Tiffany Charles Ch. 02

#incest #submissive #huge cum loads #whoring #trans girl #bisexual #nanites #sci-fi #fantasy #big tits #bull #reluctance

I decided to display the tags at the top of my stories from here on. To avoid any confusions. And of course everyone in this story is over 18.

If you try to read this without first reading the series, which starts at Neighbors Sissy Son then goes on to Tiffany Charles, will find it hard to understand. I'm big on spin-offs.

Tiffany woke to the sound of her phone ringing on the nightstand next to her king sized bed. She was having a very sexy dream in which she was being fucked by a trio of big cock firemen that hosed her down with enough cum to put out a 4 alarm fire. She considered sending whoever it was to voicemail. With a glance she saw it was a boy named Tom that she met at the mall a month ago.

Tom and his friend Vince, high school seniors on the football team, followed Tiffany Charles (at her insistence) into the mens room. Once inside, it didn't take long to turn Vince into Vanessa. Turns out flipping Vince from macho, quarterback to sissy cock slut was an easy task for the petite trans girl. It wasn't the first time she recognized a sissy masquerading as an alpha male.

Answering the phone Tiffany joyfully asked, "Tom! Oh my god, I was wondering when you were going to call...so how's Vanessa (Vince), is she being good and accepting her new role as a sissy slut?" Tiffany had made Tom promise to continue training Vanessa by use of anal toys and as much live cock as she could handle. In return, Tiffany handed over the key to Vanessa's chastity cage so Tom would have better control.

Tom only accepted the responsibility so he could have a modicum of control over the one person standing between him and the slut milf fantasy (Vince's hot mom) he's been trying to bang. In the past Vince was always an obstacle but as Vanessa there would be no cock blocking just cock worshipping.

"Hello Tiffany! I know it's been awhile since we last saw each other but I've got great news! Vanessa has graduated from sissy slut to a part time sissy whore that will fuck and suck who ever I tell her to. I've made a tidy sum of money pimping out my best friend and neighbor." Tom said with a laugh. Tom and Vince lived next door to each other since they were in first grade. They played touch football with the other kids from the neighborhood until they started high school and then played on the JV team. They've been best buds ever since!

"I'm overjoyed to hear Vanessa is accepting her new role and existence in life. It will make her transition that much easier.

In the background Tiffany heard slurping sounds and some gagging."Tom, is that porn you're watching or are you getting your lovely fat cock sucked by someone we both know?" She chuckled already knowing the answer.

"It's both actually. I'm watching a video of Vanessa taking two cocks at once in her gaping boycunt while I'm getting my cock sucked expertly by my new whore. We made this particular video yesterday when two clients wanted to fuck the slut at the same time. At first I was going to say no to their request but before I could, Vanessa moaned and said how hot that sounded and begged for the two cocks at once. Here let me FaceTime you." Tom turned on the app and once he saw Tiffany's beautiful face, he smiled and said. "Hey sexy, want to see our girl?"

"Yes, show me the slut!" Tiffany giggled.

Tom reversed the camera and filled the screen with the image of Vanessa wearing a blonde wig that hung down to her panty covered ass cheeks and full makeup. She had her eyes done with shadow, liner and the ultimate in slut wear, fake eyelashes. The newly turned quarterback now looked more like a hot slutty truck stop whore. Looking down at her body, Tiffany saw the cock cage she placed there a month ago. It was leaking lots of pre-cum. Returning her attention to the blowjob, Tiffany watched as Tom's 9 inch cock slid in and out of Vanessa's mouth and throat.

Her lips were stretched wide around Tom's girth and there was plenty of saliva dripping down to Tom's huge cum filled bull testicles. Tiffany could see the hunger for cock that Vanessa was displaying. She was taking all 9 inches with only some difficulties even when Tom held the new sissies head down till she would almost pass out.

The scene was so hot that Tiffany took out her rock hard cock and willed the nanites to increase her size to 9 inches and girth to 2.5 inches, matching Tom's dimensions. Now stroking her massive girl cock in time to the blow job, not trying to cum just edging, she was formulating a plan.

Vanessa felt herself be pulled off the delicious cock she was worshiping with a pop and made to stand. Tom placed his cell on his desk so he could be hands-free and walked into the shot with Vanessa.

Tiffany watched as he stood behind her and waved to the camera just before smacking Vanessa on her sweet ass cheeks causing the slut whore to squeal then moan as more pre-cum leaked out of her caged girl cock.

