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[ Kim Possible ] Afternoon Affair	By : vzon20011 Category: Kim Possible > Het- Male/Female Views: 59467 -:- Recommendations : 2 -:- Currently Reading : 3
Disclaimer: I don't own Kim Possible, or it's characters. This is fantasy fiction parody fanficition. Don't try these ideas. This not for profit, just for fun.

Chapter List
- 9
- 10
- 11
Chapter ten
This chapter will contain: Gender Bender, Sissy Boy, Forced Feminization, M/F, car sex.
Part one,
“ Ding A Ling Ling,” went a little bell at the entrance of a women’s clothing boutique. “Whew! I hope they didn’t see us come in here!,” said Ann Possible shutting the door behind her fast. ‘Who would have thought a much needed day of shopping would end this badly. Why did I ever bring him along!!!,’ she thought rolling her eyes. “ Sorry Ann, I guess my aim at the trash can was a little off. Heh heh” said Ron Stoppable sheepishly. They moved away from the glass door as some tough looking gangsters walked by. The red stain of a cherry slushie was visible on one‘s shirt. He was smacking his fist into the open palm of his other hand.
“ Dr. Possible, Good to see you again. Welcome back,” said the shop owner named Joyce. She seen Ann, and Ron looking outside. “Is something wrong?” she asked concerned. “ My young friend here had an accident with those hoodlums. Now they’re looking for him,” said Ann. “ Ah’ Those guys. They showed up here in this little shopping district about a month ago. From what I understand, a new shop down the street sells what they want. We’ve lodged complaints with the board, but as long as the shop isn’t doing anything illegal. There is nothing we store owners can do. They do cause a lot of trouble when the police aren’t around,” said Joyce walking over to the door looking out with them. The three of them could see the cherry slushie guy stopping people, and talking to them while raising his hand up to Ron‘s height.
Soon, more gang members appeared joining the slushie‘s group. After getting Ron’s description. They dispersed to look for him. No cars were allowed around the shops’ avenues. So people had to walk a block, or more to parking. It should be easy enough for him to be spotted.
“Well, Of course you can stay here as long as you want till they leave,” said Joyce. “ Thank you very much. Ooooh, that wasn‘t here last time,” said Ann looking at a new dress. “Hello, focus Ann! Vicious gangsters who want to do me bodily harm outside,” said Ron gesturing. “ We can’t do anything till they leave Ron. So I might as well look around,” said Ann half listening.
Two hours later, Ann found a really bored Ron sitting in a sparse waiting area. An outdated television with broken knobs played infomercials. Five year old fashion magazines were the only reading material. Ron looked like some prisoner spending time in solitary confinement. “Ready to go Ron?,” asked Ann missing the obvious.” YES!,” He jumped up heading toward the shop door. Then screeched to a halt as Joyce pointed to a pile boxes saying, “ So Dr. Possible, Do you want to take them now, or have them delivered?” If it was Ron’ s mother, she would have him carry everything to the car. Ron gulped looking to Ann. “ We’ll have them delivered,” she said smiling at him
To their bad luck, the slushie gangster had set up a command post outside the shop. “What am I going to do now! I can’t stay here all my life!,” said Ron panicking. Visions of the store’s waiting room flashed in his mind. “Calm down Ron, We’ll think of something,” said Ann. “ The only way I can get out of here is change my appearance!,” said Ron throwing his hands up. “ I think I can help,” said Joyce smiling.
“Thanks, Ladies. Come again!,” said Joyce standing at the door of her shop. She acted concerned about her patrons walking past a bad crowd. The long hair blonde had a youthful attractiveness with the right shade of red lipstick, and make-up. Wearing a yellow sundress with wooden clogs. Men stopped to admire her figure. Her companion was an opposite of her brightness. She was also beautiful with long jet black hair with black lipstick, and silver make-up on her face. Wearing a black, and silver studded collar around her neck. A black lace up corset vinyl top with small cups that barely contained her pale breasts. Small black vinyl shorts, and thigh high vinyl boots. A ridding crop was in one hand, and a shopping bag in the other. Men, and women were both afraid, and attracted to her at the same time. Images of her dominating them came to mind.
