Boy Forced To Wear A Dress By Mother

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Boy Forced To Wear A Dress By Mother
I am 16 and male. I got caught by my mom dressing as a girl. What should I do?
Studied at Bailey Boswell High School ( Graduated 1987 ) · Author has 195 answers and 83.1K answer views · 1 y ·
I am 15. I crossdress with my mom’s clothes since I was 12 and my mom keeps asking me to crossdress, and I really want to say yes. What do I do?
Why did my mum buy me a skirt and tights for my birthday? I’m a 17-year-old boy. What should I do?
My teen son dresses as a girl after school and on weekends and my wife (his mom) helps him, is this ok?
I’m 14. My mom makes me wear dresses in the summer. She says that shorts don't look good on me because my thighs are too big. This is damaging to my self esteem. She won’t even let me compromise for a skirt. How do I convince her otherwise?
My mom makes me crossdress and I’m a boy. I have no boy underwear only panties and a lot of my closet are girl jeans and leggings. What should I do?
BA from California State University, Sacramento · Author has 9.8K answers and 9.1M answer views · 1 y ·
I am 15. I crossdress with my mom’s clothes since I was 12 and my mom keeps asking me to crossdress, and I really want to say yes. What do I do?
Why did my mum buy me a skirt and tights for my birthday? I’m a 17-year-old boy. What should I do?
My teen son dresses as a girl after school and on weekends and my wife (his mom) helps him, is this ok?
I’m 14. My mom makes me wear dresses in the summer. She says that shorts don't look good on me because my thighs are too big. This is damaging to my self esteem. She won’t even let me compromise for a skirt. How do I convince her otherwise?
My mom makes me crossdress and I’m a boy. I have no boy underwear only panties and a lot of my closet are girl jeans and leggings. What should I do?
I’m a 15-year-old boy and my mom is forcing me to wear girly clothes because of my bad grades. What should I do?
Have you ever been caught crossdressing by your sister? If yes how did you both react?
Why do mothers crossdress their sons and cuddle?
What is the right way to tell my son (14) that I'm okay with crossdressing in my lingerie? I had found him secretly wearing my bras.
How many people were caught by an aunt cross-dressing?
Why does my neighbor let his adult son wear female clothes outside?
Is it normal for a Mom to help her teen son (15) crossdress?
I caught my son cross-dressing. What should I do?
Have any other moms dressed their son up as a girl?
What kind of help should I provide to my cross-dress teen son?
I am 15. I crossdress with my mom’s clothes since I was 12 and my mom keeps asking me to crossdress, and I really want to say yes. What do I do?
Why did my mum buy me a skirt and tights for my birthday? I’m a 17-year-old boy. What should I do?
My teen son dresses as a girl after school and on weekends and my wife (his mom) helps him, is this ok?
I’m 14. My mom makes me wear dresses in the summer. She says that shorts don't look good on me because my thighs are too big. This is damaging to my self esteem. She won’t even let me compromise for a skirt. How do I convince her otherwise?
My mom makes me crossdress and I’m a boy. I have no boy underwear only panties and a lot of my closet are girl jeans and leggings. What should I do?
I’m a 15-year-old boy and my mom is forcing me to wear girly clothes because of my bad grades. What should I do?
Have you ever been caught crossdressing by your sister? If yes how did you both react?
Why do mothers crossdress their sons and cuddle?
What is the right way to tell my son (14) that I'm okay with crossdressing in my lingerie? I had found him secretly wearing my bras.
How many people were caught by an aunt cross-dressing?
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It's a new beginning to your new lifestyle , just remember parents always be parents to protect their children from harm ways . Just be yourself and keep your head up high and walk away from negative people who want to do harm to you , be around people who you trust . It's up to you if you want to come clean towards your mother maybe take that monkey off your back from worrying on how she feels about her son dressing like a woman . Be very up front with your mother and tell her what you feel about wearing women's clothing and why you want to wear them , I was once a CD and always dress time to
It's a new beginning to your new lifestyle , just remember parents always be parents to protect their children from harm ways . Just be yourself and keep your head up high and walk away from negative people who want to do harm to you , be around people who you trust . It's up to you if you want to come clean towards your mother maybe take that monkey off your back from worrying on how she feels about her son dressing like a woman . Be very up front with your mother and tell her what you feel about wearing women's clothing and why you want to wear them , I was once a CD and always dress time to time when I get stressed out about life and it's better than doing harmful drugs or drinking my life way , that's why I shy myself into CD it takes the ugliest of life to a beautiful state of mind to be pretty with myself.
