Please tell Mrs. Sharp that we discussed that solution and that you will do that only because of the conditions of the new contract with Mrs. Sinclair. She will be more than happy to hear that.
But you have to ask her to give you a corresponding salary increase. And she has to get you a new female driver's license and ID. Please tell her exactly that, too. But now let's go to bed, my dear; it was a long day for you." With that, she hugged him and pulled him to her.
When they were in the bedroom, Mrs. took out her strap-on and gave it to Michael. "Be a dear and put it on. I want to ride you now like my strong husband," she said. Michael was a bit sad and asked if she would unlock his chastity device and enjoy his real cock.
"No, dear. We already talked about that. It would be better if you got used to the fact that you no longer have sex with your penis. You will learn to enjoy sex as a woman, and you will see that you might get an orgasm in your chastity device. And for a better feeling like a woman, I want to have you using that too…"
With that, she grabbed in her bedside table and took out a new butt plug and some lube. She let Michael turn on his side and inserted the plug into his hole. Then she helped him put on the strap-on. The leather harness of the strap-on made sure that the plug stayed inside him.
Satisfied that he was so well groomed, she pulled him to her. After he carefully penetrated her, she picked up her cell phone and switched something on. In the next moment, Michael felt a deep vibration in his buttocks, which steadily swelled up and down.
"Now, my dear. Enjoy your new feminine feelings and start fucking me like a bull." Michael started to move faster and fucked his wife with the artificial limb like with his own penis.
And she was right: after a wonderful time of mutual enjoyment, he too had an orgasm, and his caged penis discharged many bursts of his sticky sperm. They were both completely satisfied and fell asleep, tightly embraced.
The next day, Michael got his new testosterone blockers and some other pills from his wife and was told to swallow them immediately. After several days of that routine, he was already used to taking his medicines.
He was not sure what really happened inside him, but he felt a bit more tired, and his balls seemed to shrink each day. His wife said everything went as expected, and he should not worry much. But because of the shrinking balls, she got him another, really tiny chastity cage made of stainless steel.
She told him to put it in his purse and give it to Mrs. Sharp the next morning, together with his demand for an immediate pay raise. He should tell her that he would agree to be locked into that tiny cage right after getting a better contract.
The next day at work, Michael asked first thing in the morning if he could talk to Mrs. Sharp. When she called him into her office, he walked straight there on his high heels. When inside her office, he shut the door and walked in front of her desk.
"Hello, Michelle, what can I do for you?" she asked.
"Mrs. Sharp, ma'am. I had a serious talk with my wife about the new contract with Mrs. Sinclair. We came to the conclusion that I would agree to all conditions, even the demand for taking female hormones, under the condition that you will give me a raise in salary.
You know that I would lose my ability to get a hard-on because of that hormone treatment, and that it would be only fair to promote me at work. You also get some profit from the new contract with Mrs. Sinclair, and that's why I want to get my piece of the pie," he said with his head held high.
"Oh, Michelle, I cannot recognize my demure little secretary anymore. You are so demanding today. Is that really you?" she asked.
"Yes, it's me, Mrs. Sharp. But the demanding part comes directly from my mistress and wife. She asked me to tell you exactly that," he said. "But as a sign of my devotion to you, she gave me this..." With that, he took out the tiny cage from his purse and put it on her desk.
"The moment you sign a better-paid contract, you can lock me into that device. And the next day I will take my new birth control pills each morning right in front of you," he said with an already lowered gaze.
Mrs. Sharp beamed. "Oh, Michelle, that is wonderful news. I knew that you would be such a sweet, demure thing, and I will agree to the new contract. Mrs. Sinclair would be delighted to hear that.
Of course, I will give you an immediate pay raise and also a promotion in your job title. You will become my 'Executive Assistant,' and I will pay you $200 more each week. Is that agreeable?
If so, please prepare the new contract for me right now on your desk, and after printing out three copies, I will do the necessary changes in your personnel file in HR in the next second.
"Well, Mrs. Sharp, it is agreeable under the condition of a pay raise of $250 each week. And will you provide me with a new driver's license and a new ID under my female sex? If that is ok with you..." he suggested.
"That's ok with me, Michelle. Please write everything down right now, and I will do the necessary preparations in your personnel file. I'm so glad that we finally found a proper solution that fits both of us, and I can't wait to sign the new contract." She smiled at him.
