My First Time Cheating with Husband’s Best Friend

by Sally

What’s your gender? Woman
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Indiana
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Medical Professional
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Catholic
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Swinger
How many sexual partners have you had in your life (including oral sex)? 85+
How many hookup stories have you here posted before? 0

My first time cheating with husbands best friend

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 1 to 3 years

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? J was a neighbor who got out of the military and my husband had hired to do jobs around the house. He was in his mid-twenties and despite the age difference had become best friends with my husband. We never hooked up or had any interaction of a sexual nature. I thought he was a hot guy and enjoyed seeing him work out in the yard in his shorts with no shirt on sweating in the sun but never had any thoughts of anything more with him. He was super polite when I would bring them cold beer while working and I knew him for about 2 years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was no planning, J was a nice guy who helped me out while my husband was out of town for work. It sort of happened mutually.

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? My husband and I had always stayed super busy between work and raising our children. His job required him to travel a lot outside the US and I typically stayed busy and never had a moments rest until our oldest went away to college. Our younger child was the typical social kid with more friends than you could count and always away from home so I had found myself home alone many nights.

I was headed out to work one morning after a large snow storm and at the bottom of our driveway I was having trouble getting any traction where the plow had piled up snow. Since nobody was home, I walked down the street to the home of one of my husband’s friends who was home. I knocked on the door and asked if he could help me push my car onto the road. He asked where my husband was and I told him he was out of town traveling for another week. After getting my car on to the road, he told me I should not tell anyone I am home by myself and said he would come over in the evening to make sure I didn’t need anything.

At home, that evening the snow continued and around 8:30 there was a knock a the backdoor. It was J and he said he wanted to make sure I was ok and asked if there was anything I needed. He didn’t come in and left saying he would check in on me again tomorrow. Over the next three nights J repeated this but would never accept my invitation to come inside but I felt good that he was checking on me. On that Saturday, he came over around 9 PM and once again knocked at the back door and being bored I invited him inside once again. Like usual he declined but stuck around for a few minutes and I asked him if he had time to help me dump some ashes from the fireplace since I had been burning wood every night. He said yes and came inside taking his boots off at the door.

I had a bottle of wine open and had drank several glasses that evening already and asked him if he wanted a glass. He declined and I asked if he wanted a shot of my husband’s bottle of Woodford Reserve to which he smiled and said yes. He drank the shot and then emptied about four buckets of ash for me and returned to come inside to warm up before going home. I gave him another shot of the Woodford and that shot turned into about five or six more. We were sitting on the couch joking around and talking when the movie I had on went off and one of the Showtime after dark shows came on.

As J and I sat on the couch we became mesmerized by the show and once it ended I turned on one of the more hardcore adult channels and we got up to get fresh drinks. I was feeling tipsy but not intoxicated and J said he felt good but should slow down on the shots and grabbed a beer from the refrigerator. We went back inside the family room and sat back on the couch this time next to each other with our attention drawn to the sex on the large screen TV. At this point there was a sexual tension in the air and I wanted to tell him it was time to go but at the same time I wanted my husband’s friend intimately. Almost at the same time J and I moved together and began to kiss passionately and I could feel butterflies in the stomach as excitement filled my body and I wanted more. Our kiss lasted several minutes and then J moved back and said “I should go before…” I interrupted saying “Yes, I shouldn’t be doing this. I’m married and your my husband’s best friend…” I was still searching for words stuttering as our bodies moved back into another passionate kiss and embrace.

At this point, I didn’t care as our kiss continued and I felt J pulling my flannel nightgown up exposing my upper thighs to him as his hands rubbed my legs and my hands ran over his chest and stomach as we kissed deeply. Finally, our kiss broke and we both were breathing heavy. I took J by the and said “Let’s go back here.” I led him to our bedroom. Once inside J pulled my gown off over my head leaving me in only my panties and slippers as I got his shirt off revealing his muscular chest and slight beer belly. I got his pants undone and pulled his dick out, he was larger than my husband and it was the first dick other than my husband I had ever touched. J sat back onto the mattress and I bent over taking him into my mouth and sucking him as I fondled his large balls. After a bit, J sat up and told me he wanted to lick my pussy. I got up onto the bed and raised my hips as J pulled my panties off my hips and I spread my legs giving him access to my pussy as he began to lightly lick me and I got his dick back into my mouth. I stopped and said “We should only do oral, nothing else” and J agreed as I took his dick back in my mouth and we pleasured each other orally.

At this point, all thoughts outside of what I was feeling had left my head and I cried out J’s name saying “J fuck me, I want you inside me.” J was feeling the same thing and moved from lying beside me to kneeling between my legs as he pushed my legs up and began to push the head of his big dick inside me until he was buried fully and began thrusting in and out of me and kissing me deeply. It did not take long for me to begin to orgasm causing my entire body to shake and J pushed inside me as deep as he could and began to cum. We fell off to sleep lying together and I woke up thinking about what had happened. J woke up a short time later and we kissed before he entered me once again this time fucking me slowly and deep for a long period before we both had another climax.

J left the next morning and came back each evening to check on me but never came back in the house.

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? I felt very guilty about allowing this to happen. My husband and I had always been completely faithful to each other but I also felt a sense of excitement about the whole experience. At the time I thought nothing like this can or will ever happen again. It was awkward seeing J and we both acted like nothing had occured. I was attracted to him and wanted to repeat the act but didn’t at the same time. Today, I feel very comfortable with J and we have hooked up many times over the years despite him living a far distance away now.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, I was feeling lonely, Boredom, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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 told my husband the day after he returned home. Initially, he was angry and felt betrayed. After a few days we talked more about it and he and J talked without my being a part of the conversation. We had talked about swinging before but not seriously. We ended up seeing a marriage therapist for about six weeks. We had J over one evening about three months later and ended up engaged in a MFM threesome that night. Since we have been swingers and hook up with others with some frequency.

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

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? Very

Do you regret this hookup? A little bit

Why do you regret this hookup? I wish my husband had been a part of the hookup and could have given consent. I never wanted to cheat on him and would never cheat on him again. There is a huge difference between consensual cheating and swinging. If we could have talked this over and agreed on it before it happened I don’t think he would have been hurt like he was.

What was the BEST thing about this hookup? It opened our relationship to a lifestyle and level of openness we never knew existed. While we loved each other I think like many marriages the sex had become mundane and routine over the years. By consensually being involved in the swinger lifestyle it has brought us to a whole new level of desire and intimacy and strengthened our relationship.

What was the WORST thing about this hookup? Betrayal of my soulmate’s trust.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am in a place that for the first twenty years of our marriage I would never have thought possible. Our communications is beyond anything I ever imagined. We both love to see the other brought to an orgasm by another person, to see the desire build. Sex between us has been hot and better than ever.

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

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

Anything else you want to add about this hookup? I would never recommend anybody in a committed relationship to cheat. I wish we had talked and had the level of communication we have now before this happened. I hate that it did happen but I am glad we had the experience and that we remained together and we are now friends with benefits of J who is a great guy.

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 was raised a strict Catholic and taught sex was dirty and not to be enjoyed. I remain Catholic but now see sex as both an expression of love but also something physical that is to be enjoyed. Casual sex is great and very enjoyable.

If more people had a healthy view or point of reference about sex I think many relationships would be enhanced and more people would be content together.

What do you think about the Casual Sex Project? I just found it and so far like it overall.

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