Mom's Big Black Hobby Ch. 03

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.

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I roll over to my back and open my eyes: I'm in my bed, snug under the covers. I think back to the last couple of days and my mind begins to race. I suddenly remember the girl: Amy. Or is she a guy? I feel around my body only to find myself wearing those satin purple panties. I sit up.

The curtains drawn to my left, don't quite block all the sunlight; it was clearly no longer dark. I searched the floor for a sign of my clothes. Seeing something catch my eye at the end of the bed, I bent forwards only to be met with a view of Amy. She was asleep, slumped over face down, short skirt riding up revealing her little caged cock poking out between her legs.

I stare at her little cock, looking less than 1 inch long squashed into that tight cage dangling straight below her asshole, looking much less tight and puckered than it had felt, left slightly agape. Her makeup looked immaculate. Perfectly drawn purple lipstick and a thick layer of foundation certainly made her look dolled-up.

As if she could sense herself being watched, her eyes fluttered open looking back at me. She gave me a small smile. Her perfectly drawn mascara made her green eyes pop. "Did sir enjoy his nap?" she said in her high-pitched girly voice.

I didn't know how to react. I suppose some honest conversation might be therapeutic in this moment. "Are you gay?" It was a bold question, but she seemed somewhat un-phased by it.

"I don't see what we just did as gay, because I see myself as more of a girl than a guy."

Taken aback a little by her answer, I pressed further: "Describe what you are to me."

Breaking out into a much larger smile, she sprang to her feet. Taken by surprise, I reared back a little, away from the edge of the bed.

"So I am a Sissy;" she began, "a transgender crossdresser who is submissive to more powerful men. I used to be a boy, but when I turned 18 I changed my identity and became the property of Daryl (Daddy) who keeps me as his personal slave."

So many questions, I thought to myself. "So, you consider me a more powerful man?"

She scrunched up her face a little as she answered, speaking less enthusiastically: "Honestly, not really. But Daddy told me to do it and that's enough for me. I would do anything for Daddy."

A little emasculated over the sissy not seeing me as a stronger man, but brushing past it, I continued: "You are a slave. Like a sex slave?"

"Yes and no. I am first and foremost a companion to Daddy. I will cook his meals, wash his clothes and do all the other jobs such a powerful man should not have to do; but then yes, I will voluntarily be his personal fuck-toy. If he wants someone to have sex with, someone to humiliate, someone to abuse: I'm his."

"What do you mean by 'abuse you'?"

"I don't particularly enjoy everything he does. But I do it because I am his. The other week he had me and another one of his girls piss on each other - I wasn't a massive fan, but I love pleasing my Daddy."

So there were more of them, I thought to myself. "And what about your dick?" I asked, pointing haphazardly at her member now hidden beneath her skirt.

Lifting the skirt up, he walks over to me so I can get a better look. "Daddy keeps me locked away. A sissy doesn't need her tiny little cock to cum. Also, it's not like she can pleasure anyone with such a little tool". She takes my hand and places it on her cage. The pink plastic felt warm, the tip was wet: likely where she had cum on my belly earlier.

"I can see you also like crossdressing" she said, gesturing to the purple panties.

Instantly I become defensive. "No, no, no. These are my mothers, I just had no clothes,"

She looked down, disappointed. "I'm sorry. I didn't mean to make you upset.

Instantly regretting my reaction, I tried to comfort her: "oh no, it's fine. I... I'm just getting used to all of this. Before yesterday, I had never seen another guy's dick in front of me."

She stared back at him dazed. Her face really did emanate 'Bimbo': her mouth hung open as she stood there thinking. "What happened yesterday?"

I felt uncomfortable again. I didn't want to share the traumatic scene I had walked in on yesterday evening when I got home. But perhaps, this is the one person I will be able to share it with. She clearly dealt with much worse on a daily basis.

I paused in thought for a moment. In that time, I realised I also held my mouth open, like a Bimbo. Quickly closing it, I cleared my throat a little, concluding that I needed to share this with someone, so why not her? - "I came home for the first time yesterday to surprise my mom and found her being gangbanged by a bunch of huge black guys. I walked into the room to see her pussy and asshole in full view: both gaping. They had chained her down and there was cum everywhere."

"That sounds like it was quite the shock."

"It was! I was horrified. I don't know who she is anymore. I don't know who I am. I just fucked a girl with a cock for fucks sake."

"Who do you think you are?" She spoke so simply and matter-of-fact. I'm over here being hysterical and this transvestite is being calm and rational about the whole ordeal.

"I don't know," I said, starting to calm down. "I have been thinking about her tied up. I see this one black dildo in her room and... I dunno. It turns me on to think about it."

"Hmm, I think I can help." With that she exits the room and walks to the door and out of the room leaving me sat there alone, in nothing but a pair of purple satin panties.

Two minutes later she returns with a large purple duffle bag. She places it on the dresser next to the bed. "Would you like to explore your sexuality a little, Harvey?"

Breathing heavy, I nod slightly: my eyes transfixed on the bag.

