Tex and Tamara

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Man meets beautiful woman who has a surprise.
10.5k words
4.72
57.4k
71

Part 1 of the 2 part series

Updated 06/07/2023
Created 12/30/2014
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NTsarina
NTsarina
212 Followers

Author's note:

Here is a little story about a young man who has to open his mind and forget social taboos when he meets a woman who is not what she appears to be. I tried to find an editor but no one responded.

*****

Tex pushed the door open to the diner and walked in. There were only a handful of people sitting at the tables and two at the bar.

"The usual," he said to the fat bar maid.

"Bacon and eggs," she called to the cook.

"How are you today Tex?"

"Fine, I guess, nothing exciting to report."

"How are your classes going?"

"I was ill the last few days, so I haven't gone."

The waitress, whose name was Dorothy moved down the counter to a young woman sitting four chairs from Tex. He gave her a once over and noted that she looked Latin and was quite pretty. There was a paper next to her coffee mug and when Dorothy moved on Tex got off his chair and walked towards the girl.

"Hi, do you mind if I borrow the paper?"

She gave him a smile and showed white teeth and curious eyes. "No, please take it."

There was no accent so she wasn't a new arrival; he thought when he walked back to his chair.

When his food arrived, he poured a lot of Tabasco over it and then wolfed it down as fast as he could. He checked his watch and then left a $10 note on the table.

Dorothy noted the young woman watching Tex as he left.

"Cute, isn't he?"

"Yes, he is. What's his name?"

"Tex, but he is not from Texas. I think he is from Oregon or something like that."

"Does he come here often?"

Dorothy wiped the counter, "Pretty much every day."

"My name is Tamara, thanks for telling me, but I have to go to work. Those rich lawyers can be real assholes."

Dorothy watched the young women get up and pick a briefcase that she had left on the floor. She wasn't tall, but had beautiful long black hair, almond shaped brown eyes and her skin was the color of coffee with milk. When she walked away, she noted that she must spend a lot of time in the gym, because her legs were perfectly shaped and her black pants covered an ass that Dorothy would have given her left arm form.

Tex made it to his first class and sat down in the last row. He took out his sketch book and opened a new page. Up front the teacher was talking about depth, angles and shadows. On a table was a vase with red and white tulips. The idea was to take the flowers and draw them in a different setting. Tex began drawing and in a few minutes he had transferred the flowers to the hand of a young woman sitting at a bar counter. When he looked at his work, he realized she looked like the girl he had seen in the diner.

"That's good work Tex," said the teacher standing next to him.

"Who is she?"

"Oh, just a woman I saw today."

"She must have made an impression, since you drew her."

"I guess."

Tex Morgan had moved from Oregon to New York a year earlier. He had applied and been accepted into an Art's program where he studied drawing and painting. He didn't like water colors, but was decent in oils. His favorite was a simple pencil and then fills in the color, like a kid. His parents had always told him he had talent, but he knew he wasn't good enough to make a living out of painting. He needed a real job, but for now he was OK.

He finished at two and went back to his small grimy apartment he rented. It only had one room and he could cook and shower at the same time. As far as the furniture he had a bed, a small table, a chair and a sofa. He seldom had people over since he preferred to go out. He had a social life and he was out most evenings until late. He didn't have a girlfriend because he didn't like to be told what to do or where to go. As far as sex, he either used his right hand or picked some girl up at a bar. He was a good looking young man. Blue eyes, sand colored blonde hair, a strong jaw and cheekbones. He was just less than six feet tall and lean.

He picked up a bag full of dirty laundry and walked back out again. On the corner one block away from his apartment was a launderette. He stuffed all his things into one machine and started it. He then went out and crossed the street to the Diner where he had been just a few hours earlier.

"Black coffee, please."

"Coming up," said Dorothy.

There were several people around him and by the look of them; they were all workers, plumbers, electricians and so on.

"Here you go. Oh, do you remember the young woman who was in here this morning?" said Dorothy, when she placed a mug with hot coffee in front of him.

"Yeah, what about her?"

She winked at him, and said. "I think she likes you. She asked about you at least."

"Mm, sounds interesting. She was very cute."

"You should have seen her ass. I bet she could crack a walnut with her ass cheeks."

"Dorothy, you shouldn't talk about your customers that way."

