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.
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.
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?"
Sep 7, 2018 in anal