by The Duke
What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? London
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Office worker
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? A year ago
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Friends-with-benefits
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? I manage a department of about 40 people. “Katie” is a junior member of the team, she is in her early 20s. She is a freckled pale ginger girl, very athletic / slight frame and short – about 5ft. She is very quiet and shy in the office but completely different if you get a few drinks into her; she is completely crazy, just doing loads of shots and really bubbly/fun/outgoing.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I took my department out for drinks on a Friday night as my wife was away with the children in another country.
Afterwards I was getting the train home with Katie from my team who lives a couple of stops further along the same train line. When it came to my stop she just bluntly asked if she could come home with me.
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? As soon as we got inside my house and closed the front door, she unzipped my trousers and got her hands in my pants. She stood up on her tip toes (I am much taller than her – 6ft 3) and whispered in my ear “I want you to hurt me daddy” then stood back down and she was just staring at me whilst playing with my cock, biting her lip.
I was pretty shocked! Never had a girl say anything like this to me, but, well, I was drunk too so I just went with it. I definitely gave her what she asked for, and she kept on asking for more the whole time. There was a lot of slapping, some ridiculously hard spanking. Her body was amazing – so tight and firm, especially her butt. She is a short slight girl but looked even tinier with her clothes off.
She sucked my cock a bit and then I went straight for her arse, I probed her for a few seconds with a finger and when she didn’t object I just bent her over the back of a sofa. I found some e45 cream in her handbag and just rubbed a bit onto my cock then went for it. She was incredibly tight and it was really difficult to get inside her. When I did the noises she made were incredible.
We went upstairs and fell asleep afterwards but I woke up at about 4am with a raging erection and fucked her arse again with her lying prone on the bed. That was probably the best part of it all for me, she was just muttering total filth in my ear, calling me daddy and saying my cock was too big for her and it was ruining her poor little sore asshole, it got very rough. I kept taking my dick out and letting her ass close up then pushing it back in right to the hilt in one thrust; it felt incredible, impossibly tight. I also got right in her to the hilt which I have never managed when giving a girl anal before. She was squealing and whimpering whilst at the same time encouraging me to get even rougher. It was obvious it was hurting her but she kept asking me to hurt her. She definitely has issues but it felt so good and she wanted it so I just went with it.
She stayed the whole weekend, we fucked as much as we could. I spanked her a lot as she kept asking for it, and thrashing her got me hard again. I never even touched her pussy the whole time.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than one
Did your partner have an orgasm? I don’t know
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 didn’t talk for ages afterwards. She just acted normal when we were at work. A few weeks afterwards I just got a text from her in the middle of the day at work telling me to go to the disabled toilet. I went in there with her and she just got down on her knees and got my cock out and blew me. The same thing happened about a month after that and I ended up drilling her up the ass with just her spit as lube when I was supposed to be in a meeting about budgets. This keeps happening from time to time, it is weird and transactional, usually without any talking (except her dirty talk whilst we’re in the act). I’ve lost count of the number of times but I still have never touched her pussy.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Just happened, I don’t know why, just went along with it, It was easy / convenient
How intoxicated were you? Drunk/high but not wasted
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? 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
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? I don’t know / I’m not sure
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? The sex itself was amazing, I felt so powerful when fucking her.
What was the WORST thing about this hookup? A bit of guilt I suppose.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’d never really had no strings sex before, so yes it opened my eyes.
All things considered, how NEGATIVE was this experience? A little negative
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