Michelle's Hotel Bondage Experience

As a timid and closet cross-dresser, my biggest fantasy was to have a sordid meet in a hotel room, where I left what happened up to another person, with only major limits discussed and agreed first. After months of search and waiting for the right person to come along, I finally met 'Sylvia' online, and I had finally decided to take the plunge to meet up with her. After an exchange of emails and pictures that went on for several weeks, we both eventually agreed on a time and a place to meet. There were no exact instructions, I just left her with my online profile to browse over, which had all my likes and dislikes on there.

I had arrived at the hotel early for my meet with Sylvia, and settled into a luxurious hotel room, the honeymoon suit at a prestigious and classy hotel, a few hours drive from where I lived. After checking in, I was quick to unpack all my outfits and toys, hanging up as many as I could around the room. I had already removed all my body hair from head to toe excluding the hair on my head, so I made my way to the bathroom to apply my makeup, wearing nothing but a pair of black satin panties. My makeup quickly went on, consisting of primer, concealer, powder, blusher, long fake eyelashes, and deep red lipstick with plenty of sexy red shiny lip gloss on top.

Once my makeup was done, it was time to step into my satin lingerie. Before I put on my push up bra and fishnet stockings however, I took both of my Japanese style nipple clamps and placed them delicately and slowly onto my nipples, I took a thin chain, attached them to the clamps, passing around the back of my neck. This would allow Sylvia to pull on the clamps even though I was fully dressed. Next I put my white satin shirt and black skirt over the top of my underwear. I secured my black corset around my chest over the top of the shirt, and tightened it up as far as I could at the back, tying the cord in a firm bow.

I sat down on the corner of the large bed, and slipped my stocking clad feet into my favourite shoes, Matt black leather platform court shoes with a red sole and a 7 inch heel. Nothing says 'slut' like 7 inch heels!

To finish the look off, I put on my favourite short red bob wig, elbow length black satin wet-look gloves under my shirt sleeves, and my silver and gold bracelets on my wrists over the top of the gloves. Finally I put my over-shoe ankle cuffs on with a padlock in place, to stop me from being able to take off my shoes during the session. I had only minutes to spare before her expected arrival, so I quickly took 4 lengths of rope, and tied them to each corner of the bed as she had asked me to do so in a previous email.

Sylvia arrived on time, I took one final look at myself in the mirror before nervously welcoming her at the door. She looked pretty much as I had expected; perfect makeup, short black bobbed hair, PVC thigh high boots poking out the bottom of a luxurious long fur coat which she wore to hide the outfit underneath from the rest of the world. She smiled at me without saying a word, came into the corridor and promptly shut the door behind her. Coming into the room, she reached into her bag and pulling out a few of her own toys to add to the collection I had already laid out on the dressing table as instructed in the emails we had exchanged. Sylvia then took no time in getting me ready.

"Sit on the bed for me Michelle would you darling." she asked politely, as I followed her order by perching at the end of the bed. She took her wrist spreader bar with build in collar from the table, and locked the cold steel of the centre ring around my neck, before firmly holding up my arms one at a time, and cuffing my wrists to each end of the metal bar, securing them in place with a large brass padlock. As my second wrist was locked in place with the final padlock, I knew there was now no way back and that Sylvia was in complete control of the situation, and with that thought I could already feel my stiff cock throb gently in my satin panties.

Next came a similar spreader bar but for my feet. Sylvia knelt down on the floor in front of me, took each end and cuffed my ankles so my legs were spread wide apart, occasionally looking up at me with an evil smile every time a padlock clicked into place. Sylvia took a step back from me and removed her coat, to reveal a stunning dominatrix outfit, consisting of a black PVC over-bust corset over a black lace top, black PVC gloves, a black satin skirt, black stockings, and a pair of tight black thigh high PVC boots with what appeared to be 6 inch heels.

There was I, dressed as a slut, perched at the end of the bed, my legs spread wide by a spreader bar, and my arms outstretched to the sides of my head, unable to defend or even touch myself. Sylvia pulled a camera out of her bag, armed the flash, and took the first photo of me looking helpless.

