by

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +/-15 and growing
How many hookup stories have you here posted before? 7

Business Trip Lover

How long ago did this hookup happen? 4 years ago

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

How would you best classify this hookup? Short fling

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? She was a biracial girl (my first). She was very pretty, about 25. I met on an ad from CL. She sent a pic and at first I thought it was fake (it wasn’t). We agreed to meet at my hotel room (provided by my employer). I was excited but she was nervous about my being married so, wasn’t sure it would go anywhere.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She came to my room late in the afternoon. I invited her in and tried to keep things very low pressure. She sat in the chair and I set on the bed. She was wearing a pair of jeans and a shirt that showed just enough cleavage to totally have my attention. We talked for a bit, learning just a little about one another.

After a half hour or so, I leaned back more on the bed and told her she was welcome to come sit by me if she liked. She agreed and sat fairly close. I laid back on the bed and she leaned more toward me. We continued to talk a little and then I asked her what she thought. She said she didn’t know, what did I think. I told her she was very pretty and that I really liked the way she looked. She said she liked me too so, I asked her if I could kiss her.

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? She agreed to kissing so, I began to rub my hands across her back as we kissed. I asked her if she was open to more and she made it very clear that she was.

I worked my hands under her shirt and began to touch her waist and brush her breasts. She took her shirt off and I removed mine.

I reached behind and unfastened her bra and marveled at her breasts. They were large and beautiful. I began to touch, kiss and suck on them while working one hand down the back of her pants, squeezing her butt. We then broke the kiss off as I pulled her pants and underwear off.

I couldn’t believe how beautiful she was, laying there on her back, her head lifted by a pillow so she could see what I was about to do. She lightly sighed as I began to kiss inside her thighs and kiss and nudge her well groomed mound. Her scent was nice. I began to gently kiss and lick between her pussy lips. She laid her head back more as she ran her hands over my head, helping me deeper into her.

As she became drenched in her own juices combined with my saliva, we agreed that it was time for intercourse. She had brought a condom so, I helped her slip it on me, after she licked and kissed my cock a little.

I entered into her and she was very wet and felt good. The angle of her vagina was sharper than I was used to, allowing me to give her a lot of pressure from my pubic bone on her clit without having to push as deep inside of her. I still buried myself deeply in her and was able to give her a lot of clitoral stimulation simultaneously while giving her intense vaginal stimulation. I could tell the sex was going to be intense.

We switched positions a few times during the encounter. She was an anal virgin and I was unable to convince her to try it with me. I was able to get her comfortable with me inserting my tongue in her anus and a little bit of finger penetration.

She was able to have a massive orgasm while riding me and it left me completely drenched in her juices. We only stopped a couple of times that evening to go buy more condoms and have dinner (we enjoyed some room service).

As the action was winding down, I asked her if she would spend the night with me. She did and I left her there in the morning as I went to the meetings I was in town for. She stayed over a few more nights that week.

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 stayed in touch for a year or better. I was never able to get back to her town. She eventually settled in with a steady boyfriend and we lost contact.

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), Learning new things, experimenting, To cheer myself up, I was feeling lonely, Making new friends, Boredom

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? A prior lover/friend.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? She was beautiful and fun. The sex was great.

What was the WORST thing about this hookup? Not being able to stay in contact with her or see her since.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Somewhat. I know as good as it seemed on the surface, if we were able to have longer together, there likely would have been emotional damage.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? No.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I still think casual sex is a damaging activity, despite the fact I continue to do it.

What do you think about the Casual Sex Project? Good forum.

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