Sissy Journey Stories
Chapter 1
“Oink for me, little piggy! Oink you chubby, faggot bitch!”
“OINK! OINK!” I cried, “OINK, OINK!”
The other men in the room laughed as they looked down at me.
“That’s my good whiteboy bitch.” Master looked to the other men in the room, “You see how well I’ve trained this fucking slut? I told you.”
The men laughed again, this time with a greedy tone. They were interested in seeing what else I would do on command.
Master gave a few tugs on the lead of the leash he had attached to my balls, “Crawl into the bathroom bitch, I have to piss after that drive.” Already on all fours, I began to crawl towards where I remembered the bathroom was in this cabin. It was not my first time here.
Master had me strip completely when we entered – except for my cock cage, which rarely came off. I was naked and crawling around in front of what I figured to be at least three other men. I didn’t dare look up to count, I am certain I would have my balls smacked for that. I counted six shoes, so there were at least three, maybe more somewhere else in the cabin.
I was here to be shown off to Master’s customers. This evening was to be a prominent jewel in the crown of humiliation and servitude that I have been trained to bear ever since the day Master and Daddy found me.
I was being shown off to have my holes sold and become Master’s whiteboy whore.
I still found my situation terrifying, but my training prepared me for the new reality. This was not a place that I expected to be in my life.
I work as a manager at a bank, a comfortable position where I make a good salary, a lot of flexibility and don’t have to work very hard. A soft life. One of my favorite ways to start the workday is to come in around 9am, sit at my desk with a cup of coffee and act like I’m on a video call while I look at my favorite porn on my phone.
That’s exactly what I was doing on the day that I met Master and Daddy, flipping through my favorite captions about being a submissive cocksucker to dominant men. On this particular morning, I was particularly engrossed by a series of pictures of big black cocks dripping precum.
The captions called for getting a bitch mouth around them to eat all the leaking precum before it hits the ground. The pictures were really hitting the spot, my very average cock was more than averagely hard. I was gently rubbing the head over my pants when I noticed a wet spot – I was leaking precum. Just as I thought to myself that I need to wait until this dries before I get up, there was a knock at my window.
My office is on the ground floor by a parking lot, people walk by all day on their way into the bank. I know that they are so busy with their own plans that they don’t even notice me – I barely notice them.
The loud knock startled me. There was a large young black man on the other side of the glass. He was laughing and holding up his phone. Did he just record me? What the fuck is going on? My brain rushed from one scenario to the next with astounding speed. Before any real thought coalesced the speaker on my phone buzzed. “Your 9:30 appointment is here.” my assistant told me.
“Oh….ok, ummm, send them in.” I sputtered trying to forget what just happened and get into work mode. I straightened up in my seat, cleared my throat and adjusted my tie. An older black man walked into my office, he reached his hand out to shake mine, “Hey, I’m Pops.” he said in a deep but amiable voice.
I stood up to meet him and put out my hand. He immediately looked down to my crotch and smiled, obviously noting the wet spot of precum. Then he looked back up and his eyes met mine, “But you can call me Daddy.”
I nearly choked, “Umm wha, wha.. Are you here about a loan or w-” I couldn’t complete the sentence. I was so stunned by what he said and embarrassed about the stain on my pants. Then, before my stupor could dissipate, in walked another man. I quickly registered his red hoodie, it was the same younger black man that was laughing and pointing his phone at me outside my window.
“I got it Pops. Just like you said, he’s practically begging for it.” The younger man said and he showed Pops his phone. Pops smiled and closed the door to my office before he sat down in the chair across from my desk.
“I’m- I’m sorry, just what is going on here!?” I asked incredulously.
The young man continued through my office and around my desk until he was standing next to me. He held out his phone, “Here, have a look.” The phone was locked, I couldn’t see anything on it. He put his hand on my shoulder and pushed down. He was strong and I immediately buckled and sat in my seat.
He stepped uncomfortably close to me and held the phone right in front of a bulge in the crotch of his shorts. He looked straight down at me as I reached for the phone, “the password is bigcock, capital B, capital C.”
The shock I experienced when I saw this man outside my window had only escalated with each passing second since then. Pops said, “Go ahead and type it in like he said – bigcock, capital B, capital C – then hit play.”
