Transforming Brent Pt. 03

"Yes Mistress, thank you. But cant I stay here and clean or something. You don't really need me to go grocery shopping too."

"Now Brenna there will be no talking like that. You are dressed like any other housewife out shopping. You need to realize that this is the new you. You will never be going out looking like a man again. Even an androgynous one like last week."

We went to the Whole Foods across town, instead of the one near out house. At least the odds of seeing someone we knew would be lower there. As we pushed our cart along I became a bit less nervous. After all we did enough embarrassing shopping last week. After checking out we went to the drug store next door. Mistress grabbed a cart and said we needed to grab a few items before heading home. First stop was the baby aisle where she grabbed more diaper cream and powder the we went to home health aisle where she studied a few packs of adult diapers before grabbing a couple packs of something called Molicare Super plus. She threw a couple of more items in the cart before we headed to the checkout.

Finally read to check out when my Sally, my old boss Roger's longtime secretary turns up in line behind us. She had met Wendy many times over the years at company events.

"Wendy dear, how are you? It's so nice to run in to you. With all the changes at work lately we really miss having Brent around. Hows he doing?"

"Oh Hiya Sally. It is nice to see you. Brent is fine in fact she is right here." And turning to me she pulls me around by the arm and says, "say hi to Sally, Brenna!"

Before I could say hi, Sally blurts out "Oh my goodness, Brent, it is you in that cute outfit. I never knew you dressed up like that. Wait till I tell Rog. He will get a real kick out of it. You look darling girl."

"Thanks Sally," I said while blushing and trying to hide behind Wendy. But, please don't tell Roger. Cant we just keep this a secret?"

"Sorry Brent, this is just to good to keep quiet about. No wonder you were happy to retire. Are you getting a full sex change or just being a sissy?"

"No, no sex change. Wendy and I just decided to try something different for a while, that's all," I retorted.

"I see, and who are all these diapers for? They certainly aren't sized for a baby, so I guess you are not getting them for grand-kids. Now don't tell me that they are for you too?

I was blushing a bit as I feared that the scent of the baby rash cream was still quite strong. Miss Wendy finally came to my rescue and said that they were for an elderly neighbor that couldn't get to the store. "Anyway Sally it was good to see you. Are you staying on at the company after Roger leaves?"

"No I am going to retire also. Well nice to see you both again."

We finally checked out and headed home with a quick stop at Chipolte. "Thank you for not telling her you bought the diapers for me Mistress. But also, why did you need to buy so many. Its not like I really need them. I mean last night wasn't normal you know."

"Brenna, my darling, I bought them so you wont have to be washing that cloth one. And yes I know you don't need them, but there will be times that I may want you dressed as a very little girl, and what could be better than a nice diaper to help you feel like a baby girl? She pulled into the driveway and as she headed inside she turned to me and said, "Bring in everything from the car and after putting the groceries away, put your diapers away in your room and change into your sexy pink uniform with 3 inch heels and get busy cleaning the Master bathroom."

The Master bathroom. The one I used to use. As I was finishing, Mistress said she wanted the floor cleaned to. "Yes Mistress, I will go grab the mop."

"No need to sissy. There is a Brush under the sink I want you to use. It will do a better job on the tile."

Unfortunately, I would have to do it on my knees, exposing my bottom to anyone, that is Mistress Wendy, that peered in. "You look so sweet on your knees in that pretty maids uniform Brenna. Had you been a bit more polite to Sally earlier you would have been able to use the mop. Let's hope you have learned something about proper behavior. If not I can get my paddle out again."

"Oh yes Mistress, I am sorry for acting like that and I will behave better. Please don't spank me again Mistress."

"I will think about it Brenna, and for now I am still thinking it over. You had better make that floor shine and you better not get that pretty uniform messy while you do it. It you do You will be marching into the dry-cleaner tomorrow and asking them to clean your uniform."

Mistress left the room and I scrubbed the floor until it looked like new. After Mistress gave it her approval, I moved on to clean other areas of the house. Mistress was watching a football game and chatting on the phone. Probably with Katherine, I figured. I just continued cleaning, only stopping when Mistress called me to bring her a glass of wine of a snack.

