Part 1

He traveled to the hotel excited at seeing his friend. The plan was for him to check in while she was still at work. On arrival at the front desk, he gave his name. "Oh your girlfriend has already checked in at lunchtime here is you key card room 415".

"Thanks" he said and made his way to the lift. He messaged his friend to say at the hotel I see you already checked in? She instantly replied "yep had some spare time on my lunch break. Enjoy your surprise x"

His mind raced what could this be. She had known about his kinks for some time and even taken part once or twice for a bit of fun.

upon entering the room, he noticed her travel bag on the side. He placed his bag next to it then saw some objects laid out on the bed and an envelope with his name on it on the small coffee table.

At this moment, a text came to his phone, "follow the instructions in the letter if you have enough bottle Xx".

He first looked over the items laid out on the bed. He could see a lovely high neck red dress with a long zip running up the back like one he had seen, told her about and really wanted to wear. You see one of his kinks was cross-dressing. He also saw black stockings, red lacy underwear, a wig, opened padlocks, rope and a beautiful pair of sky high ankle strap court shoes with around a 6" heel.

He walked slowly over the envelope his mouth a gasp and heart racing. He carefully opened the envelope and began reading the hand-written instructions.

1. Strip off and take a shower and shave

2. Once you are clean and smooth, put on the underwear. You will find matching French knickers, bra and suspenders. Then put on the stocking and don't you dare latter them or else!

3. Apply some make up I've left a bag in the bathroom to help with this. and put the wig on.

4. Put the red dress on and the choker, place the D ring at the back and then once the dress is zipped up put padlock 1 through the zip and the d-ring.

5. Put on the high heels and lock the ankle straps with padlocks 2 and 3.

6. Take a picture in the full-length mirror and send it to me when you are done.

After reading the instructions again he followed them out to the letter. Shaking with excitement he sent her the photo. He felt super sexy in the high quality underwear, stockings and dress. The heels were so high he could already feel his feet start to hurt. It had been too long since he had chance to explore his feminine side.

He received a message back "lol looking good. Log in to Skype and let's see how far you will dare to go Xx"

He instantly got out his laptop and logged into Skype to find her already waiting in the instant chat for him. After some back and forth chat she put ready to continue? Sure, he put with a kiss smile. Calling her bluff somewhat he hoped.

"You see the rope on the bed tie your legs in a frogtie. "PS sent me a pic for proof!" "Lol" he put sure. He quickly and expertly tied his ankles to his thighs sitting on them he also places some ropes around the heels to keep them tied on, and sent the picture.

'Nice' came a Skype response 'thought you would have pusses out by now' she put, never he responded, "child's play lol" lol pushing your luck she retorted.

He then asked he a serious question what time are you finishing work today?. Looking at the clock it was 3.30pm. 5pm she came back so will prob be there 5.30. 'Hmm 2 hours play time then easy; he replied to her.

'Lol If so easy put those extra panties left you in your mouth and tape them in again a picture is a must!!'

He gulped slightly but decided to play along still. There was no way he was going to back out yet.

He could see she was typing a long message. And this was the follow:

"I've got to go do some work, so follow these instructions I expect a picture at every step apart form the last one as it will be impossible X haha.

1. Put on the long opera gloves you will need them.

2. Tie some large rope coils above and below your fake breast. Yes you had better of put those chicken fillets in.

3. Find the chain I attached to the head board and use padlock 4 to attach it to the D-ring on the collar.

4. Lock the other chain tightly around your waist and between your legs.

5. Use the last padlock to lock the handcuffs to this chain behind your back.

6. Handcuff yourself make sure to use the pin to double lock them and sweat bands so they don't rub to bad and enjoy lol... see you at 5.30pm

PS try and escape if you can x.

He replied are you serious it's two hours before you get here!?!

She just replied "bottler g2g I'm expecting pics - Laters Xx"

He took some deep breaths and decided what the hell you only live once! He began again following the instructions that had been written for him. After each one he sent the picture to her. After number 5 he got a reply back good 'girl' enjoy your bondage see you soon Xx

With that he locked on the handcuffs to complete his ordeal. He tested his bonds and he was happy that he had done a good job securing himself. Then began trying to escape. After 30 minutes, he realized it was impossible and tried to conserve his energy.

