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Mom's Big Black Hobby Ch. 05

Story Info
Harvey and Mommy get punished (not in a fun way).
3.2k words
4.24
48.1k
49

Part 5 of the 9 part series

Updated 06/15/2023
Created 06/05/2020
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This story has with incestuous and homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned!

All characters in this story are over the age of 18. The entire story is fiction as are all characters. Any likeness a character has to someone in real life is merely circumstantial.

This story may not be copied without the direct permission of the author (me!)

If you enjoy the story or have any (positive or constructive) comments, please let me know.

*****

The weekend was over, but Mom kept me in the house for the next few weeks. She had a visitor every day. Each time was the same: a large black man would arrive, she would bring him upstairs and he would fuck her in her (now 'our') room. Sometimes she wanted me in the room to watch.

I was on a strict diet with no carbs or meat which meant I felt a lot weaker and was hungry all of the time. I had completely transitioned to female clothes, none of which were particularly modest. I was taught by mom how to do my make-up and style my hair properly and now did them both on my own each day.

The crazy part to all of this is that I didn't want to be here. The initial adrenaline and curiosity had worn off and now I just wanted to go back to how things used to be: a world where I was a guy with a cock and not a sissy girl with a clitty and boi pussy. That's what they called it by the way - my dick in its cage: they called it a clitty. Mom's lovers would comment on it when they fucked her in my presence.

Her lovers were exclusively black and none of them seemed to have a problem with my imprisonment. Most of the time they would end up cumming on me or inside mom and I'd be made to eat it up. Mom called it my 'Protein supplement'.

Speaking of supplements, my lord were there a lot. I'd choke down a dozen pills each morning and take a range of follow-ups throughout the day. My least favourite were the large depositories she thrust up my butt each morning. You could tell they were working however, as my nipples were a lot more sensitive: protruding slightly and becoming more puffy. Who knew how they would look after a couple of months of treatment...

It was a random Tuesday, Mom had me lapping up cum from her stomach where the guy had overshot her pussy. The guy; who I had thought had walked out after finishing, took me by my arms and threw me to the ground. "Mark!" my mother exclaimed; turning suddenly as my tongue left her body, "leave her be."

"Fuck off cunt," he said gruffly as he walked over to pull at my plugged-up asshole now revealed as the tiny thong had fallen aside. I hadn't had a man's in my ass since I had been 'broken in' weeks before, though my mom had forced me to stay plugged each day and night. It was actually quite comfortable. So much so that when it was removed I felt empty and lusted after something to fill me.

The plug was pulled from me and I felt the cold air tickle my insides. I moaned something that sounded like longing. I couldn't see his face but could picture his smile as I heard him chuckle at my need for something in my ass.

"She is being trained for Joe," she exclaimed to him, as I felt the tip of his wet cock pressed up at the entrance to my boi pussy. He stopped at the sound of Joe's name, retracting himself from me. I once again felt a breeze up inside me and felt hollow and empty without anything inside me.

He grumbled something of disapproval and walked back over to my mom. With one movement of his strong muscular arm, he had her on her feet. He then went about slapping her tits. it looked quite painful, but she seemed to take it like a champ, squealing quite a bit but never moving from the position.

When he got bored, he then turned her around again and began slapping her ass. Another 10 minutes and her tits and butt were bright red. I looked to the man beating my mother with such anger and spoke out: "Stop, you're hurting her!"

Now, I'd never raised my voice to one of my mothers lovers before. Until now, I thought she had enjoyed all the sexual abuse, but I could see that she was not enjoying this. He turned on me, eyes ablaze and nostrils flaring. He took a step to me, arm raised, looking as though he was going to strike, but seemed to think better of it. He lowered his arm and walked out the room.

I was giddy with excitement! I had won, I had stood up for my mother! She didn't seem to share my enthusiasm, as she ran after the man, her tits bouncing as she bounded out of the room: "Mark, please come back! She didn't know! We are still training her!"

I looked around the room and my eyes found my butt plug. The size of a small girls fist (my fist), and I forced it back in my rectum. The pressure gave me a sense of comfort and I walked out of the room feeling confident in my new self.

As I wandered down the corridor to the landing, I passed the large mirror that stood there. I stopped for a second staring at my girly abused body. My puffy nipples stood out and my painted face was dripping with sweat and cum. I then looked down to my clitty...

Loud shouting came from the lounge. I snapped back to reality and ran to the stairs. As I descended them, I saw Mark on the phone, speaking aggressively down the line, my mother was being chocked at his other hand. She was playing with her clit profusely as he choked her: her other hand fondling one of her red tits.

As I reached the ground floor, he hung up the phone. "Stop," he commanded to my mother and she instantly stopped rubbing her swollen clit. He then picked her up off the floor using just his one arm and threw her back: having her land back on the carpeted lounge floor.

He then looked directly at me and spat: "Joe will be over shortly to discipline your ungrateful faggot ass". My heart dropped. Joe was the man at the club that my Mom had promised me to. "Your Mommy has protected you enough slut. You're now gonna feel what it's like to serve like a real street whore, just like your cunt Mommy over here," he indicated to my mom who was lying on the floor in front of me.

