tagTransgender & CrossdressersCall in the Professional

Call in the Professional

byxploring96©

The following story includes a transgender character, prostitution, Domination/submission, and derogatory terms used to humiliate. If this offends you please do not read any further.

*****

How did Greg get here? It's election day in Washington DC and he is standing in the Ronald Reagan Airport with a big problem. To understand his problem it is important to quickly explain the last few days.

Along with some friends, Greg had come down to the US from Canada to have an extended sports weekend. It started with a Knicks game in New York City after flying in on Friday. The Sixers beat the Knicks 116-87. None of the group were fans of either team. Sometimes they just loved watching sports and hanging with their buds. So win or lose they were going to go out drinking after the game.

On Saturday they went to a New Jersey Devils game. Being a bunch of Canadians they knew they were going to include a hockey game on the trip. They had a choice between the Devils, or the New York Islanders. The Rangers were out of town. The Islanders played out on Long Island.

Friday night they had stayed at a hotel in Manhattan in order to enjoy the City and the nightlife. They were, however, staying at a hotel in Jersey on Saturday night so they would be close to Giant's Stadium. On Sunday they had tickets to the football game. Staying in Jersey on Saturday night meant they wouldn't have to fight as much traffic on Sunday. That, along with the fact the Islanders sucked and New Jersey was one of the best teams in the East, was why they chose the Devils game.

After Greg arrived at the hotel in New Jersey, while he was unpacking some things, it dawned on him that he had left his leather jacket in the hotel room in Manhattan. He really didn't want to take the time to go all the way back through the tunnel to pick up the jacket. But it was his favorite coat, and too expensive not to get back. He called the hotel to see if it had been found. They told him the cleaning staff had found it, and they offered to send it to Greg's home in Canada. This, while unexpected, was welcome. He would get the jacket back and he didn't have to drive all the way back to the City.

Without having anything to worry about, Greg was able to relax and enjoy watching the Devils beat the Atlanta Thrashers 6-1.

On Sunday they went tailgating, and then to the Giants-Cowboys game. Greg was a huge Cowboys fan, but knew it wasn't going to end well that day. Tony Romo had been hurt, again, the week before. The Giants crushed them 35-14.

It was humbling to have to sit in the middle of all those Giants fans while wearing his Cowboys jersey. But that's all a part of being a fan. Greg is normally a quite, reserved guy, but not when his teams are involved. He would have been trash talking them all if the Cowboys won.

Then on Monday morning they got in the rental car and drove to DC for the Redskins-Steelers Monday night game. One of Greg's friends was a huge Pittsburgh fan and was completely obnoxious by the end of the game when the Steelers won 23-6. In the end the weekend had been a huge success.

As it turns out Tuesday was election day. Barack Obama was trying to make history by becoming the first black US President by the end of the night.

Greg's friends had a flight out in the morning, but Greg's flight didn't leave until 6:00 pm. With the time available he went and explored the city's historic monuments before heading to the airport.

He got to the airport at 5:00, pulled out his ticket for the flight, when the reality of the situation hit him. Greg had left his passport inside the pocket of his leather jacket. Which was now on its way to Canada.

Up until a few months earlier, crossing the border between the US and Canada had been easy for Americans and Canadians. They didn't need passports. Drivers licenses were enough. But things had changed after nine-eleven. A few months before this trip it had finally become law, that like everyone else, Americans and Canadians needed passports to cross into each other's country and to get back into their own country.

When Greg made it to the front of the line at the airport counter he tried everything he could to get on the flight, but no luck. Without his passport he was grounded.

So eventually here he is staring at a wall full of hotel ads with a phone sitting in front. Each ad has a three digit number next to it. Pick up the phone, dial the number, and you are connected to that hotel.

Greg figures he has another problem. It is DC on the night of the Presidential election. All the hotels were probably booked months ago. He has no option but to try. He sees the Marriot ad directly in front of him and dials the number.

When the phone is answered he asks if they have a room. They say they do and he immediately says, "I will take it." He doesn't even ask the rate. He is going to grab it before someone else snatches it up.

