Jessica and Tom 02: Meeting Up

Jessica kissed him on the cheek gently rubbing the lipstick print she left behind so as not to ruin his makeup "good sissy"

Candi went to the bed to inspect the new lingerie she had left him,

"Miss Jessica can you help me with the corset please, I want to make sure its perfect for your friend."

Jessica's took the corset just like she had the previous night and slipped the black satin onto his naked body clipping the metal fastener at the front closed before tightening the laces at the back. The black satin had a delicate diamond pattern running though the material catching the light and shimmering as he wiggled, adjusting his posture to accommodate the tight garment. The corset had thick garter straps already attached and he quickly slid the black stockings up his legs. Jessica left him to it and quietly left to get herself ready for the evenings fun and games. She relished the thought of the deliciously dirty things she had planned for Candi.

At exactly five to six Candi was at the bottom of the stairs, his blond wig quaffed and makeup perfect. The soft light of the hallway glinted off the corsets metal faster and the diamond pattern twinkled as the candles flickered.

At exactly six p.m. the door bell rang and Jessica called from upstairs "Candi will you please get that?" Candi obliged and opened the door onto the street bearing his semi naked form the to handsome gentleman on the step.

"Good evening," he said formally, "my name is Dylan, I'm here to see Miss Jessica."

"Of course, I'm Candi, please come in." He moved to one side to allow the dark haired man to enter, his aftershave light on the cool breeze from outside.

As they both turned and the door clicked shut Jessica made her entrance from the stairs, her knee length black leather boots with ornate laces all the way from instep to top came into sight then her long toned stocking clad legs topped with rich lace tops guided the eye to sheer panties and a black leather corset barely containing her breasts. Her raven black hair tied back into a severe tight pony tail oozed dominance and her dark eyes and long eyeliner screamed control. Her deep burgundy lips turned up in a smile as Dylan immediately sank to his knees in the hallway. Candi looked at her in total admiration and awe before he too sank to his knees.

"What good pets your are." she said as she stood imperiously before them lifting Dylans chin with one satin gloved finger. "It's playtime for good boys." she said looking deep into his eyes reinforcing his deep rooted trigger.

"Yes Mistress, I live to serve you." he said with a glassy eyed stair.

"Go into the basement Dylan and get prepared."

"Of course Mistress." he said standing and walking towards the kitchen then taking a left and descending into the basement.

"Now Candi, Dylan, as you can see is a well trained submissive and he is going to help you in your next phase of training. Because you have been such a good submissive sissy I'm moving far faster than normal but if anything happens that you aren't happy with you must say 'bananas' if you wish to slow down or 'tomatoes' if you want to stop, do you understand?"

"Yes Miss Jessica."

"You understand that I would never hurt you or make you feel unhappy if it wasn't for your benefit, I would never be malicious in anything we do together, you can trust me implicitly my dear Candi."

"Yes Miss Jessica I understand."

"Good sissy, now lead the way down to the basement and lets see what the evening brings shall we?" Jessica gestured for Candi to lead the way and she fell in behind enjoying the view of his perfectly framed ass as he sashayed towards the basement door.

As Candi descended the light became dimmer, the stairs lit by old dim filament light bulbs that were once again en vogue. Her heels made a light tap against the concrete steps as they went followed by the more sturdy clip of Jessicas leather boots. A welcoming red glow came from the bottom of the stairs where a door frame lead into the unknown.

The stairs opened out into a large room the full size of the floor plan of the town house, columns took the load and upon them wall sconces held flickering candles. Around the walls were various pieces of apparatus riddled with sumptuous leather pads as well as hard steel eyelets. In the centre a huge extravagant bed lay with four 3 quarter height posts upon which more steel eyelets had been fixed. At the footboard of the bed a large throne sat with plump plush cushions.

"Welcome to my play area Candi, we're going to have such fun in here over the next few weeks." Jessica said as she took Candi's hand and lead her to the plinth in front of the throne. A gentle push on his shoulder hinted for Candi to kneel on the soft cushions in front of the throne and Jessica tapped past and sat upon her throne sinking easily into the deep cushions.

From behind one of the pillars Dylan appeared holding a tray with a bottle of champagne and one fluted glass. A memory flashed into Candi's mind as he recalled now where he knew Dylan, the barman from the other night. A dreamy memory which seemed so far away now.

