Princess Chelsea Ch. 03

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Princess Chelsea takes an apprentice.
10.3k words
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Part 3 of the 3 part series

Updated 09/22/2022
Created 01/21/2014
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Chapter 3 -- Chelsea's Apprentice

The work week was extremely difficult to say the least. Princess Chelsea had demanded photos of my lock up at random intervals to prove I was still following her lead. Monday I almost got caught in the employee bathroom when I forgot to turn the sound off on my phone. Someone had come in to use the urinal and I was in a stall. When I snapped the photo the shutter tone sounded like it rang out as loud as the horn on a car. My adrenaline surged and I quietly waited for him to wash his hands and exit before double checking the photo and sending it to my owner. On Tuesday she had me do two chastity checks within 15 minutes of each other. I was certain nobody noticed my extra trips to the restroom but that didn't totally put my mind at ease.

I was starting to get more and more used to the device, or rather the pain I felt upon waking up. Strange things were going on in my head as well. Every woman I saw, even ones I didn't really find attractive, became absolute Goddesses. Little things like a perfume a woman wore, a pair of heels, a thin necklace moving across the supple skin of a woman's neck, nylons, anything that I could find even remotely sexy was amplified 5 times over. This all just added to the frustration. I didn't know when Princess Chelsea would allow me to see her again in-person. Wednesday morning I was at the point where I was once again considering begging to quit. There were a few times when I was almost in tears. That changed a bit when I got my, what became a daily, e-mail from her.

She just had a perfect sense about me and whenever I had felt my breaking point was near, she would reel me back in. Monday and Tuesday morning I had received e-mails from her and they contained different rules. Monday it was that I was no longer allowed to wear clothing inside my own apartment. I also had to text Princess Chelsea whenever I went anywhere or returned from anywhere. She only responded once or twice with a "Good Boy," message. She also gave me a schedule of which color panties I was to wear each day.

Tuesday's e-mail put the butt plug in play. Much like Monday's prohibition against wearing clothing, I was now required to wear the plug at home. It came as quite a relief that she had not ordered me to wear it to work. I was also not required to sleep with it in place. It was beginning to get a bit more comfortable, and the strange thing about it was that, without the ability to masturbate, the plug was beginning to be a source of pleasure.

Wednesday waking was particularly hard. I had an erotic dream about my Princess. It didn't get far enough to be a wet dream but awaking to reality added gasoline to the denial fire. I was about ready to give it all up. I opened up my laptop and paused for several seconds trying to psych myself up about reading the e-mail and doing whatever she said. This time there was only three little words in it. "Enjoy, my piggy!"

I was shocked for a moment. I didn't know what that meant. Was it another test? Then I realized it came with an attachment. The file extension was a video file and I cautiously downloaded it to my computer. I started to watch it. My beautiful Princess came onto my screen certainly from a web cam. She was stunning. Her smile, those velvety lips, the way her hair was pulled up into a loose bundle on the top of her head and held together with what looked like chopsticks. If it wasn't for the cage I probably would already have been stroking myself. As it was, I just had to sit up straight then hunch over some to get the pain to subside. The thought of quitting was washing away before even hitting play.

"Hello my little piggy. I hope you're settling into your new little life." She looked into the camera with the same type of smile you might see when someone talks to an infant. Princess Chelsea then opened up her mouth with a half-smile, half "O" face, cocked her head to one side, and rolled her blue eyes skyward." Well OK, I kind want it to be torture. I bet your itsy bitsy penis is attempting to get hard right now isn't it."

She turned her gaze toward the camera once again and let out a giggle. "My little slave....You have been doing a pretty good job, If I was a teacher I would give a B+. I want to play with my toy. You can continue to suffer this week and then you will get the privilege of spending the weekend serving me. Are you excited? I'm sure you are! On that note there will be no new rule today, but I will leave you something to dream about."

She took off the white shirt she was wearing and I could see her black and white pattern bra caressing her breasts. She came close to the screen as she adjusted the web cam filling my screen with nothing but her breasts. She took a step back and she turned around making me watch her perfect ass in black lace boy short type panties as she walked away. I was definitely not going to quit yet.

