Lyndseygurl's Sissy Captions

Andy sat at his desk in a daze, trying to concentrate on work and more or less failing. His cock refused to soften and both it and his arse pucker were so sensitive that every little shift in his chair seemed to rub his wet, silky panties against one or the other and send hot shivers spreading out from his belly. It was very distracting and worryingly arousing.

Worse, several of his colleagues came to talk to him, the first being Danny, the closest thing he had to a work friend who asked why he was late. Afterwards, Andy was terrified to find he couldn’t remember what he’d said to his friend. He thought he’d said something about how hard he was being worked like he’d been told, he thought he remembered Danny saying something about how he should stop complaining when he was so lucky, but he couldn’t remember a word, couldn’t remember how he’d hidden his semi-hard cock from his friend, whether he might have revealed the thin blouse or bra under his jacket and shirt.

A few other colleages also approached him, somehow almost the most interaction he’d had with his fellow sales-men and -women in quite some time, and he couldn’t remember the details of any of those either beyond the terror of discovery, the veiled resentment they projected and the hope that he’d managed to keep on the message he’d been given by his tormentors. The couple of female colleagues he spoke to were especially difficult as if simply by being female they knew what the two women were doing to him and what he was wearing, or how much it aroused him. He hoped fervently that he hadn’t blushed while talking to them.

He got little if any work done and couldn’t bring himself to ring any clients because he had no idea what he was saying. Fortunately for Andy, though it seemed like days of torture sat at his desk, it was only a little more than an hour before his desk phone rang, startling him slightly.

“Hello. Andrew Maddox?”

“Please be ready in my office in five minutes, Andie. You will be working with me for the rest of the day.”, Andy’s eyes widened and he stared at the receiver for several seconds after the phone clicked off abruptly into silence followed by the burr of the dialling tone. He shook himself out of it as he realised he only had a bit over four minutes to present himself in front of Mrs. Reddin and when she said “ready”, she undoubtedly meant having his toy firmly embedded in his arse – something he didn’t exactly relish at that moment.

Glancing around furtively to see if anyone was looking his way, Andy grabbed his bag and stood to head for the toilets, then immediately sat again as Mrs. Reddin’s words sank in; “You will be working with me for the rest of the day”. Did she mean she was going to torment him all day, or could she literally mean working? Did she literally mean “all day”? He didn’t dare call back and ask, so he gathered all his things into his bag and added some of his work notes just in case and dashed red-faced for the toilets.

Andy’s bottom felt constantly slippery now, but nevertheless, he smeared a generous amount of lubricant onto his toy as he sat in the cubicle with his trousers and panties round his ankles and his skirt round his waist. He frowned down at the red panties nestled in his trousers, seeing the distinct darker patches; one where lubricant had leaked from his over-used arse and the other where his almost constantly semi-hard cock had leaked pre-cum into the front. The now-hairless and smooth area of skin above his cock was also slick and slimy with pre-cum. 

Glancing at his watch, he realised he barely had two minutes to present himself to Mrs. Reddin. He gasped and quickly reached down to push the toy into his arse, his rush making him push it in harder than he intended, which made him yelp involuntarily as he bugle forced its way through his overly-sensitive anal ring. He froze, listening to see if anyone else was in the toilet who might have heard him and stewing in the self-disgust caused by the twitching of his semi-hard member in response to the anal invasion.

He couldn’t hear anyone and he was out of time anyway. Andy hastily re-arranged his clothing and rushed out, bumping into a colleague on the way in. He mumbled an apology and fervently hoped the man would put his flushed face down to embarrassment at the contact rather than his embarrassing state. 

Andy hurried across the office, insanely conscious of the toy rubbing in his over-sensitive hole, conflicted between going slowly and casually enough to hope to not attract attention carrying his bag towards the director’s office and quickly enough to avoid whatever horrible extra humiliation that would no doubt be inflicted if he were late. At the same time, he tried to both avoid meeting the eye of anyone in the office and steal glances to see if they were looking at him. It didn’t work very well and he arrived at the door a bit of an emotional wreck.

His knock fortunately gained an instant, “Come in!”, from the other side and, closing the door behind him, he tried not to look at Mrs. Reddin sitting behind her desk waiting for him as he stripped off him outer clothing and donned his heels. Dressed “properly”, he sank, much like his pride and dignity, to his knees and clicked on the toy in his arse before crawing towards the woman who now dictated his increasingly strange life.

As before, Mrs. Reddin seemingly ignored him until he had crawled across the floor and kissed her feet. She glanced down at him, “Three laps of the office, if you please, Andie. Then you may sit.”, she gestured at the chair beside her desk.

