Completely Unexpected Hotel Sex

by DanTheMan

What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Expermimentalist
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 0

Completely Unexpected Hotel Sex

How long ago did this hookup happen? 10 Years

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For 1 to 3 years

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? His name was Paul, and he was a 50-year-old work colleague.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met a few times at Paul’s house, but it started at a hotel where we were both staying in after a work night out.

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? Paul and I both attended a work party. The party was done, and we knew we were staying in the same hotel so we got a taxi together. I didn’t really know him, and I certainly had no idea he was bisexual (if he actually was) and the thought of anything happening never even entered my mind. We had a chat in the taxi and over a couple of drinks in the hotel bar but absolutely nothing happened and there was no talk of sex. I didn’t even think we were flirting. Or at least I knew I wasn’t.

We went to our own rooms and I went to bed….. and that should have been it. But about 30 minutes later, there was a knock at the door and it was Paul. I answered the door in boxers and a t-shirt. He asked if he could come in. I was half asleep but said he could. As soon as the door was closed, he had me pressed up against the wall with his tongue in my mouth. It took me completely by surprise, and I pushed him off me to start with. He smiled and said, “Don’t tell me you don’t want your cock sucked,” and the next thing I knew he was on his knees pulling at my boxers. I started to tell him to stop, but as the words came out of my mouth, I felt my cock go into his mouth! And he was DEFINITELY well practiced. So I thought, fuck it and let him carry on!

He spent the best part of an hour sucking me and edging me over and over again. During that time, we’d both ended up naked and had gotten on the bed. I was REALLY turned on, so when he flipped me over and started rimming my ass REALLY deep, I actually started to want him to fuck me. I’d never even entertained the idea of being with another man let alone having a guys cock inside me. I’m not sure if I was giving off signals, but as soon as I had thought that, he was lying on top of me with his hard cock pressing at my ass. He whispered in my ear, “I can carry on or I can finish you off with my mouth, what do you want me to do?” I replied, “I want you to fuck me!” Maybe I should have been a little more subtle because as soon as I said it, he grabbed my shoulders and pushed himself inside me, and it hurt like hell! It was the first time I’d had anything in my ass, and even though my ass was all wet from him rimming me, it still came as a shock! But he didn’t let the scream of surprise I let out stop him. He pushed and pushed and pushed. He wasn’t a small guy, and I took all of what I suspect was about 9″ right from the start. I felt his balls against my ass cheeks, so I knew I had all of him inside me. He must have noticed it hurt because then he was quite gentle from then on…sliding in and out of me slowly but still with his full length. He had his way with me like this for a good 20-30 minutes before pulling out, standing me up, bending me over the bed and entering me again doggy style. As he fucked me, I wanked myself off. He pulled out and came over my back, spun me around and held his mouth wide open under my cock…. a few minutes more wanking and I came into his mouth. He swallowed, got dressed, and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? Nothing. We’ve never even spoken about it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

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

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

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

How would you best summarize people’s reactions about this hookup? I didn’t tell 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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was completely unexpected and unplanned.

What was the WORST thing about this hookup? I hurt for a fair few hours afterward.

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!