Sissy Steve and Me Ch.3


Ch. 03: Outside in a Dress

When we finally got our dresses on, we then modeled them for each other looking for flaws (and giggling) before we showed Karen.  Going into the living room we called Karen in to give us her approval.  Entering she stopped, looked at us, and placing her hand over her mouth she started giggling, then regaining her composure she said ‘wow boys, you’re both beautiful’.   Just a bevy of pretty little girls you are.  Then she asked ‘what are your plans for today my honeys’?  We thought a moment then I said ‘I guess we’ll just stay inside and play with dolls.  You know just girlie stuff’.

I’ve got a better idea boy’s, it’s a beautiful day, why don’t you play outside, and all you have to do is change your shoes.  Spike heels are no good on grass.  We both let out a ‘gasp’ at that.  We had thought about doing just that, but that was way in the future.  Oh come on boys you can play in the back yard, feel the breeze up your dress and it’ll be fun.  Reluctantly we followed Karen outside, both of us hanging our head in shame, and Karen laughing and talking loudly ‘see there’s only one house that can see back here, so your secret is safe’.  Oh No, I thought, the Browns, our neighbors, can see the entire yard.  I tried to think of an excuse not to go out, but it was such a nice day, I couldn’t.

Then, a flash of inspiration, I stammered ‘But Karen, what will we do out here, we don’t have any toys’. Karen thought for a moment then said ‘how about some dolls boys, I’ll get some and bring them out to you.
Oh please do Karen and some extra clothes so we can change them, that’ll be fun.  Stephaney and I talked when Karen left and we made ‘girlie’ plans for the next week or so.  When Karen returned she had a half dozen dolls, everything from ‘bridal’ to ‘ballerina’, saying I hope these make you happy,  Oh yes Karen, thank you.

Then she added ‘oh, by the way boys, I gave them a haircut (giggle, giggle).  Then we looked closer and saw that they looked a lot like us.  We snickered and thanked her again, expressing our love for her.
Stephaney grabbed the wedding doll (with a huge bell petticoat that he loved, and really wanted) and of course I got the ballerina (that was my favorite….. oh I wanted to have a tutu like that).  You boys are so sweet setting there with your dolls, playing so nicely, I got you a special present.  That got our attention and we said in unison ‘what’d you get us Karen?  Let us see.’

Returning in just a moment, hands behind her back, and a huge smile, she asked ‘now which of you is the best little girl ever.  Which of you is the most ‘prissy’, the most ‘sissy’, and the prettiest little girl in the yard (giggle).  Karen was having fun with this and we realized she was just teasing so we went with it.  Then she asked ‘Who wants to be ‘Super Girl’ (tee-hee).  ‘I do’ we both screamed like sissy little girls.  After a moments thought, Karen handed the ‘Super Girl’ doll to me, saying sternly ‘now be good girl and share honey (giggle)’.  ‘Oh I will Karen’ I said with an evil smile (tee-hee).

In just a moment I was deep in a sissy trance where I was super Brenda, with my super short skirt and super cape, stopping bad boys who were calling me names and giving them a good ‘spanking’.  The ‘bad’ boys would soon learn to run from ‘Super Brenda’, and little girls would cheer me as I went by.  They all wanted to be me (giggle).  I was smiling in my own super world when I heard it, a low chuckle from behind the property line bushes, and my heart stopped beating.  It sounded like a little girl. It had to be Patty, our neighbor.  I yelled out ‘come out Patty, i hear you’.  Patty yelled back ‘Can I play ‘dolls’ with you Brian, ‘I’ll bring my own over’?  Don’t worry it’ll be fun boys (tee-hee) and I won’t tell.’

Now Patty was well developed, she was my age and the first girl in my class to wear a bra.  Stephanie said, in a panic ‘No Brenda, she’ll tell everyone’.  Might as well let her see what we’re doing Stephanie, it’s already too late.  And so it began…………..


  1. Very cute and innocent! :)

  2. There's 7 more chapters Annabelle hasn't published yet. Let me know and I'll send them to you.

    1. I am enjoying reading "Sissy Steve" and would be grateful if you could also send me the seven as yet unpublished chapters. How can I contact you privately so I can give you my email address? Thanks.



  3. Dear Dave, sorry it took so long to get back to you and as you probably already know Annabelle has at last almost caught up. But if I can be any help just let me know. Love, Brenda

  4. Hello Brenda,

    Thanks for your reply. I was bit confused at first because the title of the story has been changed from chapter 4 onwards, to Mommy's Little Sissy! Now that I've found the stories, all is well.