1. Carolyn Makes Her Way (Part 1)


    Date: 3/5/2016, Categories: Crossdressing, Author: tvk3983, Rating: 3, Source: LushStories

    After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity and applied my makeup carefully, I brushed my long red hair, no wig for me, and made certain that my purse was nicely stocked. I always carried five or six rubbers just in case whoever was going to pound my ass had forgotten his. A girl has to be safe with strangers. And accessories are a must to complete any ensemble: rings on each hand, a necklace with a star shaped pendant, earrings of course, a gold ankle chain and three bracelets on one wrist. Finally I slipped on a pair of black stilettos, the five inch heel variety, and I was ready to go. With any luck at all I'd meet a man or two or more, get my tranny ass fucked hard and suck a nice fat cock. Gay, straight, bisexual, married or single, it didn't matter to me. After all, I'd gone almost an entire week without anything except a dildo and my hand and I were super horny. As I drove to my favorite pick up bar I thought about what they'd say about me at work if they only knew. As far as anyone knew my name was Carl, a very mild, milk ...
    toast man, never outspoken, and a very good worker. Tonight my name is Carolyn, a very sexy, always ready to party, sexily dressed, transvestite. My measurements, which I worked hard to maintain were pretty good: red hair, green eyes, five feet five inches tall, one hundred and twenty-two pounds, C cup boobs, which were store bought, very petite and dainty, and the biggest slut around. When I walked into the bar, I saw that getting there early might have its drawbacks. There was me, the bartender, two men, obviously lovers, or about to become so, sitting in a booth, a man at the bar with another girl like me hanging on his every word, as well as two tranny other girls I knew waiting for men like vultures waiting for road kill. “Hi, Carolyn,” Jerry the bartender smiled. “Hi, Jerry,” I smiled and waved. He and I were on a first name basis since he had face fucked me behind the bar a few times. “Ladies,” I said smiling as I approached their table, “May I join you?” “Sure, babe, pull up a chair,” Melanie replied. She had raven black hair and smoking hot eyes to go perfectly with her long, shapely legs. “Pretty dead in here,” I said, taking out a long, slim cigarette and placing it between my cherry red lips. “But it's Friday and we're early. It'll pick up after the guys go home and clean up,” Sheila quipped and smiled. This week her hair was long and blonde, falling well past her shoulders and framing her face perfectly. Sheila was the wild one, even wilder than me. She had, on more ...
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