"Tell Tiffany thank you for turning you into a sissy cum slut. And thank me for keeping you that way". Tom demanded.

Vince, now Vanessa, looked sheepishly at the camera and thought how far she/he had fallen. Having been the BMOC for most of high school, he/she was now a thirsty cum slut that took dick for money only to then turn over to his new daddy, Tom. Vanessa couldn't deny how she came so hard when she had both a cock in her mouth as well as her boycunt. Who knew cock was so delicious and so satisfying? As Vince he never gave it any thought as to why sluts enjoyed sucking and worshiping his own cock but now she was starting to see the truth. She was a true cock slut and she could fuck and suck for hours without complaint.

"Thank you Tiffany for showing me my true nature. I'm a cock sleeve for real men that know how to fuck the manhood right out of me. And thank you Tom for pimping me out to all those strangers that gave me lots of delicious cock and cum. Thank you both for turning my asshole into a loose pussy so I can accommodate multiple cocks at once. Can I finish sucking you now?" She asked Tom, eager to fill her throat with his fat daddy cock once more.

"Not yet slut. Turn around and show Tiffany what you have in your pussy.. He commanded.

Without hesitation, Vanessa turned on her 5 inch heels, bent at the waist and spread her cheeks which were suspiciously glowing red. In between those cheeks, sticking out her hole was an antenna for a remote control p-spot vibrator. Her anal lips were swollen and wet from some resent activity.

Tom pressed something on his phone and Vanessa squirmed and let out a desperate moan. "Mmmmffuckk...yes Daddy!"

Tiffany watched as the sluts' asspussy pulsated and with her legs spread, Tiffany could see Vince's caged cock leak even more pre-cum.

Tiffany had seen enough, she was going over to Tom's house to get in on that action. So she invited herself over.

"I'm coming over so text me your address. Let's give the whore a night to remember." She suggested.

Tiffany also had plans for the sluts milf mom.

After Tiffany announced her imminent arrival, Tom grabbed Vanessa and threw her to her knees. "Let's go slut, my cock ain't gonna suck itself. Yes, that's it, nice and sloppy just like I taught you. Now use that tongue and slather my balls in saliva." As his 9 inch cock and huge hanging balls were being worshiped by Vanessa's talented mouth and tongue, he closed his eyes and imagined it was Tiffany on her knees before him.

He's been wanting another shot at the petite trans girl with the big tits and even bigger ass. He had no interest in her penis except for what it could and would do to Vanessa. It turned him on to see her force all that cock into such a tight hole.

Tom, being an experienced cocksman, slept with enough cheerleaders and neighborhood milfs, that he was starting to get bored with it all. He desperately needed something new and Tiffany was definitely something new. He didn't understand how she was able to make her cock grow to such impossible lengths but really didn't care since he wasn't the one servicing her she-shlong, it was Vanessa.

"FUCK! YOU GOD DAMN WHORE I'M CUMING! You'd better not miss a drop you fucking cum slut!" Tom bellowed as he shot off thick ropes of cum down Vanessa's hungry throat.

After which he made Vanessa kneel by the front door, hands behind back, head bowed and await Tiffany.

Pulling up to Tom's house in her new G wagon she wondered if they were able to keep Vanessa's MILF of a mother from noticing the change in her son. And what about Tom's threat to fuck his best friends hot mom? Lots to find out.

Before she could knock, the door was opened by a very naked Vanessa. Wearing only a cock cage, high heels, a wig and a butt plug. After moving back from the doorway, she dropped to her knees and said, "Welcome mistress".

Vanessa's memory of the bathroom activities that turned her from Vince into the cum loving cock slut that is Vanessa, floated in her head upon seeing Tiffany again.

Tom right away got up and went to greet Tiffany with open arms. Once he wrapped Tiffany up in a warm embrace, he brought his lips to hers and they kissed like long lost lovers. He let his hands slide down to her sexy ass and grabbed a hold digging his fingers into her fleshy mounds before bringing one of those hands up to do the same to Tiffany's double Ds. Her nipples were hard and extended, burning an imprint in Tom's palm.

"Mmm yes baby! You know how to make a girl feel welcomed!" She purred in his ear then turned to Vanessa as Tom continued his assault on her sexy curves and asked, "so slut, have you been a good girl?"