She smiles. "Perfect". As she unzips the bag, the first thing she grabs is a large (and I mean LARGE) bottle of lube with a handy pump-cap. She set it down on my nightstand and went back to rummaging through the bag.

She then pulled out a brown dildo. It was a lot smaller than the one in my mom's room but still larger than my own cock. Placing this on the side she continued. She then began pulling out makeup. Finally, she took a small felt bag. Reaching inside she revealed a moderately-sized butt plug.

Opening the curtains, she flooded the room with a low-orange glow. It must have been late afternoon - I had slept all day! She sat me at the dressing table and got to work. By the time she was done with all the makeup, I looked like a pretty tom-boy. She added a final touch placing a shoulder-length brown wig on my head, styling it all pretty-like.

"Daddy always likes me pretty before a good fuckin'," she said whilst she finished up with my lipstick, "and now you look so pretty!"

Feeling nervous, I feel my ass tighten at the thought. Starting to have second thoughts I looked around the room. Amy must have seen this as she reaches down to stroke my wig.

Despite my fear, my cock was alert. I've never had such virility as I have had this weekend. She moves around to clean up the make-up and I stand up to look at myself in the mirror. I thought how the swimming really did seem to make a difference, staring at my skinny hairless body. I was absolutely passable. I had no tits and I had a small tent in my panties, but I looked fuckable.

Amy must have thought so too, as when I turned around, she had the brown dildo secured in a harness. "Aren't you going to fuck me with your own dick?"

Looking at me like one would look at a naive child, she shook her head as she spoke: "You don't get it. I don't have a dick. Sissies, only get fucked. Today I'm pretending to be a man, so I need a toy to pretend with."

She spoke in such a way that made me really believe what she had to say. With that, she walked up to me and began to kiss me. Her hands explored my body. I felt her rubbing my cock through my panties and pulling on my nipples. Eventually her hands went back to my ass as she pulled the panties aside.

I felt something cold and wet as she guided the butt plug to my tight hole. I tensed up. 'There was no way it was getting in there' I thought. 'My asshole is too tight'.

"Relax," she spoke softly into my ear. I felt her other hand guide my own back to her ass, which was already covered in oily lubricant. "Now play with me," she whispered. I did, and began slowly fingering her hole, stretching it with my fingers.

"Now, play with me how you want me to play with you." I was already lost in the erotic nature of the scene: two guys kissing whilst wearing makeup, dressed as girls; I was in another world.

I slowly eased off and pushed my finger on the outside of her hole. I felt the cold metal on my own hole and pushed a little further into her ass. This continued for some time until finally my ass engulfed the whole of the sex toy. I felt so full: so naughty. 'I get why people like this' I thought to myself.

Amy then pushed me down on the bed on my back. She immediately went down on me, sucking and slurping her way up and down my cock. Her gag reflex didn't seem to exist as she abused her throat with my cock.

After a few minutes, she moved herself around to position herself above my face. I was staring straight at her strap-on cock as she went up and down on me, continuing the blowjob. "Lick my asshole" she said through muffled throat-fucking.

I didn't have to be told twice. I dove right in and began tongue-fucking her ring vigorously. After another few minutes I felt myself getting close to cum. I exclaimed this to Amy and she began to slow, eventually stopping.

Climbing off my face so I was no longer being smothered, she walked around to the edge of the bed and lifted my legs. With a small tug, she pulled out the plug, making my ass feel empty. She soon replaced it with a long thrust of her hips: forcing the dildo past my sphincter.

The walls of my ass quickly closed around the cock with each push as I laid there: a slut on her back. She started slow and shallow, allowing me to get used to the increased size. Eventually she had built her way to a deep jackhammer. I was in ecstasy, where all I could feel was the burning up my ass and all I could hear was the slapping flesh of her slamming into my ass.

It finally became too much and my cock began to spurt. I had both hands clutching the bed, my orgasm had only sparked from the onslaught on my butt. The cum came in waves over myself as I could only moan inaudibly. I was so loud that I hadn't heard the door to my room swing open.

As I came down from my high, I began to see once more. Before me stood 3 figures. Amy still had her dildo buried in my ass. My mom stood there in nothing but a g-string. Beside her, some random black guy had his cock out. "What the fuck are you doing in here?" I exclaimed to the room.

My mother spoke up: "We heard your moans sweetie and honestly I thought you may have been in pain". She looked to Amy with a smile across her face, "Never did I think you would actually be fucking this little sissy, let alone have her fuck you."

Amy turned to my Mom quickly: "I'm sorry Ma'am, he explained to me how he imagined getting fucked like you were and so I was only trying to help". All through this conversation, my ass was still filled with her monster-of-a-dildo.

"Well, if you want a cock son, I am more than happy to provide you with one", she gestured to the guy beside her, grasping his hard member with both hands.

"Amy, pull out of me". I practically screamed it. I was panicked now. My mom had seen too much. This was all too much. She slid the huge strap-on out my ass, clearly it was a little dirty. I guess there is probably quite a lot of prep that goes into anal sex...

I scrambled off the bed, grabbing the panties beside me and ran out of the room.