Life and Time of Lady Vargos Ch. 05

When she had finished she stood up. It was Tiffany. Constance had forgotten to make the arrangements with one of the regular whores who normally did her husband's blowjobs but had happened into Tiffany who had arrived early to spend the evening with the Baron as his concubine. Constance wouldn't take no for an answer and escorted the intimidated young girl into her bedroom after she reluctantly agreed to do this. It was also to be kept secret. Constance didn't want her son Anthony knowing his cute concubine was performing other services just before he was to be cared for.

"Young lady, go into the bathroom and freshen yourself." Constance said pointing to the bathroom after she had finished with Leo.

Tiffany walked away. Constance stood with her husband. She smile as she pulled his robe together and tied the sash.

"So, how was she?" Constance asked.

"She was wonderful. Thank you."

"Your welcome. Let me help you get comfortable here."

Constance prepared the bed for him. He picked a novel he had been reading and put on his glasses and picked up where he had left off.

Tiffany came out of the bathroom her makeup all fresh. It was getting close to time for her to get to the Baron's room and she didn't want to be late.

"Well come on. I don't have all night," Constance said pulling her panties off from under her beautiful full length gown. Constance shuffled over to the chair in her 4" high heel fluffy mules. The were white with white fur. Her toenails long and boldly painted a deep red. Her gown was white full length with spaghetti straps over the shoulders.

"What?" Tiffany said nervously backing up a step.

"Get over here young lady." Constance then lifted the front of her gown exposing her dark pubic hair and then she seated herself in the chair her husband had just occupied. Constance put her legs over the arms and then put her head back while she spread her pussy with her fingers.

"Ma'am, I don't do women..."

"Don't get all goodie goodie on me. You're a whore my dear. A licensed concubine. It all pays the same."

Tiffany walked over to her reluctantly. Constance sat up in the chair and pushed Tiffany to her knees. She then put her legs back up and pulled Tiffany's reluctant lips into her pussy. Tiffany pulled back at first when her lips touched a woman's pussy for the first time. She could feel the heat being generated by Constance's vagina.

Tiffany had escorted a couple of wealthy lesbians before to public events and even kissed one of them but she had never done anything like this with a woman before. Constance held her head firmly.

"Put your tongue in my pussy and then suck on my clit." Constance knew what she wanted. "That's it."

Tiffany found the taste of the woman's pussy disgusting. Constance insisted she lick her from her ass hole to the front of her pussy, inserting her tongue in her pussy when she got there and then inserting her tongue in her ass when she was there. Tiffany performed as instructed and Constance had an orgasm.

"Thank you. I am done with you for now. Go get yourself ready for my son. I will pay you. Keep this our little secret or I will have you banned from the house."

"Yes ma'am," Tiffany said walking to the bathroom again to freshen up. She felt so ashamed of what she had just done.

"Oh, tomorrow I would like you to visit me around 5:30."

Leo looked at her over his glasses at Constance.

"Oh stop it Leo. I have that damned conference call with all those society cunts and that bitch Alice will be heading it up. I just want my feet rubbed and my toes sucked by this charming young woman, while I have to listen to the ridiculous ideas Alice has for the fund raiser. You can do that for me can't you dear," Constance gave her a look that indicated that no was not the correct answer.

"Yes," she said before turning to leave.

Tiffany stormed down the hallway trying to get the disgusting taste of Constance pussy juices off her face.

"I hate that woman," she said making her way to the Baron's bedroom.

For the first time, Tiffany actually felt cheap and humiliated after performing on Constance. She would try and finish the evening with the Baron with as much enthusiasm as she could muster.

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Dorothy sat in the fine restaurant with Jessica. Dorothy was wearing a low cut sapphire blue cocktail dress that revealed ample amounts of his cleavage. He wore blue high heel pumps with 4" heels. High enough to be very fashionable but comfortable. There were three large diamond studs in each lobe of Dorothy's ears. A large cocktails ring adorned a finger on each hand, and he was made up elegantly. He didn't seem like a person opposed to dressing as the opposite sex the way he carried himself.

"So how much longer do you have to dress like a woman before you can get on with your life." Jessica said giving a big smile for the elegantly crossdressed man.

"Another six months. Part of the final will requirements to get the rest of the money and property out of probate. Little humor from my deceased husband I guess you could say."

Jessica giggled.

"Don't you feel uncomfortable sitting in a four star restaurant having dinner with a man dressed like this?" Dorothy said throwing his head back putting his arms on his his hips pushing out his chest.

"No, I guess not. I mean you get up everyday and dress like a woman and go everywhere in public as if it were a normal thing. Does that make you uncomfortable at all?" she asked taking his hand and looking at his elegant sapphire blue fingernails. "Pretty fingernails by the way."

"Not anymore. It used to with the people staring and commenting under their breath, It was like I could hear every word. I'm used to it now I guess. I suppose most guys would do the same thing for 6 months if they knew how much was in it for them."

She smiled in agreement. She was willing to date this man in public in hopes of securing something for herself.

