Caged for Freedom Ch. 03

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The story comes to a earth shattering conclusion.
10.3k words
4.6
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Part 3 of the 5 part series

Updated 06/07/2023
Created 09/16/2015
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I awoke slowly, reaching for that moment when waking and sleeping cross over and the waking part is the more prominent. It was very quiet throughout the neighbourhood and it seemed almost that I was the only one there. Not a sound.

I rolled over luxuriously and had a look at the clock. 9:15am. I had slept in again.

I rolled back onto my back and staring unfocussed at the ceiling, went over in my mind, all that had happened over the last few days. I could scarcely believe that I had been royally arse fucked twice in the last two days. Actually three times if you counted the fucking Gail had given me with the strapon!! Of course I had to believe it as even now, I could feel the dull ache in my arse where it had been used by Bob -- or whatever his name was and was still being stretched by the huge butt plug that I had left in place when I got home last night.

And what's more, it was all going to happen again tonight!!!!

My hand idly wandered down to feel the solid steel cock cage locking my man hood until Gail released me. But I knew only too well that for that to happen, I had to take Bobs hard cock up my arse for a third time. I couldn't wait!!

I got out of bed and headed for the shower. It still felt strange showering with my penis locked up in its prison. Sort of distant as there were no direct feelings you normally get from the hard shower spray. I took the shower head off the wall and turned the pressure up, running the water hard and heavy across the cage and massaging my balls with the jets. It felt heavenly.

By the time I was dried and dressed it was closer to 10am and rather than prepare a full breakfast, I thought I'd just have a coffee and croissant. After all, I didn't want to fill myself up as I wanted to be nice and clean inside for the final, the hat trick, the third fucking.

I was deep in thought drinking my last mouthful of coffee when the phone rang. It was Gail.

"How are you this morning," she asked.

"Well I certainly know I have been thoroughly reamed over the last few days. My arse is a little sore but not too bad and I have noticed that the whip marks you left on my butt have all but gone so that is good," I told her.

Gail laughed.

"I'm glad about the welts and the sore arse for that matter. No point in going to all this trouble and you not having anything to remember it by. So what about tonight? Up for more?"

I didn't need to think at all to answer that.

"Absolutely! I've not been able to get it out of my mind since leaving your place last night," I told her.

"Wow, you have certainly surprised me. I didn't know that you would enjoy the first night and here we are talking about a THIRD night for you. Any requests," Gail asked.

Up to now, apart from a few minor surprises, what had happened had all been dictated by me, from the way I was immobilised to what had happened once I was. My mind went into overdrive with Gail's request.

"How about this time you decide what's happening to me, when and by whom. I feel totally safe in your hands and have enjoyed everything that has happened to me so far so I want to be under your total control," I replied.

Gail was quiet for a long moment.

"OK," she said, "but the deal is this. As you say, I am in control and you will just have to take whatever I decide you are going to get. Don't worry, I will make sure there are no marks on you but it could be a long night for you and a very revealing one too. Deal?"

Again my mind went into overdrive. I had total faith in Gail and knew I would be totally safe but she also knew me and my sexuality better than anyone alive and had really enjoyed pushing my buttons in the past. Some I even didn't know I had. I hesitated but a moment.

"Deal," I told her.

"OK," she said, "I want you here at 3pm on the dot. You are to be wearing the largest butt plug you have and a G String that has clips at the side to take it off with. Over that you will wear a pair of satin boxer shorts and a t-shirt. That's all."

"OK, I can do that. See you at 3." And Gail hung up.

Well, I thought. That's it, cast in concrete. I was going to be totally out of control today and the thought both frightened and excited me. All I had to do was get through the day, turn up at Gail's at 3pm and do whatever I was told to do.

Like the day before, today crawled through the hours. I again invented things to do to keep me busy but try as I might I couldn't get myself into anything of any substance. What kept racing through my mind was, what did Gail have in store for me tonight or rather, this afternoon!