Still on her knees, with eyes lowered, Vanessa replied right away. "Yes mistress! I only cum when daddy has me taking cock in my asscunt!" With the chastity cage she didn't have much choice, Tiffany thought. Vanessa continued "When home I'm always naked, unless daddy tells me otherwise. And I always serve any cock daddy tells me to." Vanessa admitted.

Tiffany noticed that the more Vanessa admitted the more her caged cock leaked copious amounts of pre-cum. This slut was a natural submissive that craved humiliation. Good!

"Are you a full time girl or do you still think you're a man?" Tiffany asked with a raised eyebrow.

Vanessa hesitated to answer before saying. "I know that I'm not a man anymore but I'm not a full time girl either. Daddy lets me go to school as a boy so he and I could hang out as friends, equals even. I trust Daddy because he doesn't want people to, 'give me any shit', as he likes to say, Mistress." Vanessa explained.

"So you're a DL sissy slut! By day you play 'BMOC', by night you're a cock sleeve, cum guzzler. If that makes you and Tom happy, I'm happy for you. You have to realize, I didn't change you or force you to do anything you weren't willing to do. Deep down inside you were always a cock hungry, submissive slut. You just needed encouragement.

That day at the mall while you were sizing me up, I was doing the same. And what I saw was a boy/man that was way over compensating. And when Tom made that comment about your mother being a milf, you were further exposed by your reaction. You weren't angry, you were jealous." Tiffany explained and waited for Vanessa to absorb everything she just said.

"I don't understand Mistress, you think I want to fuck my own mother?" Vanessa asked, quite agitated.

Tiffany got closer to the slut and spoke with her breath warming her ear.

"No, I don't think you want to fuck her, I think you want to be her! Have you ever watched her get dressed to go out? Watched as she pulled up her stockings before sliding into a pair of sexy panties? Or when she applied her makeup, did you study her technique? Now tell me, when she kissed you on the cheek before going out the door, did you get hard because she smelled so fucking perfect? How long before you ran up to her room and ransacked her panty drawer? Did you try them on? I KNOW YOU DID! I know you did all those things. I know because that's what I did. For as long as I could remember I was jealous of how perfectly sexy my mother was and is. I made it my business to one day be that painfully sexy!" Tiffany said with a hand gesture presenting her body.

Vanessa was beside herself, on the verge of cuming, bottom lip trembling, looking from Tiffany to Tom and back again. Not knowing how to answer the many questions that were so humiliating even though she knew the answers. She didn't know if she could keep from making cummies without permission. Everytime she opened her mouth, nothing came out until finally she gave up and just lowered her head, whispering..."yes".

"Don't feel bad. It's good to be honest with yourself. This is progress!" She said before turning to Tom and asking, "so Tom tell me have you fucked your best friends mom yet"?

Tom, still a little taken back by these revelations, was shaking his head in disbelief before answering. "N..no not yet but I am making progress. Before if I tried to be alone with Diane, Vince would cock block but Vanessa is actually trying to help by finding reasons to leave the house giving her and I some much needed alone time. Most of the time I flirt with her, compliment her hair, her outfits and let her know how when I jerk off I think about her sexy milf body. The first time I called Diane a milf, I had to explain its meaning to her. I think she's hesitant because I'm her son's best friend."

"Use that, tell her how hot it is to carry on behind Vinces back like a cheating slut wife. Since she's divorced, for her, that's a safe fantasy. When does she get home?" She asked Vanessa.

"Around 6pm, 6:30 the latest." He hesitantly said, wondering what Tiffany had planned for his mother.

"Okay, that gives us a few hours. Vanessa, go upstairs and put on your boy clothing. I need 'Vince' for this to work." To which Vanessa ran upstairs to Tom's bedroom to get changed.

"Tom, when Vince's mom gets home I want her to find me and Vince making out on the sofa, something I'm sure she's come home to many times. We'll excuse ourselves to go to his bedroom and that will leave her alone and contemplating what we're up to. You come over and when she tells you her son is upstairs with a girl, you say 'that's okay I'd rather hang with you anyway'.

I intend to be very vocal, making it sound like I'm having one orgasm after another, hopefully making her neglected pussy primed and ready. That should grease the wheels, so to speak, for you to seduce the milf." Tiffany explained.

"You fucking genius! That's a great plan! Do you think I should go in for a kiss first or just go for it by making physical body contact?" Tom asked genuinely interested in Tiffany's opinion.

