Best Boy Sex I Ever Had

by FilmGuy

What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Houston
Highest education received: College degree (eg., BA, BS)
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? None

Best Boy Sex I Ever Had

How long ago did this hookup happen? A Year Ago

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was in his mid-20s, short hair, average build, smooth, kind eyes. He claimed to be from Mexico City here on student visa.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met him through an app as I was in a relationship at the time. We chatted for a couple of hours before deciding to meet up to talk before deciding to take in a movie instead. I met him at the theater and was taken aback by how amazing he looked. I also loved how polite he was and felt down-to-earth, something you don’t really see much. We watched the movie and occasionally looked at each other. After the movie, we decided to go to a tea house where we talked and he told me about his life and what he thought about considering his precarious situation in the U.S. It was here we decided to take this further. I lived only a few blocks from the tea house so we walked back to my place, stopping at a local convenience store for condoms on the way.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? As we got to my place, we went straight to the bedroom and started kissing fiercely. I pushed him on the bed fully clothed and started peeling off his shirt, kissing his smooth flat belly and chest as I did so. I could feel his bulge poking my chest as I did so and fought the urge to rip his pants off. I didn’t want to just fuck, I wanted to take my time, enjoy every moment of this tryst. I kissed his neck as my hands felt him all over and his went underneath my shirt and running through my thick chest hair. Now my own erection is hampered by my own pants and our cocks found themselves grinding against each other still fully sheathed.

I slid his pants off first, kissing my way down his chest and stomach. He was about 6 inches as was I, cut with a massive head. I kissed around his cock, especially his inner thigh before lowering my mouth on it. It felt so wonderful feeling it hit the back of my throat, hearing his soft moans as I could taste pre-cum. His hands were on my shoulders, both encouraging and demanding. I massaged his heavy balls as I kept hungrily devouring his beautiful cock. I wanted that load so badly, needed it. And not too long after I felt the warm gush of semen fill my mouth. I sealed his cock with my lips and kept every drop. I swallowed that load then smiled as I came up to kiss him once more.

After a few more minutes, he asked me to put on a condom, which I did, then lubed his ass as well as my cock. I put his legs on my shoulders and positioned myself to enter him. I wanted to keep eye contact as did so and he let out this beautiful moan as I slid inside him. He was so tight yet so welcoming. I started thrusting deeper, grinding rougher inside him as he started to let the moans out. His flaccid cock started coming to life as I kept fucking him, slapping me on the stomach as I fucked him harder. I came so hard, I let out a wild primal grunt as I thrust as deep as I could. Part of me wanted the condom to break and to know my seed was deep inside him. If I’m to be totally honest, I stroke myself to that thought even today.

He held each other for a while in bed, kissing, talking. He was getting hard again and I started stroking him before I made a decision; I wanted him inside me. Let it be known I haven’t bottomed in nearly 15 years and only for people I really care about. But there was something so special about him and knowing that I wasn’t going to see him again, I asked him if he wanted to. He said he did and lubed myself for him. Feeling my legs on his shoulders and the tip of his cock near my near-virgin asshole was enough to realize that I wanted this. As I felt him enter me, I was reminded why I’m not a bottom, but he also felt wonderful, not too big yet pleasant. He thrust deep and fast and within 3 minutes, his seed lined the condom he was wearing. And again, I couldn’t help but want to know the feel of his cum inside me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We talked a little more, drank water to replenish ourselves, kissed and stroked each other. As it was going on 6 hours and exhaustion was kicking in, he called an Uber and went home. We didn’t speak to each other again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I don’t talk about sex with anyone.

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I’d say everything. He was sexy, had great manners, very capable and charming.

What was the WORST thing about this hookup? Part of me kinda wished that we could’ve been more, but I am perfectly happy where I am and I know that sex doesn’t equal a fulfilling relationship in itself.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!