Rotten Stepson becomes a Perfect Sissy

When I decided to have my stepson transformed into a feminized, obedient Sissy, I had no idea where this would lead.  Mostly I was sick of his rude behavior, his back talk and his laziness.  It was such a relief when I had him sent away for his year-long transformation.

When I first brought him home I was totally amazed by his transformation.  Physically he had been completely changed.  He was now a pretty, delicate, completely feminine little Sissy.  His hair was long and had lovely coppery highlights.  He had lost twenty or thirty pounds -- maybe more -- and was developing the sweetest little breasts.  Everything about his body and appearance was now so girlish.  But his physical transformation was nothing compared to his mental transformation.

He was now utterly and totally obedient to me.  He seemed to have no desire other than to please me. He was such a delight to have around the house.  He needed no instruction to keep the house spotlessly clean, to prepare my meals, make my bed -- everything!  I let him help me dress and undress me and even bathe and massage me. He would never speak unless spoken to.  When I would enter a room, he would stop whatever he was doing, lower his eyes to the floor, and curtsey to me.  It was marvelous.

But over time, I developed a strange attraction to my litle Sissified creation.  He was so devoted to me and took such good care of me.  I soon started to enjoy my Sissy in more...intimate ways.   I had my little Sissy joining in my bath and in my bed.  I enjoyed running my hands all over his soft little body.   I enjoyed pressing his naked body against mine, letting him play with my big boobs while I played with his tiny little titties.  And best of all, I loved feeling his sweet little mouth and tongue on my pussy.  I hadn't realized how thorough his training had been!

Who knows?  Maybe I'll get my Sissy stepson some big sexy breasts so he can be more like me.  I bet he'd like that!

Helpless Sissy Love Doll

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Sissy Goes Outside Part 5

For the last few weeks, I've been with Dick every possible minute.  We spend hours in his apartment where he lets me suck on his cock and please him in other ways.  I love making him cum!  It makes me feel alive and valuable to know that I'm giving my Man the pleasure he deserves.

And now we go out together at night too, several times a week.  We go to the movies and bars and restaurants.  It is so exciting to be the feminized Sissy possession of a big strong man.  I love spending my afternoons making myself pretty for Master Dick.  And I love spending my nights being kissed and fucked by him.

I am working so hard to make myself more feminine and sexy for Dick.  I've been dieting and lost seven pounds.  And I've started taking my sister's birth control pills.  The pills have already started making my skin softer and prettier and my nipples have become very swollen and sensitive.

Dick is nice to me almost all the time.  But sometimes I disappoint him and he has to punish me.  I understand.  It is important that I learn to be a perfect Sissy and to always please my Master.  Sometimes Master Dick has to spank me if I have failed him in some way.  He seems to like spanking me, especially if we are out in public.  I am very grateful to my Master for helping me to become a better Sissy.

Master Dick had told me that he had "special plans" for tonight. So I stole this elegant outfit and strappy I I wanted to look my best for my big night with Master Dick, so I borrowed and pretty lacy outfit and sexy strappy shoes from my mother's closet. Then I spent most of the afternoon at the beauty salon and had the girls give me "the works". They even gave my hair some pretty highlights.   I feel so beautiful and feminine!  Dick almost fainted when he saw me!

Dick had made reservation at the fancy French restaurant overlooking the river.  It was all so romantic!  And then, as we were waiting for dessert, Dick got down on one knee.  The whole restaurant went silent and everyone was watching us.  Then, Dick pulled a ring from his pocket and said loudly enough for all to hear, "Will you marry me?  Would you be my Sissy Wife?"

"Oh yes!  Yes!" I exclaimed.  "Of course I'll be your Sissy Wife!"

The people in the restaurant clapped, although they seemed a bit confused by what they just saw and heard.

So now I am going to be married to my Master Dick, who I adore and worship.  I will be able to dedicate the rest of my life to pleasing and serving my Master/Husband.  I am so happy!

And it is all because my sister and her friends caught me dressing in her clothes just a few months ago.  What a lucky Sissy I am!

