I let myself in through the basement door, knowing I have just over an hour until You get home. I have to be ready by then to keep You happy. I shudder thinking about the punishments you inflicted last time I was not fully prepared for You. I quickly walk through the playroom and open the bathroom door. As I close the door, I see the first outfit You have picked out to start our weekend together. A slutty schoolgirl outfit is hanging there and a pair pink Mary Jane pumps with five-inch heels are beside the door. I quickly strip out of my work clothes and set about making myself presentable. On the counter, I see an envelope with my name on it. Opening the envelope, I find a note and the key to my chastity cage.
"My Dearest Sissy,
I have an incredibly exciting weekend planned for you. As soon as you are finished reading this note, you are to clean yourself out and put in your biggest plug and then make yourself pretty for me. As you no doubt have guessed, I want your little clitty to be free for me when I get home. Of course, you are to take off you cage as the last step in your preparations. Once it's off, put on a tight cock ring and wait for me in the center of the playroom blindfolded. I hope you like the outfit I chose for you.
I wince as I read the note. You usually only release my clitty for one thing. My thoughts drift to the last time my clitty was free, a little over a month ago now. The torment You unleashed upon my poor clitty and tiny ball sack left me sore for a week and, of course, You did not allow me any release. I shake my head to clear my thoughts and remind myself that my purpose is to please You and not me. Not wasting anymore time, I turn on the shower, and, grabbing a razor and some flowery scented shaving cream, I hop in. I quickly clean up any stray hairs I can find, making sure I am completely smooth all over and use the built-in enema nozzle to get my sissy pussy squeaky clean. I turn off the water and pat myself dry before I pull open a drawer by the sink and take out the biggest plug in it. I slather the plug with lube and bend over the sink. It takes a few minutes but soon the plug is firmly lodged in my backside and I am leaking out of my cage.
As I gingerly sit down at the vanity to do my makeup, I have to pause for a moment as a small sissygasm flows through me. The plug is just so big that any movement sends waves of pleasure through me. Once I calm down, I get down to business. I match my makeup to the outfit You picked for me. Pink eyeshadow, a little bit of light pink blush and bubble gum pink lip gloss start to transform me into the slutty schoolgirl You desire me to be. I braid my hair into pigtails on either side of my head, tying the braids off with little pink bows. Glancing at the clock, I see I need to hurry up because You will be home soon. Luckily, the time-consuming parts are now done. I mince across the room to get the schoolgirl outfit off the door, the massive plug reminding me of its presence and I nearly stagger as it sends another shockwave of pleasure through me.
I start by wrapping the light pink garter belt around my slim waist and then sit down to slide the white thigh-high stockings up my legs. Once the stockings are clipped to the garter belt, I slide my arms through the straps of the light pink bra and settle my little sissy titties into the cups. With a practiced motion, I reach behind and fasten the bra closed. Of course, You did not include any panties and this further reinforces my notion that my clitty will be suffering for Your enjoyment tonight. I wrap the pink plaid skirt around my waist and do up the buttons on the side before I buckle the top closed. Slipping on the thin white blouse on, I tie it closed just under the bra. I slide my feet into the pink pumps and buckle them tight over my feet and stand up, turning to the mirror.
Even after all these years of dressing up, I am still amazed that a little bit of makeup and sexy clothes can turn me from an average, ordinary guy into a sexy, very fuckable girl. As I stare at my reflection, I notice the time. I only have a few minutes until you get home. I quickly scoop up my work clothes, grab the key off the counter and hurry out into the playroom. First, I put my work clothes in their cabinet and click the lock hanging there closed. I barely even think about the fact my male clothes are now locked away. After all, I will not need them until Monday morning when You send me off to work after depositing one last load in me. Opening another cabinet, I select the pink cuffs and collar, buckling them on and locking them in place with small padlocks.
I grab a rubber cock ring out of a drawer and, after unlocking and removing my cage, I squeeze my balls through the ring and finally stuff my limp clitty through it as well. Immediately, I feel my clitty trying to get hard but years of chastity and my "sissy pills", as You call them, have made true boners an elusive thing. Finally, grabbing the pink leather blindfold, another padlock and, even though You did not specifically require it, a pink silicone ball gag, I kneel down in the center of the room. I buckle the gag around my head and slip it in between my lips. I pull the blindfold over my eyes and, as I hear You open the front door, I click the padlock closed, locking my hands together behind my back.
