My First Time as a Woman

With my hands secured my Mistress sits in front of me and starts to touch up my makeup, my cock is hard again as she expertly reapplies my makeup. After a few minutes she is done and she stands me up and immediately makes me kneel in front of her, the big black strapon pointing straight at my face.

"Your Master ER tells me you have been practising" with no further ado the tip of the rubber cock is resting on my lips, she applies a little more pressure until I have no option but to open my mouth and let it in. The cock slides into my mouth slowly, deeper and deeper until it hits the back of my throat, I gag. All my training at home in preparation for this moment, and I gag.

"Come on slut, you can do better than that"

She slides the dick out of my mouth, and slowly back in again, this time as it slides deeper I am prepared, I rest it on my tongue, start to breath through my nose as the tip slides down my throat. She is very gentle and inch by inch the cock slides in, I can feel it sliding deeper into my throat. Concentrating not to gag the cock keeps sliding down until eventually it is all the way in.

"well done my cock sucking whore" she says as she pats me on the head, she then takes my head between her hands and starts to move the strapon in and out of my throat, slowly at first, then building up a rhythm, after a while I am being totally face fucked and there is nothing I can do about it with my hands cuffed behind me.

"Very good you fucking horny cum slut, you really do know how to suck cock properly don't you" I nodded very slightly "and you love it too, don't you" again I nodded very slightly. After a few intense minutes of having my face fucked she slides out of me, she lets go of my head and pulls me up to my feet. She moves me across the room and manoeuvres me so I am stood up against a table and told to spread my legs, not being in a position to argue I do as instructed, my ankles are tied to the table legs with rope. When she is finished I try to move, I can't. I am completely unable to close my legs and I am scared again. Especially when she turns the but plug on again, only two notches before she puts it down again. Even still, it is enough to work me up again.

I am then pushed across the table and lowered so that my body is flat across the table top. The table is not very wide and my head is clear of the table top. My hands are un-cuffed and retied to the two remaining table legs. I am now completely and utterly helpless.

My mistress comes round the front and again feeds the strapon into my mouth, this time I don't gag and it slides straight down my throat, breathing through my nose again she leaves it in position for a few seconds. My mouth is full of cock and my ass is stuffed and vibrating, my cock is so hard it is hurting. After a few minutes she stops, steps back and let the cock slide back out of my mouth.

She then walks round the table so that she is standing behind me; I feel her hands stroking my smooth legs, inside my open thighs, her hands stroking my ass, I feel my panty elastic get tight as her hands pull the string out of my crack. Just as I was enjoying her light sensual touch I feel a sharp pain as she pulls my panties hard until the elastic snaps. I feel my Mistress' fingers moving up my inner thighs again inching towards my ass, I feel her fingers grip the plug inside my ass and twist it. I feel my ass stretching as the plug is slowly pulled from inside me. Once past its widest point it practically fires out of my ass. It is sp wonderful to be free of it at last; it had been in me for ages and now I feel empty.

But not for long, almost as soon as the plug was out of me I feel another head pushing against me. I knew it was the strapon, it had to be. I just lay there, what else could I do, I feel more pressure applied, this is bigger than the plug. Much bigger.

I feel my mistress' hands on my hips as she pulls herself towards me, the pressure buids on my ass, I try to relax, more pressure, more and more until my ass relents and the tip of the strapon slides inside me.

"Arghhhhh, fucking hell" I gasp, "no", I screamed. It feels so big, so wide, I am so full, short breaths as I try to get used to the girth.

"Ohhhhhhhhh, yesssss" My mistress starts to apply more pressure and the cock starts to sink further and deeper into my ass.

"Oh my god, yes yes yes" deeper and deeper

"Ooooohhhhh god, how big is that fucking thing" I am panting now and still it is sinking further into me. Her hands grip my hips hard and with one final hard thrust I feel My Mistress' thighs slap against mine. It is all the way in I had never felt so full in all my life.

She then lay on top of me, her weight pushing me hard onto the table; I feel her hips gyrating and the strapon slowly moving in and out of my ass, the feeling is wonderful, I wanted to move against her, but I couldn't move at all and that made the feeling even more exciting. I was completely and utterly at My Mistress' mercy and she was fucking me harder and harder.

She climbed down off of me, without the cock sliding out of me and started to pump in and out of my ass, gripping hold of my hips hard she was thrusting into me so hard I started to scream with the pleasure

"OHHHH, AHHHHH, YESSSSS, BABY FUCK ME FUCK ME HARD...HARDER"

She took me at my word and started to ram herself into me, I started to moan.

"That's it you little bitch, moan like the little slut that you are! You little fucking girl,"

"Maybe you should experience a real cock, if mine isn't enough for you" with that she pulled out from me and I could here her behind me, though I could not make out what she was doing.

"What....why have you stopped, why...."I was sounding desperate now "please, fuck me, harder. Please" I tried to turn around to see what was going on but I was tied too tight.

After a few minutes I felt the strapon being inserted back into my willing asshole, but something was different, My Mistress was no longer wearing it, she pushed it all the way inside me and then buckled it to me, I was full again, and I loved it, but what was she doing. She walked back in front of me and I saw she was carrying a ball gag which she placed into my mouth and buckled tightly behind my head. After this she put a blindfold over my eyes and again fastened this behind my head. Unable to now speak, see or move all I could do was lie there and wait for My Mistress' next move.

