Helen Ch. 04-05

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Continuing training of Helen.
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Part 4 of the 9 part series

Updated 06/08/2023
Created 04/24/2012
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This story is a graphic tale of a Dom and his very submissive transgendered male. If you are offended by tales of BDSM and sex between consenting adults then read no further... other wise enjoy.

Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue...

*****

I grabbed her arm forcefully and almost dragged her up to my bedroom, it was at this point pure lust on my part. "Strip bitch I want you naked now." I saw her look a little worried by my tone of voice then she stripped fully, standing before me in nothing but her cage.

I undressed myself slowly, watching her as she stood there, seeing her lick her lips as I push my pants down, letting my tumescence spring to life, god this bitch made me so fucking horny.

Once undressed I pulled her close to me grabbing her ass I parted her cheeks and roughly push my thumb into her ass making her jump and move even closer to me, I enjoyed her smell and bit her neck leaving a hickey there that would remind her for a week at least of tonight.

I then pulled away, got some rope from the bedside table, ties her wrists together and bent her over the bottom rail of the bed securing them to the head board, then two more ropes tied from her ankles to the legs of the bed spread her, leaving her very vulnerable and also available to me.

I then unlocked her cage and tied a tight rope round her cock and balls making it stand proud, she was still a reasonable size, we would see later how much teasing she could take.

I then moved behind her, parted her cheeks, spat on her asshole, and said "Ready or not here I come." and I thrust into her in one movement sinking at least 4 inches into her tight little ass, hearing her squeal and seeing her cock twitch I started to stroke in and out none too gently just working myself in until all seven inches of me were buried balls deep.

She was so tight it did not take long for me to feel myself building for an orgasm and when it arrived she moaned like a pro and she drained me all, emptying my balls in her as she clenched her tight asshole and milked what was left of me.

When I pulled out I saw the grin on her face, knowing she had made me cum, and I watched her as she squeezed my juices from her hole leaving a small mark on the carpet.

I released her bonds and grabbed her hair pushing her down "lick that up bitch, how dare you expel me", I almost rubbed her nose in it like you do when a bitch dog is dirty in the house.

I will punish you for that.

I threw her on the bed, pulled the nipple clamps from the side table and clamped her nipples together, I then took each ankle and tied them splayed wide. Took the rope from her cock and tied it tight to the bottom rail of the bed.

She was still smiling at me, thinking I was done I suspect, but I had a little surprise for her. The clamps I used on her nipples were clover type, the ones that tighten as you pull them, and to make then even more secure I had wrapped elastic bands round them, so that they griped tighter from the start, to the centre chain I then added a piece of rope which I took to the head board and stated pulling hard before tying it off.

It was not long before the smile went and the tears returned, she was immobile, any way she turned pulled more on her nipples or cock, she was helpless and hurting. I grinned down at her "Teach you to fuck with me bitch."

I then grabbed the bedclothes and snuggled down beside her, my hand softly massaging her swollen and tied cock "And you better not cum." S

he just grunted and tried to buck her hips, trying to fuck my hand. It was not long before she came, I fully expected her too, she was far too aroused to be able to control her lust, but now was the time when she was mine, I went under the covers, licking her nipples as I moved down the bed and sucked her clean. I then released her nipples from the clamps and licked them until she had some blood back in them, at which point I released the other bonds and held her in my arms, just cuddling her like lovers do.

It was not long before I was fully hard again, so I moved down her body, sucked on her cock and got her hard, she started to move but I pushed her down and said "Leave this to me darling," and got to work kissing her body, almost worshipping it, showing her I had a soft loving side as well. Once I had worked my way up her body I kissed her long and deep before turning her ass to the side and entering her again.

I stroked deep and slow, feeling her cock occasionally, feeling how hard and excited she was, and before long she was pushing back trying to get me even deeper in her, until she was moaning and then a little dribble came from her cock, I knew then I had made her cum from my cock massaging her prostrate, and I could finally cum myself which I did forcefully, amazing myself as this was the fourth time today, a record for me, showing me how excited she had got me.

