General RP But.....but I'm a GUY! (Princess and Georgie Boy)

[BoundPrincess]

Cassie was enjoying this game.
This wasn't the first time she caught her brother rummaging through her dirty clothes hamper, taking out her panties and sniffing them. She knew there were a lot of guys that were into this stuff, but her own brother?
In a way, it was a compliment....apparently he enjoyed what he was doing. The brunette stayed partially hidden behind her bedroom doorway and watched as he looked around, made sure no one was watching then pulled off his pants and shorts and put on her panties.

This show had been going on for a while and finally Cassie decided it was time to take it to the next level.
She came into the room and giggled.
"Yeah I know," she said...."I love the feeling of lace too....surprise! your'e caught...."

Instead of being pissed, she stood there, leaning against the door frame and smiled. She was going to make him regret he ever did this.

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[Georgieboy]

George jumped in surprise and embarrassment. "Cassie! I was.. uh I.. um"
His face turned red as he looked up at her. He had been caught, but a thrill of excitement ran through his body. The little lacy panties barely concealed his young cock.

"You aren't going to tell anybody, are you?"

 

[BoundPrincess]

The sexy young brunette laughed, still leaning with back up against the door frame. The game was on and she held all the cards.
"Lucky for you," she started...."Mom and Dad are at work.....it's just you.....and ME. Since you like those panties your'e gonna keep them on...for now."

She moved forward and pointed an arm at her brother.
"Stay right where you are," she said, "while I look for something to add to the picture....yeah, this will do perfectly..."
She brought out a pink lacy bra.
"Stand still while I put this on you...."
She went to the dresser, brought out t rolled socks and stuffed them in the cups. She took out her cell phone and before he had a chance to protest, took some pictures.

"Now for some ground rules," she began...."you do as I say or else these pictures will be sent to your friends.....I always wanted a sister and now it's gonna be YOU....you wanted to act like a girl, huh? well, your'e gonna BE one, wether you like it or not."
Cassie went to the closet, brought out a miniskirt, thigh high stockings and a yellow blouse.
"Put these on," she said...."I'm taking you out...."

 

[Georgieboy]

This was George's nightmare, but then why did that feeling of excitement run through him? As Cassie dressed him, like her little toy, he felt arousal and shame mix deliciously in him. maybe he wanted this all along?

A play thing for his sexy sister. Under her control...

"Cassie please don't send that to anyone, I'll do whatever you say!! I promise!" He pleaded a he pulled the miniskirt on over his little butt.

 

[BoundPrincess]

Cassie watched with interest as her embarrassed brother pulled the thigh highs up, zipped up the miniskirt and pulled on the blouse. She already had plans but it was better that he didn't know.

He had better get used to being led around.
She brought out a pink leather dog collar and secured it around his neck...attaching a leash, she left him outside and down the street...the mall was only a few blocks away, far enough for him to be seen.

 

[Georgieboy]

As the cold leather of the collar went tight around his neck, he felt himself get aroused... but he was still so embarrassed. He was dressed like a little barbie. This couldn't be happening to him.

Still, his sister did have the ultimate black mail. Might as well do what she says. He couldn't help but stare at her cute ass as she led him out of the door and down the street by the leash.

"Oh I hope no one sees me..."

 

[BoundPrincess]

Cassie kept looking back at her brother...she had to admit, he didn't look half bad as a girl and he looked cute with his head down, trying not to see anyone.

They arrived at the mall... thankfully, for him anyway there wasn't that many inside. Cassie led him to a shoe store and bought a pair of 4" black high heels. Pointing to a stool, she made him remove his tennis shoes.
"Get used to walking in these," she said...."A good sissy craves sexy heels and I'm grooming you to become a sexy sissy girl, like it or not.....your life will never be the same....now, put these on and stand up...."
Once he did so, she made a oval motion with her finger.

"Walk slowly around the room.....do it until you stop stumbling....falling on your face will be umbarrassing for you but you need to learn how to walk in heels...your'e gonna be doing a lot of it...."

The salesgirl watched as he began stumbling.
"I couldn't help but overhearing," she whispered to Cassie...."He's a....HE? looks pretty feminine to me. Are you training him to be a sissy girlfriend?"
Cassie smiled. "No," she said...."I'm grooming him to sell him.....but he doesn't know it...."

