Sissy Stretching for Princess T Pt. 02

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me.

"Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a drawer. Instead of setting it on the floor, I get into bed holding it in my hand. I begin fucking my mouth with it before I even hear back from Princess. With my other hand I start pushing and twisting the plug in my ass. My little dick begins to grow. It is about two thirds of the way erect when I receive my reply from Princess.

"I just came so hard, sissy. I bet you wish you were here to clean me."

That text alone causes me to reach full erection. My rock hard, but still small, member pokes out from my panties.

"Yes Princess. It would be a dream to lick your incredible pussy clean after you cum."

"Well keep dreaming sissy because its not happening today. Instead you can lick yourself clean after you spill your little sissy seed for me."

A moan escapes my lip. I keep sucking the dildo, but move my other hand from playing with my plug to rubbing my dick. I do not stroke it, just rub up and down the front of the shaft. Precum oozes onto my belly.

I receive a text from Princess with no text, just a video. It is me sucking her cock. I am a little surprised by how eager I look bobbing up and down on it and there is a look of insatiable lust in my eye. I remove my hand from my dick and hold the toy with both hands, shoving it deeper down my throat.

"Are you you sucking your toy right now sissy?"

"Yes Princess."

"Is your little clitty hard?"

"Yes Princess."

"Let me see."

I am not sure if she means one or both. To be safe, I send a quick 10 second video of me sucking my dildo and a picture of my throbbing erection sticking out of my panties.

Laughing face emoji. "Oh my god, it's so small!! I can tell it's fully hard too. That little dicklette is never getting anywhere near my pussy, do you understand?"

"Yes Princess of course. I know it could never please you."

"Good. In the past, I will admit I have had sex with submissive men. Their dicks were not big, but adequate enough to work with. Your clit is only good for laughing at."

This message makes me shove the toy deeper down my throat. I gag pretty badly and pull it out. Saliva drips off the rubber cock onto my bare chest.

"Yes Princess T. I'm glad that it can make you laugh, I know that it isn't good for anything else."

"The good thing is that I am making your mouth and your sissy hole useful. I was pleased with your service today."

I place the toy in my mouth, but not very deep, and start rubbing my erection again. I hold the toy in my mouth with no hands to text back.

"Thank you Princess T. I loved serving you and I am very excited to stretch my hole for your use."

"Here is what I want you to do now bitch. Take your plug out and suck on it, I know your slutty little mouth likes tasting your ass juices. Then start fucking your little hole with your toy. While you do this I want you to say out loud 'I am Princess T's sissy and my dick is too small to please her' over and over. While you do this you may stroke your little clitty until you cum. Once you cum, I want you to scoop it up with the toy that was in your ass and suck it off. Not just lick it off the tip. Your cum covered toy better be rammed down your throat. You have been so obedient that I don't need to see a video to prove your compliance. Seeing you degrade yourself for me does turn me on, but I do tire of it and have seen enough for today. Once you are have finished, you will thank me and not contact me again for the rest of the day."

My eyes widen as I read the message. It may have been the single hottest message of instructions I had ever received from any Domme. I want to thank her immediately, but figure I should wait until the instructions are complete.

"I have date with a real man later, depending on my mood I might choose to tease you about it. But if I do, you will still not reply. I know how much you love messaging me and I enjoy denying you that pleasure. After your message of gratitude for letting you spill your sissy seed, you may not text me again until tomorrow morning."

My heart drops a bit, but my dick does not. I quickly pull my plug out with a loud pop and a sharp burst of pain. Owww. I pulled it out too fast. I try to distract myself from the pain by shoving the plug in my mouth. It tastes more like shit and less like lube than last time when I did it without instruction. My tongue swirls all around the head of the plug. I lift my legs and begin to probe my hole with the toy. The head is barely in before my hole begins to resist.

