Sissy Boy/Girl's First Steps free porn video

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Hi,

My name is Lara and I am a Sissy! wow that was easy, but how did I become one now that was hard, a hard road. It all started out in the summer of 87 I was 17 lost and looking for a job. My mum who knew I was going to be a soft boy, I mean I was still sucking my thumb and had been caught many times in my sisters clothes from knickers to dress's, my mum would just smile and tell me she loved me. My Father had taken to the way of just ignoring me.

Then one day my mother came into my bedroom, I was in my sisters underwear masturbating over pornographic pictures of naked men, my mother told me to stop, told me to put my penis away, she hugged me and told me to come down stairs. On going into our front room there was a woman, she was my mums friend I used to call her Aunty Catherine, she was no real Aunty the title was honorific, I knew this was a big moment in my life, she told me to strip naked, so I did I had an erection, she asked me if I liked boys or girls, I said both, she smiled and asked what it was I liked, I said I liked men's willy's and ladies softness and smell. After what seemed like an inspection, she announced I had potential and she would take me, my mother beamed.

She told me not to dress and placed this thing on my cock that I knew would stop me getting an erection and and sadly stop me masturbating. I was escorted out of our back door naked to a van, told to get in, this was to be the start of my submission to this women's will.

A big black guy was driving the van, and when I say big I mean big, his name I found out later was Bob Johnson, a gentle caring man, who helped me adjust and became my friend. after a hours driving we arrived at my new home.

My new bedroom was absolutely gorgeous, pink and satin with lace everywhere, a beautiful four poster bed with a mirror on the ceiling. My beauty regime began the next day, with something special. I was already struggling as after lying in that very feminine room all night my balls had filled up, my cock had ached all night and I was so horny it just hurt, my discomfort was noted and she told me I would only where the device if I masturbated without permission, I agreed I would only do so with permission and signed a contract with Catherine for four years of instruction. At this point in came Bob Johnson with an erection in his trousers that made mine all the more harder but very noticeably a lot smaller. I was instructed to masturbate while they watched, its really difficult when your the only naked person in the room and instructed to do something like that, even though I desperately needed to, I stared at Bobs very prominent erection and came quite quickly, I nearly lost my legs my orgasm was that overwhelming, the shock of having to lick it all up was equally as overwhelming but I found I liked the taste and was surprised I had not thought to eat my own cum before.

As I was saying, my beauty regime was starting, with a doctor, well a plastic surgeon, my breast augmentation was booked and a mild course of female hormones was also sorted out, apparently I had been taking medicine for over two years that had kept my body hair growth to a minimum, had put some curves on my hips and bum and had given me little titties that were hardly noticeable. My penis was an acceptable 5" and I thought normal, but it was thin and I had small hairless balls. I thought it was that I was a late developer but years later I am still the same.

My breast augmentation was completed the next day my lips were tattooed red and the base of my spine was also done giving me a bitch stamp.

My eyebrows were subjected to electrolysis hair removal giving them a beautiful soft arch shape, and my pubic area was shaped, well what little hair I had was styled into a little v, my anus area was treated and to this day no hair has grown anywhere near my genitals apart from the little v. My hair which was already long was styled into a very feminine look. Nails done make up applied it was time for my first walk out on this occasion into town, all this had taken 6 months, and I looked stunning.

I also sounded good to as I had under the instruction of Catherine received elocution and deportment training, I looked, walked and sounded like a girl, and it was my Eighteenth birthday, and tonight I was going to have a birthday party.

I knew in my heart that tonight was going to be special, all the pain and training i had endured needed to lead somewhere. I could now accomadate a 11" Dildo, I could also suck and swallow Bobs cock as well and that ladies was 10" and thick a real mans cock, his balls were massive and he pumped a load that tasted pure and manly, it had been my favourite training, its all about angles, relaxation and practice, and I like to practice.

I had spent the day relaxing, a enema, a massage and the sunbed, I had bikini lines covering my 32c breast's and my pubic area and a tan that complemented my long curly auburn/red hair which was as it is naturally. I started getting ready about 5 for the party at 8, I wanted to be the prettiest girl there.

At 8 o'clock I made my way downstairs a chorus of Happy Birthday to Lara rung out, i was tickled pink, exited and then introduced to a man, a average sized man late 40's and his name was Peter Wright, I knew this man was my date but nothing was said. Catherine at about 10 asked me to take Peter to the special room, Peter had been charming all night a perfect gentleman, I walked him to my room, my special room, the room all my training had led to, and i could not wait.

The room and been set out differently, there was a feeling of v******e in the room where none had been before, the gentleman had left and what stood before me was scary, tears came to my cheeks, i was about to lose my virginity to a monster and I knew it. I was ordered to remove my clothes aprt from my suspenders and stockings and my 6" high heels, a spreader bar was placed between my ankles, and i was bent over a bench that presented my rear perfectly to Peter, this was no accident everything fitted me perfectly. Peter then informed me he had paid 9,000 for the privilage of taking me first others had paid less. He then undressed and started rubbing me all over saying what a beauty I was.

Then he smacked my bum with a paddle really hard within 3 hits i was sobbing, the pain was unbearable, as the tears rolled over my cheeks he told me to look up at him, as i did his erect cock was there to greet me he forced it into my mouth and I sucked it i knew what I had to do so I put all my efforts into it, it was not long before the tell tale sign of his ejaculation was close and then his cock twitched and his spunk hit my throat, I swallowed it all, there was a lot to swallow. His cock a thick 8" uncut stayed hard.

He walked around my back and proceeded to padlle me again pulling my cheeks apart so he was hitting my pussy I was in agony I felt some lube on my pussy and then with no preamble he thrusted forward, crying my virginity was gone, he fucked me hard and lasted a lot longer than I wanted him to at first, but the rythym of his efforts and my own know hightened sexual sensitivity took over and between us the actual fucking was enjoyable, I had needed this for a long time I called out his name and he mine, his strong hands held my hips with purpose moving to my nipples and then back to my hips rubbing my body during the transistion, yes i was enjoying this the act of us cumming together was close and when I felt his spurts deep inside me, my passion and sheer ecstasy overwhelmed me and my own cock released, I begged him to put his cock in my mouth and to fuck me again, he did not nor has ever again, but that does not mean my night was over it had only just begun

SissyLara

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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...

4 years ago
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Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

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