A Game within a Game Ch. 01

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A cross dresser is being set up, but takes revenge.
47.9k words
4.57
80.7k
54

Part 1 of the 8 part series

Updated 09/22/2022
Created 12/08/2011
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Author's Note: This is my first story. I'm Dutch and therefore I have sometimes trouble to find the correct expression, forgive me, dear reader. I hope you still have fun in reading my story.

If I get positive reactions, I will post a follow up story.

This story is dealing with a lot of subjects, like cross dressing, bdsm, bi-sexuality (female to female), but I like to think that loving wives is the most appropriate main line.

Special thanks to my dear editor, who gave me courage to continue, Morgan_Lynn.

*

Epilogue

Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter.

Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fast to one of his patients. He died in the hospital and tomorrow is the funeral. When I received this letter I tried to phone you at work, but your secretary said you were already gone. Anyway, I told her that you won't be at work tomorrow."

Rob said "Of course I remember them - a nice couple." He was silent for a moment.

John and Marion were about the age of Rob and Jenny, who were in their mid-forties. Marion was an old friend of Jenny, from before the time that Rob met Jenny. He suspected that Marion was more than a good friend; Jenny always had been a bit vague about their relation.

He remembered John, and although he was the local family doctor, he seemed to be a bit shy. But in his work he was great; he had many patients and a flourishing practice.

But maybe he wasn't shy; it was perhaps the contrast between him and Marion. Marion was self-assured, very friendly, no doubt about that, but bossy and thus John came over as soft. Rob could imagine that a marriage with Marion could be difficult, to say it nicely.

That evening Jenny told him some more about Marion and John: "Did you ever expected that John had the same hobby as you Rob? And that she encouraged him in these things?"

Rob almost choked in his coffee they were having. "You mean dressing up?" Rob asked.

"Yes," Jenny said, "In a private conversation she told me about John. He was a transvestite, while you are cross dresser. When I told her about you, she wasn't surprised at all. Unintentionally we maybe have the same taste about men. You are also a bit soft, you know. Has anybody ever mentioned that to you?"

Rob said "No not really. But thinking about it, I told you about the S&M mistress I once visited in my discovery days. We spoke about the things she could do and what I liked. But she was very soon ready with me. She told me I was no real S&M person, and apart from dressing up, some bondage and a light spanking nothing else occurred. This mistress had a good judgment of human nature I think. Thus yes, in a way you are right."

Jenny then said "Let's go to bed, Rob. Wear a nice nightgown and let's cuddle a bit. I'm not in the mood for sex, but I want your arms around me. This event remembers us again that life is short. It's going to be a long day tomorrow."

The next day was the funeral and when Jenny and Rob arrived at the cemetery, already a big crowd gathered waiting for the sad occasion to begin.

Jenny saw Marion and walked towards her. She embraced her and they held hands. Rob made his condolences to Marion and kissed her slightly.

"Rob, I will support Marion. Be a dear and let us have a few moments in private," Jenny said.

Jenny and Marion talked softly and when the ceremony began, the two women walked to the grave and stood side by side listening to the vicar.

Both women were dressed in black and Marion wore dark sunglasses although the sun wasn't shining.

They seemed like sisters, Jenny dark haired and Marion dark blonde. Rob could see that Marion seemed much stronger now Jenny was standing beside her.

Finally the vicar was ready, and after also some other people spoke a few words, the ceremony was at an end.

Marion dropped sand on the coffin and walked back towards the funeral car. Jenny followed her and took her hand. The funeral car brought them to where Marion lived.

Rob followed them in his own car. Finally they arrived at Marion's house.

"Rob, do you mind if I stay a couple of days with Marion?" asked Jenny.

"You are invited also Rob," said Marion "I'm so grateful you both are here."

"Sorry Marion, but I have to go to work again. But I'll manage at home, and you stay with Marion, Jenny. I understand completely. Take all the time you need and let me know if there is anything I can help you with. Next weekend I can come here again" said Rob.

"Thanks Rob," and Marion kissed him on the cheek "You and Jenny are such good friends. Please come as soon as possible. I have spare bedrooms so if you can be here on Friday? Jenny and I have a lot to speak about and it will do me so good when I can tell my grief to people who really understand."

