Jessica and Tom 04: New Relations

"Oh my!" Michelle exclaimed, red faced and breathless as her climax subsided, she twitched with each movement as the cock still buried in her mount teased her tender clit. "That was awesome, how was it for you slave?" Jacob was red faced with frustration and exertion, he was desperate to cum but simply couldn't, his balls were full to bursting and his relief just a hair away but unattainable!

"Please let me cum, Mistress, I'm desperate to cum."he whined

"How desperate are you slave?" She teased.

"Mistress I'll do anything, please let me cum!" Michelle slipped up his cock then drove down again to reinforce his predicament, delighting in the post orgasm shivers she felt in the process. "Anything he moaned."

"I'm absolutely thrilled you said that slave, I'm going to so enjoy the next bit, you did win after all, your monster dick was spectacular." Michelle slipped off his drenched cock, kissing Lucy deeply as she slipped from Tom's.

"Tom, would you mind being an obedient submissive and giving Jacob his prize." Said Jessica, "we'll discuss your disappointing performance later!"

Tom knew what was desired and he was soon knelt in position between Jacobs legs. His dark red lips pursed over the monster cock of his fellow slave. His lips parted and he slipped the member into his slutty lips smearing his creamy lipstick down the shaft, wrapping and twisting his tongue over the sensitive glans as he went. He expertly sucked Jacob to a quivering twitching edge, salty precum dripping continually from the tip and being swallowed.

"Whenever you are ready ladies, it looks like the poor mite, will explode." Said Jessica as she enjoyed watching her sissy sucking off the slave before him. She passed a piece of paper with the cum trigger written on it to the girls who were sat on the bed next to the two boys. They had succumbed to desire and were fingering each other as they watched.

Lucy took the paper and showed it to Michelle both giggling between gasps of delight at each other's touch "Jacob gets to cum" Lucy blurted. Instantly Jacob grunted and bucked as he was triggered to cum. Tom felt the jet of hot cum burst from his throbbing cock but continued to suck and lick. The sheer amount of jizz was impressive and it was soon dripping down Tom's chin in sticky ribbons as he fought to keep it all in his mouth. Jacob calmed as the last of his sticky cum throbbed into Tom's mouth and Tom withdrew leavening the lipstick streaked cock to soften.

"Don't waste any of that cum sissy, lick it up but don't swallow." Said Michelle. Tom obediently licked up the dribbles of cum on Jacobs cock and scooped up the drips on his chin and held them in his mouth. "Now give the lovely sissy a thank you kiss Jacob!"

Jacob was reticent, he wasn't gay, he didn't like the taste of cum "Mistress I don't like that."

Michelle kissed her slave tenderly, "I know slave," she said softly "but I do! and you said you'd do anything to be allowed to cum and we're just getting started, so kiss the pretty sissy or you wont be allowed to cum for a full month!" Jacob realised his predicament and got up to his knees facing Tom and kissed him softly. "Properly!" Lucy chided.

Jacob kissed Tom deeply, slipping his tongue into he sissy's soft mouth. Tasting his own jizz within. "Now Tom, give him that lovely load of cum to wet his appetite." Said Lucy now thoroughly enjoying Jacobs discomfort as Tom snowballed the salty goo into Jacobs mouth. "Swallow it Slave!" Jacob swallowed.

"Excellent." Michelle said, "now on to the 'anything' part. Tom has been such a good little sissy for us its time to reward him. Tom lie back sweetie." Tom lay back on the bed, Jessica sat at his side who gently caressed his thighs with her sharp nails. "Now slave, I want you to suck this wonderful sissy off just like he did you!"

"But I'm not gay Mistress, I don't like that!" He whimpered.

"Get your mouth around that sissy clit or you wont be cumming for six months, do you understand! You said ANYTHING and I want you to suck the cum out of this sissy so get on with it!" Michelle chided.

"Yes Mistress." He replied quietly as he took up a kneeling position between Tom's spread legs. Leaning down he gingerly took the tip of Tom's cock in his lips before Lucy's hand on the back of his head forced him down the shaft.

