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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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120 Comments

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    • Very exciting

    • We all started some place. You where meant to be a sissy if you accepted it that easily. This makes me jealous. I hope all turned out alright. "C"

    • I was 13 when I was turned into a sissy, by my older sister. She needed girlfriend to go on a double date with her. First she removed all hair below my neck. And dressed me up as a ** teenage girl. My date was a tall teenage black boy. I did as my sister said, if he kissed me to kiss back. He ran his hands up under my skirt, squeezing my **.

    • I wish I could get somebody to transform me into a adult sissy baby there is anybody in the world that would transform me into a sissy baby they could email me mikevirgil58@yahoo.com because I will do anything it takes to be transformed into a sissy baby and that is the honest truth hope to hear from somebody soon

    • I'm a mommy domme on a site called Imvu. I have sissy babies and I'd love for you to be mine. Email me at starshooter89120@yahoo.com. I will tell you what you will need to become a sissy baby.

    • I wear diapers from surgery,like to chat.my email is babyguy306@gmail.com.i also wear girl things.

    • Hi,I've read your reply to somebody else's request for A Mommy to take him under her care & turn him from A Male Baby into A Sissy Baby.That's exactly what I'm after,so hopefully you're somewhere near me in The West Midlands, England & you'll also take me on as well,become my Loving Mommy & Look-After me,which is much needed as A 1&1/2y.o.Little Sissy Baby Girl, John-(Baby Clare).

    • Diaper me and make me be your little baby sissie girl and spank me

    • Hi Mommy Domme, I'd love to be Your Sissy Baby too, so You're going to tell me what I'll need to become Your Sissy Baby, but more to the point, where are You in The World? I'm in Stourbridge, West Midlands, England & I bet You're over in America aren't You, so We're hundreds & hundreds, if not thousands of miles apart? If I did come over to You, You'd need to meet me at The Airport holding up A Notice big enough to be read from a distance with my name on it, & then whisk me off to Baby-Land to begin A New Life of being Looked-After by my Mommy as A Lovely, Pretty, Sissy Adult-Baby called Claire or Baby-Claire. John(Baby-Claire).

    • I am very athletic when I was 16 I had a guy friend stay over night with me he had a crush on my step-mom and stole the pair of her ** so he could sniff him the next day my stepmother found them underneath my bed and accuse me of wanting to wear ** so she made me put them on I never knew how much it would excite me and change my ** life completely since then I have craved to be dominated and turned into a sissy s***

    • I want be turned into a adult sissy baby and I need a mommy to take care of me and treat me like a one-year-old baby girl if there is a mommy out there it will do that for me email me mikevirgil58@yahoo.com I will do anything to have a mommy take care of me and be mommies little sissy baby

    • I wish I could get a mommy that would take care of me and treat me like a one-year-old baby girl

    • I wish i started dressing when i was younger but now I'm to old

    • I am to old to but it's still fun dressing up.

    • That's very very sweet .

    • My boyfriend made dress for night out, as a sissy,and two yrs later I am still his sissy

    • You are a skillful narrator even if your spelling and grammar need some work. I enjoyed your story very much.

    • I wish my lady was into forcing femming and making me her sissy **. She doesnt know i love when she makes me go on halloween as a woman, and this last halloween, i was all dressed slutty with a super short skirt, my tiny thong ** i picked up just for that night say "deliveries in the rear" and when she was not around i pulled them up whale tail style so guys could see and had ** with two hung guys, who i later introduced her to and at the end of the night she had them in our bed in both holes and they came inside her. Then they both did me again when she was in the shower.... and she doesnt know.

      I want my lady to make me only experience sexual pleasure from ** and men. I want her to make me wax and shave, and encourage me to pick up guys. I want her to laugh as i moan like a woman as i ** with my large **, or when a guy ** me. I want her to call me a sissy **, and ask me how i like being a girl. I want her to sneak me hormones without my knowing, and turn me into a woman. My ex loved watching her gay cousin and his giant 10" ultra thick partner pound me for 45 minutes me screaming like a woman having her first multiple **, begging for it harder and faster, to the point if he answered the door i would start blowing him and riding him in the living room.

    • My wife had me do the same things as you describe. Been living as a woman now for about 5 yrs,( in 30's) we tell everyone we're sisters and we both love ** and date men. Feels great, feels right, I love having ** and a nice round fem **.

    • I love this story, it's so like my lifestyle. I'm kept as a submissive sissy boy by my dominant girlfriend, she keeps me as her house girl and I live by her rules.
      I am kept totally hairless, waxed every three weeks by one of her friends.
      My testes and ** have been removed and my ** is permanently tucked to keep my girlie shape It's amazing what you can have done in Amsterdam.
      I have permanent breast forms and wear matching bra,** and suspender belt
      I have my "period" and my Tampax is inserted in my little girl ** and the cord attached to my ** so I feel it pull with every step I take
      When Lorna entertains I am dressed as her maid my dress is high necked to keep my head up and short to show off my sheer ** and lacy stocking tops. I am at the call of her guests and am to serve their every demand. I have been thoroughly taught the expert art of cullinus to complete satisfaction, I am caned should I not satisfy.
      My "mistress " will occasionally give me release with her ** if I've been a good sissy

    • Great start to your story. It got me hard thinking I was the guy wearing the ** undies

    • Hey I am a crossdresser I love to cross-dress I am an older male I love the way it feels I'd love to have hot ** with other men I love to be treated like a woman and I just love it all

    • You need to have some red lipstick on your lips and put a nice red lipstick ring around the BOTTOM of my ** . ... don't you?

    • I want that

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