You don't do anything. You are who you are and whether it was for an experiment, a party, or that you enjoy wearing women's clothes, etc… you should never apologize for being who you are. I'm going through this with my 15 year old son who wants to do drag. I've bought him makeup and a few clothes but his size is a problem since he's over 6 feet and 235 lbs. Trying to find attractive beautiful clothes that fit his shoulders is a challenge. I may have to pull out the sewing machine and make some. Never feel embarrassed by being who you are or feel like you have to hide for other people's comfort
You don't do anything. You are who you are and whether it was for an experiment, a party, or that you enjoy wearing women's clothes, etc… you should never apologize for being who you are. I'm going through this with my 15 year old son who wants to do drag. I've bought him makeup and a few clothes but his size is a problem since he's over 6 feet and 235 lbs. Trying to find attractive beautiful clothes that fit his shoulders is a challenge. I may have to pull out the sewing machine and make some. Never feel embarrassed by being who you are or feel like you have to hide for other people's comfort.

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"But Mooom..."

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A simple pair of cotton panties. An embarrassed squeak escaped his throat as he slipped his feet through the holes before slowly pulling them up. They were so much tighter than his usual briefs, and soft too... he sighed and picked up the next
The rest of winter break was spent preparing for my new living arrangements. I called the school and told them that I would like my name changed in the system so the professors would only have my new name; however, I told them to keep my real name on my legal documents. They made that happen. Em and her mom had gone out and bought me a new wardrobe. We also decided on me getting a part-time job, so I could start saving to pay off my debts. Since Em quit her job at IHOP so she could go on vacation with us, she would also be searching for a new job; we planned on getting a job together.

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Sarah knows that, with the right plan, she can make her brother Sam think of dresses the same way he thinks of any of his other clothes. The question is, what is that right plan?
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“Boys don't wear dresses!” Sam insisted. His sister Sarah rolled her eyes. That was always his argument.
“Well, why don't they, Sammy?” She asked. He shrugged, just like he always did. In some ways, she felt like they were stuck in a loop when it came to this. She figured clothes were clothes. If she could wear jeans and t-shirts, he could wear dresses from time to time, right?
“It's just how things are. You've never seen dad or your teacher Mr. Lapine wear a dress, have you?”
“No, but they're grown-ups. You're practically my twin.”
“I know, I know. Seventeen months older than me.” She waved a hand dismissively. “You’re still basically a little boy, is my point.” She wisely pushed on before that comment could fully register with his fragile male ego. “Bet I have a dress that'll fit you.” She grinned as his cheeks grew pink.
“That” he sputtered. “That doesn't matter.” She giggled. She knew all too well that she had him now.
“A bet.” She said it slowly, as if he was stupid. “If my dress fits you, you have to wear it. If it's too small, then you don't.” She could see his reservations written all over his face, so she patted his shoulder reassuringly, just like their mom often did. “It's just a harmless bet.”
“That's what you always say.” Her proclivity for so-called harmless bets always seemed to get him stuck in terribly embarrassing situations.
“Look,” she said with a weary sigh. “I promise that, if it does fit you” she knew it would, but she still emphasized the if, just for his peace of mind. “We’ll play in my room until you take it off. Even mom and dad won’t know unless you tell them.”
“No photos, no videos, nothing.” Sam said shrewdly. Thanks to another allegedly harmless bet, she had a phone and he did not.
“Does that mean you’re going to try?” She asked, grinning as broadly as could be. He sighed.
“Yeah.” He said through gritted teeth. With a squeal, she grabbed his hand and pulled the boy toward her room.
“Sit down on my bed.” She ordered, giggling as the boy complied. “Is your bed made?” She asked as she nearly skipped over to her closet.
“Psh” was all she said as she began to look through her closet. There was a specific dress she had in mind, one that was just a tad too big for her. She had not one single doubt that it would fit Sammy as if it was made for him, if perhaps a bit short. She hoped he was wearing cute undies, giggling to herself as she imagined ordering him to go put on cuter underwear under threat of having to wear her panties. She would hold true to her promise not to take any photos or video, but she could still have fun in other ways, right?
Finding just the dress she was looking for, she kept it out of sight and turned back toward her brother. He looked as though he was about to be sick, which seemed a bit extreme to her.
“Go ahead and get undressed. You can’t wear it over your clothes.”
“How long am I going to have to do this?”
“Again, it’s only if it fits.” She said, trying to reassure him. “But, if it does, well, how long would you be wearing those clothes?”
“Until bed.” He said nervously. “You can’t.”
“Well, that’s why we’re discussing it now, isn’t it? Silly Sammy.”
“It's Sam.” He corrected before returning to the issue at the forefront of his mind. “I’m not wearing it all day.”
“Like I said, we’ll stay in here and not even mom and dad’ll know.”
“But mom’s running errands. She’ll be home in a couple hours.”
“Are you saying you’ll wear it until she comes home?”
“No!” He protested. She tapped her chin as she thought, another habit of hers that echoed their mom.
“How about we” she said slowly. “Roll a die? If you roll higher, you'll wear it until Mom comes home. If I roll higher, you'll wear it until bed.” He looked unhappy about it.
