Transforming Brent Pt. 03

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear.

Thursday it was lingerie night. I ended up with multiple bras and camisoles, and a new selection of underwear, from the sexist lace to little girl looks. And a dozen girdles in different styles. Mid-thigh, open bottom, and full body corselettes designed to give me the smoothest look even over my chastity.

Friday evening found us at the MAC store at the mall. Not only did I get a full makeover but was instructed on how to apply it, remove it and take care of my complexion. After paying almost $300 dollars for the make-up we headed to a jewelry store.

Karen chose a pretty diamond wedding ring set to replace my plain band and then started to look at earrings and bracelets. I soon had 2 new diamond studs in each ear and enough jewelry to fill a small jewel chest. We then stopped and bought a couple of handbags and a purse to replace my wallet too.

As we got home Friday evening after shopping and a nice dinner out, we found a box on the porch from Amazon. "Well it looks like your new maids outfits have arrived Brenna. I can't wait to see you model them for me."

I put my new jewelry away as Mistress Wendy freshened up and changed into more comfortable clothing. She opened the box and took out a black and a gray maids uniform. They were long and actually quite plain with just a little lace trimming. They reminded me of a standard hotel maids uniform.

I put on a pair of low heels and modeled first the gray uniform and then the black one. Mistress then took a third uniform out of the box. I was the sexiest "french-maid" style you have ever seen. Shiny pink satin with black trim and a full petticoat. A real wet dream in satin. It had a tiny apron, arm coverlets and a little cap.

I put it on and fell in love with it. With the petticoat holding it almost straight out from my waist you could clearly see I was a sissy in chastity. Mistress must have loved the look to as she immediately had me on my knees between her legs encouraging her first of many orgasms that night.

After breakfast on Saturday morning I was told to do my own make up for a lighter daytime look. It took at least 3 tries, applying and removing and applying again, before Wendy was satisfied. Then it was off to her hairdressers.

Wendy checked us in with the receptionist as I had a seat in the waiting area. The salon was well appointed and we were offered coffee or wine as we waited. We both opted for coffee. Wendy told me she was just getting a trim and they knew what she wanted done for me. She said mine would take longer and she would go shopping while I was being finished up.

Wendy was seated with her stylist and a few minutes later a young lady led me to the hair wash station. "I think its wonderful that you are making such a change for your wife Brenna. Not many men would do what you are doing. I think most men would have run away first."

Well I guess Wendy had filled the salon in on what was going on when she booked the appointment. "Thank you, I think, Claire," I replied as I looked at her name tag. "After 30 years together I love her more than ever and would do anything for her."

"Do you think you will miss being a man?

"Gee, I don't know. I mean I will never be a real female, and I haven't been this way long enough to know the answer to that. But women ski and play golf and go to movies the same as men so I don't think it will be an issue."

"Yeah those things are true, but just wait till some creepy guys start to hit on you. Then see how you like it. Well unless you like guys that is."

"That's something I haven't really thought about. Either of those things really. I will be to busy taking care of Wendy, I think, to be worried about that."

"Right honey, just wait until she sends you to the grocers in a cute outfit and the butcher wants to show you some meat in the back room," Claire laughed.

She moved me over to her station and after pinning a pink cape around my neck, handed me a new copy of Vogue to read. "This will take a while hun, so get comfortable."

Wendy came over a short while later and her hair looked wonderful. She gave be a quick kiss on the cheek and told me to behave and that Claire knew exactly what she wanted her to do, and she would be back in a couple hours. Claire put some kind of foil with holes in it on my head and drew strands of my shoulder length hair through it.

2 hours later my light brown hair had blonde streaks throughout, and was cut and permed in a long pageboy style. Claire said I was lucky to have a perm because it would hold its shape and style for weeks.

Wendy returned with an armload of bags from her shopping. She was amazed at my beautiful hairdo and immediately took a pic to send to Kate. We paid and left a nice tip before we headed home.

I changed into my gray maids uniform and did some cleaning around the house. It really didn't need much with just the 2 of us at home, especially with Sofia still coming in a couple times a week. I told Wendy that I didn't have much to do and gave her a nice oil massage. I think I was trying to keep busy just to keep my mind off of my chastised sissy clit.

