My Bondage
by Sir Richard

Part 1

Chapter 1 – My Bondage Begins

F/m, F/mff

Capture and transport

I watched Diane open the door to her room. I had picked her up in the hotel bar, though I guess, with 20-20 hind sight, it would be more accurate to say she had picked me up. We had chatted for a while and she had asked if I would like to go upstairs where we ‘could be more comfortable.’

Of course my answer was yes. She was a very attractive woman. A few years older then me, perhaps, but with a pretty face and, from what I could see, an admirable figure. In the elevator she had asked my room number but when I told her she said something about the upper floors having bigger rooms and suggested we go to hers. I didn’t much care about room size but then I wasn’t thinking beyond the size of the bed in either room.

When we entered she started to unbutton her blouse as she walked across to a desk. She told me to take off my shirt and get comfortable. This was moving pretty fast but I saw her blouse go on the back of the desk chair as she unhooked her bra.

Now Diane was a few years older then me but she had very nice breasts. They were full and inviting and I guess I was staring at them as I tossed my shirt to one side. I certainly wasn’t staring at her hands as she walked towards me and that proved to be a big mistake.

The next thing I knew I was on the floor with my limbs twitching. Gradually it dawned on me that I had been shocked with a taser of some sort. While I was figuring this out Diane rolled me face down and pulled my hands behind me back where she secured them with handcuffs. Then she grabbed my hair and pulled my head back. I still didn’t have control of my motor nerves so my mouth gaped open and she had no trouble inserting some sort of rubber gag.

She fastened a strap behind my head and another under my chin and began to squeeze a pump that dangled from the front of the gag. It inflated pushing my cheeks out against the strap and my jaw down against the chin strap. Then she walked back across the room and came back with several ropes in her hand.

By this time I had regained some motor function and was trying to get my legs under me and stand up. This is hard enough to do with your hands cuffed behind you but I might have been able to stand if Diane hadn’t pushed me over and back down to the floor. I was regaining my strength and struggling but she simply sat on my butt pinning me down. She passed some rope around my arms above my elbows and pulled my elbows toward the center of my back. I resisted but she simply used her thighs to press them together as she pulled the slack from the ropes. She couldn’t get my elbows to touch but she did get them far enough back to be very painful. After knotting the rope she carefully cinched it.

I don’t mind telling you I was scared. I recognized Diane as the woman from the bar but I hadn’t a clue as to why I was being bound and gagged. Was she some sort of psycho killer who lured men to her room and then killed them? I know it sounds ridiculous but given all that had happened I was really scared.

Having finished with my arms Diane stood up and rolled me over on my back. Then she straddled me facing my feet and dropped down on my stomach. As you might imagine this drove the wind out of me and reduced my struggles as she opened my pants and pulled them and my underwear down below my knees.

With my pants at half mast I was unable to do much as she bound and cinched my knees. Finally she stood up, removed my shoes and socks and pulled off my pants and underwear leaving me totally naked. With my knees bound she had no problem completing my bondage.

First she tied my ankles and then, flipping me over, she ran a line from my elbow bindings through my ankle ropes and pulled me into a very tight, back arching hog tie. I tried to resist this but she simply braced a foot on my shoulders and heaved on the rope. She continued until my feet had been drawn past my hands. My flailing handcuffed hands could just about touch my calves but reached neither my ankle nor my knee bindings.

Diane dragged me over to the bed and flipped me onto my side. While this was marginally better than my stomach it was still a painful position. My mood didn’t get better when she looped a line around my testicles and tied it to the foot of the bed. She smiled at me as she said, “That ought to keep you in place. I have to go out for a bit and I don’t want you trying to wiggle around and knock the phone off the hook.”

I watched as she rifled through my pants. I though perhaps that she wanted to rob me, but she discarded my wallet and took the plastic card that was my hotel key. Slipping her blouse on (she ignored her discarded bra) she walked out the door.

I don’t know how long I lay there but some of the panic I had felt receded. I still didn’t know what was going on but she had ample opportunity to kill or injure me and hadn’t. The bondage was tight and painful but nor life threatening. Eventually the door opened and she returned towing something that looked like my suitcase. This was confirmed when she laid it down, opened it and dumped my clothes, wallet and what not, including my shoes into the case and reclosed it.

She stripped off her blouse and skirt. Then, wearing only her panties she came over and untied my testicles from the bed. With my fear gone I responded to her beauty and her touch and grew hard. She smiled knowingly at me but made no comment. Instead she rolled me onto my stomach and untied the hog tie leaving me stretched out on the floor. It was great to be able to stretch my limbs again even if my shoulders were protesting the tight binding above my elbows.

Dianne went to her desk and returned with her hands full. I couldn’t identify most of the stuff as she set it above me on the bed. While I was still stretched out face down she sat on the small of my back. I felt her spread the cheeks of my ass and a cold thick gel like substance was spread around and into my sphincter. I realized this was a prelude to some sort of a butt plug and desperately clenched as much as I could.

