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Dare To Wear A Dress
🕑 Added 2020-04-27 11:24:11 +0000 UTCSUMMARY - Tomboy girl marries a shy boy dares him to wear a dress to work
Jessie Taylor sat at the kitchen table with her math book open in front of her. Her neighbor, a boy named Jeff Filz, sat next to her. He said, "Algebra isn't hard if you take it one step at a time. Now, look at this problem. It's simple if you look at the parts."
He went on to explain how to dissect the problem. She suddenly understood what he was showing her. He was a math whiz. She continued on and did the next four problems without much difficulty.
She said to him, "I really want to thank you. You made it seem so simple. I wish they would make it that simple in the classroom."
He was about to say something when her brother Chuck came into the room. He said, "What's going on? What's the fairy prince doing here?"
Jessie answered harshly, "He's helping me with my math. And he isn't a fairy!"
Jeff excused himself and left. Jessie said to Chuck, "I wish you would watch your mouth. Jeff is a nice boy. He is quiet and I know he isn't any good at sports but that is no reason for you to call him a fairy. He was helping me with my math. You embarrassed me in front of him."
Chuck said, "I'm sorry if I embarrassed you but he is not my idea of someone masculine. He is a wimp. I have never seen him stand up for himself."
Jessie said, "Well, in the future just watch your mouth. You may be my older brother but you have a lot to learn when it comes to dealing with people!"
Two weeks later Jeff saw Jessie in her driveway. He walked over and asked, "I know you know a lot about cars. My car is sounding funny and has no power. Do you suppose you could listen to it and see what you think?"
Jessie agreed and went with him to listen to his car. She quickly ascertained that it was a fouled spark plug. She told him she would fix it. She went and got some spark plugs and soon had it running. She then said to Jeff, "I changed your spark plugs and adjusted your carburetor. It should run a lot better now."
Jeff thanked her and paid for the spark plugs. She wouldn't take anything for labor. Her brother Chuck teased her when she came into the house, "Well did you get the fairy prince's car running?"
Jessie answered, "Yes and I wish you wouldn't call him that. He is a very nice person, but you wouldn't know anything about being nice, would you?"
Chuck quickly changed the subject. He said, "In two weeks you will be graduating. I have a proposition for you. You have a talent for fixing cars. Do you want to become a partner in my auto shop?"
Jessie quickly answered, "Yes, oh yes. I'd love to. But what will it cost me?"
Chuck said, "You are the only sister I have. You have a touch with carburetors that I don't have. I feel we can work as equals better than as boss and employee. I have been in the shop for two years and you have helped me after school and on Saturdays for free. So consider your time as payment in our partnership. The business has grown to where I can't keep up, so you will be busy."
Jessie said, "Thank you. I never expected this. Mom will be so proud of you."
Just then their mother came in from shopping. She showed Jessie a new dress she had bought for her. She said, "Look at this. It was so pretty that I just had to buy it for you!"
Jessie looked at the dress. It was a green dress with lace on the upper part running up and down. She said, "Thank you mom but you know I don't like wearing dresses."
Her mom said, "You will have to start wearing dresses if you want to attract a man. You are just about out of school and you still don't have a steady boyfriend. It's time to start baiting the boys. I know this dress will attract them."
Jessie said, "Guess what, mom. Chuck just offered me a partnership in his auto shop! Isn't that great!"
Her mom said, "Chuck, how wonderful. You have surprised me and made me very happy. This family is the one big thing in my life. It's so comforting to see you looking after your sister."
Chuck said, "She deserves it. She's helped me out when I was falling behind. It's the least I can do."
Jessie took the dress and hung it in her closet next to the other dresses her mother had gotten for her. She knew she wasn't a dress girl. She loved her mom but she just couldn't convince her that she didn't care to wear dresses.
Two weeks later it was graduation. Jessie asked Jeff what he was going to do after graduation. He told her he had signed up for a two-year course in accounting. He told her he'd gotten a full scholarship so all he had to earn was some spending money. Jessie had talked to Chuck and offered Jeff a job getting the books straight at the auto body shop. Jeff accepted but told her he didn't know a lot about accounting yet. He said he would do the best he could.
