Blackmailed by Mr. B

I was done. Mr. B had humiliated me for the last time. I wasn't going to be his girl anymore or anyone's girl for that matter. As I showered all of the grime away, I resolved to never go back. I had a beautiful girl, Maria, interested in me, and I wanted to pursue that more than anything. Besides, prom was around the corner, and although my virginity was gone in one way, I was eager to lose it the more traditional way. The only problem was that Mr. B was taking up all my free time. He had at least given me the following week off, thankfully, but everyone, Maria and myself included were far too busy studying for exams later in the week to do anything. I was scheduled to "work" for Mr. B the following Friday after school but I decided against showing up and made a date with Maria instead.

For the first time in a while, I felt like I was in control of my life. We decided on a local cafe and at first I was beyond nervous. My shyness had gotten the better of me and conversation was awkward but all of that disappeared after she started talking about herself. She was in gymnastics for most of her life, she liked emo music, she had two older brothers, and she loved animals, I couldn't stop looking at her while she spoke. I was falling for her without a doubt. Towards the end of the evening, our conversation turned sexual, when she brought up the fun we had in the boys change room at school.

"Were you nervous?" she asked me inquisitively.

"A little... I mean, yes at first." I answered.

"I heard that can keep guys from cumming. That probably means you'd last long during sex" she said giggling and I laughed with her before she continued, "unless you aren't interested in girls, of course."

She looked at me with a confident calm expression, not quite a smirk, but also not wholly innocent.

"No... I mean, I am... only into girls, that is." I said, stumbling on my words.

"Hmmm. We will just have to test that theory out more, won't we." she said with a wink.

I felt something begin rubbing my crotch and looked down with a start. She had slipped her foot out of her shoe and was now caressing in between my legs as she stared me in the eyes. She bit her lower lip and giggled.

"We are gonna have so much fun at prom." she said as she pulled her foot back, "Come on, you can walk me home."

The walk home was too short. I had held her hand the entire way and when she let go to climb her front steps, she stopped and bit her bottom lip.

"Wait here one second. I'll be right back."

I waited for a few minutes and when she came out she took my hand and put a small bundle of fabric in it.

"Here." she said with a wicked grin.

She kissed me on the lips before going back in the house, leaving me there. I opened my hand and saw what she had placed there. It was a pair of light pink panties, presumably hers. There was a notable wet spot right on the crotch. There was a folded up piece of paper with them. I opened it and strained to read it in the dim porch light. It read: 'you make me wet, here is the proof - show me I make you wet before you give my panties back to me - xoxo Maria'. I thought about what it could mean for a moment. My heart raced. She wanted me to cum on them before giving them back, at least that's what it sounded like.

I ran home as fast as possible, praying that I would actually be able to get hard enough to fulfill her request. My only mistake was not noticing my route took me directly past Mr. B's house.

"You know not showing up for work usually gets someone fired, but in your case, I'll make an exception." his voice came across his lawn and my run slowed to a stop. "What's that in your hand?"

I froze, not speaking, mind racing while I tried to figure out how to avoid a confrontation. If I could just get home, I could figure out a way to end things with Mr. B the next day.

"Well? Don't you want your money?"

That stung, especially coming from what could now be described as my pimp. I was technically already paid, 7 crumpled dollar bills, soggy and stained with the fluids I had been subjected to. I fully understood why it was seven, it wasn't random. One for each load that the men put inside me. As ashamed and angry as I was, the insinuation that I was entitled to more money from the transaction was alluring. After all, what was done was done, and if I was going to be dating Maria, a little money couldn't hurt.

"Yes" I croaked out, turning to face him.

"Well then come on up. It's in the house." he said, "On the kitchen table."

He made no movement from his chair on the porch, just continued to sip his beer. I walked slowly up the driveway and he wasn't even looking at me, his eyes were lower. I remembered my hand, stuffed with Maria's panties, and quickly forced it into my pocket. When I looked back, he grinned to himself. I opened the front door and as I stepped over the threshold, his hand grabbed my forearm to stop me.

"You know, being late is better than not showing up at all. Much better than leaving early without notice." he looked me in the eyes now, but I couldn't maintain his gaze and looked down.

"Your cut is on the kitchen table. So is something else you might be interested in." He let go and I moved past him inside.

