The Making Of Rosie. Chapter Two “Timmy Becomes Ro free porn video

The Making of Rosie

By Mad Jack69

Synopsis: This is a fictional story of a young boy and his whore mother. The young boy has sexual desires for his slut of a mother and also longs to be like her. This is the second instalment documenting his journey to becoming a shemale whore. (Fb, M+F, prost, whore, size, tv, toys, creampie, strap-on, ws)


Chapter Two “Timmy becomes Rosie”

Tim woke up at nine o’clock with his morning hard on tenting the duvet and his mum at the bedroom door looking sexy as ever in just her jean shorts that sliced into her cunt giving him a wonderful view of her camel toe obscenely bulging out either side of the deep groove in the fabric barley covering her pussy, and a baggy cut of wife beater T shirt hanging just over her bare breasts exposing her midriff.

With so much flesh on display her tattoos were very visible, and Tim wondered if she had others hidden away in her pants.

Tara was given her first tattoos very much against her will, she was just coming up to thirteen when she was forced to have a choker tattooed around her neck and at the same time she was forced to endure the words “CUM DUMP” tattooed above her pussy. Shortly after that she was forced to have a tattoo done on each hip. It was a very explicit depiction of a young blond girl, obviously Tara, having sex with a big black dog. She also had had her nipples inked bright red all before she was even f******n.

As time went on she got into tattoos and got more of them, pushing the boundaries like the ones on her arms, belly, cunt and arse. With the original tattoos redone and touched up, giving the blond girl that was fucking the black dog huge breasts making the girl look more like her in an exaggerated way. In addition, on both calves running up from her ankle to just below her knees she had a blond slut with her legs rapped round the stem of a black rose, impaled on one of the thorns head thrown back in ecstasy. Encircling both thighs’ she had tattoos of lace garters. On her right thigh she had an ten inch vibrator that looked more like a weapon of mass destruction from a nineteen sixty’s syfi film that was skilfully done to look as if it was stuffed inside the garter.

“Come on get moving, I have some bread in the toaster and tea in the pot. Do you want some eggs?”
“Yes please just one on my toast”
With that she left calling back to tell him to hurry up.

As soon as the breakfast was finished and the dishes washed up and put away Tara turned to Tim and with a mischievous smile ask him if he was ready.
Ready for what Tim thought?

Not waiting for a response “I have had a sort through and have a really sexy outfit that will fit you. Do you want to try it on for mummy?”
She walked over to him and took his hand leading Tim upstairs, like a lamb to the slaughter.
They went into Tara’s bedroom and Tim looked around taking in the shear sexual decadence of the room. The carpet was deep red and the walls a pale pink, full height mirrored wardrobes covered the wall on one end of the room, with a large dressings table the other. Mirrors were fixed to the ceiling, covering the area above the bed. Also on the ceiling a number of large metal rings had been fitted.
Four chairs were pushed against one wall with a small table.
On the bed that was covered in black satin sheets she had laid out some sexy underwear, a small black mini mesh skirt, bra, see-through red blouse and stockings. In addition a couple of boxes also lay on the bed.

“Come on Tim don’t be shy with mummy take off those nasty boy clothes”
Tim took off his clothes and feeling a bit insecure and nervous his semi hard cock was dying on him. For that he was actually very grateful.
When he was naked Tara produced a small pair of rubber pants.

“Before we start we need to ensure that that cock of yours doesn’t get in the way. Come here and step into these, they will keep your cock in place between your legs and restrict it so you can’t get an erection, they also have a hole at the back so you can work you arsehole out with a dildo”

With the pants in place and his cock going nowhere Tara handed him a pair of hold up red stockings.
“Let me see you put them on”
Sat on the bed he put them on taking out any creases and checking that the tops were at the same height.

“I can see you’ve done that before, now the red panties”
She handed them to him and he put them on.
Next she handed Tim a red bra and it was not one of hers. He looked at her and knowing what he was thinking she said. “I told you that I have a number of customers that like to dress up. Well I have a collection of different sizes this should be perfect on you”

Tim put the bra on and looked down at the empty cups. Reaching for one of the boxes Tara opened it and took out 2 flesh coloured fake boobs and inserted them into his bra.
“Now how does that feel?”

Reaching up he cupped them with his hands. It felt electric, the soft yielding flesh under the material of the bra was wonderful. His cock strained in its prison causing him to rub his thighs together. But that only made the sensation worse.
Tara saw his distress and came up beside him. The next thing he felt was a stinging slap on his arse folded by another.

The shock was enough for the erection to subside.
“That’s better; you can play with your cock when we are finished. And by the reaction you just had I think you like your tits”

“Yes mum I love them”
“Now let’s get you into this dress and blouse”
Having watched Tim put them on she reached for another box in it was a blond wig with a blunt cut and long strait hair that would fall a couple of inches below Tim’s shoulders. She also produced a pair of white shiny court shoes with three-inch high heels.

Tara fixed the wig onto Tim’s head and made a few adjustments before he stepped into the shoes.
“Let’s see how well you can walk in them?”

Confidently Tim took some steps round the room and put his hand on his hip, catching glimpses of himself in the mirror, he was amazed how good he looked.

“Wow you have had some practise you walk great in them, and with some lipstick and makeup you will be red hot”

Tim stopped strutting around and looked at her. “Please can I try some?”
“You bet, come over to my dressing table”
After about ten minutes she was finished. Tim turned and looked into the mirror.
He was speechless and his mouth just hung open, what he saw before him was the face of a cheap tart, and a very attractive one.

Getting up from the dressing table he walked over to the full-length mirror wardrobe and took in the full impact of his appearance.
Tara came up behind him and put her hands on his waist, her tits pressing into his back and her lips so close to his ear Tim could feel her breath, as their eyes meet in the mirror.