"I am going back to the bar" she announced "don't you go anywhere my sexy little cum slut; if you are well behaved I may just bring back a present or two for you!" With that I heard the door open and a second later it closed, Hard.

"Mpfhgggggg grhmfffffff" I tried to call out after her but no noise came out. I was alone, helpless, dressed like a whore and tied to a table in a hotel room. I started to struggle, to try to get free, it was no use at all. Then I started to think about what she had said....a present, or two....no....she can't. no, not that.. she cant mean.....no....surely not.

After about an hour I heard a key in the door and the door swing open.

"Stephanie you fucking slut" my Mistress sounded drunk, "I hope you have been behaving yourself" she laughed at her own joke, knowing full well I had no choice but to lie where I was and await whatever fate awaited me. I heard voices, my Mistress, yes, but more than that, she was talking and laughing...I focused on the voices and heard what sounded like more than one male voice. The door closed and I could clearly make out two separate male voices as well as my Mistress. Before I had an opportunity to decide what was going on I felt my legs being stroked again...soft smooth hands running up my smooth stockinged legs. I felt the straps holding the strapon in place being loosened, and then released. The rubber cock was slowly pulled out of my ass, the feeling of release as it slowly passed out of my rear passage was sensational.

Then without warning I felt my Mistress' hands cupping my balls, then squeezing, not too tightly but tight enough. My cock was hard, as it had been all night and she started to stroke it, her hand gripping it firmly and stroking up and down its shaft, the relief was incredible after being shackled to the table with absolutely no contact for so long. After a few minutes of this she stopped. I moaned into the ball gag, but no noise registered, I needed to cum. I heard more noises behind me, in front of me and beneath me and could only wonder at what was going on. After a few minutes I felt my Mistress' hand back on my ever rigid cock, then I felt a wetness on the tip, my foreskin pulled back and kisses planted on the sensitive head of my swollen member. A few more seconds and I felt her mouth enveloping the head, sliding down the shaft, her hand squeezing my balls.

"hmfhhhhh, arhghhhhh, yghhhhhhh" her tongue licking the head of my knob, I tried to thrust my dick deeper into her mouth, but I was still tied so tightly. She started to suck and kiss and lick like I had never experienced before. The pleasure was wonderful when suddenly my ball gag was removed. This was completely unexpected as I was lost in the pleasure of receiving a truly fantastic blowjob.

Within a second of my mouth being freed of the ball I felt another object entering my mouth, this was warmer, wetter, although never tasted before I knew exactly what was being guided into my open mouth. It was an erect cock, seconds later my blindfold was removed and I was staring at a dick much larger than my own being fed into my mouth. I had no chance to react, and I had no option but to accept it. And so accept it I did, and my god I just looked down and watched as inch by inch this monster of a cock slid deeper and deeper into my mouth, breathing though my nose again as the head passed my tonsils and down into my throat. I couldn't believe it, the practice has paid off, I was deep throating and I loved it.

At the same My Mistress was now doing the same with my cock, I could feel the length of my dick pushing down inside her whilst at the same time she was squeezing my balls, the feeling was like nothing I had ever felt before until, suddenly, without warning I felt a pressure being applied to my anus again, though this time I new it wasn't a rubber cock. This was the real thing. I could feel every ridge of the penis sliding into me from behind, inch by wonderful inch I was being impaled, and I loved it.

I was being spit-roasted and deep throated at the same time. Again, I felt hands on my hips as a cock was thrust into me until I felt his balls hit mine and I knew he was all the way in. For a few seconds that's how we remained. A cock deep in my ass, another deep in my throat and mine deep in my Mistress' throat. Then, in unison, all three started to screw me, slowly at first, long deep rhythmical strokes, then picking up the pace, faster and faster. Harder and harder until I could take no more, but I had long ago discovered tonight wasn't about where I thought my limits were.

"Do you like that you little fucking whore" that was the guy with his cock in my mouth

"You like being fucked like a little girlie slut, don't you" That was the other guy with his cock in my ass.

I was taken way beyond anything I thought humanly possible; all three of them were fucking me deeper and harder, faster and faster. I knew I was about to cum, and I could do nothing to stop it, just then I heard both guys starting to moan, the pace stepped up yet another gear in what I recognised as I final spurt. And that was it, firstly I felt the cock in my mouth starting to twitch, at the same time the cock in my ass was thrust in to the hilt one last time before I felt it withdrawn completely. Simultaneously I felt what seemed like gallons of hot spunk emptied down my throat into my stomach, whilst spurt after spurt of cum was deposited on my ass.

This was too much for me and seconds later I was shooting my own hot spunk into my Mistress' mouth and throat.

For the next few minutes all I could feel was hot liquid running over my ass and down my legs as well as spilling out of my mouth and rolling down my chin.

Then, completely and utterly spent, I passed out...........

.......Knock Knock

I woke up; the sun was streaming in through the window. I was relived that I was no longer tied to the table, I was lying on the queen size bed, the covers had been removed and I was on my back, I was still dressed in stockings, bra and my corset, and my heels had been removed. And I was alone.

I tried to move, to get up and answer the door, I couldn't. My wrists and ankles were tied to the four corners of the bed, spread-eagled.

Knock Knock.

I stayed silent, hoping whoever it was would go away so that I could work out how to untie myself and go home.

The door opened, it must be my Mistress I thought... I was wrong, into the room walked a stranger, a woman, in a maids uniform. It was the hotel maid, come to clean the room.

She looked at me for a few seconds deciding what to do......then she smiled and locked the door..........................