"Sweetheart, why aren't you dressed? Your date will be here any minute."

Just then through the sheers over the front window they saw the cab pull up.

"I don't want to."

"What the fuck do you mean? 'I don't want to.' Look I could have arrested you along with the rest, but I saved you and gave you a nice home and pretty clothes. Now get fucking dressed. We'll talk about this later."

Roy's wife, Cathy was no longer the fresh beauty she was ten years ago. She didn't know what to make of the sissy slut he brought home. But Gary, dressed up as 'Gina' had worked out fine. Cathy didn't have to turn tricks any more.

Roy was a vice detective. He was on the inside, part of the team. He knew where and when there were going to be raids. He had the knack to approach johns who would pay well for a safe date. He arranged dates for Gina, and a hooker he kept in a cheap flat down town. Just like he used to pimp his slightly dim wife Cathy out.

Where Cathy slipped up was letting her guard down when Gary/Gina started helping around the house. After all, he/she didn't have to waitress at the diner for spending money. Roy bought Gina's pretty clothes. But not Cathy's.

He explained writing Gina's clothes off as a business expense, but since Cathy no longer worked for him...

He had created a shell company to write off part of their mortgage as home office.

The flat downtown was written off as warehousing. He also did some money laundering for clients.

Soon Cathy was letting Gary take her car and do the grocery shopping. She didn't tell Roy about this. She never suspected Gina would do anything but go straight to the store and straight back, because she told her to.

'Bing Bong.'

"Your date is her. Quick, upstairs and change." Then he welcomed the gentleman in.

"That won't be necessary." said the john.

Good thought Roy. "Sweetheart, come meet you date."

He turned back in time to see the date whip out his badge and two cruisers block in the cab. Just then a uniformed cop escorted Cathy, cuffed, from the kitchen. He'd come in the back door.

"What the?"

"Roy Davidson, I am arresting you and Catherine Davidson. You have the right to remain silent....."

A plainclothed lady cop led Gary out to an unmarked and gently put him into the back. The driver took them to a mall and they got into a red Honda Civic. From there they drove to a truck stop and pulled up to a grey Chrysler Caravan with tinted windows. It was hidden between two big rigs.

"OK. You go with them. They'll take you to a safe house until the trial. I'll see you soon. Good luck.

The trials were over in just more than a year. The victim impact hearing ruled that Gary needed a new identity because the threats sent to him through his lawyer were deemed to be credible.

Now he's 'Greg Tomey' living in a far city on a small stipend and looking for work.

The lady the employment center hooked him up with was named 'Sharon'. She was looking for a live in housekeeper. If he got the job it would give him a place to live where unlike the neighborhood his flat was in, he wouldn't have the stress of seeing cops every day. Wondering if they were aware of his part in sending one of their brothers to prison.

"How soon are you available, Greg?"

"Pretty well immediately, Mam."

"Good. I have your resume'. We'll be in touch."

He wondered how good the past they gave him would stand up, but he really had worked in a fast food restaurant, and had been a cleaner for an office maintenance company.

"You'll have Tuesdays and Wednesdays off. This will be your apartment. This is it's key. This one is for the service entrance, this one's for my front door, this one's for the service elevator.

"Come, meet chef. She'll be your supervisor. That's her apartment across the hall."

Sharon owned two floors of the building. The kitchen, utility room, gym and servants apartments were on the lower floor. Stairs led up to a landing with a discreet door to the upper floor.

"Jen, dear, this is the new house keeper, Greg. I'll leave him with you. I should be home by seven."

"Thank you Sharon. Greg, pull up a seat while I finish this."

Greg sat on a stool across the island from Jen, who was doing something on a tablet.

She was the same five two as Greg, but a bit rounder in the face. Hard to judge the rest of her figure in her shapeless chef's whites. Her hair was covered in her chef's hat.

"There, groceries ordered. How about a coffee.?"

Soon Greg's life was a safe comfortable routine.

Awake at six. Dress. Have breakfast with Jen in the kitchen. Seven thirty serve Sharon's breakfast in the sun room. Eight thirty hold Sharon's coat, then see her to the elevator. Change from his formal suit to casual work clothes. Help Jen, do the vacuuming , cleaning and laundry.

At noon, lunch in the kitchen with Jen, then off until four. Help prepare dinner, set the dining room table. Eat with Jen at five. Change to a suit and when the receptionist called up, be waiting with the door open when Sharon stepped off the elevator. Hang up her coat, then while she changed, wait to serve her before dinner drink in the den.

Help Jen with the cleaning up, then be ready to serve Sharon 'till nine.

