How My Boss Wife Try To Feminized Me💄💅 (Crossdressing Stories)

 

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 How Thomas is feminized by his wife. Jenny Powers was in her office going over the week's events. Every Friday at 11:00 AM, she had her secretary come in to take notes of the week's happenings. She spoke to her secretary, "Angela, it's been a very good week for the company. We picked up two new clients, and it looks like we may need more help if this keeps up.

You know a year ago when I took over after my father's heart attack, we had five employees. Now we have 11. When Dad recovered from his attack, he saw how I was doing and told me to keep going. Well, I have. Enough of this. First, the Bradburn account. They want to increase their business with us starting the first of the month.

That gives us two weeks to prepare. Make a note to hire two more people. We have to find just the right ones for the job. Jeremy Hawkers called and congratulated us on the fine job we did for them. Make a note for me to send a thank you to him. It seems all of our clients are impressed with our work, so what can I do to thank the staff?"

Angela replied, "Well, you could get them something. A lot of the go to the strip mall across the street for lunch and shop afterwards for a little bit. Maybe a gift certificate for one of the stores. I know most of the girls shop the Woman's World Apparel shop. Maybe one from there or the restaurant where they eat."

Jenny answered, "A great idea. I'll get everyone a gift certificate from the apparel shop." Angela said, "What about Thomas? He doesn't go there. Although he is just like one of the girls here. He joins them for lunch and shopping afterwards. I think he would look cute in a dress." It was silent as Jenny thought about Thomas.

Thomas was one of her father's best advisors on financial matters and where the company was heading. She first met him when she visited her father here. He was quiet and yet attractive. After the third visit to her father, she asked him if he wanted to go for supper that night, and he accepted. He was going to pay for supper, but Jenny took the check and paid it.

They dated for six months, and Jenny asked him to marry her. He wasn't aggressive towards women, and the girls all liked him. Angela spoke, "Does he go for sports? There's a sporting goods store there also." Jenny thought a minute, then said, "No, he isn't into any sports. Maybe he can find something in the apparel store that appeals to him."

Angela asked, "Could I make an observation off the cuff about you two?" Jenny said, "Sure, I would like to hear it." Angela said, "Well, it seems to me that you wear the pants in the family. Maybe you could have him get some panties or something." This started Jenny thinking. She replied, "You know, you're right. I never gave it much thought, but Thomas doesn't disagree with me on anything.

He is very pliant. Look at that, it's noon already. I'll tell you what, I'll treat you to lunch." Where would you like to go? Angela replied, "Well, there's a little supper club in the next block that has excellent noon meals. I go there when I want to treat myself." "Okay, it's settled. Let's go," Jenny said. As they were returning from lunch, so was the rest of the staff.

Jenny saw Thomas walking with two of the girls, and they were talking and laughing. She felt a little jealousy with the way he was so friendly with the girls and seemed to have a closeness that she didn't have. She returned to her office and started working. Things just weren't going right, so she sat and thought about what Angela had said.

She made a decision that she wasn't really sure of, but she decided to see how far Thomas would go. She called Angela and told her she was leaving and would be back in an hour to an hour and a half. At the end of the day, she and Thomas were on their way home. Jenny said, "I did some shopping today. When we get home, would you take the bags in the back and put them in our bedroom for me?"

"Sure, no problem," Thomas answered. They arrived home, and Thomas took the packages to the bedroom. It took three trips, but he made it. He said to Jenny, "You sure did enough shopping. You must have been busy the whole noon hour." That night she asked, "What do they say about the one who makes all the decisions in a marriage?"

Thomas asked, "What do you mean?" Jenny replied, "What do they say the one wears who is in charge?" Thomas said, "They say they wear the pants?" Jenny asked, "Who wears the pants with us?" Thomas answered, "I guess we both do. I never gave it much thought." Jenny said, "I think I wear the pants here. Don't you agree?"

Thomas answered, "I guess you do, but I don't really care." Jenny said, "Well, in as much as I wear the pants, what should you be wearing?" Thomas replied, "What I have been wearing. Why?" Jenny said, "What's the opposite of underpants?" Thomas said, "Panties." Jenny said, "Very good. Now, what the opposite of pants?" Thomas said, "I guess a skirt or dress."

