Jessica and Tom 03: A Sub-maid's Tale

Tom slipped off the stool and followed her to a high backed booth without even thinking about it, her natural beauty and confidence was almost as hypnotic as his own mistress. "I'm Tom by the way." He stuttered out as he slipped onto the leather seat with her.

"Oh I know honey, I saw your show remember. I'm Amber, very pleased to meet you." She held out her delicate hand for Tom to shake. "I'm fascinated by what we saw in the show, how does it feel to be so.... Enthralled? Is that the right word?"

"I guess it is." He mused about the correct term before continuing, "To be honest I'm not 100% sure how it feels as it all feels sort of normal. I didn't even know I was hypnotised until a few days after we met for real and apparently Miss Jessica has been pulling my strings for some time before that."

"Really? That's weird, I would have thought you'd be aware of things being a bit off, out of kilter a bit, you know?" She sipped her drink elegantly maintaining eye contact the whole time.

"Yeah I guess when I look back now I can recall some of it, there was some odd stuff happening but I just accepted it as normal."

"What do you mean? What things were odd?"

"Well for example, now I look back I know there was this big wooden box full of expensive makeup sitting on my desk along with a mirror but I hadn't had a woman in my apartment for months. My brain just sort of accepted that it should be there. It was only after Miss Jessica showed me video of me making my face up and allowed me to recall it that I now see its relevance."

"That's so awesome that she can control your perception of normal like that, Lady Jessica is definitely one of my girl crushes, she's so pretty and also so powerful and independent." Amber took another sip and placed her glass back down on the smooth lacquered table. Her hand idly slipped to Tom's thigh as she spoke with animation about Jessica. "And she even controls the little guy down there? That was a next level demo, I've never seen anything like that, its got to be an act surely, some numbing cream or something?"

"She seems to, I've certainly had no compulsion to touch 'him' and and I only seem to get hard when she commands it, i'm sort of a bit out of the loop I suppose."

"So if I were to have a little play down there you wouldn't get even a bit excited?" She asked excitedly, her delicate hand getting closer to his crotch?

"Oh I get excited, but I don't think I have any control over what the little guy does" he admitted as honestly as he could.

"Can I try?" she whispered conspiratorially making a show of looking around the quiet bar to make sure no one was watching, "I won't tell if you won't."

"Sure I guess, if you think its ok with the rules." Amber didn't need any more encouragement and she slipped closer to Tom, her skirt crumpling against his leg as she compressed the petticoat below. Her expert hand unzipped his fly and slipped into his crotch, gasping in excitement as she found the lacy panties beneath.

"Are you wearing girly panties under here young man?" She asked sternly as she slipped the delicate material to one side and found his soft member nestling within.

"Yes Miss Amber" he replied softly, blushing deeply.

"Oh Tom I do love a sissy boy, it gets me all hot and bothered to think of you wearing soft silky lingerie under there." She whispered in his ear as she took his cock in her hand and began to play with him.

Tom lay his head back and exhaled lightly, he could feel her playing with him and he loved the sensation of her soft hands on his intimate parts but his member remained resolutely flaccid. Despite her teasing whispers giving him delicious goose bumps and shivering down his spine and feeling his arousal build his little man remained somnolent.

Seeing she was having no effect Amber soon decided it was time to double down on her efforts, the seclusion offered by the dim booth empowering her to step up her game. She slipped her hand from his fly and began to unbuckle his belt then undid the waist button of his jeans splaying them open. She delighted in the sight of his black lace and red satin panties delicately framed by thick garter belts which led deeper down to his lace topped stockings.

She slipped the panties to one side again as she gained better access to his cock through his wie open jeans. He turned to watch her and she took the opportunity to kiss him deeply her soft red lips slipping over his and her warm tongue slipping into his mouth. Tom felt the familiar satin sensation of her red lipstick as it smeared onto his lips further peaking his desire but still not awakening his manhood.

Withdrawing from the kiss Amber descended and allowed her soft lips to caress the top of his cock leaving red lipstick on his cock end before enveloping him completely into her mouth. The warm slippery sensation of her perfect mouth was deeply sensual and Tom moaned in pleasure as he felt her tongue go to work on him. She tried in vain but still he remained unable to get hard despite his squirming and shivering in delight at her attention.

