The Adventures of Sissy Madison Ch. 01

Kent slowly opened his eyes to let his eyes adjust to the bright light from the lamp. He slowly rolled over and stretched as he saw Kim sitting up thumbing through something on her phone in a white tank top and boyshorts.

She looked at him and said "Good morning!" as her eyes shifted down to his chest. She stared at a lilac purple lace babydoll that had just risen above his bright red lace cheeky panties covering his morning wood.

"Good morning" Kent responded as he rolled onto his stomach closer to Kim. She reached over and smacked his panty covered ass with a definitive pop that stung, but got Kent's penis to full attention.

"Such a cute ass, but so lonely. And what the hell did you do with your panty choice!"

"What?" Kent asked.

"Your cute little hole is so empty I think we need to fix that and you didn't even match your nightie with your panties!" she moved his panties a little to the side and slid 2 fingers into his awaiting hole.

"Mmmmhhhhmmmm, I'm... I'm so sorry" he moaned as she slowly pumped in and out of his tight fuck hole.

Kent lay there in peace until he unconsciously started moving his ass back into Kim's fingers when she abruptly stopped.

"Alright I'm going to go get some coffee and some breakfast real quick. You will get in the tub and clean yourself up for me. I expect to get back and see your hole filled and you smelling like a beautiful flower!"

With that she quickly got up, threw on some shorts, flip flops and went into the bathroom. She quickly got ready and was out the door in less than 3 minutes. The entire time Kent lay there wishing she would have kept fingering him.

After she left he went to the bathroom and stripped off his babydoll and panties and pulled out his three butt plugs from the drawer. He stood there and pondered which he should put in before his bath. It was early in the morning so he thought the middle purple plug would be better to wear the entire day, but he knew from Kim's smack there would be even more hell to pay if he didn't pick the biggest pink one that was angled for his prostate.

Just before Kent slid into the bath he checked his phone and saw a message from Kim, "Get your cage out and slip it on."

"Yes mistress" Kent typed with a smile as his little cock twitched.

He went and found his small pink Holy Trainer and walked back into the bathroom to draw his bath. He took his cock and balls and slowly fed it through the ring being careful not to get hard. Quickly sliding the cage up his penis he forced it down on his cock to quickly lock his manhood in chastity.

Kent brushed his teeth and got the lube to put his plug in. He gave it a quick kiss and lathered the big boy up to slide in his little hole. Laying back on the bed he slide the plug half way in he started to moan and slowly fuck himself but quickly remembered how it will only end up making him cum and that would not end well for him. With 3 twists and pushes his ass engulfed the plug and a smile developed on his newly awaken face.

He sat up on the bed and slowly stood up as he felt the angled plug press on his prostate. He looked down to see his cock twitch at the pressure. With an even bigger smile on his face Kent sauntered back into the bathroom just in time for the tub not to over flow.

Kent grabbed his phone and started his Meghan Trainor playlist. He took one step in and immediately his foot slipped out from under him and he fell straight onto the side of the tub. Initially he yelped at the fall but after he realized he was ok he let out a little giggle feeling the plug pushing even deeper in his ass from the fall.

He carefully got in the rest of the way and relaxed back to enjoy his bath. Starbucks was only 9 minutes away so he knew he had less than 20 minutes to get all of his work done. After one song he sat up and began shaving his legs being careful not to miss a spot because Kim hated stubble with a passion. Luckily he didn't have to shave his balls or ass since he had just gotten a boyzillian wax a week ago. He shaved his underarms and after he lathered himself up with his honeysuckle body wash. Laying back Kent closed his eyes and enjoyed all the girly smells battering his senses.

"Honey I'm back!" he heard as the door slammed.

"Shit! I dosed off" he cursed himself. Luckily he had done all that she asked so he started to get out and called back "Great! I was just getting out."

"Ok awesome" she said as he started drying off.

Just as he was finishing drying his legs she poked her head in and said "Be a doll and slip these on for me"

In her outstretched hand he saw a ball of pink lace which made him smile even bigger than before. Kent was a sucker for cute panties and Kim knew it.

