Transforming Brent

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Wendy and Katherine want Brent as their maid.
9.4k words
4.06
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71

Part 1 of the 5 part series

Updated 06/09/2023
Created 07/03/2019
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Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life?

Yes, The narration switches between characters. If this bothers you read something else.

*****

Wendy sat in a quiet booth in the diner having lunch with her friend Kate (Katherine). They dined together at least once a month for many years. It was across the street from the hotel Katherine stayed when she came to town. They met during their junior year in college and although I never knew of it, they had quite the affair. Even after 28 yrs of marriage, I never knew of my wife's bisexuality.

We had a wonderful relationship and as far as I knew, neither of us had ever been unfaithful. To our friends, we were that happy, normal couple down the block that was everyone's friend and raised 2 great kids that were now grown and gone. A perfect picture of suburban America. Golf, skiing, charity work, and all that usual stuff.

With the kids gone, we sold the house and bought a nice condo in a private development, saving our home sale profits to be able to travel and enjoy hopefully an early retirement in a couple of years.

Wendy was a director of a local bank and I was a VP of sales for a large company. I am Brent, in case you were wondering.

I had only met Katherine a few times in the past. The first time was when she was a bridesmaid at Wendy and my wedding years ago. She was a psychiatrist with a large practice in a city not too far from us. A tall woman with an athletes body. She was 6'1" and attended college on a volleyball scholarship.

Wendy was also tall and fit at 5'10", and was on the rowing team in college. I was a slim 5'8" but made up for my lack of altitude with a great attitude, intelligence, and charming good looks.

Being single the past few years Katherine wanted to be a part of Wendy's life again. That day at lunch Katherine told Wendy that she loved their monthly lunches but wanted more from the relationship. When time allowed they would go to a local hotel for a bit of womanly love. But that wasn't enough for her. Not anymore.

"I know you love Brent dearly and don't want to leave him, and I can't blame you for that. You 2 have had a great life together. But, you have also told me that sex has always been very vanilla and unexciting all those years. Have you ever even had an orgasm from intercourse with him?"

"Well, actually he is rather well equipped for a guy, but no, I don't think I have. But he does make up for it with his tongue. I usually wish it was your tongue when he does."

"And Kate, you know I have always loved you. If there was a way to have you as a partner without hurting Brent then I would love to figure that out. But I can't see how it would be possible."

"Tell me Wendy, have you guys always been vanilla? I mean do you watch any porn together or anything? Any fetishes you share? Does he read porn and jerk off like most guys?"

"No, we never really watched any real porn together, and I haven't seen any suspicious files on our computer either. I am sure all men masturbate at times but I haven't seen any evidence of that. But we do only have sex a few times a month these days."

"Well, what if I could come up with a plan that would allow us to have each other and you keep him at the same time?"

"Isn't that what we have now?"

"Wendy, you have been the only true love of my life. I so enjoy it when we meet up but I need more than once a month with you. I want you in my life full time. Let us go up to my room and talk some more." They paid for lunch and headed over to the Marriott.

As soon as the door to the room closed Kate stepped behind Wendy and reached around her to embrace her. She softly kissed her neck and nibbled her earlobe, her right hand trailing down Wendy's body coming to rest between her legs. Her fingers pressed through the tight, soft, yoga pants, feeling her lips through them. She wiggled them lightly eliciting a moan from Wendy. Her left hand cupping Wendy's soft breast.

"You love this don't you love? Don't you want this every day, forever? To enjoy the kind of caresses and lovemaking only a woman can give you. Even to teach Brent to love you the way a woman would. Think about it, darling. I can make our dreams come true."

She maneuvered Wendy to the king size bed and urged her to lay out on it as she started to undress. Slowly, revealing the matching La Perla red lace bra and panty set. The black trim making it even sexier on her supple athletic body. She then unbuttoned Wendy's shirt and removed it and her bra. Her mouth taking in a nipple as she reached to caress the other.

She could smell Wendy's sex. She rose up and pulled off Wendy's shoes and pants. Her plain pink bikini panty showed how moist she was. The aroma is intoxicating. She moved up her body. Licking gently across her spreading thighs. A soft and slow loving lick over the crotch of her panty. Savoring the flavor before moving across her smooth belly to her breasts. Lingering just a bit on each of them.

