Journal of a Chastity Slave

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To Jackie, who owns my mind, body and cock to this day.


The second my new coworker arrived at the center I was immediately interested. At 5 feet 4 inches, Jackie had dark hair, brown eyes and an unbelievably cute attitude that captured the attention of every person in the workspace. I had seen her around at my high school before but I’ve never had the opportunity to approach her, despite both of us being second semester seniors. It wasn’t that I felt timid or unattractive; I’m decently good-looking, 6 feet and 1 inch tall with enough muscle mass to not be considered too skinny.

The two of us were both hired the week that we became of age. Our boss insisted on employing adults to minimize the amount of legal paperwork. She was positioned at a table across from me, where I had the perfect view of her. Having had a chastity and foot fetish since my preteen days, I immediately imagined her as the goddess of my dreams.

When tennis season began for me and track began for Jackie, we quit our respective positions to be able to participate in our athletics. The school mandates a two hours long session for practice for each team, so I had a set time frame before and after practice to spend time with her.

As a very outgoing girl, Jackie was very approachable. I had no problem talking to her about sports, schools and family. We quickly became close friends as I had a chance to have long conversations with her after every school day.

Slowing starting to feel a bond with her, I purchased a chastity device from Amazon, put it on with some difficulty, tossed one key away, and asked her to hold onto the other one without telling her what it was for. She was mildly skeptical of the circumstances but I managed to convince her to help me out. I asked her keep it for a week and documented my thoughts as follows:

Friday (Day 1): I gave the key to Jackie after school, trying not to act too awkwardly. She complained about the possibility of losing it, so I suggested that she kept it on a necklace. During our daily afternoon talk, she kept playing with the key, seemingly unable to put it down from her beautifully manicured nails painted dark red. I felt a stir every time she dangled it from her long nails or fiddled with it in her palm. By the end of the day, we had agreed to meet up on Sunday for a coffee.

Saturday (Day 2): Woke up with some soreness on my cock. I had set an alarm for 7:30 to make it to volunteering, where I had to walk around and cheer on runners during a race. Strolling around was difficult, and I ended up with mild chaffing. The locked chastity cage also served as a constant reminder of Jackie, her sweet smile and her adorable but dominating demeanor. I looked forward to the date that we set up for the next day.

Sunday (Day 3): The mornings are the most difficult. I frequented the shower to ease the soreness and clean out the interior of the cage. Jackie cancelled on the coffee date with a text. “I can’t hang out today. I have to babysit my brother but let’s raincheck ok? :)” My mind was fixated on the text messages and the selfies that Jackie sent me, including a picture of her legs and feet. Her toenails were polished black and her feet were perfectly shaped size 6s from the tip of her toes to her ankles. I was filled with lust at this point and felt a newfound desire to spent as much time as I could with her. I tried not to be too hung up about her canceling coffee.

Tuesday (Day 5): I’ve noticed that exercise causes some discomfort to my genital area with the cage. Between running every other morning and going to the gym once in a while, I developed some chaffing towards the bottom of my testicles. I’ve been getting steadily hornier every day, not to be helped by Jackie’s flirting and seductive selfies of the chastity key on her necklace.

Wednesday (Day 6): I’m regretting this decision more and more. A weeklong lockup would be the longest I’ve gone without an orgasm. At this point, I experience deep attachment to my beautiful keyholder, probably as the result of the cage reminding me of her every hour of my waking day. She continued to openly flirt with me and some of her other boy toys, jingling the key on her necklace every time she did one of her irresistible hair flips. I fell hopelessly in love with her and hoped she would eventually reciprocate.

Friday (Day 8): I woke up today expecting that I would be finally released from the plastic prison. After showering and checking my phone, I found another one of Jackie’s texts: “Hey! I’ll remember to bring the key to school today. xoxo :)” Feeling ecstatic from my upcoming release and even more from her lovely messages, I headed to school. I went through my classes with a uncharacteristically bouncy attitude, finally meeting my owner after classes. Jackie was dressed with casual skinny jeans and a tight dark green sweater, standing near the locker rooms with a dazzling smile on her face.

