Mistress Viagra Pt 01

This story is 100% pure fantasy. None of it ever happened. If you are offended by stories of a mature nature containing references to bondage and humiliation, please do not read.

This is fiction!!

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I had been chatting with a new online mistress for a number of months and during that time she had me buying all kinds of sexy woman's cloths, new sex toys and various other implements that she would have me send her pictures of once I had purchased them. Mistress had me buy several extra large dildos and extra extra large butt plugs and would instruct me via Skype to insert them in my ass then on several occasions while on video chat had me keep them in my ass while going out to the local adult store and go into the theatre undress and get on my knees and suck random cock while she watched.

Soon she began hinting that she would be willing to meet me in person, and eventually made arrangements for me to come to her house. She lived several hours from me. I was instructed to pack everything she had made me buy and be at her place at 12:00 noon on a Monday morning. I was told to make sure I didn't have any upcoming appointments or any plans and to tie up all loose ends of any projects I was working on and that I should be expected to stay until she was fully satisfied.

I left early the night before to avoid any traffic and received a Skype call from her about an hour into my drive. She was impressed that I was taking such precautions to arrive on time by leaving the night before and began to give me instructions for how she expected me to look while driving and what I was to be wearing during the 7 hour drive to her house. I stopped at a rest area, and began to prepare for what she told me to do.

I took out my skin tight wet look micro mini dress, and a large but plug and harness to strap it in. Went into the men's room and began to strip in a stall. I lubed up my ass and made sure I was completely clean back there, pushed the butt plug up into my ass and strapped it in with a harness to make sure it wouldn't move or slip out. I put on my stockings and dress, padded bra, and wet look long sleeve low cut top. Placed all my male clothes into a bag and when I felt safe that no one would see me I proceeded to head back to my car.

I called mistress on skype as I was putting on my makeup and listened to her tell me how to apply the blush, mascara, eyeliner, and lipstick.

I began driving again and drove the whole 7 hours only stopping once for gas.

I arrived at her exit about 2 hours early and pulled over to wait till it was time to leave. I got to her house right on time and I was pressing the button to the intercom at the gate to her driveway right at noon. Mistress answered and commended me on being so prompt.

I was told to drive up to the front entrance, get out of my car, get my bags with all the things Mistress had be having me buy, leave my keys, wallet and ID in the car, and kneel at the front door of her house.

At this point I began to feel nervous that something bad was going to happen, but I was horny and was dying to meet the Mistress that had been guiding me through so many nights of orgasms.

I did as I was instructed to do walked up to the front door, placed my bags down and kneeled.

I was waiting for a few minutes until the door opened and I was finally in front of my Mistress. She told me to kiss he feet and beg to be allowed into her home. I did as I was told, and she ordered me to my feet and had we walk into the front entry way of her house.

After I was in she shut the door leaving my bags sitting outside, and ordered me to strip. I did as I was told and stood naked in front of her wearing only the harness that held in my Butt plug. Mistress had me spin around for her slowly so she could inspect my body, the proceeded to hand me a glass of water and a hand full of pills. I took the pills one by one swallowing each with a sip of water, the proceeded to gulp down what ever water was left in the glass. Almost instantly I began to feel both excited and relaxed yet wide awake. I was lead into the living room where Mistress had me kneel at her feet while she sat in a large wooden chair with red velvet padding. I followed her instructions to un do the harness lean forward and while kissing her feet removed the Butt plug for inspection. Since I had be wearing it for several hours while driving it was dirty, and I was promptly spanked for allowing it to be that way. I was fitted with a locking leather collar, and lead into the bathroom where Mistress proceeded to give me several very large enemas followed by the insertion of a dildo bigger than I have ever felt before, she re attached the buckles on my harness and lead me on my hands and knees back into the living room where she sat in her chair and I leaned forward and kissed her feet until I heard the front door open and close. After a few moments a very young girl walked into the room and said Hi Mistress in a gentle sounding voice. mistress responded Hi Honey, Happy Birthday. The girl responded Yes Mistress. She left the room and went upstairs.