"Brenna, we will take a train up to the city Thursday night to go to Karen's. You will have to do the packing as I will be working extra hours next week to be sure we can leave on schedule. We will be coming back the following Sunday."

"That's great mistress. I can't wait to see my key again. I mean, see Miss Katherine again."

"Yes my sissy I am sure you would like to see the key again. As she was sitting on the couch, she beckoned me over. "Lift your dress and let me see how that clitty is doing in its pretty cage!"

I immediately stood before her and pulled the hem up high so she could see. She lowered my panty girdle enough to pull out my caged clitty. Slowly turning it from side to side. I felt her fingernails through the chrome bars. Poking at the slit, and dragging them along my scrotum. I felt her warm breath through the openings as my clitty began to fill the cage. I winced as it tried but failed to get fully hard.

She teased me for what felt like an hour. Squeezing my balls and sliding the front of the cage in her mouth.

"Please Mistress. My clitty hurts so much. May I please lick your glorious pussy instead Mistress?"

"Yes you may sissy. Yes you may."

I was soon on my knees licking her sex with slow sensual tongue caresses. I eventually brought her to to wild orgasms and then sat by her and hugged her.

"Brenna, things have really turned out well for us lately. With you retiring and us becoming fairly wealthy almost over night, I am going to give you a nice treat when we get to Karen's. I am going to unlock you and let you fuck me. I wasn't going to let you do that anymore but I think you have earned one last fuck. And I promise I will make it worthy of a last fuck."

I was kind of surprised by this and wasn't sure how to respond. "That sounds wonderful Mistress, but what do you mean by "last". You aren't gonna lock it up again are you?"

"Yes, until we can come up with a better solution baby. I know you don't like the cage and it does create a tell-tale bulge in a lot of clothing, but it will have to do for now. And don't worry. You know how much I hate being all messy down there."

She reached down and caressed my caged clitty until she heard my moans of pain. "I think my little girl needs a spanking tonight."

"But I have been good all week Mistress."

"Yes Brenna you have. But since we started down this road I just really get turned on by spanking you. Now get over my lap!"

I climbed over her lap with my dress pulled up like a sack over my head, encompassing my arms as well. I was helpless over her lap with my girdle pulled down and my cage trapped between he legs.

Mistress gently caressed my bum cheeks and I thought "hmm maybe this wont be so bad." Then a hard swat on my right cheek evoked a little moan from me. Another on the left. Then 4 more on each side had me twitching on her lap.

I settled down a bit as she again stroked my warm bottom. I felt a finger poking at my hole gently. Slowly moving around the rim and poking at it some more. Then suddenly another swat. "Yeoww," where did she get that paddle. It rained down on my ass alternating side to side. Even between my cheeks.

"Now its starting to turn a pretty red Brenna. Your ass is so much fun to play with." Her finger was playing around my hole again. Probing a little deeper this time. I rocked back against it a bit, encouraging her teasing. Whack! Whack! Even harder than before. She would hesitate a bit between swats to let the pain build. Then another would land. Slowly my whole ass was covered and I was crying into the dress that covered my head.

Running her palm over my ass she commented, "Oh baby its so nice and hot and such a pretty shade of red. My panty is soaked." She pulled back my dress to expose my head. "Are you crying Brenna? What pretty tears. So sweet crying like a naughty little girl from her spankees. I love it. Here little girl suck on my finger for a bit."

Still sobbing I immediately started sucking on her finger. My ass was on fire and I knew it would be sore for a couple days. She withdrew her wet finger and I felt it pressing against my sissy hole again. This time sliding deep inside. She wiggled it in me and caressed my burning bottom with the other hand.

"Such a sweet girl Brenna. Kate and I are so lucky to have you. And that magic tongue of yours. I can't wait to fuck you next week. And just think, soon you will get to watch me and Kate making love too."

All to soon she pulled her finger out and told me to stand up. As I did she noticed some cum dripping from my cage. Then even more between her legs on the leather sofa. She stood up and grabbed my hair and shoved me towards the couch. "You better lick up your mess or I will give you a real spanking you sissy! You will think I used a feather on you if you dare resist!"

