Lyndseygurl's Sissy Captions

Andy couldn’t remember a thing about his journey home. He found himself quietly opening his front door late at night. The house was dark and silent and it seemed Claire was already in bed. Whether he’d sat in the dark office for hours or wandered on his way home he wasn’t sure. His cock and balls were still hot and aching, his arse hole throbbing, and his arse cheeks burning and uncomfortable to sit on as he slumped into the chair of his home office. He found he was still dressed in his female clothes under his top clothes and hoped fervently that no one had noticed on his way home. It seemed the only thing he’d taken off had been his heels. How anyone wouldn’t have looked at him he didn’t know; his face was still a tear-streaked mess and his male top clothing was badly buttoned and dishevelled-looking as he stared at his reflection in the dark computer screen on the desk.

That and the aching in his panties reminded him of Miss Aulker’s threat and spurred him into action despite the weariness of his abused body. He fired up the computer and rummaged in his bag as it booted, breathing a sigh of relief when he found the USB stick along with his toy in it. He plugged it in and found that all it contained was a file with a sort code and account number. He stared at it, horrified by what it had come to, having trouble believing he was even considering this. Except he wasn’t considering it; he was gathering his courage to do it. He examined his choices, which both helped with the courage and depressed him at the same time. 

He could go to the police and explain how these women had tried to blackmail him… Yeah, sure! He could go to the police and out himself as a cross-dressing pervert and give them all a good laugh, have his wife find out, and no doubt have the two women produce the tape of him in the office to paint him as a deranged liar. All before finding out the bank account number didn’t connect to his tormentors and he had nothing but his own accusations that they could portray as attempted retaliation for the charges they could level against him with evidence, even a confession, to back it up!

He could simply not do it; there was nothing to say he had to transfer his money to this new account and they couldn’t make him… Except they really could. Both Mrs. Reddin and Miss Aulker had suggested they could devise far more painful games to play if Andy didn’t co-operate and while he could, of course, refuse to play those too, there was always the spectre of them simply letting him go and the public consequences of the situation he had very much got himself into and could blame on no-one else if they chose to reveal it.

“Besides,”, he tried to convince himself, “they said they’d use it to have me buy stuff for their games… Perhaps it won’t be all bad. I mean, I like getting new lingerie and clothes.. maybe even another toy or two… They probably want to use it for online shopping and have stuff delivered to work. Yeah… it’ll be fine… Some of it is… well it’s fun, really isn’t it? It’s OK to admit it… I mean it’s not your fault you have to cheat on Claire and they are sexy women. There’s a bit of you wants this isn’t there? Go on, just go with it… It can’t be any worse than the alternative, right?”

Having convinced himself, her called up his bank account, looking at the balance then spending some minutes flicking through his old statements to see how much he generally spent in a month. Beyond his travel fares, it really wasn’t that much; lunches, the occasional magazine, some purchases that were often as not the kind of stuff he’d probably be buying out of the transferred money at his tormentors’ urging. Still, he gave himself a good cushion of funds and set up the transfer to the new account. He looked at the regular transfer to his joint account with Claire and wondered how much the raise Mrs. Reddin had talked about would be. Not that he’d see any of that money if he obeyed Mrs. Reddin’s order, but it would earn him brownie-points with Claire; ironic that it would be for essentially cheating on her and that he probably wouldn’t be able to take advantage of her goodwill for fear of her finding out the source of his largess.

Done, Andy shut down the computer, becoming aware of how sensitive and border-line uncomfortable his intimate areas were. He undid his trousers, sliding them down his hips and pulling up the skirt underneath. He inched his hips of the chair, sliding down his panties too and frowning down at his cock as he sat back on the chair. It was reddened and a little blotchy, perhaps swollen a little, but it didn’t look damaged. 

