Sissy Sessions Ch. 01

Note to readers: This story is the first in an anthology-style short story series. I plan to write them so that each one is unique. I'll re-use characters in more than one entry from time to time. I'll also always do my best to write these so that you can read each story on its own. Read the series in whatever order you want. Enjoy, and thanks for reading!

"Your father works extremely hard to make sure we have a roof over our heads!"

The last words I heard my wife say as I walked out the door tonight.

Now the words I'm hearing are, "your mouth feels so good, bitch."

The words came from our landlord, Darrell.

I only earn about $40,000/yr from my work from home job as a Support Specialist. It's not enough to cover rent and all the necessities that come with supporting my family. My wife works part-time at the grocery store, and my son is now in his sophomore year of high school. It's a private school, and it gives him the best shot at getting into a top-tier university. The tuition is not cheap.

A few times per week, I have to take up shifts at my second job. Non-negotiable. There's no possible way our family can pay for all our expenses if I didn't take up this job. I go to work at this second job in the evenings only. I can't afford to lose my day job either, so my days are not open. Shifts can be anywhere from 1 to 3 hours long.

If I'm being honest, the pay for my part-time job is more than the pay from my day job. It pays more because the work is a lot harder. It's some of the most difficult work I've ever done in my life.

"Yeah, you've gotten so good at sucking my dick. You look so good. You're loving it."

Darrell's words rang loud in my ears as I looked up at him.

To make sure my son has the best opportunities in life, I debase myself at Darrell's feet. This evening, he has me in a lacy black thong, matching black stockings, a black crop top, and pink high heels. The stockings are fishnets, and the heels are open toe. Darrell likes to see my painted toenails peaking through. In bright pink lettering across the front of my top, read the words "Daddy's Bitch". Around my neck is dog collar. Tonight, it's the pink one. The name tag is the shape of a miniature dick. It's engraved with 173, my family's apartment number.

I always wonder how many more tags I would find if I searched his penthouse. I used to tell myself I can't be the only tenant he owns. I don't bother thinking about it anymore.

A few minutes ago, I finished getting dressed after doing my hair and makeup. About 40 minutes passed since I arrived. I don't get paid for these 40 minutes. I can't get ready to his satisfaction any faster. Darrell has specific desires. I lost count how many times I've done this now. It's been going on for over a year at least. I think it started a few months before my kid's freshman year. We needed the money for a down payment on his tuition. I spent most of my prep time on the makeup look tonight. For my shoulder-length hair, I used a headband to give me a sportier look. It saved me a lot of time, and it helps keep the hair our of my face.

Darrell's colour theme for tonight is black and pink. My eyes and cheeks are various shades and pink. There's some glitter and shine mixed in. Layered on my lips is a shade of barbie pink lipstick with a healthy coat of gloss on top. Peaking through the front of my heels are my pink toenails. The exact same shade should be close to dry on my fingernails.

I sauntered my way out of his master bedroom's bathroom into his bright bedroom. The lights are always on when I come to see Darrell. They stay on throughout the entirety of our time together.

"There's no chance I let you hide in the safety of the night" he says.

I need to start the clock. Punch in, so to speak.

Darrell's seated at the base of his bed. His toes resting on the carpet. The heels of his feet don't quite reach the floor. He's spread his legs. For a brief moment, I see him smirking. The sight of his mischievous grin will always be unsettling.

It's the look of superiority, and for good reason.

After the brief moment, there's only one thing that has my attention. It's safe to say I have some sort of Pavlovian response to it by this point. In the middle of his legs, standing at full attention, is Darrell's cock. 7 inches of dark meat. In his left hand, he has my leash. His right hand rests on his thigh. I can feel my mouth watering. I can't help myself. Darrell's conditioning is working. My body is betraying my mind.

I tell myself I would never tolerate anything like this if I didn't need the money. Yet, I instinctively lick my upper lip. It felt like a reflex. I couldn't stop it.

Darrell looked at me with intent.

Step by step, I walked towards him making sure to swish my hips. It's almost second nature for me, especially when I have on my high heels. When I found myself standing in front of Darrell, right between his open legs, his smile grew.

Silence.

I slowly lowered myself to my knees. Placing one hand on Darrell's knee to steady myself. When in position, I lowered my hands to the floor to get on all fours, and then I leaned forward. Darrell used his free hand to point his cock right at me.

Mwah

Darrell glances at the clock on the counter behind me. He's making note of the time. I'm officially on the clock. Starting now, I'll earn my paycheck.

