Online Chastity Ch. 01-06

I was in a relationship with someone five years ago. We had been seeing each other for about 3 months, and while I had been fantasizing about playing with restraints in the bedroom and exploring the idea of being tied up since I first started thinking about sex, it hadn't come up yet. Not just with this guy, I had never brought it up with anyone I had ever dated. Before this relationship, I was embarrassed. I used to think that admitting those desires had the chance of ruining a healthy relationship. Of course, there is a risk of that if your partner isn't into the same sorts of things, but looking back, it seems ridiculous to want a relationship where you can't explore that which turn you on the most. Don't you think? How healthy can a relationship be if you aren't able to be open and honest with one another about your deepest desires?

I digress... The man I was dating's name was Terry. He was a finishing carpenter. Well... he owned a renovation company but had all the skills to do the work himself. His hands were rough, and he had the build of a man with discipline. He ate right, went to the gym regularly and his naked body made my toes curl just at the sight. His cock was perfect too. Some cocks just... feel right inside you. They make you feel full. Speaking of, how's your cock in its little cage? I wonder how it would make me feel... Too bad it's locked up.

I digress again... I live in a loft and had just moved in when Terry and I had started dating. It was starting to feel like my own space, but it was just a big open room that I wanted to feel like the modern lofts you see on TV shows. Something beautiful and elegant that kept all the textures of the loft space intact. Terry was helping me with the reno. He had drawn some plans up at work one day was coming over for dinner so we could go through it all. As I would come to learn, Terry had a love for building anticipation. He insisted we wait until after dinner before he would show me the plans. As much as I always complained, he was right. Waiting for the right time always made things better. So, we ate, had a few glasses of wine, and then after the 5th time I asked, he relented and asked me to grab my laptop. The plans were on his work server, so he could pull them up through his website.

I ran to the bedroom and brought back my laptop, handing it over as I curled up beside him on the couch. He opened it up and a video of a hogtied woman blowing some guy started playing. Yup... The last thing I had been using my laptop for was to get off the night before. Perfect. Another relationship ruined.... or so I thought. Terry gave me a mischievous grin. The next couple hours were filled with embarrassment as Terry coerced all my fantasies out of me. He wanted to know what turned me on, what I had experience with (nothing at that point) and what my fantasies were. He wanted to know everything. I'm not sure if it was the humiliation of him finding the porn I was into that gave him the leverage, or if I just desperately wanted to finally tell someone what I was into, but I told him everything! I couldn't believe the things I told him.

When I was thoroughly embarrassed and humiliated for admitting to everything I had always wanted, Terry let me stew in the moment for as long as he could. Then he smiled and told me that his last relationship had a Dom/sub dynamic. 24/7 she was his submissive. He had experience tying up partners in the past, but she was the first one to explore this sort of dynamic with him fulltime. As incredible as that relationship was, and as much as Terry learned about himself and what he was into while he was in it, they were not meant to be. He met me shortly after that relationship ended and he liked me enough that he was willing to explore a "normal" relationship again, thinking I would never be into that sort of dynamic. I think he had missed the kink more than he was willing to admit, even to himself, because there was a fire in his eyes. He stood up and asked for my hand. I gave it. He pulled me over to the bed and as we stood beside it, he kissed me and told me not to move unless it was with his guidance.

Terry grabbed my arm, pulled my hand up to his mouth and kissed from the tips of my fingers up my arm until he reached my sleeve. He said my shirt was getting in the way, as if he was surprised to find it on my body. With a smirk he guided it over my head and started again. Kissing my fingertips, my wrist, then up my arm until he got to my bra. Again, he reacted like he was surprised to find it. A barrier to his ultimate goals. He removed it and started over, this time with the other hand, kissing up my arm until he found my breasts. He kissed and bit me gently, while exploring my body in a way he had never done before. He tugged, licked, and bit my nipples until they were hard. Then he moved down to my skirt. I thought he might remove it and start over again, as he had with my bra, but he just pulled it and my panties off in one motion. I was left naked and dripping. I was more turned on than I had ever been, and Terry knew it.

