My first time was in college, with the woman who is now my wife! The first time we fooled around was shortly after we met, we were back in my apartment and she offered me a blowjob which I happily accepted. While it felt really good at first, I started feeling some pain after a few minutes. Turns out that, through a combination of my foreskin not being able to fully stretch around my head at the time, and it being her first time around a penis with a foreskin, mine had torn just a little bit. While it was nothing severe medically, it was definitely enough to keep me from cumming. I offered to go down on her, but that was the end of that hookup.

Our first time having PiV sex was about a month later, my roommates and I put on a little thanksgiving dinner that I had invited her to. We were planning on going to a show on campus after dinner, and so I walked with her back to her apartment for her to grab something before we went to the show. We got to her room, and she just looked at me and said “want to have sex?”. Of course the answer was a resounding yes. It was definitely a little awkward to figure out positioning but we settled into missionary, and I just told her I’ll take it slow and she could tell me if she wanted a change in speed or anything. After a few minutes she said that it was getting uncomfortable so we called it there with neither of us finishing, but both of us excited to keep practicing at a later time.

Had been watching so much porn since 14, I basically knew everything to do; without it turning into some wild bullshit. Told her I was a virgin, went down on her, ate her out like nobody’s business, then hopped on top and had my fun. It was magical, and life changing.

Next day, she broke up with me. Saying I lied about being a virgin, that there was no fucking way in hell I was given how enthusiastic I was, and knowing what I was doing.

I legit had to convince her I was just a REALLY big pervert.

It was fun, but has definitely been almost exclusively better since. I distinctly remember being alarmed at how warm it was to be inside her, I had not expected that at all. I mean, I’d fingered her and stuff, but never felt anything like that on my penis.

It was a lot of fun, not awkward at all. I did wind up bleeding, which I did not expect given I had a dick at the time. Didn’t stop us from going again the next day though.

Played hooky to finally get after it (weeks and weeks of allllmosts with the gf), somehow made it past the awkward without a scratch and more than a few shared giggles & good spirits. I was on top of the world, doing everything I could to hold out until she came, but then I thought I heard her voice change a little?

I opened my eyes to see that she was looking right up at me (missionary, don’t judge) with a finger pressed against her lips and eyes wide, tense.

Then I heard the moan again. A woman’s noise —and then a manly grunt.

My mom was upstairs (not at work?! how? why -oh.) with her boyfriend. Fucking. Right above us. The rooms’ floor plans were pretty much the same, beds angled the same direction, headboards against the same wall, maybe even fucking in the same position. Fuck. Fuck. Fuuuck. 😶

I have no idea how we escaped without notice that late morning, but the unstoppable hormone engines in both the gf & I at that age were burying the needle at all hours, at the helm of every decision both major and minor at all times — and would not let that stupidly improbable scene deter us.

We found every. single. opportunity. we could to shuck clothes and devour each other at a moment’s notice. Behind the portables, on the art tables after most electives were done for the day, up in the botany greenhouse balcony, in her car during her “smoke” break at work, in her friend’s parents’ master bath during a family dinner, etc. 🤷🏼‍♂️

I guess the lesson is: don’t let the expectation of “magic” discolor your IRL experience of it, and always keep your sense of humor intact. Resounding, ardent interest will always win out over self-doubt & cyclical worry. Have fun, be safe, and check in with your partner. 🥰

Awkward and not that enjoyable.

My first time was with my gf at the time, right before starting college. We did the whole progression, handsy to blow and eventually sex. However, we never got to actually fuck, just blowjobs, since she had some issues at the time.

Fast forward a bit, and I met this other girl in college. We became friends with benefits, and she would often come to bounce, but on my first time, I was really nervous. We had a lot of fun, but I came pretty quickly and it was over fast. Not really that memorable, but it did turn me into a much hornier person afterwards in general I’d say.

First time, between 14 and 15, Sophomore in HS and was dating a Junior (we’ve been dating for a couples months). I feel like the build up was pretty normal, hand stuff, oral, etc. Then she asked if I ever wanted to experiment, of course I did (there was a 0 chance I was passing this opportunity up). Timing was perfect, parents left two hours before and would be gone all night. I think for a first time for both of us it was pretty good. I didn’t cum (didnt have a rubber and was nervous about busting in her) she said she did (she was embarrassed because when she orgasmed she peed a little on me). From then on my brain has been rewired, always horny, thinking about sex, etc.

After climax I had the fastest onset, most powerful migraine I’ve ever had in my life and then passed out. Fortunately that only happened a half dozen times or so or I would have thought it was serious. Luckily that hasn’t happened in over 20 years but it really sucked when it did.

After a costume party when I was 19. She was dressed as Lara croft, and will Smith’s boom shake the room was playing. I remember because I almost burst out laughing when I heard it start.

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