First Night of a Business Trip


This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Usa
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Account Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Straight
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

First Night of a Business Trip

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 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? I met C years before at a meeting and was attracted to her instantly. We were both married and lived hundreds of miles from each other so nothing between was ever a serious consideration however the attraction was still considerable. Over time we continued to find more and more opportunities to work together and a very fun and sexual relationship developed between us. After 3 years of this long distance affair I took a new position in the company and our hook up opportunities ceased. We had gone about a year without seeing each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A large company wide meeting was scheduled that we would both be in attendance at and instantly we began planning our reunion. We had to be careful as the meeting involved over 300 co-workers but we secured rooms on separate floors at the end of the hall near a stairwell that allowed easy passage between rooms. By being on different floors it gave us sufficient separation to avoid any suspicion. That first day was full of anticipation of what that night may bring after a year apart. After dinner and time with our teams we retired to our rooms. I used the stairwell to join C in her room

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 both got ready for bed and discussion about business and the days events kept us occupied until we crawled into bed together. We were both unsure if the sexual chemistry between us would still exist but we instantly began to kiss and our hands quickly moved to find each other’s pleasure centers. The kissing moved to her breasts as my hand massaged her clit. Once my finger was good and wet she pulled my hand up to her mouth and licked her juices from my fingers. I then moved to her pussy and licked and sucked her to orgasm. once she finished she pulled me up to her face and we began to kiss while she stroked my cock. Rolling into me she simply said fuck me. I put a condom on and we fucked missionary. I came quickly as I was already quite stimulated and then we cleaned up. As we snuggled back into bed I began to spoon her and she pushed her ass hard against my cock. Taking my hand I started to massage her clit again and she began to moan softly and continued to grind her ass into my cock. After a few min I rolled her onto her stomach and she pushed her ass into the air. I slid in behind her and began to slowly fuck her. Having just cum I was much more in control and we fucked like this for quite some time alternating between slow long strokes and fast hard pounding fucking. As she approached orgasm I sped up my pace and we finished together.

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 finished and spooned for the rest of the night. Early in the morning I returned to my room to get ready for a busy day of meetings… We spent all day sexting each other talking about what the next 3 nights were going to be like.

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

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? No one

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? The closeness

What was the WORST thing about this hookup? We had to be quiet not to alert the rooms around us

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

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? It has its place

What do you think about the Casual Sex Project? Love it

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