Sissy Stretching for Princess T Pt. 02

"I think we should get some heels for you soon sissy. Would you like to learn to walk around in sexy heels to amuse your Princess."

"Yes Princess, I would like that very much." This has been something I have been interested in exploring for years but had yet to do so with any previous Domme. I trust Princess T will be true to her word though. She is not one to bring up fantasies that she does not intend to live out.

With my eyes still locked in on her sexy feet and shoes, in my peripheral vision I see Princess scan the parking lot with her eyes. She raises her left foot.

"Suck my heel sissy," she demands huskily, her voice barely louder than a whisper.

I place my lips around the stiletto and slide my face down. I feel the sharp point of the heel stab the back of my throat. At the same time I feel my erection stabbing upward inside my panties. Princess lowers her other heel onto my erection and presses down. It hurts but I manage not to yelp.

"Now the other one," she instructs lifting her right shoe while keeping the left one pressed firmly down no my erection, which refuses to subside despite the pain. I suck the new heel back and forth a few times before she yanks it from my mouth's grasp.

"Stand up and go to your car. Follow me home bitch."

I stand up without a word. The pressure of Princess's heel caused some precum to leak out of my little penis. She notices the stain and smirks as I quickly walk away, trying to remember where I parked my car.

As usual, Princess has me strip as soon as I enter her apartment. She has me take her dessert into the kitchen as she walks upstairs to her home office. When I arrive she is already sitting in a desk chair in front of a computer. I have cleaned this room before but have yet to see her in it. Without a word she snaps her fingers and points to the floor in front of her. I cross the room and drop to my knees in front of her desk.

"Remove my shoes. Kiss each of them as you do so."

The desk is wide enough for me to fit under but without much wiggle room. Instead of crawling fully underneath it, I lean forward with my arms and head under the desk and my knees just outside it. I kiss her right shoe right at the tip and slide it off of her foot. The taste of the plastic mixed with the slightest tinge of foot sweat is quite an intoxicating combination. My dick hardens again as soon as the shoe slides off and Princess's long, perfectly symmetrical toes come into view. She has gotten a pedicure since I last saw them and now sport the white tips of a French pedicure. I gently turn and place the removed shoe to the left of the desk, ensuring that it stands up straight on the carpet. I resist the urge to sniff it and instead repeat the kiss and removal process with her left shoe.

"Now rub," comes the simple command from above.

I prop my elbows up on the floor and begin to gently rub her arches with both thumbs. A few specks of dead skin and miscellaneous grime fall onto the carpet below. I hear a small sigh of satisfaction eek through the pitter patter of the keyboard. I run both thumbs up the length of the arch several times before holding the foot still with my right hand and throughly rubbing every inch my left thumb. My face moves a bit closer to breath in a gentle whiff of that just-freed-from-a-heel foot scent. It is not exactly sweat, it contains hint of freshness to it, like the last lingering new car scent in a vehicle that has been driven around for several months.

Once I am satisfied with the attention I have given to the arch, I move my hands up to the toes. This time my right thumb takes charge, purposefully rubbing up and down the bottom of each toe several times. I then take each toe between my left thumb and index finger caressing up and down the line. This step removes any grime that has collected between the toes. There isn't much.

"Suck," comes a nearly inaudible voice from above. My mouth slides over her toes and my tongue performs rapid gyrations not dissimilar to the ones of my thumbs. As I gently suck her toes, I begin rubbing her heel as well. Throughout this entire process, the typing above me continues. As focused as I am on my task, I am pleasantly surprised that Princess is able to focus on her work while simultaneously instructing me on how she wants her feet worshiped. Actually now that the thought hits, it isn't surprising at all. Princess T is not the kind of woman to get easily distracted and certainly has the mental capacity to multitask.

She pulls her toes from my mouth without a word, lifting her foot a bit to give me better access to her heel. I rub it up and down and side to side, using my thumbs, my fingers and then the palm of my hand. Once I feel that the heel has been properly rubbed, I start sucking on it on my own volition. I am rewarded for my actions with her left foot locating and pressing down on my penis, which has been erect and sticking straight up in my panties for the duration of my massaging.