As if in a trance, I did what I was told and when I did I saw a play button and hit it. There was a video of me in my office, phone in hand, looking at cock pictures and rubbing my crotch. I had been so careless, I had no idea I was so exposed this morning. I was usually more careful. This was enough to get me fired for sure. My hands were shaking and I dropped the phone onto my desk, “Wha- how dare you!” I tried to muster up some anger to scare them somehow. There was no real strategy, I was just reacting. “Who do you think you are!?” I yelled. As I looked at the younger man on my right I saw that he had taken his cock out – his big black cock was hanging directly in my face.
“You definitely want to change your tone with us. Right now.” Pops said in a very direct tone, a departure from his previous disposition. I couldn’t take my eyes off of the giant cock no more than 6 inches from my face. It was dark and thick, it hung straight down and seemed to just go on and on. It almost seemed like the head was pulsing – he was getting hard.
“My friend and I are not here for a loan. We are here for you.” Pops continued, “I came into the bank the other day and saw you playing on your phone. I like to snoop a little and I saw what you were looking at – you love some cock don’t you sweetheart?”
Still staring at the other man’s cock, “I uhhhhh, I don’t – I don’t know what you mea-” The man next to me grabbed me by my hair and turned my head to face Pops, in doing so, he shoved his very large cock right onto my face.
“Look, there’s no reason for this to be difficult. You have a choice here. Option 1, my friend here puts his cock away and we walk out the door. We show this video to your coworkers and ask to send it to HR. You lose your job in disgrace. It’s a bad day, maybe a bad few months, you find a new job and hope no one finds out what you did. Easy peasy.” he said jovially.
“Option two is much more fun for all of us.” Pops said. He leaned forward and continued as the other man used his free hand to slap me with his big black cock and rub it on my face, “Option two is you come by our place on your way home from work we can explore something you obviously want and we can see how far your love for cock goes. If you behave like a good little bitch there will be no need for anyone to find out about your tiny indiscretions.” Pops sounded more sinister but somehow still nice. It was jarring.
Though not as jarring as being slapped in the face with a cock at my desk in my office. I can still hear the sound his cock made as it hit me each time. Pops laughed at the sight of me, “Well whiteboy what will it be? You can tell us to get out in your cute little angry voice and we can pursue that path. Or you can be a good boy, reach up, hold my friends big cock and give it a kiss. Just a little kiss on the head and say ‘please sir, can we meet up later to talk about this?'”
Shaking all over, I turned my head towards the cock, I slowly reached up and held it in my hands. It was warm and noticeably heavy. I had never held another man’s cock in my hands before. My porn consumption was just a fantasy, it was never something I thought I would do in real life. But here I was, big black cock in hand. I looked up at the man it belonged to, leaned forward and kissed the large head of his cock, I kissed it again and again. I think I used a little tongue. “Please sir, can we meet up later to talk about this?” I said. “Ask again.” he said. I kissed his cock again and again, it was growing further, he was getting hard. “Please sir, can we meet up later to talk about this?”
“Again.” He said.
“Please sir, can we-” as I opened my mouth to continue, he shoved the head and then some inside my mouth. His firm hand tightened his grip on my hair.
“What’s that bitch, I didn’t hear you – say it again.”
With my mouth full of his cock I tried to continue, “Pwwweeesss thirrr, cnnn wii mmmett up wwwater nnnd twak about ffissshh?” Then I sat there stupidly with his cock in my mouth waiting for an answer.
I received it from Pops, “HAHAHA we sure can do that sweetie, we sure fucking can.” The man removed his cock from my mouth, placed it on the side of my face and said “Smile, bitch.” As a reaction, I did as I was told. He turned my head towards Pops who was holding up his camera, obviously filming what was taking place.
“Send me your number – I’ll send you this video, so you can finish what you started in your pants. Send me back a video of you licking your load out of your hand, then I’ll send you my address. Get to it and be there at 6pm sharp.”
I don’t remember much of the day after that. I gave them my number. They left my office laughing. The younger man knocked on the window as he went by my office to his car in the parking lot tauntingly. I got the video from Pops. Awhile later, after a visit to the bathroom, I did what I was told and jerked off in the bathroom.
I sent a video of me eating my cum out of my hand. I got the address – two months of training later, here I am, attached to a leash, crawling into a bathroom about to demonstrate my training as Master’s urinal.
