My First Time as a Woman

My wife has gone away for the weekend and I am so excited about my plan for the next 24 hours I can hardly contain myself. I feel like cumming right now just thinking about it, but then that would spoil my plans.

I check into the hotel at 4.00pm, two hours before the pre-arranged rendezvous. I had already painted my toe nails a deep luscious red and had visited a nail bar and had false nails attached to all of my fingernails, I was so embarrassed, yet at the same time, so excited as the young girl expertly attached each acrylic nail. The nails were long and matched the same colour as previously applied to my toes. I blushed bright red when the girl asked me why I was having such feminine nails attached and whilst I wanted to tell the truth I only managed to stammer some lie about going to a fancy dress party!....My heart almost stopped when she laughed and told me these acrylic nails were permanent, at least until the grow out! I hope she was joking, though I don't think she was!

In my hotel room I run myself a hot bubble bath. I strip out of my trousers and T-shirt awkwardly, still trying to get used to my new fingernails. I step into the bath and begin to soak. After soaking for a few minutes I reach for the shaving gel and squirt it into my palm, I smooth the gel all over my legs. Reaching for my razor I start to shave my legs, marvelling at how smooth and silky my skin is after the razor has done its work. Smiling with pleasure I continue to shave the rest of my body. After soaking for a few more minutes in the hot water I step out and towel myself dry, my cock rock hard as my long red finger nails move across my smooth silky body.

I walk into the bedroom and carefully unpack my suitcase, laying out all of the sexy clothing on the bed. Firstly, I pick up the black, glossy stockings and being extremely careful not to snag them I gather them up and pull them up my smooth legs, absolutely loving the feeling of the nylon against my silky soft legs.

I glance in the mirror and smile widely as I check out my long stockinged legs, without further ado I pick up a black bra and place my arms through the straps before expertly attaching the hooks behind me. Stuffing the cups with water filled balloons I let them settle into position before picking up a boned corset. Sucking in my waist I fasten the corset up the front and then lace it tightly, therefore creating a sexy female hourglass figure. My breath was short now due to the restraints of the corset, I attach the garters at the front and back of both stockings.

I pick up a black silky thong, step into it and pull it up my long, feminine, nylon clad legs. Tucking my cock inside the front and pulling the string tight up my ass.

Shaking with excitement now I pick up the tight red mini dress from the bed. I pull the dress up my now feminine frame and zip it up. Again I admire my new self in the mirror and gasp at how sexy I look from the neck down. I run my long red finger nails over my new curves as I bend down to pick up my 4 inch stiletto heeled sandals and placed them carefully on my feet. Another look in the mirror I love how my legs and ass are redefined and shaped by the heels, I also notice that my dress is so short that any bending over and my panties are clearly on show and when standing up straight my stocking tops are plainly in view! This dress leaves nothing to the imagination.

I look at my watch, 5.00pm and I am beginning to look like a total slut, but I am not finished yet. I sit down at the dressing table, placing the long blonde wig on my head I brush it out, straightening the fringe and making sure there are no snags as my new hair falls down over my shoulders and to the middle of my back. I pick up a hair band and loosely tie my hair away from my face, to allow me to do my makeup.

Trying to stop my hands shaking I open my makeup bag and find my foundation. I lay it on thickly, covering my face in a honey brown liquid, which quickly dries to a soft, seamless matte effect, hiding any blemishes and creating a very feminine base to my face. I pick up a pair of long false eyelashes and carefully glue them to my eyelids; I repeat the process with the bottom lashes. Picking up my mascara I apply thickly to both top and bottom lashes and grin as I bat my now sexy long lashes. I apply lots of eyeliner and silver / grey eye make up giving myself very sexy, fuck me now eyes. Now for my favourite part, glossy red lipstick, I pucker my lips and thickly paint it on and almost cum as my lips start to shimmer. I blow myself a kiss before applying pink blush to my cheeks.

For a few finishing touches I put a pair of large gold hoop earrings on, a wide choker round my neck, a gold necklace and some bracelets and rings on my fingers. Finally, I let my hair down, lightly shake my head and smile seductively as my lips glisten in the light with my hair cascading sexily across my shoulders. Fuck me I thought, I would!

