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I Like Daddy And Sissy Boi Roleplaying

Personal Stories, Advice, and Support 591 People

    ...But I Like The Schoolgirl Uniform More Daddy

    As soon as the bell rings I run out the door of my classroom, and don't stop until I'm in at my front door. I run up the stairs and pause, sweating and slightly out of breath, and say to myself: I know Daddy won't be home till 6, so I can be a naughty little schoolgirl till then...
    schoolboy33 schoolboy33
    36-40, M
    4 Responses Aug 18, 2013

    Kaylee And Maksim

    Maksim' wife Kathy died five years ago, in an automobile accident. He was married to her for twenty years. When he lost he never thought he would love anyone again. Maksim found himself after five years of mourning, feeling lonely, and felt he needed to start looking for the...
    dad4sissybabe dad4sissybabe
    56-60, M
    7 Responses Jun 18, 2013
    FemGayBottom FemGayBottom
    31-35, T
    2 Responses Apr 25, 2014

    Met An Elderly Man In The Local Woods

    When I was a young sissy boy I met an elderly man in the local woods who persuaded me to accompany him to his home. When we entered his home he asked me to undress and to sit on his lap, naturally I followed his orders while I ******** off my clothes the man was enthralled at...
    mazeyj2006 mazeyj2006
    51-55, M
    Jun 23, 2013

    I had always loved a daddy.

    I learned to be a sissy because of daddies. I workout so my body is always tight and delicious for them. And I adore roleplaying with a rough daddy that knows what sissys are for
    Cutiefboi Cutiefboi
    18-21, M
    5 Responses Dec 25, 2013

    Hey there, I'm a 50 yr old Daddy in British

    Columbia , Canada who's looking for a small sized younger sissy boy for LTR. I am looking for a boy that lives in Canada that can relocate to live with me. You must be shorter then 5'6" , lighter then 140 lbs and naturally hairless.
    NanaimoDaddy NanaimoDaddy
    51-55, M
    1 Response Mar 18, 2016
    renobtmboi renobtmboi
    26-30, M
    Feb 6, 2014
    hellotherehs hellotherehs
    26-30, M
    Dec 7, 2015

    John was a relentless

    and constant trainer of Claire, the future sissy. And while John was approaching his late 50s, he was still a very sexy man. John smiles and picks up a pair of headphones. "I recently found out there are various videos on line that are supposed to be subliminal messaging to...
    amberdaniellejohnson amberdaniellejohnson
    46-50, M
    3 Responses Dec 4, 2013
    Joeycalvin Joeycalvin
    18-21, M
    3 Responses Mar 28, 2014

    Hey Boys :3

    Come on, Im young but Im exciting and submissive (; Im little, controllable, and willing to suck anything. You want a lil boi to have and own? I'm here, putting on my lipstick. Come have some fun ;3
    DoubleBBenson DoubleBBenson
    22-25
    4 Responses Jul 9, 2013

    Cinema Toliet

    I enjoyed my visits to the local Cinema the men that visited the Cinema in the afternoon usually frequented the Cinema for sexual purposes it always seemed to be safe enough because they only wanted to fondle ****, they would see me sitting alone then come and sit next to me...
    mazeyj2006 mazeyj2006
    51-55, M
    2 Responses Jun 23, 2013

    Do You Like Online Roleplaying With Dad ?

    53 y/o horny top man is here for online roleplaying .... check my profile and see what i like .... send me message pls
    dad4sissybabe dad4sissybabe
    56-60, M
    10 Responses Sep 10, 2013

    Late Night Telephone Calls

    Having late night telephone calls was a real turn on, over the years I experience a number of encounters with other sexually-active males who still kept in contact. I used to be called quite frequently in the early hours by men and boys who wanted to talk dirty while they...
    mazeyj2006 mazeyj2006
    51-55, M
    2 Responses Jun 23, 2013

    My Sissy Babe

    she is looking innocent but soo hoti like ******* her tight *** soo muchshe knows how to tease me  
    dad4sissybabe dad4sissybabe
    56-60, M
    5 Responses Jun 17, 2013

    Fascinated With Girls’ Panties And Knickers

    From the time I was very young, I've known I was "different". I was always fascinated with girls’ panties and knickers. I remember asking my mother when I was 9 years of age, that fateful question one morning; "How come girls get to wear such pretty underwear and boys gets...
    mazeyj2006 mazeyj2006
    51-55, M
    Jun 23, 2013

    Daddy!!

    I would love to find a hot Daddy to please and obey!! Please get ahold of me so I can be your good little girl!
    pitchick pitchick
    36-40, M
    9 Responses Aug 23, 2013

    Looking For A Daddy

    hey if anyones interested msg me on kik jesse1996a ;)
    jesse18 jesse18
    22-25, T
    1 Response Oct 25, 2013

    My Cam Babe (Pics)

    my sissy babe likes to dress and make shows for mewould you like to dress and make shows to me on your cam ?will you be my sissy babe like her ?
    dad4sissybabe dad4sissybabe
    56-60, M
    8 Responses Jul 8, 2013

    sissy boys are so cute.