Jenny stayed with Marion and Rob went to work the next couple of days.

On Friday he joined them and they talked (and cried) a lot about John. Although they had some drinks - wine and whiskey - they never really relaxed. The hurt was too fresh.

The next day they went to a nearby forest and made long walks. Afterwards they had dinner in a small restaurant.

"Rob," asked Marion, "do you mind when Jenny stays with me for another couple of weeks. I am still feeling so sad and she gives me so much support, just by being here. I would be in your debt forever. I can imagine that you don't want to be here every weekend, but still I would like that very much. I'm getting to know you much better and you are such a kind and strong person. Please say yes."

"I can't say no to you Marion under these circumstances. But you don't have to ask me, you have to ask Jenny," Rob said.

Jenny replied "You know that is okay Marion. But I need to go home to pick up some clothes, Marion."

"That's no problem Jenny. There is a big mall nearby, I can buy you and Rob too, if he wants some new clothes. It gives me some distraction and this way I can do something back. Would you like that?" Marion asked.

"If Rob agrees, it's okay with me. And you don't have to pay, I'm glad that I can do something for you, what makes your loss more bearable," Jenny said.

"Okay, that's settled," Marion said.

So Jenny stayed at Marion for about two to three months. Rob joined them almost every weekend and slowly but surely Marion recovered from her loss.

During that period Rob never noticed anything except a sisterly affection between Jenny and Marion.

One year later

Things got normal after a while, Jenny returned home and Rob was very busy at work.

Marion and Jenny kept in touch, although not so frequent anymore.

Then one day Rob received a very mysterious email at work.

First he thought it was a joke: the sender was a Hotmail address what he didn't recognize.

The message was short: "I see you soon XXX."

Nothing else.

The next day another message came: "I'm waiting for you XXX."

Pretty strange Rob thought. He didn't have any clue who the mysterious sender was.

Maybe his wife, so when he came home that evening he asked her if she was teasing him. She had a strange look on her face and clearly had no idea to which he was referring. He decided not to make her any wiser about his question.

On Wednesday the message appeared: "Can't wait to make use of you XXX."

Rob blushed when he read the message, this was getting serious. He quickly glanced at his secretary who worked in the adjacent room, maybe she had something to do with it, but no. His secretary Holly was about ten years younger, but she had always been somewhat dull. He had no other word to describe her. She had nice legs and her figure was okay, but the way she was dressed and her haircut, it made her look much older. On TV there had been programs to give someone a makeover, she would be a perfect candidate, Rob thought.

Still, apart from being a bit strange, she also was a loyal friend. Once and a while he invited Holly to have dinner with him and Jenny, and the conversation they had always was very interesting. Holly had a great sense of humor and he knew that he shouldn't underestimate her, she was very intelligent. Holly always had a particular way of seeing things and sometimes he and Jenny had been astonished by her clear insight.

Although Holly didn't seem to have any sexually interest in people, she always had been broad-minded, she never gave any comment on some eccentric customers they had. Often he thought that Holly suspected him of having a secret which he of course couldn't tell her.

The following day again a mystery email: "You will be mine XXX."

Rob smiled, this was getting funny. He couldn't take it serious anymore.

Then came Friday.

The email which he received was no longer innocent, as far you can speak of innocent, but this time it contained a message that implicated that the sender knew too much about him: "Dear Roberta, in a few moments you will get a parcel, it contains some lingerie. I want you to wear it. In fact, I must insist. When you are ready, you ask Holly if everything is okay. She will do a quick check. When you are ready you go home, and tell your beloved wife Jenny that the game can start. She will know what to do.

Remember: the word 'game' is crucial.

You WILL be mine. XXX."

Rob turned red. He watched Holly, but she was busy typing and didn't look at his direction.

What is this, he thought. Obviously Holly and Jenny are in a complot.

His phone rang and he took it up: "Reception. Somebody with a parcel. You have to sign personally for receiving the package."

Rob answered "I'm coming, one moment please."

He put the phone down and saw that Holly was smiling at him.

She knew, Rob thought. He wondered fearfully just how much Jenny had revealed to Holly.

"I have to go to the reception Holly. I have to receive a package personally."

Holly said "Exciting, we don't get much packages here. Have you any idea what it is?"

