A Walk on the Sissy Side

by Sissycraver

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Ma, Consensual, BiSexual, CrossDressing, Fiction, BDSM, MaleDom, Oral Sex, Anal Sex, Sex Toys, .

Desc: Erotic Sex Story: A man's first time with a Cross Dressing Sissy

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.

The shock of pleasure as his cock entered "Sherri's" warm wet mouth was indescribable. James moaned and pushed his hard meat deeper into "Sherr's" mouth. Although hampered somewhat by the gag "Sherri" was quick to prove that he was no unwilling victim. His tongue lapped over the shaft of James' cock with eager abandon. James could feel the suction pulling him in deeper. He grabbed both sides of "Sherri's" head and began to slide his cock in and out. "Oh, yes, that's a good little bitch," he moaned as he mouth fucked the bound sissy.

"I'm fucking your mouth bitch." he growled. "Your wife is watching you suck another man's cock. How does that make you feel?"

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