"There, that wasn't so hard was it slave" Lucy said, chuckling as Jacob gagged. "Now use your tongue to tease that cock and get his precum dripping into your dirty face hole!" Jacob began to slip up and down Tom's cock. Tom could feel the tongue exploring his shaft and his own arousal built. "There what a good little cocksucker you are slave! Now keep going we want this little sissy quivering and bursting to cum"

"Can you taste the salty precum dripping into your mouth yet you dirty whore" Michelle whispered in Jacobs ear as he found a comfortable rhythm. He couldn't speak but nodded in reply. "Excellent, won't be long now I don't think, look at how that dirty sissy is trembling and grinding as you suck him off, he really likes your virgin mouth doesn't he. When he cums if you miss a drop of his man fat I'll put you in a cage for as many weeks as drips you miss. Your only relief will be Mistress Lucy milking your cum out of you with a prostate massager, do you understand slave?"

Again Jacob nodded "I never thought forced bi would be so hot." Lucy gasped as she fingered herself closer to yet another crashing orgasm.

"It really is isn't it, watching a freshly minted queer suck another mans cock just to please mistress' is just such a wonderful moment. I'm looking forward to having this cock sucker earn his keep and blowing off any cock we put in front of him." Jacobs eyes widened at the thought. "Yes slave this wont be the last dick you suck, its going to be so much fun watching you suck and fuck other men. But to the task at hand, Jessica would you like the honours?"

"Oh would I!" She said softly. She whispered into Toms ear making him quiver and goose bump "Would you like relief Tom?"

"Yes Miss Jessica" he moaned

"I bet you would, you're bursting at the seems aren't you after all that punishment, having this hunk of man sucking you off so eagerly to preserve his own orgasm privileges is probably making your head spin isn't it?"

"Mmmmm hmmmm!" Was all he could manage between gasps and spasms. Jessica beamed with pleasure at her sissy's torment.

"Slave, you aren't to swallow when Tom cums, I want to see you hold that jizz in your mouth and enjoy your gift"said Lucy sternly reading that the moment of release was imminent.

"Candi gets to cum" Jessica whispered in Tom's ear and instantly he arched his back and bucked, forcing his cock deep into Jacob's warm mouth. Tom moaned with pleasure as he released his load, his hot cum firing in streams of salty cream to the back of the slaves mouth. Tom shivered and shook as his cock throbbed and spewed the last of his goo into Jacobs mouth.

Jacob gagged at first but controlled himself and managed to collect most of the cum. As with his own orgasm, the load was large and he had trickles of white cream down his chin which he quickly caught with his finger and slipped back into his mouth as he slipped from Tom's twitching dick. "Show me" instructed Lucy and Jacob obeyed opening his mouth to show Tom's load swilling over his tongue. "Good boy now swallow it." With a pained look Jacob swallowed Tom's load which was just enough to send Michelle over the edge for one final time knowing she had bent her slave to her will.

Summoned to the office

Tom's stomach churned as he read the text on his phone 'Can you call the office ASAP, I know you are on leave but we really need you to attend a meeting today! Call soon, Dave." His phone had been going nuts for a while but he'd not heard it while he was in the shower and putting on his face for the day.

How was that going to work he wondered. It must be critical if Dave, his immediate boss, was sending such an urgent text. Thumbing to the contact page he dialed Dave's mobile with trepidation, hoping he wasn't in too much trouble.

"Tom thanks so much for calling, we're really in a tight spot" Dave said as soon as he answered the phone. "Are you still up North visiting your friends?"

"Yes I am, what's the issue?"

"All we've been told is that they need YOU in a meeting at 2 p.m. today come hell or high water, I've not been told why. Its all HR and core business functions in the regional HQ, they don't have any tech guys there so maybe it's something to do with the new software build you uploaded?"

"Er, let me check with my friend and make sure we don't have any unchangeable plans, I'll call you back in 10 minutes."

"It seems really urgent Tom, HQ are really screaming for some reason"

"No problem, I'll speak to you shortly" Tom hung up and slipped his satin neglige on before going downstairs to speak to Jessica.

Jessica was sat at the bar in the kitchen, legs crossed in a tight black above the knee skirt and equally tight long sleeved scoop neck top. A simple but alluring look that accentuated every curve of her heavenly body.

A warm smile crossed her creamy nude coloured lips as she saw Tom in the hallway. "Morning sleepyhead, everything OK?" She said as he approached her and knelt before her. She loved that he had started doing this on his own, almost as much as she loved no longer having to compel him anymore to make himself up and dress like the compliant sissy she so desired.

