Jessica and Tom 02: Meeting Up

He felt his cock throb and quickly moved the neglige, he didn't want to get it dirty. The cool air wafted under the warm duvet as he did so which served to motivate him to get up. He slipped the neglige off and laid it folded on the pillow and went to the bathroom to shower away the last vestiges of sleep. He made sure he had an extra close shave before getting out and toweling off.

After his shower he sat at the dresser and idly began applying moisturiser to his face before beginning his makeup routine. The foundation gave him a soft flawless base to work from as he worked with a rich brown palette on his eyes. A little peach blush put some more natural glow into his complexion and he finished his look with a nude pink gloss lipstick. He took the copper coloured wig and slipped it over his head arranging the loose curls to flow over one shoulder.

Once his face and hair were done he went to the closet and found an assortment of clothes and lingerie. He picked out a black Lycra and red lace basque, already fitted with cute B cup breast forms. A pair of black frilly satin French knickers and a pair of nude glossy fashioned stockings completed his undergarments. Having rolled the stockings up and fastened the garters he fussed to get the seams straight before pulling out a tight black jersey dress. The dress went to his ankles but had a generous slit to show off his legs. In the bottom of the closet he picked out a pair of black kitten heels.

Checking himself in the mirror he admired the way the jersey dress clung to his figure and the way his legs casually slipped in and out of the slit in the dress. Rubbing his lips together he grinned, picked up his lipstick and compact and put them in a cute little clutch bag and tottered out of the room and down the stairs completely unaware he had transitioned to his Candi persona.

Jessica sat at the breakfast bar in the kitchen naked but for her black satin dressing gown. She heard the click of heels as Candi descended and wondered what he had chosen to wear. He sashayed into the kitchen smiling to himself. She admired his choices, the dress fitted him perfectly and was classy but tarty at the same time. She berated herself slightly when she noticed the bulge in his pants, she had forgotten to instruct him to put his chastity device back on. She would need to sort that out before they went out.

"Well Candi don't you look pretty this morning."

"Thank you Miss Jessica, I tried to find something that would be suitable for a day out with you." he gave a cute little twirl as he approached her and leaned forward for a kiss. She gave him a gentle peck on the lips. She patted the stool next to her, inviting him to join her.

"You've done such a good job of your makeup sweetie and I love your dress but we forgot one vital thing. Why don't you have some breakfast while I go fetch it for you." she slipped off the stool and went upstairs to retrieve his cage.

Candi dug into the croissants and cereal Jessica had laid out but made sure he didn't over eat, he didn't want to look chunky in his new dress after all. Jessica reappeared a few minutes later, her satin gown had slipped open at the front, it's silky material flowing over her breasts but leaving her pussy on show. She stood behind him and slipped her hands down his front as he finished a bit of croissant. Her hands soon found his bulging cock. She kissed his neck before showing him the cock cage.

"Here's what we forgot sweetie, I don't think it's going to fit like it is though, would you like me to help?"

Candi nodded and swiveled on the stool to face her. Jessica slowly lowered herself to her knees, her hand slipped into the slit in his long jersey dress. She raised the hem to gain access and slipped his cock from his satin panties. Kneeling in front of him she kissed its top gently before slowly allowing it to slip into her warm wet mouth. Her supple lips slipped gently down his shaft and her tongue coiled easily around the tip and found the sensitive spot just below the head.

She slipped her lips slowly up and down his dick. Using her tongue she teased his most sensitive areas and began to concentrate her expert technique to bring him to climax. She felt the telling pulse of his head in her mouth and the growing shivers of his thighs as he began to reach his peak. No man could resist her for long but she persisted to see if his conditioning was taking hold. He squirmed and moaned, his cock oozing precum but he remained unable to reach his peak.

Grinning as she slipped his dick from her mouth, she knew she'd never get his hard cock into the cage without satisfying his desire. She stood and took a glass from the counter and put it next to the tip of his cock "Candi gets to cum!" She watched with great pleasure as he arched his back as his orgasm approached. He gasped as her words triggered his climax without her even touching him. His cock spewed its warm gooey load into the glass as his hips bucked. Once his orgasm was over she coaxed the last drops into the glass then slipped the cage over his now softening cock and clicked the lock closed once again.

