Sissy's First Trip Out

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Kenny wrapped his right hand around Dean's shaft and began rubbing it up and down. It was already wet with saliva, so his hand glided up and down nicely.

"Now give it a lick."

Kenny stuck out his tongue and hesitantly licked the tip. The salty taste made him scrunch up his eyes as if he were eating something sour.

"Now open that pretty little cock-sucking mouth of yours, sissy," said Nadia, "and stick out your tongue." She seemed to be enjoying the faces Kenny was making.

Nadia took hold of Dean's cock and started slapping it against Kenny's tongue. After about 10-15 cock slaps, Nadia once again grabbed the back of Kenny's head and pushed him towards his fate. The now fully erect cock was forced into his mouth and he began to suck. He felt his lips being stretched by the sheer girth of Dean's monster cock. Salvia started dripping down his chin as he sucked and slurped.

"Spit on that juicy cock," said Nadia.

Kenny pursed his lips and allowed a long stream of warm spit to fall out. He took his hand and massaged it in. He continued to suck for a few more minutes. With every stroke Kenny took more and more of Dean's length into his sissy throat.

"That's enough," said Nadia.

Kenny pulled back and looked up at his mistress waiting for the next instruction. His face was a mess. His eyes had started watering and he had drool all over his mouth and chin. Nadia hitched up her skirt and dropped her panties. She stepped out of them, picked them up and shoved them into Kenny's mouth. She pushed Dean down onto the wooden bench and straddled him reverse cowgirl. His glistening cock slipped into her shaven pussy and she started gyrating her hips slowly. This was all happening maybe a foot away from Kenny's face, and he was loving it. Nadia started to moan.

"Oh yeah, fuck me harder you slut," said Dean. All the funny business with the little faggot was finally paying off. The gyrating became quicker and Dean started breathing heavily and grunting. Nadia was massaging her clit and staring down at Kenny.

"You could never please a woman like this, could you sissy?" asked Nadia.

"No, Mistress Nadia."

Her moaning got louder and Kenny could see Dean's cock pumping in and out before his very eyes. He could hear the squelching and pounding noises.

"I'm gonna cum!" Dean said.

Nadia climbed off and forced Kenny's head towards Dean's crotch.

"Stick out that tongue, bitch," she said.

Kenny did as he was told. He opened his mouth and stuck out his tongue. He looked up at his new mistress and braced himself for what was about to come. Nadia jerked Dean's cock quickly. One hand on the cock, one holding a handful of Kenny's hair, forcing his head to tilt back. Dean grunted loudly as his cock exploded. Ropes of hot sticky cum shot out onto Kenny's face and tongue. Kenny flinched but he couldn't move his head away. Burst after burst of jizz coated Kenny's face.

Eventually the cum eruption stopped. Dean must have felt uncomfortable after his orgasm, because he quickly pulled up his boxers and walked off. This was all too gay for him when his mind wasn't in a horny state.

"Don't you dare spit that out," ordered Nadia.

Kenny knelt there like a glazed donut waiting for instruction. His mouth was filled with semen. Nadia took a finger and started scooping the sticky liquid from his face into his mouth. Kenny had seen enough porn to know what she was doing. She didn't want him to waste a drop. He knew the procedure.

"Close your eyes and keep that mouth open."

Kenny closed his eyes. He wanted to swallow the pool of salty cum as quickly as possible, but he wasn't going to disobey Nadia again.

"Now, open your eyes and look up at me." Nadia had pulled out her phone and just at the moment Kenny opened his eyes he heard the click of the camera. Now he was really fucked. Who was she going to show that picture to?

"Swallow, bitch."

It took a few gulps before Kenny managed to swallow the entire load. He stuck his tongue out to prove he had done a good job.

"Wow, what a good little slut you are," said Nadia. "Stand up and follow me."

Kenny's eyes darted around the cubicle as he tried to locate his clothes, but they were gone. Maybe Dean had taken them. When would this end? He got to his feet and shuffled behind Nadia, whose glorious tits were still bouncing free. He couldn't help but stare at her perfectly round ass as he followed. She may have been the sexiest woman he had ever seen. She led him through a door with a sign that read: STAFF ONLY. Beyond the door was a small corridor with a door on the left and a fire exit straight ahead. She turned side on to allow Kenny to pass her, swung open the fire door and shoved him in the back. He flew out the door and feel into the alley behind the store. He felt the cold ground underneath him as looked up into Nadia's grinning face.

"It goes without saying that you are no longer welcome here," she said. "Enjoy your walk home." She winked and blew him a kiss. Then slammed the door closed.

Kenny jumped up and desperately searched for a way to open the door. But he couldn't. It was a fire door. There were no handles. He turned around and pushed his back up to the door. He glanced left and right down the dark, cold alley. "At least it's dark," he thought. He touched his cheek and felt the remnants of Dean's cum drying on his face. Then he slid his hand down to his panties and felt his cock, which was still rock hard. Maybe he was a faggot after all.

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5 Comments
SissyjohnboySissyjohnboyabout 1 year ago

I’ll suck cock for Nadia

julieslegs3julieslegs3over 4 years ago
Fantasies

I guess many of us readers of this kind of story have dreamt about being in this situation. Some of us have gone out in public dressed as a girl. Most of the time nothing happens, except in your head. However, the chance of getting caught and humiliated is always there and such a powerful influence. Thank-you for this inspiring story and the chance to relive that fantasy again.

BrendaNWBrendaNWover 4 years ago
exciting story

A nice story and well thought out .. it very much illustrates my earliest fears of shopping .. I was very afraid like that but just went one little step at a time and had mostly pleasant responses, a customer is a customer .. I acted confident and proceeded calmly (

on the outside ) .. it worked better and better over many years and now am calm .. I see how this fantasy would fit someone who crossdresses and is submissive .. I am both and more, I am a full trans female please write more, thank you, TG Tiffany

AnonymousAnonymousover 4 years ago
Continue this!

Loved it, I'm hard and horny about to whack off as I read it a second time.

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