About Sharon. She's a mid forties executive. From 'old money.' Quite pretty. A few inches taller than Greg. Ash blond, crystal blue eyes. Dresses for success at work, then elegantly feminine at home. Belongs to all the 'right' organizations and clubs. Dates occasionally, but no one steady . Entertains at home occasionally.

A warm and friendly employer. "Call me 'Sharon', unless we have company, dear."

Greg had lived in this city long enough to find stores that were accommodating to 'Gina's' patronage. He's left Roy's with literally just the clothes on his back, and couldn't very well buy any pretty things while in protective custody.

Everything was going great until one Tuesday evening. The service elevator Greg had called arrived. When the door opened there was Jen.

"Greg? What's going on here? What's in the backpack? Care to explain?"

"It's my day off. I'm going out."

"What's in the backpack?"

"I'd rather not say. They're my things."

"Get in." She pressed the button for Sharon's floor. Sharon was waiting when it opened.


They went to the sun room.

"Greg, I trusted you and let you into my home. I should have done it before, but in light of recent goings on, I've had you investigated. Funny thing. The investigator hit a wall beyond what was on your resume'. Care to explain?"

"Um, er. I haven't done anything wrong. Honest."

"Jen, take his bag and empty it on the table."


"Yes, or I call the police."

"No, no. Not the police. Please no."


Out tumbled blue platform heels, a red leather purse, and a blue velvet sleeveless mini dress. In the purse was some makeup, plastic hoop earrings, and some cash. There was a stunned silence.

"Um. I um. I can explain."

By the time Greg told them his story Sharon and Jen understood and were nearly in tears, as well as very embarrassed.

After that Gina could dress before she left for a night out.

It was a few Fridays after the confrontation.

"Mam, anything else before I turn in?"

"Dear, will you join me for a glass of wine before you go?"

"Yes mam. It'd be my pleasure."

She had the glass he's just served her.

"Come, sit with me."

Her soft yellow cashmere sweater, like most of her casual clothes displayed a generous amount of cleavage. She pulled her long grey and creme diagonally striped skirt, which was spread out across the burgundy leather couch to her thigh.

Greg was a bit shy about sitting so close to her. 'God, she's beautiful' he thought.

"Now Greg, are you ever going to forgive me, and start calling me 'Sharon' again?"

"Yes. Yes. Look, I realize I should have told you before, but, um. The threats..."

"Well, it's all over now. You're safe here. I'm very pleased with your service. So lets move on and not speak of it any more. Can we do that?"

"Yes, of course, um, Sharon."

"Good. Cheers then."


"Am I late?"

"No Jen. Come in dear and get yourself a glass of wine. Greg has forgiven us."

Jen poured a glass and sat on the wing back chair set at right angles to the couch."I knew he would."

They sipped their drinks.

"Greg, I like to think of you and Jen as part of the family. I hope you can start to feel the same."

"Um, yes. I'd like that. Um. I left home at fifteen, and never had a real, um."

He wondered if he's said too much.

"Now, how do I say this. This is a bit awkward. Jen, can you help me?"

"What Sharon wants to ask, well. Well, would you like to dress in your pretty clothes around the house?"

"Yes, dear. Would you be comfortable wearing a dress here? Would you be my maid? When there's just the three of us? If that would be too much, you know, no pressure. Whatever you feel more comfortable with."

Greg could hardly believe his ears. "God! Really? I could be 'Gina' all the time?"


Blush. "That's my girl name."

"Gina. Sweet name for a pretty girl."

A week later.

" Yes Sharon?"

"Dear, come look at this." She was looking at her laptop in her home office. "Tell me, would you wear dresses like this around the house?" The next Monday three sexy maid dresses arrived for Gina. A blue velvet one, a black satin one and a pink velvet one.

"Let's try on some shoes."

Sharon's foot size was close enough to Gina's. She gave her half a dozen pair of shoes she no longer wore.

Tuesday, late September. Gina spent the morning doing her personal laundry and cleaning her apartment. Then she had lunch with Jen.

"Going out tonight?'


"Got a date?"

"No, just going bar hopping. Maybe find a dance club."

"Can I join you? I can be off by seven thirty."

"Sure. Sounds like fun. Knock on my door when you're ready."

Gina wore her long sleeve knee length maroon dress and two inch heel red pumps. A short gold necklace and big hoop earrings were her jewelry.

She was surprised when Jen knocked on her door right at seven thirty.

"When I told Sharon we were going out clubbing she told me to get going as soon as I served her main course. Said she could find her own dessert."

"Wow that was nice of her. And wow again, you scrub up pretty nice."


She usually wore rather shapeless clothes and no makeup.

