Discovering Anal Play



What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? London
Highest education received: Some college (not currently in college)
What’s your occupation? Luxury Travel
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
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)? 14
How many hookup stories have you here posted before? 0

Discovering Anal Play

How long ago did this hookup happen? 2 months

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

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? She was 42 from Australia but living in London. Chubby with enormous breasts and totally waxed downstairs.

We met online that morning at about 7 am and messaged for an hour or so. We agreed to meet at a pub near her home for a quick drink to make sure we were happy to proceed.

I liked her pictures online and love the fact that she asked how I wanted her pubes to be.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at the pub, had a couple of drinks then she leaned in to say that she was going commando and asking if I wanted to go back to her place – which of course I did.

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 got back to her place, she took me to her room (her roommate was away for the weekend). We lay down on the bed and started kissing, I started feeling her tits then she pushed my head down towards her chest. I removed her top and bra and started sucking away, loving how hard her nipples got. While I’m doing this she begins rubbing my already stiff cock through my jeans.

I reach between her legs and can already feel her trousers are damp. She pushes me off and starts taking my pants down, eager to get to my dick – without even taking my jeans off she starts sucking my dick hard, her head bouncing up and down like a jackhammer. Then she looks at me as she takes it all in, resting her nose against my pubes as she tugs on my balls. I can feel that I’m about to cum so warn her, she pulls my dick out of her mouth and says “cum on my face” – I can’t take anymore so shoot all over her face and watch as she licks it off.

After a moment, I stand up and take my pants off, before removing hers, sure enough, no underwear and a perfectly smooth pubis. I lean in to kiss her again then start working my way down her body. When I get to her pussy, I push her legs open and start eating her out like crazy. I can see her clit peeking out so start to circle it, slowly sucking it as I slide one, then two, fingers into her. By now she is dripping wet. I can hear her breathing change as I pick up the pace and start ramming my fingers into her faster and faster while sucking harder and harder. As she’s getting close to cumming I start rubbing her anus with my little finger as well and her breathing picks up again. “Oh yes, stick it in my arse,” she says, so I do and that’s it, she starts cumming, I can feel her pussy clenching hard on my fingers and cum is pouring out of her but I don’t stop. She keeps cumming and cumming, leaving a huge wet spot on the bed. After what seems like an eternity her thighs start clamping against my head and I know she needs a break, so I pull my fingers out of her pussy and ass and smile at her. We are both dripping with sweat.

She looks at me and says “kiss me, I want to taste it”, so I kiss her long and deep, she takes my hand and starts sucking all the fingers that were inside her. We lie there for a moment and she asks if I’m ready to go again. I still need a few minutes so she starts slowly stroking my cock.

When it starts to get hard again she asks me to sit on her face and 69 her, so I do. She’s sucking on my dick, lapping my balls and then I feel her tongue on my exposed asshole, circling it, then pushing inside. My god, it felt incredible, and I can feel my dick getting even harder. “You like it when I lick your ass,” she says and I agree that yes I do, then she starts fingering my butt, first one, then two fingers. I’d never done that before but it felt incredible as she slid them deep inside and slowly pulled them out stretching my asshole wider each time.

My cock is twitching and dripping again when she stops and says “fuck me”, so I get off her and we start in missionary with me feeling her tits and her moaning away, before long she’s cumming again and begging me not to stop, go faster, harder etc. After a few minutes she’s recovered and gets on her hands and knees and asks me to fuck her from behind, I’m slamming into her watching her ass jiggle, amazed that I haven’t cum again when she tells me again to stick my fingers in her ass. So there I am, fucking her from behind with two fingers deep in her ass, I can feel my own cock with my fingers each time I thrust inside her.

I can feel her building up to cum yet again and I know I’m getting close. Now I just want to put my dick in her asshole, so I lean forward and say “you’re a dirty girl and I’m going to cum in your ass”, “yes, yes, please cum in my ass, fuck my dirty ass” she says. With that I pull out my fingers and push my dick in, she starts bucking against it and I know I won’t last long in there. A few more thrust and I can’t hold it back any longer and cum deep in her ass.

We both collapsed onto the bed, with me still inside her. My dick softened it slowly slips out of her butt and I roll off of her, watching as a trickle of my cum runs out of her asshole.

We lay there for 10-15 mins stroking each other before she got up to clean herself up. 20 mins later I was on my way home.

All in, we spend two and a half hours together in bed. I came twice and I lost count of how many times she did.

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? I felt great about it. I doubt we’ll see each other again as she is on the move around Europe but I believe that we both got what we wanted from the encounter and enjoyed ourselves very much,

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness

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? A couple of my friends, they were happy for me – but surprised at the fingers up my butt part.

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

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? Finding out how much fun anal play was for me.

What was the WORST thing about this hookup? It’s selfish but I wish she had been a little less chubby.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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? I think casual sex gets a bad rap. We all have needs and sometimes just want an avenue to release them without having a proper relationship or having to date.

What do you think about the Casual Sex Project? I think it’s a great idea to destigmatize casual sex – especially for women. Men are often admired for having casual sex whereas women are often looked down upon for “not having respect for themselves” or other such bullshit.

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