Spit and Image: 1

 

Eighteen year old Paul is asked to help his mother with a sewing project. Everyone
knew that Paul bore a strong resemblance to his grandmother when she was young, but
when he lets his hair down and becomes his mom's dress model, they realize that he
truly was made in her Spit and Image.

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Author's Note: Thank you for all the wonderful emails and comments about this story. Please continue to let me know what you think of the story. All comments, pro or con, are really helpful. ~Clara.
 
This version of Spit and Image: 1 has been updated with many corrections towards spelling and grammar.~Sephrena.
 
Image Credit: Image created through the use of ai at https://perchance.org/beautiful-people .~Sephrena.

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Chapter 1
 

"Paulie, honey," his mother called from the dinning room where she'd set up her machine, hangers and bolts of material. "I need your help again, please. I won't hold you up for more than ten minutes, more."

Paul sighed and shook his head, "Yep. I'm coming." He put down his video game controller, pulled himself off of the couch, closed the soft robe more tightly around him as he rose and made his way from the family-room to the dinning room. "This has to be the last time, though," he told his mother. "I've got to shower. Lori is picking me up at 5:30 and I need to shower and change before she comes."

Eighteen year old Paul, a high school junior, had not yet gotten his license, but Lori, his first serious girl friend, who was a year ahead of him, had. They'd been dating since homecoming back in October. He loved the feeling of independence that he had whenever he climbed into Lori's car and they went out for the evening.

As Paul entered the dinning room, pulling the robe a bit more closed around his neck, his mother smiled at his modesty. Typically, Paul was walking around the house in his tighty-whities, but, for last couple of weeks, when she needed his help, he was suddenly bashful.

"I just need to pin the hem on this one, honey. Then, you're off duty. Ok?"

"Ok."

"Thanks, honey. I really appreciate your help. Now, step into the gown and I'll help you get it past the petticoats."

Paused let out a frustrated sound and pulled his mother's peach colored, silky robe off of his shoulders revealing the pretty, padded, lace covered bra beneath. As he dropped the robe to a chair, the full, fluffy petticoats appeared as did his stocking feet and the simple, twoinch pumps underneath.

The image of her son dressed in this manner always brought a smile to her face. At five-foot-four inches tall, one-hundred-and-seventeen pounds, Paul was even a bit small for a girl of his age. It never seemed to bother him, though.

"Ok, young lady," his mother teased, eliciting an irritated grunt from her son, "step into the gown for me."

For the last two weekends, Paul had been doing this over and over and over again, but it still gave him shivers when his mother pulled the silky material onto his shoulders and zipped up the back of the Victorian-style gowns.

"Ugg," she complained, "I wish that you'd let me shave your arm pits while we're doing this. This beautiful dress, your lovely body and those hairy pits just do not go together."

"Yeah, not happening, mom. I don't understand why your making all of the bridesmaids dresses, anyway. I mean Kieth is your son. Shouldn't Abby's mom be making the gowns."

"I'm doing it because I have a great deal of experience sewing dresses, you know that. Besides, Abby's parents are struggling to pay for the reception as is. Your father, God rest his soul, left us very well off and I am happy to contribute to the wedding in any way I can."

"I know, but, mom, you volunteered to make dresses for all the bridesmaids and half of my cousins. That's like twenty dresses."

"Oh, stop exaggerating," she chided as she straightened the gown on his shoulders and over the petticoats, "its only twelve dresses and you only have to help me with eight. And, believe me, I am grateful to have your help. That's why I'm going to pay for your Driver's Ed classes so you can get your learner's permit. That's our deal, so, no more complaining. Now, step up onto the platform so I can pin up the hem."

She held out her hand to support Paul, while he used his other hand to hold up the skirts and petticoats to maneuver himself up the step and onto the sixteen inch high, carpeted box that his mother had asked a neighbor to make for her.

Just as she knelt to begin her work, her cell phone rang in the kitchen. "Oh, for crying out loud," she complained as she stood again and headed to the other room. "That damned phone is a curse."

"Hello?" Paul could hear his mom a room away. "Yes, this is Lilly Rooney. Oh, yes, thank you for calling back. I need to reserve the hall for a wedding rehearsal dinner in June..."

He sighed. This would take awhile. Stuck on the platform as he was, there wasn't much he could do except stand there.

He brushed his hands across the skirt of the dress. It sure felt different than brushing the front of a pair of pants. It was soft and smooth, but still somewhat stiff. Elegant in a way that he could not imagine men's clothing ever being. He felt awkward and strange in any of the dresses that his mom was making, but after wearing the panties, petticoats, stockings, shoes, bra and his mom's robe for the last six hours, he was getting used to the sensations and there were aspects of his ordeal that he actually enjoyed.

He ran his hands over the breasts that his padded bra created and he felt even weirder. It was like touching Lori's breasts, but not. They were on HIM and as the day had progressed and even the bra had become comfortable and second nature, he was kind of enjoying having breasts of his own.

It was weird.

When this all began two weeks ago. Then, it was just, "Paulie, I just need you to try on this part of the dress. You're the same size as Mary and several of the other girls, and I have to make sure it's right. I don't have time to keep changing the dress form..."

Last week, it was, "I bought some more undergarments that will shape you more like Betsy, but I'll pay for your Driver's Ed if you give me a few hours each weekend till I'm done..."

Today was actually Friday, but Paul had the day off from school so the teachers could all attend a system-wide meeting, so his mom had cleared her schedule so she could get an extra day of sewing in. 'Lucky me,' Paul had thought. He figured that the day would be a big pain in the butt of sitting around in a bra, but instead, his mom had presented him with the shoes and petticoats. The stockings were added because the shoes didn't fit quite right without them. By the time his mom had gotten him into everything she said that it would just be easier for him to just keep everything on as she worked.

She gave him her long, silk robe to cover himself. It was comfortable enough, but it smelled like his mom's body wash, makeup and hairspray.

It was weird, too, but things normalized as the day went on and he got used to it.

His mother stayed in the kitchen talking on the phone.

Still bored and trapped on his pedestal, he fluffed the skirts and watched them settle. He caught a glimpse of himself in the darkened glass of the China cabinet that was on the wall to his left. Huh. He really did look like a girl from the neck down.

He reached up and pulled the hair tie from the man-bun that he wore on top of his head and he shook his hair free. Typically, it was always in a bun unless he was washing it. When freed, it fell to just below his collar, only the dress had no collar, so it tickled his upper back as it settled. He used his hands to comb it out and shook it to have it fall more naturally and he looked at himself in the China cabinet glass. Huh. A very plain girl looked back at him.

He played with the skirts a little more and watched the girl in his reflection. Huh.

He didn't look all that bad.

It was a weirder and weirder and the fact that he felt his penis growing in his panties was also weird and a little disturbing.

He wondered what it would feel like to go whole hog and try some makeup and maybe even have his ears pierced and his hair done. That would feel nice, right? Maybe have his nails done nicely. That looked very relaxing. Maybe...

"Ahem," his mother fake-coughed from the doorway as she watched her son flouncing his skirts with his hair down.

Paul froze and his face reddened.

His mom laughed and crossed the room to him as she picked up her pincushion and began working on the hem. "Don't worry, honey. You're just reacting to the costume. If I'd left you standing here in a cowboy outfit, I probably would have caught you playing with your six-shooters, but I left you wearing a Victorian dress, so you were playing with your dress. It's perfectly natural."

Paul breathed and relaxed as his mom worked around his feet. She was quick and nimble and soon had finished pinning the hem.

"Here," she said to Paul, "take my hand and I'll help you down."

Once he was on the floor, she fussed with the shoulders of the dress and assessed her son. Paul was very bright and had lots of friends - although most of them were girls. He was never going to be tall, broad and handsome like his father had been or his brother was. Keith, who was ten years older than Paul and had been taking care of himself for nearly a decade, now, was nearly six-foot-three inches tall and was the spit and image of his father. Paul was frail and delicate and was, she had just realized, the spit and image of her own mother.

She laughed gently at that realization as she played with his hair.

"What?"

"Oh, nothing," she smiled at the boy. "I just realized how much you look like your grandmother. Come with me for a moment."

She led him to the hallway mirror and and stood beside him as they stared at what really did look like a young version of his grandmother.

"Here," his mother reached behind her neck and unclasped a small silver necklace with a blue stone hanging in a pendant. She came behind him and connected the clasp behind him, then adjusted his hair as she looked over his shoulder. "That was your grandma's. Isn't it lovely?"

Paul looked at the pendent which made his already feminine looking bosom even more so. He began to feel flushed - a little excited and very scared by his reflection and the fact that he felt excited at all.

Lilly watched her son and wondered what he was thinking. Eighteen and still so small. Kieth was already over six feet tall at this age. Keith's teenaged years were consumed by sports, Boy Scouts, girls and cars. He was strong and independent and off on his own before he was out of high school. Paul was more interested books, drama club, art class and movies. Keith was her big guy. Paul was just... her baby.

"Do you like the way you look, honey?"

Paul shook off his reverie. "Mom, I need to go shower. Lori will be here in fifteen minutes. Can you help me get changed?"

"Sure." She smiled at his behavior as she lead him up the stairs to the master bathroom off of her bedroom. "Use the walk-in shower in my bathroom. It'll be easier than the tub in yours."

She pulled down the delicate zipper in the back of the dress and lowered it to the floor for him. He stepped out of it and she stepped into the bedroom to lay it carefully on her bed. When she returned, she had him turn and she undid the waist of his petticoats. Again he stepped out and again she laid it on the bed.

When she return, he was had taken off his shoes and he was struggling with the rear hooks and eyes on his bra.

"Here, I'll get that, sweetheart."

"Thanks, mom."

Lilly smiled, "That's ok, baby. Girls need help with things like this. That's why mothers and daughters stay so close."

Paul blushed a bet deeper and let his mom take off the bra and she helped him with his stockings.

"I think you can handle the panties by yourself, though, can't you?" she asked.

"Yeah, mom. Thanks."

Just then, the doorbell rang.

"Shoot, mom, it's Lori. She's early and I'm not ready."

"Don't worry, honey. You just take your shower and I'll entertain Lori." His mother turned him towards the shower and patted his pantied bottom. "Go on, now. Be quick."

As he showered he noticed three things.

First, his grandmother's pendent still hung from his neck. He tried to open the latch, but couldn't quite do it. Oh, well, he'd deal with it later

Second, he noticed that, after wearing a bra for six-hours, his chest seemed to have an outline of the bra imprinted on him, giving him a hint of breasts. He didn't know quite what to make of that, but time was running short, he'd just have to see if the outline faded on its own.

Third, his mother's soaps and shampoos were all floral scented. Oh, so what. The smell would fade in a few minutes. He didn't have time to run down to his tub. Besides, he was already soaking wet.

He showered and dried himself quickly. Then, naked, of course, he tiptoed to his room. He could hear Lori and his mom talking downstairs.

"Oh, Mrs Rooney, it's beautiful!" Lori was gushing. "You are such a talented woman..."

Paul ducked into his room and dashed to the closet where he grabbed a pair of chinos and a checked, button-down shirt. He threw them on his bed, then grabbed a pair of socks and a tee shirt from his drawers. As he searched for a pair of underpants, he found nothing but an empty drawer.

"Shit," whispered as he went to the door to call down for his mother to look for a clean pair in the laundry room.

When he reached the railing he could, once again, hear Lori and his mother talking. "Oh, I love how deep the color is. It just shines. I can't believe you found something this elegant in a fabric store..."

"Damn," he whispered, again and ran to the hamper in his bathroom.

Empty. Mom must have put the laundry in the washer this morning.

The only solution was to go commando, or...

On top of his dresser was a package of panties his mother had bought for him to wear when he was acting as her dress model. He'd worn the white ones earlier today, but there were five other colors in there. What the heck, they were only cotton panties. No big deal, right?

The only solid color pair remaining was pink, so he grabbed a purple and white pair and pulled them up his legs, careful position his moderately sized penis correctly where a pouch should have been.

There. Problem solved.

He grabbed his other clothes and threw them on, wrapped his wet, floral scented hair up into a bun and ran downstairs to Lori and his mom.

"Hey, babe," Lori smiled as he entered. "Your mom was showing me the material she picked up for my prom dress. Have you seen it?"

Paul said that he had and he knew that she'd like it.

Lori was wearing her favorite cowgirl boots tonight. They were red and had a very high heel. Paul loved the way the she looked in them, but didn't like her wearing them on dates. She was three and a half inches taller than him in bare feet. With the heels, she was five or six inches taller. They did make her butt look good, though!

After a moment of conversation about the material, Paul tried to usher Lori out the door quickly so that he could be alone with her.

"Paul Anthony Rooney," his mother's voice stopped him in his tracks. If she was using his middle name, he was in some kind of trouble, but he couldn't, for the life of him, figure out what he'd done.

"What did I do?"

"It's what you didn't do," his mother's scolding voice was cartoonish enough for him to know that he wasn't in any serious trouble.

"Look at this beautiful young woman who you are accompanying tonight. She took the time to look perfect from head to toe before driving over here to pick you up and you're headed out the door with wet hair wrapped up into a ratty bun."

Paul looked from his mother to his smiling girlfriend who raised her eyebrows and said, "She's right. You're hair is kind of stringy and wet right now."

"Oh, for crying out loud," he sighed. "You both know that I let it dry for a while, then redo my bun."

"Not good enough," his mother scolded. "By the time you get to The Dairy Bar, your hair will still be wet. It'll look terrible for hours. Now, upstairs with you and dry it with my blow dryer."

"Mom," he laughed, "I think that the last time that my hair was dried by a hair dryer was four or five years ago when we were late for Aunt July's wedding. I don't even know how to use it. Besides, we're running late. It'll dry."

He took Lori by the arm, but she shook him off with a big, conspiratorial smile. "Oh, we're not in THAT big of a hurry and I'd kind of like your hair to look nicer than it does. You know, your mom is right. I took the time to look nice for you - you should do the same for me."

Paul shook his head. "Come on, mom... Lori... like I said, I don't even know how to use a blow dryer..."

"No, problem," his mother cut him off, "we'll teach you. Come on, Lori, let's go to my bathroom and we'll teach my son how to make himself presentable."

In spite of his protests, he was led upstairs to his mother's room and into the lavatory where he was told to sit on the toilet seat and let his hair out so that it could be dried.

As his mother plugged in the drier and took out a large, round brush, Lori spotted the bridesmaid's dress on the bed and said, "Oh, Mrs. Rooney, this is gorgeous! Is this for the wedding?"

Lilly peeked out of the lavatory and smiled at Lori as she held up the dress. She smiled at the younger woman's romantic reaction to the elaborate garment. "It is, dear. I just pinned the hem. Isn't it coming well? I still need to add all of the lace, and there's a lot of it on each dress, and there is a decorative flower pattern fits right at the bottom of the bust line. They will be beautiful when I'm done."

"Oh, and what a beautiful petticoat. Oh, I hope that my wedding will be this beautiful."

"It will, dear, I'm sure. Come on in here so we can talk while I deal with this mop of hair that you're dating."