Awaking Friday morning I was extremely eager to get the work day over with so I could see my Princess. It had been a week. The cage made it feel as though it had been 6 months. I showered and shaved my genital area as best as I could then, made my way to the computer. Opening my laptop I had serious anxiety about whether she would cancel or not. The e-mail read:

Dear playtoy,

I hope you are excited about seeing me today. Let's make work a little more fun shall we? Since you are a dirty little whore, today is now "wear your plug to work day." That's right my pet you will have the plug inside you while you slave away at work, for me, your Princess. Secondly, you will come over here right after work. No stopping at home or anywhere else. You will come straight here. Third, I think today is cream colored panty day, try not to soil them. And lastly, you will bring your laptop with you. This is going to be a fun weekend!

Your Princess,

Chelsea xoxo

I went and got the panties she told me to wear. Putting them on I found something odd about them. After I pulled them up fully I realized that they were crotchless panties. The cage of my device was fully exposed outside of the panties. That meant that they wouldn't hold the device close to my body like the others did, possibly leaving me with a noticeable bulge.

I went to work thinking of nothing but her. I couldn't wait. The day was again dragging on. The plug inside had me trying to stay in my seat as much as possible. I could only forget about it for 20 or so minutes at a time and then I would move reminding me and again my cock would strain. I almost laughed thinking about it because all the pain the device was causing, was much more preferable to having and trying to hide my hard on from everyone in the office. Funny how that worked!

I typed a "leaving work now Princess" about 5 minutes before getting off for the weekend. As soon as the clock turned to 5 I hit the send button and was out the door. My nerves were probably worse than the first time I headed there. I was just praying the whole way over that she would take that contraption off me. At this point I was sure even the slightest touch while it was out of the cage would send me over the edge.

I pulled into the drive way and this time there was another car there. I collected myself for a moment, pulled my laptop to my lap so I could get out with it. "Hmmm," I thought to myself, "I took my beautiful Princess for more of a BMW girl, not an older used Honda."

I passed it by noting the local State University decal on the back window. Chelsea was in her mid-20's so that definitely fit. The last time I was there I was so nervous that I was about to knock on the door, not even seeing the doorbell. This time I took a couple of deep breaths and push the button.

It took a few very long minutes to hear someone making their way to the door. The door handle turned and Princess Chelsea poked her head outside. "Hello piggy. I think if you want to come inside....you can take your clothes off right where you are at, except the panties. Fold them neatly and put your laptop on the top of them. Then knock and beg to come in. Maybe I'll let you."

Here we go again part of me thought. This time I made it all the way to the door, got to see her face, and now I don't even know if she will let me in. I folded my clothes and did as she told me to do. It was unnerving to strip right there on her door step where anyone could see me, then again it wasn't as bad as the shopping trip. I got on my knees this time. I knocked on the door, again she cracked it open. "Please Princess, please let me in. Please, I'm begging you Princess..."

"As long as you promise you are going to be completely obedient." She opened the door a bit wider. Even with my head down I could see she was wearing a pair of shiny calf length PVC type boots with about a 6 inch heel and black semi opaque stockings.

"I promise to be completely obedient Princess, please Princess." I wasn't about to look up and was holding my breath awaiting her decision.

There was a pause that seemed to last forever. Finally the door slowly opened up wider and a one boot was placed in front on me, I planted a kiss on it, then the other, with relief I said, "Thank You Princess."

Ushering me in she ordered me to keep my eyes down. I moved forward with her and I wanted to look at her. It would probably be worth a beating to look, but after this last week I didn't want to risk it. Reaching about the middle of the room she said. "Stop! Stay!"

I just kept my head down and stayed right there. Her boots clicked slowly across the room and back. She placed a blindfold over my eyes. She came around behind me and gave my balls a few taps with her boot followed by one big one. The initial impact wasn't bad, I really didn't notice it that much, but the gut wrenching stomach pain made me fall over on my side. She laughed for a second. "Awe, poor baby. That must have really hurt, but you're my slave so stop resting without permission and get back up. We need to do that one again."

