by Miss Mary Jane

What’s your gender? Woman
How old are you? 30
What’s your race/ethnicity? Whitewashed Asian
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? Teacher
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Spiritually undefined
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 30ish
How many hookup stories have you here posted before? 0

The Sheriff

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

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? He was about 6’+, muscular, big chest and well-groomed. He had short light brown hair, green eyes, a British accent and a cheeky attitude. I met him in a line-up at a ski lift. Him and his friends were having a weekend-long ski vacation in the small resort town I lived in. I could smell his expensive city-boy cologne through all the layers of brand new snow gear he was clearly wearing for the first time. It’s not that that matters, but this guy was reeking of money that he wanted to show off and was the big-spender party-time type.

That is entirely not “my type” at all, but he had said something funny to the lifty and started bugging me when he heard me laughing.

Being the cocky-mofo that he was, he challenged me to a race while we rode the lift up together. He was such a cocky prick, i couldn’t just blow him off. I accepted his challenge and found out he was from Nottingham. He said I could call him Sheriff… As in the ‘Sheriff of Nottingham’. *rolling eyes*

He asked for my name, but started calling me, ‘Poppin’, which i really didn’t care about either way. These ended up being the only names we knew of for each other for the rest of the weekend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? To make a long story shorter, he not only loses the race, but he totally takes out a skier (like a fucking train) and the two of them roll into a heap down the mountain. Blah blah blah, he convinces me I owe him a drink somehow for endangering his life and we end up meeting up for drinks.

We drink, we dance, we snort a line or two in the bathroom of the club. We start making-out a bit and he invites me to check out the hot-tub in his hotel room.

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 get to his room, but he’s drunkenly lost the key or whatever so we end up back at my place. I lived in staff housing at the time, but my roomate was away for that month. I toss the shit off of my bed onto hers and he immediately pulls my pantyhose and thong down and off my legs. My skirt and top are still on and his fingers find their way onto the lips of my cunt. His other hand is grabbing my ass as his tongue is sliding in and out of my mouth. I remember him being so strong. He would just tuck his forearm under my bum and lift me up to move me without missing a stroke on my clit. My top and bra came off somehow and my nipples were in hard in his mouth. He was wearing these really smooth thin material pants so I can feel ridges on the tip of his dick underneath. This is a huge turn on for me and I could feel EXACTLY how big and hard the dick waiting for me was.

Suddenly, he throws me down onto the shitty springy mattress and I hear the clink of his belt coming undone. He pulls out his dick and jerks it a bit while watching me with this smart-ass little smirk. I must mention that the lights were on the whole time. I think he asked me to suck on it, but I had politely denied because I was still in my “I don’t give head” phase.

That’s when he went to town. His face was burried so deep in my cunt I could feel the stubble on his beard scratching around the hole of my pussy. I was such a selfish bitch back then, but I always LOVED getting good oral from older men. I think the golden age is 30+.

Not only that, he had these short but strong thick fingers. He pushed two inside of me and watched me squirm around on the bed while he took a break from making cum.

After a little while more of the finger-fucking oral combo, he pulled his fingers out of me, spun me around and picked me up by my hips/waist into doggy position. I could feel my wetness all over his hands on my side.

Before I could react, his dick was already sliding inside of me. He thrusts were hard and steady as he pulled my hips into him.
By this point my throat was already so dry from moaning and I think I was beyond bliss to know if I was coming or crying or dying but when he came I could feel his whole body tensing up and exploding inside of me.

A few moments of bliss before I realised that he actually had come inside of me (“wtf? Did you just come in me??” To which he replied, “what? Poppin, are you not on the pill? Oh, well…sorry about that then Flower.”)


How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? The next day we party again and fuck some more (with condoms the rest of the time).

THEN, I somehow find out through his friends that he is actually married and has a kid back home. Brutal. I had never home-wrecked a marriage before (gf’s and bf’s sure, but nothing with a ring). I never confronted him though because he was already leaving. Never exchanged names or information and never saw him again.

Karma’s a bitch though cause he forgot a bunch of his new ski gear at my place and I ended up scoring big on his loss.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, Intoxication, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish, Cocaine, MDMA, ecstasy, molly

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

What substances did your partner(s) consume? Alcohol, Cocaine, MDMA, ecstasy, molly

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? Maybe a few work acquaintances at the time, but no one since then.

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? Mostly just because of the wife situation, but who knows what was going on in their relationship at the time.

What was the BEST thing about this hookup? Having a vacation hook-up, when you’re not on vacation! No strings and no one in your small town knows your business.

What was the WORST thing about this hookup? Potentially home wrecking

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This hook-up was really fun. I think I got to fulfill more than one fantasy there

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

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

Anything else you want to add about this hookup? I could still smell his cologne on my pussy the next morning.

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 think casual sex has its time and place.

What do you think about the Casual Sex Project? I think it’s great! I love reading about other people’s dirty little secrets and it makes me feel less fucked up about my sexual history.

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

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