Jessica and Tom 04: New Relations

Tom was in a bit of a conundrum, his agreement with Jessica was simple, he was to be 'en femme' and turned out like the perfect sissy at all times but he was also going to be working in the office, which tends to have somewhat more stringent dress codes. Was he supposed to be Tom, or Candi? He only really had one choice, he had to ask.

Jessica delighted in his confusion as he came down to the kitchen for breakfast. "Whats up sweetie?" She asked with a smile before biting her toast.

"I'm a little confused about what's expected of me in the office? Am I Tom or am I Candi?" He said sitting at the breakfast bar.

"I see your predicament, do you please your mistress or follow office dress codes?"

"Exactly, I want to please you but it's an office environment and I don't feel right taking a sexual fantasy to work."

"Well, I think I should be able to shed some light on things. Tom, Who owns this office you will be working in?

"You Miss Jessica."

"Correct, and do you think my office might be a little more liberal than most when it comes to dress codes?"

"I guess Miss Jessica."

"Tom, its really very simple, do you enjoy pleasing me?"

"Of course miss Jessica!"

"Good, then I suggest our rules still apply, I'm very much looking forward to meeting the new office whore!" Tom blushed realising he was once again having his boundaries pushed.

"Yes Miss Jessica"

It took a good half hour before he was happy with his look, He knew what Jessica was after but didn't want to stand out too much on his first day. For an outfit he'd chosen a knee length black leather pencil skirt, together with a simple white satin blouse. Underneath lurked a champagne coloured lace corset and nude stockings. His blonde wig had been coiffed into big curls to frame his face. A bold winged eyeliner and shimmering silver shadow smoothed out to a deeper brown adorned his eyes while his lips were a deep plum. Heavy contouring over his cheeks put the icing on his 'office Kardashian' look.

He clicked down the stairs in his 3 inch black patent heels, Jessica smiled at him. "Perfect, the guys and girls will just eat you up... literally. Come on, time to go." Tom grabbed his laptop bag, black leather handbag and tottered after Jessica, enjoying the perfection of her swaying ass perfectly encased in her long pencil skirt.

"Shake a leg, we're here sweetie." Nudged him from his driving day dream as the car pulled up to the large warehouse building. The driver opened the door and Jessica got out followed by Tom. The building while old had been heavily modified to provide modern office space while still keeping its industrial charm. Large glass doors slid open into the lobby, a large chunky wooden reception desk lay to the right with a pretty red head sat behind it.

"Good morning Miss Jessica." The red head chimed cheerfully as they entered. "I've sent all your appointments to your calendar but there's plenty of free time today."

'Thankyou Lilly, I'll have a look in a moment once we have... the lovely Tom here situated." Tom blushed at the use of his male name publicly outing him in her first breath. "Tom, you remember Lilly don't you?"

Tom looked at the reception girl more closely, her copper hair flowed in waves over her fair skin. Her lips were a shimmering nude shade and her bold green eyes were surrounded in smudged dark grungy grey shadow. He did recognise her but couldn't place her.

Jessica decided not to follow up on her throwaway comment, the hunger in Lily's eyes all but guaranteed they would be properly introduced very soon. "Time for the tour sweetie, there aren't many people in today but I guess we should start calling you Candi around the troops."

"Of course Miss Jessica." Tom followed her as she lead through the the sliding class doors into the expansive shop floor area of the main office. The large square room was segregated into 4 designated areas on the ground floor with a large mezzanine area hung from above. Large windows allowed the morning light to stream into the area through the cross crossed old panes of industrial glass.

"Down here we have the admin area in the these cubicles, it covers all the core business functions like HR, accounts etc, its all open plan and only one girl gets a big office and that's me!" Jessica grinned to Tom as she looked over her shoulder at him following him. "This next area is where the designers work," She pointed at the open area with a large table in the middle surrounded by large draughtsman boards and powerful looking workstations. A couple of ladies were busy aligning fabric on the table and comparing colour swatches, they didn't notice the pair as they passed, so deep in their conversation.