I started a light dinner of baked haddock and rice pilaf, set the table, and soon was allowed to sit and enjoy dinner with my wife/Mistress. "So Brenna, are you enjoying being my girly sissy maid? Katherine and I really hope you embrace it darling. I think when you do, you will find a whole new world opening up for you."

"Well it is a big change, and I am doing it because I love you so much. But, I certainly haven't been getting the sexual pleasure from it with this chastity on you know. It seems like you and Kate are getting the most benefit from it."

"Yes, and as real women we deserve it, don't you agree?"

"Yes Mistress, I agree, but its just that.."

"It's no just anything," Mistress interrupted, "You are our sissy, and a very new, untrained sissy at that. When you have adjusted to your new life a bit more, we will talk about you having more sex in the future."

"Yes Mistress Wendy."

"Good, now clean up the dinner and meet me in the living room when you are done. After the kitchen was clean, I found Mistress relaxing on the couch with a book and some wine. She pointed to the floor and I knew to kneel in front of her. She pulled up her skirt to reveal an 8" dildo strapped on. "Start sucking sissy girl. The other end of this is inside me and I expect you to do well enough to get me off from sucking the cock. It will be good practice for the real thing some day."

"But Mistress, I'm not gay, I don't wanna suck real cocks."

"I didn't say you were gay sissy. But if some guy sees you as a female, then its just normal sex. Now, if you were wearing one of those old business suits you used to have, and looked like a male, then it would be gay, ha ha."

"Mmm, that feels nice my little pussy girl. Yes, keep doing that. A little faster now. Yes, pretend that's a nice hard cock and you really want to get his juicy cream out of it. That's right, up and down, take it nice and deep. I want to see you deep throat it. That's what you always liked to feel isn't it? Yes baby. Suck it like you remember having yours sucked. Now faster. Mmm deeper sissy, Oh yes. Now I feel it. Look into my eyes while you suck girl. Keep going. Oh fuck, faster sissy. All the way in. Ohhhhhhhhhhhhhhh fuck."

As Mistress was in the middle of her orgasm, I did not see her squeeze the bulb attached to the dildo, but all of a sudden my mouth was being filled, squirt after squirt of what tasted like the cum I had to lick up the other day. I kept my eyes focused on her smiling as bits of the come dripped from my lips. She finally slumped back into the sofa and pulled her fake cock from my mouth with a big smile on her flushed face.

"You are dismissed for now Brenna, thank you. You should prepare my bed and then get ready for bed yourself. Remember, tomorrow you need to concentrate on laundry so we will both have the clothes clean that we need for our trip. I will be up to check on you when you are ready for bed."

I turned down the sheets on Mistress' bed and lit some of her favorite incense, and headed to my room. I was soon in a pretty flowered night gown and called down to Wendy that I was ready for bed.

Mistress came in about 15 minutes later. At least she didn't bring a glass of water again. "Roll over sissy, I need to put more rash cream on your bottom!" She gently rubbed the cream over my still itchy bottom. She I turned over again and she fondled my balls and played with the cage causing me to moan as my clitty tried in vain to get erect in the small cage. "I am going to let you watch the video again tonight but first I want you to know how disappointed I was with your behavior at the stores today. I am not going to spank you again because you need to heal so I am going to try something else this time."

She left and returned with a small funny shaped jar and a couple Q-tip swabs. "This is called Tiger-Balm sweety. Its for sore muscles. That little clitty muscle looks a bit sore in that cage so I am going to put some of this on it to help you remember your place."

She opened the little jar and swiped the swab through it. Then she pushed it through the bars of the cage and rubbed the ointment all over my clitty. She quickly took another swab and coated it and coated the head of my clitty and pushed it a little way into the pee slit, giving it a twist back and forth then going a little deeper. "There you go sissy. That should keep you from getting hard for a while."

With that done she pulled a pair of pantys on to me, added my earbuds and turned on the video. Finally she pushed the pacifier in my mouth and left me. It didn't take long for tears to be pouring down my cheeks as the burning ointment left my clitty on fire inside and out. I watched the video again and finally cried myself to sleep, promising my self I would try to be better to Mistress tomorrow.

Miss Wendy woke me early Monday telling me to make her breakfast before she left for work. Most of the day was done doing laundry, making sure we both had clean clothes for the 10 day trip to the city. The evening was spent quietly and uneventful, but I was still put to bed rather early I thought. I guess Mistress wanted some alone time to face-chat with Kate.

