This friend of mine was over and I decided to show him some new clothes I’d bought myself. He really liked this one dress in particular I’d gotten. So much so he asked if he could try it on! I was shocked and asked why he’d want to do that. He then told me for a few years now he’d secretly been dressing up in women’s clothing, and was even bisexual. I had wondered about him, as I’d noticed him checking out guys a bit too much for a straight guy, and apparently this was the confirmation of that.
He said he has been a bit too shy to fully dress up and go out in public, but if I’d think of helping him, he just might have the courage. I agreed, and looked through my closet to find the frilliest, most feminine thing I had. I had the perfect thing. My grandmother had sent me this dress a few months ago, but it wasn’t my style at all, so I’d never even tried it on. I helped do his hair and makeup and got him in the frilly outfit and a pair of old, stretched out shoes I had. My God, if I didn’t know any better, he really could have passed as a woman. He wasn’t very tall, slender build, I said we could go to the gay bar the next block over and we walked there once he was made up. I freshened my makeup and off we went.
We did get stares from the moment we walked in, and he was hit on by several guys in pretty short order. I stayed at the bar and he went off to some guy’s table as I got to know the bartender better. I then saw him and the guy go off to the VIP room in the back. I snuck off behind them to see what was going on, and my friend was down on his knees sucking this guy’s cock pretty greedily, all the way up to the balls. I must admit I was a bit turned on watching him through the crack in the door, the other guys hand on the back of his head, just gagging him with that dick as he slurped away on it.
He was kneeling in the frilly dress, wearing lots of makeup, looking like quite the horny little tart with that dick down his throat, cupping his new friend’s balls and enjoying giving that blow job. I just watched him go at it. After sucking on the guy’s dick for a while, he got up and lifted his dress and pulled down his panties and waited to be fucked. I saw the wet cock go towards his ass and slowly disappear inside of it as he groaned a little as it penetrated him. I could see the balls slapping against his ass as he got fucked. He was stroking his own dick as he got fucked and it didn’t take long for him to cum and then the guy fucking him came as well, filling him u until I saw a river of cum drip down his thigh and he pulled his panties up and his dress down and the friend walked by me on his way out. I walked in and asked if he’d liked acting and looking like a girl and being a little cumslut and he smiled and said yes, it had been one hot night and thanks for helping him.He was the perfect sissy boy. Everyone deserves to live out their fantasy.
Gisele
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