Jessica and Tom 02: Meeting Up

"But I'm not hypnotised"

"No Tom you very much are it's just you are not in trance right now. How do you explain that a moment ago you weren't wearing makeup and now you are?" His brow furrowed. "I bet it would amaze you even more if I told you that you did your own makeup."

"This is getting a bit daft now!" he said

She sat beside him on the bench seat and slipped her soft hand down his thigh before reaching to the phone on the dresser and opened the screen allowing the video to play, it showed him pampering himself and fussing over every stage of painting his face. "I'm confused."

"Of course you are Tom but you must understand you wouldn't have done this if you didn't want to. The best part is I find it so very sexy." She slipped her hand back up his thigh and played with his chastity device "and I can't wait to play some more"

Jessica stood and went across to the closet once again and pulled out a copper coloured wig standing behind him she slipped it over his short hair before tidying the red hair and getting it to sit just right. "Doesn't that look good sweetie" she kissed the nape of his neck leaving a deep red lip print. He squirmed not knowing what to do.

"Don't worry Tom your transition will be so lovely, I'll periodically wake you back to your pre sissy state, I find this helps reinforce your submission until eventually you don't need to be compelled with hypnosis you just accept your place as my 'pretty sissy Candi.'" He grinned at his reflection in the mirror and clapped his hands with excitement.

Jessica stood and went back to the closet and began picking up various items from within. She returned with an emerald green satin boned corset, matching frilly French panties and a new packet of black stockings and placed them all on the dresser. "Stand up my sweet and let's get you ready for our night of fun."

Tom stood and was guided to one side of the dresser by Jessica. She slipped the corset around his waist and fastened the steel hook and eyes up the front, the breast forms already fitted to it slipped into place over his chest. She slipped behind him and began tightening the laces pulling and tightening each level as she worked her way to the top. Not too much cinching this time but enough to show some figure. He gasped breathlessly as she got to the top and tied off the laces in an ornate but neat bow.

Taking the black stockings from their packet she rolled each one carefully then knelt at his feet slipping the first over one over his toes. "Now you are smooth and hairless these will feel oh so special." She slipped the stocking up his leg making sure the seam at the back stayed nice and straight. Eye to eye with his imprisoned cock she could see his arousal building, precum starting to ooze from the tip. She slipped the other stocking up his leg and then fastened the 6 garter straps to the luxurious lacey welts. The glossy finish to the hosiery glinted in the soft light as he was turned to fasten each strap

"Now step into your panties sweetie, every girl knows that panties go on last in case you need to visit the loo or some other pressing reason to remove your panties presents itself." she teased his inner thighs with her scarlet nails as she said it to emphasise the point. He stepped into the panties and she slipped the emerald satin up into place. "Lovely, let me look at you." She stepped back and admired her handiwork, with the false breasts and corseted figure he could pass for a real woman but something was missing. She rolled her eyes, shoes!

She went into the closet and found a pair of black patent leather kitten heals with a cute little buckle around the ankle, slipping them onto his feet she chuckled to herself seeing him teeter on the small heels.

"I don't think Tom is a very girly name and you look so deliciously girly so how about we use Candi from here on in"

"That sounds wonderful Miss Jessica." he replied enthusiasm brimming from him despite his obvious discomfort with the tight corset, heels and cock prison.

"It's settled then, my sweet Candi." she stepped in and teased him with a kiss, gently caressing his lips daring him to grab for a taste of her sweet affection. Finally she succumbed and their lips met, lipstick smearing as they kissed, her tongue slipping into his slutty mouth. She reached down to toy with his cock and balls, the straining and throbbing making her feel so powerful. Withdrawing from the kiss she smiled as she checked her makeup in the mirror.

"We seem to have got a bit smudged sweetie, best do a touch up." She handed him a compact and he followed her lead as she dabbed powder around her smeared lips then reapplied her dark red colour.

"I think we need to find a use for those lovely lips now Candi, pass me the harness."He passed the black leather strap-on harness and she slipped in one leg then the next. "Kneel down sweetie, I'm sure you'll enjoy this.", he sunk to his knees leaving his eyes at her crotch level.

