The Cheating Bridesmaid



What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? Around 450

The Cheating Bridesmaid

How long ago did this hookup happen? Around 3 months ago

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? For less than a year

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 was at a friend’s wedding and she was a bridesmaid (and one of the bride’s oldest friends). I had met her a couple of times before, including at the engagement party, and flirted with her a bit. She is due to get married herself next year and was at the wedding with her fiance. I had been staying at the hotel where the wedding was happening the night before and had flirted with her while having dinner with the bride and groom and their friends. At the wedding, everybody had been drinking a lot and I found myself dancing with her. She’s a tall, slim, nicely tanned brunette of around 30. She was wearing a long, lavender coloured bridesmaid’s dress.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? While we were dancing, she leaned in to me and asked if I wanted to take her up to my room. At first, I thought I had misheard her, because although she had been flirting with me I obviously knew she was engaged, and her fiance was somewhere there on the dance floor. She asked me for my room number, told me to go to the room and said she would join me after a couple of minutes.

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 got to my room, took off my shoes and waited on the bed. Sure enough, after a minute or two, there was a knock at the door. I opened it and she came in. I asked her if she was sure she wanted to do this and what about her fiance? She shrugged and smiled sheepishly in a way that suggested that her cheating on him is something that happens quite a lot. I doubt he has any idea.

We started kissing and getting our hands all over each other. There was a desk in the room, and she sat on the edge of it. With her eyes fixed on me, she slipped off her underwear – lacy, purple French-cut knickers – and threw them on the chair. I got my hand up her dress. She was completely waxed smooth between her legs. It didn’t take much fingering to get her very wet.

She pushed my hand away, then stood up, hiked up her dress and bent over the desk, presenting her beautiful arse to me. I asked if she wanted me to put a condom on and she said no. I pulled my trousers and boxers down, grabbed her hips and entered her from behind. She murmured and giggled to herself. She told me to be quick so that she could get back before her fiance wondered where she was. I fucked her hard for about five minutes, with her moaning loudly the whole time, and then she groaned “oh yeah!” as I came inside her.

She couldn’t seem to stop smiling as she put her knickers back on, smoothed out her dress and retouched her lipstick in the mirror. Then she left. After a few minutes, I followed her back downstairs and we both carried on as if nothing had happened.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 are still in touch and I would like to hook up with her again, although we live a long way apart.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient

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? 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? Nobody.

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? Not at all

What was the BEST thing about this hookup? Quick, easy, hot sex with a gorgeous woman.

What was the WORST thing about this hookup? I felt some guilt afterward that I knew I had participated in her cheating on her fiance.

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

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

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