tagTranssexuals & CrossdressersThe Struggle Ch. 04

The Struggle Ch. 04

bydoberinca©

Author's Note: This is the fourth story in the chain "A game within a game."

Special thanks to NJLauren for her considerable editorial assistance.

Characters:
Rob - main character
Helena - his wife
Marion - widow; very much in love with Rob
Cathy - friend (psychiatrist)
Kim - friend (local doctor)
Kate - sister of Helena
Carmen - friend; member of the circle (women society)
Bridget - friend; owner of a theater shop (- and more mature items)
Michelle - friend
Lisa - owner of a bridal shop
Olga - friend; member of the circle
Helga - friend of Olga
Jenny - Rob's ex-wife
Sylvia - member of Helena's security organization
Nicky and Inca - Rob's Doberman dogs

Reader, this story is the follow-up of 'a game within a game part 1-2-3'. Actually it's part 4, but the title didn't cover the contents anymore.

One more thing: this is fiction of course; but there are a lot of elements of RL described. The fact that so many woman are committed to the main character isn't so strange either: a good friend of mine had subscribed to a dating site and each evening, seven days a week, he had a different date. All these women were between 40 and 60 years old. And they all wanted to have sex; and a shoulder to cry on. These are strange times...




The morning of the wedding

It was still dark, when the door to Rob's bedroom opened. Rob was already awake, as he couldn't sleep well. The words of Helena puzzled him, what did she mean by "You have to obey tomorrow?"

It all came back to him and today was the day he had to obey some mysterious woman. He had promised to do so - it was a very special day and he wouldn't like to be the spoiler. Still, he had all kinds of thoughts about what she had said.

The light was put on and he saw that the woman who had entered his bedroom was Carmen. Rob looked at his watch and saw it was 05:30. He moaned and said, "Why so early?"

"You know it will be a busy day," Carmen replied.

He got up and stood next to his bed. Carmen was fully dressed, but not for a wedding. She wore a tight black dress and low black heels. As far as he could see she wasn't wearing stockings or even tights. Her arms were bare. She was dressed very functionally, hmm, what would be the right word to describe her, not sexy, not tempting, but business like.

"Good morning, Rob. I'm here to prepare you for your wedding."

She then gave him a soft smile. "When will you marry me?" With this she pinched his naked ass.

"Rob, please take a quick shower but don't put clothes on. I'll explain in a moment".

With a funny look, Rob went to the adjacent bathroom and took a hot shower. Carmen had followed him in and when he was ready she handed him a few towels. When he was completely dry she directed him to the bedroom where he was ordered to lay down.

Carmen had some sort of sweat smelling lotion and she rubbed his back and legs with it. It smelled nice and when she was done Rob felt good.

He was handed a bathrobe.

"Rob, you have to follow me. We have prepared a little ceremony that will take place in a few moments. We will go to the playroom and there you will be cuffed. Some questions will be asked of you and you have to answer them honestly. You will be marrying a Mistress, and another Mistress will be helping to find out if you are worthy of the mistress you are marrying. Yesterday you promised Helena you would obey us - and I ask you to do this for her."

"Err, and who is the Mistress?"

"That is part of the surprise. She will be masked and you are to fulfill her wishes completely, Helena insisted on this. The new Mistress and Helena have had a long talk about you and Helena fully trusts her.

That's all I know. I am only asked to remind you of your promise. Whatever happens - please her - and you will pleasing Helena. BTW – Marion, your bride, will know nothing about this happening. We will make a dvd of it and perhaps she will see it after the wedding, tomorrow or something. So, remember - everything that will be said and done, will be saved and used as proof. But also, keep in mind that you can hurt people with whatever you say; so, please speak freely, speak about what's on your mind, but try not to insult anyone who might see it." She paused.

"I also have to say this again, there will be nothing to be afraid of, or any weird things happening. The point of this whole scene ,and it is a scene of course, is to find out what you can and will give to Marion and to your wife Helena, who will play a great part in the whole scene. It is not all about Marion, but also your commitment to Helena and the other women as well."

Carmen looked at him. Rob noticed the small crow's feet around her eyes, the only sign of aging. Her reddish hair was bound in a pony tail and he didn't remember her wearing it like this before.

"Are you going to be the Mistress?"

