A boy, an older sister, dress up and Father catches them in the act! Ralphie and Dad reach a new understanding.

An oldie that somehow never got migrated to Top Shelf.

Sidedressing

Br Tyrone Slothrop

Older sisters can be a boy’s good friend and most effective torturer. Bernadette, charged with watching her little brother, was getting bored and decided to see how far she could manipulate him. Nothing nasty just keeping her hand in. Practice makes perfect.

“Ralphie, come here, I want to try a new game.”

Ralph heard his sister and put down his videogame. He wandered into her room. At thirteen he was fairly average in height, about five feet nine inches. He was at that stage when the pudgy baby fat is leaning out on his frame, but he still had a friendly round face. He liked Bernie most of the time and didn’t give her much trouble when she was in charge of the house.

“Stand up Ralphie, I was wondering how brave you were.” Bernadette, called Bernie by everybody said in that challenging yet alluring way older girls have with boys.

Ralphie fell for it. “I’m pretty brave, Bernie.”

“Well, some of the older girls were saying that boys would be too scared to even try on some real clothes. Like it would bite them or make them instant girls or something. I said it was silly. What do you think?” Bernie laid the trap, quickly and efficiently.

“Just to try them on? But some of the clothes aren’t that different. That’s ridiculous!” Ralph said.

Bernie smiled. She stood up and started to remove her skin tight jeans with the flowers on the pockets. “Then I want to see these on you! Then I’ll tell them they are wrong!”

Ralph swallowed hard. He had always wondered what girls’ clothes felt like.

“Bernie, those? Your pants? Won’t they be a little tight down here for me?” Ralph indicated his groin. His Dad had always told him to protect ‘the family jewels’.

Bernie smiled and pulled her jeans up. “Ok, Ralphie’s scared of some old jeans. Ok how about these? These are pretty loose in the crotch, young man and you’ll look fabulous!”
Bernie showed Ralph a pair of billowing harem pants with an elastic waist.

Ralph undid his clothes and Bernie helped him don the gauzy garment.

In the mirror, Ralph was overcome. He was wearing girl’s pants!. He started to feel himself get really hard. He blushed.

“Ralphie, you’re not the first guy to get turned on by women’s clothing. Do you like it?” Bernie was fascinated by her brother’s erection, poking out in the loose fabric of the harem pants. Being fifteen, she had heard about these but this was her first actual sighting.

“Bernie, I feel kind of weird.”

“Aroused, I would say. Can I see it? Please? I’ll never tell anyone. I promise.”

Bernie had never broken a promise to Ralph. So Ralph sheepishly pulled down the pants. Bernie’s eyes went wide.

“Ralph, it’s so big.” Bernie desperately wanted to touch it but the brother sister thing was starting to reign in her enthusiasm.

“Can you make it go away, Ralph?”

Ralph knew he could and excused himself into the bathroom. He returned a half hour later, feeling very relaxed and still wearing the harem pants.

“Bernie, I’d like to try your jeans now but I think my waist is too fat.” Ralph said, clearly beginning to relax and have fun.

“Just the thing, little brother, or sister. I’ll give you my bodyshaper and make sure you wear it over your underpanties or whatever you call them so it doesn’t hurt you. Then you should be able to get into them fine.“

Ralph took off his top and Bernie pulled the bodyshaper camisole over him, being careful about fastening the crotch. She kept it loose, only doing half the snaps to let Ralph have some room.

Ralph looked at his new shape. The little love handles on his waist were pulled in nicely. He pulled on Bernie’s jeans, actually with more ease than she had.

“The cups are the wrong size.” Ralph said, indicating the chest area.

Bernie laughed. “Well we are a bit different sizes there. Forget that for now, let’s see you.”

Ralph spun around. It felt good, a bit less exciting with his crotch held so firmly.

“I think you should try being a blonde. Let’s see this.” Bernie produced one of her clubbing wigs, a blonde full pageboy with bangs. She tucked Ralph’s hair under it and arranged it on him.

“I like being a blonde, Bernie. “ Ralph smiled.

After another hour of trying on blouses and some makeup, they were laughing and giggling. They had not heard Father enter the house.

“Young lady , or should I say ladies, what is going on here?” Dad was there, in the door with his arms full of shopping bags. He was supposed to be out picking up some things and usually took much longer on a Saturday. He wasn’t angry, or yelling, but the kids knew he was not in the mood for evasions or jokes.

