Simon's Mistake Pt. 06

It had been almost a month since Simone had been in training. Kelly was a hard task mistress and there had been many painful lessons. She had moved in with Kelly and the two of them were accepted by Kelly's neighbours as just friends.

Simone's first attempts at walking in heels and using make up had Kelly in fits of laughter, she had been presented with a pair of 3 inch pumps, they looked and felt so sexy but, the moment Simone stood up she tottered and wobbled so much she had to grab a chair to steady herself.

Kelly giggled but left her to it, she had to learn. After a week Simone had mastered the heels and happily walked around, her ass swaying looking every bit the woman she wanted to be.

Simone had also had to learn self-control, Kelly tormented her for hours, using vibrators and fake pussy. Simone had been tied so she couldn't touch her cock, at first the machines made her so hard, to the point where she would cum without touching her shaft. It took days of pain and frustration, but Simone mastered her body and even though the vibrations felt so good she managed to keep her cock soft and tucked out if sight.

One day Simone woke to find a new outfit hanging on the back of the door with a note attached, 'wear this with the 3 inch heels.' She smiled at the tight, white satin top, short blue skirt, panties, hose and a padded bra.

Simone dressed and looked at herself in the mirror, she twisted so her skirt swished and swayed showing her thighs. She ran her palms over her top, sighing as she cupped her new breasts.

Kelly was having a coffee when Simone entered the room,' WOW, baby you look so much better than I expected' Kelly exclaimed. She took Simone by the waist and kissed her tenderly.

Simone wasn't expecting this reaction from her Mistress and stroked her tongue along Kelly's, exploring her mouth until Kelly lips slowly parted from Simone. 'I trust you like the outfit?' asked Kelly, Simone nodded 'it's perfect' she cried.

Kelly poured Simone a coffee and sat back down. She watched, wide eyed as Simone sipped from her cup, she loved her so much. Kelly now saw that Simone was wearing makeup. Blue eye shadow, red lips and for the first time Simone wore mascara, 'you look gorgeous' she sighed.

'You ready?' asked Kelly, 'ready for what?' replied Simone. Kelly got up, 'this' taking Simone by the hand leading her to the door. Simone looked afraid as she saw they were going outside for the first time, 'I,I can't go out dressed like this' she exclaimed. 'Yes, you can' whispered Kelly and kissed her cheek, 'you look lovely'

They grabbed their jackets and purse and the world saw Simone in all her glory. They bumped into one of Kelly's neighbours, Ms Tate, a real busybody. 'Good morning, Ms Tate,' said Kelly. 'Oh, good morning' she replied' and added 'you two look nice, going anywhere special?' 'No where special' they replied as they walked up the street.

They passed a local cafe where guys hung out drinking coffee, Simone heard the loudest wolf whistle as they walked by and giggled. Suddenly she had confidence and wiggled her hips, Kelly watched what she did and smiled.

After an hour or so, and many whistles, they stopped in the park. Simone hadn't noticed but she was holding Kelly's hand, she let go saying 'sorry Miss', Kelly slipped her hand back into Simone's, 'it's OK' Kelly said smiling and kissing her fingers. 'What's more natural for lovers to do?' Kelly coo's.

They arrived home having spent time just walking, kissing and cuddling. Simone felt so content, no one had suspected she was a man, and if they did, they didn't taunt her. Once inside Kelly quickly began to change, 'you'd better change too Simone' and handed her packages from the cupboard.

Simone took the garments and unwrapped the brown paper parcels. PVC mini skirt, black studded, halter neck top, black hold-ups and knee length boots, 'you mean you want me to entertain your client?' she cried. Kelly nodded, 'yes babe, I think it's time you earned your keep.'

Simone carefully dressed, tucked her soft cock and sacs under her ass so her panties were smooth and looked feminine, having smoothed her stockings she slipped her feet into the boots, zipped them and moaned as the leather clung tightly to her calves. Kelly came in wearing her purple, PVC catsuit, long PVC gloves and 5 inch heels, 'you ready?' she asked.

