First Time Casual Sex



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Africa
What country and/or city do you live in? Johannesburg
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Project Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Confident
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? 0

First Time Casual Sex

How long ago did this hookup happen? 24 years

What was your relationship status at the time? In a relationship (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 month

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 a short sexy bombshell. This was her first year at college and our hookup happened with in the first month. I was actually interested in her room mate at the time. They two of them hang around our dorm rooms as they had a curfew and needed a place to sleep some nights. I never hooked up with her before the night in question. I liked her but was more interested in her roommate.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was a a party outside of college. When I returned to my room around midnight, Tiny and her roommate were in our room. They were at a party and returned late and needed a place to crash for the night. My roommate ended up messaging Tiny’s roommate and myself with Tiny. I had lots to drink at my party and the 4 of us continued to drink in the room. Around 2 in the morning we all decided to stop drinking and switch off the lights to sleep. The girls got dressed in PJ’s and got into bed, one with each of us.

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? Once the lights were off, and being fuck horny, I started to make out with Tiny. I picked up that she was inexperienced sexually. I started playing with her beautiful breasts and took her top off, licking, sucking and nibbling her nipples. I moved south and started to rub her pussy. Her PJs were very loose so I had no problem to start playing with her pussy. First I just ran up and down and played with her clit. I started to finger her and had her climaxing in no time. She was extremely wet. By this time I was naked and horny as fuck. I got on top of her. She then confessed that she was a virgin and did not want to have full on sex as she used no protection. I honored her request at this stage. I just rubbed the tip of my cock between her pussy lips and over her clit for a while. She then asked me to just put the tip at her opening. We continued to play like this for a while. She then started to urge me to penetrate her by pushing harder and harder on my cock. Eventually it slipped into her pussy tearing her virginity. We must have slow fucked for close on an 30 minutes before I filled her pussy with my cum. She was shocked after I cummed in her pussy as she was not using any form of birth control. I told her not to worry that we could get the morning after pill first thing in the morning. We both fell asleep in each others arms.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? The next morning when I woke I was a bit scared as she did initially say she does not want to have intercourse. I was drunk the night and not sure how persistent I was to fuck her. Once she woke and kissed me and confirmed that she enjoyed it as much as I did. We did speak about it a couple of days later and she confirmed that she wanted it just a much as I did. But regretted she done it somewhat as she wanted to give her boyfriend her virginity.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Plan B / Emergency contraception

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

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? A little bit

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? A couple of my friends. And most being college students they all gave me high fives

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The surprise virgin I got to fuck and fill with my cum

What was the WORST thing about this hookup? That we only did it the one night. And that she had some regret regarding cheating on her boyfriend and not saving her virginity for him

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This was my first casual sex. Before this I only had sex in a committed relationship. And it opened up my eyes to the world of pleasure you can have sexually.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Years later I found out that my girlfriend at the time at another college had just as much fun as I did with casual sex.

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 have had such fun times, and believe that you need to play and experience lost of things before you settle. I think that woman get the bad end of the stick as they are called sluts and men are called heroes. But in the end of the day it takes two to fuck. And society should relax on the sex issue.

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