The next day Jeff was at work. Some of the items were easy to place and some required him to ask Jessie or Chuck. By the end of the first day, he had pretty well set up the categories and made quite a few entries. He had also found about $800.00 in bills due to the auto shop. He gave those to Chuck.
That night at supper Chuck said, "It was a good idea to hire the fairy prince. He found bills I had lost and he seems to be getting the books in order."
Jessie immediately replied, "Don't call him the fairy prince. It isn't nice. He is a nice young man. I like him. He treats me nice and is always pleasant to me."
Chuck defended himself, "Well I have been calling him that for so long it's second nature to me. I'm sorry but you know how a nick-name sticks to someone."
Their mother spoke up, "Chuck, you don't call him that to his face, do you?"
Chuck answered, "No, I guess I do it to get a rise out of Jessie. You don't think she is sweet on him, do you?"
Jessie blushed. She'd never thought of Jeff as a boyfriend. They had gone for a malt a couple of times but it was mostly to talk about things.
The next day Jeff finished getting everything on the computer. He showed Chuck where everything was. He told Chuck it wouldn't be a bad idea to get someone to keep the records up to date. Chuck offered him the job but he turned it down explaining that he needed time to study for school. Chuck thanked him for all that he had done and paid him generously.
Jeff went into the work area and asked Jessie if she wanted to go for supper that night. She accepted. They went to a small supper club known for its steaks. As they were eating Jessie noticed that Jeff adored her. She knew she wasn't as infatuated with him as he was with her. It bothered her a bit but she shrugged it off.
From time to time over the next two years, Jessie talked to Jeff. He was getting outstanding grades and he shared this information with Jessie. He graduated at the head of his class with a perfect 4.0 average. To celebrate his graduation, on graduation night Jessie took him out for supper. He told her that he was going to start looking for a job.
The next day he put his resume in at three different companies. They all said they would call him if something opened up. He had been told in school that companies were always looking for the right people to do their books. But it wasn't like he expected.
The following Monday one of the companies called him to come in for an interview. He was ecstatic. He was pleasantly surprised when Jessie knocked at his door that evening. He told her the good news.
Jessie said, "Well, I guess that shoots what I came over for."
Jeff asked, "What did you want? Tell me."
Jessie answered, "Well, Marybeth, our lady who took care of the books, is leaving. Her husband got a job two hundred miles from here. They are moving. I was going to offer you the job."
Jeff said, "Wow, two job possibilities in one day. This is great. The company that called today is Ganzen and Son. They are the biggest in town. I'll tell you what, let's go for a malt, my treat. I'll think it over and let you know what I decide. Is it a deal?"
Jessie agreed. They drove to the malt shop. It wasn't busy and they picked a booth away from the other customers. Jeff thought about the prestige of working for the biggest accounting firm in town and then he thought about the idea of working close to Jessie. It was a hard decision to make. He finally made up his mind. His heart won!
He said, "Well, I know what I am going to do."
Jessie timidly asked, "Well, are you going to tell me or am I going to have to wait?"
Jeff told her he would work for them. He remembered a teacher saying take a sure job, don't count on promises. Jessie was very happy. She told him to come in tomorrow and Marybeth would show him the ropes for the next two days. She told him Marybeth had said she would like to start packing on Thursday.
Jeff went to work the next morning. Marybeth was real nice and complimented him on how he had set up the books. She showed him some things she had added to make tracking work orders easier. By noon they were old friends. Marybeth told Chuck and Jessie they had one smart boy there.
Within a week Jeff had it down to where after about an hour and a half he could relax and take the new things as they came in. Deliverymen got to know him and he was in heaven. He had a good job and he was working near Jessie. Occasionally after work, they would go out to eat but it wasn't really a romantic situation. Jessie would talk about cars she had worked on and much of it went over Jeff's head. He was not mechanically inclined.
