Sissy Stretching for Princess T

I balance my phone up against my dresser, take a deep breath and wait patiently for further instructions. I had already received orders to be dressed in my pink negligee with no panties (or underwear of any kind) on and my butt plug inserted by 7 pm. I was in position 10 minutes early and was attempting to clear my mind and focus solely on obeying whatever orders I eventually received.

A few weeks ago I had gone shopping with a woman I refer to as Princess T. She was a dominant woman who was looking for a submissive cuckold boyfriend and I had eagerly applied for the role. I had been exploring my submissive side for some time and had served many Dommes but was desperately seeking an actual long term relationship. Things were moving a bit slower than I wished, but I thought of Princess T everyday and was always quite eager to obey her orders on the rare occasion that I received them.

On our shopping trip the last time we had seen each other, she had me purchase the butt plug that was currently inserted into my ass, a large dildo with a suction cup base that was now stuck to my bedroom floor in front of my propped up phone, and the pink negligee I was wearing, along with some pink stockings and a pink thong. Since the shopping trip, I had worn the plug almost everyday for varying amounts of time, sometimes instructed by her and occasionally on my own.

A few nights I had worn my new pink panties to work at her instruction and taken pictures for her in the bathroom. She had yet to give me any instructions regarding the dildo. I had practiced sucking it a few times on my own, but was unable to get much of it down before I gagged and would quickly lose interest since there was not a woman urging me on. My plug was inserting a bit easier with each use, but I had yet to even try to get the head of the dildo in my still tight hole. As I sat starting at my phone I wondered if that would change tonight.

At 7:04 I received my first text from Princess.

"Are you in position sissy?"

"Yes Princess"

"Send me a picture of you kneeling on your floor with the dildo in front of you. And lift your negligee up so I can see your tiny little penis."

Princess had never seen my penis before. When we first met she asked me how big it was and I told her it got to six inches when it was hard. She had seen it crammed into panties several times and was skeptical that it got that big. At this moment, kneeling on my floor for her, I was extremely turned on but my penis showed no signs of it as it dangled limply between my legs, not even touching the floor. I lift my negligee up with one hand and snap a picture with the other.

Princess responds with a laughing emoji.

"There is no way that little thing ever gets to six inches. Either you lied to me or it's shrunken since you last measured it."

I continue kneeling and do not respond, not sure what to say. I don't mind that she thinks that. Sometimes I wish my penis was smaller. It cannot please a woman as is, so it may as well be extra tiny and good for a laugh.

"Now turn around and take another picture. I want to see that plug all up in your tight little sissy ass."

I turn around and snap another picture. The first one comes out a little blurry. I slide a little closer to the camera and try again. The second one is much better. The base of the plug is clearly visible in my ass and the dildo is still in the shot on the right side. I send the picture.

Another laughter emoji initial response.

"Such an obedient little sissy. Do you like obeying my commands little sissy boy?"

"Yes Princess T."

"Good. I am going to push you a little harder now but it is for your own good. Are you ready?"

"Yes Princess T. I long so badly to please you and obey your commands."

"Okay sissy, now I want you to make a video of your mouth sliding over the cock in front of you. I want you to take as much of it as you can down your throat until you feel like you are going to gag. I want you to stop right there and hold that position for 20 seconds. You should be able to see the timer of the video on your phone in front of you. And remember, that's 20 seconds of the toy down your throat. Do not start timing until you are about to gag."

I gulp and take a deep breath. This is exactly the type of order I had been awaiting. A quick thought of wishing I had practiced more flashes through my head, but I quickly toss it aside and focus on the task at hand. I put my phone on video mode and position my body in front of the camera with the toy suctioned on the ground in between us. I am on my knees, with the nub of my limp penis barely poking out from under my pink lingerie. I lay my hands flat on the floor by either side of the dildo. I look up at my phone screen to make sure everything is visible in the shot. It is. I reach forward, press record and quickly place my hands back on the floor.