Her foot presses down harder as I swirl my tongue around her right heel. The skin is very soft and well cared for. I gaze at her pretty white capped toes perfectly in my line of vision. I haven't felt this comfortable, this at home, since the last time I worshiped Princess T's feet. This is simply where I belong.

As is always the case, she pulls her heel from my mouth before I am ready. She lifts her left foot from my crotch and quickly replaces it with the freshly rubbed and licked one. I reach for her left foot and repeat the entire process. Rub arch, rub toes, suck toes, rub heel, suck heel. The tops of her feet are a bit neglected by this method but she doesn't seem to mind.

Once the left heel is pulled from my eager mouth, once again before I wish it to be, I am instructed to lay on my back under the desk. I comply and Princess immediately begins to rub her feet up and down my entire face. They are still moist with my saliva but maintain their unique, intoxicating odor. After a while she stops rubbing and begins to press down on my face like she previously had with my dick. I cannot breath or see as my entire world is composed solely of the bottom of her feet. She removes them briefly and I gasp for air. She quickly places her feet back on my face, covering it from forehead to mouth. This process repeats several times.

After she pulls her feet from my abused face for the last time, she instructs me to go get her some water. I slide out from under the desk and try to stand. My ass is numb and I wobble a bit, still trying to catch my breath. As soon as I gather my bearings, I rush down the stairs and into the kitchen. I grab a bottled water from the fridge, taking the initiative to replace it with a warm one from a large pack on the counter. I feel a bit parched but she did not say I could get one for myself. I don't dare ask.

After I bring Princess her water, she merely snaps and points at the floor where I stand. I drop to my hands and knees. She doesn't say anything and I stay in my humble posture for some time. My eyes start by staring straight down into the carpet below me but eventually begin to wander.

To her freshly worshiped feet that I would love to have another go at with my hands and my mouth.

Up her chiseled, muscular calves to the base of her skirt.

I spend a few moments ogling her breasts that somehow seem even closer to breaking out of their white buttoned confinement.

I even dare to look at her face, a privilege I am not often granted while serving her. Once of the best parts of having lunch with her (they were all best parts really) was being able to hold the gaze of her piercing green eyes for so long. She really was a beautiful woman.

My knees and shoulders soon begin to ache from continuing to remain on all fours. I wobble a bit, but maintain my posture the best that I can.

After a while she breaks her gaze from her computer and smiles down a me.

"Doing okay down there bitch?"

"Yes Princess." I do not mention my sore knees and shoulders. Surely she is aware of the discomfort of extended kneeling.

"You may stand now and begin to rub my shoulders. Gently."

I breath a sigh of relief as I climb to my feet. I try to get in a quick, imperceptible stretch before leaning over the back of her chair and beginning to massage her shoulders.

I stay in the general area of her shoulders, upper back and upper arms rubbing around for all that I am worth. I am much more confident in my foot rubbing ability than my shoulder rubbing. At times I am not quite sure what to do with my hands, but I keep rubbing and rubbing despite the soreness developing in them.

Right about the time the soreness in my hands begins to turn to actual pain, she orders me to stop and get back on my knees. She rolls her chairs back, gets up and heads out of the room. I hear her enter the bathroom and shortly after some running water. The is a gap of a few minutes from the time the water stops until Princess reenters the room.

As she reenters I keep my eyes straight ahead, not turning to gaze upon her. She walks over to her chair and sits back down.

"I should be done working soon. I brought you something to keep you busy while I finish up." She drops her strap on, harness and all onto the ground in front of me.

"Thanks you Princess!" I exclaim with genuine excitement. I am excited to have a productive way to past the time. And with my hands being tired from the neck massage, I am relived to have a task using my mouth.

"Back up a little bit, you don't need to be that close to me to suck my dick."

I scurry back a foot or two.

She looks over at me lovingly, but with just a hint of sadistic pleasure. "You will keep sucking my cock until I tell you to stop. Do you understand?"

I nod.

"I do want you to deep throat it some, but don't be too loud and messy." She laughs. "But do make sure you get it nice and lubed up, because once I'm done working, it's going in your little sissy ass."

A jolt of excitement flows through my ass and my now limp dick. My dick still doesn't harden, just twitches like it had been shocked. My asshole tenses and releases even though there is nothing in it. Mistress T was going to fuck me!

