3 comments/ 19947 views/ 10 favorites Caged for Freedom By: Spreadeagle56 I had a dilemma. You see I am a very kinky individual and my wife is not so kinky so, for a lot of my life, I am kinkily frustrated. Even more so because I know I can easily fix my frustration, simply by visiting a very good friend of mine. Gail has been in my life for longer than I care to remember. We were once lovers, very good lovers who went way beyond our "normal" selves to satisfy the other. Why didn't we stay together? Well that's complicated and would need way too much explanation for this story. Suffice to say, if we were still together, I would not be kinkily frustrated and that's the truth of it. Gail is in a very loving relationship that offers her freedoms to take other lovers as she chooses and is supported by her husband along this course. Every now and then, Gail and I bounce off each other, meeting for lunch or simply bumping into one another while shopping. Our friendship is easy. No matter how long it has been since we last chatted, it is as though it were yesterday and we just pick up from where we left off. Anyway, back to my dilemma. Part of my kink is a focus on anal play. Butt plugs, enemas, penetration of all sorts and a real like to be stretched. One thing I have always hankered for is a good fucking in the arse with a strap on. Having bought a strap on, I was hoping my wife would play along one day and bend me over and ram it in though alas, she doesn't seem to be inclined. Now, one sunny spring day, I was walking through town and low and behold, bumped into Gail. We hadn't seen each other for many months but as usual, made plans for a lunch date. Gail suggested the following Wednesday as she had that afternoon off and we could talk without being rushed. We met at a little Indian restaurant which we knew would be quiet and quickly ordered. Over our first glass of wine, we caught up on each other's lives and as is normal for us, went straight into discussing our sex lives. Gail always has wonderful, vibrant stories of her many escapades and the fun she has with her lovers as well as the odd threesome with her husband. When she asked about mine, I had to confess to some level of frustration in the kink department so as is normal for her, she offered to help in any way she could. Now that got my mind to turning over so I suggested I came up with a scenario and see where that could lead to. Over the next few weeks, I let my mind run rampant, dreaming up all sorts of kinky and sordid scenes that, if the opportunity presented itself, I'd like to try. As you can guess, I kept coming back time after time to the anal kink and wondered how far I'd be prepared to go. I am a straight male though, acknowledging I have a real want to get penetrated with a big solid strap on, I have had to face the fact that perhaps I do have a bi streak in me but would find it difficult to actively engage in a homosexual act unless I was made to. I am not suggesting I'd be happy to be raped, just that if I had no choice about being hammered in the arse by a real penis, I would more than likely enjoy it. The thing was, how could I safely arrange that to happen. This is what did! I emailed Gail and let her know what I was thinking about and we swapped ever increasingly kinky emails about what scenario would contain the elements I was wanting and she felt she could arrange. The trickiest things were getting a male who would be happy to fuck me in the arse and having me in a bound position that would present my arse for fucking and also prevent me from seeing who was doing the fucking. About three weeks into our email swapping, Gail dropped the bombshell that she had a guy willing to fuck a strangers arse, he would be happy to not know who I was and she knew he was safe. Now the pressure was on me. The thing is, I knew that at the last moment I would probably chicken out so had to dream up a plan to make sure I had no choice - and I did! You see I have a stainless steel chastity cage that once locked on, there is absolutely no way to get it off unless it is unlocked. So, I would give Gail $20 and asked her to buy a small padlock that would fit the cage and then give it to me. The kicker was, she would keep the keys! If I locked it on using that padlock, the only way she would give me the keys to unlock it would be if I submitted to being fucked. As with anything, it was fun discussing this scenario and we worked through how it would be best to tie me up so I couldn't move and still be available for being penetrated and all the lead up things that would need to be set in motion. The thing we avoided discussing was how this could ever happen as my wife rarely went away without me so there was never going to be an opportunity. The second bombshell landed when my wife told me she had to go away for a week long training course and it was in Australia. It was four weeks away and she had already paid for the course and booked the flights. My mind went into overdrive. The very next day I contacted Gail before I could chicken out telling her and suggested we meet for lunch again. Two days later, we met at the same Indian restaurant and plotted. My wife was leaving on the Sunday for a Monday start on the course and was returning on the following Sunday. We had a full week but had to decide which day we would set aside for the scenario. I had sweaty palms and was almost shaking with anticipation as we discussed what I knew was going to happen and I had put in place a scheme to make sure I couldn't back out. After much deliberation, we decided that the Thursday evening was the fateful time. This meant that I had a few days to get over the evening before my wife got home but I also had a few days before hand to enjoy the anticipation of what was going to happen. We also had to decide when I was going to lock the cage on. It had to be a reasonable time frame, not too far out in case it got uncomfortable but long enough so I had to suffer a little. We decided the Tuesday evening would be the time. We also decided that that evening I would take the necessary bondage equipment round to Gail so it was all in place and she could actually do the locking of the cage on. The next few weeks were sheer hell for me. Gail kept in touch by email and text telling me all about the preparations she was making. She had contacted the guy who was going to do the fucking and he was still keen and was available on the night we wanted him. We had decided the best place for me to be bound was over the bench that separated the kitchen from the living room. It was a perfect height so when I was bound bent over it, my arse was at the correct height for the guy to simply walk straight into me. Also, with him standing, he would have better control and leverage to pound as he saw fit. Finally Sunday arrived and I took my wife to the airport and saw her off. On the way home, I called Gail and told her that everything was go. She laughed and told me I sounded scared - I was! As Tuesday crept closer and my date with the chastity cage loomed, I have to say I was beginning to think that things had got out of hand and was questioning my own sanity. I countered that by the thought that if I didn't go through with it, I would forever wonder what it felt like and I didn't want to have to think about that on my death bed. Gail had bought the padlock and was looking forward to securing the cage onto my cock and balls. Tuesday work dragged by then all of a sudden, it was 5pm and I had arranged to be at Gail's at 7pm. I couldn't face dinner so instead got the bondage items together. Pillory for the neck and wrists, spreader bar for the ankles, leather hood, gag, blindfold, ear plugs, nipple clamps, a good length of chain and of course, the chastity cage. At 6:45pm I left home and drove to Gail's. Her husband was out visiting one of his other lovers so I knew we would have the evening alone with no hindrances. I pulled to a stop up Gail's driveway right on the dot of 7pm and hearing me pull up, she came out to greet me and help me with the gear. Gail has always been one for putting me at ease and as per normal, she did just that. We went inside and Gail poured a generous glass of wine each and we sat and chatted for a few minutes. The bondage gear was lying on the floor where we had left it and Gail suggested we practice setting it up where it was to go and making sure it would all fit and work properly. What could I say but OK, lets. Gail's husband had already been busy, putting in an eyebolt in an appropriate but not visible place to attach the spreader bar to. The pillory I had removed from its post and attached a board to the bottom of it so it could be clamped to the bench top. Going to the kitchen, I mounted it on the bench, checking I had it in the right place. To make things authentic, Gail suggested I strip off and we literally immobilise me how I was going to be on Thursday so we could ensure it would all work properly and be comfortable, so strip off I did. We started by getting the earplugs in and the hood on. Gail laced it on really tightly, way tighter than I could by myself and it felt wonderful. Next on was the gag. This is a serious harness gag with a breathe through plug which silences me entirely. Again, Gail buckled this on really tight but it felt oh so good, there was no way I was going to complain. Last thing on my head was the blindfold. I had splashed out recently and purchased a really top, buckle on leather one which let not a chink of light in so once Gail had buckled that on, I could no longer see, hear or speak! I had been standing on the kitchen side of the bench roughly a meter away from it so once Gail had me ready, I could simply walk to the bench and bend over it. I expected her to push me forward but she didn't so I was wondering what was happening. I found out very quickly when Gail placed the first nipple clamp on my left nipple. I had forgotten those and seriously wondered what it was going to feel like once I was leaning on them on the bench! Once she had put the second clip on my right nipple, Gail gently pushed me toward the bench until I was in contact with the edge. I knew what I had to do now so leaned forward until I was effectively lying on the bench top. To say the nipple clips bit would have been an understatement and the thought rapidly went through my mind that perhaps this might be a bit far. As agreed, Gail took my hands and guided my