She handed him the glass "drink up sweety." she said and he placed the glass to his lips and took the warm cum swallowing it down without argument.

Once she had made sure his cock was back in its cage she slipped back onto her stool and grabbed a piece of toast. "Are done eating sweetie?"

"Yes Miss Jessica, thank you for such a lovely breakfast." he responded chirpily.

"Good but I do have something else you could eat." she slipped the gown open to allow him to see her moist sex "would you be a dear?"

He slipped off his stool onto his knees and took the cue. She parted her smooth legs and shivered as she felt his tongue slip inside her warm pussy lips and begin to lap at her clit. She continued with her toast as he eagerly ministered to her now dripping sex but eating soon became less important as her quivering climax built quickly.

Her thighs clamped around his cheeks and she used her hands to hold his head in place as she ground against his persistent lapping tongue. She moaned deeply as she felt her orgasm crash over her, bucking her hips against his eager mouth and probing tongue only heightening her pleasure.

As her spasms waned she released his head and gazed up at her lovingly, his face slick with her slippery juices. "Thank you for allowing me to taste you Miss Jessica."

"Oh sweetie you are so welcome. Now why don't you fix your makeup while I get ready and then we'll go out and see Miss Sarah at the salon." He grinned ear to ear as he stood and went back upstairs to try to rescue his spectacularly ruined makeup. 

A trip to the salon

Candi slipped into the back seat of the large black Mercedes limo. Jessica slid into the other side of the car and smirked as she saw Candi start to gaze into nothing as he slipped into his programmed daydream. She took out her laptop to catch up on her emails as the limo drifted through the late morning traffic on the way to Sarahs salon.

He stepped out from the limo and tottered on his kitten heels to join Jessica on the path in front of the salon. She pushed the door and stepped inside, the dark windows giving no hint as to what was inside.

Sarah's heels clipped gently on the sparkling black floor of the lobby areas as she came to greet her new customers. "Candi this is Sarah, its her salon, you can call her Miss Sarah or Ma'am ok? He nodded eagerly "You are to do exactly what she tells you and be totally honest just like you do with me like a good obedient submissive, do you understand?"

"Yes Miss Jessica, hello Miss Sarah, a pleasure to meet you." Said Candi as she reached forward to air kiss the stunning tall platinum blonde beautician. Sarah returned the air kiss mouthing 'wow' to Jessica as she glanced across.

"Why don't you have a seat over there sweetie while I speak to Miss Jessica quickly." Said Sarah pointing to the only reclining treatment seat in the sparse salon. Candi quickly tottered across to the seat and made himself comfortable leaving his purse on the counter under the large mirror.

"How did you do this so quickly? You said you'd only met him on line a few months ago and he's putty in your hand already!" Said Sarah to Jessica as she sat on the sumptuous leather sofa and started to setup her laptop to do some essential work.

"He's such a responsive subject, I'm surprised myself. I'm going to try something quite advanced later and see how far I can push him but I think he's keeper. Plus he can lick pussy like a demon. I had one of the best O's this morning I've had in years with his head between my legs! Feel free to give it a go if you want I know you love to squirt on a guy."

"Don't mind if I do! Did he do his makeup this morning himself?

"Yes all his own work, he's been very dedicated with your videos over the last few weeks plus he's had a fetish for makeup and being a sissy for a long time. He's just always hidden in the shadows with it. I think that's what makes him so compliant so quickly it's actually what he wants he just hasn't accepted it yet or been able to express it openly."

"There's some work to do but its a good starting point" she reached down and kissed Jessica deeply before returning to the treatment chair. Her white beautician uniform was cut just right to accentuate her stunning figure, its thigh length hem guiding the eye to her perfectly toned and tanned legs. Jessica felt her sex tingle at the memories of hot steamy nights with her over the years.

Sarah gently reclined the chair and examined Candi's face and then her nails "You did a lovely job of your makeup today, that lipstick is a lovely shade on you"

"Thank you Miss Sarah, its the one from the box you made for me, I love it." he gushed.

"How about we give you a whole new look?" Sarah said as she began to use a pad and cream to remove Candi's makeup. He nodded enthusiastically and grinned.

