Helping My New Roommate Lose His Anal Virginity



What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Belfast
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Programmer (temp)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many hookup stories have you here posted before? None

Helping My New Roommate Lose His Anal Virginity

How long ago did this hookup happen? 2 Years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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? My partner was a guy who was 21 and i had just met that day as we moved into a house share together. As far as I was concerned he was just a friend at most.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started in our new shared kitchen, we were talking about life and love and our sex lives. I am a very avid fan of anal sex but he had never had it and presumed it sucked.

I (being very drunk) had to get him to experience it and suggested I show him what its like. (Even though I knew I was cheating on my boyfriend)

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 told him to whip out his penis and get ready, I was wearing a short frilly skirt so I decided to just hoist it up and pull my panties to the side. I applied lube and got him to take it nice and slow. I was on all fours and let him control it. He went slowly but thrusted very deep inside and stopped when fully in, he sat there for a second, I could feel the pulse off his penis. I gave him about five deep thrusts and then decided to stop as I felt guilty about my boyfriend.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

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? I regretted doing it and cheating on my boyfriend, I also felt bad for the guy because he kept hitting on me and trying to have sex.

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

What were your motives for this hookup? Thought it was an important experience to have, Just happened, I don’t know why, just went along with it

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? 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? I told my best friend who was quite mad at me but did forgive me over it.

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

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

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Very much

Why do you regret this hookup? I cheated.

What was the BEST thing about this hookup? I guess the risk involved.

What was the WORST thing about this hookup? Cheating.

What do you think about the Casual Sex Project? It’s great.

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