He gets a cab. It is then about a thirty minute drive to the hotel. As he enters, passing the security guard at the doors, he notices the lobby is big and almost empty. Making it feel cavernous. He heads to the front desk and says, "I have a reservation under the name Greg Thompson" and hands them his credit card.

As they are filling out his registration he says, "I was surprised to get a room. I thought every place would be full on election night."

The clerk looks at him, "Oh no. This is our slowest time. Everyone heads home to their constituency to get elected. All the politicians and their staff are out of town. So there is also nobody in town to meet with them. Nobody needs rooms."

Greg thinks about it and this makes sense. It also makes him think he could have been more selective and found a cheaper room. Especially after he is informed it is $250 a night. He decides oh well, he is within walking distance to the Canadian embassy where he will have to go tomorrow anyway. This will save him some cab fare then.

After checking in and getting the Internet password he heads up to the tenth floor. Upon entering his room he puts down his suitcase, instinctively grabs the remote, and turns on the TV. Greg travels a lot and this is just habit for him upon entering a hotel room. Of course it has election coverage.

Sitting on the bed, not interested in watching the election, he wonders to himself, now what. He grabs his laptop and boots it up. Greg brings his laptop everywhere. Quite often he gets calls from work even during his time off.

He is thinking of watching some porn and jerking off while in bed. Then he realizes that there isn't Wi-Fi. He is going to have to sit at the desk and have it plugged into the ethernet cable to connect to the Internet.

For the last few months he has been watching a lot of shemale porn. Nothing seems to get him off lately like women with cocks. Especially black women with really big black cocks. He loves when a black woman takes charge of a white guy. Making him give her a blow job, fucking him in the ass, and of course making him swallow her huge load.

Greg has never sucked a cock. But whenever he sees one of late, all he can think about is how it would feel in his mouth. He wants to know what it feels like as the texture of cock goes from soft to hard. Black cocks especially, just exude power as far as Greg is concerned. Being an anal virgin, he is like most virgins, he both wants to experience getting fucked by a cock, and is scared to do it.

But the thing that he is most attracted to is a big black booty. Even before he developed his shemale fetish, he loved ass. He finds the wide hips, strong glutes, and ebony skin of a black woman's booty superior to all others. Greg has always wanted to stick his tongue between the cheeks of a sexy black woman's phat butt and lick her asshole.

Now at forty he has still never done it. Even though nobody who went with him to a sports event would guess it, because he can be so loud there, Greg is an introvert out of, and definitely when in bed. He has never got up the courage to ask a woman he was sleeping with if he could eat her ass. And being the submissive person he is he would never take the initiative to do it without being told to, or given permission.

He doesn't really want to masturbate while sitting at the desk, although it wouldn't be the first time. As a result of all the traveling Greg does for work, he spends a lot of time in hotel rooms. This leaves him with a lot of time to himself and quite often he jerks off. Many times in smaller hotels it has to be at the room's desk because that is where the Internet connection is.

Deciding he isn't going to rub one out, at least not yet, Greg goes to a site he has spent a lot of time surfing lately - eros.com. He clicks on Trans then Washington DC. This is a site for escorts and it has a transexual section. Greg has looked at it many times before when on the road; in Orlando, Columbus, Atlanta, and other cities. Being as timid sexually as he is, he has never built up the nerve to call one of the tranny hookers.

Looking at all the incredibly sexy women he starts to get hard. He comes across a thin, white, strawberry blonde, girl. With maybe B cup tits, and what looks like a really thick cock. He stares at her for quite awhile trying to build up the courage to call.

Eventually he pulls his cock out of his pants and starts to scroll down. It looks like he is going to chicken out, again, and just end up jerking off. Then he comes across Alyssa.

She is a Black/Asian woman. Her looks are exotic. It says she has a thirty eight inch chest, an eight inch cock, and forty inch wide hips. This isn't some skinny white bitch. She is a curvy big black woman. She isn't fat. She just has curves in all the places a woman is supposed to have curves. This is Greg's fantasy come to life in the flesh. And between her tits, cock, and ass, there is so much ravishing caramel colored flesh to fantasize about.

Greg enters her number into his phone. Then stops before pushing dial. His heart is racing, as he has never met a prostitute before. Finally he pushes dial.