"You're such a fucking bitch, Kyle. My little bitch. My slut."

I'm not allowed to respond. My evening's pay is void if I say a word before I swallow his first load of the night. The worst part is the night continues regardless. Darrell expects me to swallow at least 1 load every time I enter his penthouse. If I say a word before I do so, I lose my pay and still have his baby batter in my belly. It didn't take long for me conform to his rules.

"What would your boy say if he saw you slobbering on my black dick like it's a popsicle on a hot summer day?"

I continue to bob up and down on his cock. He knows his demeaning words are turning me on.

"The new smudge resistant lipstick is working wonders. The colour is staying put on those pretty little lips. It's only the gloss rubbing off on me. We'll have to see how long it holds tonight."

Darrell's words were coming between grunts of pleasure now. My head is now swirling a bit as I bob. I'm planting my tongue underneath his shaft. I make sure the hold is firm. When I bob up the shaft, I drag the inner parts of my lips against his skin. I want him to feel the tug from my soft inner lips. I need to coax the cream out of his balls. At the tip, my tongue dances over his frenulum.

If I could use my hands, I would go all the way up to the tip of his cock. I would make sure he can hear the sloppy kiss I leave for his cock head. He likes it when I put on a show for him. I follow up my kiss with a swirl of my tongue, lathering his head with saliva.

It's too bad I can't use my hands for the first blowjob, so I can't keep his manhood steady enough to perform those techniques. Instead, I rise up until only the tip is in my mouth. I then loosen my lips and flatten my tongue as I make my way back down.

I make sure to make audible slurping noises on the upward motion. To make sure Darrell is slick and slippery enough to achieve the noise he likes, I have to force my throat open. I take all 7 inches down my throat when I go down. When I come up, the throat slime that comes out with his cock leaves his shaft plenty lubricated. I need to repeat this a few times to build up the slimy fluid.

It's easier for me to make eye contact on the upward motion. When I take him into my throat, my nose is on his pubic mound. It's hard to look upwards in this position. So, every few bobs, I look up into the eyes of the man who owns me. He trained me well. I bat my eyelashes at him. The only time his eyes aren't open when I look up at him are when he's cumming. He only closes his eyes when he blinks and cums. He says it's because he can't get enough of watching me worship at the altar of his cock. It's the best entertainment in his life. Nothing makes him happier than experiencing the fruits of his labour. He spent a lot of time and energy training me to pleasure him to perfection.

My knees are starting to feel sore. I don't know how much time passed, but I know I need to hurry up if I don't want light bruising on my knees. I can't have my wife getting suspicious. Darrell doesn't allow me the cushioned mat until after I swallow his first load. I have to earn it.

"Mmmh, mmmh, mmmmh. Ain't nobody suck this dick like you do. You make fucking love to it."

I beam with pride, revelling in the shame I also feel. My own dick was now at full mast. All 4.5 inches.

I can feel his upper body start to shift. From my past experiences, I know what this means. Darrell is close. The shift in weight is Darrell picking up my butt plug. He's lubing it up, getting it ready.

Not long after, I can feel it. The first spurt comes strong. It splatters the back of my mouth. It used to catch me off guard. Not anymore. I take it in stride now. The second and third spurts follow shortly after. I can't feel any spurts after that, but I know they're coming. I can feel his cock spasming between my lips. I was around the middle of his shaft when the first spurt came. I had to move upwards to make more room. I could feel his load building up in my mouth. The now familiar taste of his seed invading my tastebuds. My lips remain sealed around his cock. I don't want to lose a drop.

His orgasm is over. He looks so satisfied with himself.

Only his tip is in my mouth as I wait for his permission to swallow.

"Ahhh."

I detach myself from his cock. Not a drop spilled. I open my mouth and tilt my head back to look up at Darrell. I do my best to say, "ahh."

"Hold."

I close my mouth but do not swallow. Darrell gets up and walks around me. He places the palm of his hand on my back between my shoulder blades. I lean forward, raising my ass for Darrell. He pulls the back of the thong to the side. I'll never get used to the cold sensation of the first lubed finger he inserts in me. By the time he has three fingers in me, I'm comfortable and ready. He pops in the butt plug with ease.

"Ouuu, I'm going to have fun tonight."

He followed his words with a firm spank of my ass cheek.

This is my first chance to speak tonight.

"Thank you for letting me suck your dick, Daddy."

Darrell attaches the leash to my collar and gives it a tug.

"Clean."

I wrap my lips around his cock again.

This is the beginning of tonight's shift.