tagTranssexuals & CrossdressersThe Office Sissy XX

The Office Sissy XX


It had been one of those days where you wish you had chosen flats and support tights. But no, that wouldn't have felt appropriate for the new head of human resources. Impressions are everything in this business. Back to back meetings from nine am to seven pm had taken its toll on my calves, my back and for that matter my mood. It was one of those days I get a little jealous of male colleagues who sit comfortably in Saville Row suits and black expensive shoes. My jealousy lifts as I catch a glance at my image in the glass walls that line the corridor on the ninth floor; five foot eight, six foot in my four inch red heels, toned legs, tight black silk skirt, red blouse. Whilst those guys in the board room were relaxed in their uniform suits, they could never have been comfortable with me in the room. They would have been mentally and physically distracted by my presence, and from their posture, I can tell they found it difficult to hide their erections every time I crossed my legs.

My last meeting of the day had been cancelled, thank god, so it was back to the office, pick up my jacket, handbag and a few personnel files. As I walk towards my office, the plush one in the far right corner of this floor, I noted the click of my heels are punctuated by the click and hum of the automatic lighting which illuminates my route like a runway. My gait alters as I fantasize about being on a runway at Milan or London Fashion Week. Walking as the models did only a few short weeks ago.

My fantasy is broken as my subconscious mind interrupts my flow, that's strange! Whilst the corridor lights ahead remained at standby, dimmed to save power, those of my office shone through the blinds, illuminating the last two feet of my route. They are on the same system as all the lights in this amazing building. They switch off after ten minutes if there wasn't anyone in the room, and then come back to life when you enter.

As I approach I can see someone in the room, the cleaner? A lovely young girl, Eastern European with a sexy little ass. But as I sweep into the room I realised it wasn't, it was the new boy from sales... Daniel or was it Danny... sitting at my desk. "Daniel... can I help you?"

"Sorry Miss Jones, just leaving you a note, you go on, I'll finish off and brief you in the morning"

Something was wrong; Daniel was sitting on my side of the desk, and appeared embarrassed. I turn to collect my handbag from the sofa, which is forward and to the left of my desk. I see a reflection in the glass wall, yummy, my lovely shapely legs in my strappy silver heels. I look down and see my legs terminating in my four inch red heels, and then it hits me.

"Daniel please stand up" hesitation... averted eyes... defensive posture...

"Daniel I want you to stand up now, and show me your legs, and for that matter my favourite heels."

Slowly, very slowly Daniel placed his delicate hands on my desk, leaned forward, and rises from my seat. Omg... he stands in front of me, white panties, hold up shear tan stockings.

"Come around to this side of the desk" my voice steady but with a touch of impatience. "Show me your feet!"

Daniel walked, no glided, from behind the desk, head lowered and eyes focused on his feet. I have to admit; from the waist down he is stunning. I tried to get angry, but felt elated, aroused. I swept my hair from my eyes and then folded my arms and inspected him from head to painted toes.

I reached for my handbag and found my phone. Two flicks of my long red nailed finger across its interactive screen and I had enabled the camera function. Click, flash and it was captured. Not only the image of a sissy boy, but his soul. He was mine...


Daniel's file revealed he was just 22 and a recent graduate recruit to our growing sales team. He had been posted to the head office for the last month as induction, but was due to go out on the road next week as a junior sales rep. We sell and maintain high end commercial printers and scanners, and one of our products is most likely installed in your office. His file showed he preferred to be called Danny and was living away from home in one of the many studio flats which surround Swindon.

It took me less than a minute to read his file and come to a fascinating conclusion... I have a new plaything. Danny hadn't moved or spoken a word since he had revealed his surprising secret. He just stood, elegantly but demurely next to my desk. He looked both silly and erotic in his white cotton shirt and tie, but with white panties, his hold ups and my strappy heels. It is at this point I notice his toenails are a distinctive shade of pink, and there are no signs of hairs on his legs.

"Danny I have to ask, why are you wearing my silver heels?"

He glances up, our eyes meet for a fraction of a second, and then he bursts into tears. Omg, what a sissy boy you are. I sit on the leather sofa, and pat the space next to me and say.

"Danny, come sit with me and explain. Yes you are in trouble, but nothing the head of HR can't sort out. Tell me why you are wearing women's underwear, and have a desire to wear my clothes?"