He prodded his cock gently. Finding it extremely sensitive to touch, but not actually sore as such, except for the reddest patches. Surprisingly, it twitched and began to stiffen slightly, which make the ache grow and he stopped prodding, instead cupping his balls. They, too, were extremely sensitive and ached as he cupped them, even without squeezing. Then he remembered Mrs. Reddin’s order not to touch himself and his hand jumped away from his balls as if they were burning hot instead of just warm. He chuckled to himself nervously, torn between amusement and concern at his own reaction when there was clearly no way he could get into trouble. “I mean, maybe the bitch can tell if I cum, but it’s not like she’s going to know if I just touch it, is it?”, he thought to himself.

Even so, Andy sighed and stood, stripping himself naked, tucking away the dirty female clothes in the secret stash in his home office and plucking out a discreet pair of plain, black briefs. He picked up the male clothes and cracked open the office door. He listened and, hearing nothing, padded quiet and barefoot upstairs, dropping his clothes in the laundry hamper and retrieving a pair of pyjamas from the airing cupboard. Signing again, he decided to sleep in the spare room rather than risk waking his wife and having to answer question in his emotionally and physically fragile state. Andy was so worn out from the day that blackness claimed him almost the moment his head touched the pilow.

He woke the next morning and found the master bedroom door open and heard his wife moving downstairs. He took a moment to take stock of his body, finding it tired and slightly achy, finding his cock and balls sensitive and throbbing, though not especially uncomfortable, and his arse felt… He considered it, finding he didn’t have a word to describe it. He could feel where his arse had been fucked, feel the sensitivity, the… sensitivity?… inside, was conscious of the twitching of his arse pucker. He couldn’t describe it as actually sore, but it also wasn’t exactly comfortable. If he admitted it to himself, he might have said it was oddly pleasurable.

The noise of crockery pulled his attention away from himself and back to his wife, who he both wanted to see and didn’t want to face. He forced himself out of bed, wrapped a dressing gown around himself and padded downstairs. His wife turned at the kitchen island as he came in the room, pushing a cup of coffee across it, “You were in late last night.”

The tone was mild, not at all accusatory, but Andy felt the accusation in it nonetheless and his heart rose into throat along as his guilt congealed in the pit of his stomach.

“I, uh… It’s the new job… There’s, er, training and stuff… and longer hours…”

Claire turned back and looked at him and he desperately hoped he wasn’t blushing, “Oh…?”

“Uh, yeah…”, he tried to segue to less dangerous territory, “...But at least I get a raise out of it… I… um… don’t know how much, yet, but… I, uh, think I should put it in the joint account.”

Her eyebrows raised, “Really?”

He felt hot, like he was flushing, but he hoped now he might get away with it if he were, “Yeah… Well, you pay way more than I do… I… uh… thought if I put my, um, raise towards bills, you can… could… spend a bit more on yourself… Y’know, like I know you like spa days and stuff.”

Claire smiled and laughed, “That’s sweet, dear. Well if that’s what you want.”, she downed the last of her coffee and grabbed her bag, coming round the island and giving Andy a little peck kiss on the lips, “Thank you, darling.”

Andy smiled tentatively and Claire smiled back, “Gotta dash. Big meeting this morning.”

She gave him another peck, this one on the cheek and hurried out leaving Andy standing relieved and for some reason a little hurt in his kitchen.

With the house to himself and enough time before he had to present himself to Miss Aulker (a thought that horrified him even as it made his cock twitch in the tight briefs), Andy decided to groom himself and carefully pick out an outfit to wear. The feeling of caving in to the demands of the cruel woman who had so much sway now over his life made him feel as low as he had since the first meeting, but still the smoothness of his skin when he was done felt sensuous, especially in the new places further down his chest and legs where he had extended the depilated areas slightly and there was a forbidden excitement in the shorter hair on the rest of his body, even while he was terrified that Claire would catch it and not accept his excuses. He couldn’t resist running his hands over the smooth skin of arse, trailing his fingers into the tight crease to touch the sensitive pucker that had been invaded so many times in the last few days. He felt his cock twitch and instinctively wrapped his hand around it, the other cupping his balls, feeling the silky smoothness there that always made his cock stiffen… Until he once again remembered the prohibition against touching himself and his hands flew from his crotch as if shocked. He laughed at himself again, knowing there was no way the scary Mrs. Reddin could ever know. Still, his hardon had wilted and the moment was gone. It was time to get ready for… work.