Sissy Goes Outside Part 4

Something strange happened last Friday when I went over the Tasker brothers' house.  I wore a pretty dress and did my make-up like always.  I arrived as instructed at 4:00 sharp, and after posing for some photos and scrubbing the toilets, I readied myself for Dick and Ben to start fucking me, using me as their Sissy sex toy.

Dick, who always fucks me first, told Ben that he didn't need any help holding me down.  He told Ben to "get lost" until he was done with me.  Ben seemed confused at first, but eventually left Dick and me alone in the bedroom.  Dick pushed me down onto the bed and climbed on top of me.  Then he started kissing me -- a lot -- on the mouth, on my face, on my neck.  Instead of holding my wrists down he told me to wrap my arms around him.   Then he slowly pushed his giant cock inside my lubricated bottom and started to gently pump it back and forth.  He had never had sex with me like this before.  It didn't even hurt very much this time.

And after he came inside of me, he kept his cock inside of me for a long time and started kissing me again.  Then he whispered, "You are so hot," in my ear.  For some reason I suddenly felt warm all over when he said that.

Then Ben started banging on the bed room door, shouting, "Hey, hurry up in there!  It's my turn!"

At first Dick just kept on kissing me, trying to ignore all the noise his younger brother was making.  But after a few minutes, Dick leapt out of bed and swung open the door.

"About time!" whined Ben.  "What the hell have you been doing in there?"  Ben started taking off his shirt as he headed towards the bed I was lying on.

Dick grabbed Ben's arm and said, "It's not your turn.  I'm not sharing him any more.  He's my Sissy now.  Only mine.  So get lost."

Well, Ben went nuts when his older brother said that and they started fighting.  I wanted to get far away from this fast, so I grabbed my shoes and my purse and left. 

Later that night, Dick called me on my cell phone and told me that I would be spending afternoons only with him from now on.  He said that he was going to move out of his house and start subletting a friend's apartment downtown.  Dick said that I was to meet him there every afternoon at 4:00.   So on Monday afternoon, I did as I was instructed and met Dick at his new apartment.  

Here are some pictures of me that Dick took on the balcony.  I'm wearing a pretty blue dress from my sister's closet and a purse and shoes from one of her friends.  I spent extra time on my hair and make-up because I really wanted to look nice for Dick.

When Dick saw me he told me that I looked "really pretty" and kissed me.  He took my hand and led me inside.  He sat down on the coach and told me to sit on his lap.  He started kissing me again and running his hands all over me.  "You are so sexy," he panted into my ear.  It made me feel a little dizzy when he said that.

After a few minutes of making out on the coach, Dick told me to go down on him.  I slid off his lap and got on my knees between his legs.  I undid his belt and his pants.  Once freed, his enormous cock sprank to life.  I held his rod with one hand and started licking it up and down.  I know he enjoyed that.  I then put his stiff cock in my mouth and started sucking on it.  Dick wasn't forcing me to do anything.  I was trying my best to please him.   I used my hands and lips and tongue to drive him into a frenzy.  When he started to cum, I made sure that I swallowed every drop.

Later Dick carried me into the bedroom and gently made love to me.  I moaned with pleasure as Dick's big tool slowly worked itself in and out of my bottom.  After Dick came inside me, we just lay together in bed, my head resting on his broad chest, his big arms wrapped tightly around me.  I felt so safe and warm.  And I felt so happy knowing that I had pleased my man so completely. 

Sissy Goes Outside Part 3

It's been two months since my sister and her friends set me up to be caught by the Tasker brothers when I walked in front of their house wearing my sister's clothes.  My life has been a total nightmare ever since.  The boys make me come over to their house every day after school.  My sister thinks it's funny and that I'm getting what I deserve for being such a Sissy.


On that first day, after the boys had dragged me inside, they told me that I was now their "little Sissy sex toy."  They said that I had to do everything they told me to do or they would kill me!  Well if you had ever met either of the Tasker brothers, you would believe their threats.  And for the next two hours they took turns raping me.  One would hold me down while the other would have sex with me.  It felt like they pumped a gallon of cum in my bottom.  When they used my mouth, they forced me to swallow their hot, sticky cum.   It was horrible -- but there was nothing I could do about it. They were both so much bigger and stronger than me.  I was trapped and completely helpless.  I was crying the whole time, begging them to stop -- but they ignored me and just kept fucking me, over and over, like a pair of wild animals.


