Remembering to Sit

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Remembering to Sit

I

Martha was frustrated. For what seemed like the thousandth time, urine was splattered around the toilet in their little bungalow. For years, she’d ignored her son’s inconsideration and cleaned up after him. Now, energized by the Me Too movement, she felt put upon. Of course, cleaning up after an eleven year old was a long way from sexual harassment, but it was all part of males mistreating women.

“Jerry, come here this instant!”

He strolled in almost a minute later. “Yes, mom?”

“How many times have I told you to be careful when you pee?”

“Lots, I guess.”

“Well, look here. What do you suppose that is?”

“Pee?”

“Yes, but it’s not mine. I sit when I pee and it all goes in the bowl. It’s yours. From now on, I want you to sit when you pee.”

“Like a girl?”

“If that’s how you want to think of it, yes, like a girl.”

“OK, mom,” he said over his shoulder as he walked back to his room.

Two days later, Martha had cleaned up two more sprays and a small puddle. Each time she’d reminded Jerry he was supposed to be sitting. Here was another sizeable splash.

“Jerry, come here this instant!”

“Yes, mom?” he said in an annoyed tone as he sauntered in.

“Don’t you take that tone with me, young man! I’ve asked you to sit to pee and reminded you nicely. This is the fourth time in two days you’ve peed on the floor. What have you go to say for yourself?”

“Well, I’ve peed standing up forever. It’s like a habit – so I just forget. Also, only girls sit and I don’t want to be girly!”

“I see,” said Martha in a cold, determined tone that should have raised Jerry’s alarm bells, but didn’t. “I have an idea that will solve both your little problems. Here, you clean the floor,” (she handed him a sponge and pink rubber gloves) “while I get a few things.”

Jerry felt like telling his mother to go to hell, but sensed that would be a very bad idea. “OK, mom,” he said putting on the gloves and taking the sponge. He he’d just started cleaning when he heard the garage door open, then close. The job wasn’t half done, but his mother was gone, so he returned to his Grand Theft Auto game. About an hour later the garage door cycled again. Jerry turned off his X-Box.

Martha came to his room and put two shopping bags on his bed.

“Come along. I want to see what kind of job you did on the bathroom floor.”

Jerry got a knot in his stomach, but followed his mother.

“Just as I expected. The floor is only half clean. In fact, you’ve smeared pee over an even larger area. If you’d done a really good job – showed you wanted to do better – I might have relented, but as it is, you’ve only strengthened my resolve.”

“I can finish it now,” he said with a bit of trepidation.

“You’ve had an hour. You can finish it later – after I show you what I’ve bought to help to remind you to sit on the toilet.”

Jerry followed her back to his room.

“OK, take off your pants.”

“What?”

“I got you new pants. Now, do as I say. Take off your pants!” She dumped a Walmart bag out on his bed, revealing slacks in light blue, tan and burgundy.

“See – they have elastic waists, so you can easily pull them down to sit,” she said showing him. “And their flies are merely decorative – they have no zippers. So you can’t ‘just forget’ and pee standing up.”

Jerry examined the blue pair. The tag read “Girls Size 10.” “These are girls pants!”

“Of course they are. Boys pants all have zippers in the fly – that’s why you ‘just forget.’ Now you won’t. Put them on!”

“You’ve gone fucking nuts, you bitch!”

Before he knew it, Jerry was over his mother’s knee and had four red hand prints on his rear. His cheeks burnt like fire. Worse, he was in shock – he’d never been spanked before.

“Why … why … did … you … do that?” he said between sobs.

“Because I won’t be talked to like that! I’ve never spanked you because I thought you’d respond to love and kindness. Instead, you’re growing into a spoiled brat. You treat me like I’m your maid – not even doing the simplest thing to make my life easier. And now you’re using abusive language! Well, it’s going to stop! I won’t raise an emotionally or physically abusive man!”

“I’m … I’m … sorry.”

“Not as sorry as you will be! You know what’s in the Kohl’s bag? Girls panties. My first idea was to put you in panties as a reminder to sit. But, after I bought them, I thought wearing panties would be too humiliating. So I looked for unisex pants instead. And what did I get for my trouble? You verbally abusing me! I was going to take the panties back, but now you can wear them! Here!” She threw a pack of cotton panties at Jerry. “Pick out a pretty pair and put them on! Then put all your old pants, shorts and underpants in these bags and bring them to the living room. You have five minutes!”

