Jessica and Tom 04: New Relations

"Stephanie, I have some time later today when I Think it might be good to meet up and see if we cant help you out. I don't think this is the sort of thing we're going to help with over the phone. Would say 5pm work for you at my office?"

"Oh that would be wonderful, I just don't know where to turn with all these new feelings all of a sudden."

"No problem I'll send you the address in case you don't have it to hand. In the meantime why don't you indulge yourself at home, have a wonderful orgasm just thinking about the things you'd do to lovely beta men."

"Mmmm hmm, oh!" Jessica knew Stephanie was already on the case.

"See you at five."

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Jessica heard the Car pull up outside of her frosted office windows just a little before 5. Checking the CCTV display on her second screen she saw the elegant shape of Stephanie Winters exiting the cab with the practiced grace of a true lady. Jessica noted immediately the much shorter skirt she was wearing, her hair pulled into a tight pony tail. The CCTV was good but that was the best she could glean from the grainy image.

Her intercom buzzed shortly after "Miss Jessica, A Stephanie Winters is here to see you, she has an appointment apparently?" Lily said quizically.

"Yes she does Lily, sorry I forgot to add it to the diary. Just give me a few moments I'll be right out." Jessica tingled with anticipation, as she always did when a possible new conquest was on the cards. She reapplied the matte red Armani lipstick that Tom had bought her, the shock of red giving her an additional fizz of confidence. Once she was happy with her appearance she made her way to the door and slid the heavy door aside.

"Good evening Miss Winters, I'm so pleased you could make it, won't you join me?" She gestured to the open door and drank in the subtle but significant changes in the HR manager. Stephanie had definitely changed her look.

Her lips were a deep burgundy and her eyes went from a glittering carmine to a shimmering silver and then to a defined black eyeline. Her high cheeks were highlighted by a dusting of rich bronze. Her white blouse was tighter than their last meeting and her black lingerie clearly showed beneath. Her short clinging black skirt highlighted her pert buttocks and hinted at her garters beneath. Her long toned legs were clad in fine black seemed stockings all the way down to her simple but expensive louboutin heels.

"It seems you've made some changes Stephanie" Said Jessica as she slid the door closed behind them. "I have to say I like it, please sit" She gestured to a couch a the side of the room which gave a good vantage of all the bondage equipment and furniture which littered her expansive office.

Stephanie took a seat and sank into the soft leather as she took in the view presented to her. A confused look crossed her face. "What exactly do you sell here?" She gestured out at the room.

"Ah yes, we may have been a bit generic when we said custom clothing and furniture during our meeting. We are definitely doing that but as you can see our goods are very much marketed for a specific purpose. Do you think this will be a problem?"

"I don't think so, as long as your cheques clear. I am very interested in finding out more though." Jessica knew she had her full attention when she saw Stephanie lick her lips in anticipation.

"Well, we cater for people who like to indulge in BDSM, as you can no doubt gather. Our equipment is generally custom made to order from a base plan." Jessica indicated the plush caramel leather fucking bench she had enjoyed using with Tom earlier in the day. "This for example is our premium fucking or spanking bench. The wood is all French oak and is worked till it is silky smooth. Our upholsterers will then use the finest hides to skin it to your desired finish and colour. You can decide how many straps, where you want holes and anchor points to be placed. It really is exquisite, I enjoyed using it only this morning."

Stephanie had stood and approached the bench, she began running her hand over the plush leather, relishing the firm but smooth texture. "So one person would be strapped to this and the other would do what?"

"Yes so the 'submissive' or 'bottom' would lie face down, placing their knees here and here. The Dominant can decide to restrain them or not with these straps and cuffs. Depending on what you are into you might give them a light flogging with one of these," She handed Stephanie an expensive leather flogger with an engraved steel handle and hilt "or perhaps they might choose to slide their legs apart like this," She unlatched the leg pads and slid them apart "and then maybe give them a good hard fucking." The possibilities are only really limited by your imagination.

Stephanie idly played with the soft fronds of the flogger as she slapped them in her hand. "So this is mainly for men to dominate women?"

Jessica laughed "Oh heavens no, we women might not have a penis but we can improvise." Jessica held up a leather harness with an 8 inch dildo hanging from it.