“ Yo! Hold up! Hoe!,” said a man’s voice behind them. Both ladies looked at each other. “Oh Shit, they thought. “Hey Bitches, I wantta ask you something.” The women turned to see the slushie gangster with his crew behind them. “ Have you seen a little blond guy about this high?,” asked slushie raising his hand level with Ron’s height. The women shook their heads no. “ Damn, I wonder where that little bitch went,” said slushie frustrated. Then the gangster started to stare at the blonde more closely. “ You know Ho, you look familiar. Have I seen you before?” The blond shook her head no. “Your very attractive. Watta you say we get together later tonight. I can show you a good time. I’ve got plenty of money, because my Momz owns a shop down the street. The blonde shook her head no again. Looking to the ground shyly not saying anything. Slushie grabbed her by the arm bringing her closer. “ Come on Bitch! I know you’ll enjoy it!,” said Slushie into her ear. He reached his hand under the blonde’s dress to grab her ass. His little finger strayed up under the panties into her crack. “EEEEK!” went the blonde with eyes, and mouth opened wide. Before she could say anything. The Dominatrix brought her crop tip down on slushie’ hand holding the blonde’s arm. “ OW!” said the gangster letting go. Rubbing his hand. “She’s not into that,” said the Dom bringing her crop up between his legs. This caused slushie to freeze. He watched as the Dom forced French kiss the blonde. Pushing her tongue into the younger woman’s mouth. This caused even more attention on the street. The sound of something falling, or crashing could be heard. “ Damn, That is some hot shit. To bad for you being lezbos. I ain’t got time to mess with you crazy bitches anyway,” said Slushie. Trying to show he wasn’t affected about being shot down. He turned walking away. The women walked fast to their parked car.
Part two,
Earlier, while still inside the clothing boutique . Joyce had brought Ann, and the other female employees of the shop into a huddle. Ron didn’t notice this, since he was too busy looking out the glass door. They talked in excited hushed tones looking at him. There were some giggles like they were schoolgirls, and “ He’s going to be so cute.” said someone. After the huddle broke. Ron felt he was being watched. He turned to see all the ladies looking at him smiling. “ What?,” he asked.
“ Is this really necessary?,” asked Ron wearing a canary yellow sundress. The hem extended down just above his knees. His bare shoulders were exposed under the thin spaghetti straps. He was holding a pair of white lace panties that Joyce had given him. “ Of course, everything has to be authentic for this to work. “Right girls?” asked Joyce out loud. “ Of course! Agreed the mix of employees, and just arrived patrons watching. All taking part of operation (Sissy Boy).
“ You need to put the panties on, and show us if they fit,” said Joyce turning her head to the others winking. There was some disappointment as he stepped back into the dressing room, but the door at the bottom had an opening. So the ladies could see him stepping into the panties. Then pull them up his claves. It didn’t take long for him to come out. “ They’re a little bit snug,” said Ron red faced. “ Let me see,” said Joyce looking serious. “ I think they’ll be just fine,” said Ron redder. “ Look Ron, I’m a professional. I need to make sure your comfortable,” said Joyce. Her serious face almost broke with laughter, but she had been in business long enough to perfect her poker face. Reluctantly, Ron raised the hem up. There was a quick intake of air from all the ladies present. Their eyes slid over Ron’s exposed body instantly. Then settled on the bulge at the center of the panties. Some of them shifted their posture because it suddenly became hotter in the room, and faces flushed red. “ Oh My!,” one said putting her finger up to her mouth biting the tip. “ Let’s see the back,” said Joyce before Ron dropped the dress down. He turned slowly showing the panties had exposed a lot of his young firm ass. “ Whoooo!!!”, yelled out a woman like she was in a male strip club. Ron slammed the dress down fast. He could hear smacks as the other ladies hit the offender making her laugh. “ OW! OW! Sorrry! Sorry! Ha! Ha!”