A few minutes later, Jerry appeared in the living room holding two bulging bags. He was wearing the light blue slacks. His eyes, red from crying, matched his blushing cheeks.

“Is that all of your pants and underpants? Shorts too?”

“Yes, mommy.”

“Good!” She said in a gentle tone. “Put them here, in front of the sofa.”

He did.

“Show me what panties you picked.”

He pulled down his waistband. He was wearing the only white pair.

Martha thought of saying blue panties would go better with his slacks, but decided not to criticize. “Thank you dear! I know this is hard on you, but it’s for your own good.”

“Yes, mommy. … When will I get my boy pants and underwear back?”

“What makes you think you’ll get them back?”

“Will I?”

“Yes, when I decide it’s appropriate … which won’t be for a couple of weeks at least. … Why are you standing at that weird angle? Face me when we are talking.”

Jerry turned to face his mother, revealing his obvious excitement.

“Don’t be embarrassed dear, lots of boys like wearing panties.”

Jerry wanted to defend his honor, but could think of nothing to say. Did he really like wearing panties? “Yes, mommy,” he sniffled.

“Now you’ve had a hard day. Go finish the bathroom floor, then come back and we’ll do something fun.”

A few minutes later, Jerry reappeared.

“Do you want to see if I did a good job, mommy?”

“No, I think I can trust you, dear. Come sit next to me and we’ll watch a movie. I’ve ordered a pizza.”

Jerry sat next to Martha as they watched Matilda. Soon he was snuggling against her – something he hadn’t done for years. He was almost asleep before the pizza arrived. After eating less than a piece he fell asleep against her breast.

When the movie ended, Martha led him the bathroom – where he sat without objection – and then to bed. As there was a noticeable sticky spot on his panties, she helped him into a mauve pair with a kitty print. He was too tired to object.

In the kitchen, loading the dishwasher, Martha reflected on the day. She could hardly be more thrilled. Jerry had gone from a selfish, distant child cursing her to a sweet boy calling her “mommy” and snuggling against her affectionately. Clearly, she was on the right track. She slept contented.

II

The next day was Monday. Jerry wore his blue slacks to school, and used a stall to take care of his business. No one seemed to notice his new pants, except that Judy, who sat next to him in Social Studies. She was a healthy, athletic girl who wore boy’s shirts and jeans most of the time. He’d been rude to her early in the year, and so she almost never talked to him. Still, she said, “You look nice today, Jerry.”

His first urge was to tell her to shut up. Instead, he said, “So do you, Judy. I like how you’ve done your hair.”

No one else had noticed her first perm, so she was pleasantly surprised. At lunch she asked if she could sit next to him. Jerry had no regular lunch crowd, and was happy for the company. Mostly they talked about how embarrassed Mr. Jenkins, their Life Sciences teacher, was in broaching sex education. Finally, Judy struck a more personal note.

“You have really nice hands, Jerry, but they’d look better if you stopped biting your nails and let them grow a bit. I wouldn’t say anything, but I used to bite my nails, and now look at them.” She fluttered polished nails with rose decals.

Normally, Jerry would have rebuffed her, but, in panties, he was in no position to be nasty. “They’re really cute, Judy. I love your little flowers. Did you paint them yourself?”

“No, silly! They’re decals.”

“Decals?”

“You know, little stickers. They stick to your nails. I have lots more. If you’d like, I could bring you some.”

“Boys don’t use things like that.”

“I bet some do.”

Jerry imagined what his hands would look like with polished nail and decals. Uncomfortable with the thought, he changed the subject. “How’d you stop biting your nails? I have some bad habits, so I know how hard they are to break.”

“My mom got this bitter stuff to put on my nails. Then, every time I put them in my mouth, I hated the taste. So, I stopped in a hurry!”

“Yeah, my mom got me some things to stop a bad habit. I guess it can really help.”

“Oh, what habit was that and what’d she get you?”

“It’s too embarrassing.”

“Well, maybe when we know each other better, you’ll trust me enough to say.”

“Yeah, maybe …” Jerry couldn’t imagine ever trusting anyone enough to say he wore panties. When he broke out of his revere, he heard Judy talking.

“… bring it for you tomorrow.”

It took him a second to figure out what she was talking about. “You mean the bitter nail stuff?”

“Well, … Yeah!”