He quickly slid the pink Victorias Secret cheekinies on and opened the door to see Kim sitting in the lounge chair sipping her coffee. One step out the door Kim said "Go on and get Tyrell for me."

With a surprised look he obliged and went and got the 9 inch black dildo that she had so cleverly named Tyrell. Although Tyrell was big it wasn't as big as Wyatt which was a 13 inch monster dildo that Kent had been working on taking for almost a month now to no avail.

He plopped the dildo into Kim's outstretched hand as she commanded him to kneel.

Happily obeying Kent kneeled and watched Kim unzip her shorts and position Tyrell just above her panty covered pussy and re-button her shorts. Her cock was ready for a good suck just like a real man that pulled his cock out for a quick blowjob from his whore.

Kent sat up a little and grabbed Kim's cock and just about got his lips on it when Kim stopped him asking "What the hell do you think you're doing?"

"Um, I figured you wanted me to start sucking..." as he sat back.

"Ya, but how about you ask like a good little bitch instead of assuming you know what I want!" she scolded.

"I'm sorry, can I please, please suck your cock!"

"I don't know, I'm not really feeling it."

"Pretty please can I suck your big, hard, throbbing cock?!" he pouted sitting back up grabbing the base of the dildo and giving the tip a seductive kiss.

"Yes, now you can"

He gave the tip a kiss again as he smiled and opened his mouth wide. As quickly as he could he dropped his head as far down Kim's cock as he could. It wasn't even close to all the way because he hadn't quite unlocked his deep throating ability yet. But none the less he tried and with Kim's hand on the back of his head he felt the motivation to give it all he had. He worked for a good 5 minutes trying to please Kim when she said "Panties off now!"

Without taking her cock out of his mouth Kent stood up and wiggled his hips as he slid the panties off. Kim reached up and petted his balls in his cage as he continued to suck.

"Pull the ottoman over"

With the command he used his feet and pulled the footrest beneath him and crawled on top into a kneel. He tucked his caged cock back behind him and continued his work. He could hear Kim moaning so he knew he was doing good.

He felt Kim's hand push him down even farther trying to shove her entire cock inside his mouth. He gagged but without the push he quickly forced himself back down, moaning in pleasure and excitement as he almost got to the base when he heard an unfamiliar sneeze.

Kent quickly looked up and started to pull his mouth off that huge cock when Kim wrapped both hands around his head and held him down on her cock.

Kim looked into his eyes and quietly said "It's ok. Trust me..." With that she started moving his mouth back up and down her cock.

He quickly slipped back into his submissive state and began his oral service again with the only goal of making Kim orgasm. After two full movements up and down that 9 inch monster of a cock he felt a smack on his ass that hit his plug simultaneously. Kent immediately tried to deep throat Kim's cock with the pleasure of increased pressure on his prostate and in his ass.

"Hehehe Oh My God!" he heard the new voice in unison with Kim's gasp.

He slowly pulled up to the tip of the cock when he felt an even harder slap on his ass and plug which made his caged dick leak precum and for some reason he forced his head farther than before down Kim's cock. Gagging just a little he heard Kim moan even louder.

"Madison you are just sooo CUTE!" the woman's voice said. "And oh my god your little cock or I guess it's just a small clitty is dripping!"

Kent knew she was looking at his legs that must have at least 8 drops of precum from his blowjob session. He felt the new woman slightly rub his swollen balls as she giggled which only made his caged dick leak even more precum.

Kim grabbed his head and held it as she pumped her cock in and out of his mouth going farther and farther with every thrust.

Kent was in a blissful state having what he thought was a real face fuck. Simultaneously he felt his plug being moved around. With no control he felt his cock leaking a stream of cum but not having a full orgasm. Quickly thereafter he heard Kim breathing heavier and moaning as she was approaching her orgasm. Quickening her pace the other voice, now more familiar, said "She's leaking like a hose!" With that Kim let out a deep sigh and stopped her thrusting.

Kent slowly lifted off her cock smiling at his accomplishment in both the successful orgasm and his improving deep throating ability. He looked into Kim's eyes as her cock slipped out of his mouth. She looked approvingly at him and gave him a gentle pat on the head.

