Sissy School Ch. 03 - Guyagon Alley

Larry was locked in the trunk of Tyrone's car, bouncing down the road in nothing but pitch black. He was still cuffed and gagged from before, but thankfully no longer had the used condoms in his mouth. They had made him chew them like gum until he could swallow them whole.

He was practically naked inside the trunk, the only thing they let him wear as they sarcastically waved goodbye was the pair of pissy undies from earlier. A mixture of Tom and Tyrone's cum was still leaking from his abused asshole.

Tom's average sized-dick fucking Larry's ass was painful enough, but Tyrone's giant cock? That was just torture. He wasn't even able to get it all the way in, Larry's ass simply couldn't take anymore, even though it did feel like he was tearing him a new one. Larry probably blacked out from the pain, because all he remembered was waking up to their smiling faces, feeling like his hole was gaping open as Tyrone slid his slimy member out of him.

Larry could feel every bump on the road as they sped along in the car. Where they were going, he had no idea, he'd lost track of the twists and turns a long time ago.

After driving maybe 1-2 hours, Larry finally felt the car come to a halt. Door opening, footsteps on pavement, keys rattling, the turn of the lock on the trunk.

He was blinded by the light when the trunk door opened. Again, Tyrone helped to eclipse it as he stood towering over him.

"We're here." he said, grabbing Larry by the hair and the cuffs and lifting him out of the trunk as if he were a small child.

Larry examined his surroundings and saw it was just a towering set of apartment buildings in a run down neighborhood.

"This is the school?" he asked as Tyrone removed the ball gag and feeling returned to his jaw. It definitely wasn't what he expected the school to look like.

"No," Tyrone laughed, "first we have to go shopping..."

"Here?" Larry asked, again in disbelief. Where was there to shop here?

He led Larry along the sidewalk as an officer would with some thug he just detained.

People walking by must have assumed he was just some homeless person being relocated. Larry certainly looked the part. He was filthy, sweaty, and the only thing he had on were those disgusting underwear.

They turned a corner and went down a random alleyway. There was a hooker on her knees giving a guy a blowjob. They both saw them and didn't even stop what they were doing. She just sucked and slurped harder while the man let out a slight moan.

Tyrone didn't seem to pay any attention to them, just kept walking down the alley until they came to a dead-end at a brick wall.

Larry looked at Tyrone to see if they needed to go back, thinking they'd made a wrong turn or something. But he just stood there firmly, picking up a metal pipe on the ground next to him. He counted 6 bricks right from the top-left corner, then 4 bricks down. Then tapped the brick he landed on 3 times with the pipe.

To Larry's surprise, the brick he tapped slid open, and a set of eyes appeared behind them.

"Password?" The man behind the bricks asked.

"Pixie Dust" replied Tyrone without hesitation.

Suddenly there was a loud screeching sound as what sounded like a bar was slid from behind the wall. Then the majority of the wall peeled open, and the false wall opened up like a door.

"Welcome to Guyagon Alley!" said the man behind the door. At least, it sounded like a man, but as Larry stepped through and saw him, he certainly didn't look like a man. He was wearing a long dress with a corset that made his boobs (?) look ginormous.

His hair was long, and he had more make-up on than a clown.

He (she?) just smiled at Larry's reaction while Tyrone dragged him through the opening in the wall. When Larry finally took his eyes off the gatekeeper and turned around, he was astounded at what he saw.

What struck him first was just how much pink there was. The buildings were all pastel pink, as well as the outfits of most of the people hustling and bustling around. Most of them looked like the gatekeeper. Almost everyone was in either frilly puffy dresses, or skin tight latex ones. And, upon further inspection, almost all of them were men. At a glance some of them could perfectly pass for women, it was only the presence of an Adam's apple that gave them away.

The only ones who looked like real men were the ones who Larry assumed were in the same situation as himself. They were all accompanied by Bouncers like Tyrone: big, burly, and mostly black. The few real women around also had their husbands in tow. As Tyrone led Larry through the crowd, he noticed one woman dragging her husband by a leash while he crawled on all fours. He saw men who looked like they were in hell, and saw some who looked like they were in heaven.

Tyrone clutched the pink paper that was the supply list in his hand. "So..." he said, looking at it, "where would you like to go first?"

I want to go home...Larry thought, but knew that wasn't the answer he was looking for.

"Can we...get some clothes?" he asked, feeling naked next to all these people while wearing only underwear.

Tyrone smiled, "Madame Taulkin's then..." and he led the way.

They passed by all sorts of crazy stores, Dildo Baggins, The Leaky Clitty, and some candy shop called Dollipops that was advertising a sale on Chocolate Starfishes.

Finally, they arrived at Madame Taulkin's Fashion Shop. Instead of mannequins in the window wearing clothes, it was actual sissies. The only reason Larry knew they were sissies was because of the little plastic cage dangling between their legs as they twirled around in the latest line of lingerie or dresses with extremely short skirts.

