Retired to a Whole New Life Ch. 02

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's.

They helped me too my feet and we went back out to the living room, Michelle locking the playroom door behind us. With better light I was now able to get a better look at the device that secured my sissy clit. I tapped on it but could feel absolutely nothing on the inside. My crotch was as smooth as a natural woman and the belts felt totally secure. I could not get my fingers under the device except for a small spot near my perineum.

There were also 2 small slots at the top. I was told that these were to allow for proper cleaning. But the overall design was quite comfortable, and I could flex, squat, stretch and move with no physical discomfort. The rear strap had enough slack to move it to the side for using the toilet. I could just feel the small tube pointing out the bottom to allow me to pee. I could also feel it inside my trapped clitty as well.

Mistress Michelle stood close and ran her hand over my smooth front. "I love how this feels now Brenna. And you will be able to wear much prettier pantys now, instead of those tight panty girdles. And the sissy pink straps that keep you secure will make a nice statement to those who see them."

She held my face and gazed into my eyes. "Thank you for giving yourself to us Brenna. We will have amazing times together!" She kissed me deeply, then ran a finger down my cheeks and across my lips. I took it into my mouth sucking it gently, before she removed it.

"And thank-you and Mistress Cara for showing me a wonderful new path forward Mistress."

Cara examined my well bruised ass and said it would be sore for a while, especially for sleeping tonight. "Let me get something to help it feel better," she said while heading to her bathroom.

She returned with a large towel and some other items. She put the towel on the couch and told me to lay in it. I then realized it was a cloth diaper not a towel. I laid down and as Michelle lifted me by my feet. Cara squeezed some ointment from the tube and spread it softly over my bottom. The smell immediately told me it was diaper rash cream. After rubbing it in thoroughly, and causing a little stirring in my chastity, she grabbed some baby powder and sprinkled it on my bottom. As Cara pulled the diaper tight and pinned, it Michelle, who had left us for a minute, returned. Michelle put something over my feet and up my legs then had me stand up. When I did, she finished pulling the clear pink plastic panty over my diaper. Shiny lace accents at the waist and leg openings, and rows of lace on the bottom.

It was getting late, and my Mistresses had to work the next day. A gorgeous pink baby-doll nightie was slipped over my head and accentuated my new breasts. Michelle led me to my bedroom and as I sat on the bed I realized how soft the diaper actually felt on my swollen bottom. I softly fondled my breasts as Michelle put a collar around my neck.

Cara returned with a large glass of juice saying it would help me sleep after all the wine and poppers I had consumed. After I drank it down, she fastened leather cuffs around my wrist and they were attached by short chains to my collar. The were long enough to sleep comfortably but not long enough to reach much below my waist.

I didn't really care, just wanting to lay down and sleep. And sleep came soon. Unbeknownst to me, my Mistresses looked in on me in the morning before leaving for work. I didn't awaken until shortly after 10.

Once I realized the state I was in I sat up to find Mistress to change me so I could go to the bathroom and clean up. I searched the house and could find neither Mistress. I found a note on the kitchen table:

Brenna darling.

I will be back to check on you at lunch time. There is coffee in the pot and plenty of breakfast food. I am sure you can manage that with the cuffs on. You looked so peaceful, asleep in your diaper that I didn't want to disturb you.

Love Mommy.

I poured some coffee and feeling the pressure in my bladder I realized I was already wet. Gee, I must have slept soundly. No wonder I didn't hear them leave earlier. After I ate, I went to my room and looked at myself in the mirror. Except for what I considered a rather manly face, everything I saw screamed "little girl" back at me. My pink baby-doll and pink plastic panty, the way it sagged a bit from the wet diaper, the painted finger and toenails.

My clitty started to get hard in its prison. The bigger I got the more it hurt. I felt the head expand outside the tube and the throbbing from the brand could really be felt. I cried a bit. Not just from the pain but from the happiness I felt by having given my self to Mistress. But I would need to take my mind off things in order for it to shrink back to a comfortable level. I went to watch TV until Mommy returned to change me.