Jessica had dated many men before but never one like this. She had moved up the status ladder through two divorces but never dated anyone who stood to have the vast fortune that Dorothy was set to get.

Jessica and Dorothy had a few things in common. They both wore similar styles in dresses and shoes and the were both devious enough to get what they wanted by using other people.

"So what does a man like you look for in a real woman?" she said giving him a giddy grin as if she could be that woman for him.

Dorothy took her hand in his.

"Tonight beauty and pleasure. I prefer a woman that gives good head and enjoys doing it," he said making a bold sexual statement as if he didn't care if it insulted or shocked her.

"Oh really," she giggled, "I can do that for you, you know," she said without hesitating trying to ply him with her willingness to please.

"Do you swallow?" he said pushing her further sensing the woman's motives.

"Well of course I do. Is there any other way to give a proper headjob?"

Dorothy looked at her and smiled. He reached in his purse and pulled out a lipstick and compact. Using the mirror he freshened his lips while she watched.

"Very good then. Our dinner will be here shortly. After dinner you can show me."

"Sure. I'm looking forward to it," she said giving him a wink. She was watching him closely. She could perform and convince any man that she loved them. She had done it many times, but this was different. She saw him as weird to say the least, but then again rich and weird.

I've been meaning to ask you though, don't you find that collar you have to wear demeaning? I mean it's like you are a pet."

"Yes I do. Who wants to be publicly tagged, but I have to wear it. It's the law. I am a crossdressed man moving about in public," Dorothy said without reservation.

"Well you won't have to be crossdressed much longer. I bet you're a handsome man when your not in all that makeup and frills. I can't wait to see you dressed as a man," her tone turned very seductive. She felt she could be so much more convincing if he were dressed as a man.

"I've been looking forward to that day myself for many years now actually. You know, I may keep the nails even after I revert back to dressing as a man. I kind of like having long blue or purple fingernails and having my toenails painted red. I kind of like them," he gushed placing his hands in front of her so she could clearly see.

"Aren't they pretty?" he said trying to cause her to show her real intent here.

"They're beautiful," she gushed excited.

Jessica's mind took a turn. "Yuck. What a faggot," she thought. Stay focused on the goal here she kept telling herself.

"We could have our nails done together." Suggesting a supportive view and that she would still be around then.

She felt like she flowed well with Dorothy. They ate dinner and she just knew when she gave him the headjob he would desire her talents, or even mistake those talents for love as so many other men had done.

She had no idea the type man Dorothy really was. She was playing the role of Martin's marriage counselor for him and receiving nice payments for doing so.

They had dinner in the private booth in an exclusive part of the restaurant. They talked about the coaching that Martin still needed. She was very energetic to push Martin into the role Dorothy wanted for him. Show him she could do this and be an asset to him. Then dinner was over.

Dorothy stood up and lifting his dress slightly reached under and pulled his panties off.

"What are you doing," Jessica asked surprised at his sudden action in a public place.

"I want you to suck my dick now." he said sitting back down smoothing his dress under him before sitting. The table cloths were long enough to conceal him and his back was to the wall.

"Now? Here in the restaurant?" she looked at him surprised.

"Yes. Why not. It will be your dessert while I'm having my dessert."

She looked at him and realized he was serious. She couldn't lose this cash cow on the first date.

"Well I guess so," she said looking about hesitantly. She moved next to him and put her hand under his dress. She looked around to see if anyone could see them. She could hear other patrons but could see nobody.

"What are you doing?" he asked with a confused look. "Slide under the table get on your knees and give me a blowjob."

"Under the table?" she said her voice shaking a little. "That's so sleazy."

"Don't be silly. I've done it many times before. I've even done it when we had another couple at the table." He looked at the astonished look on her face. "It's what we girls do. Right?"

"I'm your date, not some paid whore," she said with little conviction though.

"You are my date. You are not a whore, so please get under the table and suck my dick as my date."

She now felt embarrassed. She knew she would be so humiliated if she crawled under a table at a restaurant like this and sucked a man's dick. Especially a man dressed like a woman.

"Well? I'm waiting," he insisted.

"Well...ok sure. Why not. A little adventure right." She tries to play off her nervousness with a little humor.

"Don't mess up my dress. I just bought this dress."

"Yeah and you're a real fag too," she thought as she slowly crawled under the table and took Dorothy's cock and put it in her mouth. She used her tongue and lips to manipulate him into a growing erection.

Jessica blushed when the waitress came to the table. Right above her the woman was innocently taking an order and here she was with a mouth full of cock not three feet away.

"Will you be having dessert?" she asked.

"Yes," Dorothy ordered an ice cream dessert.

"And will the lady be rejoining you sir?" she asked not knowing Jessica was under the table.

"She is having her dessert right now," he said.

Jessica now was pumping her head up and down on Dorothy's full erection at a pace that he had set for her with his hand. It was their first date and Jessica was performing nicely.