"Get me your pain chair." He turned his look to my mother as he spoke. I heard her gasp as she regained her feet. Clearly a little distraught, she walked upstairs and off to one of the locked rooms to the right.

She came down moments later with a stool rather heavy-looking metal stool, atopped with a large ornament. As she got closer, I could see the ornament was in fact a dildo - but the largest one I had ever seen. It must have been the girth of a melon and the length of rolling pin. The stool also boasted a second, slightly smaller (but still huge) version adjacent to the first. With my new found intuition found in all things depraved, I deduced the smaller one to be for anal penetration.

She set it down in the middle of the room, backing away and assuming a submissive dog-like position on her knees. Mark went over and inspected the stool. The dildos were not lubricated at all and I expected him to have mom rectify this, though he made no such effort to instruct so. Instead he took his cock in his hand and a jet of piss came gushing out onto the stool. It didn't take long to coat both dildos in the sweet-smelling liquid before the flow stopped.

He pointed to the chair and my mother crawled towards it. I assumed he had lubed it up for her, but no: she went about sucking the piss off the dildos. I noticed that the chair seemed to cup slightly in the middle, collecting all the fluids and dripping down into a bowl at the base. It turns out the bowl could detach, which I learned watching her picking it up to pour its contents in her mouth.

I attempted to walk up to her; confident in my new-found power, Mark held out his arm: blocking my way. Though I felt confident, I didn't dare physically challenge the man. He was easily a foot taller than me and his body was that of an olympic god, whereas mine barely constituted that of a pubescent girl.

He whistled once and my mother replaced the bowl she was now licking clean. She stood and moved over the sex toys. I cringed as I watched her lower her pussy onto the large horse cock. She visibly showed the pain on her face; though stayed quiet, only releasing a low grunt every inch or so she pushed down.

When she was 3 inches down her asshole met the second dildo. She reached back to spread her cheeks, clearly struggling to get it through the entrance of her slutty swollen hole. Mark seemed to feel she was taking too long and paced over to her. He stood over her looking down as she sweat through the pain. "Take it you cock whore," he spoke, placing his hand on her shoulder. She couldn't seem to get it inside her; her face red and twisted in agony as her sphincter tried to accept the large eggplant-sized toy.

Losing patience, Mark lent some of his weight to her shoulder. She began to scream, but still didn't move. He then lent more of his weight. This time, she eased down slightly as her ass finally gave way. She pulled both hands forward and began furiously rubbing her clit. Once she had got through the opening she shot down as both her pussy and ass accepted the giant cock-meat toys.

I couldn't tell whether she had damaged anything, but she was crying nevertheless. Up until this point my mother had taken everything she was given with a smile, but now I saw her being punished I became scared. Despite all the pain however, she seemed to be in great pleasure as she erupted: clearly cumming, as her ass finally touched the cold metal of the stool.

Once she had cum, she then sat there; tired and motionless, as Mark looked down at her with that malicious smirk on his face. The whole event had taken approximately 20 minutes and as mom sat there: mouth open, drooling like some sort of pornographic zombie, the front door swang open.

In the open doorway stood Joe: the black man my mother was 'preparing' me for. I froze in sheer fear as Mark opened his arms to the man: "Joe, how are you?"

Clearly not Mark's biggest fan, Joe ignored the remark and made a beeline towards me. I squealed as he approached and saw him brandishing a belt once 5ft from me. I felt the ting of leather on my ribs: such a heavy blow knocking me to the floor and making me keel over. His rough hands picked me up and carried me away and out the door. The last thing I saw of my mother was her ass, split over as if trying to swallow a tree; Mark with his cock buried all the way inside her throat: suffocating the life out of her.

I was carried to a mercedes parked out front, its windows tinted and licence plate read 'PUN15H U'. I was thrown in the back seat, where I hurtled into a small white girl. She was totally naked except for the sexual accessories adorning her body. She had bolts pierced through both her nipples ending in rings. Those rings had chains running up to her mouth, where a plastic black ball gag kept her quiet. The ball gag also had a little ring on the end where the chains were attached to. Her pussy was penetrated by a large dildo coming out of the seat. Judging by the one on my own seat it was 12 inches long with the girth of my arm.

She looked scared back at me and pointed to the dildo on the seat. I turned to show her my plug, but her hand quickly went to it: pulling it out. With a 'plop' sound, my ass gaped and I positioned it over the dildo, sliding down inch by inch until I was to the leather of the car seat.

Joe had climbed in the car and was already out of the driveway by the time I was completely atop the dildo. Looking around, I was unable to locate a seat belt. As we went around the first bend, I understood the purpose of the dildo's buried inside us.

It took approximately an hour, but we finally arrived at our destination. The car stopped and the door opened beside me. Multiple white ladies: all wearing latex all came to carry the two of us out. As they pulled me off the dildo, I heard one of them remark at the size of my 'fuck tunnel'.