“So what do you think Timmy, or maybe I should call you Rosie I know the boys at school call you that, so Rosie baby, is this the look you wanted?”
“Looking like this, men will line up just to get a crack at fucking your arse”

Tara desperately wanted to get one of her strap-ons throw him on the bed and fuck the shit out of him, fuck her little boy like she had done to so many other men.

Tim lent back further pressing against his mum as her hands come further round his waist.

“Yes, I love it” Tim was almost delirious with pleasure his cock encased in the rubber pants oozing pre-cum and his arse itched to be fucked.

Pushing him gently away she told him to take a toy from her dressing room and that he could play in his room in private.
With that she ushered him out taking his boy clothes with him and closed the door.
With the door closed Tara lent against it as if subconsciously preventing him from coming back in. She had to put a stop to this she thought, but she knew she couldn’t.

Tim was slightly shocked, at her sudden change of mood. But nothing could dim the sexual excitement he was feeling right now.

Tim played in his room the whole afternoon and by the end of it his mum’s seven-inch vibe had flat batteries and was slipping in and out of his arse pussy with ease. And his dick was soar from the constant abuse it was getting.

The weeks ticked by as normal after Tim’s first dress up time with his mom. If you can call getting your mum to dress you up as a slut every Sunday and spend the afternoon, shoving dildos up your arse while beating your meat until you can’t get it up again normal.

It was approaching Timmy’s fifteenth birthday and Tara continued to struggle with her emotions, she had decided that the best thing to do was to let her little boy experience what it would be like to be with a girl. She had to try and do what was best for her son. But she got so hot dressing her little boy up like a slut. She bought a few more girly things for her little sissy boy. Like his own breast forms with matching skin tone and a couple of nighties, and such like.

Tara and Tim were sat down at the kitchen table having one of their chats, Tara asked what Tim wanted most for his birthday.

“I want you mum, I still fantasise about you. I can’t help it, I try, but seeing all those men come through our door, hearing them... you know..... I can’t get the thought of it out of my mind”

“I’m sorry Tim but we just can’t, I’m your mother. But I have an idea”
Tara was desperate to take her baby boy to her bed and do such nasty things with him. She felt shame for the wickedness of her own dark desires. But she had a plan, she would hire him a girl for the night, maybe she could get over her own issues if he got over his fixation of her and having some time with a nice young girl might just do that.

Tim didn’t push for information on what her idea was but he was incredibly intrigued as to what it might be. And as it happens he didn’t have to wait long to find out.

Tara did some searching on the internet for just the right girl, but they were all wrong. Instead of picking a sweet young prostitute she settled on a real dirty slag.

The following Friday as Tim got home from school the door opened before he could get the key in lock. Tara looked all excited and almost dragged him in.

“Well Tim that idea I said I had, tonight is the night. Go get washed and changed out of your school uniform, I have left some clothes out for you in your room”

Tim’s heart leaped and he beamed, god he thought what has she got planed.
He shot of running up the stairs to his bedroom desperate to see what was in store for him.

He was more than a little disappointed to see a pair of smart trousers and a freshly ironed shirt lying on his bed. But his bed was made up with some of mums black satin sheets.

What the hell, he thought, just go with the flow, but his mind was in a whirl wondering what exactly his mum had in store for him.

He took a shower and cleaned his arse out just in case, all dried and his hair combed he put on the clothes and went down stairs to meet his mum in the kitchen.

“My you do look handsome she said as she passed him a large glass of chilled white wine”

Tim’s initial thought was that they might be going out, to a restaurant or something but obviously she was not dressed to go out in public, all she had on was a see-through dressing gown showing of her corset bra and panties.
“What’s going on mum?”

“Sit down, here have a cigarette” Now he was beginning to get a little worried.
“You know I said that I had an idea about you fantasising about me. I think it is because I am the only real woman in your life. What I mean is that I am the only one that you see like this! She stood up displaying all her charms”

“I think if you had the opportunity to have some fun with another girl, a younger girl closer to your age then you might find that you will stop thinking of me in that way”
“Look, I have this gorgeous girl coming round and she is all yours till eleven o’clock”

“You got me a prostitute mum?” Tim almost chocked the words out totally taken aback by this unexpected turn of events.

“Please Tim try it just for me, see if you enjoy it. You might find that you enjoy girls more than you thought you would”

“What is she like mum, have you met her?”
“No I haven’t met her but I have spoken to her on the phone and she seems real nice” “Come with me she has a site on the internet, that’s where I found her”

Going into the front room where the PC was kept Tara quickly typed in her password and the screen flicked on, and up came Steph’s web page.

The title was Slutty Steph. And the picture below was of a young girl totally naked lying on her side sucking on a large dildo. She did look sexy with her long light brown hair large breasts and slim figure.

Tara clicked onto her profile page
It also had a picture of her, this time kneeling down thrusting her tits out with a little caption, Slutty Steph and her thirty-four DD’s

The text read: Hi I’m Steph the hottest eighteen-year-old bareback slag in London.
Fuck my pussy and arse no condoms required as long as you are clean.
It went on about gangbangs YES please, water sports and much more.

Tim had his mouth open and looked up at his mum in shock.
“Yes I know she is a dirty slag. Maybe she will be as big a whore as your mum one day, but I spoke with her on the phone and she seems very genuine, even gets regular STD tests at the same clinic I go to”

“I didn’t think you would want a nice girl! That kind that would want you to wear a condom for a blowjob”
Not knowing what else to say he responded with a simple “No mum, she’s perfect, thanks”

Tara beamed and did a little victory jig her tits bouncing, she was more excited than Tim was and he was getting pretty excited.

Steph was due round at 6:00 and Tim would have five hours with her.
The next hour dragged and mum made sure that she had no bookings until 06:30. She wanted to meet the whore who was going to take her little boys virginity.