Tonight she wore a white silk blouse with a ruffle collar and cuffs on the full length sleeves. The front swooped well down. Her powder blue skirt was many mid calf folds of wool, held up with a french blue belt. On her feet were black three inch open toe stilettos. Her makeup was subtle, pink lip gloss matched her stick on nails. Without her chef's hat her auburn hair fell almost to her shoulders. Diamond stud earrings were her only jewelry.

"I've got a car. We can drive."

"Cool. Any ideas?"

"How about that new oyster bar on Seventh? You're not allergic to shell fish, right Gina?"

White wine and they shared a mixed sea food platter.

"Um, Gina?"

"Mm?" She'd just put a medallion size crab cake into her mouth.

"You'd know. Is there a gay bar here? I mean, just curious. Never been to one, obviously. Er? Don't get me wrong. I'm OK with, you know, different sexual orientation. That's the right way to say it? Right? Um."

"Oh, honey, relax. We're all friends here. I know you're heart is in a good place. Want to go to one? A gay bar? Sure, finish your wine. We'll go to the 'Pink Monkey'."

"Like right now? Tonight? Um?"

A short drive later.

"Hey Gina, hows it hangin'."

"Sam! Hi. This is my friend Jen."

Samantha couldn't help checking out Jen's shapely compact body with a sweep of her eyes. "Well, hello Jen! What can I get you ladies?"

Jen blushed. She hadn't been given that kind of attention by another woman before.

"I'll have a 'pink monkey'."

"Naturally, you always start with one. How about you, Jen?"

"What's a 'pink monkey'?"

Gina. "Oh, sweet, slightly tangy, lots of booze hidden in it."

"Good panty remover." Sam opened her mouth slightly and the tip her tongue darted out for a second.

"Sam, behave."

"I'll try that another time. I'm driving tonight."

"Get her a virgin monkey. Same taste but no kick."

They got their drinks.

"Over here. Meet the gang."

It was a fun night. Gina's friends took an instant liking to Jen. They got home just after midnight.

As they get to the point in the hall between their apartment doors, Jen said "That was fun. We should do it again." Then she surprised Gina by kissing her in the lips. "Girlfriend."

A few weeks later.

"Hey, Sharon's going out Saturday night. Said we could knock off at five. Want to go out? Eat out then bar hop?"

"Sure. Can we go back to the Pink Monkey?"

"For real? You want to see Sam again don't you? Could lead to something."

"NO, I don't want a date with Sam. Sheesh!"

" OK, OK, just kidding. Get a taxi this time?"

"What are you two girls talking about a taxi?"

"Jen and I are going out Saturday night. Bar hopping."

"Well,if you can be ready by five my driver can drop you off someplace, then you only have to get a ride home."

They went to a pizza place, shared a medium and a carafe of Merlot. Gina got Jen's life story as they ate.

"Split the check?"

"Sure, with tip, looks like thirty each."

The 'Monkey' was only a few blocks away, so in spite of the cold they walked. Jen reached for Gina's hand. Two gals walking holding hands seemed natural. Years ago that would have raised eyebrows. Things have gotten better.

The Pink Monkey was crowded. It was a fun night. They each got pulled to the dance floor more than once.

They danced a slow dance together.

"Mm. Girlfriend, you're a fine dance partner."


They giggled as the night door man held the door for them. The elevator door was staring to close. Then it stopped and opened. Sharon was holding it for them. God she looked elegant. Her hair up, subtle makeup, her full length sable open, revealing her classic gown.

"Wonderful timing. Sounds like you two had a fun evening."

Jen giggled. "Sure did. How about you?"

"How about we have a night cap? I feel like sitting on the balcony with a dram of Highland Park."

"Bit cold isn't it?"

"Not if we dress for it. Jen, you wear my red fox, Gina, my mink. I'll grab the scotch and three glasses."

"So, where did you go tonight?"

They told her about their evening with lots of alcohol fueled giggling.

"A gay bar! That IS exciting. Sounds like you fitted right in."

"Are you kidding, if Jen flirted any more with Samantha, I'd be coming home alone!"

Gina laughed.

"You witch! What about that drag queen you were dancing with!" More laughs.

"Lola's all show. She's got a straight wife at home. The sitter cancelled at the last minute and Amy told Lola to go anyway, since she was already all dolled up."

"What was your evening like?"

"Stuffy and boring. It was a charity event. Corporate 'must show the company colours' as Uncle Fred says."

"Who'd 'Uncle Fred'?"

"CEO, president of the company. Mother's oldest brother."


"Cocktails, dinner, too many speeches, dancing. Bla bla bla."


