Correspondence with Anne Ch. 01

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My first time in this section of Literotica.
Special thanks to the real “Anne”, the only transsexual I know, for her insights.


Carl sat at the computer and scowled. He had found Literotica by accident, looking for actual porn.

He was captivated.

Alone since his wife had passed almost three years ago, he was lonely and bored. Oh, he managed about two or three of what he called “baby boomer booty bumps” a year, but he missed the intimacy of a long term relationship. He was turned off when the few times he seriously dated anyone he got the feeling they were more concerned with the health of his bank account than the opportunity to bond. Still at 52 he could understand the concern.

He wasn’t rich, but he was very comfortable. They had several insurance policies on each other, plus a healthy savings account, retirement accounts, and investments. He was seriously thinking about retiring at 55, as soon as he vested at his company. He couldn’t draw retirement until he was 62, but there was more than enough to last until then.

Being almost compulsive by nature, before he committed to any course of action he would do massive research. It used to annoy his wife no end.

After reading for several months, he decided to try his hand at writing. In his own opinion, his first efforts weren’t that great. He took a creative writing course, he reread books by his favorite authors to see how they approached writing.

James Michener, Louis L’Amour, John D. McDonald, and Dick Francis all had two common traits, something he shared. Attention to detail and research.

His writing improved, and his scores reflected that. He hadn’t won a contest yet, but he was hopeful. Especially intrigued by the Survivor contest, he decided to participate.

Loving wives, romance, poetry, non erotic, even science fiction went fairly well. He wrestled with incest because he found it repugnant, and decided to save it until last. Lesbian and gay wasn’t really that hard, he just wrote it like he would romance.

Non consent and domination made him a little uncomfortable, it went against his core beliefs to force anyone to do things. But in the interest of accuracy, he found some bondage chat rooms and explained who he was and what he was doing, research for a writing project.

He got a few rude comments, some wild stuff he discounted immediately. But a few were readers and contributors to Literotica, and answered in a reasoned, intelligent manner, describing the lifestyle to the best of their ability. He actually corresponded with some on a regular basis after the story, which got good numbers and congratulations from his sources.

He tried the same approach for his story on transsexuals, going into chat rooms. Most rejected him out of hand, but four, after reading his entry, actually talked to him.

One he stopped talking to because she kept hinting around about dating. Another was just too scatterbrained to be taken seriously. The third stopped talking to him because her boyfriend got jealous.

The last, who went by Anne, was a joy to talk to. Literate, intelligent, honest almost to a fault. They quickly left the chat room for more private talk, mostly through emails.

He told her about himself. Fifty two, comfortable, widower, not ugly, not handsome, just average.

She was forty seven, with what she describe as a mature soccer mom type look. She was single.

They talked about relationships, his marriage.

Her longest relationship lasted six years, he left her for a younger T girl, said she was old and boring. She took it hard, said it was the closest thing she had ever had to love. It struck him as an odd comment. She had been alone for two years.

He asked, you’ve never been in love? Not lust, not infatuation, but deep, committed, rest of your life love?

She signed off because she was crying.

He apologized, he didn’t mean to cause her pain.

She told him not to worry, and no she had never had ‘the one’ feeling with anyone. She often wondered what it felt like.

They talked in depth, what made her choose that lifestyle? Was she still comfortable with it?

She replied she was who she was, and to try to change it now would be foolish.

She laughed when they talked about the stories on the internet, very few wanted to be sex slaves for herds of blacks or crazed mistresses. When it came down to it they wanted what gays, straights, lesbians, or any other group wanted. They wanted to be loved and appreciated for who they were, without hiding it. To be accepted.

Her eloquence was moving, and he wondered what she sounded like, how she gestured when she made a point, did she pout when she was angry?

They continued to talk after he had written the article. She read it and asked.

“This was about us, wasn’t it? About what could have been?”

He admitted it was.

“Well, it’s a lovely fantasy. I can dream about what if late at night. Thank you.”

They corresponded almost every day for four months, and then one day Maltepe Escort he stopped.

He didn’t talk to her for two weeks. She sent him numerous messages, from lightly teasing to almost frantic. Please talk to her, she missed him.