"Here you go sir," the waitress said bringing his dessert. She noticed a slight rhythmic motion in the table cloth. She looked away. Many eccentric types with millions in cash frequented this establishment and sometimes unusual things did happen. After all this was obviously a man in a dress she was serving. The collar around his neck made that clear. She stepped back and asked Dorothy if there would be anything else.

"No thank you."

She saw the 4" gold metallic spike heels of Jessica's red pumps she was wearing. Jessica's neck was getting tired as Dorothy had great staying power and was making Jessica work for it.

He made a call on his cell phone as he ate his dessert.

He talked for a few minutes to a man. Dorothy's breath became heavy now as he talked.

"I'm still here trying to work this all out honey. Got a bimbo helping me thinking there's gold at the end of my dick. I'll keep her on till this all settled. Are you ok?" Dorothy was sincere.

"I'll be home in a few weeks hopefully. At least you won't have to witness me dressed like a woman for too long." Dorothy took a deep breath.

"I know, I know. I love you Mitch," Dorothy said softly. When Mitch responded his love for Dorothy, he exploded in Jessica's mouth.

There was a long pause while Dorothy had his orgasm.

"I miss you. Bye," he said after the orgasm and hung up.

"Could you please hand me a napkin," the voice from under the table said.

"I thought you said you like to swallow."

"Some got on my chin. A napkin please." she said holding up her hand.

"Don't get any on my dress," Dorothy said handing a napkin under the table.

When the waitress returned Jessica was once again seated across from Dorothy. She tried to act as if she had been outside not knowing she had been seen. It was demoralizing enough that she had done what she did, but it would crush Jessica to know she was seen.

"Thank you and you folks have a good evening."

"Thank you," Dororthy replied in his male voice.

"Oh by the way, that waitress saw you under the table giving giving me head. The table cloth was moving."

Jessica's face turned red.

"Don't worry about it. I gave her a very nice tip." he said standing and straightening out his dress. "She probably thinks you're just some high class whore doing your job."

"Besides," he thought to himself, "She's cute and a possible recruit. She looks like she needs the money," as he watched her walk away.

Jessica's face was red with embarrassment. She shielded her face as she hurried out of the restaurant with other hand on Dorothy's arm.

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The next morning...

Martin had been dressed in the same red polka dot dress and high heels that he had arrived in. He had spent a great deal of his time here totally nude. He was instructed on walking and sitting properly and was only allowed to wear high heels during the lessons. As he was getting ready to walk out of the room he used for a bedroom Tabatha came in with two other large women.

"What," Martin said posturing in a somewhat feminine pose he had learned since arriving here.

Tabatha said nothing as the two other women took him by the arms and led him back to the bed. Tabatha was putting on a pair of rubber gloves as she approached him.

"No. You don't have to do this. I'm going to do it," he said as he was push back on the bed.

His panties were removed.

"Please," he pleaded but allowing his hands to be handcuffed behind him.

He looked into Tabatha's eyes.

"I don't need this. I'm going to walk like a woman. I promise. I'll exaggerate it so people stare at me if you want." he said in a panic when he was pushed back on his back.

The two women grabbed his legs pulling his feet to his butt then spreading his legs. There hung Martin's sore testicles in their male ball sacs.

Tabatha sat down on the bed with a ball gag.

"Open up now Mrs. Vargos," she said holding the gag up to his lips.

"I will to it I promise just give me a chance," Martin said as he

emotionally broke down and cried, "I'll prance about...please don't

do this to me..." the man cried and was unable to speak. When he felt

the pressure of the ball gag against his lips he reluctantly opened his mouth so it could be inserted and fastened tightly in place. His groin ached.

Grieving in the gag Martin held down comfortably on the bed. He had suffered this same routine all week. He thought it was all over and he was going home.

"Shhhh...now Mrs. Vargos, just settle down," Tabatha said as she lightly rubbed his bottom.

"I believe you when you say you are going to work on that walk. Move those hips and strut your girlish ass. Right?"

Martin shook his head vigorously in agreement.

"That's so good to hear," she said now squirting oil in her hand. "Then we won't have do this by appointment at your home then."

Martin panicked as his legs were spread.

Outside the door Martin's muffled screams were clearly audible as his nuts were again squeezed and stretched by the expert hands of Tabatha.

Jessica looked at Dorothy and smiled in the hallway.

"I ordered a testicle massage for him this morning before he goes just for good measure," Jessica said.

"Good. You were wonderful last night by the way," Dorothy said with a smile as Martin moaned in the background.

"I especially enjoyed you sucking my dick under the table in a public place," he said knowing how uncomfortable that made her. "Thank you,"

"It was my pleasure," she said thinking only of how perverted she really thought he was.

"I had a good time," he quipped.

"Me too," she said as she remember how alarmed she had been seeing how large his breast actually were when he removed his negligee that night. His rose tattoos on his pierced nipples, and the initials on his buttox. She felt like she was making out with a woman when she was sucking his nipples on such large breast.

Dorothy turned and walked away. His hips swaying side to side as he walked in his high heels.

"Faggot," Jessica said under her breath as she walked away.

"Air headed bimbo slut," Dorothy thought to himself.