How 10 Porn Stars Lost Their Virginity

My first time wasn’t as titillating as you might expect from a porn star. It was a boring cliché, in fact, and yet I wouldn’t trade the experience for a different one. I was at a drive-in movie with my high-school sweetheart. We did what every parent fears their kids will do at the drive-in: what started as a make-out session turned into something much more explicit. I initiated it; I’d always wanted to
know what sex felt like, what it was really. I read a lot about sex, saw glimpses of it in movies, and was more or less culturally inundated with it. I was inquisitive and knew I had the ideal partner to explore new territory with. I wasn’t promiscuous, despite my later career choice. I was a perfectly average teen.

Watching our movies might lead a person to believe that adult-film stars were born with innate sexual abilities. Turns out, we aren’t that much different from everyone else when it comes to our first encounters. We start slowly, shyly, and awkwardly just like most teenagers discovering the birds and the bees. And while I think there’s a common belief that adult stars start having sex at particularly young ages, you’d be surprised to learn how many fall into that thoroughly average age category—and that some are late bloomers. I asked a few famous adult-film performers to recall their first times. Here’s what they told me

Ron Jeremy

The most famous man in porn will never forget his first time. The day he lost his virginity he had a hard time putting on the condom, and later discovered why. “It’s a real story. I put the rubber on backwards. It wouldn’t go on at first. The lubricated side was against me, not against her. We did it by this gigantic rock near my elementary school. I was 15 or 16 years old, she was about the same. I remember the lubricated side against me, not against her, sliding back and forth. So basically I was having sex with a rubber not her.”

Courtney Cummz

Curiosity got the best of multi-award-winning adult actress Courtney Cummz. “I was 13 years old and I was in junior high and my girlfriend had had sex, and I was dating this black guy and I heard they had big cocks and I wanted to know. I wanted to know what sex felt like, because my girlfriend made it seem amazing. But the first time you have sex you’re like, really? That’s it? That’s all? One day after school we went to a monument—I lived in West Virginia. We started having sex in a nearby cave. I can’t believe I went inside of a cave, laid down, and got fucked. Afterward I was like, that was pretty nice, but that’s it? It was fun, but I didn’t have an orgasm the first time I had sex.”

Dana Vespoli

Award-winning adult director and performer Dana Vespoli had a fairly mechanical first time, but things got better after that. “I lost my virginity at 16. My boyfriend was 17 and also a virgin. We were both very technical about it, and the experience reminded me of when you work through a tight muscle with a massage therapist—it hurts, but you have to get through it. My boyfriend and I were super-passionate about making out, but the losing-our-virginity thing was overwhelming. We used a condom, and were proud we got through it. After the first time we had sex constantly, anywhere and everywhere.”

Jessica Drake

Multiple-time AVN-award-winning performer, director, and sex-educator, Wicked contract star Jessica Drake had a good first experience, despite the shame that came after it. “The information my parents gave me [about sex] was all very clinical. As soon as I discovered sex, I started reading about it. I would read the encyclopedia, medical books, and in bookstores I looked for the human-sexuality section. I read it all for myself because no one was telling me. When I lost my virginity, it wasn’t an extremely planned-out event, but we both had a condom. I was in high school. I’d been dating a boy who went to a different school than I went to, and it happened after a school dance at my high school. We were doing all that heavy petting and humping and kissing and he got me with that line, “Just let me put the head in.” Everybody falls for that, so many girls I talk to fall for that. For as careful as we were with the safe-sex aspect, I wasn’t so careful with concealing the evidence. There was blood on the shorts and the panties I was wearing, so I hid the evidence in my closet. My mom found them, and it was a horrible experience at that point. She immediately confronted me, screaming at me, calling me a slut and a whore. It drove a huge wedge between my mother and me. It didn’t make me stop having sex, it made me more careful about being caught.”

