How I Became Princess Sissy

by

Susan Petty 2000

Part One

 

My name is now Sissy it was Simon, but that seems so long ago. As I sit here dressed to the nines in my Black chiffon cocktail dress waiting for my live in boyfriend Greg to get home from work.

He's taking me out to celebrate our second anniversary of us living together as man and wife. How did this all come about you may ask? Well I will tell you if you have a few minutes.

I was born Simon Jackson I have one sister Joan who is a year older than me. Our mother was widowed when I was only 10 but that didn't cause us any financial hardship as my mother is a very successful lawyer.

Unfortunately her career meant we didn't see too much of her as children as she was away from home long hours and didn't get home in the evenings until after 8-00 p.m most evenings.

This meant my older sister Joan taking care of me. As we got older and went to high school she got a circle of friends and I became an embarrassment to her.

When I got to 14 and she was 15 she decided I was old enough to take care of myself and she began going out straight after school. This left me at home most evenings alone until after 8 when mother came home.

It was also at the time that I was starting to become sexually aware of girls but too shy to ask one out. But I took great interest in their clothing especially their lingerie.

It wasn't long before I was sneaking into Joan's room and trying on her lingerie and wanking myself silly into these silky things. It became like a drug to me wearing her stuff.

However she seemed to get suspicious of me and when I was 16 I had a near miss into her lacy panties. I was fully dressed in her things including all the fineries of high heels and make up along with mother's blonde wig.

I was looking at myself in the mirror and caressing myself through the layers of silks and satins. I felt myself approaching orgasm and tried to get my hot throbbing cock clear of the lingerie I was wearing. I guess I wasn't quick enough and got a few drops of cum on her panties and slip.

I cleaned it off the best I could and put them back in her drawers. However the following evening she asked had I been messing with her lingerie. I pretended I was really astonished she could even suggest such a thing and shouted at her in anger. I thought that would make her believe me.

The night after her boyfriend came home with her and she took him into her room. Alan as he was called was a T.V engineer for a living and they were in there about an hour. I thought he was screwing her whilst mum was out.

They came out and Joan said they were going out and wouldn't be back till after mum got home as they were going to see a movie.

This was all I needed I went into her room and I knew I had 2 hours until mum got home so I decided I would be able to dress in full. I wore all her best lingerie with nylons and her party dress it was a really pretty dress of pink chiffon and had matching 5 inch shoes to go with it. I donned mums blonde wig and made up my face. As I preened in front of the mirror I Imagined I was waiting for my date to pick me up some big muscle bound football player from senior high.

It wasn't long before I felt the on come of an orgasm just thinking about it and not needing to touch myself. I quickly grabbed a handful of tissues from her dresser and pulled my lacy panties free from my throbbing cock. I was soon squirting a mighty cum into the tissue.

After cleaning myself up I took off all her clothes and went into mother's room and found her wedding night peignoir set she wore on honeymoon. This was so sexy in white chiffon with oodles of lace and ribbons. I also got the matching Malibu slippers with 6 inch heels which went with this really pretty set of lingerie.

I floated back into Joan's room and started to put her lingerie and dress away, as I was walking about her room in mother wedding trousseau I got hard again and ended up in front of the mirror pretending I was a bride asking her husband what he wanted me to do to him. Do you want me to suck your big cock honey you know I want to feel it inside me. I heard myself saying and again I became so aroused I found myself wanking myself in mothers silky peignoir set.

I got some tissues and lay back on Joan's bed again saying come on my darling fuck me hard I want your big cock inside me again. Again I had a huge cum into the tissues and then went and put on my own clothes making sure I put everything back in its correct place.

That was it until Friday morning when mum told us she was going to stay at her boyfriends house about 60 miles away and wouldn't be back until Monday evening, she did this about every 4 weeks.

That's o.k. mum we both said. After she had gone Joan said she was having some friends stay over for Saturday night as there was the Prom Princess night on at the Marriot in town.

The prom Princess was something the senior highs were only allowed to attend. It wasn't anything to do with the school it was something they organised themselves. It was a kind of tradition. Like the prom king and queen at school the seniors booked the ballroom in the hotel and booked the bridal suite and then the girls dressed in their best gowns and attire to see who the prettiest girl was.

Whoever came first got to spend the night in the bridal suite with whatever heart throb had agreed to bed the winner. They would then have a night of sex as a princess bride.

Are you entering I asked? No but I know someone who is and they will be getting ready here as my friends and I will be dressing them up in lovely lingerie and stuff to make them look as beautiful as we can

I wondered who it would be, who it is I asked do I know her. Yes you do, but I'm not telling you who. Joan said if I wanted to know I would have to be there at "2-00 p.m when they would be starting on the transformation of a future princess bride.