 

[Georgieboy]

George was mortified being led through the mall, but something in him must have liked it, as he was getting slightly aroused. he could feel his cock move in the lacy panties as he strutted.

As Cassie put the heels on him, he peaked down her shirt. He was such a pervert, and this ordeal wasn't helping. He tried to stand and wobble around on the large heels.

He stumbles at first, but soon takes to it. He can feel the eyes of Cassie and the other women on him. He feels so objectified. It was a new feeling for him, and he liked it...

"I.. I think I have it down.. kinda. what now Cassie?"

 

[BoundPrincess]

Cassie looked over at the salesgirl and they both looked at George.
"Personally," the salesgirl whispered...."I think as a girl he----she--looks cute. Do you want me to box the shoes or will you wear them out?"
"She will wear them out," Cassie replied...."and thanks...."

She took hold of the leash and they walked on to Macy's.....people stopped and stared, pointed and whispered as they went by...it was impossible to hide, no way to conceal the silver cable leash attached to George's slave collar. He was like a domesticated puppy undergoing training.
THey went to the cosmetic displays.
"We need to find out which color of lipstick looks good on you," Cassie explained...."as well as make up....I'm gonna make you into a totally feminized sissy girl...."

She made no effort to disconnect the leash as one of the salesgirls motioned for George to sit in a chair.
"Let's see what shades will look good on those lips," she said...."What's with the collar, by the way?"
"It's a college fraternity thing," Cassie replied. She leaned towards her brother's ear....."you say one word about what I'm doing with you," she whispered, "and I'll send the pics all over the internet...."

 

[Georgieboy]

George strutted on his fuck me pumps as Cassie led him by the collar. He could feel the eyes follow him.

As he sat in the makeup chair, Cassie made it very clear that he was powerless. He was his sisters little play thing, and he might as well get used to it. he couldn't help but wonder, what on earth was she planning to do with him? How far would she take this?

 

[BoundPrincess]

He had no idea what Cassie was grooming him for, but he would soon find out. The perfect shade of lipstick was decided upon as well as the makeup....all the while, Cassie was on the phone whispering to someone but well out of George;s hearing range.
Once done and the cosmetics bought, she led her slave out and back outside. Cassie called for an Uber and soon a car pulled up. They were taken to a wig shop and Cassie decided on making her brother wear a long brunette wig. She had adhesive applied so it would stay on and they were soon back in the car.

"One more stop to make," Cassie said....they drove downtown to the somewhat less glamorous side and arrived at a nondescript one story building. Once inside, it was obvious what it sold....it was a BDSM dungeon store. Whips and floggers hung on a wall, chains and coiled rope on another, adult sized cages of various shapes.....
"I need a cage for....him," Cassie said. The female manager motioned for Cassie to pull up George's skirt and pull down the panties, keeping a tight grip on the leash so he would try to escape. THe manager looked at his cock.
"Hmmm," she said..."I think a size small should fit....it will be very tight...."

The manager brought out a plastic device.
"This is a cock cage," she explained....."you'll be locked up, like all sissies should be, and it has a small padlock attached....once on, only your key holder will be able to remove it..."
Cassie took the leash and secured it to a bench then got behind her brother, holding and restraining him. despite resistance, the cage was secured and padlocked.

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[Georgieboy]

He felt so degraded being led around his sister, but he did feel sexy as the wig was placed in him.

When they pulled up to the BDSM dungeon, his heart dropped. What was in store?

He felt aroused as Cassie and the Manager treated him like a sex object and spoke about him. He saw the little cage and was shocked. As it was locked on, squeezing his cock, he felt completely powerless.

 

[BoundPrincess]

With the leash padlocked to the counter, Cassie knew he wasn't going anywhere.
"I can't have you going around with a guy's name," she said...."Let's see.....yeah, Jenny is more like it. THat's what you'll be...JENNY...."
She got a little chrome tag, the kind people would tag their animals with. Now dangling in front of her brother's collar was the metal tag that read 'JENNY'.

