What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 1

Sex with my Sister’s flatmate

How long ago did this hookup happen? about 21 years ago

What was your relationship status at the time? In a relationship (monogamous)

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

How long did you know the person before this hookup? Just met that day

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 had met that woman at my sister’s apartment. She was tall, strong build, long dark hair, and pretty big breasts. I think her name was V. Shortly after the hookup, my sister told me that V was already 26 years old.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was 17 and my older sister had already left the city my family lived in to study in another city. I was still in school. I had just had my first girlfriend and lost my virginity maybe 3 months before this story happened.

I was visiting my sister over the weekend. She took me sightseeing and things like that. In the evening, we had a little party at her apartment. She was sharing the apartment with two other girls. The party just consisted of the two girls, my sister’s boyfriend, and me. V was the oldest person in the room. I think she mentioned she had just graduated from university.

We were drinking until late at night and when everybody decided to go to bed, my sister just handed me a mat, a blanket, and a pillow and told me to sleep in the corridor. She and her boyfriend went to sleep in my sister’s room. I was obviously not allowed in.

After everyone had gone to bed, V, dressed in her nightie, opened the door and saw me lying on the floor. She whispered to me that I don’t need to lie on the floor, I could come and sleep in her bed.

V was definitely the one who instigated sex. I would never have dared to approach this girl that was so much more mature than 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? I went into her bedroom and she told me just to lie down. I was already under her blanket when she was still standing in the room, closing the door. I remember how she turned around and unceremoniously took her nightie off, presenting me with her big tits. I was pretty impressed by them. Needless to say, I got pretty excited and already had an erection when V jumped on me. She started kissing me and took my shirt off. She was pretty giggly in her drunken state. She told me that she really enjoyed touching my skinny, well-trained body. V pulled down my pants and kissed all over my penis.

I was pretty overwhelmed, not having expected any of this. I hadn’t had much sexual experience yet and V was only the second girl I had been in bed with at that point in life. V was the one in control, and I was not sure on how to behave. I did not even have the time to consider that I was actually cheating on my girlfriend.

V handed me a condom and mounted me. She rode on me until I came into the condom. I remember her big boobs bouncing in front of me.

After the sex, I actually wanted to sleep because all of this was getting a bit too much for me. But V still wanted to fool around and insisted on it. She sat on my face so that I would lick her pussy. We did a bit of 69, then she allowed me to enjoy the very first tittie fuck of my life. I really loved that. I was definitely ready for the second round of intercourse. We did it missionary, and this time it took me a bit longer until I came.

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? The next morning, V acted as if this was the most normal thing. She gave me a little kiss, but it was clear that for her the action was over and there were no big emotions attached to it. My sister laughed when she learned that I had slept in V’s bed. She hugged me as if to congratulate me on my sexual exploits. She later told me that V was about 9 years older than me and often had casual sex.

I never saw V again. She wasn’t there when I visited my sister next time. I had hoped she would be, expecting more sex. V later moved out of the shared apartment.

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

What were your motives for this hookup? Intoxication, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 gave enthusiastic consent

To whom did you talk about the hookup? How did they react? As I said above, I talked about it to my sister, who told me that V does this all the time. My sister didn’t seem to have a problem with me cheating on my girlfriend. I guess she hadn’t even thought about it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I felt a bit disappointed with myself that I did not even think about my girlfriend and that I shouldn’t cheat on her.

What was the BEST thing about this hookup? I really loved Veronika’s big tits.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This hookup changed everything that I had thought about sex before. I had thought that sex is something very precious, that you have to work hard and be lucky to find a partner to have sex with. V showed me that sex could be very easy and mundane. It just happened and didn’t have much meaning, but was very pleasurable.
The encounter with V also gave me the confidence that I could seek women to have casual sex with.

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

All things considered, how NEGATIVE was this experience? A little 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? I love to have causal sex and wish I could have more of it now that I am married.

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