Some of my best friends are transvestites. I met them at a nightclub in L.A. It was pretty famous back in the day. They had a drag and dinner show. Some very talented people worked there. Some actually lived their lives as women, but a lot didn’t.
I used to hang around with Daniel. He was a very attractive man who also did a great Dionne Warwick. He also did the grand finale of the show – the woman to man transformation. I always loved that part – where he cleans off his makeup, takes off his wig, and becomes a very very handsome young latin man. It always brought down the house.
Anyway, sometimes he was also a pretty girl named Brittany. Brittany and I used to go to an exotic drag nightclub where the performers, pretty chicks with dicks, got naked to music. We also went shopping and dancing. We had a lot of fun. Some of us used to tease Daniel about Brittany, because while most of the TV’s that worked with him wore exotic and sexy clothes when they went out as women, he wore conservative secretary-style clothes, and always acted like a perfect lady – even at the strip show. Go figure.
Anyway, one night I drove us to the club and Daniel (Brittany) got drunk. This had never happened before when I was with him, and a few of us gently teased him/her that the “perfect lady” was perfectly drunk. She smiled at our hilarity, even though when she wobbled on her high heels, something she NEVER did when sober.
Well, somewhere during the course of the night, someone told Brittany that she could never pass as a real girl. This was silly, because you really couldn’t tell, not even close up. But Brittany had gotten angry and hurt, and the evening had taken a turn. She asked me to take her for a drive.
I drive a convertable, and we eased the top down. I assured Brittany that I wouldn’t go too fast (she was very particular about having her wig styled just so) and away we went.
A couple minutes of driving and, wouldn’t you know it, some guy starts hitting on us (sike I said, Brittany can pass). And he’s cute in a sleezy nightclub way. He came upon us at a light and said to us “Hey, ladies, what are two fine chicks like you doing running around on a night like this?”
Well, I’m not into cheesy pickup lines, but Brittany starts flirting with him! “Oh, not much” she answers. “Just looking for a hot stud like you”.
I’m startled. Like I said before, usually Brittany is the perfect lady. I guess that alcohol was talking.
“Want to follow me to my place?” Lance Romance asks us.
And that is how I ended us at a strange man’s apartment with an undercover TV.
Brittany starts making out with this guy at the door before we even have time to introduce ourselves. They are sucking each other’s tongues and Brittany starts feeling the guy’s nipples. Just as he’s about to try to reach into her bra, she comes up for air.
“It’d make me REALLY hot if you could play with my friend’s tits while you’re kissing me” says Brittany.
“So THAT’S how she’s gonna keep him from finding out she doesn’t have tits” I thought, as the man starts feeling my boobs.
Brittany winks over his head at me, as she starts kissing him passionately. His hands quickly found their way into my bra. He was squeezing my tits and fondling them as Brittany sucked on his tongue and felt up and down his chest. Soon she had his shirt open and was working on his pants, the whole time kissing him passionately, wetly.
Next thing I know, Brittany has this guy’s hard cock in her hand – a short step to her mouth. She was sucking him hard, while squeezing his balls. He’s licking and squeezing my tits, and beginning to moan a bit. I’m leaning over him and watching her suck, her perfect lips coated with red lipstick, running up and down his swollen shaft. Occasionally I could see her tongue dart out and lick his purple head, then she would put the dick all the way back in her mouth, all the while careful not to disturb her wig.
After a while, the guy is ready to get off. He’s making noise, his fondling of my breasts is a little rougher and more frantic, and his body is moving with Brittany’s sucking motions. He is ready! And she knows it! He has NO idea that the beautiful brunette eagerly slurping his rod has a cock herself, and he wants to shoot his load.
Brittany starts making cooing sounds and looking in his eyes as she sucks his cock. She is squeezing his balls firmly, and rubbing them. And then it happens – dude begins to squirt his hot load deep in Brittany’s mouth. She lets him – no, she makes him give her every drop, drinking it thirstily.
After it was over, we beat a hasty retreat – didn’t want to get to know him, didn’t want him to figure anything out. And Brittany told everyone about the guy that she sucked off while she passed as a real girl!