(In response to a request I am reposting an old story)



He was relatively new to Tumblr. He didn’t quite get the way things worked. He just wanted to enter Gillian’s competition. He knew her from work and she was so hot, he wasn’t sure anyone else could see it. Most of the guys in the office had their eyes on the young temps or maybe that junior manager in finance with the killer figure.

He adored Gillian, the slightly stern older woman with the old fashioned horn rims and such wonderful taste in stockings. She had a curvy figure, perhaps plumper than most of the other guys appreciated but very feminine. She was the Personal Assistant of the office manager, and had a reputation of being fierce and not to be crossed. The line managers seemed to respect her more than the boss.

He had overheard a conversation at last year’s office party between Gillian and an employee that was leaving to set up a fashion business. He couldn’t even remember the woman’s name anymore, but that conversation had stirred him. Back then he barely noticed Gillian, but something she said had changed all that.

Gillian, a little drunk, had asked if she would just sell clothes or whether she was going to sell lingerie, she claimed there was a lot of money in lingerie. The other lady had been dismissive until Gillian told her she had thousands of followers on her lingerie tumblr and that people were always asking her where they could buy the clothes in the pictures she posted.

The other woman was still unconvinced but Gillian had fished out her phone to show her. He was so intrigued, he plucked up the courage to walk up behind them and ask if either of them wanted a drink while he was at the bar. He had caught a glimpse of a lovely pair of panties on Gillian’s screen below a username gillspantiepics.

He was intrigued and before he even arrived home that night he had downloaded the app and was browsing through the lovely pictures. He had always liked lingerie. He had a collection at home. Every week or two he would put aside a lazy Sunday and dress in stockings and suspenders or a flowing diaphanous robe with just panties. The more feminine the better. That night he couldn’t resist slipping into his pink sheer nightdress and browsing Gill’s amazing blog.

As he toyed with his small erection trough the slightly scratchy nylon and the matching satin panties beneath, he came across a picture that threw him for a loop. The woman in the picture had to be Gillian herself. Her face was coyly covered by her long red hair, usually held up in a tight bun at the office, but the note below said ‘A little something for all my fans out there, especially the naughty sissy girls that have been sending me their pictures.’ The thing that proved it was Gillian were those glasses, pulled down over her nose sexily, so she was peering over them. He had seen her do that when silencing loud chatter in the office. From then on that more stern version of this picture would have an entirely different meaning.

The notes included a link to another blog which also seemed to be written by Gillian, but this time it was almost exclusively amateur pictures of Gillian in teasing underwear and Sissy submissions to the blogger mistressgillian.

For the next few months he only had eyes for Gillian in the office. She was elevated in status to goddess in his eyes. He studied her every move, imaging her glorious curves under her suit. He even swapped his sought after window desk for a view of Gillan at her spot just outside the Manager’s office. He sometimes found himself staring at the modesty board of her solitary desk wishing it wasn’t there so he could get a better glimpse of today’s hosiery. He lived for the smallest glimpse of lace under her blouse, wanting to know which of her many wonderful bras or girdles she was wearing today. He even plucked up the courage to ask her about her perfume so he could buy some for his special Sundays.

There was rarely an evening that didn’t pass when he wasn’t online checking out her pictures. He spent so much time on tumblr it was inevitable he would also find non kinky interests being discussed. A life long passion for angling had him creating an account and occasionally posting pictures he came across online. He soon had a diary of his fishing trips that was read by a few new tumblr acquaintances with whom he swapped tips.

But compared to his obsession with Gillian and her sissy boys the fishing blog took up much less time. He longed to submit a picture of himself to Gillian’s blog. The idea of actually talking to her about it was out of the question, he couldn’t bear the idea she would reject him or judge him. Sometimes her posts suggested veiled contempt, and although he was sure this was all part of her mistress persona he wondered if she secretly laughed at the sissy girls in her inbox. Maybe she just used this blog to humour them and cross promote her other mostly innocent blog.

Deep down he fantasised about telling her and her laughing. She would drop hints to the other ladies and make him the laughingstock of the office. Even new temps would giggle as he walked past. This fantasy was guaranteed to get his small erection leaking into his panties. It was so erotic he only had to hear Gillian laugh at work and he would start to get hard.

One Sunday he decided to make a blog of himself in his favourite lingerie. He had been building up to it, working out how to keep from being recognised, scoping angles of his house that seemed generic, taking a few test pictures, shaving areas he hadn’t realised would show up so much. That Sunday he finally made the blog and posted three pictures. One in his favourite bra and panty set, from the neck down, one with added stockings and garter belt, and a separate one with just his nightdress on, his small erection just visible though the sheer nylon.

