Sunday, July 17, 2011

A Sissy Gets Ready to Go Home

Charlie had been nothing but trouble for his poor Stepmother.  He had gotten involved with drugs and shoplifting and had gotten expelled from high school just too many times.  And around the house he was rude and obnoxious. 

Fed up with this nonsense, Charlie's Stepmother did the right thing and delivered her rotten stepson to me for some...improvements.

It wasn't easy and it wasn't quick.  But in a little more than two years, Charlie was gone forever and in his place was -- TA DA -- Sissy Charleen!  All it took was some hard work -- and some hormones, some surgery, some sleep and food deprivation, and lots and lots of beatings.  Sissy Charleen was now a quivering, submissive and totally obedient feminized girly-boy.

I enjoyed preparing Sissy Charleen on the day his Stepmother was coming to retrieve him.  Starting very early in the morning, I had the girls from the beauty parlor come over to give Sissy Charleen "the works".  First, a total (and I mean total) body waxing -- ouchy!  Then his hair was shampooed and put up in rollers.  While he sat under the hair dryer, the girls did his make-up and gave him a mani-pedi.  His hair was then brushed out and styled, soft curls piled on top of his little Sissy head.  Adorable!

Now, up until this point, little Sissy Charleen had no idea why he was being all gussied up.  As I zipped him into the cutest little pink dress, I explained that his Stepmother had come to take him home and that she was waiting right outside.  Well the little Sissy nearly passed out when I said that!  Sissy Charleen was terrified of being under the control of his Stepmother in his new feminized condition.  Sissy Charleen started to cry and begged me not to return him to his Stepmother.  I sternly instructed him to stop crying, lest he spoil his lovely make-up.  I then reminded him that no one cares what a Sissy wants and that he had best work hard to obey and to please his Stepmother-- or there would be trouble. 

I stepped back to look Sissy Charleen over one last time and to admire my work.  His arms and legs looked so delicate and feminine.  His hair and make-up were perfect.  And the dress I had chosen was simply lovely -- so sweet and innocent.  I adjusted the pretty bow at the neckline, gave him a little hug and said good-bye.  He stood there, so prim, so feminine, so terrified, as I invited his Stepmother to enter. 

As she walked into the room and saw her transformed Sissy stepson for the first time, she screamed. "OH MY GOD!"  She nearly collapsed with laughter as she drank in her little Sissy.  Of course Sissy Charleen was dying of humiliation, but he stood there, eyes lowered, as he had been trained.  The Stepmother eyed Sissy Charleen's bust and asked aloud, "Are they real?"  She brazenly walked up to Sissy Charleen and gave his boobs a rough squeeze.  "OH MY GOD!" she screamed again.  "They are real!"  Her riotous laughter resumed.

"Come along, Sissy Charleen.  Time for us to go home.  But first we're going to go downtown so all of your old friends can get to see the new you!"


  1. I am always soooo happy when you post a new story! Love this one so much.
    Jackie Rose

  2. one of the besy you've done love the depth and detail and the total feminization

  3. oh beautifully written!!!!

  4. Sissy Charleen looks so cute and pretty some of her old friends are likely to hit on her.

  5. This one worked especially well! I love the look on his face.

  6. Dear friends
    I am a new cross-dressing boy, I would like wear panty and corset, but my girlfriend cannot accept me in this role,
    If it is possible tell me about your cross-dressing experience
    Many thanks

  7. hi linda. i read all your sissy stories. do you just transform young males. who can get one of theses beauties. im interested...

  8. linda.. i love all your stories. excellent... thank you... jeff

  9. i just love that story linda. excellent how you explain charleen in depth. keep up the great work. jeff