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This isn’t the first time that this gay guy has had sex with other studs, but it is the first time he’s gone out in public dressed like a woman to find them. He’s crossdressed at home hundreds of time, but last night, he finally worked up the courage to go out in public dressed in from head to toe as a woman. Just that was a turn on for him, meeting a dude to take home made it even better.

Check out these pics from this crossdressing adventure. The man has never had sex with another dude before, luckily this twink is more than willing to be his teacher to the pleasures of gay sex. He’s soon stripping his friend out of his clothes and going to work on the man’s hard fuck tool. The real fun cums when the crossdresser pulls up his skirt and invites the man to come fuck his ass.

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Donny had been trying to start up his own business for a while now, he didn’t have much as far as start up funds go but he was a hell of a painter and he already had a few clients lined up and ready to have him drop by to paint their houses. Soon enough word of mouth started to spread and Donny started getting more and more clients. One day last week a new client dropped in to see if Donny would be interested in painting her new house as well as giving her an added bonus.

Donny had never even seen a tranny in person but when she slid her hand over his dick he couldn’t resist her. Donny smiled at her and told her that he was sure they could work out a deal for painting her house. He didn’t have to say anything else because she was already on her knees and sliding his cock between her lips. As she mouth pumped him her bulky shemale cock started to get bigger and harder and Donny couldn’t take his eyes off it until finally she dropped her panties and bent over his desk with her ass spread.

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