Saturday, October 27, 2012

Mother and her Sissy Son Plan a Trip

"But mother," Eric protested.  "I don't want to dress up like a girl!"

"Oh, not this again," mother replied with a sigh.  "Stop your fussing and let me see how you look in the blue dress.  Hmmmm.  That's very cute on you.  The skirt has a pretty flare.  Now hold the skirt out like you're going to curtsey."

"Marvelous!" she exclaimed as she took another photo.  "That dress will be perfect for when we go shopping in New York City next weekend."
"But mother, PLEASE!" he said.  "Why do I have to be dressed as a girl when we go to New York?"

"As I've told you a million times," mother replied impatiently, "You are going dressed as a girl because you are much too pretty to be a boy!  And besides, a mother/daughter trip will be such fun!"

Ever since Eric had been a little boy, his mother enjoyed playing dress-up games with him.  He didn't mind too much.  In fact he even enjoyed it.  But recently, mother had been insisting that Eric spend more and more time dressed up as "Erica". 

"Now try on the black one with the spaghetti straps," mother instructed.  Eric did as he was told.  He didn't have the spine to stand up to her.  And deep inside, a small part of him enjoyed being feminine.  But things really were beginning to go too far, he thought.

He slipped on the little black dress and his mother zipped him up.  "Oh my!" she squealed.  "That is just ADORABLE on you.  Turn around and let me see.  Oh yes.  You are simply lovely in that! That will work for going out to nightclubs.  You will certainly get a lot of attention looking like that!" she teased.  Eric hated it when she said things like that.

Eric started getting angry.  "And I hate wearing my hair like this!  I look so...girlish all the time.  All of the boys at school make fun of me.  And they can tell that I shave my legs when I go to gym class."

"Oh don't pay any attention to those silly boys," mother said dismissively.  "Sweetie, that's the way teenage boys get when they see a pretty girl and start getting...excited."

"MOTHER!" Eric shrieked.  "I'm not a pretty girl!"

"Hush now," mother replied calmly.  "Don't be silly.  You are very VERY pretty!  Now try on the long sleeve wrap dress."

Again, Eric complied.  He was too much of a sissy to fight back. 

"Oh my! Oh my!" mother said.  "You look so sophisticated in that dress."  She had Eric put on a pair of black lacy stockings and she slipped a necklace around Eric's neck before taking some more photos.  "That dress will be perfect when we go out to dinner.  I made reservations at some of the best restaurants in New York while we're there."

Finally mother had Eric try on vintage black dress with sheer sleeves a feathery trim around the neckline.  It was a beautiful, exquisitely feminine dress.  Mother took several photos and purred, "Oh Erica, darling.  That dress is just heavenly on you.  You look so beautiful."  At that moment, mother decided that Eric would wear this dress to his interview at the New York Sissy Academy.  Mother desperately wanted Eric to attend their famous one-year "Total Conversion" program so she could at last have the daughter she always wanted.  Eric didn't know anything about this part of the weekend plans.  But Mother was so confident that he would be accepted to the Sissy Academy that she had only purchased a one-way plane ticket for her Sissy son.


  1. Oh yes, she looks simply delicious in all the dresses, but the last is a pure delight

  2. Love the pictures. Please continue. Can't wait to see how she or he looks after attending that school.

  3. This sissy would loved Mommy to have been playing dressup games with me cos like Eric i secretly enjoy it even if i might thought sometimes it was going too far but spineless enough not just let her have the final say. i'd of loved to had been forced to wear vintage black dress even if i'd of no idea what else you had in store for me.
    looking forward to finding out what happens next on the trip to NYC.

  4. Exquisite ! Lovely story of mother-girlyboy trip.

  5. Poor Eric, soon the last signs of masculinity will be forever erased from him and he'll be forced to live as a sissy the rest of hur life! Mmmm.


  6. My mother enjoyed dressing me up as did my older sister ever since I was 11 years old. We would take trips regularly. As I got into my later teens years I asked my mom and sister when we could go out. Seeing the smiles on their faces as I asked to dress and go out with them was priceless. Today mom is gone but my older sister enjoys taking me out.

  7. What a great sissy story!" I can't wait too do this on my pantywaist sissy for a long, long time!" Jennifer A.

  8. oh boy i so want the dress and that academey sound interesting

    1. Hello L.D. I would love too turn you into a pantie-waisted-bitch? Kaley C.