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Turned into a sissy, the start.

How I started as a sissy.

We met on line and I invited her over so we could meet. She showed up at eight on a friday evening, she was tall and thin with a great chest. I invited her in and we talked for about an hour then went down to the local bar for a drink. Once we finished at the bar we went back to my place around ten thirty. I figured she would be leaving but once we were in the house she asked if she could stay over. Naturally I said yes, and I showed her the gust room. She asked if I was kidding and I asked what did she mean? Her reply was I did not drive all this way to sleep by my self. I showed her my room and she stripped off her closes down to her ** and bra, then went to the bathroom to clean up for the night. I was shocked at how open and forward she was. I had never been with some one like this before.

I was in the living room kind of weighting for her to go to bed then I was planning on joining her. She came out of the bathroom and came straight to the living room. Standing in front of me she asked if I was going to come to bed now? I stood up and followed her to my room. She sat on the edge of the bed as I took off my cloths down to my under wear which were a skimpy string bikini for men. Oh so your a sissy ** wearer are you she asked? I looked at her and said no their for men, she smiled and said too bad you would make a nice sissy. I was shocked at what she had said and took of my underwear as she took off her bra and her large ** bounced free. Wow their nice I said! She took off her ** and asked how I liked her shaved **. It looks great to me I think you have a fabulous body. She smiled and clime into bed. We enjoyed each others bodies and had a very good night for a first meeting!

The next morning I got up to get dressed and she lyed their on the bed watching me. I put on a regular pair of tighty whites as to not get accused of wearing ** by her. She said that she liked the ** I had on last night better. She did not care for the tighty whites and told me to put the others on. I was taken by surprise once again by her open and boldness. Sure I have a different pair which I put on then finished dressing. I went out and made some coffey and she came out naked, sat down at the table and we drank coffey as we talked. She told me how she had a dominate side and likes to use it. She could see I kept looking at her big ** and asked how I liked last night? It was great I said, I think you have a lovely body and I enjoyed it very much. She then asked if she could spend the rest of the weekend with me? Of coarse I said with delight knowing it was going to be a fun sexual weekend.

That after noon she said she was going to run into town to pick up some things. I asked if she wanted me to go with her and she said she wanted to learn the town on her own but would be back in an hour or two. She came back with a bag of groceries and a bag that I figured was her things she needed. She made the meal that evening and we both did dishes together. She talked about her past some and her parents. When we were completed she asked me to go to the bedroom with her. I was thinking that ** was starting early tonight and it would be a long night, smiling I said sure.

Once in the bedroom she took off her tops reveling her large ** and said. I have something I hope you will like and accept with out making a big deal out of it all. Then pulling out a couple pair of lacy **, garter and nylons. Holding them in front of me she told me that she wanted me to try them on! I was surprised and some what confused by what she was asking. What I asked? I would like for you to wear these today come on I will help you in them and you can do what ever you want with me. I was still in shock when she pulled my shirt over my head and pulled me to my feet. She dropped my jeans and told me to step out of them as she pulled down my under wear. Still confused she started to ** my ** at which I came back to my senses. She stroked it and sucked it until it was hard then stood up dropping her pants to the floor. Patting her ** saying if you want any more of this then you will do as your told!

She then reached for the garter and bent down telling me to step into it which I did still num from what was happening. As it was pulled up she kept telling me how fun it was going to be and how lovely I looked. Then told me to sit down and showed me how to put on a nylon, telling me not to put any snags or runs in them. Once I had them pulled up I was told to stand and she hooked the stockings to the suspenders. With my ** still hard she had me put on a pair of pink satin ** that hardly held my ** in. Oh you look so sweet just as I thought you would. Back from the shock and numbness of all that was taking place I looked into the mirror and seen myself dressed in female lingerie. You will remain in this all day do you understand? Okay I said.

Lets go to the kitchen as she pulled me buy my hand. Laying back on the table with her knees in the air and her feet on the edge of the table she told me to sit down. She grabbed my head and pulled it to her ** saying, alright my little sissy boy eat my ** and do a good job if you know what is good for you. I could see she was glistening with wetness as I licked her wet **. She moaned in delight saying that's it sissy boy do your job and do not miss a drop of my juices. I spent the rest of the day in my garter nylons and **. She asked how I liked our session we had and if it was something I wanted more of? I told her that it was fine and I would like more if that is what she wanted.