He emailed her a formal letter

Dear Anne,

I too have missed our talks. I didn’t stop to hurt you, I had some thinking to do. You know more about me than most of my relatives. It wasn’t because you were an anonymous entity I’d never meet, it because I wanted to tell you.

This is what I’ve decided[she almost had an anxiety attack, what if he was telling her goodbye]. I want to meet you, to buy you dinner, to talk into the night in person. I want to hear your voice, see your facial expressions.

I don’t know where you are, but you’ve indicated that it isn’t that far away. We have reservations at D’Angelos’ in Barrington. Seven thirty, Friday, that should give us time to eat and have a nice conversation. Ask the hostess for the man with the friendship rose, and she’ll bring you to our table.

This is unchartered waters for me, so if I say or do the wrong thing, be patient with me, I really would like to meet you.

Don’t email me back. Just come. Please.



Anne was shocked. Was this a date? A get together of friends? Should she go? What should she wear? What if he was a nut case? What if he was someone she could fall in love with? What if used her and broke her heart? What if he thought she was too fat, or ugly, or too old?

She confided in her best friend.

“Are you an idiot? Of course you’re going. You haven’t been out in two years with a man, what can it hurt? He already knows what you are, and he still wants to meet you. Look, I googled the restaurant, very nice. Pricey, even. Is he rich? Even if it’s not romance, you’ll get a good meal and maybe some intelligent conversation. What have you got to lose?”

They spent Friday afternoon getting her ready.

Simple black dress, barely showing her knees.

A strand of pearls. Black seamed[control top]pantyhose,black two inch heels, just enough to make her walk a little more sexy. Pearl earrings, a simple gold bracelet, small black satin clutch purse.

Hair and makeup styled and applied, taken off and done again. Finally she was as ready as she could ever be. She kissed her friend and set off.

She arrived fifteen minutes early, and it was too hot to wait in the car.

She felt a little self conscious asking for the man with the friendship rose, but the waitress smiled brightly and took her right to the table.

He was already there and rose to meet her.


He was almost exactly how he described himself, but more handsome than she expected.

Six feet tall, well dressed and groomed, Gray to silver hair with just a few strands of brown, hypnotic blue eyes, a nice tan.

He didn’t know what to expect, but this wasn’t it.

Five nine in her heels, warm brown eyes under a dishwater blond bob. The dress didn’t mold as as much as suggest, and she had pretty legs. He secretly rejoiced, he had always been a leg man.

A few heads turned as she made her way to the table.

They shook hands and he gave her the rose, already in the vase.

They were seated and just smiled at each other for a moment.

He finally gushed.

“My gosh, why did you lie about your look? You’re stunning. I didn’t know what to expect, but this wasn’t it.”

She glowed under his praise. He was about to learn about her teasing manner.

“And you sir, are much more presentable than you indicated. What were you expecting, a man in a dress?”

He colored, while she laughed softly.

“I’m only teasing, Carl. Don’t get all serious on me.”

He relaxed.

“Honestly, Anne, I didn’t know what to expect. Half the men in here watched you walk to the table, and I’d bet my house not a one though ‘that’s a man in that dress’, especially me.”

“Thank you, and I haven’t thought of myself as a male since I was sixteen. I’m a woman, Carl.”

“And an attractive one. I know five people in here dining, the phone calls will start about noon tomorrow wanting to know where I found such a beauty.”

“What will you tell them?”

He looked surprised.

“Why the truth of course. I met you on the internet.”

She actually giggled.

They ate, had coffee, dessert. And talked, and talked. Time flew by, and soon it was closing time.

He walked her to her car. It was only ten, and neither wanted it to end, but neither wanted to rush things.

Then things went wrong. Her car refused to start.

He checked under the hood, the cable ends were corroded. He had the tools to clean them, and put jumper cables to it, but it wouldn’t turn over.

She was in tears, wondering who she could get to come and get her. Cathy wasn’t answering her cell. He gently extracted her from the car and put her in his.

She was still trying to call Kartal Escort someone when she noticed they were moving. Suddenly she was scared.

“Where are we going?”

“You have a choice. I can take you to a motel, or you can spend the night in my spare bedroom.”

