Tiffany Charles

Work of fantasy not to be taken too seriously! If you haven't read NEIGHBOR'S SISSY SON 1 through 6 then stop and go read those first because all the character development was done in those chapters. Everyone is over 18.

Tiffany Charles

Tiffany Charles just finished applying her makeup. Not one to overdo it she went for a more elegant look.

It's not that she had a hot date or was going out on the town, she did that last night and the night before.

No, this was work. If you could call it that.

Tonight she was going to an award dinner for Dr. Alan Landry. The doctor that made Tiffany the "woman" she is today.

Dr Landry invented a method to enhance the body and or body parts....at will.

And Tiffany was his star patient! Tonight he was going to receive an award for this groundbreaking work and present Tiffany to the world!

At first Tiffany Charles was against this idea of exposing her and her abilities for all to see and judge. But Dr. Alan convinced Tiffany that it would be in her best interest to take control of her exposure rather than have her abilities discovered as if she was hiding and ashamed of who and what she has become.

"Tiffany, trust me if a nosey reporter ever discovered what you could do, they would make you out to be a monster. But if you're introduced to the world as a miracle of science then you have more control of how you're received." Alan assured her.

This line of reasoning did well to ease Tiffany's concerns. Especially when it was pointed out how good it would be for her "online business".

Her online cam shows have gotten very exclusive since we last heard from our favorite little shemale sexy bomb.

After she fucked her mother and mother's boyfriend (daddy see Neighbors sissy son) with her enhanced cock she uploaded the video of the fuck fest and it's now the number one selling video on her site. To date Tiffany has cleared more than 1.5 million without having to fuck any clients.

Tiffany loved her fans but the type of men she was attracted to were not the type to jerk off to cam gurls. Tiffany if asked, would say her type was straight (or at least thought they were), athletic (if they had any chance of keeping up with her and her "abilities") and dominant (she just loved fucking THEM in the ass most. Alpha's with a virgin hole)!

As of late she has "flipped the script" on more than a few "Bulls".

Tiffany lulls them into a false sense of security and when they have her on her knees between their legs sucking cock and balls, that's when she introduces their virgin holes to her 12 inch tongue.

Once they have felt that magical appendage tickling their prostate...well let's just say anal orgasms will change a man.

One time whilst Tiffany was out shopping at the local mall, looking for sexy outfits for her cam shows, she noticed two teen aged boys looking her way. Both looked to be athletic as they were in great shape and wore varsity jackets. The jackets were open and you could see both boys wore tee-shirts underneath. The thickness of their pecs and the flat six packs were a testament to their virility.

'They make it soooo easy.' Tiffany thought.

She knew the type. They would approach her one at a time so as to not scare her off. One would take the lead and his friend would play wingman till he got his turn.

Tiffany smiled as a different scenario played out in her nasty, sissy imagination.

'Time to play.' She told herself as she made eye contact with the taller of the two.

Vince was the varsity quarterback at the high school. Having turned 18 two months ago his parents bought him the new GT350 Mustang. That car went a long way in boosting his never ending egotrip! Girls were already pursuing the young qb incessantly. Now they were practically throwing themselves at him. So when he first took notice of the way young Tiffany dressed in tight skimpy clothing and how her nipples stuck out at least an inch from her braless double D's, he knew she was an easy slut! Having made eye contact it was time to make his move. Walking up to the young girl from behind as she gazed in the front window of Victoria secrets.

"That would look great in a pyle by the bed we're fucking in!" He confidently implied with a nod to the babydoll nightie on the mannequin.

Tiffany, always on her 'A' game, responded "I thought it would look great on your friend." Hiding a smirk.

Laughing he introduced himself.

"Hi I'm Vince and my buddy over there is Tom." Tom waved so Tiffany in turn waved him over. She noticed he seems less cocky than Vince but just as confident. She could easily get lost in his smoky eyes.

'Damn! This was a boy girls would fight over.'

Both boys were each over 6 feet tall and each weighed at least 200lbs. And judging by the slight bulges in their jeans both were packing respectable meat poles.

Tiffany, trying to keep a straight face, caught Tom up to the conversation "So Tom is it?....Vince and I were trying to figure out which of you two would look better in that babydoll."

Tom, not missing a beat said, "That's easy....Vince mom. That milf looks good in anything."

Vince hated when his friends talked about his (milf) mother!

"Really Tom? You know..."