And then a long deep kiss. Wendy was melting with love for Katherine. She knew deep down that this is what she wanted her life to be like. Katherine's hand slid down to her vag again and feeling that Wendy reached around and hugged her close for another deep kiss. Katherine's caresses were bringing her to a huge orgasm.

"What do you want darling. Tell me the truth now and you can cum darling. Tell me what I already know!"

"Ohhhhh, please make me cum Katy! Please! I want you, my love, I want you for everrrrrrrrrr! Oh fuck, oh fuck. Do me. Ohhhhh."

Such an intense orgasm, like nothing she had ever had before. Kate kissed her lips and face all over telling her she loves her and won't let her go.

"Katy that was so special. You are just too fucking amazing. Yes, I want you in my life all the time. I don't know what you are planning but if you can find a way for Brent to be okay with it I will do what I can to help. But only if he is okay with it."

"Darling, I have been thinking about this for a long long time. You know as short as he is, I think he would make a great homemaker for us. After all, with what we earn, he doesn't really need to work and could take care of the house and serve us. You wouldn't have to keep paying that maid to come in once a week. Or you could pay him what the other one gets."

"You intend to make him our maid? I can't see that happening hun."

"Well, why don't you slide down and start eating my cunny like a good lover and I will tell you how we are going to do it. Mmm, that's better."

"So Wendy, most men would jump at the chance to have two pretty women to love and care for and especially to watch them have sex and even have three ways. And you know I will never allow a man to enter my body. So we are going to have to feminize Brent and remove those issues. It may take 6 months or more but we can do it. With his small size and figure, we will make him into our own little sissy. She will serve us in any way we wish and will love and enjoy every minute of it."

"Now don't worry, he will still have his balls. Lol. Now keep licking and I will tell you how we are going to do it."

Wendy kept busy pleasuring her lover with her tongue. For the next half hour or more she kept Kate on edge as she listened to the detailed plan Kate had come up with.

Brent was home with dinner almost ready when I got in around 6:30. After putting away my things I gave him a nice long hug and kiss, poured a glass of wine and asked if I had time for a shower before dinner. Another kiss before he said yes I had about 20 min to freshen up. So I did.

Unlike most nights, I decided to put something sexy on under my house clothes. Some nice thigh high stockings and a sexy bodysuit. I put on a tee shirt and yoga pants and went back to the kitchen. We grabbed our dinner and went to our TV room to eat and catch up on the news and each others day.

We rarely used the dining room anymore and preferred a casual dinner. The news was more of the same. More Trump fucking with everyone's lives and some more rainy days. We finished eating and put our dishes in the sink. Normally Brent would go to the den and watch sports and stuff while I would play an RPG or read.

I thought about the days events and wondered about seeing Brent in the kitchen in a skirt and apron instead of khakis and a polo shirt. I felt a slight twinge between my legs and thought of my Katherine, and the movie disc she gave me to watch with Brent

"Brent, honey, can you come in here please?" When he arrived I hugged him close. "Let's do something different tonight hun. I got a sexy movie I want to watch with you!"

"Really, I never thought you liked them."

"Well, I have been told this one is different. Its actually from a woman-owned porn company."

"If you re sure that's what you want okay, I will watch with you. It might be fun."

I popped in the movie on our 65" screen. The first couple of scenes were hot but pretty basic "girl-on-girl"

stuff.

"I'm gonna pause it a minute. Can you get a bottle of wine and some cheese for us dear?"

"OK, but I need to pee first."

As Brent was out of the room, Wendy took off her pants and tee shirt and settled back on the couch. When Brent came back in with a plate of cheese and some wine and glasses he almost fell over himself when he saw me.

"Well isn't that the most beautiful woman I have ever seen. That's quite a welcome surprise."

"Then why don't you get comfortable and join me?"

And thinking like a man he said "I am comfortable," and sat down.

"Not like that silly. Lose some clothes first."

He stripped to his boxers, which had seen better days. "Are you still wearing those old things. At least I made an effort to look sexy for you, and that's what you are wearing. Yuck! Wait here, I will be right back."

