How I Became Princess Sissy

by

Susan Petty 2000

 

Part 2

 

After our night of love, we were awakened by a knock on the door. We were still in each others arms, Greg shouted who's there. He was answered by the words room service, its your breakfast.

Greg asked me to open the door, so I slipped on my bridal peignoir over my sheer nightgown and opened the door to a good looking young waiter. He entered the room pushing a fully loaded trolley full of food. He started to set it up for our breakfast and poured our coffee. But I couldn't help but notice he couldn't take his eyes from me in my peignoir and I knew he liked what he saw by the bulge in his trousers. I got $5 and gave it to him as he left.

We dined like a king and queen and as Greg was drinking his last cup of coffee I disappeared below and drank my last fill of his cum as he groaned and told me how I took him to heaven and back with my sexy mouth.

It was soon time to leave and I changed back into my chiffon dress and finery and he drove me home. We kissed goodbye in his car and as I got out he asked me if I would be his fiancé. I turned around and squealed oh yes yes Greg my darling. I then got out and ran up the path to our house and banged impatiently at the door for my sister to let me in.

It was opened by Joan my sister who couldn't wait to ask me what had happened after they drove off and left me. I told her how I had fainted and Greg had carried me up to the room and how he went down on me first. I told her how we had a night of love together. Did he fuck you Sissy she asked? Several times I replied. Is he big like they say she asked, massive I replied. Did he hurt you, no I said he was really gentle but I soon accommodated all he had inside me I told her. Did he cum inside you Sissy, Oh yes and I still have his baby seed inside me held in with a tampon?

The rest of the day I spent dressed in some of mummy's lingerie and one of Joan's dresses. That night I slept in a pretty chiffon baby doll gown with matching chiffon panties. Joan didn't seem to mind me wearing her stuff anymore.

On the Monday I went back to school and everybody knew what had happened to me. The girls were all giggling and asking me about? Greg's chopper and how big he was and how did it feel inside me. The boys were all calling me faggot and picking on me. But none of them said a word to Greg. They daren't as he would have beat them up.

I was looking for an ally to keep these boys and girls from taunting me. Joan tried but she couldn't stop them. I saw Greg across the yard and walked over to him and said "Hi Greg are you o.k." I couldn't believe the reply I received. "Fuck off faggot I don't talk to poncey juniors you know that.

It hurt me like a knife being stuck into me and as I walked away from him my eyes welled up in tears.

That night I told Joan what Greg had said to me and she couldn't believe it. She said she was going to have a word with him the next day, but I begged her not to. When it was time to get up for school the next day I told my mum I felt too ill to go to school as I had a fever. I actually did I guess it was with the upset from the previous day.

That evening when Joan came home she came up to my room and told me she had played holy hell with Greg. He told her he had felt guilty about how he felt about me and what we had done and seeing me as a boy was too much for him. He told her he had fallen for a pretty girl called Sissy who he was madly in love with. Joan asked if he wanted to see Sissy again. More than anything else in the world but I can't see her as Simon my mind can't accept it.

She arranged for Greg to take me out to dinner on Saturday night and spend the night at our house as mother was going away Saturday morning until Sunday evening. She told Greg to call at 6-30 p.m Saturday and she would have Sissy dressed in a gorgeous outfit awaiting him.

I stayed off school all that week as I didn't want Greg to see me as a boy and upset him again.

On Saturday morning mother left about 8-00 a.m and as soon as she had gone Joan called me into her room. She had laid out on her bed a matching set of lacy pink lingerie and a shirt dress which buttoned up the front. I slipped into the Bra and panties and inserted the bust forms into my bra. Then came the pretty pink full length slip which I slipped over my head and arranged the straps around my shoulders and let the slip shimmer down over my body and I straightened out the lacy hem. Next came the dress and Joan buttoned it all the way down but left the bottom button undone. That's so as the pretty lace hem will show as you walk a peep of lacy slip always gets the boys looking. I sometimes wonder why the like to see a glimpse of slip. What about stockings I asked. Not today where were going. Where are we going? It's a surprise she said. It's a good job you have showered and washed your hair. She combed my longish hair into a passable girly style and handed me a pair of pink sling back sandals to put on. We got into the car and drove to my sisters beauty parlour. As we walked in my sister said the the owner this is Sissy whom I told you about give her the full makeover treatment. She then told me she would return for me in 5 hours.