Tuesday was more of the same. I worked on a few projects and double checked that our luggage was in good condition and cleaned. I made myself an nice salad for lunch and was sitting in my den eating and playing computer games.

"Hi Mr. Brent. You had some packages on the porch so I brought them in for you."

Startled, I jumped out of my chair spilling part of my salad and looked right at Sophia, our regular cleaning lady. She had a big grin on her face when she saw me in my regular gray maids outfit with makeup and my new hair style.

"I'm sorry Sophia, Miss Wendy, I mean Wendy asked me to wear this while I was doing laundry and things for the day to keep my travel clothes. I'm so sorry, I didn't mean to shock you."

"It's okay, Miss Wendy already told me you would be doing some of my work nowadays and I think you make a cute little maid. She told me you had some new outfits being delivered today too and that you should model them for me. I guess ' what is in these boxes. But you better clean up that salad you spilled first Brenna!"

"Oh I see she told you my new name too. Great. I knew I should have told her to give you the week off." I cleaned up the salad as she opened the boxes in the living room.

"Look at these pretty dresses Brenna. Did you pick them out?"

"No Sophia, I didn't know anything about them."

"I see. And in the future its MISS Sophia, you sissy. I cant believe I worked for you for 5 years now and didn't realize you were a sissy girl. But I want to thank you for keeping me employed. I really like you and Wendy. When she told me the whole story about you retiring and Kate and everything I was amazed and so happy for Miss Wendys good fortune."

"OK sissy you better lose the dress so you can try these on. I cant believe a grown man would want to wear this babyish outfit." As sh said that she pulled the frilly pink baby dress out of the box. "Lets slip this over your head so we can check the fit now. Don't worry I'm not gonna diaper you."

I was soon modeling the dress as Sophia took a couple pics of me with her phone. It was the shiniest dress I have ever seen. It looked like soft pink glass and was certainly perfect for a little 2 yr old baby girl. Which I was not. The next dress was a party dress in pink. Like a 6 yr old would wear to a party with other little girls. Sophia took a couple more pics and I saw her texting on her phone.

A minute later her phone rang and she put it on speaker. I heard my Mistress' voice speaking out. "So what do you think Sophia, isn't she adorable. I hope she has been behaving for you."

"Yes he has been well behaved. I don't know how you do it but you will have to teach me. I know a couple of men that should be more like yours. I love this party dress on him. That would be cute with pantys or a diaper under it."

"Yes I think you are right Sophia. Anyway, I would like you to put together a nice slow-cooker for us for tonight, then you can leave. I am going to text you some instructions for Brenna, and I want him to remain in his party dress until I get home. Please see that he understands."

"Not a problem Miss Wendy, hee hee, leave it to me." She hung up the call and her phone soon beeped with a text message.

"Sissy, Mistress Wendy wants you to do an assignment for her. You are to sit at your desk and write 500 times:

I love being Mistress Wendys sissy.

I love being in chastity.

I want to be a sissy girl.

Double spaced and neatly written. Now wait a minute and I will get your chair ready. She took a small box out from the newly arrived shipment and went into my office. She moved a wooden seat chair in place of my leather desk chair and attached a suction base dildo to it and called me in.

I wanted to run when I saw what she had set up for me. It would take hours to write all that 500 times. "Please Miss Sophia, Please don't make me sit on that."

"Ha Ha, silly sissy. This is what Miss Wendy ordered and its exactly what she is going to get. I think you better get on your knees and get it nice and wet first. It will go in a lot easier," she laughed. I could see her taking pics as I was on my knees licking it. "Suck it sissy. I want some nice pics for your Mistress." As I did she forced my head down making me deep throat the dildo. Satisfied it was wet enough, and that I was humiliated enough, she told me to sit down and get to work. Remember, you are on cam in here anyway, so be a good girl. I am going to start dinner and let myself out."

As she finished saying that she reached behind me a hit a switch or something and the dildo started vibrating softly. I tried to write some lines and it got more intense. I was never a smooth vibration. Sophia said goodbye and I heard the front door close. The vibrator kept going. It would change its pulse on a random cycle. Some like a small caress and once in a while like a static shock.