wrists into the cut outs of the pillory which gave me more of a lead to where my neck had to be. Reaching forward with my neck and completely blind, was an interesting experience but again Gail guided me in the right direction and, lifting my chin a little higher, my neck slipped easily into the cut out. Carefully so as not to pinch my skin, Gail then closed the top half of the pillory into place and secured it closed with a padlock. I guess you could say now that I wasn't going anywhere however, Gail now started buckling the ankle spreader in place. To do so, I had to spread my legs wider which, in this position made me all the more certain of what an easy target I presented bent double and with my legs spread wide. With an almost silent click, the last padlock secured the chain from the spreader to the hidden eyebolt and there I was, ready, or at least practicing to be ready. Gail gently stroked my back and brought her mouth very close to the side of the hood so I could hear her. "Comfortable?" I could only "ahem" through my gag but she got the message. "I'm going to leave you like that for a few minutes so you can then decide what is and what isn't comfortable. Back soon." Then she left me. I tried to relax but those damned nipple clips just simply didn't allow that. I was trying to lift up a little to take the pressure off them but that was virtually impossible with the way I was secured. Apart from that though, I felt really quite comfortable and decided this was a really good bondage position. I have no idea how long Gail left me like that. Time always plays tricks when bound and sense deprived so I reckoned it felt like an hour but was probably like ten minutes. When Gail came back though, it wasn't to release me. "I haven't whipped you for years, have I David?" she asked knowing full well I couldn't respond. "I have decided that seeing as there is plenty of time between now and when your wife gets home for any marks to fade, you really should have your arse warmed", she said. She was right, I actually couldn't remember the last time she had whipped or caned me and in fact, I wasn't sure she ever had. Right now though, I had little choice but to put up with whatever she wanted. I didn't have long to contemplate that thought when the first stroke of the whip hit my left buttock. It wasn't so much the pain of the stroke but rather the shock of the impact that made me jump. My cheek felt immediately warm and the warmth seemed to spread outwards from the site of impact. She hit me again, this time on my right buttock. This time I was ready for the blow and could instantly feel a soft pain radiating from where it fell. Gail paused for a moment or two them started a rhythmic whipping of my entire arse, slowly building the tempo and the weight of the blows until it felt like a constant crashing of whip against my flesh. All the while, the pain built and built, pushing inexorably toward the pleasure threshold when suddenly she stopped! I suddenly realised that I had been holding my breath and took a ragged intake through the hole in the gag. Gail caressed my buttocks with her soft hand which felt wonderful on the hot, sensitive skin. I heard her voice at my ear - "Enough?" I was in a quandary. Part of me wanted her to carry on whereas another part of me cried out for her to stop. I hesitated... "Alright then - some more!" she said. I had hesitated too long so the decision was taken away from me. What followed made me wish I hadn't said enough. Unknown to me, Gail had swapped the whip for a cane. The first flicking blow crashed right across both cheeks. As they were already inflamed, the sharp, stinging impact made me cry out, though as gagged as I was, the noise was barely audible. If Gail had heard it at all, she ignored it and continued a measured caning, turning my mildly warm buttocks into a raging inferno of heat. Had I not been well immobilised, I would certainly not have been able to lie there and take it but Gail had the upper hand and knew it. She was loving it! Then it stopped. I was breathing heavily through my gag and could feel some tears of pain inside the blindfold. I thought I could hear Gail breathing heavily as well but with the ear plugs in, I couldn't be sure. I did feel her working at the buckles of the ankle cuffs and eventually heard her unlock the pillory and felt the top being lifted off me. Standing carefully, I was suddenly aware of the pain in my nipples, something that had faded to nothing as I was being whipped and caned. Deft fingers now roamed over the buckles and laces to release the blindfold, gag and hood until suddenly the light and air of the kitchen invaded my private prison. I took the ear plugs out and gasped a little as Gail unclipped the nipple clips. Gail stood back and with an almost fearful face asked me if that was alright. "That was amazing!" I told her. "I might not be able to sit properly for a day or two, but the feeling of being worked over was worth every bit of it." Gail smiled and gave me a huge hug then picked up the chastity cage and handed it to me to put on. This particular cage is really easy to put on. I put the hinged cuff round the base of my balls and penis, hinging it closed and putting the locking pin through the top to keep it closed. The cage I slid over my penis, slotting it over the pin holding the cuff together and seating two smaller pins on the cage into the cuff. All it needed now was the small padlock through the hole at the end of the pin and I was locked. Gail held the small padlock in her hand and told me that this was decision time. Once she had locked the cage on, the only way it was coming off was for me to receive another man's erect penis in my butt. I could feel myself shaking with anticipation and a little fear then looking Gail in the eye, I gently nodded. I watched as Gail slipped the little padlock through the hole and with a small but definite "snick", she locked it closed. My fate was sealed. Little more was said as I slowly got dressed again. Gail sat and watched me then when completed, took me by the hand and lead me to the lounge. We sat and discussed the timing of Thursday as though it would be happening to someone else. I had decided that I would eat little that day and administer a number of enemas to make sure I was really clean inside. Gail told me that the guy who was going to fuck me would be there at 8:30pm so she wanted me there by 7:30pm so we could get me well ready. She told me that I was to be immobilised well in advance and that when the other guy arrived, she would have him undress in another room and that he would be blindfolded too when she brought him into the room. With that, she told me to go home and enjoy the cage. The next 48 hours seemed to drag. I honestly tried to work but with the enormity of what was about to happen constantly being reinforced by the presence of the chastity cage, I found it virtually impossible to keep my mind on my job. Finally Thursday arrived. I ate a small breakfast of fruit and had organised a number of drinks for the day to sustain me. I wanted to be able to completely clean my system out so there would be no chance of a mess during the events of the evening. By mid-afternoon, I was seriously wondering if this was all a bad mistake. The problem with that thought though was the unforgiving cage that was locked onto me. I knew Gail would not allow me to back out now!! I had been wearing a mid-sized butt plug most of the day and at about 4:30pm, loaded the first enema into my arse to start the cleansing process. I have always enjoyed the feeling of being filled with an enema so took my time and luxuriated in the process. Surprisingly, I was clean in no time, thanks perhaps to the fact that I had eaten so little during the day. By 5:30pm, I had showered, shaved and was now being stretched by the largest butt plug I had which I hoped was at least as large as the guy's penis I was going to have up there later. With the anticipation eating away at me, I left for Gail's place at 7pm. Arriving about 15 minutes later, I noticed that the garage door was up and the garage empty. Gail came out to greet me and told me to put my car in the garage. She told me that she didn't want the guy to see my car so that there was no way he could figure out who I was. She is so thoughtful!! Once inside, I noted that the house was nice and warm and that the bondage gear was all set up on the kitchen bench. "Are you plugged?" she asked. "Yes, with the largest plug I have", I informed her. "That's good because, shall we call him Bob, is quite large. His penis is about 7½ inches long but he's quite thick. I love feeling him inside me as he stretches me beautifully. Knowing you, I don't think you will have any trouble accommodating him but I do think it will be a stretch for you to start with. That's what you want though isn't it?" Gail said matter of factly. I hesitated a little, that finger of fear poking into me inside. "I guess we will find out soon enough won't we", I said meekly. Gail then told me to go into the downstairs bedroom and take my clothes off. The moment had arrived. I found my way into the room and slowly stripped out of my clothes, returning to the kitchen wearing nothing but the chastity cage and the butt plug. "Let's do it", she said as she held out the ear plugs to me. Caged for Freedom Ch. 02 I awoke from a deep sleep. One that could only come from a very relaxed and satisfied place. Lying in bed, I reflected on what had happened to me over the last 24 hours and thought about the dull ache that still emanated from my arse. But more importantly, I wondered about what was to come! Less than 12 hours ago, I had been an anal virgin and had been scared and trembling at the thought of having my butt plundered by a hard penis yet now, I was looking forward to it happening all over again. What was going on in my head? It was all Gail's fault, she had made it possible for me to finally cross a line that I had secretly wanted to cross for a very long time. The circumstances had been of my choosing but the reality of the journey was not lost on me. I had been butt fucked. Nothing else but taken and used and drilled and I had loved it. The way I was held in bondage was just how I had wanted it. Immobile, available, out of control and ready for whatever was to happen. And now I was looking forward to it happening all over again. I had driven home from Gail's place last night in a daze. My arse had been still plugged with an over large butt plug that had kept the cum I had received inside. That and a large amount of lube that Gail had squirted inside of me had dribbled out of me as soon as the plug was removed but I felt empty without it so had replugged myself with a slightly smaller one before falling exhausted into bed. Gail and I had agreed to talk this morning and discuss last night and the night to come so I rolled over to check the clock. 