Ordeal Of A Prison Sissy

In March of 2011, I was sentenced to 5 years in jail for car theft. Being only 18 years old, the judge thought he was being lenient by giving me the minimum sentence but since I have been here I have been forced to undergo the most grueling and sexually degrading experience of my life. Being rather frail and not very tough I was immediately set upon by the huge muscular cons and lifers who daily prowl the cellblock looking for young boys.

A Black Con’s White Sissy Boy

I suppose I should say I was lucky enough to come under the protection of a huge black con name Tiny, who took me under his wing and made me his pet sissy. He sent away for various articles of female lingerie from catalogs he had and every night after lights out, he demands that I dress up in a baby doll nightie and sheer pink panties for his sexual amusement. At first I tried to resist, but after numerous beatings at his hands I had to submit and now spend almost every night as his sexual play toy in the cell, much to his and other inmates amusement.

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He insists that I squat when I pee in our communal toilet and doesn’t hesitate to beat me savagely if I forget and stand up to urinate like a man. He says it breaks his fantasy to see me act like another man, as he is now made me his bitch. When I am tired or unwilling to spend the night sucking his huge black cock or allowing him to rape me in the ass, he threatens to “pimp my little bitch ass out” to his friends for a pack of cigarettes, something I dearly dread. I’ve seen what happens to other white sissy boys when the brothers get a hold of them and I have no desire to end up in the infirmary having my anus sutured after one of their bitch parties.

Recently he has demanded I dye my long hair blond and start wearing makeup even during the day. I am loathe to do this as if any of the others see me dressed like that, they will immediately think I’m fair pray for their sexual hungers and perversions. I say perversions, because some of the men in here are so hard and psychopathic that one risks immediate death or torture if you refuse their advances or embrace. I know of one sissy boy in the other cellblock who must spend his nights rimming the dirty asses of some of the grossest man on the planet, an ordeal they call “tossing the salad” and something I never want to endure. I admit I cling to my black daddy for protection and thank the Lord he only wants me to service his huge black cock like a woman and not some degraded sissy bitch.

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When my time is up and I must return to the real world, I hope to put all this behind me, although I have to admit I have grown fond of feeling the sheer silky fabric of my lingerie on my body as I nestle in my black stallion’s arms and drift off to sleep. I’m sure most my friends already know that being a young white boy in a mostly black prison means I’ve had to partake of numerous homosexual liaisons, but the part of me dressing like a woman and acting like a little girl for huge black cons is something I prefer they had no knowledge of.

sissy tommy
[feminized prison sissy]

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Mistress Sold Me As A Sissy Slave

Today I am packing my clothes and making ready to leave with my new master, a wonderful man named Prince John. Having completed my feminization and sissy training under the care of my Goddess Mistress Femme, I am now ready to begin my new life serving my black African master. He is a rich man from Nigeria, and a dear close personal friend of my Mistress. Coming to the United States for business, he also was in the market for a new white sissy slave and attended one of Mistresses’ slave auctions, where he purchased me.

Sissy Slaves Purchase Policy

Mistress has a policy of allowing her clients to try before they buy, and I was made to accompany him back to his hotel room for the evening so he could see how well I had learned to serve a master. Making me dress in a sheer pink nighty, lacy thigh high stockings and black high heels, my potential master took me to bed and enjoyed me in as many positions as he could think of. I must say that servicing his giant black cock was an absolute delight, and something I dearly look forward to doing repeatedly as his new sissy male maid back in Africa.

He told me that he has many slaves at his compound in Lagos, but that I will be the only white sissy he has, and as such will be allowed to serve him in the master house and sleep in a private room just off of his bedroom. He is fabulously wealthy and has allowed me to go shopping to my heart’s content, telling me to pick out as many sexy outfits and cute skirts and dresses as my heart desired. Naturally I spent the last two days shopping like crazy and have filled several suitcases with lingerie, shoes and pretty dresses. I have no idea what the shopping situation is in Nigeria, so I want to be well stocked and have many beautiful things to keep my new master sexually aroused and pleased with my appearance.

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I know that Mistress received a good sum for my purchase, and I only hope that I might live up to her standards is a well-trained sissy male maid. It is an honor and privilege to be able to embark on a new life as a feminized male, and something I’ve dreamed about ever since a young boy. My friends and family in my former life have no concept of what it means to secretly be a sissy but be forced to live in unnatural lifestyle as a heterosexual man or husband. So it is with great excitement and anticipation that I now begin my journey to mother Africa to serve my black master in any fashion or manner he so desires!

sissy nolan
[obedient and submissive sissy]

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Feminized By The Maid

Roger didn’t think twice about making his poor black maid Sara work overtime with no pay or insulting her by calling her “Aunt Jemima” when he got mad at her. He even forced her to wear a skirt that was way too small for her rather large build and would laugh if her large bottom showed beneath the hemline when she bent over while cleaning.

But all that came to an end one day when Sara brought someone to work with her – her large ex-con boyfriend Nigel. A huge hulking black man who had just gotten done serving eight years of hard time in prison, and had a mean reputation for “Busting white sissy bitches in the ass” while doing time.

Before Roger could even ask what Nigel was doing there the huge thug had him by the throat.

“You think it funny to be dogging my woman?” he thundered “Well, I knows how to fix your white ass, bitch!”

He threw Roger to his knees, grabbed him by the hair, pulled out his nine inch erect black cock and shoved it in to Roger’s mouth with a grin. “See, baby” he said “This is how you treat a white boy who needs busting”.

Sara smiled. “I’ll be right back” and she disappeared into the maid’s dressing room to fetch the small uniform Roger had made her wear these past few weeks, Upon returning to the room, she held it out. “Make him wear this!”

“Just as soon as he’s done here”. And after Nigel had ejaculated all over Roger’s face, he picked him up by the hair and pointed him toward the uniform. “Get that on, bitch or I’m going to throw your ass out the fucking window!”

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Shocked and scared out of his wits, Roger put on the little maid uniform and stood there shaking, not knowing what was to come next.

“Make him do some cleaning, Nigel” Sara said, then watched gleefully as Nigel forced Roger to dust, sweep and scrub about the house for the next thirty minutes. All the time yelling insults at Roger like “Sissy bitch” and “Punk ass sissy”.

And while poor Roger was bent over cleaning some books on the bottom shelf like he had made Sara do many times before, Nigel grinned at Sara and said “Look at that white sissy ass bent over, baby. Want to see me fuck this sissy boy good like I did in the pen?” Sara nodded “Make him a bitch, baby” she said.

Before Roger could flee the room Nigel had him bent over the couch with his skirt up and frilly panties down. “Now you be getting a good ass punking, bitch” Nigel roared as he levered his massive hard black cock into Roger’s tight virgin asshole, using only a dab of hot spit as lube. “You going to be my prison bitch sissy from now on and I’m going to fuck your tight white ass everyday!” He slammed his cock again and again into Roger’s stinging anus, going balls deep each time and working up to a fierce climax.

Pulling out he thundered “Get down and swallow this load of man gravy, bitch!” Grabbing Roger by the hair once more and launching a giant load of hot semen down his throat and all over his lips and chin. Finally he was drained, shaking his huge cock dry, then released Roger.

“You ever make fun of my woman again I’m going to come back here and make you my sissy bitch again, you hear boy?”

And with that he grabbed Sara, turned and left!

Poor Roger, turned into a sissy male maid and punked by a black man all in one day!

Mistress Tia
(Bitch Mistress In Charge)

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