As Lilly went to work on her son, Lori asked questions about the colors that the bridesmaids were wearing and the venue where it would all take place. The hair dryer was loud and hot, so Paul only caught snippets of the conversation.

"Honestly," his mom said with sincere feeling, "if I didn't have to work for a living, I would have loved to have made the bridal gown, too, but that's a pretty huge job and I never did anything like that, before."

'Thank God she's not making the bridal gown!' Paul thought as his hair was pulled so hard that he thought that it might get pulled out.

"Well," his mother smiled as the dryer whirred to a stop, "that came out better than I expected."

"Yeah," Lori agreed. "You look great, babe! Leave it down, tonight. I like it."

Paul turned and looked in the mirror, surprised by what he saw. Typically, he just pulled his hair back and wound it into a bun. This time, though, there was a neat part down the middle and his hair looked healthy and hung nicely around his face and neck. It even looked just a little lighter due to being fluffed the way that it was.

"Wow. I look so different."

"Do you like it, because I really like it!" Lori was beaming.

"I guess... Sure, I like it, fine." Paul was very surprised that it looked so good. He never really looked all that good - just, kinda artsy.

"Wait, just a minute." Lilly had an idea. "Let me show you something amazing."

She ran to her bureau and pulled out a photo album, thumbing through to find a specific picture.

"Here, look at this! Isn't it uncanny!?"

Paul and Lori looked at the picture and, truly, it was uncanny! The person in the black and white picture was wearing a checked, button down shirt and tan pants, very similar to Paul's. The person also sported a very similar hair cut and, and this was the uncanny part, the image had Paul's face! If it were not for the feminine smile, light makeup and obvious breasts beneath the shirt, even Paul would have sworn that it was a picture of him.

"Oh, my God!" Lori whispered. "Who is that?"

"That's my mother," Lilly beamed! "Just a few minutes ago, when I was helping Paulie take off.... Well, never mind that.... Anyway, I just said to Paulie that he was the spit and image of my mother, but this is getting a little freaky!"

For his part, Paul was relieved that his mother had not blurted out anything about him wearing a dress, but he was bewildered by the picture.

"Wow," Lori put her arm around his shoulder and shook him
affectionately, "your grandma was a babe and you look just like her! How cool is that, babe!?"

Paul wasn't sure how 'cool' it was, but it was a strange turn of events. He loved his grandmother and always enjoyed it when she was with them, but this was downright odd. They looked identical.

"Isn't it amazing, honey?" Lilly was truly thrilled by the likeness. "And you know what's even stranger, Lori? This is the house that my mother grew up in. We brought it when my grandfather passed away. The room that Paulie sleeps in, now, is the same room that his grandma used to sleep in when she was his age."

"Wow!" Lori laughed. "If your grandma weren't still alive, I'd swear that you were her reincarnated!"

"Yeah... haha..." Paul was getting concerned about all of these coincidences. It was as if life was making him feel inadequate as a guy. He was ok with being on the short side - usually - but having been in petticoats all day, then Lori wear those damned spectator-boots so he felt tiny and now this! His sense of masculinity was waning.

"When was this picture taken, Mrs Rooney?"

Lilly took the picture out and look at the back of it. "Let's see that was fifty five years ago and mom is seventy three, now so..."

"Oh, my God, babe!" Lori shrieked. "She was eighteen - the same age as you!!! You really are twins! Nearly identical!"

Paul had had enough of this talk. "Alright! Alright! It's a pretty weird coincidence, but that's all it is - a coincidence. So, what? I look like
my grandma? Big deal. Lots of kids look like their grandparents. I think we've talked about this enough. Come on, Lori, let's go to The Dairy Bar
and have some dinner. I'm starving."

"Ok, babe. I'm sorry. I didn't mean to tease, but you have to admit... it is pretty amazing."

"Ok, you two," Lilly laughed as Paul pulled his girlfriend towards the door, petulantly. "Be good! Be careful! Come home safely!"

"Good bye, Mrs Rooney! See you later!" Lori hollered back as the door closed, maybe just a little too forcefully, behind the two teenagers.

The Dairy Bar was crowded, as it usually was on a Friday evening. Since most sophomores, like Paul, couldn't drive yet, at least not without an adult, most of the kids were seniors. Paul was one of the few boys with an older girlfriend, but there were a few sophomore and junior girls there who were dating older boys.

Lori found a spot right by the front door. They got out and went in to place their standard order -two burgers, one small fry to split, a coke for Lori and an iced tea for Paul, with a malted chocolate milk shake to share for dessert. They greeted those kids with whom they were familiar and he chatted with a group of girls about an AP English Lit project that was due on Monday before getting in line at the counter.

"$23.88, please," the cashier said.

Paul reached for his wallet and felt just an empty pocket. 'Shit,' he thought as he realized that in his rush to get out of the house, he'd left his wallet on his bureau.

Lori saw his panic and stepped forward, opened her purse and pulled out $30.00. "Here you go," she said as she handed the cashier the bills. "Keep the change."

She smiled at her diminutive boyfriend as she threw her arm around his shoulder, "Pretty smooth way of not paying the bill, stud."

"I'm sorry, Lori. I guess I was in such a rush that..."

"Lori! Rooney! Over here!" It was Lori's friend, Beth. Until they started dating, Paul had never seen Lori without Beth. She always called Paul "Rooney" for some reason. He didn't mind. It sounded kind of tough.

"Wow, Rooney! Your hair looks cool tonight! New look for you?" Beth asked as they took their seats.

Paul smirked and shrugged as Lori grinned. "It's cute, right? I like it better than his boy-bun."

"It is cute, Rooney." Suddenly, Beth reached across the table and reached into Paul's shirt. "Hey, what's that?"

Paul saw the pendent in Beth's hand and he nearly died. He'd forgotten to take it off! How could he have been so stupid!?

"Aww, that's really pretty, babe," Lori was admiring the jewelry. "Where did you get that?"

"Umm... well, it was my grandmother's and she gave it to my mother and... well, earlier today my mom got it in to her head that I looked like... well, she usually wears it, but she put it on me as a gag and..."

Lori laughed. "Oh, Beth, you wouldn't believe it, but when Paulie and I were getting ready to leave, well, his hair was all wet and his mother wouldn't let him leave until his hair was dry, so she..."

Paul melted into his chair as Lori brought Beth up to speed on the Paul/grandmother story.

Mercifully, the loudspeaker announced their number and Paul jumped up to get the food. When he returned, the girls were giggling and Paul was sure that it was directed at him until he realized that they were watching a couple of little kids who were playing outside the window. The conversation for the evening never returned to Paul's jewelry or his grandmother.

At 9:30, they pulled out and went for a ride along the coast until they came to an inlet with a parking lot. They sat, Paul moved over and nestled in the crook of Lori's arm, and looked at the water and chatted for a while until Lori pulled him close and planted a long, luxurious kiss on his lips. He smiled as they parted and Lori immediately leaned in again and this time her tongue plunged deeply into Paul's surprised mouth. He accepted her tongue as deeply as he could as his hand caressed her the side of her breast.

Lori pulled Paul as close as the stick shift between them would allow. Her tongue searched deeper and deeper into his throat and he slipped his hand inside her bra, releasing her left breast from its bondage.

Soon, he was suckling on her nipple, tenderly biting it with his lips and teeth and she moaned in delight.

Soon, her left hand had undone the button on his chinos and her hand was caressing his organ through the soft cotton of his underpants. They had ended their dates this way several times and both loved to play with the other in this way.

As his penis became more turgid, she searched for the 'Y' front of his briefs to pull his member free, but she could not find the opening. As her hand went to slip beneath the waistband of his underwear, she noticed a difference. The band was smaller and gave way more freely and... what was that... was there lace around the elastic. What the hell was this!?

Suddenly, Lori stopped and pulled away from Paul.

"What?" he asked, confused and frustrated.

"Sit back by the door for a minute."

Paul did as he was told and Lori turned on the dome light.

"What's the matter?" Paul was concerned. Had he bitten her when he meant to nibble? What?

"Pull down your pants for me."

"Ok," Paul said as he started to comply, then realized why she'd stopped. "Umm... I can't."

"Why not?"

He remained silent and tried to think of something to say.

"Are you wearing panties, Paulie?" Her face was passive, well, maybe a little curious, but not angry.

"It's not what you think... I was just in a big rush and... all of my underwear was in the laundry, so..."

A smile crept across Lori's face. "Let me see them."

He pulled down his pants, revealing the purple and white stripped, obviously feminine, panties. He had not even noticed, until that moment, that there was a band of white lace around the waist and leg holes. Could this night get any more embarrassing?

"Cute," Lori grinned broadly. "I like it. Take off your shirt for me."

Paul did as he was told and soon he was seating in the passenger seat of Lori's car in just a pair of panties and a pretty pendent.

"Hmmm...." She hummed. "I like this look. Is there anything you want to tell me?"

"I'd rather not," Paul answered honestly.

"What are these marks?" She ran her hands along the traces of the bra straps and band that still remained. "Looks like a bra. I think you need to be honest with me, Paulie. Are you a transvestite or a transsexual or something? I mean, I'll love you regardless, but I need to know."

Paul broke down and told her how he'd been helping his mom with something private, leaving out the most embarrassing details about the petticoats and how pretty he thought he looked in the dress. He said that it wasn't what it looked like and he swore that it wasn't anything weird - he was just helping he mother.

When he was done, Lori told him how impressed she was that he'd help out his mom like he did, but her gaze remained focused on Paul's panties.

She leaned over and reached into his waistband, grabbed his equipment and pushed it down between his legs. When she pulled her hand out, he was smooth where a budge used to be.

She rubbed his smooth abdomen. "That's better. If you wear panties, they should look pretty. Your wiener messes up the front. I like it better this way."

"You're not mad?"

"Mad? No. I think it's sexy. Tell you what - if you wear panties for me again tomorrow, I'll make it worth your while. How would you like to have your first BJ?"

He smiled. "I'd like that."

"Then wear your prettiest panties for me and make sure that the front of your panties are smooth and pretty for me. Ok?"

Paul was very flushed. He was so enthralled by the idea of an actual blowjob that the strangeness of the request didn't even register with him. "Ok. I'll wear panties for you."

"Nice" her smile grew wider. "Let's get you home."

Saturday morning began with a nice breakfast with his mom. Turkey-Bacon with eggs and fresh fruit before Lilly suggested that Paul take a shower before she got him ready to hem another dress or two.

"Use my shower, honey, and use the conditioner after you shampoo. Just follow the instructions on the bottle."

Paul enjoyed the warm water and the massage feature on his mom's shower. He'd been in the shower for about fifteen minutes and was rinsing after his second application of conditioner out of his hair when he heard his mother enter the bathroom.

"Paulie, honey, I need to open the shower door. Turn your back to me if you want."

He did and Lilly opened the shower door. "Here, honey, cover yourself with this," she handed him a face cloth. "Now, hold up your arm for me."

"Mom, no!"

"Paulie, yes. I can't put those beautiful dresses on you with that ugly underarm hair sticking out at me. It'll grow back. Don't make this into a big thing. Just let me take care of it."

Paul sighed and shook his head. "Geez, mom, this is getting to be a bit much, don't you think?"

"No, honey, I don't. I asked for your help and you agreed to it, and that involves looking good in the clothes. So, please, let's just do this and get it over with."

Reluctantly, Paul raised his arm and his mother shaved away the little tufts of hair under his arms.

"Now, face me," she directed him and she made quick work of the few hairs that populated his chest.

Then she pulled a small stool to the side of the shower and told him to put a foot in her lap so she could take care of his legs.

'What the Hell?' He figured that there was no stopping her at this point and, like she said, why make a big thing out of something that would grow back in a few weeks.

"Now, that looks much better. Now shut off the water and lean over towards me." She wrapped his head in a towel, turban style, then instructed him, "Rub some of this body oil into your skin before you get out of the shower, put on a pair of panties and my robe and meet me in the kitchen."

When he arrived in the kitchen, Lilly guided him to a chair by the counter where there was a hair dryer, a brush and various other hair care tools. She removed the turban from his head and rubbed it to dry it a bit, then placed the towel on his shoulders, like a hairdresser's cape, before grabbing a brush and starting the process of preparing his hair.

"See, the conditioner makes it much easier to run a brush through your hair. No snarls, right?"

Paul nodded. She was right. His hair was, typically, a mess of knots and snarls. The brush seemed to pass through it easily, today.

"Did anyone comment on how nice your hair looked, last night, honey?"

"There were a few comments, alright. Lori's friend, Beth, teased me a little, but most people just kind of acknowledged it and moved on. No one made a big deal out of it, either way."

"Hmm. I'm surprised," Lilly had moved to the back of her son and was looking at the ends of his hair. "It looked so much nicer than usual."

Paul shrugged, but then sat up straighter as he heard the sound of scissors closing behind him. "Mom! What are you doing?"

"Oh, just relax. I'm just taking about a half an inch off of the end of your hair to get rid of the split ends and neaten it up for you. You liked how it looked yesterday, right? Well, this will make it look even nicer."

Paul breathed a frustrated sigh. "You know, mom, I think you're losing sight of the fact that I am actually your son. Don't let the panties fool you. I still have a penis down there."

Lilly delivered a well placed dope slap to the back of his head. "Don't be crass to me, Paulie. Listen, your hair has been driving me nuts for years and FINALLY it looked nice yesterday. Lori thought so, too. Let's build on that. As for the panties, well, we have a deal right? It won't last forever. Oh, and I noticed that your still wearing your grandma's pendent. I think that's sweet. Why don't you keep it?"

Paul had just gotten used to it being there and forgotten to ask for help to remove it. "Actually, the only reason it's still there is because I can't work the clasp by myself. Can you take it off for me?"

"Oh. I thought you liked it. It's very pretty and grandma will happy to know that someone is wearing it. You are her favorite grandchild, you know."

"That's just because I'm the youngest."

Another dope slap. "Stop it. You know that she dotes on you. Leave it on for now. It looks pretty with the gowns. We'll talk about talking it off
later."

After the split ends were removed, Lilly went to work with the blow dryer, taking her time this time. She worked it and worked it, occasionally spraying parts of his head with water to fix mistakes. It seemed to take forever and felt like it was burning his ears and drying out his eyes.

After a shower of hairspray for "just a little hold," Paul was told to stay where he was while Lilly helped to raise the stockings up his newly shaved legs. They did feel much nicer than yesterday, he had to admit. Then his shoes were added and he stepped into the petticoat which Lilly tied tightly behind him. Finally the bra was hooked in back, but then, instead of putting on his mother's robe, Lilly held open a light blue, checked shirt similar to the one he'd worn last night, but this one buttoned on the other side and had darts sewn into the front to accentuate a woman's figure.

"Mom..."

"Humor me. Just let me see something."

He put on the shirt and Lilly buttoned it up for him, then stood back to take a look at him. "Wow."

"I know. I look like grandma."

"No, honey. You ARE your grandmother at eighteen. I mean, I know that I said you were the spit and image, but I am wrong. Your really are your grandmother. Look in the hall mirror."