9am, I had slept in!! Not surprising I mused as I lay there and thought about all that had happened. As I did my hands explored my body, feeling the effects of the experiences of the last few day. My fingers found and wandered over the hard steel of the cock cage and revelled in the solid and absolute security it afforded. I had to smirk to myself how I had always prided myself in being able to circumvent the other plastic cages I had tried. As good as they looked and as solid as they felt, there was always a weakness that would allow me to escape. This one though was quite different. I had experimented with the various rings it had come with and found a combination that, try as I might, there was absolutely no way I could get my penis out of the cage or the ring off my balls and cock. As far as the way it fitted me, it was full proof. My hands continued their exploration and eventually found the small, soft welts that adorned my butt from the whipping and caning Gail had given me on Tuesday night. I worried that they may still show when I picked up my wife on Sunday so thought it best I check them out. I got out of bed and padded into the ensuite and stood with my back against the mirror. I could certainly still see the reddish lines across my cheeks and could definitely feel them but I knew well that I did heal quickly and with a bit of healing cream, I was sure they would fade enough not to be seen. After all, Gail hadn't hit me that hard for a first time experience. My mind drifted back to the whipping I had received and I thought to myself that I would so love to experience that again and with that the phone rang. It was Gail and she wanted to know how I was. "Well I'm aching a little inside and my butt feels like it has been well stretched and well used but apart from that I feel fabulous!" I told her. "I'm glad to hear it," she said, "I have heard from Bob this morning already and he wanted to know if you were up to having another fucking so I told him you were and it was tonight and to be here at the same time. He's definitely up for it and has confirmed he'll be here at 8:30pm." "Alright!" was my enthusiastic reply, "do you want me there at 7:30 again or earlier?" "Gosh you are a bondage slut aren't you," Gail said laughingly, "you just want me to get you all immobilised so you can revel in being bound. All right then, I'll be home from about 3pm so you can come round any time after say 3:30." "Done," I replied, "I'll be with you about 4pm. Any requests?" Gail immediately knew what I meant. We had played these games in the past with her dictating how I was to arrive at her home. Sometimes she had me cross dress with skirt, stockings and heels though one time she dictated that I arrive completely naked. That was a challenge as I was not sure what her neighbours would have thought or said if they had seen me. Anyway, it was too late now, I had put it out for her so just had to wait for her decision. "Mmmmm, now that might be interesting," she said, "I'll think about that and text you. See you at 4 then." And with that Gail rang off. I couldn't believe how hungry I was but then realised that I had hardly eaten at all the day before, then realised that to be all clean inside again, I'd have to eat little again today. I headed back to the bathroom and got the shower cranked up good and strong then got in. The hot water on my skin felt great and when I took the removable shower head and started to run it round my arse and balls, felt only too well that I was still locked into my chastity cage. Damn I thought, it would have been nice to have had the chance to masturbate but that wasn't to be. I was locked until tonight was over and that was that. I did have the presence of mind to remove the plug in the shower and even though the water was running, could feel things oozing down my legs which brought a wicked smile to my face. My shower finished, I thought I'd delay my shave until later this afternoon and after dressing casually, headed for the kitchen for a little breakfast of fruit. Just as I was finishing, my phone buzzed and I had a text from Gail. Once I had read it through, I realised that Gail was at her most adventurous and inventive self. "I want your arse packed with bananas, held in place with the large butt plug. Wear the locking crotch strap to hold it in and a diaper just in case. Skirt, stay ups and heels too." I knew straight off where this was headed. I had shared with her years ago how I had discovered on line, a page that mentioned stuffing bananas up your arse that had been well lubed with glycerine. The glycerine was like a suppository and it made keeping the bananas inside an impossibility. The neat trick though was to use a rolled up sanitary pad or multiple tampons to keep the bananas inside so the pressure could build up - and it did! What I had further discovered was a device that was sold as an incontinence aid that really effectively blocked the anal passage and was far better at letting the pressure build but this time, Gail wanted an even more solid plug in me that simply couldn't get out! The thing was, I had only filled my arse like this in the safety of my own home and now Gail was wanting me to load up then drive to her place and face a very uncertain outcome once there. I couldn't wait!! I tried to keep myself busy during the day, thanking goodness and anything else around that I had taken the Friday off work as well. Not having anything set to do, I invented things that needed work just to stay busy and have the time go quicker. I had reckoned I'd need another clean out with an enema anyway and if I was to be at Gail's at 4pm, I'd have to start getting myself ready at about 2:30pm. By 2:30pm I had assembled all the bits and pieces I needed and had also got out my clothes Gail wanted me in. It was still a little cool outside but regardless, I had elected to wear very sheer stay up stockings with a stretch velvet skirt even though the skirt was pretty short. The heels were a difficult decision. I had two pairs, one stiletto and the other more sensible that I could walk in better. I reckoned I'd leave that decision until the last moment so had both pairs out just in case. Filling the enema bag in the kitchen is always a really great feeling because I know that in a very short time, that nozzle I am preparing will be going up inside of me and the water I am filling the bag with is going to flow into my arse, stretching my insides as it gurgles and glugs it's way to cleaning me out. As always, I added a generous dose of salt to the water so it wouldn't be so harsh on my system then once ready, I walked up the hallway to the ensuite off the bedroom. I had already prepared the ensuite and had a series of towels I kept just for this purpose, arranged on the floor. Hanging the bag from the shower door, I made sure that there was a minimum of air in the enema line then, getting down on my knees on the floor, slid the well lubed nozzle inside me. As always, the first little burst of water took a bit of getting used to but once I was relaxed and bent over onto my elbows, the water flowed freely and in no time I was feeling very full and the bag was starting to gurgle indicating it was getting very empty. I always have difficulty with that next movement when I have to raise myself and remove the nozzle without spilling the contents of my butt all over the floor. I have to clench down really hard as the nozzle comes free then very carefully stand to move toward the toilet. The relief when I let go is always worth the effort in getting a good fill inside. One day I'll get a proper enema nozzle though that I can blow up and seal inside then I can really get a good load on board but for now, this will do and as I sat expelling the water, I reflected on exactly why I am doing this!! I deliberated next on my timing of things and thought about what order I should do what was needed before leaving for Gail's. I figured that it would take me about 15 minutes to get the bananas inside and the plug and crotch strap locked on then another 15 minutes to drive to Gail's so knowing that the glycerine sets things off fairly quickly, I reckoned I should get as dressed as I could and do the banana thing as quickly as I could, last. By 3:30pm I was shaved and all dressed except for the shoes and had prepared the bananas and equipment ready for the final dash for Gail's. The bananas were short at about 15 - 20cm long but were quite thick so I knew they would be fun to get inside. I also reckoned that as they were so short, I would try to get four in and if possible, keep them whole. The webpage I had read had recommended breaking them in half but I wanted to push the boundaries a bit and anyway, I had had a much bigger thing than this banana up my arse last night and was going to have it in again tonight!! I had had my medium plug in for most of the day so my anus was well stretched and I knew that getting the first banana in was going to be relatively easy. I peeled the first one and doused it well with glycerine then bending over, pushed the tip of the banana against my loose butt hole. It slid easily in for the first few centimetres then stopped. I had to take a breath and ease it out while baring down as I put more pressure onto the banana. Slowly it eased into me until almost with a pop, it disappeared inside my very empty rectum. I knew I couldn't delay now that I had one in so I grabbed for the second banana, lubed it up and pressed it to my butt hole. It has always amused me that the first is always the most difficult to get in and the following ones just seem to flow in afterwards which is just what this one did. Reaching for a third banana, I wondered whether four was too many but was willing to try. The third banana slid in really easily and even the fourth one was not too much of a struggle but when I stood to find my butt plug, I knew very quickly that I was VERY full and that the glycerine was working already! The