They continued their circuit past a small nook on the outside of the room which held a funky looking kitchenette and large comfy sofas, obviously a break room. "This is the furniture design studio." Another large open area this time dominated by the same powerful looking computers with large expensive looking displays. Again a similar table sat in the centre but smaller and this time holding scale models of prototypes being played with. "Finally we have the area you'll be working in. The guys and girls here are mainly photographers who hot desk so you'll be quite comfortable and there'll be a constant stream of new people in and out. I've made sure you get the nice corner unit with the latest toys. You can leave your laptop here if you want."

Tom placed his laptop bag at the large desk Jessica indicated, impressed by the multiple large expensive screens and what could only be described as cutting edge workstation that nestled below the desk. Jessica tapped her foot quietly on the concrete floor which Tom took as a hint to get moving. He quickly fell back in behind her as she climbed the stairs up to the mezzanine floor. She stopped half way up "I hope you aren't perving at my cute ass as we go up these stairs!" She chuckled.... Busted, Tom had been mesmerised by her tight ass as it came up to eye level, the slight hint of expensive lace lingerie just played beneath the fabric of her skirt and his mind had inevitably fixated.

Up in the glass enclosed mezzanine she showed him the studio area, large racks of lingerie adorned the walls while expensive looking furniture he recognised as similar to her home playroom stood idle, waiting to be moved into place and used. A large dressing area sat in the back with customary Hollywood style makeup mirrors, hair dressing equipment and large metal cases full of makeup. "We have lots of fun up here, especially after hours." she said playfully. "That's the lay of the land so far, I'll show you the warehouse areas later."

She led Tom back downstairs and into the reception area to the large sliding barn style door that formed the perimeter of her expansive private office cum play space. With a deep rumble the door slid aside and Tom realised his appearance was probably the tamest thing this room had seen in quite some time.

Every piece of furniture not only had a very specific purpose and, he suspected, probably had a very kinky story to it as well. Sumptuous leather, raw metal and divine velvet adorned spanking horses, fucking benches, restraint racks and several pieces he couldn't even figure what they were for covered each wall of the office. In the centre was a large chunky oak boardroom table. At the far end a large picture window let light flood into the space, a large mahogany desk sat in front of the window, the light haloing his mistress as she sat in her chair and invited him to sit in front of her.

"As you can see Tom, working here isn't all work," she smirked, "I'm looking forward to trying all fo these lovely pieces with you and perhaps a few guests. I'll have Lily show you to your workspace shortly but I wanted to show you my office to show that you publicly being my sissy is not really a big thing in my world. The real challenge might be when your own management come over for a chat." Tom's stomach twisted with the thought of his feminisation becoming common knowledge in his office. Jessica delighted in his discomfort.

"As I said before I expect you to follow our existing rules even here in the office, You will remain my submissive and serve me at my whim, you will always be dressed as my sissy unless given explicit instructions not to, not that you have a huge choice in the matter." She chuckled to herself as she felt her pussy begin to moisten with desire. "I Think we should get you broken in, loose your skirt and blouse and I'll let you choose the fucking bench we'll use to burst your office sex cherry."

Tom stood as instructed and unbuttoned his satin blouse hanging it neatly on the back of the guest chair before wiggling out of his tight leather skirt revealing his corset, stockings and caged cock that she hadn't released since his meeting with Stephanie and Nicole several days before. Even though he couldn't get hard without her trigger she enjoyed the discomfort the tube in his urethra lent to the experience after all the fun with Michelle and Lucy.

Knowing Jessica much preferred him to keep his sexy heels on when they played Tom clipped across the worn wooden floor to a fucking bench skinned in a soft caramel brown leather. Its padding was soft and luxurious, in contrast to the heavy buck skin straps which hung from it ominously. The buckles tinkled as he mounted the bench, face down, his ass now perfectly framed by the tight garters from his corset as they strained against his stocking tops.

He heard Jessica's heals follow him but he resisted the temptation to glance over his shoulder. Her warm hand caressed his butt as she slipped between his legs teasing him with her closeness. She began to tie him to the bench. The thick soft leather straps quickly slipped over his legs, over his back and around his wrists and arms. The sensation of immobility and helplessness washed over him as he slipped into sub space.