As Lilly picked up the counter, she heard a shriek from the hallway. "Mom! You... you flipped my hair under! I have grandma's actual hairdo from that photo!! Are you nuts!? I'm going out with Lori tonight! I can't go like this! Are you crazy?"

Lilly hurried to her son and rubbed his back to calm him down. "Honey, honey, honey. I just put the flip in to see how it would work. I'll comb it out before your date. Don't worry your pretty little head, you'll look fine tonight. I'm sorry. I should have asked before I did it."

He breathed again, a bit relieved.

"I'm sorry, honey. Tell you what. You can take off the shirt if you want and go play video games. I won't need you for an hour or so."

"Ok. Sorry I yelled I was just... you know... Anyway, I need to do some reading for AP Lit, so I'll be reading in the family room when you need me, ok."

"Ok, honey and I'm sorry, too."

Just shy of an hour later, Lilly walked into the family room to find Paul, still in the checked shirt with his feet curled up under the petticoats, tucked femininely into the corner of the couch with a book in his hand and cords from his ear buds hanging out of his softly flipped hair. He just made such a precious picture, that she took out her phone and took a picture of him. He never noticed.

She touched his shoulder to get his attention. "Paulie. I need you now."

"Ok, mom." He got up, managing the petticoats quite well, she noticed, put down his book and phone and followed her to the dining room.

"Here, honey. I need to do the soft rose colored one, now. Take off your blouse and I'll help you into it."

Paul rolled his eyes at the word 'blouse' but did as he was told.

The dress went on the same way that yesterday's did. Lilly zipped up the back for him, helped him onto the platform and knelt to pin the hem.

Paul noticed that a tall mirror on a stand had been placed in the dinning room about eight feet in front of his platform. There was no where else for him to look except at his reflection.

It wasn't so bad, though. It was very different, of course, but the dress was very pretty and it was fascinating to see how different he looked with just a few alterations. And when he thought about it, his mom was really quite an artist, making all these beautiful gowns. It was like when he molded clay, or painted. Start with nothing - end up with something amazing.

Lilly smiled as she spotted her son looking at his reflection. Paul was always a sweet, gentle boy, but all of this dressing and hair care seems to have taken that up a level. She didn't want to play games with his psyche, but she was enjoying having a pretend-daughter for as long as it lasted.

"You look very pretty, Paulie."

Paul shrugged nervously, but could not think of a thing to say. Finally, "I guess," came out as a whisper.

The hem was pinned, but rather than take the dress off of him immediately, Lilly stood and looked in the mirror with her son. The platform and shoes made him almost half a head taller than her. That was unusual. She raised her arm, put her it around his waist and leaned her head on his shoulder. "You know, it couldn't be possible for me to love anyone as much as I love you and Keith, but part of me always wished that I had a daughter. Thank you for indulging me. I'm really looking forward to spending the next few weekends getting to know the new, feminine person that you are when you're dressed like this. I hope you're having fun, too."

He thought back to last night and how turned on Lori was when she saw his panties. 'What is it with women wanting men in pretty clothes? And I thought I was weird!' he thought.

"I wish your grandma could see how much you look like her. She'd love it."

"Oh, I don't know," Paul chuckled. "She's a bit old fashioned about boys and girls."

"Nonsense, I'd like to..."

Their quiet chat was interrupted by a woman's voice calling as she swung open the kitchen door, "Hi, mom! Are you here? Paulie?"

It was Keith's fiancé, Abby. As one of the family, she just entered without knocking.

"Mom...!" The panic in Paul's eyes spoke volumes .

There was no where to go. The kitchen was twelve feet away. She was headed into the dinning room and neither of them could get to the door before Abby did.

"I brought the lace material you wanted, it was delivered... oh! I'm sorry," she spotted the woman modeling the dress and stopped yelling so loudly. "Hi, mom, here it is." She came around to the front of the pedestal and extended her right hand to the model, "Hi, I'm Abby, the bride. Thank you for helping out, the dresses are just... PAULIE!?!?!?"

Paul's entire body turned blood red as he tried to hide, but was unable to get down.

"Yes, it's Paul, but..." Lilly tried explain and calm everyone down.

"Mom, Paulie's in a dress... a gown... his hair... mom! What's all this about!?"

"Now, that's enough, just stop right there!" Lilly raised her voice to gain control. "Paul is my model - my PAID model, by the way - and he has been allowing me to have a little fun at his expense. Now, just stop the dramatics and calm down and whatever you do, don't tell his brother about this - he's only doing this because he loves you and and Keith."

"Oh," Abby sputtered. "I see. Well, umm... Paulie... thank you for your help and, mom, thank you for explaining." She evaluated her soon to be brother in-law more closely and smiled. "You don't look half bad, there, Paulie. I wonder what your girlfriend would think of you."

As if on cue, another woman's voice sounded from the doorway. "Could someone explain it to me? Because I am curious as to why my boyfriend is wearing a Cinderella gown."

Paul turned on the pedestal and wished that he could just melt into the petticoats and disappear. Not only was Lori standing there with a shocked smirk on her face, Beth was there, too.

"Looking pretty good there, Rooney." Beth joked at his expense. "So, Lori, what kind of a tux are you wearing to the prom."

"Oh, shut up and leave him alone," Lori scolded her friend. "I'm sure there's an explanation for all this and, even if there's not, damn, baby, you are a hot looking girl - and no make up. I like the flipped hair, too."

"Alright, Alright, Alright!" Lilly took charge. "Everyone's had their fun, now, out into the kitchen with the lot of you. Let me help Paulie down and we'll be there in a moment to explain everything. Shoo, now, all of you."

They left and Lilly shut the door before helping Paul down. She hadn't noticed the tears that coated his face.

"Oh, baby, I'm sorry. I didn't think that something like that would happen. It'll be fine, you'll see."

Paul couldn't help it. When his feet were on the floor, he buried his head in his mother's shoulder, held her tightly and sobbed
uncontrollably.

"It's over, mom, it's over. She's never going to go out with me again... Lori and Beth will tell everyone... I might as well be dead, mommy. My life is over."

Lilly couldn't help but chuckle just a bit as she rubbed his back. " Oh, baby, baby. Nothing's over. We'll explain it all and everyone will laugh."

He could barely breath, let alone talk, through the gasps and sobs. "No... I wish I was dead. My life is over."

Minutes of this fear and hysteria passed until there was a knock on the door. Lilly opened the door enough to see Lori's face.

"Can I speak to him for a few minutes, alone?" Lori asked.

Lilly nodded and opened the door wider to let the younger woman in.

"Be gentle," she whispered. "He's very upset."

Lori whispered back, "I will. Umm, can we have like fifteen minutes or so. I need to make sure that he knows that I'm fine with this."

Lori closed the door behind his mother and quietly locked it. Then she put her arms around Paul and hugged him close. He calmed down with the feel of her touch and the smell of her and her voice and her... everything. He'd honestly thought that he'd lost her. Thank God she was back.

"Oh, baby," she whispered, "why are you crying? Everything is just fine."

"I... I..." He still gasped as he tried to gain control of himself. "I thought that you'd leave me after seeing me like... this."

"Are you kidding me? As much as I loved you yesterday, I love you even more, now. Look at how cute you look."

Paul pulled back and smiled, looked at the gown he was wearing, fluffed it a bit and shrugged. "Cute is not exactly what I was going for."

Lori played with his hair for a moment. "I love this look for your hair. Was it your idea?"

"What?" Paul was incredulous. "Of course not. I showered this morning and mom wanted to trim my split ends, then dry my hair. I had no idea that she'd done this to me till I looked in the mirror. She was going to fix it before anyone saw me, but that was a giant fail, wasn't it?"

"Well, I think it's adorable on you."

She touched the exposed skin on his neck, shoulders and chest. "You're smooth, too. Did your mom shave you?"

He nodded.

"Your legs, too."

He nodded and his blush deepened.

"Really? I want to see."

She knelt and raised the skirt of the gown. "Oh, my, Oh, my," she whispered. "Look at all those pretty petticoats."

When she'd reached his legs, she said, a bit louder, "Oh, my, Oh, my. Stockings. And heels," she gave a sharp, exaggerated intake of air, buried in his petticoats, "and panties! Yay!"

Paul giggled, but when he felt her pull down his panties, he gasped for real.

When her tongue touched the tip of his penis, he was in heaven. He'd never felt anything this wonderful before and Lori had completely disappeared. He could see no trace of her beneath his voluminous gown, but he could feel her touching him. Playing with him. Kissing him. Suckling on him.

It was amazing.

He grasped the silken skirts of the gown and his head rolled back, allowing his curled hair to swing freely, femininely beneath his lolling head. His hips began to buck and his breathing began to increase in tempo. He could feel a bead of sweat run down between the cups of his bra.

His entire manhood was being consumed amidst his feminine clothing. When he thrust forward, or pulled back, he remained entirely in her mouth, but the friction created by the movement combined with the suckling of Lori's mouth and throat made everything bubble up faster and faster. He was either going to cum or pass out pretty soon.

When he came, it was powerful and violent and gentle and sweet, all at once. He let go torrents of seed into her mouth while stifling his need to scream at the top of his lungs and just let his eyes close and his mouth hang open until Lori climbed out of the tent of fabric and took him in her strong arms.

His eyes rolled as they opened and gradually focused on his girlfriend.

"Wow," he whispered.

Her smile turned to a laugh. "You're adorable. Come on, your mom is worried."

"...and then you all showed up at once. I know it seemed odd, it really was all explainable." Lilly had the photo album out on the kitchen table, opened to the picture of her mother in the checked shirt. They were all seated around the table drinking tea and laughing at the strangeness of the situation.

Paul had taken off the rose-colored gown and had put the checked shirt his mom had given that morning back on. The tailored nature of the shirt did accentuate the line of the padded bra beneath, but no one seemed to mind. Below the shirt, his petticoats exploded into a heap of femininity, but, again, no one seemed to mind.

"Well," Lori smiled, "I, for one, am glad that I got to see the 'new you' and you had better believe that I'll be back to see more of you over the next few weeks, until the dresses are done."

"Actually, I'm glad you all saw Paulie, too, because I've been trying to bring up something all day and I couldn't quite get the words out."

Everyone waited for Lilly's thoughts to continue as she flipped through the album of photos. "Here, look at this photo of my mother."

She showed them a picture, this time in color, of a young woman, who looked remarkably like Paul, wearing a knee lengthen, scooped collared, three quarter length sleeved, lace covered, white dress standing in front of a flowering bush that was still very much alive in their own back yard.

"Aww, she looks so young and beautiful there," Abby gazed at the picture. The timelessly elegant dress made the young woman look more mature, but still virginal and nearly goddess-like. "When was this taken?"

"See, that's the thing. After Paulie left last night, I took out this album and looked all these pictures of my mom. This was taken fifty-five years ago next Saturday when mom went to her debutant debut at the country club. All the eighteen year old daughters of the members would dress up and be 'presented' as women for the first time. It used to be a big deal."

"Huh," grunted Beth.

"Yeah," Lori continued her thought for her, "sounds pretty primitive to me. 'Here's my daughter. She's ready for a mate. Come get her.' You know what I mean."

They all chuckled at that and Lilly said, "I do, but it was pretty common for affluent families back then to have their daughters participate in these events. The newspapers took their pictures and wrote about them. It was a big deal."

"She looks happy in the picture," Paul was more taken by the joy on his grandmother's face than anything else. She still smiled like that when the family was all together.

"She was. She talks about this night a lot. She met my dad that night. They danced, they laughed, they fell in love, and they got married five years later when Dad finished college. It truly was her first night of womanhood."

There was a general sigh of approval for the romance of the evening from the women and Paul.

"Which brings me to my idea..." Lilly's smile was Cheshire in nature. She had something big planned.

"See, I have that dress in storage. It was here when we moved in, so I brought it to the cleaners and had them store it correctly in case I ever had a daughter who may fit into it and... well, now, I kind of do... and, since next weekend is the fifty-fifth anniversary of her debutant debut, it seems like it would be the perfect time to recreate this picture for mom."

"Mom..." Knowing his mother, Paul was already wary of where this was headed, but Lori cut off his objection.

"Oh, what a great idea!!! You could have Paul dress exactly like your mom was, hair, makeup, jewelry, everything, and retake the photo by the bush in the back yard! I love it!"

"That's it, exactly!" Lilly beamed at the enthusiasm from Paul's girlfriend.

"Mom..."

"Oh, mom," Abby cut him off this time, "grandma would adore that, I'm sure of it. What a great idea!"

"Mom, I don't know if grandma would appreciate her grandson all dolled up in her old clothes."

"Oh, don't be a stick in the mud, babe," Lori dismissed his concerns as she looked more closely at the photo. "He'll need an older shade of red for his lipstick and these pearl earrings are pretty distinctive. We'll have to find something similar."

"No, no, I have those in my jewelry box. Mom gave them to me on my wedding day. They are for pierced ears, though..." Lilly threw in, but Abby came to the rescue.

"They sell adaptors for unpierced ears..."

"... or he could just get his pierced..." Beth offered.

Paul felt as if he was in the midst of a tornado with words that seemed intent on destroying him swirling around him. Every 'but,' 'maybe' or 'I don't think' disappeared in the storm of women's voices.

Finally, Lilly, looked at Paul and smiled. She was thrilled by the amount of support coming from the women in the room. "So, Paulie, what do you think? Will you do this one more little thing for your mom and your grandma?"

"And for me, too, babe," Lori took his hand in hers and held it tightly. "It's going to be so much fun."

"You're already doing so much for me, Paulie," Abby smiled, "helping out with all the bridesmaids dresses and all, but knowing grandma the way that I do, I'm know that she'd adore a picture of her grand-baby, as she calls you, paying tribute to her like this."

Beth was uncharacteristically quiet as the final arguments went round the table.

How about you, Beth? What do you think?" Paul asked.

"I think you should do it, Rooney. Not for any particular reason, I just want to help dress you up."

That brought laughter from the others.

"I don't know, mom. I mean, I'd have to go out of the house and all... I'd feel kind of stupid, you know?"

"No, I don't know, Paulie. What's stupid about doing something nice for your grandmother. She does nice things for you all the time."

"Do it, babe" Lori said, then squeezed his hand to get him to look at her. She nodded her encouragement. She winked and smiled sexily. "Come on, babe, do it."

Paul breathed a heavy sigh. "Ok, I'll do it, but you'd better make me look like a real girl. I don't want to look like a joke when we take the picture."

They all applauded him.

"Welcome to The Girls' Club, Rooney," Beth teased. "You've got a big week ahead of you!"

After lunch, Paul went back to his book and Music, hoping to keep his mind off of the week ahead. Part of him was scared to wear the clothes and part of him was excited. The biggest problem was the fact that he was excited scared him more than wearing the dress.

Lilly went back to preparing another dress.

Abby went off for a bridal gown fitting.

Beth and Lori went to the dry cleaners to get grandma's dress and do some other shopping. Their playful offer for Paul to join them was treated with a sarcastic, "No, thank you," from Paul.