After several minutes she slipped him from her now lipstick smeared mouth and sat back up adjusting herself to look less like she had just been giving amazing head. "Well I never." She exclaimed, "I've never struck out like that, are you sure you aren't gay Tom?"

"No Miss Amber, I'm very much into women" he said breathlessly "Miss Jessica has a very tight hold on me it seems"

"I think we are going to have to move this up a gear as I do want to enjoy that lovely cock of yours." She said thoughtfully as she wiped her lips with a napkin and pulled out her compact and lipstick from her purse. Carefully she reapplied her crimson lipstick and touched up her face to remove any hint of misbehavior before tending to the remnants of lipstick on Tom's face where she had kissed him. "Would you like to join me in my suite and further explore Tom? I am not going to be defeated you know"

"Yes Miss Amber I would very much like to but I think I need to get Miss Jessica's approval first" he waved his wrist showing his amber bracelet with its shiny silver clasp.

"Of course my sweet, perhaps she could join us and I can explore my girl crush too?" Said Amber excitedly as she slipped off the smooth leather bench seat and straightened her skirt and petticoats before offering her hand to him.

Tom fastened his belt and buttons before slipping out of the booth to join Amber and taking her hand where she lead him away from the bar, leaving their drinks half finished where they sat.

Amber led Tom down several halls in the expansive country house before finally reaching the suite. Tom was utterly turned around. All the while she had been talking about how she was looking forward to seeing what he had hidden under those boring boy clothes and what she wanted to do to him once she finally got his little man to behave himself.

She lead him into a large opulent suite easily the size of his whole apartment back home. Several items of bondage furniture were clearly visible surrounding the oversized and sumptuous bed in the centre. Taking him by the hand she stood him in front of the large mirror next to the bathroom door.

"Before you call Lady Jessica I think we should get you properly dressed don't you?" Amber cooed as she slowly unbuttoned Tom's red shirt maintaining eye contact with her large green eyes as she did so.

Tom nodded enthusiastically as his mind ran away with him at the thought of a threesome with this beautiful young lady as well as his queen. "I think Miss Jessica would like me to be properly turned out yes. She likes me dressed as a good sissy."

"Delicious, I'll have you looking ready to serve in no time" she slipped the shirt from his shoulders with a gentle push and let it fall to the ground revealing the red satin and black lace corset he wore beneath. She ran her fingers over the intricate boning. "Lady Jessica does have fine taste in lingerie." she delighted as she worked her way down to his jeans once again and unfastened the leather belt and slowly worked the waist button and fly open.

Pulling the waist of the jeans she unwrapped Tom delicately like a much cherished Christmas gift delighting in each inch of the luxurious lingerie beneath. "All you are missing now is a good set of tits and you could pass for a real woman. I think we can help with that." She took his hands and encouraged him to step out of the pile of crumpled jeans at his feet.

Amber made a beeline for a drawer in the expansive closets at the back of the suite she found a B cup bra in similar red and black to complement Tom's current outfit. Next she slipped a pair of breast forms into the cups before slipping the garment onto his shoulders and making sure it sat just right above the corset and adjusted all the straps to keep things just so.

"Now lets see about your hair and makeup shall we sweetie?" She guided Tom to the dresser and he obediently sat on the velvet covered bench. Tom could feel his submission washing over him even without Jessica pulling his hypnotic strings. He reveled in the descent into obedience as this wonderful creature pampered him into servitude.

Having taken her time to moisturise and massage his face Amber soon had a healthy layer of foundation and concealer in place giving her a flawless blank canvas to work from. From there she worked delicately on his eyes working a deep burgundy shadow onto his lower lid and then a deep charcoal as she went higher on the lid giving a powerful sultry smoke to his eyes. Adding to some glitter in his tear ducts and along his eyeline then boldening it with a fine liquid eyeliner to give him a perfect pinup girl wing. Large false lashes were then glued in place and coated in heavy mascara.

Amber applied a delicate rose colour along his cheeks to give him back some colour then highlighted beneath with a slightly glittery highlight to give some contour. Never too much to make it look false, just enough to pop and sparkle in the bright lights of the mirror. Using a deep red pencil to line his lips she then set about the final touch to his burlesque appearance, lashings of cherry red lip ink and a heavy coat of lip gloss.

