1. Cindy's first time


    Date: 12/26/2015, Categories: Gay Male, Author: rushman1uk, Rating: 9, Source: LushStories

    My girlfriend got a new job where she would travel a lot, so I had the house to myself for days at a time. It was the perfect opportunity to explore my feminine side and start dressing up in the same sexy lingerie I would buy for her. No sooner would she hit the road and I would be in her dresser fishing out sexy outfits. I had a gym bag in the trunk of my car where I kept a wig, otherwise I'd use her heels and make up and do myself up until I was a sexy little cross dresser. Semi passable too if I do say so myself, although despite how I looked on the outside I was all sissy girl on the inside. I would go total fem and cam online with horny guys, jerking off for them, showing off my sexy panty-clad ass for them, puckering my lips at them. I'd do anything they asked and it got to the point where I was ready to have the real thing. I'd yet to really have full on sex with men as a gurly boy. Oh I'd cruised for cock here and there but those casual hook ups were usually over as soon as they began and like I said I'd never done it fully "dressed". The sissy inside of me was just aching for a man's touch and I'd been training my pussy asshole with one of my girlfriend's dildo's for months, so I was more than ready to take a big hard cock. I conducted my search online for the right guy, and before long I came across an older man in his sixties. An average looking guy, silver haired, kinda blue collar, but seemingly normal. My preferences weren't too specific, but I'd grown accustom ...
    to watching porn of older men fucking young sissy traps like myself, so my guy needed to have a high sex drive and be wild enough to go for a cross dresser. His name was Hank and he was probably the sweetest man I could've hoped to meet. I asked him to call me Cindy and sent him a couple full body pics of myself, which I took with my webcam, dressed in a hot little, black baby doll negligee, fishnet stocking and heels. I wore my brunette wig and bright red lipstick. I took one pic from the front and one from the back so he could see my sweet ass beneath the skirt. In both pics I sucked on my finger and gave him a pouty look. Best part was, I described my feelings, and how badly I wanted to be a sissy slut and how I was ready to try out the real thing with a true sex daddy, in the flesh, and he knew exactly where I was coming from. He said, "Cindy, I am going to treat you right, and take good care of your steaming hot wet pussy, so that when I'm done with you you'll be a true cock slut sissy gurl." To say he hit the spot would be an understatement and my only reply was my address and an invitation to come over that same night whenever he wanted. An hour later he was at my door. I braced myself, took one last look in the mirror to fix my hair and check my lipstick then I took a deep breath and let him in. He was barely in the door before he was manhandling me, pawing and grabbing at my ass while kissing me passionately on the mouth. I was a little off guard, this being my first ...
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