Simon's Mistake Pt. 01

Simon looked nervous as he approached the apartment, he took out the magazine from his pocket and read the ad again. 'If your confidence needs a boost or you're just looking for a new experience call Kelly'.

He bit his lip and rang the bell; he'd never been with a hooker before. The door opened and a plain looking chick looked him up and down, 'Your Simon I suppose' she enquired?' Simon grunted a 'yes'; 'You'd better come in then' she ordered.

Simon followed her down a long hallway, he noted for such a plain Jane she had a sexy wiggle and wore very high heels. He was shown into a dimly lit room and was told to sit down and wait.

Kelly left her new client and entered her dressing room. Off came the cardigan and tweed skirt and she sighed when she opened her closet. She ran her fingers over her extensive number of outfits, satins, silks, faux and real leather 'Let's try, this' she whispered

. She chose a short leather skirt, tight satin blouse, black panties with matching suspender belt, black stockings, and ankle boots. Once dressed she admired herself in the mirror, blowing herself a kiss.

Simon was deep in thought when he heard the click of heels approaching, 'She's back' he thought.

Slowly the door opened, his jaw dropped at her transformation. She slowly approached, her hands stoking Simon's cheeks making him blush. 'You like?' asked Kelly, 'Yes' exclaimed Simon and made a grab for her. She sidestepped his advance and slapped his ass hard. 'Ouch' cried Simon and turned to face her. 'Good things come to him who waits' Kelly smiled. 'You're new to this aren't you?'

Simon nodded, 'relax' purred Kelly as she slowly circled Simon placing her fingers on his shoulders forcing him to the middle of the room.

'Stand there' ordered Kelly. Simon could hear her open a drawer then everything went black. He was shocked at first but didn't dare move fearing Kelly would stop. He slowly began to enjoy her soft touch and the silken bag over his face made his other senses come alive.

He felt her fingers gently stoking his body, he moaned as she stroked his chest and rubbed his nipples.

'Your clothes are so inhibiting' Kelly coo's and with that Simon felt his shirt buttons being unfastened one by one. He felt Kelly's hot breath against his bare flesh then the tip of her tongue circled each nipple until they were pert and hard. Simon moaned louder and he felt his underwear stir.

Kelly slipped the shirt from him and ran her nails over his back, Simon arched his spine to try and get away from the pain, but it was no use, but he felt his flesh sting his crotch swelled with excitement.

On reaching Simon's waist she slipped her hands round his waist, deftly unbuttoning his shorts and gradually lowering the zipper. With no resistance the shorts fell to the floor.

Kelly squealed with delight when she saw Simon's growing bulge and slowly stoked it through his undies. 'I hope your wanting to change these?' enquired Kelly as she stretched the elastic on his undies and then let go.

Simon could feel his ass cheeks burn at the sting of the elastic. 'What would you suggest?' mumbled Simon 'I'm am very new to this'.

Kelly pressed down on his undies and Simon felt his cock become exposed. Kelly ordered him to flick off his shoes and undies, all the time walking around him tutting and stroking his naked body.

Kelly pressed herself against Simon allowing his fingers to caress the soft leather of her skirt. Kelly moaned, 'that's nice' and pressed her bust against his nipples.

Simon's cock twitched again but he was sure he could control himself; he wanted the experience to last as long as possible.

Kelly smiled when she felt his hard cock pump saying, 'let's find you something sexy to wear'. She released him from her embrace and went back to her drawer.

'Lift your legs slut' she commanded, Simon grinned at being called a 'slut' and instantly obeyed. He felt something slip over his ankles, Kelly ran her palms over his thighs then smoothed the tight, white panties over his ass and cock.

Simon's head was spinning at the tight, soft material caressing his flesh, it drove him so wild he tried to slip his fingers under his new panties.

'No, no, no, you're not ready to enjoy yourself yet' hissed Kelly 'I think you need training' with that Simon felt a belt being fastened tightly around his waist and his wrists were fastened into cuffs which stopped any chance of self-enjoyment.

Simon's mind wanted him to run, but the swollen cock betrayed his true feelings. The more Kelly took control the more he wanted her to abuse him.

Kelly picked up one her toys. She teased him by running its soft leather thongs over his thighs and ass, he relaxed as the material felt so good on his skin.

He wasn't ready for the first swipe from her whip, she slowly spun the thongs around and flicked his ass.

Simon winched at the pain, it stung so bad he thought she must have broken his skin, but Kelly was too good to let that happen and as one part reddened, she would move on to fresh virgin flesh.

Soon Simon's ass, thighs, chest and back were stinging.

It was then Kelly saw a change in him. Instead of moving away or tensing his skin Simon moved towards her and sighed with the pleasure with each stroke of the whip she gave him.