By the time dinner had rolled around, Paul had been a dress form three more times and had finished his AP Lit homework. Still wearing the checked shirt and petticoats, Paul joined his mom at the table at 5:30 for a typical Saturday evening meal - tuna sandwiches and fruit salad.

"So, what are you and Lori doing tonight, honey," Lilly made small talk.

He shrugged and finished his mouthful of food. "I don't know. I think we're hanging out here and watching some Netflix or a dvd. Is that ok?"

"Sure. You know that Lori is always welcome here. I have to go over to Keith and Abby's for a few hours, though. I'm getting together with Abby's parents to go over things for the wedding. You guys will be ok alone here, won't you?"

Paul nodded.

"Now, be careful and behave yourselves while I'm gone. No alcohol, drugs or sex, right?"

It was a usual warning from his mother and he chuckled. It was kind of her fault that he'd gotten his first blowjob earlier today and now she was telling him 'no sex.' Well, that was as far as things had ever gotten anyway. Probably no harm in that, so he kidded his mom back, "Don't worry mom. I won't make you a grandmother for a long time, yet."

"Good," She kidded back, "because I'd have a heck of time explaining how you got pregnant."

"Hey! That's not funny!" He waved her off with a gesture that was decidedly more girlish than usual. Lilly wondered if he was teasing, but decided it was better not to ask.

"Anyway," Paul continued, "Lori will be over in about an hour and a half, so, after supper, if you wouldn't mind helping me to get changed and maybe straighten my hair before she gets here, I'd really..."

"Knock, Knock!" Lori called in through the screen door, then she pulled it open and came right in. She was carrying several shopping bags and a garment bag with the name of the local dry cleaners' printed on it.

"Lori!" Paul accepted a kiss on his cheek. "You're early."

"I know, but I had all of this stuff and, to tell you the truth, I wanted to get here before you had a chance to get changed. I'm hoping that we might have a little fun with some things that I bought for you."

Paul's mouth hung open as his mother took the garment bag and said, "Oh, how sweet! I wish I could stay to see what you got, but I need to get to
Keith's. Here, let me take the garment bag, I'm dying to see the dress. Paulie, will you clear the table for me, dear?"

She pulled the garment bag to the side and looked at the dress, which looked as if it had just been stored away yesterday. The material was bright and clean and freshly pressed. “Oh,” Lilly put one hand to her heart as she looked at the beautiful dress. “It’s just perfect! Oh, I wish we had time to have you try it on now, Paulie, but I have to get going. Tomorrow, I’ll see if I can find a shorter petticoat to go with this and I’ll check all the seams to be sure that the thread is still strong before you put it on. Oh! I’m so excited!”

She skipped into the dinning room with the dress and hung it up before heading upstairs to get ready to leave.

Paul stood to carry dishes to the sink, but Lori stopped him. “Come here, beautiful. I want a kiss from my girly little guy.”

He laughed as she planted a kiss on his lips, but when they broke the kiss he said, “Hey, lay off the ‘girly’ stuff, ok. This is weird enough.”

“Oh, you’re right. I’m sorry. I’m looking at my boyfriend while he’s wearing panties, petticoats, stockings a bra, high heels and a pretty little blouse, his hair is flipped up like that girl on an old TV show and he’s got a pretty little necklace hanging in his cleavage. Why would I ever call him girly. I’m sorry.”

They laughed at that and she kissed him again. “I have to do the dishes, then, if you want, we could watch some Netflix.”

“Ok, honey, do the dishes, but I don’t foresee a lot of Netflix in our future. I do foresee a lot of silk and lace, though, so hurry up.” She swatted his pantied and petticoated butt as he walked away with his hands full.

“Don’t be so fresh,”he called back to her.

“Oh, you two,” Lilly said as she reentered the kitchen in a rush. “Now, look, I’m serious, you too are pretty frisky right now, but I’m warning you both – behave yourselves while I’m at Keith’s. We’re all having a good time and all, but I don’t want to have to be the bad guy and ruin all the fun. You both know how far ‘too far’ is, so stay away from that and be good.”

“Don’t worry, mom. We’ll be fine.”

“Don’t worry, Mrs Rooney. He’ll still be in his bra and panties when you return.”

“See that he is,” Lilly said with mock seriousness, but the kids knew that she really did expect them to behave. Heavy petting was ok, but that was it. If she knew about this morning’s blowjob, there’d be hell to pay.

“Bye, sweetheart,” she leaned in and kissed Paul’s cheek, careful not to let the dish water splash her, “love you.”

“Love you to mom. Drive safely”

And they were alone.

“Look at what I bought!” Lori squealed with delight. Out of the first bag she pulled several pretty, silky panties with lace panels on the front and sides. There were six of them. Then she pulled out a matching bra for each pair of panties. Each was as pretty and silky as its partnered panties.

She had shown him her shopping hauls before and those had included bras and panties before, but never so many at once.

“Aren’t they pretty?” She was delighted with them.

“Beautiful. I can’t wait to see you in them.”

She laughed, taken aback by this thickheadedness. “They aren’t for me, silly. They’re way to small for me. They’re for you.”

“For me!? Why would you buy me six bra and panty sets? I’m only dressing on the weekends and mom bought me plenty of panties. We have a washer and dryer, you know.”

“Correction, sweetheart,” Lori reached down and flounced his petticoats as she spoke, “you WERE only dressing on the weekends because it was all a big secret, but now that the secret is out, I want you to be pretty a lot more than just on the weekends. We’re just getting your wardrobe started, girlfriend, and by the time we’re done, you are going to be the cutest girl in town, I promise.”

“You don’t mean, like full time, do you? Like to school and stuff?”

“Not at first, babe, but, trust me, once you start to feel little and cute and feminine and SEXY, you’re going to want to feel it more and more and more and more.”

“But, Lori... I agreed to do this to help out and I’m glad that it didn’t freak you out, but you’re kinda freaking me out right now. I don’t want to be a girl. I want to be a guy and be with you.”

“Oh, don’t worry, baby,” she kissed him and fondled him through his blouse and padded bra, “you’ll always be my guy no mater how you dress, but you agreed to the photo thing on Saturday, so you’re going to need to be able to leave the house to prepare for that and it will be a lot easier for you to have your hair and nails done if you look like a girl, right. That’s at least a few evenings out this week. We’ll go someplace out of town where no one will know you, ok? Hmm, we should talk about your eyebrows a little, too.”

“Hey! My eyebrows are fine as is, thank you very much. Now, I agreed to do this for grandma and if that requires dressing a bit more convincingly than I’d like, then so be it, but that’s it. After Saturday, I go back to just weekends until the bridesmaids’ dresses are done.”

“And your cousins’ dresses, too,” Lori pulled him into a tight hug. She guided his arms up behind her neck and she started humming and swaying him from side to side. She liked how he felt, soft and curvy. The modest heels made him a tad taller, but they also seemed to elongate and thin him out a bit more than usual. His rump stuck out more than usual, too, and that’s where she rested her hands. The petticoats felt delicious.

For his part, Paul found the feel of the petticoats swaying around his legs distracting and exciting. “What, do you mean?” He asked.

“You said till the bridesmaids’ dresses are done, but your mom said that she needed you for some of you cousins dresses, too, so...”

“Ok, ok, you know what I meant.” He rested his head on her shoulder and listened to her humming while she guided him around the kitchen floor.

She kissed his neck as she hummed.

He loved it.

She was in charge. She could do whatever she wanted as long as she kept doing this with him forever.

“Tell me you love me,” she whispered and then resumed kissing his neck.

“I love you.” He whispered back.

“Tell me I’m beautiful.”

“You’re beautiful,” he giggled as she nibbled his ear.

They swayed some more and the soft layers of the petticoat tickled his legs.

“Now tell me that you don’t like how you feel when you’re dressed like this.” She looked him directly in his eyes.

He grinned and turned away.

“Come on, you pretty little thing. Tell me that you don’t like how you feel when you’re dressed like this.”

He heaved a heavy sigh. “Ok. I do, actually, like the way I feel when I’m dressed like this. It’s all so soft and... delicate. I just feels kinda nice.”

Lori smirked. “See, I told you, so. Come on, let’s have some fun.”

She began by untying the back of his petticoats and letting him step out of them, then she handed him a pair of the panties that she’d shown him.
The pair she chose were purple with a lace panel in the front and a narrow lace panel on each side.

“I got you briefs, rather than bikinis so that your willy won’t pock out. Aren’t they pretty?”

Paul looked at the elaborately laced item and could not deny that they were pretty – beautiful even, but when he touched them, they gave him shivers. They were cool and soft and silky. Now, he had seen some of Lori’s panties, before – never while she was actually wearing them because, she pointed out, correctly, that it was ok to fool around with his privates, but fooling around with hers could lead to consequences – but her panties always seem cute and kind of playful. These were down right beautiful. They were they kind of panties he looked up on sites like Victoria’s Secret when he needed a little erotic inspiration at night.

“Go ahead,” Lori thought that his hesitance was adorable, “put them on. They won’t bite.”

“Ok.” He moved to go into the bathroom, but Lori was in his way and didn’t move. “I need to go in the bathroom to change.”

“Why?”

“Why!?” That seemed like an odd question to Paul.

“Yeah,” Lori scrunched her face in confusion, “why? I mean, a few hours ago, I was nose to nose with your willy. I know what your dinky looks like, babe, and, frankly, I like it. Just get changed here in case you need help getting them over your heels.”

‘What the heck,’ he figured and he slide his colorful, cotton panties to the floor and slipped them past his heels fairly gracefully.

Lori took in the vision before her. Paul was small and slender. The modest heel gave him some kind of fanny. His hips seemed a bit androgynous and his shaved legs, with their stay-up, nude stockings looked sexy and inviting. He could use a little trimming in the ‘bush’ area, but that could be dealt with easily enough at some point. Except for the rapidly stiffening penis, his lower half looked like a slightly late blooming eighteen year old girl’s body. His still clothed torso was still sporting a blouse, but the padded bra gave him some nice curves there, too. His face, which had never appeared to be overtly feminine to her before today, looked soft and sweet and virginal. His strawberry blonde hair flipped up at the bottom and his gorgeous blue eyes, a feature she had always envied, looked, suddenly, girlish and timid. Maybe just a little thinning of the eyebrows and some tasteful makeup, but nothing more was needed to make him pretty enough to any break boy’s hearts if he wanted to. He was just so... cute.

“Um,” Paul’s voice got her attention. “I have a little problem.”

Lori followed his eyes to his new panties where a tent stood straight out in front. She laughed causing him to blush the sweetest shade of pink.

“You like them, I see.”

“Come on, Lori, you knew what this would do to me – to any guy. You bought the silkiest and frilliest panties you could find on purpose.”

“Well, maybe I did,” she grinned, “but so what. I want my boyfriend to be the prettiest girl in town. Just tuck it between your legs.”

“That’s what I’m trying to tell you, I have a problem. I can’t get it to tuck. It’s too stiff.”

That made his girlfriend break out in a sincere, belly laugh. “Well, then take care of it so that we can try on some of the clothes I got you.”

“What do you want me to do?”

“You know... take care of it. Do what you have to do.”

“Are you nuts? I’m not going to jerk myself right here in front of you.”

“Why not?”

“Why not!? Because... Because... Lori, I couldn’t. Not in FRONT of you – or even while you waited for me. I just... couldn’t do it.”

She heaved a huge, theatrical sigh, took his hand and said, “Fine, I’ll help you,” as she led him to the bathroom, positioned him in front of the toilet and lifted the seat.

“Ok. Not exactly as romantic or spontaneous as a girl might like it to be, but here we are. Now, take off your panties, little girl. You don’t want to get them messy while mommy makes you cum.”

Her playful attitude and in charge manner did nothing to calm Paul’s excitement. “Oh... ok.” He removed his panties and put them neatly on the towel rack.

He really was stiff. Lori wondered how much stiffer he get before he exploded. She maneuvered him back to the the front of the toilet and she began to run her hand gently along his shaft. She wanted him to come so that she could dress him, but he looked adorable like this, too. From his heeled feet to his curled hair, just adorable.

His little tush was more pronounced than usual due to the heels. So, so cute. As she masturbated him, she gently caressed his bottom with her other hand, gently touching his cheeks and letting her fingers tickle his crack. His reaction, surprised her. As he rocked a bit to increase excitement caused by the work of Lori’s hand, her fingers ran through the crack between his cheeks, he would freeze for a moment and gasp. She knew that many men could orgasm just through manipulating their prostates, but it never occurred to her to try something like that – but there is was. She could see and feel his opening right there under her finger tips. The time seemed right. She could do something that she’d never even considered before. She could penetrate her boyfriend.

His eyes were closed, he was lost in her touch. She kissed his narrow, weak shoulders. “So, pretty. So, so, pretty,” she whispered both seductively and maternally- as if speaking to a child.

Her sense of power gave her shivers. She was bigger than him. She was stronger than him. She’d been in jeans and sneakers all day, he’d been in petticoats and gowns. Suddenly, she wanted to take him as if he were a woman more than anything she’d ever wanted before. At that moment, he was a woman – no, a girl – no, her girl and she was the one in charge. The alpha. Yes, he had a penis, but she held it – it was hers. He was hers – SHE was hers.

The temptation was too much. She gave in.

As three of her fingers slid, suddenly, into him, his eyes opened, he gave out a guttural groan as his penis spasmed in orgasm, his eyes rolled to the back of his head, his knees buckled and he blacked out.

Lori hugged him and continued to milk his organ until she realized that Paul was passing out. She grabbed him and tried to hold him, but his dead weight was more than she could handle.

“Paul! Paulie! Paulie!” She said as panic overtook her. “Paulie! Stay with me, babe. Come on, Paulie!” but they were stinking, as slowly as she could manage, towards the tile floor.

Mercifully, Paul shook himself back to consciousness just as his limp body was about to pull Lori completely over. He grabbed the toilet bowl and hung on until he was fully aware of his surroundings.

“Are you ok?” Lori asked.

Paul blinked to clear his head, then nodded, “Yes. I think so. What happened?”

The laugh that Lori let out was more out of relief than amusement. “I think you blacked out for a minute, you little bunny, you.”

He used the toilet bowl to help himself back up as he asked, “Bunny? Why did you call me a bunny?”

“I read, one time, that, sometimes, male bunnies get so worked up during coitus that they pass out – just like you did.” She hugged him, relieved
that he was ok, if just a bit pale. “I take it that you enjoyed that?” She handed him some toilet paper to clean himself up.

Paul just smiled, feeling too awkward to give a real answer. He cleaned himself while Lori washed her hands.

Soon, his panties were back on and they returned to the kitchen, where Lori pulled a lavender dress from out of a bag. It was a sporty, casual dress, a lavender background adorned with images of pink and white roses all about it. She held it up in front of her to show Paul. “You like?”

“It’s very pretty. Is it for you?” Paul asked, knowing that it was for him. It did scare him just a bit. It was a normal dress. No big, fluffy petticoats, just a dress that a girl his age might wear to school or church. Up till now, he’d kind of been a cartoon of a girl. This was the real deal.

