What Sex Is Really Like For Him The First Time

What Sex Is Really Like For Him The First Time

Sex 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, worldwide patriarchy states that we become damaged goods once it happens. On the other hand, men are high-fived and considered to have “scored.”

Males are also not socialized to believe that they will “lose” a part of themselves by having sex, and they don’t necessarily feel as though they must be in love with their partner for it to be “right.” They are also pressured to lose their virginity as soon as possible, rather than to wait for their wedding night. Not only do these expectations contribute to our dangerous gender binary and cause many women to fear or feel ashamed of their first sexual experiences, but they also erase men’s emotions and vulnerability when it comes to sex. What is the first time really like for men — cisgender, transgender, and of any sexuality?

Media and pop culture often depicts “virginity loss” for men as humorous and, well, ending quickly. Think American Pie and The 40-Year-Old Virgin. (Also think how, until 2013’s The To Do List, there were barely any movies that discussed the “first time” for young women so lightheartedly). But in real life, unlike on the big screen, first-time experiences for men are much more nuanced, and they don’t always involve women. What is scary about the first time for guys? Do they want to be in love, or are they more concerned about “getting it over with”? How has it affected the rest of their sexual experiences? Did they feel ready? How did stigma surrounding their gender and sexuality shape their first times? I talked to 11 men to find out. (P.S.: The concept of “virginity” and “losing” something is a social construct, hence the quotation marks.)

1. Dante, 25

I put a lot of pressure on myself. It’s scary, too — I was nervous about hurting her and potentially making her bleed.

2. Svan, 26

Emotions: Excited, nervous, worried I would “f*ck it up.”Physically: I was buzzing with excitement. “You mean I finally get to do it?!”Partner: Committed girlfriend of three months.Bad Parts: I did the stereotypical virgin thing: One, Two, CumGood Parts: 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. Anonymous, 31

The whole thing was a big letdown. Which isn’t surprising when virginity was as built up as it was for me, and losing it even moreso. Glad I got it over with, at least. It was the night before my birthday on a barracks room floor with someone I had been talking to for a bit; cold linoleum and all. Pirates of the Caribbean on to cover up the noise. She rolled a condom on me and climbed aboard. 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

My first time was with someone I met online. I was still in college and closeted at the time. Nervous and excited couldn’t even begin to describe how I felt driving up to the guy’s place. Part of me wanted to “get it over with,” and the other just 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. I remember driving home with a big smile on my face, but I kept thinking, “There’s no turning back now.”

5. Dione, 29

It was mediocre. Being gay was really hard in such a middle-class family. I ended up [having oral sex with] an old dude I met online. It felt kinda good, and at the same time kinda horrible. What won’t teens do out of horniness.

6. Mike, 37

I was giddily enthusiastic, but completely ignorant. My partner was also a virgin, so we were working with zero experience. I had a condom, because I knew you were supposed to. It was much too small for me, but my teenage boner managed to maintain itself long enough for us to discover that we really didn’t understand the angles involved. In retrospect, I’m sure she wasn’t sufficiently lubricated. I poked at her for a few minutes while she tried to be patient, thinking it was normal for the first time to hurt. Eventually we gave up because it was hurting her too much. We never did successfully have intercourse. We broke up a few months later, and my next partner, who was NOT a virgin, was very informative. 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

The first time was a disaster. I was flaccid from nervousness. She was much more experienced (same age, though). Then we talked about it. I verbalized my fears (anxieties included size and performance), and the second time was amazing.

8. Matt, 35

I remember how it felt so much different than what I had imagined. I had watched too much porn, so I switched positions a number of times, thinking that was normal. I didn’t come, and when we decided we were done, I stood up and realized that my legs were covered with blood. Her blood. I have no idea whether she was having her period or she tore. 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. 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

I was surprisingly confident. It was with my first girlfriend, who immediately wanted to get it on. I held out for a few weeks, saying I needed to get to know her better. I think that was really reassuring for her. It strengthened our relationship (while it lasted) and allowed me to get a basic understanding of how her body worked while we fooled around. The only negative I can think of is that I only told her I was a virgin six months later. Even though I still think virginity would have been a turnoff that early on with someone more experienced, I am a little ashamed I wasn’t upfront with it.

10. Chris, 41

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

11. Red, 23

It wasn’t an emotional experience. I didn’t really care about her (a girl about my age, my supervisor at work) beyond a casual friendship. I just knew she was into me, and I wanted 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. 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.

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