He spun me around, bent me over the bed, held my arms behind my back with one hand and took off his pants with the other. I looked back and saw that he was more turned on than I had ever seen him as well. He used one of his legs to spread mine, kicking my feet apart, and before I could even really comprehend how helpless I was in this position, he was easily sliding inside me. He filled me perfectly and I moaned.

I was always impressed with Terry's discipline. He never just... went for it. He enjoyed every moment. He went slow at first. I clenched around him and asked him to go faster. I begged... and he pulled my arms a little higher up my back until I felt the strain. It just made me wetter, and in a moment, I had learned not to beg for my own pleasure.

I moaned as he fucked me. We had made love many times before this, but this was different. It was consensual, I needed it, I wanted it... but I couldn't have stopped him if I tried. He was fucking me. Using my body for his pleasure and I loved it. I needed more. He needed more. I felt my orgasm rapidly building. I pulled on my arms and couldn't move them an inch. I tried to close my legs, but found Terry's feet inside mine, holding me just as I was. His cock filling me. That did it. I was helpless, and it made me cum harder than I had ever cum before. My body tightened up around his cock. Seeing me cum, feeling me cum around him, it pushed him over the edge of desire. Terry started to pick up the pace. Faster and harder. I came again. It wasn't stopping. I just rolled from one orgasm into the next. I was almost screaming with pleasure. When I came for the third time, so did he. He slid deep inside and held himself there as his body stiffened up. He grunted and I could feel his cock release inside me. Every muscle in my body tightened as we came together. his warmth filling me. It felt like he was spreading throughout my whole body. I couldn't move and we stayed, locked in orgasm together for what felt like an eternity.

When he finally released my arms and slid his cock out of me, I flipped onto my back and stretched my arms above my head, feeling the freedom of movement again. He looked at me hungrily and asked if I to really experience what it was like to give up control. I said: "Yes please." And he grinned.

After that first night of discovery, Terry took it upon himself to redo the plans for my loft renovation. He wanted to include a few little bonus features and additions that would add to our play. I loved the idea and insisted on paying his company for the work. It was quickly turning into a substantial renovation, and I didn't want to take advantage of our situation. We had only been dating for a few months, after all. He agreed with three conditions. First, I wouldn't get to see the plans beforehand. Second, he would be doing a lot of the work himself. Third, he wouldn't be charging for his own labour. The idea of implementing some kinky ideas into a renovation is something he had always dreamed of doing. It was as exciting for him as it was for me. I agreed and loved the mystery of what kinky secrets he might create for me in my loft.

When he had everything planned out and materials ordered, he sent me on a solo vacation so he could do the work without me around. I didn't mind. Spending time on the beach while he created my kinky loft was an ideal way to build anticipation and relax before the big reveal. Truthfully it turned me on imagining what he might be doing, but Terry insisted that I not get myself off while I was away. He was going to refrain as well. He promised it would be worth it. At that time, I didn't masturbate a lot, so I didn't think it would be as big a deal as it was, but my mind constantly wandered back to what he might have in store for me when I got home.

When I did finally get home, I found myself standing outside my own door, absolutely ravenous for his touch. I knocked, nervous and excited for what I might see next. Terry opened the door and took a minute to look me up and down. His eyes were hungry. I moved in and kissed him deeply and it took him by surprise. We had established a routine of him making the first move by that point already, but god damn it I was horny. He kissed me back with a smile and welcomed me back into my apartment.

The renovation was beautiful. I won't give too much away, perhaps you'll make the right decision and get to see my loft for yourself, but Alex... if you have ever wondered what turns a woman on, let me tell you that competence, skill, and a passion for what you do is a good start. I knew Terry was good at his job, but I was floored. What was once a large open space with potential had become an architectural masterpiece. Modern, bright, and yet it all felt natural with building materials that matched the previously exposed walls. He had built completely new rooms that hadn't existed before, and even though it closed the living room and kitchen in more, it somehow felt just as big. The space flowed so perfectly. It was more beautiful than I had ever imagined it could be.

