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Dating Disasters
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Straight Male / 55
Not What I Was Expecting
So about 5 or 6 years ago I was chatting with a tgirl from craigslist when they used to have sex ads. This girl said she was a petite crossdresser and had some sexy outfits and liked being really nasty and submissive when she was dressed.
Me and my wife were up for a bit of fun and something out of the ordinary. I was hot to watch her doing a kind of lezzie session with the tgirl and wanted to watch my wife suck some cock too.
So we go to the motel where this person is staying in town on business and the first turn off is when we get there the room is full of cigarette smoke. The supposed to be petite crossdresser is about my size, 5' 10" but is taller in heels. Has a pretty noticeable 5 o'clock shadow too.
Pretty decent ass and a little stiff dickie.
So we go in and he or she goes to lie on the bed and has my wife get on the bed too. They start making out and my wife is OK with it and is tongue kissing and squirming around looking sexy and turned on.
I would've expected to get excited myself and maybe join them. Figured I would kiss and pet my wife and let the CD suck my dick or something. But I wasn't at all turned on and didn't get a hard on or anything.
Watched them groping and fingering each other a bit and was trying to rub myself hard, figured maybe I'd just drop a load on them. The CD said she liked being facialed and taking guys loads on her. She liked being used and even wanted to be pissed on.
Anyway, after maybe an hour or so of them doing some soft core kind of stuff I was still not getting into it or getting hard and finally just figured we should cut our losses and go home for some private sex before it got too late.
We had traveled like an hour to get there and it felt like a waste of time, but shit happens.
My wife said she wasn't getting turned on much either but was trying to be a good sport and see if things would get better. She'd have done whatever I asked her to do or whatever the CD asked her to do, but she was just going through the motions too.
So in the end we were kind of frustrated and were on the way home when we spotted a couple of sexy looking girls hanging out on a corner. They looked like hookers and I went around the block to check them out again.
Confirmed that they were whores and stopped to talk to them for a minute while my wife went to get some stuff at the convenience store on the corner.
Made a deal with the prettiest whore to sit in the back seat and make out with my wife while I watched and this time I got hard right away.
My wife was sucking the whores tits and she was fingering my wife and both of them were moaning and the car smelled like pussy.
I had my dick out and was stroking when the two girls started to blow me together.
That was real hot to have my wife suck my cock and a whore lick my balls.
Wife was turned on to be doing this shit on a quiet city street around the corner from where we picked up the tart. There was probably other guys parked on the block getting laid or getting blowjobs from other whores too.
Me and my wife were up for a bit of fun and something out of the ordinary. I was hot to watch her doing a kind of lezzie session with the tgirl and wanted to watch my wife suck some cock too.
So we go to the motel where this person is staying in town on business and the first turn off is when we get there the room is full of cigarette smoke. The supposed to be petite crossdresser is about my size, 5' 10" but is taller in heels. Has a pretty noticeable 5 o'clock shadow too.
Pretty decent ass and a little stiff dickie.
So we go in and he or she goes to lie on the bed and has my wife get on the bed too. They start making out and my wife is OK with it and is tongue kissing and squirming around looking sexy and turned on.
I would've expected to get excited myself and maybe join them. Figured I would kiss and pet my wife and let the CD suck my dick or something. But I wasn't at all turned on and didn't get a hard on or anything.
Watched them groping and fingering each other a bit and was trying to rub myself hard, figured maybe I'd just drop a load on them. The CD said she liked being facialed and taking guys loads on her. She liked being used and even wanted to be pissed on.
Anyway, after maybe an hour or so of them doing some soft core kind of stuff I was still not getting into it or getting hard and finally just figured we should cut our losses and go home for some private sex before it got too late.
We had traveled like an hour to get there and it felt like a waste of time, but shit happens.
My wife said she wasn't getting turned on much either but was trying to be a good sport and see if things would get better. She'd have done whatever I asked her to do or whatever the CD asked her to do, but she was just going through the motions too.
So in the end we were kind of frustrated and were on the way home when we spotted a couple of sexy looking girls hanging out on a corner. They looked like hookers and I went around the block to check them out again.
Confirmed that they were whores and stopped to talk to them for a minute while my wife went to get some stuff at the convenience store on the corner.
Made a deal with the prettiest whore to sit in the back seat and make out with my wife while I watched and this time I got hard right away.
My wife was sucking the whores tits and she was fingering my wife and both of them were moaning and the car smelled like pussy.
I had my dick out and was stroking when the two girls started to blow me together.
That was real hot to have my wife suck my cock and a whore lick my balls.
Wife was turned on to be doing this shit on a quiet city street around the corner from where we picked up the tart. There was probably other guys parked on the block getting laid or getting blowjobs from other whores too.
- That's Juicy! 10
- Remove It! 0