After a further short period, he heard the door unlock he heart was racing extremely fast who the hell was this. He knew it was too early for his friend. The person turned all the lights off and he could hear them quietly move over to the bed. Then rummaged in a bag for something then he felt them put something over his eyes. They had blindfolded him! He heard a switch and could detect some light from behind the blindfold.

He then felt a hard smack on his buttocks, then a whisper in his ear. Don't worry it's me. He mumbled "you almost came me a heart attack bitch" 'congrats 30 mins added to your bondage and laughed was the reply.

She took out the gag and then added more ropes around his elbows and wrists and took off his handcuffs. Then gave him 10 hard smacks on his buttocks again. After that she took off the blindfold and they chatted while she untied his legs. It was good to see his friend again it had been too long. Once his legs were untied she said right time for your high heel training. "What?" He said. "Time for your high heel training you have an extra 30 mins for calling me a bitch" then laughed. "Damn" he said.

She then unlocked the chain at the headboard stood him up and proceeded to walk him around the room. His feet were killing him. From about 5 mins in. Every now and then she would stop leading him and take photos or film a short video and ask him to do walk around on his own. She was really enjoying herself he could tell, and so was he! Although he was doing his best to play the damsel in distress. After 30 mins or so she pushed him onto the bed and finally released him of his bonds.

Really to go out for dinner she said? I'm starving

Yep I'm starving as well, give me the keys to the padlocks so I can go get change. She just laughed no you are going like that. He didn't have much choice with the dress and heels were still locked on.


Part 2 (added: 2018/03/17)

As they walked back from dinner, their tandem high heels made a loud audio click-clack as they made way back to the hotel. Will you hurry up she said to him, who was still locked in his 6" heels. My feet are killing me! You try wearing these heels! Pah easy she quipped back feeling confident after several Gin & Tonic's and strutting effortlessly in her 4 1/2" court shoes.

There is no way you could wear these heels as long as I have - he remarked hoping she would take his bait. Fine hurry up and when we get back I'll wear them and show you how is it done, I even have 2 spare padlocks that are open with the keys still in my office so no way I can back out.

She woke up, with a slightly sore head with the 6" heels padlocked to her feet, bugger she thought, I did actually make that stupid boast of being able to wear the heels and even remember that she didn't have the padlock keys with her. She tried to reach down and see if she could pull them off but her hands wouldn't respond and then she realized she had in fact agreed to be bound by him as well. Her hands were cuff behind her back with some fur lined leather cuffs. Great she thought to herself, she looked over at him and he was still fast asleep. She thought sod it, she must have been able to sleep once like this and surprising to her she quickly nodded off again. When she woke back up he was awake this time staring at her, there eyes met together and they share a warm smile. He then said ready to back up your big mouth from last night....

Get on with it then I can handle anything you can throw at me she postured. He went and got some black electrical tape and told her to put her palms together. He quickly wrapped several loops of tape around her thumbs, followed by her palms and finally her fingers. Good luck trying to use your supple fingers to pick your way out of this he thought. He wasn't anywhere near finished wit her bondage yet. After he removed the fur lined leather cuffs, he grabbed the pair of tights she had on the night before.

Bet you never realised tights make a good armbinder, you soon will however, he gloated. He gathered one of the legs and places her useless taped fingers inside and slow started to pull the tights up her arms. After reaching the top he pulled the elastic waist band over her shoulders, encasing her arms completely inside the tights. He then took the second leg, wrapped it around her body below her breast and tied to its self behind her. She tested out her bonds and the elastic tights actually made a snug but effectively restrictive armbinder.

Hey you were right this is pretty tight. Oh I haven't finished yet he quipped back with a rye smile, as he started adding extra tape. The black taped was being wound around her slender wrists and slowly up her arms stopping just past the elbows.

She was now very firmly stuck in this homemade armbinder. Standing her up, he said to her now it's time to see how good you are in those shoes. He warmed her up making her walk around the large hotel room, the same as she had done to him the night before. He then took a coil of rope and strung up her arms high behind her back attaching the rope the top beam on the four-poster bed. Forcing her to bend over into a strappado.

