“I’d Rather Watch You And My Girlfriend Play”



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? Middle Eastern
What continent do you live on? North America
What country and/or city do you live in? Washington
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Muslim
How religious are you? Somewhat
What’s your sexual orientation? 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

“I’d Rather Watch You And My Girlfriend Play”

How long ago did this hookup happen? One month

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

How would you best classify this hookup? Cuckold

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? Annika is a former dancer who is tall, blonde and fit. I’ve worked with her for over a year and we’ve become good friends. I’ve had a crush on her the whole time and we flirt all the time. She is in her late 20s

Her boyfriend is a 30 year old average sized guy with a good sense of humor, but otherwise unremarkable.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Annika has long told me her boyfriend wanted to hang out with me because of our shared interests, including video games. So one night when my family was out of town they invited me over to their place to play some retro games.

We were having a good time and she and I were playing Mario Kart against each other when I offered him the chance to play. He demurred, saying “I’d rather watch you and my girlfriend play.” I laughed and said “that sounds like double entendre”.

To my surprise she got serious and said, “Why do you think we called you over?” Not sure what to say, I was honest and told them I was game. Next thing I knew, she was on top of me, kissing my lips as he slunk into the background.

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? We began making out on their sofa, then I picked her up and took her to their bedroom where I undressed her and began eating her pussy. Using my tongue and my fingers I brought her to orgasm after about ten minutes. I love going down on women, so I became rock hard in the process.

As she began to come down, she pulled off my pants and told me to fuck her. I got up off my knees and standing on the edge of the bed, thrust myself into her as she moaned. I played with her feet as I thrust which she enjoyed. After a few minutes, I turned her over and fucked her doggy style, spreading her ass cheeks with my hands.

She began to moan again and I eventually came inside her with my legs quickly beginning to feel like Jell-O. Afterwards I laid on the bed next to her collecting my strength as we made some inside jokes. I eventually asked her where her boyfriend went, she told me he was watching from the hallway. I had forgotten about him in the moment.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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 got my things and didn’t stick around too much. The next day at work I just winked at her. Later she told me through chat about how much fun she had. I told her I’d like to do it again with her but this time without an audience. She teased me by saying we’d have to wait until we go on a work trip for it to happen that way.

I felt very proud the rest of the week. Part of me wanted to brag to our co-workers but I realized it wasn’t a good idea. Sleeping with my co-worker was dangerous as it was, bringing attention would make it more precarious.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Power / Dominance, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? Nobody

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I had sex with my crush, but I feel weird about her boyfriend’s involvement.

What was the BEST thing about this hookup? A woman I’ve long been attracted to let me cum inside her

What was the WORST thing about this hookup? I don’t know why her bf wanted to watch or if we can hook up again without him around. I haven’t seen him since and that will be weird

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It gave me a confidence boost. My wife always told me I was very attractive, but I never believed her as I’ve gained weight in recent years. Learning that Annika agrees with my wife makes me feel really good

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

All things considered, how NEGATIVE was this experience? A little negative

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? Casual sex should be more accepted. Sex is a biological function, but there are too many traditional tabboos around it.

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