Two months later Chuck got married. At the dance that evening Jessie was dancing a slow dance with Jeff.
Jessie said, "You know, maybe we should get married."
Jeff asked, "Is that a proposal?"
Jessie said, "I don't really know. I like you a lot but I am not sure. What do you think?"
Jeff said, "I have never told you how I feel about you. I have thought about it but it never seemed the right time to say anything."
The dance ended and Jessie said they should go outside and talk. They went outside and Jessie was surprised as Jeff talked to her.
Jeff said, "Jessie, I have been in love with you since we were in high school. I have fantasized about being married to you. You never let me know how you felt about me so I was afraid to say anything to you. I think you treat me more like a brother than a lover. Don't get me wrong, I don't mind it."
Jessie said, "I'll tell you something. I have feelings for you. Strong feelings. But I am not sure that they are true love. I know you like me a lot. I felt you came to work for us because you would be near me. For that I thank you. You are a special person to me. What you may need is someone who will cook a special meal for you and keep your house in order. I am not a cook or homemaker. I hate cleaning. You deserve better than what I can offer you. You deserve a feminine woman who will lavish love on you. I don't know if I can do that. I'm sorry."
Jeff said, "Don't worry about the cooking or cleaning. I do that now for myself and it isn't so bad. I am more comfortable cooking and cleaning than doing yard work."
Jessie said, "When you put it that way maybe we can make it as a couple. Do you want to get married to me?"
Jeff said yes and they went in to tell Chuck and his bride. When they told Jessie's mother she said, "Well it's about time you two woke up. I always thought you two would get together but someone didn't see the signs. I won't say whom but my daughter sometimes is blind to those around her. Jeff, welcome to the family. You make me very happy."
The following week they made plans. They checked halls where they could have the reception and dance. They picked one that had a cancellation four months later. They set the date. They planned a small wedding and the time sped on.
The wedding day arrived and Jessie looked beautiful in her wedding dress. Jeff thought about how it was the first time he could remember her in a dress. They were both extremely happy. They celebrated their wedding night a little clumsily but it was successful. Jeff was in heaven and Jessie caught the feeling.
Jessie said to her groom, "Honey, I don't know why it took me so long to recognize my feelings for you. I am glad we are husband and wife. You have made me so happy."
Jeff told her she was his goddess and their love filled the room. They took a weeklong honeymoon to Jamaica. They returned from the honeymoon and everyone could see the love between the two.
A couple of months later Jessie was working on a carburetor and Chuck was working on a transmission. Chuck took a break and invited Jessie to join him.
Chuck said, "Our workload is getting bigger. I have offered Tom Watson a job as a mechanic. He accepted. He is going to start tomorrow. With the four work bays we have, it shouldn't be a problem."
Jessie said, "You mean we will be able to get out of here before nine at night finally?"
Chuck said, "Yes, hopefully, it will ease up on our time. Tom is a good mechanic and I expect he will ease the backlog. Lately, the only one getting out on time is the fairy prince."
Jessie shot out, "I told you don't call him that!"
Chuck said, "I'm sorry but he is more a wife than you are. Who does the cooking and cleaning of the house?"
Jessie said, "He does but that is because we worked it out before we were married. You know I am not a good cook and I am not a house cleaning person. You must admit our house is always clean and neat. Besides Jeff is a great cook. I could never match some of the meals he makes."
Chuck said, "See, what did I say. He is more of a wife than a husband. You should put him in those dresses you never wear."
Jessie said, "You just don't understand. Our partnership in marriage works beautifully for us. You are just jealous of how good we are getting along."
Chuck said, "I dare you to put him in dresses. You are afraid to admit he is more of a wife than the husband."
Chuck knew Jessie never turned down one of his dares. He repeated, "I dare you. If he loves you as much as it seems he will do whatever you want."
Jessie said, "You expect him to come to work in a dress!"
Chuck said, "As long as he does his work I don't care if he comes in a swimsuit. I got kind of used to seeing Marybeth out there in her dresses. His job is one a woman could handle. Do you accept the dare?"