"Don't be so curious, Rob. All will be revealed in due time. And no, I will not be the Mistress. I have other 'needs'." She gave him a faint smile and then said, "I can tell you this, this afternoon after the wedding you will be busy. You have to obey us and you know what I want."

Rob remembered the day at Marion's house where he had had to 'serve'. That particular day he was 'rescued' by Helena, the start of his relationship with her. She had warned him about bad things that she sensed were going to happen. Today, he once again had to trust her.

He made up his mind and Carmen saw his mixed feelings on his face. She smiled to herself, let him sweat a bit, she thought, maybe she was a bit cruel after all, and she chuckled.

Rob was unaware of the secret pleasure Carmen had with his uncertainty and reluctance.

"Let's go downstairs, Rob. Be yourself and all will be well," she urged him. "Keep your bathrobe on, we don't want you to catch a cold on your wedding day after all."

Accompanied by Carmen he went downstairs, they used the new lift. Since it was Saturday, no staff was present. It was silent and when they arrived at the lowest floor, where their playroom was situated, Rob became a little bit afraid. He had setup their playroom, but when it was ready and all the devices were placed, the room looked like an S&M chamber, and not like a playroom at all. He named it a playroom, because he wanted to remove the sinister effect by giving it another name. Still, in this silence and being naked while he was taken to that room, he felt his braveness wash away.

Carmen noticed of course and she supported him by giving him a hand and asked worriedly, "Are you still OK?"

"I'm a bit weak. I haven't eaten yet, and it's still early," Rob explained, he didn't want her to think he was afraid.

Finally they reached the door that gave admittance to the feared room.

Carmen took the bathrobe from him and then fastened a collar around his neck. He wasn't used to wearing a collar, it felt a bit strange. To the collar she attached a small microphone.

"Go on Rob. You have to walk in freely and by yourself. You'll be fine," she encouraged him.

When Rob entered the room, it was silent. He closed the door behind him and looked around. Some modifications had been made since he was been here the last time and the most striking change was the large X-cross. It was fully exposed and a spotlight was lighting it. He had fastened the X-cross to the wall but now for some reason it was standing in the middle of the room, just like it was at that dreaded day at Marion's house.

He walked towards it and saw the X-cross was fastened to the floor with a chain through shackles on the floor and on the legs of the X-cross.

All the other lights were dimmed and he could not see the back of the room as a result. He heard someone coming closer and a female voice asked him from the shadows while he was standing next to the cross in full light, "Are you here of your own free will?"

Rob nodded but then the voice said, "Please say yes or no - I want to hear your answer. All that we say or do will be recorded. I'm wearing a microphone, too. Please answer in full."

"Yes - I'm here freely."

"Didn't you forget something?"

Rob looked at the vague figure and tried to see who she was, but she kept standing in the shadows.

"I'm here freely, Mistress."

"And You are aware you will have to obey me?"

"I will obey you today, Mistress." Rob didn't want to let her think he would obey her always. He only promised today - and nothing else.

"Oh, today is perfect for me, I hope it will be for you, too," the Mistress laughed, not entirely friendly. She had him where she wanted him.

"I will examine your soul, Rob. I want to know your deepest feelings. Don't make mistakes - you are here freely. I want honest answers, to avoid problems in the future. Can you surrender to me?"

"I don't know, Mistress. It depends..."

"Depends on what?"

"It depends on the questions you will ask. I cannot foresee the future and I cannot go against my nature. If I have the feeling something is wrong, wrong is wrong and I will act as I think I need to. Even if it would violate a promise I made."

"Excuse me?" The mistress sounded a bit on edge as well as confused.

"Sorry, Mistress. Let me give you an example. If I would be asked to give up my dogs, I would refuse. When I marry Marion I expect that she accepts me and all that comes with it."

"That is a good answer. I will tell you, I will only question you and there are no good or wrong answers. The only thing I ask is total honesty. Do I make myself clear?"

"Yes Mistress."

"Pick up the leather cuffs and fasten them around your wrists and ankles."

Rob did as was asked.

"Good. Face the cross - I will tie you to it."

Rob turned and looked through the upper legs of the X. He heard the Mistress coming near him and she fastened the handcuffs above his head to two chains. Thereafter she made him spread his legs and his ankles were fastened to the x-cross. She pulled a cord and Rob felt his arms stretched until his arms couldn't rise any further. All the while he looked through the X-cross and had still not seen the Mistress' face. He had smelled her, but it was an unknown perfume. He knew she wasn't any of his girlfriends or even from the circle.