Andy swallowed, then pushed himself resignedly to his feet. He stepped in his heels, this time taking only half a lap of the office before he found the remembered rhythm of it. Another lap and the oddly sensual and freeing feeling of the movement came back too and he stepped out, shoulders back, chin high, hips swaying, treading almost confidently. For that brief time he didn’t even mind the way the walk made him intensely aware of the toy humming inside his body as the motion almost swirled it around the most sensitised parts and made his cock twitch just a bit harder in his panties. A tiny part of him was almost sad when Mrs. Reddin’s voice interrupted the sensual flow, “That’s very good, Andie. It’s really coming along. Now, sit.”

Andy moved to the chair and sat. Mrs. Reddin’s face turned stern as she frowned and her stare bored into him like a laser. For a long moment, Andy wondered what he had done wrong then, with a jump of his stomach, he pulled himself more upright, pressed his knees together and crossed his ankles as he tucked his feet under the chair and folded his hands in his lap. The frown turned into a pleased smile, “Excellent, Andie! It is so gratifying to know you are listening properly.”

She stood and looked down at him. Andy raised his gaze to keep his eyes on her face, though he couldn’t help taking in the figure in the severe, nipped-waist, black, pencil skirt with a wide belt, white blouse above and obviously a lacy and expensive bra underneath on the way up. Her only reaction was a slight quirk of her eyebrow as his eyes finally found her face. Then she spoke, stepping out of his view and walking behind him as she did. It made Andy feel even more unsettled and nervous than he already did, “I called you in today, Andie, because your work has gone downhill in the last few days; you are not being very productive.”

Andy’s jaw dropped. He dared neither spinning to stare at her nor voicing the protest that rose to his mouth to point out that her own extensive humiliation of him and of her friend in HR were entirely the cause of the very thing she was complaining about. Instead, he just sat, staring at the surface of her desk and internally flip-flopping between protesting the injustice of it and rising terror at the prospect of being punished for it. After a short pause, perhaps to elicit exactly that reaction, Mrs. Reddin continued, “So today, I have decided you will work under my direct supervision. After all, we have an office ready for your new job; I see no reason why you can’t perform your current one there.”

Relief clashed with suspicion in Andy at getting off so lightly. He braced his back up straighter, wringing his hands in his lap and squeezing his knees together, waiting for the other shoe to drop. The ‘shoe’, when it came, was also not so bad as he might have imagined and came from an unexpected direction. Mrs. Reddin sat back in her chair and busied herself with something on her computer as Andy sat there, fretting. Her screen was angled away from him so he couldn’t see what she was looking at and when she spoke it came out of the blue, “So you have never worn makeup as part of your feminine look, Andie?”

His surprise at the question jolted Andy in his seat and he spluttered, “What? I… er.. no… no I… How did you know? I…?”

She smiled gently, but there was a mocking glint in her eye, “How did I know? You said so in your induction interview this morning, Andie. Don’t you remember?”

Andy remembered nothing of the sort. He could remember babbling answers to seemingly endless questions, but what filled his mind and blotted out any memory of what those questions had been was the overwhelming sensation of Miss Aulker’s highly-skilled fingers inside his body and the exquisite torture of the never-fulfilled orgasmic pressure it created that lit his mind with a blaze that blotted out all other thought. Sitting here in front of this controlling woman, now, that loss of control and, worse, the memory of desire and near ecstasy seemed more humiliating still and he flushed bright red.

Mrs. Reddin chuckled gently and spoke as if knowing exactly what he was thinking, “Yes, Jenny is rather impressive, isn’t she? Still, remembering or not I think it’s an oversight on your part that we need to begin correcting.”

Andy watched as she opened a drawer and retrieved a folding case, a roll, and what looked like a large makeup case. She put these on the desk near where Andy was sitting and opened them, unrolling an extensive set of makeup brushes, unzipping the makeup case full of carefully arranged sets of colours, and a case of all sorts of grooming contraptions. With a satisfied nod, she spoke, “Turn your chair and sit facing the end of my desk there, Andie.”

Andy glanced at the things on the desk in trepidation, then shifted around as ordered. Mrs. Reddin made a, “Hmm...”-noise and cocked her head as she regarded Andy, then lifted the desk lamp from the other end of the desk and placed it nearer Andy. She turned it on and angled it towards Andy, making him blink as bright spots flashed behind his eyes. She adjusted it and the glare reduced, but Andy was now brightly lit and feeling more self conscious than ever – a feeling that only increased as Mrs. Reddin perched herself on the edge of the desk facing Andy, her stockinged knees bushing his stockinged knees, sending shocks that had nothing to do with static electricity through him.

Andy squirmed internally and trembled a little with nervousness and sexual tension, trying not to stare too obviously at Mrs. Reddin’s fine legs and breasts so close to him. His cock hardened further in his panties as Mrs. Reddin contemplated his face, her touch electric as she cupped his chin and turned his face side to side. She carefully selected a tube of something from the makeup case, “Chin up and hold still, Andie.”

