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Sissy baby boys
#1
By the time the boys had been staying with their Aunt for six months their hair had grown considerably, and they'd got quite used to being made to dress as girls.

What they still found so humiliating was being put into nappies under their nighties when they were put to bed.


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#2
There really is little quite so humiliating as being made to wear a nappy under a very short skirt or dress.
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#3
Mummy keeps telling you that you are a beautiful baby girl and now with the hormone treatment you are quite proud of yourself . Mummy has even got you a boyfriend babysitter .


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Angel A little bit of hanky panky does you good .  Angel
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#4
Did anyone ever have a male babysitter?

I didn’t, but when I was twelve my mother used to get one of our neighbour’s daughters to babysit me and my little sister. Sometimes she’d ask if it would be alright if her boyfriend came round too. My mother always said yes, even if I was being punished by being dressed as a girl or a baby.
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#5
(05-23-2018, 09:07 PM)Ali Wrote: Did anyone ever have a male babysitter?

I didn’t, but when I was twelve my mother used to get one of our neighbour’s daughters to babysit me and my little sister. Sometimes she’d ask if it would be alright if her boyfriend came round too. My mother always said yes, even if I was being punished by being dressed as a girl or a baby.
I have had quite a few male babysitters over the years . Some the boyfriends of female babysitters who would happily change and enjoy me under the supervision of the girlfriends . One i most remember was a couple of years older than me and had been brought up a girl by his lesbian mother . My aunt was having an affair with his mother and he/she was left to babysit me . He was very fem and liked to play mummy with me as baby but had no ploblem using me sexually as his little lesbian baby doll .
Angel A little bit of hanky panky does you good .  Angel
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#6
(05-23-2018, 09:07 PM)Ali Wrote: Did anyone ever have a male babysitter?

I didn’t, but when I was twelve my mother used to get one of our neighbour’s daughters to babysit me and my little sister. Sometimes she’d ask if it would be alright if her boyfriend came round too. My mother always said yes, even if I was being punished by being dressed as a girl or a baby.

Like Ali I didn't have a male babysitter, but I do have a fantasy of having one, which goes something like this.

I'm 17-years-old, but I have a mental age of a five-year-old. Normally I'm put to bed fairly early around six o'clock, except when my cousin Richard comes around. He's 12 and he's very advanced for his age. It was his mom who suggested he babysat me so my parents could have at least one night out a week. That being on a Wednesday evening.

Richard loves Star Trek:TNG, which happens to be on at the same time I normally have to go to bed, it's also on a Wednesday evening. Richard comes straight from school, does his homework and has his tea and then he settles down to watch Star Trek. As an extra treat and if I've been good, mommy lets me stay up and watch it with him. 

Of course, when the show has finished I have to get ready for bed or in my case my cot. Of course, I have a temper tantrum and mommy lifts the hem of my dress and smacks my diaper covered bottom. She's quite happy to let Richard change me and put me in my cot. As soon as I'm settled he puts up the side of the cot and then he reads me a fairy  story and then he puts on a CD of nursery rhymes. Mommy comes in and tells Richard she and Daddy are off for their night out. "You forgot this," she tells Richard. He takes the pacifier from her and sticks it into my mouth. As they leave a lullaby on the CD is played and very soon I feel a yawn coming on and I drift off to sleep sucking on my pacifier as I close my eyes.

I wake up a couple of hours later, Richard and mommy are standing over my cot. She asks him if I've been a good girl, he tells her I have. He calls mommy Evangeline, rather than aunt Evangeline. He says his mom has made me a new pink party dress and some rumba panties to go under it and over my diaper for my birthday which is the following Wednesday. Mommy suggests they give me a birthday party. Why not bring some of your friends, she tells him, I'm sure they'd love to meet your cousin Petunia. 

"Would like that Petunia?" Asks Richard, "they know all about you and that your my sissy baby cousin." I howled and  sucked on my pacifier as I did so. Richard looks at mommy and says, "look Evangeline I think Petunia needs her diaper changing."

"You know what to do," she tells him.

A week later, mommy shows my guests into the living room. Those who haven't seen me before are amazed when they see me sitting in my playpen wearing my new pink party dress. Richard switches the hi-fi on and then selects a CD and puts it into the player. Everybody looks at me when the song starts playing. Jake who is one of Richard's friends tells him he's never seen a real sissy before, "isn't she gorgeous?" he tells the rest of the party guests. Terry says he can't get over the fact I'm 18, "why she looks more like a three-year-old, who's a pretty girl then Petunia?" he says lifting my dress so he can have a squint at my pantie covered diaper.





Must end there, just had a call from mom to remind me about Star Trek. Oh well, it was great fun while it lasted.
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#7
That’s a lovely story!

Being seen dressed as a sissy or sissy baby by other children, especially if they’re younger, is exquisitely humiliating.
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