large plug slid in as easily as the last banana but in doing so, pressed the four bananas I had inside, further up into me, making the pressure almost uncomfortable but I could not delay. Taking the crotch strap, I buckled the waist belt on securely then took the strap that was riveted to the back, up between my legs, seating it firmly on top of the plug. The strap between my legs split just rear of my ball sack and was pulled tight into place then buckled to the waist belt. Even though I had the keys myself, I then used small padlocks to lock the buckles closed, ensuring that Gail would have the power over when it came off. The only thing left was to pull on a diaper, slip on my shoes and drive to Gail's. Getting the diaper on was easy. I had bought some adult ones that fit just like the babies ones so all that involved in getting it in place was basically pulling on a pair of shorts. I headed to the garage to my car and lastly had to make my mind up about the heels. They were both roughly the same height but the sensible ones sported a solid heel that was easy to walk and stand in but didn't have the "look" that the stilettos had. I hesitated, not knowing what Gail had in store then, knowing I was choosing the wrong ones, slipped the stilettos on, got in my car and drove to Gail's. The drive was horrendous. Not only was the glycerine working on my bowels but the plug in my butt was hurting me, the crotch strap was too tight once I was sitting on it and the chastity cage was squeezing everything a little to tightly. I tried to wriggle around to find a comfortable position but in the end gave up and just drove wondering all the while what a traffic policeman would have said if he had stopped me! Arriving at Gail's eventually, I drove straight into her garage, closed the door and got gingerly out of the car. I still had to cross a small open area to get to her front door but hoped that all her neighbours were either at work or wouldn't be watching. Fortunately Gail had heard me arrive so had the front door open and welcomed me inside without making me stand in the entrance way. As I entered the house, Gail stood back and looked me up and down. "Nice legs," she said, "when did you last shave?" "I didn't shave but used depilatory cream and waxed the tender bits," I answered. "Nice job!" Gail led me inside and into the kitchen area. I noted that the pillory was already set up though perhaps it was still there from the night before. On the bench top though were other bits of bondage gear that had definitely not been there the night before. "How is the pressure building inside?" Gail asked. "Certainly building," I answered hesitatingly, "though not too bad for the moment," I added. "That's good because I think you need to be tortured a little before you can release the pressure," Gail said menacingly. "Turn round and put your hands behind your back," she ordered. I did as I was told and felt Gail putting some handcuffs on me. I had noticed them on the bench top and realised they were hinged cuffs that were very heavy and solid looking. Hearing the ratchet click as they were closed about my wrists made me tremble and my well caged penis did it's best to rise as the sensation of being taken-over, washed over me. Gail walked round me so she was now standing before me then with absolute determination, reached under the hem of the skirt I was wearing, pulled the diaper down and grasped my balls in her small hand. The cage had now been locked on me for three days and the ball sack was stretched tight over my balls. As she took them in her hand and squeezed gently, I could only wonder what was coming next. "Where are the keys to the crotch strap?" she asked. "They are on a chain hanging round my neck," I volunteered. Gail released my balls and reached up to the neck of my shirt and retrieved the chain holding the keys. Carefully she undid the locks holding the buckles closed, then slowly undid the buckles of the strap and the waist belt. Pulling the diaper further aside, she now slid the straps out from under me, leaving the plug still well seated but now not having anything other than my quivering sphincter to hold the pressure back. "I am going to leave you locked, diapered and cuffed like this until you can't hold out any longer. The only way I will uncuff you is when you have filled that diaper with bananas," Gail said. At this I broke out in a sweat. Now the security of the crotch strap had been released, I felt as though I couldn't hold the mounting pressure much longer. My bowel was gurgling and cramping and I knew that there wasn't much time before I was not going to be able to hold it any longer. "Come and sit here," Gail said as she directed me to a plastic camp chair that she had obviously got inside especially for this purpose. I lifted my hands up behind me and slid them over the back of the chair as I carefully sat down. Once seated, I suddenly realised that there was no way I could stand again with my arms where they were and that like it or not, I was doomed to fill my diaper as I sat in Gail's kitchen. "Enjoy," Gail said, then turned and left the kitchen. I sat there on the chair and really did break out in a cold sweat. The pressure now was becoming unbearable and my bowels were cramping in a rhythm that was getting faster and faster. I could feel the plug starting to be pushed out but of course, it met the hardness of the chair under the diaper and with nowhere to go, sat firmly inside me, preventing the release I knew had to come. Eventually the cramps got to a point where I simply couldn't think at all, let alone straight. My shirt was damp with sweat and I was almost gasping for air seeking relief. I figured I had to just take a little pressure off the plug and it would explode out so grasping the back of the chair I managed to lift myself a few inches. Nothing happened to start with as the action made my sphincter hold the plug that much harder then I felt a movement and froze. The plug started coming out slowly then with a rush accompanied by gooey squirting sounds, the plug and the bananas shot out of my arse and filled the diaper to the brim. I almost passed out from the relief of the expulsion and sat down on top of all the bananas, feeling the long, thick plug rest between my buttocks as I did so. Within seconds my bladder decided to empty too and I remembered past experiences when this had happened and I had had absolutely no control over that either. All together I knew I had a real mess inside my diaper. The feeling was not only of relief to get the pressure out but also a warm, gooey sensation that coated my arse and balls. There was no smell save for the sweet aroma of mashed bananas as I had been so clean inside to start with so I simply sat there and allowed the sensations to flow over me. I had been sitting for some time when I heard Gail's foot falls on the carpet as she walked down the hallway and into the kitchen. "I can smell banana," she quipped with a huge smile on her face. "How does that feel?" "Well it is a unique feeling," I admitted, "I had never been able to bring myself to do this to myself so having to endure it like this is a great feeling. I can feel the mushed bananas coating everything inside the diaper and can also feel that it is a VERY full diaper at that so I hope you have somewhere to dispose of it." "That won't be a problem," Gail said off handedly, "the main thing now is to get you cleaned up and cleaned out again and prepared for the fun I have planned for you." With that, Gail walked round behind me and carefully undid the handcuffs holding me to the chair. I stood with great care as the diaper was sodden and very full and I was worried that it might leak. Gail directed me down the hall way to a bathroom that not only had a toilet in it but hanging from the shower stall was yet another enema bag that looked filled to almost busting. "I think you'd best peel the diaper off and drop it in that bucket over there then get undressed and into the shower," Gail suggested. I did as I was told and in no time was luxuriating in the hot water pounding against my skin. The residue mush of the bananas sluiced away down the drain, leaving me clean and refreshed again. Caged for Freedom Ch. 02 As I turned the water off and started drying myself, Gail stopped me. "OK, I guess we had better sluice you out inside as well to make sure we have all that banana out. We don't want Bob to have to contend with that now do we?" she added then directed me to kneel in the shower and present my butt for the nozzle. Now what I hadn't noticed was that Gail did have an inflatable enema nozzle. It was of the double Bardex type and had balloons that would be both inside and outside me to make a very secure seal at the anus. I heard Gail put on some latex glove then felt her first dry round my butt then start applying a good deal of lubricant. As she started to insert the enema nozzle inside me, I eventually realised that this was a much bigger nozzle than I was used to at home. "That certainly feels like a big nozzle you're using back there," I commented. "Well," said Gail, "it's actually a double Bardex so there is plenty to get inside then we blow the balloons up, start the water flowing and see just how much of that bag you can take," she added menacingly. It felt strange having the nozzle pushed inside but when Gail started to blow the internal balloon up, the sensation went from strange to interesting to an unusual full feeling as the balloon filled the lower part of my rectum. When Gail felt it had been pumped up enough, she now started on the external balloon. Now that felt really strange as it forced it's way between my buttock cheeks and pulled the internal balloon tight against my sphincter. "Alright now, that should do it," Gail said matter of factly, then she stood, reached up and released the clamp holding the water back. The enema bag had been hung quite high and I noted quickly that the rush of water into me was forceful and built pressure very quickly. I was just about to mention that to Gail when she unhooked the bag from the shower rail and placed it lower on the vanity beside me. "We don't want to blow you up now do we," Gail empathised with me. I could feel the flow of water slow and the pressure gradually ease as I knew the water was now creeping its way through my lower bowel. Time seemed to stand still for a while as we were both quiet and the only sound was the