Danny steps over to the sofa, turns effortlessly and sat close to me. So close that our legs touched as he crossed them so delicately, and I feel the wonderful tingle of desire fill my body. Resist it Penny, I tell myself, we must stay objective... for now. I hand Danny a tissue, a tool of the trade in HR, and he wipes his eyes gently, so gently, blows his nose.

"Please don't be angry Miss Jones. It was harmless fun; you weren't supposed to be back 'til 8:00."

"Do you like my heels? Is it a shoe fetish? But why the panties and stockings?"

"I can't help it Miss Jones, I have a compulsion to wear stockings and heels. I have done since I was a child. I love to walk around the office at night seeing my legs in the reflections. I have just one pair of flat shoes, and when I saw you had left these beautiful heels behind, it was too much to bear. Please, please don't fire me" he finally begged.

My hand instinctively rested on his knee, a mistake I regretted immediately, but an action which sent that tingle through my body. A feeling I had first felt as an adolescent and would never forget.

"I'm afraid you are in trouble, this is not something we can accept here at PrintSolutions. Do you wear the panties and stockings all the time or just when you think you are alone?"

He started to cry again, but I noticed he had not objected to my hand, which now rested a good four inches above his knee.

"The panties are permanent, I have no male pairs. The stockings I keep in my rucksack with my flats and a few other bits."

"Like nail varnish?" I ask "Go fetch your things, but first, please take off my shoes"

Danny slipped out of my feels with a surprising feminine grace, and walked out of the room and about twenty yards to his work station. His movements were almost feline and he walked on his toes, as if he still wore my heels. He returned quickly with his treasured possessions. At my request he slowly emptied out the contents.

The normal paraphernalia of a sales rep, files, pens, diary, but then a pink draw string bag. This treasure trove contained two pairs of hold-ups, expensive, a thong, a camisole, a bottle of the pink nail varnish, a battered pair of black ballet slippers which turned out to be his only pair of female shoes, and lastly, and most surprising, a nine inch dildo.

Being a single, I know the value of a good quality dildo, and this was divine. So much so that I wanted to slip it in there and then; to release all my tension into that tube of bright pink silicone. I resisted... for now. Still no reaction to my hand on his thigh again.

"Look Danny, this I silly and must stop. Can you stop dressing this way, its important I know."

"No, I'm sorry; I have tried and failed so often. Don't worry I'll resign and leave"

"Ok, but there is an alternative."

I hand him his camisole and ask him to put it on for me. He is bemused, but complies, removing his shirt and tie, and slipping on the camisole. I go to my cupboards and open a full height door which acts as my emergency wardrobe. I pick an old dress that I keep as a reserve for formal disciplinary interviews. It is black, elegant long sleeved with a high neck but on the short side of modest. I hold it against Danny who is now standing in bewilderment.

"This should fit you Dannie" the inflection on his name was lost on him as he eagerly took the dress, unzipped it and stepped inside. I zipped him up and took a long look. The neck line was wrong, but then again he had no boobs to speak of. The waist was tight, and the ass needed work... but overall... sexy.

"Do you like it Dannie..."

This time the feminine form of his name hit him like a wake up call, and he smiled for the first time. He nodded, but looked down, embarrassed.

"I know hunny, you feel funny don't you." another nod. I went back to the wardrobe and tossed him an old pair of black patent leather heels, 3 inch in a Mary Jane style. He slid them on and his poise changed. Two more things I thought. Long hard days take it out of a girl, and we have to look our best. Occasionally I have to go straight from work to formal events, such as drinks parties, there are dresses in here that are just for these special occasions. I also like to wear my hair up for such events. Rather than spend hours teasing my long auburn hair into a formal style, I invested in a couple of fantastic wigs. It was my reserve, older wig I place on Dannie's head. Still auburn, but teased up with strands which fall naturally around the ears.

My second treat for Dannie was to apply some of my makeup. Dannie was in exec as I made his eyes a smoky grey with dark lashes and liner. His lips were painted red, as were his finger nails. When I had finished, Dannie looked like my younger sister. She is so pretty. I leaned forward to kiss her cheek, but was met by her full red lips.