I stand up and practice walking like a lady in my four inch heels, tottering back and forth in the room, unable to take my eyes from the mirror. I look wonderful, like a complete slut, a whore ready to be screwed all night long! Which was quite luck really, as that is the plan!!

I look at the clock, 5.55pm. Oh my god, I thought, only five minutes left. I sprayed myself in perfume and continue to pace the room, waiting for the knock on the door, which I was dreading, whilst at the same time horny from excitement beyond compare. I had been cross dressing since I was a teenager and never before had I let anyone see me 'en femme', I had fantasized about this moment for over half of my life and now, because of my Master, who I know only as ER, my dreams were about to be realized.

What will happen? How will I react? What will she make me do? All of these questions are running through my head when....

Knock, knock, knock, at the door

My heart skips a beat, I inadvertently break into a cold sweat, I start to panic, think about not answering the door, I walk up to the door and just stand there, frozen, unable to open it, unable to breath...

Knock, knock, knock

"Who is it?" my voice is a whisper, a nervous shaking whisper.

"Are you going to open the door Stephanie, or should I get the concierge to open it for me?" the voice is female, and very sexy

On being called Stephanie I snap out of my trance and force myself to open the door. My hand unlocks the door and I tentatively ease the door inwards, as the door opens fully we both stand there, observing each other. The woman in front of me is gorgeous, everything I had dreamed of. She is about 5'8", has brunette hair, 34D breasts and is seriously curvaceous. She is dressed in a very sexy red evening dress which hugs her sexy body, the hem stops mid thigh (a lot lower than mine). Her make up is sexy, she is sultry, sexy, and classy, she was making me feel like such a dirty slag in comparison.

After a few seconds of checking me up and down the sexy lady in front of me smiles at me as she enters the room and places a small suitcase on the queen size bed..."well well, aren't you the hot slut then Stephanie" she grins "looking like that you cant fail but get screwed tonight!"

I smile back "I err, yes Miss...Thanks Miss...err......what shall I call you Miss?"

"Mistress is fine." She replied

"Ok Mistress" I responded

"Good girl" she said as she took me by the hand. Before I knew what was happening we walked out of the room hand in hand and walked down the corridor towards the elevator. Whilst I am fairly well practiced at walking in heels I could not keep up with my new Mistress, and all I could do was totter alongside.

"Where are we going?" I ask on the way to the elevator

"To the bar, for a drink"

"The.....the bar" I am panicking now "what! You are taking me to the public bar dressed like this.....you can't!" My voice is erratic, my fear audible.

"I can....and I will" came the reply, "anyway, you said you wanted to be humiliated...its too late to change your mind now...and, if you are going to talk may I suggest you at least try to use a feminine voice, at the moment it is so obvious what you are........a bloke dressed like a slag!" She practically spat the last bit, leaving no doubt at what she thought of that.

I walk alongside in silence, worried now, I had never practiced a female voice, had never thought I would need to. We approach the elevator and I press the down button, still admiring my sexy long fingernails as I press the button. After a few seconds the doors open, my heart stops as I notice the elevator is not empty....a young guy is inside, he is tall and, some might say, handsome, he is wearing a well fitted suit and looks like he is on his way out on a hot date. As my Mistress enters he nods in welcome with an admiring glance. Then his eyes notice me and I see them practically stick out on stalks as he drank me in. His grin widened and I could see he was making no attempt to hide the fact that he liked what he saw, in fact I am sure I saw a bulge appearing in his pants, but then again my dress does shout out fuck me now, I am desperate!

After what seems like a few hours, but in actual fact was just a matter of seconds we reached the ground floor, the guy in the lift strained to tear his eyes off me and leave the lift. I just smile at him as he walked away, turning back a number of times to keep checking me out. Wow, I thought, maybe I am passable as a female.

"Do all guys react to girls like that?" I ask my Mistress as we walked towards the bar.

"Oh, believe me, that was tame....In an outfit as daring as what you're wearing you were lucky not to be raped on the spot!" she smiled at me and her smile widened as she saw my face flush.

