by

What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York City
Highest education received: High school diploma
What’s your occupation? Sales Rep
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Into sexual freedom, exhibitionism, nudism etc.
How many sexual partners have you had in your life (including oral sex)? 25+
How many hookup stories have you here posted before? 0

My Boss’ Wife

How long ago did this hookup happen? Nine 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? 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? Michelle was 35 at the time, she had a baby of about 1 year old. She wasn’t the hottest broad in town, but as you will see she had other appealing traits.

I haven’t known her in person before, just from hearing about her from her husband and from some phone chat.

I met her at her home at times when her husband was away.

I was extremely excited to meet her, she seemed like an extremely horny woman.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were both on a phone chat line where people called in to mingle and talk and if two people wanted to talk privately, they exchanged private codes, dialed each other’s code and had a private connection on the chatline. Michelle apparently liked what she heard and we went private. After conversing for a while we exchanged telephone numbers and over the next few days we conversed for hours over the phone.

At one point Michelle asked me where I work. I wasn’t ready at the time to tell exactly at which firm I am employed, so I just told her the street where our office is located. Michelle told me that her husband works there too, and after sharing a few more details I figured out that she was the wife of my boss. I told her that she shouldn’t freak out but I think that her husband is Mike so-and-so. She couldn’t believe that I have figured it out and she started pestering me to tell her who I was so I told her.

Now, you have to remember that this was a chatline where people came to seek sexual pleasure at some level, either to just talk about sex or to do it. She told me the next day that she was getting extremely turned on whenever she talked to be, just by the thought of having sex with her husband’s employee. I admitted that the thought turned me on too. She begged me to come over the next day while her husband was out of the house.

Her husband usually left for work at seven in the morning and I had to be there only at nine. This gave us almost two hours to play. I told my wife the next day that I had to be at work early. I parked a few houses down the block where Michelle lived and as soon as I saw her husband leave I knocked on her door.

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? Michelle opened the door, she was still in her nightwear, she motioned me to come in and be quiet because her baby was sleeping. She locked the front door just in case her husband will return so that we should hear him putting the key in the lock. Then she took me to the back of the house where there was a couch right next to the back door. Michelle said that we should sit there so that if her husband returns I should be able to escape from the back.

She was horny as hell and she was ready to get it on right away. I was a little nervous. She grabbed my hand and guided it into her pants for me to feel how wet she was. That turned me on like crazy. I started fingering her while she pulled her pants down. She started moaning until she came while her whole body was shaking. She then opened my pants, pulled it down and gave the most amazing blow job ever. She did such a great job and she swallowed every last drop. We then talked for a short while and ate some breakfast together until her baby woke up.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 continued hooking up 2-3 times a month like this, most of the time we gave each other oral, but every once in a while we had penetrative sex. When her husband was out of town for two weeks I was over at her house every night after work and we did it in the bedroom, shower and everywhere else in the house. We walked around naked in the house because we weren’t afraid that her husband might walk in.

At one point she suggested that I should get to know her neighbor, a younger woman who she was having lesbian sex with. She was hoping that we will be able to have a threesome. This never worked out, although I did get close to the other woman, but that story is for another time.

We were both ecstatic about this relationship. The thought about fucking my boss’ wife (even though he was a great boss) and for her the thought of fucking her husband’s young employee, was intoxicating for both of us.

After about a year we both felt that this relationship was way too risky for both of us and we decided to break up. We did talk on the phone and chat via social media a few times since, but nothing more.

I still get excited whenever I remember this story. It is not about her looks or her body, it is about the circumstances and the fiery sex. On top of that, the fact that this was my first extramarital affair.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Fertility awareness (days counting, temperature)

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

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? 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 once told one close friend about it. They were excited for me and maybe even a bit jealous.

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

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? It added zest and excitement to my life, at a time that I was going through some marital blues.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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? She was the only woman that I once had penetrative sex while she was having her period. It didn’t excite me but she practically begged for it.

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? I think that people should be able to have sex with whomever they want as long as it is done in a legal and consenting way. You don’t think twice before you go into a restaurant to buy a good meal even if your partner/wife is the best cook.

What do you think about the Casual Sex Project? Seems nice and interesting.

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