No I said I'm not really interested, very well she said you will never know who it is then will you. The following morning some friends of Joan's came round and I said I was going out. But I might be back at

2-00 just to see who it is. Annabelle who I fancied like mad said I will personally look forward to that; we can have some as she winked at me.

That did it I knew I had to go back she was giving me the come on. When I got back just after 2-30 Annabelle stormed over to me and demanded to know where I had been.

Why I asked, well we have so much to do with you to get you ready. Ready for what I asked? To be the princess sissy prom bride.

What! Are you crazy there's no way I'm going to be that what makes you think I would let you do that to me.

Then Joan said "don't be so innocent I know you have been wearing my clothes for years and mothers too. Prove it I snapped back.Alright I will. Turn on the T.V and video Annabelle. Soon I could see myself in Joan's bedroom selecting lingerie from her drawers; I could feel myself blushing with embarrassment. Well little brother do you want to see more there's 3 hours worth of you girly activities on here culminating in you wearing mothers wedding night peignoir and mules. Should we show it to her? If your thinking of grabbing the tape to destroy it don't bother there's 5 more copies at all my friends houses and we might even put it on the internet.

You would have lots of male admirers after you then sissy.

Please no don't do that I will do anything you ask. Joan came over and put her arm round me and said its only a bit of fun we will make you look so feminine everyone will think you're a real girl and if you act right they will never know any different. Annabelle said but if she wins she will have a night of passion with Greg in the Bridal suite. Greg I said. Yes Greg Johnson the school football captain.

I knew who the meant he was a real conceited guy all muscles on a permanent ego trip. He wouldn't even speak to me as he was such a swell head. Apparently all the girls thought that to.

I was ushered into the bathroom and fully stripped and covered in creamy stuff called Nair. This I soon learnt was to de hair my body which it did when I stepped into the shower it all fell off and went down the drain.

My body was smothered in a perfumed smelling cream which was to moisturise it I was told. It left my skin with a silky soft finish. My fingernails were then given a lengthening with false nails and painted in a shimmering frosted pink. Annabelle said this is so apt the colour ids called" Sissy Pink" it comes with matching lipstick. My toenails were also done in this same colour.

I was then taken back into Joan's room and fitted into a strapless Basque in white lace with 6 suspenders. When they had fastened this around me I was sat on the bed and white sheer nylon stocking slid up my legs and attached to the suspenders.

It was more than I could stand and my cock sprang to attention. Look said Annabelle he loves it, I told you Joan replied. Well we can't get his panties on with that monstrosity stuck out.

Sit on the bed lover said Annabelle and she dropped to her knees and took me into her mouth. It felt so good I had never had this done to me before and was soon shooting a big load into her mouth. She greedily took it and came up and kissed me forcing my cum into my own mouth and making me swallow it.

Ugh! That was unexpected. You need to get used to it lover said Annette all us girls are expected to do that to boys its part of being a girl. Never I replied, oh I don't know I bet you would love the chance to do it to Greg wouldn't you, and they all started giggling.

Now we can put her panties on, they were so girly in white satin with chiffon ruffles around the waist leg openings and across the seat. The front t was adorned with an Embroidered heart and in it the words princess sissy in silver thread.

Now for your dress and we got this especially for you tonight. Joan opened her closet and brought out a strapless dress, it had a boob tube bodice which was covered in silver sequins thousands of them. From the waist to just below the knee the very full skirt was just layers and layers of white floaty chiffon skirts which were handkerchief hems. As it was fastened at the back I felt so weak with pleasure I thought I would faint. However Joan said they still had a lot to do. I was taken over to the dresser and seated. The mirror was covered and they began to work on my face. Joan places a cork behind my earlobe and pierced it with a needle quickly repeating it at the other side. Don't worry it will grow over if you don't put something into the holes.

She then fastened a pair of long dangling rhinestone earrings into the holes. Her make ups done said Annabelle and they then produced a shoulder length platinum blonde wig and fastened it in place. I could feel it tickling my bare shoulders and neck when I moved my head and I liked that.

A rhinestone Tiara was placed on my head and I felt a rhinestone necklace being fastened around my neck. The cover was re moved from the mirror and I saw this most beautiful girl looking back at me. I really was pretty.Anabelle said we have done too good a job she will win.

Don't talk ridiculous screamed Joan.

She came over with a pair of white satin 5 inch heel court shoes and helped me slip them on. I got up and walked around the room no trouble at all. I had worn heels like these many times before as Joan knew.

