A Game within a Game Ch. 01

Jenny said amused "Well, it's all a matter of trust, and we have discussed this often. I wouldn't do anything what would hurt or upset you, so no worries."

But Rob wasn't satisfied: "You know I trust you, but so far I haven't been out dressed the way I am. Does your friend know we play our games as we do?"

Jenny hesitated with her answer what Rob noticed "I was not specific about it; the only thing I told her is that you are a bit submissive and very pleasing to me. She also knows that you like to wear female attire; but I think that only made her more curious about you. Therefore she insisted to meet while you are 'en femme' and to be honest, I couldn't refuse. And after all, she did send you some presents."

Rob then asked "So you know all about the strange emails I received?"

With a smile answered Jenny "I was asking myself when you would have told me. Yes, I had given your email address to my friend. I might as well tell you now; it has been Marion all the time. Surely you remember I told you that we knew each other for years and lost contact. After the funeral we picked up things again. Remember, last week, when I went shopping without you? We met in town and old things had come up. She likes you very much and while talking about us we got an idea. While I stayed with her I had told her about us trying to play our little games and that we made some progress, but lacked time, place and inspiration. Since Marion now lives all by herself in that big mansion, she offered us to play there. But she insisted on joining and as far as I know you Roberta, I think you will like that."

Rob was shocked "So it wasn't you who send all the lingerie? I had been pretty sure it was you all the time."

"No," Jenny said "I knew that Marion had made some plans, but didn't realize that she had started already. So it was for me also a surprise when you told that the game had begun. I had planned this weekend to go to Marion with you, but now it seems this visit will be a bit more than just a social meeting."

Jenny then said "You know we would be honest to each other. So far you didn't tell me about the emails.

You understand that you will be punished. In fact, that is one of the nice things about going to Marion: her house is on the country-side and no neighbors. So I can play with you without being disturbed. You can yell and nobody hears you."

A short silence. Jenny spoke again "This is a new house btw. After the funeral Marion sold her house, it had too many memories. The new house of Marion is much larger than a normal family home. I had the idea that she had a purpose with buying that particular house. We will soon see. I think she build a dungeon in the basement."

Rob sputtered "But you just said you won't hurt me."

Jenny said cool "I keep my promises. So no worry about too much pain or inconvenience. But you will pay for not instantly informing me."

"But, but," Rob stammered, "I didn't know what the meaning was of the emails or what purpose."

Then Jenny said with a grin "Well, it's no big deal. It's all part of our little game. Action and reaction? We have to pretend it's very serious and I really desire to do this again with you. I need a reason to punish you, don't be such a wimp. Imagine, a full weekend for ourselves."

Rob was thinking and finally asked "And where does Marion fits in?"

"I can assure you, Marion is to be trusted completely. Otherwise we wouldn't be going to her place. And it's part of the surprise. Please don't ask any further. You will see when we get there," Jenny sounded a bit agitated.

In silence they drove further to their destination. Happily for Rob, Jenny didn't ask him to pay at the gas station where they stopped for fuel. Jenny went out for herself and Rob ducked in his seat and covered his nylon-clad legs with his coat. Nobody took notice.

When Jenny returned she saw his coat over his legs and said "I love to see your legs, come on honey, show them to me," and with a sigh Rob removed his coat.

"I would feel so embarrassed if somebody should see me."

"I can tell you this; when a woman passes by and she is seeing your legs, she thinks that I'm a lucky girl, to have a friend with these legs. You underestimate women; a lot of women would like to see their lovers dressed up in stockings when making love. For a lot of women it's also an incredible sexy sight; not only men are fond of stockinged legs. You know that," Jenny said. "And when a man is seeing you, I don't think he'll notice your legs. They look at me, not at you."

Rob knew she was right, Jenny always had a lot of attraction from other men, he was lucky that he was the one to have married such a beautiful, loving, loyal and understanding woman.

After about half an hour drive they entered a small village which they crossed and then reached a small driveway which leads to a fairly large estate. Behind the mansion, was a small park and a forest, so there were no houses in the direct surroundings.

Jenny parked the car in front of the house and they departed their car.

In the meantime the front door opened, and Marion was standing in the doorway.