On the other end of the phone he hears a soft voice say, "Hello."

Greg clears his throat and squeaks out, "I am calling about your ad."

"Oh I am so glad baby."

"I have never done this before."

"Don't worry baby I will make your first time memorable. Do you want to come to my hotel or want me to come to you "

"I don't know DC well. So can you come here please? I am at the Marriot, room 1005."

"Sure baby it will probably take me about an hour."

"That sounds OK."

"See you soon baby," and she hangs up.

Greg takes a big breath after the call is over to calm down. He can't believe how nervous he was making that call. Then he realizes he was so nervous he didn't even ask the cost. Having read these ads for months when he was on the road, and then chickening out every time, he knows it is probably around $300.

He goes out to find an ATM, but finds one in the lobby, so he doesn't need to leave the hotel. He takes out $400 just in case.

When he gets back to the room his cell phone rings. It is the number he had called to get Alyssa. She asks the address of the hotel. He finds some letterhead in the desk and gives it to her. She tells him she is at the wrong Marriot but not to worry, the cab driver says it will only take about twenty minutes more to get there. He is extremely nervous again and for a minute thinks about using this as an excuse to cancel. But being the submissive guy that he is, he is never going to tell her that. He just compliantly says, "OK."

Now he is sitting in his room with two things happening. One, his nervousness is causing a queasy feeling in his stomach. Two, his little three inch cock has become as hard as it had ever been, over five inches.

About thirty minutes later the hotel phone in the room rings. Greg picks it up wondering who would call him on the hotel phone. Nobody even knows he is here, as he was supposed to be on a plane right now. He answers, "Hello?"

A female voice says, "Mr. Thompson, this is security downstairs at the main entrance."

Greg immediately panics thinking all his insecurities are coming true. They know I called a transexual prostitute and I am going to get kicked out, or worse arrested.

The security woman continues, "We have a lady, Alyssa, at the entrance who says she is here to meet you. Would you like us to send her up?"

He meekly replies, "Yes, please. Thank you Miss."

He is instantly relieved, then quickly followed by scared. He is about to meet this sexy shemale. His apprehension, and the stress from getting the phone call, has reduced the size of his cock back to three soft inches.

About ninety seconds later there is a knock on the door. He opens it and is confronted with a beautiful black woman in a strapless skin tight blue dress that comes to about three inches above her knees and displays her ample black breasts proudly.

Greg moves to the side to let her in and she confidently struts by him into the room. She is about the same height as Greg, who is six foot one. When he looks down he sees that the reason they are looking at each other eye to eye, is that she is wearing five inch high, stiletto, ankle strap, open toed shoes.

Then he notices just how absolutely stunning she is. She has warm brown flawless skin with slight pearl undertones. Her black sensual hair comes down just past her shoulders. Her eyes are slightly oriental in shape, but larger than most Asian women. Giving her an alluring look. She has thin perfectly shaped eyebrows, high cheekbones, a large mouth, with thick cocksucker lips. Her makeup is applied impeccably. She really inherited, in her appearance, the best of both of her Asian and Black ancestry

Her exaggerated hourglass figure is on display thanks to her skin tight dress. Every curve is featured. Especially, he notices as she walked past him into the room, that big black woman's booty.

Greg understands that her figure, and maybe some other features such as her high cheekbones, are the result of plastic surgery. He doesn't care. Fantasy is often built on illusion.

Stopping to think for a second, he realizes he never gave Alyssa his name. Yet the security guard called him Mr. Thompson. Alyssa must have just said I am here to see the guy in 1005 and the guard checked the registry. While Alyssa is by no means dressed cheap, or overtly slutty, the security guard would have had no trouble discerning why she was coming to his room. He puts that thought aside in order to deal with the shemale diva now in front of him.

Standing next to the bed Greg says, "You are even more beautiful than your pictures."

"Thanks baby."

Looking at this woman whose body encompasses every sexual fantasy Greg has, he tells her, "I have never done this before. I don't know where we start."

"Why don't we start with your name baby"

"Greg."

"OK Greg let's first get the gift out of the way."