The kitchen table had a twenty dollar bill on it. I should have known. He had received $2000 from Fred and the other men, and twenty dollars was all he was giving me. That was one measly percent, when I did all of the nasty, disgusting, demeaning work. There was something else on the table too. A stack of flyers. As I looked, my jaw dropped. Scrawled across the top of the glossy leaflet in pink bubble letters it said 'Candy the Cowgirl'. Just underneath, a picture of me, in a cowgirl outfit, squatting on a big hairy man dick while two more were positioned on either side of my face. Underneath, was a description,

'Candy is a bonafide femboy cowgirl that can milk even the meatiest hog. No job is too dirty for this little slut, and yessiree she does groups too. She is a regular boygirl-next-door, shy with a real perky ass that makes up for the lack of tits. Best of all, she enjoys every last minute of use, probably even more than you!'

Underneath there were reviews:

"Hottest little fuck I have ever had."

"Get her while she is still tight"

"She cums without being touched or fucked. Just humiliate her and that bitch will squirt her juice."

At the very bottom of the leaflet, just under a section titled contact information, my address and phone number was printed with the words 'incalls available when driveway is empty'. I turned away from the table, looking at the living room, a fire was crackling in the fireplace and I heavily considered disposing of the flyers, but I knew that he could just reprint them. I put the twenty in my pocket and went back outside. He hadn't moved, and as I let the door close, he patted the spot next to him on the porch love seat. I took a seat.

"What's in your pocket?" he asked.

"Just a handkerchief." I said.

"Strike one." he said, hand put a small note on my lap.

It was Maria's note, it had fallen from my pocket when I shoved the panties in.

"So you're moving on from Sonya?" he asked but didn't wait for an answer, "I'll be honest, I didn't expect that, at least not with another girl. You're a lesbian." he chuckled.

My face got hot as I processed what he said. He saw I was angry and smirked.

"You're a girl aren't you?"

I shook my head no.

"You're not a girl?" he asked, clarifying my answer.

"No."

"You've jizzed while a cock is embedded 8 inches into your ass. You've gargled piss in your mother's bridal lingerie. You are not a filthy porn whore, a slutty girl?"

I scowled, not responding.

"You need to cum on the panties right? If you aren't a girl, go do that. Go ahead. You do that and you're free. We're all done." He got up and beckoned me.

I followed him into the house and he led me to his office, watching as he pulled up pornhub. He got up and pulled the chair out for me.

"Go ahead." he said, "Jerk off like a guy, cum on them, and we are done."

"But the flyers, I-"

"I'll burn 'em. Go ahead, I'll be in the kitchen when you're done." he said, leaving.

Thirty minutes and 15 or so videos later, the friction happening was starting to make me feel chafed and my cock still wasn't hard. I tried everything, lesbian, 69, anal, orgies, gang bangs, it didn't matter. I couldn't get hard, let alone cum. One word kept ringing out in my head: 'clit'. That's what he had called my cock when I was all dressed up for him. Another 20 minutes of attempting to get harder than a limp noodle and the door opened up. He stood there, smirking, holding a bag in one hand, the flyers in another. He held up the flyers first and spoke.

"These can go out on every doorstep in the neighbourhood by tomorrow. With my local advertising connections, I could anonymously mail them to everyone in the city within three days," my eyes teared up but he didn't stop talking and held the bag up now, "Or, option two, field trip. Trust me, you'll like it better."

I thought about it hard before speaking.

"I'm a guy, I'm not a girl." I said, fighting back tears.

"That's fine, you can be a guy for option two." he assured me.

I stood up, pulling my pants up and followed him to his car.

The drive took less than twenty minutes, sitting in silence the entire time. He pulled up behind a nondescript building with no windows. There was a plain looking sign that read 'City Spa' and I began to feel a little relief. It was a spa. Maybe he saw that I was starting to crack, and this was his way of helping me relax. A massage, maybe a soak in a hot tub. My mind kept running to the worst places but he had assured me I wouldn't be dressing up. The way he said it, it felt true. I followed him in and he spoke with an attendant, slipping him a fifty dollar bill and taking something in exchange, keys, and a small brown bottle, no bigger than one inch tall. He led me through a heavy door and down a set of stairs, the air got thick and humid, slow steady trance music played. As we went through another door, the music got louder. We entered a long hallway with many doors on either side each with a light on the wall next to them, some on, some were off. All of the doors were closed. His key opened one at the very end of the hall just ahead of a hard right turn into presumably an adjoining hallway.

