Scene 29

Getting to the office Jackson felt like he was on a mission, the nude five inch rounded toe hidden platform heels sounded with each of his quick paced stepped, him very much missing the ability to move so much faster before his own life went out of control to make him wear high heels and outfits like the one he was wearing today. The peach colored sleeveless dress with a pencil skirt and asymmetrical neckline, along with the panties holding his tucked back manhood and bra holding up the heavy as heck fake tits that caused extra train on his back was not what he would have liked to wear. It did however get the Madison seal of approval for looking both as she put it fine as hell and professional, just the words every brother wants to hear after he got done putting on woman’s clothes and putting on makeup after a night of drinking and bad decisions.

The rapid tempo of the click clack, click clack of Jackon’s heels on the tiled floor of Mega Corps entrance area caused more than a few heads to turn and while the feminized man’s cheeks burned, a bright blush coming to his cheeks he still pushed forward to get to the elevator as quickly as he could. ‘Head down and push forward’ He thought as Jackson held his purse close to his side to keep it from bouncing about, but he could do nothing to keep the realistic breasts stuck to his chest from doing the same. Lucky wasn’t on his side when he got to the wall of elevators, not one was opening up and a small queue had built up around the area.

Deciding it might look odd and not wanting to look at his feet perched in the tall heels Jackson looked up from the floor and saw a short pudgy man leering. Revulsion, that was the feeling that ran through Jackson’s mind as the man looked him over, seemingly not just undressing him with his eyes but fucking him too. ‘All he sees is the blonde bimbo you are pretending to be, he doesn’t know you're a man… god I hope no one can tell.’ He didn’t worry about being really seen nearly as often but Jackson couldn’t help having that tremor of terror from time to time. ‘Remember you are Jacqueline Hart, you like the male attention… I’m Jacqueline Hart and I like men looking at me.’ He repeated the last part a few times in his mind before giving what the leering man saw as a shy but flirty smile. Jackson found a girlish giggle escaping his lips unbidden as he tucked some of his blonde hair behind his ear. “Good morning.”

“Great morning now.” Jackson heard the man say, his eyes moving down to his heeled feet and then back up to be level with his ample, but fake chest. The idea that he could have an impact on the kind of day the man was having just by saying good morning and smiling felt wild to Jackson. How he felt about being eye fucked didn’t change, but the power to improve someone’s day felt nice… empowering. He could recall sticking his head out of his cubicle to watch a sexy gal go by on more than one occasion, it certainly made his hours at Mega Corp more tolerable. A girl smiling in his direction really did have an impact on his day, heck he had been complimented on his long hair more than once and their comments had made him want to keep the look more, and now that power was his. ‘Do all women feel like this?’ The dress wearing young man asked himself before being forcibly brought back to the present when he felt a pinch to his ass while standing in the close confines of the elevator. “Eeep!”

The second the elevator doors opened Jackson got out of the cramped area, having no clue who it was that had touched him. No matter how much he told himself that Jacqueline should consider it a complaint it didn’t reduce the blush on his cheeks or the embarrassment as he quickly moved to the stairs in order to avoid that or more from happening. While it wasn’t the same he thought to a porn video that he admittedly watched more than once that had an asian woman on a cramped train being groped, fingered and fucked while the rest of the people around ignored what was happening. Moving up the stairs at a decent pace caused his bits to bounce more, causing Jackson to let out a sigh before centering himself and entering the floor where his little secretary desk was.

Getting there he tossed his purse into the bottom drawer before heading off to start his daily activities. ‘Get Mr. Dunn his coffee, check my email and go see HR if he doesn’t give me anything pressing to do.’ Another light giggle bubbled up at the thought of anything he did being important, that was before another thought intruded on his mind. ‘I do need to make him happy… should I show him the text messages and give him a blow job before or after I go to HR? I mean, like, what is the point of doing that if I don’t follow through?’ The thought brought a sour expression to his face. ‘Am I really planning my day around giving a man a blow job!?’