I sprawled my arms on the floor. The shock of the ball kick and the blindfold had messed up my senses but I soon got back on my hands and knees. This time I held my breathe awaiting the kick. It didn't come. Finally I started to exhale and she kicked me again. This time I stood my ground. "That little hold your breath game won't work with me my pet. I have seen it before."

There was clicking of her heels once again and I inhaled the scent of her perfume. I felt the back side of her hand lightly touch my chest and continue up until it turned over and lightly put pressure on my neck as if she was going to choke me. My cock was once again crying to get out and I tensed a bit as I felt the warmth of her breath. She whispered quietly, "Relax slave, up and back on your heels....hands behind your back."

She guided me back until I was in the position that she wanted. "Now slave. I am going to put on your collar. Before I do, I want you to understand I OWN you for the entire weekend if you accept. So......" She paused for a moment and I felt and heard what I imagined her fingernail gently tapping the plastic penis prison. "Do you accept slave?"

Every part of my entire body said yes, I agreed, "Yes Princess, I accept. Please Princess."

"Very well." I smelled the leather as it closed in and she buckled and locked the rigid collar around my neck. "VERY good boy."

I felt her standing up and brushing against me. She put her hand into my hair and the way she twisted my head a bit I knew she was turning around. I heard the sound of clicking heels again but this time they were further away. My Princess had a handful of my hair and before I could hone in on what I thought was a second pair of heels. "Don't worry slave. Just keep kissing my ass."

I did as I was told. At the moment it felt almost like an out of body experience. Though blindfolded I tried my best to kiss every single inch of her ass. I could clearly see how perfect it was in my mind. She pushed my head all around. Feeling the small portion of her thong, I attempted to slip my tongue under it which got a quick tug of my hair and a "No, no, no."

She guided me back on target and she had me work on each cheek all the way down to the tops of her thigh-high stockings. I was so lost in her ass that I really didn't even realize leather cuffs had been placed on each wrist, secured together behind my back, along with one on each ankle. Princess Chelsea let go of my hair and turned around. I took a deep breath and exhaled as I heard the distinct sound of a leash being attached to the collar. She guided me back on my feet. "OK pet. I'm going to take you down stairs now."

I was disoriented with the blind fold on. The whole scene was making my head spin. I was imagining sounds. Ankle and wrist cuffs had been placed on me and for the life of me I couldn't even remember Chelsea taking the time to do that. My cock throbbed in its own bondage and the sensual experience of worshiping her ass had me under her influence. She was becoming my drug and now I couldn't even trust my own senses. She carefully guided me down the stairs and into what I figured was the basement dungeon where I had been taken before. There was a noticeable drop in temperature. It was by no means freezing, but being naked it was noticeable.

"Don't fight it, just follow my hands." I heard her softly say as I felt her push my left foot out a bit wider. I heard the sound of a chain and clasp being attached and the same treatment on the right leg. I almost fell over backwards. My hands were helpless behind my back, but I felt Chelsea's hands secure me and push me forward into what felt like a cold stone wall. I now knew where I was. I was being attached to the big St. Andrews cross on the wall. I let a small smile escape my lips in recognition of that as she attached each wrist. Her hair brushed against my shoulder and then I felt the weight of her chin. I felt another hand run down to my ass, underneath the cream colored panties. She started tapping on the plug and I let out a moan. She nibbled her way up my neck. "So my little playtoy are you all worked up right now in mean little Princess Chelsea's little chastity cage?"

"Yes Princess. It's been torture." I gasped.

"Does it want to come out and play?" she would speak and go back and forth between nibbling on my ear lobe and flicking at it with her tongue.

She pulled my panties down with one hand and started massaging my balls. I was absolutely going crazy. I couldn't stand still. She would tighten her grip a bit and I would get up on my toes. When she loosened her grip I pulled away just wanting to feel her grip again.

"Yes Princess, It wants to play. Please Princess." I was in desperation. "Please Princess, I'll do anything."

"Well slave, I guess we will just have to see. Now be a good boy and stay put, and let that little thing go down. I'll be back." I heard a pair of scissors make a snip and the light material of my cream colored panties fell away. She gave my balls one more hard squeeze, delivered a hard slap to my ass and walked away. The minimal light that I had seen trying to penetrate the blindfold suddenly disappeared and I heard the door shut. Once again I was alone.

