My Sissy Life free porn video

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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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Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

3 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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...

2 years ago
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Sissy Gets A Black Master

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

2 years ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

3 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

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