A Game within a Game Ch. 02D

Rob gave her a hug "I'll do my best."

Helena opened the door and made herself comfortable in an easy chair; Rob looked at her for a moment and closed the door. He directly went to the practice room. On the desk in that room was a large piece of paper with his name on it. He unfolded it and started to read what the instructions for him were.

He had to go upstairs to his bedroom, put on the costume there; including the wig and shoes, and come back to this room.

He did as was asked, and found the pink dress and matching lingerie.

Rob thought it rather funny and was not upset to wear this, he had worn it yesterday and the surprise effect was gone. Still, the wig was a different story.

It was a very childish blond wig, with long corkscrew curls along both sides of his face. The curled hair flowed on his shoulders. It really wasn't his style, but it was Cathy's party he thought.

Finally he was done clothing. He wore a white suspender belt with white stockings with seam, white bra and white panties. He made sure the seams were straight; he knew she would find a reason to punish him, but not about seams that weren't straight.

Furthermore he wore the pink dress and a pink petticoat, what showed beneath the dress. On his feet he wore pink low heeled shoes with laces. He watched himself in the mirror and thought that the outfit was cute.

He went downstairs to the practice room and made sat himself in the chair at the desk. A few minutes later Cathy entered the room carrying a large bag and a cane. Rob couldn't see what was in the bag, but it was not heavy he could notice.

"So Rob, I'm not calling you sissy today, that effect will be gone and you will be prepared on it, so there is not much sense in repeating that. I have another practice for you today.

First you are going to write a text on that white board. I give you the text right here, but if you do things wrong, I'll punish you. Not by a cane, not yet, but be prepared for it later. You have already made so many mistakes, that you will be given six strokes on your butt. But first I have to ask something of you. Are you prepared to do what I ask? The only thing you will suffer is a bit of humiliation, nothing serious, and nothing to be concerned about, you won't have any troubles from it, I promise, but I want your word that you will do as I ask."

"I can have a bit of humiliation, as long it in the game," Rob answered, a bit reluctant.

"I promise: it is in the settings of this game. Me as the teacher, and you the 'student'."

"I promise: my word on it," Rob said, surprised.

Rob studied Cathy, she was normally dressed, a white blouse, a grey skirt, tan stockings but with a contrasting black seam, so she was wearing something sexy he thought; and normal flat shoes.

Rob had to write on the white board: 'I have to worship my Mistresses'.

"Is this all I have to write down?" Rob asked.

"I maybe have more texts, start with that," Cathy replied.

Rob grabbed a white board marker and started to write on top of the white board.

He forgot one thing, while he reached out to do his writing, his skirt was also reached out, so his stocking tops and garters became visible and a part of his bare thighs above it.

"I see you are not ladylike at all, I was so afraid for it," Cathy said, "don't you see what is happening? While writing I see your naked thigh, that is a very bad behavior. I have to correct that. My penance for this will be petticoat punishment. You already wear one petticoat; you will have to wear another one."

Cathy opened the bag and took out a white petticoat with lace on the bottom and gave it to Rob.

"Please put that on Rob," she commanded.

Rob thought it rather funny and had no objections.

"Remember, for every next infringement you will be further punished. I have another petticoat in this bag."

"Thank you, Mistress Cathy," Rob just said.

"This is just part of your punishment. I want hold hands," she gave Rob a hand "and now you cannot let loose until I tell you. Please come with me."

Cathy went ahead, holding hands with Rob and left the house at the backside. Rob expected her to go to the house at the back, but instead she went left and walked behind her house on a gravel-walk.

Cathy followed the gravel-walk, which cornered around her house. Rob hesitated and looked behind. He saw the path probably was around the house. Suddenly he understood: she wanted to walk with him to the front-side of the house, so he would be visible to the public.

He stopped, firmly holding Cathy's hand, so she also had to stop.

"I won't go to the front of your house."

"Rob, you just earned yourself another petticoat, and another round of the house. You just gave me your word, does that mean anything? And should you be seen, who will recognize you? Do you think you are the first one I play this game with? I'm a very experienced Mistress."

With clear reluctance Rob followed Cathy. Finally they walked in front of the house, but lucky for Rob there was nobody near. He felt embarrassed, especially when Helena looked at him through the window and gave him an encouraging smile.