“Oh, that would be lovely. Thank you.” “‘Lovely,’” he thought. “Where’d that come from? I’m starting to sound like a girl.”

That night his mother, a paralegal, was home to greet him. Usually, she worked late and he let himself in, but occasionally she worked from home.

“How did your day go dear?”

“Good, thanks.”

“No one said anything about your new slacks?”

“No … Well, yeah, this girl Judy, who sits next to me in one of my classes, said I looked nice today.”

“What did you say?”

“I told her hair looked nice.”

“That was very sweet of you, dear.” Martha was both pleased and surprised. Jerry had been in the “girls are yucky” stage and could be quite rude.

“Yeah, she sat next to me at lunch. Maybe we’ll be friends.”

“That would be lovely, dear.” A girl friend might help tone down Jerry’s masculine rudeness.

Meanwhile, Jerry was wincing internally because “lovely” was the girlish word he’d said to Judy. “Yeah, I guess,” he said drifting off to his room. Maybe playing Grand Theft Auto would remedy his creeping sissiness.

When he got to his room, the game was gone. Jerry wanted to go out and shout at his mom, but what could he say? He wasn’t supposed to have Grand Theft Auto in the first place. The problem was, it wasn’t his, but Roger McCarthy’s. Roger was not a forgiving boy. Jerry had “rented” it for $5.00 and it was due back Friday. If he didn’t have it, Roger would beat him to a pulp.

Jerry sat on his bed and began to cry quietly. After a few minutes, his mother came in.

“There’s no use crying. You can’t have that game. It’s too violent – and grown-up – for you.”

“I’m sorry, mommy. Really! … But now I’m going to get beat up!”

“Why’s that?”

“Because it wasn’t mine. It’s Roger McCarthy’s and he’s in 8th grade. He’s going to beat the shit out of me.”

“Watch your language! I know you’re scared, but it is your own fault. If you’d obeyed me, you wouldn’t be in this fix. I found the game when I was looking through your room to see if you’d put all your things in the bags as I asked. I decided to shred it. …”

“Oh no. I’m dead!” Now Jerry was balling his eyes out.

“No, you’re not – if you do as I say. A disk is too heavy for our home shredder, so I put it in my purse to use the office shredder. I’ll give it to you if you promise not to play it again and return it to Roger tomorrow.”

“Oh, mommy, I will! Thank you! Thank you!” He stood up and hugged her as hard as he could.

“OK, OK. Now what about your punishment for disobeying and being a sneak? You deserve another spanking.”

Jerry could almost feel the burning welts on his rear. “Please don’t spank me again!”

“Then what do you suggest?” As a modern parent, Martha felt guilty about spanking Jerry, even though it had been quite effective.

“Hmm … You could make me wear girl’s tops at home for a week?”

Martha was taken off guard. Where had the idea of girls clothes as a punishment come from? Girls slacks weren’t a punishment, but an aid in breaking a bad habit. Then she remembered that, in her anger, she’d added panties as a punishment. He was much sweeter wearing them. Still, she’d spent more than she could afford on girl’s clothes already – especially since she’d be giving them away in a few weeks.

“You’d rather dress like a girl than be spanked?”

“I don’t want to dress like a girl, but it doesn’t hurt like being spanked.”

“OK, but on two conditions: (1) you pay for your new clothes – I spent more than I could afford already – and (2) you help pick them out.”

“I’ll pay for them out of my allowance, but I don’t want people seeing me buying girls clothes.”

“There are very few people at the thrift store at dinner time and no one who knows you. So, is it a deal?”

Jerry had no wish for another spanking. “OK,” he said quietly.

“It’ll be easier if you look like a tomboy.”

Jerry had no idea what kind of boy a Tom was. Maybe it had something to do with turkeys. At any rate, he didn’t object as his mother parted his longish hair it in the middle and bobby pinned the sides.

There were only two elderly shoppers in the store. They were aisles away, looking through a rack of house dresses. The tops were arranged by size, so it didn’t take long for Martha to find a lavender “Princess” in his size. Wanting to leave as soon as possible, he agreed to whatever she suggested. Realizing this, Martha felt a mischievous, and selected two more feminine blouses. One was lavender satin, the other ivory with a lace bodice. She also told him to select a top. He found a yellow “Hello Kitty” tee.

“That’s enough tops for a week.”

“OK. Can we go now?”

“No. No daughter of mine is wearing a top with nothing under it. You need lingerie.”

