Neighbors Sissy Son Ch. 02

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Movers pack mother, son and boxes.
4.2k words
4.6
146.1k
175

Part 3 of the 7 part series

Updated 06/08/2023
Created 08/04/2017
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This is a prequel to 'Neighbors sissy son'.

It's a stand alone story but trust me it will be a better read if you've read the first chapter.

*****

Looking back Charles remembered always being the smallest kid in the class. Even now at 18 years old he was still the smallest.

When other boys were just starting to notice girls and their changing bodies, Charles was starting to notice the difference between average boys and the more developed man/boys. It would be a few years before he understood such terms as Alpha and Beta males.

By his 18th birthday he had come to terms with his sexuality.

Charles was not confused nor in denial about his sexual preferences but he was careful about whom he shared his identity with.

His mother was one of those people he hid his proclivities from.

Not because he thought she would disown him or anything.

He knew for a fact she would not only be ok with it, she would embrace it becoming too involved and that would just not do!

Charles liked his freedom to go about his business without his mothers interference.

As far girls went, they saw Charles as a non threatening friend of the opposite sex. Non threatening because he neither had any interest in their newly developing bodies, nor did they consider him competition for male attentions.

Carol Bennings gave birth to her son Charles when she was just 19yrs old! He was the result of a alcohol fueled gang bang that occurred when she passed out underneath some boy she met at one of many frat parties she attended her freshmen year.

She tried to continue her studies, even completed a semester but when Charles was born the pressures of motherhood and college life proved to be too much for a 19yr old with slut tendencies.

So she dropped out and went home to live with her parents, who helped her raise her new born son.

When Charles was 8 years old Carol went to work for her fathers real estate agency and learned the family business.

Unfortunately her sex life became non existent so her new job as a real estate agent and raising her son became her focus.

For the next ten years she worked long hours and saved enough money to finally move out of her parents home, getting herself and Charles a little 2 bedroom in the city.

With more opportunities in the larger city she started her own agency.

While Charles loved his grandparents, as an 18 year old he grew to appreciate city life. It offered the perfect combination of anonymity and tolerance that a fem boy needed to develop his sense of self.

With his mother working all day he could dress how he wanted and be back home to change before she got home.

For Charles dressing in girls clothing, like most 18 year old fem boys, started by wearing his mothers panties. Though they didn't fit his slender frame, his mother being much thicker than him, he still learned to love how silk felt on him. Later it was stockings, high heels and eventually her make-up.

The internet was another source of information and exposure to cross dressing.

Charles had a Tumblr page were he posted pics of himself in panties, stockings and heels.

Confidently posing suggestively, she would write captions like, 'Maybe someone will be my Daddy and buy me some pretty dresses. If you do I'll take and send you exclusive pictures.'

You'd be surprised how many older guys with wives and even children would buy into that just to feed their fetish for fem boys.

So Charles had quite the wardrobe, not to mention a trunk full of sex toys. Two months later it was private cam shows for young Charles. By then she was going by the name 'Tiffany'!

She would get home from school and have time to do two or three web shows before her mother got home from work.

The webcasts mostly consisted of Tiffany playing with her little girlcock while riding one of her many large dildos and ending with her licking her own cum off her fingers.

One day after a three show day, Charles mother came home and told him she had really good news.

'Charles, I have something you need to hear.' she said as she kicked off her heels and poured herself a drink.

'I bought a condo uptown and we're moving at the end of the month.' she said before taking a sip of her drink.

'OMG how big is it?' he excitedly asked, already wondering how this would play into 'Tiffany's' cam shows.

'Compared to this place it's huge. And the best part is we own it, no more rent!' Carol exclaimed.

'And since you graduate in two months, once we move you'll only have to commute to your current school for five more weeks.

So I know you said you're going to take the summer off and then attend a local two year college until you decide on a career path...but I was thinking maybe you'd like to come work for me this summer as my assistant?

It pays $300 a week!'

At this alarms went off in Charles's head 'Fuck how do I turn down that offer without hurting her feelings?' Tiffany on the other hand was thinking, 'Bitch are you crazy? I'm pulling two grand for a nine hour week! And on top of that I make hundreds of men cum!'

What came out of Charles mouth was 'Sorry mom got plans this summer.'