He did see her hair, it was pitch-black and probably was bound in a pony tail. He knew nobody with this kind of very black hair. He was wondering who she was.

Suddenly she stepped into his sight line. She was masked and it was a black rubber one. Her red lips were visible through some kind of lace, and her eyes could be clearly seen. Nothing else; the rubber coated the rest of her face and she was ageless. Her hair was in fact in a pony tail, it came through a hole in the mask and as he suspected, bound together to make the tail.

She also wore a black shiny rubber corset. Her breasts were bare and so was her pussy. He saw a tiny bit of carefully shaven pubic hair above her cunt. Her cunt was lovely, full and with large outer cuntlips. She must have colored them, because they were a fiery red and very visible between the garters of her corset. The garters were attached to long black stockings, which almost reached her cunt. She wore high-heeled boots, made from a shiny pvc material and that reached over her knees. When she turned, he saw they were seamed stockings. She wore long black rubber gloves on her arms and in her hand she was holding a short whip.

Rob was afraid of that whip, it looked pretty innocent, but he knew it could hurt him a lot in skillful hands.

She noticed his gaze and finally said, "Have you seen enough? You are very impertinent to be looking at me like that without permission. I will have to punish you for this, but that you already expected I think. Of course, I don't need a reason to warm your buttocks."

She grabbed a chair and a trolley with all kind of whips and other things on it and sat before him, her cunt in full display.

"Before we begin, I understand you have a safeword?"

"Yes, Mistress."

"When it's becoming too much - I'll expect you to use your safeword," the Mistress warned him. "I was told you use the word 'black' - correct?"

"Yes, Mistress. I will use it. Red is for a break; black is ending the scene."

"Ok - I hope when you must use it, you'll use red, otherwise we may have to postpone your wedding and we don't want to disappoint your new wife again. Do we?"

"No Mistress. I probably won't use black, Mistress."

"While I'm questioning you, I think I will make myself comfortable." She grabbed a vibrator from the trolley and licked the shaft. Teasingly she looked at Rob and then pointed it at him.

"Maybe I'll let you feel this soon."

Softly she let it glide between her cuntlips and pushed it in. She began to moan softly, all the while looking at Rob to observe his reactions. His reaction was visible even before the vibrator act, his dick was throbbing all the time while she was showing herself in front of him.

Suddenly she came to herself and laid down the vibrator.

"Enough of this - for now. It's your turn." She picked up two tweezer clamps with a ring attached and fastened them one by one. The pressure was not too much, Rob had endured other nipple clamps which had caused much more pain, but somehow he knew this was not all there was to be.

The Mistress then picked up four rings, on each a led weight was attached and at the other end they had a chain and hook.

"These rings represent your friends. This is Helena, your wife," she showed Rob a ring with a pretty large weight attached to it. "This ring represents Marion, your new bride," and again she showed Rob another ring with a similar weight attached to it as the ring what represented Helena.

"These rings represent Cathy and Kim." Both rings she showed to Rob had a smaller weight attached to them.

Finally she picked a weight, almost the same size as the weight that represented Helena and Marion.

"This weight represents me. I'm not sure if you can carry all of us, but you have chosen at least to carry Helena and Marion." She hooked each weight to a nipple clamp and Rob immediately felt the pain through his chest and gasped for breath.

"Are you OK?" the Mistress asked, concerned.

"Yes mistress. I was not prepared for it, but it's OK." The pain lessened and it became a dull pain. Rob knew when the clamps would be removed, the pain he would endure would be terrible for a few moments.

"Are you prepared to carry the weight of Kim and Cathy?"

Rob knew this question was a symbolic one; it had nothing to do whether he could endure the pain, but could he spend his life with Cathy and Kim, just as he would do with Helena and Marion.

"Yes - I am prepared Mistress."

"Good - I didn't expect anything else," and quickly she hooked each weight representing Kim and Cathy to a nipple clamp. He carried four weights now.

"Are you man enough to carry my weight Rob?" She showed him the last weight. This had a ring attached with two hooks and chains.

"I assure you, it can be very worthwhile. You know Helena trusts me. What do you say? Do you want to carry my weight, too?"