After some flustered babbled explanations , Dad did the first thing a parent needs to do when confronted with any situation like this. Separate the perpetrators, just like the cops do.

“Ralphie, please go to your room for a minute, I’ll be in shortly. Do not change, I want you to stay just like that until I come over. Oh yes, you can undo the crotch snaps on that camisole, it will relieve some of the pressure.”

Ralph knew resistance was futile. He went and waited for his doom.

Dad looked at Bernie sternly.

“Bernadette, did you take advantage of your brother? In that way?” Dad was calm but serious.

Bernadette crumbled. She confessed to wanting to see it, she never had seen one. She confessed to many things, some of which Dad filed away for later proceedings.

”Okay, every girl has natural curiosity. I’m glad you stopped yourself, that’s a sign of character and all young ladies need character. I assume that dressing your brother was just a game? A regular torture to see just what you could get him to do? You aren’t interested in girly boys?”

Bernie was adamant and convincing. She was not interested in girly boys or other girls.

“Ralphie did make a really good looking girl, didn’t he? “ Dad grinned.

Bernie smiled and nodded, her ponytail bobbing.. She had escaped! Dad was moving on.

As Dad got up to leave, he said “Oh, by the way, your pants need a rest with the workout you gave them here. You are to wear your skirts or dresses for a week. No exceptions. Okay?”

“But Dad, none of the girls my age wear dresses to school? And what about softball? I have a game this week.”

“No exceptions. You wore dresses when you were little, you wear them on Sunday and you’ll wear them when you get older. Keep in practice. I also know your uniform comes with both a skirt and pants. So the skirt is just as regulation. I’ll be at your game with my camera, too.”

Bernie pouted but realized she was getting off pretty light. She would just have to suffer through the ballgame. Two other girls wore the skirts, but they were geeks. Oh well. Dad wasn’t that bad at this discipline stuff, better than Mom had been. Bernie shuddered at that thought.

Dad went over to see Ralph. “My, what a pretty girl! Please stand up for me Ralphie. I want to see the full effect! “ Dad went on, not sounding sarcastic, just firm.

Ralph stood up, blushing so much it shone right through his makeup. He stood there in one of Bernie’s white blouses which showed the camisole with its ill fitting cups right through the fabric. His waist was held in and it he had a rounder shape to this hips and butt. The pants made his rear end jut out a bit, like two bubbles. He was wearing flat sandals without socks or stockings, showing off his bright red toes. The blonde wig changed the way his face looked, thinning it out a bit.

“Okay Ralph, do you like this? I’m not mad, you are not going to be punished. I just want to know if this is something you’ve always wanted to do or you did it on a dare with Bernie. Care to tell me?”

Ralph teared up. “Dad, I don’t know. I’ve never thought about it, except in some of those comedy bits on the video where everybody has to dress up to hide, that stuff. I’ve never done this before. Honest! Please believe me!”

Dad hugged the shaking Ralph. “Ralph, almost every guy does this once or twice. It’s no big deal, unless you find you really like it, then it becomes important. You probably don’t know what you want, what with the hormones and stuff that happens at your age. So here’s what we’ll do. Take a shower and get dressed. I’m sending Bernie over to her girlfriends for a few hours. We’ll order some pizza, watch some videos and have some man talk. You can take your time and if you want to do this again, tell me. I’ll help you deal with it. Ok my man?”

Ralph hugged Dad and nodded yes.

Dad walked down the hall to get casual for the evening after he told Bernie to ‘get lost for a few hours and yes she had to wear a dress over to Sarah’s place’. He was working over in his mind how pissed he was that his wife, sorry, his ex-wife, wasn’t here to help with this. She had dumped him for that writer and now there was the alimony dispute. It seemed ridiculous with her leaving him with the kids and all to try to still play games over money. It was a good thing his magazine was doing well.

Downstairs about two hours later, Bernie already gone to Sarah’s next door, he heard Ralph descending the staircase. He knew Ralph had showered, he heard the water running earlier. Ralph came in and sat down next to him on the couch in front of the screen.

“Your looking sharp, Ralph, like a real solid young man. The pizza should be here soon. I hope you’re hungry.” Dad said.

“Dad, why do girls get all the choices in clothes? They can wear pants or skirts and guys are restricted to one choice.” Ralph went on.