After a couple of hours they started to get tired and bored, so they told me to get out.  But first they told that I had to come back every afternoon.  They told me to be at their front door at 4:00 sharp and to "look real sexy."  And they also told me that next time I better not be such a "Sissy crybaby."

So everyday, as soon as I get home from school, my sister helps me with my make-up and clothes before driving me over to the Taskers' house.  She teases me saying things like, "What a lucky Sissy you are to have two boyfriends," and "You are such a Sissy slut!"  She's given me some of her old dresses and underwear -- and her friends have contributed some old clothes to my new wardrobe as well.  I try very hard to look pretty, because I'm worried that the boys will get angry with me if I don't look nice.  My hair is now a bit longer and I think I am getting better at looking like a real girl.

Now when I go to the Taskers' house, I arrive by 4:00, as instructed.  I stand on the porch until one of them, usually Ben, the younger one, opens the door.  If the weather is nice, Ben makes me pose for photos before he lets me inside.  This is a picture that Ben took of me today on the same sidewalk where they first caught me two months ago.   I'm wearing a dress that my sister bought at Goodwill for me and a pair of shoes from one of her friends.


Recently, they've started making me do chores around their house before they start having sex with me.  Today I had to wash all dishes in the sink and do some laundry before the brothers decided it was "play time" and started taking off their pants.  I've become their sex slave and maid, all in one!

A Sissy's Passage to India

Sissy Kismet was one of my bus depot runaway finds. He was young, small, alone and desperate. Just perfect for me!

I had an outstanding order from an Indian textile billionaire.  He had given me very precise specifications but I just couldn't find the right raw materials to make the Sissy wife he wanted. He also had a practically unlimited budget, so I was motivated not to disappoint this client.

Just as I was about to give up hope, I stumbled upon this perfect little sissy-to-be. It was easy to lure this frightened, exhausted little runaway back to my home where I could perform my feminization magic.

Within 24 hours, my latest acquisition was begging to be returned to his wretched life as a hungry bus depot runaway -- anything to escape the horror of his forced transformation.  I had to do a rush job.  My Indian client wanted to take delivery in just seven months so I pulled out all the stops.  Little Sissy Kismet's life became a non-stop, 24/7 exercise in extreme feminization.   I used massive dosages of hormones, some quick surgeries combined with brutal behavior modification training to perform the rapid transformation.

In preparation for my client taking delivery of his new young Sissy bride, he had purchased a traditional Indian wedding outfit -- complete with a long silk sari, veil and jewelry -- and had it shipped to me.  On the day my client came to inspect his new possession for the first time, I dressed the precious little Sissy in his wedding dress and jewels and carefully did his make-up to make him look both exotic and innocent.  I was delighted with how he looked.

Poor Sissy Kismet was in such a panic waiting for his new Husband and Master to arrive.  The pathetic little thing was literally quivering with terror.  But things really started to be fun when my client arrived.

My rich Indian client was repulsive.  He was a fat, disgusting brute.  He even smelled bad.  But when he first laid eyes on Sissy Kismet, I could tell that I had exceeded his expectations.  As he walked around his Sissy bride, inspecting his purchase, his excitement mounted.  The Sissy just stood there, motionless as he had been trained, his eyes looking down to the floor.  The disgusting businessman gave his Sissy's ass a firm squeeze.  He reached one massive hand down the front of his Sissy's sari, roughly feeling the Sissy's tiny but growing breasts.  Sissy let our an adorable little yelp when that happened.

The businessman started to unbuckle his belt and unzip his pants, but I stopped him.  "Oh no!  You can't do that yet.  Not until you've paid!"

"Fine." the businessman grumbled.  "I'm late for a meeting anyway."  He re-zipped his pants and picked up the briefcase he had brought with him.  "Here," he said as he handed me the case.  I opened it.  Inside were stacks of hundred dollar bills.  My full payment in cash.

"Deliver him to my private plane in the morning," he said to me.  And to his lovely little Sissy he said, "And when we arrive in India, you and I will be married.  Won't that be wonderful!  You will be my little Sissy wife and slave for the rest of your life."