BDSM Library - Sissy Jennifer's First Cock

Sissy Jennifer's First Cock

Provided By: BDSM Library
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Synopsis: Jennifer, a cross dressing sissy, submits to her first man. This story was written for someone I met online, and imagined our first meeting. (Which didn't take place, unfortunately)

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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