Ashley Madison

by Oyoa

Age: 36
Race/ethnicity: White
Location: Suburbs
Highest education received: College degree (eg., BA, BS)
Occupation: Homemaker
Religious affiliation: Catholic
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 1

Ashley Madison

How long ago did this hookup happen? 5 years ago

How would you best classify this hookup? Two 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? After my first “affair” (see Cheater Cheater), I needed a way to distract myself from our “break up.” I decided checking out Ashley Madison. If you have ever been on this site, women basically email these guys and find one that is a good fit. I found a guy I liked and his pictures were cute. We emailed back and forth on the site and then I told him we should try Yahoo. He had never used IM before. He was probably about 8 years old than me. We were both married but my husband was checking out other men so I decided I needed to do my own thing. Anyway, we built up quite a bit of sexual tension. On this site, sex is the expectation. So talk moved pretty quickly to sex right off. We decided to meet at a restaurant to see if the chemistry was really there.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a restaurant. We ate and talked a lot about various things. How unhappy we were in our marriages, jobs, anything that two people on a date would discuss. But then we jumped to sex. Things we wanted to do or try. Things we like. He asked if we could go to a hotel right then and there but I had my period. I said we could go to his car and fool around. He was very nervous about people seeing us. We kissed and I pulled out his cock and it was the biggest I’d ever seen. Then someone pulled up so that ended that. We had more talking, more sex IMs. The anticipation had been built. We decided to meet at a hotel. I had a vibe though that he was very concerned about looks. Having had a few kids and also once being overweight, even though I’m a normal weight now, my body was nowhere near perfect.

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 met at the hotel. He had a foot fetish and a butt fetish. Immediately he wanted to lick my asshole. I let him and it felt good. We had oral. He said he didn’t enjoy oral very much in general. I will tell you though, I’ve given many men oral and they were all thrilled so the issue was all his. Despite him being weird on things, I continued on. We had sex. He was very large so it was a little uncomfortable. It was weird b/c he never made a noise. Ever. It was hard to tell if he was enjoying anything. He basically told me it was my job to make the noises. I think I orgasmed once and that was tough b/c I felt uncomfortable. He wasn’t a good lover. Afterward I called my best friend and said so.

We didn’t talk about sex as much after that. He was distant but made excuses for it. We met again a week or two later. This time things were even weirder. He was going down on me and when I didn’t come in a certain amount of time and asked him to do something a certain way (I was by no means being bossy!) he threw his hands up in despair. It made me feel horrible. I went ahead and had sex with him again, hoping it would be better and it wasn’t. He gave me $5 for lunch at the end and that made me feel like an asshole.

Of course I had an email after that stating that he wasn’t attracted to me b/c of my body. It hurt my feelings but in the end it was for the best b/c he sucked at sex.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I stupidly let him go without a condom. He complained so much about them. I actually thought I was pregnant at one point. He was my third sexual partner ever and the only one (after my husband and we were both our firsts) that I’d ever had unprotected sex with. I learned several months later that I had HPV. Thankfully it was the non cervical cancer causing kind/the non herpes kind. I was so pissed.

What were your REASONS for having this hookup? I felt lonely and hated my husband for looking at men and blaming ME for it. B/c I was a prude in the bedroom he said. Well I wasn’t interested in having threesomes with other men or sucking other guys cocks in glory holes. I wanted to feel alive again. To feel wanted.

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 didn’t feel very good. This guy was a jerk after I thought about it. My body wasn’t perfect so he couldn’t be attracted to me/have a good time. Believe or not, we continued to talk for a long time after. I don’t know why  I guess it was nice to just talk to someone. Eventually the emails were longer apart and then we completely stopped.

To whom did you talk about the hookup? How did they react? My best friend. Since this was my second time cheating on my husband and she was helping me pick out men on AM, she was fine with it.

Was this a consensual and/or wanted experience for you? For your partner? Yes, it was.

Do you regret this hookup? If so, why? I do. He gave me an STD and was a jerk. I wish that I had picked up on the red flags sooner and not gone through with it. I had SO many options on AM. I went out on many “dates” before I picked him. I could have had any one of a dozen me on there. I kinda feel like I upped my “number” for no good reason.

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? Um he had a big cock. I never saw one that big. He made me realize what I wasn’t looking for in a hook up and how to be more selective.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What did you think about this story? Tell us in the comments – just be nice!

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