Dylan approached the throne, his well build body glistened slightly in the candlelight. His overly generous endowment plainly on show through the skin tight Lycra trunks he now wore. Candi looked up at Jessica, bathing in her magnificence, knowing all he wanted to do was serve her to his bitter end.

Dylan expertly poured the champagne into the flute then handed Jessica the glass. He placed the tray next to the throne and retreated to the same plinth and also knelt before his queen.

"As you can see Candi, Dylan is quite a specimen of manhood. He is totally faithful and obedient to me. We have spent many years together honing my control of his mind and body. When triggered, like you, he lives to serve me and will do almost anything to please me." Jessica took a sip of champagne, a smirk of anticipation passing across her lips as she once again imagined the possibilities of the evening as she pushed Candi's boundaries far further than a usual new submissive.

Reaching across to Dylan she placed a finger under his chin and gently raised him to a stand and turned him towards Candi. His Lycra encased manhood now sat mere centimetres from Candi's face. She stood and positioned herself behind Dylan sliding her slender fingers into his trunks and squeezing his tight muscular buttocks before slowly sliding the trucks down to the floor.

His ample manhood was flaccid and easily measured in excess of 6 inches. Jessica knelt between Dylan and Candi, gazing a his cock. "You see the control I have over him? He is not aroused as yet despite the extremely arousing environment we find ourselves in. I so look forward to having such control over you my darling Candi." She reached out and held his soft cock in her hand unable to fit all of it in her hand, the mushroom head spilling beyond her grip.

"Dylan will once again satisfy me with this cock tonight, likely more than once, but to start with we must focus on your progress." She stood and whispered something to Dylan causing him to smile, the glassy look he had so far worn starting to wane as he became more present. "Do you know what fluffing is Candi?"

"Yes Miss Jessica." Candi replied

"Tell me my dear."

"It's where someone prepares a male porn performer to fuck by getting him hard and keeping him hard." Said Candi now unable to gaze at anything other than the large flaccid cock directly in front of him.

"Excellent!" exclaimed Jessica, "Well Candi I think that if Dylan is going to perform you'd better start fluffing him don't you? He wont satisfy me if he's not absolutely rock solid." Jessica gently took Candi's hand and placed it on the tip of Dylan's cock. He gripped the soft cock gently, closely inspecting the large round head before instinct took over. From his deep burgundy lips his tongue came out, gently caressing the tip of the cock. Holding his tongue on the sensitive area just below the head. Dylan sighed as Candy slowly slipped the head of the cock into his warm mouth past his burgundy lips, lipstick smearing across the head as it slipped inside and past his teeth.

The response from Dylan was inevitable, the whisper had triggered his ability to be erect and the sensation of his cock gliding into a warm wet mouth was all that was needed for it to quickly grow hard. The sensation of the swelling cock inside his mouth in turn aroused Candi as he took more and more of the length into his mouth. Jessica sat to enjoy the show, her pussy already dripping in anticipation of the spectacle she was seeing unfold before her.

Candi began to slowly ease the now engorged cock in and out of his mouth leaving more smears of burgundy lipstick on the shaft as Dylan stood obediently with his hands behind his back watching his cock being swallowed by the hungry sissy's mouth.

"Excellent work Candi, look at how hard you've made him, I bet you can feel that cock throbbing with desire as he slides it in and out of your wet mouth." Jessica said as she slipped her fingers into her pussy and quickly found her own special spot. Drool began to drip from Candy's mouth as he slowly pumped the cock in and out. "We'll know when he's ready to serve me when you start to taste his precum oozing from the tip so don't forget to tell me." Candi nodded while greedily taking the member deep into his hungry mouth.

Perfect Jessica thought, a few more strokes and its time, "He really is a manly man isn't he" she said knowing the effect it would have. Candy's eyes widened as Tom reappeared and realised he again had his mouth full of another man's member. This was the moment where she knew he would either balk or continue. She desperately hoped it wasn't too soon. The wave of tenseness eased as Tom appeared to accept his fate, he looked up at Dylan and slid the cock back into his mouth. As if on cue the taste in Tom's mouth changed as the first pearl of precum began to bead on Dylan's cock and mix with Tom's saliva. He slid the cock from his mouth.

"Miss Jessica I think he's ready."