Jenny said, "I want you to go in the second drawer on the left of my dresser and get a pair of panties and put them on." Thomas said, "No, please, no." "Do as I ask." Thomas answered quietly, "Yes, I'll do it." Jenny said, "The drawer next to the panties is the bra. I want you to get a matching one and put it on also.

Okay?" Thomas replied, "Okay." Thomas went to the drawer and picked up the first pair of panties on top. "Just a minute, I'll get you a nightgown to wear." She handed him a pink long satin nightgown, and he put it on. The bra was very tight and uncomfortable, but he eventually fell asleep. They both woke up at the same time.

Jenny said, "Why don't you go down and make some coffee?" He arose out of bed and started to take the gown off. Jenny said, "Leave it on. I'll find some clothes for you to wear today." He went down and made the coffee. While it was brewing, he sat at the table and wondered how long this was going to go on. He hoped Jenny would get over it today, but a feeling of foreboding swept over him.

He knew how she could be, but that he loved her anyway. When the coffee was done, he poured two cups and took them up to the bedroom. Jenny was up and looking in her closet. She took out a green dress that he remembered her wearing as a bridesmaid. She laid it over a chair and got her cup of coffee. When she finished her coffee, she told Thomas to sit at her vanity.

As she applied lipstick to his lips, he remembered when his mother did the same thing. She then parted his hair in the middle and brushed it into a feminine style as best she could. She said, "You look good in lipstick. I don't wanna see you without wearing it, understand?" He answered numbly, "I understand."

She handed him a girdle to put on and watched amusedly as he pulled the too-tight girdle on. She then gave him the slip to put on. He put it on, and when he was done, she was kneeling at his feet, holding the green dress. He stepped into it, and she helped him get it over his arms and then zipped up the back.

It was tight on him, and when she steeped back and took a look at him, she wondered if she shouldn't get a different dress, then decided against it. She said, "It's called a hobble dress because the bottom has such a narrow opening that you can only take short steps. I don't know why anyone would really want to wear one, but I figure it will help you get into the habit of taking shorter steps."

She then handed him a pair of white four-inch heels to put on. He put them on, and she had him walk around the room for a while to get used to them. As they were going downstairs, he couldn't help but be amazed at how difficult it was to navigate the steps. When they got down, Jenny told him to get the vacuum and do the living room, kitchen, and dining area.

When he finished with the vacuuming and had put away the vacuum, Jenny asked, "Well, how does it feel with me wearing the pants and you wearing a dress?" And Thomas answered, "Honestly, it is uncomfortable. The bra is too tight, and my legs are starting to ache." Jenny retorted, "Bras are supposed to be tight, and you'll get used to walking in heels.

I am having you wear them now to build up those leg muscles. I'll let you take them off after a while." Just then, the doorbell rang. Jenny told him to answer it, and with trepidation, he opened the door. It was Sylvia, his wife's hairdresser. She usually came on Monday evenings, but he thought Jenny must have wanted her there today.

Jenny greeted Sylvia with a quick hug, then stated, "Well, you work is cut out for you today. We'll see how good you really are. Look at him!" "Can you make him look feminine enough to fool his mother?" Sylvia smiled and said, "When I'm done with him, nobody will recognize him." Sylvia started by washing his hair, then started trimming some off.

Then she started putting rollers in his hair. She put some awful-smelling lotion on everything and put the drying bonnet on him. While that was running, she started on his eyebrows. When she finished with his eyebrows, she attached some long fake fingernails to his fingers, then proceeded to color them a bright red.

As they were drying, she wiped his lipstick off and proceeded to use a brush to apply new lip color. When she finished, she checked his hair, uh, saw that it was dry. She worked on styling his hair, and when she was finished, she applied another coat to his nails. While that was drying, she glued some false eyelashes on him.

When she finished touching them up with mascara, she checked his nails and declared that he was done. She handed him a mirror to look at himself. When he looked in the mirror, he couldn't believe it was him. All he saw was a beautiful woman looking back at him. Jenny exclaimed, "Marvelous, just marvelous. I can't believe that is the same person."