“Lingerie?”

“Pretty underwear, dear.”

The lingerie bin was an unorganized jumble. Martha seemed to be taking forever going through it.

“Can’t you do this faster?”

“It’d go faster if you helped.”

Reluctantly, Jerry began sorting through the mass of slips, bras and camisoles. He fingered the items gingerly at first, but the silky textures made him forget his shyness. Once he was actually looking, he became intrigued by the some of lace patterns. Martha noticed him lingering over some camis. She said nothing, but adjusted her choices in response. Finally, they had a small pile of possibilities.

Jerry blushed when his mother held lingerie against him for size. She rationalized embarrassing him by recalling that this was supposed to be a punishment, and perhaps he was enjoying it too much. Their final selections were a white satin training bra, a beige push-up, and two lace camis – one cream and the other blue.

“That should do it, dear. Take your basket to the register.”

“Can’t you pay for them, mommy?”

“There’s no reason for a girl your age not to pay for her own things.”

“But, I’m not a girl, mommy.”

“Do you want everyone to know that?”

“No.”

“Then don’t make a scene. I’ll be with you.”

“OK, mommy,” he said grudgingly.

“You’ve made some darling choices. You daughter will look a lot less like a tomboy in her new things. She’s so pretty, it’s a waste for her to dress like a boy.”

Jerry was wondering why his mother picked two lavender tops, and was not listening.

Martha nudged him. “Thank the lady, sweetie.”

“Thank you, mam,” He said, looking at his feet.

“Pay her, dear.”

He extracted crumpled bills from his pocket.

“Oh dear, you don’t have a purse. … Let me throw one in,” she said, turning to a shelf behind her. She put his change in a lavender vinyl purse and handed it to him.

Martha nudged Jerry.

“Thank you for the purse, mam. It’s very pretty,” he said before almost running out of the store.

“Is this his first time shopping?”

Martha wasn’t surprised that Jerry had been made. “Yes, it is.”

“Well, he’s not the only one, you know. Just last week another mother was in with a ‘daughter’ about his age and before that, an older teen – shopping by himself. Your son is very lucky to have such an understanding and supportive mother.”

“Thank you.” Martha wondered if she was either understanding or supportive. She didn’t even know if Jerry wanted to dress like a girl. Would a boy who didn’t become aroused wearing panties, or suggest wearing girls clothes as a punishment? Would he become entranced by the lace lingerie he’d handled in the bin? She vowed to keep her eyes open.

When they got home, Martha told Jerry, “Wear one of your bras under everything – and a cami under your blouse and your ivory blouse.”

“Yes, mommy.”

In a couple of minutes, heard Jerry called plaintively, “Mommy, I need help.”

“What’s the matter, dear?”

“I don’t know how to put this on,” he said holding a bra.

“‘This’ has a name. Please use it.”

“I don’t know how to put this bra on.”

“You mean your bra? The one you bought with your own money?”

“Yes, mommy,” he said quietly.

“Then tell me properly, what you’d like.”

“Could you please help me put my bra on?”

Martha showed him how to hook it in the front and turn it around.

“Tomorrow I want you to practice hooking it behind you back. When I get home, I expect you to demonstrate that how to put it on properly.”

“Yes, mommy.”

Martha went to the living room to wait. Shortly he appeared with the lace top over a blue camisole that coordinated with his slacks.

“That was a good choice of cami, You look very pretty dear.”

“Don’t tease, mommy.”

“I’m not teasing. Go look in the hall mirror and see if you’re not pretty.”

Jerry looked at himself. Martha was right. He looked like a pretty girl with a second-rate hairdo. He was embarrassed, but strangely fascinated. After dinner, he went back to look again, primping for a while before blushing at his behavior.

III

That night, he was emotionally drained. Unhooking his bra was a struggle, so he just wore it to bed.

On her way to bed, Martha checked on him. The next morning it was a gym day, and she wanted to leave a pair of boy’s briefs on his dresser. There was no missing the bra strap on his shoulder as she tucked him in.

He woke surprised to be wearing his bra, but he was wearing panties anyway, so what’s the big deal? When he took it off, he saw the bra’s outline on his chest! Even the cups were marked! The pattern was still there after his shower. PE was at 11:00 and Jerry hardly heard a word said in class as he worried about his bra marks. Fortunately, when he undressed for gym the outline was all but gone. He put his sweats on quickly. No one said anything.