She just laughed and said, “You are going on a trip and I want you to arrive in good shape. Unfortunately you will be traveling luggage class and won’t be able to use the facilities so this thing is going in. If you clench it will hurt but if you relax you may even enjoy it.”

Trip! What trip. What the heck was this crazy woman talking about? I was angry, aching and humiliated at the way she seemed to so easily be in complete control. Unfortunately I paid no attention to her warning and she forced the butt plug past my clenched anal muscles. Yes, she was right. It hurt!

Once it was in, she did something with the face plate of the gag and detached the pump. A few seconds later the pump went to work again. This time it was pumping up the plug in my ass. I had felt pain when the butt plug went in but once in it was pretty benign. I felt fullness, as if I had to go to the bathroom, but the pain was pretty much gone. That was until she began pumping it up. Then the pain returned as she stretched my lower anal passages until I thought they would burst.

Diane rolled me onto my back which seemed to drive the butt plug even deeper. Then she approached me with some tubing. I had shrunk to flaccidity with the pain of the insertion and pumping up of the butt plug. She took my now limp penis and inserted a tube. This wasn’t particularly painful but it certainly was uncomfortable. I recognized the tube as a medical catheter and sure enough she kept feeding more and more tube into me until the catheter was inside my bladder. I could see the urine flowing down the tube into the collection bag. Once the catheter was inserted she pumped up the balloon inside my bladder and gave a sharp tug to ensure that the tube couldn’t come out.

Talk about humiliating! As if that weren’t bad enough she now inserted tubes into my nose. These scraped and hurt the sensitive tissues as she fed them past my sinuses. Of course I tried to turn my head but she solved that by sitting on my chest and holding my head with her thighs. Once she was certain a runny nose wouldn’t cut off my air supply she taped the tubes to the flat mouth covering of the gag, ensuring they would stay in place. The tubes were quite long and she correctly interpreted my puzzled look at the coils because she smiled at me and said, ”These not only ensure you have a clear airway, the coils act as a sound deadener so that even if you force some noise out your nose it will be inaudible.”

Now she lifted my back to a sitting position. With a bit of effort she moved me back so that the bed supported me. I brought my knees up to give me more stability. Diane reached behind me and I saw a long colorful strap. I recognized it as the sort of thing people wrapped around their luggage to make the bag more easily identifiable at the airport carousel.

She wrapped this around my back under my arms and then led it under my legs and fastened it. As she tugged on the strap I tried to resist. She gave me a nasty look but said not a word. Instead, she pulled my feet out in front of me. The strap forced my torso to bend forward so that I was half bent over. Then the damned woman sat down on my shoulders compressing my body towards my thighs. She tightened the strap and then bounced up and down on my shoulders. Each bounce pushed me further down. After each bounce she tightened the strap, rose up and bounced again. I was clearly no problem for her. She wasn’t going to waste her breath arguing with me. She simply made it happen.

Once she had me folded over she ran a line from my elbow ropes over the handcuff links. Dianne rolled me over so that I was lying on my bound arms again with my legs uppermost. You can guess where this was going. The line was led through the crack of my ass, securing the butt plug even deeper into me. Then it ran trough my ankle bindings. As she heaved my ankles were pulled back towards my butt. This not only secured my in a tight ball tie it also increased the tension on the strap. When she was done she pulled me up to rest on my butt and my feet. The ropes and strap were so tight I couldn’t even twitch.

She moved out of my sight for a minute and came back dragging what looked like an old army footlocker. It was rectangular with clasps at either end of the front and a sturdy hasp for a padlock in the center. I remembered her comment about traveling luggage class and realized that she intended to put me into that box. I wondered how she planned to accomplish that, but given the way she had controlled me from the first, I had no doubt she had planned something that would work.

In the event, it was ridiculously easy. She stood the footlocker on end and opened it. Then she moved it behind me and slid it forward until the edge was pressing against my butt. Diane grabbed my hair and pulled me forward until my ass rose. Pulling me a bit more forward, my heels came off the ground and I was balancing on the balls of my feet. Then she simply slid the trunk as far forward as possible and released my hair. I fell back and found my butt and heels inside the box. Then Diane tilted the box backwards and I simply slid back to fall on my bound arms. I realized as I landed that I hadn’t fallen on the hard surface of the trunk. Rather there was a squishy sort of material under me. As I looked I could see partly filled bladders lined the box.

In a few minutes Diane appeared in my rather limited line of vision. She tucked a black plastic thing next to my neck on one side and the catheter bag on the other. I figured that the black thing was the now unnecessary taser. The coiled up breathing tubes were placed over my face. Then I heard the whoosh sound of the air pump. In a few minutes the bag under my back firmed up and the ones on the sides, bottom and top of the box began to swell and press against me. Diane looked down at me and said, “Can’t have you banging around in there and attracting unwanted attention. Cheer up the bags will also provide some insulation. There is plenty of air in the cargo hold but it gets pretty cold.”