Exhausted we soon dropped into a deep sleep, spooning each other, only to be awoken by her under the bedclothes, with my cock very much in her mouth. I always awoke hard but this was a whole new dimension, when she realised I was awake she sat on me driving me deep inside her, encouraging me to play with her nipples which still looked puffy from their bruising the night before. I let her set the tempo, she seemed to know how close I was getting and took care to just edge me not letting me cum, before I finally grabbed her hips and drove in as deep as I could, yet again filling her with my cum.

She collapsed on me and I held her very tight until I felt myself softening and then I plopped out of her.

We laid together for some time, calming down and getting back to somewhere near normal, before I said "Do you really have to go this morning."

"Sorry yes I do." she said looking sad.

"So when will I see you again assuming you want to see me?"

She stoked my cheek "Oh yes I want to see you again." my heart leapt at her words "Can I come back this evening."

I smiled "Of course you can my darling on one condition."

"What's that Master."

"That you go to work today wearing your cage and I will keep your key here ensuring your return."

"But Master how will I hide it under my clothes I usually wear trouser suits to work."

"Well not today my girl, that's the deal, you wear the cage or you don't come back."

I realised that this might be a huge mistake as I really did want her to come back, but I felt I should assert my authority now, show her what she was to me, my slave, even if she regarded it as a bit of fun I had other plans for her which over a period of time and training she would accept as part of her life.

I could see her thinking about this hard, her cock was growing again and I knew then I had her, it was exciting her and she had said before that was what was lacking in her life.

Finally she looked me in the eyes and said "Yes Master, thank you Master that would be my privilege."

"Good girl, then this evening we will chat about your future."

"My future Master."

"Yes my darling, I have such big plans for you."

I slapped her ass and sent her off to shower. I went through her back to see what she had there to wear, and picked some things out for her.

When she came out the shower I kissed her and then knelt before her a fitted her cage again.

"Make sure you tuck yourself well, I don't want your boyfriend knowing you have a cage on, not yet at least."

I saw her puzzled look but she did not ask anymore, just getting dress in the items I have laid on the bed.

A G-String that was almost a waste of time wearing as it was so small, but it would catch and drips from her, then a blouse and skirt that came a couple of inches above her knees, nothing to racy, after all she was the boss and had to keep up appearances.

She did her make up and looked the professional as I said goodbye to her at her car, giving her crutch a squeeze, feeling her cage, I smiled at her and kissed her goodbye.

Chapter 5

That day while she was at work I got various chores done around the house and dug out some of my older toys, I also ordered a couple of things that I knew would be delivered the following day, that was the Friday, so I would have them for the weekend as I was sure she would stay with me over the weekend.

We had a lot to discuss this evening, not least her boyfriend who I knew lived with her, but that she was bored of, he was a bit of a wimp she had told me, but it was really up to her what she did about him.

While I got horny every time I thought about her body I knew that she was a strong willed lady, she had put up with so much during her time becoming a full time woman, and I knew her business was doing well and growing, I had done my research in that area as well. I also knew from our discussions that one day she wanted to have reassignment surgery, and she also knew that I was not in favour of that, but that was a discussion for another day and I would not stop her if she really wanted that.

She texted me when she left the office to say she was on her way, and I finished my chores, went through the few items of clothing that she had left behind and chose a simple but transparent negligee in white lace that I laid out ready on the bed. Next to it I put a thick metal collar engraved with 'slut slave', a pair of metal wrist cuffs, and a pair of similar ankle cuffs. All of these locked automatically when shut and I pocketed the keys and went to the lounge and sat and waited for her arrival.

On her arrival I kissed her, asked how her day had been, and sent her upstairs to change out of her work clothes and put on the items I had left for her while I made her a drink.

"Get dressed and come back down, I think we need to have a long chat tonight."

"Yes Master." She said as she trotted off upstairs.

When she came back down she looked stunning, she had brushed her hair out, the collar fitted her perfectly as did the cuffs, and that combined with her negligee made her look so adorable I knew I had to find a way of keeping her. She smiled at me doing a little twirl so I could see all of her.

Apart from some bruises on her ass and a couple on her breasts she was perfect, and she had obviously not been able to get the cage off as it was still there, full as she was obviously still excited to be like this in my presence.

I stood and said simply "Knees." She dropped to her knees and opened her mouth for me. I undid my zip, got my cock out and pushed it into her mouth until she gagged. I fucked her face while saying "We have a lot to discuss tonight so this will be quick so I am less distracted when we sit to talk." It was not long before I unloaded in her mouth, withdrew and zipped up my pants, this was not a loving thing it was my lust using her body for my pleasure, showing her what her position in life was with me, should she want to stay here.

