The Making Of Rosie Chapter 3 “Rosie, Steph And Ge 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 third instalment documenting his journey to becoming a shemale whore. (Fb, M+F, prost, whore, size, tv, toys, creampie, strap-on, ws)

Chapter 3 “Rosie, Steph and Georgy too”


After his birthday surprise night with Steph Tim’s head was in a spin and his stomach in knots. He kept looking at the business card she had given him, with her number printed on the glossy front with a picture of her semi naked posing sexily, and on the back she had written her address.

It was just a week later at eleven o’clock on a Saturday morning and by the sounds of it, his mom was getting some serious dick up her arse, and enjoying every inch of it. When he made his mind up, he had to get out and call Steph. The thought of eating her pussy and arse out after she had been filled with cum by one or hopefully more of her punters was almost too much to take.

Feeling quite daring, and after the wonders that he had experienced just the week before, he put on his pink fishnet holdups and pink waist cincher corset, tightening it as hard as he could without giving himself too much discomfort, but nowhere near as tight as his mum would have done. He wriggled his way into his rubber pants tucking his cock away before pulling on his pink panties, followed by his jeans and sweeter to mask his under garments, as much as he did to protect him from the cold.

Grabbing his school duffel bag, he quickly put in a pair of white patent leather court shoes, his false tits, pink bra, blonde wig, make-up bag, and white frilly-tiered mini skirt. Before heading down to the kitchen where he quickly wrote a note to his mum sticking it on the fridge door saying he was going down to the shopping precinct and then to MacDonald’s and that he would be back about seven.

At the end of his street by the video shop was a phone box and with his heart racing he phoned Steph, but disappointingly only got her answer machine.

“Hi Steph this is Tim....um Rosie..can I come over?...I will call back at twelve.”
He hung up and decided to take the bus over to the tower block where she lived and worked to try to phone her again. It was only a twenty-minute journey and he was there at ten to twelve looking for a phone box.

When he dialled her number this time Steph picked up straight away and gave him directions to her flat, and the door code to the block so he could let himself in and come up to her floor.

As Tim got to her door, she opened it before he could even knock greeting him with a beaming smile telling him how glad she was he’d called, and that his timing could not have been better. Leading him to her bedroom she slipped of her robe, laying on the bed in just tattered black fishnet hold ups parting her legs wide and with a big grin she waged her finger at Rosie beckoning him towards her.

“Come and get it Rosie, your first cream pie that’s not your own. You know you want it.”

All inhibitions gone he hurriedly stripped down to his girly underwear and crawled up between Steph’s thighs licking his lips.

“You got dressed up for me Rosie I’m impressed, now start by cleaning up the cum that’s run out of me and work your way up my pussy”

His tongue and lips gently worked away on her silky smooth inner thighs and the lower folds of her pussy lips, working his way towards the prize as Steph laid back and relaxed.

“O my God Rosie you are so fucking good, yes....yes go for my dirty fuck hole”
Steph was in heaven as Rosie worked away at her freshly fucked pussy. The gentle assault on her well-fucked cunt was soothing and divine.

Steph loved sex and would be the first to admit that she was a filthy slag and a whore who loved having men pound her holes; it was what she lived for. But at this moment nothing could compare to having Rosie between her legs feeding on her cum filled whore pussy. She stretched her limbs and raised her crotch pushing her sex into his mouth, her eyes closed revelling in the shear decadence of having her cunt worshiped so lovingly by such a beautiful young sissy boy.

Rosie had his tongue swirling around Steph’s slimy snatch, his eyes closed in bliss as his senses guided his oral administration of her saturated sex, working another mans cum out of a freshly fucked cunt for the first time.

The perfect moment of mutual joy was severed as Steph’s mobile phone burst into life. For a few seconds she ignored the most unwelcome interruption not wanting the blissful experience to be broken. But she finally gave in and reluctantly picked up her mobile. “Hello”

“Is that Steph?”
“Yes are you looking for some business?”
“Yes I am, are you free now and do you really do bareback?”
“Yes and yes, and before you ask I don’t charge extra for bareback it’s on the house, cunt or arse and you can cum inside me where you like and I swallow. Thirty for a quickie pump and dump, half an hour is fifty and it’s eighty for the hour”

The punter asked for directions and said he would be twenty minutes. Steph reluctantly asked Rosie to stop pleasuring her pussy and got of the bed.
“I need to clean up properly Rosie baby, come with me and bring your things”
On the way to the bathroom Steph showed Rosie the spare bedroom and told him that he could put his things in there and it was were he could wait when she was fucking punters.

