Cheating With My Manager



What’s your gender? Man
How old are you? 20s
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual

Cheating With My Manager

How long ago did this hookup happen? Last month

What was your relationship status at the time? In a relationship (open)

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

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

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? She was small and cute, slightly tomboyish. Irrepressibly fun and responsible at work. I only saw her as my manager for a project.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She called me up to see if I wanted to work a gig. She was managing an event and invited me to be one of the VIPs. I wanted to know more about the whole event before agreeing, so we met up for tea and she gave me the brief. We got along pretty well, and we had dinner a few days later when we both happened to be in the same town.

About two weeks after we met, she came back for another meeting. I recommended a hotel to her for her stay in that would be near her work. It also happened to be near me so we got dinner again and decided to watch a movie. The movie was part of a series, I just happened to have the previous one on my cloud which she really wanted to watch, so we went to her room to continue. We had two drinks during dinner but the effect seemed to be wearing off, so we got a bottle of hard liquor for the room.

We watched the movie while we were drinking but it became obvious she was tipsy and not watching the movie. She leaned over and something stirred in me. I put my arms around her and slowly led her to the bed.

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? I kissed her and rubbed her tits with my right hand while undressing her with my left. I then fingered her for a little but was surprised to find that she was already dripping wet.

My cock was already hard so I moved in to penetrate her. We fucked missionary style for a bit and she was so petite that I had trouble kissing her on the mouth. She was moaning louder and louder and I realized that I never thought to get a condom because it happened so fast. I had to take a break to search the room before we finished just in case. When we started up again, I realize that I couldn’t last much longer and came in the condom. We both slept after that.

I woke up earlier than her, after about 5 hours of sleep. I gently caressed her body until she responded and fingered her until she was wet again. This time I flipped her over and fucked her doggy style. It felt tighter than ever and her moans were really gratifying. I asked her if I could cum inside of her but she said no so I pumped her till I couldn’t hold it anymore, and came over her ass. I collapsed onto the bed panting. She wanted to get a towel to clean herself but I held her in an embrace and asked if she could finish me off with a blowjob. She said no at first but eventually agreed. She was very inexperienced at it and I did not cum again but she followed my instructions well.

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 think she was slightly embarrassed about how unprofessional what we did was but she said that she didn’t regret it. We actually get along well so we decided we would continue to be friends, maybe with benefits.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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 enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

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? Not at all

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

Do you regret this hookup? Not at all

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