Annabelle then presented me with a purse also in white satin to match my shoes. Inside it was 2 tampons spare pair of the same panties I was wearing. Lipstick and other items of make-up and a cell phone.

How do you like your necklace hon. asked Annabelle. It said in rhinestone letters princess sissy. I was then sprit zed with a very sexy perfume and we all waited for the other girls to get changed. Two hours later 2 cabs were honking outside. Right girls its time to go said Joan. They got their coats and I was given a sheer chiffon white long sleeved coat to slip on over my dress. It was so light and sheer it seemed like a negligee. As we tottered out to the car in our finery my sister Joan grabbed my arm and said your loving this aren't you. I smiled and nodded to her, so am I she said I do hope you win it.

I don't I thought to myself. As we arrived at the hotel we were greeted at the entrance by a lady who asked are any of you lovely girls entered into the contest. Just Sissy here the squealed she's hoping to win so she can spend the night with Greg. I started to blush and the lady said look you're making her blush. She then said to me what a pretty outfit I was wearing and even if I didn't win I wouldn't be short of young men to be asking me out.

The weirdest thing was, although I was scared of being discovered I was secretly enjoying what was happening to me. It's a good job my dress had such a full skirt as my throbbing cock was rock hard again and pushing the front of my panties out.

Joan noticed this and squealed look he loves this look at his cock pushing the chiffon of his skirt out. Stand up sissy and the fullness of your dress will hide it.

There came a call for all 20 contestants to the prom princess beauty pageant to make their way to the stage. I was helped there by my entourage and climbed the 8 steps onto the stage.

The mistress of ceremonies told us to go off stage and we would be given a number. She had a sheet from which were listed details about each of the contestants and what they liked to do and what they wanted.

I was given the number 3, and when they were ready the music started playing "A Pretty Girl is Like a Melody" As the first contestant walked out I heard the Mistress of ceremonies reading.

"This is Dawn she loves to cook and shop for things for the house and hopes to get married young and start a family.

As my number was read out and I minced out onto the stage she read." This is Sissy and she just enjoys being a girl she loves to shop for pretty lingerie and dresses and loves to look nice to attract boys.

She says if she wins and becomes the Princess bride she will give Prince Greg the night of his life in the Bridal suite tonight. All his buddies cheered and patted him on the back. I couldn't help but blush and was a little angry after all who the Hell gave her that lot to read about me.

My question was soon answered when I saw Joan and Annette covering their faces to hide their laughter.

The judges whittled the contestants down to 5 and I was getting a little worried as I was in the last 5.

The mistress of ceremonies then got us to come out on stage one at a time and asked each on of us the same question. She asked each one of us the same question. What do you think is the most important thing to a girl on her wedding day? The first one said a perfect man who she would be deeply in love with for the rest of her life.

As most of them answered the question in regard to them having a perfect partner in whom they would be in love.

I thought to myself here's my chance to blow it.

My answer was for a girl to have the most beautiful wedding gown as this was the day she would want to look her most prettiest so as she grew older she could look back at her pictures on what a sweet bride she was.

But my answer just brought the house down with applause they were all cheering me and clapping. We then waited for a few minutes and the judges made their decision.

In third place was Joyce who won $50 of shopping vouchers for J.C.Pennys.

In second place was Irene who won $100 of vouchers for J.C.Pennys, and the winner is. I thought to myself well it won't be me the other 2 look for more pretty than I do and after all they're real girls.

But I couldn't believe it when the mistress of ceremonies said" The Princess Bride for this year is. "Sissy" and the other contestants all came around me and kissed me on the cheek and congratulated me. Irene said you're so lucky Sissy I heard Greg's hung like a horse. I just gulped with the shock. What was I in for I had to get out of this and quick?

A satin sash was draped over my shoulders and it read" Princess Bride 2004. I was lead to a throne in the stage centre and an erminie cape was fastened around my neck. I was then seated and my Tiara removed and replaced with a princess coronet of rhinestones and given a silver sceptre to hold...

As all this was happening the crowd was going mad cheering and whistling and I was presented with a voucher for J.C.Pennys for $1000.

That will by you some delightful dresses my dear said the m/c.

Now my dear she said the moment you have been waiting for your Prince. The spotlight picked out Greg and he made his way to the stage to the accompaniment of the tune" Someday My Price will come".

One of the girls leaned over and whispered to me what an apt tune I bet he will come many time before morning. You drain him girl and they all giggled.

Greg took my hand and helped me stand and then he leaned forward and gave me a huge kiss. I tried to pull away but he was far too powerful and muscle bound for me to escape from. Especially in this dress and shoes.