I stood shackled to the cross in the dark. I had no idea when Princess Chelsea would return. I was hers for the entire weekend, but how long would I have to wait in the cool darkness. She intoxicated my mind with an eroticism that I had not experience before. Every time she sent an e-mail, that video, or spoke to me it had turned me on so much. With the chastity device on I was always reminded of her. It was like being in an infinite foreplay game. I wanted to be able to cum so bad. Yet there was also a part of me that was afraid being allowed to cum would bring an end to that feeling in a way that would never be recaptured.

I didn't even hear the door open when the lights came back on. It could have been 30 minutes, and hour, or two. I had no idea. Her hand was slightly cold when I felt it on my balls. She tease them with a gentle squeeze and trailed what felt like to finger from the base of my balls up to the crack of my ass, over the plug, and up stopping at my lower back. Moving down to the crack of my ass once more, finally stopped at the plug and tapped her fingers on it a few times. "Now my little piggy, we are going to have a little fun."

I felt the riding crop tap my ass. It wasn't a hard blow, just one that felt like a warning. I felt her on my right hand side as she gripped the leather cuff on my wrist, "I've changed my mind. I don't think we will use the cross right now."

My arms were put behind my back and then my ankles were also freed. Princess Chelsea put her hands on my shoulders and slowly walked me back, turned me around, and ordered me to put my hands back in front of me. I heard heels clicking and I thought she was behind me. That changed when my hands were once again hooked together. Not being able to see was definitely throwing me off. "You should remember this slave."

"Yes Princess." I said as now I knew she was placing me in the same place I had been a week ago. I felt the spreader bar attaching to each ankle, and heard heels clicking around me but before I could locate her I heard the chains being pulled from what sounded like the other side of the room as I was raised to my tip toes.

Princess Chelsea removed my blindfold which made me squint my eyes a few times to adjust to the light. When they did adjust, my jaw dropped. I had already seen that she was wearing those black PVC boots and thigh-high stockings. I had run my tongue over her thong. Now I could see everything. She wore a black corset that fit her frame perfectly and the vertical black stripes accentuated her hour glass figure. Inset from black was a deep royal blue that made her equally blue eyes hypnotic. Her lightly tan skin and blonde hair contrasted elegantly with the black. Below there was a very short black lacey skirt that would let me get just a glimpse of the area were her ass met her thighs. It had been a week since I had seen her and the images burned into my mind couldn't do her justice compared to what I saw in front of me.

In her hand she was holding a small bucket. She approached me and set the bucket down. I tried to look but with my arms chained together and elevated above my head plus the rigid leather collar I could barely see her. I wanted to speak. Looking into my eyes she brought the finger of her left hand to my lips signaling me not to speak. I looked down a bit and saw her transfer a plastic clothespin from her right to left hand. She continued to maintain eye contact as she place her right index finger into her mouth, removed it, and gently massaged just the tip of my nipple with small circles. I squirmed a bit in my bonds. It was an amazing feeling that seemed to be setting off pleasure receptors from the hair on top of my head all the way down to my toes. When she felt that one was teased enough she moved on to the other.

She moved the clothespin back to her right hand and deliberately made sure I had seen it. Keeping it closed she applied pressure forward and pushed it into my nipple causing the flesh of my pectoral muscle to dimple. She opened the pin slightly, enough to let me feel it scrape my nipple. With the nipple already erect from her saliva and finger teasing, she pulled back and let the clothespin close. A white hot pain shot through me that made it almost impossible to not move around. The erect nipple alone was the victim of the pins bite without getting any of the areola. When she saw the effect of the pain wash across my face a crooked smile crossed hers. After the other nipple was clamped she looked down at the pins, back at me, and started flicking the pins with her fingers. I writhed in pain as she smiled. The bubbly bratty dominant blonde girl in the schoolgirl outfit I had seen last week was now replaced by a strict, calculating, cruel, full-fledged dominatrix. She was a Goddess and despite any pain that may be coming I wanted to suffer to please her.