She thanked Sylvia and told her she was amazing. Sylvia told her she had done about six or eight guys for their wives, so she had some practice. She left the cosmetics she used and departed. Jenny said, "Thomas, come here and sit by me." Thomas made his way over to the couch and sat facing his wife. She said, "You look so beautiful, I want you to wear dresses from now on.

Do you think you can do your own makeup?" Thomas answered, "Yes, I probably can. Sylvia showed me how to do everything, but it is going to take some time to get everything on. One thing, you don't expect me to go to work like this, do you?" "Yes, of course, I expect you to go to work like that. Oh, not in a bridesmaid dress, but something that fits the office.

I already got you a brown dress suit with a straight skirt and a blouse with a front ruffle to wear with it. I know you are going to look fabulous. I got you some brown heels to go with it. You can wear it Monday. Now, let's go get something to eat. I'm starved." Thomas resigned himself to doing what she said.

She handed him one of her coats, and he was holding it for her, and she told him to put it on. She handed him a purse and told him to put his wallet and his lipstick in it. They left the house, and she told him she would drive. She drove to a supper club that served noon meals. As they were eating, Thomas couldn't miss his red fingernails.

Jenny spoke, "You know you don't look like a Thomas anymore. We have to come up with a name that fits the new you. Do you have any favorite feminine names?" He answered, "No, I never gave that a thought. My mother's name was Anna, and she was real feminine." Jenny interjected, "No, I think you should have a special name.

How about Heather Marie?" Thomas replied, "Whatever you think. What are you going to tell them at work?" She answered, "Don't worry. I'll come up with something that will be accepted by the girls." They sat in silence as Thomas considered what was happening to him. The waiter refilled his coffee cup, and he drank it down.

After two cups of coffee and two glasses of water, he had to go to the bathroom. He excused himself, and Jenny reminder him to use the women's and to freshen his lipstick while he was there. He was amazed that no one gave him a second thought, that they just accepted the fact he was a woman. When he returned to the table, Jenny informed him that she had gotten him dresses for Monday and Tuesday, and that he better get some for the rest of the week.

She told him he can probably get them Monday during the lunch hour. She asked him if he needed any help picking them out. He agreed he probably could use some help, so Jenny asked who he wanted to help him. He replied, "Well, Samantha and I talk about everything, and she is one of the sharpest dressers in the office.

Maybe I'll ask her." Jenny told him not to bother, that she would take care of it. She said she knew what he all needed and would tell Samantha so she would know what Tot look for. This was okay with Thomas, as he didn't know how he was going to ask her to help him look for dresses and such. The next day, she had a long, straight floral skirt with a white frilly blouse for him to wear.

Jenny made him do his own makeup so he could get used to doing it. When he returned to the living room, Jenny told him he did a great job on the makeup. He was thrilled when she said that. She had him make some coffee. They sat at the table having coffee when Thomas asked, "How long do you expect me to wear a dress?"

She replied with a question, "Why? What difference does that make?" He responded, "Well, I would like to know so I have some idea what to expect." She answered, "Well, I really don't know. I think I'll know by the end of the week, but I'm not sure. I know you are doing this because you love and trust me, and that means a lot to me."

She kissed him, and he got up and went into his study on his computer. The rest of the day was uneventful. Monday morning, Jenny helped him get the suit dress on. She gave him a pair of brown heels with a three-inch heel. He managed to walk in them fairly well, putting one foot in front of the other. Jenny liked the sway in his hips.

They left for work with him carrying a patchwork purse with many different colors in it. At work, Jenny started the week with the usual staff meeting. She had already called the boutique across the street and arranged for gift cards for everyone. She had sent Samantha for them, and she said, "Due to the success we have had, I have a special gift for each of you, a $400 gift card to the dress boutique across the street.

This is to show my appreciation to each of you." She handed out the green gift cards to everyone but Thomas. When she handed Thomas his, his was gold. She said, "As you must have noticed, Thomas is finding out about his feminine side. Call him Heather Marie. I know you girls will help him in any way you can.