After a week nobody had liked anything and he felt a little deflated. So many of the Sissies that Gillian featured had hugely successful blogs.

From the little he had picked up from his angling diary he realised he needed to follow some like minded blogs, but he couldn’t find a way of following with his new blog. While testing things he had briefly followed a cute sissy he liked and nearly had a heart attack an hour later when he realised that he was following it from his angling blog. He couldn’t unfollow quickly enough and prayed all of his angling friends were not online in the early hours. He found he could make his likes and followings anonymous but that wouldn’t quite do the trick.

He settled on a tactic of messaging like-minded sissies with comments, and that seemed to get things going slowly. He longed to message Gillian, but each time he composed a message he chickened out and deleted it. His blog was making him glum.

On the other hand Gillian was posting more pictures of herself than ever. She had got a better camera and her outfits looked great. Her photography improved too and so did the outfits! Lots of old fashioned lingerie, girdles and corsets, large satin panties that shouldn’t be remotely sexy but pulled tight over Gillian’s round bottom as she bent over her dresser and extended a stocking clad thigh, they looked amazing.

He wanted to kneel behind her and kiss those shiny panties while she laughed at him. That shrill piercing laugh that he could hear from the other end of the office. The one that made him swell in the panties he had taken to wearing to work.

The thing that had finally clinched it was her call for submissions. She wanted to find the ‘cutest clitty’ and the reward would be exclusive access to her more risqué pictures.

He knew he was small. When he compared himself to some of the sissy girls in Gillian’s blog they mostly looked bigger, and the ones that looked smaller looked like they were trying to make themselves look less big. This was a competition he could win. The promised images became an obsession, he imagined them as glimpses of nipple or perhaps a bare bottom, but in his fantasy they were pornographic. He just had to see them.

One thing he had heard from a photographer, was always take more pictures than you need. He took hundreds. Every angle, every outfit, every pose he could imagine. He finally settled on one perfect shot: his little erection straining against some sheer yellow panties in the light from his window. It had the benefit of showing he wasn’t faking his size, while also looking like a properly composed photograph. Something Gillian might at least feature on her blog, even if it didn’t win ‘cutest clitty’.

He was so keen to submit it he hadn’t noticed it went from his angling blog until it was too late. Later when he finally realised what he had done he went into a panic, searched everywhere for a way to retrieve the message. That night he tossed and turned, sleepless and anxious, wondering if he dared go to work. But he would have to ring Gillian to say he wasn’t going to be in the sales meeting, and that wouldn’t make things any easier. Each time he convinced himself she wouldn’t investigate his blog he would begin to get a little rest, but then he would snap back into a panic of cold sweat and thumping hearted fear imagining her opening the submission.

By the morning he decided to just delete his blogs. He wasn’t sure why the idea hadn’t occurred before. Fumbling he reached for his phone but the battery was dead. In his freaked out state he hadn’t plugged it in last night. He spent an eternal five minutes willing the phone to come back to life before rushing to the Tumblr app to find out how to delete everything.

That was the moment his life changed. There in his messages was a note from mistressgillian. It read simply ‘Frank? I had no idea how cute you were under that stuffy suit of yours. We really must catch up. xxx’

Frank’s journey to work was a chaotic jumble of fear and fantasy. Despite his anxiety he kept getting an erection. He spent half of the trip trying to hide his arousal from his fellow commuters. Having cautiously chosen to wear his now unfamiliar boxer shorts, his erection frequently tented his trousers. He found himself wishing he was wearing his tightest pair of panties, at least they would have held him under their firm control. Thinking of those black latex panties, with the adorable ruffled hem of purple silk like a tiny skirt, didn’t help his predicament. To keep himself under control, and stop his mind wandering, he tried listing the members of his favourite sports team, before settling upon reciting those complex trigonometry formulas he had memorised at school.

As he walked into the office, Frank wondered if he should just hand in his notice and go home sick. Mercifully, Gillian wasn’t at her desk, and he slipped behind his monitor, shifting it slightly and adjusting his chair to disrupt the line of sight. He wished that he still had the window seat, tucked away in the corner of the office. He only needed to keep his head down for half an hour before the sales meeting. Gillian was usually involved in that, taking minutes and providing stats. He would be relatively anonymous in the department wide meeting, being a junior member of the team and rarely singled out for anything.

His line manger, Mr Frost, surprised him. The slap on his back nearly making him jump out of his skin.

