Sissy Confusion

I watched the sun go down outside of the window as I waited and I waited for hours for my girlfriend Gloria to come home.

It was my fault, too.

I had the idea to surprise Gloria with something I thought was going to be a real treatment for the both of us.

We had always discussed how pretty I would be if I were all dolled up like a woman. And Gloria had a slight tranny-fetish to match my slight cross-dressing fetish, and together we talked about trying something a little kinky at some point in the future.

I thought we might give it a try that night, but Gloria never showed up.

I had been dressed up as a slutty office siren from head to toe; white blouse, purple pencil skirt, stockings, and black siletto heels; my make up done up casual enough but convincing enough to really get the part right, but again she never showed up.

I had put a big red ball gag in mouth, cuffed me ankles together, and the handcuffed my hands above my head to a pillar in her apartment, and waited…

I stood in the tall heels, which were buckled to my feet, and I couldn’t kick them off to relieve the pain in my calves, and this went on for what felt like hours.

Now I was alone in the dark, whimpering helplessly to myself.

I began to really feel the fear and pain of being bound and gagged with no one to come and rescue you, and after a while a I started to think —

What if she never shows up??

How am I going to get free??

This was meant to be a surprise for her, but of course Gloria had no clue that I had this in mind for the evening.

My legs were trembling bad when suddenly I heard the locks at the front door start to rattle.

She’s back! I thought, and quickly straightened myself up, and got back into character.

I watched as the door opened, and a tall shadowed figure stood in the doorway. It was not Gloria. The light in the living room switched.

It was Gloria’s younger brother, Pat, who I completelyforgot had been staying with her during his winter break from college.

Pat stood in the doorway, and just stared at me handcuffed in the living room.

I stared back, completely helpless and terrified that it was him and not Gloria.

The young man was a tall, strapping frat boy, with long arms and thick legs. He must have gone out drinking for the night, because the stench of booze wafted around him as he entered the apartment, and slammed the door shut.

He was grinning at me, eyes glazed over, a slight sway in his demeanor.

“Well, well, well,” he chuckled as he approached me. He stopped in front of me, gazing at me eye to eye. He looked me up and down, rubbing his hands over my body.

“Just what in the hell is going on here?”

I groaned, trying to mumble through the ball gag, but nothing intelligent came out as the drool spilled over my blouse.

“Pweease…,” I mumbled. “Pweease, helm mae…”

“Please what?” He mocked. “Please help you?”

I nodded my head vigorously.

He glared at me, and simply said, “No. I’m not helping you.” He chuckled as he moved passed me into the kitchen, and opened the fridge.

I watched him, feeling weak, and helpless, as he took out a beer, and popped it open with a lighter.

He turned back to me. He didn’t say anything. He just grinned. Then, he scoffed, and sauntered down the hallway towards his room.

I was alone again…

I pulled at the cuffs, but they only bit my wrists. And the ankle cuffs were becoming even more painful as I struggled. Balancing on the heels was getting more and more difficult as my legs were starting to give. I just held as still as possible, my head lowered, and whimpered like the helpless girl I was.

I could feel the drool running down my chin, drenching my blouse.

My cock was a small cock cage beneath my skirt, and it was soaking my panties.

Dispite all of the pain I felt, and the fact I thought Pat would help me, was in fact turning me on still.

I hated myself for it, but it was true, and this was as real as I had ever been to being completely helped and vulnerable — to the real thing.

I don’t know how much time went by, but eventually Pat came out to grab another beer from the friedge.

I moaned, and beckoned to him again, but he ignored me completely.

He didn’t go back to his him room, Though. He brushed passed me, and went to the couch to flip on the TV, and that’s when I knew I was fucked…

The remote he picked up did not go to the TV.

It went to the vibrating butt-plug stuffed deep inside of my boy-hole that I had strategically placed on the couch for Gloria to find, and have something to tease me with.

“What the fuck is wrong with this damn remote?” Pat grunted, pressing the on and off button over and over again.

The vibrator was alive, and buzzing, deep inside of me. Each time Pat tried the remote the butt-plug sizzled back to life, againand again, titillating my prostrate, and engorging my cock against the little bars of the cage.

I tried my best to hide my moans, but this vibrator was especially powerful.

“What the hell is that noise?” Pat asked. He turned around to me. “Would you shut back there, sissy boy. I’m trying to get the damn game on.”