Andy felt even more ambivalent about getting dressed. He got out some of his favourite lingerie and clothes and chose carefully. He got his usual thrill from picking the perfect outfit from his selections and dressing slowly and carefully in it as he usually did when he had the alone time to do so had him as excited and aroused as ever. However, at the same time, he was excruciatingly conscious that it was different; he was doing it now not for his own pleasure, but at the orders of a cruel woman who now ran his life, made choices for him and could ruin him at any time she chose. The dichotomy made Andy sort of hate himself for being excited and also feel completely ashamed of himself for it, especially since the fear somehow managed to make his dressing feel more intimate and fresh than it had since he’d first started experimenting. As he pulled chinos and a shirt over the red lingerie set and black, skimpy stretch skirt and scoop-necked, sleeveless blouse, he found his cock hard in the lacy thong, the suppressed arousal that had been denied release the night before flooding back, making it throb and swell, straining against the thin, soft material.

He almost decided to change to something less arousing, but he told himself he didn’t have time otherwise he’d be in trouble for being late to Miss Aulker’s office. The real truth, though, was that changing would likely make very little difference, especially when his few pairs of plainer briefs did not come as sets and he would have to wear one of his sexy bras anyway and he knew from experience that wearing unmatched lingerie would stick in his mind and just make him more self-conscious. 

He did worry, though, that his hardon, which showed no signs of fading completely since it twitched every time the soft, smooth material moved against his cock, balls or between his arse cheeks, would be noticeable on the way into work, or even worse at work. Quickly, Andy rummaged in the back of the hall cupboard and found his overcoat. It was the wrong weather for the overcoat, but at least it was thin and the length would help conceal his crotch. Sighing, he left for work.

The journey was every bit as uncomfortable and embarrassing as Andy had feared. His cock didn’t soften completely and certain movements made it harden more as his lingerie rubbed against sensitive parts of his anatomy. Due to the overcoat he thought no-one actually saw, but when he walked again into the personnel office he felt shamed and small and exposed as he walked past the young man who was the only one at his desk this early to knock on the door of one of the two women who seemed determined to turn his life into an endless, if secret, humiliation. His stomach flipped when he heard the clipped, “Come in!”, from the other side of the door and, taking a deep breath, opened it.

Miss Aulker was sitting with her back to him in her office working on her computer. Andy knew what he had been told to do, but suddenly, even after all the things that he’d suffered over the last few days, embarrassment and humiliation at the thought of stripping off his top clothes and crawling for this woman welled up inside him, bringing tears to his eyes and a sick feeling in his stomach. Nevertheless, Andy put his bag down and got his shoes out then resignedly began to strip his outer clothes. Fully en-femme with tears still pricking his eyes, Andy got onto all fours to crawl the few steps to the waiting tormentress. Only then did Miss Aulker acknowledge his presence by swivelling in her chair and looking down at him with a cruel, self-satisfied smile on her face before delicately extending a deep red, patent, high-heeled pump for him to kiss.

“Well done, Andie. You may kneel up. So… how are we feeling this morning? Sore? Horny?”, the grin got wider, “Embarrassed?”

Andy hung his head and nodded jerkily. “Which?”, prompted Miss Aulker.

Andy swallowed before mumbling down at his blouse, “All of them…”

She laughed merrily, “Well that’s good! Let’s see what we can do to keep that going!”

Her face turned more serious, “I also saw you transferred the money. Well done. Did you also manage to refrain from touching Mrs. Reddin’s cock?”