Samantha, I would like to see you after the meeting." When the meeting was over, Jenny told Samantha about helping Thomas pick out his new wardrobe. She gave her a list of what was needed and how many. She told her to make sure the articles were all very feminine. Samantha told her it wasn't a problem.

Jenny told her to take as long a lunch hour as necessary. After her meeting with Jenny, Samantha stopped by Thomas' office. She asked, "Heather, is it okay if I come in and talk to you for a couple of minutes?" And Thomas, with a sense of dread, said it was okay. Samantha said, "I guess we are going for lunch as usual, then we are going shopping for some new clothes for you.

How about we leave at 11:45 to beat the noon rush?" Thomas answered, "That sounds okay to me, but I am not looking forward to shopping for dresses." Samantha said, "Well, from the list Jenny gave me, we have to get more than dresses for you. We have to get just about everything. I'll tell you something, I'll help you through this in any way I can.

I consider you a special friend of mine, and I would never do anything to jeopardize that friendship. I'll see you at 11:45." She got up and gave him a kiss on the cheek and left. Thomas sat and thought about his situation. He thought maybe he should have laid it on the line with Jenny. He knew he loved her, but this was more than what he could handle.

He knew she was headstrong, and it was easier going along with her than knocking heads with her. He hoped she would quickly get over this finding out about his feminine side. He chuckled when he realized he didn't feel any different about women now than before all this started. Before he realized it, it was 11:45 and Samantha called him to go for lunch.

They were seated in a booth in the diner and Samantha said, "Thomas, you make a very nice-looking woman, but will you tell me the truth? Is this finding your feminine side your idea or Jenny's?" Thomas was silent for a minute, then answered her, "The truth is, it is Jenny's idea. I don't know where she came up with it, but I got caught up in it before I really knew what was going to happen.

So now I play it as it happens." Samantha said, "I'll bet I know who would put such an idea in her head. Angela would, and Jenny thinks the world of her. Angela has a couple of times said how you were just like one of the girls. I think she is jealous of how well you get on with all of us, and she doesn't.

She seems to have a suspicious nature, and I think it bothers her." Thomas said, "That may well be, but Jenny loves me and I don't think she would do anything to hurt me. Not on purpose, anyway." They made small talk the rest of the meal, then headed for the dress shop. In the dress shop first, Samantha had him get some more bras, panties, slips, and nightgowns.

All were very feminine. Thomas wondered why when no one usually saw what you were wearing under there anyway. Samantha told him it was to make a woman feel like a woman. Then came the picking out of dresses. Samantha recommended two, one pink one with embroidered flowers and ruffled collar and cuffs, and one green one with lots of lace trim.

They got one that had a straight skirt with a contrasting ruffle on the bottom. Samantha said that should take him to the end of the week, then helped him pick out a blouse and skirt combination for the day he didn't feel like wearing a dress. Thomas walked away from them for a minute and looked at a rack of dresses.

He noticed a blue one made out of a brocade material that really looked nice. He asked the owner if that was his size. She told him that one wasn't, but she had one in his size exactly like it in back. She told him to follow her in back. In back, she showed him the dress. It was the same dress. She said, "Your wife told me about you and asked if it was okay to have you come in now to try on dresses."

What do you say to someone who had just spent over forty-four hundred dollars plus? You say, "No problem. I wanna tell you something. You can come here anytime you want. You seem to be a special person. I really like you. Now, go in the dressing room and try this on." Thomas went into the dressing room and tried on the dress.

When he exited the room to see in the mirror how it looked, both women exclaimed in unison, "You look marvelous. Blue is your color." Thomas blushed and went into the changing room to change. He noticed a colorful scarf on the way out and asked Samantha if it would go with any of his outfits. Samantha told him it would complement two of the dresses, sp he got it.

When the total was rung up, Thomas was surprised when the total was over a thousand dollars. The owner said, "Your wife is a shrewd person. She negotiated a 20% discount on all your purchases. I usually give a 5% discount on purchases over a thousand dollars, so I'll give you a 25% discount." The total came to eight hundred and eighty-eight dollars and eighty cents.

