Sissy School - Chapter 3 - Guyagon Alley

I was locked in the trunk of Tyrone's car, bouncing down the road in pitch black. I was still cuffed and gagged from before, but thankfully I no longer had the used condoms still in my mouth as they had made me chew them like gum until I could swallow them whole. 

I was practically naked inside the trunk, the only thing they let me 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 my abused asshole. 

Tom's average sized-dick fucking my 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 as my ass simply couldn't take anymore, even though it did feel like he was tearing me a new one.  I think I blacked out from the pain, because all I remember was waking up to their smiling faces, feeling like my hole was gaping open as he slid his slimy member out of me. 

I felt every bump on the road as we sped along in the car. Where we were going I had no idea, I had lost track of the twists and turns a long time ago. 

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

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

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

I examined my surroundings and saw it was just a towering set of appartment buildings in a run down neighborhood. 

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

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

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

He led me along the sidewalk as an officer would some thug he just detained. People walking by must have assumed I was just some homeless person being relocated. I certainly looked the part. I was filthy, sweaty, and the only thing I had on were these disgusting underwear. 

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

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

I looked at Tyrone to see if we needed to go back, thinking we 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 my 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, as 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 I 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 my reaction as Tyrone dragged me through the opening in the wall. When I finally took my eyes off the gatekeeper and turned around, I was astounded at what I saw. 

What struck me first was just how much pink there was. The buildings were all pastel pink, as well as the outfits of all 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 I assumed were in the same situation as me.  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 me through the crowd, I noticed one woman dragging her husband by a leash while he crawled on all fours. I 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...I thought, but I knew that wasn't the answer he was looking for.

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

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

We 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, we arrived at Madame Taulkin's Fashion Shop. Instead of mannequins in the window wearing clothes, it was actual sissies. The only reason I 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 we 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 me, making me do the talking.

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

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

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

Once she had my 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 side. She picked up one by the hanger and held it up in front of me. 

"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. I glanced over at Tyrone, who had a stern look on his face that said You better do as she says...

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

"How does that feel?" she asked.

"Tight..." I replied, trying to suck in my gut. 

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

She moved around behind me and started tightening up the bows around my back. As she pulled them tighter, all the wind was pushed out of me, the dress must have had a built in corset, and it felt like my 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...i thought as i pulled my crusty undies down...This is where I get put in a diaper...

But to my surprise she just pulled out a pink, lacy thong that matched the dress. She helped me step into each leg and then pulled it up around my waist. I felt immediately like I had a wedgie, but my tiny cock and balls fit perfectly in the front. A white pair of panty hose followed, my 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.

I had trouble stepping into them, and had to hold onto Tyrone for balance. Once I was in she strapped the top around my shins, and two tiny padlocks came over the straps to ensure I 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, I felt clumsy and ridiculous. When I saw myself in the mirror, I felt even more ridiculous. I looked like a pathetically fat man trying to squeeze into their daughter's baby clothes. My face immediately turned a darker shade of pink than the dress I 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 rung it up, a grand total of $2,345.

"I...can't pay that..." I said. Not that I 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?" I asked.

He and Madame Taulkin both laughed at my naivity.

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

"Working it off how?" I questioned.

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

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

I rolled my ankle several times as I stumbled in my heels as we walked the shopping alley.

We stopped at Dildo Baggins.  I 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 I picked out every type I needed from the list, ensuring they were the proper size as well. When it came to a suction cup dildo, he made me get the one that looked like a realistic giant black dick. "Something to remember me by" he chuckled.

We 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 my bags and on my running tab.

We got my 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.

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

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

As we walked through the store, we 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 mine, and his diaper smelled something awful. Tears were raining from his face as he begged and pleaded, but she 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!" I heard her say as we passed by.

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

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

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

She proceeded to show me 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 was scented ones and extra padded ones.  I ended up picking the ones with prints that were the least girly in my opinion.  They just said "B A B Y" on them in little blocks, which to me 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. I couldn't imagine having to use every last one of them. I couldn't even imagine using one of them.

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

My stomach dropped, my mind immediately jumped to the sissy I saw on the floor before. I 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 I felt myself heave a huge sigh of relief.

The diapers were loaded up in a trunk along with my 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 my new pink diaper bag.  The girl bid me farewell, smiling sweetly as we left. I almost thought it was genuine. 

I was snapped from my reverie as we arrived at The Leaky Clitty to get something called a 'chastity device'. I had no idea what that was until I walked in and saw a wall to wall assortment of tiny, dick-shaped cages made of various materials.

The owner, Olivia, greeted me 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. I didn't get it.

With no regard for my personal space, she immediately came up to me and lifted my skirt up. "Let's see what we're working with...Hmmm...not much..." she teased, pulling my panties down so that my 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 my feelings, she pinched the head of my cock and slid one of the rings over it, feeding my balls through as well, the other end came next and locked in place.

"Hmm...too big..." she said, even though my 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 my cock had been touched by anyone other than myself 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 my tiny dick had to fold in on itself under the foreskin in order to squeeze inside. "Try getting hard in that!" she giggled.

I couldn't imagine, I was completely limp and my 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 my panties up over my caged-cock for me, if it weren't for my balls bulging underneath them, you wouldn't even know I had a cock.

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

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

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

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End of Chapter 3. If you're still enjoying this story, things are about to get much more interesting! Find out what happens next when Chapter 4 "The Makeover" cums soon!