I returned with a pair of scissors and a pair of my red satin panties that were almost see through. "Take that rag off and put these on," I demanded!

I think he was too shocked at my attitude to consider not doing it. He put them on without looking at them as I cut up his boxers.

"Hey, those are my favorite pair."

"Not anymore I," grinned.

"And these are panties, what the hell Wendy?"

"I think they look great on you and very sexy. They won't bite you now sit down and pour the wine and I will restart the movie."

The scenes got hotter with 2 and 3 women in each. One had a gorgeous black haired beauty in a red leather bustier and knee-hi boots and a strap-on fucking a petite blonde girl. In the background, a French maid was tied up on her knees with her back against a post and her arms cuffed behind the post. If you looked carefully you could almost tell it was the petite blonde's husband form an earlier scene.

After the blonde came all over the dildo the woman walked over to the maid and used its mouth to clean the dildo. I had slid my hand from Brent's thigh to his panty covered cock. It was harder than I had felt it in years.

The next scene had the black haired woman pushing her ass onto the maids face as the blonde knelt between her legs licking her cunt. Her nipples totally hard the whole time.

I rubbed Brent through the panty and tickled the head with my nails.

"Oh fuck, be careful Wendy you're gonna make me cum if you keep going."

As the woman in the movie was coming I stroked a bit harder and made Brent cum at the same time. It took a bit for him to settle down.

"That's quite a mess you made in your panties Brent. I would expect you to have a bit better control."

"Shit, I'm sorry honey. I can't believe I did that. Of course, you did have something to do with it."

"Yeah, I'm trying to decide if it was me, the movie, or wearing sexy girly panties that did it for you. Now, why don't you get on your knees and get me off."

So Kate was right. He definitely came heavily in the panty. He obviously enjoyed the kinkier scenes in the movie. We cleaned up and headed to bed. Katherine had given me a little white-noise system to use in the bedroom. She said to tell him I read that it would help with more restful sleep. I was also to slip some earplugs in my ears while I slept as she had some subliminal messaging for him hidden in the white noise.

The next couple of weeks went on pretty much as normal. No more porn movies or panties. Not even much sex. But I did start the white-noise system up every night.

Brent's time was a bit different. He would bitch about working, complaining that he should think about retirement. Work was just getting too boring. One Friday he walked through the downtown mall during a long lunch break. As he walked through Macy's he passed the lingerie dept. and his eye was caught by a mannequin showing a really hot lacy panty girdle and bralette. Fine lace over a dark violet satin. It looked so sexy and smooth.

Something clicked. He had to have them. But he knew he wanted them for himself, not Wendy. Why did he want them so bad? He didn't wear panties. Except for that one time that they watched that movie. He decided to buy them anyway. He grabbed a size 7 (USA) panty and a 40b top. The clerk asked if he wanted them wrapped in a gift-box and he declined. With a knowing smirk from the clerk, he took his package and went back to work.

Saturday morning Wendy woke him with a soft kiss as she tweaked his nipple. "I had such a hot dream about you last night darling. I need you to lick me to orgasm before I get up. I am so, so horny."

"Well, why don't we just fuck then? I'm horny too."

"Cause I'm going shopping and to the salon today and I don't want all that mess to deal with. Now get busy and get me off will you please."

"OK, but I want to know what the dream was about?"

As he licked me to orgasm I told him it was about him being naughty and that I put him over my knee and spanked his ass with a hairbrush like a naughty boy. As I was describing it to him his tongue worked harder and harder and I came all over his mouth and face.

I wouldn't let him up until I was fully cleaned by his mouth. I told him to pick me out a pair of panties for me to wear that day. He gave me an odd little look then went to my bureau. He returned with a black lace light control panty girdle. He said he loved how smooth I looked in them. Then he asked for a hand job or something to help him out. I told him I needed to get dressed to leave.

As Katherine had said, I needed to give him time to shoot himself in the foot. With a modern home with security doorbells and cams around, I could peek in remotely to check on the house, inside and out. Aren't cell phones great? Lol.