I quickly grab my lube and slide my panties off, keeping my dirty plug in my mouth. I lube up my toy and slide two lubed fingers into my hole. It accepts them eagerly. I replace my fingers with my toy. I slide it about 3-4 inches in before beginning to fuck myself with it. I moan and say out loud, 'I am Princess T's sissy and my dick will never please her.' My unworthy dick throbs, yearning for attention. I begin stroking it with my left hand. I repeat my masturbation mantra again and try to get the toy deeper in my hole. My entire body is awash with pleasure. It has only been six days since my last orgasm, but the pleasure I get from stroking myself in this manner makes it feel as if it has been much longer.

About halfway through my fourth recitation of my manta, I feel my orgasm building in my erect little penis. It has only been about a minute and a half of stroking and I am already about to cum. Just another reminder of why I am unworthy to have 'traditional' sex.

I had read the instructions again after my first time reciting it and am now saying it verbatim. As the words 'my dick is too small to please heeeer' escape my lips they are replaced by a moan so high pitched that I am shocked that it came from my own mouth. My sissy hole tightens on the brown dildo as my thicker-than-usual cum squirts out onto my bare chest. The first rope lands just under my chin, on my chest above my tits. Three more ropes shoot out, not quite as far, but covering my entire chest in sticky white substance. I attempt to move the dildo back and forth a bit, but it hurts so I pull it out.

I take my butt plug out of my mouth. I debate whether to insert it back in, but decide against it. My asshole deserves the rest of the night off. I attempt to scoop up as much of my cum as I can on the head of my dildo. Usually when I jerk off daily, my cum is very thin and watery. Having built up for almost a week, it has a more viscous texture that allows more to stick to the toy.

Once the toy is coated as well as I think I can, I shove it down my throat. For some reason, my throat was not prepared for this and I gag. I move the dick out slightly but not all the way, allowing myself a second to relax my throat. Then I shove the brown cock in deeper.

I feel the cum more than I taste it. I have eaten my own cum many times. I am not exactly accustomed to the taste, it still generally shocks me a little because I do it so sporadically. This is a completely different experience. The burn in the back of my throat begins before I am able to taste the saltiness on my tongue. I wonder if this is what it is like to have a dick cum in your mouth. I lick around the dildo while keeping it shoved down my throat. This adds to the salty flavor I associate with eating my own cum, but the burn in my throat remains the more powerful stimulator.

I close my lips around the dildo as I slowly slide it out of my mouth. The cummy flavor intensifies, along with subtle hints of lube and rubber. I scoop up another load of cum, not as much as the first time, but about half of what remains on my chest. I shove the cock back down my throat, this time more relaxed and prepared for it. Once again I feel the burn in the back of my throat. This time I enjoy it more. I have not felt so slutty in such a long time. I feel a pang of regret that Princess will never see this.

I scoop up a little more cum on the cock and just lick it off this time. I don't think Princess will mind. My tongue travels up and down the shaft multiple times slurping up all cum and any other substance that coats it. Once all the cum I can possibly scoop up has been removed, I reach for my phone to text Princess.

"Thank you so much for everything Princess. Those were the hottest jerk off instructions I have ever received. The orgasm felt amazing, but not as amazing as obeying you. Have a great rest of the day, I'll talk to you tomorrow."

Exhaustion overcomes me as I descend from my orgasmic pleasure. Without bothering to clean myself up, I roll on my side and pass out, cuddling with the dildo that is still dirty with the residue of cum, lube and ass juice.

Once I wake up, I clean my toys, put them away and try to resume a normal day. I go for a run, shower and cook some rice and vegetables for a late lunch. I settle down with a book and try to read, attempting to keep my mind off Princess. Even after my explosive orgasm, it is difficult to steer my thoughts away from the sexual for very long. I long for more orders from Princess but know none are coming.

I put on a movie, hoping that will hold my attention better than a book was, when I finally get the text.

"Having a great time out tonight sissy. It turns me on to start my day with a sissy sucking my dick and end it by sucking a real man's dick. He can please me in ways that you never could, but I enjoy his company even more knowing that you are sitting at home thinking about me. Remember, no touching your little clit tonight and no texting me back. I do want you to spend five minutes sucking your toy before you go to sleep. Good night bitch boy."