Not staying for any chit chat or office gossip Jackson simply told Tab that he had a lot on his plate this morning and would catch up later. He could just imagine what she would say if she knew about the dream he had the night before, not that he remembered all of it, but it was disturbing and the fact that it was also a wet dream made it much more so. With a shudder and shake of his head Jackson went back to his desk, putting down the hot coffee for a brief moment as he got out his cell phone. Pressing the device to his chest he closed his eyes and took a deep breath. ‘Remember what you are doing this for, you can do this, you are Jacqueline Hart.’ He told himself for the tenth time today. ‘This is what secretaries like me do, this is what girls like me enjoy doing.’ Telling himself things like that helped at least to a degree get in the right mindset to pretend to be the airheaded personal admin, but today it felt more accurate. A feeling he would like to explore, maybe he was getting better at acting or compartmentalizing, but there wasn’t time for that. She needed to see her boss and then get to HR to try nipping this silly surgery thing before it went too far.

Without a second thought Jacqueline knocked on her bosses door twice before opening it to see the older man with his graying hair and beard on his cell phone with a scowl on his face. ‘Not a good sign.’ She thought before pushing forward, closing the door behind her as she entered the office. When all he did was give her a glance to acknowledge her, Jacqueline sat down atop the side of the man’s desk and crossed her legs as she started to bounce her leg. Holding up the mug of coffee and raising an eyebrow in Dunn’s direction.

The aroma of the hot caffeinated beverage tickled Jacqueline’s nose, reminding her that she hadn’t gotten herself any in her rush. Not sure why she did it, Jacqueline brought the mug up to her pink lipstick covered lips and took a sip of the coffee while looking her supervisor in the eye, a playful smile on her lips as she put the mug down, enjoying the warm flavorful dark roast coffee as she took a small swallow.

“Hey.” Alexander said to the person on the other end of the phone as he looked at the blonde in front of him who was now dangling one of her heels from her toes. “We will circle back to this, I expect the numbers to be in the realm of realism the next time we speak though.” Without saying goodbye he hung up the phone, putting the device in his pocket as he took in the figure sitting on his desk. Intellectually he knew what she was, and when he had first seen the intern in the office wearing the dress he had wanted them gone… Well first he admired their rear end, but when he found out it was a man in a dress he wanted them gone. Now though he was singing the praises of HR telling him no, something he didn’t care for normally. Sure he wouldn’t be telling anyone that he enjoyed the time with someone who was transgender, but he just loved how feminine she was. The way she flirted without saying a word made him internally curse Downings. “You having fun?” He asked, loving how she batted her long lashes, her soft brown doe eyes making him hungry in a carnal way.

Giving her boss a slight shrug she looked away from him. ‘Be direct, men like that, Linc said he loved it.’ Uncrossing her legs and crossing them the other way she looked back up to meet his blue eyes after unlocking her phone and passing it over, the text messages from the other night on the screen for her boss to read. “I could be having fun, but we could have fun today.” With much of their experience with sex coming from unrealistic porno videos Jacqueline let her heel that she was dangling fall from her foot before extending her leg so that her painted toes could touch the much taller man’s crotch.

Feeling his admin’s touch, Alexander looked up to the ceiling of his office, damning both the head of his sales team and himself for feeling the need to stick to his deal, the fallout for breaking it being more than he wanted to pay. “Ahhh.” Some tension left his body as he felt her rub her foot on him in such a provoking fashion. He had been on the phone with one of the designers. His wife, excited about his upcoming promotion, wanted to do some renovations to the house and he didn't like where the bill was going. Looking down at the phone in his hand he saw a message from her to one of his other employees Lincoln Hatch, her telling him to cum for her and the picture of an erect dick being just one of the responses. Flicking his hand to drop the device, Alexander put one hand on the blonde’s foot to hold it in place. He didn’t have a foot fetish, but doing what she was doing he could understand how someone could get such a thing. “What was that?”

“You said I needed to umm…” Jacqueline bit her bottom lip so he could see her whitened teeth press against her plump pink lip. “Prove that I wanted it, and I do, I want it… I want your cock.” Feeling her boss’s manhood grow at the touch of her foot and toes had an uncomfortable feeling grow inside of her, but saying what she knew Dunn would like to hear, what Linc had said he loved hearing made something collapse inside of her. ‘This is all wrong, I can’t do this! What was I thinking!? I’m a man, I shouldn’t be… I said that! What is wrong with me!’

Letting go of her foot, Alexander stepped away, letting out a drawn out sigh. Clearly the slut knew what she wanted. He didn’t remember telling her she needed to prove she wanted him, he already knew that, or at least he was pretty sure he hadn’t said that. What he needed from her was to get her not so little boyfriend to understand she was just at a stage in her life that one dick wasn't enough. That was clear by the fact she was Hatch’s girlfriend and having relations with Downings. “Tell you what, why don’t you prance on over to Downings little cubicle office and make sure he is okay with this and once you make it clear you can come on back and you can have what you want.”

