Cheating Sissy Gets His Cock Locked Up In Chastity

Goddess Tabatha plays chess while everyone else is playing checkers

Not for the first time that evening, Sam wondered what the hell he was doing.

It was 2am on a Friday night. The tiny thong he was wearing was uncomfortable. His cock was too big for it.

He’d worn the Barbie pink mini skirt and fishnets so many times in the comfort of his own home, but out here on the street, he felt vulnerable.

The man who had approached was blonde and big, with patchy facial hair and a lumberjack shirt. He smelt of cheap aftershave, beer and sweat. Wordlessly he hands Sam a battered five pound note and pulls him in to the alleyway behind them.

Sam was in a submissive trance, so turned on and so shocked by this new depth in his behaviour. He’d sucked a cock before, he was one of many straight men who had been on a gay hook up just to experiment. But this was new. This wasn’t something he could pass off as a totally normal experiment.

His high heels clicked as he followed his new patron behind a steel dumpster out of view.

He knew he made a pretty girl when he dressed up, but he had thought maybe he would be ignored. The thrill of being on the streets dressed as a whore might have been enough to satisfy him. Maybe a few people would have laugh at him, enough for him to get that dirty humiliated feeling.

But this was so much darker. He was turned on and terrified enough to make his heart race.

Sam got in close and the man grabbed him by the neck and pushed him to his knees. Awkwardly, Sam lost his balance on his high heels and fell the last few inches. The John undid his belt and pulled his pants off a larger than average cock.

“I don’t want to kiss you. Suck me.” He says

The cock in front of him was only semi solid and Sam wasted no time in putting his mouth to work. His mind fell into a next level submissive euphoria.

This was so, so low. His cock throbbed. His nose was full of bad smells, the bin and the alley and the man’s warm cock and balls.

He rubbed his tongue up against the hard cock, pushing it so deep in to his throat it made him gag. Sam’s thoughts raced into his sissy fantasies as he sucked. Use me like the whore I want to be, make me low and dirty, I want to make you cum like a good girl. I am a good girl. A good little 5 pound cock sucker. A back alley whore.

Sam’s cock was so hard he worried he might cum by accident. He was licking and sucking this man with such dedication his patron gasped, swearing under his breath. Sam grabbed his own hard cock under his miniskirt and began to tug, lifting the fabric up so his ass and thong were visible.

Would eye contact be a turn on? Probably not. His submissive desire was to serve his client but selfishly, Sam wanted eye contact. He wanted to see this man and look him in the eyes as he drains his balls into his waiting mouth.

Sam straightened his back, continuing to suck on the hard cock and tilted his head up. He finds himself looking into the triple lens of a smart phone camera as his mouth fills up with cum.

“Say cheese, slut.” The flash goes off.

A huge red flag goes up in Sam’s mind. This was a problem. He has a wife at home. And, critically, she had no idea he was anything other than a vanilla man with a higher-than-average sex drive.

And yet, he didn’t protest. The blonde’s cock stayed in his mouth, and he submissively swallowed down the seed as the camera flashed. Three pictures. Four pictures.

He felt the man lean forward to get a better picture of his ass and thong. His wife’s thong. Jesus Christ she could never, ever see these pictures.

“Hey, erm… pictures are extra.” Sam says timidly “So erm, maybe you should just go ahead and delete those?”

“Nah. I don’t think I will.” He replies.

“Hey, look, I don’t normally do this. Those pictures could cause a lot of trouble for me so I really think you should delete them.”

The blonde was ignoring him, and tapping on to his phone, the light illuminating his face.

“Seriously man, come on, I’ve got a wife.”

That remark was met with a sadistic grin as the man looked him up and down. Sam’s slutty skirt, wig, make up and high heels didn’t make him look like the average married straight guy.

“Okay sissy. Come with me. There’s someone I want you to meet.”

The studio apartment was a short walk away, even on Sam’s high heels.

There were so many red flags here, Sam knew he was getting deeper into trouble. But it didn’t feel like he was driving any more. He wanted to stay in this experience, he wasn’t ready to go to bed and go back to his normal life.

If he was going to be mugged, he would have been mugged in the alley. So who is this man taking him to meet? He was definitely curious.

His mind was still full of submission and slutty thoughts and his mouth still tasted like the cum he’d swallowed. One good orgasm might bring his dangerous situation into full focus, but he wanted it none the less. It was like his sex drive was ruining his brain.

Sam really needed to cum, the blowjob had just been too hot. Maybe he’d have a chance to slip away to the toilet to get himself off.

The studio was on the top floor of the building. The blonde client wordless let them in. The place was decorated stylishly in blacks and reds despite being small. A woman with short brown hair sat in an office chair, working on a Mac Book.