The next morning before leaving she said that I should start wearing the ** she bought for me and shave all my hair. She would be back next friday and turn me into a proper sissy for her needs. This immediantely made me erect and she said, I see you do like being my sissy boy. Giving me a big french kiss she got into her car and left.

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    • I would love to be a sissy for her. There would not be an untouched man around! Oh, where do I find a Sweet daddy to love me? Where? I so want to have one. I will be the best woman he has ever had! I would even marry him and become his wife! I really would. Oh, bois, please, I am so very available, and I want it, I want you!
      Your Loving Roxanne Sissy

    • MOTHER OBVIOUSLY HAS REAL NEEDS AND REQUIREMENTS. HER SON TOO ALSO HAD NEEDS AND ONE OF THEM IS HIS LOVING MOTHER. THE MOM KNEW OF THE BOYS PREDILECTIONS FOR SILK SATIN AND NYLON....WHAT BETTER WAY TO ENTICE THE ** LAD BUT WITH GENUINE 100% MULBARY SILK ** (SLIGHTLY MOISTENED). THE SISSIFIED YOUNGSTER NOW HAD SMOOTH LEGS, WET **, HARD SISSY **, AND A ABUNDANT ARRAY OF LUXURIOUS LINGERIE.

    • I came from a poor family from mexico... my mother didn't have the cash to buy boys underwear being the only boy that left me wearing girl ** for a very long time. I like girls... I like even more dressing as one and getting penetrated by thick long members. Today many years later I have an plug in anytime am not working.

    • I Love To Wear A Plug As Well When I'm Not Working Or That Time Of The Month!(I Pretend To Have A Period With Tampons And Pads!)

    • I wished this would happen to me. It sounds wonderful and I hope you turned out beautiful. I bet you found a wonderful life you enjoyed more than the one you were living.

    • I came to the conclussion I was a bi bottom in my junior year of highschool. I ended up going to prison 6 years latter. There they showed me I was nothing but a little **, a hole for men to dump their ** in and thats all Im good for. Now, Im still attracted to women but ** with a female I find all I want is to please them with my mouth. Im always thinking about sucking and ** **. I keep myself locked in chastity and ** by using **'s. (I am in my 40's and single)

    • You need to take English again and learn how to spell. Your ignorance showed through a lot.

    • Your ignorance shows by the grammar you use. Your no better than the one you referring to!!

    • I think that anyone who has to call another names is a weak ** ** now comment on my grammer **

    • The one who wrote the above...Your ignorance shows by the grammar you use. Your no better than the one youer referring to!!

    • All my thoughts are about sucking **. from age 14 to the present time wearing ** and dreaming about having a man ** my face keeps me in a constant state of arousal I truly like the taste of ** I want to be ganged banged by at least 10 men having their ** shooting ** in my mouth and being ** hard by them feeling them ** in my **/** and being jacked off on I CANT WAIT111

    • Oh yea nothing better than ** swallowing

    • I love ** swallowing

    • I was 14 when I lost my virginity to a older man he rename me from Tim to Tammy as he breaded me as he seeded me he told me I was his sissy !! He made me dress in ** stocking I had long hair so I fit his needs he breed me three times that night !! I been a sissy now for years and love taking care of men’s needs my favorite are married men who wife’s don’t ** ** in no time there deep in my **

    • Umm ** yes

    • Excellent

    • My mom kinda is responsible for turning me into a sissyboy by having me wear my sister's **. She said that I look so cute in um, I guess I do? An older boy saw um, he could see um up my shorts when I was hanging out with with him and climbing the peach tree down the street and stealing peaches. I'm a lot smaller and can climb up the tree better than he could. He told me that he could see um and when I got embarrassed he said not to because I look really cute in um. It was weird cause I let him have ** with me that very same day, my first time too? Ever since I've let him him and other boys want to. So I guess it's okay cause I really like it. I mean in the ** and everything else.

