Corporate Policy Ch. 02

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Paul dresses up as Tom requests.
3.1k words
4.49
69.6k
8

Part 2 of the 2 part series

Updated 09/22/2022
Created 11/15/2005
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cmike
cmike
12 Followers

Paul was certainly prompt; at the indicated time his cautious knock could be heard at the door.

Tom paused momentarily, for as much as he had been awaiting this moment he was going down a road that he had never explored before. The truth was that Tom had been progressing to this point for a long time, frequenting similar sites to those of Paul, finding himself drawn to images that he would have never have found alluring when he was younger. Now he was moments away from the realization of the most secret of fantasies and he had to find some courage to open the door and let the adventure in.

Eventually he stood up, and had to clear his throat before calling out: "Come in!"

The door opened, and Paul entered, clearly shamefaced, looking down at the floor. He was dressed in his normal formal work attire, but carried a gym bag in his left hand. Tom wondered what lay inside, feeling the beginnings of the same surge of lust that had directed him to taking this step. The same sense that he was merging the sexuality of control with the blurring between masculinity and femininity. Paul closed the door behind him, then stood motionless, clearly unsure what to do. Tom smiled. "There's a key in the door, Pauline. I think that you should lock it, don't you?"

Paul put down the bag, and turned to obey. As his hand rested on the key Tom saw a discernible tremor. He placed his hand on Paul's shoulder: "It's alright Pauline." His hand rested there briefly, although Paul's shoulder felt rigid with stressed expectation. The door locked.

"I want to watch you dress, Pauline. You can get ready over there". He looked over at the lounge area of the office, indicating with a nod that Paul should begin, then turned and walked back to his desk. Paul noticed with some disquiet that a camera stood on the desk.

Paul had been afraid of this moment ever since the discussion he had held with Tom – and yet late the previous night the thought of the role he would be forced to play had left him erect, wanting, restless. As instructed, he had waited until his wife was not around, and then he'd searched carefully through her cupboards, finding a combination of clothes that excited him, and that he suspected would have the same impact on Tom. Matching pink, almost transparent panties and bra, dark elasticized thigh-high pantyhose with a delicate pattern on the elastic, a formal pleated black skirt to just above the knee, feminine buttoned blouse, formal but strappy high-heeled shoes. So formal on the outside, so feminine underneath. Packing them into the gym bag under a concealing layer of his gym clothes was the first act of collaboration, and presented it's own thrill. He consciously recognised that his resentment at being forced into this situation was more than overcome by the thrill that his fantasy, carefully constructed over so many years, was being attained. As he started to move towards the corner he felt the beginnings of a very unfeminine erection.

He put his gym bag down on the low coffee table, unzipped the top, reached in and took out the clothing, laying them out across the tabletop. Tom's mouth went dry as the wispy underthings were exposed to his gaze – both bra and panties so transparent that the wood grain of the table could be seen through the material. Then Paul stood up, with his back to Tom and began to unbutton his work shirt.

There was tense silence in the room, both men nervous, hardly believing that this had begun. Paul pulled his shirt out of his trousers before letting it slip off his arms and draping it across a chair. His shoes followed, then he bent down to peel off socks. His trousers joined the shirt, and then a pause before his thumbs slid into his underwear and as they fell he was naked.

Tom wished Paul would turn around, but he remained silent as he picked up panties, bent over and stepped into them, drawing them up until they stretched across his ass like a drumskin. He struggled with the brassiere, even though it clipped together in front. As he drew up the first leg of pantyhose, a transformation began – it seemed inconceivable that his posture should be changing, but his actions seemed to become softer, reflecting in gentle motion the gentle sheer femininity that encased the two legs. He stood up, and Tom knew that Paul was savoring the feel of the texture against his flesh.

Tom's heart beat with such intensity that he felt it was difficult to breathe. He watched Paul step into the pleated skirt, pulling it over his hips and zipping it up as a woman would do. Paul's struggles with the buttons, in reverse position to a male shirt, took some time but Tom felt no need to hurry him on: for these moments were like the voyeuristic glimpses into a private act, privileged to share secret moments. The shoes – such high heels – lifted his calves within the pantyhose, and now he turned shyly to face Tom, the girl nervous at her debut, the teenager gangly in her new adult outfit, the promise of woman beneath formal skirt and blouse. Pauline whispered: "I'm here", not knowing what to do next.