Lunch time was a non event as I so wanted to stay clean inside for what was to follow. Fortunately I had some excess weight that I could well afford to lose so was happy to have a liquid lunch, just to keep me going. If Gail gave me any wine, I knew I'd be sloshed in no time!

By 1:45pm I was frantic. My mind had conjured up all sorts of scenarios that were both fanciful and kinky and I had no doubt that Gail would be working along similar lines herself. I so wanted to call her and discuss what she had in mind. To top from the bottom as it were but knew better than that. Gail was in her element.

Many years ago, we had played all sorts of kinky games where I would go to see her but before hand, she would drop a note in my letter box, instructing me to be dressed someway or locked somehow. The mind games were exquisite and she knew better than anyone else how to play them. When I was the target of those mind games, all I wanted to do was surrender to her.

I had determined that at about 2:00 I would start my enemas to ensure I was totally clean and free of any residual water. As before, I prepared the ensuite, removed the butt plug that was still in place and luxuriated in the process of cleansing. I had always loved the feeling of being full and this time was no exception though unlike other times, I made sure the long soft hose went way up inside of myself, filling me from within. Though feeling the pressure, I felt like I could take so much more enema than normally and silently hoped that I had given myself enough time to expel everything.

By 2:30 though I was all prepared, squeaky clean inside and ready to get dressed for the drive to Gail's.

Gail had said for me to wear the largest butt plug I had but what she didn't know was that I actually had bought a plug some time ago that I simply couldn't get inside me. It was huge! So big in fact that I was too scared to measure it.

I guess it wasn't that long, but the girth of it was impressive and I had wondered how anyone could get it in their butt. It was one of those that started bluntly on the tip and flared really quickly but stayed wide, not actually thinning down so much at the base. This meant that once in and seated, it continued to stretch almost as widely as it did at its widest.

I had tried to get it in a few times, sometimes wearing the largest I could comfortably get in for a considerable time first to stretch me out but still couldn't. Still, Gail wanted the largest so I retrieved it from its hiding place and cast my eye over it.

Impressive wasn't the word that came to mind just then. Scary yes, impressive no. I thought about things just then and realised that I had been wearing a butt plug for the best part of four days and the plug wasn't a small one either so if I was ever going to get this monster in my arse, it was going to be now. Ever conscious of the time, I grabbed the plug and a bottle of lube and knelt down on the ensuite floor.

Remembering what Gail had done to me, I squirted a good dose of lube directly into my arse, then liberally coated the plug. Bending forward until my head was touching the floor, I grasped the plug by its base and pressed it against my eager but nervous butt hole.

I couldn't believe it to start with, the monster just slid into me and I thought it would be a breeze when suddenly, my sphincter stretched to as far as it would go and that was that. I tentatively felt round the plug and realised that it was only about a half of the way in so I had lots to go.

Relaxing as much as I could and doing the bearing down trick, I managed to get the monster going again. I slid it out a bit then back in a bit, trying all the while to get it in just a wee bit further than I had taken it out. Time stood still for a moment as I concentrated on the amazing feeling of being stretched more and more round the massive plug. With all the lube I had squirted inside of me, the plug was very slippery and almost had a mind of its own as I worked it ever deeper into my quivering butt.

I had got to that point where I felt that regardless of how much I wanted this in me, it just wasn't going to happen and that's when it did. Imperceptibly, I felt the plug begin to move into me by its own accord and I realised that it was going all the way. I helped it into place, pushing it that last few millimetres until the base was sitting hard against my arse lips and let out a long, grateful sigh then wondered what it was going to be like getting it out!!!

I got gingerly to my feet, feeling the plug sit heavily inside of me. One thing I forgot to mention is that the plug was incredibly heavy. It was very slick and smooth and even soft to the touch but inside it must have been metal because the weight of it dragged hard on my butt and I knew it was going to niggle me constantly until it was out.

I went into the bedroom and glanced at the bedside clock and realised that I was now running late! I dressed hurriedly, making sure I was dressed exactly how Gail wanted me, grabbed my car keys and bolted out of the house.