    • Its been two years since I a male become a girly ** boy for my lady friend I have nice girly ** for a sissy I wear nice sissy girly clothes now I just keep house for her as her house maid and slave to her and other lady and men like once a week I go over to this man house dress into a ** maid out fit and clean his place on one day he came home early I just finish making the bed when he came up behind me I heard him said you have nice ** I keep working and said thank you sir he just walk in front of me and saw my ** I just stray were I was he sat on the bed and look at me you sure look lovey if I knew you look like this I would come home early more I thought about what he said I never had a man ** be fore I told I had to use the phone he left and I phone my lady friend and told her what happen she said well dear you are there to make him happy I said yes miss I put the phone down when he walk back in I was now laying cross way on the bed he sat beside me god you look ** this way I said there some thing you should know I never been with a man that when he said I know I heard you tell your miss he just put his hand on my ** and ripe my blouse open he look at my ** I unhook my bra and remove it he ** my ** as he did I start to play with his ** he told me to unzip him and pull out his ** I did as told now he got up and his ** was in my face I open my mouth and he shove it in I start to ** when I heard the door open it was my miss she just said I see my sissy pleasing my man he said yes dear he a good ** sucker or she is that right honey she is you think he a man well yes no dear in two years he been my girly ** boy no man has ** as lovey as her and a nice round ** no dear well after that day her husband shove his hard ** in my male ** ** and I beg them to let me be there ** and now I am when he not at home she the one that wears the pants

    • That’s so hot love it

    • I love women's ** and tights

    • That's a proper sissy! My sissy clitty is all hard for you.

    • That sounds kinda hot would want to try something like that my kik is discreetplay592 for any ladys

    • I a male since I start to wear women thing for a lady friend you see I ask her to dress me in girly clothes well she did I got to have fake ** glue on my ** then a ** half black bra that show my ** more then put into thong lace black ** then a white blouse and a short black skirt when I look in the mirror I look like a girl she told me no not yet we have to get you to a hair shop get your nails and hair done well after three hour at the hair dresser the lady look at me and told her he look lovey as a girl yes he do now he will be a she and soon are girly ** well she was right I was put in a chair and one lady remove my blouse and said what nice ** she has she look at my miss and said may I she said yes make her beg to be our ** girl the next thing I knew I had a ** ** in my mouth and one in my knew ** ** then a lady I saw remove her slack and I saw her big male ** that right dear I was a man once till I learn to be a girl with the help from these lady now you want to feel like one I told her I all our well after that night I never been happyer

    • This is ** and I love 💕 to be a woman all the time and I like to know what

    • I have an aunt who told me I was pretty and should model stockings because I had perfect legs. I was ten and had been wearing my sisters things. Now 13 at my aunts, I found a hamper in her bathroom and went through it finding soiled **. I wore them and felt **. Startled by a knock, my aunt asked if I was okay. I quickly undressed, threw them in the hamper and came out, saying I was constipated, It had been over 30 minutes! the next time we visited, I went to the hamper finding more **, bras and slips. I lost track of time and my sister knocked and asked if I was constipated! Our next visit 6 months later, I did the same! This time there were more things, on top a note! "Have fun, don't ruin my stockings sweetie". I was so shocked I went potty and came out. Later my sister went to the bathroom and came out looking and smiling at me. I turned red, my aunt whispered, "I thought you'd be constipated again." Mom got up to leave and told us we were staying there while she went on a business trip. My aunt had asked my sister if I wore her things and she said yes, many times. After mom left, I felt very nervous and went to my room to go to bed, there was a nightie with ** on the bed, a note telling me to wear them, I did! The next morning my sister came in, "wake up and come to breakfast sissy, don't bother to change, we know all about you." I waited and my aunt came in, put her arms around me and said she knew I should have been a girl and told my mom that. She took my hand and led me to the kitchen, in front of my sister in a nightie and **. After breakfast I became a girl. My sister and aunt changed my world, making me their sissy, styling my hair, make-up, **, bra, a dress, stockings, and heels. I spent that week as a sister and a niece. Now my sister dresses me when mom is away, we often stay at my aunts as three girls. I answer to "sissy" and my sister is my keeper, along with several of her closest friends. I love my new life!!

    • This is very much what happened to me also.

    • Me too

    • Wish someone would do that to me

    • If you lived near me, I’d buy you all sorts of women’s clothes and would make you dress and model them for me.