As he showered after class, he saw Marty Collins looking at him. Marty was a small, quiet boy, who was often picked on. Jerry had stood up for him a number of times. So they got along well, but weren’t close friends. They were among the last to leave the locker room.

“Jerry, boys like us need to be careful on gym days.”

“Er … thanks, Marty.”

“Boys like us …,” Jerry thought. Marty obviously picked up on his bra marks. Did he wear bras too? Jerry didn’t know if he wanted to follow up with Marty. Maybe Jerry had misunderstood. Still, if Marty sometimes wore girls clothes … Jerry was unsure what he’d say, ask or want to share. The image of Marty in a bra and panties like him kept flying around in his head, with no place to land.

At lunch, Judy and he sat together again. She gave him a half full bottle of Mavala, which turned out to be a clear nail polish for stopping nail biting and thumb sucking. Jerry was quite embarrassed by it. First, the idea of wearing nail polish, even clear polish, was another step toward being a sissy. Second, since his spanking, he sucked his thumb at night. He found it comforting. He wanted to stop biting his nails to have nice hands for Judy, but he wasn’t sure he wanted to stop sucking his thumb. Maybe if he put it on all his other fingers …

While he was still thinking about Mavala, he saw Roger McCarthy, and went over to return his Grand Theft Auto disk. He told Roger his mom was making him give it back. Roger called him a wuss, but did him no further harm. When he came back to their table, Judy asked him what that was about.

“Oh. I had his Grand Theft Auto disk, but my mom found it, and I had to give it back.”

“I’m glad you did. That’s no game for a sweet boy like you, Jerry.”

“I guess you’re right. I’m trying to change. My mom’s helping me.”

When he got home, he put on his training bra and Hello Kitty tee. The tightness of his bra started him worrying about whether anyone but Marty had noticed his bra marks. Soon, he was biting his nails. “There’s no time like the present,” he thought, and put Mavala on eight fingers and his left thumb.

After finishing the little homework he had, he decided to make up for his misbehavior, and started cleaning up the kitchen. He was still working on it when Martha came in. She saw her tween working at the sink, bra straps outlined under her, rather his, Hello Kitty tee.

“Oh, sweetie, thank you so much. You’re an angel!” she said, giving Jerry an affectionate hug.

Jerry missed his mother’s hugs and returned it, adding a kiss on her cheek.

After putting her purse away, Martha helped her ersatz daughter finish the extra dishes.

As Jerry was wiping the counter down, she noticed the clear polish on his nails. She quietly checked another box on her mental list.

“Would you like to go out for a burger?”

“Not dressed like this!”

“You look cute! If I did something with your hair, you’d be quite passable.”

“Someone would see me.”

“OK, OK. Maybe another time. I’ll order Chinese.” Over dinner, Martha asked “May I at least show you what I can do with your hair?”

Jerry wanted his mother’s attention. “Maybe … as long as I don’t look like a girl for school tomorrow.”

“It won’t be anything permanent, I promise.”

“OK.”

She thought, “he doesn’t mind looking like a girl as long as no one else sees.”

Martha shampooed his hair in the kitchen sink, finishing with an argan oil conditioner. She patted it, then blew it dry – brushing it up and out. It ended with twice the volume and a faint vanilla smell. She paused to inspect her work, then lifted the ends with her curling iron.

“Go look.”

Jerry knew the child staring back from the mirror was himself, but, still, it was a girl. He reached up and pushed his hair this way and that. Each time, it bounced back into shape. He loved it!

“Oh mommy! It's so pretty! Thank you!”

“You’re welcome dear.” She kissed him on the forehead. “Now, in the morning, wet your comb and the curls should brush out after a few minutes. Then, you’ll look like a boy again.”

IV

The next morning, after five minutes of wetting and brushing, his curls disappeared, but his hair retained its bounce and volume. Jerry had mixed feelings. He liked his new look, but the pointer had moved another degree toward feminine. There was no time to do more, so he shrugged and went to breakfast.

Martha noticed the feminine lilt of his hair, but, again, there was no time to correct it, so she said nothing.

At school he got looks, but most had better things to do than comment on the boy taking another small step in expressing himself. Marty Collins smiled and gave him a thumbs up as they passed. In Social Studies Judy said, “It’s my turn to say I like your hair. It smells good, too. I love vanilla.” Jerry was unaware of the scent because he’d gotten used to it. He was about to say something when class started.