Tim had his heart in his mouth when the doorbell rang bang on six. It was Steph, Tara answered the door and ushered her into the kitchen where Tim was waiting. Tim’s mum was a little more conservatively dressed now and was wearing a short skirt that almost covered her stocking tops and a blouse that was not quite see through. She was grinning from ear to ear holding Stephs arm.

Steph also had a big smile on her face and went over to Tim bending down giving him a lingering but gentle kiss on the lips. In her five-inch heels on top of her natural height of five foot six Steph dwarfed little Timmy, “Hi I’m Steph” A little tong tied and nervous he responded with a hello “I’m Tim can I get you a drink”

Her smile grew even more and she said you could help me with my coat first please.
She started to unbutton the front. It was a long coat the type his mum liked to wear on her outcalls and all he could see apart from the coat at the moment was the white high heeled boots she was wearing. Not taking her eyes away from his she continued to unbuttoned her coat. When she reached the last button she opened her coat up and slipped it of her shoulders in one motion, revealing all. Tim was gob smacked.

Her boots went up to just below her knees, light blue fishnet stockings encased her legs ending quite low on her thighs and held up with suspenders, two inches of naked thigh was exposed before the suspenders disappeared beneath her white spandex skirt. The only other garments were a waist clincher and her bra holding in those double D’s. The bra had holes cut out at the nipples and they both proudly stuck out.

Tim’s cock grew rapidly in his pants and her eyes were drawn to his crutch.
“Oh my you have got a nice big one and by the looks of it he likes what he sees”
Putting her coat over the back of a kitchen chair she reached out and grabbed Tim’s crotch, why don’t we take that bottle up to your room”

Tim looked at his mum still smiling, but now the smile looked a little forced. She nodded and with that he picked up the wine bottle and two glasses.

Steph followed Tim up the stairs and into his room.
Tara’s eyes followed them her stomach churning at the thought of this young whore taking away her little boys virginity when it should be her. She wanted to grab the slut and through her out. In her heart she knew this was not what she wanted, it was all a big mistake.

In Tim’s room he put the bottle and glasses down on the bedside table. As he turned around without saying anything Steph went down on her knees in front of him and undid his trousers pulling them down with his underpants, he stepped out of them and removed his shirt.

Holding one foot up at a time Steph removed his socks.
Wasting no more time Steph put both hands around his cock and licked the head, while looking up into his eyes.

“I’m going to enjoy this, it’s not often I get to fuck a virgin”
“Don’t be embarrassed, your mum told me and she also said that you are only fifteen”
“Actually I am still f******n my birthdays not until next Wednesday”
“Fuck that’s hot, I would not normally do someone your age but Tara Rose’s boy wow!! How could I refuse?”

Standing up she pushed Tim back onto his bed. “Would you like me to start on top?”
“Anything you would like to do just ask I am here for your pleasure; the fact that I am going to enjoy this is a bonus”
Tim was now lying on his back with his cock pointing to the ceiling as Steph straddled his chest, her spandex skirt rising up revealing her smooth hairless cunt.

He reached up and felt the weight of her firm breasts through the fabric of her bra. She lowered her tits down to his face so her right nipple brushed his lips and Tim gently sucked it into his mouth. Reaching behind her back he unclasped her bra.
“Oh you naughty boy I would say you have done that before”

She slipped the bra of and discarded it on the bed and smothered his face in the soft flesh of her breasts asking how he learned to undo bras like a pro.
“You can tell me, if you are going to have the best time possible you need to tell me all your secrets and fantasies, don’t be shy with Steph”

Moving her tits slightly away from his face so he could speak he told her about his love of dressing up.
“That’s interesting maybe we could play a little later but first let’s get that big cock of yours deep inside my cunt, I am so wet and ready”

She positioned herself over his cock and lowered herself down on it. It felt wonderful and Tim knew he was not going to last long.
“Fuck your big for such a young man. Your daddy must have been hung like a horse”
“So your a little sissy who likes dressing up in slut’s underwear? What else do you do, or fantasize about?”

The sensation of Steph’s tight and velvety soft pussy on his cock was taking away any inhibitions he had and he revealed that he used vibrators in his arse even that he had tasted his own cum.

“Do you want to eat your own cum out of my cunt when you fill it? I love it when a man does that for me. The trouble is that it is hard to find a man who will eat me out after my cunts been filled, especially if its been filled by other men”

At that he could hold on no longer and said yes please as his hot seed shot out of his cock into her pussy.
She milked his cock with her cunt muscles for a few more seconds before pulling herself off. Cupping her sex she moved up the bed she straddled Tim’s face moving into a sixty-nine position.

Steph slid her hand away from her cunt that was now inches from Tim’s face.
“Go on, don’t be shy, get a good taste of me, lick and suck your cum out of my cunt”

She squished her sloppy cunt down onto his face and Tim needed no further enticement. He devoured the mixture of sex fluids with gusto, as her lips engulfed his still hard cock”

After a few minutes she swivelled round and sat back on his face. Reaching for her handbag she removed a small tube of KY jelly and started to apply some to her arse.
“There I think you have cleaned me up enough, let’s get that hard cock of yours up my arse and see how good you can fuck”

With that she got of his face and positioned herself on the bed next to him on all fours indicating that he should go up behind her, as Tim did she told him to go slow. “That big cock of yours could do some damage”

Kneeling behind her Tim placed his cock at the opening to her arse and started to push as Steph pushed back.
Almost at once the head of his cock slipped into her arse and Steph let out a small gasp and pulled forward a little preventing him from slipping further into her anal passage.

