Business Trip

by Jean

What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Moscow, Russia
Highest education received: High school diploma
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I love sex and I love pretty girls.
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? 2

Business Trip

How long ago did this hookup happen? 3 years

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 less than a year

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? Hannah is a lawyer in a law firm that our company works with. We meet sometimes during meetings. She is not tall, with short blonde hair, and she is quite pretty, though not a top beauty, but an office suit suits her perfectly: short skirt covering her curvy ass, legs in heeled shoes, boobs peeking out of the jacket – enough to make my cock hard. A pair of glasses finish the image. She is a bit younger than me and is married. She turned out not to be very sociable; I tried to talk to her some times but with no success. Anyways, I didn’t pursue anything with her at all.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day, we received a task to go to another city to defend our company’s interests in court, it was usual business. We took our flight in the early morning to get to court in time. Litigation was long and hard, but finally, our side won. We exited the court late in the evening completely exhausted as we didn’t even have lunch. We went to the restaurant and during dinner, Hannah became more positive and relaxed as we had done a good job together and I saw her smile for the first time ever. When we got to the hotel it was almost midnight. There, we found out that we were about to lodge in one room and more than that, there was only one bed! It was too late and there was only one clerk at the reception and he said that he couldn’t change the room himself and we had to wait until morning which was nonsense as we had to leave in the morning. I was confused, but Hannah confidently told them that it was okay and she wasn’t confused at all. I followed her.

We laid on different sides of the bed and turned our backs to each other. Hannah was almost naked and had only her panties on. She told me earlier that she didn’t want us to have to give up any comfort and that she wasn’t shy to show me her boobs. Her boobs were quite good, I have to admit, and they were slightly bigger than average size. I too had only underwear on. Despite all that, I was too tired to look at her body and think about anything sexual. She probably understood this and that’s why she acted that way. I fell asleep quickly.

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? I woke up in the middle of the night with my cock hard as rock. It seems that my body got enough rest to remember that I hadn’t had sex for a while. I stood up from the bed and walked around the room trying to calm down with no effect. I couldn’t go back to sleep either. I started stroking my dick as jerking off seemed the easiest way to solve my problem, but then I noticed Hannah sleeping on her side of the bed. Fuck, I thought, why would I jerk off when there was a beautiful lady sleeping beside me? She’s married, yes, and didn’t give me any sign of sympathy, but why shouldn’t I try? Anyway, there will always be a time to jerk off.

I laid in the bed next to her and touched her back. She didn’t react. I gently kissed her shoulder and started stroking her back. She still didn’t react. I went on kissing her back and she moaned and opened her eyes slightly. I moved my hands to her hips and tugged at her panties. When I completely took them off, while kissing her ass, she sighed. She was finally awake but she didn’t really open her eyes. I turned her on her back and started kissing her cheeks, neck, shoulders while stroking her body. Then I grabbed her boobs, kissed them, and started sucking her nipples, first the right one, then the left. Her boobs were bigger than those of any other girls I have had sex with up to that moment. Although I prefer smaller ones, it was very pleasant to kiss those soft boobs with very gentle nipples that were already hard. When I sucked them, she moaned, and as she moaned, I moved my lips to hers and kissed them. I opened her legs and put my finger in her pussy: it was gentle and warm, but dry. I moved down and started licking. As I was licking her, she started moaning louder. I kissed her lips again and our tongues touched. I began to finger her again and noticed that she was more humid this time, and so it was time for the main event. I moved my hips in between her legs and directed my love tool inside her. As my cock’s head touched her pussy lips, she opened her eyes. I closed her lips with a kiss and pushed my hips towards her. My cock’s head entered her vagina, but it still wasn’t wet enough and my cock stuck. I pulled out, spat on my cock’s head, smudged saliva along it and shoved it inside Hannah again. Finally my cock entered her with its full length. She exhaled, closed her eyes and turned her head to the side. Her pussy was already wet and hot, and it gripped my cock very tightly. I was moving slowly and gently, trying not to harm her. She touched my hips and started moving them, so I accelerated a bit, and she started moaning again. I was kissing her neck and boobs all the while. Then, I lifted her legs and accelerated again. It was enough for me, I hadn’t had sex for long so I could not last any more. As I felt inevitable orgasm closing, I stopped moving, shoved my cock deep in Hannah’s pussy and shot my huge load inside her.
After the contractions stopped I pulled out, fell on the bed, and fell asleep.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? In the morning Hannah woke me up for breakfast. She acted like nothing happened and didn’t talk much. When we were having coffee I broke down and said: “Thank you. It was wonderful.”
“What?” she asked.
“What happened last night,” I replied.
“Nothing happened last night,” she said firmly, “do you understand?”
“Of course,” I said. “Is it okay that I came inside you?”
“It’s okay, but not a word about it anymore.”
During our journey home we tried to act like nothing happened, though it was difficult. I barely could hide a smile when I saw her husband kissing her in the airport. After that we occasionally met at work but didn’t talk.

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? Fun, pleasure, horniness

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They were too out of it / passed out / asleep and therefore unable to give consent

To whom did you talk about the hookup? How did they react? Nobody. I’m sure she doesn’t want her husband to know about it.

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

What was the BEST thing about this hookup? I got even more than I was expecting. I fucked a pretty married woman, left my semen inside her, and got away without any consequences, what can be better?

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? I loved sex before it and I still do.

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

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

Anything else you want to add about this hookup? There is always something special about sex with married women. It’s like a competition with another man, and I win it on his territory.

What do you think about the Casual Sex Project? I think that by sharing these stories I can express my gratitude to all those wonderful girls and women that I shared best moments of my life with.

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