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.

Afternoon Sissy

Whenever I am home alone, I love playing dress-up.  I raid my mother's closet, her lingerie drawer, her make-up, jewerly, perfume -- everything.  She even has a long curly wig that I use to complete my look.

I love dressing up like a girl.  I feel so feminine, so free, so alive.  I love getting my make-up perfect and slipping on the wig.  I especially like wearing my mother's sexy lingerie.  Dressed like this, I enjoy staring at my pretty reflection in the mirror looking back at me.  Sometimes I take photos of myself, like this one, that I can look at late at night when I'm in bed.

But today, disaster struck.  I had the house to myself all afternoon -- I thought.  My mother was at work and my older brother was at football practice.  I was all dolled up, wearing my mother's light pink, lacy nightgown.  I was in the living room, dancing to the radio and watching my performance in the big mirror, when all of sudden in walked my brother and three of his friends from the football team.

"What the fuck!?!?" my brother shouted wen he saw me.

"Who's that?" one friend asked.

"That's my faggot little brother," he answered.  The other boys howled with laughter when they recognized me.

"He sure is pretty," the biggest of the friends said.

"Hey," another one said. "Even though practice was cancelled, I think we can still get a workout this afternoon, if you know what I mean."

"Go ahead," my brother said.  "I don't care.  Do whatever you want with him."

And with that, the three boys dragged me upstairs to my bedroom to be their "Sissy Girlfriend" for the afternoon.  Thet took turns having sex with me while the others held me down.  I tried not to cry, but they were really rough with me and it hurt a lot. 

When they were done with me, one of them said that I was cute enough to be a cheerleader -- and if I was a cheerleader then I could get fucked by the boys on the team all the time.

Hmmm.  Maybe I will...

After School Sissy -- Part 3

Last Friday afternoon, when I came home from school, I went straight to my mother's room to do my make-up and put on one of her dresses like I do everyday.  As soon as I was satisfied that I looked pretty and girlish enough, I got busy on my chores before it was time to start making Stepfather's dinner.  As I was dusting upstairs, I went into my bedroom and discovered that my bed was gone.  When Stepfather came home I asked him what happened to my bed.

"Oh, I decided that you wouldn't be needing that old bed any more," he said.  I didn't understand what that meant, but I know he doesn't like it when I ask a lot of questions, so I let go.

After dinner, we went to the den and I climbed onto Stepfather's lap like usual to watch TV.  He wrapped his big arms around me, and started stroking me through the satiny dress I was wearing.  But after just a few minutes he let out a big yawn and announced that he was tired and wanted to go to bed.  "Come with me," he said.  "I have something to show you."

He took my hand and led me up the stairs to his bedroom.  I noticed that one of my mother's nightgowns was laid out on his big bed. 

"I want you to put that on," he said.  I knew better than to argue, so I picked up the silky nightie. 

"Okay," I said.  "I'll take this to my room and I'll try it on."

"No," he replied.  "You can change right here."

So I unzipped my dress (I mean mother's dress) and let it fall to the floor.  Stepfather seemed to enjoy watching me as I did this.  I unlaced my corset and pulled off my stockings.  I was about to take off my bra, but Stepfather said to keep it on.   While I was undressing, Stepfather started rubbing the front of his pants with his hand and was breathing hard.

I carefully pulled the silky nightie over my head, being careful not to mess up my wig or make-up.  The nightie was extremely feminine and sweet.   It had little ruffly cap sleeves and was trimmed with several ribbons and bows.   "Walk around," Stepfather instructed.   "Yeah, that's nice," he said as I paraded around the room. 

After a few minutes he handed me another one of mother's nighties.  "Here," he said.  "Try this one on."  I did as he instructed.  I modeled several nightgowns for him that evening.  He decided that he liked the one I tried on last the best.  It was soft pink with white applique flowers trimming the neckline. 

"Yes," he said.  "Keep that one on."  He kept staring at me, his hand still rubbing his erection through his pants.  I felt so exposed just standing there in th sheer nightie.  I held onto the back of the chair while he continued to stare at me. 

After a few minutes, he came out of his trance.  He said that he was going to go to the bathroom, and that when he came out, he wanted the lights dimmed and the candles lit.  I didn't like where this was going but I didn't argue.

I prepared the room the way he asked and after a few minutes he emerged from the bathroom.  He was completely naked!  He ran at me and literally pushed onto his bed.  He fell on top of me, all of his weight -- and his erection -- pressing down on me.

"This is the way things are going to be from now on, Lydia," he stated, calling me by my mother's name.  "Now spread your legs."

Helpless Sissy Love Doll

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Sissy Goes Outside Part 1

I liked dressing up in my older sister's clothes and I did it whenever I was home alone.    First, I would put on one of her bras and a pair of her panties.  Next I would go to the bathroom and do my make-up and fluff up my longish hair.  Then I would go through her closet, trying on her dresses, skirts, blouses and shoes.  I even dressed up in her nightgowns and bathing suits.  I would pose in front of her full length mirror, admiring my feminine reflection.

That's exactly what I was doing when disaster struck.