“Just hold it there for a few seconds big boy”
She rotated her arse and pushed back again into him and as she did he pushed forward slipping a good 3 inches of thick shaft into her rectum.
Another small gasp escaped her lips followed by a moan and again she pushed back. This time when he pushed forward he buried his cock to the hilt in her hot arse.
“Fuck’in hell Tim, that fells so fucking good. I love the feeling of a big hot cock stretching my shit hole out”
“I bet you would like to know what this feels like wouldn’t you Tim”

Tim didn’t respond but thought yes, yes you bet I would. Tim just stayed motionless, his hands on Steph’s hips and his cock buried up her arse as she rotated her hips.
“Now start fucking me, but slowly at first I will let you know when I am ready to be fucked hard”

He started to pull out about three or four inches at a time and push it back in, after a few minutes Steph started to rock back and forth with him picking up the pace.
Soon she was calling out for it good and hard lost in passion and Tim obliged.
“Ohh yes that’s it, that feels so fucking gooooood”
“You didn’t answer my question Tim!.... Would you like to know how good this feels, getting your arse reamed out by a big fat hot cock”

“Oh yes Tim replied yes, yes I would love too”
Steph timed her probing question catching him at his weakest, as he was on the verge of filling her bowels with his cum.
A few more deep thrusts and he was shooting his second load into her.
Tim left his cock in her and put his arms around her so I could fondle her tits and nipples.

Their heavy breathing was starting to settle down and they lay spooning with his cock now softening and starting to slip out of her arse.
They heard footsteps coming up the stairs and Tim’s mum talking to a punter.
This made Steph grin and she turned to face Tim, does your mum ever take a day off she asked.

“Only if she is sick or something, why? And you mentioned something earlier about wow fucking Tara Rose’s boy. What did you mean by that?”
“I don’t know if I should say anything” Steph paused knowing that she would, that she couldn’t help herself. This situation was just too awesome for words.

“Your mum Tara is a bit of a cult figure in the seedy underworld. There’s not a whore south of the river, or north of it probably that hasn’t heard of Tara Rose”
“When she called me up I was gob smacked, especially when she asked me if I would be willing to fuck you. I had to double-check her website for the contact details she gave me to convince myself that I was actually talking to the one and only NO! Condoms please! I’m Tara Bareback Rose”

“My mum has a website?”
“Yes, you haven’t seen it? Oh my god you will be in for a shock”
Just search for “Tara Rose bareback slag” or “Tara no condoms Rose” or almost any variation and you will get a lot of hits, and links”

“Anyway enough talking, I’m leaking cum out of my well fuck arse hole. Be a good boy and give it a thoroughly good cleaning out for me would you”

With that Steph rolled onto her stomach and smiled at Tim. “Go on you know you want to”

Tim didn’t need to be told twice and went to work burying his head between her arse cheeks cleaning up first the cum that had run out into her crack then going to work on her hole pulling her checks apart to gain greater access to the red and still slightly loose opening of her shit box.

Tim’s tongue darted in and out with little effort lapping up what cum he could find.
“Fuck you are good at that, I wish I had someone like you around on my busy days to clean me up after each punter had finished with me”

“Oh that sounds so sexy, I would love to do that” and just thinking of it made his cock hard again.
“How about cleaning me up after I’d been gangbanged, five or six loads in both cunt and arse?”
“Fuck yes I would eat all the cum your pussy and arse could hold”

Happy that her arse was cleaned out sufficiently Steph turn over so she was now on her back with Tim kneeling between her legs sporting a fresh hard on.
“It looks like all that talk of cleaning up my holes has given life back to your cock”
“Yes the thought of it turns me on, would you let me do it for you?”

“I don’t think your mum would like me using you as a cleanup boy, but I’ll think about it”

“Let’s not waist that stiff cock of yours, fuck me properly. You came so fast the first time when I was on top I didn’t get a chance to cum myself. You do want to make me cum don’t you?”

“Yes I do” And with that he lined his cock up with her cunt and plunged it all the way in slamming his pubic bone into hers.

“Yes that’s it fuck my whore hole hard and fast. That big cock of yours just hits the spot, yes harder, oohh baby you like my well used cunt don’t you”
“I know you fucking do, don’t deny it, hardcore slag’s like me and your cum dump of a mother turn you on”

“Yes, yes she does, you do”
“You want to fuck that dirty whore you call mummy don’t you”
“YES!! YES!!”

“Call me mummy, tell mummy how much you want to fuck her”
Ahh mummy I want to fuck your used cunt I need to worship your fucked holes, I want to be you’re clean up boy mummy”

As the filth and profanities came pouring from his mouth Tim was drilling Stephs cunt to oblivion, and only the shacking spasms of her body beneath his with an orgasm ripping through her body broke the trance like state he was in.

Her cunt griped his cock milking it and he could no longer hold back, his young body shuddered as he pumped another load of cum into the whore, the whore who he had just told his darkest desires too.

Both of their body’s glistened with sweet and Tim could feel the heat coming from Steph as he held his body weight off hers supporting himself on his elbows.
As Tim’s cock softened and slipped out of her cunt, Steph told him to lie down on his back.
“I want to drain my cunt out. It was matter of fact, and not a request. And Tim complied.
Straddling his face she said she needed a drink and grabbed a glass and the bottle of wine, poring herself a glass she took a hefty gulp, as Tim took a dollop of his own cum that was hanging of her swollen cunt lips.

Putting the glass down Steph picked up her cigarettes and lit one. She then lowered herself onto Tim’s face and started to slide her slippery snatch up and down from his chin to his nose, now with a glass of wine in one hand and a cigarette in the other.

“I wish more of my punters were like you, yes that’s it baby use that tongue on my clit and cunt lips”

“Your cock is pretty limp now sweaty. Mind you three good cum loads in an hour and a half is pretty good. And that last fuck must have taken it out of you; I didn’t think you were ever going to cum.”