I pause the movie immediately and read the text over and over again. My little dick quickly gets hard, but I resist making contact with it. It did feel good to know that she was thinking about me and that even from a distance I was able to make her evening more pleasurable. I set my phone down, take a deep breath and finish the movie.

That night, I complete my bedroom routine of changing into my pajamas and brushing my teeth before I get my dildo out. I stick it to my nightstand where I would normally have a bottle of water. I set my timer for 5 and a half minutes. It always makes me feel good to do a little extra for Princess T. As soon the the timer begins, I start sucking. Even with my post orgasm nap, exhaustion has caught up with me as the night has progressed. I had slept so poorly the night before that my mind is tired and mostly clear as I perform my pre-sleep fellatio. I don't go down deep enough to gag or choke, but I dutifully suck the dick up and down for the required amount of time. Once the timer goes off, letting me know my time was up, I am asleep within minutes with my big brown dildo still stuck to my nightstand.

I awake the next morning feeling refreshed. My hand bumps the dildo as I reach for my phone and I can't help but chuckle. I send Princess T a long 'Good morning' text, thanking her profusely for all she had put me through yesterday. I get out of bed, put my dildo away and attempt to have a normal day.

Princess had not yet given me any specific instructions going forward on whether I was allowed to touch myself or not. I decide I will play with myself if the desire arises (and it certainly would) but will not cum. I was actually rubbing myself rereading her messages from last night when I finally get her reply.

"Glad you enjoyed yourself so much yesterday. I had a great but exhausting night. Not really in the mood to talk much today. You are free to do as you wish until I tell you otherwise."

I send back a brief reply and do not hear back from her. I edge myself several times over the course of the day, but do not get my toys out nor allow myself to cum.

Throughout the week I continue to deny myself an orgasm. I soon start reintroducing my toys into my sex life, fucking my ass and mouth as I rub myself, but never allowing myself over the edge. Princess T is distant and disinterested for most of the week. She has very busy week at work and does not have time to coddle or continually instruct her desperate little sissy.

The week passes and the weekend approaches. Still no invitation to meet up with her. Still no orgasm for me. Finally on Saturday afternoon she invites me to take her out to lunch on Monday. I am free all day and excitedly agreed. My self imposed sexual denial is making me a little desperate for sexual attention, but I know a lunch date is a positive sign. I badly want a relationship with Princess T outside of sex. It is just hard to get my mind off of sex when thinking about her, because thinking about her at all instantly turns me on. I debate letting myself cum Sunday night so I will be calmer and less horny during our lunch, but instead I fuck my ass until it is sore. The intense ass fucking actually quells my sex drive nearly as much as having an orgasm would.

Monday afternoon I arrive at the restaurant 20 minutes before our scheduled meeting time. Princess had given me no clothing instructions nor any list of items to bring with me. I wear a pair of panties to be safe, but not my plug. I do not bring my dildo. The restaurant is a little more upscale than I had expected and I am grateful that I had decided to wear a button down shirt.

I sit for 25 minutes, with just a water in front of me, playing around on my phone, hoping Princess will arrive at any minute. 10 minutes after the scheduled meet time, and due to a dirty look or two from our sever, I decide to go ahead and order a cocktail while I wait. I am nervous and horny anyway and maybe the alcohol will calm me down.

10 more minutes pass before Princess finally arrives. She looks absolutely stunning. I had never seen her in her business apparel before. She wears a black pencil skirt that ends just above her knees. It is accompanied by a simple white long sleeve button down and a black business coat. The shoes are what really gets me. It is my first time seeing Princess T in heels and I can almost feel my jaw dropping. Her always sexy feet are adorned by a pair black business pumps with a heel of about 3 inches. They are not open toe, but have low dip in the middle so that much of her smooth, dark brown foot is showing. It is extremely hard for me not to stare.

