Straightening my skirt and easing the creases out against my thighs, I glance in the mirror at my overall appearance. For a brief second I panic, thinking I’m overdressed for the occasion. Thoughts rush through my head.
What if I’ve misread the situation? Maybe this will be a big mistake and ruin so much of my life?
I’ve lived with these types of thoughts for so many years now and I really need to let them go but if I want to be happy and true to myself then I need to do this. Grabbing my bag from the dresser, I leave the room and head towards the lift. Once in the lift, I check my makeup in the mirror, slip on my jacket just as the doors open on to the foyer.
Walking confidently across the reception area, I approach the doors and a man walking in holds the door back, gestures for me to proceed whilst flashing me a smile. Smiling back I carry on out the hotel and onto the pavement. I tempted to glance back to see if he’s checking me out but now isn’t the time nor the place for that. I must stay focused on the task ahead.
The city feels alive and busy, far from what I like in my usual surroundings. I’m a much more discreet and quiet person but this I where the meeting had to be held. Neutral ground so to speak. The pace and noise help me get into the swing of my purposeful walk despite the heels I’m wearing. I don’t often wear heels of this height so must keep concentrating. I don’t want to take a tumble in these black 6 inch ‘ball-busters’ as someone once referred to them.
Before too long I’m outside the office building I recognise from the picture. The steps to the reception pose a slight challenge to my pencil skirt and I feel it riding up slightly but due to the length of it I know my modesty will be protected. The automatic doors open beckoning me in.
The petite blonde receptionist looks up at me. “I’ve an appointment at 6”, I say slightly cautiously.
She nods, “Do you have the smartcard?”
I reach into my bag and pull out the card that I was sent a few days earlier.
The receptionist gestures to the lift with a smile says “Floor 6 ma’am and you’ll be greeted at the door.”
Pressing the card against the lift reader, the doors open and I step in. Now I’m beginning to get nervous. I fidget in my clothes, swap arms for my bag and check my hair once again. The lift doors close and to relax I close my eyes.
The ping from the lift as I approach the floor brings me back to my senses. The doors retreat and a smartly dressed man greets me.
“This way please.”, he turns and walks towards a frosted glass door.
“If you’d care to use the card here, you may then enter.” He steps out the way as I approach the door.
The door releases with my card and I step inside. The man closes the door behind me leaving me alone in the sparse and minimalist office space. The lighting is dim except for one room in the far corner. Breathing deeply I walk to the room. Peering inside as I open the door, I’m slightly surprised to find no one is in there.
Looking around the room, there are two small cabinets are in front of the large window looking down upon the city beneath. With the failing light it takes on an exciting and vibrant look. A red hard backed chair faces a large desk with a large leather executive chair in the centre of the room. The desk looks untouched, nothing out of place, almost immaculate. On it sits a phone, a laptop, and a leather and velvet blindfold. As my eyes fix on the blindfold, the laptop pings. I walk around the desk to face the screen. A message appears.
“Apologies for my lateness. I shall be with you momentarily. As stated in our correspondence my anonymity is paramount. Please put on the blindfold, take a seat in the red chair and await my arrival.”
What? Blindfolds? What next?
Feeling uneasy but equally intrigued I pick up the blindfold and walk to the red chair. Placing my bag alongside it and slipping off my jacket, I lay it across my knee. I breathe deeply as I place the blindfold on fixing the buckle at the back.
I’m plunged into darkness.
Sitting there, I keep my knees together trying to suppress the feelings building inside me. Without a visual distraction, my other senses become more sensitive. I can smell a faint musty smell in the room, like an item taken out of storage for some time. I can also the leather, presumably from the blindfold or maybe the chair I’m sat upon. The room is warm compared to the late Autumn evening outside.
My skin begins to feel super sensitive. The lace of my panties against my bottom and stocking encasing my legs begin to make my head swirl. The centre of my back where the lace straps lay on me all feels so alive to me. I begin to feel relaxed and horny, a dangerous combination. I ease my clenched legs slightly, moving my skirt again my thighs, releasing another charge of emotions.
Suddenly I hear the door open, making me jump in my seat. The door closes. Someone has walked into the room as I hear their footsteps. My senses feel on fire as I smell a familiar aftershave smell fill the room. The chair creaks as someone sits at it. The laptop keyboard is quickly tapped.
“Thank you for doing as I requested and for being so prompt.”, The man’s voice isn’t rushed, it seems almost rehearsed and calculated.
“Please, let me take your jacket.”
With that I hear the chair creak again and flinch as he gently takes my jacket from my knee. Instinctively I draw my legs together, and lower the edge of my skirt. I feel a slightest touch across my shoulders over the straps to my underwear as he walks behind me. I try to follow his noises around the room.
“Your outfit is exceptional. From my instructions it appears you have followed it very well.”
My outfit was a white satin blouse that, if looked at closely, had an almost sheer appearance to it. Black pencil skirt to just above the knee. Black sheer stockings topped with a lace band completed by a white lace Basque keeping the stockings in place. Oh and not forgetting those ball buster heels. My makeup was classy not slutty although the red lipstick did have a tendency to give a more raunchy look to my face. My brown hair in a bun to finish off the office look.
“My staff will not question the secretary position I said I was interviewing for. You look every inch the willing candidate.”, again the voice said calmly.
“Are you as willing as you said you were during our chats though?”
Anxiously, I bite at my red lip, nodding slowly.