Steph paused for a few seconds to put her cigarette down and refilled her glass of wine then restarted slowly fucking his face.

“We are going to play a little game now, put your hands on the cheeks of my arse, yes that’s it”
“This is a yes or no game. If the answer is yes I want you to put a finger up my arse. One finger is for yes and two fingers is for YES!! YES!! fucking right. Squeeze one arse cheek for no and squeeze both for fucking no way. Got it, I said have you got it?”
Tim slipped two fingers up her arse and then replaced his hands back on her arse cheeks.

Good boy, now how many times do you think you will be able to fuck me in the remaining three and a bit hours we have, three more?
Tim stuck two fingers straight up her arse.
How about four more?
Tim wasn’t to overly confident about four so he put one finger up her arse.
“Not bad seven fucks in five hours is fucking good stud material”

She took another sip of wine and a drag on her cigarette.
“I am being very rude, here I am having my cunt licked while sipping wine and smoking a cigarette”
“Would you like a drink to wash down all the cum and cunt juice?”
Tim quickly put two fingers up her arse.

“You might not be so eager if you knew what kind of drink I had in mind. You are too young for alcohol; I think you need to drink it nice and diluted straight out of my pee hole. Will you drink my piss?”

Tim paused and squeezed one of her arse cheeks.
“A little indecisive I see, let’s see if I can change your mind”

As Steph paused for another sip of wine they could her more footstep coming up the stairs, and they could hear Tara’s regular banter to her next fuck of the night.
Steph moved back slightly so she could make eye contact with Tim.
“That cunt you are so lovingly pleasing has only been whored out for a couple of years, and it’s had over a thousand cocks. Almost all of them bareback and Cumming inside me”

She glanced back to catch the sight of Tim’s cock jerking slightly at the thought of it.
“Yes that turns you on, you could not fuck a nice clean girl your own age. You’re just not turned on by them are you?”

“That was a question by the way, are you turned on by nice clean girls your own age?”
Tim squeezed both her arse cheeks.
“Yes I know, you need the thrill of a real ditty whore. And they don’t come any dirtier than Tara Rose”
Tim’s cock jerked and twitched again and Steph continued. “Can you begin to imagine just how many cocks have been in your mum’s cunt and arse and mouth dumping their cum in her.”

Tim’s face was now slick with the mixed sex juices and his cock was semi erect.
“Do you want me to continue?”
Again he stuck 2 fingers up Stephs arse. He desperately wanted to hear more about his whore of a mother, more about the woman he desperately wanted to fuck and be fucked by.

“Well here is the deal. I need to take a piss and your mouth is where I want to piss. You drink my piss and don’t spill a drop and I will tell you more. Yes! Or No!”
Tim hesitated before putting one finger in her arse.

“Good boy I knew you would come round now open wide and get ready to swallow” With that a hot stream of piss hit the back of his throat and he swallowed. Steph had hold of the back of his head and clamped her cunt over his opened mouth causing a airtight seal, she was making sure he swallowed the lot. She didn’t let it all out in one go she filled his mouth and then cut the stream of piss and started it again when he had finished swallowing what he had.

The taste was nowhere near as bad as Tim was expecting it to be and after all the sticky cum and pussy juice he had consumed it felt pretty good. So good it made his cock jerk.

“A cock doesn’t lie, I had a feeling you would like drinking my piss. I bet I get two fingers up my arse to my next question”
“Would you like to drink your mums piss?

Tim’s cock jerked violently and grew now to almost a full erection and he thrust two fingers up Steph’s arse.

“Wow that was a YES! YES! oh my fucking YES!! Just look at your cock grow.
If you did drink your mums piss there would be a good chance that you would be drinking someone else’s as well. Your mum drinks piss for a living baby. It’s one of her many! many! Specialities”

That was enough to put Tim’s cock back into a full erection.
Moving of Tim’s face Steph positioned herself over his cock and impaled herself in one swift downward plunge and started to slowly ride his cock.

“You check out the internet and you will see just what kind of depravity your mum’s capable of. I’m one of the dirtiest whores around. But I am Snow White compared to Tara fucking bareback Rose”

Steph’s train of thought was lost as she started sliding up and down Tim’s cock with force and one hand frantically rubbing her clit. Her other hand and forearm where trying to support her tits as they flopped and jiggled to the frantic pace.

Tim was thrusting up as hard as he could to keep pace with the a****l intensity of Steph’s fucking. Eventually her eyes closed and her pussy pulsated clenching and releasing again and again on his cock. Having already come three times Tim was close but just not there and Steph collapsed on top of him clamping her mouth over his forcing her tong into his mouth in between gasps for air.

Tim continued to work his cock in her over heated love box holding her sweaty body tightly to his until he came.
“Fuck that one was good, I think I get as turned on as much as you just thinking of what your mother has done. I would love to have a go on her myself. I should have negotiated a freebee as well as the cash for fucking you”

“How much is mum paying you to fuck me?”
“Naughty boy you should never ask how much your birthday present cost. I just hope it is the best one you’ve ever had”
“I can honestly say this is by far the best”

“It’s not finished yet! Let’s have a quick sixty-nine so you can give my cunt a quick clean out and then we will have a fag break”
“Sounds good to me” Tim said as Steph swivelled round to plat her sopping cunt down on his face.

All cleaned up they sat on the edge of the bed with the last of the wine now poured evenly into two glasses, Steph picked up her cigarettes and lit two giving Tim one. As they puffed away the familiar sound of footsteps could be heard coming up the stairs. Looking at each other they smiled. And when the punter said that he’s was looking for a good strap-on session, Steph’s face beamed, and beamed even more to Tara’s reply.

