Kolaveri Girls

First-Time-Sex Bloopers

All Pain and No Gain
"My first time was definitely awkward. The guy I was with kept saying stuff like 'How's that for you, you dirty girl?' and 'Tell me how much you want me.' He also dragged me into about 30 different positions. I felt like I was doing Pilates! When we were finished, I went to hug him but accidentally swung my hand out too fast and ended up whacking him really hard on the penis. I was embarrassed, and he was in pain. At least I can laugh about it now." —Emily, 21
Overly Gushy Guy
"My boyfriend and I finally decided to do it after having multiple talks about making sure the first time would be special. Afterward, I mused 'I can't believe I'm not a virgin anymore,' and he freaked out! Turns out, he thought we had been talking about having our first time together. He kept asking 'Did I hurt you?' and 'Are you okay?' which got to be way too much after a while. He ended up being the emotional one, not me!" —Jessi, 24
The Devil Made Me Do It
"I was raised by a very strict father, who doesn't believe in premarital sex. Being the rebellious teenager that I was, I ended up losing my virginity with a guy friend...during a church picnic. We did it on the gross floor of the girls' bathroom while everyone was in the gymnasium for a service. And believe me, it wasn't a celestial experience." —Halle, 32
He's Not So Handy
"My first boyfriend and I were both virgins. He was trying to use his finger down there and accidentally stuck it in the wrong hole. It lasted all of two seconds, but I lost it. I died laughing, and he was completely mortified. In fact, just remembering it right now has me cracking up." —Ashley, 25
Oh, We Started?
"I held out until after college to lose my virginity, and it was definitely not the orgasmic event I was hoping for. My less-than-endowed boyfriend and I decided we'd do the deed one night, and during a heavy petting session, I told him I was ready. His response? 'I'm already in you.' Oops!" —Chelsea, 27
One Hell of a Mating Call
"When my guy and I decided to get intimate, we had roses, candles — the works. He didn't utter a peep during the act, and I thought maybe he wasn't into it. Finally, he let out this crazy noise that sounded like 'gaaah-guh-guh-guh!' It was his orgasm! I laughed so hard, I couldn't finish." —Tracy, 19