They started to work on me immediately asking me to slip off my dress and put on a pink coverall over my slip. Firstly they washed my hair and then put on some stuff that smelled like bleach. They left this on for about 30 minutes and then washed it off and put rollers into my hair. The beautician then asked me to lower my shoulder straps from my slip and she undid and removed my bra. She then fixed on some realistic looking boobs with a strong adhesive. It soon dried and when she helped me back into my bra and slip I had a gorgeous set of 38b breasts pushing out the top of my slip. I was getting excited as my slip also started to push out lower down. I was then sat under a dryer and she painted my toenails and finger nails with a lovely shade of coral pink varnish. I was left under the dryer for about an hour and then she let me out and proceeded to style my hair into a beautiful feminine style.

I panicked a bit thinking what would I do about school on Monday. Don't worry she said you can comb it out for Monday but then I shrieked but look at the colour how blonde it is. Platinum blonde she said, now that's a different matter. I told Joan that would be permanent until it grew out on its own. But she said that would be o.k.

She then covered the mirror and worked on my make up for about 2 hours I could feel he fixing thinks to my upper and lower lashes. Applying all sorts of creams and powders. Until she finally said she had finished. I asked if I could look but she said not until my sister came back. Which she did a few minutes later with a large suitcase.

I was taken upstairs to the living quarters of the salon, and into a bedroom. I was told to take off all my clothes and then Joan and the beautician opened the case. I asked if she still needed to be here. She squealed I wouldn't miss this for anything I just love to transform boys into gorgeous sissy girls. But I'm embarrassed I said. No your not your really loving it aren't you come on admit it. I'm not I said. Alright then let me show you what's in this case and if you don't want us to dress you init we can make you back into a boy and take you home.

With that she opened the lid; the contents seemed to spring up on their release from the constricting space of the suitcase. I could make out my sister pink chiffon prom gown and loads of flouncey pink and white chiffon petticoats to fill out the gown. She asked me to feel how soft and silky they were to touch and she also sowed me the pretty lacy bra and ultra feminine panties of pink chiffon and lace with matching satin bows and embroidered rose buds. I could also see a suspender belt to match and the shoes in the case were pink patent courts with at least a 6 inch heel and a pretty pink bow on the instep. As she caressed my thighs with the flouncy chiffon hem of the petticoats my cock started to rise. Now then Sissy tell me you don't want me to dress you in this gorgeously girly stuff and I'll put them away. No I'll wear them if you like I replied. No you wont she said. You will have to beg me to stay and help dress you in this lovely dress and lingerie.

I couldn't miss out on this so I heard me saying" please stay and dress me in this pretty girly dress and all those lovely petticoats please make me a pretty Sissy girl for Greg"

Why do you want to look so pretty for Greg she asked? Because I want him to want to screw my brains out all night I heard myself scream.

Very well Sissy I will stay and help Joan make you into an irresistible. Sissy girl who wants her brains fucked out.

They then proceeded to feminise me to the ultimate. Firstly my pink lacy bra was put on me and fastened the lace shoulder straps fitted snugly and my new breasts were fitted into the cups. It had a pretty satin bow in the centre and a rosebud embroidered into the centre of the bow. Next was the matching lace suspender belt and six suspenders. A packet of America Tan nylons were threaded up my legs and I looked really sexy except for the huge clitty pointing up from my groin. Joan had to toss me off into a tissue before they could pull on my lovely chiffon panties. She thought it would spoil the fit and she was worried I would mess them up. Which I inevitably would before the night was out. I was cleaned off and then the panties were pulled up my legs. I was then fitted into the multi layered pink and white chiffon petticoats, the felt so gorgeous as they caressed my nyloned legs with every move I made. After these come the pink prom gown this was a low cut creation with a fitted bodice which just went into a mass of fullness from the waist to the hem with all the petticoats I was wearing. Trying to see my feet to get them into my shoes was near impossible. But once I had them on and started to walk my skirts and underskirts just swished and swathed around my nyloned thighs with a will of their own, causing me to gasp for breath and already arousing me clitty to engorgement.

Just a few final touches now said Joan as she proceeded to fit me with a matching bracelet necklace and earring set. I wore Greg's silver ring on my engagement finger. I was sprit zed very heavily with mothers Coco Channel perfume, and lastly Joan produced mother's silver fox cape to go around my shoulders. I was taken over to a full length mirror. As Looked into it I could see a most beautifully dressed and made up girl staring back at me. I found myself heavily aroused at the thoughts in my mind. I was actually wishing I could take this beauty to bed and fuck her brains out. But how could I because it was me. The dress looked so gorgeous and the ruffled hems of the petticoats showed themselves ever so slightly with certain movements of my body. But the thing that amazed me most of all was my hair and make up. My eyes almost looked Doe like with huge pink and lilac eyelids and long false eyelashes top and bottom which were so long they appeared to be fluttering as I blinked my eyes.