“You have come to the right place, but I don’t do good strap-on fun I do the best.
It’s one of my faves, you can set your own limits on size or you can trust Tara to find them”

With that Steph whispered in his ear. “I want to fuck your arse and I know you want me to. Tara must have more strap-ons than you can shake a stick at, any chance you can get hold of one, and is your arse clean?”

“Yes and Yes, I didn’t know what to expect tonight and mum knows about my dressing up and the toys, I was kind of hopping she was going to fuck me, well I didn’t know what to expect really so I cleaned my arse out just in case anyway”

“And yes mum has quite a few dildos and strap-ons. If she doesn’t have what she needs in her bedroom she will get one out of the spare bedroom, her walk in dressing room”

“Let’s give her five minutes to get going and then you can creep down and grab one” Steph giggled a little at her plan.

“In the meantime have you got some girly gear you could put on, if I am going to fuck you rotten you may as well be dressed for it”

Tim smiled and said yes and that his mum had bought them for him. He got up and pulled a small suitcase out from under the bed and opened it.
Steph’s face was a picture as he started unpacking his treasures. Her mouth was a gape as Tim quickly rolled up and put on his red fishnet holdup’s, standing up to check that they were strait and even.

Steph said impatiently. “Go get that fucking strap-on, your arse is mine”
Tim crept down to his mum’s dressing room and selected a strap-on harness with a seven inch dildo, as he knew that he could handle that. He was tempted to get something bigger but some sanity stopped him.

Back in Tim’s room Steph was on her knees looking at the stuff in his suitcase. She held up with one finger his rubber panties with a, what the fuck look on her face.
Tim returned with the strap-on and saw Steph with the rubber panties and the slightly puzzled expression.

“My mum makes me where them when she helps me dress up so my cock doesn’t get in the way. I can’t help getting an erection, wearing them prevents me from getting one”

With a sarcastic smile Steph said “O you poor thing, well an erection round me is something I insist on. Now let’s have a look at that strap-on”

After a quick inspection, Steph announced that it would do nicely.
“A nice sized dong. Have you had this up your arse before?”
“No but I use a vibrator about the same size”
“Ok let’s get you dressed, I see you have breast forms, your mum must have got you these as well”
“Yes, she bought all of these things for me“

Tim picked up a red bra and put it on then inserted the breast forms. As he was doing this Steph had now discarded her spandex skirt that had ended up just a bunched up roll of material that had gathered above her hips, and had the strap-on all buckled up and ready to go.

“Fuck the rest of your gear, get on the bed, doggie style. Your going to get fucked”
The next thing Tim felt was Steph’s tongue liking his arsehole probing and pushing its way into his arse that was now itching with anticipation.
Using her tube of KY jelly Steph lubed up the strap-on and pushed a finger with a good blob on it into and on the entrance to his rectum.

The suspense was killing him as she positioned the cock against his boy pussy, the tip just pressing against him not quite penetrating.
“Tell me Tim have you got a fem name for yourself? If not I will give you one”
“Yes, its Rosie mum calls me Rosie when I dress up”

“That’s a good name for a sissy boy whore, she has chosen well. What do you think?”
“Yes I like it, fuck me and call me Rosie”
Steph applied a bit more pressure to his hole and he felt it start to open and yield to her cock.
“Tell me Rosie how much do you want this? Do you want to be my whore?”

“Fucking yourself up the arse is one thing; giving up your back door to someone else is another matter entirely”
“When a man is lost in his lust, the whore must take it as hard and as deep as the bastard wants to go. Just like you did with me just an hour or so ago”

She was teasing him with the tip of the strap-on cock just inside his anal ring.
“You want it Rosie, you want me to fuck you?”
“Yes I want it, I want to your whore. Please fuck me like one”

With that Steph push forward in earnest getting half of the cock in his arse with ease and quickly buried the rest.
“Fuck Rosie your whore arse swallowed that cock, you dirty fucking slag”

Now she started pumping his arse, increasing the force going at him harder and harder. The violent assault was making his eyes water and he could feel saliva dribbling out of the corner of his mouth, but he didn’t want her to stop.

“God Rosie you are a good whore, you take it like a pro. I bet you wish it was your mum in my place battering the fuck out of your arse”
“Yeesss!!” was all he could manage as his cock pulsed and twitched.

Steph reached under him and gently stroked his dick as he came.
“Fuck Rosie you are a slag, another load shot off and I hardly touched you cock”
“The thought of getting a good hard fucking from your mum must have really pushed a button or two”

Steph never let up even though Tim had almost spontaneously ejaculated. A good load of his cum was now over the bed sheets and his cock was still rock hard and swinging wildly between his legs as Steph continued to pound his arse.

“The games not over because you came slut, I’m not giving up on your fuck hole until I cum, it may take a while but I’m not stopping till I do”

Steph’s pace was relentless but Tim’s arse was well adjusted to the size of the dildo, and the fucking he was getting was pure pleasure. He was even thinking that he should have brought a second bigger dildo for her to use. He reached back and started fisting his cock to the rhythm of Steph’s fucking.

Tim came again just before Steph shuddered in climax collapsing on his back and grabbing his false tits.

With only one arm supporting him and one hand still on his cock her weight pushed him flat on the bed beneath her.
She laid panting on his back with the strap-on cock buried up his arse for over ten minutes whispering sweet nothings in his ear, telling Tim what a good fuck he was, and a natural whore.

They heard Tara’s punter leave.
“I bet your mum didn’t enjoy fucking his arse as much as I enjoyed fucking yours”
“Do you really think I am a natural whore?”
“Rosie, you were born to be a sissy whore. Your mum may not like it but it’s a fact. You can’t fight it, and she can’t stop it. You will be selling that arse of yours before you know it; you need cock up it, and lots of it. Just like I do and you’re mum does”

With that more footsteps could be heard on the stairs and the loud chatter coming from a number of men.
Steph whispered six, seven? Tim whispered back usually eight and smiled, adding that his mum says two of the Friday night guys let their cocks do the talking.