Chapter 2
It was not easy to mentally adjust to my new life but the more I accepted it the more I fell into the role of sissy slut for Daddy and faggot whore for Master. The training required to get me to where I am now, an obedient slut and urinal in the process of being rented out to a group of men for the weekend, was thorough. Daddy and Master were vigilant and strict from the moment I knocked on their front door for the first time.
It was a townhouse in a nicer part of a working class neighborhood – not far from my work. I parked around the corner, I left my wallet in the car, I was so unsure of what might take place and still held out some pathetic hope that this was not happening.
Shaking with what was to come. Post nut clarity had me freaking out earlier this afternoon when I sent my video the the owners of this house where I was eating my own cum. That feeling eventually subsided to resignation. I was too scared about being outed as a pervert in my office to say no to them. Being honest, I was also interested to the point of compulsion – part of me wanted more cock. And I was about to get it.
The terror I felt earlier in the afternoon resurfaced as I approached the steps to the front door. I just had to get it over with and see what was on the other side – I rang the bell.
The younger man in the red hoodie opened the door. He was laughing as he let me in, “Oh you fucking little bitch” he said as he eyed me up like a piece of raw meat, “I can’t wait to get started on you.”
The front door opened to a small, tight foyer. The young man closed the door. He maneuvered himself behind me and pushed me against the wall. “This won’t do. You are walking in here like you are a man. But you ain’t a man here, you a faggot bitch. Say it – say what you are!”
“I-I’m a faggot bitch.” I stammered.
“You call me Master! Now say it again – you are my white faggot bitch – SAY IT!”
“I’m your white faggot bitch, Master! I’m your white faggot bitch!” I said loudly out of fear.
“Good. That’s my good little bitch.” He said calmly. “Now let’s get you fixed up a little before you walk another step into my house.” Master pushed his whole body up against mine, Pushing me into the wall like a cop with a perp. He kicked my legs apart and reached around the front to start unbuckling my belt and pants. He pushed his crotch against my ass and I could feel his massive cock against me, “Unbutton your shirt and take it off.”
I immediately complied. He reached into my pants pockets and pulled out my phone and keys and dropped them on the floor. He took my belt out of the loops, brought my hands behind my back and used the belt to keep them there – not tight, but I got the message. Then he pulled my pants and underwear down below my knees, but not off. “Good little piggy. Now suck on this – get it nice and wet.” Master stuck his middle finger in my mouth and I sucked it as instructed.
“Now you are looking less like a man and more like a bitch, we can go see Daddy in the livingroom.” In a swift motion, Master grabbed my hair from the back of my head and turned my body to face down the hallway. “Ahead and to the first left, bitch” He said.
Then he stuck the finger I had sucked up my exposed asshole. He pulled up with his finger and pushed down with his other hand on my head, bending me over partially. I was scared and simply reacting to his control.
With my pants around my ankles, and Master directing my pace with full control of my body, I waddled down the hallway trying not to fall. After a few steps I made it to the entrance to the livingroom.
“Oh, good, our new friend is here.” I heard Daddy say. I made the turn and was left standing the middle of the room. Master removed his finger from my asshole then wiped it in my hair, before he found a seat on the couch.
I looked up and around at this new space. It was a big room, TV on the wall behind me. All nice, neat and normal. Daddy was on a big comfy chair directly in front of me. Master fell into a spot on the sofa nearest Daddy. The sectional sofa had a seat directly in front of the window. The seat was occupied by another man. On the floor, between the man’s legs, was someone in purple lingerie who seemed to be sucking the man off. I began to stare at them while the shock of my situation pulsed through my entire body.
I began to panic.
“Hey! Over here baby girl, just look at Daddy now and take a breath. Breath in and out, real big for me ok?” Master chuckled at hearing this type of talk from his counterpart.
I tried to take deep breaths. The more I did, the more I could feel every centimeter of my situation. I was standing in a strangers livingroom with my pants around my ankles, my hands around my back, no shirt, anally fingered and I knew it was all just the beginning.
Daddy continued, “Now don’t mind Gary over there. He’s a friend and he likes to see when I break in a new slut. That’s just his own whiteboy bitch doing what faggots do. Go ahead, you can look now.”
