Me My Boyfriend Her 8211 Part II
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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 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 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 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. He hugged me and immediately I felt a sense of relief. “I have Champaign for you up in the room.” He said enthusiastically. He he took my hand and my evening bag and my nerves eased. You are beautiful! Do you mind if I get a picture of you? He said smiling.
I was happy to oblige. I love being photographed when I know I look good. He took a couple of photos of me with his phone after he put down my bags. I posed and delighted. I would say I was feeling a surging joy. “You are so stunning. I love your dress. You look like a million dollars Cari!” He said solicitously.
He was being a true gentleman as he walked me to the elevators. He showed me the pictures on his phone as we rode arm in arm up to the eighth floor. I took a deep breath. Maybe this wouldn’t be so bad after all - I hoped to myself.
He walked me into the elegant room which turned out to be quite a large and penthouse like suite. This place was very impressive. I guessed this fancy penthouse cost more north than a few hundred dollars a night. It must be nice to have money like he did!
Buddy took my hand and walked me into a second bedroom that had a full size bed and also a rollaway style bed. He left my bag and pocketbook on the rollaway. He wanted to show me the rest of the suite.
He walked me into the main room which had stunning views of Boston harbor many floors below. To the right the lights of the financial district shone brightly. The views at were incredible as it seemed we were atop the entire world of the city.
I was feeling happy and special to be here! This place was for the rich and famous and I was hardly that! He hugged me and had me sit on the couch where he popped the cork on a bottle of Champagne! He poured it into two elegant wine glasses and we toasted to the night to come. I never expected a little romance!
In my sexy dress I never felt more special and feline. Sipping champagne I was almost totally relaxed as we talked. I asked about his job and work. Buddy did quite well for himself but showed a modesty that I liked about him. I talked about school and laughed about the irony of my Abnormal Psychology course. I joked that I was here to do some research. Buddy loved it and laughed deeply!
Our conversation went to the bar and the crowd we knew there. Buddy loved almost all the people. He looked at the place like it was a fantastic circus of sorts. It was really pretty true. I asked him what he thought of Sandy. I was surprised to hear how much he adored her appearance, but that he found her to be dull and rather boring. He joked about her narcissistic posing, and how she never met a mirror that she didn’t like!
Buddy asked if I liked basketball. I told him I did and he asked if I’d mind if we watched some of the game on TV. We were going to sit back and watch so TV. The laid back pace of being Buddy’s call girl was more than welcome because in my fears I had envisioned the worst.
I thought being a thousand dollar a night call girl would find me being fucked incessantly and all through the night. I wondered if I could take a man for so many hours at a time. I had figured that kind of money meant I would certainly have to do a lot of extra work for him!
We watched the first quarter of the game holding hands and cuddling on the couch. Buddy suddenly got up and handed me an envelope. Inside were ten, crisp, new, unfolded, one hundred dollar bills. He apologized saying he meant to give it to me earlier. I had done nothing other than talk, but it is apparently proper call girl etiquette to be paid in advance for a girl’s services!
I had quite honestly expected a little more action than watching what was on the television. I put my hand on Buddy’s thigh as if to say everything is all right. I think he was a bit shy but he must have known what he was doing. I think my having rejected him in the past had him being cautious.
He reacted by gently running his fingers along the tops of my stockings as I swooned. I think I wanted some action even more than he! He was treating me more like his girlfriend than his call girl.
I suggested I could get into something a little more comfortable when half time came. Buddy grinned and smiled. “Sounds good to me Cari” he said with a quick wink. We were already getting onto the same page. I was finding that Buddy was actually a pretty sweet guy. I had a feeling that I was going to actually enjoy doing my job with him!
I went into the bedroom and changed into my sexy, red, silk nighty. I took off my stockings and replaced them with silky white ones and added a pair of sexy, sheer, white, lace gloves to my hands. Buddy called into the room. “Are you decent?” He asked. “That all depends on your point of view!” I quipped in return.
I stood for him looking sexy and spun so he could look me all over. I was smiling almost as much as he. Buddy’s reaction to seeing me in my sexy, lover’s outfit was priceless. “Oh my God! You are sexy and hot beyond belief Cari! You have such a beautiful body too!” Buddy said while smiling broadly.
He grabbed his phone and declared he needed a picture or two of me for posterity sake. Part of me thought this was a bad idea. Would these be extortion pictures? Somehow I already had a sense of trust for Buddy. I’ve always had good people instincts.
I allowed and lusted in the picture taking session. I so loved the picture he took of me sitting sexily on the role away bed. I lusted in being caught on camera in such a sexy mode of undress looking so pretty and even just a bit naughty and nice!
Somehow I felt the need to be the aggressor. I was his call girl after all. I was also feeling quite incredibly horny. Being the Pretty Woman, I had a job to do for my Edward! I saw myself clearly as Vivian and I was feeling very sexy and far more willing perhaps than she! I got on my knees and looked up at him. I calmly unzipped his fly, all the time while smiling up and winking at him. It was time to earn my money!
I undid his belt as well and dropped his pants to his knees. I really wanted to please him. I wanted to suck his cock and there was no stopping me! Buddy was delighted at my eagerness and zeal. I tasted him and went to work on him.
I found his cock to be delicious and sweet. Buddy wasn’t the biggest guy in the world, but he wasn’t the smallest either. He was solid and thick. I estimated he was somewhat in the average range of about six or more inches. His circumcised cock was absolutely perfect for what I was ready to do for him!
I had six months of previous practice with my nine inch long first boyfriend. Yes my first was hung like a beast. I learned everything I ever needed, coming to master dealing with his gift.