Tiffany quickly interrupted. "Oooo your mom is a milf? That's hot, have you fucked her yet? When you do, can I watch?" Vince was speechless. Did this slut offer to do a three some with him and his mom? He had to admit the thought caused a swelling in his tighty whities. Tiffany noticing the reaction to her proposal persisted.

"I bet you pumped a ton of cum out to thoughts of your milf mom sucking your cock...or was she sucking your friends cock?"

Vince's eyes went wide and was about to protest when Tiffany closed the distance between the two and squeezed Vince's hard thick cock. She gave it a few tugs before releasing it with a pat.

Tom took this opportunity to say "Hey, I'll take one for the team and do your slut mom while you jerk off!"

Testosterone was in the air as the two friends took hard stands.

Tiffany, not one for this teen age bullshit, cut in and asked. "Does anyone know where the little girl's room is?"

Tom right away offered his left arm which Tiffany gladly accepted.

Tiffany, not wanting Vince to feel left out, took hold of his right arm and off to the ladies room they went.

Turning to the boy's, Tiffany asked if they were game for a bit of fun. Nodding enthusiastically, the boys eagerly awaited Tiffany's plan.

"Vince, I need you to go into the boy's room and see if it's empty." Tiffany asked with a pouty face and batted lashes.

30 seconds after going in, he came out and announced it was indeed empty.

Armed with this info Tiffany entered the boy's room and was quickly followed by the two eager studs. Leading them to the last stall, Tiffany took up residence on the bowl seat down.

"Okay boyz, no shyness, no jealousy and don't be greedy. There's plenty of this slut to go around. Now give me COCK!"

The boyz looked at each other, shrugged and started undoing their pants. Tom was first to pull out what looked to be a very thick 8 inch cock with a lemon size head. Vince was right behind pulling out his equally impressive tool that sported a turtleneck (foreskin).

Tiffany loved uncircumcised cock! She would run her tongue around and under the extra skin just like she was doing right now.

Vince was in warm wet heaven.

Feeling a little submissive, Tiffany removed her hands but kept sucking the thick teen cock. Placing her hands behind her back she looked up at Vince and continued servicing his meatpole.

"I think she wants you to hold her head and face fuck her!" Tom advised.

Thinking how much he'd like that, Vince took hold of Tiffany's head with both hands and slowly pushed all 8 inches in till he felt her little nose in his pubic hair.

"Oh fuck, she's got the whole fucking cock in her throat!" Vince announced just before he began face fucking Tiffany in earnest.

Tiffany opened her throat and using her nanites, increased the length of her tongue slowly.

Vince was in ecstasy as his cock was awash in a very wet and sloppy mouth. He could feel her tongue peek out her cock filled mouth and snake toward his nut sack.

"OH FUUUCK SHE'S LICKING MY BALLS WHILST DEEP THROATING MY WHOLE FUCKING COCK! SUCK IT YOU NASTY WHORE!" Vince cried out.

Tiffany felt it was time to up her game as she continued her tongues progression reaching his virgin mancunt.

Vince felt the oddest thing. It felt like the girl's tongue reached his ass. Impossible...but he could feel that same tongue now worm it's way into....NO...not...

Tom saw his friend losing control so looked down where cock and mouth were joined. He could just make out what appeared to be the girl's tongue working it's way back to his friend's asshole. Tom couldn't figure out how she did it, he just knew it was the sexiest nastiest sluttiest thing he's ever witnessed!

Meanwhile Vince was getting his ass tongued out and it had him questioning his rule of nothing goes in the butt. Tiffany was stroking his prostate causing the cock in her throat to expand and pulsate.

"FUUUCCCKKK! SHE'S GOT HER TONGUE UP MY ASS! I'M GONNA CUM YOU FUCKING WHORE!"

And with that outburst, he came and kept cumming hard. He had never cum so much and Tiffany swallowed all of it. It was her hard earned reward. Yummy cummies!

Vince collapsed to the floor of the restroom, head on toilet, ass in air.

Tom was still staring at his friend's asscunt gapping open and did something he's been wanting to do for quite some time. He shoved his bare swollen cock deep in his friend's boycunt.

Tiffany squealed. "Yasss! Fuck his virgin asspussy! Make her a real girl!"

Vince, starting to cum around, was feeling that same pressure on his prostate, only this time it was being pounded instead of being stroked!

"Oooh SSSHHIIITTTT! What are you doing Tom? Get your cock out of my ass!" Vince screamed.

