Helen Ch. 11

byPhilippasubmaid©

This story is a graphic tale of a Dom and his very submissive transgendered males. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy

It is best if read with previous chapters.

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

The following morning after a restless night due to Helen's discomfort with her piercings, Nancy knocked on the door at exactly 9.30.

"Come in," I said, not caring that Helen was naked and without any bedclothes over her, as was I, sporting my usual morning hardness, it was not like Nancy had not seen both of us naked before.

Nancy opened the door and bought our breakfast tray in, she was dressed in the Maids uniform as directed and I motioned for her to put the tray on the bed between Helen and I, and then told her to kneel by the side of my bed. As Helen stretched and tried to wake up I reached over and kissed her gently, at the same time taking Nancy's hair and pulling her, making it obvious she should deal with my hardness.

I was pleased to see she did not struggle or put up a fight she just meekly went down on me taking my hardness into her mouth and started working on it. She was really quite a good cocksucker and I knew she would only improve in time, I would make sure she got lots of practise. It was not long before I grunted and held the back of hr head until I had filled her mouth and throat with my seed. This was the beauty of having Male to Female toys, no danger of pregnancy and they were always eager to take cock.

As I pulled her mouth off me I saw Helen grinning broadly then wink at Nancy, she was obviously happy at Nancy's attitude to this task, and I realised then that these two girls would be very close to each other.

While Helen and I had our breakfast I made it clear that this was just a chat session, no Master slave toy situation just three adults discussing our relationship and where it would go, trying to find some boundaries to adhere to, to see if there were any 'hard' limits that the girls would declare before we started this relationship full time in ernest.

I made it clear to Nancy that she was our servant, that she would do whatever Helen or I told her to, that's she could have a good life if she toed the line and pleased us, well me in particular. She was also told that she would be used by others but only with people I chose and that generally I would be present, she must not refuse as to do so she would be punished.

Helen already knew her position here in our home, but so it was clear to Nancy I restated it. I told Helen that she was my partner and my equal when we were alone together or with Nancy, that she should share the ownership of Nancy and that Nancy would do whatever she was told to by her. Helen was also to be used by others but on a much more selective basis, and that we would attend munches and parties in my circle of acquaintances.

Both girls raised queries but there was no real objections to their roles and so the meeting ended with me saying that while their piercings were healing the usual activities were suspended, not that that meant I didn't not need to be obeyed. There was also one other visit that Nancy needed to make to make her really feel like a woman.

And so we had a lazy day on that weekend and things settled to a routine, I kept an eye on both their piercings, and was keen to see them heal as then the real fun and training would begin in particular with Nancy.

The following Tuesday while Helen was at work Nancy's full chastity suit arrived, so I hid that until I could lock it on Nancy.

Helen continued to go to work, albeit in slightly more tarty clothing than before as I insisted that she was to portray herself, in particular to male clients, as being available for 'extra' services.

On the Thursday after work Eric dropped in just to check the girls piercings and to make sure they were both ok after the increase in hormone therapy. He passed them both fit and said that in a couple of weeks the piercings would be fully healed.

As he was leaving I said quietly "Why don't you come to dinner on the 23rd, (that was the Saturday week), and perhaps you would like to sample the delights of the house." I winked at him and he grinned, "That would be lovely, I look forward to it, I will save myself up."

It was during this time and the 10 days that followed that I studied Nancy and Helen and the interactions between them, coming to realise that they were growing together like sisters and despite the fact that Helen owned Nancy it did not seem to matter, Nancy was always respectful, perhaps enjoying her new role as the submissive, and Helen I noticed could get her to do anything for her, not sexually I was pleased to say but just little chores and things about the house.

And then there were the visits to the tattoo parlour every Tuesday and Friday evenings. This was to give Nancy permanent make up, to save her having to do it everyday and also to emphasise the fact that she would be feminine forever, no going back now. It also would have the added bonus of not smudging or coming off when she was being used hard and got a bit sweaty. We had her eyebrows done, eyelids coloured, eye liner done, the only thing she had to do in the morning was put some lippy on.

One morning during this period it was obvious that Helen was getting more and more horny. She was struggling in the morning, having a hard on in her cage like I had never seem before. She snuggled up to me and her hand wandered under the sheets to find me, I was already hard for her, it had been difficult not using her while her breasts had healed and apart from an occasional blow job from Nancy I was getting frustrated myself.

She whispered in my ear "Darling please unlock the cage I have a treat for you." Looking puzzled I looked at her and wondered what she meant.

I did as she asked, intrigued by what she had said, as I freed her she sprung to attention, she was obviously very frustrated, then she whistled, and stroked me under the covers getting me even harder.

As the door opened, Nancy came in naked, but before I could say anything Helen put her fingers to my lips then climbed on top of me with her back to me, holding her cheeks apart as she lowered herself on my tumescence, she rose and fell gently until I was fully buried in her, then she lent backwards stroking herself and Nancy climbed onto the bed and knelt, head down ass up, in front of Helen's cock and shuffled back until she was buried in Nancy's boi pussy.