“Of course not,” she laughed, “it’s much too small for me. I got it for you, silly. It’s pretty, right!? I like it a lot. Let’s get it on you.”

There were no buttons or zippers, it just pulled on over his head. The top was stretchy and fitted him beautifully. The skirt reached to just below mid-thigh.

Lori adjusted the dress till it clung perfectly across his shoulders and ‘breasts,’ and hanged playfully from where it flared out where a girl’s ‘natural waist’ would be.

“Oh, it is pretty, babe, and you look so cute.” Her eyes sparkled with joy and young lust. She was smitten with her new girlfriend.

“Now,” she reached into an other bag and pulled out a pair of low-heeled, white sandals, “take off those shoes and stockings. These shoes go better and you don’t need stockings, your mom already shaved your legs and they’re cute as hell, even without the stockings.”

He did as he was told and sat to take off the shoes and stockings. He fastened the tiny, delicate buckles on the straps of the sandals and, before he could stand, Lori put a hand on his shoulder, telling him to stay there a moment.

“Your hairdo is too old fashioned for this dress. Let me brush you out before I do your makeup.”

“Make up?” Paul laughed, now getting a bit more relaxed with Lori leading him down this strange, new road. “Do I really need makeup to watch Netflix with you?”

“Why not? I’m wearing makeup to watch Netflix with you, aren’t I? I think that you need the full ‘girly’ experience. Between me and your mom, we’re going to make sure that you enjoy being a girl before you become your grandmother, next weekend. That way, you’ll look happy to be wearing that dress – the same way that she looked.”

The brush was moderately stiff and dug into his hair, which had been made stiff with hairspray. It scrapped his scalp and pulled the hair a bit. At first, it was a bit painful, but it became more and more relaxing as he got used to it. Eventually, it felt wonderful and he decided that it was best to just relax and enjoy it.

“Hi, guys. I’m home,” Lilly called as she entered through the kitchen door.

“Hi, mom!”

“Hi, Mrs Rooney. We’re in the family room.”

Lilly headed towards the giggling voices and the ‘shhh-ing’ sounds. When she entered the room, she stopped dead in her tracks. Here was her son, the one who, just twelve hours ago, was sobbing to the point wanting to die because his girlfriend had seen him in a gown, wearing a flouncing, dark purple, sleeveless, ball-length nightgown with a shirred lace bodice, scoop neckline and a tiny white bow at the bodice-line. He was sitting sideways on the couch, the gown spread beautifully around his legs, with Lori behind him, winding his hair into rollers. His face was made up with pretty and youthful eye makeup and a pinkish lipstick.

“Hi, mom,” he giggled. “This was all Lori’s idea. I hope you don’t mind.”

“What do you think, Mrs. Rooney? He looks cute, right? “

The amused shake of her head indicated to both teenagers that she was not upset. “Well, it looks like I may have opened up Pandora’s Box. At first it was, ‘Mom, I don’t want to do this. What if Lori finds out,’ and now, this. Any one care to explain the choices in clothing, makeup and, um, hair style?”

“Well you see, Mrs. Rooney,” Lori was anxious to explain, “I figured that, if you wanted a model who looked like a debutant from fifty five years ago, then I should teach Paulie what it felt like to be a girl back then. So, I found an older style nightie, I did his makeup similar to these pictures that we found online, and, according to my grandmother, girls back then wore curlers to bed most nights, so, I’m curling his hair. I was even able to find some of this ‘Dippity-Dew’ stuff to comb in before the curlers. He’s adorable, right?”

“He is that,” Lilly laughed. She held Paul’s face in her hands as she spoke to him. “And how do you feel about all of this, Paulie?”

“I don’t know, mom. It’s kind of fun, now that the cat’s out of the bag and Lori isn’t upset. My head hurts a little, but I’m having fun.”

“Oh, and Mrs Rooney, you have to see,” Lori was very excited. “Stand up, Paulie.”

He did as she instructed, but he was shocked when Lori nonchalantly grabbed the hem of his flouncy nightie and raised it up to his shoulders, exposing his purple bra and panty set.

“Oh, my, how lovely!” Lilly gushed, with no sense of it being odd at all.

She reached out and touched the fabric of the panties, running her fingers along the lace of the front panel where, had it not been tucked safely in the gusset, Paul’s penis would have been. “Oh, Lori, these must have cost a small fortune, but they are gorgeous. Paulie, you must feel so pretty in those”

‘Was this conversation really taking place?’ Paul wondered as his mother still caressed his lower abdomen without seeming to notice that something was missing.

“I guess...” he said.

“I guess, he says,” Lori laughed. “He loves it and he knows it, don’t you, babe?”

“Sure, ok,” Paul pulled the hem of his nightie out of his girlfriend’s hand and lowered it to just above his ankles, straightening it as it fell in billows about him, “but would you mind not showing my mom my underwear, please. It’s a little embarrassing.”

“Oh, Paulie,” Lilly laughed, “stop being a guy. Girls show their girlfriends, and even their moms, their pretty lingerie. It’s part of the fun of being a girl. Just let us have our fun and you’ll enjoy it, too.”

Then to Lori she said, “I like the high waisted panty for him. Good choice. I imagine that it’s easier to tuck himself away in these than some of the others.”

She turned back to Paul, “Are you comfortable down there, sweetheart?”

Paul clapped his hands over his ears, returned to his seat and yelled, “Blah, blah, blah, blah... I can’t hear you! I’m not listening! Blah, blah, blah, blah”

Lori laughed at his silliness, “I guess that he’s too macho to talk about his panties. I’ll just finish putting in his curlers then pin it all into a silk scarf that I brought for him, so that my big he-man can take off his makeup and crawl into bed in his nightie and get his beauty-sleep.”

Lilly giggled at that and shook her head, once more. “Alright, girls. I’m going to bed. See you in the morning.” And off she went.

Lilly raised the shades in Paul’s room. It was a beautiful, sunny, Sunday morning and she’d been up working since 7:00; that was three and a half hours ago. The sudden injection of light did nothing to rouse her son, though, so she walked to the side of the bed to give him a shake.

When she saw him, though, she paused and smiled. Many times she’d wished that she’d had a daughter. She’d always wanted to teach a daughter to sew and cook. Someone to do girl things with. Someone to come with her to a salon, or nail center. Things like that.

And there was Paulie.

His hair wrapped in a flowered scarf with the curlers obvious beneath. His small, smooth shoulders emphasized by the straps of the his purple nightie. His face clear and shiny – what had he used to remove his makeup? If Lori was sticking with her ‘fifty five years ago’ system, it was probably Ponds cold cream.

She sat on the edge of the bed and sighed at his sleeping form. She’d never really viewed him as girlish, before. Small, yes. Bookish, yes. Artistic, yes, but never girlish.

But now....

Could she ever think of him as a boy again? Probably, but, at least for this week and for a few more weekends, she had a daughter and Paulie was going to learn about being a girl before Saturday’s photo shoot.

She took his hand in one of hers and rubbed his arm with free hand. Lord, his skin seemed so soft. She hoped that she hadn’t gone too far with this, but, for now, she still needed him to wear the Victorian gowns while she worked and she wanted desperately to take those pictures for her mother.

“Paulie,” She sang his name softly as she rubbed his arm. “Paulie, sweetie, I need you to get up, love.”

Paul’s eyes rolled open and he smiled at his mother. This was unusual. Usually, she just hollered his name from the bottom of the steps. She’d never woken him like this before.

“Hi, mom,” he rolled over and felt the curlers in his hair. He touched them and smiled sheepishly at his grinning mother.

“You look lovely in that night gown, dear. Is it comfortable?”

Paul though for a moment. What was the point in denying that these were the most exotic, soft, just plain lovely things he’d ever worn in his life. “It is. I like it. The bra and panties that Lori got me are really soft and nice, too.” He sat up with his back against the headboard and his perky, little, false breasts causing the bodice of the silky gown to hang in a lovely manner.

His mother sighed quietly. Her little boy made such a pretty girl. “I’m sorry that I woke you, but I need your help, sweetheart. I ran my machine over the seams in grandma’s debutante dress and I need you to try it on. I also need to get at least another gown hemmed before we go out with Lori. Come on.”

She stood as she pulled the covers to the side. Paul swung his legs out and sat up, stretching and slipping his little painted toes into little purple scuffs that matched his night gown perfectly. When he stood, he reached for a shear, purple peignoir. It had long, shear puffy sleeves that ended in long cuffs. The bodice was more opaque and would have framed his bust prettily had he had a more maidenly form. It buttoned just below the bust with one, silk covered button, then burst into shear pleats that ballooned out in feminine splendor. It was obviously part of
a set. It matched the night gown and scuffs beautifully.

“Good heavens,” Lilly was a actually a bit jealous of how elegant Paul looked. “How much did Lori spend on all this?”

The shrug and smile that Paul gave her was as cute it could possibly be. “I don’t know... but, wait, you said we were going out with Lori?”

“That’s right, honey. We’re going to see Lori’s Aunt Alison. You’ve heard me talk about Alison, my hairdresser. Well, she’s Lori’s aunt and I want her to look at you and my mom’s picture so she can get things ready for you for next Saturday. We’ll get some lunch, too.”

“Really? When was all this decided?”

“About twenty minutes ago when I was measuring Lori for her prom gown. She’s downstairs now and she’s very anxious comb you out. So, move your tushy, young lady. We’ve got a lot to do, today.”

Paul floated into the lavatory, enjoying every luscious breeze that played with his billowing clothes and dealt with his morning ablutions, then, realizing that all of his new, fancy bra and panty sets were down stairs, he decided to get changed down there.

He hustled down the stairs as quickly as his clothing would allow, turned at the foot of the stairs, excited to show Lori that he was wearing the entire ensemble that she’d purchased for him, skipped to the kitchen and came to an abrupt stop when he saw that there were three people in the kitchen – not just two as he’d expected.

“Jesus, Rooney!” Beth’s grin was huge, “you look like you just stepped out of an old movie. Do you have curlers in your hair!? Holy cow! What gives!? I mean.. girls don’t dress like that anymore, you know!?”

“ Oh, stop teasing him,” Lori chastised her with a gentle slap on her shoulder. “It’s my idea. Kind of a method acting thing, you know. Like, if he wants to look and act just like his grandmother next weekend, he needs to know how it felt to be her. So, I bought him things that would help him experience being an eighteen year old, fifty five years ago.”

Then she turned to Paul, kissed his cheek and placed her hands on both of his cheeks and shook them, playfully. “Oh, you are the cutest little lady!”

Paul smiled at the attention that Lori was giving him, but he was still embarrassed that Beth had seen him dressed so completely femininely, so he kept his eye lids lowered, giving him a decidedly old fashioned demure look, which made Lori even happier.

Something that definitely caught Paul’s attention though, was how tall Lori was as she hugged him, just now. When their embrace ended, he looked down and saw, at the tapered ends of her jeans, she was wearing higher heels than he’d ever seen her wear before. The shoes had a small platform at the toe and Paul could not even guess how high the heel was. They were beautiful, but...

“What’s with the shoes?” He asked quietly.

“What? Don’t you like them? I think they’re adorable.” Lori held her hair back as she looked more closely at them.

“They’re... well... they’re really tall. That’s all.”

“Oh! I see. Yes, they are. They’re for prom. I wanted your mom to get an accurate measurement.”

Paul was a bit surprised by this choice of footwear. “Lori, are you really planning to wear shoes that tall to prom?”

“Yes, of course. It’s my senior prom. I want to look beautiful. You don’t mind, do you?”

He shrugged, “I don’t know.... I guess I kind of do. I mean... if I’m taking you to prom and you’re that much taller than me...”

“Whoa, Paulie...” Lori stopped him. “You’re not taking me to prom. I’m taking you. Remember, I’m the senior, you’re the junior. I have a job, you don’t. I can drive, you can’t. You are my date – not the other way around. I mean, yeah, I’ll be taller than you, but so what. I’m taller than you anyway. It’s never been a problem before.”

Even though everything that she’d said was true, it caught Paul a little by surprise. She was just soooo tall in those shoes.

“Besides,” Lori continued, “I look good in these. Wait till you see the dress that your mom is making me. With that dress and these shoes, you’re going to be happy to be there with me, Paulie. You’ll see.”

“She’s right, Paulie,” Lilly chimed in. “She’s going to be a knockout on prom night. You’ll see.”

“Yeah, don’t sweat it, Rooney,” Beth laughed. “I’m eight inches shorter than Jeff. It’s no big deal. Oh, I have an idea! I’m getting some really tall shoes for prom – not like Lori’s, her’s are just elegant – I’m talking skyscrapers! You can come shopping with me. I’ll fix you up and and you can be as tall as Lori.”

Everyone got a good laugh at Paul’s expense. He laughed with them, realizing the silliness of the situation.

“You’re all sick, you know that, right?” He joked as he sat at the table, smoothing the gown and peignoir beneath him.

“Says the boy with his hair in curlers,” Lilly laughed. “Speaking of which, Lori, would you, please, take out his curlers while he eats breakfast? I’d like him to try mom’s dress on before I get him into his big petticoat for the bridesmaids’ dresses.”

While Paul nibbled at an English muffin, Lori removed his curlers with enthusiasm, letting each curl bounce freely around her boyfriend’s face. “Wow!” She giggled, “ that setting gel did a great job! These curls are amazing. You look like Shirley Temple, babe.”

“What!?” Paul shouted, slightly afraid that he’d be stuck with a head of curls that he’d be unable to loose before school the next day.

“Don’t worry. I’m brushing it out, now,” Lori chuckled.

By the time he’d finished his breakfast, Paul’s hair was brushed out leaving behind a thick, fluffy, wavy mane of hair. Lori had parted it on the right side making it more like the picture of his grandmother. With the help of a curling iron, his hair was flipped under again and when Lilly held the photo of her mother up beside Paul’s un-made-up face, Beth and Lori both agreed with Lilly, his resemblance to the young woman in the photo was truly uncanny.

“Aww, very cute,” Lilly said as she picked up a shorter, less full petticoat that would go under his grandmother’s debutant dress. “Here, hold up your nightie and I’ll put this on so we can get started.”

Paul stood and did as he was told, turning his back to Beth to avoid comments about his panties. She saw them, anyway, but Lori gave her a smile and a shake of the head to keep her from saying anything. Lori liked the panties and didn’t want Beth creating a reason to make it difficult to keep him this way.

He stepped into the petticoat and Lilly pulled it up past his waist where a narrow elastic held it in place. It was not nearly as full as his long petticoat and this one ended at his knees. This one was slightly stiffer, but was absolutely dripping in lace.

Then, with the help of all three woman, Paul’s slippers, peignoir and nightgown were removed, leaving him barefooted in a padded bra and petticoat.

“I don’t think that the purple bra is right for this dress, Paulie. Do you have another bra you can put on?”

“Geez, mom,” Paul was both embarrassed and titillated to be standing there in such frilly attire discussing what other lingerie he may currently own, “just come right out and tell the world that your son owns several bras!”

“I bought him a white set yesterday, Mrs Rooney. Paulie, where’s that bag?” Lori added helpfully.