“He’s here, Goddess.”

“I can see that. Bring him in. I want to take a look at him.”

Sam walked into the studio on his heels and knelt down in front of her.

“Okay.” The woman looks pleased “Did you tell him to kneel like that Luke?”

“I didn’t.” The blonde man replies.

“Jesus. This is a slut and a half you’ve bought me. I should have known when I saw the photos.”

What Sam should have said was that he needed the photos deleted. What he actually said was thank you Goddess.

She tilted his head up, and ran a thumb over his cheek, making Sam’s cock hard all over again.

“Pretty make up you’ve got there sissy, although it could use some improvement. Your wig is nice quality, but these clothes… I think you got them from your girlfriend. Am I right?”

“My wife.” Mumbled Sam.

“Of course you did. Get on the bed.”

Sam did as he was told immediately, trailing his high heels off the edge. It felt good to lie down on the sheets.

The woman flipped up the skirt to show his hard cock. It had broken free of the thong and was throbbing against his belly.

“I thought so. You need to cum so badly. It’s making you desperate to serve and all slutty and submissive.”

She spits into her hand, drooling out on to her palm.

“My name is Goddess Tabatha. I actively seek out slutty, sissy men like you.”

Her hand begins to rub his throbbing cock. There was so much wrong with this situation, it felt so dangerous. But nothing could make him get up from this Goddess’s gentle touch.

“What’s your name, sissy?” she says, slowly working him up and down.

“Sam.” He replies.

“And I know you’re married. What do you do for a living?”

Tabatha gripped his cock more firmly and jerked him up and down. It’s like she can make his whole body feel good just by touching his cock.

“I work in marketing.” He stammered. “Marketing Goddess.”

“So it’s probably not a good look to be sucking cock in alleyways, dressed as a girl then?”

“No Goddess.”

Tabatha licks on the fingers on her left hand and begins fingering his asshole, making circles against it.

“How much do you need to cum?” She asks.

“So much.”

As he spat the words out, Tabatha gently sucks on the end of his cock. Oh God. He’s so close. Only a little more and he was going to cum so hard.

Tabatha takes her mouth away and removes her hand from his cock. Sam groans loudly in frustration and disappointment.

“Oh no, were you about to cum Sissy?”

“Yes Mistress. I mean, yes Goddess.” This woman was going to make him lose his mind. The finger on his asshole pushed and penetrated him, making him feel even more desperate.

“You need to work harder on your make up and clothes. But Luke says you give a really nice blowjob. He says you’re experienced. Is that true?”

“Yes Goddess.”

“Have you had a lot of anal sex? I actually don’t think so. You’re very tight.” She pushed in deeper and Sam’s eyes rolled back in his head with pleasure.

“I’m … straight Goddess.”

That got to her. Tabatha laughed loudly. Sam could hear Luke in the kitchen laughing too.

“No sissy. You’re not straight. I think there’s a lot of things you’re confused about.” Her hands gripped his cock again, working him closer and closer to the edge. He was ready for her to stop when she did, but even so it didn’t make it less frustrating.

“You’re a slave to this thing. I bet you’d do absolutely anything to cum right now. Would you like me to do an experiment?”

“Yes Goddess.”

Immediately Tabatha got up and returned to his side. In her hands was a pink chastity cage.

“Do you know what this is, Sissy?”

“Yes Goddess.”

“This is the tool by which I’m going to own you. To be clear. I want to see your cock locked in this pink cage. I think you want this too. It’s going to be frustrating, and difficult for you, not being able to cum. We’ll use a safe word. If you say the safe word, all this stops. Everything goes away.”

She smiles at him, taking in his shaved and leaking cock, his smudged eye make up and high heels.

“But I think you want to know where these feelings are going to take you. I can show you. Do you want it?”

Sam paused.

“I want it Goddess.”

There was no hesitation. Goddess Tabatha took hold of his manhood and began pushing it in to the small cage. She locked it with a click.

“Good girl. No orgasms for you.”

Good girl. Sam had never known two words could give him such a feeling of joy. Tabatha saw it and Sam immediately began blushing.

“If you dress like this, you’re probably a girl deep down. It’s best to accept it.”

Tabatha suddenly looked like the most beautiful woman he’d ever seen in his life. What was he doing, being with anyone but her?

She stroked his cage.

“I own this dick now. I own you. Go home and sleep and wait for me to message you. I’m looking forward to putting you to work. Oh, and leave £200 on the side on your way out.”

His mind was swimming. There was surely something he should say, some protest. But what he said was “Yes Goddess.”

And he did as he was told.

These Sissys Crave Humiliation On Cam

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