I sat down and patted the settee next to me and she immediately sat, cuddling up to me, her warm body felling so close and vulnerable.

"During this discussion I need you to be totally honest with me, it is about bounderies, limits, and how we will interact for the future. I will set out a vision I have and you will respond in a truthful way, highlighting anything that you feel unreasonable or too much, is that understood."

"Yes Master." She said quietly, casting her eyes down.

"Very well. While we do not know each other very well we have spent a lot of time talking about things, what we both want from this relationship and after last night I am now certain that I want you in my life for the foreseeable future. I would like it if you became my full time live in slave."

She looked at me, then sheepishly asked "What would that entail Master."

"Well I accept that for the present you still have your business and I know you feel a responsibility to your employees, so for the moment this arrangement would only be while outside of your work, evenings, weekends, you would live here and go to work each day, with certain restrictions of course."

"Yes Master, but I would not wish my staff to know of my position here."

"That I understand, but things such as your cage, have no effect on you at work, but it does ensure you come back to me each evening, as will others things I choose to do to you."

"I understand Master."

"While you are here you will accept anything I wish to do to you, including pain, and while you have your safe word I do not expect you to use it. Your boundaries I will push and expand your limits, what few you have, and you will never say no to me. You will experience pain and a lot of pleasure as well."

"When I do not wish to play then you will act as my wife, and we will enjoy all the things that a couple do."

"Any questions so far?"

"Will you tell me how to dress Master, even when we are a couple?" she said with a big grin on her face.

I looked at her, "Yes even what you go to work in." Her face lit up even brighter and she snuggled closer to me. I could feel the heat from her body and I felt myself getting hard again.

"I also want to delay your reassignment surgery for at least a year, partly because I don't want you to have it, partly because I think we need that long to see if this arrangement is permanent, and finally I don't want you now to rush into anything. Is that going to be a problem?"

"May I think about that Master I have strived so long to get this far, I don't really want to give it up now."

"You may, and if you decide not to delay it then I will still take you on, if you do delay and miss your chance on the NHS then its only fair that I pay for the operation in a years time if you still want it."

I saw a little tear in her eye, she was obviously thinking hard about what she wanted, and it was understandable, she had taken some ten years to get to this point and her operation was due in about three months time if they did not delay it again.

"Now if all this is acceptable I want you to sign this slave contract and we will register you as my slave, you should be aware that only I have the right to terminate this contract." I pushed the contract in front of her.

She looked at me, smiled, then picked the contract up and read it, it was a standard one I had pulled from the web, it gave me total power over her while she lived with me.

She read it through, looking at me a couple of times, before saying, "Just before I sign it says you will decide if I have sex with anyone else, what does it mean."

"Well you will be my property so if I should wish to 'lend' you to a friend I can and you can't refuse."

"But you won't give me away to anyone will you Master?"

"Be good to me and that is very unlikely."

I saw her expression change to one of dismay followed by determination. She picked up the pen and signed herself over to me.

I took her head in my hands and kissed her passionately, probing with my tongue as she responded, her hand going to my groin feeling for my hardness that was all too evident. As we came up for air she nervously said "Master what about John?"

John was the wimp of a boyfriend that we had chatted about before. He was quite effeminate and very slim and what I would call 'girly'.

She was bored with him and had told me he was submissive but because she was not really dominant they were getting bored with each other, despite that she did have feelings for him and I am sure he did for her, and they had been together for a couple of years.

I smiled at her, "What about John?"

"He will be devastated Master, he has no home and depends on me for a roof over his head, and as you know he works for me, it will be hard for him to see me every day and not be with me."

I took her chin in my hand and looked her deep in the eyes, "So what do you suggest my pretty little thing."

She stammered as she said, "Could we take him on here as a servant to us?"

I looked at her, trying to see if she was serious, this was adding a whole new dimension to our relationship, and in reality I wanted to get to know her so much better before introducing others to our play time. I had already considered bring others into our play but I was not sure if it was too soon.

To be continued...

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READ MORE OF THIS SERIES

Helen Ch. 03 Previous Part
Helen Series Info

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