A SISSY AFTER DARK free porn video

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After my wife died in that terrible accident I was missing her very much I did not have the heart to get rid of her clothes and they smelled like her which was even more reason to keep them I would go into her closet and smell her tops sometimes stick my head into her underwear drawer and inhale her scent it made me a little horny to do that and I would masturbate after unhappily cumming into my own hand...One day I decided to get dressed up like her so I did we were both similar in size so I fit into one of her dresses easily she even had a blonde wig she wore sometimes for fun I put that on and slipped into her shoes we were the same size I have small feet for a guy when I looked in the mirror I gasped for staring back at me was this cute girl and I smiled but the hair on the legs would have to go though so I shaved them clean then I sat down in front of her mirror and put on her makeup I had watched her do it a hundred times and I knew how to apply it and when I got done the transformation was almost complete I put on her bra stuffing the cups with some of her panties then I slipped a pair of them up my now smooth legs it felt really nice! I paraded around the room and admired myself I had to admit I looked pretty hot and her sexy high heels made my legs look terrific I stayed in drag the whole evening and then decided to go out for a walk so I got in the car and drove to another town where no one might recognize me then I got out swinging one of her pocketbooks and took a nice walk down the street I came to an industrial area and saw other girls on street corners and I thought wow hookers just then a car pulled up and the window rolled down..."How much for a suck job baby?"

I was stunned for a moment I never imagined this happening to me and I was going to run but then something made me stay he was kind of cute older but in good shape I had never sucked off a guy before but had thought about it when I was in college hmmm should I do it? Why not! I thought so I smiled brightly and said "Twenty bucks!" He said "Get in!" So I did and we drove to a dark alleyway then he took out his cock and it was a nice one I got him hard with a few strokes of my hand then rolled a condom down over it I took a deep breath it was now or never and I began to slowly suck his cock at first it felt funny but then after a while I began to like it and really got going when he came he really let go and filled that condom like a water balloon I giggled and said "Did I do that?" He said "Your good baby real good!" "Maybe we will do more next time!" I nodded sweetly and removed the condom carefully then tossed it into a nearby trash barrel then he drove me back to where he picked me up...I wiggled my fingers at him and said "Taa Taa" and slowly
swished my ass as I walked away WOW that was fun I was going to have to do this again...Driving home I thought about what if the guy wants to fuck me could I take him in my ass I had never did that before other than having a few of her fingers stuck up there...I would have to prepare myself for it so I did I got a large carrot and put a condom on it and began to shove it into my anus after lubing it up of course it slid in easily and I gasped with pleasure hey I liked it this was going to be easy! So I thought anyway...

The next evening I went back down there and took up a spot on a corner after a short while a car puled up and the window rolled down the guy was a big man kind of bearish but not bad looking "You working?" He asked me I nodded he said "How much for a fuck?" I had no idea the going rate for sex so I just made up a number "Fifty bucks!" I stated he said okay too quickly and I knew I said too little a price but what the hell this was my first experience so I got in and we drove to an even darker alley he made me suck his cock hard and then we got out of the car he put me against the wall lifted up my dress and pulled down my panties I held my cock in my hand so he would not see my hanging balls but it was dark anyway and I don't think he even cared I had pre-lubed my asshole before going out but when his cock slipped between my cheeks I knew it was going to hurt he was huge OMFG what had I gotten myself into but I had to go through with it now he had already paid me and his cock began to stretch my asshole out I whimpered as the pain flashed in my brain the guy liked that and grunted and said "Take this cock bitch I am going to fuck your ass but good! I like a dirty whore like you taking guys cocks in his ass then he reached in front and snatched my cock out of my own hand and began stroking it while his big cock kept going deeper and deeper inside me! I gasped with pleasure and pain and he began to fuck my ass hard I was moaning and he was grunting and before long he came and I came with him...WOW! I loved that! After he pulled out of my ass and I got rid of his full condom he took me back to my corner but I had had enough for the evening my ass was a little sore that was it for me tonight I was going home...While soaking in the tub I relived my experience and got hard again and I knew I would be going back out there soon!
I was having the time of my life being a dirty street whore was fun! Now that my ass was broken in I had it made!
And the money was good too!

Never THE END!

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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, ...

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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
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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....

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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...

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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...

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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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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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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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