Steph had done three more punters and Tim had his face between her arse checks greedily eating his first anal creampie as the clock struck six. He had to start getting himself cleaned up and ready to get of home.

As he was getting his things together Steph came up behind him and put her arms around him pulling him to her. She had put on her strapon and Rosie felt the appendage poke into the crack of his arse checks.

“You’ve really got the taste for cum haven’t you Rosie, and I bet your cock has been dribbling away in your tight rubber panties hasn’t it”

“Yes, I loved it. I knew I would. Are you going to fuck me, please fuck me?”
“I’m going to fuck you baby, and your going to wank your cock with a pair of my soiled cum stained panties.”

Steph soon had Rosie knelt up on the bed his panties round his ankles and was thrusting into him as he feverishly tugged away at his cock with his pantie clad hand. As she fucked away at his hungry hole she told him that his mum would love to do this to him, and have him lick her out. Talking about his mum when she fucked him always turn him on. This was his sexual button and like any good whore she would keep on pressing it for as long as it kept working, and she had a feeling that it wouldn’t stop until he experienced his fantasy, and maybe not even then.

“This is going to be a regular thing Rosie, your going to service my cunt every Saturday and I’m going to service your hungry hole as payment. But there is something I want you do for yourself. It will help you get what you want. Dress slutty when you’re at home. Playing dress up on Sundays has to stop. Be fem all the time baby, show your whore of a mother that you’re committed to being a sissy full time.”

I will, I will Rosie cried as he came into Steph’s already soiled panties.

As soon as he came she puled her strapon out of his arse and gave both his arse cheeks a playful slap telling to get on home, and be back next week at twelve o’clock prompt to clean her out and get his arse fucked.


Rosie had settled into the routine of spending Saturdays with Steph and loved it. He hadn’t stopped fantasising about his mum, but took Steph’s advice and got into mincing around the house dressed like a slut.

Tara was disappointed that her little boy was always dressed sexily and playing dress up on Sundays was not required, as he was always looking good enough to fuck. But this also turned her on and she wanted and lusted after him more than ever.



It was coming up to the end of November on a cold but dry winters day as Rosie was working the last remnants of Steph’s previous punters cum out of her pussy when he heard the front door to her flat open.

Steph, called out “is that you Georgy? I’m in my bedroom getting my dirty cunt licked out by my sissy boy.”
She locked down at Rosie who looked a little startled and had stopped his oral administrations. Steph thrust her pussy up into Rosie’s face and told him to continue.

He couldn’t see the girl when she entered the bedroom but he knew the voice, and a slight panic was beginning to hit as Georgy came in. She was talking excitedly about how one of her Pakistani boyfriends Danish had taken her behind the bins at the back of Tesco’s and fucked her with five of his mates looking on. When he was finished with her, Danish told her to let his friends take turns on her or he wouldn’t take her to the pictures. But by the time they had all been through her Danish was gone and not taken her like he had promised to the pictures.

Having completed her sordid tale she paused momentarily studding Rosie, his face between her cousin Steph’s thighs licking her pussy out.

“So this is the sissy boy who loves eating cummy pussy you told me about. Do you think she will do me? Danish and his mates didn’t use condoms, they never do and I’ve got cum running down to my sock tops. I’m sloppy as fuck, and I’ve never had my cummy pussy licked out before”

Georgy had a long winters coat on that was now open, and she stood with her hands on her hips revealing her white and pink thigh high tube socks, a tiny nine inch pink micro mini tartan skirt, braless with a skimpy white tie front crop top that was barley covering and exaggerating the cleavage between her generous bust.

Rosie looked up from between Steph’s thighs, and one glimpse of the dishevelled slutty girl confirmed his fears. It was Georgina Evens, a very pretty girl with unnaturally large boobs for her age and in the same year as he was at school.

Georgy studied Rosie for a few seconds, she thought he looked familiar but couldn’t put her finger on who he was or where she had seen him before.

“Well Rosie, I bet your hungry for more cum. You can never get enough, you’re a greedy slag and I need to get ready for my one thirty. I bet you’d love to go with Georgy into the spare room and clean the cum out of her slutty cunt while I’m entertaining my next punter, wouldn’t you?”

Rosie found it hard to form any words at first, she was sure to recognise him. But the puzzled expression, turning into recognition with a broad mischievous smile spreading across her face told him it was to late.

