forced sissy Archives - The Dirty Diary

August 2, 2019

Published by Dirty Diary at August 2, 2019

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Teasing My Roommate

It wasn’t hard to tell that Rodger was in to me but he was so bashful and shy that he seemed like the perfect roommate. Nerdy and quiet, he never bothered me when my girlfriends and I partied just a little too loud or too late. But one night a couple of my friends had passed out in my bed and I figured I’d crash on the couch in Rodger’s room while they slept it off. I cracked the door and couldn’t believe what I saw… he was sleeping in a pink princess adult baby diaper and a matching frilly nightgown! I couldn’t help but giggle- loudly enough that he woke up! My sissy roommate’s face was priceless, I had caught him indulging his secret fetish and he blushed even brighter than his cute nightie. He started pleading with me not to tell anyone, but I had something much more fun in mind. If this was all it took for him to beg, I wondered just how far I could push him as his sadistic […]

December 5, 2008

Published by Dear Diary at December 5, 2008

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Scat

Punishment

Once I give an order I expect it to be followed promptly and to the letter. Well a circumstance arose the other day in which it was not properly obeyed. So what else was I supposed to do but bring down My wrath? The punishment was a paddling with no warm up and once I was done he said his little butt was burning so I made him sit in a bowl of ice water with his cock down in there also. If you think of being insolent with Me your Master this could be awaiting you, slut. Master Paul

October 17, 2008

Published by Dear Diary at October 17, 2008

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Scat

From Hell

Sometimes a regular spanking won’t do. Just some tapping from my every day paddle won’t get the point across. On days like that my bitches need a spanking from hell. One that will make you wish that your actually were on fire, as it would hurt less than this. Now you might be wondering what could a sweet subbie do to deserve this sort of punishment? Why don’t you try me and find out. Master Paul

September 28, 2008

Published by Dear Diary at September 28, 2008

Categories

Scat

Sissy Store

I took one of my little sissy girls to the mall the other day for a unique shopping experience. He was to pick out and try on his new outfit, shoes and makeup. We started at the clothes store so that he could try on dresses for my enjoyment and his embarrassment. He settled on a white lacy sundress. Next to the shoe store we went for him to model about a half dozen new shoes before getting a pair or white sandals with little flowers on them. Then on to the makeup counter for a full makeover. By the time we left he was the sissy boy that we wanted him to be. Master Paul