The Evolution of a Sissy Ch. 02 - 03

Chapter 2

Thank you to the people who have commented on chapter 1 and mentioned how I kept jumping from 1st person to 3rd person. I realised I had done this and have noted it. Hopefully, the following chapters will be 1st person and easier to read.

Twelve hours after getting home from work and spending all night wearing my new latex maids uniform, I finally succumbed to my lust and shot a teaspoon worth of cum onto my fingers. Now the embarrassment hits me. Sat here with my sexual pleasure fading fast whilst in front of the PC screen with a carrot in my butt and the muted video playing of a young Black Master practically raping an older sissy's white ass still playing on the screen.

Standing up to get undress, I see my reflection in a mirror and cannot look at myself in the eyes due to the shame. Quickly undressing, I make sure to hang up my expensive latex, so it does not get damaged. Pulling the carrot from my ass-pussy adds to the shame of it all. The water-based lubricant I used has dried inside me and makes the carrot stretch on my tight hole quite painfully as I extract the 8-inches of vegetable. Now off to bed now for a few hours' sleep.

10 am Sunday morning, and even though I have only slept for 4 hours, I have woken up with an intense sexual urge and need to get my cock in my hand again soon. Half asleep, I can't help but involuntary start to grind up against a pillow that I have between my legs. Come on bitch, get your ass out of bed and spend the day in front of the PC again; you know you want it and need it.

Hours later, and once again, dressed up like a latex clad whore gooning to endless pornographic images, videos, stories and perving through FemDom and Dom BBC profiles. I have nearly lost my nut many times so far, but practice means I know when to stop wanking off and calm myself for a few seconds.

Lost in my sexual pleasure, I now try to think up excuses to not go to work tomorrow and stay home wanking off. I already know in my heart that I will be calling in sick tomorrow morning. Ummm, I love that moment when I have decided a plan, and I can now relax and enjoy my hand late into the night without needing to get up early tomorrow.

So begins a self-destructive yet pleasurable lifestyle that will soon become the norm for me. This lifestyle will eventually affect my work and my social life, even if I do not know it yet. The selfish sexual urges will soon become more important to me than keeping good attendance at work and partying with friends Etc. If I could see the future, maybe I would not spend countless nights home alone dressing up and edging myself to many different kinds of fetishes.

Pretty much all of my free time outside of work is spent at home, dressed in an ever-increasing sissy wardrobe of latex and other fetish-themed outfits whilst I spend endless hours rubbing on my tic-tac like cock to porn online. It is not uncommon for me to masturbate for so long that I eventually just get tired and fall asleep, only to start again the day after. I could be an Olympic champion at edging if that game was ever an actual event.

My friends do not even bother to text me to ask if I am coming out partying on the weekends anymore; they have been told no one time too many. Whilst they are out drinking, going to nightclubs and picking up girls, I am likely at home sitting on one of my big black rubber cocks. Sat on one of them whilst gooning myself and trying to instigate a kinky chat with an online dominatrix, or occasionally a black Master. It is fun getting deep into my sub-space when horny, to imagine a black Master owning me, even forcing me and making my sissy feminisation complete, but then, I spray my cum, then, once again like clockwork, I have zero desires for that fantasy. I am more consistent and genuine in my desire to find and serve a real-time Mistress/ Girlfriend, though, not that it helps with the search.

I felt like the luckiest man alive when I received a message on the Bumble dating app from a stunning local woman who said she was intrigued with my profile. She had pointed out the subtle indicators of my submissive nature and interests in dominant women what she noticed in my profile. I had added a few token kink words to my profile with the hope a dominant woman would see them and put two and two together. Luckily Kim had picked up on these signs and started the ball rolling.

Not wanting to mess up this possible life-changing opportunity, I did not hesitate to go along with Kim's offer to meet up for a coffee. Fast-forward three days, and here I am, sitting in a coffee shop awaiting Kim's arrival. Literally shaking with excitement and fear of meeting this woman.

Having arrived thirty minutes early and after drinking 2 Lattes, I need to pee badly. Getting up to go to the toilet was the exact moment Kim chose to arrive. I literally walked into her since the men's toilets are next to the entrance.

"Not planning on running away from me, are you?"

"No, Kim, far from it, I just had too much coffee and need the toilet."

"That is Miss Kim to you, little boy; now, go fetch me a double espresso and get yourself a glass of water".

"I will just go pee first."

"Stop! I said I will take a double espresso, and you can have a glass of water. Go fetch them whilst I find us a quiet table out of the way."

That is how I met Mistress Kim, my first ever real deal Mistress, and she still controls when I go pee.

Chapter 3 ( 3 years on )

With mascara black tears running down my face, I am currently in a world of pain as my Mistress is spanking my backside relentlessly with her hairbrush whilst I lay across her leather skirted knee.

For the second time this week, I have been in this position whilst feeling her arm's strength. This week's first spanking was the regular maintenance spankings, so not that hard and not given because I had done wrong, no, to keep me on my toes and remind me of my position in this relationship. My backsides current unbearable pain that was getting branded into each butt-cheek was because I dared to mutter the words "for fuck sake" only 30 minutes ago after Mistress told me no time out of chastity this week. Within seconds of me muttering those words, I was getting marched up to the bedroom by one hell of an angry woman.