Mistress looked at me and began to pour me another glass of water and had me take another hand full of pills. This time right after I took the pills I began to get an instant erection, and as I did the girl walked back into the room naked and stood in front of me and her Mother. Since I was on my knees, I was eye level with her beautiful young shaved vagina, staring at its soft smooth outer lobes, and glistening pink wetness.

Mistress asked me if I thought the girl was pretty and I answered that I thought she was Beautiful.

I was told to stand up and face the girl, and I did almost trembling with excitement and shame as I was sporting a huge erection and had a harness holding a very large Dildo up my ass that I am sure the girl had seen when she first came into the room.

Mistress asked the girl to lead me downstairs and said she would be there to join us in a couple minutes.

The girl took hold of my leash and guided me towards the door to the basement, and down a long flight of stairs.

When we got to the bottom of the stairs the girl turned on the lights and lead me to a table in the middle of the room.

Surrounding the walls were all different types of bondage gear, helmets masks, straps, whips dildos, and other devices I didn't know what they were.

We waited several minutes before Mistress came down and when she did, she walked over to us and said to the girl, Honey, you know what today is right?

The girl shyly responded, yes Mistress.

Mistress said, what day is it?

The girl said, It is my 21st birthday Mistress.

Mistress then informed me that I was to be the girls present and the girl after today would become my new full time Mistress, that I was to follow any and all instructions given to me by her, and never disobey of argue. But that before I could fully appreciate her as a true Mistress I would be granted the opportunity of being the first man to ever have sex with her vagina, and that once I knew how good she felt, I would beg to be allowed to follow her every command, for the rest of my life, always living in anticipation of the possibility of being allowed to have sex with her, while almost always being denied the pleasure of such a glorious reward.

Mistress had me get on my knees, and told the girl to turn around so her ass was close to my face, the girl did so and I stared with my cock fully hardened and the girl placed my face close to her ass. Mistress positioned the girl so she was leaning forward and her hands were on her legs just below her knees. She stood there while Mistress lubed up the girls ass and right in front of my eyes proceeded to push a very large butt plug up into the girls ass. Mistress told me that girl had been training her ass for a number of years and that this was a plug she was used to wearing for long periods of time.

Mistress then lead the girl over to the table and had her lay on her back, she placed the girls feet up into stirrups that were connected to the end of the table and strapped her feet into them.

I was then guided with my leash over to the table on my knees and my head was placed between the girls legs. Mistress told me to start licking the girls pussy, and I did without hesitation. The girl responded by moaning softly and gyrating her hips as she began to get moist and feel the warmth of my breath and tongue.

After about a half hour I was told to stop. Mistress gave me another glass of water and more pills, then proceeded to hand me a glass pipe she lit and had me inhale from. She did the same for the girl than for me and then for the girl again. I was now even harder than I was before, and feeling wide awake from the smoke from the pipe.

I was told to stand up while Mistress injected a large syringe of lube into the girls pussy and I was then allowed to climb on top of the girl.

Face to face with her my mind was going crazy, I was feeling the effects of the pills, the smoke and the excitement of being given the honor of taking this absolutely gorgeous young girls virginity.

Mistress told the girl that she was going to guide my cock into her and that it was going to hurt at first but eventually would begin to feel good. I was told to not pull out and not to pull back, only to move forward regardless of the reaction the girl might be expressing.

As Mistress grabbed hold of my cock she slowly began pulling me forward, she rubbed the head of my penis up and down along the girls slit, and proceeded to gradually keep moving me forward while moving my cock up and down until it penetrated the girls soft warm mound. I could sense the immediate discomfort the girl was feeling but Mistress continued to slowly ease me forward filling the girl a little at a time as he pussy tightly wrapped around my incredibly hard engorged cock. As it pushed in further and further the girl began responding with more looks and feelings of increased discomfort, I could feel the butt plug that was in her ass only separated by the thin wall of skin between her pussy and ass, and after about ten minutes all 8 inches of my fat cock were buried into the girl my balls resting on the base of the butt plug that was filling her bottom. The girl had tears in her eyes as she was being split in two between her legs, and Mistress held her hands on my ass pushing me as deep into the girl as I could go.

