Boss with Benefits



What’s your gender? Woman
How old are you? 31
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Hotel Supervisor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

Boss with benefits

How long ago did this hookup happen? Latest was two weeks 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 less than a year

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? He’s quite sexy and attractive. Met him last year (my manager) and we clicked as soon as we started talking. We both like sports, music and drinking. He’s been my crush since we met.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Summer 2016, we hung out with a couple of friends. I drunk texted everyone about how they were amazing friends. He replied and since then we started texting… and then sexting. We made out once or twice at a storage room, before we planned a date. And then ultimately, we ended hooking up regularly.

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? A lot of vaginal and oral sex. I have a pretty tight ass and he loves spanking it. We have rough sex sometimes depending on how horny we are. Amidst the rough sex, he’s always very gentle and loves to cuddle after sex. I’m 5ft and he’s 6’1″ so it feels really good because he can just keep me curled up in his arms and legs.

Sex was REALLY good that we’d have a 3-5hour marathon sometimes, and we’d come multiple times. He usually comes inside me and we usually come at the same time. We enjoy it so much, we’d do a storage quickie at work the next day.

He’s a good lover. We would sometimes talk about it discreetly and make inside jokes about it at work, people not knowing it was about our sexual escapades. That said, we get horny and run to the closest bathroom stall or storage place.

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? The day after is always a storage room quickie. We couldn’t get our hands off each other.

We’ve always liked each other. Been very good friends too. But the fact that I’m married, made us decide to keep it casual for the meantime. I’m open for a relationship eventually, but not now.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel more desirable, I was feeling lonely, Power / Dominance, Submission / Relinquishing power

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? His best friend and mine. They knew about it since we started texting.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? We know each other too well and he’s in close proximity. We also trust each other.

What was the WORST thing about this hookup? I’m still married.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Depends on how you look at it.

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

All things considered, how NEGATIVE was this experience? Somewhat 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? Been married for 8yrs. Sometimes marriages fall apart, and you need a friend to keep you warm. The fact that I have never had sex in a year since my FWB came along, that goes to show how fucked my marriage is. If you have a friend you can trust with something like this, and you set boundaries, casual sex with them would be wonderful.

What do you think about the Casual Sex Project? It’s great that people get to share their stories. Some people don’t feel alone as much anymore.

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