Little role play turned bad

Sissy in pink dress and red high heels

Note: This story involves consenting adults and is no way a work describing acts of pedophilia.

House cleaning slave

One Saturday, Ma’m Ann ordered me to purchase some cleaning supplies and to report to Her home, as usual, bringing my “second-best” little-Girl disguise and my “soft” Mary Janes. When I’m going to be Feminized in public, or for party guests, a Domme usually prefers that I wear my prettiest frilliest little-Girl clothes, and my patent-leather Mary Janes, but I dislike wearing such pretty clothes when I’m doing hard work or receiving intense torture. Ma’m Ann’s stipulation of “second-best” was a warning that I should expect to receive some rough treatment!


Find your little near ?

As part of my usual preparation for Feminization and age play, I carefully shaved my entire body (including “down there”) so that I would be smooth and soft and hairless all over.

I reported promptly to Ma’m Ann’s home. On my arrival, Ma’am Ann ordered me to strip naked and submit to inspection. She took my male clothes, keys, I.D., and wallet, and locked these in Her safe, while I read the long list of chores that She had assigned for me. I expected Her to command me to put on my little-Girl clothes, and to get to work. Instead, Ma’m Ann merely tied a string of sleigh bells around my little inchworm, then She tied a tiny frilly sissy-maid apron around my waist … and then She ordered me to get to work, just as i was. my little-Girl outfit would be put aside for “later”.

For several hours, I scrubbed and cleaned throughout Ma’m Ann’s house, beginning with the dungeon in Her basement and then working my way upstairs. The steady jingle-jangle of my inchworm announced my diligence and my constant activity, but I knew that Ma’m Ann had other ways of observing me. Her entire house, and the front door were monitored by video cameras, and Ma’m Ann was able to view these from security monitors in Her workroom and throughout the house. While I worked, clad only in a teeny lace-frilled apron, Ma’m Ann remained in Her office, the only room I was never permitted to enter.

Time to service the guests

After I had worked for several hours, the doorbell rang. On the speaker, Ma’m Ann’s voice commanded me to “open the door”. If She had said, “answer the door”, I would have understood this to be Her command for me to screen the visitor through a closed partition so that I did not reveal my nakedness. But “open the door” was Ma’m Ann’s command meaning precisely that: I was required to open the front door and stand there, fully naked and sissified, to politely greet whoever had arrived. I was to keep my hands at my sides, making no attempt to conceal my inchworm, and to maintain eye contact with the visitor … or, if there was more than one, with the visitor who seemed most Dominant.

I opened the door and was confronted by two very large tall muscular young African-American men in street clothes. When they saw a much smaller white man standing there — shaved, naked, hairless — wearing only a frilly little sissy-maid apron, they both smirked in delight. Then they laughed out loud when they saw the string of sleigh bells dangling from my tiny little inchworm. As I saw their eyes glance down towards my thighs, I foolishly violated Ma’m Ann’s rule to maintain eye contact, and I glanced downwards myself. Both of these men wore tight-fitting jeans, and the enormous bulges in both of their crotches told me that these two huge black men each had a LARGE proud reason for laughing at my own tiny pathetic little inchworm.

Stepping into the hallway behind me, Ma’m Ann greeted these two black gentlemen, and invited them to “go downstairs and get comfortable”. The two burly black men merely past me — one of them muttering “‘Scuse me, faggot” — and they went down to the cellar, which was also Ma’m Ann’s dungeon.

Ma’m Ann commanded me to lock the door, while She inspected my housework and found it to Her satisfaction. Then She ordered me to put away my work items, take off my slave bells, and to put on my little-Girl costume while instructing me: “you are a Girl, four years old, and your name is Sissy. When you are ready, you will report to the Nurse’s office” … this being one of the playrooms in Ma’m Ann’s house. Having given these orders, Ma’m Ann walked away.

Getting ready for my men

I have a very nice strap-on Vagina made of molded latex, the same color as my own skin. It is hairless, and the back of it contains a small latex pouch into which I tuck my male baubles. (The pouch is very small, but then so are my male parts.) I stripped naked and then I put on my sissy-Vagina, careful to tuck my inchworm so that it was positioned correctly behind the urethra (piss-hole) of my Vagina, in case my little-Girl self had to go “wee-wee” later. Next, I put on my frilly pink ruffled sissy-panties and my lace-frilled white ankle socks. I carefully crammed my feet into a pair of Mary Janes made from soft black velvet, without hard soles or heels.

