First Date: Last Day Of Boyhood [repost]

 

“Don’t worry Olivia, I’ll keep your lil brother busy all day while you get rid of all his boy stuff get his nursery set up and his Nanny gets prepared for his return to pampers. We’ll have so much fun I’m gonna give him a great last day of boyhood even though it will be a bit juvenile for an 18 year old. Sad to think this is first ever date and it’s a total set up” Isabella the mischievous alt girl said with a twinkle in her eye.

She was taking Donald, Olivia’s dork younger brother, and supposed now head of the family, who had indeed never had a date to the funfair to keep him out of the way. 

While his life as male and an adult was being ended forever.

“One thing when you show him the lovely pink nursery, all the party frocks and he meets his big strict Nanny is it ok if I stick around and watch that? don’t think I’m a bitch or anything but that really turns me on. I guess I have a Sissy crying fit fetish lol.”

Olivia and Donald had a great day at the funfair she even bought the skinny little bitch hot dogs and ice-cream, which she insisted on spoon feeding to him whilst passers by giggled. He’d never have food like this again when he went on an all babyfood and soy formula diet.

She could see that he wouldn’t be much of a challenge for any sissy baby nanny, he shrieked like a frightened bitch on all the rides, got a hopeless score on ‘Ring The Bell’ before Isabella slammed it winning her boy a big pink stuffed bunny rabbit to snuggle at night. He looked really embarrassed carrying the huge stuffed animal, as people snickered.

He was so weak and adorable she even gave him a handy in her car, why not she had ten seconds to spare.

The hopeless Donald there and then told Isabella he loved her.

“Awww Donnie your sweet but we got to get you home your big sister worries about you, little pixie boy! I love you too but not in a boyfriend way”

The new Nanny sure was formidable and the hurt betrayed look on Donald’s face was exhilarating, Isabella knew what she would fap about that night. 

He was crying and throwing a tantrum as his new life was laid out and he was shown his all little girl going to a party wardrobe.

Isabella continued to help bitch out boys to pay her college fees but despite her busy lifestyle made the time to attend Baby Rosie’s one year as a little baby girl anniversary party. There was a giant cake with one candle and ‘Legally Incompetent’ iced on it.

Sitting him on her knee as she reminisced about his wonderful last day of boyhood. “You were hopeless as a boy but you a just a peachy bundle of joy as a sissy baby girl, no way would all these popular girls, the jocks, gay guys and basic bitches attended a party you threw back when you thought u were a boy. I’ d love to give you another handy but your Nanny says you are totally limp. We’ll see about that if they let me change your diaper!”