"Always start with the kiss with a reluctant female! If she freaks out and admonishes you it will be a lot easier to walk it back and start all over.

She's probably not getting much action since you guys never see her bringing men home or even seen her stay out overnight. So she's thirsty and you need to quench that thirst.

"So lots of eye contact, maybe some hand holding and whispering in her ear..." Tom suggested.

"Yes exactly! And once Vince and I hear you two going at it we'll 'accidentally' walk in on you with your fat daddycock buried in her horny milf snatch. She'll be too far gone to stop what's coming next!" She told a very excited Tom.

After going over the plan with Vince, the trio made their way next door to await their prey.

Diane Worthington got off of work early only to be stuck in traffic. She hated that she had to go back into the workforce at 40 years old. She got used to having a husband that was the breadwinner of the family. John, her ex husband, was and is a hedge fund manager, earning 6 figures a year plus bonuses. He pays her alimony but since Vince turned 18 last year, he no longer has to pay child support. Yet Vince still lived under her roof so she still had to feed him and dress him. If Vince was better motivated he would get an after school job and pitch in.

'Why couldn't he be more like his friend Tom?' She thought to herself.

'Tom, now that young man is all man. I know he has the hots for me but he's my son's best friend so kind of off limits. Sometimes I wish he would just ignore my rejections and just take me then I could have my cake guilt free.' The hot mom thought.

"God I'm such a slut! No wonder my churchgoing conservative ex left me. I fucking need to get laid!" Diane claimed out loud.

Diane was 5' 6" 125 lbs with a hip to waist ratio that was made to be bred. Unlike her two girlfriends, she didn't need a boob job, having double Ds that defied gravity. Men were always hitting on her but she knew her son was going off to college at the end of this upcoming summer so she was holding off till then to bring a man home. She went out a few times with the girls and even hooked up a few of those times but she didn't want to do the walk of shame in the morning and bump into her son. She knew Vince idolized her and she didn't want to lose that admiration, it's all she had left.

Diane parked on the street because there was a pink G-wagon in the driveway. Admiring the vehicle she wondered who it could belong to.

'I mean who drives a pink car let alone a pink high end car like that?' She pondered.

Upon entering the Worthington residence she stopped dead in her tracks when she saw her son Vince on the couch making out with a beautiful petite girl with huge tits. They were going at it pretty heavy so it was no wonder neither of them noticed Diane walk in. She was about to make a beeline for the stairs when Vince, at Tiffany's insistence, spoke up.

"Oh, your home, sorry we lost track of the time. How was work?" It was not uncommon for him to ask his mother how her day was since she was most likely going to tell him anyway.

"Oh, you know, boring. Are you going to introduce me to your...friend?" She asked.

"Mom this is Tiffany, we've known each other for months but only recently started dating." Turning to Tiffany, Vince said, "Tiffany, this is my mom, Diane."

"Hello Mrs. Worthington. So glad to finally meet you. Vince has always spoken highly of you but he never mentioned how unbelievably hot you are." Tiffany gushed.

Diane didn't know what to make of that last comment but ended up just accepting the compliment.

"Thank you Tiffany, nobody has said that to me in a long time. Is that your car in the driveway?"

"Yes. I'm sorry, should I move it?"

"No it's fine where it is. I was just curious, it's a lovely vehicle. It must have set you back a bundle."

Tiffany surmised that the milf was fishing for info so she cut to the chase and gave her what she was obviously seeking. "Yes, it cost 200k! But I make double that a year so why not? I figure, you only live once!" Tiffany admitted.

Diane figured it cost that much but never would have guessed this petite young girl made 6 figures let alone 400k! Trying to be subtle, the bombshell mom said then asked, "wow you must have a great job. Are they hiring?"

Tiffany smiled thinking 'if you did what I do you would make a killing!' But decided not yet.

"I actually work for myself, no sense beating around the bush, I'm a cam show model. Do you know what that is?"

Diane did know but didn't want to tip her hand. "I think I have an idea but why don't you tell me so I'm sure."

Tiffany cocked an eyebrow while looking at the hot milf. "For two hours a day, 5 days a week I do something like a strip tease and my subscribers get to watch and give me tips. The tips are so I will pay attention to them more than the others. The business I'm in will one day put all strip clubs out of business." She stated, with confidence before she continued.

"I graduated from high school last year and decided to do the cam shows for 2 or 3 years. Then go on to college to get my business degree."