“Downings? You mean Abe? You want me to ask someone else if I can… can.” Jackson swallowed, the role he was pushing collapsing under the weight of what he was preparing to do. The insanity of the man standing in front of him wanting him to go ask permission from his friend in order to put his dick in his mouth made Jackson’s head spin, it made him stop moving entirely, paralyzed by it all.

Touching his palm to the girl’s pale cheek, he moved her face so she was looking up at him, moving his thumb to press on her lips, the pretty little thing's mouth opening at his touch so he could slide his thumb into her warm wet mouth. ‘She doesn’t feel beholden to anyone, makes me want to claim her that much more…’ Alexander licked his bottom lip, looking down into her eyes, her pink lips encircling his finger. The desire to claim the pretty blonde, make her feel and know she belonged to him filled his mind. ‘If only Jacqueline had been born this way, I would break her, make her mine.’ He thought, not understanding how being transgender worked, but just thinking about the fact Jacqueline had male genitalia. “Tell you what, if you don’t tell anyone, doubly so for Downings then you can have my cock you so desperately want. Alexander had flings with almost all of his administrative assistants, he either got bored of them or they couldn’t provide what he needed, but in all his time he never had someone so eager. Sure she acted coy at first, him having to push her to do what she really wanted, but he could see what she wanted.

“You… you want me to not tell Abe anything?” Jackson asked, confused. There was no way he was going to go ask his friend permission to be intimate with a man, but now Dunn wanted him to keep it a secret. ‘He must have realized how crazy his little kink, powerplay was.’ Sitting there still on the desk, now one heeled shoe laying on the floor along with his phone Jackson wasn’t sure what he was supposed to do. It had all been so clear before he came into the office and now… now he had to put up or shut up. He had to act in order to keep Linc employed and get the promotion he was not deserving but was promised, so that his own problems could be solved without talks about fraud or police needing to be involved happened and finally… to help that poor girl that shared a name with his sister. A twisted version of a movie quote came to mind about not being a hero he wanted to be, but the hero people needed. ‘Smile, smile, he just had his finger in my mouth… and that is okay, that is just foreplay… yeah, girls like foreplay, Jacqueline likes to flirt, likes foreplay and she… I need to be the hero.’ What had to be done was clear, or at least the only viable path that didn’t lead to a lot of bad scenarios. “Does that mean Linc will keep his job?”

Cocking his head to the side, Alexander pressed his lips together with a nod. “Exactly, our special time together can continue if it stays just between us and yes, that boyfriend will keep his job. He is going to be sitting in this desk before you know it.”

“What, what about Maddy?” Jackson needed confirmation that he was debasing himself for no reason, he couldn’t have this kept over his head. He wasn’t gay, he didn’t want anything to do with anything sexual with men. Despite the six foot two man in front of him appearing in his dream last night he didn’t want to be touched by him at all, that had been a nightmare, one he was about to make much too real.

“Maddy? Oh yes. I would imagine she will be starting in her new role before the end of next week. You don’t need to worry your pretty little head about them, in here it is just you and me.”

As if the world was saying that wasn’t true, Jackson heard his boss’s phone on his desk start to ring. Giving him immediate thoughts of it giving him an out, but it was followed by dread that the confirmation of his concessions wouldn’t follow through. Against his better judgment, Jackson reached over, picking up the phone and put it to his ear while looking his boss in the eye. “Good morning, Alexander Dunn’s office!” He said in an overly chipper voice that he truly didn’t feel. “No,I’m sorry he is in an important meeting right now, please call again in fifteen minutes.” Without giving the person on the other end a chance to respond, Jackson hung up the phone. “Now… where were we?”

Not even a second passed after those words left Jackson’s mouth before the larger man was upon him. One hand firmly on the back of his neck the other on his shoulder before sliding down to the small of his back and a rough kiss was initiated. Jackson could feel the man’s beard brushing across his smooth skinned cheeks, the creams he had been using had been a powerhouse, he hadn’t had to touch a razor to his face in what felt like too long. The contrast between himself and Dunn wasn’t lost on Jackson, even if he didn’t have time to dwell on it as the man’s lips pressed against his own. Dunn’s face turned slightly to the side as he pressed into him and not being spoiled for choice, Jackson kissed back with the same intensity. The passion on his part was purely for show, but it needed to be done or so Jackson told himself even as his stomach turned, and his skin crawled at the experience.