His cock also betrayed his feelings, it dripped precum.

After 40 minutes of torment Simon was relieved when she freed his wrists. As he stood in front of her Kelly slipped a garment over his head, it covered him to his thighs and Kelly helped put his arms through the sleeves.

Simon stroked the garment, it felt smooth and cool to the touch.

Kelly removed his hood, Simon blinked and looked down, he was wearing a short PVC dress. Horrified he screamed 'What's this?'

Hush slut' Kelly snapped 'you didn't think it too bad until I took that hood off, did you?'

Simon had to admit he didn't, 'but it didn't say anything about this in your ad' he wailed.

He thrust his magazine towards her. Kelly looked at the ad and smiled. 'Right apartment wrong ad honey as she pointed to the ad he had circled, 'Cross Dressing and Bondage Your Thing'.

Simon slumped onto the chair, 'OMG, but I think this is a wonderful experience' he cried and stood up as before wanting more from Kelly. She whispered in his ear 'bend over slut', then sucked his lobe.

Simon instantly obeyed and bent himself over the chair.

Kelly grasped his hips, softly stroking and kissing the PVC dress. Simon's throbbing cock was desperate for her attention. She stroked him from ass to cock until Simon's panties could barely cover his bulge. Slowly she exposed his ass and lifting her skirt, she pressed her panties against his flesh.

Simon tensed as he felt something solid pressing against him. 'OMG' he cried as he felt the tip of her bulge pressing against his ass. Simon could barely hold his excitement; 'she's wearing a strap on; I'm going to be fucked' he thought.

Kelly couldn't see but Simon was wearing a huge smile.

Cold lube was dripped down his ass and Kelly rimmed his tight hole with her finger tip, 'Now relax' she whispered as she slipped her own panties down. Simon felt more pressure against his ass then bit his lip as his ass was parted and a long hard shaft slid slowly within.

'YES' cried Kelly as she worked her hips slowly back and forth, Simon groaned at each thrust, and he began to feel heat in his ass.

Kelly started pulling him back onto her cock and it wasn't long before Simon had his first anal orgasm, his hole tightened against Kelly making her experience even better. 'Ready slut?' grunted Kelly as she thrust deeper.

'What, what do you mean ready?' cried Simon as he felt another orgasm building. 'Oh YES' cried Kelly as she pressed even deeper as his flesh clamped onto hers. 'Ready for this slut'. Kelly thrust hard and pumped. Simon wept at the realisation she wasn't wearing a strap on, and his ass was being filled with her cum.

They stayed locked together, every time Kelly pumped Simon had another orgasm until she was spent, slowly slipping from his soaked hole.

Simon turned to see her tucking her cock back into her panties. He felt her fingertips stroke his ass as she pulled his white panties up.

He looked at Kelly and mouthed 'thank you Mistress' as he once more stood before her, he was again admiring the way she was dressed and wondered if he dared to do the same.

Kelly knelt and lifting the PVC dress from Simon she kissed his panties 'tastes nice' she murmured.

An embarrassed Simon saw that his cock now dripped cum, soiling his new panties.

'Never mind honey' Kelly smiled and scooped his cum onto her fingers. 'Try this'.

She rubbed Simon's lips with the thick, white cum, he licked taking his first taste of salty jizz.

Kelly couldn't help herself placing her soft lips to Simon's, she expected some resistance but was pleasantly surprised when his tongue forced its way into her mouth. He still had the taste of cum lingering as her tongue played over his. After a long hot kiss Kelly broke off apologising to Simon, 'I'm so sorry but I couldn't help myself, your, you're so different to my usual clients.'

'Maybe that's because I came here expecting one thing but found another, which excites me even more' remarked Simon. He stepped back to again to take in what Kelly looked like, 'Can you make me look like you?' he asked.

Kelly gasped and smiled, 'WOW. you really have changed your views. You thought I was a strict Dominatrix but instead you find that being pleasured by a tranny excites you more'.

She took his hand leading him to his pile of clothes saying. 'I don't normally do this but, let me dress you.'

Simon sighed has she gentry caressed his skin, slipping her hands inside his soiled panties so to remove them.

'No Miss Kelly, please can I keep them on? begged Simon.'

Kelly smiled 'Of course babe'. throwing his old jockey shorts into the trash.

Slowly she eased on his shorts, being careful not to arouse Simon again and slipped the shirt onto his back.

Before fastening each button Kelly kissed his chest and listened contently as he moaned.

He slipped on his shoes and carefully placed Kelly's ad into his pocket.

Kelly stroked Simon's cheek saying, 'If you really want to make this mistake again, call yourself Simone.'

Simon smiled and kissed Kelly's hand. He knew he would be back he so wanted to be transformed into Simone that it was all he could think off on his way home.