First Time Anal



What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Canada, Toronto
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Teacher
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

First Time Anal

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Single

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 met this person in a club in Windsor on a night out. He was very tall, a black man and he claimed to be a semi-professional footballer. We met each other that night and started talking and enjoyed each other’s company.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had not arranged to meet each other but got to know each other on the night. We started talking in a bar and then decided to stay in each other’s company for the rest of the night. We went to a club after the bar.

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? During the night we were making a lot of physical contact. During the time at the club, we kissed and he did put his hands on my arse several times. He told me he liked my arse several times which I enjoyed. Towards the end of the night and after a few hours of enjoying each other’s company, I asked where he was going afterward. He wanted to stay with me. We spoke about sexual interests and he told me he liked anal sex (giving) and he asked if I would be interested. I told him yes. We stayed with each other after the night and got a taxi back to my house where we continued to talk about anal sex. After an hour or two, we started to kiss and he began feeling my arse and pushing his fingers into my arsehole. I asked him if he wanted to do anal sex with me and he said yes. We tried it and it didn’t work for a long time as I was very tight but after using some baby oil we started making progress. We did anal sex for 1-2 hours and he eventually cum inside my mouth as I couldn’t take any more.

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? Afterward, he stayed in bed with me for an hour. I was really sore but after a while, I fell asleep. I woke up several hours later and he was gone. We had exchanged numbers and he had taken a picture during the intercourse and sent me the evidence. We haven’t seen each other since but we do message.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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 spoke to my friend the next day who lives with me and had to apologise for how noisy we both were. She was very happy for me

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some 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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I was in mild discomfort from the anal sex and I feel embarrassed that I let a stranger into a very tender vulnerable part of me

What was the BEST thing about this hookup? I came from the experience and I tried something new.

What was the WORST thing about this hookup? I had a very tight arse and it was really sore the next day. I had cum in my bottom for a long time afterward

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, as much as I enjoyed anal sex I need plenty of lubrication if I try it again. I really did enjoy the new experience though

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It seems quite a few male friends are interested in my experience that night and I have suddenly gained a lot more male friends

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