As soon as I sat down in my car, I knew that the plug I had sitting inside of my over stretched butt was going to torment the hell out of me on the drive. Yes it was huge, yes it was sitting in as far as it could but if you've ever had a large plug in you, you know what it's like sitting on it. It always gets pushed in just that little bit more and makes the experience just that more pleasurable or painful, depending upon how big it is. In my case, it was painful. I tried to sit lightly but within a few kilometres, I had to simply sit down and take the pain. Fortunately it was only a ten minute drive to Gail's place as the traffic was light.

Like last time, Gail had left here garage door open so I drove my car straight in. As I carefully got out of my car, Gail appeared at her front door to let me in. I was obviously walking a bit gingerly because Gail laughed a bit as she saw me approach.

"You look like you've got a broom handle up your back side," she chortled.

"Actually no, it's the largest plug I have which you dictated I wear. I had never been able to get it in before today and believe me, it is enormous," I told her.

"Oh," was all Gail said as she visibly paled then led me inside.

We walked through the house into the lounge where Gail sat down and indicated for me to sit across from her on a facing couch. I lowered myself gingerly down and fortunately found that the softer cushioning on the couch didn't push the plug in as hard as the car seat had.

"That must be a beauty plug judging by the care that you're sitting on it," Gail commented.

"Yep, I've had it for some time and had never got anywhere near to getting it in. I'm too scared to measure it and actually wonder how we will get it out but we will have to -- won't we?" I replied.

Gail nodded thoughtfully then picked up a small writing pad she had on the couch beside her.

"I thought I'd make some notes about what I want to do with you today. I am not going to discuss them with you because I want them to be surprises when things happen to you but I need you to know that in a few minutes we are going to start and once started, I will not stop until we get to the end of the scenario I have created which will be in about seven hours time. We have the safe word and safe noise sorted out so that will be all you need to remember. Once we start, you will be in some form or another of bondage. Do you want to proceed," Gail asked.

I didn't really need to think about that question and nodded as well as affirming by saying a definite Yes!

"Alright then, come with me," Gail said as she stood and walked out of the lounge and down the hallway to the kitchen.

When we arrived in the kitchen, I could see the pillory and other gear all set up on the bench area and began to wonder if she was going to lock me up there already.

"Take off your boxer shorts and sit down on that bar stool," Gail told me as she indicated one at the end of the bench. On that end of the bench lay several of the items I knew I would be wearing that included the hood, gag and collar.

I did as I was told and sat and waited patiently as Gail sorted out the various bits and pieces she wanted, then she turned to me and handed me some ear plugs.

"We are going to get you into your sense deprived state right at the outset and you will be in this state most of the time. That way, whatever happens to you, you will be feeling more than with your senses so please put these plugs in your ears and we will go from there."

I dutifully applied the plugs to my ears, making sure I got them seated well inside. Once they were in and had grown out to their full size, I could hear almost nothing.

Gail put her mouth close to one of my ears so I could hear and told me to put my hands behind my back. As I did this, she secured my hands there with the hinged hand cuffs she had used on the previous nights and I knew it had well and truly begun.

She picked the blind fold mask up next and gently pulled it over my head and onto my eyes. It was one of those really fancy ones, made in leather, contoured to my face shape and with the hood over the top, would provide a perfect and unremovable blindfold.

Blind now and almost deaf, I needed some gentle prodding for Gail to get me to turn my back to her so she could go to work on the hood. Pulling it purposely down over my head, she was careful to ensure that the blindfold wasn't displaced from my eyes before seating it solidly on. She had done this before quite a few times now so was a real expert at it, lacing the hood as tightly as she could into place. When she did the buckle up at the neck, an involuntary shiver ran through me.

Up to now, Gail hadn't put a posture collar on me as there was no way that I could wear that in the pillory but for now, I felt her tilt my chin up as she placed the collar in under my chin and wrapped the rest round my neck. With double Velcro bands holding it in place, it was going nowhere.

I was expecting that Gail would gag me next but instead, I heard her at my ear.

"I am going to leave you ungagged at this stage as I need your mouth but you are not to speak unless I need an answer to a question. Do you understand," Gail asked.