There are security monitors all over Ma’m Ann’s house; I am forbidden to change the image or audio without Her instructions. The monitor in front of me was showing the dungeon. The two large black men were sitting in the dungeon, watching a DVD player as it showed an old Shirley Temple movie. Little Shirley Temple, all dressed up in frills and curly blonde hair, was acting out a scene with the legendary black dancer Bill “Bojangles” Robinson. The scene required this adult black man to cringe and “yassuh” to this little white Girl. I could tell from the body language of the two black men watching this movie that they were not amused. On the audio, I heard one of them say to the other: “Shit, you know what I’d do to that little white bitch?” and then both black men laughed.

I put on my petti-slip and several white frilly petticoats, then I laced myself into an elaborate ruffled pink baby-doll dress, appropriate for a four-year-old Girl but tailored for my man-sized body. Next, sitting in front of a mirror, I tucked my short male hair into a wig cap, then I put on an elaborate Goldilocks-style wig with long blonde curls and ringlets. I fastened the wig in place with a pink hair ribbon under my chin, and several bobby pins. Next, using a safe water-based glue, I carefully glued to my eyelids a set of realistic false eyelashes that would make my eyes look softer and more Feminine without any drag-queen exaggerations. Finally, I crammed my hands into a pair of white wristlet gloves with lace-trimmed cuffs.

Since I am required to remain in character whenever I’m Feminized and Girlified, from this point onwards I was REQUIRED to speak and behave exactly like a little four-year-old Girl. I blew a kiss to the mirror, and then — clutching my skirt and petticoats — I skipped down the hall to the Nurse’s office. I knocked politely on the door, and was told: “Come in.”

Punished by the school nurse

I entered. Ma’m Ann was seated, wearing a nurse’s uniform, with a scowl on Her beautiful face. Knowing that I was required to be a polite little Girl, I curtseyed prettily and announced, in a high-pitched lisping Girlish voice: “Hewwo, Ma’m. my name ith Thi’thee, an’ I’m faw years old.”

She got right to the point: “you must be Sissy Wetmore. I am the School Nurse. I’ve had some very unpleasant reports about you. The teachers and the Schoolmistress have seen you touching yourself in your girly-place.”

I meekly confessed that I was guilty of that crime. “Come here, young lady. Stand in front of Me. Pull down your panties, then lift your skirt and petticoats and hold them above your waist.” The School Nurse was flexing a short steel ruler.

I meekly obeyed. The School Nurse seized me roughly by one arm, and She pulled me over her knees. WHAP! WHAP! WHAP! She proceeded to spank me unmercifully with Her steel ruler, while I whimpered and squirmed and i “promised” to be good. Finally, the School Nurse dumped me onto the floor, commanding me to adjust my clothing. Brushing a long blonde curl away from my face, I obeyed.

“you and I are not finished, young lady,” said the School Nurse sternly. “I have received reports that you stole some licorice, and you ate it during class. Is this true?” Again, I meekly confessed my crime. The School Nurse slapped my face, hard. “Bad girl! Don’t you know that candy will rot your teeth? Open your mouth!”

I obediently opened my mouth. “you’d better put on a dental bib,” said the School Nurse, fastening a bib around my neck above the collar of my pink frilly dress. Now the School Nurse inspected my teeth. “Terrible! you need braces!” She declared. “Hold still.” From a nearby drawer, the School Nurse took a glittering steel object: a Whitehead dental gag, designed to keep a dental patient’s mouth forced open. I meekly stood still as the School Nurse inserted this into my mouth, locking the bars so that it could not be removed. I expected Her to adjust the gag to its maximum extension, forcing my mouth open: instead, She left it in the open setting, so that I could not remove the dental gag but I could otherwise move my mouth normally and even speak coherently.

“Now, as for touching your girly-place … THIS is how we punish a naughty little girl whose hands go where they’re not supposed to.” From a desk drawer, the School Nurse took a pair of gleaming steel handcuffs. She seized my arms and pulled them roughly behind my back. Click-click, and suddenly my wrists were handcuffed behind the pink taffeta sash on my frilly dress.

