First Session Nightmare

'Hi! I'm Jayla, a 20-something passable crossdresser looking for a fun night in bondage'. That's pretty much how I started most of the ads I posted on several online personals sites over the last couple years. Along with a photo of me dressed and all made up of course. And like most people on those sites I never actually carried through with going to meet up with anyone, because they were either too aggressive right off the bat or just didn't have the same interests.

That changed though about 3 weeks ago I got a reply to my ad almost a week after I posted it, which was strange because normally I get 15 or so replies within a day, find 2 or 3 possibilities and then that's it. Anyway, the message came from someone only identifiable as Sir, with a simple one-word title, Prisoner.

His message was this, "I will give you the best night in bondage you'll ever have, and then some!"

I replied immediately and we exchanged messages back and forth for the rest of the day. Before I knew it we had gone over interests and limits, his experience and my not so much experience. He reassured me with one more message saying our first meeting would be an easy "introduction" nothing to worry about. I don't know why but there was just something about how he worded all of his messages that I trusted him.

I asked him when he wanted to meet up and he quickly suggested that I come over to his place that night. I thought about it for a short time and convinced myself that if I didn't do this now, I probably never would, so I agreed and he gave me his address and told me to be there at 9 o'clock. I figured it would take about 30 minutes to get there which gave me about 2 hours to prepare and second guess myself for rushing into this.

I found that the more I got ready, the more aroused I got, which in the end is the main reason I went through with it and didn't flake out. I decided that since I would be driving over at night, that I would go out and show up fully dressed as a girl. I showered and shaved my whole body, then did my makeup and put on my wig, which gave me long straight black hair down to my lower back. Now, what to wear? I decided to keep it simple and went with a plain white top, small black leather jacket and short jean shorts that are rolled at the bottom. Also, I put on my favorite pair of black fishnet dancer tights, then the shorts and finished it with a pair of black converse to complete the look.

After admiring myself for a bit, I realized I needed to leave if I was gonna get there in time, so I ran out of my apartment with only my phone and keys and drove off, not even thinking about anything, just completely aroused but nervous at the same time. I didn't have the  "what the hell are you doing?!?!" thought until I turned onto what my phone said was the driveway and realised the house was set back, well off the road and up a twisting tree-lined driveway with really no other houses in sight, certainly none within shouting distance I thought to myself and nervously laughed.

I pulled up to the side of the house at 9:04, fashionably late I thought. Only the light above the side door of the house was on, which looked like it led to a dimly lit extra room full of storage bins. I realized my hands were now shaking and I had a cold sweaty feeling all over. I was weirded out by the appearance of the house from the outside and what small amount of the inside area that I could see.  'You've come this far' I said to myself and without much more thinking I quickly locked my phone and tossed it in the glove box. I opened my door and felt the warm early summer night air run up my fishnet covered legs and before I knew it, I was standing at the side door of this guys house knocking on the glass door, while at the same time realising I'm standing in a total strangers driveway that I've just started talking to on the internet, whilst also being fully dressed and made up as a girl.

Before I could come to my senses the doorway was filled by a tall figure, I'm 5'10" 160lbs. and this guy seemed to tower over me, I figured he was at least 6'3" looked to be between fifty and fifty-five years old but still was physically in incredible shape. He spoke quietly but with purpose and asked what a little sissy girl like me was doing so far outside of town at this time of night?

I was caught off guard and didn't know what to say, so I just nervously laughed and looked down at my converse, he said you look even better in person and that outfit is very hot! "Thanks", I replied shyly and he stepped to the side and invited me in, I stepped past him and waited while he closed the door behind us and then slowly looked me over as he walked back in front of me.

"That outfit is missing just one thing." he said as he lifted a pair of handcuffs with one finger from his side pocket, "I was gonna ease into this and chat for a bit, But, you are 10 minutes late so, I guess we'll have to get acquainted this way. Now, turn around and place your hands behind you."

I felt my stomach sinking as he finished speaking and without thinking my body just started reacting, I did as I was told without actually knowing how I did it, I felt like I was watching it happen to someone else and it wasn't until the first click of the handcuffs around my left wrist that I snapped back into reality, I was now staring back out the same door that I had just come in 30 seconds ago, as the other cuff was tightened around my right wrist and I felt a pull on my arm as he said, "Ok, follow me."

I was led by the arm through a dimly lit kitchen and down a dark hallway to a set of stairs. "Watch your step", he said as we started climbing the dark stairway. Once at the top, I saw a light coming from the other end of the hallway from up in the attic, as there was an old looking ladder hanging down from the ceiling where the light was coming from. He led me up to the ladder and we both just stared awkwardly upward for a moment.

"I don't think I can make it up this ladder with my hands cuffed." I said and he sternly replied, "You will and I'll help you."

With that he let go of my arm and placed a hand on my butt and began boosting me up the ladder, I got the hang of it just in time to be able to see into the attic, and I stopped climbing for a moment as I looked around. There was one light hanging down from a beam just above the ladder that was lighting up most of the attic space. Nothing but insulation and bare roof on the left side and then the same on the right, but there was a large square wooden platform with what looked like a very expensive bondage cage in the center of it. There was cuffs, rope, harnesses, gags, padlocks, and chains laid out on one side of the cage and some more stuff on the far wall behind the cage on a little table, but before I could figure out what it was I felt a push from behind urging me up the ladder.