He kept fiddling with the remote, tormenting me without knowing as I tried silencing myself as best I could.

Then Pat stood up from the couch. He came around to me with a strange look on his face. He leaned in close to my hips.

“Is that coming from you?” he asked, listening closely.

I moaned behind the ball gag. I didn’t want him to know, but he knew.

“Holy shit!” he said. “You got a vibrator in your ass don’t you know, sissy boy?”

I nodded my head weakly that it was coming from me.

“You and my sister are into some kinky shit,” he laughed. “Let me see what else you got on under that skirt.

He lifted my skirt above mehips, and saw my cock in the cage beneath me panties.

“My, oh my,” he groaned. “I bet that hurts, doesn’t it?”

And, I nodded weakly that it did.

He had left the remote on the on position, and the vibrations inside of my asshole were weakening me so badly I wanted to collapse, but my hands were secured above my head, and there was no way I was going down.

Pat glared at me. He began rubbing his hard on through his jeans. Based on the contours I could see that his cock was undeniably thick, and long and hungry.

“You know your kind of pretty all dolled up like that,” he grinned. “If I didn’t know you were a guy, I would definitely take a shot at you…”

I peered up into his eyes. They were glazed over, feverish, and curious. I could practically see his mind at work.

I know what he had in my mind already.

“I’ll tell you what,” he began. “You agree to suck my cock, and I’ll let you free. How does that sound, sissy boy?”

My eyes widen atthe thought, but that was my only way out of this.

“If not, then you can spend the rest of the night here with that plug in your ass driving you nuts all night. I’ll leave it on, too, and just watch my game until you agree.”

He smiled into my weeping eyes. He knew he had me.

“So, do we have a deal?”

I nodded yes at once, I would suck his cock, Because the thought of ending this torque all night long was far more terrifying than sucking a cock.

Pat stood back with his arms crossed. “I want to hear you say it, sissy boy. Say you’ll suck my cock like a good little girl.”

“I’ll thuck yer cock,” I mumbled through the ball gag.

“Good girl. Now where’s the key?” he asked me.

I nodded down my chest.

“Here?” He ripped open my blouse. I heard the buttons land somewhere. My bare chest presented; my nipple erect. He smiled at the key to the cuffs on a chain around my neck.

“You thought of everything didn’t you,” he smiled, unhooking the key from the chain. “Except for me…” he grinned.

I felt Pat reach above me, and unlock the cuffs above my head.

“No tricks now you hear?”

I nodded, so grateful to be freed what else could I do?

My hands released, and at once I buckled to me knees, but Pat wasn’t taking any chances. He still hand one of my wrists locked in a cuff, and he quickly twisted my free arm around behind my back, and cuffed my wrists back together.

A puzzled look came across my face, but Pat just grinned. “Be happy you’re not strung up, sissy boy,” he stated.

It was true. This was a relief on my arms, but only a little.

“Now hold still,” he said.

He leaned my forward as he reached around and unbuckled the wet ball gag.

It dropped free and hit the floor with a solid thud.

I breathed in deep relief, feeling the feeling in my jaw return as I stretched my mouth. Just my lips closed, but Pat held up my chin.

“No, no, you keep that mouth open,” hesaid. “Nice and pretty, too.”

I did as I was told, and kept my mouth wide open, and to fulfill my end of the bargain.

I watched Pat open his fly, and pull out a thick, meaty cock, and hold it right in front of my gaped mouth.

I couldn’t help but gaze it.

It was so up close, and even though Pay was drunk, it still smelt so clean, and manly. It had a pinkish yet pale hue to it, and it thick and long which I didn’t expect, but had to give the young man my compliments.

Pat began struggling it softly right in front of my face.

I peered up at his smiling face, and maybe something about my look triggered him because right then he grabbed me by hair, and yanked my head back. He got right in my face, and said:

“If you bite me, I will fucking gag you again, drag you out of this apartment, and throw you out in the fucking street.”

His eyes were on drunken fire.

I wasn’t even thinking of doing such of thing, but Pat was thinking I might, and I had no doubt that he would drop me off somewhere. Probably in a shabby part of town where who knows what the hell would happen to me dressed, bound, and gagged like a girl.

He frowned. “Hey, I’m talking to you. Do you understand me, sissy?”

“Yes, I understand,” I whimpered. “Please, let me suck your cock.”

