Transforming Brent

He was still busy in the kitchen and Katherine was due at 6 pm. I grabbed a blouse I had picked up for him to wear while shopping recently. It looked like a man's button down but had barely visible darts below the breast and a bit softer material. Any woman would recognize it as a ladies blouse. He was a little confused at the buttons being on the wrong side.

"Oh, don't worry about buttons dear. It's a sharp shirt and will look good with the slacks you are wearing." I helped him button it. The waist was a bit shorter than his shirts and he couldn't tuck it in very well. How perfect was that? Just what I had hoped for.

Katherine pulled up in her new Mercedes coupe. After re-introducing her to Brent we sat in the living room and enjoyed some wine and chatted about her drive and how happy we were for her to visit. I loved how she towered over Brent. Her 4" heels made her almost a foot taller.

Brent went back to the kitchen to finish up the cooking.

"Dinner is ready for you ladies! Come get it."

Our informal habits of serving up in the kitchen didn't suit Katherine's liking.

"Wow that looks like a dinner for royalty Brent," she said admiring the souffle, chicken, and pilaf he prepared. "Don't you think it would be best served at the table instead of soup kitchen style?"

"I suppose so Kate. Please give me a minute to set the table then?

"That's Katherine, thank you. Please remember that."

"Yes, Katherine. We will be ready in a minute."

Brent quickly set the table and brought out the food. It was really divine. As Brent went to clear the dinner plates and bring out dessert Kate accidentally dropped her fork on the floor. Brent knelt down to pick it up and Kate could clearly see the lace top of his panty showing beneath the hem of his shirt.

"So Brent, how is work going these days?" I asked.

"It's okay, but I am getting tired of the daily grind. Maybe I should just retire and be a man of leisure."

"Well, we couldn't afford the maid if you did that. You would have to take over the household chores yourself. Did you think about that?"

"Well I already do some of the work around here, but I am not really maid material."

And Katherine cut in and said, "Why not Brent? I can see you are already wearing woman's panties as a maid would wear."

"No, I'm not. Why would you even say that?" Brent tried to defend his fragile manliness.

Kate was ready to take control. "Well your panty lines show through your slacks and when you picked up that fork, I could clearly see the pretty violet waistband. Are you going to deny it?"

"Yes Brent," added Wendy, "why don't you drop your pants and prove that Kate is wrong!"

"I'm not going to drop my pants in front of our guest Wendy. This is crazy. I'm going to take care of the kitchen," I said standing up to leave.

Katherine stood up blocking my path and towering over me. "Okay, little girl. Your wife gave you an order you better follow it now!"

"But, but I can't do that."

"You can and you will, or do I need to help you?"

She reached down and grabbed the front of my pants and opened the clasp. I was defeated. She pulled my pants down to my knees exposing my pantys and my smoothness at being tucked away.

"My, my Wendy, did you know your hubby wore pantys at instead of boxers?"

"Panties Brent, really? Are you turning into a sissy or something? What's the meaning of this?"

"I'm sorry Wendy, I meant to change earlier but you got home early and then ..."

"Be quiet before you make things worse Brent. Or maybe we should call you Brenna. It seems to fit the situation better."

"Is that what you want darling? You want my oldest and dearest friend to think I married a sissy. And then you try to lie your way out of it. That's totally unacceptable. No, you better not pull your pants up. In fact, I want you to remove them now. I will be right back."

Wendy went to the bedroom and was back in a minute. She sat in a dining chair and before I knew what happened she pulled me over her lap. She had brought back her hairbrush and after yanking my panty down exposing my ass she brought it down forcefully on my bare cheeks.

I yelled in pain and embarrassment and tried to get away. Katherine came over and stood with a leg on either side of my face and held my head tight between her legs. Wendy pulled my other arm up behind my back and proceeded to paddle my bottom until I was crying and begging her to stop. She finally relented and pushed me off her lap, tears still streaming down my cheeks.

"Care to tell the truth now sissy girl?"

"Look, I'm really sorry. But lately, it's like these voices in my head keep telling me that I would feel so much better when I wear pretty things. I don't know what's happening. It just feels so nice to wear them. I'm sorry."

