My Life As A Sissy (rewrite) free porn video

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This is equally on the topic of "FIRST TIME STORIES" or "TRANSSEXUAL" and is an updated version of the story I sent less than 24 hours ago ***

My Life As A Sissy

From the earliest awakening of my sexuality I felt a strong desire to be girly.  I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless.  I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys.  My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym.  I was back to being deliciously smooth, and by now I was starting to get erections and masturbate, though I hadn’t had an orgasm yet.  My favorite way to arouse myself was to tuck my penis between my legs and squeeze my thighs together - and when I was shaved I looked a lot like a young girl.  Soon I experienced my nipples, they made me feel a fantastic pleasure that I wanted to never stop, I couldn’t think about anything else when I was in nipple pleasure land.  My precious pink tender nipples, I can’t imagine sex without them!  One night when I had my wee little dick tucked between my legs and was fondling my nipples into ecstasy it happened, my body had a fiery explosion and there was all this white fluid that gushed out of me - I didn’t know if this was normal or if was dying!  But you bet the next night I tried it again and I knew this was my fantastic secret passion, something I would look forward to every night in bed.  My orgasms came from deep in my body and radiated all through me - different from the normal stroking technique I soon learned, though I wasn’t so interested in being ‘manly’ or rough in the way of ‘normal’ boys.  I came to think of this as my natural way of having orgasm, and it made me feel like a girl… so delicious.

A few years later I started having sexual relationships with girls and women - actually it never occurred to me to be attracted to men, I certainly wasn’t gay.  A man with body hair and man smell could never turn me on.  I experimented with anal sex by myself, kind of exciting sometimes, but not that pleasurable for me. It wasn’t until many years later that I started to discover where my deepest desires could find expression.  

Ladyboy Paula was taller than me, especially on her heels, and hot looking with her long black hair and makeup.  I had thought about having sex with a transsexual and sucking my first cock for years till I finally came across her ad and showed up at her place, ready to take the plunge.  We stood facing each other, looking each other up and down then she drew me close and put her arms around me and whispered, “Yes baby, relax now, this is what you want baby”…. she took my hand and pulled it down where I could feel that she had a good sized cock in her silk panties, then she started removing my clothes and had me lay down on the bed.  I was stripped, laid out nude, and with my slender hairless body and pale skin I felt very girly-submissive.  She looked down on me and starting caressing and pinching my nipples, smiling as she saw me react like any girl, my body twitching, hearing me whimpering in pleasure.  When someone touches my nipples I get so aroused I can’t stop, I’ll do anything.  She bent down and her long lovely hair brushed over my face as we started kissing on the mouth, working tongues into lips, damn sure I was totally hot now!  Then she pulled off her panties and I got a look at her (his) cock for the first time, hanging halfway hard. I let out a sigh, it was substantially larger than mine, I stared in awe.  Paula slid onto the bed and straddled me, thighs across my chest, and stripped down to just a bra, revealing a chest that was quite flat.  Her large cock was poking my chin, staring me in the face, daringly close to my mouth ….. and she gently ordered me “open, open baby”, and for the first time I took the tip of a penis in my mouth, running my tongue over the tender pink skin, exploring the fold underneath and the opening at the end and I was lost up in sucking the shaft as it swelled to full length and stiffness … my god I’m really doing this!  Paula started fucking my mouth in slow small thrusts, and soon the most wonderful thing happened…. I tasted my first *oh-my-god-sweet* drop of pre-cum and I knew that all of this came naturally for me, that I would always crave this sex honey, that I was hot as hell for a full mouthful of it!  She was breathing harder now and grasped my head with one hand, pulling me to just the angle for her ultimate pleasure…  then, close to orgasm, whispered “lick my balls baby!”.  OMG I was licking and kissing her balls, the ultimate act of willing submission and emasculation.  I thought, no real man does this, only a queer one … and I was so frickin’ excited about finally acting out my craving for queerness and having a hard dick!  Paula was moaning and stroking faster and she let out a gasp as streams of hot sperm squirted across my face landing in one eye, in my hair, running down my cheek, and inserted the penis-head into my mouth for one final spurt…… the cum was thick and warm and the taste was indescribable, sweet and salty and viscous……. it might take a little getting used to…. and before I could think about it I had swallowed my first creamy load. That was the first day of my life as a cock loving sissy faggot *

Every day I think about taking a cock in my mouth, making it cum, tasting the creamy love, and of course I swallow after savoring.  Each time I let myself go more completely, and I began to accept that I was not just curious and bisexual. I didn’t think about dating women, I was having more fulfillment being sissy gay. 