He stood back. “Now there’s a good girl. Hop to it, and make it good, sissy.”

I didn’t hesitate to do what I was told. I drove my mouth over the meaty cock, feeling it’s warm stuffing inside of me as I pushed it all the way down my throat.

From there, I got to work…

“Oh, yes,” he moaned, as I pulled back along his rigid cock, and drive right back down again, pumping the cock down my throat, slobbering, and pulling back again, over and over until it was wet enough to easily slide down my throat.

“Just like that…”

I felt Pat grip my head, and begin to guide me back and forth until he found a rhythm and just started fucking my face…

I choked and gagged and grunted and moaned, and slobber was everywhere.

I had never sucked a cock before, but I was learning quicky what a natural I was, and Pat too was overly pleased, which in turn pleased me even more.

“Keep it up, and I’ll pull that plug out of your ass, and fuck you like sideways, sissy,” he grunted.

And the idea didn’t shock me at all.

My cock in my cage was drenching my panties. The plug in my ass was preparing me for insertion. I was dressed like a sexy little office girl. I was bound on my knees sucking a beautiful cock as if Pat was the boss himself and I desperately wanted a promotion…

Yeah, I wanted to be fucked.

Pat sensed this when he heard the noise I was making with his cock in my mouth. He unsheathed his long cock from my hot drooling mouth, and lifted me onto my heels.

My legs were so weak, I nearly fell, but Pat picked me up and carried me to the couch.

With my hands cuffed behind my back, and myankles cuffed together, I knew I hadn’t much of a fight in the matter when he propped me over the armrest so that my ass presented itself to his delight.

“Sexy ass, too, wow,” he excited. “Just like a woman’s. I am impressed. Look at those stockings. Very sexy. Let me see it jiggle,” he chuckled as he spanked my ass a few times hard across my plump cheats.

I shrieked in pain and pleasure, but then gushed as I felt him slide my panties all the way down to my cuffed ankles.

“Let’s see how big this plug is.”

I felt him twist, and pull until finally the plug slide out of my ass with wet pop.

“Jesus,” he said, holding the clean slick plug right in front of my face. “That was in your ass,” he chuckled. “Now it’s my turn.”

I felt him spread My cheats and spit down my gaped hole, and the next thing I knew he was gripping my hips, and I was about to take my first cock in the ass.

The pain was unbearable. It burned, and sered my tight rim as he slide hiccock inside of me almost to the point where I felt like he was tearing me apart.

I cried, and took the pain of is long cock; tears flowing down my cheeks.

But soon that pain faded, and all I was left with was a pleasure I had never experienced before in my life. A fantasy unknown to myself coming true; dressed like a sexy woman, bound, and bent over as a man overpowered me and ravished my helpless boy-hole.

Pat was fucking me so hard to the point where I nearly passed out…

As I faded in and out of consciousness, I remember being rocked back and forth against the arm rest with powerful thrusts from his hips; feeling his balls slap against mine; the pain the cage made from being confined, until finally I feel his release fill me up; a warm scalding gush that never seemed to end…

Pat stepped back from destroyed ass, and stared down at me.

“Now clean my cock, sissy,” he said.

I obeyed without question, struggling with my hands cuffed behind myback to sit up, and get down on my knees, but I did it, and grabbed his throbbing come covered cock with my mouth, and got to work cleaning him with tongue.

Once he was clean, Pat did the unthinkable.

He jammed the ball gag back in my mouth, and buckled it tightly.

I whimpered as he did this. I thought after he fucked me, and I sucked him off that he would let me go, and we could Pretend this never happened.

But no.

Pat gripped me by my hair, and got right in my face.

“I lied, little sissy boy” he said. “You’re going out on the streets.”

PART 2

I screamed and fought as Pat lifted me up and throw me over his shoulder. He grabbed his keys, and hauled me out of the front door of the apartment, kicking and screaming.

I begged and I cried behind the gag as he carried me to his truck, and throw me in back seat. He got in, ignoring my cries, and fired up the truck.

Soon we were on the road. I leaned my head against the window, and saw the change in the cities we were passing through. No other cars seemed to notice me through the window. I was being kidnapped now, and had no clue where Pat was taking me.

We parked on a dark street corner. Two black guys stood there smoking cigarettes and drinking out of brown paper bags.

I was mortified as I watched Pat get out, and go around to my side. He dragged me out of the truck, and carried me over to the black guys.