"Yes," was all I answered and with that I felt her move away.

I could do nothing but wait until she came to lead me to wherever she wanted me so I waited. Time seems to stand still when all your senses are blunted. I didn't mind the waiting because I was in heaven! Being totally out of control like I was, had been a fantasy of mine for as long as I can remember so I revelled in the feeling of freedom I had.

A very slight noise came through my ear plugs and I realised I could very faintly hear high heels clicking on a hard floor. I could only begin to imagine the heals Gail was wearing and figured they could be the sky high ones she was wearing when she pegged me with her strapon. I'd love to see them!!

I then realised that I could hear two sets of foot falls and they were both wearing high heels. Oh what torture not being able to see them!!

I felt two sets of hands take my upper arms, one on each side, as they pulled me gently but firmly to my feet. I was lead carefully through the house and into a room that I could only imagine as my spatial awareness had failed me entirely.

I felt one set of hands let me go then very soon afterwards, I was pushed down into a kneeling position. I wasn't sure why then smelt the unmistakable smell of a woman's sex. A very turned on woman's sex at that!

I felt a pressure on the back of my head pushing me forward and cuffed as I was, there was no way I could resist to leaned forward, obviously toward the very turned on woman. I felt what I could only imagine were thighs rubbing along each side of my head then I could feel very wet vagina lips on mine.

Suddenly I felt two hands on the back of my head, pulling me into what again I could only imagine was a very wet pussy -- and I was right. I had no idea who this was nor did I care. She tasted fabulous and I wasted little time getting to work, licking and sucking on this very tasty banquet.

Because my head was well and truly held rigid within the posture collar, all I could do was lick what was placed in my mouth so I went to it like a man possessed. My tongue travelled slowly but deliberately up the slick slit I could feel before me, flicking the very aroused clit it found on the extreme of its upwards travel. At that, the hands on the back of my head pulled me tighter into the task, making me gasp for breath.

I imagined the joyous noises that were coming from the owner of this very fine and tasty pussy because from time to time I could detect faint tremors running through the thighs that were gripping my head in their vice like grip.

I was so enjoying myself that I hadn't realised that there were another pair of hands working at taking off my G string. I had been asked to wear one that could be unclipped, which of course I had, so the deft fingers were now unclipping the sides and sliding the G string away from me. I idly wondered what was going to happen now considering that I had an enormous butt plug in my arse and my manhood was well and truly secured. I found out soon enough!

While I continued my ministrations to the luscious pussy I was servicing, I suddenly felt a high speed vibrator being touched to the base of the butt plug. The effect of the vibrations though my extended sphincter and onto my prostate was an immediate response to get an erection. Of course, with the steel cage well attached, the result was a very painful surge of blood into my penis as my body did all it could to make me hard.

Fortunately, I had other things on my mind at that point, and that was the obvious nearing of an orgasm for the lady with the tasty pussy. She pulled my head even harder into herself meaning that I could barely breath so I did the best that I could to make her come as quickly as possible. Abandoning the licking, I went to full on sucking and nibbling of this yummy clit which finally pushed her over the edge and into her oblivion. Even with plugged ears and a hood on, I could hear her gasping and crying out as she came.

She finally released my head and I was able to sit back on my heals, contemplating that the vibrations on my butt plug hadn't lessened and the semi erect state of my penis was indeed beginning to hurt.

As quick as the vibrator had been employed, it was now taken away and I felt like I had been left, kneeling in the room awaiting whatever the two ladies wanted to do with me.

After what seemed like hours, I felt two sets of hands again on my upper arms, lifting me up onto my feet. Again I was led through the house to yet a different room and was manoeuvred into a particular place within the room. I felt someone working on the locks of the handcuffs and realised that I was being released from them.

As they fell away, I felt hands then lifted the bottom of my T shirt up and raised my arms almost automatically to allow my shirt to be taken off me. I was now totally naked.

As my arms were brought down to my sides again, I heard Gail's voice in my ear telling me to put my hands behind my back, palm to palm and intertwined my fingers. I had no idea what was going on but happily complied.