"Err yes; I have some thoughts about it. I'll be right back," and with these words Rob walked to the reception.

When he arrived at the reception he saw a handsome woman waiting for him.

"Mr. R.G.?" she asked "I have a pretty expensive parcel for you. That's the reason you have to sign for it."

"Can you tell me about the sender?" Rob asked.

"No sir, the person who bought this for you made it very clear that you have to take it in person, without knowing from who it came from. Normally we don't do this kind of delivery, rules you know, but in this case it is a nice surprise. I know the contents of this package and it is absolutely harmless." Rob signed for it and took over the package.

"I wish you much fun with it sir, I think we took the right size, while looking at you," said the woman provocative and she left with a big smile on her face.

Rob didn't think it was funny anymore. He went back to his office and walked along Holly.

"Is there anything I can do for you Rob?" Holly asked.

"Maybe later," Rob said.

He unwrapped the package. In it was a box from a well-known lingerie shop. The box contained several smaller boxes and Rob opened them one by one. The first box contained a black satin bra with pointed cups, in his size 40B. Another box contained a waist-cincher with six garters attached; the same brand as the bra; of course also his size. Black satin French knickers with pretty lace followed and a black knee-long full slip, again the same brand as the knickers and the bra. It was a complete lingerie set. Finally a pair of fully-fashioned black nylons with a seam, which was size eleven.

The sender sure knew how to please him.

Rob invited Holly to come to his desk. I have to know he thought.

"Holly, these are the items I received. Furthermore I received an email with instructions. That email suggested that I should wear all these things and that I should ask you if everything is okay. I suppose you know where I am talking about?"

"Yes Rob, I also received an email in which I was asked to check on you, that you will wear all things from the parcel when leaving the office. First I thought it was a joke, but after seeing this very pretty lingerie I know that this isn't a joke.

My coöperation was asked to inform the sender by email whether you wear all the pretty things from the box or not.

I wasn't planning to do so, but now I will do it. It would be a shame if you wouldn't wear that pretty lingerie. It's obvious that someone has done a great effort to find all this in your size. I think you should wear it. You know that you can trust me, I consider you as my friend, not as an employer. I don't know the person to whom I will email back, Jenny presumably, but I'll go along."

Rob sighed "Well, it's almost time to go home. I will do what is asked for. Give me a minute and then come to the bathroom."

In a rush Rob went to the bathroom and changed his underwear for the pretty lingerie. He heard someone coming in.

"It's me, Holly. There is no-one else here now, so what can I do for you? Should I fasten your bra? Or tightening your waspie?"

"You are right Holly; I don't care if you see me in my lingerie. Please help me," Rob said.

Holly came in the unlocked cabin.

Rob said "I could not ever imagine that you would help me fastening a bra on me."

Then Holly saw his knickers that Rob already wore. "I see that you like what you are wearing," she was referring to his swollen dick that stood proud in his knickers.

"Now I go this far with you, I might as well tell you that I sometimes cross dress and I get very aroused by this silky stuff. It feels so smooth and slippery," Rob confessed.

"I know," Holly said, "I prefer this kind of lingerie also. You think maybe that I'm old-fashioned, but I know what I like. I can imagine that some men prefer nice soft female underwear above their own stuff.

You have to pull the suspenders beneath your knickers."

"I know," Rob replied "that way it's easier to go to the toilets."

Now Holly blushed "you really amaze me. Everything fast and tight now. Your slip is also very nice, it's a shame you have to hide it all under your trousers and so on, but we have to be discrete."

Rob then dressed in his outer garments and threw his male underwear in a bag.

"Time to go I reckon. You have to send someone an email I think, Holly?" Rob said with a smile.

"Yes, and I will tell her that I personally helped you dressing up," Holly answered "maybe I get someone jealous. A bit revenge for putting me in a situation I didn't ask for. But still, I liked doing it for you Rob. You know that the secretary always is a bit in love with her boss," she said with a sad smile.

Rob couldn't resist. He kissed Holly on her mouth. "Thank you Holly, I'm a married man, but you always will have a special place in my heart. Monday I will tell you all about today, and whatever the surprise will be, I will tell you all details, even if they are intimate. You deserve that."