Kelly took Simone to the monitor booth explaining to her what was about to happen. Simone grinned, then moaned as Kelly ran her finger tips over her crotch. 'MMMMmmm so smooth' purred Kelly, 'you wait 'til later.'

Kelly left her and waited for her clients. She didn't wait long, the was a knock at the door. 'Come in' ordered Kelly, a couple entered, he was dress casually wearing a cotton top, jeans and looked pretty fit. She however wore a long coat and stood in the corner while her husband had his fun.

Kelly showed him to a chair, bound his wrists and ankles to the chair, unfastened his jeans and carefully lifted his soft cock from within. He moaned, 'good, that's good.'

Kelly then turned her attention to the female, she shivered as Kelly approached. Taking her hand Kelly led her to the centre of the room and while standing behind her she undid each coat button and eased it from her shoulders.

Simone, looking on the monitor, was shocked when Kelly revealed a strikingly beautiful woman, with huge breasts, slender waist, cute ass and long, long legs. She looked unhappy as Kelly, and Simone, admired her matching silk bra and panties and her flawless skin.

The couple were Andy and Casey, regular clients. Andy would get his kicks watching Casey being whipped, tortured and abused. His cock began to swell when Kelly slipped her fingers into Casey's panties and brushed against her shaven pussy.

Casey showed no emotion, she stood with her head bowed and waited. Kelly whispered something into her ear, for the first time Casey smiled, slowly nodding her head.

Kelly looking straight at the camera, this was Simone's signal to join her. Quickly Simone donned the jet black wig that had been left for her and pulled on leather gloves.

Andy's jaw dropped when Simone walked in, she placed her hands around Casey's waist and gently kissed her neck.

'What gives?' Andy wailed as he saw Casey turn and give Simone a long, lingering kiss, 'this gives' snapped Kelly as she forced a ball gag between Andy's lips. Andy's muffled protest went unheard.

Kelly now joined Simone in kissing and stroking Casey. Casey squirmed and sighed as they touched her flesh, kissed her breasts and gently slapped her ass.

Kelly lifted one breast from Casey's bra, Simone did the same with the other. Casey moaned loudly as she felt her nipples being flicked, sucked and bitten, she placed her hands behind her tormentors head and stroked their hair. Kelly gently slipped her hand under Casey's crotch, 'so warm and wet' she coo's.

Casey widened her legs as first one, then two fingers did Kelly's bidding, while her thumb massaged Casey's clitty. Casey squirmed and moaned as her pussy was stretched and finger fucked.

Simone could hear Kelly playing with the helpless woman's pussy and sucked Casey's nipple harder. Before Casey climaxed Kelly slowly withdrew her fingers which dripped with juice. She forced Casey to suck one finger and presented the other to Simone, which she eagerly sucked.

By now Andy's cock was solid, he struggled against his bonds, but he was their prisoner. Saliva dripped from his chin and stained his top. He was loving what he was seeing, but it wasn't how it normally worked, by now Kelly should be beating his bitch and who the hell was this other woman.

Kelly let the firm nipple slide from her lips and approached Andy, 'liking the show so far?' she teased and ran her finger through his precum. He growled abuse, but his cock betrayed his feelings. 'We have to go now' purred Kelly, 'but I'm leaving you some entertainment.' She placed a TV in front of Andy, on the screen he could see a bed. 'Oh, and this,' Kelly laughed as she jammed a vibrator head against his sacs and shaft.

Simone meanwhile had led Casey to the bed, laying her down, kissing and caressing her, 'see' said Kelly 'you won't miss a thing' and left him to the soft buzz on the vibrator.

Kelly went to join the girls, Andy stared at the screen, not daring to blink as Kelly and Simone seduced Casey. His balls began to ache and swell, his cock lengthened, Kelly's toy was doing its work well.

By the time Kelly arrived Casey was naked, Simone lapped at her pussy which, by now, was soaking. Kelly unzipped her crotch, knelt next to them and presented her cock to Casey's lips. At first Casey just kissed and flicked her tongue onto the tip, but slowly, as Simone did her work, Kelly's cock slid down Casey's throat.