Mommy returned as promised, bringing in a couple bags and lunch. She first took me to the bathroom and undressed me, allowing me to go potty and shower. She handed me a couple of special sponge tipped swabs to clean inside the chastity. After I was cleaned up she handed me a pair of pantys and we went back to the kitchen to eat. I winced with the from the pain in my still throbbing bottom I sat down to eat. Mistress noticed me flinch and asked if I was still sore.

When I admitted I was, she took me back to the bedroom and re-diapered me as I had been the night before. At least sitting to eat would not be painful now. She said she took the rest of the day off so she could talk with me.

I asked her what about and she said we needed to make arrangements for the wedding and the future. As it was mid March, she and Cara decided to get married in mid July. She said that would give me time to sell my house, and get my affairs in order back home. I was to prepare to move in with her and Cara. She said Cara had enough connections to take care of visa issues. I would need to be back a week before the wedding, to help with preparations.

I was also to prepare my mind for the fact that the only time I would be dressed as a male again, after I returned, is for the few days around the wedding as her brother and my children and their families would be attending.

She knew that selling my house would provide total financial security for me, even after setting a good portion aside for my kids. With her and Cara's incomes, we would live quite comfortably. You will be our lover and maid, and our kinky play toy. You will be a companion and a friend we can trust in. You will have hotter sex than you would ever imagine possible. And you will have the freedom to enjoy the beach and the mountains.

"This has been such a whirlwind, Michelle. Everything's moving so fast. You know I hate to make rash decisions. But, ever since I lost Deb, life has really been pretty boring, outside of skiing and playing golf. My friends aren't many. And my kids are spread all over the country so I don't see them that much. If life going forward is anything like the past few days, I would be a fool to say no."

"Well then that settles it. You will have to come up with a story for your family when they see you put the house on the market. I would just tell them it is a "bucket-list" wish to move to Europe and travel and make new friends. I will text Cara that everything is set."

"OK, with that little chat out of the way, I need to go to the market so we can have a nice dinner to celebrate. You need to change the bed-sheets and do laundry, then vacuum. Cara is bringing her girl to dinner. It is time you two met."

I didn't question her, I just got up and started my chores as she headed out to the market. "Cara's girl," I wondered out loud. I wonder what that's about? Is it her real daughter? Did she have her own trans slave? I guess I would find out later.

A bit over an hour later, I had finished my chores as Mistress returned. After putting away the groceries, I was ordered my room. I was told it was time for her little one to take a nap, and with the collar and cuffs back in place I was told to lie down. She said not to worry about dinner because she would cook this time. Ear buds were put in my ears, and Mistress said she had some soft music to help me sleep.

I did take a nap listening to some gentle jazz. I felt quite refreshed when I was awakened a couple hours later.

Mistress reached in to the bag she had brought home with her earlier, and retrieved the silkiest, prettiest, little girls dress I have ever seen. So much lace and ribbon all over it. There was also a full petticoat. That went on me first, then she dropped the dress over my head. OMG! It was sissy heaven. The dress was held almost straight out by the petticoats.

Michelle fastened about a dozen buttons behind me, then tied a bow behind my back with the waist sash. Pink thigh highs were added and after putting my hair in pigtails she told me to sit at the vanity in her bedroom so she could do my make up. It did not take long for Mistress to have my face looking like a sweet little girl with pink blushed cheeks and lipstick and long mascaraed eyelashes.

"Go set the table for 4 Brenna, Cara should be here shortly."

Cara did arrive shortly after, and with her a young girl dressed just like me, except her dress was powder blue. And, I don't think she was wearing a diaper like me. As young as she looked, she was only a couple of years younger than Michelle. Cara introduced me to Hermine, and I shook her hand. She gave me a kiss on the cheek.

"Hermine is my sissy doll, Brenna. Michelle and I love to play with her in our special room. Tonight she is going to help us milk you. You do remember that we said we will be doing that a couple more times while you are here, don't you?"

"Yes Miss Cara."

Cara had filled Hermine in on the events of the last few days, so we were all on the same page. My concerns about her were totally unfounded, as I found out she was 100% female. Not a trans sissy like myself.