Now as in tradition the Prom Princess bride and her groom will start off the first dance. The band then started to play Me Enjoy Being a Girl.

As Greg put his arm around me and danced me around the floor. We had about 4 dances and I asked Greg if we could sit down as I was getting tired and thirsty. He sat me down and went to the bar to get me an orange soda. Whilst he was gone Joan and Annette and the other girls came to me and said were so proud of you winning us never thought you could do it. That bit about the wedding dress was a nice touch.

Greg came over and asked me if I wanted my friends to join us. I said yes I would love that. He asked them what they wanted to drink and went back to the bar. As I took a large drink of my soda it tasted a little strange but nice.

I said to Joan how do I get out of this he will kill me if he finds out I'm a boy. Don't worry said Joan just before the party ends we will come over and say goodnight to you and Greg. Wait 5 minutes and then tell Greg you are going to the restroom and come to the door we will be waiting with the car.

But that's not for 2 hours I said. Well make the most of being a girl said Joan. I drank the rest of my drink and Greg must have known I was thirsty as he came back with another soda. I drank about half of it and Greg asked me to dance again. I said don't you want to dance with any of these girls Greg. No he replied not when I have such a pretty girl as you as my bride. We waltzed around and then a Cha Cha came on and as Greg spun me around my skirts flew out and I just knew everyone could see my stockings and panties. I heard one of the girls saying ooooo just look at those gorgeous satin panties and stockings she's wearing.

But what came next really floored me. A smoochey dance. Greg pulled me right into him and as we danced he was nibbling my earlobe and kissing my neck. My cock started to harden in my panties and so did Greg's I could feel it pushing into the layers of my dress and almost touching mine. He pulled my head towards his and planted a kiss on my lips and probed his way into my mouth with his tongue. As he did this his other hand was on my behind pulling me into his groin.

I got the tell tale sign and couldn't do anything to stop it as my cock started to pump a pent up load of cum into my satin panties. The orgasm was the most intense I had ever know and I started to go limp in Greg's arms as I was fainting with pleasure as I pumped it all into my panties.

Greg realised I was fainting and lifted me up and carried me back to the girls. As he sat me down at our table Joan said take a drink of your soda honey its hot in here. I did as she suggested and told her I needed to go to the bathroom. Joan said she would come with me, I told her what had happened and she shrieked with laughter saying you sexy girl Greg's made you have an orgasm in your panties has he. Good job you have a spare pair in your purse. I went into a cubicle with Joan and she helped me to change them. She put my soiled ones in her own hand bag saying she would wash them when we got home.

As we came out she told me my make–up needed freshening up. Why I asked aren't we going soon? Oh er yes she said but you need to keep the convincing up don't you after all what would Greg do if he found out you were a boy now. I knew she was right so I let her re do my make up. She made me look very sexy.

When we got back Greg had got me a really big glass of soda and this time it tasted much stronger than the taste it had before. As I drank it down I started to loose my fears of how I was dressed and became much more confident in myself.

It was getting nearer the time to go and I heard Joan say we have to go now you 2 love birds don't do anything we wouldn't do. She then said to Greg Sissy does the best blow job in town and all the others started to giggle as they walked out to the parking lot.

I waited a little while and told Greg I needed the bathroom again. O.K he said then it will be time for us to turn in I can wait to get you in bed my darling. I should have been scared at what he said but found myself getting aroused again in my panties.

However I made my way to the door and there were the girls waiting for me. But as I got nearer to the car they screamed we have laid out a pretty nightgown on your bed I'm sure you will be pleased with it we know Greg will love you to death in it.

They then drove off laughing all the way out of sight. What was I going to do now? I know I asked the doorman to call me a cab. Sure mam and he phoned for a cab. It will be about 5 minute's mam. I was pacing up and down yet loving the feel of the night breeze on my stockinged legs as it rippled the layers of chiffon on my skirt around my legs. I felt a glowing within me and a light headedness about me.

Before the taxi arrived Greg did asking why I was out here. Come on he said let me help you to the bridal suite for a night of love. Again I passed out but when I awoke I was laying on a large satin covered bed and my hand was resting on a pile of soft white chiffon. It was mothers wedding peignoir. Joan had put it into the room. Greg was in the bathroom he came out wearing nothing but a towelling robe. He was carrying a towelling robe and I took a couple of sips and he sat next to me on the bed his gown slid apart and I could see an enormous prick standing erect it must have been at least 10 inches long and had an enormous girth.