Soon they were at the back of the house again and went in the back door.

Cathy let go of him and they went in the practice room again.

She handed him another petticoat, this was a red one, even longer than the other two petticoats.

His skirt was really wide now.

"I'll be right back," Cathy said, and she left the room. Two minutes later she was back, and told Rob to give hands again.

Rob didn't say anything, he was sure otherwise the next punishment would follow.

So out they went, along the back-side, then along the house to the front-side and Rob thought he would froze. A woman was standing at the front door. He stopped immediately and said "I go back."

"Another punishment," Cathy said "I still have your word," and hesitantly Rob walked next to Cathy.

Cathy greeted the woman and said to her "This is my new pupil, as you can see I am giving her petticoat punishment, but right now I'm out of petticoats. He just earned another one."

"What a sweet boy-girl, and what a nice clothes. I'm Cathy's neighbor Christina and you are?" she gave him a hand.

"I'm Rob," and shook her hand.

"I'm pleased to meet you Roberta. Cathy, I think I have another petticoat, just come to my house and pick it up."

"Thank you, I will be much obliged," Cathy said, "I'll come to you in a few minutes."

And Rob and Cathy walked further, finishing their round along the house and a minute later were back in the study room.

"Give me a second, Rob," and Rob was left alone again.

So far no real problems, Rob thought, that woman Christina probably had seen more guys like him.

A few minutes later Cathy came back.

"I thought you would have another petticoat," Rob asked.

"It is 'Mistress', if you want to say something to me, and we are going to get that petticoat right now."

And again they held hands, and together they left the house, again.

Again they walked to the front, but this time she took Rob to the pavement. Rob didn't look up or around, he kept his eyes downwards.

They walked about 25 yards on the pavement, suddenly Cathy opened a low gate what gave admittance to the garden of the neighbor's house. They headed towards the front door of Cathy's neighbor and Cathy rang the bell.

He heard a whistle, he looked back and a young man probably had seen his petticoats and stared amazed at him.

Rob felt he colored from top to toe and suddenly became very warm. Cathy looked at him and just smiled, she pushed the bell again of the front door and within a minute later Cathy and Rob stood in the hallway of Christina's house.

"It's a pity my husband isn't home, then he could also enjoy the sight of this pretty boy-girl." She smiled provocatively at Rob.

He observed Christina, outside he didn't have to nerve to take a good look at her, but here in her own house he didn't mind. Christina was somewhat older than Cathy, still attractive, her face was lightly made up, and sporty dressed, wearing jeans and a sweater. But the sweater was pretty tight, and Rob saw that her breasts were perfectly shaped. He decided he liked her.

"Follow me, girls" and they all went upstairs to an empty bedroom.

"This was the bedroom of my daughter, but she lives in the city, but I'm sure she left me some lingerie."

Christina rummaged through belongings of her daughter in a cupboard, and finally she had a long petticoat in her hands.

"My daughter used it with line-dancing, and it is still in a very good shape," Christina explained.

She handed Cathy a purple ruffled petticoat, the other ones were soft, but this was a stiffer one.

Cathy looked at it and said: "I want to pay for it."

"No of course not, dear. It lies just dusting in my cupboard; in fact I give it to that nice boy-girl. She is so proud to come to my house, she deserves a gift," she smiled at Rob and winked.

Again Rob blushed, but still had the presence of mind to make a curtsey for her and to thank her by kissing Christina's hand.

"You have trained him well, Cathy."

"No this is not my training, but from my friend Marion. I think you have met her a couple of times," Cathy answered.

"That lady with the reddish hair, yes I remember. You have nice friends, Roberta," and again she smiled.

"If you permit me, I want to watch one of your lessons in the future."

Cathy quickly replied "Not soon I'm afraid, Roberta is in the good care of his wife and Mistress Marion, this is just an extra session of petticoat punishment in combination with anger management."

"I see," Christina looked at Rob with renewed interest. "So he has a wife and another Mistress; and now he is with you."

"Don't ask," Cathy said, "in fact he has another friend living with him soon; also a female doctor just like me."

"You really must be special, Roberta," Christina said amazed.

