I Became His (First Time Anal)

by Randy

What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? OC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? NA
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation:
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? None

I Became His (First Time Anal)

How long ago did this hookup happen? 1 year

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? 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 answered an ad on Craigslist for someone looking for a Discreet Massage from a Masculine male. When I got there he was tall 6’3″, I am 6′. He had a massage table set up and told me to use the oils that were on his table.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Answering an ad on Craigslist.

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 started massaging him and after about 15 minutes I had him turn over. His cock was uncut and about 7″ and after about 5 minutes of rubbing his legs I started rubbing his crotch. He told me to start sucking his cock and moved my head towards it. He then got up and was sitting leaning on the table pushing my head onto his very hard cock. He then started to finger my ass which made me start moaning. After a few minutes of that, he said he wanted to fuck my ass. I told him I don’t think I am ready for that. He said to let him try and convinced me to let him try. He was strong and tall, he picked me up and set me on my back, put on a condom and started to lube my crack. I knew I was about to take a cock inside me for the first time. He slowly slid his cock into my hole and it did hurt at first but also made me moan with pleasure. He held my legs up on his shoulders while he slid his cock in and out of me making me moan like his girlfriend. Then he started to stroke my cock and it wasn’t long until I had one of the most intense orgasms that I had ever had. When I had finished cumming, he took off the condom and shot his load all over my chest and stomach.

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? I have been back twice and he is the only man that has fucked me. I plan on seeing him again too.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Submission / Relinquishing power, Didn’t want to disappoint my partner

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? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 ever.

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? A little bit

Why do you regret this hookup? Guilty Feelings

What was the BEST thing about this hookup? Cumming with his cock in my hole.

What was the WORST thing about this hookup? Guilt

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I am a very masculine person in public but now know I like to be submissive to bigger stronger men.

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

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

Anything else you want to add about this hookup? Nope

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 like casual sex

What do you think about the Casual Sex Project? Great site.

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