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I Like Online Roleplaying With Sissy Bois

Personal Stories, Advice, and Support 299 People

    Makism, Dana And Jimmy .....

    Maksim suspected his 19 year-old son Jimmy was stealing money. Maksim worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror...
    dad4sissybabe dad4sissybabe
    56-60, M
    1 Response Jun 9, 2013

    Young Shop Assistant

    When I was 17 I had a part time job in a man’s and woman’s clothes shop, it was an old established business run by an elderly bachelor and his spinster sister Mr and Miss Gibe. The customers who frequented the shop were unusually mature people, the styles and apparel...
    mazeyj2006 mazeyj2006
    51-55, M
    2 Responses Jun 25, 2013

    RP only I would love to rp with a sissy.

    I kinda want to do one where I force you into being a sissy and you find out that you like being my sissy. Let me know if you want to do this one with me
    MistressSadie MistressSadie
    18-21, F
    2 Responses Feb 6, 2015

    Dream Of A Little Boy

    Dana Bigload paced restlessly around his father's master bedroom, glancing at the clock every two seconds. The ten-year-old, blonde haired sissyboy wore nothing but white leggings. His young **** was semi-erect and wet at the tip. His young balls, full of ***, swung freely...
    dad4sissybabe dad4sissybabe
    56-60, M
    2 Responses Jun 4, 2013

    My Friend Paul

    I used to sit next to a boy in school called Paul, I got on very well with him though he was a very effeminate in his mannerisms, Paul was funny and amusing to be with, boys like Paul were called “Pansies”, but Paul had the attitude he couldn’t have cared less. The older...
    mazeyj2006 mazeyj2006
    51-55, M
    Jul 5, 2013

    Any Top Daddies For Sexting, Email, Chat Or Phone?

    I miss the chat rooms from gay.com. There used to be tons of Top Daddies into cyber and phone, but alas, those days seem to be gone. I have a big 'crush' on Daddy (or Uncle or Neighbor) and want him to seduce me. I'm shy and am too afraid to make a move myself. Besides, I...
    gwmbottomm gwmbottomm
    46-50, M
    Sep 21, 2013

    Amy

    Amy had been feeling rather down the past couple of weeks. I'd been busy and hadn't had much time for her lately. So I thought I'd plan a little surprise for her this coming weekend. I'd meet someone that knew some very young girls that would do anything they were asked to do. So...
    deleted deleted
    26-30
    1 Response Jun 28, 2013

    AMY Part 3

    I told the girls to take a short break. I gently take Amy's head in my hands and title it up. 'You know we're only half way.' 'Yes sir, I'm fine' Wiping the tears from her face and soft kiss on the cheek. I wisper 'your a good lil sissy and your mine.' 'Thank you sir, and yes I...
    deleted deleted
    26-30
    Jul 1, 2013

    Dana .. And Demi

       Maksim W. was a bit upset when he got home from his business trip that Friday night. He had specifically told his wife Cheryl that their son Dana was grounded for one week. One entire week. A week that wouldn't end until Sunday.   "Dana's in his room with some...
    dad4sissybabe dad4sissybabe
    56-60, M
    1 Response Jun 4, 2013

    I'm A Sissy Schoolgirl Looking...

    As I type this, I'm sitting here in my schoolgirl uniform. Pleated plaid kilt, white blouse, knee high socks , sleeveless school sweater and school tie. I dress like this every chance I get. I love dressing like a little schoolgirl, I feel so slutty & submissive when I do...
    schoolboy33 schoolboy33
    36-40, M
    1 Response Nov 28, 2013

    Seeking My Online Sissy

    hi all, i am a dirty 53 y/o top man , i am 6’5’’ 220 lbs, blue eyes and dark hairs … i like chatting and online roleplaying ... i hate rape and bdsm scenes ... for rest .... my yahoo id is dad4hotbabe@yahoo.com, but we can play here on EP too…  please don’t...
    dad4sissybabe dad4sissybabe
    56-60, M
    1 Response Jun 6, 2013

    The Day At The Office

    I'm working as a secetary and I am your secetary, as far as you know I'm a beautiful woman until one day you see me fall and my skirt show more than needs me a black lace thong with the smallest buldge of a penis
    cassiey116 cassiey116
    18-21
    3 Responses Jun 17, 2013

    Sissy Babe Pics That I Like - 4

    i like her soo much ... would you like to see more of hers ? and pls tell me what do you think about ther
    dad4sissybabe dad4sissybabe
    56-60, M
    7 Responses Jun 13, 2013

    Sissy Babe Pics - 2

    i like this sweety soo much ... one of my fav sissy babesdid you like this cutie too ?
    dad4sissybabe dad4sissybabe
    56-60, M
    6 Responses Jun 5, 2013

    Im Looking For Daddy

    im looking for a daddy to please if anyone wants to chat add me on kik jesse1996a im sure we would have lots of fun ;)
    jesse18 jesse18
    22-25, T
    1 Response Oct 26, 2013

    Who Likes To Dress Like This And Play With Me ? (Pics)

    she knows what she is and what she wants ....... do you know your place and what you want ?will you show your ***** like she did and invite daddy for ******* you ?
    dad4sissybabe dad4sissybabe
    56-60, M
    9 Responses Aug 7, 2013

    Hey

    I became a sissy in prison
    richie82 richie82
    22-25, M
    Aug 3, 2013
    dad4sissybabe dad4sissybabe
    56-60, M
    7 Responses Jun 15, 2013

    Sissy Babe Pics That I Like

    i want you babe
    dad4sissybabe dad4sissybabe
    56-60, M
    3 Responses Jun 4, 2013

    AMY Part 2

    As they headed toward Amy I got a chair and set down just a few feet in front of her, but out of the way. The girls circled around her like tie cats around a mouse, dragging thier claws on her and snapping the scissors as they went. Taunting her as they went. Kim reached under...
    deleted deleted
    26-30
    Jul 1, 2013

    Any Online Yahoo Players ? (Pics In)

    hi all, i am a dirty 53 y/o top man , i am 6’5’’ 220 lbs, blue eyes and dark hairs … i like chatting and online roleplaying ... i hate rape and bdsm scenes ... but all for rest are ok for me  .... my yahoo id is dad4hotbabe@yahoo.com, but we can play here on EP too...
    dad4sissybabe dad4sissybabe
    56-60, M
    12 Responses Jul 24, 2013

    Sissy Babe Pics - 3

    this babe is a real teaser
    dad4sissybabe dad4sissybabe
    56-60, M
    6 Responses Jun 8, 2013

    I Need Help With This Story

    I want any man or Daddy who will continue the story I will only choose one My name is Cassiey and I just ran away from home because of a fight. They came home early and seeing that I'm a crossingdressing sissyboy dressed as a female hooker. I run down the street take two...
    cassiey116 cassiey116
    18-21
    2 Responses Jun 6, 2013
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