Current location: Scotland
Highest education received: College degree (eg., BA, BS)
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 19
How many hookup stories have you here posted before? 0
Making Up for Lost Time
How long ago did this hookup happen? 3 weeks
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…)? On-off 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? I met Ron when working away last summer – one night we ended up comfy in his room and one thing led to another. I spent the rest of the business trip hanging around him and we had sex a few times, but at the end he told me we shouldn’t see each other again and then ignored all my messages for months.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I sent him a couple of messages earlier this year that he responded to in a chatty way and so we just caught up at first – but then I sent a few more risqué ones including one of a vibrator. He asked me had I used it yet so I sent a quick video and the messages started getting dirtier. I suggested we book a hotel and he agreed.
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 had to wait in the hotel about an hour as he was driving from England, I had a drink and was getting a bit frustrated when he arrived. He suggested we get drinks and take them up to the room. He turned up very casual and quite scruffy and I felt a little nervous as it was about 10 months since we’d seen each other.
We went to the room where he said he needed a shower after the long drive and went in. I sat on the bed thinking he’d come out but he opened the door and asked when I was joining him – of course, but for some reason it hadn’t crossed my mind! I quickly stripped and jumped in with him – we kissed under the hot shower and he took each of my breasts and kissed them too before fingering me and I worked his cock. I’d forgotten just what it was like, it was meaty and tapered at the end and felt good. Immediately he got out a condom and I jumped up so he could fuck me against the side of the cubicle. He slipped in easily and banged me hard and I think we broke it as water leaked out all night! I turned so he could take me from behind and the water squelched as he slapped against my arse. We decided the bed would be more comfortable so we moved there, every movement felt amazing and he came fairly quickly and hard.
He said he’d been saving that for a week and I told him I loved making him come. But what about me? He laid me back and set to work with his hands – he’d been pretty expert in our previous encounters but this was amazing and he made me squirt twice.
We chatted for a while and had a quick browse of the porn available, before quite soon he was ready again and told me to get on top. Riding him was perfect, he just seemed to fit inside me just right so I could grind into him at whatever angle I wanted. He roughly tweaked my nipples which I knew he liked to do, then I turned so he could watch my ass bounce on top of him. He pushed me round and fucked me intensely from behind, so much so that I don’t know if we stopped from exhaustion or because he did come. All through sex every move felt heightened and I was moaning and groaning like the porn on the TV.
He popped downstairs for more drinks and a smoke and I had a quick shower. I also laid out all the sex toys I’d brought after the video. When he came back we chatted again and looked at some photos on his phone, but when I pointed out the toys he got quite excited and asked me to jump up and poke my butt at him. I did, and he started putting loads of lube around my arsehole. I was a little apprehensive as I never let my husband go there as it’s not something I find comfortable. But I was so turned on by Ron and the whole situation I decided to try.
Very soon he had worked one of the toys into my ass and handed me another for my clit. It was an amazing feeling as he then thrust into me, my senses were going haywire and I couldn’t really work out what he was doing! I asked him if he had a free hand (as I genuinely had no idea!) and when he said he did I asked him to take a photo so I could see exactly what was going on back there! He did and carried on fucking me, he came quite quickly which I guess is understandable, and I was just left in an absolute mess, my head spinning, my arse slippery and totally dazed in a great way. He jumped up to wash off the toys and the photo blew what was left of my mind – the toy poking out of my butt cheeks, his cock in my pussy and then the second vibrator on my clit which he said had also been tickling his balls and driving him wild. He had assumed this was normal for me – I set him straight and I hope that made him feel special too as I’ve never let anyone play with my ass like that before.
I kept getting waves of glorious dizziness, like my brain was trying to process what had just happened but refused and shut down instead, so he went off for another smoke and I just lay engulfed in this wave after wave.
I calmed down a bit when he returned so he just watched TV and I wrapped myself around him. I must have dozed for a bit but I woke up and he was still watching TV so I started playing with his cock again. He was surprised but was soon hard so got another condom and stuck some more porn on. We started fucking side by side, but when I stretched out and looked up I noticed he was just looking at the porn and thrusting which put me off a bit, so I put him on his back and climbed on again. By this point it was dark outside, and I could watch myself riding him in the window like a mirror. There were blinds and we were on the 5th floor, but I was turned on by the thought that someone could possibly see my silhouette. He pulled me close to him which made me feel amazing, then we flipped into missionary and he held my legs back whilst thrusting deep into me until he came.
He told me he’d never gone 4 times in one night before – so that made me feel pretty awesome, then it was time to sleep. The 4th time was worth it, but because that had woken me but made him sleepy I then suffered not being able to sleep along with his awful snoring so I felt pretty horrible all night whilst he blissfully grunted away beside me.
When it got light I started playing with him whilst he was asleep and got him hard, he was quietly moaning in pleasure as he came to and reached over and touched me. There’s only so much clit rubbing I can take before I’m desperate for something inside me but he kept pulling his fingers out and teasing me more. He said his cock couldn’t take any more after last night and so I just lay back and let him work his magic fingers on me. I was writhing around so much when he finally plunged his hand deep into my pussy which was so wet and aching I squirted three times. He then asked me if I enjoyed it – seriously, what did he think?!
After that he snored some more, and I had to force him up and showered so we could check out on time.
Did you have an orgasm? Did your partner(s)? Both of us – him 3 or 4, me 5 through fingering and then the total headfuck that was the toy in the arse
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? He was stocked to the max with condoms. We had had unprotected sex before because he’d only got one and we got disturbed, and after that I told him I’d only continued cos I’m on the pill. So he knew condoms were not an issue, but I actually feel good that he cared enough to use them anyway. I was so turned on that they didn’t change how anything felt, and we joked what the cleaner would think if she came into the room before we cleared it up – condom packets everywhere including the shower, piles of sex toys, TV on porn, damp and dubious patches on the sheets!
What were your REASONS for having this hookup? I’d had the most amazing sex with Ron last year. I wanted to see him again and to be honest, just as friends would have been great but he clearly doesn’t want to be in regular contact like that. Bottom line – I simply love fucking him.
Were alcohol or drugs involved? If so, how much? A couple of glasses of red wine and a JD for me, two vodkas for him.
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? We wandered back to our cars and kissed goodbye – the last thing he said to me was great night and then we drove off. I’ve messaged him since but got nothing back. This was how it was last year and I know he’s doing it so I don’t get attached. It’s hard going from chatting lots and in a very intimate way to just nothing, but I know I need to be patient and give him some space. I do have a husband after all and I have absolutely no idea of his relationship status.
To whom did you talk about the hookup? How did they react? I mentioned to someone else who knows Ron that we’d seen each other, but he doesn’t know what our relationship has been and so I didn’t go into detail.
Was this a consensual and/or wanted experience for you? For your partner? Absolutely. We were messaging each other all sorts of dirty stuff in the build up.
Do you regret this hookup? If so, why? The sex was amazing and it was great to see Ron after all this time. The only regret is that I’m now into the estranged period again now where I have to be patient and wait for him to be ready to resume contact again. But deep down I know that’s a good thing as a full blown affair would not work and I don’t want to threaten my marriage.
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 has to be fuck number 3. I totally lost my inhibitions and let someone else control me. Next time he can fuck me in the ass and use the toy in my pussy. Worst is not knowing when that will be – might be never.
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 or anything else? I’ve had to keep remembering our last amazing time together for 10 months and that memory has started to fade (although still gets me off good enough when I want it to!) The reason I have posted this is so I can return and read it whenever I like, since I have no idea how long I’ll have to wait next time, if there even is a next time.
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