“I need to check you have fulfilled all your outfit requirements. Stand!”
I slowly get to my feet, nervously keeping my arms close to my side.
“Step towards the desk.”
Carefully I reach out for the desk feeling its hard glass top.
“Bend forward.”
I slowly bend forward over the table, knowing my ass will stick out. I feel a hand run up my leg from the knee stopping at my stocking tops. Suddenly with two hands my skirt is hitched up exposing my ass, suspenders and lace lingerie covered cheeks. A gentle finger traces the outline of the buttplug keeping my ass eager. The finger moves around to feel the cage encasing my small cock through the lace of the panties. I let out a soft moan as I feel it tease my cage.
The moan quickly changes to a yelp as a hand swiftly smacks my ass cheek. The other cheek quickly feels the same treatment.
Then nothing. With hands planted on the desk I’m expecting another blow.
“You did well Miss.”, the voice approvingly tries to reassure me.
“Now fix your skirt. This is a respectable business, anyone could walk in any minute.”
I hurriedly straighten up, fix my skirt, pushing out the creases once again and place my hands to the side. My head is swimming, my caged cock swelling against its binding and my ass pussy grips the plug tighter. What is happening to me. I’ve wanted this for so long but am I in too deep now.
“So, when was the last time you orgasmed?”
“Ten days ago, as you instructed during our chat.”, I replied.
“Good girl”
The sound of being called a good girl in some strangers office, dressed like I was, blindfolded nearly makes me cum there and then. I ache so much to cum I feel it deep in my stomach.
Bringing me out of my mind wander, I feel a hand grip the back of my neck and I’m marched across the office. From my reckoning, I think I’m by the window. The hand pushes me down across the cabinet and a rough hand pulls at my skirt once again, raising it to the waist. With one hand still on my neck the other is pushing at the plug in my ass, making me squirm with pleasure.
“Panties to your knees.”
I quickly pull the white lace panties down feeling them slide down to my ankles.
“My, you are a keen little whore aren’t you?”
Under the weight of the hand on my neck I nod. The hand shifts to the centre of my back, keeping me pinned down. The other hand by my ass, tugs at the plug, giving me a sense of emptiness as it comes all the way out. The plug has been in for a good few hours as I was instructed. I hear the plug drop to the floor. For a few seconds there is no noise, movement or instructions. Suddenly, I feel something press against my pussy hole. The tip of a cock rests against my pre lubed opening. Slowly it creeps inside. I try to relax, breathing deeply as it pushes further and further.
The last few months I’ve been getting used to inserting bigger toys in my pussy in preparation for this moment. I hope that the practice has been enough. Slowly I feel the full length of the cock stretching me, pushing my insides to the limits of my toys. A let out a small whimper. Just as I become accustomed to the fullness, it starts to withdraw. Slowly. I feel every vein and ridge of it. As the tip reaches my opening it pushes back in taking less time to reach its destination.
The pace quickens as the cock pumps my ass. I grab the cabinet with both hands trying to steady myself. The thrusts are deep and purposeful. Everything that was expected of this encounter has come true. Here I was, in a strangers office, dressed like the sexy secretary as instructed, having my first sissy experience and I was loving it. Loving every thrust and push.
I feel both hands on my hips as I am used like a slut. The pushes make me unsteady on my heels and I reach a hand forward to stop myself falling forward. My hand lands on the cold glass pane. I have visions of how I look in the window of the office should anyone be looking up at that time. To the passer-by it look like so illicit office affair with the boss having his way with the office secretary. The thought excites me and I begin to moan.
“Oh, fuck! This is so good.” I yell.
The pace increases and I begin to feel my pussy pulse. My legs become weaker as I am taking this hard cock. My little clit is useless in its cage, a testament to my submission to this man. My knees buckle slightly with the pleasure I feel race through my body. The feeling overwhelms me as I try to stop the intensity inside me by moving away but the hold on my hips is too firm and I’m helpless to the fucking I’m receiving.
I surrender to the moment and begin to leak through my cage.
“Fuck me, fuck me hard.”, I can’t believe I’m saying this to a stranger.
I feel my sissy juices land on my stockinged legs as he continues to pump it out of me. I’ve never felt so satisfied from sex before and I’m surprised at the amount of cum I’m producing. It feels like it flowing from me for minutes as my pussy gets work on.
The pace of the thrusts slow. Did he come? I never felt it if he did, but then again how should it feel? This is a first for me.
The cock is still balls deep as I feel my blindfold loosen.
Becoming accustomed to the light I look up and see the reflection in the window backlight with the dark skyline. I see the figure in a suit behind me as I’m bent over the cabinet.
“Hi honey. I see you’ve enjoyed yourself.”
Glancing back it was my wife stood behind my opened legs. Her strapon poking out her her trousers had just fucked me to the best orgasm of my life.
My mind was racing. “I-I-er”, was all I could manage.
“Shush slut, I’m not finished with you yet.”
She grabbed at my waist again and proceeded to give me another fucking.
“I’m sure there’s some more cum in there to get out before we talk about some changes in our marriage.”
Looking back at the reflection I see my wife loosen her tie before working on me once again. My eyes close as I feel the excitement build once more and I begin to panic over how things will change now.
Source: reddit.com/r/sexystories/comments/v09f06/the_planned_office_meeting_tmf_crossdressing_toys
Great, hope there’s more to come.