We enjoyed a joint before Michelle called us to the dining room for dinner. First, a bottle of champagne was opened and we toasted the upcoming wedding. A scrumptious shrimp scampi, with all the trimmings and plenty of wine was thoroughly enjoyed. Another joint, and tiramisu for dessert was savored by all.

I cleared the table and joined the ladies in the living room. We talked about the plan for me to return to the states, sell my house, and prepare to move in with them.

We discussed ways to bring these arrangements up with our families, and timelines for the big move.

With another bottle of wine, Cara explained that Hermine loved to be a little girl and how they met at a local lesbian film fest. After a few play-dates in the dungeon Cara collared her. But that's a story for another day.

We moved the party to the playroom and once again I found myself over the bondage bench. My diaper had been removed and I was wiped clean with a damp cloth.

"Cara says I get to milk you tonight Brenna. Its gonna be so much fun," Hermine informed me, as she reached under me and teased my form covered nipples. "This would be so much nicer if you had real breasts you know."

"How are you going to do it with this chastity on me?"

"Leave that to me darling. I sent many boyfriends home frustrated from a good milking instead of making my pussy a mess."

Michelle leaned down in front of me as Hermine stepped away. "You really would look better with your own breasts baby. I would love to get you started down that path." She kissed me deeply and then joined sat Cara in their thrones.

A large dildo gag was shoved into my mouth and into the top of my throat. "That should give you some deep throat practice, and keep four attention focused while I work on you Brenna," Hermine told me as she moved between my legs.

I felt Hermine behind me now. A small amount of lube was spread around my sissy pussy and soon her finger probed inside of me. It moved in and out a few times loosening my hole. Her finger was withdrawn and something a bit larger and firmer was slid inside. I felt a weird pressure on my prostate and though I was going to pee at first.

My Mistresses looked on with smiles on their faces. I felt the probe wiggling inside on me but it just felt odd. Just a few minutes later Hermine removed the probe and held up a glass that had been placed under the tube at the bottom of my chastity. The glass was half full of cum.

"Looks like we are done here Mistresses," said Hermine. "I think that's all that was in her."

When I saw the cum in the glass, I could hardly believe my eyes. I barely felt anything at all and some how she had extracted all my cum. And I was still fucking horny as hell.

Michelle let out a great laugh. "Well if he's that easy to milk, we may never have to unlock her clitty."

"Oh nooo," I cried. "Please don't say that Mistress.

I was released from the bench and knelt before them. My Mistresses in their thrones, and Hermine standing behind Mistress Cara.

"Don't worry Brenna. I'm not promising anything yet. Now about those breasts my little doll. Don't you think you need to start growing your own? Wouldn't the beach be more fun if you filled your bikini top with something real?

"Well yes Mistress, but how would I be able to even do that? And, aren't the ones I am wearing just as good?"

"Darling, they could never be as good as the real thing. You may be able to feel your nipples through them, but it is nothing like the real thing, trust me."

Cara and Hermine both spoke up supporting her statement.

"I do trust you Mistress. If you think its best maybe we should do it."

"That's not good enough Brenna. You need to convince me that you want them. Where's your desire, your enthusiasm? I want you to beg for them. Unless you really do want the chastity to be permanent!"

I saw the love in her eyes and knew I would do as she asked. "Please Mistress Michelle, I want to be pretty for you. I want you happy Mistress. Please help me be the best girl for you. Please help me grow pretty breasts for you to enjoy."

"Of course I will Brenna. I just needed to hear it from your lips." She got up and stood behind me. From my kneeling position she pushed my head forward until it rested on her chair seat. "Don't move baby. I will be right back."

She walked over to a cabinet on the far wall. Soon back behind me I felt her swab my still bruised bottom with something cool. I felt the pain of the needle enter my skin. "Almost done baby, one more for the other side."

The procedure was repeated on my right buttock and she patted me lightly before allowing me to lean back so she could sit down.

"That should get you started Brenna. Each shot contained a 6 month, slow release hormone dose. By the time they are finished you should be at least a full B cup."

"What do you mean should be Mistress?"