"Miss Jessica, I've just had a message from work, they need me to go the office here in town for some urgent meeting but I'm not sure if that's OK with you, they seem very stressed." He replied gingerly, "I don't want to break the rules but this seems really important."

"Oh dear, and I guess turning up dressed like a ten dollar whore would potentially cause some issues?"

"Yes Miss Jessica, it might be problematic at this stage."

Jessica took her pen that she had been using to write notes in her leather journal and patted it against her supple lips "hmmm, when is this important meeting sweetie?"

"2 o'clock Miss"

"Oh plenty of time then, but there will be rules if you are to be out in public dressed in your awful boy clothes, is that acceptable?"

"Yes Miss Jessica, of course I'll follow any rules you ask of me."

"Ok lets start with something to help me think." Jessica slipped the stretchy hem of her skirt and spread her silky legs apart to reveal her smooth shaven and rapidly moistening pussy. "You won't be needing that perfect face for your meeting so you may as well ruin it on something worthwhile." she said as she guided his head into her snatch.

Tom was enthusiastic as always and he eagerly thrust his tongue into her waiting slit savouring her musky scent and relishing her gleeful moan as he entered her. He felt her juices slip and slide over his chin and cheeks and start to smear his foundation and lipstick as he teased and lapped at her engorged clit.

She wrapped her legs around his neck and back to hold him in place and began to grind herself vigorously against his talented tongue, he felt the sharp edge of her stiletto heels begins to dig into his back as she rode his face. Her hand slipped to her clit and she held herself open for him guiding him to her sweet spot as her orgasm built, determined to ruin his perfect makeup.

Tom felt the familiar quiver through her thighs as he sensed her climax, her grinding became more forceful and her other hand held his head firmly in place. Her back arched and she moaned loudly. "Lick my quivering snatch you dirty little pussy licker." she said huskily between deep breaths.

Tom felt her juices dripping from his chin as her orgasm intensified and she began to buck and twitch, her moans getting louder as he lapped at her sweet clit. Her pussy squirted her sweet cum over him as she crested into her climax, her legs clenching his face into her gushing hole as she ground hard against his tongue.

Her gasping subsided and she looked down at her precious sissy's face, his makeup ruined by her hot cum, his mascara and eyeshadow running down his face just like the wanton whore she wanted him to be. "Mmm... what a way to start the day." She exclaimed as she clenched one final time and shivered with afterglow as he continued to gently lap at her clit until she released him from her tight grip.

"Now sweetie, why don't you go and get cleaned up and text your boss back while I find an appropriate outfit for you for your meeting." Tom licked his lips enjoying the taste of her sweet cum as he stood and made his way back upstairs where he got back into the shower and cleaned himself up before texting Dave back that he would be there as requested.

He came out to find Jessica laying the final items of clothing on the bed for him. His charcoal grey suit hung on the handle of the closet along with a pristine white shirt and a pink silk tie. On the bed was a white satin camisole with lace trim and a pair of ruffled white boy short panties. A pair of Woolford lace top nude stockings lay in an unopened packet next to a white satin 8 strap garter belt, next to all of this was a small mystery box about the size of a shoe box.

Without question Tom slipped into the cami top then opened the stockings and rolled them up his legs one at a time, relishing the sensation of the expensive nylons on his smooth shaven skin. He fasted the garter belt around his waist and Jessica helped clip the garters to the stocking tops ensuring the fully fashioned seems were perfectly straight. As he picked up the heavily ruffled panties she stopped him and sat on the bed inviting him to bed over her knees in the classic spanking position.

"We have a couple of accessories we need to add first my sweet." She said with a grin. Unable to resist she slapped his ass as the garter straps stretched and perfectly framed it. She reached for the box and from it produced a rubber glove, which she gleefully snapped into place, and a small bottle of lube. She lubed her long, elegant, gloved finger and used the excess around his exposed rosebud before slipping her finger into him, enjoying his gasp as she entered him then his moan as she teased his prostate. Once she had had her fun she slipped her finger from him and lubed the toy that lay in the box. The one she had bought him. The slim prostate massager easily slipped into him as she applied pressure and she could tell by his moan that it had hit home.

"You remember this one my sweet? It's the one that works via the internet. I'm going to enjoy playing with you in this meeting of yours." For effect she tapped her phone and Tom gasped as the massager hummed inside him and buzzed against his prostate.