I nearly cried as I minced back across the room to Joan and her friend who had done all this to me. I so happy I cried do you think Greg will like me. He will die they replied. Now come on lets get you back home Greg will be calling for you soon. I ran back and kissed Joan's friend and thanked her for making me feel so pretty. That's because you are pretty my dear. That man will be coming in his pants when he sees you tonight. Joan helped me into the passenger seat of her car. She had to push all my skirts and petticoats well in so as they didn't trap in the car door as it was closed. We were only home about 10 minutes when the bell rang. It was Greg; Joan let him in and bade him enter. She's all prettied up for you Greg, she looks a million dollars. He was carrying a box with a pink corsage which I allowed him to pin to my dress. He then kissed me and I could feel the harness on him then it was so hot. I knew then it had all been worth it.

Greg had booked us into a posh restaurant which had dancing. Joan told him he could sleep the night as mother would be away until Sunday evening. As we were leaving she whispered in my ear I will leave you a nightdress out on mummy's bed. We couldn't really sleep in my room it only had a single bed.

The meal was lovely we started to dance and I could both feel and see Greg's cock was bulging his pants out. As we danced he said he loved me and that he wanted to marry me. I said I felt very nervous about him as he wouldn't have anything to do with me in school after already saying he loved me. He apologised and told me he was worried that he had fallen in love with a Sissy boy but I had given him the best blow job he had ever had and I was the best fuck he had ever had. But it worried him seeing me as a boy it made him feel gay. But he only ever saw me as a girl he was happy. He suggested me finishing school and being a housewife for him. His parents were rich and he had saved a lot of money and was starting his own business up his father had set up for him when he graduated at the end of the term. I told him I would love to be his wife but how could I dress as a girl 24/7 when I would need to get a job.

Greg told me I wouldn't need to work just look after the house and look pretty all the time for him and I could even go to the beauty parlour every day if I wanted to. I could have as many dresses and as much lingerie as I wanted so long as I made him his meals and cleaned his house and always looked glamorous fro him when he got home in the evenings. I said I would love to be his wife but how would my mom take it. Greg said he would ask Joan and they could break the news about my dressing as a girl and ask her for my hand at the same time.

All this talk of being a full time housewife had made me horny as I could see Greg was. Do you mind if we go home now Greg I want you to fuck me. Greg was first out of the door and as we drove home I unzipped him as we drove along the freeway and started to suck him off. I could hear him moaning with pleasure as I slowly brought him nearly to the boil and then stopped. Pleeeeeseeeee don't stop please Sissy make me cum please. I then realised the power I had over this big man. I lowered my lips back onto him and drained him of every drop of cum he had for now.

When we got in Joan had gone to bed. I made Greg a coffee and we sat on the sofa and he leaned over and started to kiss me. I stopped him and said just wait here I will go and slip out of Joan's best things I don't want to mess up her pretty dress and lingerie with our uncontrollable cums.

I arose and went up to mummies room where I could see Joan had laid out mommies wedding peignoir set. I slipped into it and rejoined Greg on the sofa. His pants were near bursting at the sight of me in that Virginal white peignoir set. We kissed and his hand was stroking my clitty through my silky nightdress. I got up and led him by the hand to mother's room where I undressed him and pushed him back onto her bed. I slipped off my peignoir and joined him in my nightdress where I took his hot cock into my mouth and sucked on it. Once I got him rock hard I straddled him and lowered myself down onto his manhood until I had it all buried deep inside me and then began to slowly fuck him. I could hear him moaning with pleasure. Then I heard him shout oh Sissy I'm going to cum inside you. Well come Greg my darling cum inside your Sissy girls cunt. As I had uttered these words I looked up and saw mother standing with a vacant expression on her face. Simon she screamed is that you? What the hell are you doing in my bed with that man and wearing my best nightdress and your hair done up like that and all that make up. As I was thinking of an answer for her I heard Greg scream god I'm Cumming inside you I'm so sorry I can't stop myself.

Mother said finish up here Simon and then slip on the negligee and both of you come down to the lounge.