Terry took my hand and guided me on a little tour. He walked me through the kitchen, showed me all the fun non-kinky features he had added, and then he guided me over to a wall that hadn't previously been there. He had built it out with brick and large timbers that fit in perfectly with the building. A large mirror in an ornate frame hung right in the centre. It was beautiful. I was looking at the two of us in the mirror when terry asked me what I thought was behind the wall. I had no idea.

Terry hit the light switch beside the mirror and the mirror become a window. Well, it was one of those one-way mirrors. When the light was on in the room behind, you could see clearly into it. When the light was off, it was a perfect mirror. The room itself was filled with all sorts of kinky delights. I wanted to explore. I wanted his cock... I wanted to get off. Terry saw the look in my eye and smiled. He asked for my hand again. I gave it and he guided me out of the main living space and into the bedroom.

My eyes went wide with all he had done. Previously my bed was just in the corner of the loft, but this was a room with all sorts of things that pulled my attention in. But we didn't stop. He pulled me through another door that led into the room behind the mirror. He kissed me, and then started to pull my clothes off. This was often how we started when things were going to get kinky. Terry would undress me, or I would undress in front of him, and I'd be naked while he was still fully clothed. It set the tone that he was in control. Once he had my clothes off, Terry walked to one of the walls and pulled down some high heels. They were much higher than I had ever worn. They were black, lace up Mary Janes with a seven-inch heel and a small platform. He put them on my feet, laced them up, and walked me over to the inside of the mirror. The shoes forced my feet in high arches. It was like standing on my tip toes. Terry helped me step up onto a platform that had a steel dildo on a pole right in the middle of it. He asked if I trusted him, and I told him I did. He had me stand overtop of the dildo, and as it turns out the pole was adjustable in length. He extended it. I was so turned on, it easily slid inside. Truthfully, I was a little disappointed. I wanted his cock... but I still was excited to explore whatever this was that he had planned.

Terry extended the shaft until the steel cock was as deep in me as it would go. He then asked me to stand up straighter, so I moved my legs a little closer together, heels on either side of the base of the pole. He then extended the pole just a little more until I gasped. It was just shy of uncomfortably deep. Terry locked the pole at that length and stood up, pleased with himself. He told me this was called a one bar prison. With high heels on and my legs fully extended, I would not be able unimpale myself from the steel cock. I didn't believe him... I squirmed and spun myself around, but sure enough, I couldn't get any additional height. My legs were perfectly straight, and with the heels, there was nothing I could do. I couldn't reach anything around me either, I was just stuck on this steel pole in the middle of the room. I couldn't even bend over to reach the lever to shorten the pole. It was a strange feeling. My limbs were completely unrestrained... and yet I was helpless. I couldn't leave that spot.

Terry kissed me and told me I looked beautiful, stuck on this steel cock, desperate for more.

Then there was a knock at the door. I looked at him sheepishly and he told me that some of his guys were coming by to pick up the rest of their tools. He said he'd be right back. I was stunned. I looked out the mirror into the main loft space and then back to Terry, but he was already gone. I desperately tried to maneuver myself off the of damn thing but was completely helpless. That's when Terry walked out into the loft space. He looked in the mirror and blew me a kiss. Then he headed for the door... But the lights were still on in the room. They would be able to see me!

Terry got right up to the door before he turned back and saw me freaking out. He smiled, calmly walked back to the mirror and said he almost forgot, with a grin. Then he flicked the switch and the room around me went dark. I was relieved. What I didn't expect, however, was for Terry to reach into his pocket and pull out a small remote control. He pressed a button and the steel cock started to vibrate inside me. He winked at the mirror and then walked back to the front door and let two of his employees in.

They rounded up the tools and took turns carrying everything out. I was helpless to watch from the dark room behind the mirror. Terry turned the lights on in my room a couple times when both employees were on a trip to the truck. He enjoyed seeing me helpless and squirming. On the third time he did this, he smiled, and only then did I realize that I had started rubbing my clit. I was so turned on. Being helpless, the chance of being caught, and this damn steel cock vibrating inside of me after weeks of not getting off. I needed to cum, and I needed it badly. Terry turned off the lights again as his staff came in for the final time. They looked around and even they were impressed with how my loft turned out. Terry looked over at the mirror and then back at them and offered them a beer. I came right then and there. I felt so helpless. I clenched around the steel cock, and of course it was immovable and unrelenting. The vibrations continuing as my whole body shuddered around it.