Out of Kent's peripheral he saw a body appear. He slowly looked up and saw Haley, Kim's best friend walk by and sit on the side of the chair.

Kent dropped his head in shame as he kneeled there, caged cock, cum covered legs, and a 9 inch black dildo in front of his face.

"Awe honey don't be sad. You should be proud! That's very impressive that you can take such a big cock! I know all about your little fetish... or should I say big fetish!" Haley said looking down at the slippery dildo.

"Oh you should see his other" Kim giggled "Wyatt is even bigger and this naughty gurl can't get enough of him!"

"I can't wait! But I'll wait until Madison wants to show me him."

Kent started to move away when he got a hard slap on his face. "Where the hell do you think you're going?" Kim demanded.

"I was going to get cleaned up" Kent explained to only see Kim shaking her head.

"And what do you think we should do with all that cum all over your leg?"

"I was just going to clean it off and put on some clothes" Kent said softly because he knew he was in trouble.

The girls both laughed out loud "Nope, reach your hand back there and wipe up all your juices up and swallow them like a good little bitch."

Kent did as commanded and reached his hand back and felt how much cum was really on his legs and lifted his first handful up to his mouth. He knew exactly what it tasted like but for some reason was not in the mood. He gingerly licked up his index finger and then up his middle finger quickly readjusting to the taste. Kent swallowed the first two and then moved onto cleaning up his entire hand actually enjoying the taste.

"He sometimes takes a little to remember how much he loves eating his sissy juice"

"So is he not Madison anymore?" Haley asked.

"No he's still little Sissy Madison but I like to remind him sometimes that he's still a pathetic man eating his own cum to put him in his place"

Listening to this Kent quickly reached back wiping the rest of his cum up and licking it up before Haley could stop laughing.

"Awe she's cute, but I think we can make her even cuter!" Haley exclaimed.

"You're so right! Madi put your panties back on and clean your legs up. Then you can come back out here." Kim said as she started to pull her cock out of her shorts and stand up to regain her composure from her orgasm.

With that Kent got up and did as he was told to only return to see the girls sipping their coffee and chatting.

"Put the clothes on that I laid out for you and hurry up so we can get going!" Kim said without even looking at Kent.

Laid out nicely on the bed was a light pink blouse and white shorts that he knew would only cover 2 inches down his legs beneath his cheeks. On top was a beautiful pink lace bra that matched his panties. He smiled at how cute and simple everything was, but he remembered Kim saying we need to get going, which scared him. But he trusted her and slid the bra over his arms and quickly reached around his back hooking the bra together on the first try. This was at least the 200th time he had put on a bra, if not more so it was ingrained in his muscles.

He reached down to start sliding the shorts on when he heard both women whistle. Smiling he straightened his legs and bent over as far as he could trying to give them the show they deserved. Sliding them all the way up he tucked his caged clittly behind him trying his best to conceal it as he zipped his shorts up. He slid his cute blouse on as well and looked in the mirror. The bra was slightly visible through the blouse but his panties could clearly be seen through the white shorts. Slutty he knew, but he loved it and even felt his cock stir with excitement.

"Do I really have to go out like this? I just look like a guy in girl clothes."

"We'll fix that real quick don't you worry cutie," Haley said as she hopped up with an excited look on her face.

She hoped over to Kent and opened up a makeup case and made quick work of his face. At the end he saw a simple yet cute girl with short hair looking back in the mirror.

"Don't you start whining, we're going to get you a wig before we go to the mall" Kim said looking at Kent's face. He smiled ear to ear and clapped his hands together really quickly.

"Yay!" he exclaimed "But, what shoes do I get to wear!"

"Haha I completely forgot about shoes, but you can only either wear your fuck me heels, or these" as she pulled out 2 inch strappy wedges that were exactly his size.

"I vote her fuck me heels" Haley said with a deviant grin on her face.

"Well I guess I know what outfits you're going to pick out for my sweet sissy." Kim said with a laugh.

With that Kent slipped the wedges on and twirled for the girls, ready for what was next.