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My name is Sam. I didn't have too many friends growing up but I had a few people I hung out. One of my best friends was a kid named Josh whose mom was a single parent like mine. She used to travel a lot for work and would often hire a sitter. But as we got older, she started to trust Josh on his own. When we were in high school, she would leave every Friday for work and be back by Sunday night or Monday morning. She would let Josh stay by himself and leave him money for things like pizza or other takeout. I would stay over some weekends and it was always fun being left unsupervised. 

One weekend, when we were about 15 years old, Josh had invited me to stay over. I came over his house that Friday after school and his mom was already long gone. We hung out, played video games, ordered pizza. Before it got dark, Josh challenged me to a game of basketball. He had a hoop outside and we were always playing in our spare time.

"Let's make things interesting" Josh said. "Loser owes the winner twenty bucks."

"That's it? You're on."

"Why you don't think twenty bucks is enough?" he asked.

"I mean, if we're going to bet we can do better than that. How about loser has to do the winners chores for a month?"

He thought about it for a moment. "How about the loser has to wear a dress?" Josh suggested.

"What are you serious? You mean like to school?"

"No not at school. Right here. Inside. My mom has plenty of dresses and other clothing. How about the loser has to wear a dress for the rest of the night?"

I thought about it and figured it would be easy. "Deal."

Long story short, Josh wound up mopping the floor with me that day. I was usually the better basketball player but Josh was on his game that day. He seemed extra motivated. I found out why a little while later.

When the game was over and we went back inside, Josh said "I'll go pick your clothes out."

"You're kidding" I said.

"A deal's a deal. Besides no one else is going to see."

He was right. We made a bet and I had lost. I was never one to normally back out on a bet or a dare or a challenge. So I accepted my fate and told him to go ahead and pick something out. 

He went upstairs and came back a few minutes later and told me to go get dressed in his mom's room. I went upstairs alone and saw everything he had laid out on the bed. A red bra and matching red panties, a short black dress with straps and no zipper, and a pair of black pantyhose. He couldn't seriously be expecting me to wear all this. But I sighed and just went along with it. The underwear was the easiest part. And the dress wasn't complicated. But I did have a little problem with the bra and hosiery. I eventually got the hang of it though. I do have to admit the hose felt surprisingly good against my otherwise bare legs. I wasn't crazy about how short the dress was but it wasn't my choice. 

I came out of his mom's room and went downstairs. "Ok go ahead and laugh. Have your fun." But Josh was nowhere to be found. I didn't see or hear him. "Josh? Are you down here?" I went back upstairs and checked his room. I didn't see him at his desk or on his bed. I was about to turn around when I hear the closet door bang open and I felt someone pounce on my back. I fell to the floor and shouted "what the hell?!"

My hands were pulled behind my back and my wrists were bound tightly with a zip tie. I was able to turn my head slightly and see that it was Josh. Before I could question this any further, he took a white cloth, balled it up, and stuffed it in my mouth. I tried to spit it out but he covered my mouth with his hand and held it in until he could rip off a few pieces of duct tape to gag me. He picked me up off the floor and put me onto his bed.

Then he took some rope he had hidden in his closet and used it to tie my ankles together. "Don't worry the zip tie is temporary" Josh said. He took out his phone and snapped a few pictures. I mumbled and grunted into my gag.

"I'll explain later" Josh said. "For now I'm going to give you some time to get settled in and accept your fate."

Josh went downstairs to watch TV or eat pizza or do whatever he felt like doing while I laid on his bed, bound, gagged, and crossdressed. I struggled a bit but it was pointless. There was no way I was going to break the zip tie or squeeze my wrists out of it. And struggling just made it hurt even more. I tried testing the ropes by kicking my feet around and realized I wasn't going to get out of them either. Josh had done a good job. If I remember correctly, he was in the boy scouts when we were younger, so it makes sense he was skilled with rope and knots. 

He came back a few hours later and told me the pictures were insurance. "If you don't do what I tell you, I'm going to post this pictures anonymously online and make sure everyone from school sees them. So just play along ok?"

I nodded my head. "Mmhm" I grunted into my gag. 

"I'm going to cut the zip tie off so I can use rope to tie your wrists instead. Don't try anything funny."

He cut the zip tie off with a pair of scissors and I laid on my stomach and just let him tie my hands behind my back. "I hope you're comfortable because it's getting late. I'll untie you later so you can use the bathroom but you're going to spend the night tied up. Then I'll have a new outfit for you tomorrow."

I wasn't sure if he was serious or not but it turned out he was. He untied me so I could use the bathroom and eat a little snack before he made me lay on my stomach so he could tie my wrists behind my back again. He tied my ankles and then the cloth found its way back in my mouth and he gagged me with several pieces of duct tape.

I spent the whole night tied up and gagged on his bed. He slept in his moms room or on the couch I guess. I don't remember how long it took to fall asleep but I remember waking up the next morning with him at the foot of the bed, tickling my hosed feet.

"Cootchie cootchie coo" he taunted me. I growled into my gag and glared at him. 

He untied me and let me take my gag off. I used the bathroom and we ate breakfast. I asked him what was going on and asked him why he was doing this to me.

"A few years ago my cousin used to do the same thing to me. She would tie me up, gag me, tickle the hell out of me. She would make me wear her clothes. She would put makeup on me and make me wear wigs or her old shoes. I hated it at first but I eventually started to enjoy it in a strange way. And then yesterday when we were talking about betting on the game, I saw an opportunity to make this happen. I always wanted to recreate the experience I had with my cousin, but from her point of view."

"And the pictures you took of me?"

"Insurance. I promise I won't show them to anyone at all if you do what I say. But if you disobey me, if you don't do what I say, I'll post them online or show them to everyone at school. Got it?"

"So I take it we're going to be doing this again sometime?"

"Sometime? No we're going to be doing this a lot! Especially since my mom isn't usually around on weekends."

I groaned, wondering how I got myself into this predicament and if there was any way to get out of it. 

"Go upstairs and change. I left some clothes out for you in my mom's bedroom."

I went upstairs. There was a bra, a pair of panties, a silky red dress, and thigh high stockings. They were black and had what I learned later on were called Cuban heels. I knew nothing about pantyhose when this first started but quickly learned the difference between things like sandal foot and reinforced toe pantyhose and the different type of thigh highs and knee highs. I learned about tights and bras and dresses and more than I ever wanted to learn. But that all came later. 

In the meantime, I just went along again and put on the bra and panties first. I changed alone. Josh had left two clean socks on the bed that I could roll up and use to fill the cups of the bra. Then I put on the dress and slid the sheer stockings up my bare legs. I can't lie, I did kind of enjoy the feeling of the stockings. But I would never admit that to Josh.