Sissy for the Family

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried.

She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-old mother. The only thing good about this man was that he was rich, which I guess was the sole reason my mother settled for this yellow fevered douchebag. And if one douchebag wasn't enough, Jack just had to have a son. 2 years younger than me, my stepbrother, Patrick, was a bigger douchebag. Although he was 2 years younger, he was much bigger than me, not surprising given than he was of a Caucasian descent.

Both Jack and Patrick made it their life mission to make my life a living hell. Jack made sure I knew my place verbally and Patrick did likewise, physically. The only reason I tolerated this shit was because my mother was content with the rich life. However, she has started to treat me with more irritably which I'm guessing it's because Jack treats her better when he sees that I'm being forsaken by my own mother.

Of course, I wouldn't say that I was perfect either. Growing up with a single mother in her 30s who was too tired to wear clothes around the house, I was attracted to my mother's underwear. She looked so comfortable and at ease. I remember the first time I sneaked into her wardrobe and stole my first pair of cotton panties. Pink with white elastics, simple and soft. When I put on that pair of panties I experienced pure bliss. The softness of the cotton rubbing against my skin with the tightness around my cock and ass, brought me to sheer ecstasy. Since that day, I've escalated to wearing my mother clothes and makeup whenever she wasn't around. I would spend hours just looking at myself in the mirror dressed up as slutty as possible.

However, my bliss was cut short when my mother remarried, and we moved into jack's house. My mother quit her full-time job and picked up a part time gig as a nanny just a few blocks down the road. So, with my opportunities to dress up diminished, I turned to the internet, and down the rabbit hole I fell. I found sissy porn, then shemale porn, forced bi porn, and finally gay porn. Now I've been so brainwashed that I'm suppressing my sissy urges 24/7. However, that was soon to change.

It was a Tuesday afternoon and the opportunity to dress up finally presented itself after 2 weeks. My mother shut the door without a word goodbye as I watched t.v. in the living room. Jack was at work and Patrick was having soccer practice. I was FINALLY alone. As soon as I saw that my mother was out of sight, I ran up to her room and open her wardrobe. I grabbed the sluttiest outfits I could find. A black satin thong, and a tight short black bodycon dress. The dress only covered half my ass and the thong playfully peaked out from under the dress. Next was makeup. I chose a darker ensemble of make up to match my outfit and by the time I was done, I looked like a complete slut rocking a pixie cut.

Next came my favourite part. I opened the drawer of my mother's bedside table and there laid a bottle of lube and a 6" pink dildo. Just looking at the pink dildo made my already hard cock twitch. I wasted no time. I keeled upfront of the mirror and put the dildo into my mouth. I could now easily deepthroat the entire dildo with ease, a skill that made me feel extra slutty. As I continued to loosen my throat, I squeezed lube onto my fingers and started to massage my asshole. I slid my finger in and my body shivered in ecstasy. I loved that feeling. One finger became two and two became three. Soon my asshole was begging for more. I took the dildo out of my mouth and pressed the tip against my asshole. Covered with my saliva, the dildo slid right into my asshole and pushed against my prostate. I pumped the dildo exact three times before my cock started spraying fun all over the floor. My balls tightened as the emptied and my asshole clench reluctant to part with the dildo.

"ISSAC! WHAT THE FUCK IS GOING ON HERE?!" a familiar voice shouted.

I turned around in horror, the dildo still up my ass. It was my mother. I was a dead man.

"Why are you wearing my clothes? Why are u wearing my makeup? Is that my dildo?!" my mother questioned as I stared at her in silence.

"Mom! I-" I shouted finally breaking my silent shock.

"Shut up! My son is a freak! I'm calling Jack! Don't you dare move!" my mother demanded.

Jack? Why does she have to tell that douchebag? My head pounding with panic and fear as I sat on the ground dressed as a slut, dildo up my ass and cum on the floor.

My mother seemed to be on the phone for hours although it was probably just minutes. Her face of shock and disgust relaxed as she calmed down. She nodded and hung up the phone before turning to me.

"Honey, you're a sissy, aren't you?" my mother asked as she walked towards me and squatted next to me.

"Uh, mom. Look! Let me explai-"

My mother slapped the dildo forcing it deeper up my ass shutting me up.

"Answer the question honey, are u a sissy?" my mother asked again. Her hand just ready to give the dildo another slap.

"Yes..." I replied, defeated.

"I want you to say it honey and call me mommy." My mother said as she gently pushed the dildo.

"I'm a sissy, mommy." I replied.

"very good. Now, a good sissy cleans up her mess, so go clean up all that icky cum that you left on the floor."

I reached for the tissues on the bedside table before feeling a sharp slap on my ass.

"You stupid sissy! Use your tongue! And from now on u may only stand when you've been given the permission too! Now crawl to your mess and lick it up before I spank that slutty ass red!" mommy shouted.

I crawled to my my mess and lowered my head. The smell of my own semen filled my nose as I stocked out my tongue. I began to lick my own cum off the floor. The humiliation was intense, but my cock started to stiffen. Soon, the floor was clean, and my tongue stained with the taste of my own semen.

"Good girl! Now take that dildo out of your slutty asspussy. Then kneel in front of me!" my mother said as she sat on the bed."

