A Crossdresser’s Night in the Park

A Crossdresser’s Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirt
with a black stretchy lace blouse. Master Brian then asked me what I had on underneath my outfit.

Under my outfit, I told him, I was wearing a black satin bra with breast forms, a pair of black satin knickers and a black lace suspender belt that held up my black seamed stockings. Then I told him that I had on a long blonde wig, make up, and red heels with five inch heels. It seemed to please Master Brian when I told him that. Then he asked me if I had put on nail polish or not. Quickly I told him that I false finger nails on and I had a slutty red polish on them and on my toes nails.

Then he asked what toys I had with me. All I had was a paddle, gag, butt plug, and a dildo. Starting a scene for us, Master Brian told me that I had been a bad “girl” for making him ask so many questions to find out what I was wearing and what toys I had as we talked. I was to spank myself with my paddle ten times on each arse cheek, as hard as I could. After each time I hit my own arse I told Master Brian how it stung. Then he had me put my butt plug in my arsehole, and then I was to suck on my dildo so I could think about sucking his cock. As he told me how much he wanted to use and abuse me I was getting so turned on that now I had a very unlady like bulge in my knickers.

Then Master Brian asked where my computer was. I told him that it was in my living room, right by my picture window. I was ordered to open my curtains so anyone walking by could see me all dressed up. After I opened the curtain I was ordered to stand in the window and fuck my own mouth with my dildo. As I was fucking my own mouth I could see lots people walking by, one small group of girls even looked right at me, then stopped and watched me for a few minutes. Then I was allowed to step away from the window, back to the computer.

As I told Master Brian about the girls watching me he asked me where I lived. When I told him what town I lived in, he told me that he lived in the same town. I was thrilled to learn that he was so close. Maybe we could meet one day. Reading my mind Master Brian ordered me to get off line and drive to a small park in town and wait for him there. Telling him that I would be there in ten minutes waiting for him. Quickly I
fixed my make up, applied some perfume, grabbed my purse and keys and headed for my car.

I got to the park and did not see anyone there. I decided to walk around a bit and wait for Master Brian in the shadows. About ten minutes later a car pulled into the park and a guy got out and started to walk around. As he got near I called out, “Master Brian?” in my best female voice. He replied, “I was not sure if you were for real or not.” “Very real, Master Brian,” I replied as I stepped out of the shadows so he could see me for the first time. As he stood there looking at me I
was afraid that he would not want me.

Telling me to stay where I was, he walked back to his car where he got a bag out of the trunk, and walked back to me, with a big smile on his face. Taking my hand he walked me over to a picnic table where he emptied his bag. There were all sorts of bondage gear in his bag. The first thing he did was put a collar around my neck. Then he attached a leash to the collar and walked me around calling me his “bitch”.

As he led me around I held my head high, I was so proud of being his “bitch”. Leading me back to the table Master Brian attached wrist and ankle cuffs to me and then walked me over to the monkey bars where he then attached my arms and legs to it, so I was facing the monkey bars.

Now I was all spread out for him. Feeling my skirt being pulled up and my knickers being pulled down I knew that my dream was about to come true. With only a whistle as a warning, I felt the sting of Master Brian’s riding crop as he started to beat my arse. Lowering my head, I moaned in pleasure as the crop rained down on my arse. I must have been
moaning to loud because the beating stopped and a gag was shoved in my mouth to keep me quite.

I felt Master Brian’s hands on my arse and then move between my arse cheeks where he found that I still had my butt plug in place. Pushing on the base, driving it in a bit deeper, he leaned over my shoulder and whispered in my ear, “You really are a slut, bitch.” All I could do was nod my head yes. I am just such a slut. Then he asked me if what I really wanted was his cock instead of a butt plug in my arsehole. Nodding my head yes again, he told me that I had to earn that privilege. If I did not have the gag in my mouth I would have told him that I would do anything to earn his cock. Reading my mind, Master Brian whispered in my ear “you would do anything to earn my cock, wouldn’t you?” Nodding my head again, I let him know that I would do anything. Then I was shocked when I felt his cock rubbing my arse as he begins to hump my sore,red arse.