I open my mouth wide and place it over the head of the thick, dark brown dildo. It has a bland plastic taste. My tongue slides almost involuntarily around the base of the head as I push my face down onto the fake cock as far down as I can. My gag reflex kicks in a little before I expect it to. My lips are maybe halfway down the toy, meaning less than half of the girthy 8 inches is lodged in my throat. I breath deeply and try not to panic. Tears begin streaming down my eyes as I shift them upward to keep an eye on the clock. It's at 13 seconds at first glance so I must maintain my current position until it hits 33 seconds.

My gag reflex hits again without moving any further down the toy. I attempt to stay calm and relax my throat. More tears form in my eyes and drip down my cheeks . 10 seconds pass. Time seems to be dragging so slowly. 15 seconds. My gag reflex hits again but not quite as strong. Finally 20 seconds has passed. I hold my mouth in place for a few more seconds just to make sure. As soon as my mouth pulls off the cock I begin gasping for air. Tears stain the floor by my hands. I am a little shocked that having less than 4 inches in my throat for 20 seconds could feel so exhausting. I reach for my phone and send the video.

The video ends up being 50 seconds long and takes awhile to send. It takes even longer for Princess to respond. My breath returns quickly and I immediately feel horny and eager for more. An urge arises to rub my still limp little clitty but I resist. Princess has not specifically forbidden me to touch it, but I feel it would be best to wait for permission. I empty my mind the best I can and stare at my phone screen. Finally, a response appears.

"Hmmm, I appreciate your effort but must say I am not all that satisfied with the result. I thought you would have been practicing with your toy already but you can barely get half off it down your little sissy throat. However I do enjoy seeing your tears run down your face. You look so cute and pathetic."

"I will do better Princess. I apologize for not practicing more. And thank you for saying that I look cute and pathetic."

"This time I want you to go down deeper. Watch the first video again for reference if you must. Once you get deeper, hold it for a bit, not necessarily 20 seconds, but maybe 5 or so. Then I want you to suck up and down making sure when you go down you get as far down as you can."

"Yes Princess. Thank you."

I get back in my previous position with my hands on the floor. Looking down at the brown phallus in front of me I feel that I can tell how far down I got last time without watching the video. Without starting the camera, I press my mouth mouth onto the toy. I reach about where I was last time, feel the gag coming and press further. Pushing the dildo past the reflex actually helps a bit. I naturally relax my throat and am able to go even a bit deeper. I shift my eyes up to the phone and confirm that I am much deeper than last time. More like 6 inches down than 4.

I pull my head up and reach out to start recording, keeping my lips wrapped around the head. Once the camera starts, I bob my head seductively a few times on the head of the dick while swirling my tongue on the underside. It has been years since any poor woman has put her mouth on my tiny penis, but I can imagine that what I am doing to the toy would feel nice.

Then I get down to business. I shove my throat down onto the dildo, suppress my initial urge to gag and withdraw, open my throat, breath though my nose and go lower. My lips are only about an inch away from the dirty floor. I probably should have cleaned my floor before doing this. Now is not the time for such thoughts. The urge to gag hits hard. I make a choking noise and feel my saliva start sliding down the fake dick. I hold it a couple seconds longer and pull up. The dildo is dripping with spit. I resist the urge pull off and take a deep breath, instead sliding my mouth back down the saliva covered toy.

This time when my gag reflex hits I am ready for it and am able to relax my throat much quicker. I am not sure if I quite reach as far as I did the first time, but a desire to keep going up and down takes over. My mind goes blank as my head bobs up and down. I am sucking a cock and it feels amazing. I barely register the tears streaming down my face or the pool of spit collecting at the base of the toy. All that matters is filling my mouth with with as much of the delicious rubber cock as I can.

I choke and gag trying to get all the way down and it jerks me back to reality. A little vomit tickles the back of my throat but I swallow it quickly. Through my teary eyes I see that the video has been running for almost a minute and a half. I quickly stop it and hit send.

I attempt to collect my thoughts as the video sends. I am certainly horny, there is a bead of pre cum dripping from my still limp penis. Yet my desire to touch myself has been replaced by a desire to suck more. Given the choice to rub on my little clit or put the fake dick back in my mouth, I would not hesitate to suck the cock. I find this curious, but do not continue sucking the cock without permission.