Andy tried the prepared lie, “Um… Yes I did… I mean, I didn’t touch...”, it didn’t sound convincing even to him as it came out of his mouth and though Miss Aulker’s face didn’t change Andy suddenly felt pressured into qualifying himself, “...uh.. that is… well I… uh.. didn’t wan… uh.. play or anything, but… well.. I… uh.. it hurt and… I just.. checked it wasn’t… uh… damaged…”

At that Miss Aulker raised an eyebrow though she said nothing and Andy felt like he was shrinking in on himself.

Andy expected an angry accusation for the admission, or punishment or anything, but instead Miss Aulker seemed to breeze right past it, “So today you will go through the… hmm… induction and… paperwork for your new role. You understand that this is normal HR policy, yes, Andie?”

His brow furrowed, “Er… yes?”

She was suddenly brisk, “Good! OK, Andie, up you stand; hands on head and feet shoulder width apart for me.”

Andy did as he was told, tottering a little in his heels as he got to his feet and trying to avoid looking down at Miss Aulker still sitting in her chair a couple of feet in front of him.

Andy’s jaw tensed when Miss Aulker raised the hem of his short skirt and laughed on seeing his cock semi-hard in the tight, red, sheer panties. Her finger ran teasingly along its outline and tested the damp spot at the end where pre-cum had leaked out during his journey to work. His cock twitched and he shuddered slightly, letting out a tiny sound somewhere between a gasp and a whimper. Miss Aulker laughed again, “Well, it seems at least one part of you is quite enjoying your predicament, Andie! Tell me; is this how much dressing like this normally turns you on?”

Andy hesitated. Somehow the prospect of talking about his fetish and perversion seemed more humiliating than being made to demonstrate it – especially when the evidence of his desire was right in front of her face. Miss Aulker glanced up at him, her smile gone and her face severe, “Mrs. Reddin is not going to be pleased if her new employee’s induction does not go smoothly Andie… And you understand that both your Director and HR expect full disclosure in these induction interviews? There will of course be penalties – possibly even legal penalties – if you fail to cooperate fully with the process…”

For a moment, sharp nails dug through the thin material of Andy’s panties into the super-sensitive flesh just below his semi-hard cock head and he tried hard to stifle a yelp that might be heard by the young man in the outer office. Terrified, he began to gabble a response, the first thing that came into his mind, “Yes… yes… it turns me on… it always turns me on.. ever since I tried… but I don’t always get… hard like this.. that’s.. because… you.. uh.. Mrs. Reddin… because…”

The voice was a teasing purr in his ear as she stood and stepped behind him, “…Because the things we do make you so excited even while you hate us for it, Andie?”

He nodded shakily, “..And you do like it, don’t you, Andie?”

He let out a small whimpered, his skin tingling with the soft, warm breath on his neck, and nodded again, “I want to hear you admit it out loud Andie. Do you enjoy what we do to you?”

He could barely force a sound from his mouth but he was too terrified not to answer and the throbbing of his now fully-hard and once more leaking cock in his panties would immediately put lie to any attempt to say no so he forced out the confession through a half sob, “Yes… I.. enjoy what you do!”

He could here the satisfied smile in her voice at the confession, “Do you know what I enjoy, Andie?”

He guessed the question was rhetorical and didn’t answer, clenching his jaw as Miss Aulker’s strong hands cupped his buttocks and squeezed, causing stabs of pain from the still-smarting cheeks, “I enjoy turning these cute cheeks all hot and red like naughty gurls who masturbate in the office deserve…”

Andy whimpered as her fingers ground into the welts left from the previous night’s spanking, “...but I also enjoy playing with this tight, little hole like it’s a naughty, hungry pussy…”, the squeezing stopped and her fingers trailed up the material of the red thong buried between Andy’s arse cheeks and pressed against his aching, sensitive pucker making him gasp.