Master Brian started to grope my breast forms and then one hand slid down my belly and under my skirt where he grabbed my balls and squeezed them hard. It was a good thing that I was gagged because I screamed from the pain. As Master Brian squeezed and twisted my balls he hissed in my ear, “This is just a taste, ‘bitch’, of what is to come.” Master Brian
then wrapped a cock and ball harness around the base of my throbbing cock.

Then he released my left wrist and ankle and turned me around and reattached me to the cold steel of the monkey bars. Now I would be able see what was going to happen to me next. I saw Master Brian reach in his bag and pull out a length of thin rope and as he walked back to me he said with a wicked gleam in his eyes, “I bet you are wondering what I am going to do with this.” As I nodded yes, he knelt down in front of me
and played the rope over my cock. As good as that felt I knew that making my cock feel good was not what he had in mind. With a well practiced flip of his wrist, Master Brian tied a loop around my balls and then started to tightly wind the rope around the shaft of my cock. With the rope being wrapped around my cock so tightly it hurt so bad that I bit down on my gag. Then I was startled to feel my cock start to throb. With a sharp smack to my bound balls, Master Brian told me that
if I could not control myself he would leave right then and leave me bound to the monkey bars to be found in the morning.

Visions of me being found chained to the playground equipment, dressed as a woman, by mothers bringing their c***dren to the park to play scared me enough to keep from cumming. When he was done I saw that my cock was wrapped in rope so only the head was exposed. The rope was so tight that my cock looked pencil thin but the head looked three times it’s normal size. Next he pulled my blouse up over my breast forms and then removed them from my bra. Master Brian walked over to the picnic table and picked something off of the table. As he walked back to me, he held up a pair of cruel looking nipple clips so I could see them and know what was going to come next. Pinching my nipples to make them stand up even more, Master Brian quickly attached them. I could feel them bite
in to my tender flesh as I tried not to scream in pain.

Master Brian just laughed at my attempt not to cry out in pain. As I tried to get use to the biting pain on my throbbing nipples walked back to the picnic table where he had his gear laid out. Returning I saw that he had his riding crop in one hand and something I could not identify in his other hand. I did not have to wait long to find out just what he had. Master Brian held up two very large fishing weights and as I
watched he attached then to my nipple clips. As the clips snapped shut he dropped them so they yanked unmercilessly on my swollen nipples. I was shocked when I realized that the loud moans I heard were coming from me. Right after Master Brian dropped the second weight I felt my tightly bound cock and balls getting a beating from his riding crop.

The pain quickly became pleasure and I thrust out my hips offering myself for him to use and abuse. I could tell this pleased Master Brian very much by the huge, growing bulge in his pants. Master Brian then unchained me and led me over to a picnic table that he bent me over and chained me to. Moving to my head, grasping my chin and raising my head he said “open up, bitch.” Opening my mouth wide he rammed his swollen
cock in my mouth fucking it as if it was a pussy. Oh, how I loved being used like this. It was a dream come true for me.

All too soon he pulled his cock out of my mouth and walked away. I could tell that he was getting something from his pile but I had no idea just what he was getting. Then he raised my skirt and pulled my knickers down getting me ready for the next round. Now he was using a large leather paddle to beat my arse. Much to my dismay Master Brian, knowing just what he was doing, had tied me down so I could not rub my cock against the
picnic table to bring myself to orgasm. When my arse was all red again I felt his cock pressing against my waiting and wanting arsehole. Without waiting Master Brian rammed his cock in my asshole and begins to fuck me. With great cock control Master Brian was able to fuck me for quite awhile before he started to cum in my arsehole.

When he was done fucking me, he untied me and ordered me to remove the thin rope from my own cock. As I started to remove the rope the blood rushed back to my cock with a rush of pain. Now my cock was bigger that I had ever seen it before. Master Brian orders me to jerk off into my own hand. After I had cum in my palm I was then told to lick my hand clean.

Master Brian packed up his equipment and left. As he walked away, leaving me there with his cum dripping from my arsheole, he said that maybe he would see me again on line soon. After he left I pulled my knickers up and straightened my clothes and I walked to my car.

Sitting was sweet torture on my sore arse as I drove home. I knew that I would be looking for Master Brian on line so we could meet up again. Maybe this time we could meet at his place where he would be able to use and abuse me longer. Maybe he would even share me with some his friends.

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