First Gay Experience with Wife’s Boss



What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? seattle
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

First Gay Experience with Wife’s Boss

How long ago did this hookup happen? last week

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

How would you best classify this hookup? Short fling

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? I have never met my wife’s boss before the party, she spoke highly of him in that he never hit on any of the women working there, and he was good to them. He is in his late 50s and I was introduced to him by my wife that night. I did not want to even go but she pressured me into it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He approached me and offered me a drink and we started talking, we were talking about fishing as my wife was hanging out talking to the other girls she worked with. Then he invited me to his office on the next floor to look at his trophies. I told my wife I’d be back in a few, she just laughed and said go have fun talking about sports.

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? It was really weird because at first I thought I was getting drunk faster when we got to his office or maybe I was getting a cold, because I felt weak and tired. After, I said I needed to sit down because I was dizzy, he approached me and I could see that his fly was open and his dick and balls where hanging out. He pushed me over his desk, I said stop but I was weak as he was pulling my pant’s down and he penetrated me from behind.

I remember feeling his balls against my thighs as he orgasmed, and as he started kissing sucking on my neck I felt this tingling sensation inside me as my dick started to swell. After his dick started to soften and I felt him slip out of my ass, I could not even stand up as I was weak in my knees and feeling weird. He was standing next to me as I looked right and his cock still was dripping cum as he zipped up his pants and he said Amber didn’t have to know about this, that it will ware of in a few minutes.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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’m still very confused, I always grew up liking women and feeling an attraction towards them, but now I feel weird, almost attracted and submissive when around him or towards other guys.

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

What were your motives for this hookup? Submission / Relinquishing power, I didn’t want it but was unable to stop it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Prescription sedatives (Valium, Xanax, Diazepam, Quaaludes, Phenobarbital)

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? Not at all

Did you consent to this hookup at the time? I gave a clear ‘no’

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? Nobody yet, I want to tell my wife what happened but it would change everything at her job and maybe with us.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Somewhat

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? I love my wife and did not even go into this looking for sex with a random girl, let alone another guy…

What was the BEST thing about this hookup? The feeling… As he came inside me it was so erotic with him sucking on my neck as he was still inside me.

What was the WORST thing about this hookup? That I was so drunk and let him forcibly bareback me over his desk.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes… I caught myself looking at a guy’s penis in the gym and getting excited and confused. Thinking of him fucking me in the bathroom, and feeling guilty because I was wanting it to happen.

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

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

Anything else you want to add about this hookup? I’m still confused about it all, I want to tell my wife but I’m afraid because he secretly he turns me on now thinking about it get me hard. I don’t know how to feel.

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