Jessie said, "Give me a couple of weeks at least." Jessie was mad at herself for letting Chuck maneuver her into this but she figured her Jeff would not be a problem. She thought it might be fun for them.
She planned to try that Sunday. She came in from the garage as Jeff was finishing cleaning the kitchen counters. She said, "Well, I changed the plugs in your car. You had one that was fouling out, that's why you didn't have the power you once had. You will be in good shape now. I am going to mow the lawn. While I am doing that why don't you make yourself pretty for me."
Jeff said, "What do you mean to make me pretty for you?"
Jessie answered, "Well, you know, put on some lipstick and maybe a dress. Try to make yourself look like a sexy housewife."
Jeff said, "I don't think I can do that. That's crazy!"
Jessie said, "Well I am going out to mow. Just give it a try. I'll make it worth your while when I am done mowing."
She left and Jeff stood there wondering what was getting into her. He had no intention of putting on a dress or lipstick. He went to clean the living room. Jessie finished the mowing and came in. She saw Jeff hadn't put anything on. It didn't surprise her so she moved on to plan B. She went and nuzzled Jeff and started kissing him. He reacted as any man would and when she told him she would meet him in the bedroom he headed right for it. She stopped in the bathroom and met him in the bedroom.
She kissed him then said, "Let's add something. How about lipstick?"
Jeff agreed heartily. He watched her take the cover off the lipstick and before he realized it he was wearing a coat of lipstick. She kissed him and told him he looked sexy.
Just into intercourse, she said, "Will you wear a dress for me?"
Jeff moaned, "No-o-o-o. I don't want to."
A bit later Jessie said, "Won't you please wear a dress for me? They are just hanging in the closet. Someone should get some use out of them. When we get done will you try one on?"
Jeff said no again and Jessie continued, "Won't you wear a dress for me? They are just hanging there taking up space and I think you will look good in a dress."
Jeff said, "You wore a dress for the wedding and you looked beautiful. Why don't you try to wear them."
Jessie retorted, "I am not a dress wearer. All I am asking is that you try it. Will you try it, for me?"
In a moment of weakness, Jeff agreed. Jessie was ecstatic. She knew she could get him to wear a dress. They finished their love-making and Jeff was reaching for his undershorts.
Jessie said, "No-no-no. You agreed to try a dress. And you might as well wear the rest of the things that go with it."
Jeff froze in place as Jessie got the satin panties out of her drawer. She said, "Here put these on. I haven't worn them since the wedding. Then she got the matching bra and put it on him. She stuffed the cups with socks to give him an ample chest. She hooked the garter belt on him and helped him with the stockings. When she slid the satin slip over him his mind went into overload. He didn't even realize it when she slid the pink dress over his head and onto his body. She helped him put a pair of sandals with a two-inch heel on. She walked him around a bit. In no time he was able to move on his own. She got the old wig she had worn for Halloween so many years ago. She never knew why she had kept it. She brushed it out so it was presentable and placed it on his head.
She looked at her feminized husband and exclaimed, "You look wonderful. I never looked that good in a dress."
Jeff blushed and Jessie said, "If you keep blushing like that you won't ever need blusher. Thank you for doing this for me."
Jeff asked, "Can I take it off now?"
Jessie said, "No, leave it on. You look so adorable. I have never had a close girlfriend before, now I have."
Jeff couldn't understand why he felt so submissive. He just couldn't bring himself to deny Jessie anything. They went into the living room and sat next to each other on the couch. As they watched TV Jessie would kiss him every little while. Soon it was time for Jeff to make supper. He made a delicious meal.
As they were eating Jessie said, "Tomorrow you can wear the blue dress. That one is perfect for office work."
Jeff was shocked and said, "I can't wear a dress to work. What will Chuck say? Please let me wear my regular clothes!"
Jessie said, "All those dresses are just hanging there not getting used. I can't wear a dress fixing cars but you can wear one sitting doing your job. It won't hinder you from doing your job will it?"