"Well, everyone is different Brenna. We will shoot for a B cup, but family history has something to do with it too. Most large breasted women had large breasted mothers and the same with smaller breasts. Was your mother very large?"

She could see the worried look in my face as I thought of how large my mother was. Oh my, I hope I don't get that big, I thought , but said, "Yes Mistress, she was quite well endowed."

Well we will just have to deal with that down the road. After all, it may take a few years before that would come about. And in the meantime I am sure you will adjust to it and learn to enjoy them. Hopefully as much as I plan to."

"Now darling, its time for you to get that head under my chair and work on your ass licking. I am going to enjoy watching Cara abuse little Hermine for awhile as you worship me. With a swat to my ass, she pushed be toward the throne. I dutifully laid down and slid my head underneath as she sat. The panel moved aside as the chair reclined and her ass lowered to my face.

I immediately extended my tongue as Mistress Michelle relaxed on my face and watched the show in front of her. Hermine was over the bondage horse but needed no straps to keep her in place.

I could hear some of the action, and later that night Hermine filled me in on the details. Cara had slid a small vibrator in her pussy and set the vibrations low. she proceeded to use a flogger on her ass and pussy. The speed and strength varied with each stroke. Cara would finger her toy and play with her clit between strokes making her moan with desire.

I could tell that Michelle was playing with herself as she watched. A drip or two of her juices would occasionally make its way to my face. I made love to her ass with my tongue and when she reached a hand down to pinch my nipple I almost got lost in her ass.

The flogging became harder and Hermines' moans became louder. Every time she neared an orgasm, Mistress Cara would stop. After a a quick break Cara would start up again. She would twist her slave girls clit and caress her nipples. The vibrator would be turned higher. She switched to a small thin paddle, like a paint stirrer. I could hear the thwacks on her ass, and the shocked cries as it landed on her tender pussy lips.

Mistresses' juices flowed to my face more readily. Her feet resting comfortably on my crotch. Her bottom steadily grinding onto my face. My sissy clit was trying to break out of the chastity and failed. The pain from its swelling causing me to lick Mistress furiously.

With the vibrator on high Cara again grabbed the leather flogger. It only took a couple more well place strikes for Hermine to cry out in a delicious orgasm. Mistress Cara leaned down and licked the succulent juices from her charge.

Mistress Michelle's chair raised up from my face with her telling me of the hot show I missed. She led me from the room allowing Mistress Cara and Hermine to have some space to enjoy the afterglow.

As we sat in the living-room and enjoyed some more wine and a joint Michelle said she was sorry that I would be leaving the next afternoon. She said she would miss me and looked forward to my return. 3 months is a long time. I assured her that I would miss her as well.

"And seeing that you have not been dating the last few years, Brenna, I want you to commit yourself to me fully before you leave."

"How much more fully can I commit, Mistress? You have already given me a hormone treatment. What more do you require?"

"After Hermine milks you tomorrow I want you to ask me to seal the lock on your chastity. I want you to wear it home and stay chaste until you return. When you get back will drill the lock out and unveil your branded clitty."

"That's such a long time to go with out an orgasm Mistress. It may drive me mad while I am away. And what about the airport screeners? What do I do about that?"

"You just tell them you are wearing a chastity like a good sissy girl. If you need to show it to them to be allowed to board the plane then that's what you will do. Think of it as a privilege, not a choice. As for not getting to squirt your silly juice, maybe Hermine will give you some tips on how to milk yourself. I am certain you will learn before you go mad."

"Yes Mistress. If that is your wish, I will obey."

"You had better, Brenna. Because if you don't obey, I will replace the catheter with a longer one and you will spend a year as an incontinent sissy baby," She threatened.

With that she led me to my bedroom and undressed me for bed. "I think you should have a nice diaper for tonight baby. But I will leave your hands free."

I was soon wearing a thick, soft diaper and the pink plastic pants, lying in the soft bed. Hermine now entered the room carrying a baby-bottle. As she placed the nipple into my mouth, she said I better be a good baby and drink it all down. I nodded yes as Mistress Michelle wished be a good night and put the earbuds back in my ears.