A few years back, I met this guy Filo. He said he loved bondage, especially in prison uniforms. Filo said he would show up wearing shorts and a tee shirt and would change into his prison uniform once he got here. I told him that would be fine, but to wear sneakers and no flip flops being it was summer.
Well, Filo only partially obeyed. He showed up wearing shorts and a tee shirt, but, he was wearing flip flops. (Sorry to the flip flop fans, but there are only two places they should be worn, the beach or the pool).
Filo changed into his gray and white prison suit. I gave him a pair of gray Sanuk Vagabond sidewalk slip on surf shoes, which matched his outfit. I also told Filo that there would be a punishment to be determined for wearing flip flops.
The scene would be the prisoner would be strapped up into the straight jacket, placed in a leather hood, ankles secured to the camping cot. A towel would be placed over his face once he was secured to the camping cot.
Now that he was secured, (this was not the heaviest of bondage, but we both knew he would not be going anywhere). He was then administered a cock endurance session to keep him on the edge, though not allowing him to shoot. Light and heavy duty vibrators would be used through his prison outfit to get him hard and keep him hard.
Filo endured the combination of pleasure and torment, using both the light and heavy duty vibrators through his prison suit. I would tease him with the vibrators for a while, stop and let him simmer, then start again. I knew he was extremely horny and wanted to shoot. I knew this, because not only could I hear him moaning, but could see him pulling against the straight jacket and ankle restraints.
The torment and pleasure continued with the vibrators with me stopping at times for me to rest. This was also used to send him on a head trip, and to make him wonder what could come next. After about an hour and a half, it was time for his punishment. The ankles were untied from the camping cot, the towel was removed from his face, and he was stood up. I took him out of the leather hood, and then the straight jacket. I told him his punishment was that I would not allow him to shoot while he was tied up for disobeying and wearing flip flops.
Overall, the prisoner did pass his cock endurance test, where he was horny and squirming and not shooting.
Filo said that while he wanted to shoot while he was tied up, he loved the cock endurance tests, and said he should have been punished by not allowing him to shoot for not obeying and wearing flip flops.
Filo did thank me for the bondage session, changed back into his shorts, tee shirt and flip flops. As he was leaving, he said loves prison scenes, and him being sent home without shooting was punishment. He also said that prisoners need to be punished when they don't follow rules, regulations and directives.
I am sure he had a good time.
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