"There is nothing wrong with embracing your feminine side, Brenna. I deal with clients all the time that wish to do that. I am sure that Wendy and I can help you be more feminine if you like. I bet you will love it. There are so many things women can do that men can't you know. Even things like this." And saying that she grabbed Wendy and kissed her like the world would end tomorrow.

As they broke the kiss they could see how hard I had gotten. "For lying to us and trying to hide your panties you will sleep in the guest room tonight instead of Katherine, Brenna. She will be sharing my bed, and we plan to make out all night long, among other things."

"Don't you wish you were allowed to watch us instead of throwing a fit over showing your pantys. But just so you know, we would never allow a man to watch us, or join us. But a feminine man, especially a properly dressed little sissy, might someday be allowed that pleasure. You see Brenna, like you, I love your wife and want to spend my life with her. And I know that she loves you too. I think its time for you to decide how you want to be a part of it all."

"Yes, my love. You can be a man and live here and cook and take care of the house, and do your man stuff, and jerk off in your pantys. Kind of like you did last week when you jerked off to that lesbian porno, or you can become our sweet little sissy girl and serve as our maid and have the hottest sex life you could ever imagine. You can retire as you wanted and we will keep you dressed in the prettiest clothes. And teach you to be a perfect little girl for us. All you will have to do is be a loving housewife to two beautiful women. Doesn't that sound more exciting than continuing as a boring man in drab clothes with a hand for a sex life?"

"I think we should put you to bed early tonight so you have some time to think about the future Brenna. Let's get you ready young lady."

I really didn't have much choice as Katherine practically carried me to the spare bedroom. She held me firmly while Wendy finished undressing me, leaving me in just my panty. She left the room and returned with my matching bralette, (how did she know where it was hidden), and a skimpy nylon nightgown. Once dressed, Katherine pushed me into the bed. She went to one of her bags that were still in the spare bedroom and retrieved some leather cuffs and a collar. She buckled the collar around my neck and after putting the cuffs on my wrists, they were attached to my collar.

"Sorry about the cuffs darling but we can't have you trying to sneak a peek at us later. And it will keep you from wanking while you think about your future."

Before leaving the room Katherine asked Wendy to hook up the white-noise unit with the earbuds to help me relax. Soon the light was off and I was left in the darkness thinking of these to women and their devious plans for my future.

The sound through the earbuds continued all night. Even as I slept I heard the waves gently falling to the shore. The birds chirping. Sis-see, Sis-see is what they sounded like. But I really couldn't be sure. I slept so well since Wendy got this noise machine. I never realized it could contain strong hypnotic messaging.

"Katy darling, I can't believe the changes that have been taking place with Brent. You are amazing. It's just like you said it would be."

"He does seem quite receptive to the subliminal in the white noise. Soon he will be begging to be allowed to wear pretty clothes for us. My goal is to make him look to be a young girl about 7 years old. At that age, they are so reliant on their Dominant partner we will be able to mold him to our will. But there will times that we want him as an adult female too. And if we have any problems getting her to adapt as we wish, I think we can make her much, much younger than 7 as well. Can you imagine putting him to bed like a little baby girl? Oh, this is going to be so much fun."

"And it will all happen ahead of schedule, judging by the progress we have made. He will soon be dressed as Brenna full time and never doubt that it's what he really wants. You need to check on him before we go to sleep and free his hands if he is asleep. If I am correct we will catch him wanking in the morning. He will not be able to resist it even knowing he will be punished for it."

"Katy you are so devious. It just makes me love you more."

"Thank you, my darling. He will soon get excited from the look and feel of pantys. Seeing them on you, me or himself, will always make him feel like a sissy. And he will want that more and more. Whenever he is wearing pantys he will want to wank. Even knowing he will get punished for it he won't be able to resist. And the more he wears them the more he will begin to desire to dress more femininely."

"So how will we handle that?"

"Well, he should be punished for wanking, but also made to beg to be allowed in pretty pantys like we get to wear. We can threaten not to give any to him to wear, then he won't even be able to get hard enough to wank. He will start to associate having sex with being and acting feminine for us."