I slipped out of bed and put a tampon in so as not to mess up mummy nightdress. Greg went to my room and got a dressing gown but it looked miles to small for him. When we got down Joan was sitting with mother. Right mummy said, Joan has explained how she caught you dressing in her and my clothes. Apparently this has been going on for some time as I though some of my panties were stained. I believe it was her revenge that got you and Greg together. But it's backfired as you love being a girl better than a boy and that you two are engaged.

Yes mommy I love living as a girl and Greg has asked me to be his wife. I want this so much and I want to live my life as a girl. I don't ever want to have to wear horrible boy's clothes again as I love the feel of soft silky clothing caressing my body and the feel of full petticoats caressing my nyloned encased legs. I love the way high heels make me sway my hips around and drive boys crazy for me.

Then Greg spoke, Love Sissy and I want her to be my wife. I'm quite well off and my father is setting me up in my own business when I graduate in a couple of months. I' would like to get my own place and have sissy move in with me and be my wife. I know we are too young to get married without your consent but we don't mind waiting so long as we can be together.

Mother had tears in her eyes, Simon she said as long as you're sure you want to live life as a girl I will help you but don't decide on anything like a sex change until you have tried it for a while. You can't get married properly but we could have a mock ceremony before you and Greg take a place together. I would be so proud if you be get married to Greg in my wedding gown that I married your father in.

Oh mummy I said you don't know how much that would mean to me. Your wedding dress is something I always wanted to wear with all those chiffon and tulle petticoats it's to die for. I ran over and kissed her as I was so happy. Just one thing she said, I think Sissy isn't a very appropriate name for you. As you were named Simon why not be known as Simone it sounds so deliciously French so feminine. Yes mommy Simone it will be I shrieked.

Now then my children its time we went to bed, I will sleep in your bed tonight Simone and you and Greg go back to my room. Do you like my peignoir she asked me, oh mummy it makes me feel really girlish to be in this. Well then you may keep it on tonight but then after that you can use any of my other pretty gowns and we will save that for your wedding night.

No mummy I will take it off no I said and went and changed into a really pretty pink chiffon baby doll peignoir set with pretty pink matching panties. Greg's mouth opened with amazement as I walked back into the room grabbed his hand and led him upstairs. I heard Joan saying to mummy I know what she wants and I know what she's going to get. They were both shrieking with laughter, but I didn't mind after all they were right, I was about to get a good seeing to from Greg's engorged cock. But when I had finished with it, it would be a shadow of its self in the morning.

The next couple of months seemed to be years, but mother had arranged for me to finish with school. I never went back after that fateful night. Mother had other plans for me such as teaching me all there was to being a girl. I used her wardrobe and my loving sisters as well as building up my own array of lingerie and dresses and such.

One morning mother came into my room and told me to shower as we were going to try out her wedding dress for size in case it needed any alterations. I couldn't believe my ears, ooo yes mummy I shrieked. I was in and out of that shower faster than greased lightning. Mother called me through into her boudoir; I just had my towel wrapped around my naked hairless body. Right Simone first things first, take off your towel whilst I help you into this bridal Basque. It was pure white satin and lace with six suspenders also trimmed with lace and was edged with a chiffon ruffle around the bust and hem. I slipped into it and mummy tightened the laces to bring my waist in to an hourglass shape. She put some padding into the bra cups to create my bust and then helped my slip on the white stocking and fasten them to the suspenders. Next came a pair of white satin and lace panties the were so white and glistened and felt so soft. Next she held open the waistband of a multi layered petticoat of chiffon and tulle with masses of pretty lace at the hems of each layer. As she pulled it up she noticed a bulge appearing in my panties. Your not going to have an accident in those new panties are you my girl? I don't know mummy I feel so sexy and those petticoats are so tantalising caressing my nylons.

There's only one thing for it she said lie on the bed; I couldn't believe what mummy did to me next. She pulled down my satin panties and removed her own warm pink silky panties and wrapped them around my rigid cocky and started to wank me off. It felt so good I was whimpering with delight and soon did a massive cum into her warm silky panties.

That's better she said as she wiped me free from cum with her soiled knickers. We then carried on with her fitting my petticoats and then slipping her wedding gown over my head. As she started to button all the buttons up the back she sighed, its going to need letting out a little. She didn't try to force things and then went to get a pair of white shoes with 5 inch stiletto heels. We can get you a nice pair of satin courts for the ceremony she said. Now sit down I have to make a phone call, she came back and told me to keep the dress on as a wedding dress expert was coming to look at the dress and take it away to do any alterations. She arrived about half an hour later and took the measurements she needed and asked for me to take off the dress so as she could take it with her. As I removed it she saw the petticoats and remarked how pretty they were and ran the layers through her finger tips. I bet those feel gorgeous on your stocking don't they honey? Yes I replied, well that's the beauty of being a girl boys just don't know the pleasure we get from our things do they. We also get pleasure from their things to if you know what I mean and started laughing.