Being kissed, manhandled, a tongue dancing in Jackson’s mouth, his own dancing along with it as he grabbed and pulled on the larger man’s tie to hold him close while his mind told him to not just push him away, but to move on the attack. It was all bad, but the worst parts were that there was much more to come and cum… but the fact that part of him enjoyed the feeling of true desire not just appealing, but arousing caused its own set mental anguish. Wanting it to be over, needing it to be over, Jackson’s hands looking way too feminine for his tastes thanks to the painted long nails, slid down from Dunn's tie. Pressing his palm into the man’s chest that felt way firmer than it had any right to be compared to his own, slid down till it got to his belt buckle. Using both hands Jackson soon had the standing man’s pants fall to the floor and his thick, already erect dick in the palm of both of his hands.

Needing to give the girl room to work, Alexander stopped pressing himself so hard to the girl, the hand on her back moved around her chest, he knew her tits weren’t real, something that was going to change soon, a change he couldn’t wait for, but still he rubbed them through her peach dress. ‘God I want to fuck her!’

The full **** kissing that Jackson was positive would leave his face red from friction if it went on too long migrating down to his neck. Tilting his head to the side the feminized man allowed easier access to his neck as he lightly twisted his hands around the dick he held, closing his eyes and trying not to think about it being bigger than his own or how the lips touching his sensitive neck made him feel. ‘You can do this Jacqueline, you can do that. Just… Ooohhh that shouldn’t feel good…’ When the lips came back up to meet his own Jackson felt himself moving his face forward to meet the older man’s and squeezing the cock in his hands.

A not so insignificant spike of pain shot through Alexander as the girl’s grip grew two tight for a half second. ‘She wants to play rough… we can do that.’ he thought before moving the hand on his admin’s neck up into her blonde hair, giving it a light pull with one hand, pushing her chest with the other so that she laid back on his desk. “Stay there.” He growled, shuffling around his desk so that his exposed ass was facing the closed door to his office, his legs caught in his fallent pants and without taking off his shoes he wasn’t going to be able to step out of them.

Pushed onto his back a bit of fear ran through Jackson, just one more thing to add to the pile. He knew the pencil skirt of his dress had been pulled up slightly, it wasn't as if anything could happen between his legs, he wasn’t a girl, but he really didn’t want anyone to see that he was semi-hard from what was going on. What was happening soon became clear as his head was pulled just over the rim of the desk, a spike of pain shooting through him for the second time, a sensation he didn’t want to feel and that was before his head now over the desk had Dunn’s cock thrust into his open mouth. It was like his face was being fucked from upside down and the hand’s holding him were keeping Jackson firmly in place.

“Yeah, you like it rough don’t you slut. Moan for me girl, let me hear how much you love my cock.” Alexander said enjoying the sight of the girl squirming with is dick firmly in place, her legs kicking in the air, the fact she only had one of her heels still on adding that extra hint of excitement. He hadn’t forgotten her kicking it off to excite him, but seeing her flail her legs with one shoe off made it seem like it had fallen in the throws of passion.

“Mmmm MMMMAAAA!” Jackson squeezed his eyes closed tight, feeling tears coming to his eyes as he felt the firm fleshy thing in his mouth buck back and forth like a piston, it sliding across his tongue, allowing him to taste his flesh that was mixed with a hint of something creamy… slimy and salty, the man’s pre-cum clearly trying to do its job with lubrication, but only making his stomach turn as he lay on his back, unable to do much more than literally take it. Jackson moaned like his boss wanted, wanting it to just end. He wasn’t sure what was worse being the one willingly to hold Dunn’s cock, rub his fingers around it before intending to bring it to his mouth or feeling helpless as the same happened. Either way his pink stay on lipstick was going to be put to the test as the member slid in and out of his mouth.

When Jackson felt the cock be thrust deeper into his mouth, just touching the back of his throat, his gag reflex starting to kick in and start to **** he knew the answer to his question. The hard dick that was penetrating his mouth started to pulse as it was held in place and warm globs shot free the answer came to him. It was worse to feel used, to feel like a victim, it was so much better when Jacqueline took charge and was in control, than to be a semi-willing victim.