Tom delighted in the transformation, enjoying being along for the ride and completely submitting himself to be the girl of someone else's dreams. He slipped his lips together and felt the familiar arousal as he imagined what was likely to come next. Amber returned from the closet with a fire engine red wig and slipped it onto his head carefully arranging the luxurious locks to frame his now perfect face.

"There, I thing you are perfect." she exclaimed as she admired her work "I'm really looking forward to ruining you my sweet Tom." With that she guided him to stand. "Perhaps we should summon Lady Jessica?"

"Of Course Miss Amber" Tom tapped the metal clasp of his bracelet three times as he had been told and allowed himself to be taken in a deep embrace as Amber slipped her lips onto his and her tongue into his warm mouth. After a long passionate kiss where Amber's hand roamed Tom's silky ass cheeks without restraint, she withdrew.

"Perhaps you can help me get properly dressed too Tom?" She turned slightly hinting towards the small zipper in the side of her billowing skirt. Tom grinned and nodded eagerly as he slipped the zipper down and slowly slipped the skirt over her hips and to the floor revealing her equally ornate black lingerie each piece with a hint of red. A red bow on the centre of her garter belt, red ribbon running around her frilly lace panties, a red seam running up the back of her fully fashioned glossy black stockings.

As Tom slipped down her skirt, Amber casually shrugged out of her clinging black top and discarded it on the floor revealing her ample breasts barely held in by her black satin and lace corset. She gently pressed on Tom's shoulders and he took the hint to descend to his knees as she enjoyed asserting her control. Tom tentatively kissed her alabaster thigh leaving a telltale red lip mark. Amber slipped a thumb into the band of her panties and looked down at her willing submissive daring him to slip them from her waist.

Tom took the hint eagerly and eagerly slipped the panties down revealing her special surprise. A quickly hardening cock sprang from the frilly prison bouncing right in front of Tom's face as it settled and swelled. Amber moaned with relief as her cock was freed and reached down to hold her smooth shaven member guiding it to Tom's waiting red mouth.

Taken by surprise Tom had little choice but to accept Amber's cock as it slipped smoothly past his glossy lips and into his warm mouth. Tom gazed up in surprise as she held the back of his head gently but firmly in place relishing his startled face as well as the wonderful sensation of his soft willing mouth. Amber slowly began to thrust and Tom quickly accepted his place as her cock sucking sissy, his head bobbing to her rhythm.

Without warning the door to the suite opened with a clunk and in the door stood two statuesque women wearing feigned looks of amused surprise. Jessica was first to speak "I see you began without me Tom, how rude!" She said in mock indignation.

Lady Abigail chuckled as she brushed past into the room, "Amber you really are a dirty slut, did I give you permission to seduce this poor sissy? I only told you to get him here and get him ready for me!"

"Oh I'm so sorry Mistress but he was just so cute, he didn't even realise I was a chick with a dick, I just couldn't resist. He is such a talented little cock sucker though!"

"You had better not cum in his mouth! Yet anyway. Remember we have plans for this pretty little sissy, I've been looking forward to him all night." Said Lady Abigail.

Jessica and Abigail flanked the kneeling, cock sucking sissy. Tom could smell the heady mix of expensive perfume and female arousal from them as they watched him suck on Ambers throbbing cock. The two leading ladies smiled at each other before enjoying a deep and intimate kiss.

After they broke their twining tongues apart Abigail was eager to progress her long awaited treat. "So you say he'll stay good and hard for as long as I want.... No matter what?" she queried.

"Oh I'm sure he'll be more than up to the task wont you my sweet Tom"

"Mmmhhmmm" he managed still dutifully servicing Amber's cock.

"Bring him over here so we can get better acquainted Amber." Amber sighed petulantly before slipping her member from Tom's eager mouth with a wet pop. "Best freshen up his lips too while they aren't in use."

Amber passed Tom the cherry red lipstick she had used earlier and he slipped the wand over his lips in a sweeping motion spreading the colour thickly, followed by the gloss. He then took Ambers hand and was led to a leather covered bench.

Abigail slipped her hand over Tom's slight figure lingering over his crotch to see if she could get a rise but to no avail. She gestured to the bench and Tom obediently lay down on his back. Amber began to fasten the straps around his torso as Jessica did the same to his legs. Abigail slipped to the top and knelt beside him fastening the thick corset style neck restraint in place before whispering in his ear. "I'm going to ride you till I spray my hot pussy juices down your little sissy cock and its going to bend your little head how good it will feel."

