Once Upon a Tranny
Keywords: a, Upon, Once, Tranny,
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Once Upon a Tranny Art Kautz Copyright March, 2005
Bob was having a time with the winter traffic. It had snowed last night, the roads were slick, and all too many people were driving like they had never seen the stuff before. He had started out early in what turned out to be a vain attempt to get to the office on time. Conditions were worse than he had expected. The radio said that all of the Denver Metro area was now on accident alert, meaning that all you had to do was exchange driver's licenses and insurance information if there was no alcohol or drugs involved and if the damage was under $1,000; which he now assumed made everyone an expert on drug and alcohol use and an auto-body damage estimator.
He pulled up behind a small truck at a traffic light, only about a mile from the office, and to his horror, saw the SUV behind his little Toyota Corolla lock its wheels and continue toward his rear end. In seconds, there was a sharp bang as the SUV smacked into his rear bumper. It wasn't a bad hit, but with the plastic bumpers cars used these days, he knew he had some damage - the SUV probably got off with little or nothing, but he knew he was fucked.
Bob released his seatbelt and got out to inspect the damage. He walked to the rear of the car and looked at his now modified bumper. The SUV's bumper guard had put a nice notch in it. As he was trying to guess what that would cost, the SUV's driver appeared next to him. She was a rather sexy, thin, brunet of average height.
"Sorry," she said, sounding very upset. "I tried to stop far enough back, it just kept on going. I couldn't even steer it."
"Yea, I saw you coming in my rear view mirror," he said, resigned to the damage, the further delay in getting to the office, and the hassle it was going to involve getting the bumper replaced.
"I have insurance," she said meekly.
"Okay," he said, and looked at her front end. The bumper guard was showing a little abrasion and a small dent, but that was about it. "Nothing wrong there that your husband or SO can't fix without going to the insurance company," he commented looking at it closer.
"Oh, I'll just have the dealer fix it when I take it in for warranty service next week. No husband or SO. Not a problem. Sorry about your bumper."
They exchanged driver's license information, insurance information, and phone numbers. Her name was Claudia. Bob was about to leave when he noticed her license plate - 2HOT TS is read. He was going to ask her what it meant, especially the TS part, but she was already back in her SUV and getting ready to leave. He put it out of his mind and got back in his car and was even more determined to get to work as soon as possible now; better a little late than really late.
Bob had a fascination with transsexuals. He would love to meet one, a real one, that wasn't butt-ugly, but figured his chances were slim to none at best. Therefore, the TS part of Claudia's license place intrigued him. Could it be that the TS meant transsexual? It probably meant something a mundane as Telecom Sales or Tech Specialist. She was pretty hot looking alright - as much as he could see of her, bundled up as she was against the winter cold. Nah, it had to be one of those other things. But, the thought nagged at him.
Later that evening, Claudia's license plate finally got to him, and he got the piece of paper out she had given him and called her. He remembered that she had said something about no husband or boyfriend, so he hoped it would be she who answered the phone."
"Hello?" asked a rather sexy feminine voice.
It was her! So far so good. Bob introduced himself and after a few minutes chit chat, asked her just what the TS meant on her license plate.
"Transsexual," she said, and waited for him to loose it on the phone. That's what it really stood for, but she also had a whole list of other things she used if she thought the guy asking couldn't handle that, as most couldn't. However, with Bob tonight, she decided to just come out with it. If he couldn't handle it, that was his problem and she was just going to hang up. She also informed him that she was pre-op and wasn't sure when the "operation" would take place, or if it would for that matter.
Bob was silent for a minute, and then finally said "Really? You're really a tranny? Wow!" He knew better than to call her a shemale.
He wasn't put off, so she said "Yes, and apparently I do a pretty good job at passing for a woman."
"I'll say. I never would have guessed you were anything but." He babbled on for a few minutes, and then finally managed to ask her if he could see her sometime - like tomorrow evening.
"Sure," she agreed, "Where did you have in mind?"
"Uh…how about Flannigan's not far from where we had our little run-in?" She knew where it was and agreed. They then set a time, and Bob was set for his first date with a real transsexual.