Cassie and the store manager did some whispered talking then Cassie came back.
"I have a surprise for you....I'm selling you to this fine lady here.....her name is Mistress Cyan and your'e going to be her sissy sex slave. YOu better serve her well or she'll punish you..."
She kissed him goodbye and gave the woman 2 keys...one for the leash, the other for the cock cage.

"Now then......Jenny," the woman said......"I don't tolerate disobedient sissy slaves....you speak when spoken to and any yelling, protesting or refusal to follow commands will result in...this.."
She cracked a black leather whip in front of the now 'Jenny'.

"First things first," she continued...."I have some calls to make but in the meantime, follow me..."
She took the leash and half led, half dragged Jenny to a cage, locking her inside.

A few minutes later the woman came back. "I made two appointments for you...one is to get you started on HRT--female hormones.....as for the other...I'm going to take you to a surgery clinic and give you breast implants....a nice size 36 or 38 should do nicely..."

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[Georgieboy]

Georgie, now Jenny was speechless about what was happening to her. She felt her cock press against her cage as mistress Cyan led her to her new cage.

"Ye.. yes mistress" said Jenny after learning the changes she was about to go through. Anything for her new mistress, she thought. Maybe, if she does everything right, she'll get to please her new mistress.

 

[BoundPrincess]

"Ordinarily," MIstress said, "I keep my slaves in the back room but I think I'll keep you out here so customers can see you....again I warn you, strict obedience will be followed. make a sound and I'll take you from the cage, whip you until you bleed and destroy you.Sissy slaves should be seen and not heard....don't make me have second thoughts about fitting you with a ballgag...."
She looked Jenny over.
"Take off those clothes slave....but keep your bra and panties on....."

the Mistress Cyan helped other customers throughout the day with Jenny caged in the middle of the store. Customers, both male and female, paused to gaze at the 'girl'.....Cyan had to admit, even without the meds 'Jenny' actually looked somewhat feminine. Soon the day ended and a woman came in.
"This is the one I told you about," Cyan said, leading the woman to Jenny. "This is the one that will start on the meds..."

The 40ish somewhat plump woman looked Jenny over.
"I'm a doctor," she explained...."I'm going to start you on a Hormone Replacement THerapy regimen, otherwise known as HRT. Your voice will become soft and slightly higher pitch, your hips will become rounded and you will soon no longer have to shave---anywhere. That penis between your legs will steadily shrink to nothing and breasts will develop. Madame Cyan informs me that you'll soon be given implants....the hormones will make them one size larger and will make your nipples to permanently stick out and become extremely sensitive.....now then, time for your first shot...."

She reached inside between the bars and gave the injection.
"Your owner will give you the shots in the future," the woman said...."I just wanted to come and see her new purchase.....you might make a good sex slave...if you behave..."

The woman left and shortly afterwards Cyan locked the store. The shades were pulled down, leaving Jenny in the dark.
"I have a house in back of the store," she said...."but tonight you will stay caged in the store....tomorrow you will be prepped for surgery...."

 

[Georgieboy]

Jenny took all the abuse that Mistress Cyan lobbed at her. Dressed in her little slutty outfit all day for spectators made her feel dirty.. and horny.

When the doctor explained how she would change, she was turned on by the thought of growing her ass and hips. Her cock shrinking to a clit, her skin becoming soft.

After all, if this is what mistress Cyan wants, what can she do?

The night, in the dark, she dreams of her new tits.

 

[BoundPrincess]

In the morning, Mistress Cyan got ready to open the store for business....walking past the cage, she smiled at Jenny.
"Oh, I haven't forgotten you," she says....a minute later she comes back with something in hand. She unlocks the cage. No sooner does she do that, she reaches down and puts something on her cock and with a click, it's locked.
"There's more than one kind of cage, my sissy slut," she says, bringing over a mirror so Jenny can see what's between her thighs.

"This is your cage," she explained...."it will slowly compress that miserable excuse of a penis until, along with the hormones, it will shrink down to nothing....but don't think that even then I'll leave you unlocked. Sissies must always remain locked as a physical reminder of what they are. Now, pull up your panties and come with me...."

She led her by the leash in through the back door and into the house. 2 plates of food were on the table.
"We're gonna have breakfast," she said, "and then we'll go shopping for your new tits...."