Tom swallowed, but his mouth remained dry. The words, the submissiveness of this creature before him charged him with a greater sexual desire than he could ever remember in his life. For notwithstanding the transformation that he had just witnessed, this woman before him was a naïve nervous creature that he knew would submit fearfully to his desires. As much as he wanted to fill Pauline with the iron bar of his cock, he wanted to explore her, live out the fantasy that he was sure they both shared. He picked up his camera. "Look at me, Pauline – I want your face in the pictures."

Pauline stood unsure as Tom walked around her, taking pictures from the vantage points that he enjoyed. "To work here, you will have to do exactly as I require. You understand that, don't you?"

Pauline nodded, head turned to the right to look at Tom as he circled, capturing yet another image. "Now lift that skirt so I can take a picture of your ass in the panties." Pauline hiked the skirt up, holding it crumpled in his hands, hips now startlingly naked below the material. The curve of his ass stretched the material, so transparent that no modesty was spared. "Good. Bend forward, legs apart." Pauline was conflicted between desire and embarrassment, aware that bending over stretched the underwear even further, conscious of how submissive a pose this was. It seemed to take forever as Tom moved about to different angles, capturing the scene in close detail. "You have such a beautiful ass, Pauline; I can't wait to explore it more closely." As he heard the words, Pauline felt his cheeks clench nervously for that could only mean one thing. Was he ready to be a girl? His fantasies had always stopped short of the absolute reality of giving himself, feeling himself being filled with a man's need. And yet his cock had been engorged from the moment he put the panties on, and this fear did nothing to alleviate his desire – if anything it only emphasized his desire for submission.

"Now stand up, turn around – and keep the skirt up."

Paul did as instructed, conscious now that his raging erection was probably clearly visible through the gossamer stuff that made up the panties – and he realized this was true as he saw Tom's focus on that narrow strip of filmy fabric. After long moments of just gazing, Tom lifted the camera, moving to capture images from multiple perspectives. Paul's face felt ablaze with mixed emotions, aware that his cock was twitching slightly, ashamed at the exposure, but SO erect that it felt he would explode. The contradiction was clear: he had never felt so consciously feminine, so clearly an object of such evident lust – while his manhood was the vehicle through which this girlish sentiment was revealed. This mawkish confusion was apparent in his stance, his expression, his tenuous balance on the heels; and it increased the desire Tom experienced, trying to capture on film not only the images of flesh, erection, panties, pantyhose – but the paradoxical emotions so evident in the discovery of the mangirl before him.

Tom put the camera down, then pulled up a desk chair into the middle of the floor. He sat down and smiled: "Come stand in front of me, Pauline." This moment had been inevitable since the beginning of the discussion between the two men, and Paul had feared it for more than a day. This was moving beyond discussion, beyond photographs and posing to ....where? He hesitated just for a moment, but part of him wanted to take that walk, and there was really no choice; and so he stepped forward, balancing himself shakily on the heels, still holding up the skirt, until he stood obediently before Tom.

Tom's mouth was dry, his hands had a tremor in them, his heart was racing uncontrollably – this moment was the realization of years of whimsy: before him, a compliant partner, dressed as a woman, rigid cock straining at panties, open for his gaze. Open for his touch. Open for his touch. It was incredible just how feminine Paul looked like this – his legs encased in pantyhose sheen, the panties themselves no defense at all against Tom's desires, the skirt framing legs, hips, and pink, straining fabric. He could wait no longer – he reached forward with one hand, gently encircling the rod through the material, then looking up to Paul's face.