It was, Casey claimed, her first face fuck, but she knew just what to do. Her lips clamped down onto Kelly's shaft while her tongue ran up and down its length. Kelly moaned and reached for Simone.

Simone stopped lapping and held Kelly in her arms, her tongue forced into Kelly's mouth so they could both taste Casey. Simone had held on so far, her cock was firm but not yet hard. Casey stroked Simone's crotch, and her hidden secret revealed itself as Simone swelled.

Deftly Casey slid her fingers beneath the tight panties and eased out Simone's cock, rubbing it hard. Simone groaned and kissed Kelly hard. Casey let Kelly's cock slip from her mouth and held both in one hand.

Casey lapped and sucked at both tips, Simone pinched on Kelly's nipple, all three moaned and sighed as each was pleasured.

Kelly groaned when Casey stopped sucking her and looked at the pair thinking who she who fuck fist. Casey was close to cumming and squealed when Kelly pressed her cock into her warm, wet pussy.

Casey's thighs rubbed against the tight PVC, and she gasped at each thrust, Kelly made sure she pressed deep and could feel as Casey neared her orgasm. Seconds before that moment Kelly withdrew, telling Casey 'Simone's turn I think.' Simone lay on her back with a huge erection. Casey licked her lips, straddled her and slid down Simone's cock. Simones stockings wrapped around Casey, her boots locked over Casey's back

Harder and harder Casey slammed onto Simone's solid sacs, forcing her cock inside. Kelly also saw Casey's enjoyment and wanted to add to it. Simone drew Casey's body towards hers and started to fuck her slowly. Casey groaned, she was now no longer in control, Kelly ran her fingers around Casey's pussy and rubbed the juice into her ass.

'No, No, not that' Casey cried, she tensed, and her pussy held firmly onto Simone's cock. Kelly smiled, 'not what darling' as she popped Casey's virgin ass. 'AAAAAGGGHHHHHH' cried Casey. Simone moaned as she too felt Kelly's cock as they both fucked their helpless victim.

Casey was out of control, her head was spinning, she felt hot and sticky with sweat and wasn't prepared for her first anal orgasm. She held Simone firmly and shrieked as both pain and pleasure wracked her whole body.

Andy to was out of control, no one could hear him cry out as his swollen balls finally let him cum. The vibrations still beat through his member as his cum shot into the air, soaking his jeans in thick juices.

It took some time for the 3 girls to finish cumming, slowly Kelly and Simone slipped from Casey, she in turn fell to one side, breathless.

Kelly and Simone kissed Casey all over, it was so gentle that Casey willingly opened her pussy and ass for them to lick her. 'No babe, not here' whispered Kelly.

They all rejoined Andy, saliva dripped from his gag and his jeans were soiled, his cock still pumping. His eyes focused on Kelly and Simone in their shiny PVC, he groaned. Then another figure drew closer, a tall woman dressed in black thigh high boots, crotchless leather shorts with matching studded bra.

It took a few seconds before he recognised Casey.

Kelly removed the gag, 'Cas.... Casey is that you?' he gasped. 'Yes slut' she snapped and grabbing his hair pulled his head back. 'Now clean me' she ordered. Andy hesitated so Simone pressed the vibrator harder against his sacs, he produced his tongue. His first, tentative licks felt good, Casey moaned softly, his actions became more frantic, 'mmmmmmmmmm' uttered Casey.

Kelly and Simone watched as he sucked and swallowed every bit of their cum and Casey, feeling satisfied, allowed him to breath once more.

Andy wept when the vibrator was removed and fell to his knees once his limbs were free. He looked down at 3 pairs of boots, he kissed each in turn. When it came to Casey, he lapped at the patent leather and sucked on the heel crying 'Mistress.'

Casey looks at the other two and winks.

After they had left Simone looked quizzically at Kelly, 'what just happened?' she asked. Kelly laughed, 'exactly what was supposed to happen, except this time Casey had two cocks to play with instead of just mine, so she's no longer an anal virgin, I think she enjoyed it as she paid double and booked for the same next time.'

Simone's jaw dropped 'you mean that happens every time?'

'Every time' Kelly replied. 'Now if you've got any energy left, I promised you something for being so good.'