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What’s your gender? Man
How old are you? 57
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Melbourne
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sales Engineer
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 90
How many hookup stories have you here posted before? 0

MY MILF BOSS STALKS ME FOR SEX

How long ago did this hookup happen? When I was 18

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? For less than 6 months

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 was 18 and starting my first job and Sue was my boss and had to train me and we work together. Sue was very friendly – 47 years old , blonde, good figure but a somewhat hard face from heavy smoking and hard living. She wore heavy make up and her nickname was ” trowel face ” amongst the other girls working there.
I was single and had no girl friend and had full on sex only with a couple of girls my age previously.
Sue was the same age as my mother but had a reputation as a cougar woman. She would wink and say how handsome I was and how she liked younger men. She would touch me and brush past me an look at my groin area all the time.
Although I was flattered I was terrified she would tell the 50 + men and women that worked there that she was having sex with me and I would never live down the jokes from the other workers especially the men. She came in one Monday morning and told me how good the sex was with one of her son’s school friends on the weekend – he and her son were 18.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I lived near Sue and at the Christmas break up party, everyone had plenty to drink. Sue asked me to come over during the holidays for lunch to help her move some furniture. Her son and daughter both lived with her ex husband and she rarely saw any of them. We had all had plenty to drink and Sue pushed a scrap of paper over with her phone number and address, jokingly I accepted it.
Sue watched me and when I went to the toilet, without me knowing she followed me in, after making sure
no one was around . She locked the door after us and said ” I’m not one of those people who think you need to love someone to have sex with them, you know “.

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 kissed passionately with our tongues in each others mouths and then I undid her blouse, released her bra and ran my hands all over her breasts and nipples. She grabbed my belt and had my pants and underwear off in a few seconds. Quickly I sat on top of the toilet and she gave me a deep throat blowjob, I played with her hardening boobs and I came quickly with her hard thrusting on my dick with her heavy lipstick all over my throbbing shaft. After I came we swapped places and I tore her panties off and threw them down. She grabbed my head and shoved it hard into her pussy flaps and swollen clit. I licked and thrust my tongue ferociously into her fanny and kept putting fingers in – she was sopping wet and moaning
After four or five minutes she screamed and writhed with multiple orgasms.

How sexually satisfying was this hookup? Very

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? We were both putting our clothes back on when the toilet door knob rattled and a drunk voice asked ” who’s in there i’m desperate ” . I told them to use the ladies’ toilet.
We crept out quietly and re-joined the party separately. I followed Sue home and we had hot sex in her kitchen, bathroom and bedroom. Over the two weeks of holidays we had sex multiple times pretty well every day including the local drive -in theatre

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, Everyone else was/is doing it, 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? A little tipsy/high

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? no one

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? colossal amount of sex that I had never experienced in such a short time over the two weeks. She had no qualms about sex – anal, vaginal, oral

What was the WORST thing about this hookup? I ended up feeling sorry for my partner as she wanted to keep having sex with me and she was old enough to be my mother and looked it age wise. I needed to socialise with people my own age and did not want to go out in public together – she needed someone around her age and so did I. My parents would have had a fit if they saw me with her

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex is great with anyone but probably with someone close to your age is best

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

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

Anything else you want to add about this hookup? Sue ended up getting sacked through taking time off and not working hard enough. I also think she was fiddling with company money to a small degree. She told everyone she was marrying an elderly local doctor. I do not know if this was true or not.

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? Have been in relationships generally , but I still have fond memories of sowing some wild oats

What do you think about the Casual Sex Project? I love it and what a great tool for literature and fun combined !

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