"Well hellllooo, my dears!" cried a voice as soon as they walked in. A rather busty woman came bustling over. There was no telling if she was an actual woman or not, as she wore an extremely long dress that puffed out at the bottom, and a frilly collar that covered her neck and ran down to her large, protruding bosom. "I'm Madame Taulkin! How can I help you?"

Tyrone nudged him, making Larry do the talking.

"I need...clothes..." he said, looking down at his feet, ignoring the inordinate amount of dresses and female outfits around.

"Well I'd certainly say so..." Madame Taulkin replied, looking him up and down disapprovingly.

She pulled out a tape measurer seemingly out of nowhere and started taking measurements. Tyrone uncuffed him so that she could raise his arms and measure his midriff.

Once she had the dimensions, she buzzed around the store like a fly on a window.

Bouncing back and forth, scooping up dresses, stockings, and petticoats with lightning speed.

She came back with a pile of different outfits, all of them different in style but all the same in color: pink. She set the pile down to the side. She picked one up by the hanger and held it up in front of him.

"Hmmm...I think this will do nicely..." she said.

The pink dress was made of mostly satin, with really puffy shoulders and delicate lace trim around all of the edges. Bows everywhere.

"Arms up," she said matter of factly, as if dressing a toddler. Larry glanced over at Tyrone, who had a stern look on his face that said You better do as she says...

He complied, raising his arms up so Madame Taulkin could pull the dress down over his head. He was surprised at how soft and smooth it was, but immediately as it came down and covered his chest it felt extremely tight. The skirt was so short it barely even covered his underwear. Even his tiny 3 inch cock would hang below it.

"How does that feel?" she asked.

"Tight..." Larry replied, trying to suck in his gut.

She scoffed and laughed a bit, as if to say "You ain't seen nothing yet..."

She moved around behind him and started tightening up the bows around his back. As she pulled them tighter, all the wind was pushed out of him, the dress must have had a built-in corset, and it felt like his ribs were breaking as she tugged with all her might.

Once that was fastened she looked up to admire her work. "Perfect fit!" She said smiling. "Now you can take off those hideous undies...I have something much more...fitting...for you..."

This was it...Larry thought as he pulled his crusty undies down...This is where I get put in a diaper...

But to his surprise she just pulled out a pink, lacy thong that matched the dress. Larry felt silly for being relieved that he'd only have to wear panties instead of a diaper. She helped him step into each leg and then pulled it up around his waist. Larry immediately felt like he had a wedgie, but his tiny cock and balls fit perfectly in the front. A white pair of pantyhose followed, Larry's leg hair sticking out the sides.

"Now for shoes..." she said, dipping back in her pile. She pulled out a pair of pink high heels with some sort of strap around the top.

Larry had trouble stepping into them, and had to hold onto Tyrone for balance. Once he was in, she strapped the top around his shins, and two tiny padlocks came over the straps to ensure Larry couldn't remove them.

"There we are dear!" She cooed, "Now turn around and look at yourself in the mirror!"

Turning around in the heels was awkward, he felt clumsy and ridiculous. But when he saw himself in the mirror...he felt even more ridiculous. He looked like a pathetically fat man trying to squeeze into their daughter's baby clothes. Larry's face immediately turned a darker shade of pink than the dress he was wearing.

"Don't you look just adorable!" Madame Taulkin cooed.

There was no need to try on the rest of the clothes, they were all sized 'perfectly' according to Madame Taulkin. She carried all the stuff over to the register and rang it up, a grand total of $2,345.

"I...can't pay that..." Larry said. Not that he even wanted to spend that much money on all of these outrageous sissy clothes.

"Oh you don't have to...yet..." Tyrone said.

"Watta you mean?" Larry asked.

Tyrone and Madame Taulkin both laughed at his naivety.

"Your debt accumulates throughout your time at school" she explained, "Once you graduate, you will start...working it off."

"Working it off how?" Larry questioned.

"Well...that depends on where you get sorted." Again they both laughed. Larry had no idea what they were talking about.

All of the clothes were loaded up in bags that he was forced to carry out of the store.

He rolled his ankle several times as he stumbled in the heels as they walked the shopping alley.

They stopped at Dildo Baggins. Larry didn't think so many plastic and rubber dicks existed. They came in all sorts of sizes, (some of them were outlandishly HUGE, bigger than a log you would throw on a fire) Tyrone made sure he picked out every type he needed from the list, ensuring they were the proper size as well. When it came to a suction cup dildo, he made Larry get the one that looked like a realistic giant black dick. "Something to remember me by..." he chuckled.

They walked into a Sissy Supply store which looked like it was straight out of a Bachelorette party: everything in there was penis shaped. Pens and pencils looked like long skinny cocks. Straws, baby bottles, pacifiers, all had little rubber dicks at the end of them. All of them ended up in Larry's bags and on his running tab.