"Here you are again; welcome back Jenny and Roberta," she said with a smile and she kissed Rob on his mouth and hugged him. Thereafter she kissed Jenny also on her mouth "Lovely to see you again dear, and now we are all here at my new home. Roberta, you can take the luggage upstairs, first room on the left and then join us. Jenny and I will be in the sitting-room."

Marion hugged Jenny and they smiled to each other.

"Oh deerie, I'm so glad you are here. Jenny, you have no idea how I have missed you." Saying that both women went inside the house, walking hand in hand.

Rob had his thoughts about Marion's last sentence. Did Jenny not say they met in town and also bought his lingerie for him?

Whatever, he shrugged his shoulders and walked to the car, a bit stumbling on his high heels.

Rob opened the back of the car and picked up their luggage and went also inside the house.

He stood in the broad hallway where stairs led to the first floor. Several doors led to unknown directions, but he heard the women talk from behind one of the doors. Thick carpets covered the floor and stairs. He climbed the stairs and wished he was wearing his four inch heels instead of these six inch heels.

Finally he reached the top of the stairs and went to the room that Marion had reserved for them.

He opened the door and went inside. The room was a bit old-fashioned furnished with a large double bed. Satin sheets, very nice, he thought.

Heavy curtains covered the window and a large wardrobe had been placed in the corner.

Their room also had thick carpets covering the floor.

He had to walk twice to carry all their luggage upstairs. Jenny brought a lot with her, but he also did: his male clothing and his female attire. Jenny had insisted that he would bring along everything.

Time for a drink he said to himself and went downstairs to join the ladies.

He heard them talk and laugh and when he opened a door, he saw a warm cozy living room, where they were sitting on a couch. "Pour yourself a whiskey and make yourself comfortable," Marion said when Rob stepped in.

Looking around Rob saw a fireplace where a small fire was lit, just enough to make the temperature comfortable. Next to it was a cupboard filled with books and another one containing the liquors. Large windows had been covered with velvet curtains and a broad carpet was laid before the fireplace up to the couch where the ladies had taken place.

Rob picked up a glass from a small table and poured himself some whiskey.

He took a seat opposite of the ladies and didn't try to stare at Marion. In the full light he saw that she was dressed in a black dress, narrow closing from knees to her neck. Furthermore she wore black high heels and he presumed she wore stockings. She had painted her hair red, what suited her red lips. Her hair reached upon her shoulders. Her sensuous lips were curved in an alluring smile. Her large blue eyes, made up with a black shade, were observing him with interest. Although his wife was also very attractive, this woman had a strange effect on him.

In the past at the funeral and later on he had observed Marion of course, but it looks as if she had become a totally different woman.

"I hope you like what you see Roberta," Jenny said, noticing him staring.

"Sorry dear," said Rob "Two such lovely ladies in one room with me, it's mouth watering. Marion, I hope you forgive me, but you and Jenny, you both look astonishing."

Marion replied "Well, you are also a nice looking woman yourself, you only lack a bit of make-up."

Rob blushed "I'm a cross dresser, I'm not going all the way."

"Well Roberta," Jenny said, "That's only a matter of opinion. You wear woman's clothing, we call you Roberta, you behave like a woman, even walk like a woman and want to be treated with care. To me there isn't much difference. What do you think Marion?"

Marion rose from the couch and walked towards Rob and said "Stand up and turn around Roberta."

He did as he was told and made a turn. Marion grabbed his buttocks and squeezed them. "Hmmm, nice arse. He's surely a woman alright. You don't mind if I examine him a bit Jenny?"

"Go ahead, she's all yours, but you don't mind if I watch?" said Jenny.

"No, of course not, on the contrary, it will be fun," Marion said.

Fun, Rob was thinking. He was getting aroused by the 2 women but he had no clue what the fun was about.

"Excuse me ladies," Rob said, "Why do you want to examine me? I am perfectly healthy and I like to be informed what you are planning to do. I know we play a game, but I thought that Jenny and I had been playing and maybe some involvement of you Marion, but now it seems you take charge."

Rob thought about his conversation this afternoon with his wife and about her reassurance about trust, but now he wasn't so sure anymore.