After a moment’s search, they found the bag on the counter. Beth brought it to the table and they dumped the contents out.

“Oh, Lori,” Lilly gushed, “you picked such pretty things for him. These sets are all so gorgeous and, Paulie, look, these dresses are all so cute, too! Oh, Paulie, we’re going to have to find an occasion for you to wear them.”

“Mom! Can we just concentrate on the matter at hand!? Come on, I’m not going to find any ‘occasion’ to wear a dress! Let’s not get carried away.”

Beth smirked as she hung the lace covered, white, padded bra from her right index finger, her left hand on her thrust hip. “The lady doth protest too much, methinks,” she said dramatically as she bowed theatrically and held the bra up for Paul to take.”

He snatched the item from her and put it back on the table in front of him, then reached around his back and struggled to undo the hooks and eyes that held his current bra securely around him.

After watching him struggle for a few moments, eliciting giggles from the younger women, Lilly said, “Ok, big guy, we’ll help you. Lori, you help him with his bra.”

“Ok, Mrs Rooney,” she giggled as she stepped behind him and undid the hooks and eyes.

Meanwhile, Lilly knelt in front of him and, without any warning, reached under his petticoat and pulled his panties to the floor in one, quick pull.

“Mom! What are you doing!?”

“Step out of your panties, Paulie. Beth, please hand me the white ones,” Lilly was matter of fact about everything going on. She had things to do
and she was getting things done. Had it not been for the shock that Paul experienced due to her behavior, he would have been sporting a massive erection. He’d grown to enjoy the feel of women’s clothing and the fact that Lori found it exciting made it all that much more erotic, so wearing women’s underwear while standing in a room with three beautiful women – none of whom were wearing anything nearly as pretty as he was – was a huge turn on, BUT having his mother exposing him like this was shocking.

“Mom!!”

“Oh, hush, you big baby. No one can see anything. Women can do this without anyone seeing their hoo-hoos.” She pulled the purple panties off his feet and held out the white ones into which Paul’s feet descended.

As Lilly raised the panties up his legs, Lori was attaching the hooks and eyes on his new bra. “Put your arms up, babe. This is a push up bra. I’ll attach the clasps and when you lower your arms, it’ll catch as much
flesh as possible in the cups.”

Paul did as he was told. He concentrated on the sensation of Lori’s hands as he did his best to ignore his mother pulling panties up his legs. Lilly pulled the panties over his rear end, but then, as she pulled the front of the panties over the front of his crotch, Lilly slid her hand into the front and pushed his penis and ball sack back between his legs and pulled the panties up tightly, nestling his manhood in the panties’ gusset.

“Mom!” His arms shot down in an attempt to pull her hand away from his privates, but the petticoats made it impossible to defend himself.

“Oh, stop. I’m your mother. I’ve touched you there a million times. It needed to be done and I was in the position to do it, so – just stop.”

The whole situation amused Beth to no end. Paul just wished that SHE wasn’t there. His mom or Lori was fine. Even his mom AND Lori was fine, but he was a bit scared that Beth would tell others about this.

Lilly produced a pair of white, open toed pumps and had Paul step into them, then she asked Lori to help her retrieve Paul’s grandmother’s dress, leaving Paul and Beth momentarily alone in the kitchen.

“You’re looking pretty cute, there, Rooney.”

“Beth, you won’t, you know, tell anyone about all of this, will you? I mean... you won’t, will you?”

“Rooney, I think you’re cute as hell and you should actually consider dressing pretty all the time, but I won’t tell anyone. Lori and I have been best friends since before preschool. I’m not sure that I could date a guy that was prettier than me, but Lori is nuts about you and she is really hot and bothered about this girly stuff. You’re making my best friend very happy, Rooney, so your secret’s safe with me. Cool?”

Paul let out a long sigh. “Very cool, Beth. Thanks.”

Lilly and Lori returned with the dress. It was just as pretty as it looked in the photograph. It had weather the decades and remained beautifully preserved. Paul was surprised to see that the back of the dress did not have a zipper, but, rather, what looked like at least twenty little, pearl buttons.

The women lowered the dress to the floor and Lilly instructed Paul, “Step into it, honey, and Lori and I will raise it around the petticoats.”

Paul stepped into the beautiful dress and Lori and his mom raised the dress slowly, careful not to catch it on the petticoats. As he slid his arms through the arm holes and pulled the bodice against him, he was incased in cool, smooth material that felt amazing against his skin. He was so excited by the sensations he was feeling lightheaded. He couldn’t help but to run his fingers over the lace coverings and move the material against his body.

“The under-dress is real silk, honey,” Lilly explained. “It feels nice, doesn’t it?”

Paul nodded as his mother began the slow process of buttoning up the back of the dress.

“This dress was custom made by a seamstress who used to have a studio downtown,” Lilly continued, “and I guarantee you that my grandfather paid top dollar for this dress. He had four sons, but only one daughter and that was my mom. He spoiled her rotten and she loved it. I bet you that he paid nearly a thousand dollars for this dress and that was more than fifty years ago. I can’t imagine how much it would cost today.”

The bodice was tight – not uncomfortably so, but definitely tighter than any clothes he’d ever worn before. It forced him to stand straighter than he normally would. As each button closed around him, his mom would adjust the back and shoulders for a better fit. He began to feel as if the dress was not his garment, but rather that he was just a vehicle for the dress.

“Stand a little straighter, honey,” Lilly advised, “the buttons are very small and I need you as straight as possible so that I can get them into
the holes.”

It took more than a couple of minutes to button all the tiny pearls into place. “Whew, that was a job!” Lilly joked as she fussed with the top of
the sleeveless formal, working her way down to the bottom of its skirt at Paul’s knees. She tugged gently on the petticoat so that it peeked prettily out at the bottom.

“Wow!” Lori breathed, “it’s just perfect.”

“Well, close,” Lilly smiled, “but not quite perfect, but we can fix that.”

“What’s wrong with it?” both younger women asked as they inspected the dress, too.

“Well,” Lilly mused as she put one hand on her hip and the other on her chin, “I WAS concerned that his shoulders would be too wide, but, if anything, it looks a bit loose there.”

“Congratulations, babe,” Lori teased, “You’re smaller than your grandma was when she was your age.”

“But look at the bust-line,” Lilly continued. “We need to make him a little fuller there. Lori, run upstairs and grab a few pairs of socks out of Paulie’s bureau, please, so that we can make his girls a little bigger. Beth, please grab mom’s photo for me, so I can figure this out.”

Paul was silent as everyone worked around him. He was considering all the sensations that were bombarding him right now. The dress felt like nothing he’d ever worn before. It was soft and silky inside and out and it felt wonderfully constrictive and protective on the top, but loose and flirtatious below. When anyone touched the skirt of the dress, the dress and petticoats rustled and swished and made him feel pretty and vulnerable. He wanted to take it off immediately. To put on some dirty, boy clothes and go do something tough and mannish. He wanted to scream at his mother for assuming that, just because he was small, she could humiliate him like this. He wasn’t a sissy and she had no right to do this to him.

But, even more than that, he wanted to run to a mirror and see himself. He wanted to spin, to see and to feel the mass of skirts expand with his motion, to feel them wrap themselves around his legs when he stopped spinning. He wanted to tell his mom and his girlfriend and even Beth how pretty he felt. He wanted to run out in the street and show everyone how pretty he was. He wanted to go to his grandmother’s and show her how he looked. He wanted to shake his hair to feel it tickle his neck and shoulders. He wanted to try on the jewelry. He wanted to do it all. To be a pretty girl and to nestle under Lori’s strong arm while they hung out with their friends.

And all of that scared him and froze him in his pumps, allowing the women to do whatever they wanted.

He was in heaven and he was in hell.

But heaven was winning.

“Yeah, that’s what I thought,” Lilly showed Beth the photograph, “he’s a little straighter here in the torso than mom was.”

“Well, yes,” Beth looked at Paul critically, “but won’t he look curvier when his boobs are a little fuller? Sorry, Rooney. I don’t mean to criticize your boobs, but...”

“Yes,” Lilly put the photo down and squeezed Paul at the line where the dress flared out from the tight bodice, “but if I get him a waist cincher or a nipper, nothing too drastic, I don’t think he needs a full corset, or anything, but just a little more shape and he’ll fit it perfectly.”

“Here are the socks,” Lori returned and held out the selections of hosiery.

Lilly took two pairs, rolled them and tucked them into Paul’s bra, adjusting the dress when she was done. “Better,” she proclaimed, “but I’ll need to get him something more natural looking.”

“I have plenty of foam inserts,” Lori laughed. “Between my three sisters and me, we have a bag full. We were all late bloomers.”

Lilly thanked her, but explained that she wanted something more natural looking. “A friend of mine had a double mastectomy a few years back and she’s mentioned that there is a place in town that specializes in realistic breast forms. I’ll ask her where it is. I’d say he needs at least a “B” cup. I’ll find a tactful way to ask my mom how big she was back then.”

Lilly noticed the disconnected look in her son’s eyes and realized that she’d left him out of the conversation. “What do you think, Paulie?”

Paul snapped back to the conversation. Part of him wanted to tell them all that he was so excited that he was afraid he’d have an orgasm right there in front of them all, but, instead, he muttered a bewildered, “About what?”

Lilly smiled. He obviously was enjoying this, at least at some level, but he seemed so scared and, well, female. Like a little girl getting ready for the biggest, most terrifying event of her young life. She assumed that her mother probably felt the same way all those years ago. Excited and scared.

“Would you like to see yourself in the mirror?”

“Sure,” Paul tried to be as nonchalant as possible. He didn’t fool anyone.

Lilly held the girls back while Paul took in the reflection. “Give him a few moments,” she whispered.

The reflection was not of Paul. There were hints of Paul there, but not Paul. At least not the Paul he’d seen everyday for eighteen-plus years. This reflection was of a young woman. A pretty young woman, at that. She needed a few more touches to be beautiful, but it was obvious that, with
a little makeup, some jewelry and a little more attention to her hair, this young woman would be a stunning sight.

He turned to the right to see how the dress flared out behind him and he ran his hands along his rear end, compressing the material against himself, then watching it pop back out to all of its girlish fullness.

He turned to the left and did the same.

It was odd and disconcerting and absolutely wonderful.

He ran his hands over his new breasts and down his sides and shook his shoulders from side to side to watch how his hair bounced and his dress swung. He felt nice and pretty and special. The dress was so beautiful and it fitted him so well – it was as if the fates had been keeping this very special treat for him since long before he was born. Had that ever happened to anyone before? Probably not. That made him special.

Finally, he glanced down the hallway and saw his mother, friend and girlfriend watching him closely and he realized that they’d been watching him sway and primp. He felt embarrassed.

“Sorry,” he said quietly.

Lori walked towards him while shaking her head, “No, no, baby. No need to be sorry.”

She placed an arm around his shoulder and turned him to face the mirror once again. “Look at that girl in the mirror, babe. Isn’t she adorable?” she whispered.

She fluffed his curled, flipped hair and, then ran her palms across the back of his bare shoulders and gripped them in her strong hands. She whispered, “You like it, don’t you, baby? You like being my pretty, little girlfriend, don’t you?”

Paul didn’t answer. He just stared at their reflection in the mirror. Even though he was wearing heels, the reflection of the girl in the white, lace dress looked so much smaller and more feminine than Lori. If that girl was him, what did this mean?

“Come on, baby, tell me that you like being my little girlfriend. Just tell me that you do.”

Eventually, he nodded a tiny nod.

“No, baby. Tell me. Say the words. I need to hear it.”

It took a moment, but soon he he knew that he could not deny it. This was how he was meant to look. The whisper was quiet and weak and girlish, but it was exactly what Lori wanted to hear. “I do. I like being your little girlfriend.”

“See,” she kissed his shoulder, “that was easy. You are a cute little thing. You were meant to be like this, baby. I want you to always be my girlfriend. I want to take care of you, baby. I want help you get prettier and prettier when we’re together. I can teach you to be a girl, a woman. I’m going to help you to be my dream girl. That’s what you want, isn’t it, baby?”

He was in a trance. This all just seemed so right. Lori’s lips on his shoulders and neck were too much. His knees buckled as the orgasm exploded into his panties. He hadn’t felt it coming and he had no warning. He clung to Lori for support.

Lori felt him tremble and watched his eyes roll to the back of his head. She couldn’t believe that this had happened, but she knew that she had a
power over him that she had never considered before she saw his panties two days ago. If he wasn’t before, he was hers, now, and she was going take him all the way. She’d never had lesbian tendencies, but she wanted this little girl in her arms to be her lover more than anything she’d ever desired before.

She chuckled and purred while she supported him. “Oh, you’re a naughty little thing, aren’t you?”

“Paulie!” Lilly exclaimed as she hurried down the hall.

“Don’t tell my mom,” he begged Lori, but it didn’t matter. When she saw his flushed skin and the sheen of sweat on his face, she knew.

“Oh, Paulie,”she giggled, “did you get too excited?”

He nodded.

“Do you need clean panties?”

He nodded again. “I think I need to pee, too.”

She chuckled again. “Ok, honey. That wasn’t very ladylike, was it? Umm, you’ll need some help with your dress and petticoats, so...”

“Rooney, you ok?” Beth had been waiting down the hall, but couldn’t wait any longer to see if Paul was alright.

“He’s fine, Beth,” Lilly assured her. “He just had a little... well... Beth, umm, Lori and I have to help Paulie in the bathroom. Would you, please, grab him some fresh panties and hand them in to us?”

“Sure, Mrs Rooney,” there was a muted chuckle in her response, too.

“There’s several pairs of white ones in the bag, Beth,” Lori called. “Grab the ones with the pink bows. They’ll match his bra the best.”

Paul was so far beyond being embarrassed at this point that he couldn’t care less that Beth knew, too.

They walked him to the downstairs lavatory and his mother turned him towards her. “Now, Paulie, I’m going to have to wipe you off when I drop your panties, ok? I know that you’d prefer that I not touch you, but these petticoats are very expensive and I certainly don’t want any of that on grandma’s dress.”

“Here are his panties, Mrs Rooney.”

“Oh, thank you, Beth. Um... could you go into the hall closet and grab the package of baby wipes and, well there’s no need in being subtle now, I suppose, would you also grab a panty liner for Paulie?”

Beth nodded and Lori told Lilly what a good idea that was. Paul was oblivious to what a panty liner was.

When she had everything ready, Lilly told Lori to hold up Paul’s petticoats and skirts. Lilly knelt and lowered his panties to the floor, lifting each foot to pull them off. Then she took a baby wipe and cleaned up the mess on Paul’s thighs and penis. The wipe was cold and made his spent penis contract further.

When he was clean, they guided him to the toilet so he could sit. Lilly pushed his shrunken equipment between his thighs so that he could relieve himself. He could see nothing past the dress and petticoats.

While he sat, Beth assisted Lilly with the panties and panty liner. Paul watched, confused.

“What’s that, mom?”

“Oh, Nothing, honey. It’s just a pantie liner. Women use them to keep leaks from soiling their panties. Under the circumstances, I think you should wear one, too. Just till you’re more accustomed to the new you, if you know what I mean.”