Once we were both in the attic we stepped onto the platform and he went over to the pile of restraints without a word and came back with a pair of ankle cuffs with the chain shortened by a padlock, he knelt down and secured both my ankles. He then pulled a key out of the same pocket he pulled the handcuffs from downstairs and asked me to turn around, which I did and he unlocked the cuffs from my wrists and said, "THERE YA GO!" in a totally different friendly tone, which was unlike anything he'd seemed to be up until now.

I nervously said thank you? And just stood there as he set the handcuffs down on the ground near the cage. He then said, "I want to keep you in some sort of restraint at all times while you're here, as a reminder of who is in charge here." I nodded and he continued, "Welcome to my playroom. I figured we'd get you started easy and let you spend some time lightly restrained in the cage, what do you think?"

I said, "Okay, how long?"

He said, "ehh, maybe an hour... Or longer if I feel you need it." he trailed off with a grin.

I looked over at the ladder that led back downstairs into the darkened house. He noticed this and said, "Of course, you could try and run away now. Although, I doubt you'll get very far with your ankles cuffed 6 inches apart." I agreed and he smiled and said, "So, I guess climb on in!"

He turned to the cage and swung the door open for me. I slowly hobbled over as best as I could with my ankles cuffed as close together as they were, just as I got to the cage he said, "Oohhh wait! Almost forgot something!" and he went to the table behind the cage and returned with a full head harness with a red ball gag attached. I stood there as he went around behind me and slid this device over my head, tightening and buckling what seemed like 20 straps until my head felt like it was completely wrapped in heavy leather, finally he pushed the ball gag into my mouth and tightened the final straps and I quickly realised I couldn't move the ball around at all. It was wedged tight in my mouth and the placement of all the straps was allowing zero movements.

While I tried to deal with that, he had me get down on all fours and climb into the cage, I was just able to sit with my head slightly tilted forward and my back up against the back bars. He again picked up the handcuffs and walked behind me and asked me to put my hands and arms through the bars behind me. I did and he quickly cuffed both my wrists outside of the cage, so I was now stuck, up against the back wall of the cage in somewhat of an uncomfortable seated position. He walked around the front of the cage and knelt down to undo the cuffs around my ankles and he set those aside. He then closed the cage door and padlocked it.

I wasn't sure why though, I couldn't get out even if the door was wide open.

Hhe instructed me to straighten my legs out and put my ankles through the bars in the other end of the cage, which I did as I was told. He proceeded to tie them with rope individually to the bars of the cage and then together with another piece of rope from the outside of the cage, so I couldn't get my ankles back inside or bend my legs. He quickly added rope above each of my knees and tied them to the sidebars of the cage further immobilizing my legs, he looped a rope around my torso and two of the bars of the cage behind me and tied that off. Finally, he looped a rope around both of my arms, just above my elbows and tied them to the sidebars of the back of the cage.

I Quickly realized how stuck I was, as the only thing I could do was move my feet back and forth, wiggle my fingers and turn my head slightly side to side.

He reached into the cage from above me and loosened the buckle holding the ball gag in my mouth and I was able to just get it outside of my mouth but it was still resting on my lips. He then said, "So, think you'll be able to get out?"

I jerked my body back and forth futilely a few times before resigning to the fact that I was definitely stuck.

"Perfect!" he said.

Then. It got bad. He walked away from the cage behind me and said, "You know what I enjoy most about bondage? When the sissy has no idea how long she's been tied up and helpless, sitting tied in that cage with every muscle in her sissy body burning in pain, drooling all over herself cause that ball gag has been in for god knows how long... NowTHAT! is bondage".

I instantly got goosebumps all over my restrained body and started sweating, I heard and felt my heart pounding all the way down to my toes, and then I heard him slowly walking back toward the cage from behind me, still talking menacingly and I was just frozen in fear as I listened to him.

"How do I make you completely lose track of how long you've been in that cage and how long you'll stay in that cage? Only time will tell I guess..."

Before I could process what was happening he lowered one of his now gloved hands into the cage from above and slid one finger past my ball gag into the side of my mouth and quickly removed it, he then pulled the strap back tight against my head, which plunged the red ball back behind my teeth and deep into my mouth. He padlocked the entire harness to the top of the cage and now my head was rendered completely immobile. This happened so quick I felt like I didn't notice until after he backed away from the cage behind me that a small pill was now sitting on my tongue and I instantly knew.

"WHAT THE FUCK!!!" I yelled, but all that came out through the gag was WUHHDFUGGUHHHH!!! I struggled and pulled as hard as I could but nothing loosened. The pill felt like it was almost completely dissolved by now and there was nothing I could do. He made a slow pass around the cage admiring his work and then turned away before walking over to the ladder and took one more look before dropping out of sight. "Sleep tight" I heard him say from the second floor up to the attic where I now sat helpless and alone. Next was the sound of the ladder and door being lifted and re-secured into position sealing me in the attic completely restrained and locked in a cage. I was overcome by the incredible urge to close my eyes and fall asleep within a minute or two of the attic door closing and after fighting it for what felt like only a few seconds I passed out...

continues in part two