What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +/-15 and counting
How many hookup stories have you here posted before? None

First affair…..

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than a week

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 had seen her ad on Craigslist (back when it did not totally suck) and we had initiated email conversation. There was some initial apprehension on her part as she didn’t really want to hook up with a married man. However, she changed her mind realizing it might reduce the possibility of the fwb situation devolving into a “real” one. We met one time before at a restaurant so that we could what each other were like in person as we had agreed not to exchange pictures. When I first saw her, I could not believe how beautiful she was. She had just turned 20.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We actually first had our encounters in a borrowed RV in a grocery store parking lot. We couldn’t be at my house due to my wife and couldn’t be at hers due to her home situation. We had agreed that would be satisfactory for a first “meeting”.

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? That first encounter was alright. She had specified initially in her ad that a partner should be able to last and/or go multiple times. Being more than 10 years older, I possessed stamina that she was unused to. I also had learned to force myself to continue fucking even immediately after cumming. These were both very valuable traits with her.

Initially, I was very nervous, her not so much. Until this point, I had never had intercourse with anyone other than my wife of 10 years. It was very difficult for me initially to make a move. I honestly wanted to back out but felt at this point that I owed her some sort of play. I sat by her silently, sheepishly, for a bit. Finally, she asked what I was thinking. The reality for me is that I had dozens of thoughts racing through my mind. She was amazingly beautiful. I liked just being near her. Had I met her some other way, I wouldn’t have had the courage to approach her, even if I were single. I told her that I wanted to kiss her. We began to slowly warm to making out. I began to kiss her face and neck and nibble her ears as I started to run my hands over her back and sides, pulling her close tightly. After a bit, as we began to heat up, I asked if I could go down on her. She took her pants off and I gasped in amazement at how absolutely perfect her pussy looked. She was shaved to a very light stubble and it was so symmetrical, with her labia fitting perfectly (totally unlike my wife). I began to kiss all around. Her smell was unlike anything I had experienced before. She had been working all day and was unshowered. Her flavor was perfectly developed. I slowly penetrated her with my tongue, probing deeper with each flick. She was so wet, the flavor saturated my mouth. I was rock hard at this point and realized that she was expecting intercourse, despite my contentment with devouring her.

I looked up at her and asked if she wanted anything else. She reached down, grabbed my cock and told me she wanted it inside.

As I penetrated her, I was struck by how wet yet tight she was. I did not learn until later that I have a “rather large” cock. I was on top of her, holding myself above so as to be able to look at her and kiss on her. I slowly rocked in her for a while and she seemed almost uncomfortable. I asked her if she was okay and she replied that I didn’t have to go deep with every stroke and that she liked the feel of my dick head entering and exiting best. So, I shifted to a shallower stroke for a bit and then asked her if she would ride me.

When she got on top of me, she almost immediately began a shallow jack hammering of me. Watching her was breathtaking, like being in a porn. It wasn’t exceptionally enjoyable for me physically, however. I blew a load quicker than I wanted. I didn’t tell her that I had, however, and her motion was so violent that she didn’t feel me go. After a while, she was exhausted from her workout and we were both drenched in sweat. She rose up off of my cock, which was still rock hard and noticed that I had cum in the condom. She said I should probably change it. I had never cum before my wife before so, I had only brought one condom as it was all I thought I would need.

So, being in a store parking lot, I left her in the RV while I dressed and went in to buy more condoms. When I returned, we continued fucking for another hour or so (all in all almost 2). I came 2 more times without any indication that she had ever cum. She confided later that she had not. I was very disappointed at this time because I could not bring her to orgasm and I was physically exhausted. Additionally, I needed to be getting home as my wife was likely to grow very suspicious. We talked very little as we were getting dressed and agreed that we would get together again. We also told each other our real names.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, more than 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? Afterward, we did get together again (very many more times, actually, over the years). I felt incredible that I had actually boned this incredible girl but felt very strange lying to my wife about my whereabouts. However, my intense desire to see her again and hopefully make her cum the way I could my wife became an obsession with me. Over the course of the years, I developed (and still have) a very deep love for her. We got to know each other extremely well and became best friends in addition to lovers.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

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? I don’t know / I’m not sure

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? A few close friends. Most were envious and wished to live vicariously through me.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Somewhat

Why do you regret this hookup? If it had been a one time event, it wouldn’t have been too bad. I hated lying to my wife initially, although over time I became numb to that. While there was absolutely no emotional connection initially, it did not stay that way. Furthermore, I went from being a faithful husband to a man whore since that time. I have developed an addiction for other women that is insatiable. I have also become much better at reading and manipulating women. Obviously not all of this came specifically from this hookup but, if I had never experienced this first time, there never would have been a second. Or a two hundredth.

What was the BEST thing about this hookup? The taste of her pussy was indescribable. I’ve never tasted anything so good since.

What was the WORST thing about this hookup? Starting down the path of a serial adulterer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It forced me to become an expert on reading women’s needs and desires. While I hate that I constantly cheat, I’m always looking for that next “high”. I became aware that I wasn’t as plain as I had previously perceived myself.

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

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

Anything else you want to add about this hookup? If I could do this all over again, I wouldn’t. I have had some incredible experiences since but, ignorance truly is bliss. Now that I know how much I enjoy different women, I find it almost impossible to not have “yet another” hookup.

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? Honestly, it’s a horrible thing for society in general and in my life specifically. On one hand, I wish casual sex were even more readily available as I thoroughly enjoy the good aspects of it. However, seeing the pain that has been brought about in my life, in my mind, in my heart, in my marriage, in my family– it makes me wish that casual sex were an almost unobtainable action.

What do you think about the Casual Sex Project? Very interesting and potentially useful.

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