Sissy Jennifer's First Cock free porn video

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Submissive sissy Jennifer's first cock

There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck.

"I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the web a few days ago. Not saying a word, you pull the stranger into your room with the lead, shutting & locking the door behind him. You slip the end of the dog chain over a coat hook behind the door. "STRIP" you command.

Jennifer slips off her coat - it was a cold night. You notice immediately that she's toppless under the coat. Her nipples are erect and hard - is it the cold night air? or is it excitement and trepidation? As she slips her jeans over her hips you see the red suspender belt, the black stockings, the tiny red panties.

Jennifer kicks the jeans off her feet, and out of a small bag pulls out a pair of red hi heels. She slips into these with difficulty, they area size too small.

"mmm, very nice" you murmer. "Don't speak until spoken to" you command. "Turn around, step 2 paces away from the door, then lean forward so your weight is taken on your hands, Spread your legs WIDE"

Jennifer nervously does as she is told. For several minutes there is silence. She can feel his eyes on her. Then without warning his hand fondles her ass, a finger running along her crack, slipping into her sissy ass. His other hand is sliding into her panties at the front, fondling her sissy cock. He feels she is smooth, soft and silky to the touch. There is a faint smell of eau de cologne. His fingers move up to her nipples. They are still hard and erect. He flicks them with his nails, Jennifer gives a little groan of pleasure. He pinches them, twists them. Jennifer gasps, but the nipples grow harder, giving her away.

His hands are removed completely. Jennifer's disappointment doesn't last long - she feels her panties being manoevered over her sissy ass, past her sissy hips, until they are at her knees, stretched tight because her knees are spread. One hand is holding her sissy balls tight, the other delivers a smart smack to her ass, and another and another.

"That will do for a start". Pulling her upright so she can stand on her own feet, he says "turn and face me, cuddle up close. She obeys, her exposed sissy cock hard with excitement presses against his fully clothed body, and she can feel his hard masterful cock waiting to be released. She nestles against his chest, and he puts his arms around her, taking one cheek of her ass in each hand, opening her up. She imagines someone behind her, lusting after her virgin ass. A finger slips in, then two. "Next time, my slut, that ass will be mine". She shivers, although she is not cold.

Suddenly he has gone, and she finds herself being pulled by the dog chain over the back of a sofa, the end of the chain being secured to a table leg. She is on tip toe, her ass higher than her head. The comforting feel of fingers fondling her ass were replaced the sudden slap, slap, slap of a spanking, now harder than before. Her ass is hot and singing

After 10 slaps he says "now I have your attention - I want you on all fours. I want you to crawl on your hands and knees to where I shall be sitting on the sofa. There you will remove your panties completely, stuffing them into your mouth. You will face away from me, place your face on the floor and lift your ass as high as it will go. Then you will rach back with both hands and open your ass for me to inspect. GO"

Jennifer shuffled round on her hands and knees, slipped her panties off completely, stuffing them into her mouth as ordered. She was pleased the panties were so small! Then lifting her ass as high as she could she placed her cheek on the carpet, reached back and pulled her ass as wide open as she could. FLASH! Oh no! He was taking photos for posterity! "Don't worry babe, your face isn't visible" he said, and she breathed a sigh of relief. Exposing her sissy ass and sissy cock was a turn on, but she couldn't afford to be recognised.

"You don't know how close you are to having that gorgeous ass raped", but if you're a good girl you can suck my cock instead. Deflowering a sissy's face will be a new experience for me - and for you."

Jennifer crawled to his lap. While she was displaying her sissy ass he had stripped completely. His large cock was standing proud as she nestled up to him. tentatively, she put out a tongue to him, wondering if she would get it in. She opened her mouth, and lowered her lips around him, trying to emulate the porn films she had seen. He was already leaking pre cum, and it tasted quite nice. She wondered what his cum would taste like, and whether she could manage to swallow it all. His hands were on her head, holding her, and he began thrusting into her mouth. It was less of a blow job, more a rape of her mouth. She felt him get even fatter, and knew he was about to cum. Holding her tight, she choked as he came in her mouth, her lips sealed around his cock, she valiantly tried to swallow it all. Some spilt on the sofa, and he smiled. "That will mean another another spanking before I kick you out".

"You did well tonight, girl". Jennifer beamed with pride.

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Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; 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...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child 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...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

1 year ago
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Sissy in the making

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....

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