“Now we need to add the finishing touches,” said Joyce. She detailed to Ron what was next. He reluctantly agreed to the idea. The alternative would be spending summer in the hospital. Joyce knocked on an adjoining door on her shop wall. Her clothing shop was in a building with another business. After a minute, a Thai woman named Kim open it. She was the owner of a beauty salon next door. Joyce explained the situation to her. Kim looked to Ron in surprise, then to Ann. “You are a very good customer Dr. Possible. It would be an honor for me to take the challenge,” she said. Kim then waved for Ron to follow her. Walking back into her side of the building. The Thai yelled something out in her language. Several female voices yelled back “Yes!” to her in Thai. “Ladyboy,“ said Kim in Thai pointing to Ron while in the doorway. Someone asked in English,“ Is this a joke?” Ron took one last pleading look at Ann before stepping through the door. “ Now then Ann, we need to work on your disguise too,” said Joyce. “I don’t need one thanks Joyce,” said Ann. “You might, the gangster could have remembered you too,” said Joyce.
Part three,
“What’s wrong Ron? We got away successfully,” said Ann as they were driving down the road in her convertible. The top was down allowing the wind to whip up the long black hair of her wig. Ron was sitting in the front passenger seat brooding. Ann would occasionally cast side glances to him. ‘The Thai really did a good job at bringing out Ron’s feminine features with the make-up,’ she thought. He really looked like a young woman. For some reason, it was a total turn on to her. “Well Ann, You didn’t have your entire body waxed, eye brows plucked, make-up put on, nails painted, doused in perfume, and groped!!!” said Ron pouting. He had one leg up on the car seat rubbing his barefoot. His discarded clogs were kicked off onto the floorboard. “ I had some hair on my chest. Now it is gone!!!” bemoaned Ron. “Tsk, Tsk, You poor thing,” said Ann not able to contain a little giggle. This made Ron more upset.
Ann found a secluded place to park. “Why are we parking here? To change are clothes back?,” asked Ron. They had their regular clothes in the shopping bag. “In a bit, right now I’m going to help you feel better,” said Ann. Leaning over to rest her right arm on the top of the passenger seat. Her left hand reached down to slide softly along his smooth left leg. “ Stop Ann, I’m not in the mood,” said Ron with a huff. Closing his legs together, and crossing his arms over his lap. Looking away outside the car. “Oh’ Come on Ron, don’t be that way,” said Ann in his ear smiling. She playfully kissed it. Then used her tongue to trace it. Bringing the earlobe to her lips to nip it with her teeth. Ron shuddered like it tickled him. He almost broke out with a smile. Ann’s hand slid up, and down his leg more. It would go to his kneecap then slowly return inch by inch to work under his dress.
Despite Ron trying to act uninterested. His legs soon loosened up to allow Ann’s hand more access to his inner thighs. She could feel the warm moist sweat between them. After a few slow rubs, and some soft squeezes. Ann’s hand went further up till finger tips slid across the thin fabric of the panties. From his balls to a hardening penis. Ron’s head leaned to the side now. Allowing Ann’s lips to walk down his neck to nuzzle him.
Ann’s hand pushed further up under the dress to Ron’s tissue padded bra. His crossed arms didn’t put up any resistance. She rubbed his smooth chest in slow short circles. Finger nails lightly teased his nipples. Ron seemed to be in the mood now, as he turned to kiss her fully. Red, and Black lips connected together. Warm tongues wrestled with each other.
Returning her hand down to Ron’s lap. Ann pushed it across his taunt belly. Then out of the dress to the side of the car seat. Lifting up a handle that made Ron’s seat lean backward. She brought her hand back into the dress to trail a finger along the top elastic edge of the panties. It stopped at the straining head of his cock. She hooked a finger to pull the front of the panties down past his balls. Releasing the hot throbbing monster from it it’s prison. Ann placed her palm down over his ball sack with fingers encircling the penis. She leaned over enveloping it with her mouth to the end of the shaft. Tasting the saltiness of young pre-cum. “OH!,” escaped from Ron‘s lips. As if some of the pressure was relieved. Ann began to bob her head up, and down slowly. Her tongue trailed along the cock inside. “ Loosen up a little bit Ann, Too tight,” breathed out Ron. He placed his hands on her head to guide it to the right speed for pleasure. After a few minuets of good deep bobs, Ann lifted her head up with a slurp. Leaving behind a red wet glistening cock. She kissed Ron mixing their body fluids together.
Breaking the kiss, There was an urge building up between Ann’s legs that needed to satisfied. She leaned her own seat back. Then undid the shorts to wiggle out of them. Pulling her blue panties along with them. She lifted up her legs above the steering wheel. To push her clothes up past her thigh high boots. The high shine of the vinyl was streaked by the soaked panties from her womanhood. Ann threw the shorts into the back seat. She stood up in the driver seat scratching back the circulation from the tight shorts. Then looked around before walking over to Ron’s seat. Her booted feet were on either side of his thighs.
