by

What’s your gender? Man
How old are you? 41
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? Luxury Travel
What’s your current relationship status? Single
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? 1

Flipping The Switch

How long ago did this hookup happen? 2 days 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 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? Alice is about 5’1″ with shoulder length natural blonde hair, an athletic slim body, green eyes, a perfect round ass, and small but very perky boobs. She’s 15 years younger than me at 26 and we met through the local BDSM scene. I’ve met her a dozen or so times and we’ve always talked and been quite friendly but nothing more than casual friends. A couple of weeks ago I saw her at an event and told her about my last hook up where I experienced anal play for the first time and she was very interest and mentioned how hot it sounded. I knew she was a switch but tended to be more dominant than submissive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On Sunday I was out at a pub with a couple of male friends just having a few drinks when I saw Alice at the same pub purely by chance. She smiled and I smiled back but carried on with my friends. An hour or so later she came walking over and sat down next to me and asked me to introduce her to my friends – which of course I did. She sat with us for a while, I bought another round of drinks and we were all chatting when I felt Alice’s hand on my thigh, I glanced at her and she smiled back as she moved her hand further up.

She then she quietly asked if I wanted to leave and go back to her place with her. I quickly finished my drink, made excuses and left. We had to take the tube to get to her flat and the whole time she was leaning in, caressing my thing, cock and balls and whispering how she was going to own me, plug me and make me hers. Before we even got off the train there was a visible damp spot on my jeans.

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 to her place she led me to her room and we began kissing, but as I reached for her butt to squeeze it she pushed me a way and told me not yet. She told me to strip while she got changed and headed to the bathroom. A moment later I was totally naked with a massive hard on waiting alone in her room. Then she walked in and my jaw nearly hit the floor, She was naked except for black stockings and suspenders. She was holding two pairs of handcuffs with long chains. She smiled again and asked if I liked what I saw. Then ordered me to lie face down on the bed.

As soon as I was lying down she walked by and grabbed my left hand and cuffed me to the bed, followed by my right hand. I couldn’t take my eyes off her as she walked to the cabinet and grabbed a bottle of oil and pulled out a butt plug. She climbed onto the bed and straddled my ass, pouring oil all over my back and began to massage me, lying down she rubbed her whole body over mine driving me crazy. Then I felt her sit up and begin rubbing her clit on my coccyx and massaging me harder and harder. As her breathing changed and she started to cum she dug her nails deep into my shoulders and dragged them down my back tearing my skin.

As her orgasm subsided she slid further down and parted my legs and squeezed oil in my ass crack. As she rubbed my cheeks she slowly started rubbing oil into my asshole, then a finger – which felt amazing! Then a second finger was roughly shoved in, causing me to scream a little – immediately she slapped my ass really hard and told me not to make a sound unless she said I could – all the time working her two fingers deeper and deeper into me. After a few moments she pulled her fingers out and I felt the tip of the butt plug being pushed in and stretching my anus. Slowly she pushed it in, twisting it all the way. I loved the feeling but it was beginning to hurt and I didn’t dare make a sound. I was gripping the sheets harder and harder until she pushed it passed the widest bit and it slipped right in feeling unbelievably good.

She climbed off me and walked to the head of the bed, sitting down right in front of my face, her perfectly smooth pussy just inches from me – but totally out of reach. “You like it don’t you?,” she asked, “You want to taste it, don’t you?” I told her I did and she slapped me hard across the cheek and said that she hadn’t said I could speak. So I just nodded. I laid there helpless as she began touching herself, running her fingers under my nose and rubbing her clit. Faster and faster she went until it was a blur and she was almost screaming. I could see and smell how wet she was but couldn’t reach it. Then her breathing really changed and she said over and over again that she was going to cum. Suddenly she squirted right into my face, once, twice, three times and a fourth right over my nose and into my mouth.