Rob looked at her. He still couldn't figure out who she was. She wasn't Bridget, he was sure of that, he was pretty sure he let Helena know he would not accept her as Mistress. Another Mistress. Michelle? Michelle was blond and was much softer than this woman. Her voice sounded familiar and yet in this dungeon all sounds were diffused. The velvet curtains on the walls made sure all sounds sounded differently than they would outside of it. He couldn't trust his ears.

Finally he looked her right in the eyes and said, "Let me carry your weight, mistress."

"How nice! I'm really flattered." She smiled at him and then both hooks were fastened on both nipple rings.

Rob moaned and sighed heavily. The pain ran through his upper torso and finally went dull again.

"Now tell me Rob. I heard you feel lonely sometimes. How can you be lonely with four beautiful women who each love you?"

Rob sighed. "You can be lonely in a crowd, you know. I sometimes feel neglected, no, I am neglected sometimes. It is at these times that I am glad I have my other two ladies. Are they being taken care off? Normally I walk with them around this time."

"Let's not change the subject Rob. Your ladies are fine. How come you feel neglected?"

"They don't seem to see me at all, and I am sometimes their servant and not their equal. Which bothers me very much."

"And what do you do then?"

"I go for a walk with the two ladies who won't ever neglect me or betray me," Rob said with an angry voice. He was getting tired of answering her under these circumstances.

The Mistress rose up from her chair, smeared some lube on her gloves and approached him. She took his dick in her gloved hands and started to stroke and squeeze him. His dick was very hard and he felt his juice coming.

The Mistress felt it also and gave him a pretty hard slap with a small whip on his dick. Rob shrieked - this he didn't expect. His dick went soft again.

"Let's continue. You are sure you don't want piercings? You know how much Marion would like you to have them, don't you?"

"I'm sure." Rob growled.

"I expect respect from you, Rob. I asked you a legitimate question and you don't have to be angry at me, I'm still your Mistress."

"Until I safeword that is, Mistress," Rob growled again.

"What a temper you have! Maybe Marion should reconsider her marriage to you and maybe I should pull back my offer to you of carrying my weight."

She touched her weight and took it off. Then she removed the other weights.

"Be strong Rob," she whispered and then she removed the clamps, fast. The blood started to flow through Rob's nipples and he felt a sharp and hot pain through them.

But, he was expecting it and beside a soft moan he didn't give her the satisfaction to show her that he was in pain.

He didn't need to, the Mistress knew exactly what she was doing and a smile parted from her lips.

"I also heard you had beaten your friends and your wife. You punished them for a pretty innocent game that you took very seriously. I'm now going to inflict on you the same pain they had to endure at your hands."

She took a cane from the trolley and swished it through the air.

Without a warning she gave him the first blow. She did exactly the same thing that he had done to Helena and his girlfriends and when she was finished Rob had on each side of his bum three red marks, six in total.

"Now because you haven't been given me the respect I deserve, I will give you your punishment for that impertinence."

Without delay she administered another six blows.

Rob tried to escape the blows but in vain. After the last blow the Mistress inspected his behind and rubbed some oil on it.

"I don't wish that you cannot sit today."

"I have had enough of this bullshit," Rob said very angrily.

"Pardon?"

"Fuck you! Black," growled Rob.

Immediately the Mistress untied him. When Rob tried to pull off her mask, she jumped backwards.

"Oh no, you ended the session. It's not finished. I'll therefore keep my mask," and with hasty footsteps she disappeared back to the entrance, leaving Rob behind.

The door opened and he saw Helena come in.

"I heard you safeworded?" she asked.

"Yes. I have had enough of this bullshit," he growled with the low voice she recognized and feared.

"You had made me a promise Rob. I asked you yesterday to be strong and think of me. I don't know if I want to go along with you this way. I can only assume you said 'black', but maybe what you wanted to say was 'red'?" She looked at him with begging eyes and Rob couldn't resist her, and kissed her.

"That woman was playing with me."

"That 'woman' is a very experienced Mistress Rob. You should be glad she made the time to lead you through this scene. We had spoken a lot about you, and by telling her what is bothering you, you can free your mind and let go all your angry thoughts. She is still here. I urged her not to leave. Will you please go on with the session? It is just you and she, a dvd is being made of this session. We will discuss the dvd afterwards. The answers are very important to me, to us. Please continue, for me and Marion, please?"

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