Georgy was the school slag and didn’t mind who knew it, they even shared some classes together. A lot of the boys in his school claimed they had fucked her, and many of them had. She was the only girl in school he had ever fantasised about. Maybe because she looked like he imagined his mum would have at her age, but certainly because of her reputation for being such a dirty slag and cum dump.

The vivacious slut turned Rosie on and he didn’t care that she had recognised him and was even quite relieved. She was a proper dirty little slag with a well-fucked pussy, and he wanted her. He was determined to give her the time of her life, and hopefully get to fuck her used pussy as well.

“I’m always hungry for a cum filled pussy, and I’d love to go down on yours Georgy. I’ve wanted to lick you out for some time.”

Georgy’s grin spread across her face as she excitedly waved her arms about. “I knew it, your little Timmy Rose with the big dick, can I see it. You look lovely, have you got many outfits?”
Georgy talked incessantly when she was excited, and right now she was very excited. Taking Rosie’s hand she almost dragged her into the spare bedroom.

Steph giggled and told Georgy to be gentle with him, and not to make to much noise.

As soon as they got into the spare bedroom Georgy puled Rosie’s hand up to her chest planting it on her ample left breast.

“I don’t wear nickers or a bra when I’m out hunting for cock. I like to let guys know I’m a slag and ready to fuck. You can feel me up Rosie, I love to get felt up.”

Georgy had her hand between Rosie’s legs trying to free his cock from the confines of his rubber knickers as he untied her shirt releasing her tits.
Having freed her firm young breasts Rosie helped her out by pulling his rubber knickers and panties down letting his already dripping cock spring free into Georgy’s grasp.

“O my God Rosie your dick is so fucking big, it’s almost as big as my step dads. I want it inside me, you’ve got to fuck me”

Rosie gently pushed Georgy onto the bed, he was submissive by nature but all of a sudden he wanted to fuck this little slag, and fuck her good and hard. But first he needed to get a taste of her filthy cum filled and dripping cunt.

Georgy shuffled herself back up the bed and opened her legs as he crawled up between them. A flush of excitement came over her as Rosie went for her pussy, but stopping short to kiss and lick her inner thighs from her sock tops to the folds at the base of her pussy before fixing his lips over her dripping hole.

Steph had douched herself out and was now peering in at the young couple. Her index finger strumming away on her clit as she watched Rosie give her cousin’s dirty cunt a workout. The little slag had never come close to experiencing this kind of pleasure before and Steph almost felt a little bit jealous as Georgy convulsed in orgasm and tried to push Rosie’s lips away from her now hypersensitive pulsating sex.

Rosie raised his head up from between her thighs and knelt between them lining the fat head of his rock hard throbbing cock slick with pre-cum, up with the entrance to her sloppy fuck hole and drove home going in balls deep with a lot less resistance than he was expecting on his first thrust. God this is one filthy slag he thought as he ground his cock into her and she wrapped her legs around him and drew him into her body, telling him to give her a good fucking.

Rosie responded giving her long hard stokes knowing he wouldn’t last long inside her slippery gash. He was horny and didn’t care; he would fuck her hard and fast then keep on going until he came in her a second time.

The door buzzer went and Steph reluctantly left them to it, closing the bedroom door she went to great her next punter who was waiting at the front door.


After getting a much better than average fucking from her punter who managed to fuck her not twice but three times in the hour he had booked her for. Filling her pussy twice and spilling one load down her throat, she showed him out and went in to see the two lovers.

Rosie had been busy and was now eating his third load out of Georgy’s pussy. She was grinning like a Cheshire cat as she looked up at Steph entering the room carrying a strapon harness.

“She’s fucking good isn’t she, do you want a go?”

“Yes, she is that, and I’m having a go all right, its time for his sissy arse to get a fucking. You can do it today while he licks me out.”
Handing the strapon and a tube of anal lube to Georgy she added that the slut likes it rough.

Georgy had never used a strapon before and was eager to have a go and was quick to work out how to put the harness on. With Rosie already face down between Steph’s thighs she went behind him, his arse sticking up over the end of the bed and at a good and accessible height for Georgy to fuck him standing up.


Georgy took Rosie’s hand and squeezed it as they walked out into the dark winters evening. She rubbed her shoulder up against his as they made their way to the bus stop. For once Georgy was silent, basking in the glow of the afternoon’s debauchery.
As they got to the bus stop she turned and smiled into Rosie’s face. “You do like me don’t you Rosie, and its not just because I’m a slag is it?”