"Are you sure my dearest? Will you lick the tip again just to be sure?"

Tom slipped his tongue over Dylan's head and took another drop of fresh precum in mouth nodding affirmative. "Wow Tom you are so so brave." Jessica reached forward and kissed Toms smeared lips tasting the precum on his tongue "it's very different from sucking on a cock in a glory hole isn't it my dear? Now you can see the pleasure you are giving to the lucky guy knowing how sexy you look down there. But, to business, You are right he is indeed ready to satisfy my needs but we need to do one more thing before he does."

Jessica stood and took a black butt plug from a selection on the wall. Squeezed a large amount of lube onto her hand and walked behind Tom. Easing his panties down she sensuously massaged his not so virgin ass with the lube. "Make sure you keep him nice and hard while we take care of this now." She said enjoying the hesitation followed by the the inevitable compliance the minute she reinforced the command with "Obedient submissive". Toms mouth enveloped the massive cock before him and Jessica slid the butt plug gently into his sissy ass before pulling his panties back up.

Jessica pulled Toms mouth away from Dylan's cock gently wiping the drool and smeared lipstick from his face. "Such a pretty sissy Candi" she said handing him a gold tube of lipstick. "Why don't you fix your lipstick while Dylan assumes the position." Candi stood and went to the mirror on the wall twisting the lipstick as he walked while Jessica led Dylan to the bed, his rock hard 10 inch member bobbing as he walked. She lay him on his back and gestured Candi to join them on the bed. Jessica straddled the young stud and placed the tip of his cock against her pussy lips, grinning in anticipation as Candi hopped up onto the bed.

As he walked Candi felt the butt plug pushing gently against his prostate, small pulses of pleasure coursing through his own small bulging cock, locked in its prison signifying. Dylan lay legs apart with Jessica straddling him facing his feet. Jessica gesture to the area between Dylans legs "As I fuck him I want you to lick my pussy as well as his balls and shaft, will you do that for me sweet Candi?"

"Of course Mistress, I'd love to."

With that Jessica impaled herself on the huge dick beneath her, savouring every inch as it slipped into her tight cunt. Candi lay on his back right beneath Jessica's pussy and began to lick and caress the hairless balls and shaft in front of him and then lapping at Jessica's hot wet snatch each time it came down to claim the last inch of penis. With one hand Jessica pulled out a small remote and pressed a button in the centre. Candi jolted as the butt plug inside him began to vibrate.

Jessica looked down at her new slave, feasting on the buffet of submissives below her and glanced back at the strained face of Dylan who like Candi was forbidden to cum without permission. His cock throbbed and pulsed inside her but he would get no release until she was completely satisfied.

Jessica rode Dylan like a champion jockey, faster and faster. She switched to face him presenting her tight ass to Candi. Jessica held her buttocks apart inviting Candy to rim her which he did with gusto. His tongue slipping into Jessica's puckered asshole with skill and ease.

Candi felt the inevitable climax building in his Mistress as her legs began to quiver and shake and her moans became louder and more visceral. When she hit the highest point of her orgasm she screamed "Dylan gets to cum." Immediately the prone barman thrusted and bucked as he sprayed ribbons of hot cum into her welcoming cunt. Her own pussy sprayed clear liquid onto the bed as she squirted in triumph over both her submissive boy toys.

As her ecstasy subsided she slid Dylan's from her warm hole and rolled onto her back on the sumptuous big bed still breathing heavily. "Candi my darling, I have a gift for you, come here my sweet boy."

Candi crawled to his Mistress and allowed her to guide his head to her red hot snatch she gently pushed his face into her dripping pussy starting to grind herself against his mouth. She squeezed gently and gobs of Dylan's hot seed seeped from her and into Candi's eager waiting mouth. As Candi lapped at his Mistress' sex she sighed with delight as the next orgasm began to build. She could feel the thrill of her total control of this new toy. Without ceremony and when she knew Candi had a big goblet of Dylan's cum in his mouth she said softly "manly man"

Candy stopped briefly, Tom's persona coming to the fore once again, tasting the rich salty cream of Dylans cum washing around in his mouth. He tried to process how he had come to this position, dressed in fabulous lingerie, made up like a slut sucking another mans seed from the pussy of an intolerably beautiful woman while a butt plug relentlessly pounded against his prostate.