"And I can't wait to lock up your precious penis in the lovely new cage." She laughed.
With that cleared, Michelle went back to her desk and opened a new contract file on her computer. After an hour or so, she was ready with the contract. Because everything was right, she printed it out on the central copy station, stood up, and walked straight to the machine at the other end of the office floor.
When she arrived there, she met Amy, and both ladies greeted each other with a hug. Amy really loved the new skirt suit that Michelle was wearing that day, and Michelle returned the compliment. Then Amy asked what kind of documents Michelle was printing.
Michelle printed out the new employment contract and smiled at Amy.
"Well, this is my new contract, Amy," Michelle said happily. From today on I will be 'Executive Assistant' to Mrs. Sharp. Amy beamed with joy. "That is so wonderful, Michelle; I am so happy for you. What was the reason for your promotion?"
"To be honest, Amy, it was a decision I made together with my wife. Mrs. Sinclair had offered a new contract for our company if I agreed to some special conditions. They want me to become much more feminine when I work for them.
They also want me to undergo a hormonal treatment for that, and I discussed it with my wife. You know, she is a gynecologist, and so we talked about the pros and cons of such a step."
Amy made big eyes. "And she agreed to such a treatment for you? How wonderful! She must really love you that she can live with such massive changes in your marriage. That means that you get your own budding boobies too?" She nearly shrieked.
"Shh, keep quiet, Amy! I don't want anyone to know that yet. But, yes, when I take the female hormones, I will hopefully grow some nice breasts of my own. Who knows, I may even end up as a busty D-cup girl. I guess that would be the most wonderful thing for me. But that means, too, that I will lose my ability to have sex with my penis. But that's ok with me.
I am already locked up permanently, as you know, and maybe then I will not have to wear that chastity cage any longer," he confessed.
"Oh, Michelle! I would love to see you with your own budding breasts. And surely the hormones will also help you develop a more feminine figure. I always thought that you have a nice-looking butt, but it would not be bad if it would still grow a bit wider. You would love that new body, I'm sure," Amy said.
"Yes, you are right. It is something I always dreamed about in my dreams but never thought might happen one day," he confessed.
"Oh, you lucky girl, I hope that everything comes to a wonderful end for you. I'm so excited to know that and hope that I will see the welcome changes on your body soon," Amy said. Then she had to go to her own desk for work.
Michelle went back to Mrs. Sharp with the three copies of the contract. When she arrived at her office, Mrs. Sharp was on the phone. She winked at Michelle to take a seat and continued her call.
"Yes, Cynthia, darling, it's true. Michelle came back with the copies of the contract this moment. I guess we will have the time to wait for your arrival, and you can witness this wonderful event.
We'll wait for you, darling, but please hurry. I'm just too excited in anticipation... Bye, dear, see you soon."
With that, she hung up the phone and beamed at Michelle. "I'm really so excited, Michelle. You heard that I already told Mrs. Sinclair the news, and she wants to witness when I lock you up in your new chastity device.
I hope you don't mind that... I have already cleared everything up with HR; your personnel file will be altered in a few minutes, and I have already ordered some new doorplates and nameplates with your new title.
When they are mounted, I will have some photos taken for publication of your promotion on the internet." She smiled at Michelle.
"But now be a dear and give me the copies. I can't wait to sign the new contract with your promotion." Michelle walked to the desk and put the contracts on it. Mrs. Sharp took each one, opened it, and signed it on the last page. When she was ready, there was a knock on the door.
After a "Come in, please," from Mrs. Sharp, the door opened and in came Mrs. Moore.
"Hello, Becky," she greeted Mrs. Sharp. "You wanted to talk to me?"
"Well, yes, Bethany. I decided to promote my dear Michelle from today on as an 'Executive Assistant,' and I wanted to let you do all the necessary changes. You have to authorize the orders for the new name badges and the changes in the personnel file. Would you be so kind and do this on such short notice?" she asked Mrs. Moore.
"Oh, that's surprising. But may I know the reason for such a quick decision from you? I know that Michelle is really valuable to you, but it is a very high raise in such a short time," she said quizzically. "I hope she deserves it."
"Oh yes, she really deserves that promotion. Please take a seat, Bethany, and listen to my explanations," Mrs. Sharp continued.
And with a smile to Michelle, she ordered, "Michelle dear, please get us some coffee and cookies. We want to talk in a good mood. But please make coffee for four, you know, we expect Mrs. Sinclair shortly."