Anne was panicky. She lived very modestly, she couldn’t afford a motel, but on the other hand, she was nervous about spending the night at a strangers’ home. She started sobbing, saying she didn’t have money for motels.

He stopped in a Hampton Inn parking lot. Taking her face in his hands so she would look at him, he explained to her he would pay for the room if it would make her more comfortable. He would pick her up in the morning, take her to breakfast, and back to her car to see if they could get it started one more time.

She looked into his eyes and made a decision.

“Don’t waste your money when I’m sure you have a comfortable bed in your guest room. And no funny business!”

Pausing she giggled again.

“Unless I start it, of course.”

He glanced at her, grinned, and put his car in gear.


She loved his house, what she could see of it. It was close to midnight.

He showed her the guest room, made sure there were plenty of towels in the bathroom.

“I don’t have anything you can sleep in except a tee shirt, will that do?”

“I was hoping for a lace teddy, but this will do fine.”

She had recovered her sense of humor. It tickled her when he blushed, but it really got her when he said, maybe next time. He made tea and they talked until one. By then they were both nodding a bit, so they said their good nights. She hugged him on impulse and felt him stiffen slightly before he relaxed and returned it.

They both lay in separate beds, processing the night and it ramifications.

The clock said eight thirty when she awakened, and it took her sleep fogged brain a minute to process where she was. At sometime during the night he had laid a new toothbrush and some paste in her bathroom. It embarrassed her he had been in and out while she slept. She showered, put her dress back on, and wandered into the kitchen. She found a note on the coffee maker.

“Good morning, Anne. Hope you slept well. The maker is set, just press on. Eat anything you like for breakfast. I got a friend that owns a garage to swing by and pick me up, we’ve gone to get your car.

I hope you don’t think this is too forward of me, but I really enjoyed last night, and want you to stay the weekend. No strings attached of course.

Well maybe one or two. I know you didn’t come prepared to spend time with me, so let me make it up to you, please.

As I told you before, financially I’m quite comfortable, and by your own admission you live modestly. If you look on the dining room table, you’ll find my spare key ring, and three hundred dollars. Please do not take offense, but I have money and no one to spend it on besides myself, and really, how many power tools can one man own?

Take the money and buy a couple of things to wear. Jeans, trainers, and a nice top or two.

Something casual. A nice pair of shorts wouldn’t hurt, you have great legs. Oh, and undies, of course.

I have a few conditions. Nothing from Wal Mart. We have a very nice mall just four miles away, Northgate. Just punch it into the GPS. DO NOT take my truck!

And just so you know, I hate white underwear. I’ll probably never get to see them, but buy something that makes you feel good. I”m partial to pink, personally.

All this is up to you, of course. If it makes you uncomfortable, don’t do it, but it is a gift freely given. Either way, I’ll be back when your car is done.

But I really wish you would stay.


Anne sat, sipping coffee, and reread the note.

She called her best friend Cathy and asked her what she thought.

“Girl, don’t be an idiot! You said you liked him, and he didn’t try to rape you last night. Shop, girl, shop! I’d kill for a man who would do that for me. If you don’t want him, can I have him? Does he like regular girls?”

“I don’t know, and no, you can’t have him. Now, not to be rude, but I have some shopping to do. I’ll tell you all about it Monday. Bye.”

She loved his car, a small Lincoln. Not knowing how to work GPS, she simply stopped at the first gas station and asked directions.

It had been awhile since she could shop without worrying about money, and she took full advantage.

She hit every store, comparison shopping, then going back and making her purchases.

Two pair of forty dollar jeans, buy one get half off the second. Same for shorts, one modest white pair, one beige cargo type.

Two bright tees, one pink, one yellow. One nice button up shirt, all on sale.

A nice pair of white Nikes’, and two bra and panty sets. One pink, one black. The black bra was a pushup, and the pink panties were boy shorts.

She wore the jeans that she thought made her butt look best and the pink tee home.

She looked at Kurtköy Escort her watch and was shocked she had been gone five hours. “I bet he thinks I stole his car” she thought as she rushed back.

Her car was in the drive, but she didn’t see him when she entered the house. She called his name a few times, before seeing him through the kitchen window, mowing the grass.