She reached around the girl's body and grabbed a heavy leather strap that she then brought up around the back of my ass. Mistress connected the strap to another strap from the other side of the table and pulled it tight leaving only enough room for my cock to slide back and forth inside the girl about 2 inches, but making it impossible for my cock to come out of her pussy. She then walked away from the table for a minute and was doing something behind us. We couldn't see. I was eye to eye with the girl, looking at her with our faces only inches apart. The girl still had tears in her eyes and I felt bad for being so hard, and horny and having such a strong desire to move myself inside her, knowing it was causing her extreme discomfort, but only thinking of my own selfish desired to massage myself inside her tight wet pussy till I could feel a sense of release.

After about 10 minutes I felt Mistress hands on my ass releasing the harness that was holding the dildo up my ass, and with one motion pulled it out of me, leaving my now well stretched gaping ass feeling empty. Mistress used another syringe of lube to inject a copious amount of lube into me, and then I felt the head of another dildo being pushed into me. The force of the dildo pushing into me was pushing me deeper into the girl, our bodies as close together as they could be, the dildo was huge, and fat. I couldn't see it, but I could feel it was larger than the one that had previously been inside of me. When it was past my colon bend and probably about 14 inches inside of me, Mistress did some adjustments behind me, the I heard the sound of a motor and began to feel the dildo begin to move in and out of me. The fucking Machine was set for 8 inch strokes of the 14 inch dildo, keeping it moving inside me and pushing at my colon bend with every stroke.

When Mistress was satisfied with her work and confident that the dildo would not accidentally come out of me, and walked around in front of us, whispered to the girl that she was now a woman, and that she would soon be my Mistress for life. She told me to enjoy the time I was going to be inside her, and that the feeling I was feeling was going to always be a reminder to serve and obey her as my Mistress from this day forward. Mistress gave us each a glass of water, and fed us some pills. The pills the girl was taking were different than the ones she gave me. She gave us each a few more hits off the pipe, and said she would be back to check on us soon. Mistress then informed us of the total plan that we were to be staying this way strapped together for the next 48 hours, and that she would be doing various different things to us at random intervals to keep my cock fully hard, and to keep us Both awake, horny and active. She lit a candle next to us, walked towards the stairs, turned off the light and left us.

The dildo in my ass was moving at different speeds all on its own running through a computer program to control the depth and the speed of the strokes inside me. It had a control to randomly turn on a vibrator inside the dildo that stimulated my ass while the dildo pounded and abused my colon deep inside at the bend.

Staring at the girl I said to her I was sorry if she was feeling pain, and she responded that it was okay, it didn't really hurt anymore, it was just a new sensation and while it felt un comfortable, it wasn't painful anymore as it was when I was first guided into her virgin pussy.

We talked about how it was going to feel to be locked together for so long, and I told her I was really feeling the need to be able to cum, that I thought my dick was going to explode, if I didn't try to pump myself inside her, and feel some sort of release. She said it was okay and that she too needed to cum and for the first time experience a orgasm with her pussy, that for a long time her mistress had been training her ass, and only allowing her to cum or to achieve orgasms from her anus, and that she had been strictly forbidden from ever touching her pussy, that her mistress made her wear a steel chastity belt and kept her plugged every day during and after school and that she had never even been allowed to wipe herself after she went pee, because her mistress didn't want her to feel the sensation of her pussy being touched, that she used to hump her dildos at night and on the weekends, slamming them into her asshole until she achieved orgasms.