"Oh my, I'd no idea." Stephanie blushed but Jessica could see the cogs of her mind turning.

"Oh I think you did Stephanie, I think quietly you've always had fantasies about dominating other people, am I right?"

"Well I've certainly been thinking about it a lot recently. I had an urge to change things up a bit and well, I have to say, I do seem to be getting more attention in an outfit like this." Stephanie bit her lip showing she wasn't entirely comfortable in, or convinced by her new look"

"Stephanie, the attention you are getting is because you are really rocking this new look. You really are stunning. Are you finding men more compliant, do they do what you want more readily when dressed the way you are?"

"Well yes now that you mention it, the concierge at my apartment building was very attentive the last few times I have seen him, but isn't it just because I'm giving them more eye candy to drool at?"

"That's a possibility but more often than not men want to be told what to do and see the pleasant view as a reward for their efforts, like somehow you are dressing in a particular way just to please them. In actual fact you are dressing that way because you know it gives you power."

"I hadn't thought about it like that, so all it takes to get my way is a short skirt and some lippy?"

"Well yes, that and your demeanor, like I said, most men like the idea of being bossed around by an attractive, well dressed lady, it appeals to their mommy's boy nature. The question is what do you want to do with your new found 'power'."

"What do you mean? Sexually?"

"That's a big part of it yes. Ultimately though it's more about getting in touch with your inner dominant and doing what makes you happy. If you happen to have a raging orgasm without the demeaning parts of vanilla sex then who are we to cry foul. Far better let the men demean themselves as they service us."

"So these feelings are normal, these fantasies are ok to pursue?"

"Why wouldn't they be? Its your body, your mind, you are entitled to pursue whatever fantasies you so wish. If you want to make them a reality then I'd be happy to help you do so. Perhaps you can tell me what floats your boat?"

"Well, I haven't given it too much thought beyond some of the porn I watched over the weekend but you get spammed with all sorts of stuff when you search for female domination." Stephanie had begun to wander amongst the exotic furniture, brushing her hand over the various leather pads and tugging on various straps as she inspected each piece.

Jessica chuckled "yes you do, but there must have been some things you saw or read about that excited you?"

"Well I did quite like the idea of using that harness and cock on a guy." She said almost in a whisper, "Is that weird?"

"Oh no, I really love pegging, that's what these benches excel at after all. Anything else get you hot an bothered?"

"Erm, well I also saw some situations where the woman dressed the guy up like a girl, that seemed quite integral to the pegging thing. I also really loved the idea of maybe making the girly one suck off another guy while I watch."

"My word we're really like birds of a feather Stephanie. Do you like getting your pussy licked until you squirt?" Suggested Jessica deviously, knowing she'd done just that in the office with Tom lapping at her clit.

Stephanie gasped and giggled at the directness of the question. "Oh my, its been a while since I had that kind of action but yes I do like the idea of that. I had the most vivid dream about just that only a few days ago. Wow it feels so good to get this all off my chest, its been bouncing about my head all weekend, making me wonder if I'd become a deviant overnight!"

"Every woman loves to have her pussy worshipped Stephanie, there's nothing devious about that. The problem is men expect the favour to be returned over and over and that's just not how my world works."

Jessica had approached Stephanie on her wander amongst the bondage furniture and as her attention was caught by a queening throne she gently whispered in her ear "Sleepy Domina." She caught the older woman as her legs gave way to the trigger and Jessica gently allowed her to fall into the throne she had been inspecting. "Can you hear me Stephanie?"

"Mmm, yes Miss Jessica." She replied with a slight smirk on her face

"What a good Domina you are Stephanie. I'm so pleased you decided to call me and come over to visit. What I'd really like from here on is that you feel empowered to pursue your fantasies and start to experiment with your dominance, does that sound like fun?"

The smirk had grown to a smile and Jessica could imagine her mind putting together all the possibilities that lay before her. "Yes Miss Jessica."

"Excellent, you are in a safe space here with me. Shortly I'm going to bring in a willing submissive for you to play with. I want you to feel empowered to play and enjoy your dominance. If you want to include me in that play then I'll be here and willing, otherwise I will simply observe and ensure both of you are always safe and cared for. Does that sound like fun?"