Putting the camera down, she walked towards the head of the bed, ushered me to wriggle myself back toward the middle of the bed. Once I was sitting up in the middle of the bed, she pushed my torso back onto the bed, forcing me to lie down, the arm spreader preventing me from getting back up. She took the two ropes I had already prepared that were connected to the top two corners of the bed, and tied them to the two wrist cuffs on the spreader bar, to stop me from sitting up or going anywhere. The final 2 ropes at the bottom of the bed with tied to my ankles, pulling my body tort across the bed and essentially putting me into the spread eagle position.

Sylvia then sat at the side of the bed by me and starting stroking my cock through my panties and skirt, glancing up and down my body stretched flat out on the bed. She slowly pulled up my skirt, and slid her cold PVC gloved hand down my satin panties and around my throbbing cock. As I arched my back and started to moan quietly, she moved her head up towards mine and started to french kiss me, I had no choice but to comply, as every time I tried to stop the kissing, she squeezed my cock and balls tightly until I gave in to her open mouth. I could taste her strawberry lip gloss and smell her perfume as we lay on the bed together, tongues well and truly down each others throats for what seemed eternity!

After several minutes she came up for air, and stepped away from the bed. I turned my head to the side to see her removing her knickers, and had a good idea of what was next in store for me. This time she climbed onto the bed, and straddled my chest, kneeling on the bed with her weight on top of me. She leaned forward and pulled a pillow from the head of the bed, lifted my head gently, and placed it underneath. She worked her own skirt up her legs to reveal a large and erect cock. She shuffled forwards bit by bit over my arms towards my head, I could see the glistening head of her cock getting nearer to me, inch by inch.

"Open up!" she declared with a demanding tone, as she slowly guided her cock into my now waiting mouth below with her gloved fingers..

"Now show me how good you are," she asked as I realised she wanted me to do all the hard work.

I moved my head back and forward as much as I could, taking in the whole length with a satisfying slurping noise every few strokes. She slapped me on the side of the face

"Look at me!," she shouted in a stern voice whenever I tried to close my eyes or look away.

"I want to see you looking up at me." she added in a strict tone as she placed her hands on my head to assist with the back and forth movement. This went on for several minutes until I was exhausted, saliva and pre-cum dripping down from the side of my mouth.

"Good girl," she said as she stepped off me. "I just did that to get me in the mood." she added, with her still erect wet cock stopping her skirt from falling into the correct place.

Sylvia then started preparing for the next stage. She untied the ropes that held ankles to the foot of the bed, and removed the spreader bar that till now separated my legs. My arms remained in the spreader bar along with my neck, tied by ropes to the head of the bed . With my legs free to move, she tugged down my skirt with both hands, over my hips and pulled them completely off, revealing my black PVC suspender belt which was holding up my fishnet stocking. Finally she slipped my satin black panties down my legs and off me.

Now I was semi naked from the waist down, but before I knew what she was doing she started tying me up again. She removed the bottom two pieces of rope that were still attached to the bed, and with each length, took the rope and starting tying it tightly around my leg, just above the knee, then tied it in a knot. She left the ropes dangling from my knees and took the bondage tape to each leg. She pulled my foot into the bottom of my thigh so my knee was fully bent, and then proceeded to tape my calves to my upper thigh. She did each leg individually and after she was finished I couldn't stretch my legs out at all, they were fully bent, with my stiletto heels just touching my ass. To complete the position, she took the loose rope from each knee, passed it through the wrist cuff on the same side near my head, and tightened it, bringing my legs back towards my head and bum firmly up in the air, and also pulling my legs outwards slightly, exposing my ass and cock like never before. Finally she pulled the pillow from under my head, and worked it under my lower back instead, lifting my asshole up even more.

She walked over to the table and brought over the inflatable gag and rubber blindfold that I had left there. She inserted the bulb into my mouth, and lifted my head to buckle the strap at the back so I couldn't spit it out. She began inflating it until she could see my cheeks bulging with the rubber behind it, my muffled and almost silenced moan being an audible indication that it was the right size. I could taste the rubber in my mouth, and prayed to God that I wouldn't gag as I started to breath through my nose instead.

"There!", she declared, admiring her own handy work, "That should stop the people in the next room hearing you cry." she continued, before placing the blindfold over my head, but not over my eyes just yet, so I could see what she was doing next.