Brittany Andrews

Owner of Britco Pictures and Discipline Filmworks, Andrews is a Playboy model turned porn star. Her first sexual experience hardly lived up to her expectations. “I was going through a Michael Jackson phase, so I loved black men at the time. I was probably 12. I met the boy at Summerfest and had sex with him at my girlfriend’s house in her basement bedroom. It was the ’80s and I was very much into the Madonna look, so I had like 150 different layers of clothing. It took me forever to get all of my clothes off. Once that was done I started doing the dude for a few minutes, but my girlfriend’s two brothers were underneath the bed so it wasn’t long before we realized it. The guy freaked out. While he ran to kick the boys out, I got dressed in seconds—every layer of clothing was back on in like 2.3 seconds, it was like magic. He came back and said, ‘Aren’t we going to finish?’ I said, ‘No, we’re done.’ A very large black penis was my first one. Not recommended. To say he did not call me back is an understatement.”

Lizzy Borden

Adult performer, director, and former professional wrestler Lizzy Borden shares her less-than-pleasant first time along with her regret about not waiting longer. “I was a late bloomer, so my first time was when I was 17. I was going to be 18, it was right before my birthday. I didn’t want to be a virgin and be 18. I had a boyfriend. Instead of waiting to be ready, I wanted to have sex. It was his first time too, so it was pretty weird. It was not sexual or romantic or fun. It was stressful. I was not comfortable. That’s why now in my personal life I have limits and only do what I am comfortable with. I should’ve never pushed myself because I wasn’t ready and you have to be ready for sex.”

Teagan Presley

XBIZ Female Porn Star of the Year and owner of SkinWorxxx Teagan Presley had a tricky first time too. “It was stressful! I had no idea what I was doing. I did it to please my boyfriend in high school whom I had dated since middle school. I was 17 when I lost my virginity. It wasn’t until I got into adult that I started to learn what I was doing. It was even more stressful than losing my virginity. I literally had only had just the penetration part of sex, so I had to literally learn oral and everything else on camera as we went.”

Aiden Starr

Starr has been in more than 200 movies and hosts The Mean Bitches Show on Sirius XM. Known for her dominatrix ways, it was surprising to learn her first time wasn’t with a boy. “My first time was with a friend of mine when I was in high school. She and I were incredibly close and had fooled around and explored each other’s bodies growing up. One night after a concert we went all the way while her parents were asleep. It was just as beautiful and romantic as I would have hoped for. She and I weren’t girlfriends after that but remain very close friends to this day. I feel lucky to have her in my life.”

Joanna Angel

Burning Angel owner and AVN award-winner Joanna Angel was (surprise!) a very late bloomer. “I was 19 years old. Kind of old for a porn star! There was a guy in a band who had a crush on me. He used to always flirt with me and he was so incredibly hot. Every girl wanted him, and I was so awkward and felt so un-sexy. I had terrible skin and short hair and wore nothing but cargo pants and dirty T-shirts. I was always so confused when he flirted with me, and I never got it! We wound up making out a few times and then eventually, one night, I told him he could stay over, and ... yeah. It happened! It was really awkward. I wasn’t sure what to do. It felt good, but I certainly didn’t have an orgasm or anything like that. I think it lasted for all of, like, two minutes. I guess my virgin vagina was like kinda tight.”

Mary Carey

Best known for running for governor of California, adult star Mary Carey shares her first two times, uncertain of whether or not the first one even counted. “I was 16 and it was with my boyfriend of a few months. I went to this private school and he was a public-school boy, a really popular baseball player. One night all the baseball players were having a party, so we went to one of his friends’ bedrooms and I remember asking for a condom. Everyone said to use Saran Wrap, so that became a joke. Later the rumor was that I’d had sex with Saran Wrap, but I still don’t know if I had sex. I think it went in but I don’t know, his penis was really small, I remember thinking his penis was the size of a finger. The time I know I had sex was a year later. It was my boyfriend, Bobby. It was Valentine’s Day. My girlfriend’s parents were out of town, we were really drunk—I was nervous, so I was drinking a lot. He put roses on my girlfriend’s bed. I still don’t know if she knows I had sex on her bed.”