Does that feel better now my darling, a little I replied? He leaned over and kissed me again forcing his tongue into my mouth to explore. I just lay there scared what he would do when he found out what I was. But my cock was rock hard in my panties. Greg then held me down with one hand and slid down the bed and then his head disappeared under the skirts of my dress. I could feel him kissing his way up my thighs and past my stocking tops. He suddenly stopped, this is it I thought I'm dead. But then I felt his other hand release my cock from my panties and then felt his lips lock around it. He was sucking me off I couldn't stand the pleasure of what he was doing to me and was soon shooting lots of cum into his hungry mouth. I squealed out with delight and almost fainted with the intensity of the pleasure he gave me.

Why had he performed a blow job on me? A wimpy sissy boy. I thought he would have beaten me unmecilessly when he found out I wasn't a real girl.

He removed his head from under my skirts and then started to kiss me passionately. Oh I do love you sissy he moaned. I found myself reciprocating and really meant it. Here I was a hetro boy dressed in the most outrageously feminine dress telling the school pin up boy I was in love with him. But more unbelievable he was in love with me.

All I wanted to do now was to give him a night of love and pleasure so as he would want to come back to me for more. But who did he think I was he didn't know me. I was like Cinderella to him.But that didn't matter for the moment I was dressed as a girl and at that moment I had girl's feelings of love for my hunk.

I unzipped his enormous erecting and released it from its compound. As I grasped it with my heavily nail polished fingers it felt like a red hot poker in my hand. I lowered my lips to kiss the tip of it and felt the heat being generated from this hot hard monster. As I wrapped my pink lips around the tip Greg started to moan with pleasure as I flicked my tongue across the nob.He was moaning as I was the best cock sucker he'd ever felt on his cock but didn't want me to make him cum as he wanted to fuck my brains out.

He pulled out of my mouth and laid me down on the bed and put 2 pillows under my Ass cheeks in order to raise me up. He then pushed my layers of skirts and petticoats up around my waist and I felt his cock at the entrance to my love hole. This is it I thought and was so scared I wouldn't be able to take this monster I whimpered "Please be gentle with me Greg I'm still a virgin".

I will me darling he replied, as he gently pushed the end of his cock into my love tunnel. I winced at first and he stopped. But then he started to push it slowly but surely further into me. When he was fully inside me I felt a fullness that made me realise why girls like guys with big cocks.

He then started to slowly withdraw it and push it back; I joined in to the best of my ability. He lowered his lips to mine and started kissing me furiously delving his tongue into my mouth and trying to touch my tonsils from both ends. I was moaning with pleasure and found myself wrapping my stockinged legs around his waist to keep his cock fully buried within me. He started to moan and I knew it wouldn't be long now. With my legs wrapped around him I clasped the back of his neck and lifted myself up onto his cock I was now impaled on it and clear of the bed as I felt Greg twitching and throbbing and then it came his baby seed pumping relentlessly deep into my love tunnel. As he pumped his cum into me I cried "Oh please Greg fill me up give me your baby.

This seemed to make him pump more of this hot sticky love juice into me. We both collapsed back onto the bed and Greg left his cock inside me until it slowly shrunk and slipped out of me.

But his cum also started to leak out also. I didn't want my pretty dress messing up so I grabbed my purse and went into the bathroom. I undid one on the Tampax in my purse and inserted it into my cum filled Anus.

That did the trick I wanted to keep Greg's cum inside me as long as I could.

When I came out Greg was sat up in bed in his pyjamas waiting for me. I slowly and seductively undressed before him and slipped into my bridal peignoir set of whiter chiffon this made me feel so horny and my clitty was pushing out the front of it. I could also see that Greg was having difficulty keeping his monster in check and it felt so good to know that I could get him horny like that. After all he wouldn't even speak to me in school and if he realised who I really was I wouldn't like to be me.

I put my dress over the back of the chair and as I floated around the room the next thing I knew Greg had jumped out of bed and picked me up and was carting me over to the bed. You sexy little tease he said I can't keep control of myself I'm going to fuck you all night until I can't do it anymore. You're the prettiest girl I've ever seen and I love you and I want you to wear my ring. He sat me on the bed and slipped a silver ring on my finger which had Greg's girl inscribed on it.

He put his arm around me and started to kiss me again furiously and his hand was sliding the silky chiffon across my cock and I was so hard again. I didn't know who would last the longest me or Greg. But I'm the girl I though I must outlast Greg. That's when I decided I would give him the blow job of his life. I was determined to make him climb the walls and beg me for mercy.

 

Don't miss part 2:

After our night of love find out what becomes of me and Greg……..

  

  

  

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