My first time was a number of first experiences my first semester of college with a guy on my floor. We started with mutual masturbation, after a week or so we moved on the fingering and handjobs, a couple weeks later we started doing oral. Towards the end of the semester I finally told him I wanted him to fuck me, a couple days later he had condoms. It was both of our first times so we had no idea what position would work best. We tried a few different positions, but finally settled on me sitting on his desk and him standing. We took it really slow, and it felt amazing after all that time doing other stuff with him. He made me cum, then he immediately came as well inside me with the condom.

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Okay, I’ll share, too. This was now many years ago, so some of it will definitely seem foreign to you all.

I’ve known I was bi for a while, but I had remained celibate through much of my 20s. Finally at 26 I decided “fuck it, let’s do something with someone and just get the anxiety out of the way.”

But who? And how? A few times I had browsed the men4men section on Craiglist, and I knew there were always guys looking to fool around. I decided not to jack off for about 1 week or more so that I was horny enough to make dumb decisions and actually make a move. I created a new email account and took some photos, and put a post out there. After a few false starts, a nice guy of the same ethnicity, a fellow grad student, and with a huge member reached out and we decided we’d meet up. He was also bi, and also inexperienced, so yeah let’s stumble through this shit together.

We meet at a movie theater so we could end up watching a movie if we didn’t feel like more, or we could mess around a little in the dark and see how things went. I had to look up the ending of the movie later because I couldn’t really remember what happened, and we didn’t stay until the end. Pretty quickly we started touching hands, and pretty quickly I got really really hard. So did he from what I could feel. We made out a little, and then decided to head back to my place, each in our own cars.

I came the first time right away while we were grinding against each other on the couch, but I don’t think either of us realized it. We ended up fooling around all night. Just hands and mouths. He did rim me for a while which was fun. We 69’d, cuddled, kissed, chatted, frotted. Really just exploring our bodies and how they react to sensations and how our penises work – his was uncut and I’m circumcised so we were both fascinated. I remember his had its own smell and taste so different from my own, and that was really fun. For an inexperienced guy he was also a surprisingly good cocksucker. After hours and hours, he didn’t want me to cum in his hands but I was too close and let it go. He cum while jacking off with me standing behind him, biting his neck. He was a really big shooter, it was kind of fun to play with it all afterwards.

I know he really wanted to meet up more, but that was enough of that for me. It was like a seal was broken though, and I became a real sexual being. I ended up hooking up with a woman I met at a party just a few weeks later, I think because I felt confident that I can actually do that kind of stuff. She even became like a fwb for a little while. That’s a story for another day, though.

So I’ll be completely honest - my first time was with an escort. If you want to read the story about my virginity hijinx, then read on ahead. Otherwise, you are more than welcome to skip and/or pass judgement at me.

It was proper shady too - the lady looked nothing like her online profile (she looks like a fat old woman, and her profile seems to suggest she is in her 20s), and I didn’t realise I could walk away. That, and at this point I was 31 and desperate to get laid. I pay this lady for 1 hour of her time - please stick a mental pin in it.

So I go into the room she wants me to go into. It is dark af. At this point I’m like “huh, this is how I die. Never could’ve forseen this”

Then the escort with a thick Russian accent told me to take my clothes off. I was so nervous, I stupidly said “all of it??” as if I can have sex in my boxer shorts. Of course she told me to take off the boxer shorts too.

So I’m standing up, butt naked and she’s fiddling my todger like she’s trying to crack a safe. This isn’t going so well.

Next thing, I’m instructed to be on all fours on the bed, bum facing her. She then proceeds to give me a blowjob. A bit weird, but whatever - I’m getting my dick sucked. todaywasagoodday.mp3

Next thing I know, this weird, moist feeling occurs around my butthole. Oh my god. THIS LADY IS RIMMING ME. I WAS NOT PREPARED FOR THIS, LIKE AT ALL!!

It felt so weird to have my salad tossed, but honestly it was fucking amazing. This is turning out to be one hell of a first time experience!!

She then tells me to lie down, and then says we are having sex. FINALLY!! What I came here to do! But then she asks me quite possibly the worst question I could hear from an escort.

“Condom or raw?”

I literally blanked for a moment because I was like “wait, no, that’s illegal” until my dumb-dumb brain made me realise no, that shit isn’t illegal, and not only that, but many other guys have diddled her raw and have been spreading god-knows-what.

Since at this point I’m so close to getting laid, I just say “condom” and she puts on a condom and then fucking sits on my dick.

It had got to be the weirdest sensation. I didn’t know what to expect, and I was already a bit conflicted, so my dick may not have been as hard as I was expecting, but it just felt like a space station entering the vast cosmos of space. I felt like my member was so insignificant in comparison to the lady. If anything, I probably walked away thinking my dick was microscopic.

Eventually I start thrusting up (I am a spaceman wanting to explore the cosmos, after all). At this point she is clearly fed up with me thrusting into her and tells me to go missionary.

So I go missionary. All I can say is if there was anyone watching through some secret camera or something, I am so sorry. What you saw was a man flopping around like a fish out of water. I now know sex isn’t exactly dignified, but holy crap that could not look less dignified.

And then I came, the escort told me my time was up and that I needed to shower. Did the shower and left. Checked my watch, and I had only been there for 15 mins.

For those who care about my sex life, I have visited escorts - or should I say I’ve visited one escort that I immensely trust for over a year now. Admittedly, life has been exciting where dating, sex, and escorts are no longer playing the big part, but I’m sure pretty soon it will.

Thank you for coming to my TED Talk.

Did a lot of fumbling around trying to figure out the best angle to insert it. I was wearing a condom, but maybe need not have, because the first couple of times I didn’t come at all. Coming while jerking off and coming inside with or without a condom are totally different and so I wasn’t sure if I had or not. About the third time we did it. We were going and I realized that I was finally about to come and you can really tell.

Edit: her and i were friends at the time, tried dating which didnt work out. We went back to friends with benifits and remain so to this day.

Edit 2: feelings are a real thing at least in my experience. I am pretty sure i love her. I know i have felt like she has been more than an FWB for quite a while. The idea of getting her pregnant and her being the mother of my child is a total turn on. I don’t know of friends who want babies together.

I tried being romantic when I first put it in, and I accidentally quoted The Lion King 2: Simba’s Pride. Turns out it was the right move anyway, because it totally broke the tension.

Everything was perfect: it was a summer afternoon, we were in my room. She was lovely, with nice curves, chestnut eyes and an adorable smile. There was some music playing in the background, probably U2 or the Beatles.

And I lasted approximately 3 seconds. Maybe less.