"Good choice, this bench is a new model you'll be helping market for us, it's got a few added features which make it fun for a couple or more." He heard the telltale whisper of her skirt being slipped down, a hiss as her blouse fell to the floor, then clinking buckles.

He felt the cool sensation of lube being dribbled over his exposed hole then the gentle pressure of her phallus at his rosebud. The pressure increasing until his ass opened and let her in, the rubber cock she wore slipping easily but slowly into his wanton sissy hole. Jessica began to slowly thrust allowing him to feel every ridge of the long cock she wore as it slipped in and out of him. He couldn't help himself moan as it tickled and caressed his swollen prostate.

It didn't take long before he was moaning in time with her thrusts, he felt her cup his caged cock and pop off the rubber stopper. "oh my Candi, you seem to be dripping with anticipation." She reached forward as she thrust deeply inside him allowing her precum covered fingers to slip into his mouth. Even without any trigger she knew he had surrendered to her. He eagerly licked the precum from her fingers before she slipped them away and held his hips and her rhythm quickened. Each thrust pounding his prostate and milking more of his pre cum from his balls.

He didn't so much hear the door as feel it as it rumbled open along its well oiled runners. "Oh my, I hadn't realised you were.... Busy" said Lily as she walked in to the office filled with moans from both parties over the fucking bench.

"You're just in time, you remember the friend I told you about Lily?" Said Jessica as she slid her cock in deep and slowly to Tom's ass. Tom could hear the conversation but due to the restraints he couldn't see the participants. "Why don't you show him where he knows you from before he rewards your past efforts.

Lily walked into Tom's view and seductively slipped off her skirt and blouse leaving just her nude sheer stockings. She slid her lipstick from the welt of her hold up and twisted the tip out before leaning in close to his face and generously applying a fresh coat. The planets aligned and Tom's mind whirled as he recalled the picture of the powerful redhead wearing a strapon between two stocking clad legs, the one Jessica had sent him, it was her. He moaned deeply with arousal as his mind imagined the pair fucking.

"I think he remembers." Said Jessica as she continued to plough his ass. Lily circled the fucking couple gently caressing the bare flesh of both bodies as she went. She kissed Jessica deeply as she dug her nails into her pert buttocks. Her other hand eagerly reached for Tom's dripping cock and scooped a warm finger full of salty dew before she withdrew from the kiss and licked it seductively right in front of Tom's face.

Moving to the front of the fucking bench she pulled a large handle allowing a curved seat to pull out and pivot up in front of Tom providing the perfect platform for her. Lily slid her pale ass onto the smooth brown leather opening her legs to reveal her naked cunt perfectly placed for Tom to worship. She groaned in pleasure as she felt his tongue slip uncommanded into her. He began to lap at her womanhood as she lay back into the soft leather padding and placed her feet onto the discreet pegs.

After several minutes of grinding her wet snatch into Tom's face, slowly smearing his makeup he felt Lily lean forward, his lust ridden brain imagined the two women locked in a deep kiss above him as they fucked and ground themselves to orgasm.

The tempo quickened as both women approached their climax, both using him to get themselves off while kissing passionately. Telltale quivers and spasms gave away the impending explosion and as the two slipped and slid the pair reached their climax he heard their jubilant screams.

As their orgasms abated Tom felt Jessica slip her cock from his gaping ass, he moaned as it finally slipped free of him but he felt empty and longing to be filled once again. Lily lingered on his face, milking the last drops of pleasure from his servitude before sliding down from the crescent seat and folding it away. Both women gathered their clothes and dressed leaving Tom bound to the bench, his precum still drizzling from him after his pounding.

"I suppose we should put him to his actual work for the day, but he looks just so delicious strapped to that bench I'm in two minds." he heard Jessica say as she re-entered the room from her private bathroom. "I'm sort of tempted to leave him there for my next meeting and let the suppliers try him out."

"I think that might be a bit mean on his first day, and he did do such a good job of getting us both off." Lily replied.

"I suppose, I just love the way his pert little ass is so well framed by his garters and those beautiful leather straps." Jessica circled Tom's prone figure stooping till she was nose to nose with him. "You look so divine with your ruined makeup, face covered in Lily's pussy juice. You really are a dirty little sissy aren't you Tom?"

