Anal Finally



What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Single
How religious are you? Not at all
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

Anal Finally

How long ago did this hookup happen? Last night

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

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than 6 months

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? Towards the end of last summer, I was out on the town with a buddy. I saw two girls sitting at the bar by themselves. I was very drunk and feeling overconfident. After speaking only a few minutes, I went for the kiss on the attractive one, while her friend left for the bathroom. She was young looking, tall, and confident. Dark hair, slim, wore a loose flirty top. Figured she was 25 (turned out to be younger). I got her number before her friend dragged her away for the evening.

We started texting, saw each other a few times, and started becoming fuck buddies. She would come over after her work, stay for a few hours, we’d have sex, and she’d go home. If I called her while drunk on weekends, we’d often meet up, and she’d end up staying the night. Next thing I knew, months had passed seeing her once every two weeks or so.

I’ve never tried anal sex before. Either ex girlfriends were not into it, or any attempts were quickly aborted due to discomfort. I brought anal sex up several times with my fuck buddy. She said she tried it, and it was open to the idea – but didn’t share my eagerness or enthusiasm.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We arranged to meet mid week in the evening via text. She came over to my apartment on her way home from work in the evening. After hanging out for about 45 minutes, we start making out on the couch.

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? Clothes come off. I go down on her. She gives me blowjob (which, from her, are incredible – full throat and all). We 69, then she’s eager to fuck. Condom on. She rides me. I fuck her from behind. We move to the bedroom.

I fuck her missionary for a bit, all the while thinking about how do I bring up the fact that I want to put it in her ass. I eventually just ask. She responds “Really?”, like she’s not thrilled at the idea. I ask if we could try, and if it’s too much, she can just say so. She reluctantly accepts, and asks to go gentle.

I reach for some lube and spread it around her asshole. I then put some around my cock. We lie on our sides on spooning position, and I start to press it against her butt. She takes hold and directs it for the right angle. I slowly feel myself enter her. I’m asking every six seconds if she’s doing okay. She nods, or says yes. Once it’s in, I start slowly fucking her, trying to be gentle.

So years of thinking about fucking a girl in the ass, I’m finally doing it for the first time. On one hand, I’m super stoked. On the other hand, with all that lube, it feels not all that different from vaginal sex. It’s like actualizing your fantasy, and realizing it’s not that big a deal.

We try several other positions. From behind, then missionary with her legs up. At this point, she really starts enjoying it. She’s saying dirty things like “Fuck my tight asshole”, and says she’s going to cum. She even pulls my body in closer, saying she wants my whole dick in her ass (which was the hottest part of the entire experience). It’s not long before I cum inside her (in the condom).

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? I ask if she’s doing okay, and she enthusiastically says yes. She even said “We can try that again, sometime”. She also said that I know how to do it right.

I hope to continue this fuck buddies relationship for a while. We’ve talked about possibly arranging a threesome. I think we’re comfortable with each other to try new things, which is totally ideal. These things are always difficult to predict how long they will last.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? No one. Just here. That’s why I’m posting.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I finally fulfilled my fantasy of doing anal sex.

What was the WORST thing about this hookup? Constantly gauging whether my partner was enjoying it, and not “living in the moment”. However I believe I did the correct thing.

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

All things considered, how NEGATIVE was this experience? Not at all 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? For me casual sex is a bit fucked. How many partners is too much/not enough? I have mixed feelings on the personal benefits of casual sex. No opinion on others’ approach to casual sex.

What do you think about the Casual Sex Project? Some great bedtime reading!

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