The Reluctant Submissive Pt. 01

He was slightly surprised at not having received any messages back from his Dom by the time he left his room for the meeting with the owners. The meeting went well and the couple were delighted with the works in progress and the further ideas Ryan had for the editing process. By the time Ryan returned to his room having shared a couple of bottles of wine with the couple it was getting late and he was feeling slightly tipsy. Then suddenly his phone lit up with a message notification.

--- Wow. What a busy boy you have been subbie. Well done. There's lots for me to think about here. Chastity. Exhibitionism. I can't wait to see what you send me tomorrow. ---

Ryan decided not to respond. It wasn't possible to tell from the messages whether the recipient had read them, so he decided to wait and see what else arrived. After a few minutes his wait came to an end.

--- I guess you've gone to bed already. I think we need to do something about that as well. From Monday, you need my permission before you go to bed. Now, here's a list of things I'd like you to buy so that we can put them to good use as part of your training:

Chastity cage. I suggest something like a CB6000, which will allow you to work out the sizing by trial and error.

Butt plugs. A set. Increasing sizes.

Dildo. If your girlfriend has one and you have access to it, that will do. Otherwise buy one. I'm not too worried about size but make it as realistic as you can find.

A balaclava or mask. Something that will hide your face when you send me full length pictures.

Clothes pegs.

Lots of lube!

An enema kit.

Message me when you're home tomorrow subbie. I want to chat about today's messages. ---

Since he had returned from his little adventure on the beach, Ryan had been starting to feel more relaxed about his arrangement with the Master. The shopping list changed all that. Now he felt on edge and nervous about what lay in store. As he turned off the lights and settled down to sleep, his mind raced over the multiple possibilities that lay in store for him. He slept fitfully, with images continually popping into his head.

The morning arrived all too quickly and despite having set his alarm later than the previous day, Ryan didn't feel at all rested when he awoke. He took his breakfast at the last possible opportunity before packing and checking out. One final discussion with the owners and then he was on his way. Ryan spent some time driving around the local area and stopped for lunch in one of the villages that lay just off the coast road, before turning his car and heading home. Even on the drive home he kept thinking of the shopping list and images of the items swirled around in his head.

Arriving home in the early evening Ryan decided to message his Master before doing anything about the shopping list. Having sent a brief note confirming he was home, Ryan unpacked and then stripped to perform his submissive position training. It was becoming almost second nature now and he could remember most of the positions without having to refer back to the image he had received. Having completed each position for two minutes his toes and thighs ached. He put on some shorts and a tee, fixed himself a sandwich and then settled into his sofa to work through Twitter and find that day's RT.

The message from his Master came just after he had tweeted.

--- Back in the comfort of your own apartment then subbie. That's good. I have a new rule for you today. In future, every time you message me, you must be naked. That should help instil a feeling of submissiveness in you. We will start now. Strip subbie. ---

Ryan did as he was told and then sent a short message confirming he was naked.

--- Very good. Now show me. Position 'wait'. No face in the picture. You have 1 minute. ---

The moment had come. Again, the time limit which took away the possibility of Ryan considering what he was about to do. Putting his phone into camera mode and positioning it so that his body would fill the frame, he adopted the position without needing to check. This was the one he remembered as it was the most explicit. Legs spread, hands locked behind his head. He took the picture with his face visible then quickly cropped it so that he could not be recognised but with it still possible to see that his hands were in position. Then without thought as to the consequences, he pressed send. The reply was immediate.

--- Very good subbie. I thought you might have baulked at this one. ---

--- No Master. You commanded me to do this and I have done it. That is my role. ---

--- Excellent. We will make a compliant submissive of you yet. But you don't look very excited subbie. I hope for your girlfriend's sake that you are a grower. Though thinking about it, she may not be reliant on you for her pleasure for much longer! ---

The message was accompanied by a smiley face. Before Ryan could even think of how to respond, another message arrived.

