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I love the transvestite lifestyle. Since I was sixteen, I have been boldly going out dressed to the nines as Cari in public. Now finally of legal drinking age, I go out to one of Boston’s gender friendly nightclub establishments on the weekend. I am lucky to be considered one of the prettiest and the most believable of the girls at these clubs. At five foot five inches tall and one hundred and thirty five pounds I have a body that looks good in almost any kind of dress!I have naturally blonde hair which I keep at shoulder length. I often add hair extensions for effect and my lithe body is shaven smooth from my ears to my toes. As a guy I look a bit wispy and feminine, but made up – people tell me that I look stunningly female and attractive. High heels and tight little dresses make me quite the item in the bars – even though my seven inches are well hidden in my gaff!Two years ago I stepped out into the transgender world with a major level of fear. Now I am comfortable and love showing off a little smooth skin. I even like being chased and hit on by guys at the bars. I do enjoy the flattery and the free drinks. I love being adored and feeling attractive. As open as I am about my feminine side, I rarely would dare go out on a date with a man.After a year out in the bar scene, my perspectives suddenly changed. I began feeling more comfortable in the company of certain gentlemanly men. I would even meet one guy at the bar on a regular basis and he became a protector and friend.I never realized that I could have feelings for a man when I dressed as a woman. This nice adoring man changed that. One day he held me close and kissed me. I could never have imagined how that moment could have so re-wired my brain!My first boyfriend changed my view on everything about being a pretty girl. I soon came to realize that I truly enjoyed being a woman in the arms of an attractive older man. The man needed to be mature, special and trustworthy. I didn’t trust the young studs and their not so subtle ways, and the man who became my first boyfriend was the wonderful opposite of all that.I do have a fairly good opinion of myself. Being this man’s girlfriend and mistress was a positive experience for me. I’ve accepted that I can be a lady when with the right guy yet I am in not usually in any hurry to do so. Everything must be right. I’m cautious because a pretty boy in a dress is not always welcome. Some call me a sexy trap. I never intend to trap anyone!I have been dating some since I ended my relationship with my boyfriend. My ex was twice my age and very masculine. He opened my world to sensual life as a woman and I’ve been smitten about sexuality since. I love having sex with a good man. I know what I want and like now that I’ve lost my virginity.The transgender world is dangerous and a little scary. Trust is a difficult thing to develop with most of the men I’ve met. I rely a lot on my bartender friend who I always tip well. I also trust my girlfriends for advice on many of the patrons who frequent the clubs. I avoid the drug involved and anyone who can be trouble.My girlfriend Robin had been telling me about a man who was very interested in me. I knew of him and had spurned him in the past because I didn’t find him very attractive. He was in is fifties, big and heavy set and looked Ankara escort Bayan like a construction worker. He was a little rough around the edges for me.I am a sucker for guys with a bit of class. This guy once offered me a lot of money to go out with him as a call girl. To that, I flat out refused him. He certainly wasn’t my type and I refused to be bought!Robyn told me that he owned his own construction company and had money. He was certainly well off enough to regularly take out one of the priciest transgender call girls in town. One of those girls was Sandy. Sandy was a stunning Vietnamese transsexual with plastic surgery enhancements that would make Uma Thurmond jealous.Sandy was slim, brunette, perfect in the face and body, and had stunning breasts and hips. Most all of her beauty was the product on a very talented plastic surgeon. She was sexier and hotter looking than any real woman that I ever met! She was so feminine that a woman could never match her – even though she had stuff down there!Sandy had shared with Robin just how much this man was willing to “pay” to go out with me. Again – going out was meant as doing so in the form of being a hooker, prostitute or call girl. It was sex for pay and I’d never even considered such a thing. The dangers, diseases, and the fact that I was far from being desperate for money were just a few of my many reasons!The man’s name was Warren and he was known in the bar as Buddy. He had told his client Sandy that he would pay her if she could arrange for a date with me! Sandy spoke with my friend Robin and Robin was simply sharing the “offer” that the man was making for me. I was rather unmoved!A month ago Buddy had offered me five hundred dollars to have sex with him! Now apparently the offer had gone up even higher. He was offering me one thousand dollars for me to be with him for the night! To me no amount of money would bring me to such a place. My friend Robin told me I was crazy to say no to such an offer. She wished that the offer was for her! Robyn is stunningly beautiful herself.I must admit the offer did have a certain intrigue. One night of “work” was what I made working part-time in about a month! I did fleetingly think about it. I kept hearing Robin telling me how crazy I was if I didn’t do it. Buddy had bought her several drinks as well. He knew how to influence people.“No one makes a thousand dollars a night as a call girl around here.” Robin kept saying. “I would sleep with a pig for a thousand dollars!” She joked. Buddy loading my friend with drinks was just another way of getting what he wanted!I was feeling a little tipsy from the drinks Buddy had been sending to me earlier. I decided to check out his offer to see if it was really true. I went over and thanked Buddy for the drinks he had sent Robyn and I. “Cari you are so hot. I want to go out with you next week. I’ll give you a thousand bucks and a hundred dollar retainer!” I was stunned. It seemed like the kind of offer that might be hard to outright refuse.“If I say yes, what do you have in mind?” I asked coyly. Buddy was blunt and no nonsense. “I’m a nice guy don’t worry.” He said trying to be assuring. He suddenly handed me a hundred dollar bill.  