This is my first post since joining the Institute, detailing my first assignment—I was to dress as a sissy slut in bondage while giving oral service to a strap-on. This task was not the easiest thing in the world, as for the moment, my collection of “sissy” clothing is not as extensive as I would like it to be. After conferring with my partner Ms. Lisa, however, we managed to achieve a setup and an outfit that did justice to the assignment. Using what little clothing was available to us, Ms. Lisa’s collection of makeup, a length of rope, a mouth spreader, and our own special “naughty chair”, we managed to achieve a very uncomfortable, humiliating situation.
The assignment began with my outfit—a pink lingerie top with black panties and stockings, braided pigtails, and a blindfold. My hands were then bound behind my back and I was photographed standing, kneeling, and modeling the snug-fitting mouth spreader. From there I was led to the bedroom, where the naughty chair—a small stool fitted with a rather large vibrating dildo—was waiting for me, positioned next to the bed. My panties were pulled down around my ankles and I was slowly guided down into a kneeling position, impaled upon the dildo, where my panties were then wrapped around my ankles, effectively binding them as well. The mouth spreader was then reinserted and cranked as wide as it would go before Ms. Lisa went to busy herself setting up the camera, leaving me kneeling there, blindfolded and kneeling to contemplate my predicament.
By the time she began, my bottom was already beginning to get sore from the dildo, and a small line of drool was forming on my chin from the mouth spreader, and I was starting to dread being filled at the other end as well. At first she slowly guided my open mouth onto the head of the pink strap-on, letting me get used its presence before more forcefully pulling my head down until the dildo was pressing at the back of my throat, causing me to gag. After giving me a chance to collect myself, she once again pulled my head down onto the dildo, sliding my head up and down the shaft a few times before once again pushing it back to my throat, causing me to gag once again. By this time, I was drooling quite profusely from the mouth spreader, and being unable to wipe myself off, both my chin and down my front were becoming quite well covered. She experimented with a few different things, including pulling my face down onto the dildo by my pigtails, which was quite a humiliating experience as after every thrust I was drooling more and more, and my top was becoming quite moist.
After about 45 minutes of being stuffed at both ends, my whimpering prompted her to pull up my blindfold so she could look into my eyes. The soreness in both my bottom and my jaw must have been clear in my eyes, because at this point, she took pity on me. She removed the mouth spreader and the binds on my wrists, leaving it to me to free my ankles and remove myself from the chair—no easy task as my legs were very tired and at least once I only managed to get part way off the dildo before falling painfully back down onto it. By the time I’d managed to get myself free, I was very sore, wet, and exhausted but the assignment was complete, and for the time being, I was free—until my next assignment…