The thought of wearing makeup horrified Andy on one level and excited him on another. Mrs. Reddin selected a brush from the roll and began applying foundation to his face, the feel of the liquid spread by the brush both icky and sensual on his skin. Andy’s eyes weren’t really on Mrs. Reddin’s face despite his head being tilted back, but he saw her frown. She reached into the makeup case and plucked out a red band, which she fitted on Andy’s head – a hairband that pulled his hair back away from his forehead. 

Satisfied, she continued applying makeup. Andy had no idea what half the things she was doing to his face were about and it seemed to take an interminably long time. As the thoroughly caked feeling on his face grew, so did his feelings of humiliation, excitement, trepidation and curiosity, and he tried hard not to fidget especially after a stern rebuke and a slapped hand when he dared try to scratch his very itchy nose.

Finally, after what seemed an age to Andy but was in reality only a few minutes, Mrs. Reddin straightened and put down the brush in her hand. Her glossy, red nails once more took hold of Andy’s chin, more delicately this time, the points barely touching his jawbone, and turned his head side to side, inspecting her work carefully. A satisfied nod and the touch was gone. She began to pack makeup and brushes away and spoke casually as she did, “Not bad for a first time, I think; the overall effect is very satisfactory, even without taking it to extremes.”, she paused and glanced at him with a hint of a smirk on her mouth before going back to her packing, “You will have to learn to do this for yourself of course, Andie. I am not your personal makeup artist.”

Andy just sat there, conflicting feelings clashing inside him and a stiff, awkward, caked sensation in his face as she finished putting everything away and back into the desk drawer. She turned back and smiled, “It’s such a shame I don’t have a mirror to hand, but perhaps…”

She took out her phone and pointed it at Andy, the flash firing just as he opened his mouth to protest. His stomach sank inside him; despite the hold this woman already had over him, he had no desire for her to have a picture of him with his face made up in what he assumed was a very feminine way.

Mrs. Reddin laughed as she looked at the picture, “Oh, perfect!”, and turned to phone to show Andy. His jaw dropped and he gawked at it; he could hardly recognise the person in the picture! The headband swept Andy’s fringe back from his face, changing the shape of it to an oval and forming an almost bob-like style to frame it. That alone might have shocked him, but the effect of the makeup was startling; the first thing that caught his attention were the lips, now thick, plump-looking and a vibrant red colour just a couple of shades from pink. The changes didn’t stop there, though; his face looked thinner, more contoured somehow, his eyebrows now arched over eyes that looked much larger with long, dark lashes and rich earth-tones shaded around. He looked as feminine as he’d feared, but also much much less drag-queen than he had dreaded. The more he stared, the more he couldn’t link the face with himself at all and it gave him a strange, dizzy, doubled perception of himself that threw him utterly off-balance.

She put her phone away and Andy sat there, stunned and gawping at her as she sat back at her desk. Seated, she glanced at him as if surprised he was still there, “That will be all, Andie. I have work to do, and so do you.”, she gesticulated towards the connecting door to the small side office, “You may turn off your toy, but if you need to remove it, you must ask permission. Leave the door open so I can see whether your productivity is improving, please.”

Once again, Andy’s jaw dropped and he stared at her, but Mrs. Reddin ignored him – at least until he didn’t move for almost half a minute, when she turned her head and fixed him with a momentary glare than had him scrambling to his feet by the time her attention was back on her screen. Having lost all trace of grace with the swimming sensation in his head and stomach, he stumbled to the desk in the connected office and slumped into the chair.

Andy blinked at the computer in front of him, then took a breath and reached between his legs to switch off the toy humming in his aching arse. He looked over his shoulder through the open door, back into Mrs. Reddin’s office, seeing her working at her desk. He sighed, knowing she was entirely serious about him actually working, though he could not imagine how he was supposed to concentrate in the state he was in. 

He turned back to the desk and caught a glimpse of his reflection in the computer screen, again getting the odd sense of dislocation seeing the very feminine face and realising it was his own. Taking a deep breath, he turned on the computer and obscured the disturbing image, then tried hard to do some work without getting constantly distracted by his clothing.

It was hard, especially at first; dressing in women’s clothing was a thing of sexual fantasy for Andy and his thoughts kept straying to those fantasies and what he was wearing rather than what he should be focussing on if he wanted to avoid whatever probably humiliating and painful punishment his cruel new owner would inflict for failure. The toy inside him proved far too distracting; even when he could force his mind off his attire, the over-used sensitivity of his arse ensured that the slightest shift of the toy or flexing of his sphincter muscles against it all but blotted out other thought.