I headed out shopping. Nothing major mind you. I could always use a new dress, or golf clothes, or bathing suit.

Yes, a bathing suit would be nice. Something for Brent to think about. A cute sexy 2-piece. Isn't it great to be able to rock a 2-piece at 52?

After a Brazilian and leg wax, I was sitting in a massage chair having my pedicure. If Katherine was right about Brent, we would soon know, and his fate would be sealed, and Katherine and I could finally be together.

Since beginning this plan with Kate, she has been sending me information about FLR's, (female led relationships) and female domination and sissys. She linked me some stories from Fictionmania and some other sissy story sites, and some women's groups that encouraged sissification and feminization of males. As a shrink, she had dealt with many of these issues firsthand.

While having my feet pampered I logged in to our home security app. I flipped through the inside camera's Brent isn't a big technology buff and hardly knew how to access them from his phone or even how many cams I had installed with the system.

Hmm, he's not in the kitchen or living room. Let us see his little "man" cave. If he was doing what Kate said he would be it wouldn't be a man cave much longer.

Sure enough there he was. I first thought he had another woman there but it was just a back view of him standing in front of the TV. But, in a bra and hi-rise panty. I admit his little bubble butt looked cute as he bent down, with legs straight, and popped a disc into the viewer.

He settled back in his recliner and I could see the girl-on-girl porno come up on the screen. He was fast forwarding and stopped at the scene with the Maid being tied to the pole on her knees. I am so glad I was recording this. I would send Katherine a copy as soon as he finished.

He was laying back comfortably stroking his 8" cock. He came when the Mistress took the strap-on from the blonde and stuffed it in the maid's mouth. It took a few minutes to gain his composure and grab a cloth to clean himself up. He quickly undressed and hid the clothing in the back of a desk drawer. He took the CD out and left the room to put it away, then headed down the hall toward the bedroom. End of show and my pedicure was done too.

I sent a quick text to Katy with the video attached and looked forward to her reply. I headed home and greeted Brent as if nothing unusual happened. I went to put away my purchases and as I finished I saw a text from Katherine. She was totally pleased with the days' events and wanted to send me some new files to download to the white-noise system. She said it would be better to have him listen through earbuds if I could arrange it.

She also said it would be time to step things up soon and to invite her to dinner the next Friday, which I of course did. She said she would bring some things with her and plan to spend the weekend.

We decided to go to the shoreline for dinner. It wasn't far and our favorite seafood house was always great. We had been going to Lena's Local Fish for years and had gotten to know Lena, the owner.

"So hun, next Friday my friend Katherine is coming to visit. I thought you could make a nice dinner for us then."

"Katherine? Have I met her?"

"Well, I guess I can't expect a man to remember those things. She was one of my bridesmaids, remember, the tall one."

"Well, I do remember you had one really tall friend, from college I think. Didn't you say you had a fling with her? What has she been doing all these years?"

"I wouldn't really call it a fling, but the sex was hot," I laughed. "We have been friends on Facebook forever. She's a shrink in the city and appears to have done quite well with it. So anyway, you will cook something nice and behave yourself I hope."

"Of course I will darling. Your friends are always welcome in our home. Any idea what you would like to eat? Or should it be a surprise?

"No just do something a little special if you would."

"No problem there darling."

We finished our dinner and headed home, capping the night with some very vanilla sex.

I was getting excited about Katy coming to visit. We spoke almost daily and decided it was time to take things up a few notches with Brent. Just over 7 weeks into her plan it was certainly time. Brent would unknowingly make it easier with his own actions.

I went to work on Friday while Brent did a few last minute things around the house. The hired maid had been there on Thursday so not much cleaning was needed. I check the home security cams from my office and noticed Brent pulled his bag of lingerie from his office desk. He put on just the panty and tucked his cock back leaving a very smooth fit in his pants. He left the bra off and started preparing food in the kitchen.

He left the house before returning with some bags from Trader Joe's. He was expecting me about 4 pm so I went home at about 3. I didn't want him to have time to change out of his panty. I went in unexpectedly and gave him a hug. He was busy in the kitchen but the look on his face told me all I needed to know. He was stuck wearing the panty with no chance to change.