"Ohh very much Miss Jessica, thank you for letting me play here" she mumbled from her plush throne, Jessica could see the flush of arousal beginning with the possibility of breaking her vanilla shackles.

"What a good Domina you are Stephanie, in a moment I will snap my fingers and you will awaken feeling refreshed and energised but also becoming very aroused as each of your erotic ideas crystalises in your mind. You wont recall this trance, only that you are safe and empowered to pursue your new burning fantasies."

....SNAP, went her fingers and Stephanie's eyes fluttered open right on cue.

"This throne really is very nice, the leather is just so soft and the access it allows means a submissive can service you while you are in absolute comfort." Jessica continued without missing a beat, easing the transition from when Stephanie recalled being stood to where she was now, luxuriating on the black leather throne. "It might be better to show you, let me invite one of my pets in." Jessica rounded her desk quickly and picked up her phone to seize the moment before Stephanie could back out. "Pretty sissy Candi could you please come into my office." She said quietly into the receiver then replaced the handset and smiled "Candi loves to be part of the demonstration process."

A few minutes later there was a discrete knock on the door and Tom was shown in, now firmly in his bimbo persona. "I got here as quickly as I could Miss Jessica, I just needed to touch up my face."

"Thank you for taking the time to look your best Candi. This is Miss Stephanie, she is interested in seeing how we use some of the equipment, would you be willing to help?" She knew it was a loaded question, Candi was a slut and loved to be used, that's how she had been programmed after all.

"Oh I don't want to embarrass anyone." Stephanie said quietly

"Oh no problem, Candi here, is very eager to please. Candi would you please remove your blouse and skirt." Jessica motioned to a spot in front of the couch and guided Stephanie back to the couch to sit and watch the show.

Candi began to unbutton his satin blouse and reveal the champagne corset beneath. Then he wiggled out of the leather pencil skirt revealing his nude stockings and garters and satin panties with their telltale bulge. Once he was down to his lingerie he kneeled obediently in front of the two women gazing a the floor.

"May I ask what the bulge in her panties is?" Said Stephanie almost in a whisper.

"Of course, that's her little sissy cock, Candi here is a sissy, a boy that likes to dress up like a pretty little whore and serve the stronger sex." Jessica could tell Stephanie had yet to put two and two together and figured out who Candi really was. Candi, please stand up and remove your panties so we can see your sissy clit."

Candi stood and delicately slid them over his hips and then stepped out of them leavening the white satin panties on the floor in front of him. Jessica gestured him to come closer. "You see he is so submissive he doesn't even get hard unless I give him permission, I keep him locked in this cage as I know it adds a certain level of discomfort and reinforcement of his position in life." She flicked the end of his cock cage to prove her point. "Would you like to try Stephanie? I think you'd quietly like dominating a little sissy boy like Candi."

With some trepidation, but totally fascinated, Stephanie leaned forward to inspect Candi's limp dick. She was close enough for Candi to feel her breath over his sensitive regions. She gingerly took his cock in her hand and massaged it gently. "Its really a boy? I couldn't tell until I saw," She paused and caressed his caged dick, "this"

"Oh yes he's fully functional and he loves being my little sissy slut. He's quite the pussy eater too. He's become very convincing hasn't he, the makeup is all his own work. Let me release his little boy clit so you can have full access." Jessica took the key from the chain around her neck and unlocked his cage then gently slipped the cage from his flacid cock allowing it to hang between his legs.

As I said, I control not only his orgasms but also his arousal, watch. Candi would you please rise to the occasion." Immediately his dick began to swell and Stephanie grinned, she could appreciate the power she could have over men, Jessica was slowly showing her the possibilities.

Stephanie reached forward and gently kissed the tip of his cock, eliciting a gasp of pleasure and leaving behind a perfect burgundy print of her lips before withdrawing. "Candi would you like to serve me this evening" She said nervously.

"Oh, of course, as long as its OK with Miss Jessica, I always love to make her friends happy" Candi replied giddily.

"Its perfectly ok with me sweetie, in fact I'm very much looking forward to seeing what Miss Stephanie has in store for you. I expect you to obey her in just the same way you would me, is that understood Candi?" Said Jessica as she took a seat on the bench opposite, seductively crossing and uncrossing her long stocking clad legs.