--- It's interesting you said yesterday that you are beginning to find some of your tasks arousing. Why do you think that is subbie? ---

--- I don't know for sure Master, but I think it's because I am beginning to like the idea of being controlled by someone else. When I sent the picture just now, the only thing on my mind was making sure I responded within the deadline. I didn't worry about the fact you would see me naked because you had already decided that is what would happen. ---

--- Do you see your growing arousal as a problem subbie? Because I do. That's why I've put a chastity cage on your shopping list. You are not to masturbate or fuck your girlfriend for the remainder of your time with me subbie. Unless I give you permission of course. And to make sure you stick to that I'm going to put you in chastity. How does that make you feel? ---

--- If that is what you wish Master, then I accept your decision. ---

Ryan was already wondering if he would be able to manage over three weeks more without an orgasm. It was probably the longest he had been without since he had been in his early teens. But truth be told, he was looking forward to experiencing the chastity cage. Maybe not for three weeks, but he was intrigued to experience how it would feel.

--- I hope that's the truth subbie and not just what you think I want to hear. Now, tell me, what were you thinking of when you stripped naked on the beach yesterday? And what time was it. When I opened the photo, I was expecting it to be dusk. But it looks as though you were there in the heat of the day. ---

--- It was about 4pm Master. Still very light. It was a similar feeling to the one I have just described. I spent some time making sure there was no one near me and when I was satisfied I wouldn't be interrupted, my only thought was to do what I had been told to do. Even stepping away from my clothes didn't cause me any concerns. I'd thought about the implications beforehand, the fact that if someone turned up unexpectedly I wouldn't be able to put anything back on, but once I was naked I just went through with what I had been told to do. ---

--- I'm impressed subbie. Maybe I need to make your next task even more challenging. Tell me, is there anywhere near where you live that you could go to and safely be naked. Don't forget subbie, I expect the truth from you at all times. ---

There was a slight pause before Ryan responded. He was actually thinking if there was any way he could be naked outdoors. The idea of lying to his Master didn't even enter his head.

--- There is a park Master. It's not very big but there is a wooded area. Dog walkers tend to stay at the edge, so I could go into the middle as it gets near to dusk. There is also the yard behind my apartment. Not during the day, but it tends to be quiet in the evenings when everyone is back home for the night. ---

--- I will store that away for another day subbie. Now, the shopping list I sent. Any questions? Other than what I have planned for all those things of course. You'll find out the answer to that soon enough. ---

--- I don't think so Master. ---

--- Good. Can I suggest you order tonight and choose express delivery. You will need at least one for what I have in mind for the weekend. ---

--- Yes, Master. ---

--- Oh and one more thing. Tomorrow's Friday and my ban on you seeing that girlfriend of yours comes to an end. Remember, no sex without my permission. ---

--- How could I forget Master. I understand. ---

Ryan spent the rest of the evening looking at various sex toy websites before deciding on the items he would buy. Once he had ordered he went to bed and tried to catch up on some of the sleep he had missed the night before, but sleep was again elusive. He had crossed a line earlier, the Master now having a picture of him naked. Where was this game going to end?

Waking up, Ryan realised he had slept naked. With no set timescales for the day, he decided to start the morning by working through Twitter and completing his RT task. He grabbed a coffee from the kitchen before returning to bed. Then, coffee finished and RT sent, he got out of bed and completed his submissive position training. Once he was dressed he set to work finishing the editing of the hotel pictures and catching up with emails. He had set a target end time of 4pm and then his first task was going to be making plans for the weekend with Nikki.

A little after lunch, he heard the sound of a message arriving on his phone. As he looked he found it wasn't the Master but his girlfriend.

--- Hi babe. I hope your week hasn't been TOOOOO bad! I'm really sorry about this but I'm not going to be able to see you this weekend. I'm about to set off on an adventure. I'm spending the weekend at a hotel with the Mistress. Apparently, she has some tests for me so that she can assess if I really am submissive material. And she's said I must not contact you until it's all over on Sunday. Sorry babe. Love you. N xxx.

Ryan was disappointed but tried not to give any hint of that in his reply as Nikki seemed so excited with what she had in store.

