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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Perth (at the time)
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Teacher
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 2

Big girl has an anal orgasm

How long ago did this hookup happen? 15 years

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For less than a week

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? We randomly met in at online chatroom, and discovered that we lived in the same city. We were both married, and both gave each other fake names. She warned me that she was ‘big,’ and I said that I was fine with that. I was so starved for sex that I guess I was chasing the feeling of being wanted rather than any particular physical appearance.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She suggested a particular motel, so I went there and booked a room. I then waited and felt extremely nervous. I wondered why she had so emphasised how big she was. When I saw through the curtains that she was approaching, I saw that she was correct – she was indeed bigger than anyone I had been with. She wasn’t exactly my ‘type,’ physically, but then I also enjoyed the thought of something different with someone different.

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 to kissing and soon our mutual nervousness wore off. I enjoyed licking her to an orgasm, and then she started sucking me. She instructed me to tell her when I was about to cum. After a while I could feel the orgasm building, so I told her. She immediately pulled me out and shook her head: ‘Not yet.’ The build-up subsided and so I didn’t have an orgasm. I licked her to another orgasm and then she sucked me again, with the same ending: I told her I was going to cum, and she said, ‘not yet!’ After things subsided again, we had sex for a while, with me on top. When she could tell I was getting close to cumming, she took me back in her mouth and finally let me release a big load, which she swallowed. We cuddled for a while, and before long I became hard again. She asked me what I’d like to do next. ‘I want your arse!’ I said, and she said I had earned it. She got on all fours and I gave a few thrusts into her pussy to get some lubrication. I then lined up into her (virgin) arsehole, and began to try to ease it in. At first it wouldn’t go past about an inch, but after she relaxed a bit it went the whole way in. I began thrusting gently, concerned not to hurt her, but after a while she urged me to make it deeper and harder. As I did so she began to moan and scream loudly, yelling, ‘Oh your cock is getting bigger – it’s so big!’ Now I am very conscious that I’m of average size, but I suppose from her perspective it was feeling bigger than ever. This turned me on more, and I really got into fucking her arse hard. I was sure that neighbouring rooms could hear us. After a while she suddenly began shuddering and she yelled, ‘I can’t believe it – I’m orgasming and you’re not even touching my pussy!’ That was one of the hottest things I’ve ever experienced! This drove me to orgasm inside her arse, and we finally collapsed.

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? We both enjoyed it, but in the following days I felt a bit bad that I had cheated. I told her that although I’d loved it, it was best as a one-off, and she agreed.

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, To feel better about myself, To feel more desirable

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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? Somewhat

Why do you regret this hookup? I was married

What was the BEST thing about this hookup? Her anal orgasm

What was the WORST thing about this hookup? cheating

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? Somewhat positive

All things considered, how NEGATIVE was this experience? Somewhat 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 used it to feel desired, but I no longer do this

What do you think about the Casual Sex Project? Always intriguing!

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