“I thought my first time would be romantic. That’s the image I had fantasied over since I found out what a ‘first time’ was. For the most part, it was fun: the basic cute kissing, gentle fingering, PG foreplay. But the grand finale really wasn’t all that grand: After several attempts trying to get it in, his elbow slipped, launching him all the way in and that’s when I heard it ‘pop’. I froze and screamed, ‘DID YOU HEAR THAT, YOU JUST BROKE MY HYMEN!’ It’s fair to say we stopped shortly after that.” Georgette Olaiya, host of the Just The Tip podcast

The Cheesy Puff Incident

“All I can tell you about my first time was that it was another trashy prom night tale of intrigue, disgust, and getting caught in an RV after vomiting in his lap. It was my senior prom in the middle of nowhere Texas. My boyfriend and I went to prom in a group but left pretty early to sneak away to a pool party. There I consumed my weight in sprite and cheesy puffs. We decided to drive to the campgrounds in his parents’ RV to enter into manhood together.

Things were going great until those cheesy puffs came back up and I threw up in his lap. He went and hosed off. We weren’t ready to call it quits so we continued until all of a sudden a spotlight flashed through the window and we heard the WOOP WOOP of a police car. Over the loudspeaker, we heard, ‘please exit the park.’ We left, showered and had regular, bad-first-time sex later that night, but I haven’t eaten a cheesy puff since.” ― Meatball, a drag queen in Los Angeles, California

An Awkward Playlist

″‘Sex and Candy’ by Marcy Playground was on the radio. She laughed but I’m not sure it was from the irony. Now every time I hear that song I think of Skittles and disappointment.” ― Jamie Arrington, a comedian in Hattiesburg, Mississippi

The Tampon Disagreement

“The night I lost my virginity I had a tampon in but completely forgot about it because we had been drinking. When the much older loser I decided to sleep with tried to put his penis inside me, he said, ‘Wait, do you have a tampon in?’

I laughed in his face because what a crazy thing to ask during my first time. I said ‘Ew, no.’ He tried again and exclaimed, ‘No, I’m pretty sure you have a tampon in’ so I rolled my eyes and said, ‘There’s literally no way ―’ then felt the tampon. I uncorked myself like a bottle of wine (red, obviously) threw it across the room like I had just drawn a sword and hacked it toward my worst enemy. Neither of us came, and we haven’t spoken since.” ― Lili Michelle, a comedian in New York City

An ‘Experienced’ Virgin

“At the end of sophomore year of college, I was hooking up with someone but I was still a virgin. I felt ashamed by my lack of experience, so I decided to keep this little secret to myself. One night, things were heating up and we decided to go all the way. This first time could best be described as ‘fleeting.’ A mere two pumps. Somehow, she caught on to my secret because she immediately asked, ‘Wait a minute, are you a virgin?’ I told her the truth: ‘Not anymore.’” ― Cam Poter, a comedian and co-host of the Sex Talk With My Mom podcast

The DVDs Stay in the Picture

“I was in China as a teenager, summer between high school and college. My first time was with another tourist, outdoors, at a construction site at night, because neither of us had empty rooms we could use. An hour earlier, I’d bought this whole Martin Scorsese DVD box set for like $7, which, I mean, great deal. Anyway, I was holding onto the Scorsese DVDs for most of the first time, because I didn’t want it to get scratched. Eventually, I set it down, but I kept it close. That’s something you don’t want to lose.” ― Dan Perlman, a comedian in New York City

The Family Affair

“I lost my virginity when I was 24 years old (I was an un-fuckable dork for most of my life) to a short, stout, blonde Irish girl named Patty after we met backstage at a U2 concert. We hooked up in her parents’ bedroom because she said, ‘I prefer sex on larger-sized mattresses.’ I had so much horniness built up after all those years, I would’ve said yes to doing it on the N train during morning rush hour on top of a homeless man’s corpse. Location was the least of my concerns…or so I thought. We entered the master bedroom and as she disrobed, I noticed family photos sprinkled about everywhere: Disney vacations, Royal Caribbean and Carnival cruises to the Caribbean, birthday party at Chucky Cheese. Chucky…Goddamn…Cheese.” ― Allan Fuks, comedian and co-host of The Week In Sex and Judges of History


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