A Walk On The Sissy Side free porn video

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It was a normal looking non-descript house in a normal looking neighborhood but the address on the door matched up with the directions he had been given. James pulled into the curb at the side of the road and put the car into park. The radio cut off and he was surrounded by the silence. He felt a small knot of tension in his back and a growing mix of excitement and apprehension. He swallowed and pulled the key out of the ignition. Opening up the door he climbed out of the car and started walking toward the door.

Approaching the door he could see a note taped just under the doorbell. "Just come in and look around it said". James shrugged and pulled open the screen door and then turned the handle on the door knob. Sure enough it was unlocked. He pushed the door open and walked inside.

He was standing in a short dark hallway. Ahead he could see dim light leading from what was obviously the living room. He could feel his excitement growing in anticipation. When he had first received the instant message from "akinkycpl" while playing around in the fetish chatrooms he had never imagined it would lead to this real life encounter. He was conscious of his cock stirring in his pants as his excitement overwhelmed his sense of unease.

James moved forward into the dimly lit room. He paused for a moment at the door to take in the view that presented himself. It was just as he had been told to expect. Looking down he could see the man he knew only as "Sherri" stretched out on a rack like device on his belly. He was blindfolded and tied down on his belly. He was dressed up in a frilly black corset and had a o-ring gag in holding his mouth open wide. Another note was sitting on his back.

Looking around further in the dark room James could see the woman "Carol" sitting in a chair in the corner on the room. The only light in the room was from the dim bulb in the light fixture directly above "Sherri's" head so he could not get a clear look at her face. It appeared that she was dressed similarly to "Sherri" but he knew that, according to the rules laid out in strict detail online, that his fun was restricted to the man spread out on the rack in front of him. Which was fine by James. He had been fantasizing and playing with sissies online for months now. He was finally going to cross the line and play with one for real.

He walked over to "Sheri" and picked up the note on his back. Looking closely in the dim light he was able to read the note. "This is my bitch slut 'Sherri'", it began. "I'm giving her to you to play with tonight. She is a total slut whore and craves your use and abuse. The only limit is that you can't do anything that causes permanent damage to her or to the furniture. She loves to be called names will do every nasty thing you tell her to do."

James dropped the note. It was exactly what he was hoping for and had come here tonight in anticipation of. He looked down at "Sherri". "Sherri" has obviously heard him come in and could tell from the noise he had made crossing the room that James was in the room and was now standing directly in front of him. The rack-like device had been raised up to where "Sherri" was directly level with James' crotch. "Now I know why she wanted to know my inseam measurements", James thought to himself. He cleared his throat. To his side he was aware of "Carol" shifting slightly forward in her seat as she sensed the game was about to begin.

"Hello slut," James said harshly

"Sherri" squirmed slightly in the rack. James reached down and stroked his face. He was wearing full makeup and his lips, stretched out around the o-ring gag, had been been given a coating of bright red lipstick. "You look like a fucking whore Sherri," James announced. "Are you?"

"Sherri" hesitated and the nodded his head up and down.

James laughed. "I'm glad we both agree," he said.

He moved his hand down to stroke "Sherri's naked back. He could see the goose pimples on his bare flesh. James moved his hand down and around "Sherri's" chest to explore his front. Doing so caused his crotch to rub up against "Cherri's" face. "Sherri" let out a moan of excitement as he felt James' hard cock pressing against him through his jeans. He gave a louder moan as James's questing fingers found his nipples.

James gave a small snort of surprise at what he felt and knelt down to look at "Sherri's" chest. Sure enough his nipples had small clamps attached to them squeezing them tight. James gave a small laugh. He reached up and pinched the right clamp between his thumb and forefinger. He twisted it and pulled and was rewarded with a small grunt of pain and surprise from "Sherri".

James stood up and began to walk around the bound figure letting his fingers lightly slide over the skin and the smooth fabric of the corset. "'Carol' has given you to me tonight bitch. You're all mine. But don't worry too much. I'm not a sadistic bastard. I"m just going to make you my fuck toy."

He was rewarded with another loud moan and conscious of his cock growing almost painfully stiff in his jeans. By now he had reached "Sherri's" ass and looking down he could see a nice fat dildo shoved in deep into his ass. Further inspection revealed a length of thin rope wrapped and tied around his balls penning "Sherri's" cum up. James chuckled again for "Sherri's" and Carol's benefit. "I see that "Carol" has you prepped and lubed up for my cock," he said as he reached out and grabbed the base of the dildo giving it a few quick tugs and pushes.

"Sherri" wiggled as hard as he could in his bound state. James continued moving down and around the bound sissy. "I like how smooth your legs feel slut," he said as he moved around to the other side and began to return to the front of the rack and "Sherri's" waiting mouth pausing once more for a few more seconds of toying with the dildo.

By now James was hotter and hornier than he had been in weeks. He no longer felt hesitant about sliding his cock into another man's mouth. As long as it was wet and warm he was going to use this sissy's mouth!

James returned to the front of the rack and "Sherri's" wide open mouth. A little bit of drool was unavoidably sliding down from the o-ring gag and down "Sherri's" chin. This only made the sissy even more attractive in James' mind. He reached down unbuckled his belt and then unsnapped and slowly unzipped his jeans. In the quiet room the sound was quite clear and quite distinct. James could hear a quiet whimper escape from "Sherri". A sudden stirring over to the side brought "Carol" to his attention. She had leaned forward and he caught a dim glimpse of an attractive face focused intently on the proceedings.

James reached down and grabbed the base of his cock. "Do you know what's in front of you now bitch?" he crooned. "It's a rock hard cock and I'm about to slide it into your slutty, sissy mouth. Do you know your wife is watching you slut? Do you know how much she wants to see you suck cock like a good little whore?"

He took his cock and guided it to gently slap against "Sherri's" cheek. He could see the shiver of anticipation travel down his corset-clad body. James was feeling a high level of anticipation himself. Slowly he guided his cock to "Sherri's" wide open mouth. "Here it comes, slut." he said as the head of his cock slide past the o-ring gag.

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SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

3 years ago
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The Young Sissy Chapter 3

I was running through an empty parking lot...looking for someone, or something, but I wasn't sure who I was looking for...or what. All I knew that was no matter how hard I looked, how far off into the distance I stared, all I saw was miles and miles of concrete. It was an oppressive emptiness, the vastness of the open space crushing me. I fell to my knees in despair. I don't know why I was looking anymore...everything I had seen up to this point was testament to the futility of hope. At...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

1 year ago
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The 150 Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

3 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Five Day One of the Sissy Maid Workshop Comes to an End

Teaching the Sissy Maid Workshop at the MVP, Chapter Five: Day One of the Sissy Maid Workshop Comes to an End After lunch the ladies and their sissy candidates assemble in break-out groups where the candidates are stripped, shaved and locked in chastity as each of the pathetic males experiences new levels of shame and humiliation as they are displayed publicly and most for the first time. As the sissy graduates helped herd the male candidates into the appropriate classroom I...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

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