I wondered what I had got myself into as we walked across the marble reception floor and our heels made that loud clicking sound as we made our way to the bar. I was very aware that of the heads turning and their eyes following us as we entered the public bar. I would never have done this alone, it felt as thought he whole of the hotel was in the bar, and every pair of eyes looking at me, I inadvertently started playing with the hem line of my dress and tried to pull it down over my stocking tops, though I am sure all I succeeded in doing was highlighting the fact that my dress was way too short!

My Mistress sat at the bar and motioned for me to sit next to her, as ladylike as possible I perched on the edge of the seat and swivelled my legs under the bar, attempting to limit the number of people that would get a view straight up between my legs. I think I was quite successful and smiled as my Mistress orders two large gin and tonics. After a few more gins I start to relax a little and almost begin to enjoy my surroundings, when my Mistress puts a wrapped gift in front of me.

"What's this?" I ask

"A gift from Master ER" she grins a wicked, knowing grin and I fear to open it already. "Go ahead, open it sexy"

I pick up the package, it is a small box carefully wrapped, I have difficulty opening the wrapping due to my false nails but after some perseverance I get one end open. After a little more struggling the box slides out of the wrapping and to my astonishment I am staring at a clear but plug, I look around the bar to see who else has noticed what I have just been given, I cant decide if people are talking about me or not. I look back to my Mistress who is looking at me with interest and seems to be enjoying watching me squirm in my public humiliation.

"OK Stephanie, here is your first instruction, you are to go to the ladies room and insert your new toy into your ass, then return to your seat next to me!"

I think about refusing but quickly decide any alternative is much worse, a stand up argument in a busy bar over a glass but plug, I don't think so. I pick up the plug and without muttering a word make my way over to the ladies room. Again, the looks and whispers as I move across the bar, men looking at me with longing, women shaking their heads in disgust, I just head straight for the toilet.

I pushed open the toilet door and to my relief found it empty; I entered a cubicle and locked the door behind me.

As soon as I lock the door to the cubicle I start to shake, I am close to tears, and I can't stop myself. My dream is coming true and I am so confused that I am cracking up. I have never been so scared in all my life and I just know it is going to get a whole lot more exciting as the night goes on. Gathering myself together, I take the plug out of its box and find it to be quite slippery where it must have been pre-lubed. On closer inspection I see that there is some mechanism inside the plug, though there are no buttons or wires to a controller, just a clear plug which is about 3 inches long and over an inch wide at its widest point.

I place it on the side and carefully hitch up my dress, pulling the string of my panties out of the crack of my ass and moving it to the side, which is no easy feat with long fingernails. I pick up the plug, bend over the toilet and slowly ease it inside my ass. I feel my ass filling up slowly whilst at the same time my sphincter is stretched wider and wider. I start to apply more pressure and the plug sinks deeper and deeper inside me until I feel as though it won't go any further; I make a last push on the plug and gasp as my ass sucks it in and closes around the base, holding it snugly in place.

Standing up straight I replace the string of my thong along the crack of my ass, which further holds the plug inside me. As I straighten I feel the plug moving and I know I will not be able to forget that it in a hurry!

Just at that moment the door to the toilet opens and I hear a couple of girls giggling and laughing as the enter the cubicles, my heart racing again I pull my dress down, wait for the cubicle doors to close and walk out of the toilet back into the bar. OH MY GOD, every step I take I can feel the anal plug burrowing deep inside me, I try to walk back to my seat as normally as possible but I am not sure what normal is in four inch heels and an ass that feels like it is about to burst.

Finally I make it back to my seat and slide in next to Mistress Leane, "ughhhhh, fucking hell!!!!" I try not to scream aloud as I inadvertently sit down on the plug, thus pushing it even deeper inside me, which I hadn't thought possible!"

"So, it's in then honey" a statement, not a question, said rather too loudly for my liking. I just nod. She grins and lightly strokes my leg. "Time for the fun to begin then!" She laughs out loud as she clocks the terror in my eyes.

My Mistress orders two more large gin and tonics and handed one to me, we both drink, me a little too quickly, but I am so nervous.

"So Stephanie, why don't we play a little game?" that mischievous grin again "It's called truth or dare, you have probably heard of it!" I am feeling quite light headed now

"Sure" I reply "truth please"

"Truth huh", she is silent for a moment "OK Stephanie, Have you ever......" she laughs loudly, after composing her self she looked me in the eyes and tried again, "Have you ever fallen off your seat, in a busy bar, whilst dressed like a complete fucking cum slut, screaming in ecstasy because of a vibrating plug in your ass?"

