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What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Philadelphia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Advertising
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 0

My train girl

How long ago did this hookup happen? 2 months

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

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

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? Jennifer was 32, long redhair, hazel eyes, average build, long legs and nice ass. My car needed to get fixed after an accident so I needed to take the train for a week. I would get a ride to the train station to Philadelphia. I noticed her waiting there on the first day for the train, dressed professional in knee length dresses and heels. She caught my attention.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the first day I saw she got off at my same stop and actually worked in the same building as me. On the ride home we were on the same train also. The next day, I saw her again and it was just the two of us. I started some small talk, which continued for the ride into the city. This continued to till Thursday. She said see you at the train later. I told her Thursday’s I meet friends at a close by bar. She smiled at said goodbye.
As I am walking to the bar after work, I spot a familiar face sitting in a outdoor cafe. It’s Jennifer and she waves me down. We chat some and I feel her leg against mine. I start to smile at her. She asks “Do you really want to go bar with guys when you can come to my empty office with me”.

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 headed back to her office, which was empty pyschologist office. She took me into the one room with two couches and locked the door behind her. My heart was racing, I didn’t want to cheat on my wife but this woman was very sexy. We began to kiss our hands exploring each other’s body. She pushed me back onto the couch and began to take off her top. I pulled off my shirt and began to open my pants. She straddle me on the couch with her skirt hiked up. My hands squeezing her tits, our mouths locked in kissing and her gyrating on my cock. She slid down off the couch and pulled my pants the rest of the way off. She took my cock in her mouth and began switch from licking and sucking my shaft and licking and sucking my balls. I played with her tits and moved her hair out of the way so I could see her work. Sh did a great job of bringing me close to climax and then slowing down and then working back up till she finally took my load in her mouth.
After that experience I was eager to show her my oral skills. I laid her on the couch and spread her legs. I began trading her cult with my tongue. Exploring up and down her lips. Sucking on her her. Her moans told me I was doing her good. After a awhile my fingers worked into her wet vagina. Her legs wrapped around me as she reached her orgasm. A I sat back on the couch and she sat on top of me facing me as we kissed again. She inserted my cock into and ride me me, then she turned around so she was facing away from. This felt amazing. I nipped on her ears and neck. My hands squeezing her tits and both us took turns playing with her clit as she voiced up and down on me. She eventually came again and was exhausted. I asked if I could come one more time and she said yes. She laid on her back and I entered her. She was moaning louder tell me to go harder. The position was hurting her back, so she bent over the arm rest and I fucked her standing up. This position brought us both quickly to our final orgasms.

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 laid on the couch exhausted for about 5 minutes, then she said I needed to get back to my wife and her husband may me getting worried about her. We cleaned up the room together. The guilt hit me there. I told her I was not sure if I could do that again. She said she understood. I went back to my office to get a change of clean clothes that I kept there. The next day on the train, she thanked me for the great time, and she felt attractive again that’s why de did it. I think she was looking for some one to rescue her from her bad marriage. I have seen her around but we only have done small talk. Definitely not as much flirting.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

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? Somewhat

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? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Somewhat

Why do you regret this hookup? I hate that I became a cheater. And I think I hurt her feelings

What was the BEST thing about this hookup? It was amazing to have a woman tell me they wanted to fuck me. She was very vocal. It was great sex. I felt wanted

What was the WORST thing about this hookup? Knowing I am a cheater

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? That it is hard to have sex with out getting emotionally invested

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Fairly negative

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