Abigail stood and slipped one hand behind her back expertly unzipping her gown and letting it fall to the floor revealing her mature but incredibly toned body. Her torso wrapped in a black and purple satin corset, he snatch perfectly framed by her garters and gloss lace topped stockings. Her pert tits hung free above the top of her corset and her nipples were hard with arousal. "But first...." She smirked "... Amber should really get her reward for such an expert job of seducing you."

Amber clapped with glee as Jessica parted Tom's legs on the leg pads revealing his tight sissy cunt. With the neck corset restraint in place Tom strained to see what was going on but could only see their faces and northing below the neck. He heard a snip and felt his red satin panties fall away and then be pulled from his body then felt the familiar sensation cold lube and then an intruder pressing at his rosebud.

Relaxing and allowing his submission to blossom he felt the bulbous head of Ambers cock slip into him and, soon after, a moan escaped the owner as she enjoyed his tight warm hole. Jessica came to the top of the bench and kissed him warmly. "You are being such a wonderful sissy Tom" She said. "It will make me so happy for you to serve Lady Abigail and to watch you submit to her whims."

"Anything for you Miss Jessica" he whispered as he slipped further into submission.

"Rise to the occasion my sweet" and with that Tom's soft cock quickly hardened and his arousal built with each stroke of the lady cock within him. Abigail slipped a rubber ring gag into Tom's mouth as he moaned with pleasure, his prostate being tenderly stimulated by Amber. Amber's moans became louder as she thrusted onwards to her orgasm. She couldn't resist toying with Tom's now hard member as it bobbed to the rhythm of her thrusts.

"No cumming inside him Amber!" Abigail chastised as she saw he own sissy's telltale signs of climax.

"No Lady Abigail I won't but it feels so so good" Amber moaned.

"When you are almost ready then withdraw and take off that condom then come up to the top here." Tom felt the thrusting become more positive and he knew his own cock must be oozing precum but soon he felt Amber withdraw, her bulbous tip slipping from his ass leaving him feeling empty.

Her glistening cock appeared in front of his eyes and rested on the edge of his ring gag. He felt another pressure on his ass as a plug was slipped into him then Abigail stepped over and straddled him. In one fluid motion she was on top of him, his hard cock slipped easily into her warm cunt and she gasped with delight as it rubbed on her engorged clit.

"May I cum Lady Abigail?" Amber whined insistently as she balanced her cock end on the edge of Tom's open mouth.

"You may but make sure he takes your entire load" she replied in short grunts as she rode Tom's phallus.

Tom felt the cock slip into his gagged mouth and unconsciously welcomed it with his tongue surprising himself with his willingness. With the tip and a quarter of the shaft in his mouth Amber once again began to thrust, slipping in and out of his warm hole.

Jessica watched the spectacle in delight as her wonderful submissive was used to pleasure her two friends "tip over the edge" she whispered in his ear as she saw the twitching of imminent ejacualation in Ambers cock.

Tom spasmed as he reacted to the deep trigger and his mind and body climaxed in a dry orgasm. Tom tasted the salty sweet semen gush from Ambers glans and spurt into his waiting mouth. In ecstasy he slipped his tongue over the pulsing dick and hungrily devoured each rich ribbon of cum as Amber emptied herself into his mouth.

His triggered dry orgasm caused him to buck and strain against the restraints driving his sissy cock deep into Abigail as she pounded him and ground her clit against his raging cock. No matter what he did, despite the incredible arousal he felt and overwhelming desire to dump his own load into Abigail his cock remained resolutely unable other than his oozing pre-cum.

As Ambers throws of climax subsided she slipped out from Tom's mouth. Jesica Slipped the ring gag from him and replaced it with her own mouth as she kissed his glossy lips deeply, tasting the remnants of Ambers seed. Abigail was moaning heavily now and Tom could feel her pussy quivering as she rode him. Jessica, now nude except for her stockings and exquisite makeup, stood on the steps either side of the fucking bench and used the position to straddle Tom's head, facing Abigail, slipping her now dripping wet sex onto Tom's eager mouth. Without command she felt his tongue slip into her waiting hole and begin lapping at her quivering clit. She embraced Abigail and they kissed deeply as they used Tom to pleasure their wanton desires.