When I approached her feeling happier than I’ve felt in ages, konyaaltı üniversiteli escort she laughed slyly, “I know we agreed that I give you the key today, but I’ve changed me mind. I’ve already decided that I want you to tell me what the key is for before I choose whether I should give it back or not.”

Horrified, I felt backed into a corner. What would she think of me if I told her the truth? I could never lie to the person that I worship so deeply. Besides, Jackie has gotten to know me so well that she would probably tell if I lie.

Having no other choice, I confessed not only the locked cage on my body, but my feelings for her and my kinks as well.

Jackie respond with a giggle, “You passed the test! I’ve known what this is the key to for a long time now,” she held up the key as my face burned with shame and my heart practically melted.

“You don’t think I’ve noticed the way you look at me? Every time I hold up your key, MY key, I could see discomfort on your face. Every time I’ve hugged you I felt something hard below the belt, and the way you texted me throughout the week showed your desperation and how much you adore me.”

Mortified but relieved at the same time, I swallowed hard and gradually slowed my heart rate. “So now that I’ve told you the truth, you can release me right? I’m dying to get off.”

“Definitely not! Although you told the truth a minute ago, you still lied for an entire week. That means you have to be punished. I intend to hold on to the precious key for the time being.”

I couldn’t believe my ears, “For how long Jackie?” I asked tentatively.

“As long as it takes to test your devotion to me,” she stated, then explained when she saw my confusion, “I’m asking you to serve me as my pet, slave. Do well and you can get an occasional release. Fail and you will never see me or the key ever again.”

Overwhelmed by her demands, I fought off my fears and accepted, “I understand. I’ll make you proud of me, Jackie.”

“Slaves don’t call their owners by their names,” she stated matter-of-factly.

“I’ll make you proud, mistress. Thank you for this opportunity.”

“See, a little training and you’re already learning,” she beamed and looked pleased with herself,

“Now kiss my shoes and you can go to practice.”

Thankfully, there weren’t a lot of students left at school at this point. I kneeled down and obeyed after a split-second hesitation while she flashed a knowing smile. Then I retreated to the locker room to change.

Saturday (Day 9): Knowing that Jackie was fully aware of my cage put a new energy into my confinement, as did the increasing amounts of flirty pictures she sent me. It was getting harder and harder to carry on everyday without being bothered too much. Jackie relentlessly teased me with her text messages, which also made it harder to take my mind off of my situation. “are you thinking about me boy toy?? don’t you wish you could serve me in person to distract you from the cage?” I knew she expected me to answer right away, so I said what I thought she wanted me to say, referred to her as my mistress and stating my desire to worship her.

On Sunday, Jackie asked me to go to her house. Or rather, she demanded that I visit her since her parents were out watching her brother’s basketball game. She greeted me with one of her sweet smiles and ordered me to kneel down and press my head against her worn pink socks until she let me in. I eagerly obeyed, taking in her sweet scent and was eventually allowed to walk in before being told to take off my clothes and wait for her while kneeling on the hardwood floor.

Her house was small but cozy and warm. The front door opened out to a living room with a flat screen T.V. and a sofa resting on polished brown floorboards. It was facing the couch where I removed my clothing and took my place on the ground as I watched Jackie run upstairs to change. Naked except for the tormenting cage between my legs, I waited anxiously for her to descend down the stairs. After what seemed like hours, I watched as my goddess slowly walked down, like an angel from heaven, wearing a pair of short shorts and a loose fitting blouse. She sat down on the sofa and placed her lovely feet on my lap, turned on the T.V., and looked at me expectantly.

“Massage my feet until I tell you to stop. Don’t put them anywhere near your face and keep your eyes glued to them.” She then proceeded to flip through different channels.

“Yes, mistress,” I murmured, visibly bummed out that I was forbidden from kissing her toes.

After 15 minutes of messaging her flawless feet, I felt my cage tighten as I became more and more aroused, eventually making me fidget on my knees. Jackie noticed this as a smile briefly crossed her face and had me fetch her pedicure set from the coffee table between her and the television. She ordered me to wipe off her toe polish, give her a trim, and apply another polish kurtköy escort of a color to my liking. Despite having little experience in the field, I understood that her word was law and quickly agreed.