Tom, paying close attention to his friends body language, noticed Vince ass moving on its out volition.

"You say that but you keep shoving your cunt onto my fat cock! Admit it you're a fag for my cock! Say it!" Tom demanded.

Vince was so confused. Tom was right in that Vince was definitely pushing his ass back onto Tom's big juicy cock. JUICY? Definitely confused!

"I think I might be a fagot. Fuck this feels good!"

As Tom sawed in and out of young Vinces gaping hole, Tiffany sat on the toilet seat and brought the boy's head up to look in her eyes.

"Do you feel that? In your gut? That's your manhood leaving your body. Even now I can see your drooling cock twitching in the air looking for release. But we can't have that so...."

Tiffany squeezed his balls until the once mighty cock went limp. Tiffany quickly removed a metal device from her purse and placed it on the shriveled excuse of a cock locking it in place.

"There! Now you can be my good girl! You're going to get so much cock."

Vince lost in anal orgasms, could only nod his acceptance.

"Now it's time for you to serve me."

Tiffany informed him as she lifted her short skirt and pulled out her growing erection. It was only 5 inches but to a first time cock sucker it might as well have been twice that size.

"Now I want you to take the whole thing down your throat and try not to bite."

Vince looked at the little cock and thought 'I've got a cock in my ass and it feels amazing. So sucking a cock at this point wasn't going to make much difference.' And with that thought, Vince opened his mouthcunt and accepted the cocklett. It tasted like precum.

Tiffany was in heaven. While the boy on her cock was getting spitroasted in a bathroom stall, his friend was digging deep in the virgin's anal cock sleeve.

It was time. Tiffany concentrated on her ability. Waking the nanites to go to work. She's done this so often it's gotten quite easy. She pictured her cock growing to 10 inches but maintaining it's narrow girth. This made it easier for her to slide the cock down the boy's throat. Once buried, Tiffany concentrated again this time increasing the girth by 1 more inch bringing it to 2.5 inch girth 10 inch length. Perfect!

Vince couldn't understand why his throat was getting tighter around the little cock. Starting to lose vision from lack of oxygen he pulled himself off the cocklett only to see it was definitely not a cocklett but an impressive piece of meat and it was all the way down his throat. He should have been put off by the idea of sucking a cock. He never had gay fantasies before today but all he could think about was getting that cock back in his mouthcunt and finishing the job at hand.

Tom was on the verge of the biggest orgasm of his life. He'd been pounding his friend's asscunt for 20 minutes and he was close.

"I'm gonna cum soon. Where do you want it fag? In your pussy or on your back?"

Tiffany yelled. "In her asscunt! So she can become a real girl!"

And with that Tom came gallons in his friend's slut hole!

"FUUUCCCKK! YOU SISSY BITCH! TAKE MY CUM YOU COCK SLEEVE!"

Vince could feel the cum explosion in his/her (so confused) asscunt. It felt warm and it tickled as it crept up his/her anal canal. Cum started shooting out when the hole filled to capacity.

Meanwhile Tiffany felt it was time to bring this session to a close and released her pent up cum deep down Vince's throat.

"Fuck! I went cummies down your throathole! You're going to be my sissy bitch in training from now on!" She claimed as she patted her pet's head.

"Remember I hold the key to your clitty cage. No cummies till I say so unless it's anal cummies. You can only cum with a real MAN'S cock in you!"

"Tom here's my number, call me with progress updates. I expect her to go out and buy anal plugs to train with. And buy a dildo for practice. And by the way her name is now "Vanessa!"

"I'll make sure Vanessa is obedient! And I'll take responsibility for any anal stretching that's required." Tom gladly volunteered.

And with that Tiffany kissed each boy in turn. Vince on the cheek and Tom a full french kiss that curled his cock!

(More from "Vanessa" and Tom and maybe Vanessa's mom. Spin off?)

Finishing up Tiffany went to her jewelry box (you'd be surprised at how much jewelry fans bought her) and selected a gold bejeweled anal plug. It wasn't for stretching, it was more symbolic. It was a gift from the doctor. To celebrate her moving out of her mother's home and into her own penthouse loft.

One final look in the mirror told Tiffany all she needed to know, "FUCKING HOT SEXY BITCH!" Yes she was very pleased with the way she looked!

Showtime!

Thank you for reading. Next chapter Tiffany's world changes drastically. She's going international.