by

What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What country and/or city do you live in? Austria
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? University lecturer
What’s your current relationship status? Single
Religious affiliation: Atheist
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Unexpected ONS With A Partnered Woman

How long ago did this hookup happen? last weekend

What was your relationship status at the time? Single

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 met Rita (not her real name) via a dating app. She is 36, has dark hair, glasses, is of fairly average height and weight. She seems to be bright and well-educated. When I looked at her pictures on the app, I thought that she has rather big breasts, which I find very exciting.

I have been single for quite a while now, looking for a new relationship, but dating apps had not helped me so far. So I was very happy that Rita responded to me. We agreed to meet up at a restaurant where we would have snacks and wine.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our conversation went really well and I liked Rita. Her breasts are really as big as I had hoped when I saw her pictures. I had never been with a big breasted woman so that was a dream of mine. I was thus very interested to get Rita into my life. We both were friendly and chatty, made a lot of eye contact ; I had my hopes up.

Then Rita dropped the bomb: She asked me whether I mind that she has a partner. My heart must have stopped for a second. it felt like a hit to the stomach. My heart was racing: How should I respond? Of course, I didn’t have a long time to come up with a good answer, so I just said no.

Rita smiled and the conversation went on in different directions. I wondered whether I should bring the discussion back to that. But I didn’t want to be embarrassing, I didn’t want to shame her, I wanted to keep the good time I had going. I also felt we don’t know each other well enough to ask intimate questions such as whether she is unhappy with her partner.

We changed to a bar where we could sit comfortably next to each other on a sofa. Rita got very flirty, started touching. We held hands and then Rita leaned in for a kiss. We french kissed in this bar. I could feel her breasts rubbing against my arm. Rita whispered into my ear whether we could go to my place.

Of course I agreed and so we took a ride to my apartment.

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? Rita was all over me on my couch. I wanted to offer her some more wine but we didn’t even get to that. We made out on my sofa. I started playing with Rita’s big boobs and she got them out for me, took her bra off so I could suck on her nipples. I buried my face into her big boobs. I could not believe it when I saw this amount of butter mountains. All for me! Dream fulfilled, I’d say.

Rita opened my pants and started to suck on my penis. I was quite amazed. I had never had that happen so quickly. We both got completely naked and fooled around some more. Her lips around my penis felt really sweet. I could not believe what was happening when I saw that Rita was licking at my balls while gently masturbating my erect penis.
I wanted to do something for her and thus reached to lick her pussy and we tried 69. Her pussy was partly shaven which looked amazing and hot. During fooling around, I also rubbed my penis against her breasts. I had that cheeky thought that those huge breasts are usually caressed by another man but that night I got to rub my penis against them. It felt empowering. I also got to tick that off my bucket list.
I felt it was very awkward and uncomfortable on that sofa and requested we take it to my bed. Rita agreed and we left our clothes behind. Rita went for her handbag.

This looked strange at first. but then she got a bottle of lube and condoms out. I understood. Rita was well prepared and she had obviously planned to have sex on this first date. I really had not. I have never had a one night stand in my life and I was pretty baffled, to be honest.

Rita lay on my bed and put lubricant on her pussy. She spread her legs and offered her pussy to me. I put on the condom and entered her. It was very smooth because of the lubricant.

We kept on kissing while we were fornicating. Obviously, I often grabbed her breasts as well. Fearing that this could be the only opportunity to have sex with Rita I wanted to tick off everything from my bucket list and asked Rita whether she would change to the cowgirl position.

Rita obliged and I could see her beautiful breasts bounce as she was on top of me. She often leaned down and either brushed my face with her breasts or kissed some more. Rita really loved kissing.

Finally, Rita asked me to change to doggystyle because she could come more easily in this position. Rita has a nice big arse and it was fun pounding her from behind. I like the sound of flesh against flesh. I grabbed her breasts as i was fucking away. I noticed that Rita masturbated while I was fucking her. This felt a bit itch on my penis when I rubbed against her fingers but somehow exciting as well. I pumped as hard as I could trying to get her off. I climaxed and so did Rita.

We fooled around for a short while, chatted until Rita told me that she had to go. I did not dare to ask any questions. I kissed both of Rita’s nipples and her mouth one more time before we parted.

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? Rita called me this week telling me that she had really enjoyed the time with me and would like to meet again. Of course, I am very happy about that. We have not established a next date yet.

I have not dared ask about her partner. I would like to know what the situation with that is. I feel that it is Rita’s business to decide on whether it is morally right was she is doing to him, not mine. Maybe it is all justified. If not, it was Rita’s decision to go astray, not mine. I am looking for a relationship, I would like to have one with Rita, but I am obviously not so optimistic considering that Rita has a partner. Maybe she was just out for the quick thrill of a sexual encounter. But the way she was friendly and open during that telephone conversation makes me hope for more.

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

What were your motives for this hookup? Hoping or expecting it would lead to something more

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? I have told a friend about it. He was happy that I had finally found someone after a long period of grief and loneliness. We both think it is strange that Rita is seeking out other men while she is partnered. My friend expressed concern that I would soon be heartbroken again.

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

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

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? Rita was so friendly and nice.

Of course, I liked it that Rita was out for a one night stand. It was very surprising for me, but it was very exciting.

I got to have sex with a woman with big breasts. I had always wanted to do that. it was just as good as i had hoped it would be.

What was the WORST thing about this hookup? Rita has a partner, I don’t know what will happen with that. I want to see her again and be with her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was my first one night stand. I wouldn’t have thought that any woman would want to have a one night stand with me. So being with an attractive woman like Rita is a strange ego boost coming out of nowhere.

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? This was the first time I have had casual sex. I would like to have some more, but it seems to be difficult for me. Or maybe it isn’t as the experience with Rita suggests. Maybe I have to be more confident.

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