He knew exactly what she meant. “I’m done with the toilet, mom.” He said quietly.

“Oh, well don’t stand until I wipe you! Did you just do pee-pee, honey, or do I need to wipe the back, too?”

“Just pee,” he sighed.

Lilly lifted his frothy skirts and, for the third time that day, gently gripped his penis, pulled it clear of the toilet seat and used another wipe to ensure it was clean. This time, however, either due to absent mindedness, of because handling him was becoming routine to her, she allowed his skirts to come high enough to expose him to Beth, who stood in the doorway. Beth’s smile was playful and a bit superior. Paul scowled at her, but she just raised eyebrows and licked her lips playfully.

When his clothes were properly reassembled, Lilly announced that she needed to take a few photos so she could plan what she needed to do that week and after that she needed Paul in his Victorian petticoat so she could pin up the last of the bridesmaids’ gowns before going to see Lori’s aunt that afternoon. Lori and Beth excused themselves to run some errands while Lilly and Paul worked on the last two gowns.

Neither said much.

Finally, as she was pinning the hem of the last gown, Lilly said, “You’ve been pretty quiet since the girls left.”

Paul shrugged.

“Is everything ok?”

He shrugged again.

It was silent for another minute or so until Paul finally offered, “It’s just that.... Well, I’m not sure... I mean, mom, I’m boy, right...”

“Right...” Lilly didn’t look up, she just focused on the hem and allowed Paul to search for his words.

“And boys shouldn’t... you know... like to wear clothes like... this. And I... do. Is there something wrong with me that I let you dress me like this and that... I like it?”

Lilly stood and fluffed his skirts, looking at the hem with a critical eye, keeping everything very ‘matter of fact’ as she responded to Paul. “I don’t see why you shouldn’t like it, Paulie. The clothes are soft and beautiful and you look lovely in them.”

“I know, mom, but I am a guy, you know.”

“Yes, of course I know, Paulie, but this is the twenty-first century. Girls have been wearing jeans and slacks for three generations, now. Everyday, I see stories about boys in dresses. Maybe you’re over thinking this.”

Lilly let her gaze rise up to meet Paul’s. With Him on the platform, he was about half a head taller than his mom. She fussed with the gown, then fluffed his hair a little and ran her hands along his soft, hairless cheeks, finally resting them on his exposed, narrow shoulders.

“I am only asking you to do this for the photo, next Saturday, and then to help me finish the gowns and dresses. After that, you can do whatever you want, but, and I don’t think that this will come as a surprise to you, I think that Lori is pretty happy with her new, pretty boyfriend, don’t you? She might have different ideas.”

Paul knew that his mother had hit the nail on the head. He was nuts about Lori and had always been thrilled that she took a shine to him, but she REALLY seemed turned on when he was in a dress. What if she asked him to stay looking girlish all the time? Could he do it? Yes. Would he do it? He wasn’t sure, but ‘probably’ seemed like the right answer.

“Tell me the truth, Paulie. Do you like wearing these clothes?”

“Yes, mom. I really do.”

“Then enjoy them while you can and if you want to stay in boy clothes when you’re not helping me, then I’ll support that, BUT, if you want to stay in girl clothes part time OR full time, I’ll support that, too. It’s up to you honey.”

“Thanks, mom.”

She kissed his soft cheek and walked behind him to look at the hem back there.

Paul stared at his reflection in the tall mirror.

“Mom?”

“Yes, Love?

“Do you think I look nice like this?”

“I do, sweetheart. I think you look absolutely beautiful.”

Paul stared some more while he tenderly caressed the gown and his hair. “Thanks, mommy.”

Lilly smiled, “It’s the truth, honey. It’s the truth.”

They were already ten minutes late and Paul was being stubborn.

“But, do you think it’s ok to wear a dress outside of the house, mom?” Paul was having a bit of an anxiety attack.

“Well, of course, honey. People do it everyday.” Lilly dropped her hands to her sides in exasperation.

“Paulie,” Lori was losing her patience, “it’s not a dress, it’s a romper and a very cute one at that. Just put it on so we can get going to my Aunt Alison’s house. We’re going to be late!”

As these kinds of things go, this garment wasn’t likely to draw a whole lot of attention. It was made of a grey, crepe material with a seemingly random assortment of what looked like paint brush marks that were darker
grey, black and blue all about it. It buttoned up the front and was sleeveless. Maybe it would be ok to give something like this a try.

“Ok,” he said as he pulled the romper up his legs. It had spacious leg holes and, when he pulled the bottom up to his waist, the short, but spacious, leg material barely touched his legs. He pulled his arms into the sleeveless openings and shrugged it into place, then buttoned up the front.

When it was all in place, he looked at the reflection in the tall mirror and said, “It sure looks like a dress to me.”

“Well, I for one,” smiled Lilly, “think it looks just lovely. Is it comfortable?”

“Yes. It feels a little big, though.”

“Maybe it is just a little big, but it’s supposed to fit loosely, babe,” Lori smiled as she grabbed her purse and ushered Paul out the door. “We may as well take my car, Mrs Rooney, since I’m behind you.”

“Oh, what a treat!” Lilly smiled, as she looked at the cute little, seafoam-green VW Beetle that Lori had purchased herself several weeks earlier. “I can’t remember the last time that I rode in a convertible!”

Lori pulled the passenger side door open and lifted the button to release the seat mechanism and allowed the back of the front passenger seat to slide forward and thereby create access to the back seat. “Paulie, it would probably be easier for you than your mom to ride in the back. You don’t mind, though, do you?”

Of course, she was right. His mom was in her forties and not as used to crawling into little spaces as he was, but, yes, he did mind. He wanted to ride up front with Lori. Instead, he was in the back, like some child. Regardless, he said, “Sure,” and pulled himself into the back.

When she was about to back out of the driveway, Lori stopped turned in her seat, grabbing three baseball caps she kept in the arm rest. “I almost forgot!” She handed one to each of the Rooneys. All bore the Red Sox logo and all were a vivid pink. “These will keep your hair out of your eyes.”

As they started down the street, Lilly said to Lori, “That is a lovely romper you bought for Paulie, but you shouldn’t be spending all of your money like that.”

“Oh, I didn’t buy that,” she grinned from ear to ear. “That belongs to one of my little sisters, Meredith. They’re pretty much the same size.”

“Oh, I don’t think I’ve met your little sister. Is she at school with you and Paulie?”

“Not till next year,” Lori pulled out not traffic. “She’s in eighth grade.”

‘Wonderful’ thought Paul.

“And she and Paulie are the same size?”

“Well, I thought so, but obviously, Paul is a little smaller. She fills out that romper a little more than Paulie does. I bet that he’d fit in my sister, Samantha’s clothes though.”

“Oh, and how old is Samantha?”

“Sammie will be thirteen in a couple of weeks. She’s in seventh grade.”

‘A twelve year old. Well that’s just great! I’m the same size as her twelve year old sister,” Paul began to despair that Lori would ever see him as a man, but she turned and winked him. That’s all it took for Paul. She loved him. He was fine.

“Well. There are some things I could do for him here, but I’d need him at the salon for a lot of what I’d like to do, and there’s no way that you can do everything that he needs done in one morning. If you want him to be a dead ringer for the girl on the picture, I need him for a couple
hours in the middle of the week.” Alison was inspecting both Paul and the photo and making mental notes.

“What kind of things?” Lilly asked.

Alison sighed, “Well, he’ll need a body perm to get his hair that full and he needs a lot of work on his brows. The perm should take a day or two to relax enough to truly style it like the girl in the photo and if I pluck his brows on Saturday, they’ll look swollen when you take the picture. I mean, I could do the eye brows now, but I’ll need to do the perm at the shop. “

“Also, even though he doesn’t have much of a beard or arm or leg hair, I’d suggest that I give him a good waxing to make him look right.” Alison paused and continued to scrutinize the boy in her chair. “And I wouldn’t take a chance on those crappy ear-ring-adapters. I’d pierce them sooner rather than later, put the pearls in on Saturday then he can decide if he wants to put the studs back in to keep the holes open, or let them close.”

“Cross your legs, baby,” Lori whispered to Paul. “Sit like a lady.”

“Do I really need to get my ears pierced?” Paul whispered back as he adjusted himself in the chair.

“It doesn’t really hurt, baby, and lots of guys at school have theirs pierced. It’s no big deal.”

Paul sighed. He wanted to explore his feminine side now that he’d found it, but this seemed a bit out of control. His mother seemed enthralled in the whole process, as if he was really a debutante preparing for his own coming out party.

“Hmmm,” Lilly considered her options, “I don’t know, Ali. Waxing seems a little much. I’m sure that we can use a depilatory and he’ll be ok for one day. If he decides to continue to stay smooth, he can come back for a waxing. I see your point about the eyebrows, though. Could we do those today?”

“Sure, I’ll get things ready.”

Paul was relieved that he wouldn’t be getting a full body wax, but shaping his eyebrows seemed a bit extreme, too. “Mom, do you think that’s necessary? I mean, I have to go to school. I don’t want to get beat up because I have girls’ eyebrows.”

“Honey,” Lilly patted his arm reassuringly, “look at grandma’s picture. She didn’t have thin little eyebrows. They’re just sculpted a little. No one will notice at school, but it will make a big difference in the photo.”

Lilly went off to talk to Alison.

“She’s right, babe. She’ll just neaten everything up a little for you.”Lori patted his shoulder.

“Lori, what if the guys notice. What will I say?”

She laughed playfully. “Just tell them that you did it because I asked you too. They’ll believe that.”

Well, there was truth to that. Lori was beautiful and she hung out with the most popular groups at school – as well as with the theater, band and chorus kids. Most of the guys would give a testicle to go out on just one date with her. No one, not even Paul, understood why, when she could have anyone in the school, she would have picked him. But, she did and every guy knew that he would do anything for her – they all would, too.

“Ok,” he smiled knowing that it would make Lori happy if he trimmed his eyebrows a bit.

Alison returned with a tray with lots of items on it. “Ok, Paulie, first we’re going to wash your hair and get a little color into it while I do your eyebrows.”

As she turned his chair and lowered the back of the chair to the sink, Paul said, “You’re dying my hair!?”

“Just a little lighter, honey,” Lilly reassured him. “Grandma’s hair in the photo is a little bit lighter than yours and we want it to be perfect. You’ll hardly notice.”

“Then why do it?” Going to school with his hair AND his eyebrows both looking different may attract even more attention.

“You’ll hardly notice it in real life, honey, but I want to have the two pictures be absolutely identical, so that when people look at it, they can’t tell which girl is my mother and which is my son.” Her smile was infectious.

Paul let out yet another sigh of resignation, “Ok, mom. If it’s that important to you...”

Several hours later and Paul had a new, substantially lighter, hair color, ears pierced with little gold studs in them, well groomed eyebrows which, although not feminine arches, were undeniably female and one appointment at Alison’s salon at 6:00pm on Wednesday to get a body perm and a trim and another for Saturday morning at 7:30am to have his hair and makeup done before the photographer arrived at 1:00 that afternoon.

As Lilly and Alison settled the bill, Lilly remarked to Alison, “Didn’t I tell you that he was just the spit and image of my mother. I think it’s amazing.”

“He certainly is that,” Alison agreed. “Isn’t that a strange expression – spit and image.”

“It is,” Lilly nodded.

Being the age that she was, Lori had already grabbed her phone and googled the phrase to find its origins.

“Huh,” she showed her phone’s screen to the older women. “it says here that it comes from the Bible story of God creating man in his own image using mud and spit. So Adam was ‘the spit and image’ of God. That’s cool, isn’t it.”

“It is,” Lilly laughed, “and how appropriate as we recreate Paulie in the image of his grandmother. Thank you, Alison, see you Wednesday!”

“Ok.” Lilly closed the door to the VW Beetle after Paul had climbed into the front seat, “You two have a good time and get this young lady back home before 10:00. It’s a school night, remember.” They’d had a lovely lunch at a small delicatessen that catered mostly to business people in the downtown area. Paul was reasonably sure that they wouldn’t run into anyone he knew, there. Then Lori and Paul had waited in the car while Lilly had run into a couple of shops to pick up a few items. Then, at Lori’s insistence, they’d taken a quick spin along the coast so that Lilly could enjoy the smell of the ocean while riding in a convertible. Now, they were dropping Lilly off before going to Lori’s house.

Lilly fished the keys out of her purse, took off the pink baseball cap, passed it back to Lori, then leaned down and kissed her son affectionately on the cheek. “Now, be good, you understand. I know that you two are all hot and bothered, but be good, anyway.”

“Don’t worry, Mrs Rooney. We’re just going to my house for an hour or so, then I’ll have her back to you safe and sound.”

Paul rolled his eyes at the use of the feminine pronoun. “Bye, Mom.”

It was just a few blocks’ ride to Lori’s house. It was a standard, blue and white McMansion that looked like every other house on their block.

“Are you sure that your mom is ok with me being dressed like this?” Paul asked as they climbed the steep stairs that lead to Lori’s house.

“Sure. I told her about the picture and all that. She thinks it’s as sweet as I do.”

Being the middle child of five, Lori’s house was always a bit hectic, so it was rare that Paul was ever invited over. Her oldest sibling, Andrew, had already graduated from college and moved away. He was the same age as Paul’s brother Keith and he was the only boy in Lori’s family. Lori’s mom and dad had split years ago, so the house was always filled with the girls and their friends. Whenever Lori’s brother came home, he referred to it as ‘The Hen House’ and the first rule of The Hen House was boys were only allowed in when mom was home and they were never allowed to go upstairs for any reason.

This day, when they entered, Lori’s two younger sisters were sprawled out on the living room floor with homework spread everywhere. They were in a mad dash to get things done that they should have gotten done before now and their mom was not happy with them.

“Hi, Lori,” they each called. Meredith was thirteen and in eighth grade. Samantha was 12 and in seventh. They were born only ten months apart, so
her mom referred to them as “the Irish twins.”

“Hey, guys. You know Paulie, right?”

Meredith leapt to her feet and ran around to see Paul’s clothes. “Oh, let me see, let me see.” She was all grins as she inspected him. “Huh, my romper looks a little too big. Sammie, come here. Let’s see how tall you are next to Paul.”

Sammie stood, jumped onto the seat of the low-backed chair between her and Paul, used it as a trampoline, leapt over the back of the chair, landing right next to Paul.

“Go back to back and let’s see who’s taller,” Meredith was running the show as Lori ducked into the kitchen to get her mom.

“Look, mom,” Meredith was inspecting Paul and her sister who stood back to back with each other, “Sammie is only about a half an inch shorter than Paulie. I’m a little taller. Not much – yet – but give me a year.”

Paul grimaced.

Besides her mother, Lori’s older sister, Becca, was there. Where the younger sisters only seemed interested in who’s clothes would fit Paul better, Becca and Lori’s mom were really taken aback by how Paul looked.

“Paul Rooney,” her mom smiled, “my goodness, is that really you!?”