It was so hard to write neatly never knowing what would happen next. I think after about an hour either the battery was getting weak or my ass was thoroughly numb.

It was almost 7pm and I still wasn't near finished when Wendy got home. She must have been standing in the doorway watching me write for a bit. "7 o'clock sissy. Time to put your pen down. I sure hope you finished your lines."

"Welcome home Mistress Wendy. I'm not sure how many I did . I didn't want to take the time to count. I think I must have done at least 500 Mistress."

Spying the crumpled up sheets of paper on the floor she remarked, "looks like it took a few tries."

"That's because the dildo kept doing things and I would make a mistake of something. It was so hard to write."

"Stand up and stretch a bit Brenna. Good girl. Now while I check these over I want you on your knees and cleaning and thanking that dildo for fucking you. Don't give me that look. I don't really give a dam how it tastes bitch. Get on you knees and get it in your mouth and suck until I am done counting your lines."

"I think you may not have understood that I wanted 500 lines. There are only 430 lines finished and 22 more that are too messy to count so that brings the total to 408. I expected better for you. So what are we going to do about the other 92 lines sissy?"

"No, don't answer. Keep your dildo in your mouth. Lets see. I can give your sissy ass 92 swats with the paddle. Or, I could add 92 days of chastity. I will think about it. But I like the 92 days idea the best."

"OK sissy, get up and clean the dildo in the sink and brush your teeth and then we will have dinner."

We had a nice dinner during which Miss Wendy mentioned she had invited Roger over for a drink Wednesday evening. "It will be the last chance to say goodbye as he will be leaving for Costa Rica while we are in the city." I was put to bed in much the same manner as previous nights.

Great, I thought, now my oldest friend is going to see me dressed up too.

Before leaving for work mistress told me to pack our clothing for the trip, but to leave room in case she wanted to add anything. I was to go pick up some wine and some of Rogers' favorite scotch. And to be in my sexy pink maids outfit by 5pm. She would bring our favorite Thai food for dinner so we wouldn't have a major kitchen mess before leaving in the morning.

My chores were completed and I was dressed as Mistress wished. I was still pretty nervous about Roger seeing me in this outfit. We enjoyed a nice meal and then Mistress led me to her bedroom and had me sit at her vanity. She decided to redo my make up and I knew it was too late to beg to change to something less revealing.

Not stopping her work on my face Mistress informed me of how she expected the evening to go. "Brenna, we have an issue of 92 to solve don't we?"

"Um, yes mistress."

"So I will give you a choice. 92 days of chastity. And that means no hot fuck when we get to Katherine's. 92 swats on your sweet ass, delivered by Kate with her choice of paddle, crop, or cane. 92 days in diapers. Or you give Roger a nice sissy blow job. Your choice sissy. When I finish your face I want an answer."

As she worked I pondered my fate. Miss Katherine would blister my ass so bad I wouldn't sit for a week. And I really didn't want to miss out on the great fuck Mistress promised. And the diaper choice was the worst, as I am sure she would make me use them. I knew what I had to do.

"Okay sissy what's it gonna be?"

"I will suck Roger, Mistress. At least it will be over sooner."

"Fine not only will you suck him, You will thank him for allowing you too do it. And you will smile and look up at hi while you do it. And lastly, you will swallow. Got it?"

"Yes Mistress."

"And you better not cry and ruin your makeup. Now go pour us some wine and a Johnny Walker for Roger. I want you hold it on a tray and wait in the living room."

It wasn't 5 minutes more before the doorbell chimed. Mistress let Roger in with a hug and a little small talk. I saw him glance over and see me, and a grin came to his face. "And who is the sexy girl with the drinks?"

"Oh don't you recognize Brenna, your ex VP of sales. Sissy come say hi and give the man his drink."

Roger eyed sissy up and down for a minute and slugged back his scotch. "Mmm, I will have another girl. You know I should have guessed you were into something like this when I saw your nails were polished that day you retired Brent."

"It's Brenna now Roger," Mistress corrected. "We both hope you enjoy your life in the tropics Roger. We will miss you you have always been a good friend." Mistress looked at me and nodded when Roger started sipping his second scotch.

"Yes R, R, Roger. You have been a fair boss and a good friend. To thank you for your friendship, and as a going away gift, may I please suck your cock for you sir?" I said in a little high pitched voice.