The two guys looked Pat and I up and down as Pat stood me up on my heels in front them, and held me so that I didn’t disappoint.

“Found this sissy boy in my house,” he said. He tossed one of the guys the keys. “Thought maybe you could put her virgin ass to good use.”

Pat pointed passed the two men at the adult bookstore They were hanging out in front of. The turned back to us, and nodded.

“Hell yea we can,” the taller of the men said.

“We can tax that ass for days,” the other grinned, reaching out, and patting my ass.

I cringed, and started to cry and moan behind the ball gag.

Pat pushed me forward. I fell into the arms of one of the black men who lifted me up, and throw me over his density shoulder.

“She’s all yours,” Pat said, and started to walk back to the truck when the black guy not holding me said:

“Here. Take this.”

He handed Pat a wad of cash. Pat nodded, put the money in his pocket, and went back to the truck.

The black guy turned around, and started to carry my helpless body towards the adult bookstore.

I watched, tears flowing, as Pat climbed into the truck, and drive away.

The other black guy joined us, and together they carried passed the bookstore, down a dark alleyway and behind a dumpster.

“Let’s give this little shorty a test run,” the black guy said.

The one holding me set me down, and pressed up me against the wall. “That’s exactly what I was thinking. Think she can handle a couple big black cocks?”

“Shit, she’s gonna haveto learn either way,” he chuckled.

“Heard that.”

Meanwhile, I stood there, trembling as I listened to these two behemoths talk about breaking me in, and teaching me how to take a big black cock. Never in my life. The tears were coming down, and one them turned to me, and gripped me by the throat.

“Knock that crying shit off, you hear me?” he shouted. “This shit is happening, and there ain’t a god damn thing you can do about, is there bitch?”

I chased back my tears, and dared not look into the man’s eyes.

“That’s better. Now, let’s see what you got,” he said. “Get on your knees.”

I struggled as I slide against the wall as carefully as I could onto my knees in front of the two black guys who towered over me now.

One them reached around and unbuckled the ball gag. He pulled it out, and put it in his pocket. I was about to speak, beg them to let me go when one of them put a finger to my lips, and said:

“Now, I got this,” he said, holding up aring gag. “You have two choices. Either be a good little sissy bitch and suck our cocks, or I put this in that sissy mouth of yours, and we face fuck your skinny ass. Which is it?”

I didn’t know what to say. I felt the tears coming back, and I fought them with everything I could.

“Speak up, sissy. Which is it?”

“No gag please. I’ll suck your cocks Without it.”

“Alright, you see that?”

“I do, I do. This bitch is learning fast.”

“She is. First lesson, sissy. It don’t matter what you want, or how you want it. You’re going to be a fuck doll, so you better just get used to the idea. Understood?”

I nodded my head.

“Say “yes, master.””

“Yes, master,” I said, unable to fathom what was happening, but clearly, I was submitting.

“Good, bitch,” he said. “Now, open wide, and get ready for some big black cock.

“Yes, master,” I said. I opened my mouth and waited as the two black guys whipped out the biggest dicks I had ever seen. Theircocks were as long as my face, and as thick as a pipe. They began slapping me in the face with them. It felt like I was being struck with a salami. They batted me to and for for minute.

The first black guy pulled my head forward and jammed his cock into my mouth. It barely fit, but I opened my mouth as wide as I could until it fit. He pushed it down my throat as far as it would which wasn’t Even half the length of his cock.

This was impossible.

He passed me to his partner, and the second cock entered my mouth. It was enormous, but slightly thinner, and I was able to swallow almost all of it.

“She’s got a nice little sissy mouth, doesn’t she, my boy.”

“Hell yeah. I see potential in this hoe fo sho!”

For the next ten minutes, they passed my mouth back and forth between their cocks, back and forth until my head was spinning and all I could think of was how to satisfy the next cock in my mouth.

It was mind boggling. I was getting drunk with cock,and the men could tell. The were laughing at me the whole time, challenging me, trying to see how far I could take their cocks, and I just did what I was told.

I was covered in slobber and drool, and the more they face fucked me the more my cock ached in its tiny little cage. I was dripping wet right now. Apart of me was enjoying this, but a part of me knew I wasn’t supposed to.

It was being mind-fucked.

Next thing I knew the first cock shot all over my face, and then soon after the second cock shot down my throat, and down my chin.