Steph giggled still lying on Tim’s back, and snuggled up to him rotating the dildo still in his arse.
“I’m thirsty any chance of steeling another bottle of wine?”

“Yes I can get another bottle I desperately need a piss anyway”

Steph got off Tim’s back pulling the strap-on cock out of his abused arse hole. And he could feel cool air reaching inside his stretched sphincter.

As he got off the bed to go and get the wine Steph stopped him.
“Do you want to piss in my mouth?” She asked as she was already going down on her knees mouth open.
Tim didn’t reply, he just put his cock in her mouth and she grabbed it with both hands. She looked up at him as if to say, why aren’t you pissing, and then he let go.

She swallowed as fast as she could and giving up she gripped his cock hard stemming the flow, and then releasing the pressure on it to refill her mouth.

Finally with Tim’s bladder emptied Steph licked her lips and said thanks I needed that.
“You see your mum isn’t the only piss drinking whore round here”

Tim’s cock was stiffening again, and Steph took it back into her mouth for a few seconds before releasing it and looked up at him.
“I only have to mention your slag mother and you get a hard on don’t you”

He didn’t need to answer the stiffening of his cock did that for him.
“Go get the wine”
She gave him a playfully slap on his arse as he left to fetch the wine, leaving Steph taking off the strap-on.

When he returned Steph had her tube of KY squirting a blob onto her finger she applied it to her arse.
“Let’s have a quick drink and then it is your turn to fuck my arse and fuck it hard, I don’t give a fuck and I have suddenly got the need to be drilled good and proper. And I know how to make you do it”

Tim poured out two full glasses as Steph lit up two cigarettes and they sat on the edge of the bed and sipped the wine and had their smokes.

Steph put her cigarette out and put down her wine glass before taking Tim’s half smoked cigarette off him and stubbing it out.

“Time to fuck, but you cock needs a little help by the looks of it, and like I said, I now know how to get you hard”

Steph got on the floor between Tim’s thighs and sucked him into her mouth then she let his cock slip from his lips. “I wonder how many of those men in there with your mum have already shot their spunk up her battered cunt or arse yet”

His cock stated to stir as she briefly took it back in her mouth.
“You think they will all fuck her twice?” She dipped her head back down to flick his cock head with her tongue not wanting or expecting a reply from Tim but got one.
“Yes, at least”

“So the dirty slag will have at least sixteen loads of spunk sloshing around in her well used whore holes”
Tim’s cock was rejuvenating fast now as Steph slurped away on his cock, massaging his balls and slipping three fingers into his arse.

His cock now ready for her butt hole she got on the bed doggie fashion.
“Come on Rosie what are you waiting for? Your mum’s in her room just down the landing getting gang fucked the lucky slut. The least you can do is tear my arse hole up a little”

Tim got on the bed and lined his cock up with Stephs arse and rammed it home, “Ahhhh fucking ‘A’ I bet that’s how mummy dear likes it. How many guys does mummy fuck a day?”
“I don’t know maybe between five and eight or on weekdays”
Tim started plunging into Stephs arse, but in his mind’s eye it was his mum he was fucking.

“Fuck off!! Maybe five or eight in the evenings when you are home from school. But how many men does she do during the day when you are not here?”
“I don’t know”
“I’ll tell you, that cum bucket thinks it’s been a slow day if she doesn’t reach double figures, and you want to drink her piss and clean her holes out”

This was too much for Tim and he hammered into Steph’s shit hole as hard as he could.
“Ooo yeeesss now you are getting it, fuck me, fuck me harder. You know your mum would appreciate this kind of pounding”

Tim carried on fucking Steph’s arse as she kept on saying what a whore his mum was and he loved it. He closed his eyes and again imagined that Steph was his mum and it was her arse he was fucking, he was lost in his own world again and only when he shot his load did he come down to earth.

His cock was still in Steph’s arse and she turned her head round and said ready to go again.
Sweet was dripping of Tim and he said no he don’t think he could.

“Leave that cock in my arse you bastard. You are the son of the filthiest whore alive and your cock is going to stay hard and fuck me again. Rumour has it mummy made her first porn movie when she was twelve, fucking twelve!”

“Her body was sold all over London to perverts that liked u******e girls. She must have fucked thousands of men before she got pregnant with you”

“That’s it I can feel your cock growing in my arse, you will put another load in me.
Even the u******e prostitution and movies your mum made before you were born pale in comparison to what she did afterwards”

“A small group of triple X rated theatres sprang up in a round London, members only clubs supposedly. Each of these theatres had a twice a week floorshow a matinee and evening performance each theatre having a different day. It was always one girl and normally one or two very well hung men and I am talking hung”

“After the fucking display the girl was anybody’s who wanted to wait in line and fuck her”
“Yes you guessed it by the thickening of that cock in my arse and the way you are inching in and out of my shitter”

“Your mum was a regular; it was difficult to find a slag prepared to take on anybody with any hole all bareback, especially someone as pretty as Tara”
Tim’s cock was unbelievably getting hard again, and he was starting to slowly move his cock more and more in Steph’s back door, what she was saying about his mum could not be true could it, yes he thought yes it could.

“Each theatre held between thirty and forty paying customers, and they were always full on floorshow nights. Not everybody fucked the floor girl but most did, that’s why they paid for the ticket”

Tim’s cock was rock hard again and he was building up a good steady rhythm listening to Steph’s account of his mothers early years of whoredom.
Tara was just sixteen when she started doing three theatres a week matinees and evenings. And by all accounts she was really popular!

Tim started to pump harder into Steph’s arse just the thought of his mum and all those men.
Steph felt his arousal and said you haven’t heard fuck all yet.