The finger tip massaged, “I’m really not sure which I prefer doing… I think I know which you prefer, though, Andie; you squirm and moan so prettily and get so swollen and wet in your panties when I treat your cute, little hole like a pussy, don’t you? I think I want to enjoy myself while we go through the boring questions for your induction, Andie, but I just can’t decide how to enjoy myself.”

The room was quiet for long moments while Andy stood there, vulnerable with teasing fingers working the tin strip of silky material against his sensitive pucker, utterly humiliated both by his own passivity and the words of his tormentress. The longer he stood, the more his humiliation deepened as his awareness grew of his cock straining, oozing and twitching in his panties in response to the twitching throb of his sensitive, teased pucker. He was forced to admit to himself the truth of Miss Aulker’s words; her expert invasion of his arse with her fingers not only aroused him, but aroused him perhaps more than anything he’d experienced – certainly more than the poor, hurried, routine sex of his marriage in the last few years.

It came almost as a shock interrupting the ebbing and flowing sensations of arousal and shame when she spoke again, “I was going to do my favourite thing while we do the induction – to help you focus on it properly…”, she sighed theatrically, “but now I can’t decide which to do…”

There was another pause where the teasing against his sensitive pucker continued, perhaps even intensified though he couldn’t be sure.

Long moment later, Miss Aulker’s voice came again, this time with an overtone of surprised revelation and just a hint of slyness, “Maybe you have an opinion, Andie! Perhaps you have a favourite of the two that you would prefer me to do? I suppose if you were to ask really nicely it might convince me nad help me make up my mind…”

Even in the detached, floating sensation caused by her teasing and his embarrassment, Andy had been semi-expecting her to steer thing this way and had been dreading it – both because he knew he would indeed humiliate himself further by asking for one as she demanded, and because he knew now that convincing her to choose the less painful option wasn’t just about avoiding the pain.

It seemed he’d hesitated too long because Miss Aulker’s voice took on a slightly sterner note, “Well, Andie? If you can’t help me decide, perhaps I should just do both…?”

He gasped at the thought and stammered, “The… would you… uh… you fingers, please?”

She feigned incomprehension, “My fingers Andie? Whatever do you mean?”

Once more his eyes pricked with tears of shame – mostly shame that a part of him wanted it so much – and he almost whimpered, “I… please… finger… fuck… my… arse…?”

The fingers stopped moving and pressed, almost forcing the thin, silky, strip of material into his sphincter, “Oh! You like me playing with your pussy-hole, do you Andie? You like my fingers inside you fucking you like a girl? Is that what you want, Andie? Is that what you’re asking for?”

He swallowed and whispered, “Yes…”

The fingers vanished, the feel of Miss Aulker’s breath against his neck was gone and a moment later, she was in front of him. She caught his chin and sighed, “No, I’m sorry Andie I don’t believe that for a moment. I suppose I’ll just have to amuse myself while we conduct the induction.”

She let go of his chin and bent to the desk drawers, opening one and laying out a ruler, a short leather paddle and the feared riding crop onto the desk top above it before she straightened.

The sight of the cruel implements made Andy’s arse and cock throb in remembered pain, then a moment later his mind was filled with the loud splats and cracks of those wicked tools hitting his flesh and the thought of the young man working just the other side of the door that suddenly did not look nearly heavy enough. Panic filled him at the thought, not so much that Miss Aulker might hurt him with these things – a part of him was beginning to accept that as inevitable – but that the noise on his flesh and his inevitable squeals would out his shame to the innocent young man in the next room.

“No! Please!”, he blurted, louder than he intended, then went on in a forced hush, babbling his protest in a desperate semi-whisper, “Please…. Don’t! Not those… Please… I… really.. uh… really want your fingers…. Please? How can I convince you? I don’t…. it’s too… just not those!”

