Got myself quite turned on thinking about this at work before so I figure maybe it'll do the same for some others if I share the story.

I didn't actually go specifically looking for it, just one day sometime mid-November I was browsing a hookup site, and saw a woman close by who said she was free that day. She was in her late 30's, tall and slim, with pale skin and long strawberry blonde hair, he profile had a good collection of very hot pictures, so I figured I'd try my luck and message her.

She replied back very quickly with a greeting and a question. "Would you be ok with me pegging you?". Now pegging is something I've always wanted to try, ever since I first came across femdom porn as a horny teenager and realised that dom women are a thing I like, but I can't say I was expecting to be offered it in a non-kinky 'casual' scenario like this. Still, what the hell I figured, and told her "sure thing".

A few messages later and we agreed for her to come over to mine in around 45 minutes. Just like that. In less than an hour I was gonna have a woman's strap-on inside me. Needless to say I was very excited, and also very nervous. If I'm honest I always get a bit nervous with meeting new people for hookups, but this was another level, I mean I was about to fulfil a long held fantasy.

She arrived at my door precisely on time, greeted me with a lovely friendly smile, before coming inside to get right down to business. She went for a quick bathroom trip while I shut the curtains for privacy, and laid down a towel on sofa where we'd be playing, y'know just in case. When she came back she unpacked her 'equipment' from her bag and immediately started to strip. I followed her lead and got naked alongside her, her body was even hotter in person, and she readily returned compliments to my body as well which was very welcome. I reiterated to her that this was my first time being pegged, and she was lovely and reassuring about it, calmly explaining there would be plenty of lube and no pressure to keep going if I didn't like it, and overall just really helped put me at ease.

She handed me a bottle of lube and told me to prepare myself while she strapped in (on?). It wasn't a big dildo she had attached, I'd say around 5 inches long with a pretty narrow diameter, purple and smooth, with a strong upward curve to it, so it kinda resembled a purple banana. After I finished lubing myself up I handed it back to her and asked her how she wanted me as she deployed some extra on the strap-on itself. "Just get on the couch and stick your ass out to me". Don't think I've ever been so turned on by a sentence than I was at that.

I did as she requested, even reached back and spread myself out slightly for her. I felt the fumbling behind me as she got into position, rubbed her tip against me, and then asked if I was ready, before she slowly slid it inside after I gave her the nod. And oh my what a feeling. I'd played around with my ass a little by myself in the past, but nothing more than fingers, and even though the strap-on was a small one it felt so filling. I actually couldn't stop myself from groaning as she pushed into me, which prompted her to ask if it was a "good moan or a please stop moan?". I assured her it was a very good moan, so she continued until she was all the way inside and gave me a moment to adjust.

After sitting like that for a moment and feeling the hard plastic inside of my ass, I gave her the go ahead to start thrusting. She was slow and gentle at first, so I just allowed myself to sink face first into the sofa and enjoy the feeling. After again making sure I was still comfortable she asked if she could pick the pace up, and I told her to go for it, and the feelings got even better. It wasn't just her purple fake cock sliding in out of me that felt good either, it was her hands gripping my hips, occasionally stroking up and down my sides and over my ass cheeks. It was the feeling of her hips against my ass with each thrust, and the satisfying smack sound that accompanied it, a familiar sound sure, but not in this context.

I'm not entirely sure how long we spent like that, with her thrusting into my ass and me moaning into the sofa, but there was a fair amount of precum dripping out of me by the time she stopped (knew the towel was a good idea). I can't lie, I was pretty disappointed to feel her pull out of me, but I knew that she had somewhere to get to afterwards, and she also wanted to get fucked, so my pegging adventure had come to a close for now.

We shared bit of a giggle talking about how much I enjoyed it while she went to give the strap-on a quick clean before we resumed our fun. She gave me a really damn amazing blowjob, then I asked her to ride me so I could suck on her boobs as we fucked. She was amazingly tight and wet, and kept making these wonderful little breathy moans. After that we switched to doggy for a bit which seems to be her preferred position judging by the sounds she was making, it was also really hot realising that a little earlier we'd been in the exact same position just with the roles reversed. Finally she let me go down on her for a bit (tasted amazing), before she got on her knees and sucked me off some more, eventually allowing me to shoot my cum over her chest.

To be quite honest I kinda feel like nerves got the better of me towards the end and I rushed through it, but she assured me she had fun and that she'd be down to do it again at some point. And with that, she cleaned up, got dressed, and left with the same friendly smile she arrived with.

So yeah, apologies for the long post but thats how a spur of the moment attempt at a hook-up ended up giving me a big tick to put on the sexual bucket list.