Unexpected Business Trip Hookup



What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Some college (not currently in college)
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 2

Unexpected Business Trip Hookup

How long ago did this hookup happen? a month ago

What was your relationship status at the time? Dating casually

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? She is an engineer for my company, 33 years old, about six feet tall, with a slim body, and small tits, but a fairly large ass. She has medium brunette hair that she always has in a pony tail, brown eyes with black square rimmed glasses, and she was the shy and nerdy conservative type. We had a very limited working relationship as we worked in different departments, but I had been on one trip with her prior. She really wasn’t my type, however, she had a decent ass.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’d been sent out to do field work with a customer. The original trip was only supposed to be four days, however, due to weather and unforeseen circumstances, the trip was extended to seven days. We were in some little town in the middle of nowhere, which meant at the end of our day we’d return to our rooms for the night as there wasn’t much else to do. She had a boyfriend and again she wasn’t really my type, so I didn’t see anything happening between us. Saturday rolled around and the customer invited us out to the pub. We were within walking distance to the hotel and the customer wanted to show us a good time, so we all started drinking. For once, she actually wore some nice fitting jeans that really showed off her ass, and much to my surprise, at one point, I was shocked to see a thong poking out. As the drinks started flowing, she started to loosen up and become almost flirty in an awkward way. We called it a night a little before midnight and returned to our hotel. On the elevator ride to our floor, she was giving me a look. We were staring each other down, and as the door opened we just stood there. Finally, she stepped forward and gave me a kiss. We started making out until the door closed. We were both a little shocked and I asked about her boyfriend. She was a little flustered as she searched for an excuse before she finally blurted out how she hadn’t had sex in two weeks and that she thought I was hot and this whole trip she’d been thinking about having sex with me. There was an awkward silence before I asked if she was sure she wanted to do this. She bit her lip and nodded yes. We rushed back to my room and stumbled inside as we began making out again.

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? We ripped each other’s clothes off in the dark as we crawled onto the bed and started making out like teenagers. I removed her bra and sucked her tiny breasts as her nipples got hard, then slid a hand down her stomach into the front of her thong where I found a nice little landing strip followed by her soaking wet slit. She gasped and shivered as I ran a finger between her lips. When I crawled down between her legs and peeled her thong off, she stopped me as I got in position to eat her out. She said i didn’t have to and she wasn’t sure she even liked that sort of thing, but that just made me want to even more knowing she was so inexperienced. She laid back and was a little tense for the first few minutes before loosening up. It didn’t take long before her hips were bucking and she was muffling her screams with a pillow. I got to a point where I couldn’t hold off anymore, only then realizing we didn’t have condoms. She asked if I was clean then said it was fine as she was on the pill anyway. I grabbed my cock and rubbed it between her lips, then attempted to push it in, but she was incredibly tight and pulled away with a gasp. She reached down and grabbed it and mumbled holy fuck. I told her I’d go easy, but it still took a bit of convincing. Finally, we tried again, and this time, I got it in. She struggled a bit, but I took it slow. Once I was all the way in, she said she needed a minute. We started slow and worked up our pace, and it didn’t take long for her to have an orgasm which almost sent me over the edge. We started up again and I knew I wasn’t going to last as she was so wet and incredibly tight. I pulled her to the side of the bed and took her from behind and unleashed everything I had. She had a white knuckle grip on the sheets as she screamed into a pillow. It hit me like a train as I erupted inside of her. She yelped as I delivered a few balls deep thrusts then held my throbbing cock inside her until it finished. I pulled out and she just laid there over the edge of the bed, limp and panting as my cum ran down her thighs. She finally dragged herself onto the bed and mustered up the words to say she’d never in her life had sex like that. Once I recovered, we fucked again before passing out.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 woke up to the alarm clock. Being sober, she was a bit awkward and panicked because we were co-workers and she had a boyfriend. I calmed her down and assured her no one would find out. Once she settled down, we laid there a bit and discussed things. I finally got up and when I crawled out from the sheets with a semi chub her eyes locked on to it. I gave her a smile and jokingly said I would be in the shower if she wanted to go again. I didn’t actually think she would take me up on the offer, but she did and we fucked one last time before leaving. We agreed no one could find out and it was a one time thing, but I suspect if we end up on a trip together again she’ll be making a move.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Intoxication, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? Very

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

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!