Asking to remove it was a nervous moment. Mrs. Reddin stalked into the room looking severe and disapproving, and stared at him for a long minute before tersely giving her permission and insisting he sit on the desk and spread his legs as she watched to remove it. Andy felt a little like a porn star posing as he complied with the instruction, but at least his distraction level was lower when she barked, “Back to work, Andie!”

He did manage some semblance of work – certainly more than he had achieved in the last few days – but the strange, out-of-body, doubled vision feeling never left. It hit especially hard when he had to talk to clients on the phone and he was intensely aware of his full face of makeup and of the skirt and stockings he saw every time he looked down. Worse, he was aware of his semi-hardon that still refused to quit in his tight panties and the wet-spot it generated in them.

Still, Andy did manage to do a little work, though his mind constantly returning to possible punishments for not doing enough as yet another distraction on top of the sensuous femininity of his un-disguised clothing and the feel of makeup on his face, did not help in the slightest. Any thought of work was utterly driven from Andy’s mind, however, a little before lunch when there was a knock on Mrs. Reddin’s office door. With a jolt of utter terror, Andy’s heart instantly began to race when he heard Mrs. Reddin call, “Come in!”

Andy opened his mouth to protest as he spun in his chair, then shut it with a snap, not daring to say anything as he heard the office door open. He stared wide-eyed at Mrs. Reddin sitting calmly at her desk, willing her to look at him and take pity, but she paid no attention. Andy spun back round to face his screen, his shoulders trembling in fear, as he saw the arm of whoever had entered reach past where the doorframe blocked his view, proffering a package across the desk towards Mrs. Reddin.

From behind him, Andy heard a voice he vaguely recognised as one of the HR juniors say, “Jenny Aulker asked me to bring this up to you, Mrs. Reddin. She said you’d be waiting for it.”

Mrs. Reddin’s voice was warm, “Indeed. Thank you… ?”

“Uh, Phillip”, the young, male voice supplied.

“Thank you, Phillip. I don’t think we’ve seen you up on this floor before, have we?”

“Uh, no Mrs. Reddin. I only started last week.”

The small-talk went on while Andy sat terrified, at once stiff as a board and trembling like jelly, trying not to breathe and hoping with every fibre of his being that the young man would stay hidden by the door frame and not see Andy in the side office. Not that he would know unless it prompted the lad to say something; Andy didn’t dare turn his head even a fraction of a millimetre to see and with his computer screen on he couldn’t see any reflection in it at all. All he could do was pray he was either not seen or feminine enough from the back to pass as a woman sitting there.

The ordeal ended as Mrs. Reddin dismissed the young man, thanking hi again, and Andy heard the main office door close. He breathed a heavy but carefully silent breath and his achingly tense shoulders slumped. Clearly, he had not been subtle enough in his relief; Mrs. Reddin’s voice floated in from the main office, “Back to work, Andie. It’s not lunch time yet.”, making him jump and scramble to get back onto the computer.

Andy’s concentration, such as it was, was wrecked. His mind refused to drop how close he had just come to being caught, how the makeup felt on his face, his his clothes felt, how sensitive his arse was, and how aroused and sensitive his cock. So caught up was he in his own thoughts that he literally yelped and jumped in his chair when Mrs. Reddin’s voice purred softly just behind his ear, “It is a little early for lunch, but since you seem to have no intention of working, Andie, you may take it early.”

Andy was even more stazrtled, freezing into place as Mrs. Reddin lent over his shoulder, her firm breast under blouse and lacy bra against the side of his face, her warmth pressing his upper shoulders. “Here…”, she purred, “Allow me.”

She moved his hand from the mouse and clicked around for a few seconds, bringing up another playlist of Femdom and cross-dressing videos, “You will masturbate to these today, Andie.”

Andy restrained a whimper with some difficulty. The thought of once again playing with himself in front of this woman, looking like he did filled him with shame and humiliation. On the other hand, he was unbelievably horny and at Mrs. Reddin’s mention of the word masturbate, his already semi-hard cock had sprung to almost full attention.

Resigned and, if he were honest, oddly eager, Andy hooked his fingers in the side of his panties and pulled it over his cock tucking it the other side to free it. Mrs. Reddin’s sharp voice interrupted him, “What do you think you are doing, Andie?”

Andy felt a frisson of worry that he’d managed to get himself in trouble, but looked at her confusedly, “Uh… I’m… doing what y...uh.. mas… turbating.. Ma’am?”

Mrs. Reddin frowned and tutted with some asperity, “Really, Andy! I thought you listened; you do not touch my cock without permission. You don’t play with my cock unless you earn it… and that you certainly have not! You have already touched my cock without permission. Since you have admitted to your error this morning you will not be punished for it, but you most certainly will not be rewarded for it.”

