The first one is always special, as special as it can be disappointing.
One might say I did Guy #1 out of despair. That’s never a solid ground for any relationship, however casual. But at the time I was already 24 and still a virgin. I avoided seeing The 40 year old virgin because I was afraid it would be too confronting. I was simply very ready to know what having sex was like. That’s why I was willing to compromise.
The reason for my inexperience was ostensibly simple: I had spent years falling hopelessly in love with girls that looked just above average, who grew to like me as a friend and ended up confiding their love life in me, because they so much enjoyed the lack of any sexual energy between us. Those were the kind of girls I envisioned myself with, married, with children, a loving family that goes on holidays together, watches plays, goes to museums and in which I would have heterosexual sex. That’s the kind of dream I was chasing.
It took some years for me to finally realize, accept and embrace the fact that I am in fact gay. Actually, by the time I was on my way to see Guy #1 I convinced myself I was merely being bicurious, having my first sexual experience at age 24. I mean, who wouldn’t try it with a guy by then? For me it was either this or a rubber doll.
The year was 2006. The internet had arrived, but I was too afraid to advertize my sexual quest online, alerting the world of my bicuriosity.
Instead, I assumed a pseudonym and paid fifty Euro cents per minute to listen to voice messages of horny guys. I ended up texting quite a lot with different guys and after a while I had summoned up the courage to go all the way and try to meet up with one.
I had to spend an hour in a train to get to my date. It was a very philosophical journey for me. I was shaking from anxiety and excitement at the same time. I enjoyed how the people sitting around me had no idea who they were facing: Someone who was about to lose his virginity. I couldn’t help but feel proud of what I was doing.
Of course, someone you meet over the phone seldom looks like anything you had in mind. In my case, the disappointment started the moment my date opened his door to greet me: Was I willing to lose my virginity to this unshaven, sweaty and slightly chubby Guy #1?
I quickly noticed something, though: Me and Guy #1 were wearing the exact same pair of shoes. Never before and never since have I ever encountered someone with identical shoes. I guess I felt our sneakers connected the two of us somehow. Perhaps I needed to have sex with an unshaven, sweaty and slightly chubby guy who looks a lot older than he says he is because that’s how I had come to see myself over the years, after a seemingly endless stream of rejections from girls that appreciated my friendship so much. Guy #1 was a reflection of my subconscious.
His apartment was depressingly neat and unimaginative. The view was that of other apartments staring right back at me.
He offered me something to drink. Half a minute later we sat down on his bed and talked. My glass of water was the only thing standing between us and sex. As I drank I spoke of my situation. I explained Guy #1 that this would be my first time with a guy. I said I wanted to explore, not realizing what a sad cliché I was being.
Throughout our date the disappointments kept on coming. His accent was weird and unsexy. I could see he had a lot of chest hair, even though he had texted me otherwise. His breath was slightly bad. He was nothing like any of the guys from my very secret fantasies.
Only the shoes matched. So after finishing my drink I simply asked: ‘How do we do this thing?’
That’s when I received my first kiss. It was one of the most conscious experiences I ever had. Finally, after years and years of wondering if something might be very wrong with me, this guy put his sweaty arms around me, during which he revealed his arm pits were as hairy as the rest, only with longer hair. His rugged cheeks wreaked havoc on mine. The kissing lasted a good 45 minutes. Then we undressed each other. He seemed really into me, but I figured he could easily be pretending, just as I was. I behaved under the assumption the two of us were doing each other a favor by pretending the sex to be extraordinary. It was in fact, just not in a good way.
I had already seen a bit of gay porn here and there, but I knew Guy #1 and I would not be doing any of that stuff. Instead, I finished off by saying I was ready to come, which we then did.
Afterward, I was mostly glad it was over. I was happy to say I was not totally a virgin anymore. That and the fact it was over. Guy #1 offered me another drink. I really wanted to leave, but I asked for another glass of water out of politeness. I didn’t know yet it’s okay for sex dates to be heartless.
As I drank my second glass of water, after the two of us had already put our clothes back on, we talked some more. I’d be lying if I said I remember anything about his life. All I remember are his shoes. It’s probably better that way.
Before I left, Guy #1 said I was always welcome to contact him in case I ever felt like talking to someone about anything. I thought that was very sweet of him. I knew I had no intention of ever meeting or interacting with him ever again, but I genuinely thanked him for his offer.
I felt his loneliness when I left. My guess is he had felt mine too.
The train ride home was equally spiritual. My cheeks hurt like hell, but that didn’t stop me from feeling good about myself for having accomplished my mission of having sex. I wasn’t going to become a 40 year old virgin.
I have Guy #1 to thank for that.
Length: 1 hour
Format: Introduction to sex
Sex score (0 being a date with Darth Vader and 10 being the best sex ever): 1.5
8 thoughts on “Guy #1 – If the shoe fits…”
Hello, new reader. I’ve read the last post and was interested so I’m starting from the beginning. What a great start!
Thank you very much!!
Seeing as your first comment was about pedophilia, let me follow it up by saying this was very well written and unfortunately, a bit of a rite of passage for newly-gay virgins! Sadly, I can relate to embarassing early encounters like this!
Why, thank you very much, both for complimenting the writing and for letting know you can relate to my experiences. I guess first timers are seldom award winning experiences, though sadly enough Guy #1 wasn’t the worst I ever had;)
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I’ve caught up on guys 1-10, look forward to both the worst and the best :-)
Then you’ll certainly enjoy Guy #12 more than I did;)
That looks like a photo of a 14-year old, so…No.
Wow, I never expected the first ever comment on this site to address the issue of pedophilia, but thank you for letting me clear this up: The picture, or any picture I will use here, is definitely of an adult. Also, this site will be about adults only. It’s about human beings trying to find intimacy and relationships that benefit EVERYONE involved. That rules out any 14 year olds by default in my book. (https://168guys.com/about/)
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