When she had gone I told mummy how much I loved the dress and couldn't wait to get married to Greg, But. But what she asked I just wish I had my own titties instead of padding. I can't afford for you to have implants honey or else I would and a sensitizer injection. Whats that I asked. It makes your nipples really sensitive to a mans touch and I've heard when a man sucks on your nipples it can cause you to have an orgasm.Oh I wish I could have that Greg's always sucking my nipples.

A few days later my sister asked me to go to the mall with her to choose an outfit for the wedding. When we got back Greg was there talking to mummy. Simone she said Greg and I have been talking about your titties and he wants to pay for you to have implants to give you a 36c cup bust, and also have the nipple sensitizer injections. It will cost $5000 but we have phoned and booked you in this weekend to have it done. The wedding ceremony will be here the following weekend and Greg has seen a house he wants you to go look at with him.

Everything was moving so fast, we looked at the house it was a huge 4 bed roomed house with a lovely kitchen and a big garden and a pool. We decided to have it and Greg told the Gardner he could stay on and look after the garden and pool. I his wife would look after the house.

That weekend I went to the clinic and saw the lady doctor who knew I was really a boy but she didn't mind as she said she liked sissy boys. She even asked if I fancied having the whole deal and taking away my naughty bit and giving me a vagina. But mummy said I would have to try out being a girl for a while in case I didn't like it I could get the implants removed. I was then anesthetised and went into a deep sleep have a really naughty dream about me having a gang bang with a gang of bikers. The doctor told me how comical it looked when under the aesthetic my little cock had stood to attention and started pumping cum all over the place.

I was allowed home the following day and noticed how my nipples felt so sensitive to the touch of my lacy bra and my nipples would harden. Greg and I were kept apart all that week mummy said we weren't to see each other until the wedding and warned Greg not to toss off as her daughter would want all that stuff he had saved on her wedding night

The following Saturday I was helped by my sister and mother into the refitted wedding outfit and a professional beautician came and did my hair and make up. I had all the pampering a real girl bride gets and more and was taken to the place of our wedding which was in a large hotel. Mother had arranged for a minister telling him it was just a wedding practice. After the ceremony we had the reception not many people there mostly girls from high school. Most of them had hoped to land Greg but I did it me a little sissy boy they had created to humiliate me and I had their most eligible man for my own and I knew he loved me and would always look after me and protect me. He had a share in his fathers business and was making huge money. His parents also loved me and his mom told me what he liked and what he didn't like. When it was time to go to bed mummy came to have a last few words with me.

Simone she said when I married your father and he took me to our honeymoon suite for the night. He carried me into the room and laid me on the bed and he couldn't wait for me to take off that dress he screwed me in the dress. It's such a thrill to be fucked whilst you are wearing a gown like that and having all those petticoats around you as he pounds into you. Try it also I know how much you liked my bridal peignoir set, so I have had it cleaned and re whitened and it's lying on your bed. Its one of my wedding presents to you. Oh thank you mummy I was weeping with happiness. We went to our room and Greg opened the door and picked me up and carried me over to the bed and gently placed me down. Greg honey I said please fuck me whilst I'm still in my gown. He pushed my petticoats up around my waist and pulled down my panties and placed a pillow under my buttocks and he was soon inside me buried up to the hilt. I was screaming with pleasure oh Greg, Greg fuck me! Fuck me! He didn't need much telling and was soon filling me up with his week old store of sperm. I slipped out of my dress and lingerie and slipped into my wedding peignoir set and was soon voraciously sucking Greg's cock hard again. This time as he fucked me he was sucking my sensitive nipples and with his pumping cock and sucking my nipples I was soon spurting an orgasm also.

That was several years ago now and I'm still as happy now as the day we married and moved in. Greg spends vast amounts of money on dresses and lingerie and pretty peignoir sets. As he loves me to be in something pretty all the time. If I feel horny all day and want him to fuck me when he comes in I dress in such a sexy manner he has to have me there and then even over the kitchen sink. He knows if I'm in a peignoir when he comes in I'm really horny.

Mother often asks me if I have thought anymore about having the full female operation. But I'm happy and so is Greg as we are and I don't think he will ever look anywhere else. He wouldn't be any good because I drain him dry every night (giggle, giggle)

  

  

  

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