I turned back towards where Gary was sitting on the sofa and watched the man in the purple lingerie slowly move up and down on a cock I could not see. Gary looked at me with a smile, “God I love this part.” He said. “Don’t get me wrong, I like using these bitch boys every which way. But there is only one day 1. Ain’t that right cocksucker?” The man with the cock in his mouth made an affirmative noise without changing pace on Gary’s cock.
Gary grabbed his hair and pulled the cocksucker down on his cock further, “I’m gonna fuck your mouth for a bit now boy.” He then started using the cocksucker’s hair as a handle pulling him up and down the length of his cock. There were slurping and gagging sounds but I didn’t see any distress from the cocksucker on all fours on the floor. Just compliance.
“You like seeing that faggot? You like seeing Gary get his cock sucked, huh? I can tell by your little whiteboy dick.” Master said. The men in the room all laughed, I looked down and my dick had started to get hard.
It was difficult to rectify being terrified and turned on. It had a net result of making me very compliant.
“Now, in case you were unsure, we are going to turn you into our own version of that cocksucker over there. We are going to own you from here on out until we are done with you. It’s going to be hard work but I think you are going to like it. Even if you don’t, we will.” Master said and the other men chuckled.
Daddy took a different tone than Master, “Listen little sweetheart, you’re gonna learn how to make us very happy. We are going to give you all the big black cock you ever dreamed of. Doesn’t that sound nice, baby boy?”
I stood there in a stunned silence. Master snapped me out of it, “YOU ANSWER WHEN YOU ARE SPOKEN TO BITCH!”
“Y-Y-Yesss sssir. That sounds nice, Daddy.”
“Now that’s my good girl.” replied Daddy. “Well I think it’s time for your first lesson little piggy. Go kneel in front of that chair under the TV.”
I turned to face the wall where the TV was mounted and approached the chair. It was a small wooden chair. It was pink with rainbows and other bright, happy things painted on it – certainly designed for a little girl. Before I got to my knees I saw that the seat of the chair had a suction cup dildo attached to it.
“This is your chair from now on. This is the only place you sit unless you are told to sit somewhere else. Is that clear bitch boy?” said Master.
“Yes Master, that is clear.” I said, staring at the sizable dildo on the seat in front of me.
“Now lean forward and get that dildo nice and wet with your mouth. I suggest that you do a good job getting it lubed up because you ain’t sitting next to that cock. HAHAHAHA!” Master said mockingly.
I leaned forward and put the dildo in my mouth. I immediately began slobbering all over it, trying to make sure that it was as lubricated as I could make it. After letting me get at it for a few moments I heard Gary speaking to his cocksucker, I couldn’t hear what he was saying but when he stopped he grunted a few times, I figured he was climaxing in his cocksucker’s mouth.
Gary spoke to the room, “Can my cocksucker help out your new boy, gentlemen?” Master and Daddy gave their consent, curious to see what their friend was cooking up. While I continued to slobber on the dildo, I watched Gary and his cocksucker approach me in my peripheral. “Alright new whiteboy, stick your ass out and arch your back, I need to see that asshole.” I did as Gary instructed while keeping my mouth wrapped around the fake cock.
Gary’s cocksucker knelt next to me. He put his hands on my ass and spread my cheeks apart. “Look at that nice little hole” said Daddy, “Have you ever been fucked by a real man whiteboy?” he asked. I moaned a noise indicating “no” as best as I could with my mouth full. Daddy and Master gave a chuckle in approval.
“Get to it cocksucker, and give our hosts a bit of a show to thank them for allowing you to participate with their new toy.” Gary instructed.
The man, or what used to be a man, in purple lingerie, leaned forward and spit on my lower back. It took me a moment but I realized by the volume that it must be Gary’s load of cum that he spit onto me. I winced at the feeling but did not stop sucking the dildo for fear of what might happen to me.
“Don’t move that ass, whiteboy, keep that load right where it is.” Gary told me. His purple clad bitch lowered his head and started to lick my asshole. I could feel his tongue probing my hole and licking all around. He then went up to my lower back and started using his tongue to push Gary’s load down my ass crack and all over my asshole. This took a few minutes before Gary indicated he was satisfied with the performance by pushing his cocksucker away with his foot like he was a dog sniffing around too long.
With his face removed from the area I could feel the wetness of the area. I also knew that three men were now looking at my cum covered ass as I sucked on a dildo in their living room. As the men surveyed the performance they laughed. “Hahahaha, ok whiteboy, you look ready – stand up, turn around and sit on your new chair” said Master.