I pulled the dildo out of my asspussy and felt the cool air against my gaping hole. I crawled to mommy and keeled in front of her. My cock hard as a rock from all the humiliation.

"My my, look at my little sissy's hard clit. That's right, a real man's cock is sooo much bigger than that tiny clit. You're even smaller than your father and I thought his was small already! Wait till u see Jack's cock! Anyway, I've spoken to Jack and we decided you're less of a burden as a sissy. So, if you want to keep staying in this house, you will be this family's sissy and there will be rules you must obey."

"Number one, from now on, you will be called Isabel and you will address me as mommy, Jack as daddy and Patrick as master. That's right. Patrick owns you now. You're just a toy to Patrick. You understand?" My mother taunted.

"No please mommy! Why does Jack and Patrick have to be involved!" I replied.

Suddenly, my mother kicked my hard cock with her feet sending shocks of pain coursing through my body.

"How dare you disobey me and how dare you refer to your daddy and master by their names? If you ever do that again, I'll make sure those sissy balls come off!" my mother yelled.

Gasping in pain, I nodded my head as reply.

"Good. Number 2 never disobey your superiors. You will do whatever you're told without question and you will always thank them for whatever they do."

"Number 3, you will always be dressed as sluttily as possible. That means you are to grow your hair out but shave all your hair from the neck down."

"Now that you know the 3 basic rules, go get ready for your master when he comes back. You're allowed to stand now." My mother concluded.

"Thank you, mommy." I replied. I stood up and ran to the bathroom where I shaved off all my hair below the neck. I both dreaded and anticipated my brother's arrival. What was my mother going to make me do and what was my brother going to say? The thought of the humiliation made my cock hard.

Soon, I heard the door close and I heard my mother shout: "Isabel, come down!"

I walked down the stairs where my mother greeted me. She told me to go to the living room and kneel which I did. Patrick was sitting on the sofa watching TV. His clothes still soaking in sweat.

"Patrick dear, come say hi to your new toy." My mother said lovingly.

"Toy? What you guys buy me?" Patrick shouted excitedly as he turned around.

"what the fuck? Is that ISSAC? What the fuck is he wearing? What is he doing?" Patrick shouted.

My face turned bright red from all the humiliation, but my cock twitched and strained against the black thong.

"Patrick, me and your father have decided that your elder brother would be more useful as your personal sissy slave. Isabel here, will obey your every wish and you are free to use and humiliate her however you wish." Mommy explained.

"Sissy slave? Humiliate? Mine? So, if I wanted Isaac to suck my cock now he would do it?" Patrick asked.

"Yes honey, but remember, she is Isabel now. Although you could call her anything u want since she's yours now."

"Really? Fine! Hey sissyboi! Come beg me to let you suck my cock!" my brother shouted with an arrogant smile on his face.

Reluctant, I looked at my mother.

"Go on sissy! Your master has spoken! Go fulfil your masters wishes!" my mother warned.

I crawled in front of Patrick unable to look him in the eye. The humiliation was overwhelming, but my cock loved it.

"Can I suck your cock?" I muttered.

"Look at me when you're begging me slave!" Patrick shouted as he grabbed my face.

"Beg me like you mean it!" Patrick yelled slapping me on the right side of my face.

"Please master! Let this dirty sissy suck your big cock!" I begged in fear of another slap.

"BETTER! Not ideal but I'll let it go this time. Start sucking faggot!" my master yelled as he pulled his pants down to reveal a 5" flaccid cock.

I gulped as I saw the size of my YOUNGER brother's flaccid cock. My cock was only 4" fully erect. I opened my mouth and stocked out my tongue allowing my masters flaccid cock to rest on my tongue. Then I moved my head closer welcoming the tip of his cock into my mouth. His cock started to stiffen and grow. I continued to work my way down his shaft causing my master to moan. His cock grew thicker and bigger forcing my mouth to open wider. I could feel the tip of his cock approach the back of my throat.

"You're taking too long sissy! Looks like I'll have to fuck that mouth pussy myself!" my master yelled as he grabbed the back of my head and rammed his now 7" cock all the way into my mouth. His balls felt heavy as they slapped me in the chin.

I started to gag as my master pumped his cock into my mouth vigorously! I gasped for air between pumps as I prepared for the next. My master became an uncontrollable beast as he fucked my face aggressively. I was just a hole for his dick at this point.

"I'm cumming! Fuck! Your sissy mouth pussy feels so good! Take it bitch! Take your masters cum! Swallow every drop you slut!" my brother climaxed as he pushed his cock as deep as he could. My nose rubbed against his belly. I could feel ropes of warm fluid hit the back of my throat and a salty, bitter taste filled my mouth. I swallowed hard to stop myself from choking before I realised I was swallowing my YOUNGER brother's load.

My master held my head tight as his cock started to soften in my mouth. The taste of semen and sweat lingered on my tongue, and my throat felt sticky and warm.

"Oh, fuck Isaa- I mean Isabel! That was FUCKIN awesome! You're better than the girls in my school! We're gonna be spending a lot of time together from now on sissy! Now clean my cock off."

"Yes master, thank you for your load." I replied as I continued to lick the cum of my master dick. My cock had never been harder.

"Well done sissy! I can't wait for your daddy to come home!" my mommy said as she patted my ass.

As I continued to clean my master's cock, I knew my life would never be the same. I too, could not wait for my daddy to get home.