She laughed. "If I was twenty years younger, I would chase that ass from here to Canada."

Dorothy was a lesbian and Tex had once seen her with her girlfriend and the thought of the two women together naked in a bed had left Tex with nightmares. She was a wonderful woman in many ways, but god had not been kind to her when it came to her looks.

He took a serviette from a holder and wrote down his phone number. "Give this to her if she comes in again."

Dorothy smiled. "Of course I will, you lucky bastard."

"Where are those copies I asked for," the man in the dark suit asked.

Tamara opened a drawer in her desk and took out a thick block of papers and gave it to him.

"Thanks, by the way, you look stunning today."

"Thanks Mr. Gordon."

When he had left, she cleared her desk and took out her purse from another drawer. In the elevator, she was surrounded by several other paralegals that worked at the firm. She had been with it for two weeks now and she did enjoy her work. Some of the lawyers, like Mr. Gordon, could be ass holes but most of them were too busy to give her a hard time. She had even been to court a couple of times and had found it fascinating. She had decided to continue to study and take the bar exam.

Tamara lived in a small apartment in Brooklyn and when she closed the door behind her, she went to the fridge and found a big bottle of water. She drank half of it straight from the bottle. Her watch told her it was just after six in the evening and she had to hurry. She was meeting some friends for drinks at eight.

In the shower, she washed her hair and then soaped her body. She thought about jerking off, but then decided against it. Instead, she made sure her cock and balls had no hair and then turned off the water.

Standing in front of the mirror in her bedroom, she gave herself a critical look. Her body was firm with C cups and an eight inch circumcised cock. Her ass was hard and round. A guy she had fucked a few years earlier had told her that her ass looked like if someone had cut a soccer ball in half and glued it to her.

She dressed in a short skirt and a polo neck sweater. She always had problems getting her cock in place and even worse when she was wearing a thong, like today. If someone could invent sexy underwear for Tgirls, he would become a millionaire, she thought. After applying some makeup she tied her hair in a pony tail and left the apartment.

When Tamara walked into the Rainbow Bar off Broadway it wasn't very full. Just a few people hanging by the bar and to the side were several tables where her two friends occupied one. The Rainbow Bar was a watering hole for the gay and Trans community. There were several other bars, but Tamara and her friends liked this one.

"Hi girls," she said, and sat down.

"How was your day?" asked Sandra, a tall brunette in her thirties.

"Same thing, different day, but I did see a cute guy this morning."

"Tell us," said Lola, a girl in Tamara's age with blonde hair and green eyes.

Tamara waved to the bartender and when he came over they all ordered another round. Sandra had beer and the others wine. When the drinks arrived Tamara cleared her throat. "I saw him in the diner where I have breakfast in the morning. I think he lives close by."

"Does he know?" said Sandra

"No, no, I don't even think he suspects anything. Today was the first time I talked to him."

"Last time I met a cute guy and told him I had a cock he almost punched me. Lucky me, I was faster and pushed him away," said Sandra, and took a sip from her beer.

Lola sighed. "It's so funny you know. Guys will try to pick us up, but as soon as they find out what we are, they run away. Maybe I should start any conversation with a dude with, 'I'm a transvestite, what's your name?'"

The others laughed and Tamara said, "I think Tex, that's his name, will be all right with the fact that I used to be a man. He is an artist, and they are usually pretty opened minded."

"Really, what kind? Photographer, painter?" said Lola

"Painter."

"You sure know a lot about him," added Sandra.

Tamara smiled. "The waitress in the diner is a real chatterbox, and she told me everything."

They continued talking and Lola told them about a guy she was dating one and off. He knew she was a Tgirl and Lola suspected he was with her more for the rush than actually being in love with her. The three friends had several experiences with men who wanted to be with them as a way to try something new. If the guy was nice, it always hurt when they found out his real intentions, which usually came out over a month or so. They decided to move on and go and see a movie.

Tamara grew up in Miami and she was born Carlos Jose Lopez. When she was around nine or ten her mother caught her trying on her older sisters clothes. At first no one thought about it, but when young Carlos would show up to dinner in a skirt the parents realize something was off. After many visits to psychiatrists specializing in children they were told that their son was a young girl trapped in a boy's body. Mr. Lopes had a fit and went on a three day bender. Mrs. Lopez went to church and prayed for her son. Carlos decided to call himself Tamara, and wear make up.