Jeff answered, "No, it won't hinder me but I am a man, not a woman. A man doesn't wear dresses! You didn't answer my question-What will Chuck say?"
Jessie said, "Chuck doesn't care. It was his idea. So tomorrow you can wear the blue dress."
Jeff said, "What do you mean it was his idea?"
Jessie said, "He dared me to put you in a dress. I don't know why but I have never backed down from one of his dares. He knows he has a hold over me when it comes to dares. I am sorry but that's the way I am. You know that no one but Chuck and I come into the office, so what's the big deal."
Jeff responded, "The deliverymen come in with parts. What am I to do then?"
Jessie said, "You look so much like a woman they will think it is a new person there. Look at it this way. I fix cars and do all the things around here that a husband normally does, You do the cooking and cleaning of the house, all the things a wife normally does. Now we are properly dressed for our roles. I still love you as much as I ever have. Please just try it for me, please?"
Jeff thought for a few minutes then agreed to try it. Jessie was very happy. She looked at him and she knew he was only doing this because of his deep love for her.
The next morning as they got ready for work Jeff asked her to reconsider. She told him the blue dress would be fine for work. When they arrived at work Jessie told Chuck to go to the office for a surprise. Chuck went into the office and said good morning to Jeff. He didn't act like anything was different. Chuck went back into the garage area and congratulated Jessie. He told her he didn't believe she would be able to do it.
For Jeff, the day went fast. There was only one delivery and the man didn't seem to notice that it wasn't really a woman who accepted the delivery. When it was time to quit Jessie said she had about an hour's work yet so Jeff walked the block to their house. He started supper.
During supper, Jessie said, "I am so proud of you. Chuck agreed to never dare me again. I told him how I hated doing that to you. He said you surprised him in how you are taking it. I think he has more respect for you now."
Jeff said, "It wasn't as bad as I thought. There was only one delivery and that went smoothly. In a way I kind of like the feel of the skirt hitting the back of my legs. I don't know why."
Jessie said, "Tomorrow why don't you wear a green dress. Of all the dresses my mother got for me she liked that one best. I think she figured if she pushed enough I would wear it more often. I have never worn it. It became a contest between Mom and me. She pushed for me to wear it and I pushed back by not wearing it."
That night in bed they made passionate love. They both felt something special was happening but didn't know what. The next morning Jeff wore the green dress. He looked out into the garage area and saw Tom Watson in the first bay working on an engine, Jessie was in the second bay working on a car and He saw Chuck getting ready to crawl under a car in bay three.
Fifteen minutes later he saw a flash of light. Then he heard the noise. It was an explosion. He saw Tom head for outside. He dashed into the garage area and saw Jessie laying on the floor. He went by her and scooped her up and carried her outside. He laid her down gently and looked back toward to garage. He saw the form of Chuck laying partially under a car. He wasn't moving. He dashed through the flames and grabbed Chuck under the armpits. He dragged him outside next to Jessie.
A man approached him and said he had called 911. He said the fire department was on its way. Two police cars drove up and started interviewing the man. Within minutes the fire department was there. Jeff saw the ambulances take the three people to the hospital. He quietly walked away. He walked to the house and went in and changed clothes. He then walked back to the garage.
The fire department was finishing up and starting to put their stuff away. He walked up to a policeman and identified himself. He answered some questions from the police officer. He stood there and looked at the mess. It wasn't as bad as he thought. There were a couple of broken windows but most everything else had been saved. He didn't know how bad the cars were that were in the garage but imagined there was damage to them. He heard the guy who had called 911 talking to a TV reporter. The man was telling how a woman in a green dress saved two people.
Jeff smiled to himself when he heard the TV reporter say how they would find the woman in the green dress. He heard the police officer say she was a hero. When the fire department had finished he went and hit the switch for the overhead doors. They closed and he went into the office and shut down the computer. He then locked the office and headed home.