I started off with removing Jackie’s cute pink socks and wetting the cotton balls in the box with acetone. She seemed to be satisfied with my work and returned her attention to the T.V. While I worked on one foot, she rested her other one on top of my chastity cage, seemingly unaware of the amount of frustration and discomfort it caused me. I finished quickly and began trimming, taking extra care not to cut anywhere that I wasn’t supposed to. I finished after a painstakingly long time.

After placing all the clippings near the table, I selected a dark red color to paint her toes. I reasoned that it would match well with her fingers painted the same color. Both my knees and my cock were aching painfully at this point. I began applying the coat of paint, smoothly shifting the brush to avoid touching the sides of her toes. After I finished, she examined my work and praised me. She displayed her thanks by permitting me to kiss both of her ankles, an allowance that I took gratefully.

She then had me bend over sideways so that my hands and knees were sideways to her body. Jackie proceeded to prop her feet up on my back to dry the polish, remaining fixated on her T.V. show. I felt honored to serve as the footstool of the girl I was so interested in.

Just when I felt like I could no longer endure the soreness in my joints, she signaled that the paint has fully dried and had me resume my original position kneeling down at her feet. Without saying a word, she positioned her feet around my locked cock and began flipping it around to tease me some more, flicking her big toe to inflict light pain into my balls and shifting her weight forward onto the cage, as if demonstrating her obvious power over me. After silently enduring her relentless torment for some time, she leaned forward until her crotch rubbed against my face, her feet still in contact with my cage.

“Kiss my shorts,” she purred, “bury your face in the pussy that you want so badly.”

Completely overwhelmed by her beauty and dominance, I obeyed, trying hard not to show the frustration I felt from her cruel words. She added to the humiliation by stroking the back of my head, gently pushing it forwards the same way you would pet a dog. Suddenly, I felt my penis lurch forward a bit, and I was surprised to see a few drops of precum dribbling to the floor.

This did not go unnoticed by my mistress, “How cute,” she laughed, “This must mean you really like me.” She seemed intent on humiliating me, “Now be a good slave and lick it up.”

Without thinking I bowed my head down to lick up my own precum. I felt extremely vulnerable and frightened by the amount of power this gorgeous girl had over me. When I finished, she placed her left foot under my cage and rubbed at it with her other foot in an attempt to coax out any remaining cum. Before long, a small stream of thick white liquid fell onto her toes, and she raised them to my face while smiling sweetly. Disgusted by my own actions but having no power to resist her, I took her cue and licked my cum once again. I savored the taste of her beautiful toes for the first time and fell even deeper into submissiveness.

“I guess you really earned this, slave,” she taunted, “don’t worry, no one will know about this if you behave yourself.”

She took out her smartphone and snapped a few quick pictures of me before I could come to my senses. Giggling, she flipped her phone around and showed me her handiwork. There I was, naked on the ground with nothing but a chastity cage on, sucking on Jackie’s toes while kneeling before her. At first, I failed to recognize the pathetic teenager on the little screen, instead realizing that I had truly accepted my descent into chastity slavery.

“How do you feel right now, slave?” she asked.

“The cage mistress, it hurts..I can’t get it to stop crushing my cock,” I explained, barely able to speak out loud.

“That’s what I was hoping for,” she laughed, “luckily, we can fix that.”

Jackie then had me spread my legs while remaining kneeled down. She caressed my arching balls with her long fingernails and inserted her pointer finger into the peehole of the chastity cage, scratching at the sensitive head of my penis and causing me to twist uncomfortably with arousal. She giggled at my reaction and placed her right foot under my testicles, kicking upwards every once in a while to cause pain to my full balls.

“Be a good boy and look me in the eyes. I don’t want you to see it coming,” she said while continuing the barrage of ball kicks.

Despite the severe pain I felt, I held back from doing anything to stop her. I instead was fixated on her lovely face smiling with delight as my penis slowly waned.

“I think you’ve had enough,” ankara kurtuluş escort her face had a mischievous look to it, “You can take the cage off now, if you wish.” She tossed the key down in front of me.