"Kate, many of the stories you have sent me to read have the women keeping their males in chastity. I think that is a really hot idea. We should find one that will keep him smooth and chaste and put him in it someday when he is caught wanking. I hear they are the best way to train a guy. I wonder if there is one that would keep him nice and smooth?"

"Mmm, I like the way you think Wendy. He will learn that sex and orgasms are a privilege for women and non-sissified males. His orgasms will be few and far between. Now, go free his arms so we can go to sleep. It's been a long day. Maybe we should all go for mani-pedis tomorrow."

"Sounds like fun, let's do it."

Around 9 in the morning we could hear noises from the spare bedroom. Katy peaked through the keyhole and, sure as the sun rises every day, Brent was masturbating.

She walked right in on him and pulled back the sheets, exposing his shame.

"Just what the fuck do you think you are doing young lady?" She shouted just to be certain I heard her. Brent was trying to apologize and say he was sorry. She called out to me, "Wendy, I just caught this sissy wanking in her panty. I need you to come in here and bring your hairbrush please."

Wendy entered as Katherine was reattaching his cuffs to his collar. He was lying on his front side and she shoved a pillow under him to raise his butt up.

I handed her the hairbrush and she quickly landed about 10 strong whacks to his upturned ass.

"What a sissy you are Brenna. No real man would jerk off in pantys." And another 10 strokes landed. "If you want to wear them you are going to stop doing that. Maybe this paddling will remind you that sissys don't jerk off."

6 more swats and he was crying and trying to squirm away.

"Baby, you do love your pantys don't you. I'm happy to let you wear them but you have to stop wanking if you want them, OK?"

"I'm sorry Wendy, they just felt so nice. I do want to wear them. I just couldn't help it. It's like some voice in my head keeps telling me to stroke it," he sobbed.

"You poor baby. There are voices in your head telling you to do naughty things. Maybe you need to see a psychiatrist about that. Oh, wait, Katherine's a psychiatrist. Maybe she can have a little session with you later today. Would you like that Brenna?"

With tears still on his cheeks, he said maybe that would be best if it helped him stop. He didn't like being spanked like a child.

"Well we are going out today so maybe when we get back Miss Katherine will have a one-on-one with you.

Now we need to finish your spanking."

Katherine added about 20 more swats to Brenna's upturned ass turning it a bright crimson. She passed me the hairbrush and we turned our sissy over. He was still crying as I took his shriveled clitty cock in hand. I gently encouraged it to get bigger. He was still weeping as I did. Then I let it lay across my open palm I brought the back of the brush down sharply on it. Katherine firmly grabbed his scrotum and pulled it tightly while telling him not to move.

I added another 5 strong swats and then flipped it over to do the other side. It was almost as red as his ass now and through the tears, he begged me to stop and promised to obey.

"If I stop will you stop wanking and do what you are told like a good little girl?

"Yes, yes, yes, I will do whatever you say, I promise. Just please stop. Please."

Katherine opened his bonds and helped him out of bed. "I want you to go shower and while you are in there shave everything below your eyes. And I do mean everything. And no dawdling we have a lot to get to today.

"Yes Miss Katherine, I will do it right now," he meekly said while mincing off to the bathroom.

I showered and shaved as directed and then ran some cold water over my bruised ass. Wendy was waiting for me when I returned to the room. She led me to the master bedroom and handed e a pair of white cotton panties with little puffy flowers on them. After inspecting my shaving job, she told me to put them on. I was given a pair of ladies shorts and a light tee shirt and told to put my sandals on and meet them in the living room.

After a cup of coffee and a light breakfast, we headed out to Katherine's Mercedes. First stop was a local lingerie shop. I followed the ladies in and Wendy walked right up to the sales lady and said, "Hi can you measure my husband for a bra please, He has been secretly wearing mine and I think he should have his own."

"I would be happy too, dear." And with a comforting hand on Wendy's arm, she continued, "I have had many wives come in with their sissy hubbies. You aren't the first to demand he has his own. I can recommend some nice breast forms to go with it if you like. It does make it easier to get the best fit."

"Thank you, Ann," she responded looking at her name tag. That may be a good idea. I think a cute B cup would go well with her petite size."