“Now, you just come with me, young lady,” said the School Nurse angrily. Seizing me by one elbow, She yanked me towards the stairs and proceeded to march me down to the cellar … to the dungeon. Without my arms, I had to be very careful to avoid stumbling.

In the dungeon were the two muscular black men. The DVD monitor was still playing a Shirley Temple movie, but now the sound was turned off. On a table in front of the DVD were several sex magazines open to centerfolds of sexy Women. Now, as the two black men stood up, I saw that they both had their jeans unzipped, and each of them had a huge hairy black cock poking out of his jeans. These men had been masturbating while they looked at the sex magazines, and now their huge erections showed they were horny.

Just then I noticed that the bib around my neck was trimmed with pink lace, and embroidered on the bib in big red letters was my name “SISSY”.

As the School Nurse dragged me into the room, I tried to hide behind Her, but She twisted my arm painfully. When the two black men saw me — an adult white man dressed as a frilly little “Girl”, wearing a bib marked “SISSY” — they both burst out laughing, and neither man tried to conceal his huge black cock.

Handing me to the black monster cocks

The School Nurse cleared Her throat. “This little girl is named Sissy. she says she’s four years old, but I suspect she’s somewhat older. I have restrained her hands because little Sissy likes to touch herself in her girly-place. Little Sissy also likes to suck on licorice sticks, even though they gum up her braces. I will leave little Sissy here while you gentlemen explain to her what happens to naughty little girls who suck on things they’re not supposed to.” The two black men laughed cruelly, just as the School Nurse stepped out of the dungeon, closing the door and locking it. I could hear Her feet going upstairs beyond the locked door, and i knew that Ma’m Ann would be watching and listening on a monitor in Her workroom.

Now I was humiliated twice over: because I was a small white man, handcuffed and completely helpless, in a room with two large muscular horny black men, and also because I was supposedly a “little Girl” here with two large men flaunting their enormous erections. Knowing that Ma’m Ann was watching every move I made, and knowing i was required to stay in character, I meekly did a no-hands curtsey and introduced myself: “Hewwo, thir. Hewwo, mithter. my name ith Thi’thee.” I didn’t want to play this “game”; I only wanted to get out of there!

The two black men smirked cruelly as they started asking me questions: “Why do you do this?” “What else do you like to suck on, LITTLE GIRL?” Their questions took on a very unpleasant edge because I couldn’t tell whether these men were role-playing — pretending I was a genuine four-year-old Girl — or if they weren’t playing at all, and were simply taunting and bullying me while treating me exactly like what I really was: a sissified white man. These black men had already seen me naked, and they knew that the tiny soft inchworm inside my frilly pink panties couldn’t possibly compete with the two enormous black hard-ons that were now pointing straight at me.

As these two much larger men interrogated me, their humiliating questions had a double meaning: “Why do you do this?” could be a question addressed to a naughty little Girl who had been caught touching herself … or it could be a question addressed to a grown man caught dressing up as a little Girl. Were these men role-playing that I was a “Little Girl” … or was this no game at all, and they were righteously and angrily confronting a pervert? Each time they addressed me as “Little Girl”, I shuddered so deeply that my taffeta petticoats rustled: were these men play-acting, or were they being sarcastic? One of the men lifted my petticoats while he looked me in the eyes: “What else do you like to suck on, Sissy?”

Whether these men were role-playing or not, I knew that Ma’m Ann would be furious if I did not remain in character. Squirming in my frilly pants, my long blonde curls bobbed up and down as I timidly lisped out a few meek answers in my little-Girl voice … confessing that I liked to steal candy and suck on it while I touched my “girly-place”. my childish lisp was no longer an act: the dental gag in my mouth prevented me from speaking clearly.

Finally, one of the black men, with a nasty tone in his voice, said: “So you suck on licorice sticks, huh? Open your mouth, bitch!” Genuinely terrified now, I opened my mouth. He started fiddling with the bars on the Whitehead device, and suddenly I realized that he knew how to adjust a dental gag. Before I could protest, he had suddenly jacked the gag open all the way … forcing my mouth wide open, with my jaws so far apart that I couldn’t bite anything that might enter my mouth!