Paul's eyes were closed, intent on the sensation of being touched by a man. He knew that he was already close to an orgasm: the first-time thrill had overcome whatever inhibitions he may have harbored, and all he wanted was to luxuriate as a desired woman being touched, opening her legs for exploration for the first time. Tom's fingers slid up to the top of the panties and pulled them forward, freeing Paul's cock: it stood clear of his body, head projecting above the fabric, suffused with bloodlust. When he opened his eyes again, Tom was focused with wonder, lowering the panties enough to expose the length of it. For both men, each act was filled with the thrill of sexual novelty: Paul's exposure, Tom's exploration. This rigid shaft of flesh between them articulated the moment: Pauline showing herself – with a mixture of shame and lust - to a demanding audience, Paul attaining access and control over a feminine cock. He wanted to touch it, to lick it, to take it between his lips and consume it. He wanted to stroke it across his cheeks and face, feel it's engorged mass against his tongue and the roof of his mouth. He wanted to stroke it, explore it, own it, display it, worship it as the embodiment of his deepest lusts. He drew the panties down to mid-thigh, then tenderly wrapped the fingers of one hand around the cock, and moved it closer, rubbing the length of it across his cheek, until the tip found his mouth: he tentatively opened his lips to absorb the head, tongue finding the slit and parting it gently. A soft sigh escaped from Paul's lips, and he moved his hips forward pushing himself deeper into the womb of Tom's mouth.

Tom gave himself to the sensation, drawing the shaft in deeply, eyes closed, moistening it, aware of the sighs escaping Paul's lips, the rocking motion of Paul's hips against him. Paul lowered the skirt now, over Tom's head. Tom found himself inside this dark tent of lust, Paul's hands cradling his head through the material of the skirt, holding him as he fucked Tom's mouth. Paul's hips were beginning to jerk spasmodically. "I'm going to come!", he cried – but Tom pulled away, watching the cock twitching for long moments, inches from orgasm.

"It's too early Paul. I want you to come when I do."

He withdrew himself from under the skirt, stood up, aware as he did that the skirt was deformed by resting on Paul's cock. Standing up, he drew Paul's mouth to his, and spoke as he kissed him tenderly, gently, soft touchings of the lips. "You look so beautiful, Pauline. It's going to be so erotic to make love." His tongue entered Paul's willing mouth, their shared breathing intense, both men holding their faces together. "Unzip me, Pauline. Touch me."

Paul's hands fell away, finding the hardness at the front of Tom's trousers, searching for the zipper, drawing it down, reaching in to free Tom's erection. Tom was lifting Paul's skirt, and as he felt the cool air against him he rushed his hips forward until the two erections touched. Paul made a strangled sound, leaning his head forward and resting on Tom's shoulder, caught in the feminine abdication of lust. They swayed slowly, rubbing cocks, occasionally moaning. Tom felt himself wondering what it would look like if he could see under Paul's skirt, how their cocks were responding to this sharing of lust. He kissed Paul's ear, turned towards him as she lay against his shoulder. It was so evident in his posture that coercion had been replaced with an overwhelming expression of feminine lust. He whispered tenderly: "Daddy's brought some oil with for your bottom, to make it easier for you." His hands moved around Paul's hips, until they rested on the curvature of his ass cheeks, squeezing and opening them rhythmically. His middle finger reached in to press against the anus, feeling it contract against him. "You know that you want daddy inside you, don't you?"

Paul nodded wordlessly.

"Then you must let daddy apply it for you, ok?"

Paul nodded again. Tom nuzzled his ear: "Say yes daddy."

"Yes daddy."

"Good." Tom let go of the ass cheeks, taking Paul by the hand and leading him across to the desk. As they faced each other, he squeezed Paul's cock through the material again. Holding his hip, he turned Paul towards the desk, and pressed against his back until Paul bent forward. Tom opened a drawer and withdrew a bottle, pouring the oil into his hand. Then, moving behind Paul he lifted the skirt, admiring the curvature of the bottom that was revealed. He laid the hem against the top of the ass, and it stayed there. "Bend over for daddy, Pauline." Paul did as he was told, allowing Tom to freely open his ass cheeks and freely apply the oil to the crack, watching it slide down to the anus. He used the tip of his finger to massage it in to the anus, the finger in to the second joint, seeing Paul's back arch slightly, a twitch at the base of his cock, hips moving away from this invasion. Withdrawing the finger, he used both hands to hold open Paul's bottom cheeks, trailing the head of his cock down the crack, until it lay at the entrance. Holding it with one hand, to give it more strength, he pressed forward, sliding it in, hearing Paul whimper, reaching around to grasp and stroke Paul's cock as he pressed forward and held himself fully embedded for the first time. He could barely contain himself – he couldn't move or he would orgasm immediately. He wanted to savour this over long deep strokes, watching his cock sliding into this submissive, beautiful manwoman, but as he started to withdrew the moment overcame them both. He found himself plunging into Pauline, his hips bucking with abandon, cock pumping, Pauline wriggling away from this uncomfortable onslaught but also ejaculating wildly into the skirt, rubbing against the material and the desk, feminine gasps punctuating the moment that led to a final, long collective sigh, bodies stiffened into the last moment of lust as it drained away from them both.