Surprised by her sudden act of mercy, I couldn’t believe my ears, “Really, mistress? Thank you thank you,”

“Not so fast, slave. You have a decision to make: you can either unlock yourself and get off right here in front of me, where I will ruin your orgasm and force you to clean up after yourself OR you can leave the key and leave the release date up to me. I’ll let you choose, but keep in mind I’d much rather keep you desperate.”

She tilted her head expectantly. I knew this was just another of her tests. Although she offered me a choice, the correct answer would be giving the key back in order to earn her favor. If I unlocked myself, she would doubtlessly stop my pleasure and find a away to punish me.

Having made my decision, I took a deep breath and obediently picked up the key, offering it to her while keeping my eyes to the ground.

“There’s a good boy,” she purred. Then she removed her necklace and tossed it to me as well, “wrap it around my left ankle twice and hang the key from there, slave. You’re always staring at my feet so I’m giving you something to look at.”

She then picked up one of her socks that I had placed next to the sofa and dropped it to the floor, “You can go now. Good work today, slave. You can hold onto this sock and cuddle with it whenever you miss me.”

After the intense session that I had just experienced, I felt hesitant to leave. As if to hurry me along, Jackie took one of her newly pedicured feet and pushed it onto my face. She gently shoved it until I took the hint and began putting on my clothes. She showed me to her door, kissed me on the cheek, and said goodbye.

Tuesday (Day 12): What started out as a harmless activity used to fulfill my fantasies became an agonizing burden that haunted me everyday. I repeatedly hinted that I needed a release but Jackie responded that she was pleasured by my frustration. As if to purposely torment me further, she hugged every starstruck guy that was brave enough to approach her, sometimes even pecking them on the cheek while I watched helplessly. That night, she texted me again. “the funny thing is you definitely deserve an orgasm at this point but im too much of a bitch to give one to you. this is what you wanted right? a sexy girl denying you for weeks at a time” I felt a keen sense of dread as she continued, “im going to completely break you. i will make you worship me forever.” Choking back tears of frustration, I fell asleep rubbing her sock on my cheek.

On Thursday, Jackie had me come over again in the morning as neither of us had first period. Dressed in a tight t-shirt and yoga pants, she had me kneel down before her at the doorstep and strip down in the living room like last time.

She began by slowly stripping off her shirt to reveal a dark blue bra. Noticing my unwavering attention, Jackie smiled teasingly and brought her foot to my cage, scraping the head of my hardened penis through the peehole of the cage with the nail on her big toe. I shuddered with both arousal and anticipation. Satisfied with being able to toy with me so easily, Jackie handed me a silicon vibrator as soon as she gave a sensual check-up of my cage.

“It’s been exactly 2 weeks of denial for you, my slave. Here’s your chance to finally get some pleasure.”

She went to the kitchen and brought back a dish, then ordered me to anally stimulate myself to drip precum onto the dish. Skeptical but eager, I took my place at her feet once again and obeyed.

Jackie crossed her leg and waited for me to begin. Without any instruction, I tentatively pegged myself until I felt a sudden rush. Believing that I had hit the male G spot, I twisted and turned the toy until a stream of white liquid streamed onto the dish. Laughing with delight, Jackie tapped her foot and demanded that I continue.

Encouraged by my success, I continued to wiggle the toy around, pushing it deeper little by little. After the initial shock of having my ass penetrated, I began enjoying the limited pleasure that the toy offered. Having been sexually denied for two weeks, I was willing to indulge in any stimulation that I was offered.

I continued for about thirty minutes, yielding as much cum as I would have spurted had I was given a proper orgasm. When I couldn’t produce any more, she told me to stop and taunted, “This is where the real fun begins.”

Jackie dramatically lowered her left foot over the dish. Horrified, I realized she intended to have me swallow every last drop that I procured. With my eyes fixated on the chastity key dangling from her ankle, I helplessly lowered my head until I was at eye level with the dish. Smiling sweetly, she dipped her big toe into the dish and held it up to my face.

“Let’s start with a little taste first.” I had absolutely no power to resist her at this point, so I eagerly licked her toe and removed the drop of cum. It tasted slightly salty and had a peculiar consistency to it.

After the first lick, Jackie felt encouraged to feed me more off the dish at one time. She eventually placed all of her left toes into the dish, wiggling them around until the cum got in between her toes.

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