"Sorry darlings, I'm being a bitch.Forget it."

They sipped the whiskey.

"Jen, you look so cute in that fur. Doesn't she?"

"I was thinking more 'elegant' myself."

"Are you saying I'm not cute?" Laugh.

"Beyond cute, girlfriend. Beautiful."

"Oh you. So, any rich single men at the party?"

"Yes, two kinds. Too young and too old."

"If you could introduce me to a 'too old' I could become a rich widow." Laughter.

"Would you really want a hundred year old geezer for a husband?"

"Are you kidding? Get the will signed, then fuck and suck him to death. Voila, Jen the rich widow!" They all laughed.

"Oh my," Sharon wiped the tears of laughter from her cheeks, "I had no idea you were so evil, dear."

"It' always the quiet ones. Isn't it?" Said Gina.

More laughs.

Soon they quieted down

"Well my darlings, it's past my bedtime. You two can keep going if you want."

"No, I'm done too. How about you Jen?"

After they hung the furs in the closet Sharon gave them each a hug and a kiss on the cheek. "Sweet dreams darlings."

"You too Sharon."

At their doors Jen wrapped her arms around Gina and gave her a long slow sweet kiss. "Thanks for a wonderful evening. Girlfriend." Her right hand slipped down and she gave Gina's rump a friendly slap, then went into her apartment, leaving Gina standing there perplexed.

Even Sharon noticed Jen''s subtle makeup, and how she seemed a bit touchy feelie with Gina.

Gina wore her pink velvet maid's dress and pink ankle strap four inch heels. "Anything I can get you before I turn in Sharon?"

"Just a 'goodnight kiss' dear."

A quick kiss had become one of the perks of the job since the balcony night.

"Sweet dreams boss."

"You too, my love."

There was a note pushed into the door jam of her apartment when she got there.

"Come over to my place for a drink when you're done. J.'


"You like?"

Jen answered the door wearing a cream coloured dress of a snug soft stretchy material. It conformed to her body from it's scooped collar to half way down her thighs. Her makeup accentuated her soft brown eyes. Her little gold heart shaped earrings peeked out under her loose hair. A gold chain supported a little gold heart that nestled in her generous cleavage.

"Love your pink dress. I'm having a rye and ginger. How about you?"

Gina followed Jen into the kitchen.

"Sweet slippers." They were three inch spike heeled with a pink fur strip over the instep and a pink fur puff at the front of the ankle strap.

"Thanks. They're a Christmas present from Sharon ,last year. So? Beer, wine, rye and ginger, G and T?"

"Rye and ginger sounds good."

They sat together on the couch. The TV had a channel that showed soothing nature pictures and played soft music. The lights were dimmed.

"Cheers, then."

"Cheers." Sip. "Mm."

Jen's hand moved across Gina's shoulders. Neither spoke. Jen looked into Gina's dark brown eyes. They both knew. Gina took Jen's glass and set both on the coffee table.

The kiss was long and tender.

Jen stroked Gina's arm. "I've never had a girlfriend before. I mean, not, like. Um."

"Me neither. I dated a few times, but nothing ever came of it."

"Both boyfriends I had thought they could own me. Control me."

"You're too smart for them. You deserve better." Gina leaned forward and kissed Jen.

"I'm sorta scared."

"I won't hurt you, Jen, dear. Never ever."

"But what if I can't please you. You know? In bed?"

"Hey, girlfriend, I'm the sissy boy. I'm the one that should be nervous. What if I can't , you know? Get it up? Perform?"

As they cuddled, Jen's hand slipped under the crinolines of Gina's dress. "That's not what I'm feeling." She stroked. "Seems ready to me." She giggled.

"Uh!" Gina mewled.

Jen pulled the hem of Gina's dress up with her left hand as she pulled Gina's cock out of her panties.

"Ready for a special kiss?" She lowered her mouth to Gina's lap.

Gina had been fondled, stroked and sucked by many men. Part of being a sissy whore when Roy owned him. But never like this. The physical motions were the same. But never by someone who loved him, and he loved. The emotional connection made it so much better.

"Jen! I can't hold it. I'm!"

Jen pulled aside as Gina squirted.

"I'm sorry, I'm sorry."

"You just sit still Girlfriend, I'll be right back."

Jen returned with a warm damp facecloth and a towel, then proceeded to clean Gina and the spatter up. She cooed. "There, was that good? I know how to please. Does that feel nice? A soft fluffy towel to dry it?"

She wrapped the damp cloth in the towel and tossed it . "Here." She picked up their drinks from the table.

Pub: 29 Dec 2020 07:53 UTC
Views: 173