"What is this place?" I asked, taking note of the room.

It was dimly lit and there was a small cot style bed along the back wall and a soap dispenser on the wall next to the door we came in. It was empty otherwise.

"It's a spa. A men's spa. Strip." he answered, handing me the bag as I began pulling off my clothes. "No girls allowed." he laughed as he said this last part and I opened the bag.

"No. Please no." I said, now sitting on the bed, naked, pulling out the small piece of clothing.

"Listen to me, this can be our last night together." he announced, ignoring me, "The rules are simple. First, you have to stay for 3 hours. Second, you can't say no at all, to anything. Third, you have to knock on at least 3 doors, and lastly, don't cum."

It looked like panties at first but I realized pretty quickly it was some sort of jock strap. Only, there was no cup, or sleeve for a cup in this one and it was designed with leopard print. The front part cupped my dick and sack tightly, while the thick straps extended underneath, framing my butt cheeks perfectly. I was facing the bed as I pulled them up and felt a push from behind, causing me to fall on my hands and knees. He spread my cheeks and I felt the hot humid air on my hole and then coldness. I looked behind and saw he was getting a liquid from the soap dispenser, and quickly realized it was lube. As he fingered my hole deep, spreading the lube, I was beginning to understand that this was not a typical spa.

"Win or lose, you make it through tonight without quitting, I'll make sure you get those panties back to your little girlfriend with cum on them."

For the first time of the evening since I left Maria, I had a sliver of hope.

Moments later I walked down the hall with him behind me. As expected, around the first corner there were more rooms with lights outside them. Many of the doors looked to be open. As we passed the first open door way I saw a man on his knees sucking another man. The man being sucked was holding one of the little brown bottles and moaning as the other worked on his cock. We continued. The next door way revealed an older man, maybe even a couple years younger than Mr. B, and in better shape, laying back and stroking his cock leisurely.

"You wanna taste boy?" he asked.

I stared, stunned at his cock on display.

"The man asked you a question, yes or no?" Mr. B prompted.

"Uhhh, yes." I said, stepping inside the room.

"Good boy, come get daddy's cock." the man said.

I climbed up on the bed between his legs. It felt weird, he was calling me boy, I wasn't dressed in girl clothes. It didn't feel right. I wondered why clothing should even matter in my mind as the head of his cock entered my mouth.

"Mmmm, daddy's little faggot." he said.

"No, not this one." Mr. B laughed, "This one is straight."

I cringed as they both laughed, and the pelvis of the man I was sucking rocked forward, causing me to gag a little.

"Straight is he? Is that why his little boner is rubbing on my leg?" the man chuckled.

I pulled my face from his crotch and looked down. It was hard to tell looking at it, as the chastity had caused it to shrink, but he was right. I was hard.

"Get that faggot mouth back on my dick" he snapped at me.

I followed his direction, if only to not have to look at anyone.

"Remember your rules, you're a boy now." said Mr. B's voice, sounding farther away.

Two hands grabbed my head and prevented me from looking up to see him leaving but I knew he had. The man moaned loudly and I felt his cock pulsing.

"You're gonna swallow all my fucking cum!" he said followed by a grunt.

I sucked harder and his hands pushed my head farther down and I felt the head of his cock pop into a deep part of my throat. I breathed through my nose as I fought the urge to gag. His cock was almost searing hot and felt like it was vibrating. He grunted out a loud low moan and jets of hot cum pumped straight down into my stomach. Spray after spray it filled my empty stomach, his hands holding my head firm until finally his cock began to soften. It slipped out of my throat and a small burp escaped my mouth.

"Thanks cock breath. Get out of my room." the man said, closing his eyes.

I stood up to leave and felt a slap on my ass.

"Faggot." he said as I walked out the door.

I wandered down the hall, going over the rules in my head. Staying for two hours was out of my control, and then again so was the whole 'not cumming' thing. The one I was having trouble with was having to knock on three doors. I knew that was the reason for rule number two, not being able to say no to anything. If everything went perfectly, the three doors I chose wouldn't be answered. I looked for a moment and saw a closed door with the light out and thought that maybe with some luck, that meant no one was inside. He never said anything about not knocking on doors with lights off. I knocked loudly and confidently, and just as I had hoped, no one answered. I began walking away, when the door across the hall opened. An older man stood there with a shaved head and white bushy beard. He had to be ten years older than Mr. B and 50 lbs bigger.