It was awkward for me to get up from the cock sucking position to stand with my hands bound behind my back and my pants around my ankles. I stumbled but eventually rose and turned around. I looked at the three men but only for a moment before I lowered my head in shame. I began to squat over the dildo on the chair.
“Help the stupid whiteboy out” Gary told his cocksucker. The man in purple kneeled next to my chair and held the dildo steady. I felt it on my ass, then against my hole, then entering me.
I moved down the cock slowly but at a certain point I could not hold myself over it. I had to sit all the way down. My “helper” removed his hand as I sat flush on the chair – the dildo all the way inside me. It was stretching me out in a way I have never been stretched before. I was so full. It hurt and I winced in pain. I moved all over to try to find the least uncomfortable position.
Surprisingly, it felt good too. This morning I could not have imagined being grateful for a rim job and a load of cum on my asshole but I certainly was. The lubrication made the violation much less unpleasant.
The men in the room enjoyed watching me struggle. Eventually I found a way to sit that hurt the least, and looked forward to my tormentors.
“That’s my good little boy. Are you getting comfortable with that cock stretching our pretty little hole?” said Daddy.
“Yes, Daddy.” I managed to respond.
“It looks like he’s enjoying it!” said Gary, pointing to my semi-flacid cock that was now leaking precum onto the seat of the chair. The men all laughed. Gary instructed his bitch to clean the cum from the chair which he did immediately.
“Gary, your cocksucker has been very helpful, would you allow our new boy to thank him for his assistance today?” said Master.
“Sure, go ahead – he’s done a good job today and I was going to let him cum at some point this evening anyway.” Gary replied.
“Whiteboy, give Gary’s slut a blowjob and thank him for his help.”
I was lost in the statement. I think I was in shock with the entire ordeal. I just sat there silently and stared at Master. I heard the words but I didn’t react. Gary’s slut stood and began to take his cock out of his purple panties. He put his hand on the top of my head and turned it to face his cock.
He took his flaccid cock and rubbed it across my lips. There was precum dripping out as it began to get hard. He shook my head a bit and I opened my mouth robotically. He stuck in his average size cock and began pumping away in my face.
I could tell by his pace that this would not take long. He must not be allowed to cum very often. I looked up at him as he fucked my face. This used to be a man but now he is a bitched out faggot – and I was on the receiving end of his cock. My god, what did that make me??!
“Cum on his face.” Master instructed.
“And hurry up. We need to get going so my friends here can get to work on their new property.” Gary said.
The man in purple lingerie who was fucking my face picked up his pace. Precum was streaming into my mouth so much that I had to swallow to keep breathing. Suddenly, I saw his balls tighten up. He pulled out quickly and started jerking his cock. It took only a few strokes before he blew his load.
I have never had cum on my face. Each shot was very jarring. It landed hot, not warm but hot. Then it quickly cooled. He shot load after load. It did not dawn on me until later but I realized that he did not miss a drop. All of it was on my face. There was a little left at the end so he put his cock back in my mouth for me to clean off.
“Now be a good boy and thank the nice faggot for helping you on your first day of training.” said Daddy.
I looked up and thanked him. He said nothing and put his cock back in his panties. Gary smacked him on his ass. “Let’s go, cocksucker.”
Gary said his goodbyes to his friends. They all stood and laughed and talked about getting back together to let their pets play in the future while they walked to the front door.
For a moment I was in the room alone. The dildo stretching my ass was almost forgotten while I was sucking dick but the sensation became more prevalent now. Though it was still a distant second to the sensation of the significant amount of cum running down my face.
Master and Daddy entered the room and stood over me.
“Not bad sissy boy. Now it’s time to get started, let’s clean you up first.” said Master. Daddy unbuttoned his pants and let his huge cock flop out. He ran it up my cheek collecting some of the cum that was there.
“Let’s not let this faggot cum go to waste sweety – open up now” He said as he put his cum covered cock into my mouth. Master unbuttoned and began to coat his cock with cum on the other side of my face. “Never waste a drop, not event from another faggot – consider that lesson 1.” Master said. Daddy took his cock out so that Master could feed me what was on his big black cock.
They laughed and continued “cleaning me up”.
Also Read: Sissy Assignments Vault – A Secret Place for More Training and Teasing