A Sissy Escalation

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By phantacyzz

Madison and Meredith were on their second bottle of wine and the topic of conversation had become sexual in nature. Meredith and Madison had a similar look. Both were thin with pale skin and dark hair and eyes. Meredith was a bit taller with a flatter chest compared to Madison’s small pert breast. There was a sexual tension between the two which had only intensified since they began drinking.

Meredith was laughing as she described her last boyfriend, “He was funny, but not super smart. He had a great body but his…. well you know, was kinda on the smaller side, not tiny by any means, but I have had much bigger.”

Madison thought about her boyfriend in the other room and wondered whether or not she should really give Meredith something to laugh at. She smiled slyly as she finished her glass of wine.

“Josh, come here for a moment.”

Josh had been browsing the internet in the other room. He wasn’t allowed to hang out when Meredith came over. “Hi. Hi Meredith. What’s going on?”

“I just wanted to show Meredith something real quick… take off you pants.” Madison and Meredith exchanged wicked looks and Meredith started to giggle. “This is going to be interesting,” Meredith said, as she opened another bottle of wine.

Josh slowly took off his jeans while a blush spread across his face. Meredith laughed hard as she realised Josh was wearing a frilly pair of brightly coloured panties.”Do you make him wear those?” asked Meredith

“Ever since I realised he liked being a little bitch,” laughed Madison

The small bump under the sheer fabric moved a bit. “There’s no way a penis could fit in those panties,” Meredith said unbelieving.

“Show her,” Madison ordered him.

Josh took the panties off. His tiny penis attempted to stiffen, then stopped when they both began to laugh. “Wow, Madison you definitely have me beat in the boys with a small dick department. It must get bigger than that though, right?”

Meredith leaned over and gave Madison a deep kiss, her hand slowly moved up her shirt and cupped her breast. She quickly glanced over at Josh’s penis. It had grown, but it was still only a three inches long. “How can he please you with that?” Meredith asked

“He doesn’t,” Madison smiled. Turning to him she ordered, “Go ahead and stip. You can watch, but don’t you dare touch yourself.”

Josh did as he was asked and watched as Madison and Meredith slowly undressed each other between kisses. When they were completely undressed they laid out on the couch and gently stroked each other’s pussies. “I’ll leave you two alone,” Josh said as he began to stand up.

“I want him to watch,” Meredith whispered while her lips brushed Madison’s

“Sit in the chair in the corner. You can watch, but we’re going to lock that silly thing away, so we don’t have to look at it,” Madison said, as she retrieved the chastity device.

“What’s that?” asked Meredith

“It’s so he can’t play with his little dicklette.”

“I can’t believe you’re with such a sissy,” Meredith laughed, while she pulled her cell from her purse.

“They say you can’t help who you fall in love with,” Madison said, as she clicked the lock on the device and gave Josh a light kiss.

Josh could taste Meredith on her lips, causing his penis to push against the cold steel of his tiny cock cage. “Who are you calling?” asked Madison

“Well, it would be nice to have some real men here,” Meredith said as she hung up the phone. Madison felt a rush of anxiety and excitement when she thought of the prospect of getting fucked by someone else.

“What do you think Josh, you want to watch your beautiful little girlfriend get fucked by a real man, with a real cock?” Meredith asked, while pinching Josh’s nipple and caressing his exposed balls.

Josh mumbled something while his face and chest turned bright red. Meredith pinched harder and gave his balls a smack. “Yes! Please!” Josh yelped.

“Good, because that’s exactly what’s about to happen.”

Madison and Meredith played on the couch until there was a knock at the door. Two, large, very fit, attractive men walked into the room and gave Meredith a deep kiss and Madison a kiss on the cheek, while admiring the girl’s magnificent naked bodies.

“Started without us?” said the darker of the two men.

“And who’s that?” said the other, pointing to Josh on the other end of the room.

“Don’t worry about him,” said Meredith as she began to unbuckle his pants.

Madison followed suit and began to undo the other man’s pants. She gasped and looked to Meredith when she uncovered a thick 8 inch cock that hadn’t even become erect yet. Meredith winked, and said, “I told you,” as she took the other man’s cock in her mouth.

Madison looked over to Josh with a questioned look, and he nodded. Madison took the large cock in her hands and smiled. Josh watched on in a pleasantly jealous arousal at what ensued. The 1st man fucked Madison in numerous positions, then the two men switched girls. Sometimes, both men would fuck one girl while the other girl assisted. Sometimes, just the girls played while the men stroked their enormous cocks. Madison let the men do things that her and Josh had never done, and she seemed to be drunk off the pure sexual bliss. After what seemed to be hours, and Madison and Meredith had cum several times, one of the men said he may cum soon.

With a devious smile, Meredith suggested,”Let Josh finish you two off.”

“But he’s a guy,” said one of the men.

“We can change that,” Madison said, as she grabbed Josh’s discarded panties and Meredith’s dress.

“Put these on,” she said to Josh. “Meredith, grab your makeup and make our sissy into a true girl.”

The men continued to masturbate as they watched the naked nymphs make Josh into a girl. “OK, done,” said Madison, as she stepped away

Josh then began to stoke the guys off while occasionally taking one in his mouth. “What a good cock sucker,” Madison cooed

The men finished on his face, got dressed, and kissed the girls goodbye. “Go clean up and maybe Madison will let you out of your little cage,” Meredith told Josh

Josh went to the shower and got clean. When he came back into the room Meredith and Madison were sitting on the couch spread eagle. Sipping another glass of wine. Their pussies were swollen and shiny from the hours of raw sex. Madison gently slipped the little key into her pussy and Meredith spread it for Josh to lick. After a moment, Josh took the key from his mouth and quickly undid the lock on his chastity device.

“You can finish while you go down on us, but to keep things nice and neat you need to finish in the empty wine glass.”

Josh did as he was told. It only took a few minutes before his dicklette was soft and empty again. “OK, you can go to bed now. Meredith and I are going to go out, and stay at her place tonight. But before you go you need to make a decision. Drink up your little mess, or get locked up until the morning?”

Josh thought a moment, then swallowed the glass’s contents. “Good boy,” said Meredith, “But I think you still need the cage.”

She locked it over his pathetic dick. Josh began to walk back to the bedroom as Meredith and Madison got dressed and ready to go out. “Oh by the way, we had crushed up a little Viagra into that seemingly empty glass before you got so thirsty. Have a nice night, I’ll see you in the morning,” Madison smiled and blew Josh a kiss as she walked out the door, hand in hand with Meredith.

The End.

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