Standing above him with her ass facing him. Ron could look up seeing Ann’s shaved smooth pussy. The lips were swollen open, and wet. She squatted down pushing her pussy into his mouth. Her warm wet inner thighs pressed against his face. His nose almost touched her little pink asshole. Her ass cheeks rested on his forehead. Ann leaned over the convertible windshield feeling his tongue lightly slide across her snatch. With each stroke it got stronger, and deeper. She pushed down more into his tongue. “ Hmmmm, Oh! Right there,“ said Ann. As Ron sloppily found a good spot to work on. Ann’s tongue came out to lick her lips while she moaned.
Using her right hand to hold herself up over the front windshield . Ann released her breasts from the tight cups of the corset top. They felt cool from the drying sweat in open air. Her left hand rubbed, and squeeze them. Fingers played with the pointed nipples. One lightly encircled the sensitive tops. Then Ann arched her back to bring them against the top of the convertible windshield frame. Allowing both nipples to rub against the sun hot chrome. She did this with each stroke of Ron’s tongue.
Orgasmic pressure was building up inside Ann. She lifted herself up off Ron’s face. Then turned to get down on her knees over his lap facing him. Her booted feet hung off the edge of his seat. Ann could feel his hard manhood touching her throbbing womanhood. She lowered her mouth down kissing Ron on the lips. Tasting her wet juice while their tongues circled each other. “I want you inside me!,” whispered Ann reaching down to line up his penis with her pussy. Then she completely lowered herself down unto it. They both sighed as tightness, and hardness brought pleasure. Ann wrapped her arms around Ron’s head. Putting his face between her breasts tightly. Then lifted herself up, and down slowly on his shaft. Ron ran his hands along her outer thighs, and over her perfect ass. He thrusted up into her as she came down.
Feeling herself being very close to cuming. Ann built up speed riding Ron’s cock. “Cum with me! UH! UH! UH!,” she moaned out. He felt the urgency in her, and wanted to cum with her too. Ron increased his thrusts trying to go deep as he could. He had to turn his head slightly as Ann’s chest rubbed his nose hard. Breasts bounced on either side of his bare shoulders. Finally, Ann couldn’t take it anymore. Her pussy tighten in an orgasm. This triggered Ron to let go of his under pressure cum. Shooting the white sticky seed up inside her womb. They sat stunned riding the orgasmic wave. Ann’s arms tightened more around Ron’s neck. Threatening to break it. “UHHHH!,” came from her lips one last time.
For the longest time they didn’t move. Ann felt Ron’s deflating cock shrink inside her. She leaned off him against the dash of the convertible. The summer sun fell on their bodies that were red, hot, and sweating.
“Feel better now,” asked Ann with a smile. “ Much better, thank you,” said Ron smiling back. He rubbed her legs, belly, and breasts one last time. Then went to reach to take the wig off. “ No! Don’t do that. Keep it on a little bit longer,” said Ann pulling herself off Ron. She stood up in the floor board. Then leaned over his seat to dig through the shopping bag in the back seat. “ Why do you want me to keep it on?,” asked Ron. Ann stood back with something gold in her hand. “ I had heard about a great lesbian bar from one of my nurses. I figured we go check it out,” said Ann smiling. “Here let me fix your lip stick.”
Epilogue one,
Later in the future, “ Hey Mom, Thanks for the dress!,” said Kim walking in the kitchen wearing a yellow sundress with clogs. “Your welcome Kimmie, I had hoped it would have fit you,” said Ann. “Well it does, but the panties are a little big, and you know I don’t wear a bra,” said Kim holding the under garments in each hand by her fingers.
Epilogue two,
Sometime in the future, James Possible was pulling Ann’s things out of her closet in their bedroom. He decided it was time to add more shelving that she had wanted. Since she was at work. It would be a good surprise for her. James found a shopping bag buried at the bottom. He opened it up to look inside. Not able to see clearly, He reached in to pull out a black wig, and some hooker boots.
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- 11
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[ Kim Possible ] Afternoon Affair