"Hey mom," Ryan reached through the waistband of his shorts to scratch his boxer briefs clad butt. Why did mom always call at the worst time?
"Just calling to check in. Aunt Gertie's got your dad cleaning her gutters now, so we might be a bit later than I thought. You might have to order pizza or something for the girls. We'll let you know."
"That's fine."
"Are the girls still swimming?" Ryan looked out the back window and saw his sister and her friends jumping into the pool, their squealing laughter grating on his nerves even from inside.
"Yep."
"And why aren't you watching them?"
"I am."
"Not through the window. Go put on your trunks and sit by the pool until they're done."
"Their laughing gives me a headache." It was true, not that his mom seemed to care.
"Now, Ryan." He sighed, but knew his mom would find out if he did not obey.
With his trunks on, Ryan shuffled out to the pool, grimacing as the girls' happy noises grew louder the closer he got. He was only three years older than Mandy, but he felt like her and her friends were a different species from him, always squealing and laughing.
"What are you doing out here?" Mandy asked. "I thought angsty 14 year olds always stayed inside." Angsty 14 year old was a phrase she had borrowed from their parents and Ryan did his best to ignore it.
"Mom and dad are gonna be late and mom told me I have to come watch you." Mandy nodded and jumped into the pool, nearly splashing Ryan. He sat down on a pool chair and sighed, trying his best to ignore the laughing girls. He covered his eyes with a hand. The sun was too bright! Distracted by that, he did not notice that the sounds of splashing had stopped. He did not notice anything until there were half a dozen ten and eleven year old girls standing around his pool chair.
"What?"
"Swimming's boring. We have a new game we want to play."
"Okay, fine. Let's go inside or something." At least he could go back to his room. He stood up, a little unnerved that all of the girls were nearly his height. Mandy was an early bloomer or whatever, but all of her friends?
"Nope. The game's right out here." Mandy suddenly grabbed Ryan's wrists and pulled them behind his back.
"Ow! Stop! That hurts!" The girls giggled.
"Promise you'll do exactly what we say." Ryan could never keep his sister's friends' names straight, but he was pretty sure the girl who said that was named Rachel. Raquel, maybe?
"I promise. Ow!"
"Promise that you'll do what we say like a good little boy." Ryan groaned, but Mandy pulled on his arm until he perfectly parroted it.
"Alright. First things first, you're going to put this on." Mandy held up a pink and white striped swimsuit. A girl's pink and white striped swimsuit.
"What?"
"You promised to listen, Ryan. There's six of us and one of you. You're wearing this whether you like it or not." Ryan looked from face to face.
"Cover your eyes or something."
"Uh, duh. No one wants to see you naked." Once every girl had her eyes covered, Ryan struggled into the swimsuit, glaring at the stiff little skirt it had. It must have been one of Mandy's old swimsuits or something. It looked like a little girl's swimsuit.
Ryan groaned as it squeezed him all over. Did girls always wear such tight things or was it just too small for him? Probably both somehow? He had seen photos of girls in bikinis and they were tight in a good way.
"He's in it!" The girls seemed to move as one, shoving Ryan back onto the pool chair. Between the six of them, they quickly tied each of his limbs down so that he was stuck, struggling on the pool chair.
"Hey! Let me go! What are you doing?"
"You just got out here." Mandy said. "You need some sun." Ryan tried to pull even one of his hands free, but he could not.
"Mandy, this isn't funny!"
"Let's gag him!" Rachel or Raquel said. Ryan tried to dissuade them as quickly as he could, but he soon found a bandana tied snugly around his head, reducing his words to muffled mumbles. The girls giggled as Mandy held up a pair of sparkly pink heart-shaped sunglasses, which she pushed onto their captive's face. The lenses were so dark he could barely even see the girls beyond vague silhouettes.
"Alright, Ryan. You just relax in the sun while we do your nails."
"My nails!?!" Ryan tried to say, but all he could do was mumble and squirm. The only thing that accomplished was forcing the bottom of his swimsuit up between his butt cheeks, which only squeezed his front more.
“Do we have time to wax him?” One of the girls asked. Ryan’s desperate squirms made the whole chair shake to the point that a couple of the girls actually stepped back.
“Looks like Ryan just wants his nails done.” Mandy said wryly.
The girls giggled as his feet and hands twitched impotently as they painted each and every nail bubble gum pink. Mandy watched their work and grinned proudly. Other than his gag and the lump in the swimsuit, Ryan looked remarkably like a girl now. Seeing his phone nearby, she snapped at least two dozen photos.
"Go ahead and lift his sunglasses." She instructed. The girls giggled as Ryan groaned, closing his eyes against the now brutal assault of the sunshine. Once his eyes recovered, Mandy showed him the pics. "See, Ryan? We've doc-umented your first day as a sissy." She smirked as he snarled a thousand swear words at her through the bandana. "I'm sure that was you thanking us for finally making you the sissy you've always wanted to be, but we're not done yet." She held up a pair of pink earbuds. "These'll be going in your ears. Can you guess what kind of music you'll be listening to?" Ryan honestly did not know, but he knew all too well that he would not like the answer. "Barbie songs, Disney princess songs, and of course, your new favorite band, Sparkle Candy." Ryan's eyes widened. Sparkle Candy was the latest band that all the girls Mandy's age were going crazy for. No boy of any age wanted anything to do with a band that sang all about love and other girly stuff. "You always said the lead singer's a sissy, so now you'll be just like Kyle."
"Bet he'll be your favorite." Rachel said with a grin.
"Anyway, we're gonna go to the movies. You just hang out here and maybe we'll let you go once we get back. Might need to go for another swim though. Need to give you lots of time to learn every one of those songs by heart." Ryan pled for mercy as the sunglasses descended over his eyes and he felt the earbuds in his ears. The first song began and Ryan could do nothing other than try to get free, the sounds of a cheery Barbie song playing in his ears.
Betty Pearl's Sissy Stories 20.1
Topic: Sissy in the Sun (Read 8502 times)