My mind goes basically blank again as I await Princess's response. As much as I do want to put the dick back in my mouth, I am content kneeling on my floor in my negligee awaiting orders. Being patient is a very important part of being a good submissive.

3 laughing face emojis with tears break my mini trance.

"Well done sissy. Looks like you really got into it that time. That's how I want my sissy to suck!"

"Thank you Princess!"

"Now are you ready to start stretching your little hole for me?" smiley face emoji

My ass tenses up a bit just at the thought. Up to this point I had been pretty oblivious to the plug in my ass. All my attention had been focused on the dildo and on my throat. "Yes Princess. I am ready to obey." I type in reply.

"First I want you to film yourself pulling the plug out. Get nice and close to the camera so I can see your hole all stretched out."

I pull the plug out with a muffled pop. There is a quick but mild pain that quickly dissipates and is replaced with a feeling of emptiness. I spread my ass cheeks in front of the camera for a moment and then turn to see the video. As it sends, I watch it myself. The pop is barely audible, it sounded louder live. My hole looks a little wider than I imagined it would. I feel my nervousness switch gears to excitement. I wanted my mouth full before, but now I want my hole filled. Looking at it on the video makes me believe it will fit.

"Mmm I really like seeing your hole all stretched out. I look forward to making it wider and wider"

Before I can reply, my instructions come through. "Now I want you to try to ride it. I know you probably can't get all the way down on it, or even as far down as your mouth got, but try your best. I want you facing the camera with your little nightgown lifted up so I can see your little clitty and balls bouncing up and down as you ride that big dick."

I feel myself blush. This is probably the most explicit text message I have ever received from Princess T. She has certainly never called my little penis a clit before. I relish the humiliation, but know I must get to work.

I position myself in the middle of the frame, legs spread wide hovering above the rubber dick. I take a deep breath and reach out to start the video. Once it's rolling, I lower myself slowly onto the head of the cock, hands pulling my cheeks apart . There is pressure at first but not a ton of pain, just slight discomfort. The discomfort upgrades to pain as I slide down a bit more. I yelp in a high pitched voice, sounding girly without even trying. I manage to stay where I am but grow terrified to go lower. I already feel so much fuller than with the plug. The dildo is so wide. I realize I hadn't used lube at all. She had not instructed me to, but had not forbade it either. I try to slide down further but my hole resists its penetrator. I squeal in pain again. I pull up off the dildo and stop the video.

I sent the video followed by a message. "I'm sorry Princess, I know that wasn't good enough. May I please use some lube on the dick?"

I go ahead and grab my lube from a nearby drawer while I await the response. I do not have to wait long.

"Yes, sissy you may use lube. I don't want you to injure yourself. Though I do enjoy your little girly cries of pain" laughing face emoji

I rub lube up and down the shaft of the dildo, figuring this part does not need to be filmed. This is the boring behind the scenes work, not the sexy stuff. For some reason rubbing my hand up and down the shaft makes me want to suck it again, but once I feel it is sufficiently coated I get back in position to slide my hole over it.

This time the head goes in much easier, barely any pressure. The pain doesn't start until the point where it became unbearable last time. This time I am able to push past it. The difference is night and day. My hole is accepting the phallic gift instead of rejecting it. I get maybe halfway down, perhaps a bit more and decide that I am full enough. I linger for only a few seconds and then start moving up and down. My legs tense and hold me up as if I am doing squats. Once I feel that the toy is in solidly, I drop my hands from my ass cheeks and lean back on them, taking some pressure off of my legs and feet. This makes riding it much easier.

Moans of pleasure escape my mouth as I gyrate up and down on the brown sex toy. It feels good to be full. I still can't imagine taking the whole thing. Half off it fills me up so much that I can feel it pressing against my prostate. I notice some pre cum dribbling out of my limp penis. In the heat of the moment, not thinking she will mind, I scoop up the pre cum on my finger and lick it off. I try to ride more animated now, getting my hips more involved and trying to feel sexy. I come up too much and the toy slides out. The sudden emptiness feels strange. I realize I have been filming for two whole minutes now so I stop the video and send it.