Acceptance was inevitable, where else could he go, he swallowed the warm jizz and began to lap again at the lips of his Mistress' sex. She squeezed again releasing another ribbon of cum into his mouth which hungrily devoured as her second orgasm began crashing around her, her legs shaking as her pussy juice once again gushed onto her boy toy mixing her clear fluids and the remainder of Dylans seed, rubbing Candi's head as she ground out the final moments of her climax.

"Such a pretty sissy Candi."

An hour or so passed as the three of them nuzzled on the large bed gently caressing each other, no longer bothered about gender or social etiquette only warmth and love existed here. Jessica and Candi retreated to a dresser to freshen up while Dylan finally went to clean up in the bathroom.

As Candi teetered on his heels back to the bed she felt the buzzing in her ass begin once again clearly signaling Miss Jessica was ready for more play. Jessica lay on the bed face to face with Candi and kissed him passionately, her tongue invading his mouth and their creamy lips slipping together. This had all gone so well she felt she could push one more level in his training before retiring for the night. After the kiss she said "Are you horny sweet Candy?"

"Yes Miss Jessica so so horny, I could just burst but I can't." Jessica grinned as she saw the obvious wet spots of precum on his satin panties. She reached down and began to slowly massage his imprisoned dick while passing a condom to him.

"I want you to put this on Dylan my sweet. Make sure you fluff him properly before you put it on though."

Dylan lay on his back, his semi hard cock resting on his belly. Candi rolled over and gripped Dylans hardening member in his hand, beginning to lick the head once again. Dylan's head went back as he felt the warm touch of an eager tongue. Jessica positioned herself at the top of the pair supporting her head on one hand watching Candi minister to Dylan and the large cock once again grow to its full size as it slipped into Candi's mouth.

It didn't take long for Dylans seemingly inexhaustible supply of precum to start to flow again. Candi slipped the cock out of his mouth and exclaimed "Dylan is ready Miss Jessica."

"Excellent Candi why don't you slip that rubber onto him but only use your mouth." she said teasing the poor sissy. Candi unpackaged the condom and slipped it into his mouth before once again engulfing Dylan with his warm hungry mouth using his tongue to position the rubber over his head and then unfurl the latex down the full length of his shaft.

"Very good Candi, where on earth did you learn that little trick i wonder!" She chuckled. "Now get up on all fours my dear.". Jessica slowly pulled the buzzing butt plug from his ass with a discrete plop as Candi finally released it. "My what a hungry little ass you have Candi!"

Candi obediently sat in the middle of the bed on all fours facing the head board as Jessica lubed Dylan's cock and placed the tip at Candi's rosebud. Reaching one hand under Candi and started to massage his balls while the other she gently pushed on Dylan's pert ass.

The tip of Dylan's manhood started to slip unimpeded into Candy's ass, his asshole opening to accommodate Dylan's girth. Candy gasped as the widest part of the head slipped past his sphincter "good boys," she encouraged "gently now." she encouraged more pressure from Dylan's and slowly the rest of his dick slid into Candi's hungry ass.

She placed Dylan's hand on Candi's thighs and then went back to the top of the bed positioning her sex just in front of Candy's pretty slutty face. "Now my sweet you are going to lick me to orgasm while Dylan tenderly takes your ass." She said as she guided his burgundy lips to her box once again.

As Candi went down on his Mistress so Dylan took his cue and slowly began to thrust his dong into Candi's ass. Immediately Jessica could feel the excitement build, the enthusiasm from Dylan as he ploughed Candi tenderly, the humiliation was made an almost physical presence by Candi's submission to forced bisexual intercourse, tempered with his desperation to please his mistress that came from her careful hypnotic programming.

Jessica ground her pussy against Candi's eager tongue feeling the first hints of her impending release, timing was now going to be the key. Her trigger to allow Candi to cum also came with a secondary behaviour that he deeply desire to do anything to please her. She was banking on that, being a well seated trigger combined with her allowing his sexual release. She pulled back and told Dylan to pull his cock from Candi's ass. Then she flipped Candi onto his back and placed a cushion under him. From her cleavage she produced the key for Candi's chastity device and removed the lock and freeing his raging cock from its prison. Next she took Dylans shaft and guided him back to Candi's puckered ass.