occasional gurgle coming from my distending abdomen. "Wow, I think we will call that empty," Gail said, startling me out of my reverie. I glanced up to the vanity and saw the enema bag lying limply on the counter. What had been a very full and tight bag had emptied itself into my now straining bowel. Gail shut off the clamp and asked me to stand. She said there was no way she was going to deflate the internal balloon until I was sitting on the toilet because I would probably explode as soon as the pressure was released. Walking the short distance across the bathroom was an interesting experience. I manoeuvred carefully to the toilet and gingerly sat down, making sure the enema tubing was out of the way of everything. "Ready?" Gail asked. I simply nodded and waited for the release. I heard the air hiss out of the release valve and felt the internal balloon start to diminish in size when suddenly, with no sense of it happening, the flood of the enema came rushing out of me. It ran on and on seemingly with no end in sight. The expression on my face must have been amusing because Gail stood back and laughed and laughed as she watched and heard me evacuate the enema. "I think you'd best just sit there for a while and get it all out. I'll go clean and put this away and make sure everything is ready for me to get you bound. I'll be back soon," and with that Gail was gone. I sat on the toilet for what must have been 15 - 20 minutes until I knew for certain that there was no more water to come out. It had taken quite a bit of effort and massaging to get the last bits out but at least I knew that I was squeaky clean inside for Bob. Eventually Gail came back and asked me if everything was all good. With my affirmation, she told me to get dressed again as I was earlier and come into the kitchen. I thought that was a little strange as she had had me naked the previous night. Oh, and don't forget to put the plug back in, she added. I got my shirt back on then carefully rolled the stay ups back on, followed by my very short skirt and eventually the heels. I was pleased that I was dealing with the heels well even though they were really quite high for me and demanded a good deal of my concentration to walk in them. I found some lube and gently reinserted the butt plug then finally redressed, I walked down the hallway and into the kitchen. Gail had been busy and had laid out all the bondage gear she had used the previous evening ready to put it on me. "I know it is only 6pm and Bob is not due here until 8:30pm but I know you like being bound and from what you said yesterday, the position you are bound in is really quite comfortable so I reckon we should get you locked up then you can enjoy the experience of a decent time in the stocks," Gail said. Who was I to argue! She knew me sometimes better than I knew myself and I really did love to be bound tightly and unforgivingly and the pillory was certainly unforgiving. As the previous evening, Gail started by handing me the ear plugs. It was much easier for me to put these in myself and I managed to get them in really deep which almost made me totally deaf. Before she did anything else though, Gail took the hinged cuffs from the bench and applied them tightly to my wrists behind me. She said she didn't want any interference from me as she completed the bondage. Then again, as before, Gail now went about rendering me deaf, blind and silent as she laced, buckled and locked the hood, blindfold and gag onto me. Finally I felt her unbutton the front of my shirt and I knew that she had not forgotten the nipple clips. She reached inside my shirt and teased my nipples, pulling and twisting them to make them stand up. For a guy I have very sensitive nipples so what she was doing to them connected directly with my penis which was now straining to stand up inside the unrelenting steel cage. Suddenly the pleasure of the tease was replaced with the pain of the clip as she fastened first one then the other onto my erect and sensitive nipples. Not leaving it at that, she now took the small strings attached to the clips and pulled the clips up and outward, twisting my nipples painfully. I gasped in pain and my penis made an even bigger effort to burst out of the restraining cage. She knew I was loving what she was doing and I reckoned I could hear her breathing heavily as she tortured me - she was getting off on it too! Letting go the clips, she moved behind me and I could feel her unlocking the hand cuffs. Once she had those removed, she gently pushed me forward toward the bench where I would be bent over, locked into the pillory for the next few hours. I reached out blindly and Gail took my hands and guided my wrists into the wooden cut outs of the pillory. Reaching forward now, I stretched my neck and lifted my chin as I knew I had to and felt my way into the neck cut out. Gently, so as not to pinch any skin, Gail now lowered the top of the pillory into place and secured it closed with a padlock and there I was, going nowhere and awaiting another arse pounding by a hard cock. I felt Gail buckle a cuff of the spreader bar round my left ankle and at her urging, spread my legs so she could get the second cuff fastened. It was at this point that I realised I was still in my heels and that my calf muscles were being stretched taught by the position I was in. I was not sure how I was going to endure hours of this but had little choice now. I rather felt than heard Gail leave the kitchen and I was alone, vulnerable and immobile. I was loving it!! Time seemed to slow to a crawl as I enjoyed investigating my current state and the feelings I was experiencing. As yesterday, the nipple clips bit into me as I rested my chest on the bench top. Again, as my calf muscles were telling me, there was nothing I could do about it and would just have to endure. The pillory held me very tightly. The cut outs on the solid wood I had made myself to the exact measurements of my wrists and neck and had then lined with thick felt to make them softer. With the way I was stretched across the bench, the pillory was even more immobilising than it may normally have been but I wasn't complaining. What I was doing was dribbling through my gag which I knew was bound to happen but thoughtful Gail had placed a small towel beneath the gag to catch the drips. Though I found it quite embarrassing to think that I was soaking a towel with my spittle in the position I was in, I had no choice in the matter. I suppose, that's what being bound was all about. The fact that I had given the power over me to someone else and whatever they wanted to do with me, I had no choice in. Just as on Tuesday when Gail had whipped and caned me when we were trying the pillory for fit, right now, if she had wanted to do it again, I would have just had to endure her whim. It felt totally delicious!! I don't know how long I had been locked up and for that matter it didn't matter but I suddenly started as I felt an extremely light touch on my sheer stockinged leg. I thought it may have been a cat's tail to start with but the light tingly sensation travelled slowly up my leg until it reached the hem of my skirt then swapped legs and travelled slowly down again. This happened a number of time which I found to be such a sensory overload, it was driving me crazy. Just when I couldn't take any more, whatever it was stopped. I waited and listened and could not hear a thing nor feel anything more. Just when I let my guard down and was relaxing again, I felt someone move the hem of my skirt up, exposing my butt and the plug that sat firmly inside of me. The light caressing I had been feeling on my legs now started fluttering over my naked buttocks raising goose bumps as they went. I finally realised that I was feeling a feather being played over my skin and it had to be Gail teasing me mercilessly. The feather continued stroking the tight skin of my butt, every now and then though delving down between my legs and tickling my balls which were being held firmly by the chastity cage which stretched the skin taught round them. The teasing was exquisite!! When Gail stopped, I thought she would simply slink away but then a shock. I felt her working at the butt plug I had in and it felt very much like she was taking a good grip of it to pull it out. She started wiggling it a bit which had a delicious effect on my prostate but then she definitely started pulling it out and in no time had my butt open and waiting. I reckoned it couldn't have been 8:30pm yet so was not sure why she was preparing me for a fucking so soon. Just as the previous night, Gail inserted the nozzle of a squeeze bottle and squirted an over generous amount of lube into my butt but once it was withdrawn, I felt nothing. I waited and waited and figured she had set me up to think that it was time for Bob to fuck me and was fucking with my mind. I liked having my mind fucked with and Gail knew this big time. What I didn't expect was what happened next. I thought I'd heard movement but wasn't sure. What I was sure about though was the sound of high heels walking on the kitchen tiles. The foot falls were soft to my ears but were measured and determined and were definitely getting closer. I heard them stop behind me then felt Gail's soft, small hands alight gently on my buttocks. I reckoned by what I could feel that she was standing directly behind me in the same position as Bob had stood last night and was going to stand again tonight. She lifted her right hand off my butt cheek then I got a surprise. I felt something brush against my butt hole. A butt hole that was stretched and open and had been recently well lubed. A butt hole that now felt something prodding gently at it. The prodding went on, gently pushing against me and very slowly, determinedly entering me further and further. The small in out movement felt very much like a rigid penis but I knew that was wrong so it must be a dildo of some sort. It certainly felt big, though the way Gail was easing it into me, my butt was opening and welcoming it with virtual ease. Gail continued to push the dildo ever deeper within me and I reckoned I could feel ridges and nubs along the shaft that played wickedly with my sphincter and I could feel the girth and length of it deliciously probing at my prostate. I had no idea how long the dildo was but Gail seemed to feed more and more into me until I thought I could feel it bottoming out inside me. It was