Andy’s jaw flapped as he tried to get his head round what his Mistress was saying, as his face twisted into confused incredulity and he stammered, “But…?”, Mrs. Reddin picked up the package she had brought in from her own office. Her red-nailed, manicured hand delved into it and retrieved an object which she held up between her fingers, her face twisting in a predatory smile.

Andy gasped, staring wide-eyed at the hot-pink, slim, smooth, vibrator perhaps fifteen centimetres long that she held up to his gaze. It was smooth, rubbery-looking, rippled with a bulbous end, and slightly curved. Andy couldn’t take his eyes off it as she spoke, “This is how you will masturbate today, Andie. Much more suitable than that little plug you wear; with this you can imitate the videos you will watch.”

She held it while Andy continued gaping, frozen in his chair as he processed what she was saying until the terse voice cut through his inaction, “Well, Andie! Take it!”

His hand reached for the toy as if compelled and he took it in his own shaking fingers, feeling the firm yet flexible, smooth, warm texture of it. His fingers played across the surface, trembling, while Mrs. Reddin put a bottle of lubricant with a pump top on the desk where it sat almost innocuously like a hand cream dispenser yet Andy felt like it, too, was staring at him.

“Well, Andie? Take your panties off, remove your plug and masturbate for me.”

The words were mild, but Andy heard the order in them nonetheless. Unsure fingers scrabbled down his panties and probed under his aching balls to grasp the end of the toy in his throbbing arse.

With both in his hands, he looked around uncertainly. “Put them on the side of your desk, Andie. Then you may put your feet up on it so you have better access to your pussy-hole. 

Andy cringed at the word inside, but determined not to give her the satisfaction of reacting to a word obviously designed to humiliate him more. He did as he was told, once again feeling a little bit like a porn star with his stockinged legs up and spread on the desk and no panties on, looking at his heels framing the computer screen. “Now… pick up the nice, pink toy and masturbate, Andie. You know what to do; don’t try my patience so!”

His face twisting with conflicting feelings, Andy picked up the bright pink toy and the bottle of lube while Mrs. Reddin reached over and started the video playlist. Somewhat predictably since the woman had obviously planned this, the first video on the playlist was one Andy had seen before with a cross-dressed slave strapped to a table with his leather-clad Mistress fucking him with a hot-pink strapon. The parallel was obvious and a little worrying, but Andy knew better than to protest at this point.

He had to admit, the toy was a good one; the bulbous head wasn’t huge, but stretched his anal ring smoothly as it pushed through. It went in easily with the preparation afforded by the smaller plug, and with the heightened-sensitivity of Andy’s over-used hole it was right on the border between feeling amazingly arousing and being actively painful. He felt a slight tingling inside; not quite burning, but definitely a new sensation. As he gently probed the toy deeper, he found the tingling growing and the toy almost seemed to slide in easier. 

He knew what Mrs. Reddin wanted and, truth be told, he wanted it too; he began to slowly slide the toy in and out of himself, finding the control on the end to make it hum gently. It felt good. Better than good in fact, even with the tender pain of the over-sensitivity and stretching. The more he slowly worked the smooth toy into his body, the easier it seemed to get. The ache and even the sensitivity faded a little and by the time the video got to the bit where the leather-clad Mistress had her slave tied down and was pushing her strapon through his crotchless panties, Andy’s hand was working on auto-pilot, barely noticing the ache and pain over the arousal of the film. 

As the fucking sped up, so did Andy’s unthinking hand, hot pink between his legs keeping pace with the hot pink on the screen. His arousal soared, spinning his head, though his cock got no harder and his orgasm grew only slowly closer. He didn’t care; his head was lost in some of his favourite scenes. He barely noticed when Mrs. Reddin leaned over, taking the lube bottle and squeezing more onto the pink toy as he fucked himself. The cold of the lube aroused too, the tingling increased and his orgasm drew closer. Slowly, slowly, Andy could feel his orgasm swelling and growing. Not in his cock, but deeper inside, somewhere in his stomach and behind his balls. He’d lost track of how many video clips he’d watched, just knew it was lots, just like he knew it was more than once that his Mistress had added the tingling, numbing lube to the vibrator.

His orgasm swelled inside, not urgent and achingly pointed like normal, but wider, larger, pressing throughout his belly and he just knew that when it came – when that glowing spot deep inside where the toy pressed on each thrust spread right through him – it wouldn’t be an explosion, but a flood that would carry him away into bliss. It was close; he could feel it. So close, so… not urgent, but necessary, something he needed badly. His vision blurred, tunnelled onto the latest clip on the screen – another pegging clip and one of his favourites – and he could feel that spread, the heat in his belly, through his pelvis, making his hard cock throb though it had little to do with it. He knew that when the slow creep of heat completely filled his balls, the flood would begin. So close.

