A Simple Minded Sissy

Poor Sissy Gretchen.  His transformation had been particularly difficult.  He had resisted the process every step of the way.  He simply would not cooperate with the plans I had for him.  But I knew he would make an exceptionally pretty -- and valuable -- sissy once the transformation was complete.

Through a combination of drugs, hypnosis, electroshock and beatings, I was eventually able to break through his resistance and complete his conversion.  And I was right -- I was able to transform this young man into one of the prettiest sissies I ever made.

Aided by a daily dose of narcotics, Sissy Gretchen becomes a simple minded little sissy who no longer has any will of his own.  He will obediently follow any instruction given no matter how demeaning or disgusting.  That makes him the perfect sissy escort.  I have a long list of wealthy men who have no problem paying me thousands of dollars for a few hours with this gorgeous and completely docile sissy love doll.

At the end of every long day of sissy sex servitude, Sissy Gretchen has an unusual bedtime routine.  He strips off his pretty dress and slips into a sexy, sheer and very revealing baby doll nightgown. Then he allows me to put a ball gag in his mouth and to tie his wrists and ankles to the bedposts.  Sissy Gretchen falls asleep, content and mindless.  I leave his bedroom light on.

These bedtime preparations are required because during the hours before dawn, Sissy Gretchen will awaken as yesterday's dose of narcotics begin to wear off.  As his brain begins to refocus, he remembers who he was -- and what he has become.  I expect his mind is flooded, all at once, with images of his feminized self submitting to the disgusting demands of his many male clients.  The terror he experiences is amplified by seeing his own gorgeous sissy reflection in the mirrored ceiling above his bed, his enormous breasts barely concealed by his sheer baby doll nightie.  He writhes in mental agony on top of his bed, struggling to free himself from his lashings.  His screams muffled by the bright red ball gag in his mouth.

I allow this to continue to a couple of hours until I am ready to get out of bed and deal with poor Sissy Gretchen.  By then he is a wreck, overcome by his exhaustion and horror.  I stand above him and tease him.  "Oh, what's the matter sissy?" I might say.  "Don't you like staring at your sexy reflection in the ceiling mirror?  Aren't you happy that you are now a perfect sissy slut?  Didn't you have fun yesterday -- and everyday -- doing all those nasty things you did to all those men?"  It doesn't take much to get him to start sobbing.

Eventually I take pity on him I inject him with today's dose of narcotics.  He slips back into unconsciousness for a couple of hours.  When he awakens later, the episode he experienced just a few hours earlier will have been completely forgotten, as he begins another day of obedient sissy sex servitude.

Sissy Attends a Tea Party



"Now don't look so glum, sweetie," Mistress said.  "You are going to have a wonderful time at the tea party. And you look so pretty in your new dress.  I'm sure all the other sissies will be jealous of you."  She patted me on the cheek as if I were a little child.  "Now hurry and get my coat and get in the car."

I did as I was instructed.  I felt ridiculous in my new dress.  It was pink, covered with ruffles and had a wide satin sash around the waist.  Mistress made me wear pink anklets and open toes burgandy platform shoes to complete the ultimate sissy look.

I dread going to sissy tea parties.  Every Wednesday afternoon, my Mistress dresses me up in some frilly, lacy dress and drags me to the weekly sissy tea party.  The tea parties are held at a huge mansion outside of town that is owned by one of her friends.

We arrive at the mansion right on time at 3:00.  I follow my Mistress inside in silence.  She greets her friends, who are all sissy owners just like her.  I curtsey to each of the other Mistresses in silence.  The Mistresses make a fuss over my new pink outfit.  I greet the other sissies with a small kiss.  Today there are four Mistresses each with her own sissy.

The sissies move into the kitchen where we prepare the tea and plates of food for our Mistresses.  We serve our Mistresses in silence while they chat among themselves, treating us sissies as if we were invisible.  While the Mistresses eat and chat, the sissies stand in silence at the edges of the room, quickly attending to any needs of our Mistresses.

At 5:00, the Mistresses have finished their tea and conversation and the sissies have cleared the table and washed all the dishes.  Now is the part that I hate the most.  The sissies stand in a line in front of the Mistresses who pair each us off with another sissy.  We then have to make out with our sissy partner in front of the Mistresses.  The sissies have learned that it is important to put on a good show for the Mistresses, so we really get into it, running our hands over each other's boobs and bottoms, grinding our hips into each other, moaning and gasping as we deeply french kiss each other.  The Mistresses love the show.  They shout demeaning and filthy things at us.  

"Time for some sucky-sucky fun!" one of the Mistresses shouts.  Two sissies are instructed to remain standing, while two are sent to their knees to administer a sissy blow job.  Today I am told to stand while Sissy Annabel is told to kneel.  I gather up the full, frilly skirt of my dress while Sissy Annabel lowers my panties and puts my tiny little cock in her mouth.  Now the Mistresses go completely wild.  They are shouting at us, laughing at our tiny penises and joking about how much sissies love to swallow cum.  Some ever start touching themselves as the excitement of the show becomes too much for them to handle.  I close my eyes as I begin to cum in Sissy Annabel's mouth.