"Look at that, five eights, good in any poker game," Samantha laughingly said. Samantha helped him get all his purchases to the car. She said, "That's quite a load." Then she showed him the list Jenny had given her. Then she said, "It don't look like Jenny is going to let you wear man clothes for quite a while.

Do you think you will be able to handle it? I know it isn't going to be easy." Thomas replied, "I really don't know. I am still kind of numb over everything that's happened. Sometimes I think I have to really have a strong discussion with Jenny. Then I think of how she loves me and wouldn't hurt me intentionally, and that overrides all the other arguments."

Samantha stated, "I'll tell you something "Most of the girls in the office think what you are doing is great. They are very supportive of you and will probably help you in any way they can. But look out for Angela. I think she's a lesbian, and she could be bad news. You are the closest and most dear friend I have at work, and if you ever wanna talk, just give me a call.

I mean that." Thomas said, "Thank you." "I have always thought you were special. That is why I suggested to Jenny to have you help me shop today." They returned to work and were surprised when they saw it was already 2:45. Thomas wasn't in his office five minutes when Jenny paged him to her office. He entered and sat down.

Jenny asked, "How was the shopping?" Thomas related the events and told her about the discount and the total. Jenny took everything in stride and said, "It isn't as much as I thought it would be. Very good. Your lipstick needs refreshing, so go do it, and I'll see you later." Thomas returned to his office and refreshed his lipstick and got to work.

As they were going to the car, he noticed several people look at him and not give a second thought. It gave him confidence. When they got home, Jenny had him show her all his purchases. She was satisfied and felt a thrill at seeing him display all of them. She told him she was proud of him, and that made him feel good, although he didn't know why he should feel good about buying dresses for himself.

The rest of the week went smoothly, and at last, Saturday arrived. Thomas wore a blouse-skirt combination with the multicolored scarf. Jenny told him he looked beautiful. He went into his study on his computer. Jenny looked through the doorway and saw him working on something. She smiled at how well everything was going and got a warm rush over it.

Thomas didn't come for lunch, and when Jenny called him, he said he wasn't hungry. Jenny worried for a moment about it, then dismissed it, as she knew sometimes when he was really concentrating on something, he would get lost in it. He came into the living room and handed Jenny a letter without saying a word.

Jenny opened the letter and was surprised to see a letter of resignation from the company. She asked, "What's this all about?" Thomas answered, "I can't keep this up. I don't wanna work dressed as a woman. If you insist that I dress as a woman, maybe it would be better if we split. Salmon Brothers have been after me for the last little while to join them as treasurer and vice president of finance.

They are a big outfit, and it would be with a sizable raise. If you want me to move, I can do it this next week. I have enough money to go for quite a while. I have been thinking very deep and hard, and I just can't continue this way. I'm sorry, but that's the way it is." Jenny sat quiet for a couple of minutes, then spoke.

"This letter is quite a shock to me, but I understand. I can't accept it. I won't let you resign, and I'll explain. Believe it or not, you are a big reason the company is doing so good." "If it weren't for your advice on some of the critical issues, we wouldn't be where we are today. Do you know what the bigger thing is?"

Thomas replied, "No, but you can't stop me from resigning." Jenny resumed, "The bigger thing is that from the moment I met you, this is the first time you have disagreed with anything I have wanted, anything. I never thought you would wear a dress, but you did it for me. I must tell you, I am very sorry if I hurt you.

I got carried away with a sense of power over you, and for that, I am sorry. You can go back to wearing your regular clothes. I am so sorry." Thomas didn't know what to say. He never realized how she felt. He kind of felt bad for her, and yet felt pride that he had stood up to her. He sat quietly and thought how this was the first time she had ever had this deep a discussion about her feelings with him.

He knew she was sincere. He got up and took the letter from her and tore it up. Thomas said, "Don't bother. Not right now, anyway." Jenny asked, "Why not? Don't you wanna change right now?" Thomas said, "No, we can wait till tomorrow night." Jenny asked, "Why wait? I said you can change now. Don't you wanna get out of that skirt and blouse?"

Thomas answered, "No, we can wait until tomorrow night. Tomorrow, I'm going to wear that blue dress I got, and you know blue is my color." They both laughed, and in that laugh, they were closer than they had ever been in their lives. The end.