"Sorry Dannie, but this is not going to keep you your job. I just needed to see how femme you could be. I've always been a prick tease, now I can be a clitty tease as well" I could see I was having the desired effect. There was a part of Danny which still wanted to be acknowledged. A huge tent had formed in her dress. I reached out and squeezed her clitty, Dannie yelped and then giggled. Her voice had gone up an octave, was that my squeeze, or was she trying to comply with my needs, fighting for her job.

"Sit on the sofa for five minutes whilst I sort things out"

I went to my desk and started up the pc. It actually took me twenty minutes to sort things out to my liking. The printer, one of ours, spat out a pile of paperwork, which I swept up and took over to Dannie.

"Daniel, I told you that your actions could not be tolerated, and the fact that you are sitting here as a woman proves this. This document is your resignation which you will sign, or I will make public the photo I have of you in my heels. Do you understand?

Dannie nodded, took my pen and signed two copies, both spotted with mascara laced tears.

"Your employment is now terminated and you may leave, dressed as you are as punishment."

Dannie almost stumbled as she stood. The first time I had seen her unsteady in heels.

"You can't humiliate me like this, you dressed me this way. I thought if I complied, you would let me off with a warning... please don't send me home like this, I beg."

"I said you may leave, not MUST leave. Read this... it's a new contract to do tele-sales for us, in the name of Miss Dannie Brown. If you want it, all you need to do is sign. There are however fringe benefits."

I slide my hand under the bottom of her dress and then up. Her hard clitty is straining against the panties, so it took but a second or two to release it from its cotton prison... she quivers as she realises my intent.

Like a phallic joystick I reverse her to the sofa. As her sexy shaved nylon clad calf's touch the leather of the sofa she slowly sits. Her hair flows back as she arches her spine, thrusting her non existent breasts forward. I slide my thin fingers down her shaft until my palm reaches her hot sack. I roll my wrist slowly cupping her genitalia. Dannie almost faints as I gently squeeze them. I release and she relaxes onto the soft sofa, spreading her legs as I withdraw my hand. I grab a cushion from the sofa and dropped it between her divine legs, bent my knees and knelt between her smooth thighs.

I could smell her male hormones flowing out from under her dress, my dress, our dress. Dannie sat passively with her painted fingers resting lightly by her sides, stroking the soft green leather of the sofa. I looked into her eyes, and saw the naive soul of a little girl. She licked her lips and pouted a little. Then into a broad smile as my hands rest on her thighs. As they slid up her frictionless stockings, the cuffs of my blouse caught on the hem of her dress; revealing more and more of her ultra feminine legs.

Dannie was unable to move, transfixed by her predicament. I hooked my arms under her knees and pull back. Her ass slides towards my face, her hard clitty magnified at this range, the smell of musk and pre-cum mingled to arouse me further. I had to retain control, what should I do. My eye was naturally drawn to Dannie's pink bag. I reached in and removed the rubber dildo. I slipped it in my mouth to wet it, and show Dannie what to expect.

I could see in her eyes that she wanted me to go down on her quivering clitty and my pleasure with her dildo was merely teasing her. She will learn not to make assumptions. I push the dildo deep into my throat so only the end tip could be seen between my lips. I can see from her quizzical look that she cannot understand why she can see the tip and not the base of her dildo.

I wink as I lower my head, avoid her clitty and her sack, but aim for her ass, her new pussy. My lips touch her tiny rosebud and then push the dildo out three inches. I bite hard, and force the tip into her. Dannie screamed, truly screamed as she realised what I was doing. Another inch, then another, until its entire length is within her sacred pussy hole. I kiss the latex end and lift my head slowly, licking her sack and shaft as I straighten. I could feel the electricity flowing through her body.

Her long red nails are gripping her smooth thighs. I push her knees back, making her sit on the dildo. Dannie is obviously used to her dildo as she knew exactly how to gyrate her ass to make the dildo hit her g spot. Her long, hot and solid clitty had started to pulsate. I could resist no longer. I took one last look into Dannie's eyes; they showed pure love and ecstasy. She managed a quick smile before I looked down to the focus of my longing.

I wet my ruby red lips and kissed the tip of her long pink clitty. I leave a smear of lipstick on the tip, licking my lips to taste the salty pre-cum. like a shot of pure adrenaline my heart races and I open my mouth wide. I close my eyes and approach the target guided by memory.

(Let me know if you want more...?)

Penny Jones

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by Anonymous

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by Anonymous01/04/18

good start

Give me more!

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