What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Teacher
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 30 years
What was your relationship status at the time? Single
How would you best classify this hookup? Short fling
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 the middle-aged MILF landlady who was lending a room to me when I was a university student in Bristol. She was petite and had some curves. She was bored of her lorry-driver husband who hung around home all day living off the rental money I gave them. She had dark hair, was sexy as hell, and clearly under-appreciated by her husband. I heard her and her husband fucking one night in the next room and it was all over in a minute with all the noise from him. She said her other girlfriends were turned on by me. When her husband started working away at night, I started to get close to the landlady.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Landlady was happy for me to spend time in the evenings in the front lounge watching TV, as the room I rented was small. The husband was away on a long distance lorry-drive so we’d talk about her job and films on TV. One day, I was talking about an actress on the TV who looked stunning in a black dress and gold necklace. She really turned me on. Next night when we were watching TV, I saw that the landlady had put on a black dress and some gold jewelry (normally she just wore jeans). She said her husband was affectionate, but she almost spoke apologetically of him like he was a sad sack. She was laughing, playing with her hair, and tucking her legs up on the couch so I could see the tops of her thighs. She complained of a bad back from her work so I offered to give her a back massage. I gave her a gentle rub as we idly watched TV. I sat on the couch, and she on the floor. One of my hands rubbed gently over her shoulders while the other strayed down over the top of her tits. I could see she wasn’t objecting and was leaning into me so I cupped her tits even more and started to kiss her neck.
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 it on more on the floor. I could see her starting to squirm and get hot. I pulled her down on the floor and slowly moved my hand up her thigh. I spread her legs to get to her pussy which was hot and throbbing under my fingers. We started to kiss on the floor. I massaged her clit in soft circular motions with my fingers as her wetness soaked through her black panties. I took her hand and led her up the stairs to the marital bed. At this point, she clearly became more nervous as she realized that she as about to cheat on her husband. She started to make small talk, so I kissed her deeply which got her back in the mood. I told her that I was going to fuck her hard and slow. I started to take her dress off. Her body was more toned than I thought and her pussy was freshly shaved. She clearly had planned to fuck tonight. She stepped out of her stockings and I pushed her back on the bed. I quickly undressed. I had a big boner that stuck out without any touching from her. Even though I’m an average size, it felt extra thick and heavy. She was still wet from the kissing downstairs and she asked me to take her hard. I pushed into her in missionary, fucking her hard, and pressed my chest down onto her tits. Later she said the weight of me on her pushed her into her first orgasm. She rode my cock for a good 15 minutes and I held her ass. Her pussy clenched on me and we both orgasmed. She for her second time and me for my first. I finished deep in her and didn’t ask if she wanted me to pull out. I kept hard in her for a while and then slid out and gently licked her pussy as she had her third orgasm.
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? We fucked in her bed through most of the night and then she asked me to go back to my room around 5 am as she was worried that her husband might arrive back. We would touch and flirt through the rest of the week and I moved into her bed and we fucked regularly during the rest of the semester. I did a great job of keeping her husband in the dark and spent some afternoons fucking in a small local hotel on the days when he was around. She said it was the best sex she ever had and glad that we were fucking behind her husband’s back because of the thrill.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method
What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Power / Dominance
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? The landlady must have talked to one of her other MILF friends about the affair as she said one of her bored friends who liked me wanted to cheat on her partner as well. Thought it was risky that she discussed it with a friend and the term soon ended and I finished the course and moved away.
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? I don’t know / I’m not sure
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Sex with a MILF and her admitting that it was the best sex she had ever had. Not getting found out and meeting up for some no strings hard sex.
What was the WORST thing about this hookup? Slight concern about being discovered – just for the inconvenience of finding a new place to live.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I recommend casual sex if no emotions are damaged.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
What do you think about the Casual Sex Project? Good – clear the air to confess and improve the human spirit.
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