The party ends and we begin the drive home.  I know that I will be up late tonight licking my Mistress's pussy for hours as I help her to relieve her excitement from the afternoon.



A Sissy Begs for Forgiveness

"Oh, please, Stepmother," I begged.  "It won't happen again.  I am so sorry.  I promise.  Please don't punish me.  PLEASE!"  I stood in the middle of the room, perched in my towering high heels, my manicured hands clasped together as I repented for my failings.

"SILENCE!" Stepmother shouted.  "You are NEVER to speak unless spoken to!"

I lowered my eyes to the floor, now terrified that I had made my terrible situation much worse.

"Look at you, you pathetic sissy.  I can see right through that ridiculus outfit you are wearing.  Only a real sissy slut would dress like that.  Aren't I right?"  she asked.

"Yes Ma'am," I replied softly, even though we both knew that she picked out all the outfits I was allowed to wear.

"You broke a very expensive teacup when you were washing the dishes today and that sort of misbehavior must be punished.  So what will it be, sissy?  The paddle or the dildo?"

Oh no, I thought.  This was going to be bad.  Even though my bottom was still raw from my last spanking, I really hated being punished with Stepmother's strap-on.  "The paddle," I said.  "Please," I quickly added.

I pulled down my panties, lifted my billowy skirt over my waist, and lay across Stepmother's lap.  But before she started paddling my bottom, she called out loudly, "Tiffany, please come in here!"

And in walked Tiffany, my stepsister.  Oh God!  What was Tiffany doing here?  It was so humiliating having my much younger stepsister seeing me like this, laying across Stepmother's lap, with my skirt hiked up and my bare bottom sticking up in the air. I started to try to squirm away, but Stepmother is so much stronger than me and she held me firmly in place.  "Be still, Sissy!"  Stepmother growled.  Tiffany roared with laughter seeing me like this.

"You see, Sissy," she explained, "I decided that it was time to show Tiffany how to discipline you.  That way we can ensure that you will always be as obidient to her as you are to me.  Now go ahead, Tiffany.  Do it just the way I explained."

Tiffany picked up my punishment paddle and waved it in front of my face.  "Kiss it, Sissy," she said with an evil grin.  I did just as instructed, knowing that to protest would be very unwise.

And with that Tiffany began to administer 20 stinging blows to my bare bottom, while her mother held me firmly in place on her lap.  After the first ten, Stepmother said to Tiffany, "Now dear, if you don't spank him harder than that, how will he ever learn his lesson?"

Tiffany put all her strength into the next ten blows.  I could hear her laughing as she abused my bottom.  Tears were pouring down my face as the pain and humiliation were unbearable.

When Tiffany was done with my beating, Stepmother started rubbing my burning bottom.  "Have you learned your lesson, Sissy?"

"Yes Ma'am," I whimpered.  "I'm very sorry. I learned my lesson."  I started to get up from Stepmother's lap.

"Not so fast, Sissy," she said with a sneer as she kept me pinned to her lap with her strong arms.  "You didn't thank Tiffany for teaching you a lesson and helping you to become a better Sissy."

I choked back my tears and forced myself to say, "Thank you Tiffany for teaching me a lesson and helping me to become a better Sissy."

Stepmother administered a sharp bare-handed slap to my bright red bottom and snarled, "From now on you will refer to her as Mistress Tiffany, do you understand?"

"Yes, Stepmother.  I understand.  I am sorry for my inpertinence, Mistress Tiffany."

"That's more like it," Stepmother said with a satisfied smile.  "Now get yourself cleaned up and get started on making dinner."

Mr. Lane's Sissy

Last month, I told Mr. Lane, the counselor at my school, that sometimes I like dressing up in girl's clothing.  I thought that maybe I was crazy and that he would be able to help me.

Mr. Lane was really nice.  He said I wasn't crazy at all and that there was nothing wrong with having "girlish feelings."  He asked me a lot of embarrassing and personal questions. He asked me things like if wearing satin panties made me excited and if I ever thought about kissing boys.  I guess I answered the questions well because he was smiling a lot and kept saying, "That's good, very good."

He said that he would help me but that for my own good it would have to be "our little secret."  He told me that I should meet him at his house every day after school.

The first time I visited his house, he showed me a whole closet full of girl's clothing and shoes and wigs and stuff.  He said that it was important for me to "embrace my feminine feelings" and "explore and experience girlish things."  He showed me how to do my make-up and stuff.  He let me wear a dress and took some photos of me before I had to change back into my boy clothes and go home.