I stay on my hands and knees holding the lengthy flesh covered cock in front of me. It is in a harness and is not meant to stand up on the ground with a suction cup like mine is. Also, the room is carpeted (mine is hardwood) so even a suction cup dildo would not stand up here. This means I must hold the base of the dildo while I suck it. Somehow this makes it easier. I always choke more when I'm not using my hands at all.

My sucking begins slowly but not disinterestedly. I often begin my dildo sucking with a little seduction and teasing and this time is no different. Also since I'm not sure how long I am going to be at this, I do not want to wear out my throat.

After a bit, I pick the pace up. Up and down, up and down. I start to moan a little but try to keep my sound effects to a minimum. As my sucking pace increases I can feel my little pee pee start to harden in my panties. I start going further and further down the shaft, trying to get as much fake cock in my throat as I can.

I lower my mouth slowly, allowing me time to relax my throat and keeping the sound of my gagging to a minimum. At one point I go too deep. I really want to take the entire length, but my throat is just not ready for that yet. I gag much louder than I intend do and cough a few times as I pull my head up off the cock.

Princess turns and shoots me a disapproving look, but it quickly dissipates into a smile. "You look so cute sucking my cock that it is hard to be mad at you. But please try to keep it down you little cock slut."

I mutter back 'yes Princess' quietly and unintelligibly with my mouth already full of strap on.

My thoughts drift into the serene as my face bobs up and down on my Princess's dick. Sucking and licking, licking and sucking. Occasionally taking my mouth off it completely and just stroking it with my hand. It is such a nicer dick than mine. It can certainly fuck Princess better than I ever could. But I almost wish a cock the size of my own would go into my ass, at least for the first time. I am excited but a little scared. I pray Princess takes it easy on me.

After an indistinguishable amount of time, Princess rolls her chair back. "Enjoying that cock sissy?"

I pull the dick out of my mouth to answer in the affirmative.

"Ready to get fucked by it?" she asks as she stands and approaches me.

I simply nod nervously.

Princess turns her back to me and instructs me to zip her skirt down. I do so using my hands, immediately wishing I had asked if I could use my teeth. The skirt cascades quickly over her fit legs and crumples to the floor. She steps out of it, picks it up herself, smooths it out and places in on the computer chair. Then she turns and reaches for the harness, beginning to pull it up her legs. I sit in stunned and complete awe.

"Kiss me feet and then beg me to fuck you," she orders as she arranges the harness around her hips and ass in the appropriate manner. She has kept her underwear on, a pair of dark blue panties, so I have still yet to see her vagina. Only her cock.

I plant a long passionate kiss on the top of each of her feet. I look up at her front my knees. I am a bit scared, but fuck she looks sexy.

"Please fuck me Princess T."

"Are you a little cock hungry sissy?"

"Yes Princess T. I am your little cock hungry sissy and I want you to fuck me and make me scream."

She laughs. "I don't want you to scream too much, but maybe a little. Now take your panties off and get over to the futon."

There is a brown futon lining the near side of the wall. I quickly shuck my panties and crawl over to it, bending over the seat with my ass in the air. Princess laughs. "You look cute and desperate to be fucked all bent over like that, but its too low for me. Get up on your knees on the couch." I comply.

"And scoot up a bit so I'll fit behind you."

I scoot up. My face hangs over the edge of the futon. Princess climbs up onto it behind me. I attempt to arch my back and present my ass to her as best I can. I hear her sucking on her fingers behind me. Then I feel her slide her index and middle fingers into my hole. I reach back to spread my cheeks.

"Good bitch. Open that ass for me. I'm going to try to do this with just saliva. We will see if your hole is as cock hungry as your dirty little sissy mind."

Her fingers slide in fairly easily. She slides them in and out a few times. Then she pushes them in deeper. I feel them press against my prostate. I moan involuntarily. I am extremely aroused but my penis is as limp as can be. She slides the two fingers out and replaces them with three. A little resistance this time, but not much. I feel a bit of pressure but am surprised by how little it hurts.

