Sissy Start free porn video

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When I was a young man and still living at home my parents went away for a weekend which was fairly rare thing to happen. We lived in a cottage on a big estate where I had grown up and mum and dad both worked. They left on the Friday so I have a boozy night out with my mates and got to bed a bit the worst for wear. Next morning I was awoken by a loud knocking on the door, not what I wanted after the night before.

I dragged myself down to the door in just my dressing gown and opened it to find Doreen standing on the door step. She was the daughter of one of the other estate workers and several years older than me. As k**s we had played together at times with the other k**s of the same age who were from families who worked the estate. I had not really seen her for some time as she had got married a couple of years back to one of the older farm hands. But here she was all cheery and smile saying hello. I managed a “hi” as she invited herself in. She then told me that my mum had said they were away and had asked her to drop in to see I was okay which knowing my mother sound about right!

“So are you going to make me a coffee then” she asked “or just stand there”? I moved to the kitchen to put the kettle on and made the said coffee which I was much in need off. I was not too sure what to say to her but all was fine as she chatted away about when we were k**s and the games we use to play.

She laughed at my obvious embarrassment when she talked about how I was dressed as a girl by some of the older girls and then I would play with them as their younger sister. It happened several times and I did remember enjoying the whole thing but it was not something I was now happy talking about. But Doreen persisted in the line and said what a nice little girl I made. I was squiring I have to say at this point and then it got worse as she pointed out my now long hair which I had grown since I left school several years ago. “You look even more like a girl now than you did then” she teased “bet you still like to dress up”?

If I thought I was squirming before I now was for sure. The answer to her question was “yes” and I had a small stash of woman’s cloths I would dress up in when no one was about. My mind was racing and I answer her in an annoyed voice “no I don’t, who told you that”?

“No one told me I saw you a couple of times through your bed room window. I was going to say something to you mum and dad but thought that would be unkind”. I was stuck for words and then she said “I could still say something if you like or I see your friends down the pub sometimes and I could tell them”. I was frozen with embarrassment and the feeling of guilt.

She smiled broadly and said “cat got your tongue”? I just blurted out “you won’t say anything will you, I was just fooling around it was nothing”.

“ I won’t say anything, not if you’re a good boy, or should I say good girl” she giggled. ”Go and open the front door I have left a bag outside and I what you to bring it in”. Outside was a fairly large hold all which she told me to take to my bedroom and put it on the bed. She then told me to leave her in the bedroom and wait back in the kitchen. After a couple of minutes she came in to the kitchen and I was instructed to go to my room and put on the clothes on the bed and then return to her.

On the bed was what was obviously her old school uniform. She was a big girl and always had been so she must have realised that there was a good chance these clothes would fit me, which they did apart from the old blazer which was short in the sleeves. Navy knickers, plated skirt, white blouse, white socks (tight fit), and blazer.

I walked back in to the kitchen not know what to say or where to look but Doreen seemed pleased. “Very nice, now let’s do your hair”. She sat me in a chair and brushed my hair out and then put it in to small bunches. “Now stand up and let me see you”.

She walked around me and smiled. “So pretty, what a pretty girl you are Jane”. Jane had been the name of another girl off the estate and I think it was Doreen’s best friend. “lift you skirt up and let me see your panties”. I lifted it up and she ran her hand over them which gave me an instant hard on.” Do you want to see my sexy panties” she asked and almost at once raised her shirt to show off here floral patterned nylon panties. “Nice? Come and touch them there’s a good girl”. I ran my hands all over them and the feeling was wonderful I have to say. Doreen was letting out little moans. “Take my panties off please”. I obliged and her thick brush came in to sight. My hand was straight up feeling her thick black mass of hair and she almost instantly parted her legs letting out a loud moan at the same time. “Put your finger in me Jane, feel how wet I am for you”.

God she was wet, my inexperience made me think she had pissed herself. I pushed my finger deep in to her and she just moaned louder and louder. “O kiss me, kiss me” she pleaded. I straighten up to kiss her lips and she pushed me down “not on my mouth Jane, where you know I like it” and she pushed my face in to her cunt. Again my inexperience told but from her moans I soon found out what she liked and did not like.

She held my head firmly while I licked her out and finally she had a massive orgasm bucking away at my face. She stood there panting for what seemed an age with her cunt still pushed in to my face. I was desperate to do something to relieve my hard cock so started to rub it slowly at first but then getting more frantic. “stop that” she suddenly shouted “stop now”. I did as she asked and stood there desperate for relief. “I what to see it, so knickers down for me” she ordered and I obliged. “still a tiny little sweet thing” she mocked “but you have been a good girl so I think a treat is in order”.

She walked or to the kitchen table and bent over lifting her skirt back up. Her legs parted I could see her hairy cunt which I had just licked out. “Come on then do you best and give me a good fucking”. God I was good to go but I was soon over shooting my spunk up inside her. “Have you come” she asked “Don’t put out of me, keep you cock up me until I say to take it out”. She then started to finger her cunt and the moaning restarted. My cock slowly got limper and then gravity took over and it flopped out.

“Lay on the floor on your back, now” she ordered and once I had done this she sat on my face with her cunt over my mouth. She rubbed her cunt backwards and forwards over my mouth and nose “this is our little secret and you are my little bitch, understand”? She lifted herself up just enough so I could answer her in the positive then she pushed her cunt back in my face. “Lick me clean; get that spunk out for my cunt”. I would have but I could hardly move as she pushed down on me. In this position she then rubbed herself off again having another orgasm.

She sat on my face for several minute after coming, breathing heavily. Then she raised up again and asked “who’s my good girl, who’s my dirty Lesbian bitch? “You are” I answered and then she pushed her cunt back down again on my face.

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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...

2 years ago
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Sissy hypno The beginnings

The beginnings of cock lust – Sissy Hypno pornFOR THOSE NOT INTO STORY OR BUILD UP, SCROLL DOWN TO THE ******** MARKER FOR EROTIC ACTION!Felicity heard Billy come rushing down the stairs from his home quarters above the pub, he swung around the doorframe and appeared behind the bar area calling out to the Indian beauty who was sat looking out the window for a moment.Felicity stood in an empty pub window looking out at the welsh countryside. As far as her Indian eyes could see, were blankets of...

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