“No, not just because you’re a slag, I loved licking your pussy out. But I like you a lot, I wish you were my girlfriend.”
“I’ll be your girlfriend Rosie, but I wont keep it a secret. I’d want people to know that you’re my boyfriend. I’ve never had a proper boyfriend before.”

Rosie told her that he didn’t care who knew, and they chatted and hugged until his bus turned up. Rosie didn’t want to leave Georgy waiting for her bus but he was late already and had to get going, and knew he would have a wave of questions from his mum when he got home.

As Rosie walked slowly down the road leading up to his house he thought of excuses for being over an hour late. He knew his mum saw straight through him when he did tell her a lie, even if it was a little one. And had settled on bending the truth a little, besides he was desperate to tell his mum that he had a girlfriend.

As he approached the front door three middle aged men filed out in good cheer as his mum stood holding the door studying Rosie come up the garden path.

The men gave Rosie little mind and one of them gave him a wink and a smile as he passed. Tara ushered him in and closed the door, she didn’t look mad, she even had a cheeky grin as she asked him why he was so late and what on earth he found to do in the shopping precinct for hours on end every Saturday.

Rosie gave her a quick kiss and a hug before telling her that he had something to tell her but could he get changed first.

“I’m intrigued, go on and be quick. I’ll be in the kitchen.”

Rosie scampered up the stairs and striped off putting on a clean pair of black holdup stockings, bra, panties, a tight little skirt and black see-through blouse before applying a little makeup before stepping into her black pump shoes and fixing her blonde blunt cut wig.

Tara was sat at the kitchen table in her usual chair with glass of wine in hand as Rosie came in looking every inch a slut. The thought of sitting on the sluts face with his tongue up her loose hole licking her out flashed through her mind making her pussy throb with excitement. Forcing the devilish desires to the back of her mind so looked up smiling as she told Rosie to spill the beans, and tell her his news.

Rosie couldn’t contain himself and came straight out an told Tara that he had a girlfriend.

She was speechless for a few seconds as she studded her little sissy boys face, who couldn’t wait to get out of his boy clothes to dress up like a tart as soon as he came through the front door these days.

There was no doubt he was excited and wasn’t making it up, but the news was like a bolt out of the blue. Her mind was racing who could she be. A shiver ran up her spine as she thought of Steph.

“So who is she, how long have you know her, where did you meet and more importantly how old is she?”

“She’s the same age as me mum, her names Georgina but everyone calls her Georgy. She’s a friend from school. She’s lovely, I know you’d like her.”

Tara was relived, and her face lit up telling Rosie that it was wonderful news. But bringing things down to earth she asked if Georgy new about his fetish for dressing up like a slut.

Without thinking he replied excitedly “O yes, and she likes, she likes to dress up like a slut too.”

As soon as the words came out of Rosie’s mouth he replayed them in his head, and wished he could take them back. But he needn’t have worried. Tara burst out laughing, her shoulders and tit flesh jiggling as Rosie looked at her feeling like she was mocking him, and he felt a flush of heat rush across the cheeks of his face as he blushed.

Tara tried to control herself and got up from the table and went round to Rosie pulling him up out of his chair and into her arms pressing her body against his and hugging him tight.

“I’m sorry Rosie for laughing, I’m really happy you’ve found yourself a girlfriend, and one the likes you for what you are. She’s a slag like me isn’t she?”

“Yes mum, she’s a slag. Its one of the things I like about her. She’s a lot like you.”

“Well, you wont be wanting me to get Steph round to give you a Christmas present will you. I guess you having a slag for girlfriend has its perks; I guess you better invite her round so I can meet her. What do you think she will make of me?”

“She will love you mum, I know she will”



Tara was pleased with the change in Rosie, he was getting more confident in himself and paid a lot more attention to his appearance. That is to the dresses and slutty clothes he now always wore around the house and his makeup.

But also she felt a pang of jealousy, as he now never mentioned his desires for her, and was always out with Georgy who she still hadn’t meet. In truth Georgy was gagging to meet Tara, she had heard all about her, mainly from Steph who always teased Rosie about how badly he wants to go down on her. But also from what Rosie had told him.

This turned Georgy on, and she often told Rosie that he should do something about it.
Go for it she would say, my step dad and his mates fuck me all the time.
“Your mum would love it if you went down on her just as much as I do, especially if she’s had a real good fucking. Steph says she will have you going down on her all the time after she finds out how good you are.”