Sylvia pulled out her own toys from her bag, including several enormous dildos and butt plugs of various colour, as well as lubricant, followed by a wooden paddle. On seeing the largest dildo, a long black fist shaped one, I started to panic and moan through my gag again, I knew I'd never been able to take anything like that before in the past!, but she ignored my whimpering. When she was done getting her toys, she pulled the blindfold down back over my eyes so I was in complete darkness for the first time, only guided by the noises I heard around me.

With a sudden whack, she had started with the paddle first on my ass, gentle at the beginning, and then more firm as she went on. I could feel my ass getting hotter and knew it was starting to bright red in the first few minutes, changing to a more bruised feeling after around 5 minutes. Being blindfolded I couldn't tell when or where the next strike was coming.

After what seemed like an eternity, she put down the paddle and starting working on widening my ass, using a assortment of dildos and plugs she had brought with her. She worked her way up in size, slowly inserting the lubricated toy into my ass, and as I relaxed more and more she used the bigger and bigger toys, pausing only to add more lubrication to my hole. The final toy was a butt plug, which she had to use quite some force with to get it inside me, resulting in me moaning in pain for a second through my gag. Once the plug was in safely in, she removed the ball gag from my mouth resulting in me gasping for air, and then I felt her maneuvering herself into position on top of me in the 69 position, as I felt her erect cock for the second time, this time on my cheek as she got herself into the correct position. My cock was slightly limp after the pain, but it soon rose to the occasion as I felt her lips around the tip, with one hand around the base of the shaft, and her other hand on the base of the butt plug, slowly pulling and pushing the plug in and out of my ass. At first it was difficult and painful, the plug only moving a centimeter or two, but soon my ass relaxed again and she was pushing and pulling it all the way in and out with ease every second, speeding up the thrusting as I relaxed.

We were quickly sucking each other off in full swing, I was in heaven, and it wasn't long before Sylvia stared bucking her hips, and my mouth was quickly filled by her warm salty cum which I swallowed as fast as I could. Within a minute or two I was also coming in her mouth, moaning as I did with her now limp cock resting in my mouth still dribbling out the last of her cum onto my tongue. But what I didn't know that Instead of swallowing Sylvia simply kept it in her mouth. She left the plug in my ass, pulled herself back off the bed, before lying on me again the right way round. She pulled the blindfold off my eyes, and I saw her face inches from mine.

I knew what was coming seeing the cum drip from her lips as she gave me a cum filled snog, letting my own juices drip into my mouth, adding to the bitter taste that was already there.

"Make sure you swallow it all Michelle!" she said with some glee, as I reluctantly swallowed the second amount of warm bitter cum down my throat. Sylvia climbed off the bed to let us both have a few minutes to get our breath back, but left me in my bondage position on the bed whilst I did.

"Now that you're not longer horny Michelle, it's time for you to become a proper sissy!" she declared as she went across the room and picked up the shock collar from the table.

"Of course I'll have to put this on you now to ensure you don't change your mind!" she added as she lent over me and placed the collar around my neck, securing it with a padlock at the back. She took the remote control unit, and secured it to her outfit so it was to hand at any time I was unruly. Once that was done, she started untying my bonds from the bed so I could move.

"Ok Michelle, let's get you out of that outfit, freshened up, and into that gorgeous wedding dress of yours." Sylvia ordered as I made my way to the bathroom, still in my black heels. I re-applied some of my makeup, and checked my wig, Sylvia standing before me, tightening my corset even further. I took a deep breath in and felt the cords on the corset move, and my waistline go in once again. Sylvia quickly tied the cord in a bow at the back before I had a chance to breath out.

Sylvia went back to the bedroom, and admired the full length off the shoulder white satin wedding dress that was hanging on the wall. I followed her back into the bedroom to see her take the wedding dress off the coat-hanger and present it to me to help me step into it. I pulled it up and over my arms, Sylvia helpfully zipped it up at the back, it went on quite easily with the corset on so tightly underneath. I sat back down on the corner of the bed to change my footwear, knowing I'd now have a bit of a problem bending down.

