Helen Ch. 09

Story Info
We take on Helen's b/f as our Maid. Nancy starts training.
2.7k words
4.22
10.6k
4

Part 7 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

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...

As we walked through the house I felt very contented, I slapped Helen's bum playfully and she ran ahead of me squealing in a girly way, before letting me catch up with her and I grabbed a handful of her ass and pushed my finger into her puckered hole before lifting her easily, kissing her passionately and carrying her upstairs to the bedroom where I dumped her unceremoniously on our bed.

I let her sit up and she proceeded to undress me before we crawled under the duvet, where we made love gently to each other, I even took her small cock in my mouth and pleasured her to an orgasm, before I mounted her and took her sweetly like only a lover can.

Once we were spent we spooned and soon fell into a deep and untroubled sleep.

When the alarm went in the morning I went down to the basement while she got dressed. I unlocked the door and put the lights on, Nancy was curled up in her cage like a dog, well a bitch now, and she blinked hard as the light was no doubt very bright after the total darkness of the basement.

She groaned and said "Please Master let me go, I don't want this and I can't stand it, I have not slept, and my ass is so sore."

"Are you sure you want to leave girl, you have nothing to look forward to, and it will hurt Helen, the fact that you want to go after just one night."

"But I am not a girl Sir, I am a man."

"Well I won't force you to stay." I said moving over to the cage and unlocking it. "Get out and let's remove that plug."

She got out and struggled to stand she was obviously very sore and aching from the cramped position she had been in all night. I turned her round and removed the anal plug, she gasped as it came out and said "Thank you." I ignored the fact she had not addressed me correctly, and I took her arm, taking her to the downstairs shower next to the garage and pushed her in it turning on the shower, it would warm up but was very cold to start.

"When you are clean join us in the kitchen." I walked out and left her to it.

When I entered the kitchen Helen was very cheerful and humming a tune to herself as she made some breakfast, fresh coffee, and the oven was on for croissants.

She saw the look on my face and said "What's wrong Darling, errr sorry Master."

"You can call me Darling it's fine when we are alone" I said. "It seems Nancy does not want to live with us, she wants to go, she is just showering then joining us."

I saw Helen's expression drop to one of a pout, disappointment I think in Nancy's decision.

"I won't force her to stay, you know that don't you, she has to want to be here, a willing choice as you have made."

"Yes Darling I understand, let me talk to him, her."

At that moment Nancy walked in, naked but for the cage she still had on and I still had the key for. I stood up and a left the room to allow them to talk, "Ten minutes Helen then you need to be off to work, and I want you to finish at 4 tonight"

"Yes Master." She replied as I left the room.

I went and sat in the lounge and got my laptop out, I had a few things to organise today, most of which related to Helen, some to make changes to the basement, those would take a little longer, and a visit to an extreme restraints website to order some toys.

About 5 minutes later Helen came in holding Nancy's leash, with Nancy on her knees behind her like a bitch. "Master Nancy has decided that she wants to stay here if you will have her, she wants to be a woman like me."

With that she handed me the leash. I smiled at her, "Is this her decision, or yours, have you made her choose this life?"

"No Master it is her decision, although being with me may well be a dominating reason to suffer like a good girl for us."

"Good then over the weekend we will discuss her future, but for now take her and lock her in the basement, then you better get to work."

I also said to Nancy "You will put on the outfit that you wore yesterday for now, I will come and see to you later."

I dismissed them with a wave of my hand, but Helen came over to me and gave me a peck on the cheek before disappearing, dragging Nancy on her leash behind her.

Once I heard her car pull away I made a telephone call to a Doctor friend of mine and asked him if he would come round. He knew about my proclivities and I had often used him to consult on various medical things in the past, he was happy to do some private work for me, I did so hate waiting for appointments when I could afford to pay privately. He said he would be with me by midday.

I then went onto the internet and started my buying, with two male to female submissives in the house I would need more equipment than I had at the moment.

I found easily what I needed in the more mundane items, then I went onto a specialist restraints and more adventurous restraints site. I started by adding a 'Tower of Pain" which was a device with a plate that went between the breasts, attached to that was two clover clamps that could be attached to nipples, and by using the threaded rod the girls nipples could be pulled and stretched, eventually leaving them with extended nipples.

I also added a 'Leather Breast Binder with Spikes' and a 'Studded Spiked Breast Binder.' Both of these items were made of leather with spikes that were on the inside, unlikely to break the skin, but when pulled tight would be uncomfortable and a constant reminder of my power over them and my ability to hurt them if I so desired. The second item also had a hole where the nipple was so that additional clamps could be fitted if desired. Next was a strap on, a specially designed one that could be worn by a male, or female who was in chastity, and it did not interfere with their cage, this would be for Helen to use on Nancy to train her into gett

The last thing to add was a complete chastity device in metal, this consisted of a metal Collar, Cuffs for the wrists and thighs, a metal bra, and a metal chastity belt that could be worn full time with a suitable opening for the anus, and a small tube to fit the cock in, bent downwards which would necessitate sitting to urinate like a woman has to. For this I needed accurate measurement to have it adjusted to fit so I thought it was time to get Nancy from the basement.

I went downstairs and unlocked the door. Nancy had dressed as I had told her to and she had tried to do some makeup, obviously left with her by Helen. It was not a bad effort but I had plans that would remove the necessity of having to apply all her make up every day.

"Follow me." I said moving back upstairs to the lounge. She followed.

"Now undress, I need you naked to take some measurements."

She did as she was told, carefully folding her maids uniform and putting it on the arm of the chair.

"Arms up." I moved in front of her with the tape measure and took the measurements that were needed for the full metal chastity device that I was going to order. As I moved round her I saw that her clitty was trying to expand in her cage, it seems she was now resigned and even excited by what would happen to her, she really had no idea of what was to come.

