Gromet's PlazaTG/CD Stories

Sissy Chronicles

by Misti Love-Fitzpatrick

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© Copyright 2020 - Misti Love-Fitzpatrick - Used by permission

Storycodes: MF; cd; tg; leather; foreplay; tease; oral; rom; cons; X

1: Sheplacement

Professor L.W. Johnson smiled as Paula Pokovsky opened the door of her apartment and greeted him with his favorite cocktail, a 7 and 7. He kissed her on the cheek. “I love your new dress; beautiful, just like you,” he told her. He sipped his drink and she loosened his tie. As she took his suit jacket and hung it in the closet, he watched her long legs, encased in shiny, tan pantyhose.

Paula was hosting dinner for Professor Johnson. She had done so five times on Friday afternoons. Despite the wide difference in their ages – he was 49 and she was 19 – they had become close friends.

Professor Johnson had come from work and wore an expensive black suit with a red tie, his afro cropped close. His beard and mustache recently were trimmed. Paula wore her short wig of dark red hair in a bob style. Her outfit was a pink satin mini-dress, with a mock neck, long sleeves, and ruched sides; and pink patent leather pumps with stiletto heels and ankle straps.

They had met two months ago through a mutual acquaintance at the university where L.W., known to his friends as Lou, was a philosophy professor. Paula had dropped out after her freshman year. She was working as a temp under the name her parents had given her – Paul, who dressed as a male on the job.

Paula and Professor Johnson had met at a backyard barbecue, held on a stunning summer evening. The party’s host had given Professor Johnson a heads-up that Paula was cross-dressing in public for the first time, among a handful of CDs at an eclectic party that had attracted about 100 people. Professor Johnson never had met a truly passable transvestite. The prospect intrigued him.

The year was 1999, a time when transgender women commonly were referred to as trannies and were not accepted as much as today. It also was a time when people would often stare at interracial couples. Professor Johnson was black, and Paula was white.

Paula had caught Professor Johnson’s attention shortly after she arrived at the party. She wore a silver silk blouse with a ruffled front, a long string of pearls, a black pencil skirt with a mini-skirt hem, black silk stockings, and pumps of the same color with a five-inch heel. Her mascara consisted of a thin under-liner, fire-engine red lipstick, and a dash of silver eyeshadow.

Professor Johnson approached Paula, introduced himself, and asked if he could get her a glass of white wine. He could sense she was extremely nervous. As he expected, she told him that she was a cross-dresser, and asked if he still wanted to talk with her.

“Of course I do, Paula,” he replied. “Who wouldn’t want to talk with such a smart, engaging, and pretty girl?”

After they chatted for a while, Paula was tempted to pinch herself for having such good luck this day. Professor Johnson struck her as kind, with an impressive intellect and warm sense of humor. He also was handsome and possessed a muscular body. He offered her a warm smile and easy conversation. His presence calmed Paula, especially after he assured her that she was “passable.”

He was tempted to ask her if she wanted to go someplace else for a drink, but dropped the notion. After chatting for an hour or so, he asked for her phone number and got it. She noticed his wedding band and told herself not to be so over-eager.

Although Professor Johnson and Paula became close friends over the next two months, they did not become lovers. Professor Johnson was up-front with Paula that he was married to a woman who also was a professor at the university. They had two grown children, a large house in the suburbs, and a dog named Robert.

Over the years, Professor Johnson’s wife of 27 years, Linda, had become more masculine in her appearance. Her political views had shifted too. She had left the business world to get a doctorate in sociology. These changes did not affect Professor Johnson’s love for her, but he missed the woman who easily could blow $500 at Victoria’s Secret. That woman didn’t exist anymore.

Professor Johnson had shared an anecdote with Paula. He recently had gone to a restaurant with his wife and the waitress had referred to her as “Sir.” It perturbed her a bit, but not much. After all, she had buzzed her hair to almost a crew cut and was wearing baggy pants and a t-shirt.

Later, Professor Johnson had asked his wife why she no longer wore skirts or dresses.

“I refuse to allow the oppressor dictate how I look,” she replied.

“And the oppressor is?” he asked.

“The male gender is the oppressor.”

The story surprised Paula. She asked Professor Johnson what his wife would think of her.