    • I a male after I was made into a sissy girly house ** boy maid I learn a lots its not all fun I wake up in the morning and start off making me petty for my miss I must be clean shave be in a clean nightie then go into her room and wake her up I pull the cover back then I lift her nightie she had her ** dido ** I bend down and wrap my lips around her ** an ** then I felt her hand on my ** she then said you are a good wife I keep sucking her ** she just yell yes ** then she pull out and turn me over and shove her ** in my ** ** she tell me are you my wife now I said yes miss then you are ready to go one step more yes miss good girl because to day I will take you to see a lady friend and she going to make your ** a little bigger well after that morning I now have lovey girly ** after they were done I thank them both that when I found out her friend was a she male I did not care I ** her ** and she pull out just in time to shove it in my ** ** I toke all her ** and she shot her load in to me my miss said I just become her ** and wife

    • Hi like you I met a new girl friend who has turned me into her sissy boy, she keeps me completely hairless and in little girl style **. She has taken me to Holland and had a friend of hers who is a surgeon remove my testes so I am unable to produce testosterone, my p...is has been permanently fixed back so I have a girl shape and she has had all my body hair permanently removed. I now wear ** all the time and at home I am not allowed to wear any male clothes, she picks out dresses and nighties for me and my hair is stlyed in a feminine shape. When she has her period she puts a Tampax in my little sissy ** so like her I have to keep it in all the time.
      Some weekends she reverts me back to being her baby girl, she puts me in “ lovely thick fluffy nappies “ and plastic baby ** and a “ nice short dress “to show off my frilly **. I have come to accept and love everything she does with me I am a self confessed sissy baby

    • I asked my gf 2 years ago, as I started wearing **. She said she'd love to, and said she'd always wanted to turn a bf fem or gay. I told her I loved **, more than **. She said she knew, she heard how much ** I sucked before we dated. She threw away my boxers, only **, shave daily. She said my ** was small, and didn't get her off, I asked if she'd help shrink it.via caging, she got me estrogen. I dressed as a female alot. She taught me alot of fem ways. She watched me go all the way w my first guy. I was hooked. After 8 months, off the cage came, I lost 2 n half Inches in length, quarter girth. Soft I'm the size of a new born baby. I told her I am happy it's so Tony, her bf was 9 inches, so hot. Well we have these times she will humiliate me bad. This last few weeks I wear girls diapers,everywhere, my hair in pigtails, she treats me like a 3yo girl. I love it. She's changed me in front of 2 of her friends who laughed at my tiny **. She got a ** growth chart, it's the size of a newborns. I get called baby ** alot. She has me play w dolls, and I got to practice sucking ** daily. I can ** 9 inches. She sent my religious father who once said her putting makeup on me, I'd turn gay. Well she sent a pic of me dressed as a girl w a huge ** in my mouth, w pics of my tiny **. She said I shrunk his **, and turned him into a female who loves **. Oh yeah, he's loved ** before we were together. I loved it. It's not for everyone, but we live together, it helped her become more domanering. , she loves that I'm happy. She loves that she turned me out, says she loves when I bring a guy home. Said she'd turned me gay anyway, said yr ** was small ad, like the smallest I've had, n to be honest I didn't feel it, I said I knew,

    • I told my wife about being a sissy when we first started dating .She loved dressing me up and we even had guys over for **. When ever she invited a man over id be totally feminized and usually waited on them like the maid.When they decided I was allowed to ** his ** but nothing more, they never ** me.The men were there to satisfy my wife and I loved to watch . My wife began keeping me locked in my cage longer and longer which was torture but was feminizing me more and more and it took my mind off the fact that she wasnt allowing me to have an ** .She was being kept sexually satisfied by the men she had coming over and I was kept busy sucking their ** so I was happy . My wife bought me a ** and made me ride it until I had an ** which I loved and we discussed it and it was decided that since I am able to have ** I dont need the cage to ever be removed and I cut the keys in pieces . We are so happily married now ,to most people I am her husband but to certain friends I am her live in sissy . we have ** together like two women since I dont have the use of my tiny locked up sissy **.Now when she wants ** with a real man she invites them over and I get to watch and ** their big hard ** and jack them off .

    • This is ** I like to know if you hide what woman you like for me to be dress 👗 I love 💗 you have fun with me and I think 🤔 was a sissy night out and I love 💗 do all things she do for her

    • Nice location?

    • My wife came home early one day and caught me dressed up as a female . I apologized and went to change but she told me that since I was all dressed up that I should remain as a girl . She made me wash my face then re did my makeup and fixed my hair for me.After lots of questions from her she told me that I really looked cute ,and that she kind of liked it. She told me that I could dress feminine if I wanted but only if I took over all of the household chores . I smiled and asked her if she wanted me to be the maid and she said that was a good idea. She bought me a couple of different french maids outfits to wear.When I see one laying on the bed I immediatly get dressed up and am her sissy maid ,usually after work till the next day or even for the entire weekend.When she decides I am to be her sissy maid it is until she decides otherwise and I have had to take the day off work when I see my outfit waiting for me when I get up in the morning. She said I dont have to call in but if I go to work it has to be dressed as a sissy maid .