Marion quickly replied "Dear Roberta, just a quick inspection. Jenny made me so curious and I wanted to see myself. You are a big girl and I don't think you are shy. So let's go to the next room, it's just to make us acquaintance to each other."

She walked back to the hall and said "Follow me Roberta, you too Jenny," and opened one of the doors in the hall. "In here please and Roberta, will you pull off your blouse and skirt? Jenny, if you feel more comfortable wearing something more suitable for the occasion, you can undress here in this room; I will change my outfit also. Rob please take a seat, we will be right back," and Marion and Jenny disappeared to an adjacent room.

Rob entered a small research room, what it obviously was. In the center a gynecology chair had been placed and alongside a couple of simple chairs. At the opposite stood a large cupboard with all kind of medical instruments and upon a small dresser towels and cotton where ready for use. Rob went pale when he saw the gynecology chair, his heart beat wildly. This was going too far; the game became very serious.

In the next room he heard Jenny and Marion laugh.

"Jenny," he shouted "I don't like it anymore. A game is fun, but this is the real stuff. Marion wants to examine me, I'm sure I have to sit in that chair."

"Well dear, of course it's for you," shouted Jenny back, "You are a big girl now and all big girls will be sooner or later taking place in that chair. It's nothing to be scared off."

Some ten minutes later Rob heard click-clack from their heels and Jenny quickly entered the room.

Jenny had been busy: she wore a black PVC outfit which consisted of a black bra through which her breasts almost completely had been exposed and a waist-cincher which made her hips looks much fuller. She didn't wear panties, her shaven labia was a wonderful sight. Long black stockings attached to the garters of her waist-cincher made her legs look much longer. Last but not least: her knee-high black PVC boots with pointed heels completed her mistress outfit.

"How it's going here?" Marion asked when she approached the room.

With a shock Rob saw the bizarre outfit Marion was wearing. Marion wore a PVC corset what enclosed her midriff tightly. Her breasts had been lifted by half-cups while leaving her nipples bare.

To the corset she had very sheer black nylons attached and she must have been walking on very high heels, from his position Rob couldn't see them well, but she looked much taller. No panties either and her cunt lips where clearly shown.

On her arms she wore long black PVC gloves.

Both women had their faces dramatically made up. Their eyebrows were darkened and around their eyes the make-up was smoked and dark, lips were dark-blue with black lines bordering, and a light red blush on the cheeks completed it. The blush also could have been coming from excitement. All together it gave their faces very sinister looks.

Rob felt his dick rising; never in his dreams he could imagine that these vixens made all the efforts just for him. He had never seen Jenny wearing this outfit before, and realized that she must have bought it especially for this weekend.

Marion said: "I notice that you like what you see, no doubt about that," pointing to his bump what became visible through his skirt.

"Okay, I will start now, at the moment I'm not so interested in your dick but what I do want to know is what you can take in your arse. Therefore I will do some tests until I know from what point off we can train you further. You understand that you are here for that reason: to get proper training. When I'm ready we will discuss that face to face in all honesty."

"Well, do we have to wait long? Take off your clothes and fast please!" Jenny commanded.

Sighing Rob took off his skirt and blouse. "Your knickers and bra also," Jenny said. Rob stepped out of his high heels and put off his knickers and bra and stood with his slightly aroused cock before Jenny. Now he only wore his waist-cincher and stockings.

"Good girl," Jenny said. "I know that you are unfamiliar with this device so I'll help you. Just sit in the chair and put your legs in these brackets. Relax honey, everything will go just fine."

Rob climbed in the chair and put his legs in the brackets. His black stockings and girdle accentuated his cock what became stiffer. Must be the tension, Rob thought to himself and hold himself firmly to the arms of the chair.

"Hold on," Jenny said and she picked up some leather belts and cuffs from a drawer. Quickly she fastened the cuffs to his wrists and elbows and attached the cuffs to the chair. The same procedure she did on his ankles and knees attaching them to the brackets.

Then she picked two larger belts and placed one around his chest and the other on his stomach, both attaching them to the chair. Now Rob couldn't move his body, arms and legs.