The inside of the harness was fitted with a ribbed dildo and she slid the phallus slowly into her wet pussy exhaling as she felt each rib rub against her raging clit. Fastening the large buckle at her waist she towered over him, the outer six inch flesh coloured cock sitting erect and hard only inches from his mouth, it's mushroom head shimmering in the dim light.

"Candi every little bimbo slut learns very quickly that sucking cock generally gets you what you want and those ruby red lips of yours are very slutty. Have you ever sucked cock Candi?"

"No Miss Jessica, I've never sucked a cock before."

"Oh what a treat. Well then you'd best learn fast, how about giving it a little kiss first." she held the cock at its base moving it closer to his lips encouraging him to move closer"

Candi leaned forward allowing his glossy sticky lips to caress the tip leaving a ruby red smear on the flesh coloured dong. He retreated slightly then leaned in again allowing the mushroom head to part his slick lips as she gently thrust her hips towards him. The thrust slipped her own dildo deeper into her snatch stimulating her and making her pussy wetter by the moment.

Soon the whole head was in his mouth and her gentle thrusts were smearing his lipstick up and down the top of the shaft as he became accustomed to the sensation of the rubber dick in his mouth. She bit her lip in excitement, "Remember to use your tongue to caress the sensitive spots on the tip, tease it, think what you like when a woman sucks your dick Candi."

Candi looked up from beneath his copper coloured hair, his eyes full of desire to please her as he slipped his ruby lips up and down on her rubber strap-on. The dildo inside her was rubbing against her sex so perfectly as she thrusted slowly, resisting the urge to ram the cock into his hungry mouth; baby steps. She could feel her orgasm building slowly but it would take more than this to get her off.

Stroking his hair tenderly she placed a hand round the back of his head making sure his mouth couldn't escape the cock in his mouth before whispering "manly man"

His eyes widened as his male persona snapped into the fore realising he was kneeling before her with with a cock deep in his mouth, he tried to retreat from it and gagged when he encountered her hand holding him on it.

"My Tom you do look like a marvelous cock sucking slut. Look at you with your smeared lipstick and drool running down your chin. Are you convinced of my power over you yet my sweet Tom?"

Relaxing slightly he couldn't speak with the dildo deep in his mouth so nodded slowly, his eyes welling slightly with tears

"Don't cry sweetie, you wouldn't allow this to happen unless you secretly fantasised about it and you do make such a pretty little cock sucker. Besides if you cry you'll ruin your lovely mascara."

Tom fought to control himself as his realities span around him. She was right that he had fantasised about all of this, the domination, the cross dressing even the cock sucking but he'd never thought it would be made real.

"While I love watching you eat my girl cock it's not quite enough for me, would you like to move on to the main course sweetie?"

Tom shivered as he realised he really didn't have a huge choice in the matter. She released her hold on his head and allowed the cock to slip from his smeared lips "Why are you doing this?" He asked meekly.

"I'm broadening your horizons Tom, for all you find the idea of your current predicament a little shocking it's also very sexy, ask yourself..... how horny are you right now? How hard does your dick feel in its chastity cage?"

Tom looked down at his satin covered groin and felt the relentless discomfort of his cock trying to engorge within the plastic restraint, he felt the fizz of his arousal throughout his body, the new sensations of the soft satin and tight glossy nylon on his skin and ultimately his desire to be dominated. He nodded, "Yes Miss Jessica."

"Good boy, what a pretty sissy Candi" the resigned look was immediately replaced by an eager smile as Candi once again returned.

Catching his reflection in the mirror he exclaimed, "Oh Miss Jessica, I am a mess should I clean up?"

"Go ahead Candi, then join me on the bed" He grabbed the compact and padded his smeared face again smoothing out the reddening colour around his mouth then reapplied his lipstick before quickly going over his face with a large brush to even out any runs caused by his gagging.

Once done he tottered on his heels eagerly to the bed where Jessica lounged on her side. She guided his back to her front so they could spoon together. Jessicas strap-on slipped neatly between his ass cheeks as she gently hugged him, she moaned quietly as the dick inside the harness moved inside her keeping her just on the periphery of her orgasm.