Carol was a little disappointed but understood. She herself turned down working for her father the summer before going off to college so she could hone her oral skills.

Ah, to be young again!

At 37 Carol was in better shape then some girls 15yrs younger. Between the gym and all those stairs she climes when showing apartments that are not on the first floor she was in the best shape of her life.

Long removed from the drinking and all night parties of her college days she now avoided alcohol and didn't smoke.

Though sometimes she missed the parties, the no strings sex but mostly she missed the many, many cocks she would suck.

Back in college Carol was known as a blowjob queen. Mostly because she figured she couldn't get pregnant from a cock in the mouth.

But you can get pregnant from passing out during sex with a frat boy that's not shy to share his good fortune with his frat brothers.

There was no denying Carol had an extreme oral fixation. To her there was nothing better then having a cock grow hard in her mouth and with her tongue feeling it's way around the spongy head. She would push that head all the way to the back of her throat and with a talent unmatched, she would open up and swallow until her nose was buried in pubes! With the cock deep in her throat, pulsing, leaking pre-cum, she would then have the first of many orgasms!

She would cum hard just from having her throat stuffed with cock!

But that was before she got pregnant with Charles. Now she barely has time to pleasure herself with her fingers or her one vibrator.

And even then she would be left wanting, no it just wasn't the same thing!

To say she was sexually frustrated was a huge understatement!

Maybe this move would bring the opportunity to meet someone professional like herself that had similar interests and hopefully a large cock!

Charles was glad his mother didn't push the issue of him working for her but as he watched her day dream he couldn't help but recognize that look on her face. His mother was day dreaming about sex, cock to be exact. Being a cock whore himself he recognized the look. Yea his mom needed a man badly!

Moving day came and Charles and his mother were packed and waiting curb side for the movers to show up. When they did show up they were 20 minutes late!

Three Hispanic men got out of the truck, two were in there mid to late 20s cut off sleeves showing strong arms with lots of tattoos.

The third was older and most likely the one in charge!

'Mrs. Bennings?' the one in charge asked Carol as he looked her up and down, stopping at her cleavage to admire the swells of her breast.

'Miss, it's Miss Bennings' Carol corrected. 'Your company said you would be here at noon and it's almost 12:30pm.' Carol said trying to get his attention off her breast.

Looking up at her face he smiled, which had the affect of disarming her and introduced himself.

'Hello I'm Hector and I apologize for being late, the job before this one took longer then we anticipated.'

At this he looked back at his helpers for conformation at which one of the helpers said, 'yea the last job required "our special touch''! He said with grin that did little to instill confidence.

Carol was at this point ready to get started loading the truck.

'There are items I would like to supervise how they're placed on the truck because they're fragile.' Carol explained.

'No problem, in fact Ralphy, Junior go up with the son and have him help you start bringing down the rest of the stuff. Miss Bennings why don't you and I handle the loading of the truck?' Hector suggested.

And so it was with everyone doing their part the truck was getting loaded.

Hector noticing that Carol wasn't wearing a bra spent some time admiring how her DD breast hung and swayed when ever the young MILF bent over to inspect a box.

'This bitch has got my cock harder than a diamond.' he thought to himself.

And every now and then Carol would find herself in the far back of the truck with Hector pressed up against her from behind adjusting a piece of furniture or a box.

Wearing yoga pants and a v- neck tee tied off under her large DD breast, Carol could feel the hard cock pressed up against her ass.

At first it was subtle, then Hector got bolder the longer he got away with it.

At one point he was behind Carol helping adjust a box and he started grinding into her with what felt like an iron pole but was in fact his very hard 10 inch cock he had removed from his overalls.

'Oh god is that...are you...oh nnnggghhh' Carol groaned.

'Yes Carol that's my big fat cock pressed against your sweet ass do you like it?'

'Nnnggghhh oh god please stop before...oh god, someone sees us.' Carol begged even though she herself was pushing back against Hectors fat cock.

She could now feel the shaft sliding across her sensitive asshole causing it to twitch with desire!

'We're in the far back of the truck behind these boxes, no one can see. Besides you don't want me to stop. In fact I think you want me to fuck you with my big cock.'

Truth be told Carol desperately wanted to be fucked! It's been way too long since she's had her pussy filled with cock meat.

