Alex, the 23 year old virgin, had just left his first session with his new Mistress, Miss A. He left chastised, blackmailed and with a new obsession with feet.
Chapter One: The Envelope
Alex had gotten on the bus, it was his first time in public wearing his chastity cage and he was very self conscious about it. He thought he could hear the lock click against the cage as he walked onto the bus and sat down. He gripped the envelope with shaking hands, his pink frilly panties riding up his tenderized ass. Under his clothes, his body was still crimson from his beating the night before. Alex couldn't help himself and kept stealing glances at the woman across from him staring down at her strappy sandals and teal toenails. He felt his cock cage grow tight as it restricted his hardon which ached in pain.
Alex had never gotten hard at the sight of a woman's foot before, and he supposed he still hadn't but only because of this damned cage. But one night of Miss A's reconditioning had already made a deep lasting impression on his psychology. Alex continued to stare down at this woman's toes feeling the pain in his cock and reciting his mantra in his head. "I live to serve Miss A. My pain is her pleasure. Miss A's pleasure is my pleasure."
With this reminder of his duties to Miss A he broke the seal on the envelope and pulled out the letter inside. The first thing he noticed were a handful of pictures which he quickly crammed back in the envelope before anyone else on the bus could see. He could tell what they were, he had only seen a man on an exercise bike, but he knew, this was a picture of himself fucking his own ass on her stationary bike.
A feeling of deep humiliation and dread sank deep into Alex's core like a boat anchor, he could feel his humiliation plunging deeper and deeper as his cheeks went cherry red. He pulled out the letter which read:
Slave,
Your little virgin cock and ass now belongs to me along with the rest of your body and mind and future. You currently have 32 days in chastity, and unless you want more you must complete every item on this list before we meet again.
Alex's mind raced, he didn't know when she would invite him over next and panic set in as he skimmed down the long list of things to do.
1. Recite your mantra when you wake, when you eat before you sleep;
2. Record every time you become aroused and what triggered it in a diary;
3. Purchase panties, throw away male underwear. (if asked admit they are for you);
4. Purchase webcam and microphone;
5. Get a pedicure and bright pink toenails
6. Shave all body hair;
7. No pornography;
8. No frivolous spending;
9. purchase a Fitbit;
... the list went on and on...
36. Bring a copy of your resume;
37. Purchase a gift;
See you soon slave,
Miss A.
followed by a heart
Alex could tell the heart was meant to be sarcastic.
in small print at the bottom of the page a disclaimer was printed like on a legal document.
Failure to complete these items will result in an extension of chastity and punishment to be decided by Miss A. Failure to complete multiple items will result in additional punishment. Willful disregard for Miss A's pleasure will result in distribution of the attached to all slaves contacts and persons of interest.
The next couple pages listed information which horrified Alex. All of his personal information, drivers license sin number, etc. His bank statement, the contacts from his phone, his internet history, the essay he had written her, and all the pictures he had hastily crammed back into the envelope.
Alex was well and truly fucked he could see that now, no light at the end of the tunnel, just Miss A and her pleasure.
Alex took a deep breath and gulped, oddly he could feel his cock stirring and made a mental note to record this in his arousal diary along with the woman with the teal toenails whom had gotten off the bus a few stops ago.
Chapter Two: No more privacy
Each morning when Alex woke up he would immediately recite his mantra Miss A had gifted him with, he would take a shower and shave any body hair which had a hint of stubble. He would clean in and around his chastity cage as best he could, he always felt a pang of humiliation when he looked down at his hot pink toes.
It had been so humiliating, and oddly arousing, when he went to the nail salon asking for them to do his toenails, the lady behind the desk had snickered, "Just the toes?" she asked with a cocked eyebrow and mischievous smirk. Alex had bought a gift card for the salon for Miss A while he was there, he was sure not to forget his Mistresses tribute ever again after the previous caning.
Alex wore his slutty panties every day, Miss A had only said he must purchase panties but Alex had picked out a dozen or so of the sluttiest pairs in the store, mostly g-strings and thongs. When the clerk commented saying "Wow, lucky girl I wish my boyfriend would buy me so many nice things." Alex had to admit to her that they were all for him, which again prompted a cocked eyebrow and mischievous smile. "An even luckier girl then," the pretty clerk said failing to hide her amusement and erupting in laughter. Alex flushed red and feeling his cock strain against its prison.
Alex was especially embarrassed by his arousal diary which seemed to always involve feet, or his own humiliation and sissification. The nail salon and lingerie store were both on the list. Despite his Mistresses orders Alex had still been watching porn on his laptop, always foot worship and other femdom videos, he never recorded these in his diary. Alex hadn't been able to touch his cock since Miss A locked him nearly a week ago and his head was constantly swimming in erotic thoughts, he was perpetually horny and his arousal diary was several pages long.
Ding, his phone chimed as he received a text. "Download this now and text me when it's done." the message read. A link to teamviewer was in the text message. Alex began to perspire, he knew about teamviewer and this ment Miss A was about to take over his computer too. He knew she would see his internet history. He knew if he delayed it would displease Miss A and she would rightfully assume he had been misbehaving, so he decided to take his medicine and beg for forgiveness, although he knew any mercy was far from likely.
He downloaded the program and replied telling her it was done. He gave her the code to his computer and moments later the mouse began to move auspiciously around the screen. The light on his webcam turned green and Alex knew she could see him. He straightened up in his chair and his eyes cast down.
Next thing he knew he could hear her voice coming from his computer. "hands behind your back slave, and don't move." Miss A command came from the speakers. Alex sat arms behind his back as the mouse whirled around. Alex saw some programs being installed and the computer restarted. Miss A was busy tweaking his admin settings and installing some nanny cam software, keyloggers, everything she could to completely remove any hint of privacy from her slaves life.
Alex was not tech savvy and had no idea the extent to which she had just taken control of his digital life. She then opened the internet browser and looked at his history.
"Care to explain yourself slave?" I believe i expressly forbid any pornography, and here i count 27 different porn videos in the last 6 days." Miss A said with an unbridled frustration clear in her voice.
"I'm so sorry Miss A, I've just been so horny..." Alex said ashamed of his disobedience.
"Yes,I know your horny you stupid slave boy, you are supposed to be horny, your frustration brings me great pleasure. We will discuss your punishment at my house tomorrow, be there first thing in the morning, you will have a long day ahead of you if this is any indication of your behavior.' Miss A said in a disciplinary tone.
"I hope for your sake you haven't fucked up anything else on my list. Since you can't be trusted I want you to bring all your electronics when you come tomorrow" Miss A said before the mic went quiet. The light on the webcam stayed on and Alex sat frozen in place with his hands behind his back unsure if and when he had permission to move. His cock twitched in its cage at Miss A's dominance over him but Alex's brain knew better, he was frozen with fear at the thought of his punishment.