“She has said sissies have a mental illness. It’s very hateful. Please don’t let it upset you.”

As Paula began to feel an attraction to Professor Johnson, she had hoped he would make a move on her. Perhaps the attraction was not mutual or he did not want to go outside his marriage, she told herself.

When Paula carefully broached the topic of his feelings about her and her emerging desire for him, he explained that he simply was seeking friendship. He enjoyed spending time with her. She was disappointed, but she accepted his reason and respected it.

As time passed, however, she began to wonder if his explanation was true.

On this Friday afternoon, Professor Johnson was in a particularly talkative mood. He had received a large pay raise. It wasn’t just the money; it was the respect that came with it, he told her. As Paula listened, she fantasized about him as she studied his body, his large hands, how his chest muscles filled out his white dress shirt and his big thighs.

He had brought Paula a present. She opened the pink package to find a black leather mini-skirt, a stylish choice.

“Thank you so much, Professor.” She kissed him on the cheek, making sure she removed the smudge of red lipstick.

“Don’t worry about the lipstick. My wife is visiting her mother in Minneapolis for two weeks.”

He added: “Why don’t you try it on to see if it fits?” he replied.

Paula headed for her bedroom, fingering the soft leather of the skirt. He had accidentally, perhaps, left the tag on, and she was intrigued by how much it had cost.

As he waited for her to return, Professor Johnson spotted a card on the table by the couch. It was a picture of a cross-dresser with the caption: “You feel like a woman, dress how you feel.”

How fitting for Paula, who’s going to look hotter than July in this leather skirt.

Paula returned to the living room about ten minutes later. Professor Johnson smiled as she modelled for him. She also had changed into a black silk blouse and traded her pink pumps for black high-heel ankle boots.

“The skirt is a perfect fit and I love the style,” she said. “Where did you get it?”

“In Chicago, when I was at the conference for philosophy professors. I got bored one afternoon and skipped a presentation to get you something.”

Paula thanked him again. “I’m surprised you know my size.”

“When you made dinner for me a week before I went to Chicago, I snuck into your closet and found your skirt size.” 

“You’re a devil.”

The skirt actually was a ‘micro mini,’ so short that Paula had to change gaffs to make sure her clitty was not visible. She called that gaff “Fort Knox” because it kept the valuables safe. The skirt zipped up the back, from top to bottom. Professor Johnson glanced at the gold zipper.

“Why don’t you join me on the couch?” he asked.

She nodded. First, she walked over to the record player. She put on “Super Freak” by Rick James and sat on the couch.

“Your favorite song,” she said.

Professor Johnson seemed lost in thought. Paula watched the growing outline of his erection. His suit pants were not tight, but his hardness was unmistakable. He was thinking about what he called “the line.” It was a boundary, a fuzzy line between flirtation and the sex that followed it.

“Penny for your thoughts?” she asked.

“Oh, impressed by how you look in that mini-skirt.”

“I love it,” she gushed.

Paula had approached the line a few times, most recently the prior Friday. As usual, she had spent several hours in the kitchen. The dinners were all favorites of his from growing up in the South. He gave her his mother’s recipes. She said she still was learning how to cook.

“My wife knows how, but she doesn’t do it anymore,” he told her. “This dinner was delicious, as usual.”

When he asked what was for dessert, she replied, “me.” He was sitting at the dining room table. She was standing in the kitchen, a black apron protecting her dress, her hair pinned up like a housewife in a small town. After she made the flirtatious comment, she turned to smile at him.

He stood and walked over to her.

“And if you’re dessert, what exactly does that mean, Paula?”

“Something delicious,” she said.

He undid her apron and let it fall to the kitchen floor.

“Paula, do you want me?” he whispered in her ear.

“Yes, Professor Johnson” Her voice was soft. She felt breathless.

He could see that Paula was wearing a garter belt under her skin-tight royal blue dress.

“Devil in the blue dress?” he asked.

She laughed. He kissed her neck and placed his hands around her wrists. Even in high heels, she was five inches shorter than him.

“Did you get your nails done today because I was coming for dinner?” he asked.

“Yes, at Madame Ling’s shop. Do you like them?” The nails were longer than usual, royal blue and pointed at the ends.