"What do you want me to wear on my feet?" I asked Sylvia as I took off my black heels and quickly rubbed my feet whilst I had a chance. Sylvia glanced over at all the footwear I had brought with me and carefully lined up against the wall in a neat row.

"Hmmm," she murmured, looking up and down the row of shiny shoes and boots. Even I was impressed as to how many pairs I'd managed to cram into one suitcase and bring with me to the hotel.

"These." she declared with intention in her voice, reaching forward to pick up my black PVC knee high boots. These particular boots were lace up, with a zip at the side, and had a six inch heel. I was pleased with her choice, not only were those my most 'slutty looking' boots, but they would look great against the satin white material of the wedding dress. They were also quite comfy to wear for long periods of time, so I wasn't too fearful as Sylvia approached me. She knelt down in front of me, boots in hand, and slid my feet into them one at a time. She took no hesitation in pulling on the front laces as if it were a corset, tightening the boots around my lower legs tighter than I ever would myself, but the restrictive feel it gave me around my toes and calves was very arousing, so I certainly wasn't going to complain!

To finish the outfit I put on my white latex gloves that Sylvia passed to me, before finally putting back on my steel ankle and wrist cuffs with padlocks. I stood up, my black boots disappearing under the meters of white satin which flowed to the floor, only a patent toe peaking out whenever I walked. I made my way over the full length mirror which hung from the bedroom wall, as Sylvia took a brush and helped straighten out my wig, which was understandably slightly ruffled from the previous session.

"Now bend over for me, Michelle." she ordered, as she picked up a large rubber butt plug from the table and started to pull up my wedding dress, which considering its size and weight was quite a task. I put my hands up and lent against the mirror and did as she asked. She pushed the large plug in slowly, which went in with ease due to my previous ass-stretching exercise, but I still let out a little moan of pain as the widest part went in. At this point I wasn't sure what Sylvia had planned for me, but she had asked some probing questions the week before, and now I was started to worry what she had in store for the next few hours.

Once Sylvia was happy I looked picture perfect, she took a few more photos with the camera I had left out for her.

"These are the 'before' shots Michelle," she told me as she put the camera back down. "You can sit back down now." she added as she picked up the phone and dialed an extension.

"Hi there, yes she's ready now. 5 minutes?, yes room 141, great see you very shortly." she said in a quiet and relaxed voice. I started to panic yet again, I had agreed that someone else could be involved, but had no idea what she had planned for me.

"Hands behind your back please Michelle." she asked politely. I did as she asked, and felt her bringing my wrists together before attaching a padlock to each wrist cuff, locking my wrists together securely. We both waited patiently for her mystery guest to arrive, Sylvia taking the time to have a more detailed look at the clothes and toys I had brought I laid out in the hotel room. Suddenly there was a knock on the door.

"Just a minute," Sylvia shouted, as she walked towards me and quickly slipped a blindfold over my eyes, putting me back into darkness for the second time that night. "Now you be a good girl for me won't you?" she asked quietly as she made her way to the door. I nodded my head in silence. I heard the door open and Sylvia greeting the deep voice of a man. I could hear them both come in, then Sylvia ushered a few words to him in private. There was lots of movement, and what sounded like some preparation going on in the room. Sylvia then approached me, told me to stand up and follow her, and guided me, still blindfolded. I was petrified, but even more petrified of being shocked if I didn't follow orders!

Sylvia finally removed the blindfold to reveal her master plan. Standing next to me was a 6 foot 2 black man with muscles everywhere, wearing a bright white sailors officer uniform. I looked around and it quickly dawned on me this was set up to look like a wedding! Sylvia introduced me to Jake, and explained to me that his fantasy was to have a mock wedding and wedding night with a transvestite, dressed all in white.

The first thing I noticed was that Sylvia had moved us to the balcony window of the hotel room, and had opened the full length curtains by the window. We were on the 7th floor of the hotel, but with several buildings opposite I felt very exposed in my female and sissy attire. Sylvia had gone to great lengths to make it like a wedding, including a ceremony program that followed the same idea as a church wedding, but with a kinky theme added to it. She ran through the ceremony as if she was the vicar, as I stood there next to Jake unable to do anything, still in fear of her using the shock collar if I disobeyed her.