...And then the screen went blank. The shock of disconnect and loss of visual reference stopped his hand moving and, before he could complete the all-engulfing orgasm, his Mistress’ hand came in, pushing his unresisting hand aside and pulling the toy out of his body. His body shuddered in reaction, the hot, swelling feeling slowly seeping away leaving cold shame and flat, dull ache in its wake.

It took Andy some time before he could get control of his limbs properly because they felt so weak. His vision stayed blurred for a while too. When it cleared, Mrs. Reddin was standing, smiling, the toy and lube were gone, the screen back on his work.

She looked at him until she was sure he was focussed on her face, then said brightly, “Lunch time is over Andy; back to work! Oh, and you need not put your toy back in this afternoon; I think you have worked your pussy-hole enough for one day. I suggest you put your panties back on, though.”

Then she was gone from the room, back to her own desk, leaving the door open so she could check on her charge.

Andy got little, if any, work done that afternoon. He felt ashamed of himself for getting so lost in his fantasies in front of the controlling woman who already had more than enough hold over him. He felt frustrated by the lack of release and his cock cycled between semi-hard and soft, leaking into his panties often. The horniness had nowhere to go and he felt sour in the stomach, on edge and unfocussed. As the tingling faded in his arse – his… “pussy-hole” – the aching sensitivity re-asserted itself, then redoubled. Still, his frustrated horniness wouldn’t let his erection completely fade and even when he tried to focus on work, he found his hand straying towards his panties and the leaking bulge in them. Each time he caught himself, he would twitch his hand away guiltily and glance over his shoulder towards his Mistress sitting working unconcernedly in the other office.

Andy struggled through until the end of the day, occasionally managing to focus on work for a short time despite his state, but only when a sharp bark from Mrs. Reddin about his distractedness made fear of punishment over-ride the shame, ache, horniness and soreness sloshing around his body.

All afternoon, Andy held the contradictory hopes both that there would be no further humiliations today and that he might be allowed to orgasm, which would almost inevitably carry a cost. When he clock-watched, time seemed to crawl, but his distractions caught up with him and made time jump forward, so he was startled when he heard Mrs. Reddin’s door open.

Andy panicked, assuming one of his colleagues had come into the office without knocking. He froze, staring at the screen. He noticed it was past the end of the working day about the same time he recognised Miss Aulker’s voice behind him. He dared to turn in his chair just in time to see the two women step away from each other as if they had been embracing, perhaps even kissing. Andy’s brow furrowed, but then he forgot about it as Mrs. Reddin laughed and gestured towards Andy.

Miss Aukler turned and smiled a predatory smile, walking slowly into the office where Andy sat, the motion of her lithe hips as she moved full of sensual menace. Mrs. Reddin stood and followed, speaking as Miss Aulker reached him, “Jenny and I noticed that my penis seems to be misbehaving in your panties, Andie. We imagine it’s a little… embarrassing to be so excited by your new life – around the office at least. While that’s fun in a way, we decided to help out; take your panties off for us, Andie.”

Andy had a horrible feeling that the “help” was going to involve some new humiliation that would be even worse than the problem, but he had no choice. He stood and skimmed up his skirt, reaching for him panties. Before he could get there, Miss Aulker slapped his hand away, “Allow me, Andie.”, her voice full of suppressed glee that worried him. 

Even with the worry, his not-completely-soft cock twitched as the attractive woman stepped close behind and he felt her warmth and the jut of her breasts against his back while her fingers hooked in the sides of his panties, pushing htem down overhis suspender straps and stockings to fall around his ankles.

Mrs. Reddin stood in front of him watching and even after repeated exposure, Andy still felt small and humiliated as she regarded his naked, hairless, twitching cock impassively.

“Step out of them, Andie and put these on. Pull them up only to your thighs.”

A hand came round his shoulder to dangle something in front of his face; a pair of panties, plain, looking like a thong, literally flesh-coloured in a shade close to Andy’s own skin. He frowned in confusion and took them, finding them slick and soft to the touch, small in size, and made of a tight, stretchy material, probably with a high lycra content.

Under the daunting gaze of Mrs. Reddin and with Miss Aulker breathing down his neck, he did as he was told, finding the material tight and binding around his thighs. The feeling was made worse when Miss Aulker ordered, “Move your legs apart a little, Andie; until the panties are as stretched as you can comfortably make them across your thighs will do.”

When he straightened, the stretchy material cutting into his thighs, the warm presence pressed against his back again, tighter this time. “Don’t move, Andie.”, purred in his ear and he felt hands, now covered in gloves, pushing between his arms and body, slipping round his waist towards his cock, making it twitch like crazy and begin to harden a little.

“Pay attention, Andie, this is a teaching moment.”, Mrs. Reddin’s words were redundant, startling him a little since he was so focussed on what the hands were doing already, though it did make him wonder what she meant.