--- Hi Babe. I'm ok, thanks. I've made it through the first few days. Still really nervous about what's in store but I keep thinking about the big picture and buying your freedom. It's a shame we won't be able to discuss things this weekend, but I have more tasks to perform for my Master and it sounds as though Mistress will be keeping you busy. Have fun! Love you, R ---

He had expected an immediate reply but none came. After a few minutes thought he took a deep breath and sent another message, this one to his Master.

--- Hello Master. I just thought I ought to let you know, I won't be seeing my girlfriend this weekend. She is busy with her Mistress. I am therefore at your disposal all weekend. ---

There was no immediate reply and so Ryan decided to pop out and buy some groceries for the weekend. Catering for one. A message arrived as he was leaving the supermarket. He glanced at the phone and saw it was from his Master, not Nikki, so he decided to get home before reading it. When he did read it, he was glad that he had waited. It was a long message and not the sort of content he would have been comfortable reading out in public.

--- Hello subbie. So, stood up by your girlfriend eh. Never mind, I will keep you occupied over the weekend. We are going to spend some time allowing you to experience one of the key aspects of being a submissive. Specifically, the fact that your dominant owns your body. And this weekend subbie, I own your ass. You are going to surrender your asshole to me. This does of course assume that your shopping arrives in time. If it doesn't, you will be punished for failing to ensure express delivery as I instructed. Now, here's what we are going to do. In addition to your existing two daily tasks, you are going to wear the small butt plug on Saturday and the medium butt plug on Sunday. At least 6 hours for each. But before you start you will need to do some reading to learn how to give yourself an enema. Because you need to ensure your ass is nice and clean now subbie. As a submissive male, you need to understand that you have two holes for sex, plus your tongue when you are pleasuring your Mistress. Your dick doesn't come into the equation. It's not there to give you pleasure any more, it's there to provide something that enables your dominant to inflict pain or frustration. So your primary sex organ as a submissive male is your ass. It needs to be available to your Dom 24x7 and it needs to be clean. I understand that some guys learn to cum from anal stimulation. For those that don't, they just have to get used to a life of frustration and denial. I wonder which camp you will fall into subbie? ---

Ryan was shocked and was beginning to feel numb. He'd obviously known the objects on the shopping list would end up being used, but he'd not expected the straightforward manner in which the Dom had explained to him just what they would be used for.

--- Thank you for making that clear Master. A parcel has just arrived and I assume that is my shopping. I will spend this evening researching how to give an enema so that I may serve you as you have outlined this weekend. ---

--- Good. I do like an obedient submissive. One more thing subbie. Starting tomorrow, you will be sent a 'position of the day'. You will hold that position for 3 minutes and when you are done, you will take a photo of yourself in that position and send it to me. We will get the hardest out of the way first. Endure. Sleep well tonight subbie, you will have a lot to .....Endure tomorrow.  ---

Ryan threw his phone to his left and watched it bounce off the sofa and onto the floor. Then his head swung backwards and he screamed. 'How have I got myself into this mess,' he thought. Staring out of the window he took stock. Starting tomorrow he had a daily task of photographing himself naked and sending it to his Master, he had to learn how to give himself an enema and he had to wear a butt plug. And that was before he found out about the chastity cage and the outdoor nudity. Plus, no sex with Nikki. He was only doing this for her. His thoughts went back to the earlier conversation with his Master. Would she really get her pleasure elsewhere? He had seen how much she had enjoyed that first session with the Mistress and that had only been 4 hours. She was about to spend the next 48 in the company of the dominant. After that, would she ever want to spend some vanilla time with her straight boyfriend again?

Ryan had a troubled sleep that night. Thoughts of what lay in store mingled with thoughts of what his future with a submissive girlfriend might look like. None of it painted a pretty picture. He woke early, deciding he might as well get up as continue the search for sleep that seemed doomed to failure. He had again slept naked and didn't bother to cover himself as he padded into the living area and opened the parcel that had arrived the day before. He'd done as he was told and researched the subject of enemas but when he stood there with the kit in his hand, he couldn't bring himself to start the day that way. So he made himself some breakfast and then did his position training. Saving Endure to last, he retrieved his phone and positioned it so that he would get a good image. Ryan got into position and took the photo, leaving his face exposed with the plan of obscuring it later. Continuing to hold the position for the allotted three minutes he looked at himself in the mirror, his hands behind his head and his legs spread, completely exposed. As he imagined the Master receiving the picture, his penis began to harden. 'What the hell is wrong with me?' he asked himself.