“Morning Frank, what’s this I have been hearing from Gillian?” He said in his booming voice.

“Um, sorry? Gillian?” He looking up at the always intimidating figure. He blushed, realising the high pitched way he had said ‘Gillian’ must have sounded forced. He could feel the eyes of his colleges upon him.

“She was very cryptic with me. Said there had been a shift in your figures, a small rise where it counted?” With that last part he used air quotes. He sounded sceptical. “Dammed if I see what the fuss is about, but you know how shrewd she is with figures.”

“Really, um. I am sure it’s nothing big.” Even as he said the words the irony began to sink in. He heard someone giggle across the room, and although it was probably a coincidence it reminded him of his submissive fantasy. Not used to being the centre of attention he felt himself shrink into his already lowered seat, willing the manager to leave him alone.

“Well apparently Gillian will be briefing you in the corner office while the rest of us are in the bloody sales meeting. Bad month I hear, bound to drag on.” With this thought Mr Frost checked his watch and sighed. “I am going to need a strong coffee. Check your calendar.” He said striding away.

Frank’s knees went weak as he knocked on the frosted glass door of the office. Gillian’s voice sounded cheerful as she called him in, and offered him a seat, which somehow made things seem worse. Was she going to laugh at him? She was sitting behind the office manager’s desk, wearing a stylish tweed jacket in black and white, which only served to draw his eyes to her silken blouse. That blouse was a favourite of Frank’s. He always admired the way it buttoned on the shoulder and the way the fitted waist emphasised her generous breasts. He resisted his usual habit of trying to peer through the fine fabric to identify which of her bras she was wearing today.

“I guess you know why you are here?” She said smiling in a way he had never seen from her before. Warm and pleasant but with an edge. He felt like she was assessing him. Frank noticed she was wearing her hair down, which he had only ever seen online. A recent image of her in a lacy body and hold up stockings flashed through his mind. His obsession with her clothes wasn’t helping his attempt to remain calm and professional.

“Um, no. Sorry, Ma'am.” He said, deciding ignorance might be the best policy. “I only know what Mr Frost told me earlier, which was very little.”

“Well I am not sure a big picture guy like Frank appreciates the little things like I do,” she said still smiling. “I have been examining this weeks submissions very closely, and your little rise caught my eye.”

“Really?” He said loosening his tie slightly. It was suddenly very warm in here. She was toying with him. He tried to stay calm, steadying his breathing and avoiding direct eye contact. He wondered if he could just ignore her inference. Maybe if everything stayed at the level of innuendo he could bluff it out.

Gillian unexpectedly handed him a piece of paper with a graph printed on it. His sales figures. It looked like his results had indeed risen last week. Frank held onto the idea like a lifeline. Maybe this meeting was professional after all. Whatever was he thinking, getting everything out of proportion as usual. He needed to separate his infatuation with this older woman, from work. Try and keep a lid on his submissive fantasies.

“In a month of poor overall sales it is significant. Only a modest rise,” she said watching him closely, “but it certainly caught my eye.”

“I see,” He said consciously relaxing his shoulders. “Yes, the last month was challenging.” Sales talk, he could deal with. His pulse settled, he tried to stop hearing her every phrase as a veiled reference.

“So I have set aside some time this month to go over your daily figures with you.” Gillian said, standing and walking around the desk. “Can you be here an hour early each morning?”

“Um, yes I guess.” He was relived. Everything seemed above board and work related.

“Well congratulations, you are my new protégée.” She said offering her hand to shake. As Frank stood and took her hand she clasped it tightly with her other. “That extra hour will allow me to check you are wearing your pretty panties for me.”

“Um. Sorry?” Again Frank’s voice faltered into a higher register. He suddenly realised how much taller Gillian was than him, how firm her grip was. The office seemed smaller.

“Oh don’t be coy Frankie dear,” she said peering over her glasses and leaning towards him. Her hair dropped over her face. Frank was disorientated at the sudden turn, just as he had felt the relief of freedom, Gillian was closing her trap.

“Frankie?” Gillan said, tugging at his hand, snapping him back to reality. She smiled warmly and continued with a comforting lilt to her voice. “I know you have a lovely collection of panties. I have seen them online.”

Frank pulled his hand free and stepped backwards. “I don’t know what you mean.” He desperately tried to meet her eye and feign confusion, but Frank found himself confronted by his fantasies brought to life. Gillian the confident seductress from her online blog. He felt himself respond against his will, blushing as his erection grew.