Before the video can even send, I am back riding and recording. Once again my hands spreading my cheeks as I slide onto the dick and then I lean back on them to allow myself to dance and shimmy and buck my eager little asshole onto the toy. Quiet moans of pleasure escape my lips. I'm enjoying it even more than the sucking. Once this thought comes to mind, I realize my throat does feel empty. I glace over at my plug. It's obviously still dirty from my ass but there are no visible shit stains. In the heat of the moment, I pick it up and shove it in my mouth while I continue to ride up and down on the cock. It tastes mostly like lube with a hint of shit. I suck on it eagerly, full of joy and pleasure at having both of my holes occupied. Sooner than I wish I realize I must stop the video for it to be small enough to send by text. The first one has sent but has yet to be commented on. I pull myself off the cock and take the plug out of my mouth. My ass does not even feel particularly sore, just empty.

I stop my phone and send the second video. It is too long and I have to delete some off the end, but I still think Princess will be pleased with my performance. Watching it myself I realize my face isn't in the frame, so my in-the-moment act of sucking on my dirty butt plug is not visible. My hand can be seen moving and kind of shifting but it is not clear why. The licking of my precum is more obvious. My hand is seen scooping it up and then my hand disappears out of site above the view of the camera. Not difficult to piece together what is happening.

The sexual high I was experiencing declines as the second video sends. The craving of having my holes filled subsides. I even feel a bit embarrassed that I got so into it, but am still mostly pleased that it didn't hurt too badly. The real joy will come from a positive reaction from Princess. It takes quite a bit for her to respond. I still don't dare put anything away, just in case she has further instructions.

About 20 minutes pass from the sent time on the second video before her response appears. I grab my phone off the floor and eagerly being to read.

"Good job sissy. I am very pleased. It seemed like you were enjoying yourself. It still think you could have gone down a little lower and got more dick in your ass, but knowing you were riding it and enjoying it turns me on. Perhaps if I want you to take more I will just have to push it in myself." Winky face emoji

My heart starts to pound a little. It feels so fucking good to please her. The thought of her fucking me excites me greatly.

"I have to go now. I am sure your horny ass wants to play more, but I cannot be bothered by anymore videos. You may play with your toys more if you wish but DO NOT touch that little clit. I saw you lick up your pre cum like a little cum slut. I will let that slide but no more clit touching tonight. I don't want you releasing any of your sissy seed before I see you again. If you are good and continue to obey me, I might have a task for you this weekend."

"Thank you Princess. It felt so good to obey you and make slutty videos for you. I'm so glad you enjoyed them. I'll be thinking about you all night but won't bother you anymore. Goodnight Princess T."

"Good night sissy."

Even though I know another response is not coming, I spend a few more minutes on my knees in lingerie staring at my phone, rereading her messages of approval. I am still a bit horny but the desire to assault my holes has mostly passed. I put my toys up, put on some regular pajamas and try to watch some TV. It is difficult, but somehow I make it through the night without touching myself.

The next few days drag slowly. I text Princess every morning as soon as I wake up. She answers eventually. The conversation mostly centers on the mundane. We talk about work, the weather etc. She makes no mention of me not touching myself and I try not to bombard her with how horny I am and how much I think about her. She gives me no orders to plug or practice on the dildo but I do both occasionally on my own. Once while fucking myself with the dildo while in bed, a huge pool of pre cum gathers on the sheet. I rub it in with my finger, denying myself the pleasure of tasting it. It is difficult controlling my horniness without talking about it, but not unbearable. Finally, Friday night Princess texts me asking if I am free the next day. I am. She tells me to be at her house by 11 am. I ask what I should bring. She replies panties and cleaning supplies and wear your plug. I do not get much sleep Friday night.

Saturday morning I jolt awake every hour starting at 5 am, finally dragging myself up at 9. I quickly eat and shower. It's not quite ten yet, but I decide to head out anyway. I slide my plug in and put on the pink thong I had purchased while shopping with Princess. I stop at the store for flowers and a bottle of wine for her and arrive at her house 15 minutes before 11.