With that, Michelle went straight to the kitchen to prepare the coffee. When everything was prepared on a silver tray, she grabbed it and walked back to Mrs. Sharp's office. Meanwhile, she was used to securely walking in her 4-inch high heels with the silver tray with cups and coffee.
That was something she learned so well at Mrs. Sinclair's company party. With that knowledge, she could easily start as a waitress in a crowded saloon.
Back at the office, she served the two ladies coffee and put the cookies on the desk. When she was ready with that, Mrs. Sharp smiled at her and said, "Michelle, darling, the front desk just called and told me that Mrs. Sinclair just arrived. Please be a gem and go and greet her and bring her up to us."
"Yes, Ma'am, right away," she answered. Michelle just turned on her heels and went to the front desk. When she arrived there, Mrs. Sinclair stood near the receptionist and smiled broadly at her.
"Oh, Michelle, I am so glad that Mrs. Sharp just called me and told me that you finally agreed to our new contract and all the special conditions that concern you. She said that I should come to join you to celebrate the news and to witness your devoted agreement," she blurted out.
Michelle was alarmed and hoped that Mrs. Sinclair would stop talking about that topic in front of the receptionist, and so she tried to push her to soon return to Mrs. Sharp.
"Welcome, Mrs. Sinclair. Nice to meet you again. Hello, Casey! Would you please follow me to Mrs. Sharp's office, Mrs. Sinclair?" She said with a warm smile to Casey and Mrs. Sinclair and turned around fast to walk to the elevators. Mrs. Sinclair followed her with clicking steps.
Once inside the elevators, Michelle calmed down a bit and smiled at Mrs. Sinclair. "You did not want to let Casey hear the news?" she asked.
"No, I didn't," Michelle answered. "Casey is a really nice girl, but she is too much into office gossip. If she ever gets to know something confidential, it is around the building much faster than a thunderstorm.
And I don't want to be the topic of the next office gossip so soon," Michelle answered. Soon they reached the office floor and went out. After a few seconds, they arrived at Mrs. Sharp's office.
Mrs. Sharp and Mrs. Moore were laughing when they entered.
"Oh, Cynthia, so nice that you could come on such short notice," Mrs. Sharp greeted the new guest. "I already talked to Mrs. Moore about the new development with our sweet Michelle. She is more than pleased to hear the news, too.
But please, take a seat, dear, and have a coffee before we start with business." She smiled at Cynthia. After Mrs. Sinclair sat down and Michelle poured her a coffee, Michelle was told to sit down too and get a coffee for herself.
"Well, as you already know, our dear Michelle here finally agreed to all of the requirements of the new contract with your firm, Cynthia. That includes her going on a hormonal treatment to become much more feminine than today. Michelle may or may not know it, but she is on her way to becoming a real woman, and soon her budding breasts may become quite large and feminine and may even require a C or D cup, and her cute little ass will fill out as well, and her waist will become smaller, especially with some corsetting, which I will speak to her wife about.
Even if she is not much of a man afterwards, she is okay with this treatment and promised to sign her devotion under these requirements and be locked up by me in a much smaller chastity device, and also to start her hormonal treatment by taking her first estrogen pills right now. Is that true, Michelle?"
All eyes of the ladies went to Michelle, and she turned red that moment. Surely she had seen this moment coming after her talk with her mistress, but she also had feared the following embarrassment.
"Well, ladies, Mrs. Sharp is right. I promised everything right from the moment my demand for a promotion and an appropriate pay raise was confirmed. And from then on, I will take my prescribed hormones daily right in front of Mrs. Sharp so she can always check that," Michelle said with a trembling voice.
"So, then it's settled! I will acknowledge that from now on, Michelle is our 'Executive Assistant,' and that means that she is also expected to assist in each meeting of the board of directors," Mrs. Moore confirmed. Mrs. Sharp and Mrs. Sinclair smiled at each other, and Michelle felt a warm feeling in her stomach.
"I agree to all the necessary changes in our company right now, and you are now to sign your new contract, Michelle. Please come over here and do your business, girl."
With that said, Michelle rose from her seat and went over to Mrs. Sharp's desk. Mrs. Sharp also got up and handed her her own gold fountain pen with a beaming smile and asked her to take a seat at her desk.