"Thanks Rob, I'm sure it will be fun," and with that Holly waved him goodbye.

In a hurry Rob walked to his car. He could feel the suspenders against his legs. He had worn stockings before under his trousers, but never had shown it to anybody. Holly now knew, but he didn't care anymore. Rob was getting fond of that girl.

In a hurry Rob went back home. He was thinking what he would say to Jenny, in what delicate situation she had brought Holly and him.

Home

When he arrived at home, Jenny still wasn't back from a shopping trip. Rob started up his computer and opened his mailbox. He got another email from the unknown sender: "I'm glad you did what I asked for. I hope you like your new lingerie. Please shower and shave, and wear your new lingerie. Don't put on any male clothing and wait until Jenny comes home."

Clearly the sender knew all about him. It could be Jenny after all.

Rob took a relaxing bath and dozed off a bit. Then he heard a door banging. He went out of his bath and quickly dried himself.

"I'm upstairs Jenny, I had taken a bath."

Jenny came upstairs; Rob was still naked.

"A little bird whispered me that you have received some new lingerie. Can you show it to me while wearing it?" Jenny asked.

With a sigh Rob started to put on his new lingerie.

"Don't pretend that you don't like it," hissed Jenny, "it was very hard for us to find this lingerie your size."

"Us?" asked Rob, "so Holly is part of the 'game'? In the emails I received I had to mention that the 'game' has started."

"No, Holly is innocent," Jenny stated, "We made use of her a bit, and I will make it up with her in the future. But for now I don't tell you anymore. You will soon find out."

"Okay, done and ready," Rob said to Jenny.

"No not ready," Jenny answered "I have some more things for you," and she gave him a black satin skirt and a black see-through blouse. "Also wear your high heels, honey!" Jenny commanded.

Jenny herself was wearing a wide black skirt with white tones and a white blouse with some ruffles. Rob also noticed she wore black low heels. Jenny could put on anything; she had a splendid figure; long legs and 36C bra size. Sometimes jeans but not often; Jenny was a very feminine woman and she knew that Rob liked female clothing, so she usually wore dresses.

"I want you to be clad like this the entire evening Rob. It will be nice to see your butt and long legs in that skirt."

She was right, the satin skirt clearly showed Rob's butt. When walking on high heels, he was unaware that he swung his hips and it was a very erotic sight for a woman who stood open for this kind of behavior.

Finally they were having dinner. Jenny told Rob "And now for the real surprise. Tonight we will visit an old friend, and you are especially invited. Since it's weekend and she doesn't live nearby, we spend the full weekend at her place, so bring your nighty and toothbrush. You will go there 'en femme'. This friend is broad-minded; actually, even a bit kinky. She is the one who emailed you. Also, since I drive, wear your highest heels."

"But," Rob stammered "I have to go outdoors to our car and everybody can see me."

"Nonsense, it will be almost dark when we leave, and put on your coat, so nobody will notice," said Jenny.

During dinner Rob had worn easy low-heels but since Jenny asked him to wear high-heels he choose to wear his four inch heels and slipped them on.

He heard his wife also rummaging in her belongings and filling a suitcase.

"When I'm done here can you bring the suitcases to the car," she commanded Rob while he stepped in the dressing room. Then she saw his footwear. "Dearie, I said high heels, not half high. Please put on the ones I lately bought for you."

Rob moaned. "I can't walk in those for a long time."

"Rubbish," she said, "where we are going to, you don't have to walk a very long time; she has chairs you know," and with that it was settled. With a sigh Rob went to his closet again and fetched Jenny's latest gift: a pair of black shiny six-inch high heels.

Walking in them wasn't really a problem for Rob, but he didn't want to get any attraction while carrying the suitcases to the car thus being outdoors.

So with some hesitation he finally brought her suitcases and then two large weekend-bags with his own belongings to the car. He threw them on the backseat and quickly seated himself on the passengers-seat.

To the mansion

Jenny started the car and their journey had begun. Once at the highway, she could relax a bit and started fumbling his suspenders and caressing his stockings, while keeping both eyes on the road. "Is Roberta enjoying this?" she asked him.

Rob had been dozing a bit and fantasizing about where they were going to. "Roberta is having a good time," Rob answered, "but she is very curious where you will take her."