They got his books at Flowers and Dotts. Entire volumes of books on The Art of Sucking Cock complete with various pictures of women and sissies with giant dicks in their mouths, looking like there's no other thing they'd rather have in there.

Larry was hungry, so Tyrone let him stop at Dollipops and buy a bag of gummy dicks to eat. They tasted funny, and reminded Larry too much of the cummy condoms he'd had earlier.

Eventually they came to the Diaper Depot, where inside there was wall to wall covered in different types of giant, adult-sized diapers.

As they walked through the store, they passed by one crying sissy who was on the floor getting his dirty diaper changed by a beautiful woman. His dick was even smaller than Larry's, and his diaper smelled something awful. Tears were raining from his face as he begged and pleaded, but the woman was all smiles, enjoying his humiliation as she changed him and talked to him as if he were an actual little baby.

"There there, Mikey, it's okay! It's okay that all the wittle sissies can see you! They'll be getting their diapers changed eventually too!" Larry heard her say as they passed by.

"Can I help you?" a pretty voice said, he turned to see a girl who looked like she was barely even 19 smiling at him.

Larry was speechless. "Uh...we need uh..."

"Diapers." she finished for him, "I figured that" he saw her eyes sweep over him and his ridiculous outfit, she tried unsuccessfully to hide a smirk "let's see what we have..."

She proceeded to show him the various types of diapers they carried. Almost all of them were pink or white, only a few were blue, as no one at school was permitted to wear blue. Apparently they were only for shipping to boys who still needed diapers, but weren't admitted to the school.

The diapers had all sorts of babyish prints on them, there were scented ones and extra padded ones. Larry ended up picking the ones with prints that were the least girly in his opinion. They just said "B A B Y" on them in little blocks which, to him, was better than princesses, rainbows, flowers, or unicorns.

"How many?" the girl asked.

"500" Tyrone replied.

It was nauseating to see them load up packs of 10 diapers that totaled up to 500. Larry couldn't imagine having to use every last one of them. He couldn't even imagine using one of them.

"Do you need me to change him into one now?" the girl asked.

Larry's stomach dropped, his mind immediately jumped to the sissy he'd seen on the floor before. He did NOT want to be that sissy. I'll put them on later, I can do it myself. PLEASE, just don't let this really hot girl do it to me.

"That won't be necessary" Tyrone said, and Larry felt himself heave a huge sigh of relief.

The diapers were loaded up in a trunk along with his other bags of sissy supplies, "They'll all be shipped to the school and will be in your room when you arrive" Tyrone explained.

That is, with the exception of 10 or so diapers, some dildoes, plugs, and other "basic necessities" as he called it. Those were all loaded up into Larry's new pink diaper bag. The girl bid him farewell, smiling sweetly as they left. Larry almost thought it was genuine.

He was snapped from his reverie when they arrived at The Leaky Clitty to get something called a 'chastity device'. Larry had no idea what that was until he walked in and saw a vast assortment of tiny, dick-shaped cages made of various materials.

The owner, Olivia, greeted him ecstatically. "Come in! Come in!" she said "Probably the last time you'll hear a girl say that to you, huh?" she laughed at her own joke. Larry didn't get it.

With no regard for his personal space, she immediately came up to him and lifted up his skirt. "Let's see what we're working with...Hmmm...not much..." she teased, pulling his panties down so that his tiny cock flopped out.

She scrambled back to the wall and scooped up a cage, not even bothering to take measurements. She brought back a tiny steel device. It looked like a series of rings fused together. Again, with no regard for Larry's feelings, she pinched the head of his cock and slid one of the rings over it, feeding his balls through as well, the other end came next and locked in place.

"Hmm...too big..." she said, even though his cock felt like it was fighting for space inside.

She took it off and tossed it to the side. Now, understand, this was the first time Larry's cock had been touched by anyone other than himself in months. So by the time she came back with the next steel tube, it was poking all three inches at her. She paid it no attention, however, just flicked it on the head and waited for it to retreat back and go limp again before trying the next 2-inch long cage.

This went on for several attempts until finally she came to one that she liked.

"Hmm..I think the Ultra Small HoD Z83 will do for you!" she came back with one that looked like a tiny button. Even Larry's tiny dick had to fold in on itself under the foreskin in order to squeeze inside. "Try getting hard in that!" she giggled.

He couldn't imagine, he was completely limp and his cock was still aching inside the cold little cage. She locked it up with a padlock and handed Tyrone the key around a chain, which he put around his neck.

Olivia pulled Larry's panties up over his caged-cock for him, if it weren't for his balls bulging beneath them, you wouldn't even know he had a cock.

"Where to next..." Larry asked Tyrone as they left the store, feeling utterly humiliated and defeated.

He looked Larry over and smiled, as much of an ordeal as all of this was for him, Tyrone seemed to really be enjoying himself.

"I think someone needs a makeover!" He said, taking Larry by the hand like he was a toddler and leading him to a place conveniently called the Sissy Salon.