"Yes Miss Jessica, I'm a very dirty sissy." With that Jessica kissed him, knowing it was time for some aftercare for the poor boy. Tom returned her loving kiss happy he'd pleased his mistress once again.

Jessica unbuckled the straps, let him up from the bench and handed him his neatly folded skirt and blouse "Lily will show you where to get cleaned up."

Lily helped him from the bench and lead him to the discrete private bathroom just off from the massive office. Showing him into the luxuriously appointed bathroom she stood closely behind him, her naked body held against his, her arms wrapped around his front. "If you need anything just push the call button and I'll make sure you are looked after. Meet me back at reception and we can get you set up with all you passwords and ID. Make sure you look pretty for your photo!" Lily smiled sweetly as her hand lingered on his buttocks before she left him to his ministrations

Creating a Domina

Jessica had thoroughly enjoyed her morning so far, a satisfying orgasm while pegging your sissy slave was definitely the way to start your day she thought. She opened her computer and scanned the inevitable myriad of messages she would need to deal with. She had people to deal with most of the issues but she liked to keep abreast of the situations as they went. One stood out in bold, high priority, not unusual except for the source. Stephanie.

Dear Jessica

It was a pleasure meeting you at our offices on Friday, I trust we answered all of your queries and satisfied your requests regarding the secondment of Tom into your office. I wonder if it would be possible to schedule a phone call at your earliest convenience to discuss some 'related' matters and perhaps an office visit to see how Tom is settling in. My mobile is the best point of contact as I am working from home this week, please feel free to call any time or we can schedule a time in the diary.

Best regards

Stephanie

HR General manager

'Wants to discuss related matters?' Jessica thought, 'I'll bet she does'. Jessica checked her diary quickly and saw she had a spare half hour before her first meeting and dialed the mobile number at the bottom of the message.

The phone rang twice before Stephanie answered "Hello Stephanie speaking."

"Hi Stephanie, its Jessica, I just got your email, is now a good time?"

"Oh wonderful I've been hopping you'd call soon, I wanted to discuss our meeting last week."

"Ok sure, what is it you wanted to discuss exactly?"

"Erm well it was more a personal thing if that's OK?'

Jessica smiled, the trigger she had left had indeed worked. "Of course, how can I help you Stephanie?"

"Well, I'm sort of a bit conflicted, I've been, well, something changed since we met and I cant explain why, just that it had something to do with you. I can't really put my finger on it. Its kind of why I'm working from home, I just felt sort of different around my co-workers after you left."

"Oh, really?" Jessica teased "in what way?"

"Well, I kind of wanted to be the boss, tell people what to do, especially the guys and when I did it got me feeling all.... Giddy."

"Ah, I see, you mean you felt the urge to dominate people?"

"Well, yes I guess so. And it made me kind of, well, hot. I think it was something to do with your self confidence when we met and how you were oozing sex appeal at the same time but I don't know why." Jess could hear the confusion creeping into her voice, she was opening up to a complete stranger about her urges, that in itself was obviously unusual for Stephanie, poor repressed Stephanie. Not for much longer though.

"I see, and when you say, hot you mean, aroused, sexually?"

"Yes" she blurted out

"Stephanie, this is wonderful, I had a feeling you were quietly a dominant woman just like me. Tell me have you been having fantasies?"

"Yes, all weekend, every time I close my eyes I'm thinking of new things I'd like to do. I've spent hours watching porn over the weekend. Its not like me at all."

'Would you like to tell me about them?" Jessica asked rolling her dice and hoping Stephanie would bite, she did.

"There are so many but I keep coming back to well, threesomes where I boss men around in the bedroom and have them service me and.... Do things to each other."

"Things Stephanie? What things?" Jessica felt her finger slip into her still tender slit as she gently coaxed the reserved HR manager out of her conservative shell.

"Well, you know, I sort of, well.... I liked to think of making men suck each other off and fuck each other while I watch or maybe have one fuck the other while I fuck him."

'My my Stephanie, you mean you like to force men into performing bisexual acts for you. Do you like the idea of cuckolding your lover too? I bet you do."

"Oh god yes, I've only just discovered the idea but it gets me so hot, I'm so horny just talking about it."