Sarah took a long time to moisturise his face and condition the skin until she felt it was just right then covered his face in a green mask to deeply cleanse and rejuvenate his skin before starting on his finger nails.

An hour of careful sculpting and filing was followed with layers of crimson, then clear lacquer to give them a strong and flawless finish. Not really needing to concentrate Sarah was also day dreaming of her steamy times with Jessica. Her snatch dampening rapidly as she recalled all the sworded deborchery they had enjoyed together.

Once the nails were done Sarah removed the green moisturiser mask from Candy's face. She was so horny she could wait no longer "Candi, Miss Jessica says you love to pleasure her, would you like to pleasure me too?"

"Of course Miss Sarah, I'd love to please you, what can I do?"

Reclining the treatment chair full flat Sarah slipped the white hem of her uniform up and straddled his waiting face, lowering her wet snatch gently onto his mouth resting one knee on her own stool for support. "I think you get the general idea honey." She said sighing as she felt his tongue slip into her pussy and start to flick against her quickly swelling clit.

Jessica looked up with a smirk as she heard Sarah moan in pleasure as her climax grew. Knowing her submissive boy was frantically and compliantly lapping at her lovers cunt, so desperately eager to please both women. "You dirty dirty sissy!" she muttered as she heard Sarah's familiar orgasm resonate through the deserted salon.

The trip to the salon had taken 3 hours and another orgasm for Sarah but Candi's transformation was complete. His copper red hair had now been replaced with platinum blonde just like Sarah. The long locks of the wig draped over one shoulder and expertly styled. His skin was flawless alabaster and his eyes beautifully blended metallic sable into dark charcoal gray. Thick eyeliner accentuated his large false lashes and his lips in a matte burgundy red. Candi grinned from ear to ear as she checked herself out in the mirror.

"Go and show Miss Jessica to see if she approves." said Sarah as she slipped the paper bib from his chest. Candi slipped from the chair and tottered over to where Jessica sat with her laptop. He tossed the bouncy locks as he presented himself to his Mistress.

"Very pretty sweety, did you pay attention to all the steps so you can look so good on your own?"

"Of course Miss Jessica, Miss Sarah told me all her tricks."

"Excellent" Jessica said loudly "How do you think we should pay Miss Sarah?"

Candi looked first confused then worried as he realised he had no money. "I think I left all my money at home Miss Jessica, I don't know what to do."

"Miss Sarah is the next-door barbers still doing happy endings?"

Sarah grinned widely "of course but I want to watch!" She took Candi by the hand and led her to a door at the back of the salon. She flicked the light on and revealed a small empty room with a small soft cushion on the floor and a small hole in the wall at waist height. She led Candi to the cushion and guided him down to kneel in front of the hole.

No more than a few moments passed before a thick hard cock slipped through the hole "Well Candi, here's the deal," Sarah began "the barbers next door has a very exclusive clientele and they like a happy ending. They know who I am and pay top dollar for my 'services' when I make them available. As its not me I'm only going to charge half, so every blowjob you give, you earn $50? It'll likely get a bit messy so I'll do your makeup again afterwards as a reward. Does that work for you?"

Candi nodded enthusiastically as the cock bobbed in front of her. Jessica stood next to Sarah and watched carefully as Candi tenderly took the cock in his fingers and guided it to his soft red lips. The head slipped into his mouth and there was a definite moan from the other side of the wall as it entered the warm open mouth.

Candi worked eagerly at the cock, slipping it in and out slowly, licking the base of the tip as he went. The tell tale signs were there, the cock began to pulse and twitch before it erupted into his mouth. Warm creamy jizz hit the back of Candi's mouth and slipped down his throat. He slipped the cock from his mouth before licking the last of the sticky goo from the tip and allowing the cock to disappear back into the wall.

"Well what a good little cock sucker you are Candi." Sarah hooted "that was so hot to watch." Candi looked over his shoulder at the two woman and smiled nervously.

"It looks like you have another customer, why don't you try another technique this time, I'm sure you know a few from the internet. Be a real cum slut for us."