I never even felt it escape my clitty. But I knew from Mistress Wendy's tone I better obey. I did as commanded and made certain she was satisfied with the results. I was then ordered to stand in the corner by the dining room and not move and to leave the extra cum smeared on my face.

I heard Wendy moving around. Soon the flash reflecting off the wall told me she had taken some pics of my brightly bruised backside. Showing me her phone she said, "see how pretty Brenna? Just remember, that was for fun. You don't want to find out what punishment will mean in the future. Now go get yourself ready for bed."

"But Mistress, its only 7 o'clock and we haven't had dinner yet," I cried.

"And sissy girls whose clittys make messes get treated like naughty little girls should. And that means early bed and no dinner. Now get your red ass moving sissy!"

I was crying again as I hung my head and headed off to my room to change. After putting my dress and lingerie in the hamper I went to the bathroom and brushed my teeth and peed before heading back to my room. Climbing into bed I realized how sore my ass was. Just lying there without moving it hurt.

Mistress came in and kindly gave me a small tuna sandwich, with a very large glass of water. I winced as I sat up to eat it.

"Does your bottom hurt sissy?"

"Yes Mistress. It is sore even against the sheets."

"Well you go ahead and eat your sandwich and drink all your water and I will get something to ease your pain."

She left the room and I ate as instructed. I was so hungry. It was all I had to eat all day it seemed. The water glass was at least 24 ounces. Like a big milkshake glass. I don't know why she brought that, but I drank what I could.

Mistress returned with a small box that said Halloween costumes written on it. It was from our storage room where we had things tucked away. "Did you finish your sandwich and your drink baby?"

"Well I finished the sandwich, thank you mistress, but the glass was so big I couldn't finish it, see," I said while holding the half full glass out to her.

I told you to finish it Brenna darling. You barely drank half of it. Now be a doll and finish it like a good girl." A devilish smile on her face as she said it.

I did my best and drank it all, feeling a bit bloated in the belly when I did. Mistress smiled again and reached into her bag and telling me to lie back on the bed. She pulled out a thick, cloth adult diaper and a ruffled pink plastic panty. I recognized them as something I was supposed to wear to a Halloween party a few years ago, but chickened out.

"I see you remember Brent's old costume, sissy. Now you will finally get to wear it." She pulled my feet up and slid the diaper under me. "At least this will feel better on your sore bottom." She giggled again as she patted my cage and then finished pinning the diaper up and sliding the plastic pants over it. She turned around and started the TV for me to watch. After popping an oversize pacifier in my mouth she said I was to watch the video 3 times through before going to sleep. "Remember you are on camera in here so no cheating." Earbuds were placed in my ears and Kate's video of Mistress Xena started playing.

I locked the sissys door from the outside when I exited. She would surely be waking up in a wet diaper. Let's see her try to be a man again after that, I thought. Oh how I loved my life these days. I had a beautiful lover in Kate and a loving sissy wife, and plenty of money.

I called grub hub and ordered a nice Thai shrimp dinner to be delivered then texted Kate the pic of Brenna's red hot bottom.

I waited a few minutes and then called her.

"Hi my love, how's life in the big city? Did you get my text? Yes. Isn't that a great pic of her ass. I know darling I miss you too. Yes, but its really only like 5 days till we are in each others arms again. Oh hell yes, her transformation is going great. You wont believe where she is now. Nope. She's already in bed and watching your training video 3 times over before she can sleep. And she had a 24 ounce glass of water."

"What? Of course. She is in a diaper and plastic pantys for the night. I told her it would be softer on her sore red ass."

"I know. She looked like a cute little girl made to stand in the corner. Oh that's a great idea. I will go online after we chat and order some little girl dresses and clothes for her. Maybe some more diapers to. Lol."

"Oops. There's the door bell. I ordered some Thai food for dinner. Too bad my sissy was sent to bed without dinner. She loves Thai cooking. OK. I gotta run. Love you Katy."

I answered the door and got my food. I decided to eat at my computer so I could order some new clothes for my little girl.