Katherine picked out some pretty styles as Ann led me over to the dressing room area and took her measuring tape to my chest. The look from Wendy left no doubt that I had better obey and not say a word of complaint. I measured out at a 38" band size and Wendy relayed that info to Katherine. A minute or so later Katherine came to the dressing rooms with 3 or 4 different styles for me to try. Ann told me to remove my top and try them on. The first one I put on was a rather plain tee shirt style. Ann popped some forms in it and they filled it nicely. The next was a balconette style. Black, lacy and very sexy. A couple of lacy bras for everyday wear, one pink and one dark red. Both had plenty of lace and an underwire.

The next one was a sturdy white long-line that went almost down to my waist. It had at least 10 hooks and made it hard to breathe once it was fully connected in the back.

The last bra appeared to be a little girls training bra. It almost matched the panties I was wearing. It would be used without the forms in it, and they all commented on how totally sissy it looked. Wendy yanked the tags off it and told me to put on my top as I would be keeping it on the rest of the day.

Katherine told me to go look at pantys while she went to pay for my bras. They had an awesome selection and the first time I touched one my sissy clit got hard.

"We are all set now, come get your bag with your new bras sissy." Looking down at my pants she teased some more. "Looks like you saw some pantys you liked over there dear?"

Ann noticed too. "Judging from her blush, I think she liked them a lot," she laughed. "You may want to get something to control that. There is a wonderful fetish boutique about a block away that may be able to help. Come back and see us again. I think some nice firm foundation garments will help her figure."

Finally, we were heading back to the car. It was bad enough having this bra showing through the shirt, now I had to hope this erection would go down before I got in further trouble. I kept the bag in front of me all the way to the car.

Katherine hit her button to unlock the car. "Put your bag in the car and we will walk over to the fetish shop she mentioned.

Oh great. Now I would be paraded around another store and more people would see I am wearing a bra. It took a minute for our eyes to adjust to the darker lighting in the store. Katherine asked if they had leather blindfolds and the clerk pointed to a leather display at one side of the store. She seemed to find just what she wanted and tried it on me to check the fit. She led me back to the front of the store and after refitting the blindfold told me to stand where I was and wait for her and Wendy to finish shopping. I was standing right near the front counter where everyone coming in or going out would see me.

I heard Wendy ask the clerk something strange. Well, strange because I couldn't see what she was referring to. "Excuse me, sir, these are kind of nice. Are there different sizes, and is there anything that will do the same thing, but not as noticeable?"

"Yes, I do have some specialty items that would do the same job and not show in the least. Follow me I will show you and discuss the benefits away from your, uh, sissy."

About 30 minutes later the blindfold was removed and placed into a large bag with their purchases. We headed to the car and went for lunch at a local salad bar. I was getting used to the stares as we finished and headed off again. This time stopping at the nail salon Wendy frequented.

"OK, Brenna. You now get to have your first mani-pedi.

Your feet will feel so nice afterward. And they will look better too. Oh, don't frown, lots of men that aren't even sissys get their nails done these days. Now stand tall and let's go have fun."

After checking in, we were led to 3 adjoining chairs attached to little sinks. The nail tech had us take off our shoes and have a seat. The warm water was soothing and then the tech handed me a controller, saying it was for the chair massage.

Wow, this seemed really deluxe. I was enjoying all the pampering. My legs were massaged from the knees down. My feet were scrubbed, callouses removed and my nails trimmed. She asked if I wanted polish and I was going to say no thanks when Wendy handed her a bottle of hot pink polish. I knew not to say anything and the tech put my sandals back on me and some spacers between my toes.

When she finished Katherine asked her about doing a design on my big toes. When she finished me up I had 10 pretty hot pink nails with "sissy" and "girl" written in silver across my big toes and little silver stars around them.

We were led to the manicure area and Wendy explained what she wanted for me. When she finished I had gel nails. They were about a quarter inch past my fingertips, much longer than I usually wore and coated with a very light pink polish. You had to look close to see they were actually polished. They even used a special UV light to dry them quicker. The nail lady said I would have to come back every 2 weeks for something called a fill, or if I wanted to change the color. Wait, I have to go to work in 2 days. I can't wear this, I thought but said nothing. Well, I guess I would have to now.