By the end of the three minutes Ryan's legs were screaming for relief. He had never been happier than to stand up and stretch his legs, one after the other. Then he went back to bed, spending an hour on his RT task and then editing the Endure photo before sending that to his Master. He didn't hesitate as he pressed the send button. The photo was ready and he had been told to do it, so he did.

It was time for the enema. He couldn't put it off any longer and he wanted to ensure his six hours with a butt plug were over as quickly as possible. The more of that time he could manage before the Master was awake and messaging, the better. Still naked from earlier, he entered the bathroom with the kit. He sat on the toilet and tried his best to empty his bowels naturally. Then he filled the plastic bulb with lukewarm water. The articles he had read suggested either bent forwards with legs spread slightly apart or on your back with legs in the air as being the best two positions for newcomers to the task. He chuckled as he thought the same could no doubt be said for being penetrated. An image of the Master popped into his head, advancing on him with an erection, which was a little odd as he had never seen a picture of him. The image was soon replaced by one of the Mistress, a large red strap on worn over leggings.

Shaking his head to clear his thoughts, he screwed the nozzle into the bulb and applied some lube to the thin tube that would soon invade his body. Then setting the bulb down in the sink, he bent forwards and spread his ass cheeks. The fingers carrying lube missed their target initially, Ryan surprising himself at how difficult it was to judge where the opening to his anus was positioned. Having slid his fingers down the crease, they rested on the ring that was the opening to his most private of places. Positioning one finger on the centre of the ring, he gently pushed but struggled to open the hole. After two or three failed attempts he withdrew and applied more lube, then tried again. This time he combined the pressure with a gentle circling motion and this appeared to do the trick, his sphincter muscle opening sufficiently for the tip of his finger to enter. Continuing with the pressure and the circling motion he slowly forced his finger inside until he reached the first knuckle, before gently moving his finger and applying the lube to the walls of his anus. He was amazed at how strong the sphincter felt, holding onto his finger in a vice like grip. He shuddered as he thought about the practicalities of taking a dildo or penis through that opening.

In comparison to a phallus, the tiny nozzle looked a much easier proposition to Ryan. And sure enough it was. After two failed attempts and a slight change of position each time, he succeeded in penetrating his ass. The feeling was unexpected. He could sense there was something inside him, but the nozzle was so thin it was difficult to discern it once it was inserted. Repositioning his grip on the bulb, he squeezed and experienced water inside his ass for the first time. The squeeze had been gentle and the amount of water miniscule, but he felt the warmth none the same. The sensation was almost pleasurable. A longer squeeze followed and this time he knew what to expect. After four more, the bulb was empty and his ass was full.

Ryan stood and walked the length of the bathroom slowly. He knew he was supposed to hold the liquid inside him for a few minutes and had read that this part of the process could be quite challenging. His initial reaction was that he must have done something wrong as he felt fine, but suddenly an urge to expel the liquid overcame him. He rushed to the toilet and sat down. The relief that he gained from letting go was joyous but was soon replaced when he saw the state of the toilet.

The process was repeated two more times and it was only after his third treatment that the remnants of his expulsion were clean. It was time for the plug. Copious amounts of lube were applied to both the plug and his hole before Ryan took a deep breath and presented the steel to his sphincter. The plug was clearly well designed as the shape slowly opened him up. Applying gentle but persistent pressure, Ryan managed to make progress and groaned aloud as his body accommodated the ever-widening plug. Suddenly it was there, the feeling as his sphincter closed around the bulbous plug one he wouldn't forget in a hurry. It had seemed as though his ass had decided to suck the plug into him, the feeling of his ass suddenly being invaded after the slow progress he had made in the first place. Then a fear that the plug would disappear completely, before the relief as the wider end plate met the resistance of his now closed hole. The design of the plug had done its job perfectly, his powerful muscle clamping around the narrow neck of the plug and the wider end ensuring it would not enter him any further.