The next evening, Bob showed up at Flannigan's a little early, and found Claudia already there. They had dinner and a few drinks, and in the process, go to know each other some. To Bob's disappointment, he didn't get her into bed. She had a flight to Seattle early the next morning. However, she was willing to meet him at Flannigan's again that evening as she was coming back the same day. Bob took that to be a good sign.
That night Bob lay in his bed and fantasized about Claudia. She had had a dress on that evening, and it was tight fitting. He could imagine what she must look like without it. He could plainly see that she had a nice figure; nice tits, great ass, and narrow waist. There were a few details about her anatomy that he wasn't sure of, but those details could wait. It wasn't long before he was touching himself as he thought of her naked, he got hard, and all too soon he was rapidly stroking his cock and wondering what it would be like to be sliding it into Claudia's waiting ass and playing with her nice looking tits. She had gotten him so hot and horny that in no time he shot a huge load of cum into the air, with it landing all over his body.
As the day before, Bob got to Flannigan's early the next evening, and Claudia was already there. And he thought he was anxious about this date! Once again, they had dinner, chatted and a few more drinks. This time however, before he could suggest anything or that they go anywhere else, she invited him to her place for a nightcap.
"Sure," he agreed quickly.
"I don't live too far from here, so how about you just follow me home. I'll drive slowly," she said with a grin.
"There isn't any way you could loose me!"
Arriving at her place, she made him at home, got a nice cold drink for him, and then went off to get into something more comfortable than that business suit she had had on since early that morning. A few minutes later, she came out in a somewhat conservative teddy with a sheer robe on over it.
"Wow," was about all could manage as she came into the room.
"Like the view?" she asked.
"Yea, this is the sort of thing that happens in the movies and never in real life. In the movies she comes out like you are dressed. In real life she comes out in baggy sweats."
"Well, tonight I think we're after the same thing, so there's no point in playing hard to get," she said as she came over and sat next to him.
"I like the way you think," Bob said as he put his arm around her.
A kiss led to a deeper kiss, which led to him feeling up her rather nice feeling boobs, and finally they were both groping and feeling each other over and under their clothes, which soon became more off than on. They were all over each other. Bob was delighted to be with such a gorgeous tranny, and Claudia was very grateful to have a nice looking man that accepted her as she was.
Bob had finally gotten to see those missing pieces of her anatomy that he could only dream about last night. Her cock, if she called it that, was a nice size. It wasn't too long or thick for a little oral work, and, much to his delight, it was, as so many trannies were in the pictures he had seen, uncut - she had a delightfully long foreskin on it. Her balls were still there, though they weren't very large. Her boobs were a nice size, and showed no signs of scars under them. He didn't bother trying to guess the cup size: every time he had tried he had been off one way or the other. Moreover, her boobs even felt natural. Maybe it was the hormones that she no doubt was taking that did it. He wasn't fond of the "store-bought" boobs; they felt...store bought - not natural.
"How about we just get undressed and get on the bed," she finally suggested. "I'm getting way too hot to keep this up much longer."
They got up, stripped off the rest of their clothes right there in the living room, and he followed her into her bedroom. Claudia stripped off the covers and got onto the satin sheet.
"You look so good," Bob said getting on the bed next to her. He reached down and took her cock in his hand and began to stroke her, really enjoying the feeling of her in his hand. "Just what do you care to call this appendage?" he asked.
"I usually refer to it as my dickclit," she said. "I won't be offended if you call it a dick or something like that. I guess you could also call it my clit too, but clits don't squirt like that does."
"Shoot your cum kinda far do you?" he asked with a smile. He loved cocks that could really squirt a long way. There was just something exciting about watching that. He got the impression that from the way she had said "clits don't squirt like that," that her cum didn't exactly dribble out the end, above and beyond the fact that clits don't squirt in the first place.
"It does okay. When I play with it, it can land cum between my boobs." Now her soft hand reached down to his hard cock and began playing with it, stroking it up and down slowly but firmly. She was thinking it was going to feel very good buried deep in her ass. It wasn't long before she suggested that he get the Astro Glide out of the nightstand and put it where it would do the most good for both of them.
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Keywords: a, Upon, Once, Tranny,