Tim’s cock felt like it was growing even more than he thought possible and he started to fuck long hard deep strokes into Steph’s now loose and sloppy arse hole, with her pushing back just as hard on every stroke.

“About six months in disaster stuck and three girls all want down with the clap at the same time, another two girls refused to work. Your mum did the matinee and evening shows at all 6 theatres for 3 weeks running”
“Do the maths on that, she was into her fourth week when a number of customers complained that they had picked up something nasty from Tara”

“Your mum went down to the clap clinic, and she was diagnosed with more types of VD than you can shake a stick at; anal, vaginal, oral”

Tim was now flying into Steph’s arse struggling to reach a climax, with his balls straining to produce yet more cum.

“A month or so after getting the diagnosis and treatment Tara was given a clean bill of health. And what does the slag do, with a clean bill of health she does a gangbang movie with twenty-one black men and then strait back to the theatres”
At this point Tim’s cock was pumping what liquid was left in him and it continued to pump but with nothing left to give into Steph’s abused hole.
It was Tim’s turn to collapse on her.

The next thing Tim knew was Steph prodding him.
“I have to go my taxi will be here in ten minutes, be quick and give my arse a quick lick out”
Tim rubbed his eyes and looked at the clock, it was just coming up for ten to eleven. He quickly got up and buried his face between her arse cheeks and wormed his tongue around sucking up the anal juice and cums.

“That’s enough Rosie” She gently pushed his face away from her arse cheeks and got of the bed putting on her bra. Fishing in her handbag she pulled out a pair of panties and slipped them on. “I go out not wearing any and go home with them on, Stops the cum from running down my legs”

Going back into her handbag she pulled out a business card. What the fuck am I doing she thought to herself as she clutched the card in her hand.

Getting of the bed Tim took off the stocking and bra he was still wearing and put all his things back in his little suitcase and pushed it back under the bed.

Tim put on his dressing gown as Steph picked up her cigarettes and had one last look round to check nothing was left behind. Just before they made their way downstairs Steph pulled Tim into her arms and whispered in his ear at the same time pressing the card into his hand.
“This card has my mobile number on it and my address on the back, if you would like to see me again.....you know....to lick me out give me a call. But you cant tell your mum”

Tim was quite stunned and pulled away so he could look up into her eyes “you mean it, you will really let me, and I wouldn’t have to pay?”

Steph giggled and stroked his delicately smooth cheeks. “No you won’t have to pay you just do a good job. But you must keep it a secret; your mum would go ballistic if she found out”

Tara was in the kitchen having a cigarette and a very large glass of wine as they entered, she stood up and smiled at them both.
“Well Tim how did you like your birthday present”

Tim’s smile said it all as he look up at Steph and then his mum announcing that it was the best ever thank you mum.

Steph chipped in; “It was one hell of a night Tara. You have, let’s just say a very talented son, and there is nothing wrong with his equipment either,”

Tara smiled again but it looked a little forced. In fact it was, Tara’s was torn with her emotions. But the smile on Tim’s face told her it was worth it; well maybe it was worth it.

Tim felt more than a little awkward standing in the kitchen with his mum wearing a see-through robe a half cup bra that just about supported the bulk of her breasts displaying het tattooed nipples for all to see, a pair of panties, her fishnet holdups and her high heels.
And Steph now back in her nipple less bra, waist clincher, fish net stockings, boots and spandex skirt.

Tim passed Steph her coat right on cue as the doorbell rang,
Getting up Tara said “That must be the taxi, I’m not expecting anyone else tonight” she walked over to Steph and gave her a kiss on the check, saying I will be in touch.

“Tim be a gentleman and see Steph to the door”

At the door Steph gave Tim a long and deep kiss that broke as the impatient taxi driver stated ringing the bell again.
See you soon I hope she whispered in his ear.

Tim opened the door and Steph went out up the garden path following the taxi driver. Turning at the gate she waved and said goodbye Rosie until the next time.

Closing the door Tim went back into the kitchen and poured himself a big glass of
water and downed it in one. Refilling it mum pitched in “worked up a thrust”
“You could say that” he beamed a smile back at her. “It was out of this world mum thanks”

A little relief came to Tara’s face and she got up out her chair moving towards him, her robe opened up with the movement, her arms stretched out. “Give mummy a hug”

Tim went to her and slipped his arms inside her dressing gown putting one hand on the small of her back and one up between her shoulder blades. Her arms came around him and pulled him tightly into her.

For a couple of seconds mother and son just hugged, Tim felt the sweet on her back, her skin was clammy. Even though Tim had been eating his own cum licking out Steph’s cunt and arse all night the heavy smell of cum on his mums breath was unmistakable, and her body smelt of piss and sweat.

She had been repeatedly fuck by eight guys, in addition she had been pissed on or in by the smell of it. And hadn’t bothered to clean herself up.
Tara pulled slightly away and her lips inches from Tim’s.
“What did you think of Steph then?”
“I loved her mum, in a lot of ways she reminds me of you”
“All good ways I hope”
“Absolutely mum”

Tara pulled him to her again and squeezed him tight, Tim couldn’t resist the temptation and whispered in her ear “she even wares panties like yours to stop the cum from running down her legs” as he was telling her this he patted the back of his mum’s panties low down between her arse cheeks. They were drenched.

Mum pulled away with a chuckle. “You cheeky beggar” Get yourself up stairs and cleaned up before I cancel all future birthday presents”
“Yes mum I’m gone”

With that Tim skipped up the stars to the bathroom picking up the strap-on on route.
Showered and all cleaned up he put the strap-on back in its place and went back to his room.

He pulled of the soiled silk beading and put back on his nylon and cotton sheets, through the duvet on top and flopped onto his bed and he was quickly in the land of nod.


To be continued............