"I hope to see you soon," and they walked downstairs again and at the door Christina hugged Rob and whispered in his ear "Visit me soon, I'm not married anymore, I would love to dress you up."

When they walked outside, Rob dug in again for as far that was possible, Cathy asked Rob "what did she say to you?"

"She asked me to visit her."

Cathy was silent "I have no idea why I ever called you a sissy, you are everything but a sissy," shaking her head while they went in her house again.

Rob could hardly move through the hallway, his petticoats touched both sides of the wall.

"Do you want to have the purple petticoat Mistress?" Rob asked.

"Well thank you dear, but it was a gift from Christina to you, don't offend her by not taking it. She might ask you to wear it in the future. Please wait for me here." With these puzzling words she left Rob.

Rob did as was asked and waited for Cathy's return. It has passed 14:00 and maybe Helena was in the other building already. He decided to wait for Cathy as she asked him to, she had a bunch of tricks and he was sure she had taken care of Helena.

After a few minutes Cathy came in the room again.

"So far you did pretty good Rob, I expected more resistance from you, and clearly you are a man with high principles. I like that. Whenever we will play a game again, I just ask for your word instead of trusting me. Maybe you learn to trust me, and you are right in distrusting: you need to earn trust instead of asking."

She asked Rob to follow and they both went to the other building.

"Should I undress Mistress?" Rob asked.

"No, keep everything on. I want Helena to see how petticoat punishment works."

They walked to the playroom and Rob had to sit in the middle of the room on a chair, in the middle of his petticoats. He wore just too many petticoats to sit comfortable.

Cathy picked up two more chairs and placed them near Rob. She sat on one and both awaited Helena's arrival. Then Helena came in. She wore like Cathy a white blouse, but with a black skirt and high heeled black boots.

"Helena is the Head-mistress, I told her you behaved badly, and she will give you the six strokes with the cane.

But first I will do the warming up, never use the cane without preparing." The last sentence was meant for Helena.

"I think it pretty warm here, I just walk in my lingerie," Helena said, "but I don't want Rob to get too excited, so I just keep on my slip."

"I will do the same," Cathy agreed and soon both women paraded in their luscious slips.

Cathy wore a knee-length white slip, with lace at the hem and breast part. When she turned, Rob saw the side split, what showed her suspenders.

Helena had exactly the same slip, but in black. Now Rob could see: she also wore her suspender belt, as she promised to wear it at all times.

"Rob, come here please, and bow over my lap," Cathy ordered.

Rob did as was asked; he felt her slip over her nyloned legs shove and couldn't resist caressing Cathy's legs. She didn't seem to mind, maybe she likes it, Rob thought.

Cathy took away Rob's petticoats; Rob heard Helena say "Four petticoats? How pretty, I will buy you some extra Rob, at home I want you to wear five at least," and she laughed. "Very pretty, this is a game we can do in our living room also Rob. This has nothing to do with a playing room."

Cathy lowered his panties and softly began to spank him with her hands.

But soon she spanked him with more force, and Rob could feel his bum starting to glow.

After a while Cathy got tired and said to Helena "He is all yours. Stand up Rob, leave your panties where they are and 'walk' to Helena."

Rob sidled to Helena and went over her lap, exposing his bum to her. Helena lifted his petticoats and Cathy handed her the cane and showed her under what angle she should hit Rob and what part of the body was suitable for this kind of punishment.

She also showed Helena how far the cane had to be hold, because this instrument could easily be misused and do harm.

"Time for your first lesson, Helena, give the first one."

Helena lifted that cane and hit Rob with a perfect straight strike.

Rob moves his ass, but it wasn't very painful.

Helena noticed and her next blow was dealt with considerable more force.

A welt appeared on Rob's arse and he moaned "Ouch."

"Careful, Helena," Cathy warned Helena, she showed Helena the maximum angle from which she could hit Rob.

The third blow went much better, Rob moaned, but only a deeper red vague stripe appeared.

"Your next strokes should be next to the ones you have given. They may not cross, always the same direction."

Soon the six blows had been given and Rob thanked Helena by kissing her. It was not according Mistress sub protocol, but Cathy understood what was happening here: it was the expression of deep love between two people.