Miss Aulker straightened and turned back to him, her eyes capturing his and holding them until his protests petered out and he blushed, “What can you do, Andie? I don’t know; what can you do?”

He smile was back, predatory and self-assured, “Oh! I see… you want me to help you? You want me to give you tips on how to ask to have your pussy-hole finger-fucked?”

Andy’s throat felt blocked and his jaw moved soundlessly, incapable of responding. Fortunately, it seemed her question had been rhetorical as she continued, “Well, let me see… Hmm… What might convince me?”, her fingertips trailed across his cheek as she circled him like a sensual shark anticipating a kill, her voice low and intense, “It would have to be something quite blatant to distract me from my own preferences… Hmm… now what might work?”

The teasing touches of her fingertips and the low, taunting, teasing voice made Andy tremble as he stood there, then she stopped behind him, the gentlest reach of her breath once more falling on his ear as her voice turned almost musing, “Do you ever look at porn that isn’t kinky, Andie? Just pictures of women who encourage the men looking to think about fucking them?”

The abrupt apparent change of topic caught Andy by surprise and shocked his voice back into some semblance of operation, “...yes… er… that is… I…. used to.. I mean.. I do.. but not so…”

Miss Aulker continued speaking as if Andy hadn’t replied, cutting off his babble, “Those women, they show off their bodies to make men – and perhaps women – want them, don’t they? They spread their legs, then show off their ripe pussies to the camera – to the men looking at them from the other side of the picture – to invite them in, to make them think about what it would be like to be inside… They might even use their fingers and pull open their pussies to let you see inside, to pretend they want you the viewer inside, to make you think about what being inside would be like.”

As the almost hypnotic voice continued, Andy felt her hands on his upper thighs, sliding up, taking his skirt with it until her hands were pinching the lower half of his buttocks, her thumbs together either side of the thin, silky strip of his thong. The fingers squeezed, his buttocks parted, stretching his arse cheeks apart briefly, then letting go. Miss Aulker slowly moved round in front of him again, teasing fingers trailing up his buttock, back and shoulder to his face as she did. Once more, her eyes captured his, “Do you think you could pose like a porn star, Andie? Do you think you could make your body say how much you want the viewer inside you like a porn model does?”

Andy gulped, thinking he saw where this was going, and reluctantly nodded. Miss Aulker smiled, “Then that might help, Andie… If you were to bend over the end of my desk like one of those models and… invite my fingers inside your pussy-hole… That might get my attention. That might help me forget about the toys on my desk and want to have my fingers inside you.”

Her face took on a thoughtful look and she cocked her head to one side as if appraising him, then she sighed, “But you’re not a porn model, are you Andie? I’m not sure you have the experience to really sell that look with your body, do you?”, Andy was both mesmerised and terrified by her words and couldn’t have responded at this point even if he’d thought she really wanted one, “No, I think not… but fortunately for you, I’m not the other side of a picture, am I? You can use words, not just your body. You can say all those things that the porn model is trying to say with just her pose; what you want the watcher to do to you how much you want it, how you love it.”

Miss Aulker stopped speaking abruptly and sighed again, then turned her back on Andy and picked the riding crop up from her desk, caressing it between her fingers and tapping it into her hand. Andy’s heart began to race faster and faster as the spectre of the young man outside hearing him accept the pain and humiliation of corporal punishment loomed large in front of him. Without thinking, he threw himself face-down over the end of the desk, scrabbling at his waist to shove down his panties, which stopped before his knees as he pushed his legs apart. Once they did, his hands came up, yanking his skirt out of the way and prizing his arse cheeks apart.

A moment later, he couldn’t believe he’d done it and the humiliation washed over him. Miss Aulker turned to face him, the crop still in her hands and actually laughed quietly, ramping up Andy’s shame and humiliation still further. She walked behind him, still tapping the crop into her palm, “Well, that is a pretty, smooth pussy Andie…”, she stepped back into the edge of his tear-blurred vision, “Was there something you wanted? This perhaps?”, she gestured with the crop.

