by Madison Adams

Gender: Male

Age: 45
Race/ethnicity: White
Location: USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Attorney
Religious affiliation: Jewish
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? None

We Cheated

How long ago did this hookup happen? 7 or 8 years ago

How would you best classify this hookup? One-night stand

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? We were both married. I was 37 or 38. She was early 40s. We were both a bit out of shape. I was kind of looking for women slightly older then myself and maybe a little out of shape thinking they might be easier. We met on Ashley Madison (“AM,” a website for married people to date). We first made contact on a Sunday and had sex that Thursday.

She was on there because she just wasn’t feeling it with her husband anymore. I was on there strictly because I wanted to have sex with someone other than my wife. See, I had been fairly inexperienced when my wife and I met in our 20s and while our sex life was still good, I was curious.

I liked her profile on AM so I messaged her. We texted on the AM site for a little bit before moving to yahoo. It’s been awhile and I forget some of the details, but our texting got erotic pretty quickly. We eventually exchanged cell phone numbers, sent each other nude pictures. She worked near my home and I worked from home some days so we began discussing about meeting for coffee.

At the start she was adamant about no sex on the first meeting, but I was persistent. By Wednesday she was open to sex when we met. What can I say, I’m good with words.

Thursday rolls around. She had told me the day before that her company was sending her out of town that night for a meeting, meaning she had the afternoon off so we made plans to meet.

We texted and flirted with each other all morning. Very graphic. Me telling her what I was going to do to her when I got her in bed etc. By the time we stopped texting to meet, I was pretty sure I was going to get laid that afternoon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We decided to meet at a Starbucks that I knew was just up the road from a no tell motel. She got there before me but we knew what we each looked like from the pictures. We said hello and made a little small talk. Finally I asked her if she wanted to get coffee or go to the motel. She replied whatever I wanted. 10 minutes later we are in the motel room. 15 minutes later we are having sex.

I had never had anything close to a one night stand when I was younger, much less gone to bed with a woman 15 minutes after physically meeting her for the first time.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We got to the room and pretty much got right to it. We started making out on the bed fully clothed, but quickly removed each other’s clothes. I went down on her for a bit, she played with my balls and penis. It had been so long since I had been with another woman that I forgot that people have different styles. Anyway, I was there to have PIV [Penis in Vagina] sex so as soon as I saw she was wet enough, I put a condom on and we began having intercourse.

The sex was good. She came several times, which I wasn’t used to as my wife is a one and done type of person. My friend’s breasts were much larger than what I was used to, but for some reason I never thought about titty fucking. Our positions were pretty standard: missionary, her on top, side by side and finally doggy, where I finally came.

We spent the next 20-30 minutes lying on top of the bedsheets just talking. Finally I get up and she asks where I was going as my penis became hard again. I told her I wanted to feel her without a condom and just started having sex with her again. We went at it again pretty good and I was enjoying it much more without the condom. She came again and then asked me to not explode in her. When I felt myself getting close, I pulled out and masturbated until I came on her chest. Usually the second time takes me a long time to orgasm, but the excitement of going bareback took over.

After that round it was time to go. We went to the bathroom, took one look at the shower, and decided to just clean ourselves with wash clothes. She was going away for business and I was going to the Y to shower (and work out) after work so we weren’t worried about our spouses smelling the sex.

Went back to the office, handed the key back to the clerk, kissed, got in our cars and went on our way. We had plans to hookup again but it never worked out.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We hadn’t been with anyone else but our spouses for a long time so we both knew we were clean. She was on the pill.

What were your REASONS for having this hookup? Horniness, plain and simple

Were alcohol or drugs involved? If so, how much? No

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I was happy I did it, but also realized that I could never cheat like that again. I swore to myself if I got away with it, I’d never cheat again. So far I’ve kept that promise.

As to my friend, she was a nice person and I hope she found happiness. I told her I couldn’t do this again and she understood. By now the son she was staying in the marriage for is an adult so I hope she has moved on.

To whom did you talk about the hookup? How did they react? I have told no one but you.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and wanted for both of us. We each had our fun.

Do you regret this hookup? If so, why? Yes and no. Yes, because I cheated. No because I scratched an itch and brought some joy to another person.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was the sex, the worse the guilt. I remembered why I never has casual sex when I was single, I am a relationship type of guy.

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 or anything else? I know I am a jerk (among other things) for cheating on my wife and cucking another guy by having sex with his wife, but this site is for sharing, so I shared.

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