And judging by the way Hectors poll filled the space between her ass cheeks, she was about to get her tight cunt stretched!

And with that he reached around and grabbed her huge tits and pinched each nipple between his fingers.

It was too much for Carol to stand. Though her mind was saying don't give in to this man who was uneducated, rude, dirty and sweaty!

Her body, on the other hand was betraying her, reminding her how good it feels to be a total slut.

Having gone too long denying herself her one true desire, cock, she gave in and let her true self free.

'Oh fuck... yes! I want your cock...it's so hard. Fuck me, make me cum, I need it so bad!' Carol begged

So Hector yanked down her yoga pants and stuffed two fingers in the horny mothers wet cunt.

'God damn slut, your pussy is soaking wet! I'm going to enjoy using you like the fuck toy you are!' he exclaimed as he added another finger to the tight confines of her juicy cunt.

Umm yes, fuck me with your fat fingers. Oh please my pussy is so wet for you!'

Knowing they didn't have much time Hector removed his fingers and stuffed them in Carols mouth to clean off as he lined his huge cock up with her leaking cunt and pushed until he felt the head pop in.

'um oh shit,' her scream muffled by the fat fingers still in her mouth as he plunged the rest of his cock all the way in until he hit her cervix.

'Oh shit...fuck...cock...' her incoherent muffled cry could almost be heard outside the truck!

'Shit you are one tight slut! I'm going to enjoy stretching your cunt out and dumping a load of my cum in this fine white pussy. Tell me how much you love my Mexican cock you slut.' he demanded as he removed his fingers from her mouth.

'Oh fuck I love your big fat Mexican cock in my slutty white pussy! Oh shit I'm gonna cum nnnggghhh ...I'm gonna cum on your long hard Mexican prick. Fuck...I'm... cumming no...god...no!' and so she came squirting for the first time in ages. Carols body shook with tremors and then came again not having been fucked in way too long.

Getting the MILF to squirt encouraged Hector to pound the young mother tight pussy even harder.

Still slamming into her from behind, Hector reached around in front and forcefully grabbed the massive tits so he could pull the slut back into his thrusting hips forcing every inch of his cock deep into the cock drunk mother. Hector felt his orgasm building announced his impending rupture!

'Fuck shit I'm gonna cum where do you want it face, ass or your nasty cunt?'

Without hesitation Carol pulled away and spun around to her knees. Grabbing Hectors cock and swallowing it to the root like a pro.

'Oh you nasty white slut suck my cock. I'm going to fill you up with my cum and you'd better not spill a drop you fucking slut!' Hector demanded as he took out his cell phone and started taking pictures of the white slut sucking his fat cock!

As he was taking a few pics he noticed the slut deep throating him start to convulse and her eyes rolled to the back of her head.

'Holy shit the bitch is cumming just from sucking my cock!' Hector realized

Seeing that only pushed Hector over the edge. 'Shit I'm cumming!' he warned

Carol felt the cock in her mouth buck and shoot before her mouth filled with hot cum. So much cum she started to worry if she was going to get it all down. So she gulped down what was in her mouth only to have it filled again with warm cock cream.

Just as Carol was finishing up the last of Hectors delicious gift she heard someone enter the truck.

'Hector we need a hand wi...what the fuck? It was Ralphy one of the helpers.

'I knew you was gonna fuck this bitch.' Said Ralphy when he saw Carol on her knees with yoga pant at her ankles sucking cock.

'Don't worry you can have her now while I run up and see how things are going' Hector said to his worker.

Having heard this Carol couldn't believe she was being offered up like property. And though it should have angered her it didn't, in fact it just made her pussy gush and the humiliation only served to turn her on even more. She could feel herself leaking down her inner thigh.

Ralphy took Hectors place in front of the slut mother on her knees while his boss ran upstairs.

'Ok slut my turn. Take my cock out and show me what you got bitch.' demanded Ralphy.

Charles was finishing packing Tiffany's clothes when Hector walked in saw him folding a mini skirt to put in the box.

Hector had his suspicions about the boy from the beginning, but when he saw the boy try to hide the skirt his suspicions were confirmed.

He was delicate to put it mildly but he also had the feminine body language of a sissy. Hector decided to confront the boy.