Stephanie was committed at this point so she thought she may as well go with the flow and satisfy her urges. Standing briefly, she unzipped her tight black skirt and stepped out if it revealing her exquisite black lace garter belt holding up he black glossy woolford stockings, saved for special occasions no doubt. She wore no panties which pleased Jessica, she had obviously had every intention of getting her rocks off.

She sat back down on the queening throne, "why don't you lick my pussy to start while Miss Jessica and I discuss what to do with you next."

"Of course Miss Stephanie." Candi said eagerly before lying down in front of her and sliding his head into the void below her. As his head settled into the padded sling within he could smell her arousal, then she lowered her wet pussy down onto his eager tongue and he began his ministration.

Stephanie gasped as she felt his warm tongue enter her marveling at the sensation of not knowing where the eager probing will venture next, her throbbing clit or deep into her dripping cunt. "Oh he really is talented isn't he" she said to no one in particular as she relaxed into the throne and began to grind in time with the thrusts from below. "Now what do you, mmmm ohh, suggest I do next Miss Jessica?"

Jessica rose from the bench opposite and collected the ornate flogger Stephanie had played with a few minutes earlier. "Well first you can use this to set your pace, just like a race horse." She giggled as she passed the flogger to Stephanie who instantly got the idea and gave a playful swat over Candi's corseted midriff. In response Candi quickened his worship of her clit and she shivered with pleasure.

"Once you are satisfied with his performance licking your slit you could perhaps indulge one of your own fantasies." Jessica retrieved a heavy leather strapped strap-on harness and a suitable dildo to fit to it. The harness had a smaller dildo within that would serve to provide the giver as much pleasure as the receiver. "Maybe fuck his little sissy hole and really feel like you are in charge." The thought of this evidently pleased Stephanie as she let out a long moan.

She took the harness from Jessica and inspected it as she moaned and ground against Candi's tongue. "This could be fun, don't you think sissy? Would you like me to fuck your tight little sissy hole?"

"Oh yes Miss Stephanie." Came the muffled echoing response from the box below her.

She swatted him hard with the flogger across his midriff, "I didn't say you should stop licking me." She giggled, giddy with her sense of power. Jessica watched the show from her bench opposite allowing her fingers to caress her own wet pussy as she enjoyed Stephanie take her first dominant steps.

A few more minutes and Stephanie was moaning regularly moving closer and closer towards her climax but she didn't want to cum just yet. Making a reluctant decision to curtail her building orgasm she stood and motioned Candi to get out from the queening box. "Now help me get into this harness sissy so I can fuck you." She said handing the heavy leather item to Candi.

Candi took the harness and from his kneeling position arranged the straps so she could easily step into it. Once both legs were in their proper place, Candi raised the harness up and placed the inside phallus against her glistening cunt. Gently he pressed and it slipped inside her, he felt her twitch in pleasure as it settled on her clit. He then arranged the soft leather straps in their correct position and gently tightened them.

Stephanie reached down and held the veined cock she now sported sprouting from her crotch. "Oh my this is fun, I'd never appreciated how empowering having a dick could be especially knowing I'm going to be fucking a little sissy."

"It's very cool isn't it knowing you're about to plough the ass of a dirty little fuck toy. Candi sort out your lipstick then come and lube up Stephanie's wonderful cock." Candi tottered to the mirror and took his lipstick out to freshen up the bright red colour, making sure he had a good thick coat on each lip before twisting the stick back into its tube and putting it back in the welt of his stocking.

Approaching Stephanie once more he sank to his knees as instructed. "May I please suck your cock Miss Stephanie?" he pleaded.

"Of course you may you slutty little sissy, make sure it's nice and lubed up because you know where it's going next!" Candi needed no more encouragement and eagerly slipped his red lips over the tip and let the cock slide deep into his mouth gagging slightly as it touched the back of his throat.

"Oh my, you really are a slut aren't you. Look how deep you have that cock in your mouth on the first suck." Candi began to bob up and down the shaft applying just the right amount of pressure to cause the in peer phallus to caress Stephanie's clit causing her to gasp in delight. "Oh, that's wonderful. I thought this would be a bit dull since I can't feel him sucking on me but, ohhhh. I might just cum right here." She looked down and drank in the sight of the sissy before her leaving streaks of red lipstick down the shaft of her strap on as he eagerly sucked her off.