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[Georgieboy]

Jenny accepted her fate, after all, what did pretty girls like her need with a cock?

"Yes mistress Cyan" she said as the new cage locked on.

As Jenny sat at the table, squirming in her panties, she wondered about her new fake tits and how big they might be.

 

[BoundPrincess]

Cyan had already made an appointment with the surgical clinic. They drove over after Jenny was dressed, again wearing a mini skirt blouse and heels.
Once there the receptionist stared at the woman leading another girl on a leash.
"Uh Ma'am," the receptionist said....."we don't allow things like that here. If you don't mind, please remove that.....'leash'< is that it?....and the collar..."

With a sigh, Cyan removed it, pointing to a chair for Jenny to sit. She took a clipboard, filled out the information and handed it back. About 45 minutes later, they were escorted through a door. Another girl wearing scrubs was there.
"Please remove all your clothes," she said to Jenny then noticed the cage she was wearing. At first she shook her head.
"Let me check with the doctor and see if that....thing has to be taken off...."

She came back a few minutes later. "The doctor said since the procedure will be up above there shouldn't be a need to remove it...this way please...."
She took Jenny's hand and brought her to the operating room. She was put on the table and given anesthesia. Suprisingly the nurse didn't ask about the cage.
Soon Jenny was asleep and the procedure began. 2 silicone mounds were brought over, slits cut into her chest and the object slipped in. One of the scrub nurses gazed at the mounds.
"She's going to have fantastic breasts," she remarked.

Cyan was allowed into the recovery room. She went over to Jenny, pulled up a chair and waited until she woke up.
"You have magnificent boobs," Cyan said....

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[Georgieboy]

Jenny felt the familiar feeling of shame as she paraded around at the behest of her mistress.

She couldn't wait for her new breasts to complete her look.

Upon waking "Thank you mistress Cyan. Anything to please you."

Jenny looks down and is shocked by the size of her new tits. She can't wait to play with them.

 

[BoundPrincess]

Cyan smiled.....yes, those were some of the biggest tits she'd ever seen and she already had plans for them. Soon, the female hormones would start to kick in, changing her voice, widening her hips, rounding her ass and making it so her skin would be soft, supple and hairless. Jenny already had an almost feminine look so the hormones would complete the picture. The only thing remaining on her would be that miserable excuse for a male appendage' between her thighs, already shrinking.

"Excellent," she said, admiring the breasts...."as soon as your well enough to come back home, I'm going to put nipple clamps on you...."

 

[Georgieboy]

"Yes mistress cyan"

Jenny healed quickly, and returned to her mistress shop. After just a few doses of hormones she could see her ass getting fatter and her voice higher. She finally filed out the slutty thongs her mistress would put her in. Her nipples became so sensitive to the touch. She felt them harden when her mistress would enter the room.

 

[BoundPrincess]

Days and weeks passed.
Jenny had become a woman, impossible to tell that she was once a 'he'. Even the bud sized thing between her legs---Cyan called it a 'pea'---had retracted inside the skin folds of the still barely visible scrotum, or 'ovaries' as sissies tended to call them. Cyan had considered a total vaginal implant, getting rid of Jenny's 'pea' entirely, but decided against it. No, she would keep that little growth and keep it locked away in a cage permanently as a physical reminder of what she once was and that she was owned property. Jenny even had to pee like a female, sitting down because of the size.

Cyan put clamps on Jenny's nipples....she knew the girl felt pain but she had to learn that she was now Mistress's sex toy, her pain slut. Sex was a daily thing....Jenny was bent over couches, tables, even washing machines. Cyna was a nympho and enjoyed pegging Jenny constantly. Finally she took off her strap on harness after fucking her slave one afternoon.
"Time for you to learn how to use this," she said. "This is called a strap on....it has a 10 inch long dildo attached to the crotch area but all sizes can be used with it, you just simply twist it off at the base and put on a different one...."

To prove her point, Cyan removed the dildo and installed a foot long black momba.
"Now....you take the plastic and rubber harness, put it around your waist and buckle it in place....like so..."
She secured the harness around Jenny's waist, the huge dildo swaying from the crotch area. Jenny stripped nude, led Jenny to the bed and laid on her back, legs wide apart.
"Now slave," she ordered...."Fuck me like you know what your'e doing....make me cum or I'll whip you...."