I was all dolled up in my sister's make-up, underwear and a party dress.  The dress was my sister's favorite.  It had a feminine, white ruffled top, a black skirt and a wide belt that gave me a sexy shape.  I was also wearing her sexy new peep-toed pumps with really high heels.  I felt so girlish and sexy.  I was posing and admiring my reflection in her big mirror when I heard a girl's voice scream, "Oh My God!"   I spun around and saw my sister and two of her friends standing behind me. My sister's friends started laughing uncontrollably.  My sister shouted, "What the fuck are you doing in my clothes?!?"

I was too shocked to speak so one of her friends answered for me. "Your brother is a total sissy faggot!"

My sister glared at me for a minute and then said, "Don't move."  She went downstairs followed by her friends. I was so afraid and confused and ashamed that I that just stood there as she ordered.

A few minutes later the three of them returned.  "Well Sissy," she said, "I'll make you a deal.  I won't tell Mom and Dad about this -- but you have to do something for me."

"Sure," I said eagerly.  I would do anything to keep my parents from learning about this.  "What do I have to do?"

"It will be easy," my sister replied.  "All you have to do is to walk down Walnut Avenue, from Church Street to Parker Street." 

"You want me to go outside?  Dressed like this?" I exclaimed.  I had never even thought about going outside before.

"No!  Not in my favorite party dress.  We'll pick out something cute and appropriate for you to wear.  Now don't be such a Sissy," my sister said while her friends giggled.  "Walnut is a quiet street.  Now get into the bathroom so we can fix you up."

I really had no choice so I complied.  And my sister was right -- Walnut was a quiet street.  I should be able to do this.

Well, the girls teased me mercilessly as they made me  strip down to my sister's bra and panties.  They  went to work on my hair and make-up and made me look really pretty -- much better than I had ever done myself.  Then they picked an outfit for me to wear.  The girls helped me dress and then ordered me into the car.  Now I stated to get nervous and I said that I had changed my mind.

"Too late, Sissy!" my sister snarled.  "Shut up and get in the car."

I started to cry as the girls shoved me into the back seat of the car.

A Sissy's Place is in the Home

Poor little Sissy Tina.  Three years ago I sold Sissy Tina to a Master who firmly believes that a Sissy's place is in the home.  So much so that Sissy Tina hasn't been allowed out of his Master's home since the day he was purchased.  In fact, Sissy Tina doesn't even own any real clothes -- just sexy lingerie to wear around the house!

And doesn't Sissy Tina look absolutely delicious in this lovely white ensemble? Sissy Tina's Master has purchased literally hundreds of exquisite lingerie sets for his Sissy.  White ones, pink ones, black ones.  Little baby doll nighties, heavily boned corsets, sweet little teddies.  And maribou slippers with four inch heels -- in colors to match every outfit. 

Sissy Tina doesn't even have any clothes to wear when his Master invites company over.  Sissy Tina has to parade around in his lacy and frilly undies while everyone ogles -- and fondles -- his very exposed and marvelously feminized body.  Poor Sissy Tina wants to die of shame.

And Sissy Tina's Master enjoys having his silky little Sissy perched on his lap.  Poor Sissy Tina has to just sit there obediently and perfectly still as his Master runs his big rough hands all over his Sissy's soft skin.  And Master also enjoys the fact that his little Sissy is also dressed for sex whenever Master is in the mood!

If you had a Sissy of your own as pretty as Sissy Tina, would you allow him to wear clothes in your house?  Of course not!

A Sissy Anniversary Surprise

Things had difficult at home for several months.  My wife had known about my interest in crossdressing for several years and had seemed pretty accepting.  However, recently she had been getting very annoyed about how much time -- and money -- I was spending on my crossdressing habit.  She said it was interfering with our relationship.  She insisted that I scale back on my crossdressing activities but I didn't listen.  But as our tenth anniversary approached, she seemed to relent.  As a peace offering, she gave me the most lavish nightgown set as my anniversary gift.  My present included sexy matching shoes, stockings, a sparkly necklace and a gorgeous new wig.  My wife even arranged for a make-up artist to come to the house who not only did my hair and face, but also managed to attach my breast forms in a way that made my cleavage look real.

 

At a few minutes before 8:00, I was ready.  I looked and felt so sexy and feminine and happy.  I turned the lights down low, lit some candles in the master bedroom and struck a sexy pose.  At precisely 8:00, as we had agreed, my wife knocked on the bedroom door.  "Come in," I said in a soft and sultry voice, my heart racing with excitement.

As my wife entered, she immediately turned on the bright ceiling light.  At first I was upset that she was spoiling the romantic mood I had created.  But that's when I saw that there was a tall and handsome man standing behind my wife.  I was paralyzed with shock. 

"Oh my God!" my wife laughed, "I can't believe my sissy husband is actually wearing that ridiculous get-up.  What a pathetic sissy faggot I married."

The man threw one arm around my wife's shoulder and started filming me with a video camera that he held in the other.  "How did you ever convince him to dress up like that?  This is the funniest thing I've ever seen.  Smile for the camera, Sissy!" he taunted.

"Oh believe me," my wife explained, "he doesn't need any convincing to dress up like a little sissy princess.  And now, Sissy, you can dress up whenever you want because now I have a real man to keep me company.  Maybe if you're lucky, someday you can get a real man too!"  They both doubled over with laughter when she said that. 

"Come on Sissy, do a sexy little dance for the camera.  I'm sure that would be a big hit on YouTube!"

Bedtime Sissy