Third 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? 2

Third 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? This was the third night of a company wide meeting and we had spent the previous 2 nights together (written about in previous posts) C and I had met years before and were attracted to each other 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? This was a large company wide meeting with over 300 attendees. We had rooms on separate floors but near a stairwell that allowed for easy unseen passage between rooms. This was Wednesday of the week long meeting and the night before had been a very intense and long night of sex. We were both functioning on less then 3 hours of sleep and were extremely tired. The fact that the day was filled with long boring meetings and long winded VP’s did not help much. If it wasn’t for all the sexting that C and I were doing between us, I am sure I would have fallen asleep in the middle of the meeting several times. C was in no better shape and we had actually agreed that tonight we should plan on getting more sleep then the night before.

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? C texted me that she was heading to her room and that her door would be unlocked waiting for me. I had returned to my room a bit earlier and taken a shower to relax. Once we were safely in her room we crawled into bed and cuddled up together intending nothing more then to spend the night spooning and sleeping. I wrapped my arm around her just under her breasts and she pushed her ass firmly against my cock. Almost instantly I started to get hard and she could feel it. She let out a soft yum and started to push her ass against my cock. I started to move my hand across the lower part of her breasts and then slowly moved my fingers up to her nipple. After reaching her nipple, she took my hand and pushed it against her breast and ground her ass hard into my cock. With a smile I said “I thought we were going to sleep tonight”, at which she rolled over to face me and said, “I can sleep when I get back home to my husband”. We began to kiss and she slid her leg up against my cock and began rubbing it hard. I reached a hand down between her leg to find a very wet pussy and slid 2 fingers inside her. I commented on how wet she was to which she responded that it had been wet all day. She pulled her top off and positioned her breasts so I could suck on them. C was always very up front about what she wanted sexually and over the years I had learned that this meant that she wanted my tongue. I flipped her on her back and started to suck on her breasts while fingering her. I looked up at her and smiled to which she put an a hand my my head and gently pushed me down to her pussy. A few minutes of oral and she had an orgasm. We rested and cuddled and talked while she teased my dick with her hand and recovered a bit. All the while I’m rock hard and my dick is aching for some action. Finally she slid down and started to suck on me. After a few min I grabbed a condom handed it to her and told her to put it on me. She gave a slutty smile and asked “How to you want me”. Considering the night before and how tired I was I said. “Its your turn to be on top”. She lowered her pussy down onto my cock and started to ride me. We fucked like this for several min, she was slow and controlled, careful to make sure I didn’t cum too quickly. Simply enjoying the feeling of me inside her. But I was ready to cum. I pulled her down to kiss her but quickly rolled her over on her back, put my arms under her legs so they were spread wide and up over her head, slid my dick in and pounded away hard. She put her arms up to push against the headboard closed her eyes and arched her head back. I didn’t take long but we both clearly enjoyed it. We finished and took a quick shower then crawled back into bed and started to spoon. She started to grind her ass against my cock and I asked a bit in shock Again? to which she laughed and said. “No, we need to sleep, but maybe tomorrow during the lunch break”.

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? This was the third night of a 4 night business trip. I had one more night with her and was hoping that it would be the best yet.

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)

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? 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? unexpected.. had expected to sleep not play

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? 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

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

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