“Ok Ralph, you know you are built differently than girls especially right here.” Dad said, indicated his own crotch area. He continued. “You need underwear like the ones you have to protect your stuff and also to keep your sperm fertile. That’s important. So you wear what you have. Now those pants of Bernie’s you had on today, they felt pretty restricted, didn’t they?”

Ralph nodded.

Dad went on. “You know, the way you are looking, the girls will want to really get to you. I’ll bet you’ve had few already approach you, right?”

Ralph smiled. “A few, especially that Marcia Fredricks.”

“That girl is just plain boy crazy. Has she offered you a blowjob yet? Don’t be shocked, son, you’re old enough to deal with this.” Dad said, watching Ralph’s face open in awe.

“Yes she has but we were on the bus.” Ralph stammered.

“Ok, Ralph, let me ask you. Do you like girls or want to be one? Or are you not sure. Any answer is ok.”

“I like girls. I would have let Marcia do it if we were alone.”

Dad grinned. “I thought so. And I know you got a hard on when wearing Bernie’s clothes. Don’t worry about it. At your age it happens at pretty uncontrollable times. When you get to be my age it’s less like that, more controlled.“

The pizza arrived. The girl who delivered it gave him a big grin and said she’d see him at school. Dad gave her a good tip.

“She likes you, son. What do you think of her?” Dad said while chewing on a slice of pepperoni.

“She cute and not as nasty as some of the other girls. She makes me feel pretty good.”

“Nice rear end too. You should get to know her.” Dad said. “ But wear your control pettis, you don’t want an accident with her around.”

Ralph nodded in agreement. “I sure don’t want a hard on right in front of her. Guys have it tough. “

Dad smiled. “Yes, you know a girl gets us excited, and a good one takes the time to get us hard. Then she rides us and we make sure she has her orgasm. The few good ones out there make sure to take the time to let us come afterward. Your Mom was like that at first. “ Dad got quiet. “I’m sorry Ralph. I didn’t mean to go on like that.”

“Dad, it’s ok. Mom was a bitch to dump you. And now she’s trying to screw you out of your alimony. You’ve been great to Bernie and me.”

Dad hugged Ralph so their breasts squeezed into each other. He kissed him on the cheek and left a lipstick print.

“I’m sorry Ralphie. I’ve smudged your makeup. Let me fix it.” Dad said.

Dad got up and Ralph was amazed at how good he looked. Long brown hair, a nice full curvy figure with a really great set of boobs. His casual dress was great, but then he was a fashion magazine owner and he knew clothes. His skirt was full and at the fashionable mid calf length and he had his casual heels on, a thin three inch style. Ralphie had matched his nails and face to look like his Dads. He felt comfortable in his control pettipants, frilly panties specially designed to cushion his private parts and provide protection, along with several inches of foam which made his skirts drape better. All boys graduated to them once they started to develop. Bernie’s pants had not been comfortable or felt safe.

He was in a dress similar to Dads and was wearing his favorite brassiere. It felt much better than those small cups on Bernie’s camisole. He had washed and set his hair just like Dad’s style.

Dad came back and took a tissue to Ralphie’s face, then applied some cover and blush.
“Ralphie, I have an old bodyshaper which you can use until I buy you some of your own. It is open on the bottom to give you maximum freedom for your manhood. I also want you to go to our endocrinologist for a check up and maybe get you hormone mix adjusted. You need to do that anyway. Do you want to go up another cup size? Normally I‘d wait until you are fourteen, but I think you can carry a D cup now. And you will get some more padding on your backside with it, like Dad has. “

Ralph was visibly bubbling over. “You’re the best Dad! Then I’ll be two up on Bernie! Great! I can’t wait.!”

Dad smiled He had one more enticement. “I did like you as a blonde Ralphie. But not so short. Your own length would be much nicer. I can take you to the barbers and Mister Fred can do wonders with color. What do you say?”

Ralph was feeling aroused again. Fortunately his pettipants had it under control. He hugged his Dad and some tears came.

Later that night, Dad thought about how his son was growing up. He mused over the times before the viral attacks had changed it all over one hundred years ago. Then , men and women were dressed differently but it was not so different. He was sure some parent had dealt with a son who did, what was the term? Crossdress? Redress, no sidedressing. That was it. His son was just having some sidedressing fanatasies. Normal.

Epilogue

Dad took his ex wife to court and kept his alimony.

Bernie took some grief at the ballgame but hit a three run homer. The coach sent the whole team to change into skirts to keep the rally going.

Ralphie let Marcia do her stuff. But he went steady with the pizza girl.