Shemale Transvestite

Milena is one of the best shemale’s at tranny trouble and she’s got this absolute talent of just pulling in handsome men who are just waiting to have sex with her. They of course don’t realize that she is a tranny, but that doesn’t really matter because they still end up fucking. It wasn’t to long ago that Milena had a bet with one of her girlfriend that she would be able to cum all over Reggie who was one of the IT guys down in the basement of the building. Milena being the sexy shemale that she is was all in for this bet and went to work on him right away.

Milena first went down to his desk and adjusted her bra so her boobs would be a little more exposed. Reggie who was a pretty handsome man always had hot women approaching him before so he was pretty used to it. He however was not used to the charm that many transvestites possess. She looked him in the eye and asked him a few simple questions about her computer and if he could come help her with her laptop upstairs.

Reggie locked up his computer and followed Milena into the stairwell where she made her move. She started walking up the stairs and Reggie followed trying his hardest not to look up her mini skirt because it was so short. Milena used her shemale charm and walked so hot that each step she took made her ass look so delicious. Reggie’s heart was beating faster and faster and he started to get turned on by this sexy tranny ass.

Milena then stopped on the 3rd floor (which wasn’t her floor) and said she had to make a quick stop to the ladies room which Reggie needed as well to splash some water on his face and cool off. He had just finished drying his hands when he heard the door open and hears the door lock. He looks over and Milena is staring right at him coming closer and closer. She puts her hands out and around Reggie and starts kissing him all over his neck. Reggie instantly puts his hand down the back of the shemale’s skirt and grabs that ass that he was dreaming over. It felt so good and he still had no clue that she was a tranny and that he would be having sex with her soon.

Milena drops his pants and starts sucking on his dick making it harder and feeling it grow in her mouth while she plays with her shemale dick thinking about having wild shemale sex. She’s getting it harder and harder until Reggie gets down on his knees and feels between her legs for her pussy, but instead finds a cock and is so surprised. He doesn’t want to continue but he’s so turned on. Milena says “didn’t you know I was a transvestite?” Reggie replies “I had no idea..you’re so hot and I want you so bad”. Milena just smiles back and let’s Reggie fuck her in her tranny ass until he cums inside her.