He replies stuttering, "Oh, oh yes. I forgot to ask on the phone how much."

"Three hundred baby."

Greg pulls three hundred dollars from his pocket and she puts it in her purse.

Noticing how nervous he is Alyssa then suggests he sit next to her on the bed and they can talk a little so he can relax. He sits on the side of the bed leaving about two feet between them.

She then asks, "So baby when you say you have never done this before do you mean being with an escort, or being with a special girl like me?"

"Both," he replies.

"OK baby we will take this one step at a time and you are going to have the best time of your life. I promise."

As she says this she slides over so they are right next to each other with their hips touching. Gently putting her hand on his cheek she turns his face so they are looking directly into each others eyes. She leans in and starts to kiss him. Starting out with soft kisses she slowly presses her tongue into his mouth and he responds by doing the same. Then she lightly sucks on his tongue.

Alyssa says, "That was nice wasn't it?" Greg nods his approval. "Now let's get this shirt off you baby," and she grabs the bottom of his t-shirt and pulls it over his head and his sandy brown hair. This reveals his chest. While he isn't a body builder he has a fit upper body with nice pecs and a flat stomach. As her hands go back down, her fingers slide lightly caressing his chest and circle around his nipples. His nipples get hard and his cock starts to swell.

She then begins to kiss him again. She also lightly bites, then sucks on his lower lip. Followed by little butterfly kisses on his neck. For awhile they make out like high school sweethearts.

"OK now let's get these pants off and see your cock stud."

He immediately stands up and pushes his pants and briefs down to his feet. It doesn't pass Alyssa's notice how obedient he is to her. With his cock about face level to her, she grabs it with one hand and starts to stroke it. Her hand is able to cover its length completely. As she strokes it she asks, "Do you hope my cock is this size or do you hope it is bigger?"

Sheepishly looking down he replies, "Much bigger."

"You're going to be pleased then baby."

Glancing at her feet he asks, "Can I take your shoes off for you?"

"Of course baby. Get down on your knees."

From his knees in between her legs she puts her right shoe on his thigh and he opens the strap. As he takes the shoe off her foot he looks up to get her approval, when he notices from this angle he can see up her dress and is able to make out her black panties between her legs. He can tell from her eyes, that she has caught him looking up her dress. Even though she is a call girl and he is paying for her services, he looks away embarrassed to have been exposed peering up her dress like this. She ignores this, although she does smirk at his obvious self-consciousness, then proceeds to put her left shoe on his thigh. He undoes this strap also and after taking the shoe off, again looks up her dress then proceeds to up to her face.

This time she says, "Are you looking at my panties baby?"

Greg immediately blushes and looks back at the floor.

Alyssa is confident at this point that he is not just shy about being with a transexual escort for the first time, but is truly submissive. She knows how to deal with this. Standing up she turns her back to him and firmly says, "Pull down my zipper."

Greg stands up, reaches to her neck, and pulls the zipper down just to the top of her ass. He can see some cleavage in her butt at this point.

Turning and facing Greg she lets her dress fall to her waist. Her dress is so tight it will not fall past her swollen hips. She unfastens her black strapless bra dropping it to the floor. Exposing huge brown DD cup tits with two inch diameter dark brown areolas on the end. Pushing her tits together with her arms they appear to get even larger.

"Do you want these baby?"

Greg's eyes become huge. He isn't even blinking while staring at these big mounds of flesh.

"Yes please."

"What do you call a strong sexy woman whose boobs you are begging to suck?"

"Mistress?"

"So what do you want?"

"Please can I suck your tits Mistress?"

Greg certainly never thought he would be going down this Dom/sub rabbit hole today. But he is SO alright with it. He is not only going to get to suck a black tranny cock, he is going to get to serve her just like in the shemale porn movies he watches.

Alyssa tells Greg to sit on the bed. She then leans forward and lets her big tits hang in front of his face. Greg grabs each side of her left tit, brings it to his mouth, swirls his tongue around the areola, and starts sucking on her hard nipple. Then he moves his left hand up to massage her right boob while continuing to nurse on her left one. Eventually he switches between them.

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byxploring96© 4 comments/ 31702 views/ 35 favorites

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