It was coming up to Christmas and Rosie had invited Georgy round after school for tea at Tara’s insistence. She was beginning to think he felt she would embarrass him, or there was something else worrying him. She couldn’t put her finger on it but she knew something was amiss.

What was troubling Rosie was Georgy’s outright straight forwardness. He was sure she would let something slip and the fact that she was Steph’s cousin was sure to come out sooner or later and maybe that he had been seeing Steph ever Saturday since his mum had paid her to spend the night with him. Having a slag for a girlfriend was one thing, but cleaning Steph out was something else entirely, and he was worried how she would react.

As Rosie and Georgy came out of school heading for the bus stop with the winters sun disappearing they heard a honk of a car horn and their names being called out. It was Steph’s voice and they looked around in the gloom to see where she was. Georgy spotted her first and pulled at Rosie’s hand in the direction of a bright pink Mini convertible with a delighted looking Steph waving out of the window.

“Come on love birds I’ll drop you both off for the big meet, I’ve just passed my test.”

Georgy was jumping with joy skipping over to the car pulling Rosie behind her. As they got to the car Steph saw the hesitation in Rosie’s face.

“I take it you’ve not told your mum yet that Georgy’s my cosine, or that you’re cleaning me out. Don’t worry I’ll drop you at the end of your road by the video shop. But it will cost you; I only passed because I let the driving examiner fuck me. I’m a bit sticky babe”

A cheeky smile came over Rosie’s face “I guess a bit sticky is better than nothing, and I’m going to tell mum I promise. I’m just waiting for the right time.”

“The right time is when you’ve got you face buried between her thighs and your tongue up her dirty cunt, showing her what’s she’s been missing. I promise you, she will be so sexed up, she will be able to forgive anything”

Georgy chipped in, saying that she was more than a bit sticky and had been given a good fucking in the stock room by four of the sixth form boys all dumping a load in her.

“You’ve got Rosie for the rest of the evening, and I want some action. Do you want a lift or not?”

“O yes please, I was just saying that’s all. You know I don’t mind Rosie licking you out. It’s just that I need licking out as well, but I’m wearing nickers so he can do me later, cant you Rosie”



Tara was excited to be meeting Georgy and was debating what to put on, I’ve got to look hot and show the slag what she’s got for compotation. She smiled to herself for thinking of Georgy as competition for Rosie’s affections, as she wriggled into her skin-tight shiny black leggings. She had a special client coming round at eight for his regular fisting and arse stretching, and had laid out what she was going to wear and decided she would put it on.

Tara was dressed and ready having a quick sip or two of wine and cigarette when she heard the chatter of voices and the front door open. Putting her glass down and subbing the half smoked cigarette out in the ashtray on the kitchen worktop she strutted out into the hall to great them.

Georgy’s jaw dropped as she took a good look at Tara standing tall in her red five inch stilettoes, her shiny black leggings were so tight they cut a deep grove into her pussy mound leaving nothing to the imagination, a black shear mesh blouse that did nothing to hide her tattoos and displayed her thirty two E breasts supported by the black the half cups of her corset, her fat pierced inked nipples plain to see.

Rosie gave his mum a hug telling her that she looked lovely; as Georgy stood by silent a little in owe.
Releasing Rosie, Tara looked directly at Georgy’s smiling face and smiled back at her. “So your Georgy, I’m so happy to meet you at last. I hope you like pizza I’m not much of a cook”

“O yes, I like Pizza Mrs Rose, and I’ve been dying to meet you. Rosie talks about you a lot.”

Tara laughed, “Call me Tara, now tell me what Rosie’s been telling you, all good I hope”

As Tara put her are around Georgy’s shoulder and steered her into the kitchen, Rosie wanted to curl up and die; He knew Georgy’s mouth was going to run away with itself, she just couldn’t help it.

“O yes, he’s said lots of things and all good like your gorgeous and sexy, he was right about that, your a single mum and brought him up on your own, you’re a working girl and like my cousin Steph you don’t use covers.”

Tara looked over her shoulder at Rosie raising an eyebrow at him, but was not fazed.
“Well I like the gorgeous and sexy bit, you say your cousin Steph is a whore like me. Rosie tells me you’re a bit of a slag yourself.”

Tara’s light tone and smile put Georgy at ease, “O yes, I’m a proper dirty slag aren’t I Rosie?”