“Yes, ma’am,” Paul stuttered. “It’s me, alright, Mrs Carter. I hope you don’t think this all too weird or anything...”

“Not at all, dear. You look absolutely precious, doesn’t he Becca?”

Becca laughed and agreed.

“So, Anyway, I need to gather up a few things for Paulie to wear in the evenings this week so that he’s ready for Saturday. Is it ok if we go upstairs and rummage around through Sammie and Merrie’s closets and see what we can find?”

Mrs Carter sighed. “I guess, but no nonsense, now. Becca, will you please chaperone for them?”

“Sure, mom,” Becca bobbed her head towards the stairway, “let’s go, ladies.”

When they reached the room that the two younger siblings shared, Lori opened the closet door and began looking at dresses. She explained to Becca that, if Paulie was as comfortable as possible in a dress by Friday night, then Saturday should be a breeze.

“That does make sense,” Becca said. She’d not taken her eyes off of Paul since they entered the room. You do look cute, Paulie, I’ll give you that. The hair, the earrings, the romper – very nice. And I see that you shaved your legs, too. Also cute. Did you pluck his eyebrows, Lori?”

“No, Aunt Alison waxed them for him. Nice, huh?” Then, pulling a red peasant dress with elbow length, puffy sleeves from the closet, she held it up for Becca’s approval. “What do you think?”

Becca took the dress, “Let’s Give it a try. Come on, Paulie, you need to take off your romper.”

“Umm, can’t I try these on in the bathroom and come back to show you?”

“Paulie,” Lori laughed, “Don’t worry about it. You’re all tucked in. All Becca will see is a bra and panties and she’s seen those before. Come on.”

“Yeah, Paulie,” Becca helped him remove the romper, “where’s your sense of fun and adventure. Here, hold your arms up for me. I’ll help you get this on.”

Holding up his arms, Becca slipped the red, flowered dress over his arms and head, letting it balloon out as it dropped, then settled around him.

“Oh, that is cute, Lori,” Becca beamed.

“I don’t know. Maybe it’s a little too... Holly Hobby-ish for him, though. Maybe a little too little girl. What do you think?”

Becca adjusted the dress some more and smiled at Paul. “I hope you’re having as much fun as I am, Paulie. I don’t know why, but this is a lot more fun than dressing one of my sisters. I like the way you blush.” Then to Lori, she said, “I think you should at least consider it. I mean, it is a little young for a debutante, but just look at how cute he looks in it. Makes me want to take him out and show him off.”

“Oh, stop,” Lori joked. “Here, try this sundress.”

Becca helped Paul get out of the peasant dress, commenting, “Oh, nice. You shaved your pits, too,” while his arms were up.

If anything, the sundress made him look even more like a classmate of Samantha’s.

“You know what the problem is,” Becca said. “It’s not the dresses, it’s because Paulie isn’t wearing any makeup. It makes him look like a little girl. We could fix that pretty easily.”

What was it with women wanting to make him look like a girl? Obviously he enjoyed the feeling of the clothes and the pampering, but here was another woman getting excited about him looking like a girl.

Lori considered it for a moment, then said, “You’ve definitely hit the nail on the head. It is the lack of makeup, but it’s already dinner time. I think I’ll spare him another round of primping today. You must be tired, baby, aren’t you?”

Paul was both relieved and disappointed, but he nodded, “”Yes, I am kinda beat. It has been a long weekend.”

“I’m sure it has been, babe. I’m tired, too, but I had a great time. Here, try this last dress on for me, ok? I think you’ll like it. It’s very comfortable.”

Paul removed the sundress and slipped into this casual dress. It was a short dress, well above his knees, with very short, cap sleeves. It had a cream colored background, with dozens of little, realistic looking birds of many varieties scattered about the fabric. Some birds were upright, some upside down. Some facing up, some facing down. Some in flight, some at rest. It had a little brown belt which couldn’t have been more than a half-inch tall, that nestled against his torso prettily and the material was a cotton so light and soft that it felt as if he was wearing nothing at all.

“That’s perfect,” Becca clapped as Lori buttoned six tiny buttons up his back.

“I agree,” Lori was looking at Paul in a mirror on her sisters’ door. “We have our winner! What do you think, Paulie?”

He liked it. In fact he loved it, but he wasn’t sure that he should say it out loud. “It’s nice, I guess,” he said.

Lori wrapped her arms around him from behind. “Nice, Huh? Ok. It’s nice, but look at that girl in the mirror. She looks better than nice, doesn’t
she? She’s adorable and you know it... AND... she’s you.”

She kissed the back of his head.

“You know She’s right, Paulie,” Becca stood beside him. All were looking at his reflection. “You’re a cute little guy, Paulie, but as a girl... well, just look... you’re a knockout. You should consider dressing like this full time.”

There it was.

Someone had said it out loud.

Full time.

Now he was scared.

He was scared that he’d be forced to be dressed as a girl and having to go to school.

He was scared that he’d be forced to be dressed as a girl and having to face his brother and cousins.

He was scared that he’d be forced to actually become a girl.

But mostly, he was scared that if he resisted dressing as a girl, he’d never be able to feel this soft and pretty and wonderful again.

A shiver ran down his spine. He needed to do or say something and finally, all he could think to say was, “I don’t know. Do you really think I look ok?”

“No one said that you look OK, babe. You look adorable and you look like a girl and I kinda love it.” Lori was sincere. She was smitten with Paul
and she would never tell him that he had to dress as a girl “or else,” but she found him so amazingly attractive this way.

It was still too much for him to commit to, right now, so he said, “ I don’t know. Can we just keep it between us for now? I mean, if people found out... I don’t know... your sisters won’t tell, will they?”

“I won’t say anything, Paulie,” Becca smiled, “and I’ll make Sammie and Merrie swear not to, either.”

“Hey, girls,” Lori’s mom shouted up the stairs, “I’m ordering Chinese takeout. Are you eating with us?”

“Yes,” the sisters yelled back.

Becca and Lori picked up the discarded clothes and put them back on hangers. As Lori picked up the romper that Paul had been wearing, he walked over to her and turned his back to her.

“What?” Lori asked, confused.

“Will you unbutton me so I can put the romper back on?”

“Oh, baby, no. The romper was just to go to Aunt Alison’s. Kind of like a ‘training dress.’ If you’re going to be comfortable in your grandmother’s dress next weekend, you need to be used to wearing real dresses. So, from here on until Saturday, when you’re not in school, I want to see you in a dress. The cuter, the better. And that one is adorable – BUT – it is pretty flimsy. Becca, can you dig through Sammie’s drawers and find a short half-slip so Paulie has a little modesty. Tonight, baby, you are getting some tutoring from The Hen House ladies so that, by Saturday, you’ll be right at home in your grandma’s dress.”

After a moment’s rummaging through her youngest sister’s underwear draw, Becca produced a small, white half-slip, dripping in lace. “This is a pretty one, Paulie. You’ll like it.”

She handed the slip to her sister who said, “Bec, can I have a minute alone with Paulie?”

Becca smiled, “Sure,” and she left, closing the door behind her. “I’ll be right here... keeping watch for you.”

Lori gave her sister a little wave of thanks, then knelt in front of Paul, holding the slip open for him. He stepped into it and Lori guided it up his legs, letting the gentle elastic waist band secure the silky garment to him.

“There,” she whispered as she adjusted the slip and dress. “That feels nice, doesn’t it?”

He nodded.

Lori lifted the front of his dress, once again, as if inspecting the slip. Then she lifted the slip as well.

Paul’s breath skipped just a bit.

She gently caressed his flat panty front. “Mmm, I like you like this; nice and flat, but you know what would make it better?”

“What?”

She kissed the front of his silky, lacy panties. “If your skin was smooth here. Tonight, when you shower, do me a favor and shave all this nasty hair off for me, Ok?”

As she said this, her hand slipped between his legs, gently rubbing his tucked organ through the gusset of his panties and the panty liner. He breathed in, sharply and she could feel him grow stiff immediately, forcing the tip of his organ to pop out of the side of the leg hole.

Lori glanced up at him and smiled seductively. “Oh, dear,” she giggled and she whispered, “someone’s getting excited. Does my sweet, little boy friend like wearing my little sister’s dresses? I think he does. I think he likes it a lot. So much that he’s not going to be able to keep from showing me how excited he is.”

She slipped a finger around the protruding part of his penis and gently stroked the sensitive vein on the underside of his inverted manhood. That was all it took. He exploded into Lori’s hand. She was able to catch most of it in her hand. She looked up at him and smiled as he spasm-ed and released all that he could.

When his orgasm subsided, she carefully tucked him back into the gusset, allowing his panty liner to absorb any residual cum, and she stood, careful not to let his seed spill from her hand. When she reached her feet, she hugged his head to her shoulder and breasts. “Shh, baby. That felt nice, right?”

He nodded and tried to regain his senses.

Lori stuck a finger into the goo in her hand, raised it to her lips and licked it. “Mmm. You do make delicious treats, Paulie.” She stuck her finger into the goo, again and, without warning, stuck the seamen coated digit into Paul’s mouth, holding it there. “Suck, babe. You’ll like it.”

Paul was shocked, but complied. The taste was not bad, per se, just odd – a bit salty.

Three more times, Lori took a helping for herself and then fed a helping to Paul. She was heady with the desire to share this with him. She felt so powerful and in command of the situation. There he was, her cute little boyfriend. He was barefoot and tiny and almost helpless while she wore very high heels and towered over him and felt the now familiar feeling of power over their relationship. He had on lacy, silk panties, a lacy, softly padded bra and the cutest little dress while she wore sensible, cotton panties, a casual bra with jeans and a tee shirt.

This was all so damned fun and Paulie just looked so, so, so adorable. This was how it was all meant to be.

Suddenly, the door opened a crack and Becca whispered into the room. “Are you guys about done? The Chinese food delivery guy just showed up. We should go down stairs before mom comes looking for us.”

“Oh, we’re done, aren’t we, baby?” Lori grinned, then headed to her sisters’ lavatory to wash her hands.

Becca came in and looked at Paul. She ran her fingers through his hair and adjusted his dress. “Breathe correctly, Paulie, you’re kinda of red in the face. Mom will want to know why.”

He nodded as Becca went to the closet, retrieved a pair of white sandals with a one inch kitten heel. They had just a narrow strap that crossed his foot, just behind his toes and another, more narrow strap that went around his ankle. Becca knelt and fastened the ankle straps for him. He glanced at the mirror. “Those are pretty,” was all he could think to say before being lead downstairs by the sisters.

“Hey, that’s my dress!” Samantha shouted.

“And my shoes!” Meredith joined.

“Yeah, but you guys never looked this cute in them, did you?” Lori said with a smile.

“Here, let me take a look at you,” Lori’s mom pulled him to a clear area in the kitchen to check him out.

“Very nice, Paul. Spin for me, let me see the dress flare out on you.”

He did as he was told, but stopped when Samantha shouted, “Mom, he’s wearing my slip! Oh, my God, Lori, he’s not wearing my panties, too, is he!?”

“No, of course not,” Lori laughed. “I bought him his own bras and panties. What girl would ever pass up the chance of buying lingerie for her boyfriend?”

Before Paul could even blush, Lori’s mom was fussing with his hair and looking at him in a very critical way. “I like your hair this color, Paul, but it needs a little more styling. Are you brushing it every morning and night? At least hundred strokes each morning and night will make it shine and you’ll be amazed at how healthy it looks in just a couple of days of brushing combined with a good shampoo and conditioner. So you’d better start that regime with your next shower.”

“Yes, ma’am,” he said.

“I’m surprised that my sister didn’t even up the length while you were there. What’s the plan for your hair?”

“I’m going back on Wednesday for a body perm and a trim.”

“Excellent. I hope that a mani/pedi is scheduled, too, because your toes and fingers need to be just as dressed up as the rest of you. I like the
color on your toes, but they need some shaping. Your fingernails need a lot of attention.”

“I’m taking him to our nail salon after school tomorrow, mom,” Lori said. That was news to Paul, but not overly surprising under the circumstances.

“Good. Ok, Paul – or are we saying Pauline, now?”

“No, mom,” Lori answered for him, “we’re sticking with Paulie.”

“Hmm, I guess that works fine. I went to school with a girl named ‘Polly.’ Polly Brennan. She was a beautiful little girl as I recall. Just like you, Paulie. Ok, let’s eat.”

As they each took their seats, Samantha was eyeing every move that Paul made. When he sat, she criticized his posture and her mother was more than happy to have the other girls demonstrate how to sit up straight with their backs not touching the chairs and their legs crossed at the thigh or ankle.

Amused by her sister’s observation, Meredith joined in the fun and soon, every bite of food, every sip of water, every shake of the head was being scrutinized and corrected by Lori’s family of girls.

“So, Paulie,” Samantha asked, “does it bother you that you’re wearing your girlfriend’s youngest sister’s clothes, now?”

Paul swallowed the little bit of rice in his mouth. “Actually, yes. It kind of does. It never occurred to me that I could wear your clothes.”

“Oh, don’t let it bother you, Paulie,” Mrs Carter patted his arm. “All of my kids are tall. You’re just a bit on the shorter side. It’s no big deal. Look on the bright side. You have a lot of hand-me-downs to look forward to in the next few months.”

All of the girls seemed to think that this was a much better idea than did Paul.

“That’s a great idea, mom,” Meredith agreed, “and judging by how he looks in that dress, he’ll be a lot cuter in Sammie’s clothes than see ever was.”

Mrs Carter, Becca and Lori all laughed at Meredith’s joke. Sammie yelled, “Hey! That’s not funny! He’s not cuter than I am! If mommy let me wear a padded bra like his mommy does, then I’d look cuter, too! So, shut up, Meredith!”

The women all laughed boisterously, but Paul felt a little uncomfortable with his underwear being discussed so freely amongst all these females ranging in age from forty nine to twelve years old – especially since he was being compared to the twelve year old – the twelve year old who would definitely be much taller than him in a year or less. He squirmed as he felt his penis shrivel with nervousness. What would it be like if he decided to stay in skirts and dresses? He’d be smaller and weaker than every other woman in this room – heck he was already smaller and weaker than four of them AND he was the only one wearing a dress.

That was it, he decided. He couldn’t let his desire to wear these clothes take over his life. He’d live up to his commitments to his mother, but that was it. Then he was going right back to being a guy.

“Well, Paulie,” Lori was still laughing at her younger sisters’ argument, “what do you think? Are you looking forward to getting Sammie’s hand-me-downs? Because, you know, with her being the youngest, she’s already gotten all of our old clothes. So, you’ll kind of be getting all of our hand-me-downs.”

Paul thought for a moment, then smiled before he shrugged and said, “I don’t think I’ll need them. This is only for a week, then I’m going back to wearing my jeans,” but then he shook his head so his hair was moved behind his shoulders and he took a nibble of rice from his chop sticks, being careful to lean over his plate so nothing could fall into his napkin-ed lap. The move was so instinctively feminine that, unseen by Paul, all the girls and women exchanged smiles and nods. It was obvious that whatever was going on in his head, wasn’t going to end on Saturday. He was hooked.
 
 
To Be Continued...