“Now let’s take a look at this little bitch’s pussy,” said the other black man. “Hold still, bitch!” He grabbed my skirt and petticoats and thrust them roughly into the pink sash waistband of my frilly ruffled dress, exposing my bare legs and my panties. I tried to plead “Please don’t!”, but my forced-open mouth only made a few childish gurgling noises. One black man took out a knife and held it to my throat. “I said DON’T MOVE, bitch!” Absolutely terrified, I decided to be a “good Girl”: I meekly stood still with a knife at my throat while the other black man tugged my panties down to my knees. The two men stood there, appraising my naked white buttocks and the hairless “Vagina” between my thighs that was clearly a strap-on counterfeit.

I stood trembling in my Mary Janes and frilly ankle socks while the two black men made nasty comments about my “little white girly ass” and my “pussy”. I felt humiliated twice over: I felt exactly as if I REALLY was a terrified little Girl being sexually inspected at knife-point by two child molesters, and at the same time I felt the genuine humiliation of exactly what I truly WAS at this point: a totally helpless sissified white man at the mercy of two large strong merciless black men with huge erections.

Extreme role-playing

At that moment, I did exactly what any genuine little Girl would do if confronted by two child molesters: I made “wetties”. Suddenly I lost control of my bladder, and a stream of piss — not a proud male gusher, but a pathetic Girlish dribble — started trickling out of the hairless little-Girl vagina between my bare thighs. I couldn’t control it: like a frightened little Girl, I was wetting myself.

“Gaw-DAMN!” yelled one of the black men, jumping out of the way. I saw that a couple of drops from my “wetties” had landed near his shoes. Ma’m Ann would be furious if I stained either of these visitors … but with no hands, and with a little Girl’s equipment between my thighs instead of a penis, I had no way to aim my golden flow. Hot tears of shame filled my eyes as I dropped to a squat and made my wetties girly-style, spreading my thighs while I squatted directly over the drain in the floor of Ma’m Ann’s dungeon and I emptied my bladder downwards between my Mary Janes … feeling exactly like a genuine little Girl, forced to make her wetties while two child molesters watched and laughed.

“you finished now? Gitcher ass back on up, bitch!” one of the two black men commanded me. Of course, i could not wipe myself. Afraid to disobey, I stood up … a few drops of my girl-piss staining my bare thighs.

“Git up, bitch! Turn around!” I whimpered and squirmed helplessly while the two black men stroked their hard-ons and debated whether or not they should “mess with” my “pussy”. Finally, they decided it would not be a good idea to “pop my cherry”. I took this to mean that they were role-playing after all, and therefore they were agreeing that I was actually a four-year-old Girl with a real Vagina, not a man disguising his tiny manhood behind a latex fake.

Then … they raped me.

my struggles were real, my high-pitched squeals of terror were genuine. I kicked my little Mary Janes as hard as I could, but the soft velvet shoes made were as weak and helpless as the rest of me. my handcuffed arms were totally useless. I felt genuinely as weak and helpless as an actual little Girl as these two large powerful black men proceeded to rape my “little white-bitch ass” and my “little white-bitch mouth”. The taste of the dental gag’s surgical steel, forcing my jaws open, was not the only taste that filled my mouth. Muscular black hands gripped my white butt-cheeks and spread them apart, and now I was getting filled down there, too.

“Swallow, bitch,” one of the black men hissed, pressing his knife to my throat as his enormous cock choked my throat.

They both must have been VERY horny because they came several times inside me. They also switched places, so the cock that had raped my little sissy-girl ass was now in my throat, and I got to taste my own shit on this black man’s dick.

When they were finished with me, my frilly petticoats and the bib marked “SISSY” were thoroughly stained, and my lips were dripping with my own shit and two black men’s sperm. my two rapists dropped me to the floor and left me there, whimpering and sobbing like a helpless little Girl, while they zipped up their jeans and laughed at me. I was no longer play-acting: genuine tears of shame and terror stained my long girlish eyelashes and my Sissy-bib.

The door unlocked and Ma’m Ann entered, still dressed as the strict School Nurse. There was a damp spot on the front of Her nurse’s uniform, and I knew that Ma’m Ann had pleasured Herself while She watched my rape on the vidcams. Now She spoke: “I see that this naughty little girl has learned her lesson. Thank you, gentlemen. Will you see yourselves out?” my two rapists left, laughing, while Ma’m Ann, with a touch of gentleness, unlocked my handcuffs and the dental gag.


Kinky girls in

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