Both the girls stopped in their tracks and looked back at Rosie when no reply came, who was frozen to the spot a few paces behind them.

Tara, couldn’t help herself and had a chuckled, and Georgy joined he with a little nervous giggle. Wondering how deep the hole was she had just dug herself and Rosie into.

“You are so busted Rosie, why don’t you go to your room and get out of those clothes and put something nice on while us girls have a little chat. What do you think Georgy?”

“O yes, that’s a great idea Mrs Rose.. um Tara. I like it when she’s dressed up slutty do you?”

Picking up on Georgy’s catch phrase she replied, O yes, I like. Tara chuckled again as they turned their backs on Rosie as he was making his way to the stairs.


Rosie took his time getting ready, he wasn’t sure if he was in trouble or not or how much Georgy the motor mouth was divulging to his mum. But she didn’t seen upset by the revelation that Steph was Georgy’s cousin. He sorted through the girly clothes, he felt like the pressure was on and he had to look his best, really good and sexy.

He got so into making sure his makeup looked perfect, checking his pink hold up stockings were at the same height, with enough flesh showing between the stocking tops and the hem of his short white pleated skirt to look slutty. His pink bra filled with his breast forms wasn’t crooked and his sissy sheer white blouse with pink polka dot harts was tucked in perfectly, that he didn’t notice the time passing by. He came back to reality when his mum called him down saying the pizza was ready. Her voice sounded quite natural and now dressed to impress he felt his confidence coming back.

Taking one last look at himself in the mirror and liking what he saw he took a deep breath and headed down to join “The Girls” in the kitchen.

Georgy jumped up out of her seat as soon as she saw him and skipped over to him throwing her arms around him telling him how lovely he looked.

“You look delicious Rosie, definitely one of the girls. Georgy and I have had a really good chat and we were just discussing Christmas. Did you know that Georgy’s mum is going with her step dad and half brother to visit relatives and Georgy is being left behind to stay with Steph?”

“Yes, Georgy told me, it will be just the two of them and a can of beans on toast from what I’ve heard”

They all had a chuckle and Tara poured Rosie half a glass of white wine as he sat down next to Georgy.

“Well I was thinking that Georgy and Steph could come over here for Christmas Dinner, after all it will just be the two of us what do you think?”

Rosie was a little shocked, but very pleased with the idea and was enthusiastic with his response. An excited Georgy clapped her hands and added that it would be the best Christmas dinner ever. To which Tara told her not to set her sights to high they could still end up with beans on toast with her cocking skills.

As they ate, they chatted, well it was mostly Georgy and Tara doing the talking as Rosie listened in. It was obvious that his mum and Georgy had hit it off and he was relived that his mum had taken to his girlfriend so quickly.

All finished Tara got up and collected the plates putting them in the sink. As she turned back she parted her legs slightly and sensually rubbed the deep V of her camels toe.

“Georgy wants to see your girly wardrobe, so why don’t you take her up to your bedroom and show her your favourite things. And from what she’s told me the slag’s keeping your desert worm and it needs a good stir first. I’ve got to get set up for a client who will be round at eight, so keep quiet and stay out of sight please, and Georgy, you don’t need an invite. Come round whenever you like ok”

Rosie and Georgy gave Tara a hug and thanked her before they scurried of up the stairway to heaven.

Tara genuinely liked Georgy, and the way she talked so openly and freely about herself and Rosie when they had there little chat. She found out a lot about her son and Georgy confirmed much that she already knew or suspected. He truly wanted to start taking hormones and be girly boy full time with real tits and curves. But what did surprised her and made her felt a little guilty. Was that he was actually doing very well at school and she had not realised, or taken enough interest to find out.

Georgy described him as a brain box and that he would do really well when he goes to collage. Tara wasn’t even aware he had any thoughts of carrying on at school or that he was constantly teased and sometimes bullied at school for being effeminate and girly. But that had pretty much stopped as soon as he and Georgy became an item. Georgy said she saw to that by refusing to let one of the sixth for boys fuck her because he had picked on Rosie, telling him he wasn’t getting any until he apologised to him.

The most revealing thing that Georgy told her was that Rosie was always hungry for cum and loves licking her pussy out after she had been with other boy’s, and that he was cleaning Steph out regularly. This would have normally sent Tara into a fit but Georgy added that he desperately wants to lick her pussy out.