Her left her for a few minutes to struggle in her bonds and try and escape but it was no good she was good and stuck and at his mercy. Then he said that's the appetiser, time for the main course and took another coil of rope and started to tie it to her right ankle, then he hoisted it up into the air tying it to the same beam. She was then perched on just one of the heels trying desperately to maintain her balance. He knew she could cope for a while as she regularly took yoga classes and often sent him pictures and this was similar to a pose she had shown him her in, which consequently this had given him the idea.

After about 5 mins she realised she needed out but had to try and make it seem was his idea. Her single foot and leg was beginning to wobble with the strain.

Hey, she said I have another surprise for you, a new special outfit you will absolutely love. It's 9.45am now and we need to checkout at 12am. If you want sufficient play time let me down and I'll show you what I have for you. Will it be worth it? Oh yes she instantly replied very much worth it.

Once she was free of her bonds - thank goodness she thought, she went over to her large bag and took out a baby pink maids outfit and matching pink heels, with large bows and thick ankle straps that could again be locked on. He couldn't believe his eyes although he preferred normal female clothes any cross dresser loves a maids outfit and it being pink made it all the better.

She helped him into the maids outfit and applied some make up and a blonde wig. And with a click at the neck the maids uniform was locked on, hey you didn't say this was a lockable dress. Oh didn't I whoops and she laughed at him. Come on if I've got to be locked in theses shoes you can join me in a pair. Once she had given him the once over and was happy with his attire, she toyingly picked up a few bundles of rope and with a cheeky smile said well then...

Well how can I resist, do your worst and by worst I mean best - haha, she tied him tightly to a post of bed about 10 full coils of rope at every attachment point she could think of. Once she was done, she said right I'm off to get the keys to these padlocks. These shoes are harder to wear than I thought, you actually did well last night!

Right it's 10.30am, now shouldn't take me more than 30 mins to get to the office get the keys get these damn shoes off and some comfy trainers on and get back here. You just stay put here, like you can go anyway anyway haha. Then before he could complain she grabbed a large red ball gag and shoved it into his month again locking it in place and with that she said seeya in 30 mins, blew him a kiss and walked out the door.

She walked to her car thinking what a good time she had been having with her friend, trying to maintain her balance in the ridiculous heels that she was now dying to get off her feet. Luckily it was only a short walk to the car and another short drive to her office, and the fact it was a weekend meant she wouldn't be bumping into anyone that would know her. When she arrived she quickly made her way into the office, found the keys to the padlocks and took the heels off, stretching her sore feet for a few minutes on the soft carpet before put on her trainers and heading back to the car. She then past someone she knew and they exchanged a few words all the while she was thinking glad you didn't see me 5 mins ago. She got in the car and began to head back to the hotel. She looked at the time it was 11am which still gave her plenty of time to get back, untie him and then check out. Unfortunately this is where things took at turn for the worse, as soon as she pulled out the car park the road was jam packed with stationary cars. It took her 10 mins just to join the road from the office car park. As the time ticked closer and closer to 12 she realised she wasn't going to make to back before check out her friend was trapped, she knew there was no point ringing him, she had done a too good job with the ropes.

Meanwhile, back in the room, after 30 mins he was hoping his friend wouldn't be back too late. After 1 hour his feet were really starting to hurt being stood up even though the ropes supported a large share of his weight. She had only 30 mins remaining to get back before checkout. Where could she be, he hoped that she was just playing with him and was sat downstairs laughing at his predicament. When 12 o'clock came he was frantically trying to escape the ropes but it was useless.

At around 12.15, there was a knock on the hotel door and a shout of cleaner. And with that his heart stopped, and he hoped she would just move on to the next room. But she didn't, the door opened wider and the cleaner walked in. She could still see clothes other bits and pieces on the floor and she called out again. She moved further into the room and then saw a man dressed in a pink dress, no a pink maids outfit and pink heels tied to one of the bed posts. Well well well what do we have here then!

Looks like someone has been having fun and has left me a little helper. They are even dressed for the part! She made a call down to reception and said the room was clear and they must have already checked out. And then came up to him and said you are going to be doing all my work for the remainder of the day. I have 5 rooms left on this floor including this one so you better get started. And with that she untied ropes holding him to the post, but attached the fur lined leather cuff so he still wasn't completely free, she also attached a chain between his ankle to make only tiny steps possible for him. Come on you we, no sorry you have work to do.