"I thought I heard someone knocking. How are you, boy?" the man asked.

"Good sir." I replied, turning to walk away before he asked me anything.

"Ooooh wait up a second, let me get a good look at that ass." he requested.

I stopped, following his direction without turning back to him. I prayed that he would just look and nothing more but those hopes were dashed when I felt his hand wedge its way between my cheeks and his fingers rub my hole. His other arm wrapped around me, his hand coming up to my face and middle finger working their way into my mouth. His hands switched quickly and his newly slickened finger pressed into me with deliberate force making me gasp.

"Mmmm good whore boy. Tell daddy you want him to fuck you." he ordered.

His finger felt genuinely good inside me and I began to feel overwhelmed by the loss of control. I knew I didn't have a choice if I wanted to stick to Mr. B's rules.

"I want you to fuck me daddy." I said, and felt his finger hook inside and pull me backwards into his room by my hole.

As he turned me around inside his room I almost fell, but regained my balance. There was laughter at this however it didn't come from him. As my eyes adjusted to the harsher light in the room I saw three other men, two on the bed and one in a small chair. This room was slightly larger than the previous one I had been in. The man in the chair was masturbating furiously and when he saw me his eyes widened.

"Quick! bring him here, I'm gonna cum on his fucking face!"

The man who was holding me slipped his finger back out and I was brought down to my knees in front of him and my face pulled up by my hair. I looked up at the swollen cock above me now and a drop of precum hit my nose. My entire focus was on head of the cock that would no doubt be coating my face in seconds. I felt a warm cock from behind, pressing against my hole. I had a moment of panic, but before I could ask for a condom to be worn it was inside me.

"Please... do you have condoms?" I asked, not holding onto hope.

The laughter in response gave me my answer. I felt myself blushing and filling with shame but there was nothing to do about it but whimper as the cock stretched my hole.

"Ahhhhh, he's fucking warm and tight." the man behind me said as he pumped my boy pussy slowly.

The man in front of me let out a loud long grunt and his warm jizz splattered across my forehead and dripped down my face. Rope after rope, my face was covered. I saw flashes of light through my closed eyes and realized they were taking pictures.

"Yeah that's it, squeeze my cock tight." the man plugging me said and I realized the shock of being photographed caused me to tense up.

I let out a moan as his cock hit my p spot and felt my dicklet firm up slightly. Another man sat in the chair in front of me, his cock half hard, dangling inches from my face. The man that brought me into the room crouched down next to me, still holding a handful of my hair.

"This little bitch is gonna find out tonight!" he said and the other men laughed.

"Wha-at am I... go- Ohhh - onna fi- Ahhh -ih - ind out to - Oooh - night?" I asked, the dick behind me ramming me so hard it was hard to finish my words without moaning or yelping.

"How much jizz that little butt can hold." the man said and laughed, my eyes welled up with tears and I fought the urge to cum that had begun to slowly build.

*****

45 minutes later

The door closed behind me and I walked unsteadily back down the hallway. I was wearing a butt plug now that one of the men was kind enough to put in for me.

Although the men tried to find the limit, the 5 loads that made it inside me filled me up decently, it didn't feel like it was my capacity. The first two men to fuck me were rough and from behind. With so little control I had resigned myself to breaking Mr. B's rule and cumming but luckily, the second man filled me up quicker than the first. By the time the man I was suckling was ready to fuck me, the men decided that I wasn't doing enough work, so he laid on the bed while I rode him in a squatting position until his cock filled me up.

When it was the man that brought me into the room's turn, I was instructed to get on my back with my legs spread, but he didn't actually fuck me. I was told to jerk him off with both hands as he stood over me, while once in a while sucking on his big round cock head. It was the biggest cock head relative to the shaft I had seen and felt like I was sucking on a lollipop at some points. The intimidating size of it made me a little nervous about the potential of him fucking me. Eventually, this possibility came to fruition in a way as he yelled he was going to cum. He pulled his cockhead free of my mouth with an audible 'Pop' and put it against my asshole, pushing it in. the sudden stretch caused me to let out a small whimper and then my guts felt the familiar warm jet of jism. I thought I was done at that point, but the man that came on my face originally was edging himself again and had one load ready in the chamber. No sooner did the older man pull out, the facial man moved in and filled me up some more.