at that point that I felt Gail's thighs against my buttocks and realised that I was being impaled on a long, thick strap on that Gail was wearing. All the bits of the puzzle came together then. I had been wondering about hearing the high heels on the kitchen tiles but that now made sense. Gail was certainly not too tall and the only way she could be tall enough to get a strap on into me was to wear sky high heels, especially as I was also wearing heels. I could only assume she was wearing impossibly high platform shoes which, since I had a shoe fetish, would have to get to see later!! Just as Gail had bottomed out within me, she started a slow, rhythmical in out motion, just like a man would do when fucking someone. There was no hurry with what she was doing, just a slow measured pace. Sometimes she would pull almost all the way out before sliding fully back inside while other times she would withdraw only an inch or two before pushing all the way back again. Gail kept the rhythm going for many minutes, all the while holding my hips with her small hands. I was finding it mesmerising being pushed against the bench and then pulled back again, feeling the pillory hold me tight as Gail put pressure on my wrists and neck. On the in stroke, my caged cock was being pushed hard against the cupboard doors and reminded me that I was still well caged and would stay so until Gail decided otherwise. After some time that I could only guess at, Gail slowly picked up the pace. Her in out pumping got faster and faster and the pressure she was putting into each stroke got harder and harder until she was pounding my arse like the best of them. Even with the ear plugs and hood, I could hear Gail's breathing getting laboured and I knew that she was getting very turned on by what she was doing. I was definitely getting turned on too and had a most painful semi erection inside my chastity cage and I knew my penis would be leaking precum profusely. I was loving it!! With almost an animal like grunt, Gail suddenly thrust particularly hard against me and started shaking and moaning and I knew she had cum herself. Staying still well and truly buried within me, Gail collapsed over my back and I felt her hands drag down over my shoulders as she slowly returned to earth from her orgasm. All I was able to do was lie there and wait as the extra weight she provided onto my back, ground the nipple clips even harder into my nipples providing even more exquisite pain to my ordeal. Reluctantly, I felt Gail stand and slowly withdraw the huge phallus from my aching arse then with almost sadness, I heard her walk away across the kitchen tiles in those heels I was longing to see. I waited for some time before I felt and heard Gail return. She brought her mouth close to my ears so she was sure I could hear her. "I hope that was as much fun for you as it was for me. Seeing Bob fuck your beautiful arse yesterday was just too much for me and I knew I needed a piece of it too. Knowing that you wanted more pounding, I thought a relim would set you up for later. By the way Bob is almost here, I got a text from him a few moments ago and he'll be here early, in about 5 minutes, so your evening has only started," Gail told me. I heard her move away then. She had obviously taken off the towering heels because I couldn't hear her walking on the tiles anymore and I could only assume she was wearing clothing that she could move silently in to give me no clue as to where she was. The waiting was terrible and interminable. It played tricks on my mind as I strained to hear anything that would give away whether anyone was close or not. Most importantly I strained to hear the door bell ring which would announce the arrival of Bob. I was trying to relax as much as I could when suddenly I felt a hand on my left hip. It was a large hand and I knew immediately that Bob was standing behind me. Gail and he had obviously worked together to get him inside and to me with no noise at all to give him away!! I heard murmuring and tried to catch the odd word. "Nice legs and the heels look great," I heard Bob say then with a sudden realisation, knew that Bob was not blindfolded and could see me. My heart quickened with the concern that I might be recognisable but what could I do, I was totally out of control and they both knew it. Bob had brought himself close to me now and I could feel his very erect penis between my butt cheeks. He pushed in against me, sliding his shaft up and down, teasing my puckered anus as his head slid over it. "Awesome arse too," I heard him say to Gail as I felt him now line up his penis with my butt hole and start to work himself inside me. Though I was worried about the recognition thing, I was totally taken away by the feeling of a real penis inside me. While the dildo had been a great sensation and had rocked my socks, the feeling of a real penis was just so much better. While it was hard, it had a softness to it too and felt warm and alive as Bob invaded my already well fucked rear. In no time at all, Bob was in as far as he could go and his thighs were being pushed hard against my buttocks as he tried to force his member ever deeper into me. The sensations for me were overwhelming and now that I was over the nervousness of the first encounter, I let myself go and revelled in the feelings that were cascading over me. I was being fucked - properly! Bob started his in out fucking and he really knew how to contact my prostate. The feeling of having his penis stroking back and forth against it were heavenly I knew that chastity cage or not, there was no way I was going to be able to avoid cumming from his ministrations. I realised we were both groaning and straining. Even if the noises coming from me were far from understandable, there would have been no doubt in anyone's minds that they were hearing noises of intense pleasure. Bob was now holding my hips tightly in his large rough hands and was pounding into my arse with enormous strength. His thighs slapped into my buttock as he pushed me heavily against the bench, plundering what he had claimed as his, then with one almighty thrust, Bob emptied his semen deep within my bowels. He continued pumping into me, filling me up with his seed and causing me to push back against him as much as I could to try and milk that last little bit from him. Over too fast, I could feel Bob's erection ebb and with no ceremony, I felt him slip out of my butt and a few drops of his cum, slip down my leg and into the tops of my stay ups. Bobs hands left my hips and I felt more than heard him walk away. I was alone again waiting for what? I listened intently for any sound but couldn't hear anything save for the blood rushing through my ears. I figured that seeing as they had engineered Bob's soundless arrival, they could also organise his soundless departure so just gave up trying and revelled in the feelings emanating from my very well fucked arse. "It's still early so can I have a play now?" Gail said as she startled me. I had not heard her approach and hearing her voice close to my ear, knew she was standing very close. Caged for Freedom Ch. 02 "Mmmhmmm," was the best I could do but hoped that I had conveyed to Gail that I was happy to continue. "Goodie," she said with definite glee. I felt Gail move round me almost with resignation, felt her push the large butt plug back into me. Even though I had now been pounded three times in the last 24 hours, I welcomed the feeling of having my arse stretched again. Once Gail was sure the plug was seated, she started unbuckling the spreader bar on my ankles. With that done, she unlocked the pillory and helped me to stand. I was a bit unsteady on my heels but leaning against the bench helped. "I'm going to leave the hood and gag etcetera in and I want to lead you to another room," she said. Taking me by the hands Gail turned me slowly to my right and started gently pulling me toward her as she backed away. She led me out of the kitchen and to a room I could only guess at but never having had a tour of her house, had no idea where I was. Eventually she stopped and with her hands, indicated she wanted me to turn round. I did so and she pushed me slightly backwards until my legs hit what was obviously the side of a bed. Steadying me, Gail now undid my skirt and let it drop to the floor before unbuttoning my shirt and also dropping that aside. I was now wearing nothing but my stay ups, heels, cage, plug and nipple clips. Gail now pushed me gently on my chest indicating for me to sit on the bed. I reached behind me and gingerly sat back, realising as I did that the bed was covered with a sheet of rubbery material. Gail now pushed me back further and so I lay back and swung my legs up onto the bed. I felt Gail lean down to me and she told me to move higher up the bed until she stopped me, so I squirmed my way upwards until I felt her tap me on the shoulder and I knew I was in the right place, lying in the centre of a king sized bed. I felt Gail take one of my wrists in her hand and pull it towards the top corner of the bed and I instinctively knew what was coming. She was going to spreadeagle me to the bed!! Yummm!! I felt the soft but unyielding leather cuff encircle my wrist then just heard the clink of a clip as she attached the cuff to a strap. I knew what she had here as I had made them for her many years ago. The strap was a luggage strap that I had modified just for this purpose. The straps had a cam arrangement that meant that the strap could be pulled through one way but locked going the other unless you held a little lever down to release the strap. For now, Gail pulled the slack out of the strap but I knew that she would tighten them again soon. Gail moved now to the other wrist and repeated the procedure, again just taking the slack out of the strap. I heard her move away then and wondered why she wasn't doing the same for my ankles. I heard nothing for quite some minutes then felt her lift my left foot and start to buckle a cuff around my ankle. Once she had finished that, she lifted my right foot and moved it away from my left then proceeded to buckle a cuff round my right ankle. I realise quickly that she had buckled me back into the spreader bar and was now attaching it to a strap fixed to the foot of the bed and was taking the slack out of that strap as well. I might have not been fully spreadeagle but I was nevertheless totally tied down and available. "I hope you're