A year later I met Jennifer at Obsession Bar and went with her several times. It got so I looked forward to being with her like nothing else, my appetite for her and her package was truly obsessive.   Jennifer was a long legged beautiful Thai T-girl, her sex tool was big in every way, and so I developed my preference for long tall T-girls. I loved feeling overpowered like a girl, looking up her impressive cock and into her eyes, having her insist that I suck it, and she encouraged me to relax and enjoy my feelings of femininity….and when she bucked and gushed in my mouth and her hot cream streamed on my tongue I thought, I don’t want this to ever end, I want to spend the rest of my life with her cock and her cum in my mouth!

Our penises together were a sight… mine looked like a half size version of hers, and more pink and feminine.  When soft the hood shrivels down it becomes tiny. Jennifer said that I wasn’t at all manly, that what I had down there wasn’t a dick but a ‘clip.’   She slowly sensually masturbated my clip with thumb and forefinger as she looked intently into my eyes.  God, I could almost cum just by looking at her long bare legs around me!  The excited sounds I made were high pitched for a guy, she seemed surprised and smiled amusedly.  She pinched my nipples with her other hand and soon I was twisting helplessly and sounding just like a girl in orgasm, making a gooey mess in Jessica’s hand, oh sweet release, I feel like a girl when I cum, it’s the real me, it’s the me I love being.

Sayuri is a Japanese post-op transsexual nurse that I fantasize about often.  I imagine she knows the depths of my sexuality.  She is obviously comfortable with her full transition to female, and as I indulge myself more and more in my relations with ladymen I think of how exciting it would be if I made the final step myself. I would love Sayuri to be the doctor who emasculates me and forms the new pussy between my legs.  

                                             

Her words to me ***************  

Bobbi… I want you to consider having sexual reassignment surgery - removal of your undersized penis and testicles and surgically reforming your sex to become female.  You know that your baby-like weeny is only good for giving a woman’s vagina a bit of a tickle, nothing like the penetration she craves from a man.  Bobbi I know you dream about having a pussy down there, an itchy pussy slit between your smooth shaved legs!  We could perform your castration today, starting by getting you nude and strapping you to the operating table with your legs spread wide open, on display; my pretty nurse assistants will anaesthetize and shave you baby-smooth down there, giggling as they play around with your useless limp pinky.  Maybe they’ll fondle and suck your nipples and listen to you whimpering like a young girl. Without your balls your penis will be just a soft, hanging appendage, no shaft, just shriveled skin over a penis head the size of a pink jellybean.  You can get used to living this way for a while, we’ll dress you in silk panties so you can experience your emasculation, aware that girls are thinking about little Bobbi, stripped of his manhood.  

Then you’ll be ready for your penectomy - becoming dick-less.  Feminized guys like you find this so deliciously exciting, being separated from your male part, impotent as far as exciting females;  a man without a penis is hardly a man any more!  The moment the scalpel passes through the base of your little organ you fathom the irreversible separation as your tiny member falls into the nurse’s hand with a quick spurt of blood;  you gasp as you realize it’s final, and it passes from eye to eye as all the girls present in the room see the shock on your face. “His manhood is gone…” 

You may as well get used to wearing a skirt now Bobbi, we know you’re already into stockings, high heels and lipstick, you even paint your toenails fuck-me red and shave your legs, you little sissy faggot.  Now that you’ve been snipped, you’re almost one of the girls!  Vaginoplasty is the final step; you’ll have a pair of hungry pussy lips around your tight slit… we make a precious pink clitoris out of what was once your dick.  You’re gonna love to play with it all day……

Time to begin your hormone breast enhancement, you’ve always wanted to have soft round titties with perky female nipples, then it will be obvious to everyone that you’ve become a gurl.  All that sperm you’ve been swallowing has already started to affect your hormone activity, hasn’t it?  So that more and more it’s the sight of a cock that makes you hot, not pussy anymore.  I want to see your nipples all erect and pink, standing out against your powder soft white skin, your nipples turn you on, little bitch!  Oh Bobbi, the sensation of having your tits fondled and your nipples sucked is pure ecstasy, making you lay back in total submission; you’ll eagerly open your legs for the hand reaching into your panties, sliding a finger over your wet clitoris, working into your tight cunt…  then with your pretty legs and ankles pointed at the ceiling, you feel your tender cuntlips taking the man-sausage inside you, quivering at the entrance, ohh the sweet penetration!

I hear you whimpering and moaning, you’re intoxicated by the thought of all this! I know what makes you pant and squirt in your panties……. you’re a dickless sissy gurl, Bobbi!

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My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

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