Tara was wet at the thought of it as she finished tidying up the kitchen and headed up to her bedroom to get set up for her eight o’clock booking.

Gerald Thompson was one of her favourite clients and she had met his wife Fiona a number of times. It was Fiona who set up and made the bookings for him, telling her what she wanted her to do with him.

It all started three years earlier with a phone call from Fiona, asking if they could meet and discuss her husband’s needs.

Fiona had been married to Gerald for eight years and been fucking around behind his back since the day they first met. Soon after their wedding he confronted her telling her that he knew what she was up to, but far from being upset he was turned on and asked Fiona to cuckold him.

On that first meeting Fiona told Tara that she wanted her husbands arse fucked out. He had been asking her to fuck him with a strapon for some time and it wasn’t her thing. Tara readily agreed and since then had been steadily stretching him out and introducing him to some other perverse pleasures, for her own and Fiona’s amusement.

As Tara went down to let Gerald in she could hear Georgy moaning with pleasure and smiled to herself.

Rosie was nibbling and tickling Georgy’s pussy lips when they heard Tara come back up the stairs with Gerald.

“Now what have you brought me bitch, is that a new video of your wife getting fucked?”
“Yes mistress Tara, I haven’t been allowed to watch it yet”
“Well we can watch it together, after we’ve got comfortable and I’ve worked that Bully Boy strap on cock all the way up your arse pussy so you can feel the rubber ball’s smack into you. You’d like that wouldn’t you?”

“Yes Mistress Tara, but I don’t think I’m ready. I’ve never taken that much before”
“Well your wife thinks your ready and so do I, so it’s going all the way up your arse or I wont be letting your little dicklet out of its cage and there will be no watching the movie. Its up to you.”

Georgy held her hand over her mouth as she successfully struggled to contain the giggling fit rising within as she and Rosie listened to the conversation Tara was having with Gerald.

Tara led Gerald into her bedroom and took the package off him and opened it while he striped. It contained a videocassette and a short note from Fiona.

Gerald was naked apart from his caged cock and had bent over the fucking bench ready for the games to begin, more than a little bit nervous but also excited his dick already leaking pre cum. Tara had positioned the bench so he had a good view of the TV and he stared at the blank screen in silence as she finished buckling up her strapon harness over the black shiny leggings she was still wearing and she removed her black shear blouse. The only change to her attire was the thigh high boots, and long black latex gloves she now wore.

Popping the tape into the video machine she turned to face Gerald, the fifteen inches of fat rubber cock hanging between her legs inches away from his face. She stroked his head gently smiling down at him telling him it would be ok, and before long he would be begging to feel Bully Boys balls. Going behind him she took hold of the butt plug lodged in his arse and pulled it out, his sphincter closed slightly after its removal but remained open. It was quite large butt plug for permanent use, with an insertable length of seven inches tapering down to a good two inches and one inch diameter at the stem for his sphincter to grip and hold the plug in place.

“You wont be needing this anymore Geraldine, its time to size you up.”

Gerald didn’t reply he knew he was due for something larger; it was just a matter of time and was excited to find out how much bigger the new one would be. Putting the butt plug on a little side table with the remote control for the video and TV along with her mobile, digital camera and an industrial jar of anal lube. Tara dipped her fingers into the jar and started to worm her right hand into his back passage.

“You’re a good arse slut Geraldine, always spotlessly clean for me, now just relax and let me fist you out and get you ready for Bully Boy. Theirs a good girl, you opened up quickly I’ll be elbow deep in no time, you do want me elbow deep don’t you?”

“Yes Mistress Tara, please get me ready for my Bully Boy.”

Tara gave him more, forcing her forearm deep into his rectum as Gerald moaned and cried out in pleasure and pain.
It didn’t take him long before he was thrusting back onto Tara’s forearm taking her elbow deep in his arse and wanting a little more; he started begging for Bully Boy.

His moans and cry’s were clearly audible in Rosie’s bedroom as they listened and quietly discussed what was going on in Tara’s room.

With Gerald’s hole now greedy for more Tara removed her fist from his arse and greased up her strapon, nestling the three-inch diameter head into his anal opening.

She teased his arse putting a little pressure on his hole but not as much as Gerald wanted, and waited for him to plead for it inside him and start pushing back. Tara didn’t have to wait long, Gerald new the drill and rotated his hips gently pushing back.