 

[Georgieboy]

Jenny had come to love her mistress, and the pain and pleasure she doled out.

Jenny looked at her mistresses waiting body. Now was her chance to give her some pleasure. The big strapon felt heavy as she approached.

"Yes mistress cyan, I'll serve you as best I can"

She gets on the bed, on her knees before her mistresses waiting body. Her pussy and asshole are beautiful. Jenny can't help but crawl over to worship it. She approaches and licks at her waiting pink pussy, her heart pounding. She had to get her mistress ready. She tentatively licks at her clit, tasting the sweet juice.

"Is... is this okay mistress?"

 

[BoundPrincess]

Cyan draped her legs to the sides of the bed, her pussy and ass on perfect display. She gently moaned as her slave's tongue cautiously lapped at her pussy lips.
"If it isin't," she replied, "I'll punish you....now, get at it, less talk and more action....get me nice and wet then stuff me with that dildo...."

She held back a smile, a sign of triumph. Jenny wasn't the first sissy girl she ever enslaved...matter of fact, she had many others in the past. One thing that made her well known in the BDSM circles was the fact that she was a veteran sissy and trans slave trainer. Other owners that for some reason didn't have to time or patience to train their slaves properly would send them to her....when she was done, they came out obedient, submissive and eager to serve. She would make Jenny the perfect slave.

 

[Georgieboy]

Jenny worshipped at her mistresses pussy. Lapping up the sweet juices that ran from her a she squirmed in pleasure. Jenny felt her new girly nipples harden in their clamps and she started to fondle her new big tits.

When mistress cyan was nice and wet, Jenny positioned her self properly. The big strap on was nothing like her little old cock. She lightly rubbed it on Cyans puffy pink pussy. She pressed it on slowly, spreading it as she went. She was amazed her mistress could take it all, but she seemed to like it.

Jenny started to lightly pump, flexing her new fat girly ass, driving it home. Her tits bouncing in time with her mistresses. She pumped harder and harder, feeling herself get aroused at seeing her mistress pleasure

 

[BoundPrincess]

Cyan attached a long chain to the nipple clamps, tugging on it constantly as her new slave did her best to fuck her. Cyan could take larger ones, but for some reason this one was driving her towards a climax, and with an inexperienced slave behind it, that alone was amazing. Did Jenny know about a woman's 'G' spot? if she didn't, then she was hitting it by mistake......
"Oh SHIT," she groaned out...."Oh shit...YESSSSSS..."
she hissed like a snake, her legs trembling....how could a new slave with no experience be so fucking good?

Soon she couldn't hold it back anymore.
"I'M GONNA CUM!," she yelled...."suck up all my juice slave.....I'm gonna....'UUUUUUUUGH!!!"
Cyan exploded, her hips rising off the bed as she squirted a girly guyser.

 

[Georgieboy]

Jenny rushed to meet her mistresses gushing pussy with her mouth. She caught the squirting juice and sucked it down. Flicking her clit with her tongue while doing so. She could feel her mistress shaking with pleasure as she lapped up her cum like an obedient pet. It drenched her face and she was intoxicated by it.

 

[BoundPrincess]

Finally her body stopped trembling and the last of her nectar drizzles from Cyan's pussy. She laid there for a moment then got up.
"Your turn slave," she said, taking off the harness from Jenny's waist.
"Lay on your belly with a pillow propped up beneath you," she said as she cinched the harness around her waist. She knew from experience that males had their own spot...it was known as a 'P spot because of their prostrate gland.

Because it was her first time with Jenny, Cyan put a generous amount of special KY lubricant.
"This will produce a warming sensation," she explained...."nice and tingly...."
It was dripping from the tip as she got on her knees and guided the dildo up to Jenny's ass.

"I'm sure your'e tight," she said as she began to gently push....."But you need to get used to some degree of pain....now just relax and don't tense up, it will make it easier on you..."
Slowly she pushed until it punctured past Jenny's puckered rosebud....there was a slight popping sensation as it burst it's way into her anal tunnel and into her rectum.