    .dressed on cute panties...
    photousa photousa
    61-65, M
    2 Responses Mar 18, 2016

    Green Knickers

    My father was posted to Scotland for a short time so my Mother elder brother and I joined him. In Scotland in the ‘sixties it was quite common for boys to wear bottle green girl's knickers under their kilts. This was because those schools, for which the kilt was part of the...
    mazeyj2006 mazeyj2006
    51-55, M
    3 Responses Jun 22, 2013

    Daddy, I just got home from school

    and I'm doing exactly what you told me to do. I finished my chores and I'm waiting for you to come home from work. I'm wearing the nightie you told me to with no panties, lying on my bed. I want to play with my very wet *****, but you told me not to or else you'd spank me. You...
    DavidMc69 DavidMc69
    41-45, T
    Dec 8, 2013

    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764
    18-21, T
    1 Response Jul 23, 2014

    I am a sissy and would totally love to role

    play like this. I would love to do it for real in person. I live in Georgia south of Atlanta. Are there any daddy's looking for a naughty sissy to play with?
    SissySubAlyssa SissySubAlyssa
    36-40, T
    Mar 18, 2016
    dad4sissybabe dad4sissybabe
    56-60, M
    10 Responses Jun 21, 2013

    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 wouldn't know how to. I want (need...
    gwmbottomm gwmbottomm
    46-50, M
    Jun 12, 2014

    I've tried posting new stories

    but EP won't allow me to use certain words so send me a private message if you'd like to chat about my experiences being a molested sissyboy. 😊
    Joeycalvin Joeycalvin
    18-21, M
    7 Responses May 25, 2014

    Mr Schwartz And My Panties

    Abel Schwartz was a retired tailor; Mr Schwartz was 75 years of age, as you can tell by his name he was Jew widowed when he was 70 years old. Mr Schwartz had no children; his family perished in the concentrations camps Poland. I didn’t recall Mr Schwartz being regular in...
    mazeyj2006 mazeyj2006
    51-55, M
    1 Response Jun 26, 2013

    Rhys

    I was feeling horny and decided to ring one of those chat lines.  I showered and prepared and dressed in some fave lingerie, and put in a small butt plug.  I was only wanting to chat with a suitable daddy while ******* off. I gave my introduction line, which was something like...
    ajaylovesit ajaylovesit
    31-35, M
    5 Responses Nov 13, 2013

    Love it being treated like a girl told what to

    do and how to do it all for a real man to blow his load in me love being forced to do "things" kik me _whos_in_charge
    imyourguy imyourguy
    22-25, M
    2 Responses Jan 11, 2014

    Seeking My Sissy Babe

    hi all, i am a dirty, horny 53 y/o man who had a big ****.. i am a top man .... send me a message in here at EP or at yahoo pls ... my yahoo id is dad4hotbabe .... i like online roleplaying with sissy babes
    dad4sissybabe dad4sissybabe
    56-60, M
    8 Responses Jul 18, 2013

    My uncle makes me go pantyless under my super

    short skimpy frilly skirt. I feel so embarrassed & bashful when I feel a strong breeze up my skimpy little skirt.
    Joeycalvin Joeycalvin
    18-21, M
    8 Responses Feb 11, 2015

    Me And Dad'S Old Army Mate

    One weekend Dad’s old army mate sergeant Bob Perry rang my Dad, they’d not spoken for nearly 15 years, when I was about 14 we use to visit Uncle Bob, I use to sleep his two sons Larry and Mike 15-16, they were at that age when they started ************, I was their prime...
    mazeyj2006 mazeyj2006
    51-55, M
    2 Responses Jun 24, 2013

    It's been quite some time

    since I found one of those Daddies that simply understand my needs, my way of think, my sexual appetite and are able to handle it... Wish I knew more like that, like those who with just saying the right words make my whole body quiver in need.
    Cutiefboi Cutiefboi
    18-21, M
    Sep 26, 2015

    A Story From A Friend ... Terri This Is For You

    STORY FROM CARNAREBORN … Terri sat there, knowing that a lecture was coming, but not what or why. His Dad had called him in from the backyard to "talk to him about something."   "Well son, I guess you know why we're here." Maksim said, as he sat down on the bed a few...
    dad4sissybabe dad4sissybabe
    56-60, M
    Jul 12, 2013
    slavesindee slavesindee
    56-60, M
    Feb 25, 2016

    I Met Mike Who Was Desparte For Sex

    I met a man in the public toilets who was ************ himself while standing at the open urinal, I undid my jeans and lower them down for him to have a glimpse of my frilly panties, he was desperate for some **** fun. He was a married man separated from his wife and four...
    mazeyj2006 mazeyj2006
    51-55, M
    2 Responses Jun 28, 2013

    School Sports Master

    I hated sports in school every time I could get out of participating, I did, most of the time I managed to attend a music class, but on one occasion I failed to get out of the sports lesson, on this day Mr Evans the School Sports master made the class do a cross country run, I...
    mazeyj2006 mazeyj2006
    51-55, M
    1 Response Jun 24, 2013

    One More Pic Of Hers

    would you like to be a nice sissy like her and bend in front of me for my huge **** ?
    dad4sissybabe dad4sissybabe
    56-60, M
    15 Responses Jun 17, 2013
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