I stand to greet her. In her heels she is probably about my height, but it feels as if she towers over me. I have to fight the urge to drop to my knees right in the middle of the restaurant. Instead, I pull her chair out and greet her as professionally as I am able. She takes her jacket off and places it over the back of the chair. Her shirt only has the top button undone. Her breasts are not exactly bursting out, but the shirt is tight and does show off her incredible figure. I feel my dick begin to stir as I take my seat.

Princess T eyes my old fashioned suspiciously. I stammer the explanation that I have been waiting for a while and felt bad not ordering anything. A sly smile crossed her painted red lips. "It's fine. I could use a drink myself." Our server appears as if on command and Princess orders a margarita.

"I have been working like crazy this morning. There has been so much to do. But thankfully I should be able to finish everything from home and for that I think I deserve a drink."

I nod excitedly in agreement. "I am glad you were able to make it even with all the work you have."

She asks me about my day and I embarrassedly admit that all I really did was get ready for this date.

She rolls her eyes a bit but in a good natured way. "If I had more time to spend guiding you, I could make you much more productive. You waste so much of your time not being productive." She takes a sip of her margarita while bearing down on me with intense, yet playful eyes.

"I agree. It's crazy to me how thoroughly I will clean your apartment but I won't tidy up my place one bit."

"That is because you don't value your time or your space as much as you value mine. And of course you should cherish my time and my space because I am your Superior, but you should still value your space more than you currently do."

I simply nod in agreement. By now the waitress has returned and we order our food. The rest of the conversation is pleasant and touches on our everyday lives. She asks me more questions about my daily life, my job, my workout routine. She offers many firm but nonjudgmental suggestions. We reach the conclusion that I will begin to inform her of more mundane accomplishments in my day-to-day life. For example if I complete a cleaning project at home, I will text her the details upon completion. The same goes for working out or having an above and beyond achievement at work. She makes sure to point out that she will not necessarily respond or congratulate my little victories of production, but we both agree that the simple act of telling her will serve as a little mini reward for me.

The food is delicious. She has a steak topped with grilled shrimp and I order the trout, trying to stick to a loosely pescatarian diet. She gets a glass of red wine with her entree. I stick with water, feeling my single cocktail has loosened me up sufficiently. She orders a dessert to go, claiming it will be a treat for her once she finishes her work later. I pay the tab and tip handsomely.

"Follow me to my car," she says curtly once the bill is paid, her voice changing only subtly but filling with more authority. I grab the bag containing her dessert and follow her staying about two steps behind her. Her ass is molded to perfection by her skirt. The single slit in the middle slides back and forth between each leg as she steps with purpose. The back of her legs alone are a sight to behold. Her calf muscles are well defined and her Achilles tendon snakes out handsomely from the back of her black heels. I realize that it is odd to be so enraptured by an Achilles tendon, but I could watch every inch of Princess's body walk in this outfit for hours at a time. My mind soaks in the splendor of her feminine beauty while my face attempts to mask my lust. We are at her car before I know it.

She unlocks her doors with her fob and has me put the dessert in her backseat. She lowers herself in the drivers seat, keeping both legs on the ground outside of the car. "Come here, sissy," she says playfully. As I stand in front of her she asks if I am wearing panties.

"Yes Princess."

"Good sissy. I purposely did not ask you to. I wanted to see what you would do on your own. I also appreciate that you did not ask me. It is good to see you take some initiative. Now lift your panties up and show me."

Part of me wants to look around to see if the coast is clear, but I realize it is pointless because Princess will expect obedience regardless. I lift up the sides of my lacy yellow thong to her inspecting eyes.

"Ohhh I like that color on you," she informs me approvingly.

"Thank you Princess."

"Now you know I have to work when I get home, but I think I still have some things you can do for me. Would you like to be my home office assistant, bitch?"

I was not expecting this at all. My dick starts to harden and I eagerly reply, "Yes Princess."

"Get on your knees and kiss the top of my feet right now if you truly want to be my assistant today."

I drop to my knees without a word and place my pursed lips firmly on Princess T's exposed foot.

"Do you like the way my feet look in these heels sissy?"

"Yes Princess! They look incredible," I stammer out almost breathlessly as I continue to gaze upon them in awe.