She reached around him and began to toy with his balls and imprisoned cock causing him to moan in frustration. She let her long red nails trace from his balls back along his perineum and gently caress his virgin ass. "Have you ever been fucked Candi?"

"No miss Jessica, I've only played with the toys you gave me."

"Perfect, I so hoped you were a little tight virgin. I'm going to enjoy taking your little boy cunt for the first time. Take off your panties and get on all fours you little tart." Candi reluctantly obeyed slipping the satin panties off and leaning forward, his ass pointing into air as he rested his weight on his forearms. His garters strained to hold up his stockings perfectly framing his vulnerable ass.

Jessica positioned herself behind him taking a bottle of lube and some gloves from the bedside pedestal as she got into position. She drizzled the gloopy liquid down his ass crack watching it dribble towards his waiting rosebud. She put on the latex gloves and made sure her fingers were nicely lubed as she toyed with his hole gently applying pressure her finger slipped easily into him causing him to gasp. Slipping her finger in and out she made sure his ass was properly lubed for what was to come before finding his prostate.

He hadn't cum in several days, since she had made him don the chastity cage. His prostate was firm and full of fluid, as she gently caressed him she heard him moan in pleasure. Looking underneath him she saw the wet drop of precum appear at the tip of his squashed cock. Another gentle press elicited a more guttural moan and she saw the precum drip in a long ribbon onto the bedclothes causing the satin to discolour. She felt him lean back against her finger hungrily.

"Oh sweetie you seem to be leaking from your boy clit, do you like that feeling when I press on your gland just in that spot?" She pressed again to demonstrate her point, another moan, another drip, another thrust back but no response. She knew this sensation was quite overwhelming for men the first time.

As he thrust back again onto her finger she allowed a second finger to press against the opening to his ass and it slipped in easily. She allowed him to set his pace as he rocked back and forth angling his hips to try to get her fingers in the right spot to hit his pleasure spot. Sometimes she allowed it others she moved her fingers to prevent him getting his pulse of pleasure. Before long she had a third lubed finger in him and his rhythm began to increase. She could sense the shivers of pleasure building in him as she stimulated him but this wasn't getting her the stimulation she needed.

With her other hand she liberally applied lube to her strap-on making sure it was nicely coated. She slipped her fingers from his ass and he moaned in protest at the empty feeling she left. "Don't worry sweetie, you won't be empty for long." she whispered. Slipping the tip of her dildo onto his waiting hole and allowed him to press back onto her. The dildo inside her pressed on her g-spot as the tip at the other end slipped slowly into him. First the head then inch by inch his ass swallowed her cock. Soon her thighs here're touching his ass and she reveled in his deep moan of pleasure.

She slowly pulled back allowing the cock to slip slowly back out of him. She tenderly stroked his ass cheeks as, sensing the end of the cock, he thrust back onto it. His breathing was fast as he thrust and ground on her cock, she moaned loudly as the dick inside her brought her close but it was too soon.

She slipped the cock from his hungry ass, "Roll over sweetie I want to see you while I fuck you" she placed a pillow under his ass as he rolled over. Kneeling between his splayed legs Jessica reached forward and kissed him passionately as she positioned the cock back at his hole. She was in control now, on his back he couldn't thrust. She slowly inched the head into him as she kissed him, his mouth opened in an involuntary moan as the ribs slipped over his prostate once again.

He quivered with desire and arousal as she began her thrusting rhythm, fluid dripped from his cock as she did, she scooped some up on her finger and fed it to him and he lapped it up hungrily. Feeling her orgasm was close now she found the key to his chastity lock in her cleavage and unfastened the device from him as she was balls deep inside him. His dick sprang from the cage it's head pulsing in time to her thrusts, she knew he was close, as was she. It was important for his mind to associate their kinky acts with moments of pleasure and release. Slowly conditioning and molding his male mind to her guidance and domination.

She drove the cock into him faster, grinding on her own dildo, she looked hungrily at his quivering form as she said "manly man" and thrust into him knowing this was it. His eyes widened as his male persona returned to see her above him driving a rubber dick into his ass and he shook as his orgasm washed over him and he came. Ribbons of hot creamy semen sprayed from his dick, up his corset and onto his face, some landing in his open mouth.