I was going to deep throat Buddy and I knew I was up for the task. Soon I had his entire cock was disappearing into my mouth, throat and eager gullet. I looked up at Buddy and saw him with is eyes closed and mouth open wide. He was moaning and grunting loudly with each of my sucking actions. The deeper I took him the louder he would groan.
Soon Buddy began to cry out. “Oh my god Cari, Oh my god.” He moaned sounding desperate and quite moved. The more I worked him the more I would hear his OMG Cari groans over and over again. He certainly liked the job I was doing. I would let him be the one to decide about orgasming. If he did I would neither swallow nor keep him in my mouth.
My lips were making his balls red from my Colorstay lipstick. I decided to try something I never had tried. I would try to envelop his balls and see if I could get them into my mouth as well! When I managed this almost impossible task, Buddy was beside himself. He just kept frantically shouting mine and god’s name! I seriously thought he was going to have a heart attack so I relented!
I stood up and gave him a long kiss. “Oh Cari! You are incredible!” He mused. I helped him get his pants off. Then I helped unbutton his shirt and remove his sport coat. Buddy was far from handsome. He was about six foot two and about two hundred fifty pounds, a good deal of which was weight in his belly and chest.
Seeing him naked could have been quite a turn off for some people, but now he seemed as sexy as any man on earth to me. It is amazing what like can do for a gal! I was really enjoying pleasuring this largish, generous and attractively sweet man!
“I want you to fuck me Buddy!” I said without begging. He seemed stunned, even thrilled and grateful. I’d find that my transsexual friend Sandy was far less accommodating than I. Buddy later told me that she had many hang ups and getting fucked was but one of her dislikes. I put Buddy on his back on the bed and rolled a condom onto him. I straddled his ample stomach and hips and let him slide inside me.
The more I rode atop him the more I realized that the six inches of his wonderful cock seemed perfect to me. Every man I had made love to, (not that many, just four), was truly hung. I think I am attracted to confident men who just happen to have huge manly cocks! Riding Buddy’s six inch cock was pure pleasure. There was no awkward pain or discomfort at all!
I kept a steady rhythm as Buddy up-thrusted into me in unison. Riding atop a man’s cock is pure ecstasy to me especially when a guy of Buddy’s more modest size is inside me. I only had to focus on keeping him in my very willing bum, and I was really getting into it. My hard cock was bouncing relentlessly against his belly as I held on to his shoulders.
Buddy’s up thrusts were firm and my down thrusts met his. The sound of my bum meeting his balls and hips echoed throughout the bedroom. I was enjoying this almost too much. I leaned forward for a long passionate kiss.
The tongue swirling French kiss was wondrous for both me and for him. Incredibly perhaps even too much even for him. I could feel him near and erupting. His loud guttural groans filled the room. He was coming as my ass milked every spurt of his genetic fluids into the condom deep in my ass!
I was perhaps just as thrilled as he. To say Buddy was moved by my work was pure understatement. “Oh baby you’re so good Cari. Oh you are just so good!” he exclaimed breathlessly. I bent down kissing him gently as his moans subsided and he slowly caught his breath.
In moments he hugged me, bringing me against his chest. “Cari you are the best lover I have ever had!” he exclaimed. “I bet you say that to all the girls” I quipped back. “No Cari, you really are!” He said still breathing heavily and a bit breathlessly. I wondered if he needed an inhaler or something.
I was so thrilled by his compliments and earnest sounding words. This all coming from a married guy who is accustomed to sleeping with hookers! I smiled, actually thinking his compliment could possibly be genuine and perhaps even sincere!
We caught the fourth quarter of the Celtics game and high fived as Boston scored a last second basket to win. We celebrating a last second victory with a hug and kiss. Buddy soon put on a robe and I stayed in my nightie as he had room service delivered for us.
I never imagined enjoying such comfort, especially while being on the clock. Buddy was so complimentary. I couldn’t help but wonder the doubtful level of quality with whom he had been spending his time with! We watched more television and we melted into each other on the sofa.
When we went to bed I got Buddy all worked up into a lather again. He was so surprised at my spontaneity and my willing enthusiasm. I guess I just like sex I told him. “I like you a lot!” he said again smiling. I stayed the night which was more than expected. I liked Buddy too. He already felt like a friend.
In the morning I got an unexpected bonus. I awoke to find Buddy relentlessly sucking my cock. It didn’t take long before I gushed like a mad person. Buddy swallowed and licked my every drop! One thousand dollars and a free orgasm to boot. Even more of a surprise was the extra hundred I was handed on the way out. Buddy wanted to see me on Sunday!
Buddy knew I was a big Patriots fan and on Sunday when I showed up in my mink coat, he gave me a present. Again we stayed at the Boston Harbor hotel. All during the game I wore but two things – my sexy white high heels and my brand new gift – a number twelve, Tom Brady jersey. Soon I’d go from quarterback to receiver all the time wearing only my official NFL shirt!
Buddy and I would “date” three more times! Three weeks later and with over five thousand dollars in my bank account, I’d take a luxurious trip on my own to Montreal, Canada. Now with many new high heels, wigs and dresses I was on to greater heights. Armed with a lot of unexpected money to spend - my life was richer in many more ways than the money.
My new friend Buddy would unfortunately soon have both health and wife related problems. Our naughty liaison and arrangement as call girl and client would soon come to an end. I have never “worked” as a hooker since. Like in Pretty Woman, The Buddy Scholarship would take me on to many bigger and better things.
Being a woman has just so many possibilities. I was so fortunate to find being a call girl was so much better than I ever would have expected. I had lucked out in my judgement and the risk had been worth the reward. From it all I surprised myself in many ways. I learned mostly, that even I could be swayed and be bought!
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