“Please mistress Tara, I need my Bully Boy. I’ll take it all this time, I promise”

Tara lunged forward and the massive rubber head bulldozed its way into his rectum followed by six or seven inches of nobly haft that was two and a half inch’s thick. Pulling all the way out she punched it back in gaining a little more depth and started to slowly fuck his hole gong a little deeper until she had only three more inches to go. She was at his previous best and she paused for a moment, before giving him another inch and then another ignoring his cry’s and his please for her to stop.

Finally Tara had the big rubber balls pressed against the back of his thighs and held it there as she picked up her digital camera and took a number of shots of it fully inserted and the a load more as she slowly pulled it out. Putting the camera down she picked up her phone and dialled Fiona’s number.

“Hi Fiona, Geraldine has taken Bully Boy balls deep and I’ve taken the pictures like you asked. I’m just going back in and start the video.”

Fiona thanked her and asked her to email the pictures over when she had a chance before they said their goodbyes.

Putting the phone down Tara pressed play and the video came on as started to work her way back into Gerald’s arse.

Gerald was transfixed to the TV screen as his wife was sat on the end of their bed at home dressed like a whore. Hello Geraldine, if your watching this you will have your Bull Boy rammed up you boy pussy. The quick introduction out of the way two naked men entered the shot offering her their cocks to suck.

Tara focused on the job in hand now taking long strokes occasionally pulling out and going straight back in. By the time the video had finished Tara had work herself into a good sweet, and Gerald’s hole was accepting every stroke with ease.

Turning the video off she pulled out of Gerald for the last time that evening. His arse was gaping wide open and she was please with her work. Tara slapped his arse asking if he was ready for his shower.
“Yes mistress I’m ready, will you let me cum?”

Tara striped off telling Gerald that her arse was badly in need of a rimming out before she had her enema, and he better put his swimming goggles on. Gerald’s cock was good and dripping, desperately trying to grow and break out of it confinement as he eagerly anticipated the taste of Tara’s sweaty arse crack and unwashed anal ring.

She led Gerald to the bathroom where he quickly assumed his position in the shower in time for Tara to present him with her arse. Without any invitation or instruction required Gerald started working on her crack and was soon enjoying the bitter taste of her anal hole.

Satisfied with his efforts Tara smiled down at him and dangled the key for his cock cage in his face.

Go on take it and unlock yourself, you can start playing with yourself the moment my brown shower hits your face.

As Gerald freed his cock and put on his goggles Tare loaded up her bowels with her enema, the first of three she would expel into his face, with his mouth wide open.

As the first jet of filth hit his face he was frantically beating his meat, when the flow had abated he stopped and lapped Tara’s arse like a well trained puppy and waited patiently for the second round.
On the third he went for it and his cum shot out of his cock with force as he again lapped Tara’s now clean arse hole.

After showering and letting Gerald give himself a thorough wash and dry she oversaw the replacement of his cock cage and took back the key, before taking him to her bedroom and back on the fucking bench.

“Its time I introduced to you new butt plug and sent you on your way. This one is lovely a good nine inches in length, almost three inches at the widest part with a solid two-inch diameter stem. I think this will really let you know that your arse is packing something serious and not just a toy.”

Without any resistance Gerald let Tara push it home. After Bully Boy it felt good, but he knew a few hours from now it would start to get uncomfortable, very uncomfortable but he welcomed the experience, even longed for it.

After sending Gerald on his way Tare knocked on Rosie’s bedroom door, Rosie called out for her to come in.

Tara opened the door and pocked her head in, Georgy was gone and Rosie was watching telly with his headphones on.

“I’m sorry I missed Georgy leaving, she is lovely, I would have liked to have said goodbye. You tell her tomorrow she is vey welcome anytime.”

I will mum and thanks Rosie replied, and as she went to close the door he added, what no kiss and cuddle mum?

Tara was naked with just her see-through black gown the front not even tied, she made a half hearted attempt to hold it closed as she went into Rosie’s bedroom and over to join him on his bed. She let it fall open as she snuggled up to him and gave him a little more than motherly kiss.

“That was nice, I could cuddle you all night Rosie but mummy’s got a customer to entertain in fifteen minutes, I’ve got to get ready”

Tara had two more customers with more vanilla tastes that evening and both regulars. After showing her last client of the day out Tara was on her way back to her room when she stopped outside Rosie’s bedroom door. She paused and put her hand between her legs felling her wet a sexed up pussy through the crotch of her panties, whispering to herself, soon Rosie baby I’m having your lips on my cum filled pussy and arse.

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