After a final slap of his perfect ass she had him stand in front of her, his flacid cock was at her eye level where she sat on the bed. She reached into the box for the final item, a metal chastity cage. She took his cock in her hand and gently kissed his soft member leaving a soft smear of her creamy lipgloss on the tip.

"This cage has a hollow sound at the tip, I saw how much you squirmed as Miss Lucy played with you with her devious toys so thought this would be fun." Using a fresh glove she lubed the metal tube protruding inside from the tip of the cage then put a blob of lube over the tip of his cock. Slipping his dick into the cage she delicately guided the metal protrusion to the tip of his cock and slipped it down into him. Tom moaned at the sensation of the intruded entering him but he couldn't object. Once the probe was fully down his urethra she fastened the locking ring behind his balls and fastened the small discrete lock.

"There, now my property cant be 'tampered with'" she giggled. "If you need to pee then you need to open the rubber cap at the end, don't forget to put it back though."

"Yes Miss Jessica"

"Now put your panties on and your suit and tie on and I'll see you downstairs, I'll have my driver take you to the office" and with that she slipped from his room knowing he was checking out her perfect tight ass as she went.

It took Tom another 20 minutes to finish getting ready and come downstairs, obviously in a little discomfort from her final accessories. She kissed him tenderly as she reached around and grabbed his pert ass, enjoying the feel of power as she felt the lingerie beneath his suit trousers. She could see the tell tale lines of the garters as he walked but they weren't obvious to anyone who didn't know they were there. She felt a twinge of arousal as she thought of the fun she was going to have toying with him.

"The car is outside Tom, I put the drivers number in your phone so you can give him a call when you are done and he'll bring you straight home so you can tell me all about it."

"Thank you Miss Jessica for understanding about this. I don't want this to get in the way but it looks like I cant afford to miss it."

"Don't worry Tom, we'll have plenty more time for fun and games, your job is important too!" She kissed him a final time and allowed her hand to linger on his firm ass as she guided him out of the door.

Tom sat in the limo and drifted off into a daydream and was at the office before he knew it, a male voice front he front said "shake a leg sir, we're here." and he was back in the real world again. "Call me when you need a pick up sir."

"Ok will do, thanks" Tom said as he got out of the car.

As he approached the office reception he showed his ID to the lady on the desk and she told him they were expecting him. Miss Winters from HR was to be his first port of call which didn't bode well. As he stepped into the elevator his legs weakened, the toy deep in his ass vibrated softly just as his phone announced a new message. 'Good luck in your meeting sweetie, fingers crossed J xx.' It seemed Jessica intended to keep having her fun.

Miss Winters was on the third floor of the modern office building and having arrived at the HR reception he was guided by a cute young girl to her office and told to sit until he was summoned.

It took about 20 minutes before the door opened and an attractive 50 year old woman, tall and elegant with a warm smile greeted him "Tom?" She queried,

"Yes Miss Winters" Tom shook the hand she offered and enjoyed the supple softness of her skin.

"No need to be so formal with me, call me Stephanie" She smiled and ushered him into her office. She was a tall slim lady around fifty years old but showed her age well. Dressed in a tight fitting black business suit and white blouse, she was obviously keen on taking care of herself. He dark brown hair was tied up in a tight bun and her face was subtly made up but just enough to emphasise her high cheek bones and plump red lips.

"Can I ask what this is about?" Tom asked bluntly as he sat in the leather office chair in front of the big wooden desk.

"Of course Tom, nothing to worry about, I know people usually assume an HR meeting is a precursor to something bad. This is about a big opportunity for you."

"OK, great, I think, can you elaborate?" A knock on the door moments before it opened heralded the arrival of another attractive older lady, Nicole Edwards, Head of corporate accounts. A lady Tom had met once or twice when new accounts had come to his team. She was about 6 inches shorter and 5 years junior to Stephanie and favoured a more extravagant look. Her skirt was short and tight and her satin blouse showed just a hint of the lace lingerie she was sporting beneath. She wore heavier makeup catching Toms eye with her plum lipstick and pinup style eyeliner perfectly framed by her shock of blond curls.

"Ah Fantastic you're here Tom, I'm so pleased you could come in." She said taking a seat next to him "You seem to be a popular guy at the moment." Tom stood and shook her hand before taking his seat again.