Fill That Sissy Boy's Ass! with Mistress Kristin
Oh, what a great adventure I had during my time off! I went to Dallas and attended an enema party held at the home of a close Mistress friend of mine. I took a lovely young sissy boy with me for his first public enema.
The morning was beautiful and my boy—he was excited and terrified at what was about to happen to him.
I took him downstairs to the main room. He faltered when he saw that twenty people had already gathered to watch his predicament. Mistress Sada had set up a special enema table in the center of the room just for my sissy boy: steel with restraints on the sides.
Strip! I commanded. His dick was hard and ready for serious use. I placed a cock ring over his dick and balls, for I did not want him to cum until I was ready. In his eyes I could feel his hope, hope that I would allow him to speak. The time in which he could object, beg, or plead had long since passed. Now he would do what I wanted—how I wanted and for as long as I wanted.
I instructed him to climb up on the table. Forty eyes were on him and his soft round ass up in the air, on display. His asshole was exposed and winking. I strapped his hands to the sides of the table, and slid a bar under his waist to keep him in position—the position otherwise known as: unable to lower his ass.
A slave girl rolled over the enema stand, heavy with a nice red five-quart bag filled with a solution of salt water. I pulled out my brand spanking new nozzle: it was five inches long, shaped like a dick, and had a big hole for the water to rush out of—mimicking a dick cumming in his ass.
I touched his cheeks and he jumped, and everyone laughed. My sissy boy's face turned red, but the humiliation was just beginning.
I lubed up the nozzle and instructed the slave girl to spread his ass checks. The lovely shade of red that was covering his face moved down his naked body. I slid the nozzle in.
Are you ready? I asked.
He nodded. That would not do. Speak up, I firmly said.
Please Mistress, fill my ass, he whispered.
Louder! I want every pair of ears in here to hear you, I said.
Please Mistress! Please! Fill my ass! Please!
The room joined in with: Yes, fill that boy's ass! Make him beg!
As the laughter subsided, I opened the flow valve and the water rushed in. His cock got harder and harder. I reached under him and ran my hand along his dick and balls. He tried to move against my hand but the metal bar stopped him. Soft moans escaped from his lips.
Quickly his moans shifted to soft cries. His stomach was becoming extended, and the bag was only half empty. I closed the flow valve.
His soft, supplicant voice begged me to give him release: release from his hard cock and from the cramps. Silly boy! He would not feel release from either of them soon. No, my fun had just started.
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Categories: Anal Fetish, Medical Fetish, Submission, Enemas, Domination, CBT, Humiliation, Fantasy, Sissy Fetish, Bondage
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As a young boy I was given a weekly enema and physical examination by either my mother or an aunt until the age of 15 or so. Usually on a Saturday night, I was required to strip completely naked for the two of them. I was then positioned over their lap with my bottom fully exposed. A lotion was then applied to my butt hole, both externally and internally. While one of them held the red rubber enema bag above me, the other would insert the nozzle deeply inside me and the warm soapy water would then fill me up. I was then required to void myself, take a bath and then return to them to be examined. On some occasions, my female younger cousin was allowed to participate as well. The examination was limited to my uncut penis, my testicles and my buttocks. A rectal temperature was always taken as well. I actually enjoyed these sessions and regretted when they were stopped for no reason apparent to me. I did, however, continue to strip naked for my cousin for quite a while. She would almost always have one or more of her girlfriends participate as well. As a 70 year old male I still fondly remember this phase of my life and would love to relive it again.
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