I hear Mistress spit behind me. I feel something much wider than a finger approach my hole. I spread my cheeks, take a deep breath and try to relax. My own dildo that I practice with is a bit thicker than hers, but I've always used lube when using it. The moist tip of the head begins to slide in. I moan in half pain and half pleasure.

She continues to slowly slide it in. I drop my hands to my sides. There is a bit more pain than with my toy, probably due to the lack of lube, but it's not unbearable. Right as the pain starts to get worse, she pulls back a bit. I moan again.

"Please fuck me Princess," I say without even realizing it.

She thrusts back in. It slides deeper and the pain builds. Soon it hits my prostate. The pleasure increases dramatically, overtaking the pain. She goes back and forth a few times. The pain numbs a bit with each stroke. It is not altogether gone, but certainly bearable. The pleasure takes over with each passing stroke. My moans grow more constant. I feel Princess's hands on my ass pulling me back to her. I oblige, trying to back my ass up onto her dick.

"There you go sissy boy. Take that Goddess dick."

I continue moaning and sliding my ass back and forth. It actually feels better the deeper it goes. I'm sure I am not taking the entire length, but however deep she's going, it feels great. As she picks up the pace some more, I stop grinding my ass back to meet her. I simply lay there and get fucked. She slaps my ass hard. I cry out, unsure if it's in pain or delight. She slaps it again and starts fucking me harder. I feel pressure building in my little clit but its still not growing. It almost feels like I have to pee, but while I'm really turned on.

My moaning is non stop at this point and getting higher in pitch the deeper her dick goes. She takes her hands off my ass and presses down on my lower back. I arch my back as much as I can, but don't have the energy to push my ass back. It is being assaulted. The pain has not dissipated completely but is more a dull hum than searing or intense. The pleasure is intense.

Princess continues fucking me harder and harder. I feel incredibly full. More so than I have ever felt from fucking myself. It is as if I can feel her cock in my stomach, in my chest, it fills my entire body. I want to start rubbing my still limp penis but can't stop moaning to ask for permission. The urge to pee increases but I know that is just prostate stimulation.

After a while Princess pulls her cock all the way out of me. I immediately feel disappointed. "Lie on your back sissy," she instructs me. I turn and lie on my back. Somehow now that my hole is empty it hurts more. That doesn't make sense.

She spits on her cock again and I watch her rub it in. I press up against the back of the futon and lift my legs as high into the air as I can. She grabs one of my ankles and uses the other hand to guide her cock back in. The initial penetration hurts a bit, but once it is in, the pleasure overrides it immediately. After a few strokes, she has her rhythm back and moves her free hand to my other ankle. The position of holding my legs up at this angle actually hurts much more than my asshole as it takes its pounding.

"Do you want to rub your little sissy clitty?" Princess taunts me as her cock jettisons in and out of my surprisingly loose asshole.

"Yes please Goddess," I almost scream in a high pitched voice that doesn't even sound like my own.

"Rub yourself then. Show how much your Goddess's dick turns you on."

"Your.. dick... feels.. soo.. good," I stammer out between moans. I start to stroke my dick which is now in that weird space between erect and limp.

My legs begin to tire and drop but Princess T pushes them back up, and moves them even further apart. Her dick is getting so deep inside of me. I look down and see I'm taking nearly the whole thing. I haven't been stroking long but already feel like I'm going to cum, despite not being fully hard.

"Goddess, may I cum?" I blurt out amidst the moans of pleasure.

"Does my little sissy want to cum while getting fucked?" I look up into her eyes. They burn fiercely. She looks hungry, like a predator about to devour her prey. I break her gaze, almost scared to answer. As my eyes scan her chest I realize for the first time that her shirt is unbuttoned. She still wears a blue bra that matches her panties. I am about to blow my load with this gorgeous, dominant woman's nine inch dick inside me and I still have yet to see her breasts or pussy.

"Yes Goddess, I want to cum so bad. Your dick feels so good."

"You may cum, but when you do, I want you to say 'Goddess T owns my ass.' Got it?"

I nod and continue moaning like a bitch a stroking my dick. It has responded to my touching enough to grow a bit, but it is still not erect. Certainly not hard enough to penetrate a pussy. This is what my dick was intended for. To cum half erect while getting fucked in the ass.