Then he looked me in the eye and said he’d meet you in Escort Balgat the lobby of the Boston Harbor Hotel, Friday night at seven sharp! I stared at the hundred dollar bill as he placed it in my hand. “Deal?” he said. “Okay.” Was my weak, somewhat dumbfounded – and less than confident reply!I went back to Robin at the bar and showed her the hundred. She was pleased and proud of me! “Way to go girl! You’re officially a call girl slut! I wish I could make that kind of money! She added. That’s when the remorse set in. The money and offer was great. Then it hit me. I surely wasn’t a hooker!I decided I was going to return the money to Buddy. I was going to back out. I couldn’t see myself being a whore for a night with a man I didn’t even know at all! I looked for Buddy and I couldn’t find him. He was gone. I didn’t have his number. How could I notify him?I went home and wondered what I should do. Dressing as Cari was always a hobby turned lifestyle. Being in college, my weekend transformations are simply my escape from the pressures of real life. I certainly wasn’t a hooker. I worked part time and had enough money to go out every weekend. It rarely cost me a lot because I was always willing to accept free drinks!That night I had a hard time falling asleep. For some crazy reason, the idea of being a high priced call girl was making me feel horny! It was rather flattering considering I was the opposite of Sandy. I had no breasts, fake lips or any physical enhancements! I was just a pretty, smooth skinned, nicely polished up pretty guy in a dress.I knew that Buddy wanted me just the same. I looked more like a high school cheerleader in bright red lipstick than a high priced call girl. With each passing hour in my sleeplessness, I began to realize that I would do it.Buddy was willing to pay to have me, and I was thinking that I would be willing to have sex with him as long as it was all safe. It would be precarious meeting him in such an elegant and expensive hotel. I was certainly filled with stomach butterflies and our date wasn’t even for six more days.At college I tried to focus on my classes, but my mind seemed to be constantly adrift. What had I just agreed to do? What if he didn’t want to have safe sex? I should have clarified all that very important stuff. This guy had been with prostitutes before. I did know Sandy would never have unsafe sex as a hooker so I might be all right. I would not have anything less.Friday in class found me even more beside myself. In Psychology class I couldn’t help but think I was pretty abnormal! I was excited, scared and practically shivering at the thought of all the unknowns and what it would be like to be a female looking hooker this evening. I did realize that I wouldn’t likely back down partly because I already had been given my retainer!I also realized that being a high priced hooker had apparently been some kind of subliminal fantasy of mine. I admired the beautiful transsexuals that came into the bar on Saturday nights. I so loved Julia Roberts in Pretty Woman. I wished that I was her!As crazy as it seemed my becoming a call girl was about to come true in spite of my doubts. I would indeed meet him in the fancy lobby. I knew I had the perfect dress and outfit to wear in my role as well.I Batıkent escort went home early as I was just unable to focus on my classes. I suppose I wanted to ready myself to be perfect for my introductory night as lady of the evening! I bathed in luxurious bath soaps, softening my skin as I shaved my legs, arms, and every crevice in my body. My male hood just stayed so hard and so erect. I was finding myself to be thrilled at the prospect of my first night as a professional gal!Now all perfumed and perfect, I did my make-up flawlessly adding eyelashes and bright red, glue on fingernails. The final touch was painting my toenails bright red as well. I began to dress. Rolling sexy, lightly tinted stockings over my smooth legs and thighs was magical. There is no better feeling than getting ready to be a girl with a purpose!I got out the dress I had never worn in public. It was actually more conservative than most I owned. It was however very striking. It was made of a shiny gold, rich looking fabric with a nice amount of stretch built into it. The neckline was straight and conventional. The length though was sexy at mid-thigh and it clung to my lithe body like a feminine dream.My reflection was spectacular. The dress was amazing and being long sleeved I looked a hundred percent female. I added a bit of padding to make my breasts look a bit more feline as well.In my full length mirror and in five inch gold matching pumps my appearance was beyond stunning. I had outdone myself! The only thing of concern was that I was all ready to go out two hours too early! I thought about the details packing a night bag with my make-up, extra stockings and a pretty, red silk camisole.The sexy red nighty was a gift that my boyfriend had bought it for me. Knowing that I’d been fucked in it dozens of times made it seem perfectly appropriate for the occasion! I also packed white silk stockings and white lace gloves for a special sensual and even erotic look.I was certainly not going to be late dressed like I was. I drove downtown to the waterfront and parked in the hotel’s parking garage. Twenty five dollars a night is a bit steep – so I appreciated that I had been given the retainer as Buddy called it. After dozens of deep breaths I got out, taking my pocketbook, and evening bag. Was I really going to go through with this?The garage felt cold in the October night air but it made me feel sexy. I was regretting my boldness for not taking a jacket or cover up. I walked in delight, feeling so sexy in my five inch heels and matching, rich looking, and gold colored dress. I looked and felt like a high class whore! I made Julia Roberts look so common in her hooker boots and mini skirt!I took the elevator up to the lobby. I had time it perfectly. I checked my phone, It was exactly seven P.M. I emerged from the elevator looking suddenly with eyes all over me. In my mind I looked like a movie star and I tried to work that confidence into my heart.I got stares immediately in my short sexy shiny gold dress. I could feel every man in the place looking at me. I walked across the lobby to the edge of a Starbucks counter and waited. Where was Buddy? I was feeling virtually naked, and guys were staring at me in my minimalistic, overtly sexy outfit.My nerves were on edge. I looked around. I was desperately fretting. I would only stay a minute or two longer. Thankfully he was soon right there. He had been waiting for me, but the long, hurried strut across the lobby had felt like an hour and not the half minute that it must have been.Buddy was all dressed up in a suit jacket and dress shirt.

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