“Frankie, don’t lie to me.” Gillian said softly, closing the distance between them. “I bet you are wearing your pretty panties now. Are you wearing the yellow ones? The ones in your cute picture.”

“I most certainly am not wearing panties.” He said, trying to sound assertive, “Why would you even ask that?”

“You can drop the act. That lovely picture you sent me wasn’t anonymous, not only did you send it from 'Frank Fish’ a blog with your face all over it, you signed it 'Panties In The Pink’.

“Th-There must be a mistake.” This was the bluff Frank had been rehearsing overnight. Deny everything. But she had caught him off guard, and hooked him in. Even to him the denial felt hollow.

“Don’t look so worried Frankie. I think Panties In The Pink is a delightful blog.” She smiled to herself as if reflecting on the pictures, before pulling out her phone. “I do like blogs by simpering sissies. All those ruffles and lace. Smooth skin and satin.” As she said this she seemed to be browsing through photos, occasionally pausing and smiling in delight. “And, do you know what else I discovered Frankie?” She said looking up at him over her glasses again.

“I have no idea?” He said, suddenly worried. He watched as she waved her phone at him. He tried to focus on what looked like a map.

“Some of your earliest pictures had geotags. They show where you live.” Frank realised he was looking at a map zoomed in on his street. He stared open mouthed at the evidence not knowing what to say. “Sissy girls can be such airheads sometimes.”

“But…”

“More seriously,” Gillian continued, suddenly looking stern, “do you remember taking a very naughty picture somewhere else?” Gillian paused to check the screen and swipe it before turning it back to him. “Pink panties with ruffles, under your grey suit. Somewhere inappropriate.”

“Oh my…” He trailed off. The map was now showing their current location. He remembered taking a picture of the very panties Gillian was talking about, one lunchtime last week.

“Do you see my dilemma Frankie?” Gillian said turning and walking away from him. “That is not appropriate behaviour for the office is it? Somebody taking naughty pictures in the restroom. Presented with such evidence I would need to investigate the office staff. That is a disciplinary issue.” She paused for effect. “Perhaps a very public one.” She slipped the phone back into her jacket before continuing her walk towards the door.

Despite his rising anxiety, Frank couldn’t help watching her curvaceous bottom in that tight tweed skirt, and the sinuous motion of those dark stocking seams. He had spent many hours looking at Gillian online, in her delicious underwear, and it was impossible not to undress her in his imagination.

“On the other hand…” Gillian turned, taking hold of the door handle. “If it was just a private matter. If a valued member of staff came to me asking for a little guidance and supervision. Perhaps an issue they were struggling with. I might be in a unique position to help. Especially if they were cooperative. Are you going to be cooperative Frankie?”

“Um. Yes I guess.” Frank figured it was best to drop the ignorant act. She held all the cards. He imagined the office gossip, the talk behind his back, the temps laughing. The idea simultaneously terrified and aroused him. His erection was urgently straining against his boxer shorts.

“That’s good to hear Frankie. I am glad you came to me with this, I would love to help you,” she said smiling. “Tell me truthfully, are you wearing your panties right now? Is that why your cute little clittie is threatening to poke through your trousers?”

“No, honestly.” He said, instinctively covering himself. “I didn’t think it would be a good idea today.”

“Such a shame.” She said shaking her head in disappointment. “Perhaps I should buy you some. Would you like some pretty new panties from Mistress Gillian?”

“Oh yes!” He didn’t have the willpower to resist. Judging by her blog, her taste in panties was so exquisite.

“Remember dear, I will also be looking at your sales figures. If they drop I may be forced to take you over my knee.” Gillian was smiling as she said this, but something in her eyes told Frank she wasn’t joking.

Gillian opened the door and held it for him, gesturing for him to lead. As he walked out of the room she playfully tapped him on the bottom, causing him to skip out into the open plan area. Luckily it seemed like the sales meeting was as long as expected. Nobody was at their desk to see.

At his own desk he found a padded envelope. Absent minded, still reeling from the shock, he ripped it open and shook out the contents. A cascade of silk and satin spilled across his desk. Panicking, he gathered the mound of ruffles and lace and tucked them as quickly as possible back into the envelope. Looking around furtively to make sure nobody else was around. To his horror there was a girl he didn’t recognise at the photocopier across the aisle, intently staring at the electronic display. Had she seen? Was she smiling to herself? Frank noticed a small note that had also fallen from the envelope.

'Frankie. Slip into the pink ones and be sure to submit a picture to my blog before home time. Mistress Gillian.’