Andy gulped back his tears, realising that she was absolutely going to make him go through with this, that exposing and spreading himself for her in this humiliation way wasn’t enough. A part of him wondered if she would really go through with it; if she would spank him and out herself as well as him to whoever was now in the outer office, but the looming mass of his own fear of discovery wouldn’t let him seriously consider that she wouldn’t. That left only the begging and confession she demanded as an alternative.

Andy gulped again and managed, “I… would like you to… push your fingers in my… pussy, Miss Aukler… I… that’s… uh… why I showed you… I want… uh.. you… in my… uh.. pussy…”

She feigned surprise, trying to suppress a grin, “Really Andie? Why on earth would you want that?”

Another gulp and despite the burning shame he felt, Andy’s fear of the crop motivated him to sound a little more convincing, “I… uh.. love my ars… uh.. pussy fucked… your… fingers make me… excited… uh.. so excited… it makes me feel… uh.. almost like… like I want to.. cum… Will… you… please fuck my ah… pussy?”

Miss Aulker once more moved behind him. With an effort of will, Andy kept his cheeks spread, displaying his “pussy” for her “like a porn model”, a part of him dying inside, a part of him desperate to avoid spanking and a small but growing part aware of how hard his cock was against the desk because of it. He felt a soft but strong hand trail across his buttocks above his fingers, “Such a pretty pussy… perhaps it does need fucking after all… Would you like that, Andie?”

“Yes! Yes… please… fuck my… pussy?”

Andy heard the tell-tale snap of a rubber glove, then felt the cold shock of slippery lubricant drop into his arse crack and slide slowly down over his hot, sensitive, twitching pucker making him gasp. A moment letter, her fingers teased the exposed ring, spreading the lubricant and making Andy’s cock strain underneath him, “Is this what Andie’s pretty pussy needs? A good rubbing?”, her fingers circled teasingly and Andy found his sphincter twitching and a part of her willing her to push her fingers into him. The realisation both made the begging she was obviously demanding easier to say and more humiliating for its truth.

“Nooo… fuck me… please? Fuck my… pussy… I…. my… pussy needs fuckinnnnggg..”

The last word trailed off into a moan as cold fingers slid into his hot, needy arse hole, so sensitive from days of previously uncommon use that it was like he could feel every ridge of both the gloves and her knuckles underneath as she penetrated him slowly and teasingly. Andy almost sobbed when he realised that he was pushing his hips back, trying to impale himself deeper on her invading fingers. His tormentor, however, spoke conversationally as she controlled absolutely the slow, deliberate, teasing speed of her entry, “So tell me, Andie; when did you first try something in your… pussy.. as part of sex?”

Andy’s mind flipped in confusion; it seemed an odd thing for someone who had just got through basically forcing him into saying he wanted anal penetration to ask. A brief thought of lying crossed his mind, but the tormenting, humiliating, arousing distraction of her fingers moving inside his arse hole wouldn’t let him come up with a convincing lie and fear of punishment wouldn’t let him not answer. With a gasp he admitted, “Claire… sometimes… played with my… arse during sex… before we… married… I… sort of liked it when she was… blowing me…”

The answer actually surprised him; he’d forgotten himself until that moment about that little aspect of his once-adventurous sex life with his wife and had thought that getting his anal toy to play with had been a first time thing. That was Miss Aulker’s next question as the fucking, screwing, twisting, curling fingers in his puss… arse took up the majority of his mind, “When did you buy the plug toy you’ve been wearing for us, Andie? Why?”

It went on… and on. Intimate, embarrassing, excruciatingly personal questions, all while Miss Aulker’s slim, strong, exquisitely skilled fingers thrust, twisted, pressed and rubbed inside him, driving him insane with arousal. Within minutes, he was squirming on the desk, minutes later he could feel the slippery wetness spreading through his thin blouse as his achingly, painfully-hard cock leaked all over the desk while his stomach squired in it. He couldn’t resist her; neither her incredible assault on his arse, nor her insistent, intimate, weirdly casual questions. 