When Michelle sat down and started to sign the contracts, Mrs. Moore took some pictures with her mobile. "I will get these pictures posted on our web page this morning with the publication of the personnel measure," she told them.
Michelle smiled at the ladies and signed all copies with her name, 'Ms. Michelle Garrett.' When that was done, she stood up again, and all the ladies applauded. "Welcome aboard, Ms. Garrett. As you are from now on assigned to the title 'Executive Assistant,' I will be sure to call you that from now on in official talks outside this circle of ladies too." She smiled at each of the ladies.
"And I would like you to do the same, ladies!"
"But inside our inner circle, our sweet Michelle will stay the demure little sissy secretary she always longed to be and do her submissive duties for each of us. That includes our sweet Bethany, Michelle. Is that clear?" She ordered with a much sterner voice.
"Inside our circle, we will continue to call you 'Michelle,' and you will always obey our demands, as we three are your mistresses from now on.
Of course, your main mistress is your lovely wife, and you will always obey her first, but during business hours, we three will take her place. And to finally seal that deal, you are now to be locked up in that tiny little cage, and then we will watch you swallow your female hormones. Please come over here and lift your skirt, my dear." With that, she took the chastity device from her desk and went over to Michelle.
Michelle looked down at the floor and started to hike up her tight pencil skirt. When her panties were in full view of all the ladies, she pulled them down, too.
It was the first time that Mrs. Moore saw Michelle's chastity device, and she was really excited.
After using her key to open that device, Mrs. Sharp was smiling. "It looks like your pretty penis is already much smaller than the last time I saw it," she gasped.
"That's a wonderful development, Michelle. I already wondered how I should be able to fit you into the new cage, but that size seems to be really appropriate for you right now."
With that, she pushed the cage over Michelle's clit and fastened it behind her scrotum. After locking up the internal lock, everything was well secured, and Michelle was unable to break free from it anymore.
The ladies applauded, and Mrs. Sharp pulled up Michelle's panties and pulled down her skirt. Then she gave her a long hug and kissed her passionately.
After her fate was sealed, Michelle calmed down a bit and smiled, too. Now she was on the verge of real womanhood, and that would be her path into the future. When Mrs. Sharp left her, she took her seat again and took her prescribed pills out of her purse.
With a warm smile, all the ladies watched while Michelle squeezed the pill out of the blister pack and put it in her mouth. After a quick sip of coffee, she swallowed it down and immediately felt much more feminine.
Again, she heard applause from the other ladies, and Mrs. Sharp beamed, "Welcome to womanhood, Michelle. We are really proud of you." With that, she gave each of the ladies a key for the chastity device.
"And now be a dear and get us the cooled bottle of champagne from the fridge in the kitchen. You'll find some suitable glasses there too. And if you meet Amy on the way, please take one more glass for her and bring her back too. I guess we have to celebrate something."
Michelle rose again and went to the kitchen. The walk through the office was like walking on the clouds. She was all smiles to herself and showed her new, embraced feminine grace to all of her colleagues.
As expected, she met Amy on the way and told her the news. Amy nearly cried for joy and was eager to come with her to celebrate. When they both arrived back in Mrs. Sharp's office, they were warmly greeted.
Michelle opened the bottle of champagne and poured each lady a glass. Mrs. Sharp made a toast and again welcomed Michelle into the world of women. All the ladies chimed in and wished Michelle a wonderful life as a real sexy woman and told her that they would help her with the changes the hormones surely would do to her.
Michelle had tears in her eyes and thanked all of them. She confessed that her wife does not want her to go all the way and have SRS, and all the ladies said that this was so lovely to know.
Soon it was decided that they wanted to celebrate again together with Michelle's wife in a nice restaurant afterwards, and even Amy was invited to come. After that was settled, Michelle and Amy went back to work, and Mrs. Sinclair said goodbye to everyone.
When Michelle was alone at her desk, she thought about the past time since she was spotted in her feminine underwear by Mrs. Sharp and all the events that followed. Then she thought about her life in the future that she would certainly live as a real woman, with the only exception that she would still have her pretty penis well locked in her steel cage and satin panties.
And she was so very happy with how it all turned out.
To be continued...?
Steph
2025-06-16 14:23:02 +0000 UTCBGDESOMALI
2025-06-14 09:24:11 +0000 UTCBryan
2025-05-08 23:45:10 +0000 UTCAmanda
2025-05-07 23:54:43 +0000 UTC