I don’t get a lot of opportunities to indulge in self-bondage nor do my wife and I get to explore bondage as much as we would like. What with my wife’s schedule and having an almost teenage daughter around. But today all the stars aligned and lo and behold here I am with a Sunday all to myself. What to do?

I only realised Saturday as I was slogging through a workday that I normally don’t work that I had the day to myself. Visions of sugarplums. No that’s the wrong story! I ran through a library of scenarios. It has been so long I didn’t know where to begin. Even by the time I finally went to bed Saturday night I still had no idea what I would do but I knew I needed to do something. It’s the few and far between thing.

I had a sort of plan that I would stay in bed and rummage around through our bondage equipment in hopes of inspiration. Alas nature called and I decided to deal with my morning routines first.

I stripped off my nightgown and climbed into the shower. While I was clearing unwanted hair off my body I remembered my wife’s nipple clamps. Oh boy a plan started to form. Now I had a plan all I had to do was make it work!

After towelling off, I donned my favourite high waist panty girdle and front closing long line bra. Since I didn’t want to soil my girdle I also used a non-lubricated condom. I then carefully clipped on the nipple clamps. Making sure they had a good grip. They are the kind that the harder you pull the tighter they get. Ouch! I had to undo some of the bra to get them on the way I wanted. I attached them so the free end of the clamp was pointed down. Then I padded my bra with pantyhose. Lifting the clamps (OUCH) to get the padding around to fill the cups of the bra.

I was pretty excited by this time. I wanted to jack off right then but I knew that would end my scene. So with immeasurable amounts of self-control I continued. Once I had the padding where I wanted it. I pulled on one of my favourite dresses. It is a long flowing gown with an elastic waist and the only way into it is from the bottom. The dress is low cut to show cleavage. That was necessary for today’s ambitions. Needless to say that meant the elastic created all manor of hurt to my already tortured nipples.

I thought about nylons but currently I don’t have any that are not holed. I dug out of the far reaches of the closet a pair of five-inch heels. They have elastics running criss cross up your arch. Really cool. My 26-year-old daughter keeps asking her Mom why we have such large shoes in the closet. I think she knows but is too polite to say anything. (Blended family)

It has been a while since I have had the opportunity to wear them and it took me a couple of turns up and down the hallway to get used to them. Once I got comfortable strutting around in them again I continued with my make it up as you go along plan. (Don’t try that cuz you can run into really problems) I dug out our bondage equipment. Ball gag, rope, cuffs, locks etc.

I couldn’t decide if I wanted to tie my ankles with rope or use the cuffs and hobble myself. Considering what I was going to do I opted for the hobble. I wrapped leather cuffs around each ankle and locked them into position. I love cuffs and locks they sound so final when the lock clicks shut. I just wanted them on until I was ready to hobble myself. Next I added the ball gag. (Home made) 2” ball and I tightened it real tight because there are only 2 holes in the securing strap. One to fit me and the other to fit my wife! I did not lock it on because I never thought about it until after!

Now for the good stuff! My plan!

Since I would be standing I took one of our ropes and snagged it over a hook in the ceiling of our bedroom. First try too. After hobbling my ankles with a very short chain I tied the business end of the rope to the looped strings attached to each nipple clamp. By now my nipples were extremely tender and manipulating the clamps hurt even more. On the free end I added weights.

I considered backing out but only briefly.

I checked to make sure I would be able to reach where my freedom keys would be before I finished binding myself. Once I was satisfied with the proper length I adjusted the rope to pull me up just short. More pain! I threw the keys into the middle of our bed right close to the headboard. It took me some contortionism to finally lock the cuffs around my wrist behind my back. With my hands behind my back even if I could grab the rope I would not be able to get the keys. The ball gag prevented me from using my mouth to hold the rope as well.

There was nothing for it I would have to back up to my bed pulling the weights up as I moved. I have played with the nipple clamps before but never to this degree. Now remember I am not using a pulley so the rope has to drag across the hook. (Much harder to pull) I could not believe the world of hurt as I tried to pull the rope through the hook in the ceiling with nothing but my tortured nipples. On top of it my motion was hampered by my hobbled and high-heeled feet, which made me move in a kind of jerky fashion. Which in turn made the weight bounce and jiggle. (OUCH). Of course as I pulled against the rope the nipple clamps twisted up and pulled out adding to the torture. The bra might have been saving me from additional pain but I doubt it.

On top of it all I had a raging hard on that I could not reach. Of course with the girdle my cock was trapped tight against me and rocking my hips made matters worse for my nipples.

Although it was only a short scene for me it was very intense. As I said before I have only lightly played with nipple clamps. This took it to a whole new level.

Finally I managed to suck it up and backed up to our bed. With my hands bound behind my back I could not just reach out and get the keys. I had to lay down and squirm around. Additional torture! As I said earlier I made my rope just short of what I needed. Which meant that I really had to suffer the pull to get the keys. By this time my nipples were screaming for forgiveness. I was drooling and because of my dress I had worked up a pretty good sweat. Never mind I wanted to get off.

In trying to reach the keys one of the nipple clamps pulled off. After my initial shock that it could happen the pain hit. OMG. I could not believe the pain. I lay absolutely motionless while I caught my breath. I also realised that I was holding the entire weight on one nipple now and it was not happy with me. I still had to get the keys and I could not reach them. After resting for minute with my nipple screaming for relief I just wished it would pull off as well. I still had an extreme hard on though. Guess I liked the pain! I finally mustered enough courage and moved again toward the keys at the center of the headboard.

The short rope added an incredible amount of pain to remaining nipple. I managed to get the keys and with release my hands but not before enduring another bout of unbelievable pain. Once my hands were free I gently moved the padding around the clamp and even more carefully removed the clamp. As the blood started flowing back into my breast I groaned into my ball gag.

The nice thing about a condom is you don’t have a mess to clean up afterward. As I sit here writing this my nipples still yell at me when I brush up against something. I am looking forward to the next time I have the house to myself. I’m thinking maybe a little more time before I can free myself. Maybe binding my knees so I have to hop. Or something.

Play safe!