The hands slipped towards his cock, moved past them and cupped his balls, one in each hand. He breathed in sharply in surprise, then hissed a little at the strange, yet oddly familiar, sensation of pressure as Miss Aulker pressed and manipulated them. Andy placed the feeling; it was a lot like what Miss Aulker had done that morning, but without the distraction of her expert fingers fucking him. Without anything else to think about, Andy actually felt his balls push back up into his body. It was a unique sensation, not painful as such, but not comfortable without the distracting pleasure. 

Andy’d body began to tremble slightly with the effort of self-control, the fear of humiliating consequences still larger than the desire to end this uncomfortable feeling. He felt Miss Aulker’s hands move again, her left hand slipping over both his balls, pressing, holding them in place inside his body. The other moved up, taking hold of his cock, which hardened a little more, though the touch was business-like rather than sexual. The right hand pressed his cock down, again causing discomfort that bordered on pain as it bent against the profusing blood trying to straighten it. The more the hand pressed and the more his cock bent downwards, the more uncomfortable it became and the more the unpleasant sensations filed his concentration, taking it off the warm, lithe body pressed against his back of the fact of a woman’s hands on his cock. 

His cock went almost completely limp in response and Miss Aukler pressed his cock fully between his legs, the tip almost covering his arse hole as she slid her left hand from under it, instead using his own cock to hold his balls in place inside his body. The now free hand pulled at the skin of his scrotum left at the sides and wrapped it up over his cock, the right holding everything in place. 

Andy was at once horrified and fascinated by the process, not daring to look down, but feeling the strange effect intensely. So intent was he on how it felt that he jumped a little when the purring voice murmured in his ear, “Pull your new panties up over my hand, Andie. Get them nice and snug.”

For the first time, Andy had an inkling where this was going and, sure enough, when he did as he was told, Miss Aulker pressed her spare hand over the top of his panties and carefully slipped the hand inside out of the waistband. A moment later, the warm pressing was gone from his back and a shiver passed through his body. Finally, he looked down and had a moment of disconnect; his groin was smooth, the new panties not quite blending in to his skin tone, but close enough, and certainly they bound tight enough to keep everything in place. With shock he found that, looking down, it was almost like he didn’t have a cock. 

When he looked up, the two women were studying him with pleased looks on their faces, though of course it was Mrs. Reddin who spoke, “Very nice, Andie! Now put your panties back on – no, over the top if you please.”

Andy pulled his panties back on, the lacy thong sitting more snugly on his body than it ever had. It felt odd not to feel the lace against his cock, odder still the sensation of his cock pulled back between his legs and his balls inside his body. That and the disconnect of not actually pulling up his panties over a cock of any kind had him slightly freaked out and he felt slightly disconnected from reality.

Reality intruded when Mrs. Reddin ordered him to pull his skirt down and straighten his clothing. She then ordered him to step forward and stand up straight. He felt a little unsteady, but did as he was told. The unsteady feeling wasn’t helped as the two women stalked around him like lions circling a gazelle. They stepped back and Mrs. Reddin smiled broadly, “You look wonderful Andie!”

Her phone came out again and Andy quailed, but didn’t dare turn away. After a nod from her, Jenny Aulker did the same and the pair of them moved around him again, snapping pictures, Andy’s stomach turning with each click and flash.

Done, Mrs. Reddin turned the phone for Andy to see; he gaped at the picture – a side shot where he had turned to look at the camera as he’d been told. Three things struck him; first, he could barely recognise himself in the makeup, second, that there was literally no trace of a bulge of a cock under the tight skirt even from the side, and third, that the figure in the picture looked far more feminine than masculine despite the less than feminine hairstyle. The feeling of disconnect grew and Andy felt for a fleeting moment that he’d lost himself.

“Walk for us, Andie.”, once again he was so distracted, the order made him jump. It felt awkward to even take a step as he was, but he took one anyway and found that, strange feeling though it was, it was no more uncomfortable on his cock walking than just standing still. That didn’t mean it wasn’t utterly weird though; moving made him intensely aware of how constrained his cock was, bound up between his legs. He was intensely aware of the flatness of the front of his skirt as he moved. The whole thing just seemed so… unnatural… and yet, like the makeup, there was a strange excitement to it. 

He’d done two laps of the office before Mrs. Reddin’s words cut through his distraction, “Walk properly, Andie. You know how; shoulders back, head up, lead with your hips!”

It was hard, but Andy forced himself to focus on his walk, dragging his concentration from the position and sensations of his cock was not easy. For another couple of laps, he was afraid he was going to earn some sort of punishment for not walking properly, but fortunately all the practice he’d had kicked in and he found that the “proper” walk was becoming second nature and didn’t require his entire concentration. It was just as well because he couldn’t drag his attention away from his cock – or lack of one! - but managed to find the walk that Mrs. Reddin demanded.