It's been four weeks since that first visit.  Everyday I rush to Mr. Lane's house as soon as school is out.  I do my make-up and put on girl's undies and whatever dress Mr. Lane left out for me to wear.  I hurry so that I can be all ready and look very pretty by the time Mr. Lane gets home.

Mr. Lane said that today would be very special.  I put on the pretty flowered dress and matching hair bow that he had left out for me.  I met him at the door when he got home and he handed me a big bouquet of flowers.  Then he hugged me and gave me a big kiss.  I didn't really like that but he said it was part of the process of understanding my girlish feelings.  Then he told me how beautiful I looked and that made me feel happy.

We then moved to the couch where he told me to sit on his lap.  I had never done that before and it made me sort of nervous but I did it anyway.  Then he started kissing me some more and running his hands all over my body.  I could feel that he was getting an erection.

"Today, I'm going to teach you to be a real girl," he said as he unzipped his pants.  "Now get on your knees."

Blonde Sissy for Black Master

When the world middleweight boxing champ wanted to get his very own sissy, he came to me. He was a black man, amazingly strong and fabulously wealthy.

I transformed a young man into a perfect sissy sex toy for him.  Sissy Tammy's body had been forcibly feminized to perfection.  Sissy Tammy was petite, blonde and completely terrified of his new owner, who has made Sissy Tammy's life a nonstop nightmare.

Master enjoys using Sissy Tammy as his own living sex doll, forcing himself on his defenseless little sissy whenever and where ever he wants.  Master likes to pick his sissy up in his big strong arms and fuck him in mid air, roughly bouncing his sissy up and down, again and again, on his rock hard cock.  Poor little Sissy Tammy feels like he is going to be split in two every time Master rams his huge cock into his tight little Sissy pussy.  Sissy screams in pain with each thrust, but the sissy's sceams just get Master more excited.

After Master is done filling Sissy Tammy's ass with gallons of his hot cum, Sissy Tammy crawls between his Master's legs and carefully licks his Master's massive dick clean.  If Master gets hard again, then Sissy Tammy gets to swallow another load of his black Master's seed.  And when Master tires of having his enormous dick sucked, he lies down on his king sized bed for his nightly massage.  Sissy Tammy has been trained to expertly massage his Master's strong, muscular body.

Oh dear, it looks like the massage is making Master's dick hard again.  Get ready for another fucking, Sissy!

Poker Night Sissy

Every Friday night, Master invites five or six of his friends over for poker night.

Master insists that I get all dolled up in a fancy cocktail dress, 5-inch heels and sexy make-up.   My strapless dress barely covers the large breasts Master forced me to get.  He says I have to look my best when his friends are over.

At 8:00 the guests begin to arrive.  I greet them at the door and take their coats.  Always keeping my eyes lowered, I inform them that I am the "sissy of the house" and that I have been instructed to serve my Master's guests in whatever way they require.  As I say this, I can feel their hungry eyes on my exposed cleavage.  I can tell they are smirking at my humiliation and submissiveness.

For the next four hours, I serve them drinks and snacks.  The men play cards and drink and smoke and laugh.  Mostly they ignore me, but they often grab my ass or squeeze my boobs when I am serving them. They say mean things to me and call me "whore" and "slut" while they fondle me.  When I'm not serving the men, I stand silently in the corner and wait.

Then, promptly at midnight, the men put down their cards.  The game is over and they count their chips.  They carefully figure out who won, who came in second, third, and so on.  Then they line up, the winner in front.  It is now time for me to do what I have been dreading all evening.  I drop to my knees in front of the winner, I pull down his pants and I open my mouth.

The night's winner jams his big dick into my mouth and I suck and lick it eagerly the way Master trained me. The winner's dick get bigger and harder.  He roughly bucks his hips, ramming his cock in and out of my mouth for several minutes.  Then he grabs the back of my head and forces his cock down my throat.  And then he explodes.  He blasts his hot, sticky cum into and I swallow it all.  All the other men hoot and shout as they watch the winner cum in my mouth.

"Next!" Master yells to everyone's amusement and the next man in line drops his pants.  I put his cock in my mouth and let him rape my face.  I repeat this until each man has unloaded his sperm into my mouth.  And for being the night's winner, I have to give the first man a second blow job.

I feel sick and disgusted, with the load of several men in my stomach and on my face.  "Get yourself cleaned up!"  Master yells at me.  "What a whore!" he adds to the amusement of the others.

I race to the bathroom and quickly wipe off my face and redo my lipstick.  I rush to get the men's coats and to see them out.  They usually have something mean to say or enjoy one final laugh at my expense as they leave.  With the final guest gone, I get busy cleaning up after the night's game.

With the house clean and the clock striking 3:00, I enter Master's bedroom where he has been sleeping.  I pull back the covers and begin performing my last blow job of the night on my Master's massive cock.  "You are such a filthy little sissy slut," Master mutters, half asleep, as I begin to cry.