For long moments they barely moved. Tom had fallen forward, lying against Pauline, her upper body spread across the desk, her legs trembling slightly. Finally, still breathing heavily, Tom sighed. "That was amazing. I can't remember when last I came that strongly."

"And me", said Paul. "But I'm so sore now."

"Your ass? I'm sorry. I couldn't stop at that point."

"Not my ass. My hips, from banging against the end of the desk."

Tom started to laugh, lifting himself. "Turn around."

Paul leaned with his ass against the desk, lifting his skirt ruefully to view the damage. A straight red abrasion stood out across the front of his hips, including the underside of his now progressively flaccid cock. "Oh – look at this skirt", he sighed. His semen had gushed into the material, leaving both trails of droplets and sodden blotches. Some had found it's way down his legs, marking the pantyhose.

Tom was tidying himself, redoing his trousers and shirt. "I don't envy you hiding all of this from your wife. Don't let her examine your cock for a while."

Paul had found some tissue paper in the gym bag and was applying it judiciously to clean up the most obvious stains. "Yeah. Thanks very much."

Tom stepped across, leaned forward and surprised Paul with a last kiss. "That was good for me, Paul. Very good. I think it was for you as well?"

Paul smiled ruefully, and gestured at the mess he was cleaning. "Obviously, wouldn't you say?"

Tom looked at Paul's still-exposed cock. "I'd like to do this again. But with a bit more time?"

Paul said nothing, just looking at Tom questioningly. "I thought, if this worked out, you and I should go on conference. Far away. And stay in the same hotel. And – you know – spend some real time ... together. Being girls together. Would you like that?"

Paul smiled ruefully. "All I want now is to get tidied up, and stop this pain you know where." He paused. "But yes – I would like that. I would like that very much. But next time we both wear panties and a skirt!"

Tom smiled, feeling the first furtive strands of renewed lust. "I'd like that. Kissing with skirts on." He fell back into his chair, watching Paul's every move as he began to disrobe and prepare to leave. "I feel the need for a conference very soon."

cmike
cmike
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6 Comments
EmmaCDnzEmmaCDnzabout 5 years ago

Cant wait for part 3 and to see what happens with Pauline & Tom on their 'conference'

cdCindy1cdCindy1almost 7 years ago
great story

I too am a married CD and I wish my boss would catch me dressed up as his woman. It would be wonderful if he too was a CD so we could both enjoy hot tranny sex while we suck each other's cocks and he fucks me deep and hard. Please tell more stories like this one.

Cute Little ThingCute Little Thingalmost 18 years ago
Very talented and twisted mind

Fantastic, terrific, erotic story. If it was me, I'd never have the main character show girly tendencies, the man would be the man and the "girl" would be the "girl". But that's just my weird fixation with gender roles.

What I think you capture in this is the erotic connection between the two men. What's good about your stories is you go beyond the surface details and try to connect with the real emotional feeling of this happening.

It's hot.

chair1953chair1953about 18 years ago
Corp. POLICY 2

Awesome I was cumming in my pants before the end of the story! can't wait for the next installment!

ColinGrahamColinGrahamabout 18 years ago
Very erotic. Please work on P.O.V.

This was very erotic and definitely got me hard. Pacing was very nice, though the tone at the end seemed (to me) a little abrupt. The biggest problem I see is in establishing and maintaining a P.O.V. (point-of-view) that doesn't confuse the reader. We're inside the head of both "Tom" and "Paul" (close 3rd person) but you shift us back and forth within the same paragraph -- even within the same sentence, as in this example:

"Tom wished Paul would turn around, but he remained silent as he picked up panties..."

Who picked up the panties? We were in Tom's head and then suddenly we're doing a Paul action. See the problem? Work on that but, PLEASE, keep writing.

Thanks for the fun read.

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Corporate Policy Previous Part

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