Second Night of a Business Trip

by Director

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? 1

Second Night of a Business Trip

How long ago did this hookup happen? 5 years

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 three years of this long distance affair I took a new position in the company and our hook up opportunities ceased. This was the second night we had spent together on this business trip and it was clear from the first night (which is detailed in an earlier post) that we were not going to be doing much sleeping tonight.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The day had begun very early for C and I. We had woken up about 4:30AM and spent about 20 minutes kissing and fondling each other before I headed back to my room. It was a busy day of meetings for both of us and we had team dinners scheduled that night so we knew that it was going to be late before we were back together in bed. All day long we were sending texts back and forth between us about how and what we were going to do that night. Sexual tension was high but we kept our distance between us during the meetings. Both of us are married and with 300 co-workers around us all day we could not afford for our affair to be discovered. It was very common at these company events for people to hook up but most were one night stands. Ours had been going on for several years and to get caught would not be good

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? It was about 11PM before my work responsibilities were done for the day. I said goodnight to my team, half of whom were still getting drunk in the bar, and headed to my room. I sent C a text saying I was done and where was she. She responded that she would be in her room in 15 min. I used the stairwell again to sneak down to her room and she was in the bathroom getting ready for bed. I crawled into bed with just my boxers and turned on the TV. C came out of the bathroom wrapped in a towel but totally nude underneath and crawled right up top of me. She scolded me for leaving my boxers on and pulled them off. We began to kiss while she rubbed her body against my cock and getting me hard. Once she had me good and hard she started grinding her pussy against my dick, sliding up almost to the point where I could slip inside her but backing off just before I could enter. She was super wet and she rode me like that for several minutes. We always used condoms but the temptation to go bareback tonight was huge! She took the remote for the TV and turned the volume up a couple of clicks, saying, “I’m going to be a bit louder tonight,” and then bent down to kiss me as she slid my cock all the way to the entrance of her pussy. I pushed in about four inches as she moaned in pleasure and then I slowly slid back out. I told her that I needed to taste her first and as I slid down the bed she slid up until she was straddling my mouth. She had one hand on the headboard and the other gripping my hair as she started grinding her pussy into my mouth and I pushed my tongue in as deep as I could. We did that for a bit, then I rolled he onto her back and finished eating her out much more gently and more focused on her clit. She came quickly this way and I was glad she had turned the TV up because she was right, she was louder tonight. She began to massage my cock and slowly slid down to take my cock in her mouth saying simply “your turn”. It was amazing! The warmth of her mouth surrounded my cock, her tongue swirled around the head while she stroked up and down my shaft with her hands. It didn’t take long before I was about ready to blow and I let her know I was close. She looked me straight in the eye and sped up her pace, never taking her mouth off the head of my cock and never breaking eye contact. I exploded in her mouth and she began to suck harder, making sure none escaped. She grabbed the towel she was wearing when she came out of the bathroom, wiped her face and my cock clean, and then opened the night stand where we had put the condoms.  She grabbed them and said, “Now fuck me.” She laid on her stomach and put two pillows under her so her ass was elevated in the air, then looked back at me and spread her legs a bit. She moaned as I entered her and I started off with slow and gentle strokes. That lasted about two minutes then she looked back at me and said, “No, I said FUCK me.” Okay then!! I began to pound her hard. With each thrust she let out a grunt. She was pushing against the headboard so that I went in hard and deep each time. I had ahold of her waist with each hand and her grunts and moans slowly shifted to, “Yes,” and, “Harder.” She was close and now it was my turn to speed up. I started to jackhammer her as fast as I could. The word “yes” was said about 50 times, then “Oh God” as she fell silent and her orgasm washed over her. I cuddled up next to her and and asked if that is what she wanted. Her reply was, “Yes.”  We cuddled took a quick shower and crawled back into bed. But the night wasn’t over, we used three condoms that night. Missionary, cowgirl, more doggy then finally we started to spoon and I ended up sliding in her from behind. We finished the night that way. It was almost 3AM before we fell asleep and we had to be back up and me back to my room no later than 5:30. We were tired horny people that next day!

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 had two more nights together on this trip, and if possible we were more horny then ever after this night.

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

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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? Give a person to experience different sexual things and needs that they may not get from a single person.

What do you think about the Casual Sex Project? Great place to share something I can’t tell anyone.

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