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When I (38M) Hooked Up With a Sexy Fare
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Well, let me set the scene. Driving rideshares was my side hustle, but I took it very seriously. On this particular night I had just cleaned my car and was also wearing a suit.
I picked up these three from the house they were staying in. It was a couple and their friend who were visiting from out of town and wanted to go clubbing. When I saw how they were dressed I decided to really push the experience, so I gave them the full chauffeur treatment, including opening the door for them.
The girl who was the third wheel seemed especially impressed, and slithered into my back seat in this sexy red cocktail dress. Once they were all in we took off, on about a 40 minute drive.
I made some idle chat with all of them but she kept saying to her friends that she decided she wanted to stay in instead of go out, so when we got to the club they asked if they could just give me some cash to take her back. I agreed, and was happy to have a chance to flirt, but had every intention of just taking her back and dropping her off. It's a delicate situation.
She was....more obvious about it than I'm used to, but made some clear cues what was on her mind, laughing at my dumb jokes, crawling between the front and back seat and shoving her ass in my face. I tried to play it cool but I was definitely getting hard.
We got back, parked I told her I'd wait to make sure she got in alright, and watch her walk to the door. After a few minutes she came back and told me she couldn't get the lock, and asked for my help. I turned off the car, my heart pounding, went, and very easily opened the door for her. She invited me in, and I followed.
I didn't honestly know what to do, so, I asked if I could use the bathroom, and went in to calm myself down for a minute. When I came out though, she was standing outside the door waiting for me, and had already pulled her dress down off her tits.
I don't know how I was so smooth, because my heart was racing, but I just asked her if she needed a hand and she nodded. I slid my hands against her hips and tugged the dress down until it fell to the floor. While I did that she started rubbing my cock through my pants, and when the dress hut the floor she said "come here" and led me by my tie to the bedroom. She then pushed me on the bed and practically attacked my pants, ripping them off and like clenched my cock.
I started dirty talking things like i never have before, but apparently she liked it because she just started sucking me like she wanted to literally absorb my cock.
I told her i wanted to play with her and kind of grabbed at her leg, so she presented herself and i started by rubbing through her panties, which were still on. After i could feel how wet they were i quickly pulled them aside and started rubbing her silky clit. She moaned immediately.
After a few minutes of this she stopped for air, and i pulled her on top of me. I had taken off my jacket but was still in my shirt, which she frantically helped me unbutton. Pretty quickly I was de-robed and she shoved my cock in and started riding me.
It was amazing, we were moaning, my hands were roaming her body.
After a few minutes she asked to switch, so I got behind her and reached around to rub her clit while I fucked her. It was so fucking hot. I'm surprised I lasted as long as I did, but after a couple minutes I was throbbing as she pushed back against my cock, so I braced her hips and pulled out just in time to cum all over her ass.

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4 months ago