“I Did The Stereotypical Virgin Thing”: 11 Men On Their First Sexual Experience

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Having ex for the first time can be an awkward, intimidating, and overwhelming experience — but hopefully a positive one, too. What is the first time like for guys? Our cultural understanding of "the first time" is extremely gendered and heteronormative; women's first sexual experiences are often thought to be painful, and to create a lifelong obsession and attachment with the person with whom they "lose" their virginity. And, of course, the patriarchy claims that women become damaged goods once it happens. On the other hand, men are often high-fived and considered to have "scored."

Dr. Britney Blair, PsyD, CBSM, AASECT, a psychologist and founder of the sexual wellness app Lover, says that men actually have a "rough time" when it comes to cultural expectations around losing their virginity.

"There’s this message that you should be ready, willing, able, and wanting," Dr. Blair tells Bustle. "And the truth is, not all men are, especially when it comes to losing your virginity. Some men don’t feel ready, but feel pressure that virginity is burden you ‘must lose.’"

It's important to note that not everyone who has a penis is a man — and not all men have penises. But the concept of "virginity" is really based in the gender-binary and the experience of heterosexual, penis-in-vagina sex (PIV). So when the term "men" is used here, it's in reference to cisgender men. Assigned-male-at-birth (AMAB) people who don't identify as men may have similar experiences.

Here's what 11 men's "first times" were like.

1. Dante, 25

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"I put a lot of pressure on myself," Dante, 25, tells Bustle. "It's scary, too — I was nervous about hurting her and potentially making her bleed."

2. Svan, 26

Svan 26, had sex for the first time with his "committed girlfriend of three months." He was excited, but worried he might mess it up.

"I did the stereotypical virgin thing: One, two, cum," Svan tells Bustle. "I specifically waited till I was with someone who 'felt right' to give my virginity to. While the act itself wasn't that great for either of us, I still look back on it and get the warm-and-fuzzies."

3. Jack*, 31

Jack*, 31, lost his virginity on the night before his birthday on a cold, linoleum floor. Pirates of the Caribbean played to cover up the noise. He says "the whole thing was a big letdown" because he built up "losing it" to a point that was unrealistic.

"She rolled a condom on me and climbed aboard," Jack tells Bustle. "It felt alright; never got close to orgasm. I tried breathing heavier because that's what I saw in porn — that turned out to make me hyperventilate."

4. Marc, 38

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Marc, 38, had his first time was with someone he met online. He was still in college and closeted at the time. He was nervous, excited, wanted to get it over with, and "felt a sense of breaking free."

"Surprisingly, there wasn't anything awkward about it, because he knew what he was doing and I was truly going with the flow, which helped me enjoy the moment even more," Marc tells Bustle. "I remember driving home with a big smile on my face, but I kept thinking, 'There's no turning back now.'"

5. Dione, 29

Dione, 29, had a "meh" first time, which he says is because it's hard to be gay a "middle-class family."

"I ended up [having oral sex with] an old dude I met online," Dione tells Bustle. "It felt kinda good, and at the same time kinda horrible. What won't teens do out of horniness."

6. Mike, 37

Mike, 37, says he kind of had two "first times." The first first one was with his girlfriend, who was also a virgin. And it was a disaster, from the too-small condom, to him "poking her a few times," to giving up because it hurt his girlfriend too much.

"We broke up a few months later, and my next partner, who was NOT a virgin, was very informative," Mike tells Bustle. "I've never been good at keeping in touch with my exes, and I really wish I had talked to my first partner back then and let her know what we were doing wrong, and that there wasn't anything physically wrong with us. I hope it didn't cause any problems for her later on."

7. Reginald, 43

Reginald, 43, says that his first time was "a disaster."

"I was flaccid from nervousness," Reginald tells Bustle. "She was much more experienced, although the same age. Then we talked about it. I verbalized my anxieties about size and performance and the second time was amazing."

8. Matt, 35

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Matt, 35, was so traumatized by his first time having PIV sex that he didn't do it again for two years afterward. During the sex itself, it switched it up a bunch like he'd seen in porn. But when he stood up, he was "covered in blood." Her blood.

"I'm fairly ashamed to say that I wasn't a very caring or empathetic lover for her, and I freaked out about the blood," Matt tells Bustle. "I didn't have sex with anyone else for two years afterward, turning down other possible lovers due to the bad experience. In retrospect, she was probably on her period and it really wasn't a big deal. But as a first experience, it was frightening and shocking, and it took years for me to be comfortable trying to have sex again."

9. Tom, 28

Tom, 28, didn't tell his first girlfriend he was a virgin. She "immediately wanted to get it on," but he told her he wanted to wait to get to know each other better.

"I think that was really reassuring for her," Tom tells Bustle. "It strengthened our relationship (while it lasted) and allowed me to get a basic understanding of how her body worked while we fooled around."

10. Chris, 41

Chris, 41, had a first time that kind of sounds a lot like what the movies show.

"I was kinda self-confident, but looking back, I was pretty inexperienced," Chris tells Bustle. "I also came right before penetration. In retrospect, it was as awkward as could be."

11. Red, 23

Red, 23, lost his virginity to a girl about his age who was his supervisor at work. He was mainly interested in her a friend, however, and knowing that she was interested, he decided to "lose this thing that had hung around my neck like a lead weight."

"I wasn't scared or anxious. I knew that would just get in the way — like they often say about confidence, you have to fake it 'till you make it," Red tells Bustle. "Her saying, 'By the way, you've got a big dick' before lowering herself onto me was memorable and an ego boost. But still, at the end of the day, it wasn't some memory I'll cherish forever. It was just getting it out of the way — a learning experience."

Ultimately, this list illustrates the fact that it's time for the world to get rid of silly, gender-based stereotypes about a person's first time having sex. No matter what gender you are, your experience is going to be uniquely yours. Man, woman, non-binary — everyone does it the way they're gonna do it.

*Name has been changed.

Experts cited:

Dr. Britney Blair, PsyD, CBSM, AASECT, a psychologist and founder of the sexual wellness app Lover

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