To anyone viewing Mistress Kim and me at this moment, I am sure we make a comedy like scene, not that it is anything to laugh at from my point of view. Seeing a thirty-year-old sissy wearing the school uniform previously worn by Mistress Kim's daughter three years ago. All be it a uniform with a few additions, namely the black patent leather 6-inch stiletto platform T-Bar dolly shoes, transparent latex baby-style panties, the latex version of those crinkly plastic pants that go over diapers. In addition to that, I am wearing a locking leather collar and leash and the piece of metal I wear 24/7 these days, the 1-inch long micro cage.

I know I sound pathetic and indeed will look it if some non-kink people saw me, but it is what it is. Given the humiliations, sexual frustrations, and even pain of being a sissy for Mistress Kim, the desire to be submissive and serve her in any way, shape, or form is too much for me to say no to. Mistress is 45, divorced with two daughters aged 19 and 21, who are currently away at University. She tells me I am the easiest task in life so far, considering she has had to put up with a sexist, cheating Alpha-male husband for 20 years, plus raised two very confident headstrong girls, a sissy beta-boy is easy in comparison.

Thirty minutes later, I am pushed off of her leather-covered knee to lay on the floor a broken, crying mess. I think my brain has shut down my nervous system to try to stop it from hurting so bad. It is almost a numb feeling at the moment, but I know the excruciating pain will return soon enough.

Whist I am lost in my own world of agony on the floor feeling sorry for myself, I have not noticed Mistress Kim has lifted her knee-length skirt and getting onto her hands and knees on the bed to reveal her hairless pussy and small light brown bumhole.

"SISSY BOI! Stop lying about down there; time to get that tongue to work".

I know all too well how much it turns on Mistress to discipline me physically. It turns me on as well, not that the 1-inch steel cage locked between my legs would give that away. The only tell-tale sign I am trying to swell in my cock-cage is the inevitable dark blue balls.

"SISSY KELLY! Get to it, or do you want to feel the cane next time."

Quickly moving up onto my knees, drips of black mascara stained tears landing on the green pleated skirt. I lean forward and cannot help but be hit with the pungent aroma of Mistress Kim's arousal. I have to say, at 45, Mistresses pussy is the most beautiful looking, smelling and tasting pussy I have ever had the fortune to know.

Reaching back, Mistress takes the leash and tugs at it to indicate my face needs to be between her ass-cheek now. OMG, my balls are ready to burst into my rubber pants as I catch the familiar aroma of Mistresses anus. An anus that only 2 hours ago had poop coming out of it. I know because soon after Mistress had shit into the toilet, I was sent into the strong, lingering aroma filled en-suite to clean it from floor to ceiling like I did most days. I had also been tasked with cleaning the en-suite whilst wearing a rubber penis gag strapped into my mouth, meaning I could only breathe through my nose and not be able to escape my Mistresses sewage fumes whilst cleaning.

Even though Mistress is physically clean between her bum cheeks, I know she has not showered since shitting, and I know from experience Mistresses anus will smell and taste strong. This fact is confirmed two seconds later when my nose is pressed hard against her tight brown stink hole.

PpppppRRRRRRRRRRRRRTTTTTTTTTTTTTTTTTTTTTTTTT HAHAHA "smell that shit sniffer", "now get cleaning it inside and out shit-munch", I hear Mistress say.

Rubbing my nose up and down, side to side and pushing it inside her hot sticky butthole, breathing in her funky, dirty stink, has me feeling animalistic. Lost in the heat of the moment, I dare have visions of grandeur and start thinking I am the boss in this situation while I hear her feminine moans of sexual pleasure, that is until I feel the leash tug hard on my neck whilst my mouth is over her hole with my tongue in her anus as far as humanly possible when Mistress breaks wind directly into my mouth and into my lungs. Trying to pull away is impossible, not that pulling away from her fart gift would do me any favours; no, having her sense me try to pull my face out of her stinking ass crack would only displease her. So, here I am, dressed in a schoolgirl uniform, eating her asshole and sucking on her shit fumes. To add salt to the humiliation wounds, my balls are burning at this moment because this filthy treatment makes my caged cock want to spray is teaspoon worth of seed into these rubber baby pants.

After an hour or so of anal worship, Mistress tires of my presence and dismisses me from the room so she can have a nap.

"Not too bad, sissy, your ass worshipping skills are improving, but for now, get out of my sight. Go change into your pink maid's uniform and attend to your household chores until I call for you."

Busily cleaning the kitchen and preparing the evening meal, I hear the house phone ringing, rushing to answer it before it wakes Mistress Kim. I am suddenly red-faced to hear the voice of Miss Kims youngest daughter, Miss Sally.

"Hello, sissy, where is my mum? She is not answering her mobile?"

"Hello Miss Sally, Mistress is having a nap. Do you want me to go and see if she can take your call?"

"No, not this time, sissy Kelly. Mum will likely skin your backside if you wake her, hehe."

"Thank you, Miss Sally. My butt cannot take any more at the moment."

"Haha, glad to see mum is keeping you well trained. Wait until me and my sister Taya return home for the holidays; you will be walking around on eggshells trying not to mess up around the three of us, haha. Nice to talk to you, sissy Kelly, but best be going. Now, get back to your chores, or I will tell mum you were slacking off."