She waited until he noticed her and waved. He waved back, but kept going. She could see he was almost done. Putting her purchases in her room, she went back to the kitchen and made tea.

When he was done he rinsed off the mower before putting it back in the shed.

She didn’t notice him enter until she felt his eyes. He was standing in the kitchen doorway, just watching her.

Jumping a little, she put her hand to her mouth.

“My goodness, do you always move so quietly? Most men I know would have made all kinds of noise.”

He grinned at her.

“Oh, I can be quite noisy under the right circumstances. Nice outfit.”

Getting up, she twirled around, slowly. She could almost feel his eyes on her ass. Glancing over her shoulder, she did catch him staring. He colored.


“Why? If it didn’t have some effect on you I’d have wasted my time and your money. Thank you, by the way. It was the best time I’ve had in ages. I wished you would have come.”

He groaned.

“You’re already pulling the shit rule on me? So soon?”

“What in the world are you talking about?”

“You know. I think it’s rule number five in the Secret Society Of Women. Men are good for shit. Carrying Shit. Moving Shit. Fixing Shit. And most of all, Paying for Shit.”

“Oh, that rule. Stop it right now! Next you’ll be wanting me to show you the secret handshake. Then where would we be?”

“And speaking of fixing shit, when it comes to vehicles you’re the stereotypical woman.

All women think all they have to do to a car is hit the switch and go. You’re lucky, that was the original battery, and your car is fourteen years old, you need to think about replacing it. We changed the oil, filters, belts, and most of the hoses. Plus a new battery, and a tune up. And before you say it, if you offer to pay me back I’ll be pissed. I didn’t do it for you, I did it for me. If you have reliable transportation there’s no reason you can’t be be back next week, provided of course we get along the rest of the weekend.”

He paused, looking at her reflectively.

“What would you like to do tonight? A movie? Dinner out? Anything you like, your call.”

“Well, what I’d really like is to stay in. We can order takeout and watch a movie, but I get to pick.”

“Damn, you’re not going to pick a chick flick, are you?”


“Can I at least pick the takeout?”

She smiled.

“Sure, anything you like as long it’s Chinese. Now, what’s for lunch?”

They found cold cuts and made a sandwich and iced tea. Afterwards he showed her the house and yard. The yard was about an acre and a half, with four apple trees and a grapevine across the back.

He told her he used to plant a garden, but since he was alone now he usually just went to the local farmers market.

They relaxed, became more comfortable with each other. Took a drive in his big four wheel drive truck.

After consuming massive amounts of Chinese food, didn’t want to get hungry later, you know, they settled on the couch with a bottle of wine.

She picked a Nicolas Sparks movie, a predictable heart tugger. He almost went to sleep, twice.

He was half asleep when she sniffled at the sad part, and without even thinking he put his arm around her and pulled her close. She froze, not knowing what to do, but when he didn’t pull back she snuggled in tighter and held his hand.

After the movie they just sat comfortably, and then they both dozed off. She woke with a start, gravity had gotten them and they were both half reclining on the couch. It woke him up and he sat up. Yawning, he asked if the movie was over.

“Yes, for about an hour. You snore, you know?”

“Sorry, did it annoy you?”

“It was sweet, but then again you weren’t up against my ear.”

He glanced at the clock. ten thirty.

He stood, yawning again.

“I don’t know what schedule you’re used to, but I’ve been getting up about six every morning for the last thirty five years. A habit I can’t seem to break. After staying up last night, it’s got me. I’m for bed. Did you buy a gown or do you need another tee shirt?”

“Shirt, please. Thank you for tonight, for the weekend. I can’t remember the last time I’ve enjoyed myself so much. Good night, see you in the morning. Oh, and I don’t get up at six, let me have my beauty sleep, goodness knows I need it.”

“Who was he?”

She didn’t understand the question.

“He who?”

“The idiot who told you you weren’t an extremely attractive person. Point him out to me sometime, I’ll kick his butt on general principle.”

She fairly glowed at the praise.

“I’m beginning to think you eat too much beef, you seem to be full of bull. But thank you.”

He yawned again.

“Welcome, Annie. Night.”

He pulled her to him for a hug, and she molded to him. He leaned back, kissed her on the cheek like it was the most natural thing in the world, and went into the bedroom.

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