At lunch Judy didn’t mention his hair, but asked, “How’s the Mavala working?”

Jerry had all but forgotten his nails, but he remembered recoiling from the bitter taste of his fingers several times that morning. “I hadn’t thought about it, but now that you mention it, it's working pretty well.”

“I’m glad. The shine already makes your nails look nicer.”

“Thanks, I guess. Is it that obvious? Boy’s aren’t supposed to wear polish.”

“No, it’s not ‘obvious.’ It’s clear after all. Besides, who says boys can’t look nice? Especially sweet ones.”

Jerry blushed.

“By the way, I wish my hair looked as good as yours. What did you do to it?”

“Nothing. My mom gave me a shampoo and used her conditioner. You really like it?”

“It’s gorgeous.”

Jerry glowed inside at the compliment. “Not too girly?”

“What’s it matter? It looks nice, and I know you like it.”

“I do.”

“Would you like to get together after school?”

“I would, but I can’t. I’m … er … grounded this week.”

“That’s too bad. I have a book of hair styles I want to show you.”

He wondered what they could be. Judy’s hair was not much longer than his. Maybe she had some styles a boy could wear. “Maybe next Monday?”

“Sure.”

When he got home, he was going to wear his Hello Kitty tee again, but it was stained from working in the kitchen. His mother never liked him in dirty clothes. He didn’t want to wear lace or satin, so he wore his Princess tee with a training bra. Looking in the mirror, he noticed that its lavender complimented his skin tone. He recalled that the yellow tee had given his face a sickly cast. It was the first time he’d related his clothes color to his complexion. Maybe that’s why his mother picked out two lavender tops. Thinking about it, he realized that the same must be true of make up. For a second he imagined wearing lavender eye shadow, but turned from the mirror in utter embarrassment at this thought.

Again, Martha arrived as he was cleaning up from breakfast. She was very pleased with her daughter’s new-found helpfulness and gave her an affectionate hug and kiss. Inspired by her tee, she said “Thank you so much, Princess.”

Jerry blushed, but was happy Martha was pleased. “Your welcome, mommy.”

His blush made her reflect that Jerry was a boy – but, was he? Really? He didn’t look like one – and he was still wearing nail polish. That wasn’t part of his self-selected punishment. How could she have missed his femininity before? The poor child must have hidden his true nature. She’d help him be more feminine from now on.

The rest of the week was more of the same. Jerry got used to putting on a bra and top when he got home, and enjoyed his new-found closeness with his mother. He even felt a sense of accomplishment when he did his share of the housework.

V

The following Monday, Jerry’s punishment was over, but Martha had decided to test her son’s inclinations by leaving a present on his bed.

When he got home he found a white box with a pink ribbon. Under the ribbon was a card, “With all my love, Mommy.” Opening the box, he found a lavender panty and bra set with gorgeous lace detail. Jerry knew he did not have to wear it. Still, it was a gift from his mother. He told himself she'd be offended if he weren't wearing it when she got home. Once he had his lingerie on, he knew it was too fancy to wear with a tee. His lavender satin blouse went with it perfectly.

He wanted to look his best for his mom, so he went to the bathroom to fix his hair. He was waiting for his mother’s curling iron to heat when he heard the doorbell followed by a knock. UPS man rang and knocked like that to signal a delivery. As their porch was enclosed with an arch and obscured by bushes, he wasn’t shy about gong out en femme to retrieve packages once the deliveryman left. He opened the door and was about to step out when he saw Judy.

“Hi! You’re as cute as I imagined.”

Jerry froze in the doorway.

“May I come in?”

“Ah … yeah,” he said stepping back.

“I … I didn’t expect you.”

“Oh? Last week you said I could come over today with the Seventeen article on short hair styles.”

“I … did?”

“Yes … don’t you remember?”

He shook his head, no. Tears were forming in his eyes.

“Oh dear! I didn’t mean to embarrass you. … Do you want me to leave? I promise not to tell anyone, … but I do think you look adorable,” she said with all sincerity.

“You … you really don’t mind that I’m dressed like a girl?”

“Of course not, silly.” She kissed him in the cheek. “I’ve known ever since I saw your panty lines last Monday.”

“Panty lines?”

“Yeah, panties have narrow waist elastic. Besides, I have a pair of the slacks you're wearing – only in pink.”