I couldn't believe the selections I found. Little girl party dresses. Adult sissy baby dresses. Ruffled diaper covers. Penis shaped pacifiers. I ordered about a half dozen items to be delivered on Tuesday.

Then I ordered a few new dildos in different sizes, some vibrating, some that would squirt fake cum. An inflatable butt plug and even a vibrating plug I could control from my phone. Okay a couple of the toys were for Kate and me to use, but the rest were to keep Brenna stretched and horny. I have by now noticed that it seems the less she cums the more submissive she becomes.

I checked the cam in her room and found her still watching the video as demanded. I relaxed and watched some TV shows for a couple of hours.

Around 11pm I was ready for bed and checked on Brenna first. The video had shut off about an hour before and she was fast asleep. First I switched her earbuds to the white noise machine with the subliminals from Kate. Then, I gently pulled back her pink plastic panty and saw that the diaper was a little wet already. How perfect. By the time I would let her up in the morning she would be totally soaked and humiliated.

Sunday morning I had a nice breakfast before letting Brenna out of her room. As I finished eating I heard her calling to me to let her out of bed. I decided she had spent enough time in her wet diaper and went up to her room. She was almost in tears when I went in.

"What's wrong Brenna. You look like you are gonna cry."

"I'm sorry Mistress. It's just that the diaper is all wet and my bottom is burning and itching. Please let me take it off, Please."

"You know a real man would not have wet in a baby diaper don't you Brenna. I might have been convinced to treat you like a man if you had stayed dry. But no, you had to wet yourself like a sissy baby. I guess there is no more doubt about your position is there?"

"No Mistress, I guess you are right. I guess I am nothing more than a little sissy girl. I guess Miss Katherine was right that it was some repressed desire hidden in my mind. I'm sorry Mistress. Please let me change now Mistress, my bottom is so sore."

"OK baby. At least you are finally realizing that we were right about you. Now go and shower and make sure you rinse and wash that diaper and hang it up to dry. We may need to use it again soon. When you are done I will put some soothing cream on your bottom."

"Yes Miss Wendy, but please I promise to be a good girl. Please don't make me wear diapers anymore. I won't wet the bed or anything."

"I will think about it Brenna. But don't count on it. Remember, this is about what Miss Katherine and I want and enjoy, not you. If we want you diapered and dressed as a baby girl, because it turns us on to see you that way, we will not hesitate to do it. If we want you dressed like a pole dancing stripper you will do it. And if we want you dressed and serving as our maid then you will be. And we will expect you to do it all with a smile and a "Yes Mistress". And if we want to spank that sissy ass just for the pleasure we get from it, we will. The choice is no longer yours. GOT IT sissy?"

With her head hung she replied "Yes Mistress Wendy," and headed for the bathroom. "While you are in there I expect you to shave everything from the neck down. I know you don't have much hair on your body, like a real man would, but it needs to go. I put a couple of my razors in the bathroom for you."

"Yes Mistress, I will shave," I called out as I stood in the shower and unpinned the diaper. My ass was still sore from the spanking, and it itched all over too. She was right about the hair though. I never had much on my body. You could barely see any looking at my arms even. I did the best I could with fer women's razors and soon was toweled of and went back to the bedroom to dress.

Mistress met me there to check my shaving efforts and was pleased. "When we get the cage off of you at Kate's you will have to finish the shaving around that sissy clit Brenna, but you look ok for now. Let me put some moisturizer on you and then something for your bottom."

She coated me in a lotion and then examined my ass. "Gee baby, it looks like you got a diaper rash from wetting your diaper last night. Let me put some rash ointment on you. Wow, that smell brings back memories of when the kids were babies, doesn't it. Nothing seems to say baby like diaper ointment. Now let's get some clothes for yo to wear."

She gave me a pair of little girl style cotton panties instead of a girdle and then a pair of shiny control style pantyhose. They felt so smooth and slippery on my freshly shaved legs. I was given a pretty bra and a satiny blouse and skirt and luckily some low heels and was allowed to get some breakfast. I forgot how famished I was and had a nice full breakfast while Mistress sat with me and had coffee.

"After you clean up the kitchen we need to got the the grocers Brenna. I will help you with your makeup before we go."