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.