Jessica moaned deeply as her own orgasm hit, she ground on the dildo inside her as she watched him spray his seed over his face while his male persona grasped the reality of him being fucked in the ass and cumming from it. Her hips bucked as the orgasm subsided. She leaned forward and licked up the cum on his corset and chest then kissed him. Their lipsticks smeared together and she forced the semen in her mouth into his. Once she had made sure he had every drop she broke the kiss. His eyes were wide as he processed what had just happened.

"Swallow it now there's a good boy." she commanded softly but firmly. He didn't know what to do so he obeyed, so bamboozled by what had just happened. He swallowed and felt the warm salty fluid slip down his throat causing him to gag as he realised what he was doing.

To reinforce his good behaviour she slipped the rubber cock slowly from his ass and lay next to him embracing him and gently fondling his still firm cock as it continued to twitch in excitement. She nibbled at his ear causing him to shiver and goose bumps to form on his arms. "What a good little sissy you are Tom. You are learning so quickly that obedience is the quickest route to pleasure." She felt him relax as he enjoyed spooning with her at the end of a very confusing but arousing evening.

They lay there together for a long time, Jessica holding him, reassuring him that all was ok, that he was such a good boy. Eventually it was time to part though and she whispered tenderly in his ear "sleepy submissive." She felt the tension in his body dissipate instantly as he slipped into his trance state for her.

She allowed her nails to explore his body casually "A good submissive will never cum without their Mistress' express permission so that was the last time you'll let it happen. The cage was to prevent any weakness on your part in the time before we met and we'll keep it in the mix a while longer to make sure your conditioning is taking correctly. Ultimately I own your cock, its my property and good sissy's don't play with their mistress' toys without their express permission do they Tom?"

"No Miss Jessica."

"To that end you will find yourself unable to climax unless I give you very clear permission. No matter how aroused you are or how much someone is stimulating you you will be unable to ejaculate, you will forever hang on the edge until given permission do you understand Tom?" He nodded slowly

"We will need to be able to allow you to cum at some point, its such a useful tool in controlling a man. So at any point when I wish to allow you to cum I will clearly tell you 'Candi gets to cum', this will release your inability to climax and allow you to ejaculate. Once you have shot your load the physiological bar will come back and you will once again be unable to cum until given permission. Whenever you are allowed climax you will become even more eager to serve me as thanks for allowing you to climax and will of course do anything I ask in return for this glorious privilege."

"Yes Miss Jessica."

"When I wake you it will be time for bed, you will kiss me then go upstairs, on that floor you will find another bedroom with the door open. This is your room, all your things are there, my driver collected them from your hotel while we were at dinner. Get undressed and have a shower then get into bed and you'll have such a wonderful nights sleep especially if you wear the night clothes I left on the bed for you."

"In the morning you'll wake fully refreshed as Candi, you'll find a whole wardrobe of lovely things to wear and your makeup box will be on the dresser to make yourself look pretty for a day out. Don't forget to have a good clean shave before you get ready. Once you are properly dressed you'll come down stairs and have breakfast with me in the kitchen. Do you understand Tom?"

"Yes Miss Jessica."

"Good boy." she snapped her fingers and his eyes flickered awake, he rolled over and kissed her deeply before getting off the bed. She delighted in hearing his kitten heals clicking on the wooden stair as he wearily climbed them, the hot sensation once again building between her legs as she slipped the leather strap from the buckle on the strap-on harness and began to slip the dildo in and out of her pussy. 'One more before bed' she though idly as she relived the joyous moments of his realisation of captivity.

The morning after the night before

Tom slowly woke the next morning after a night of very erotic dreams. He'd dreamt of being dominated by a strong woman, been feminised, been passionately fucked in his virgin ass, wow! His cock was rock hard against a silky material he didn't recognise. He idly rubbed his dick against it as he tried to come back to his senses. As he opened his eyes he realised he wasn't in his hotel room.... Which was odd. He also noticed he was wearing a silky emerald green neglige with rich lace trim... which was very odd but strangely sexy, a feeling he was having trouble ignoring.