Between them they managed to stay in each other with me in Helen, she rising and falling and milking me for all she was worth. As they continued I could tell they were both getting more and more excited until suddenly Helen gasped and drove herself forward deeper into Nancy and almost losing me from inside her. As she did Nancy screamed in pleasure and I saw a dribble of cum from inside her cage, I suspected it was her first sissygasm, it was wonderful to watch her little cock pulse as she came.

Having cum herself Helen slumped back on me driving myself deep into her welcoming boi pussy and it was not long as she rode me before I felt my cum rising and injecting itself deep into her belly.

As we all collapsed in a heap Nancy was the first to get off the bed and stand beside it. Helen somehow managed to turn on me so that she was facing me without letting me out of her despite me now being flaccid. Once sitting facing me she very seriously said "Darling that was organised by me, I told Nancy what to do, so I don't want her to receive any punishment for joining us in our bed."

I smiled up at her, pulled her head down to mine and kissed her, passionately, and hard, then looked into her eyes, "It was a wonderful idea, and of course I will not punish Nancy, she just did as she was told, if anyone needs to be punished it should be you, but I won't, we will wait till Saturday for that." She looked at me not understanding what I meant but I did not enlighten her she would find out in due course. "Now you better get to work." And I slapped her bum as she climbed off me.

Nancy was still standing by the bed, and I grabbed her cage, "What is this?" She blushed bright red and said "I think it is a sissygasm Master, its what happens when someone like me is fucked and my prostrate is massaged as Mistress Helen did just now Master. I am sorry for not having control of myself."

I said nothing but smiled at her, I knew what it was but I was happy to see that she could cum in this way it would make using her boi pussy far more pleasurable for her.

"Well you better get back to your room and get dressed, I am sure you have work to do."

"Thank you Master" she said as she scurried out of the room.

Things continued as normal, and I could see the girls were fully healed now. As a result I took great pleasure in having Nancy lift her skirt for me, I then put a small padlock through her new ring and clicked it shut, effectively locking her penis in a bent position preventing her from getting an erection. I smiled as I smoothed her uniform down and I looked at her, "I know you have been playing with yourself, but no more, from now you will only cum through sissygasms if at all." She blushed bright red and I knew that my guess had been true.

On the Friday evening before Eric's visit Helen got home early, she now finished at 3pm on a Friday, and once she had changed out of her office clothes into the baby doll I had left out for her to wear we called Nancy into the lounge to join us.

I had by my side a large box, her full metal chastity outfit, which Helen and I would now fit to her.

I smiled at Nancy, "Nancy we have a few things here that you will wear for the weekend, they will be locked on you, and they will not be removed until Sunday, now undress, you need to be naked."

"Yes Master" she replied. She quickly stripped her clothes off folding them and putting them on the chair. I was pleased to see that her body, despite the shortness of time being on hormones, was starting to soften, her tiny breasts had a softer look to them, her nipples a bit perkier. I motioned for her to come closer to me, and I felt her breasts, pinched her nipples, which made her jump, they were already very sensitive, that sensitivity would grow as her breasts did.

"Starting Monday we will put you on a breast enlargement program, this will help a bit, mainly using pumping. I will go through it with you later."

I looked at Helen who stood up, and I delved in the box, coming out with firstly the collar and bra. This was quite small at this stage as Nancy had almost nothing to go in the bra, but it could be remade as she grew.

I passed it to Helen, and she moved behind Nancy placing the collar round her neck and clicking the lock shut. There were chains from the collar supporting the bra and Helen then pulled the bra strap behind Nancy's back and again clicked the lock shut. Next we fitted her chastity belt, this was a bit tricky as we had to get her limp penis into the tube that would allow her to pee while she was locked up. Helen tried but Nancy got excited when she was touched by her former lover, so in the end with the use of some ice I managed to get her soft enough to go in the sheath and we could lock her into the waist belt.

I turned her around and admired the perfect fit of the belt. I liked this design as the belt was locked and had a centre piece that went down in a curve encasing her penis and forcing it downwards leaving her smooth to look at. At the end of this curve were two chains that then went to the back of her waist, securing her in it while leaving her anus available.

Next we fitted her thigh and wrist cuffs, adding the chain that connected her thighs together and to her waist, these had the effect of restricting her ability to take any big steps, she would have to be dainty in the way she walked.

I then told her to get dressed again and once she had I secured her wrists through holes in her uniform that I made, restricting her movement of her arms.

Helen sat beside me and we made Nancy do a twirl, we were both pleased with Nancy's new chastity. "This will be on until Monday morning at least, if you are a good girl I will release you then."

To be continued...

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by Anonymous

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by Anonymous06/12/18

I want more !!

I want more!!!

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by Anonymous05/28/18

Awesome story

This is a seriously hot story. Looking forward to the next chapter and to learn more about what happens to Nancy and how far her transformation is to go :)

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