Kneeling in the darkness of the blindfold, experience allows me to track Your movements through the house. First into the living room and then into the kitchen. Stopping at fridge to get a drink, I assume, and then I hear Your footfalls on the step to the second floor. That must mean You have a special outfit for tonight as well. As I wait for Your entrance, anticipation builds and my clitty swells a bit more, the cock ring doing its job. By now I have started to drool around the gag and I imagine a nice puddle is forming on the tiles below me. I have no idea how long You make me wait but it really is not easy for a horny, blindfolded sissy waiting for her Daddy to keep track of time. Eventually though, I hear You open the basement door and start to descend the stairs.
Your heavy steps on the stairs tell me You are wearing boots and I wonder what kind of costume You have on. Of course, You will let me see once it is time and not a moment before so I resign myself to waiting. I hear You stride across the room and soon feel You looming over me. I smell Your manly scent and my clitty jumps a little under my girly pink plaid skirt. You reach down and pull me upright on my knees by my chin and I hear the clip of the leash click onto my collar.
"Nice touch with the gag," You say, breaking the silence in the playroom, "Good job Sissy."
"Thank You Daddy," I mumble around the gag.
"You are welcome Sissy," You chuckle, able to understand me after all this time. After all, You have heard me try to talk around gags, cocks and the occasional pussy.
"Are you ready to be my sexy sissy bitch?" You ask, tugging the leash and pulling my face into Your crotch.
"Yes Daddy," I try to say as I nod my head and nuzzle Your crotch, feeling Your wonderful cock growing in Your pants.
"Good," You say, taking my head in both hands and grinding face against Your swelling cock. After a moment of that, You release my head and I feel You bend down and pull up the hem of my skirt. You tuck the front hem into the waistband, exposing my clitty. Next, I feel the toe of Your boot against my balls, pushing them into me, not really painfully but it is definitely uncomfortable. With the toe of Your boot grinding my balls, You once again pull my face into Your crotch, smothering me in Your manliness. Right as I begin to struggle for air, You pull me to my feet and tug forcefully on the leash, leading me across the room.
Stopping, You turn me around and I hear the jingle of Your key ring as You unlock my hands and push me down onto a seat. I sit in the chair designed for easy access to my crotch and You clip my cuffs and collar to the built-in restraints. I am now locked into the chair and I feel my legs part as You open the chair, leaving my clitty bobbing in the air in front of me, entirely at Your mercy. If the past is any indication, there will be very mercy tonight and I quiver in fear and anticipation. Seeing me shaking, You grab my chin and lean down to my ear, whispering, "I know this isn't your favorite thing, but I've had a hard week at work and I need to relieve some of the stress. So be my good sissy and make your Daddy happy."
"Yes Daddy," I whimper around the gag, and you let go of my chin and pull away.
I try to stop my squirming and then I feel You grab my balls and squeeze really hard. I do my best not to scream and manage to just whimper a little. You tug them down and away from my body and I feel You fumbling around them with Your other hand. You let go and I feel the weights You have attached pull my balls even further down and even the slightest movement causes agonizing pain. I do my best to endure but with You tapping the weights, sending them swinging below me, I am soon moaning in pain. I hear You chuckle at my torment and then hear the swish of the flogger a mere moment before pain explodes from my entire groin.
I scream around the gag as my eyes begin to water behind the blindfold. I do not hear the next blow coming over my own painful moans and I am total caught off guard as the second explosion of pain blossoms from my genitals and I give up any pretense of being able to shrug of the pain. A third strike and I am freely crying, tears stream from behind the blindfold. I am writhing in pain as You continue to flog my poor little clitty and balls, my movements setting the weights swinging wildly, further increasing the pain. I lose track of how many times You strike me, my entire world nothing more than one bright flash of pain after another. I am sobbing and crying out in pain as You take out Your frustrations on my clitty.
Finally, You stop flogging my crotch and I slowly calm down a bit, waiting in anticipation for You to, hopefully release me but my hopes are in vain when I feel the riding crop lightly tapping my balls. I whimper in fear and then scream into the gag as You swat the tip of my clitty with the crop. You develop a pattern, clitty, right ball, clitty, left ball, and soon I am once again reduced to a sobbing sissy writhing in pain as her Daddy torments her for His pleasure. After I have no idea how long, You stop and pull the gag out of my mouth. You lean in and gently kiss me on the lips. You undo my cuffs and collar from the evil, evil chair and pull me to my feet. You lead me to the bathroom and just before You push me in and shut the door, You say, "Clean your face and fix your makeup. Then put the blindfold back on and come back out here."
To be continued...