“If I win, I get to take it off after an hour.” He hoped that that was long enough to appease her.
“If that's the case, then if I win, you have to wear dresses until school on Monday!” She giggled as his eyes became as wide as dinner plates. It was only Friday and that would mean far too long in dresses for his tastes. Even the rest of the day was too long, if he was being honest. “Wanna agree to my original terms then?” He nodded, his eyes filling with defeat. “Alright. If you roll higher, you're in a dress until Mom comes home. If I win, you're in a dress all day. Agreed?”
“Yeah.” He grunted. She walked over to her dresser and grabbed a white die from on top of it.
“I'll roll first so you know what you need to beat.” She shook it and rolled it on the floor where he could clearly see it. “Four. You've got a chance.” He nodded.
“We'll both reroll.” He shook the die in his hands and rolled it. It tumbled and bounced before landing on five. He breathed an audible sigh of relief.
“Alright,” she said, trying to hide her disappointment. “Get undressed. We’ve only got so much time for you to wear a dress before Mom gets home.” She stood there, watching him as he pulled his shirt off and then stopped at the button of his jeans. “Pants too. I’ve seen your underwear before. You’re my brother, after all.”
“Couldn’t you at least stop staring?”
“We shared a room until you were seven. Geez!” She smirked deviously. “And I know for a fact that your undies haven't changed since then.” For his last birthday, he had begged and pleaded for boxer briefs, but she had asserted her strange ability to get their parents to do whatever she wanted. Rather than opening packages of the underwear he insisted all the other boys in his grade wore, he opened packs of childish briefs with rockets, racecars, and sailboats on them. There had even been a few pairs with teddy bears on them. “C’mon.” She urged. “Drop your pants so you can get dressed.”
“Fine.” He unzipped his fly and dropped his jeans, revealing a pair of white briefs with red fire trucks all over them. She giggled and turned to grab the dress she had picked out for him.
“It won’t really match, but I’m sure you don’t mind.” She held up the baby blue party dress, a gift from their aunt to her a year or two ago. To her eye, it was painfully juvenile, which only made it better that her brother would be wearing it. It had puffed sleeves, a white sash to tie around the waist, and plenty of petticoats that would ensure that his underwear was on display if and when he was not careful. “Don’t look like that.” She scolded. “You know you’re only in it until Mom gets home.” She carefully removed it from its hanger. “Now, come on. It slips over your head just like a shirt.” He took it, his face almost looking green. “Be careful. It’s not like your shirts where you can be so rough.”
She grabbed the skirt and pulled it down his body, making sure it did not get stuck as it fell into place. She smirked as she turned him around and zipped it up his back. Sure enough, it fit, although not as perfectly as she had hoped.
“Here. Look at yourself in the mirror.” She said, steering the bashful boy exactly where she wanted him. He stared at his reflection as she, figuring fair was fair, slipped into a dress nearly as frilly and little girlish as the one he now wore. She hated wearing dresses like this one, but it was definitely sweeter to see her brother in one as well. “What do you think?” She asked, smoothing out her skirt out of habit.
“Can’t believe you talked me into this.”
“Oh, please.” She punched him in the arm. “We used to do this all the time! Remember that time me and my friends held you down and painted your nails?”
“Sammy! We did it like three different times, I think.”
“What do we do now?” He asked sullenly. She shrugged.
“Whatever we want. You’re shy, but we could go out to the living room and play a game or watch TV or something.” She loved how shy and bashful he looked, but she would have to devise some way to normalize dresses for him. After all, they were just clothes and she wanted nothing more than to make her brother see them that way as well.
She could feel the wheels of her mind turning. After all, she had asserted her will over him in so many ways, how hard could this be? She was the one who had found that study that argued that boys need more sleep than girls, pushing his bedtime to an hour before hers. She would find some way to make him wear dresses. Not all the time, but sometimes.
“So, what do you want to do? I’d say you can go to your room, but how do I know you’ll leave your dress on?”
“I guess we can go watch TV.” He said. “But we’ll need to make sure we can hear when Mom comes home.” She nodded.
“Yeah, I’d rather she not see me like this.” She said, giggling as he gave her a strange look. “I’ve worn dresses enough to know what dresses I like and what I don’t. Maybe you’ll get to that point someday.”
“Doubt it.” She felt her heart leap. Could this be the chance already? She tried to control herself. Her brother was dumb, but even he picked up on her plans sometimes.
After a brief tutorial on how to sit without flashing his underwear, the siblings settled in to watch television. Sarah could not resist glancing over and seeing the ridiculous sight of her brother sitting there, skinny pale legs poking out from the blue dress. He kept his hands in his lap to hold the skirt of the dress down and she almost wished she could find some way to make him relax, if only to tease him about flashing his boy underwear.
“How do you feel?” She asked as the show went to commercials.
“You seem comfortable.” She remarked. “You haven’t really complained since
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