'What have we here? Junior get in here and see this.' he called out

'What's up boss?' asked Junior.

'I'll tell you what's up looks like we got our selves a little slut boy that dresses in girls clothes!'

Charles frozen with the fear of being outed said 'Please don't say anything to my mother she doesn't know!'

'Calm down kid, I ain't telling your mother. But I'm willing to bet you would be down to suck some cock right about now.' Hector said as he rubbed the bulge at his crotch.

Junior seeing where this was going added his two cents. 'How about it kid sucking two fat Mexican cocks should be a dream come true for you!'

Not wanting to seem too eager Charles asked 'What if we get caught?'

'Caught by who, your mother? She's probably done sucking off Junior and is working on fitting his huge cock in her tight little ass right now! Hector pulled out his phone and showed the boy all the pictures of his slut-mommy sucking his fat cock.

'Right now she's giving it up to Ralphy so I think we'll be ok.'

Charles couldn't believe it his own mother was deep throating Hectors huge cock.

Carol should have been offended but all these insults were actually turning her on even more. It was like the old days, she was on her knees swallowing another strangers cock. How could she let this happen? But any doubts she was having had disappeared the moment he pulled out his long thick uncut cock which had to be close to 12 inches in length, with balls the size of lemons!

'Mmmmm' she moaned as she licked up and down the shaft. Then one by one she sucked and licked each one of his balls.

'Damn bitch you really love cock don't you?' asked Ralphy.

Without removing his balls from her mouth she mumbled. 'Mmm I love it and your balls. It makes me so hot worshipping your cock meat.' She said before returning to his nut sack.

Finally removing his nut sack from her mouth she placed the cock back in and again began worshipping the meat god!

She had about 8 inches down her throat before she started gagging and came up for air. After taking a deep breath Carol put the wet meat pole back in her mouth and hungrily devoured inch after inch stretching her esophagus until she felt his big hairy balls resting on her chin.

Ralphy could feel the sluts throat muscles working hard to keep his cock right where it was.

It took all of his will not to cum too soon, so he decided it was time to try one of her other holes.

Reluctantly pulling out of the slut milfs throat, Ralphy ordered her to her feet and push her over stack of boxes with her yoga pants still around her ankles.

'Have you ever been fucked in your ass bitch?'

'Yes but it's been so long and you're so large, that I don't think it's a good idea! Just fuck my pussy it will feel real good for both of us!' she said trying to steer him and his huge cock away from her tight asshole.

A quick smack on the ass ended her pleas. To ensure her silence he stuffed one of his work gloves in her mouth and holding her by her hair pressed her face down onto to boxes.

'Slut this cock is going up your ass. The more you struggle the more it's going to hurt!'

Again Carol couldn't believe how turned on she was by the rough treatment.

Shame wasn't enough to keep her from giving in to these men, it wasn't enough to keep her from cumming all over Hectors big fat Mexican cock and shame won't stop her from taking 12 inches in her tight white ass!

Mean while Charles was now in full blown Tiffany mode. Sucking one cock while stroking the other.

Junior being the only one that didn't get to cum yet announced his impending orgasm. 'Fuck l'm cumming you little slut!' And deposited 5 long thick ropes of cum down Tiffany's throat. Then pulled out and painted the young boys face with the rest.

Hector seeing this said. 'Shit Junior I was gonna face fuck the little bitch but your cum is all over her.'

'Sorry boss. I couldn't help myself.'

With cum dripping down her face, Tiffany volunteered, 'I know, why not fuck my boy pussy?'

'Is that what you want sweetheart? The apple don't fall far from tree with you two!'

'Fuck me like you fucked my mother's ass! Fuck me like a real girl Daddy!' Tiffany begged.

To which Hector replied 'I'm gonna fuck the boy right out of you!'

Mean while down stairs in the truck, Ralphy was about to do some ass fucking himself.

Since he needed to lube up Ralphy decided to dip his monster cock in the single mothers pussy first.

'Nnnggghhh uuuugggggg' was all Carol could get out past her gag.

'Damn bitch that is some tight pussy, and I'm only half way in.' Ralphy exclaimed.

'As good as this feels, I really need to tap that ass.'

Taking his cock out slowly was a mind bending experience for Carol, leaving her whimpering with loss.

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