by Sammy

Gender: Male
Age: 22
Race/ethnicity: Mixed (Indian/White)
Current location: London, UK
Highest education received: Post-graduate degree (currently pursuing)
Relationship status: Dating
Religious affiliation: Hindu
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Sexually fluid
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Unexpected Interest

How long ago did this hookup happen? 1 month ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling
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? She is 32, tall, naturally red hair with green eyes. She’s very slender with surprisingly large tits.

I’ve known Beth since I was 10, she was the girlfriend and now wife of my best friend’s older brother. She’s always been around growing up. This is the first time we hooked up. I always thought of her as the incredibly hot, older girl that was out of my league. She was my first crush.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was visiting home last month because my mum wasn’t feeling too well and I came up from London to see her for the weekend. On Saturday afternoon, I went over to my friend, Adam’s, house to catch up with him and see how he’s getting on. When I got there, I found his older brother John in his flat. John let me in and told me he had to step out for work, but that Adam would be back in an hour or two and I could wait for him. Apparently, John and his wife, Beth, were staying with Adam for a few days because their house was getting some renovation work done.

I went and laid down in Adam’s room and was chilling on my phone when I heard Beth come in through the front door. I got up to go see her. She was surprised to see me and told me to come sit with her on the couch.

I hadn’t seen Beth in a while, maybe a few years, so it was nice to hang out. About 10 minutes in, Beth started complaining about John, about how she’s having all this trouble in her marriage and is thinking about getting a divorce. I listened patiently, not really sure what to say. I didn’t realise it at the time, but she was leaning into me. She then innocently put her hand on my thigh and just held it there as she kept talking.

I made a very obvious look down and saw her hand on my thigh and gave her a look. She just smiled and didn’t move her hand. I decided, fuck it, just go with it. So I put my hand on top of hers and slowly dragged it up my thigh until she was cupping my cock. That’s how it started.

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? The minute I pulled her hand up to my cock, she started squeezing it and I was already getting hard. I kissed her. Hard. And she kissed me back. We snogged on the couch for a few minutes and I pulled her tee shirt off and then pushed her bra down. I sucked on her tits for a good few minutes and she was moaning. As I was sucking, I pushed my hand down and into her trousers and started rubbing her.

She told me she wanted it, so I got up and pulled off my shirt and trousers and she got naked as well. We laid down on the couch and just touched each other and kept kissing. At some point, I placed my cock and slipped into her. That’s when we started fucking. She wasn’t as tight as I would’ve liked, but it was still fun. We must have fucked for 20 minutes, when she came. I told her I wanted to come as well, she said fine. I told her I wanted to come inside her and she was hesitant, but before she could tell me to pull out, I came inside her. She didn’t seem to mind though.

Afterwards we laid on the couch naked for 10 minutes and she started playing with my cock. It took a little work, but I was starting to get hard again. She then got on her knees and blew me. It was really good. I warned her I was about to come and she popped me out of her mouth and I came on her tits.

We would have gone on but Adam called and said he would be there in another 5 minutes, so we quickly got dressed and kept chatting as normal.

Did you have an orgasm? Did your partner(s)? Yes, twice. She had one.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No, we didn’t discuss anything. We didn’t use condoms either and I came inside her.

What were your REASONS for having this hookup? She was miserable and needed a fling. I was bored and horny.

Were alcohol or drugs involved? If so, how much? No.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt really bad after the hookup. John had always been a sort of older brother to me and I felt like I betrayed him in the worst way. I couldn’t hang out with him after that.

Beth called me later that night and told me that we should never tell anybody what happened. I agreed. She came over to my parent’s house on Sunday to talk and we ended up hooking up again. Since then, she came to London for a work-related thing last week and we had sex during her lunch break. She claims that it was the last time and I respect that, but I have a feeling that it wasn’t.

To whom did you talk about the hookup? How did they react? A few friends of mine from uni, but in very general terms, and I didn’t tell them who the older girl was.

Was this a consensual and/or wanted experience for you? For your partner? Completely consensual and wanted by both of us.

Do you regret this hookup? If so, why? I do, quite a bit, the guilt is pretty bad. But I could never say no to Beth, not after I pined after her for so long.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about the hookups is definitely when she blows me. Best. Blowjobs. Ever.

The worst is the guilt that permeates the post-coital bliss.

I guess this hookup has shown me that I’m not as nice nor as loyal a person as I liked to think I was.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

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