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What’s your gender? Man
How old are you? 31
What country and/or city do you live in? Scotland
Highest education received: College degree (eg., BA, BS)
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny
How many hookup stories have you here posted before? 4

A Quickie Upstairs

How long ago did this hookup happen? 2011

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 a week

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? About 5 foot 2 inches, blonde, and petite. Previously in November I spoke about my first date with her (see “blind date turns risqué”). She had ended up sucking my cock after I fingered her around the side of a building. We arranged a second date a few days later.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to meet for lunch and had a nice meal, and the conversation flowed. Unlike previously we were not drinking alcohol as she had work later and I was driving. We headed back to my house to hang out. On the way in we passed my mum and stepdad who were out working in the garden. After introducing the girl we went in the house, where we put on the TV and chilled. We soon started kissing. She was a good kisser, and we both were clearly excited so I asked if she wanted to go upstairs and she immediately said yes. As we walked upstairs I felt an anticipation. The oral sex previously was amazing and I wondered what was going to happen. With my parents coming in and out of the house all the time it wasn’t an ideal situation…

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? I shut the bedroom door and we started kissing. We then stopped and without speaking we each started taking our clothes off. After taking my boxers off I stood naked and erect. I was conscious it was the first time she had seen me naked and the first time she had seen my cock as previously it had been dark. If anything, it turned me on more. She had already taken off her outer clothes and I started to help her out of her bra. Her breasts were amazingly pert and cute, and a nice handful. So she stood there in her panties and socks. She clearly hadn’t planned for sex as she was wearing ordinary cotton panties and geeky socks, but she made me so hard and a bit over excited as I pulled off her socks on the bed, before laying her on her back where I pulled her panties off. Within a few seconds of getting in the room without saying a word, we were both naked and clearly it was going to happen. I kept hearing my mum wandering about the house and there was definitely a worry she would walk in on us.

The fear of getting caught just added to the exciting danger. I took a moment to admire her blonde pussy, she had a neat landing strip just crying out to be fucked and her tits were lovely. After nearly forgetting, she reminded me to wear a condom. I slipped it on and we started kissing with me on top in missionary position. She was already very wet and I was able to slide into her pussy very easily. I licked and groped her breasts as I started thrusting. Knowing we had little time I pumped her hard. I was struggling to hold on so I changed position. I spread her legs wide and put them over my shoulder and sat up so I could take full command. I started kissing down her legs as I shagged her. By the time I got down to her small feet I knew I would last long. I wanted to last longer but the excitement and enjoyment on this occasion was getting the better of me. So I pumped furiously while staring at her tits bouncing up and down, holding her legs high and as she quietly moaned on my dick, and then I came hard inside her. We then got dressed and I took her to work.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? I regretted not lasting longer this time but she obviously wasn’t put off as she came for a third date (agreed not to have sex of any kind – which I regret). However, I decided not to take it further after this as we didn’t have much connection or things in common.

What was the BEST thing about this hookup? The best thing was getting to sleep with her after such a good night a few nights before. I had wanted to have sex that night but it wasn’t possible.

What was the WORST thing about this hookup? Not lasting as long as a had wanted, and not having privacy.

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? If you’re not hurting anyone, casual sex can be liberating and fun.

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