“Very much so,” Professor Johnson said. She wanted to tell him that she wanted to wrap the nails around his cock, but knew it would be too forward.

Paula wore nude-colored silk stockings. They gleamed in the light of the kitchen. 

“Paula, why do you wear stockings? A lot of women don’t anymore. The fashion these days is bare legs, because of Demi Moore.”

“I like how they feel on my legs. And I’ve heard that some men like hose, stockings and panty hose. Do you?”

She already knew the answer. Professor Johnson nodded. “Do they make you hard?” she asked.

“Paula, everything about you makes me hard.”

He moved his hands from around her wrists to the back of her dress, down to the spandex that covered her ass.

“You have such a full ass, so sexy.”

She thanked him and felt her clitty harden.

He couldn’t see or feel any panty lines.

“Are you wearing panties, Paula?”

“Professor Johnson, are you being fresh?”

Paula leaned over to get the cherry pie from the bottom rack of the oven. She placed it on the counter, her back still to Professor Johnson. He raised the hem of her dress to reveal her round and tight ass. Her gaff had a thong back.

“Professor, do you consider a thong to be panties?” Paula asked. “This sounds like an important question for those who work in the ivory tower.”

Professor Johnson laughed.

“More research is needed on this question. My only conclusion is you’re tempting me with that sexy booty of yours,” he told her.

The moment, however, passed. Paula had hoped he would undress her. He wanted to, but stepped back from that line. He didn’t know why; nerves, maybe; something about his upbringing, perhaps; or confusion about his growing lust for a 19-year-old transvestite, whom he referred to as “a tall glass of water.” He lowered her hem so her ass was covered again.

That was last week. This was now.

As they relaxed on the couch, he asked her to dance. She had told him a few times how much she enjoyed doing so. He watched her, as his favorite song, “Super Freak,” played: “She's a very kinky girl / The kind you don't take home to mother.” 

Professor Johnson was not surprised when Paula turned her back to him and straddled his legs. She moved her hot ass seductively and slowly lowered herself as the needle dropped on the next 45 rpm, a slower tune, “Hot! Wild! Unrestricted! Crazy Love” by Millie Jackson.

“Drop your clothes / your inhibitions / I want you wearing just a smile,” Paula sang along.

His eyes were fixed on that ass, the leather tight on every curve. He felt the skirt brush against his erection and in a flash, she crossed the line. Professor Johnson exhaled deeply as Paula reached her arms back to support herself on the couch. Slowly, she began to grind her ass against the outline of his cock, which was tented in his suit pants.

Professor Johnson undid the buttons of her blouse and kissed his way up, past her bra strap to her neck, intent on providing the foreplay he knew that she craved. She wore gold earrings and a necklace. He had bought them for her after she told him she heard that Black men treated their women like gold. She sighed and grinded her ass harder against his crotch. He moved her, so she faced him. He gently told her to get on her knees.

“Have you heard of sissies known as sheplacements?” he asked her in a near-whisper.

Paula said she had not.

“It refers to cross-dressers who are more feminine than some biological women. Even though they have penises, they know they were born as girls and are women. They love dresses and skirts, lingerie, hosiery, high heel-pumps and jewelry. They understand that men like women who are feminine. They are respectful of women who aren’t as feminine as they are – and they don’t talk shit about them. 

“But they also know that sheplacements are becoming increasingly popular with some men who want a feminine woman.

“Paula, will you be my sheplacement?”

“Yes, Professor Johnson.”

Paula removed his shoes, socks, and unzipped his pants. Freeing his cock from his briefs, she wrapped her long nails around the shaft, licked a circle around his cockhead so she could savor his pre-cum, and sucked his dick deep into her mouth. He gasped with delight as she swirled her tongue around his steel-hard penis. She swallowed every drop of his thick, pungent semen and watched as he got hard again.

Paula finished undressing Professor Johnson and led him by the hand into her bedroom.

After he made love to her, he held Paula in his strong arms. For the rest of the night, they mixed passionate sex with sleep.

For the first time, Paula felt sexual love. Professor Johnson wondered anew about the mysteries and power of femininity. His love for his wife endured, as did his love for her sheplacement.


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