"No,.... of course not....what sort of question is that?" Then the penny dropped "Oh my god.........what.......VIBRATING......please no....no...not here.....I beg you......pleeeeaaaasssseeeeee!!" As I was begging I notice a small remote device in her hand, my begging became desperate.

"NOOOOO....please no, I will do anything, just not here.......too many people watching...." With that I saw her fingers flick a switch on the remote and almost instantly I jump as I feel a dull whirring deep inside my ass. Shaking my head and biting my lower lip I realize no amount of begging was going to deter my Mistress, only now do I realize what she meant by fun.

Another notch - the whirring increases inside me and it feels as if the plug is expanding, I grip the bar with both hands as the plug inside me starts to hit the right buttons. I start to shake and break into a light sweat as small waves of pleasure start to ripple through me.

Another notch – I can focus on nothing else other than the vibrating inside my ass, my whole body feels like it is vibrating as the pleasure intensifies. I look up at my Mistress pleading with her to stop; she is still laughing at me as her fingers flick the switch again.

The plug expands again, now my knuckles are white as I grip the bar so tightly. My body is trying to expel the intruder, but it won't move. I start to pant and moan in pleasure, I know where I am but I can't help myself, squirming in my seat, and crossing and uncrossing my long sexy legs, nothing will relieve the pressure inside. In a cold sweat now my whole body starting to spasm in waves of ecstasy, I look at my Mistress and see her hand move for the remote.

"NO PLEASE DON'T, I CAN'T TAKE ANY MORE PLEASE, NO MORE" I hadn't realized I had shouted. The whole bar was now in silence looking at me. I no longer cared, I couldn't care, and my whole world was consumed by the pleasure generated by the vibrator in my ass.

My Mistress moves the dial again, I start to scream, my body in involuntary spasm, sweat pouring off me, tears running down my cheeks.

"That's half way" I vaguely heard her,

"Half way!, no, half way, it couldn't be."

Two more notches – That is too much, I could no longer control myself, I try to stand, to run to the toilet and remove it, my legs no longer worked and I fall off my heels and land in a heap on the floor. Once on the floor I start to crawl towards the ladies toilets.

Another fucking notch – I could no longer crawl! I was just a quivering mess of pleasure on the floor of a busy bar, I feel like I am about to pass out when I cum, right there on the floor, like never before, I feel cum exploding from me, spurt after spurt after spurt. I am writhing on the floor, moaning, crying out in pleasure and in pain.

I was sobbing, squirming when I notice the vibrating had stopped. Just like that it stopped, I relaxe, my breathing heavy, I start taking deep breaths, recovering slowly as the last few waves of pleasure leave me. I suddenly realize where I was; I stand up, my legs still shaking. I am so embarrassed, humiliated, and my Mistress is nowhere to be seen, she has gone.

I walk out of the bar trying to ignore all the laughing. Click click click again as my heels hit the marble floor on the way to the elevator. My hands shaking as I push the button, the doors open and I step inside. On the way up I look in the mirror, my make up is smudged and there is a large wet stain on the crotch of my dress. The doors open and I walk along the corridor wondering if my Mistress has left, where she has gone. I get to the door and remember I have no key, she had it. I knocked on the door, no answer; I tried again louder this time.

"Who is it?" She is in there, I thought

"Stephanie" I call through the door

"Who?"

"Stephanie" I practically shouted.

"Hello my sexy little slut" she says as she opens the door just a little "so, let me ask you again... have you ever fallen off your seat, in a busy bar, whilst dressed like a complete fucking cum slut, screaming in ecstasy because of a vibrating plug in your ass?"

I laughed "yes Mistress, I have"

The door opens. My jaw drops, this is far from over I think as I look at her new outfit. She is wearing a sexy red PVC catsuit which looks as if it was painted on, but that is not what has me excited, again. Strapped to her crotch is a long black cock. A rubber strapon which is at least 8 inches long and pointing straight at me. I gulp as she pulls me in the room and slams the door behind me. She removes my cum stained dress and sits me down on the edge of the bed, before I know what is going on my hands are cuffed behind my back.