The Lopez family was well off. They lived in a nice neighborhood and by the time Tamara was eighteen she drove a BMW and wore designer clothes. Her parents had finally come around, and accepted that their beloved son was a woman. After graduating, she applied to the University of Florida and got in. She studied to be a paralegal and worked for her father in his hardware store. Every penny she made she put aside for an operation. She had found a doctor who specialized in transsexuals and he had put her on estrogen and other meds. After a year Tamara was ready for her first operation. She had talked to other Tgirls she knew and to her doctor. She had decided to only do her breasts and not her cock.

When she woke up after the operation and looked down, she was horrified. The doctor calmed her and said it would take a few weeks until they had settled. A month later, Tamara went to the beach in a bikini and she was proud over her new C cups. Men would turn and stare at her. The only problem was to keep her cock in the minimal bikini bottoms.

When she graduated, she applied for a job and got it. She moved to New York and only visited Miami for the winter holidays. She had met Sandra and Lola at a party a year earlier and the three had become good friends.

Tex bought a twelve-pack of beer and walked one block back to his apartment. He turned on the TV and looked for something to watch. He settled for an old Bruce Willis movie and opened the first of his beers.

His mind wandered and settled upon the girl in the diner. There had been something about her that he couldn't put his finger on. The more he thought about it, he was sure there was something off with her and he wanted to find out what it was. By the time he was on his last beer he had formed a plan. The next time he saw her he would ask her out. She was better looking than most of his dates, but he was sure that she would say yes. When he went to bed an hour later he didn't bother to follow his usual routine with a late night jerk off. He was so sure he would get laid the following evening.

When Tamara walked into the diner the following morning Tex was already sitting by the counter with a cup of coffee. She nodded to Dorothy, and said. "Morning, bacon and eggs, please."

"Coffee?"

"Of course."

When she had sat down two chairs from Tex she turned to him. "Good morning."

"Hi, I was just thinking about you," he said.

She was surprised. "And what were you thinking?"

He got up and walked over to her, but didn't sit down. Instead, he leaned with his back against the bar and smiled at her. "I was thinking that I would take you out for dinner tonight?"

He wasn't shy, that was for sure. "Let me eat my breakfast and think about it."

Tex was a bit surprised. He had thought that it would be a simple yes or no answer.

"Yeah, OK, that sounds fair. I'll be over there waiting for your answer."

He walked back and while he did Tamara looked at his ass and it looked good in the jeans he was wearing. When he sat down she turned back to Dorothy and raised an eyebrow. Dorothy winked and smiled at her. Tamara had already decided she would turn down the invitation. It wasn't that she didn't find Tex attractive, but he was moving too fast for her taste. She would have preferred if he just had sat down next to her at the counter and talked for a while.

Half an hour later Tex looked up when he saw movement at the bar. Tamara was collecting her briefcase and then she walked over to him. "Sorry, I can't today. But if you come in tomorrow morning, we can talk about a time in the evening."

"Oh," he said a bit disappointed, and continued. "OK, same time tomorrow."

She blew him a kiss and walked out. Tex watched her walk by the window and then disappear down the street.

"Shot down on your first attempt," said Dorothy, serving him some more coffee.

"I guess so, but the battle isn't lost yet. We are meeting her tomorrow morning."

"Good for you, honey."

When he had finished his coffee he had to run to make it to his first class. He just made it before the professor turned up and closed the door.

"Class, today I will give you an assignment. How you interpret it is up to you. I want you to draw, sketch or paint something that is a duality."

The class was quiet for a while and then a man in the back said, "Can it be human or can it be a thing?"

"It can be anything you want, even abstracts."

Tex was scratching his head with his pencil. A duality, he had to give it some thought.

"Today is Wednesday, please present your work on Monday," said the professor.

The rest of the day Tex spent going from class to class, art history, modern art, and abstracts and on and on it went. He enjoyed all of his classes, but by the end of the day he was no closer to figuring out what duality he could draw. He decided to go home and sleep on it.

The following morning when Tamara walked into the diner Tex was already at his usual table and she sat down opposite him. "Hi, I only have a few minutes. At what time do you want to meet and where?"