Marion said "I see you are comfortable Roberta, can I get you something before we start? Jenny, will you come with me please?" Both women disappeared and Rob wasn't feeling comfortable at all. His cock was clearly exposed and he felt humiliated. The fact that both women had to talk to each other without being overheard by him made him nervous. "You are still ok there Roberta?" Marion asked from the hall.

"To be honest, it's not so comfortable," Rob said. "Be patient dear, we are almost ready for you," Jenny shouted from a short distance.

Then both women walked in the room again. It was now obvious that they had discussed something he didn't need to know Rob thought.

"Okay, let's start," Marion announced.

Jenny asked "Can I be of service?"

"Yes dear - in the upper drawer you will find a collection of dildos, from small to large. Please get them for me," Marion replied.

While waiting for Jenny to bring the dildos, Marion started to lubricate her right glove with some oil which she took from a low cabinet with all kinds of medical stuff.

Then she pushed Rob's legs from each other thus making his arse more accessible. She applied also some oil on Rob's anus.

"So, now you get what you always wanted," Marion said to Rob, and with her gloved middle finger she softly accessed his rectum and gently pushed it in. "This feels good right? Try to relax, I really want to do things just fine, and we all benefit."

She withdrew her finger and then pushed two fingers in his arse. Rob moaned.

"Be a good girl, I have to grease you on the inside before I start with the dildos," Marion cautioned.

In the meantime Jenny smeared the dildos in with some lubricant. She gave the smallest to Marion.

Marion had withdrawn her fingers.

"This shouldn't be a problem. Good. Please give me the first one," Marion said and Jenny gave her the smallest dildo. Very gently Marion pushed the dildo in his arse.

It went in smooth without any problem. Marion removed the dildo and asked for the next one.

Jenny gave her the following dildo; this was a 1.2 inch dildo what Marion inserted in Rob's arse. She guided it very slowly into his puckered anus. The ring of his anus gave resistance, Marion smeared some more lubricant on the dildo and his entrance and slowly, pushed deeper. Marion took her time, easing the dildo in by fractions of an inch. Rob groaned and gave a cry when the dildo suddenly passed the enclosure muscle. Very gently, inch by inch, Marion invaded the tight opening, withdrew the dildo then and pushed it back again.

Jenny in the meantime had taken his cock and caressed it softly, making the dildo attack somewhat better to endure. Then Marion was all in and slowly she pushed the dildo in and out. Rob was shaken by an intense combination of pleasure and pain. He felt as a woman who got fucked and thought it was the ultimate of enforced feminism. His cock was rock-hard. Jenny pushed her lips around the head of his cock and slowly curled her tong around it and sucked a bit.

Rob moaned.

Then Jenny stopped sucking "I won't go any further, otherwise you come to fast and we all want our share. It's still early."

Rob said "This felt so good, but you know it's my limit, I can't take any larger dildo. I won't let you do that."

Marion hissed "You aren't in a position to make demands, but as I promised, trust is the keyword and we won't do things somebody really doesn't want. That brings us to our next examining point."

Jenny came closer and gave a small box with she had been taken from the second drawer.

Marion took out a small nasty looking clamp.

"Nothing to be afraid of, Rob," Marion saw his fear. "It has some rubber on the inside and the pressure isn't high. We just try what you can bear," and she placed one on his nipples.

"Ouch," Rob shouted, "take it off!"

Quickly Marion took it off. "Mmm, this is too painful? But surely you can bear this," and then she took his skin next to his nipples and put a clamp on it.

Rob gave no comment.

"I thought so," Marion said, "This is better, even gives you pleasure, right? It's very stimulating."

Then she took a second clamp and did the same at his other breast.

"The funny thing is, I can give you a whole bunch of these, and that even includes the skin of your balls. It will be annoying, but also stimulating. It's a pity your nipples can't be used, maybe in the future; it's all a matter of practice."

Then Marion removed the dildo and took off the nipple clamps and started to untie him.

Within seconds Rob was loosened and he sighed of relief. "That feels better," he said "but it felt very stimulating and I think it is very erotic doing these things to me."

He put on his knickers again.

"First complaining and when we stop you are disappointed?" Marion grinned.

"Typically Roberta, I told you, she is kind of a sissy," Jenny said. "But this girl will behave better in the future. Let's review with her what we have discussed before."