As she told me her story, my mind was racing a million miles a minute. It was making me so horny I began grinding and thrusting into the girl, she used her hands to hold me by the head and guided her lips to mine, we kisses as I used her pussy to try to relieve my frustration, and after about an hour of heavy pumping and grinding I finally succeeded in achieving an earth shattering orgasm as she did the same, I pushed as deep as I could into her tensing up my body to the point that I could hear the motor on the fucking machine begin to stress, and it relentlessly pounded my ass and I basked in the feeling of my cock filling this girl with cum. As I began to relax, the fucking machine continued its assault of my colon, pounding away with no regard to my feelings. The girl and I kissed and stared at each other in total bliss, and as I recovered, I gradually went back to slowly moving my cock the couple inches it was able to move. My back was beginning to hurt, and the dildo in my ass was non stop. After a few hours it became obvious that I needed to pee, and I told the girl I was feeling as though I needed to release my bladder.

She told me that she was feeling the same way, and that she was sure it was all part of her mistress plan, to know that us being locked together with all the water she had been giving us, that this was something we were just going to have to accept and do together.

For the girl to pee it wasn't really a problem, she held her breath and began to squeeze, and soon I could feel the warm liquid as it hit my lower belly and began to run down between her legs soaking my balls and eventually we could hear the sound of the puddle forming on the floor.

For me on the other hand I was stricken with guilt that I had to pee into this girls soft warm tight young lovely vagina, and I didn't want to do it. I held out as long as I could till she finally could sense my unrelenting discomfort, the dildo plowing into my ass was hitting the inside of my bladder, and finally she told me not to worry that it would be okay, that she would forgive me for having to cause her such degradation as to fill her with my urine, she held my face and stroked my checked and told me to go ahead and just pee into her. I couldn't hold back anymore, and as the dildo in my ass was working back and forth, I concentrated on releasing myself, I squeezed and slowly felt a slight amount of pee exit my penis, the fact that I was still rock hard from the Viagra pills, and the dildo was pumping me so hard and deep and fast made it almost impossible, but after trying for a while, finally a steady stream of pee began to fill the girls pussy, she looked at me with a look of relief for me, and said it felt good, and for me to keep going, and as I continued, I felt it leaking out from around my cock and heard it mix with the puddle that had already formed on the floor below us.

As the candle next to us looked like it was almost ready to burn out, we heard the sound of the basement door opening.

Mistress came down the stairs turned on the list and walked over to us. She turned off the fucking machine that had been abusing me, and stared at the puddle below us. She smiled, and said that she was glad we decided to relieve ourselves.

She went behind us and removed the dildo from my ass, and as she did it gave way for the rest of the urine inside my bladder to relax and find its way out of my penis and into her daughter who looked at me and smiled as she felt the warmth of the flow seeping from inside her.

Mistress gave us each more water, and more pills, a few more hits off the pipe, and then shoved a monster size butt plug up into my ass. I know it was the biggest thing I had ever had in me, because she showed it to me before she pushed it into me. She fastened to straps the the harness, and then re adjusted the girls legs with some rope she attached below the girls knees, pulling her legs up to words her head.

This left the girls ass fully exposed and her butt plug accessible, while pushing her hips and waist into a position that made my cock reach even deeper into the girls body.

Mistress then took the hot wax that was left in the candle and poured it onto my back and down my ass causing me to tense up around the plug, and push as deep as I could into the girl. She gave us each another hit off the pipe, another glass of water each, lit another candle, and walked away, turned off the light and went back up the stairs.

So far I had only cum once, but was feeling the effect of the dozen or so Viagra pills I had been fed. I began to work again at finding some level of release as the girl and I embraced and tried to each achieve an orgasm together again.

We did it again and again and again building up each time to earth shattering orgasms, and I could feel the wetness of the girls pussy as it was filled time and time again with my cum.

She told me that not only was today her birthday but that her mistress had been tracking her menstrual cycles, and today was her most fertile time of the month, that her mistress was assuming that on this day I would be getting her pregnant, and I was also becoming her full time cross dressing sissy sex slave.