Once she recovered she climbed off the bed, deliberately offering me a wonderful view of her dripping pussy and beautiful ass as she grabbed something from under the bed but I couldn’t see what. She returned to my ass and gave me a cheeky slap and I could hear her doing something but couldn’t see what. She pushed my legs wider apart than ever, reached under my body and grabbed hold of my throbbing dick and pulled it to the side so she could see it as she stroked it and my shaved balls. Ever so slowly she began pushing and pulling at the butt plug lodged in my ass asking if I liked it – of course, I nodded that I did. Then she began pulling it out and my anus stretched incredibly again but not painfully this time and as soon as the wide part was out the whole thing pretty much popped out. I heard the slosh of oil before I felt it landing on my open asshole as she kneaded my butt. She leant forward and told me that she was going to enjoy this as much as me as I felt her thighs alongside mine and something firm nudging my ass. Inch by inch I felt her sliding a strap on into my anus, although I was already stretched this was something totally new to me and I did a sharp intake of breath which was met with another drag of the nails down my back and her saying “Take it like a man”. Soon I was literally biting the sheets as the pain built but she was careful and as I felt the fake balls of the dildo resting on my balls I knew she was fully inside me. She just lay there and told me how well I was doing as my ass relaxed and accepted the full length of the dildo. After a few moments, she began to withdraw and slowly fuck me in the ass. She gently built up speed until she was fucking me hard, she was clearly very turned on as the strap on rubbed her clit because I could hear her getting ready to cum again. With a last few thrusts, I felt a gush of her cum shooting over my balls and cock before she flopped down on top of me – with her fake cock still deep inside my ass.

She pulled out and stood up on the bed ordering me to roll over. As my hands were still cuffed to the bed, when I rolled over my hands were pulled across each other above my head. I lay there seeing her with her strap on and it’s black leather harness for the very first time and it was one of the hottest sights I have ever seen. She undid the buckles and dropped it to the floor and began to lower herself down onto my now painfully engorged cock and began to fuck me slowly and deeply, grinding hard on my pelvis. After 5 mins or so I was about to cum and shouted “I’m going to cum” and was slapped once again. “Did I say you could speak?”, she said and stopped fucking me, just sitting with my dick deep inside her.

As my orgasm began to fade and my body relaxed a little she slid up, taking my cock out of her and rubbed it on her asshole. With the combination of her cum, the oil and the pre-cum leaking from me I was soon sliding into her anus. She leant back showing me her bright pussy as she began riding up and down with my cock in her ass. Just a few seconds into this, I was about to blow my load and tensed up again trying to hold it back. She clearly saw this and stopped mid stroke with my cock half in and half out of her asshole and pinched both my nipples with her nails and twisted them – causing agonising pain. “Don’t you dare cum in my ass until I say so,” she said and slowly sat down again.

As my orgasm subsided once again and my balls felt like bursting she started to fuck me again while rubbing her clit. Thankfully it didn’t take her long and she was soon getting ready to cum once again. “Fuck yes, yes, yes”, she said as she picked up the pace once again and I watched as her pussy contracted and creamed once again. Mid way through the second wave she screamed: “Cum in my ass now!” I didn’t need a second invitation and emptied a massive load into her anus.

As my cock softened and started to slip out of her ass she moved forward and kissed me then sat on my face and told me to eat her pussy. Finally, I got to taste her delicious pussy mixed with her cum and loved every second of it. I felt her weight shift and thought that she was going to climb off, but instead, she shifted forward and I could see why – my cum was seeping out of her. “Eat my ass, I want you to taste your cum”. She sat her ass on my mouth and ground it into my tongue as my hot cum poured out of her and into my mouth.

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? Once she felt cleaner, she climbed off my face, uncuffed me and lay down next to me cuddling tightly. We both fell asleep naked on the sheets wet with her cum.

The next morning I woke up with her mouth on my dick as she gave me a morning blowjob before she showered and headed to work.

We exchanged numbers and intend to make this a friends with benefits situation.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? Nobody yet.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Everything, it was an incredible experience and now I have a fuck buddy to experiment with.

What was the WORST thing about this hookup? My asshole was a little sore the next day and I still have deep gouges down the length of my back

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? A great idea

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