At home, he changed into a red and yellow floral sundress and headed for the hospital. He checked at the desk and found out what rooms Jessie and Chuck were in. He went into Jessie's room fearful of what he would see. Jessie was sitting up in bed with her arms wrapped a light gauze. He could see burns on her arms. He went over and kissed her.
She said, "I was lucky. I won't need skin grafts or any of that stuff. The doctor said I have to stay a couple of days to make sure no infection sets in. I hear Tom is going to need skin grafts. They are thinking of transferring him to a burn center. I haven't heard how Chuck is doing."
Jeff said, "He is in the next room. Do you want me to go and see how he is doing?"
Jessie said, "Yes, please, I am worried about him."
Jeff went to Chuck's room. When he walked in Chuck was sitting with his legs dangling off the side of the bed. Chuck smiled at him.
Chuck said, "I am lucky. A couple of minor burns and a concussion. I hear you dragged me out. I want to thank you. I never thought you were strong enough to pull me out. Where did you get the strength?"
Jeff said, "I don't know. All I know is that I couldn't leave you there. I had to get you out. I never thought about not being strong enough. How could you get a concussion? I thought you had a hard head."
Chuck laughed and said, "When the bang came I hit my head on the car. I don't remember anything until I woke up in the ambulance. How is Jessie doing?"
Jeff said, "She will be all right. I hear that Tom might be transferred to a burn center. I guess he got the worst of it. Jessie is next door."
Chuck told Jeff to help him get to Jessie's room. Jeff helped him and as they entered they heard the non-newscaster saying, "There was an explosion at Taylor's Auto Shop. Three people were injured and are in the hospital. We and the police are looking for a woman in a green dress who saved two of the people. We will update you when we have more information."
Chuck smiled at his sister. Jessie said she was fine that she just had a burning sensation on her arms.
She looked so sad that Chuck asked her what was wrong. She said, "I should never have made Jeff wear a dress. You should never have dared me! I feel terrible about what I have done. Jeff is too good to me. I took advantage of him."
Chuck said, "Jessie I am sorry about that. I'll never dare you again. I am afraid I may have some bad news. You are only going to be a thirty-seven and a half percent owner in the business."
Jessie aid, "Why, what have I done?"
Chuck said, "You haven't done anything wrong. From now on there's going to be three owners of Taylor Auto Shop. Do you want to know who the third owner is?"
Jessie said yes, of course, and Chuck continued. "I don't know how I can thank someone who has done something so special for me so I figure on making Jeff a quarter owner also. Is that all right with you?"
Jessie said, "Yes, oh yes. Thank you!"
Chuck turned to Jeff and said, "Jeff, I want to apologize to you for all the bad things I have said to and about you. You are a great guy. I know I owe my life to you. I am proud that you are my brother-in-law."
Just then Chuck's wife Diane came in. She said she came as soon as she heard. She and Chuck headed back to his room.
Jessie said to Jeff, "I have something important to say to you. When I came in they did all kinds of tests. You have to go home and change. I don't want to see you in a dress anymore. Besides you are going to want to look like a man when the baby gets here."
Jeff said, "What baby? Are you pregnant?"
Jessie said, "Yes, that's what they told me. They said I must just be pregnant but I am definitely pregnant."
Jeff had tears in his eyes as he kissed his wife. He knew their love would conquer anything that came along.
Comments
edwin sargent
i bet if there was a second chapter he would wear a dress all the time
Leslie Deana
I loved the ending and things going 'back to normal'.
Thea Camille Leon
This story could go so much further in role reversal. Jeff could continue working as the bookkeeper, but also working from home while taking care of the baby. His nurturing personality might lead him further down that path, becoming a surrogate mother. After all, it is possible for a man to develop breasts and actually lactate, as a few cultures do in the rest of the world and which occurs in a few mammal species. It is certainly known that trans women can breast-feed their adopted babies. A very interesting twist perhaps?
Julia Miller
Who do you think will take care of the kids? Lol. More dresses in Jeff’s future.
J Chimera
And just when he was getting to like his dresses.
