Once Upon a Tranny

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.

Bob was more than ready for her. He was very hard and like her, anxious to be in her hot little ass. He got the lube, put a goodly amount on his hard cock, and then got between her legs. She hadn't gotten on all fours, so he just assumed that she liked it like so many women did - missionary style. Well, this worked fine for him. Her sexy boobs were within easy reach, and he could either watch her play with her dickclit or he could jack her off while he was fucking her. In either case, he was going to get to watch her cum.

As he got between her legs, Claudia raised her knees up quite a bit, giving him easy access to her waiting asshole. As he started to slowly push it against her, she wrapped her smooth sexy legs around him, inviting him deep into her body.

"Oh God yes!" Bob shouted as he slowly slid deep into her hot body. "So nice, so tight." He paused with the head of his very hard cock just inside her ass, letting her get used to it being there. He moved in and out a few times nice and slowly, giving her time to get used to him and say something if he was making her uncomfortable or it hurt. She said nothing. Now he turned his attention to her dickclit. It was hard and laying there against her belly. Not waiting for her to do something, he took it in his hand and slowly started to jack her off as he moved in and out of her ass. "Oh God this is so nice," he groaned, not taking his eyes off her dickclit. He loved moving that foreskin back and forth over her swollen cockhead. He had been robbed of his as a baby. Some doctor no doubt badgered his parents in to clipping him - one more way to pad the bill.

"Mmmm…I know," she murmured. "It's been a long time."

He didn't bother to ask just how long a long time was, he was just glad to be where he was. He started moving in and out of her tight little ass a little faster, and jacked her off faster as he did so. He thought he was going to have trouble holding off for her, but it seemed that she got off very easy this way. In no time she was even harder and moaning.

"Oh yea…" she groaned, "I'm going to cum real soon. You do that so well!" She lay there playing with her erect nipples, pulling and pinching them much like he had seen women do it.

A few minutes later, her body stiffened and jerked. She groaned even louder now and raised her ass off the bed a little higher as her orgasm started. Bob was rewarded for his efforts by a huge squirt of hot cum erupting from Claudia's throbbing dickclit. It shot out of her and nearly hit her chin. Huge gob after gob of the thick cream erupted from her dickclit and landed high up on her body, some between her boobs, some on her tummy, and some spraying over onto her jiggling boobs. In seconds he had managed to make her cum a huge amount and she had covered her body with her own hot cum.

That was all it took to send Bob over the edge. He gave a loud groan himself shoved his hard cock deep into her and began spewing his thick cream deep into her waiting ass. He felt like he was sending gallons of the hot thick stuff into her, and it went on and on and on. He couldn't remember when he had had an orgasm like he was having tonight. She was positively draining him of everything he had to give her.

"That was fantastic," she breathed softly just as he was finishing. "I haven't cum like that in a long time."

"Me either," he said breathlessly. "You really have a hot body." After a moment or two inside her as the last few drops leaked out of his now spent cock, he finally slid it slowly out of her ass.

"Was it as good as you thought it would be?" she asked with a smile.

"Oh, yea. And then some," he said as he flopped down on the bed next to her.

They talked, laughed, and enjoyed each other's company. It was even easier to do that now that the "main event" was out of the way. About an hour later they did it again, but this time tried it doggie style to start with, and then switched back to missionary. Once again Bob jacked Claudia off as he pumped his hard cock in and out of her tight little ass. And, once again Claudia rewarded his efforts with a nice hard cum, shooting her thick white sperm high up on her sexy body, though this time there wasn't as much as the first time. Bob unloaded in her ass once again, and while it probably was less than the first time for him too, it certainly felt like he had given her just as much of his cum as before.

He didn't spend the night with her, but they did make a date for Saturday evening. He would meet her over at her place and then decide where to go.

Saturday seemed to drag on forever for Bob. He had a few errands to get done and that did provide something of a distraction. Finally as the agreed upon hour approached, he drove over to Claudia's place.

Claudia greeted him with a smile and a warm welcome; she was wearing a scarlet sundress and some serious catch-me-fuck-me pumps. The house already smelled of something delicious cooking. Great, a home cooked meal, he thought, this sure beats going out. "What's cooking?" he asked.