"Rob, I think you learned a valuable lesson today. One is trust, and the other is that not everybody out there is making a fool out of you, when you are vulnerable. And by trust, I hope you have learned to trust me. Yet, I hope you come back to me soon, with or without Helena, I'm not completely convinced that you can keep yourself in control."

Rob looked at Helena who said "If I notice he needs some learning again, and Marion and I can't make him understand, I will send him to you. Then it will be without me, I do trust you and I think: you are doing a great job."

"Well thank you Helena, I don't think Rob likes the idea coming here without you taking care of him, but he is a grown-up boy-girl now, and I think I can make him understand," both girls laughed.

Rob didn't laugh, he had enough of the shit, and he already angered again.

To walk in these clothes was of course a funny sight, he was already used to it now, and he felt pretty comfortable wearing all these pretty petticoats, but he didn't like to be taken as a fool.

If they knew he enjoyed wearing them, they would have clothed him in something he would hate, he decided not to let know Cathy, that he liked this outfit.

But Helena had noticed that he liked them, she was too clever Rob thought, and she asked "Can I buy this costume from you, including petticoats?"

"Sure, I can get a new one at Bridget's."

"I will pay for your time also," Helena said.

"Just one day, if you stay tonight and we have great sex I will forget that day also. I consider us intimate friends. I do want to spend some nights next week at your place. Maybe I can help with the design of your new dungeon."

"I prefer the word playroom, dungeon is a word what gives me a bad taste in my mouth," Rob said defiant.

"You are very welcome to stay with us; you have a couple of days off?" Helena asked, ignoring Rob's anger.

"I just reschedule my appointments. I want to know how it is, how you live with Marion and maybe Doctor Kim. Just to see it from a professional point of view. Maybe I even join you, when you are having sex."

Rob and Helena looked at each other. Rob said "I think I retire for a couple of day at my old apartment."

"No, you don't," Helena smiled, "don't take notice of him Cathy, he acts if he doesn't like it, but in fact he feels very comfortable amongst women. Kim has made the restriction whenever she is fucking him, he should be 'en femme', so prepare yourself for that."

"It will be an amazing experience, no doubt."

"I have two more patients this afternoon. I suggest you make yourself comfortable in the living room or go out, whatever you like, and I join you at 16:00." I have fifteen more minutes, and then the first patient will arrive. I better dress myself more formally," and she left them.

Rob and Helena also went inside Cathy's house, Helena in her slip, Rob in his pink dress, which now belonged to him.

They changed their clothes, headed for the living room and relaxed a bit.

When Cathy was finished with her last patient, she joined Rob and Helena.

Helena proposed to get some take-away food and Rob would get it. He drove to the pub where they met Bridget today and ordered some home-made food.

In the meantime Helena and Cathy had the opportunity to talk about the last two days. Rob still was short-fused, Cathy told Helena. But he learned to cope with humiliation, which was something he had to learn fast, if they ever would go out, while he was dressed 'en femme'.

Helena then asked if she has anything in mind, except of course a good fuck.

Cathy thought about it.

"I don't have much equipment here; otherwise I would propose a game of bondage. The only things I have are some handcuffs for personal use in bed."

"I will make a note of that. Something for Rob to buy for our new playroom."

"By the way, who was that woman this afternoon; a neighbor?" Helena asked.

"Yes, a neighbor but also a friend. When I want to confront some of my sissy's with an unexpected event, I ask if she will visit me, that can be outside as with Rob or sometimes I invite her in the outside building. She finds it rather funny," Cathy answered.

"We also have dinner together sometimes. It depends on the circumstances."

"Do you also have sex?" Helena asked curious.

"No, she is too 'normal'; it is maybe the right word to describe her," Cathy said.

"It doesn't matter, when I need her, she stands ready for me, and vice versa."

"That is good, to have such a friend," Helena said pondering.

They heard the car of Rob returning. A few moments later Rob came in, carrying a few bags with their dinner. Soon they were eating.

"What have you decided to do this evening," Rob asked.

"Do you have a proposal Rob?" Cathy asked.

"Cathy made a remark Rob, we don't have bondage gear," Helena said.

"We need almost everything. But bondage gear can also be used outside the playroom," Rob answered, "but I only want to play in the playroom, remember that."

"What about another session and then a good fuck," Helena asked.