When he found his stride, he got an encouraging, “Well done, Andie.”, from Mrs. Reddin, but then, as he kept walking laps of the office, swaying his hips and trying to get used to the odd sensations between his legs, Mrs. Reddin began lecturing him.

“The garment you are wearing is called a gaff, Andie. It is there to hold in place your ‘tuck’. Your testes have been pushed back into your body where they were when you were young. This ‘tucking’ will become an everyday thing for you and will help you not be so concerned and distracted by how much your body enjoys your new situation. Put indelicately, it will stop your hard-on showing through your clothes in the rather unsightly way it has been. Do you understand, Andie?”

Andy stumbled in his walk then recovered, gaping at the women (Miss Aulker was standing next to Mrs. Reddin, smirking), his attention finally mostly dragged away from the feel of his cock.

“I asked you a question, Andie.”, her voice veiled a threat.

“Uh… no… uh. Ma’am… not… entirely…”

“I’m saying I expect you do learn this skill, Andie, and to use it every day at work or when I order. On your own time, you may do as you wish, though I suggest you practice for now at least. It is quite safe, though it may take some getting used to I understand. If things get uncomfortable, you may simply re-arrange – discreetly – or release yourself for a short time. However, I expect you to spend as much of the day as possible properly tucked away. If you become aroused, it may get a little painful, but it is not dangerous. It is something you must simply get used to.”

Before Andy could even process that astounding statement, Mrs. Reddin went on, “Speaking of which, walk to my office and bend over my desk please, Andie.”

With a sinking feeling of horrible anticipation, Andy did so as the two women followed him. He’d barely bent over when Miss Aulker was behind him, pushing his feet apart almost roughly, one gloved hand yanking his skirt up to his waist, then pressing in the small of his back, holding him down. The other felt wet and cold between his buttocks. It felt like a finger or fingers curled under both his panties and the new ‘gaff’. The slimy fingers brushed against his tucked cock-head as they forced their way insistently into his sensitive arse hole and fucked him hard and fast.

Andy yelped and gasped, struggling minimally against the hand holding him down and the feet holding his of apart apart. It wasn’t especially painful, though the over-used sensitivity of his now frequently invaded arse did add a discomfort that bordered on pain, but it a was hard and fast invasion, rough, demanding, unforgiving and seemingly unconcerned with his consent or reaction. It was a violation, a taking, and Andy felt it. He could feel his confidence withering under the onslaught, worse as the tingling semi-burn of the lubricant dulled the pain and turned the almost brutal fucking of the undeniably expert fingers into something that might have been pleasure in less humiliating circumstances.

Andy began to feel his cock straining against the tight lycra holding it in place. Worse, the urgent, insistent fucking of the fingers rubbed his cock head, spurring arousal despite his mind protesting this violation. His balls began to ache inside his body and he could hear himself panting. Somehow, Mrs. Reddin standing in front of him watching his face impassively as he was taken just made it worse. 

He felt the stretching of his hole increase as another finger forced its way in, the fucking relentless, the stimulation intense. His cock strained to get hard, frustrated by its bindings, but full of blood and leaking its juice. Andy heard his own panting get harder, taking on the fast, urgent, hard, brutal rhythm of the fucking. Arousal grew, as hard and urgent as the fucking, the pressure inside growing aided by the constant, if rough, stimulation of his cock head as the fingers forced their way past it to enter him over and over. The orgasm-like sensation of the morning grew once more and grew and grew until his body craved the violation to continue even as his mind screamed at its betrayal. He was so close, and the explosion would be epic.

And then it was gone. The fingers whisked out of him leaving his arse empty and without stimulation. His body shuddered and flopped on the desk in reaction to the sudden lack of input. He could feel his arse pucker twitching as if trying to seek out the fingers that has brutalised it. He felt weak and vulnerable and he barely heard Mrs. Reddin’s matter-of-fact voice above him, “That will be all for today, thank you Andie. Jenny and I have some work to complete, so we will see you tomorrow. Be in Jenny’s office bright and early in the morning and make sure you are properly tucked when you do. You will find your disguise and makeup remover in the last stall of the ladies toilet one floor down. By the way, the lift is out for maintenance; you will have to take the stairs. Good night, Andie.”

In a daze, Andy felt Miss Aulker’s strong hands help him to stand and stumble to the door. She all but pushed him through it and he almost collapsed as the support left him. He heard the door close firmly behind him and the lock turn; there was no way he was getting back in there. He stood swaying in the empty and open office, his clothes in disarray, his appearance almost entirely feminine, felling confused, helpless, small, and violated with no real clue what to do next.