Terry's employees accepted the drinks and they sat in my living room shooting the shit while I came five more times just on the other side of the glass.

Eventually they finished their drinks and left. Terry deadbolted the door and walked back to the mirror, turning on the light. My juices ran down the pole to the floor. I bit my lip and tried to look as cute as I could. He pulled out the remote control from his pocket and tapped another button. The vibrations doubled. My hand moved, almost subconsciously, to my clit and started rubbing in tune with the vibrations again. He smiled, walked away for a second, and then came back with a chair. He put it down in front of the mirror and sat, opening a fresh beer. He watched me cum 3 more times, sipping on his drink and enjoying the fruits of his labour. I couldn't stop. Every orgasm felt like too much... but the pleasure was unrelenting. Just when I thought I couldn't take anymore, I would feel that next orgasm start to build. When my knees started to shake, he knew I was exhausted. So, he watched me cum one more time and then turned off the vibrations. Terry put his empty beer down, left his chair, and before long, he was standing right in front of me. He took my arms and put them onto his shoulders so that I could hold myself steady. He lowered pole and that steel cock slowly slid out of me. My knees almost buckled, but he scooped me up into his arms and took me to bed.

That was the beginning of a three-year relationship with Terry constantly in control. It changed me. He changed me. And I want you to understand something, Alex. Before that holiday, Terry had tied me up a little. We had played... but that was essentially my baseline experience, and it only got kinkier from there. I am not looking for someone to tie up for an hour. I am not looking to be some uninvolved keyholder. I am looking for real control. Things you have likely never even imagined. So, once again, I am giving you a choice:

Path 1

Perhaps this sounds like it might be too much for you. It was fun while it lasted, but you don't think you can really explore the sorts of things I'm interested in exploring. You don't think you can give up that level of control. I understand and wish you the best of luck. Don't respond to this message. You will regain control over your chastity tomorrow after the time limit is up, and you will never hear from me again. Not wanting this is perfectly acceptable, but you can't take it back. If I don't hear from you, you won't hear from me. Ever.

Path 2

You send me a message that simply reads "I want to see how deep the rabbit hole goes." By sending this message you are telling me that you want me to continue to have control over your chastity device beyond this single day time limit. You want to see what giving up control for real feels like. You want to explore what I have in store for you and understand that this is not light bondage and a spanking. I will be in control for real.

Choose... wisely.

Sam

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Alex's cock had never been so desperate to be touched. He needed to jerk off. He needed to take this cage off... but he couldn't. He felt helpless and that just made him more turned on. There was only one thing his horny little mind would allow him to do.

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I want to see how deep the rabbit hold goes.

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Sam smiled when she read the message. She opened the CFE app, pulled up Alex's profile, and removed the one-day limitation on her control over his device. You see, the thing is, Sam started the CFE company. She designed the CFE 2.0 and created the app that controlled it. Her phone had master access and complete control over every device on the network. This was just one of the many companies she had built from the ground up over the past few years to make her dreams become reality. Alex really had no idea what he was getting into... but he would find out soon enough.

CHAPTER 05

Alex was sitting at his computer. It felt like the longest day of his life after the longest night. His constant need to get off and the strain of the CFE 2.0 keeping his cock locked down made sleep nearly impossible. Just when he managed to doze off, he woke up to cock reminding him that he couldn't properly get erect. He would have done almost anything for release... but Sam had given detailed instructions. Alex was to meet her back at the coffee shop at 5pm. What she hadn't specified, and what was essentially the loophole Alex was planning on using, was that she hadn't told him to renew her control over his chastity when the 24 hours elapsed. And thankfully that 24 hours was about to run out. He would take off the device, jerk off, lock it back on, and then go meet her at the coffee shop.