The scene was chilling, as all I could see was a small barn. Upon being pulled from the car, we were escorted to the entrance of the barn to be joined by Joe. He ignored us as we walked and it wasn't until we were inside that I truly understood the severity of our sentence.

Inside were women and sissy alike, strapped to the walls, their bodies undergoing intense sexual torture. 3 naked bodies currently stood there with room for 2 more. The girl next to me started to scream through her gag, to no avail. One of the latex-clad slaves escorting her gave her a prod with some sort of metal stick. Upon contact, I heard the zap of electricity as she was stung.

The 3 already there were a sight to behold. The 1st was an asian girl, whose arms and legs had been outstretched and tied to hooks in the floor and ceiling. She wore head-gear where hooks opened her nostrils and a familiar-looking gag opened her mouth wide. In front of her, the base of a dildo; the balls resting on her chin, thrust to the back of her throat. The Dildo had a tube leading out of it which seemed to pulse every minute or so.

The second was a a white girl. If I had seen her out and about, perhaps she would have been cute: long blond hair, puffy pink lips and giant double D breasts. Her ass was round and plump, whilst her waist skinny. She was, however, an absolute mess. Unlike the first girl, she was bent over a metal bar, with her hands and head locked into a wooden stockade. Her tits were attached to pumps and hung down low beneath her, in addition to her pussy which was also covered by a transparent pump. Her pussy was swollen and red and she was screaming through the ball gag in her mouth as it pulsated, vibrating her pussy lips.

The third was the worst, however. Dolled up in make up to make her look like a painted whore, she was suspended in the air by her legs. Her mouth was covered with a dildo gag that made it impossible for her to voice any of her concerns, but her eyes were wide open. It probably had something to do with the horse cock dildo that she impaled her ass on the end of a machine akin to that of a jackhammer or the seemingly tight string tied around the base of her chastised penis, causing it to have turned blue from the lack of blood flow. I either case, she was clearly in pain: tears staining her face and body convulsing with each thrust of the sex toy.

I looked right to my nearest escort who's outfit was a bright yellow. Apart from her hair, three clear holes had been established on her outfit: two for her tits to poke out and one as a slit from her ass to her pussy. Her face was mostly obscured by the rubber mask but her lips and eyes were visible, heavily painted and with her lips boasting what must be a few injections of lip filler.

She didn't say anything as she lead me to one of the two remaining blocks. The other girl, now much quieter; though sobbing, was lead to the other. Joe stood in front of us and the latex-clad drones now kicked at the back of our legs so we were on our knees whilst looking up at him.

"Ladies, you have been brought here to be rehabilitated," he began. "You will see that this is not a pleasant experience and will test your devotion to me as your master. Besides you you can see other sluts who disrespect me and my colleagues, either by refusing to swallow cum or perhaps touching themselves without permission," he looked at the asian girl and then the white girl in turn as he spoke.

"Perhaps even, trying to have sex with one of my other girls without instruction to do so," he cast his gaze to the sissy beside me. I could hear the squelching of the huge dildo as it pounded at his broken little asshole. I looked once again to his blue limp cock and swallowed at the thought.

"Today Miss Cameron, you will be punished for your pride by making a video for your father. In the video you will openly admit to being an anal-loving slut and beg him for his cock up your ass." The girl looked mortified. Clearly, she did not have the relationship with her father that I had with my mother and the thought of making such a video seemed to rock her. "That will teach you to deny your ass to one of my business partners," he finished.

"And for you," he addressed me. "Mr Gates has told me you challenged his dominance over your mother. Why, that whore doesn't deserve the effort you seem to have boasted, though nevertheless I will need to teach you to know your place." Regretting my decisions, regretting my whole existence, I waited to hear my sentence.

"You will be reminded of who you have become with simple fasting. Whilst the others will be gone in a number of days, you will remain here for the next month without food. You will perform the duties as one of my slut-dolls," he gestured to the nearest of the women in latex, "where the only sustenance you may gain is from the cum of my patrons." I felt my cock twitch at the sound of eating cum. Was I seriously that much of a slut that I already looked forward to my next helping?!

"But first," he interjected mid-thought, "you will endure each one of the punishments beside you here."

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8 Comments
robisj089robisj08926 days ago

Great story so far!

WeezyfWeezyfabout 3 years ago

Also whats that about protecting him lol, if anything she is the one forcing him into slavery by bringing him to that mansion and stuff

WeezyfWeezyfabout 3 years ago

: "Mark, please come back! She didn't know! We are still training her!"

Why didnt she tell her son about the rules? And what training? Nothing…

AnonymousAnonymousover 4 years ago
More hardcore sissy stories

I love this type of sissy writing, too many stories are written tame.

This is clearly deserving of the title "Hardcore".

AnonymousAnonymousover 4 years ago

At this point I would consider this story to be Horror Erotica. While I love the descriptions, sometimes they can cloud the scene and with horror sometimes the authors best tool is the readers imagination so don't be afraid to limit some details for that to take a larger effect rather than clouding the picture with too much detail.

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