"Well, I decided it would be nice to just make something here rather than go out this evening. So, I went to the store and got what I needed for some stuffed pork tenderloin; with all the trimmings of course. I do cook a little."

That was a nice touch, as Bob could hardly boil water without burning it. From what he could see when he went into the kitchen, he was in for a treat tonight that would be hard to match in any restaurant - at least one he could afford.

It wasn't long before Claudia had it plated and they were eating. Dessert followed, and Bob was truly amazed at her ability in the kitchen. "Are you a traveling chef or something?" he finally asked.

"No," she said, "I'm a telecommunications sales representative, which is what I tell most people is what the TS on my car's license plate means. I used to be a chef and had a small restaurant for a time. But, I got tired of the incredibly long hours and, in the end, the low pay. I was beating myself to death for peanuts. I was doing something like sixty and eighty hour weeks and after it was all said and done, I was taking home $25K a year. I sold the restaurant, did a fast retrain, and found another line of work. It was sorta fun, but the pay and hours really sucked. Not to leave out that it completely killed my social life. I thought I was just too young to be owned by the job."

"Wow. Well you certainly didn't forget what your learned as a chef. This was very impressive," he said collecting the last few crumbs of his dessert.

"Thanks. Give me a few minutes to clear this table, and we can have some real dessert," she said with a wink.

"Now you're taking!" Bob walked over to the soft white leather couch and had a seat in the middle of it while Claudia cleared the table and rinsed a few things so they wouldn't be impossible to clean later. He was getting hard at just the suggestion of getting into Claudia's ass again. He had to wonder, does life get any better than this? A hot little tranny that can cook with the best of them, and fucks like a rabbit was his dream; maybe his dreams weren't this good!

"Now," she said coming over to him, "let's get something straight between us!" She quickly sat facing him on his lap and in a flash had his belt undone and his zipper down. "Can your friend come out to play?" she asked stroking his now hard cock though his briefs. "It feels like he wants to. Do you think he'd like a piece of ass?" she cooed.

"Oh yea!" She got out of the way for a moment, and Bob quickly removed his pants and briefs.

When he sat back down, Claudia returned to his lap and, again, faced him. She unbuttoned his shirt, and Bob just sat there with a grin on his face as she did it. With it now wide open, she leaned forward put her forearms on his shoulders and gave him a long sexy soul kiss.

"Man you get me hot," he said when their lips finally parted.

"And what does this do for you?" she asked as she, in one quick motion, pulled her sundress off over her head.

To Bob's surprise, Claudia had been wearing nothing but thigh high stockings on under her dress. Her dickclit was mostly hard, with that sexy long foreskin covering the swollen head. "Makes me want to…fuck you!" he said as sexily as he could.

"I do hope so," she said reaching under a cushion and retrieving a little bottle of Astro Glide she had hidden there earlier.

"I think you had this planned!" he said with a grin as he watched her open the little bottle and pour some of the contents onto her palm.

"Really?" she quickly put her lubricated hand on his cock and moved it slowly up and down the shaft, getting it all nice and slick. Even after it was nice and slick, she continued to slowly stroke it. "I do like this one," she said with a smile. Finally she rose up a little, moved up on Bob's body, and slowly lowered herself down on his hard cock, pushing his incredibly hard erection into her waiting ass. It slid in easily, and she lowered herself down until he was as far into her body as she could get him. Then she gave him a nice firm squeeze with her ass.

Bob groaned and took her dickclit in his hand and began stroking her. He loved watching that long sexy foreskin slide over the head of her dickclit, covering it completely and then watching it come back into view as she slowly stroked her. Neither of them seemed to be in a hurry; they were just enjoying this sexy feeling as they built to a climax.

Claudia slowly poured a little of the lubricant onto his hand so it lubricated her dickclit. Now it was making a sexy wet sound as he stroked her. She capped the bottle, tossed it aside and began moving up and down on Bob's cock. Still, neither said anything; they just enjoyed the sexy intense feeling.

"I'm getting ready, to cum," Bob said softly. "So really close."