comfy because I have a few preparations to do then I'll be back," Gail told me then left the room. I had a bit of movement as Gail hadn't tightened the straps too tight but there was only a few inches of slack so really, the feeling was certainly of being bound. This was a feeling I totally adored, strapped down and available and with nothing to do but indulge in the feeling of the bondage. Again the time played tricks on me as it slowed to a crawl and I had no idea of how long had passed. My position was comfortable and as always with Gail, I felt safe so I must have dozed off. I was awaken by the feeling of the straps being pulled up tighter, rendering me taught and even more secure on the bed. "I'm back and ready for my fun now," Gail told me with a grin and a happy lilt to her voice. I could feel Gail sit on the bed now, touch the chastity cage and wondered just what she was going to do. She gripped the cage itself and gently pulled it away from my body, stretching my cock and balls as she did so. "Mmmm, that looks so solid and secure locked onto you. How does that feel with me stretching it out like that?" Gail asked knowing full well that I couldn't respond. Instead I simply groaned a satisfied groan and abandoned myself to the feeling of having my cock and balls tortured. Gail continued to pull and twist the cage with one hand and squeeze my ball sack with the other. Things were getting very turned on down there and I could feel my penis now painfully enlarged within the unrelenting cage. Gail let go of my balls but continued holding the cage out and instead picked up the little strings attached to my nipple clips. With these she pulled the clips tightly away from my chest. I tried to follow the pull by arching my back but the way I was tied down, I had so little movement I simply had to abandon myself to the exquisite pain I was receiving from my nipples. I had better explain here that the nipple clips were the Clover type which actually tightened the more the strings were pulled so as Gail pulled on them harder and harder, the clip bit ever more into my already sore nipples. I was loving it! Having me squirm round on the bed as I was doing was just what Gail had wanted to do. I knew that she knew that I totally loved what was happening to me and I also knew that she really got off on doing this too. After some minutes of this beautiful torture, Gail stopped and I felt her reaching off to the side. Finally, I felt Gail undoing the little padlock on my cock cage that had held me for the last three days. I imagined the lock sliding out of the hole in the end of the locking pin and the felt the cage being lifted away from the solid steel cuff round the base of my balls. She slid the pin out of the cuff and opened the cuff to finally release me from my chastity. The feeling was heavenly and I immediately felt my penis become very erect. "That looks so yummy," I heard Gail exclaim. I heard Gail put the pieces of the cage aside then heard her fumble with something else. The next feeling was incredible! Gail had got a bottle of lube and she was now dribbling it over my hot, erect shaft. I could feel every drop as it hit my penis as though it were a heavy ball. Now with a well coated penis, Gail gripped the shaft with both hands and started smoothing the lube all over my shaft and balls. I nearly exploded as she was doing this but for some reason I didn't, only making my turgid member even harder still. From past experience, I knew that Gail absolutely adored playing with my penis and she knew how to do it without making me cum. Somehow she knew all the signs and could bring me right to the brink without pushing me over the edge. The experience of this sort of tease was almost unbearable, particularly when tied as tightly as I was however, had I not been tied down as I was, there was no way I could have endured such a teasing torture as that Gail provided right now. Gail concentrated on my penis to start with, pumping her small fist up and down the shaft, stopping every so often to run a finger over the tip and force it a little into the opening. Again she knew I loved that and was making sure she was pushing all the right buttons. Just when I felt I could take no more, she changed the tactic to holding me tightly round the base of my penis and playing roughly with my balls. Again, she knew just how much pressure she could put on a squeeze there without it being a turn off pain, but still hurting me enough to pander to my pain want. Over the next ten minutes, Gail worked me over, bringing me high then letting me drop down again, all the while keeping my penis in her hand and always working it as she wanted. When she stopped, it was almost an anti-climax and I slunk back onto the bed, not really realising that I had been arching my back off the bed in ecstasy. Gail let my penis go and I could feel her moving as she climbed off the bed and I could make out small noises in the background but couldn't decipher what I was hearing. Just when everything got quiet again, I felt Gail get back on the bed. This time she moved her body up the bed until she was kneeling beside my waist then I felt her put a condom on my penis then move quickly and realised she was now straddling my waist. I could feel her legs tucked closely against my waist on either side of me and realised that it was skin on skin. I was not sure where this was going but being as bound as I was, I had no input nor any way to protest what might happen. Gail moved again and this time I felt her grasp my still very hard shaft and bend it upwards to aim it. We certainly hadn't talked about her fucking me and realistically I did not want to cheat on my wife in that sense however, if Gail had decided that that was what she wanted then I was going to have to accept it. She had, after all, provided me with the most amazing journey over the last few days that if that was the price, I'd have to live with it. I felt Gail moving slightly and almost in resignation, realised that she was indeed lining up my penis so she could impale herself on it so when I felt the head of shaft contact her body, I knew what the result was going to be. I felt Gail sink lower and imagined my penis was being swallowed by her vagina then realised that what I was feeling was incredibly tight and required a good amount of force to get it in. She was taking me in her arse!! Gail let out quite a loud gasp as my head passed through her sphincter and entered her. She held still for a moment to allow herself to accommodate my girth then in no time at all, started sinking down again, welcoming my penis into her. When she finally sat firmly on my abdomen, she let out a very satisfying groan that I could easily hear, even through my ear plugs. Gail just sat there for a few moments, allowing the feeling to process then slowly and surely started pumping herself up and down on my shaft. Every time she started an up stroke, she clenched her anal muscles to give me a good squeeze and I knew she was working on me to take me over the edge. To say I was enjoying myself would have been an understatement as I tried my hardest to meet her every down stroke with an upward thrust of me own. Sadly, my very tight bondage didn't allow much in the way of movement but she certainly got the message that I was enjoying myself. I could hear my breaths coming in gasps through the breathe through gag and could hear my heart pounding in my ears as I climbed inexorably to my climax. What I didn't know at the time was that Gail was climbing higher and was now frigging herself with abandonment working herself to her own climax. I could take no more. I had been fucked silly with a man's penis and huge strap on. I had been stuffed and sluiced, tied up and tied down and my mind was in overload as I finally reached that point where time stood still and my penis exploded. It gushed forth a huge amount of cream, filling Gail's arse with my cum. Just as she felt me start to cum, Gail herself had reached that plateau where everywhere is down and she launched herself into oblivion as her orgasm consumed her. We both moaned and groaned and gasped for breath as our mutual orgasms swept everything else aside. Gail collapsed forward onto my chest and murmured indecipherable things into my ear. She lay like for a long time as we both descended back to our earth. Eventually, Gail sat up and as my penis shrunk back to almost normal, she eased herself off me and off the bed altogether. She left me tied like I was for a while as she got herself sorted out then came back in to release me. Starting with the spreader bar, she released the pressure on the strap then unbuckled the cuffs from my ankles. With relief, she then moved to my wrists and released the pressure on those before unclipping them and I was free. I just lay there for a bit, getting the feeling back in my hands and shoulders and taking stock of how I felt. Gail helped me to sit on the bed then sitting behind me, started the task of unbuckling and unlacing the bonds that had been on my head for the past hours. When the hood and finally the ear plugs were removed, I could once again feel air on my face and the sounds of the home washed over me. "How do you feel?" Gail asked me. "Absolutely bloody amazing!" I said and broke into a huge grin. Gail helped me off the bed and suggested I go and take a quick shower before I went home so I headed off to the shower, stripped and spent a glorious few minutes feeling the hot water sluice over my body. As I was drying myself, I realised that the only clothes I had to wear home were the ones I had arrived in so I was going home in a skirt and heels! On well, I thought as I dressed then slightly unsteadily walked out the kitchen where Gail was waiting for me. "I hope you don't hate me letting Bob see you but I thought that he couldn't see your face and dressed as you were he certainly wouldn't recognise you anywhere, so long as you weren't dressed like that," Gail said all very quickly. "I'm fine with it," I said. "I had come to the same conclusion so it's all good and actually added to the experience so thank you." Gail and I sat and talked about the last few days over a welcome glass of wine. I was due to pick my wife up from the airport in a few days and that would spell the end of our play time which felt somehow quite sad. Gail told me that Bob had shared with her that he had absolutely enjoyed himself immensely and if I ever