"Are you in a hurry?"

"Yeah, one of the lawyers is giving a disposition in an hour and I have to get his paperwork ready for him."

"Oh, you are a paralegal, that's interesting."

"Very, we can talk about it later."

"Fine, I'll meet you outside Ralph's at eight."

She knew the restaurant. It was on the good side of casual. "OK, see you there."

When she had left Tex sat back and smiled. The night would work out just fine, but he still didn't have a clue what to draw."

"What are you wearing tonight?" asked Sandra.

She and Tamara were having lunch in a small bistro across the street from Tamara's work. "I have no idea, maybe a skirt and a blouse, something simple."

"Good idea, you don't want to show your sluty side on a first date."

Tamara giggled. "I'm not a slut."

"Well, we could argue that point, but I don't have time. Will you invite him home or go to his place?"

"I'm not sure, I have to break the news to him gently, and then see where it goes."

"I prefer to just go with them. When they see the "surprise" they have to make a decision there and then, not too much time to think."

"You are right, but I like this guy so I am going to give him a chance."

Sandra sighed. "Have you ever counted how many men you have managed to sleep with after telling them you are a Tgirl?"

Tamara took a big bite from her sandwich and thought. "No, not really, but I would not say many."

"See, the odds that this guy will sleep with you is minimal. The odds against us are huge, you know."

You are right, but I'm a positive thinker. Maybe Tex is different."

"Tex? You got to be kidding, is that his real name?"

Tamara giggled. "Yes, and I don't see what is so funny."

Sandra shook her head, and said. "I have to go, but good luck tonight."

They hugged goodbye and Tamara watched how her tall friend walked away. Several men looked after her and one even whistled. If they only knew that the tall brunette carried an eight inch cock under her mini skirt, thought Tamara.

Tex was standing outside Ralph's when Tamara walked up behind him. "This is a good start, you showed up," she said.

He turned and took a step back. She was dressed in a bone white dress that reached her feet. Over it she had a short black leather jacket. Her hair was hanging loose around her shoulders and she was wearing a touch of makeup. Tex had noticed that even though many Latin women wore a lot of makeup they didn't really need it.

"I could say the same thing," he said and gave her a peck on her cheek. She smelt good.

"Let's eat, I am starving," she said, and led the way inside.

Tamara ordered a fish dish and Tex stayed with meat. They decided to share a bottle of wine.

Tamara hated this moment, but it was something that had to be done, and she figured it was best to get it over with. Some of the Tgirls she knew did it after dinner, figuring that if the guy left at least she had had a good meal.

The wine arrived and after the waiter had moved away and left them alone in the booth, she leaned forward. "There is something I need to tell you, Tex. It is important."

Fuck, he thought. She is married or has a boyfriend. Instead, he said, "OK, what is it?"

"I'm a transvestite."

"A what?"

"Transvestite."

Tex looked at her and then laughed. "You are shitting me?"

Tamara blushed. "No, why should I?"

He looked to the left and right and then turned and looked behind him. "Is this some kind of reality show?"

She was becoming angry. "No, it's not. I just told you I am a transvestite; do you know what it is?"

"Yeah, a dude who liked to dress in women's clothes, but you don't look like a dude."

She sighed. "Well, I can guarantee I am what you call a dude, under the dress."

"Oh, oh, I see." Tex swallowed. The reality of what Tamara had told him had sunk in. He continued. "Well, I don't know what to say. Is your name Tamara or is it Teddy?"

She smiled at him. "It used to be Carlos."

"What do I call you?"

"Tamara."

He drank some of his wine and played with his napkin. There was an uncomfortable silence that Tamara eventually broke. "You have two options. One, leave and we will never talk again. Two, you stay and we have a nice dinner together, it's up to you."

Tex looked around him to see if anyone had heard their conversation. The people close by were deep in conversation, and he realized no one except he knew that the pretty young women sitting opposite him was a guy. He thought about leaving, but where should he go, home? "OK, let's have dinner, and you can tell me all about how Carlos became Tamara."

The more he heard the more he liked her. Even knowing she was born a man there was never a moment where he could see or hear her do anything manly. At one point she got up and went to the bathroom. He noticed she went to the ladies and when she came back, he said. "I suppose you use the booth?"

NTsarina
NTsarina
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