Once I had finished taking measurements I took her arm and stood her in front of the stand.

I attached her by the neck, wrists, waist and ankles to the stand then stretched it upwards and adjusted the distance between her ankles and wrists. She was now immobilised and 'star like', naked except for her cage which I now unlocked and freed her. She sprung to attention, she was quite well hung, I am sure Helen had enjoyed that on many an occasion. I then fitted a spider gag, I didn't want her protesting when the Doctor arrived.

I then sat down without a word and entered the sizes for her new chastity device, paid for a superfast delivery, with luck it should be with me after the weekend.

Satisfied I then went to the kitchen and made myself a pot of coffee, knowing that the Doctor would be here shortly. I then went back to lounge, poured myself a cup and sat back in my chair to wait for him, studying Nancy as I did.

Nancy was young, slim and obviously quite fit. While she was still a boy she had a slim waist which I knew could be pulled in with a good corset, and that would give her hips a chance to look more feminine. She has no obvious Adams apple, was not over hairy, and didn't need, it appeared, to shave every day, she had almost no shadow, she would look very presentable and convincing as a woman.

The doorbell rang and I went and opened it. Eric the doctor was standing there with a big grin on his face "What are you up to now." We embraced and I chuckled, "I have a couple of new candidates that I need your help with."

I took him through to the lounge and poured a coffee for him. As we sat down he noticed Nancy on display and said nothing just looked at me.

I started the conversation "Firstly there is Helen, she is at work at the moment, she is male to female and has been on hormones for over two years, here is a list of what she is taking." I passed him the list Helen had given me. "Now she is talking about surgery, but I would prefer it if she didn't go through with that, is there anyway to increase what she is taking to make her shrivel even more, even to the point of stopping her getting any kind of erection."

Eric thought about it for a moment. "Yes we can increase the doses of these", he pointed to the list, "that will have the effect of getting more female hormones into her system, hence reducing penile size while increasing her breast size. But it will make them more sensitive and at times painful."

I smiled, "Then initially we will go that route, give it a year and see if we get the results we want. Can you organise the prescriptions please."

Eric nodded.

I motioned towards Nancy. "Now this is John, Helens old boyfriend and he would like to become Nancy and be our live in maid. Can you give her a full medical make sure she is disease free then we can start her hormones. I would also like to discuss castrating her at some point if it would help accelerate her change." I watched as Nancy's face changed and her eyes nearly cam out on stalks.

Eric walked over to her, and started his examination. He took her temperature, looked in her mouth having remove her gag, then replaced it, lifted her cock and scrotum feeling it to make sure there were no lumps, Nancy could not help herself but start to get hard as he played with her, then he went to his bag and took out a syringe and took some blood from her.

"It will take a couple of days to get the blood results but at first glance I can see that he, sorry she is healthy, so she can start the hormones straight away, I will put her on the same dose as Helen."

"As for castration, you need to think about that hard as it is obviously not reversible but it would accelerate the process of her becoming more feminine, it will flesh out her hips and ass as long as she has a suitable HRT regime."

"Anyway I look forward to seeing the progress you make with her, and I can't wait to see Helen, you have said so much about her, now I better get on."

"Well you must come to dinner once Helen is settled in." I smiled knowingly at him. He was a long time friend apart from being a doctor and he enjoyed a lot of the things I did socially, he had been over before and enjoyed ladies that I had in my control, so I was more than happy for him to use Helen one evening, although at this point Helen did not know this.

Once he had left I released Nancy, replaced her cage and let her dress herself again before telling her to clean out the basement thoroughly. I told her that I had some things arriving for her that afternoon so it should be spotless, I would inspect it when she told me it was clean, or at 3.30pm whichever was first.

I then sat in the lounge and planned out what needed doing with my two girls. Originally I had intended to get Helen pierced this evening, but on reflection and taking into account the 6 weeks or so I would have to wait for the piercing to heal I decided she could go back in the cage and Nancy would be the one getting the piercings.

I jotted down some notes on my laptop, a reminder I guess, to help me formulate my plans. I knew what I wanted from Helen and to a large extent know the path I would lead her down, but Nancy was something I had not allowed for and changed the whole dynamic somewhat. That caused the need for some rethinking, but overall I thought that having Nancy as well would be a bonus.

At 3.30pm I went to the basement to find Nancy. She was on her knees cleaning the skirting boards and there was a smell of disinfectant in the air. I was impressed. "Stand up girl." I said roughly. As she did I grabbed her and pulled her to me. "You have done well." I smiled at her as I pushed her to her knees, "Now you can have your reward." I undid my trouser zip and pulled my cock out, it was already half hard as I guided it into her mouth, "Now suck and don't spill a drop." I pushed it into her mouth till she gagged then I grabbed her head and fucked her face with no pity or concern for her, she was there just to get me off.

It was not long before I felt myself cumming, it had been an erotic day so far, buying toys, the doctor's visit and now this, and I held the back of her head hard as I thrust into her throat, I heard her choking, but didn't care as I emptied my balls into her.

I released the pressure and withdrew, there were tears streaming down her face, I patted her cheek saying, "Good girl you will do well here."

I left the room briefly and then came back in with some clothes for her. "You have done well today, we are going out as soon as Helen arrives, put these clothes on you will come with us, and repair your make up as best as you can."

With that I tucked myself in, locked the door behind me and went to shower and get ready for Helen getting back from work.

To be continued...

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AnonymousAnonymousalmost 6 years ago

loving it so far ,would love to be in Nancys heels

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Helen Ch. 08 Previous Part
Helen Series Info

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