Sissy Pool Wager Pt. 01

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself!

As you could imagine, an 18-year-old horny boy like myself really got into my porn, which for the last year had been all about sissies, while imagining that I was that sissy. I had dresses in my sister's slutty clothes for a while, taking pics and sending them to strangers online, this was addicting.

I finally got to a point where I needed to get more physical, while still being unable to seduce a man voluntarily, so I came up with my idea.

The next Saturday night, I went into the city to a big gay bar, with my sissy clothes in my backpack (white thigh highs, white garter, neon pink mini skirt, white crop top, and 6-inch neon pink platform heels) while also wearing a sexy pair of black panties and a black lacy bra under my guy clothes.

I went straight to the pool table, and asked who was willing to make a bet with me, and instantly had my pick of 6 men. It was a quick decision for me, as I chose the tall, muscly black man who was even taller than me. I had seen him playing pool earlier and he was incredible, which is just what I wanted.

Feeling very nervous, I showed him what was in my backpack and told him that I'd suck him off in the bathroom if he won, and that if I won we could agree on something reasonable at the time (I knew I wouldn't win). The game was over in 10 minutes and before I could consider my options I was being dragged into the bathroom.

He shoved me into a stall, threw my backpack at me and told me to get dressed, and put my guy clothes back in the bag. Trembling with fear I did as he said, and opened the door again looking like a big sissy slut. He just smiled, and took the backpack with my boy clothes out of the bathroom, before coming back and pushing me onto my knees. Over the next 15 minutes I was powerless to stop him and the massive man put his 9-inch cock in my mouth and fucked my throat, while insisting I stare him in the eyes the whole time. He recorded the whole thing on his phone, as he gave me instructions.

"Suck my balls bitch"

"Lick up and down my cock slut"

All of which I did for him.

I could feel he was building towards a climax, but before I could act he took his huge cock out of my mouth and blew his load all over my face. I was amazed at the amount he released, and stunned to be covered in it. Before I could react, he grabbed my arm and handcuffed me to a pipe.

I was in tears by now, as he told me how he'd make a profit by taking money from horny men outside the door, and letting them fuck my mouth and ass. He then took my phone, and set up a livestream on Facebook.

"Please don't! I'm begging you" I cried as he turned on the livestream and propped my phone so it captured the moment.

"Okay slut, tell me how much you enjoyed sucking my cock, and how much of a sissy slut you are, and I won't turn this on," he stated.

I was quick to answer, "master I loved sucking your big juicy black cock! On my knees with your cock down my throat is the happiest I've ever felt, and it made me feel like such a submissive little bitch!" I said with a smile, hoping to convince him.

Little did I know, he had already started the stream, which was filming me live to everyone I know, talking about how much I loved sucking cock, while sounding genuine! I was on my knees, handcuffed to a pipe, wearing the sluttiest sissy outfit I possibly could, with my face covered in cum.

Over the next 3 hours I sucked and fucked over 20 cocks, live on Facebook. By the time I was finally released, my master had made $1000 by charging every man $50, while my mouth and ass was in the most pain I could imagine. I was completely covered in cum and with my knees so sore from being on my knees for so long, it took me about 10 minutes just to stand up on my massive pink heels.

"My name's Josh" my black tormentor finally told me, as he put his number in my phone, after turning off the livestream. "Call me tomorrow, or else. I looked through your phone and I know where you live" he told me.

Through tears I agreed, before he pushed me out of the bathroom and then out of the pub into the city street, still in my sissy clothes.

"I'll give you the backpack tomorrow night bitch," josh told me with a smile, as he pushed me away.

I was now walking the street dressed like a massive sissy, covered with cum, as I tried to get to the train station. I didn't have my wallet or anything.

That was when the police car pulled up next to me.

"Face the wall and put your hands above your head!" The cop yelled at me.

I did as he said as he handcuffed my hands behind my back and pushed me into a dark alley with the other cop behind him.

"You're under arrest for street prostitution sir. But that ass looks very good bitch. Bend over."

I then took the 6-inch cock of the cop in my ass, while I sucked off the other cops 8 inch cock. By the time they were finished, I was covered in more cum, and even more sore.

They then took me into their cop car, and took me to their police station, before locking me up for the night with the other men, not allowing me to change clothes or even shower.

This is how the story ends. All my family, friends, and other people I know thinking I'm a huge sissy faggot after the livestream. A master I'm going to have to see countless times. A criminal record which will prevent me from getting a good job ever, and myself sitting in a large cell all night with 5 other men, dressed in pink heels, white stockings, white garter, black panties and bra, pink skirt, and white crop top, while also covered in cum.

To be continued...