“Didn’t you think I was weird?”

“Well, different fur sure, … but I thought you were brave to wear what you like to school. That’s why I complimented you.”

“I appreciated it. … So, why’d you make friends with me?”

“Because you’re nice. You notice other people and care about them. … Also, I don’t like the boys that pretend to be tough. I’m lot more interested in feminine boys – except Marty Collins. … You do like girls, don’t you?”

“I’m interested in you … I didn’t used to be interested in girls, but I’m not interested in boys like Marty is.”

“Good! … So how long have you been wearing panties and all?”

“Not long. Just since last Sunday.”

“Really? Well, it suits you. You like it, I can tell.”

“Don’t you think I’m weird? … or a sissy?”

“What’s wrong with being a sissy?”

“I don’t know. … People pick on sissies,”

“Well, I don’t. … How’d you start?”

Jerry was relieved to have an accepting friend. So, slowly at first, he told his story.

“It’s so cool that your mom gave you a push and is helping you.”

“Yeah, … I guess it is.”

“Do you have any skirts or dresses?”

“No, just slacks like the ones I’ve worn to school.”

“I could loan you some.”

He imagined his skirt flaring out as he did a twirl. His heart beat faster. “I don’t know if I’m ready for a skirt.”

“Well, think about it. I have some cute ones and we’re the same size.”

Jerry was blushing so hard that Judy decided to change the subject.

“Want to see the short hair styles?” she said holding up the issue of Seventeen she’d brought.

“OK.”

Judy sat on the sofa and patted the place next to her. Jerry felt like a complete sissy, but, strangely, he didn't care. They finally agreed on a style that they both liked and that wouldn't require cutting his hair.

When Martha came in she heard girlish giggling coming from the bathroom. As she peered in, she saw Judy spraying and primping Jerry’s hair. She took a quick picture with her cell. The flash startled the children.

“Mom!”

“Who’s your stylist, sweetie?”

“Ah … This is Judy Michellini … my friend … I told you about her.”

“Hello Judy. You two look like you’re having fun. Have you been behaving.”

“Yes, mommy!”

“I don’t want to lie to you Mrs. C. We did try each other’s bras. I was jealous that Jerry’s chest looked bigger than mine and his new bra is so pretty. My mother says I’m too young for a push-up.”

“Is that all?”

“Yes.”

“Well, that seems harmless enough. I appreciate you telling the truth, Judy. Do you both have your own on now?”

“Yes,” they said together.

“Well, Judy, you seem to have some talent. Jerry’s hair is very pretty.”

“Thank you, Mrs. C.”

“We’ll be eating shortly. Would you like to join us, Judy?”

“I’ll have to ask my mother, but if she says okay, I would.”

And so began a life-long relationship.

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Comments

If only

parents, girlfriends, and people were that accommodating in RL...

Remembering to sit...

Is this story going to be a solo. It has some good potential to become a rather nice story. Judy could suggest to is mother that he needs a skirt.

Jessie C

Jessica E. Connors

Jessica Connors

Solo?

I was thinking that it would be a solo, but I realize it hat the potential to continue. We'll both have to see if the muse moves me to continue it.

Andra

Very nice... the slow

Donna T's picture

Very nice... the slow evolution to enjoying feminine clothing and things.

Donna

As Jerry's age 11; I can see

As Jerry's age 11; I can see Jerry slowly becoming Jeri and showing up, in public, at school, and by the time s/he is in late Middle School or early High School; it will Jeri, the girl full stop, with her girl friend Judy as her BFF.

I would love

to see more of this story.

Thanks

Thanks to all for the kind comments. I will see if there is more of this to be told.

I re-read this and think

Donna T's picture

I re-read this and think there should be a followup story. Will there be one? Let us know. After all Jerry "... imagined wearing lavender eye shadow... " right? And maybe new friend Marty would like to try some too. I'm sure they would both find several willing enablers to help them into more femininity.
Thanx!
Dee

Donna

Thank you

Thank you for liking the story enough to want a follow up. I will reread it and see if the spirit moves me.

This Chapter is listed under

Uhuru N'Uru's picture

This Chapter is listed under
Remembering to Sit

Lokks like you set the wrong Book on Organization Page, You can edit it there.


Dark Elven Sissy Slut – Uhuru N’Uru

Thank you

For commenting, but I am confused. This story is "Remembering to Sit."