In my last assignment, I was instructed by Mistress Amber to dress as a sissy slut in bondage and orally service Ms. Lisa’s strap-on dildo—an assignment I took too lightly, neglecting to package my boy-parts and performing the entire assignment flat chested. Due to my negligence, my punishment was to first repeat the assignment—this time in proper form—before switching positions to service the sizable naughty-chair dildo while exposing my backside to Ms. Lisa for her to administer as she saw fit. It was to be a most unpleasant night of correction, however one I much deserved, and have learned a valuable lesson on thoroughness from…
The evening began with the transformation from wayward boy into sissy girl—Ms. Lisa had me try on a number of outfits before she settled on a bra-pantie set and a pink plaid skirt, perfect for allowing full rear access. My hair was done up into sweet little girl pigtails, and my face painted up to match the part. Once hair, makeup, and outfit were completed, we moved on to packaging up my boy-parts, which proved to be a bit of an adventure as—while the definition was clear—neither of us really had any clue as to exact technique. In keeping with the stipulations of “as uncomfortable as possible”, we selected an unfinished jute twine (a natural, very scratchy material) for the task and set about wrapping until everything was concealed below a bundle of scratchy lines. With my bits suitably buried, Ms. Lisa produced a pair of black water balloons to fill out the bra she had selected—they were a bit of a stretch, and the bra could only barely support them, but eventually she made them fit. She produced a length of rope and proceeded to bind my hands as a final bit of preparation before the punishment commenced in earnest.
Once I was prepared, Ms. Lisa sat me down on the naughty chair (for this, she left the dildo off—she didn’t want me too loosened up for later) and donned her strap-on, massaging the head of the thing along my lips before taking a firm grip on the back of my head, firmly forcing my lips down the shaft until my whimpers and gagging signaled to her that she’d found her mark. She thrust the rubber phallus in and out of my mouth with the energy befitting a punishment, alternating gripping the back of my head and using my pigtails as handles as she worked. After about 10 minutes of thrusting and gagging, she decided that it was time for me to practice my talents on something larger, and time to show my bottom the attention that it deserved.
Ms. Lisa was gracious enough to unbind my hands while she began setting up for the second phase of my punishment, a slight break that would not go appreciated until it was over. She had me kneel in front of the naughty chair as she positioned it into place, firmly fixing the large dildo into its familiar place before moving behind me to rebind my hands and feet—much more cruelly this time. My wrists and ankles were firmly secured before being lashed to one another, and my face was slowly, yet firmly guided down onto the waiting dildo. In this position, I had no support to hold myself up—rest could only come by lowering myself completely down to the naughty chair, which would force the dildo down my throat, and so I was left to support not only my weight, but the weight of my water balloon breasts which felt as if they were becoming heavier by the second. A few times, she took a grip on the back of my head and forced my down onto the thick dildo, delighting in the gagging before allowing me to raise once again. Once satisfied that I was focusing on my duties, she moved behind me, raising my skirt so that she could begin my correction.
The attention she showed my exposed backside was most unkind—with her nails, hands, and her favorite hairbrush she demonstrated to me the error of my ways. While she dug her claws into my poor bottom, all I could do was focus on supporting the weight in my bra and servicing the rubber shaft in my mouth. When the hairbrush strikes began to fall, I tried to pull up and off the dildo, but all I found was her forceful hand guiding me back down the shaft. The squeals of each strike only served to fuel the subsequent blows, and kneeling there I was forced to reflect upon my shortcomings one loud crack after another. My final lesson, however, was still to be administered, and as Ms. Lisa unbound my hands for a second time, I had a sinking feeling of what that lesson might be.
As Ms. Lisa rebound my hands in front of me, graciously allowing me a touch of respite as I was able to support my weight by kneeling forward on them, I had a pretty good idea of what was in store for me. While diligently servicing the naughty chair’s dildo, I could hear her slipping on her strap-on harness, the snap of the condom being secured over it, and finally Ms. Lisa herself positioning herself behind me. She once again lifted my skirt, making sure it was securely out of her way before forcefully thrusting forward, plunging her dildo into my ass. Digging her nails deep into my flesh, she thrust her phallus deeply into me, not letting me forget that I’d done this to myself. Over time, her intensity increased, spurred on by the muted whimpers that escaped my filled mouth, every thrust more vicious than the last. At one point, she was thrusting so violently that she literally fucked the water balloons right out of my bra. When she finally stopped, I was a docile little puddle, unable to do more that suck on the dildo before me and shake. It was at this point that she, thankfully, decided that I’d learned my lesson, unbinding my hands and feet and allowing me to change. While the punishment may be over—I can safely say that being lax in the completion of my assignments is not a mistake that I will soon forget.
Treatments Completed During This Assignment
This is a table showing the extra treatments that I subjected myself to for failing to finish this objective in a timely manner.