The new cock was shorter but much fatter, Candi once again slipped her hand down the shaft and guided the mushroom headed member into his waiting mouth. His careful ministrations left burgundy lipstick streaks on the cock as his lips slipped easily up and down the shaft. Recognising the approaching orgasm Candi slipped the cock out of his mouth so only the tip remained pursed between his lips. Concentrating only on the tip the owner of the cock didn't last long, cum once again gushed forth this time some of it squirting out of Candi's mouth and dribbling down his chin. he used his new long red nails to scoop up the excess and spoon it back into his mouth as the cock once again retreated.

"Candi you do look good with jizz on your face, like a real slut" Jessica said "make sure you eat it all up. See how easy it is to make money!"

"Now this time lets see you get a full facial, the boys love that even when they cant see it, it gives them a sense of superiority spraying their seed on a girls face." said Sarah.

In no time a third cock slipped into position and Candi slipped her not so red lips onto the waiting shaft sliding the foreskin back as he went uncovering that gloriously sensitive spot under the tip. Drool dripped from his chin as the large cock slipped all the way to the back of his throat causing him to gag occasionally.

"This is so hot to watch!" Sarah said, Jessica noticed the blond slipping her finger into her own snatch and playing with herself vigorously as she watched.

Soon the owner was once at the edge of orgasm and as instructed Candi slipped the cock from her warm mouth and began rubbing his hands up and down the shaft and occasionally licking the tip. It didn't take long before the inevitable happened.

As Jessica saw the telltale twitching begin indicating he had reached the point of no return she triggered his change "manly man"

Long ribbons of hot white cum spewed from the cock onto Candi's face, a big glob went into his eye, another landed on his shoulder quickly soaking into the jersey dress leaving a telltale stain. Some went into his eager open mouth, there was nothing Tom could do to avoid the torrent of cum as his male persona returned. "Make sure you get it all like an obedient submissive." Jessica said, even though he was sickened by the thought he found himself compelled to slip the thick cock back into his mouth and devour the last drops of man fat.

"Come here sweetie, let's see what a mess you've made. The cum from his eye had begun to dribble down his face causing his mascara to run and another rivulet from his cheek ruined his delicate blush and foundation. "What a dirty little cum slut you are Tom, who'd have thought it."

"What did you make me do?" He said totally confused.

"Tom you just sucked three fat cocks and swallowed about a half pint of jizz like a good little submissive cum slut. I'm so proud of how far you've come. The best part is I think you actually enjoyed it." Jessica raised the hem of his dress and sure enough found a tell tale wet patch on his satin panties from his dripping precum "See, you've got a wet patch where your boy clit has got all wet."

Tom blushed beetroot red knowing she was right it had been a hot experience even though he had no control of what had happened.... Or was that why it was hot?

"Now clean up the rest of that goo and we'll get you tidied up ready for tonight." without even thinking his fingers scooped up the cum dripping down his face and he licked them clean That was enough to tip Sarah over the edge and she moaned as she came.

Another hour in the makeup chair and Candi was cleaned up except for the jizz stain on her shoulder which had now dried in place. Now his eyes were a vivid red on the inner lid which Sarah had then blended out to a dark charcoal grey on the outer lid and highlighted with a shimmering silver on the tear ducts finished of with a generous sweeping winged eyeliner. His skin remained pale with warm bronze highlights giving a metallic hue to his cheeks. His lips were a deep metallic burgundy which shimmered in the light.

As they walked out of the salon Jessica texted Dylan "Playtime at my place 6pm, Don't be late!" his services would be needed tonight to bend Tom to her ultimate desires.

Politely receiving your guest

Candi sat at the dresser casually touching up his perfect makeup that Sarah had so expertly done for him earlier. He pouted and slipped the new shade of lipstick over his lips freshening the deep shimmering burgundy colour to perfection.

"Hello Candi." Said Jessica as she entered the room, "We have a guest coming over at six this evening, I really think you'll like him. He's another one of my submissive friends and he's going to help me help you to progress so much. I really want you to make a good impression so I've put some special lingerie in your closet I'd like you to wear. No need for a dress as we're all friends, just your lingerie and the new heels I've left for you. be downstairs at five to six to properly receive our guest please."

"Of course Miss Jessica, I'm looking forward to meeting your friend, I'll do my best to be a good sissy for you."