    • I am so happy that my girlfriend agreed to feminize me completely and turn me into a sissy slave.I begged her to do it and wasnt prepared when she told me that it wouldnt be just a part time thing,when she agreed to turn me into a girl it was going to be 24/7,365. It was very hard at first and didnt get any easier for a long time ,I lost most of my friends and alot of my famil wont talk to me even now.I was so scared when I walked in the front doors at work as a female but Heather walked right next to me for support.I was fired from the position I held as a male but re hired back right away as a secretary .I hoped that I would be fired and not have everyone I worked with teasing me but that didnt happen.I was forced to go to work every day in a skirt and heels and was teased and made fun of by everyone non stop.I was a sissy secretary and they made sure I was totally humiliated at all times.Heather told me I wasnt allowed to quit ,had a talk with my boss and he wouldnt let me quit ,my only way out was to get fired and my girlfriend made sure I did my job and was the best sissy secretary possible with the use of a paddle . Everything eventually calmed down and I began to like being a secretary,Just not the sissy part of it.Being a sissy meant I had to ** each and every ** that I was told to and let the men pound my sissy ** as often and as hard as they want to .I still work there as a sissy secretary and love it ,especially being used like a **

    • I am a older male one day as a joke I ask a lady friend of mine if she ever dress a man in women things she said no but I always want too I told her look if like I let you dress me in girly clothes I always want to try on girl clothes once I wore ** well then when do you want me to dress you up I told her right now I do any thing you like that when she said fine remove your clothes I did as told then I was shove in the shower she rub cream all over me then I was wash off and dry she hand me thong ** as I put them on she got two fake ** they had glue around them she put them on my ** I was told to hold them then came the bra she made sure it was tight she told me it help keep the ** in place then I sat in a chair were she did my toe nails in a bright pink she wait for awhile I ask if I could see what I look like she said if I do what in it for me I told you I will do anything that when she said show me your mine just then she pull her slack down and I saw a big dido ** well what are you waiting for I got down and shove her ** in my mouth as I ** she told me you are going to be my house ** boy I stop just to said yes miss the next thing she pull out and turn me over the chair my ** were off and she start to shove her ** in my ** soon it was all the way I beg her please make me your ** she grab my ** and said yes because you never be a man again she was right I became her ** and I love her ** now after a few month I start to work as her house maid one night a male friend came over she told me to be nice I ask how nice she said when we go to bed you come in the room I did as told once there I saw his big hard ** I knew what my miss want I just craw on the bed and ** his ** after that he shove in my ** ** now three month go by and I have two master I love

    • You are one lucky sissy

    • I'm a 55 year old sissy baby and I am looking for a mommy to take care of me forever I need a Mommy too change my diapers when they need to be changed I need Mommy to put me in a high chair when it comes around to feeding me and I want Mommy to feed me baby food and I want to drink out of a baby bottle and I want to be treated 100% like a 1 year old baby girl I want to do everything like a one-year-old baby girl I want to wear diapers 24/7 I want Mommy to put me in Girly baby clothes and girly diapers I want to sleep in adult baby crib forever and I like to play with baby toys in a playpen and I want to crawl around to get where I got to go and I want Mommy to make me talk like a baby and I want Mommy to take me out in the public and show me off as a little one year old baby where the public can see me as a one-year-old baby girl for the rest of my life I want to be a one-year-old baby girl forever if I can get a mommy that will do this for me please email me at mikevirgil100@yahoo.com I hope to have a mommy respond to this message as soon as possible because I am honestly truly serious and I really want this to happen to me this is a big dream of mine and I want this dream to come true as soon as possible so please Mommy respond back and tell me that you will be my mommy forever and I really would like my mommy to be able to come to my address and pick me up and take me home with her as her little baby girl I would do anything to be turned into a sissy baby forever and be a one-year-old for the rest of my life that would be the best punishment for me and I really honestly truly wanted to happen as soon as possible and I promise you I will give you my address for mommy to come and pick me up and take me home with her and live with her for the rest of my life and I will obey any commands that my mommy tells me to do and she will be able to spank me or punish me when I am naughty

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