He felt helpless to move, helpless to protest, helpless to refuse answers, helpless to lie. She questioned him on when he had started cross-dressing and he found himself admitting to his childhood flirtations with his mother’s underwear as well as every single detail that she dragged out of him about his re-discovery and evolution not so long ago. She questioned his porn tastes, demanding confessions of which parts of his favourite porn turned him on the most and the least. She interrogated his fantasies and his dreams, had him confess his opinions and any fantasies about people he knew. She laid bare his entire sexual history; first kiss, crushes, girlfriends, experimentation, his sex-life with his wife, his solo fantasy life, everything. 

The whole time, her skilled fingers worked on him, probing and fucking his arse expertly, keeping his arousal at maximum, keeping his mind disconnected and off balance, keeping him from realising or even fully remembering everything she asked in that cool, matter-of-fact voice, and everything he confessed in a series of gasps and moans. He never ejaculated through the whole thing, though for most of the interrogation his mind floated in that disconnected, almost thoughtless feeling that usually only happened for moments after an intense orgasm. Had she even touched his cock, he might have soaked the whole surface of the desk with cum after the intensity of buildup, but she never did, though she did begin to manipulate his balls as well once her probing fingers had brought him to the gasping brink and held him there. She cupped them, squeezed them to the brink of pain, pulled them, ran her nails over them and dug them in, even pressed them up as if trying to force them back into his body. Andy felt it all, but the odd sensations blurred into the intense, humiliating arousal and pleasure of the relentless fingers inside him and the intense effort needed to answer the quiet interrogation at the same time.

Then suddenly all sensation was gone, leaving Andy gasping and limp on the desk, only faintly hearing the snap of rubber gloves as Miss Aulker removed them. It seemed like hours before Andy’s eyes refocussed properly and he felt he could move his limbs, though it was probably only a minute or two. When he raised his head, he saw Miss Aulker with his back to him, sitting at her desk apparently working on a report of some kind. He pushed himself up, feeling weak and exhausted, the only part of his body seemingly able to hold rigidity his cock that, though softer, was still semi-erect.

He looked down; the desk where he had lain was sheened with glistening stickiness and his belly and the blouse covering it were soaked and matted with pre-cum. His arse felt even more sensitive, throbbing with the tiniest movement in a way that sent an answering throb through his semi-hard cock. He felt light-headed and hot, though his body felt heavy and chilled by the drying perspiration on it. 

Miss Aulker glanced over her shoulder at him, “That’s all for today Andy. You may go once you have cleaned your mess of my desk.”, she waved a hand at some blue waste-roll set on the desk beside her.

Andy gawked at her; it seemed such a non-sequitur after what had just happened. When he didn’t move after a minute, Miss Aulker looked round again, looking slightly exasperated, “I said you may clean up, put on your disguise and go, Andie. Mrs. Reddin will summon you when she needs you so go do your job.”

When he still stood there, jaw open staring, she snapped, “I have work to do; do I need to summon someone to remove you from my office?”

That threat got Andy moving; he grabbed the waste-roll. Hastily swabbing down the mess on the desk and tossing the used paper in the bin, then frowning down at himself and using a bit more to try to clean his soaked blouse and skirt a bit. Self-consciously he pulled up his panties and re-arranged his clothes before taking off his shoes and pulling his male clothes – what Miss Aulker referred to as his “disguise” – over the top, slowly and almost painfully.

He stared at her one last time and, when she made no sign of acknowledgement, blinked and turned to the door, doing his best not to stumble as he traversed the now almost full outer office on his tired and confused way to his own desk, to exhausted to even think whether any of the HR staff might have noticed his semi-hard on still pressing through panties, skirt and trousers.