wanted to repeat the experience he would be available anytime to help. Eventually it was time to gather my things and head for home. I decided to leave the bondage gear there for now and I would pick it up tomorrow sometime. "So do you want to be relocked into your cage and I can let you out tomorrow?" Gail asked. I pondered that for a moment then thought why not, I really liked being locked up and the fact that Gail held the keys added to the feeling. As Gail went to get the cage, I put a little lube on my balls and penis so the cage would fit on easier. When Gail returned with the cage and lock, I showed her how to fit the cage on me so one day perhaps, she could do it herself. Once it was all on, she slipped the padlock in and snicked it closed. "I just thought about something," she said, "Wasn't the deal that I wouldn't take this off until you had been fucked in the arse?" I nodded slowly, not being sure of where this was going. "Well in that case, I have just locked it on you so the only way it's coming off is for you to get fucked in the arse. Best be here tomorrow evening again and I'll see what I can arrange." She had tricked me and she also held the key so it looked like I was going for a hat trick!! As I left, I wondered what tomorrow was going to bring. Caged for Freedom And so it started, the inevitability of what was happening descending upon me as I was rendered first deaf then silent then blind. Like our practice run, Gail helped me into the pillory, locking it securely as soon as it was closed round me. The spreader bar on my ankles completed the journey with the final realisation that nothing now prevented me from being fucked in the arse. I knew that Gail had locked me up early and could now hear her moving round me preparing for the arrival of "Bob". I thought I'd have quite a wait but suddenly I heard a sound that was certainly faint through the plugs and hood but I knew it was the doorbell being rung. Bob had arrived! I could just hear some very muffled conversation then everything went quiet. A few minutes went by then I felt a hand on my back. It was Gail. "Bob is here now and getting undressed in another room. I'm just going to get you finally prepared for your adventure." she said. I felt Gail moving the butt plug that had been buried inside of me for the last few hours. She grasped it by its base and started slowly working it out of my well stretched hole. As it was so large and long, it took a fair bit of work to get it out but eventually, out it came, leaving me felling rather empty though I knew it was not for long! I then felt a small nozzle being inserted inside of me and wondered what Gail was doing. Being so loose from the plugs stretching, she had no difficulty in poking whatever she wanted into my arse but I had no idea what was happening until I felt something being squirted inside of me. "I'm putting a whole lot of lube inside you so Bob can slide more easily inside of you. It's water soluble and will come straight out afterwards", she told me. I felt the nozzle being taken out then again, everything went quiet. I waited in anticipation, scared and shaking and straining to hear the tiniest little noise then suddenly, someone touched my left buttock cheek. It didn't feel like one of Gail's small hands and this one felt a bit rough and definitely male. I now felt another hand on my right butt cheek and realised I now had a real male with a stiff penis, poised at my quivering butt hole with one thing on his mind, fuck the arse in front of him. His hands moved a little as I imagined him moving closer to me then finally - contact. I was almost in denial but this was for real and right now, I could feel the head of Bobs penis rubbing against my puckered hole. He rubbed it up and down along my opened crack as though he was getting it all slippery and lubed from the ooze that had slipped from my arse. It became apparent that Gail was holding Bob's penis and was pointing it at the right place. I felt then a shift. Gail had put his penis right on my bud and Bob was starting to put pressure on and I was suddenly aware of really how thick this man's penis really was. The pressure increased and I did all I could to relax my butt and welcome him in but his girth was certainly major and a worry went through me whether this was going to be possible and was it going to hurt! Bob pushed more and more then suddenly, in a flash of pain, I realised his head had popped inside of me and I was being impaled on a turgid shaft that was another man's penis. Wow, I thought as I heard a small gasp escape Gail. Bob knew he was inside of me and thankfully, held still for a moment to allow me to relax round his pole. The pain, though immediately intense, started to ease and within moments, I began to enjoy the over full feeling his penis was giving my welcoming butt. I had to remind myself though that he was barely inside of me and that there was much more of him to follow! In no time at all, I felt the pressure start to increase as Bob pushed more of his pole inside of me. He didn't simply shove it in but rather worked himself gently into me with small in and out movements with the in movements being a bit longer and bigger than the out. Almost in surprise, I realised that I could now feel Bobs thighs pressed against my buttocks and knew that he was now buried as deeply inside of me as he could get. I was now totally stuffed with Bobs penis and I was loving it!! I silently praised Gail for filling me with lube as he now started sawing himself in and out of my butt, pounding harder and faster with every stroke. As he bottomed out into me, he pushed me harshly against the bench where my steel cock cage banged against the cupboard and twisted my own penis hard down. Though the cage prevented me from getting a full erection, my shaft had pumped up and was now painfully full inside the unforgiving cage though I hardly noticed as my mind was full of the sensations having my arse fucked was giving me. Bob pounded on and on and I could hear him grunting with exertion every now and then. What I could also feel was his penis becoming harder and thicker and knew that anytime soon, he was going to climax and fill me with his cum. Too soon, too soon I fretted as I realised just how much I was loving these sensations that were crashing over me. What was happening to me? Over the last weeks I had been seriously questioning my own sanity and even my sexual orientation but now, now here I was held in place, immobilised and being fucked hard in my willing arse and loving every moment of it! Then it happened, with an extra hard thrust, Bob came in a rush, grunting and crying out as his penis throbbed and exploded in my butt. It felt amazing! He held still at last as the final throbs died away and I could feel his penis begin to deflate and shrink within me. I didn't want it to finish yet but it was over as I felt him pull gently from me and his hands left my buttock. I lay there on the bench, processing all the feelings and thoughts that had coursed through me, revelling still in the total bondage and the soft pain of a well used arse. Eventually I heard the soft murmurings of Gail seeing Bob out and her imperceptible foot falls on the kitchen floor as she returned to me. "Are you all right in there?" she asked as she gently stroked my back. "mmmHmmm", I hummed as encouragingly as I could from within my hooded head. "Would you do it again?" she asked. It was a little hard to nod but I did and made as many positive noises I thought I could through the gag. "I'm going to release you now but before that, the butt plug goes back in. I don't think you want all the cum to leak out of you just yet do you?" and with that, I felt the huge plug slide easily into place into my well stretched butt. Gail very gently started to release me from my bonds and eventually I could stand and was free of the hood and gag. Looking at the clock, I realised I had been locked into position for over two hours yet it had seemed to go in the blink of an eye. "Go get dressed," Gail said, "then we can have a debrief!!" I walked almost in a daze to the bedroom and put my clothes back on. I realised that I had a soft ache inside where Bobs penis must have been hitting home in my arse. It felt good. Gail had a glass of wine waiting for me in the lounge and I gingerly sat down on the butt plug, feeling it pushed firmly inside of me. I needn't have worried though. I had been stretched well and truly and the plug was child's play in comparison. I realised though that I still had the chastity cage locked on me and needed that off before I left to go home. "So, what's going through your mind?" Gail asked. I had a million thoughts racing through it. I had loved everything from the mind games to start with, the real bondage to the actual act of having my arse reamed. I had felt full and taken and stretched and thoroughly used and if I could do it again and feel that again, I would in a heartbeat. At that, Gail dropped another bombshell - "Bob wants to too," she said. I was shocked! I knew I was feeding a real kink inside of me but to realise that someone else probably had the same sort of kink was a welcome revelation. "Would he want to do exactly the same again? Pound my open arse while blindfolded again?" I asked. "He offered more than that if you want. He is happy to fuck you again exactly the same or in a different position. He is more than happy to not know who you are and is equally private about you knowing who he is so we will have to accommodate both of you in that regard but it can be done. He also offered to have you fuck him in the arse if you wanted to. I don't think he has the same want as you but he is happy to meet you half way if you wanted. What do you reckon?" Gail asked. "Well, for the moment, I'd be more than happy just to recreate what we have done tonight. Next time I wouldn't be as scared as I was tonight so will no doubt enjoy it even more. In fact I would really like it to last longer and have more of a pounding but that would be up to Bob and I'll just take whatever he wants", I answered. "Alright then," said Gail, "another decision time. I can leave that chastity cage on you and you can come back here tomorrow night for another fucking or I can take it off right now and we'll work on another opportunity in the future. What do you want to do?" I didn't need more than a second to decide. "What time shall I be here tomorrow?"