Then she closed the lid. I felt rather than heard the latches click shut and found that I was not only tightly bound but held so that I couldn’t twitch. Oh I could wiggle my fingers and toes with some effort and I could open and close my eyes but with the lid shut the interior was an impenetrable inky darkness.

I have always read in stories how boxed victims could tell what was happening by feeling and sounds. I have to tell you that the stories are only slightly true. Oh, I felt a sinking motion when the hotel elevator went down and there was a whine when jet engines roared up to take off power followed by a tilting that indicated we were climbing but that’s about it. For most of the time I was simply in the box and the movement or lack of it made no sense at all to me. I don’t know how long I was in the box or how far we traveled. I guess I slept part of the way but I have no way of knowing. I was hungry but not ravenous so I guess it wasn’t a matter of days but that’s about all I could tell.

Introduction to slavery

When the box next opened I was dazzled by bright light and a rush of filtered tropical air. The air bags deflated and I tried to make sense of what little I could see from the box. I didn’t have much time as the box was tipped over and I found myself on a concrete floor in a large well lit room. As my eyes adjusted to the light I realized Diane was there in a tropical outfit. More interesting was the fact that two other more or less nude women were there with her.

I say more or less nude because both women had a metallic belt locked around their waist. When the women turned as they worked I could see a chain running from the center of the belt to a metal device that disappeared between their buttocks.

As you can tell I was pretty awake and observant. I described Diane’s outfit and the belts first so that you know I was observing everything and not just staring at the women. That said I couldn’t help noticing the women’s breasts. First they were firm and lovely. Secondly they sported nipple rings! Not just those cute little ones that could be tucked into a bra. These were large golden rings that wouldn’t have looked out of place as gypsy earrings. I did stare a bit and noted that there seemed to be no opening or fastener. These were, apparently, permanent devices.

The other thing was that both women had bare pussies and wore some sort of slim chain device that seemed to cross back and forth over their slits. . At the time I couldn’t really tell how the chain was fastened but I soon learned that each labia had been pierced five times with small rings inserted. The chain was threaded through these rings like a shoe lace and pulled the labia tightly together. The ends of the chain were secured by a small padlock that I didn’t immediately observe as it was dangling between their thighs.

It was obvious that this would prevent anything from being inserted and even prevent access to the women’s clits. Clearly it was some sort of chastity device that prevented the women, or anyone else, from pleasuring themselves or each other. What I didn’t learn until later was that it also prevented the removal of Benewah balls that kept the women aroused and frustrated.

One of the women had a large bust, a narrow waist, wide hips, a luscious butt and tan skin and very pretty features that seemed to me to be Hispanic. Despite her large bust, her breasts were firm and full with very little sag suggesting either artificial enlargement or youth. I must admit that she was what I would have considered my ‘type’ of woman.

I thought it rather surprising therefore when I was drawn to the second woman. She was Anglo, fair skinned, shorter and slighter in build. I would describe her body as feminine but muscular rather than voluptuous. Her breasts were smaller but perfectly proportioned to her body and beautifully shaped. It was her face however that caught me. She wasn’t a beauty in the classical sense but there was something about her that instantly appealed to me. Perhaps it was her personality though I certainly had little enough knowledge with which to form any sort of judgment.

At Dianne’s orders the women undid the rope between my elbows and feet and then removed the strap holding my chest to my thighs. I moaned as my aching joints unfolded and my muscles moved ever so slightly for the first time.

Dianne waved at the Hispanic and said, “Time to meet your fellow slaves, Billy boy. This is Pillar. She is our cook and is also my sex toy. Pillar this is our new gardener. Just call him boy.”

Waving at the other woman she added, “This is Janice, my personal maid, housekeeper and, of course, another sex toy. As for you, little Billy boy, you will be joining them as the gardener and handyman as well as being my boy toy and sexual servant.”

What was all this talk about slaves? This woman wasn’t playing with a full deck. Slavery had been eradicated in the 1800’s. It had been abolished not only in my country but pretty much worldwide. But as I lay there an awful feeling crept over me. Diane might be crazy but no matter how crazy she might be I was the one bound and nude on the floor. Further, both of these women, did she say Pillar and Janice, were following her orders without hesitation.

Dianne told Janice to remove my catheter and nose tubes and directed Pillar to untie my ankles and knees. Both women moved obediently to their tasks. Janice slipped the nose tubes out and I found that despite the pain when they were inserted, they are not painful coming out. The catheter is another matter. I don’t know if the balloon didn’t fully deflate or if she simply pulled too fast but the feeling was as though a flaming brand was being dragged through the inside of my penis. Despite my inability to scream and my bonds I made some sort of noise through my nose and rose almost to a sitting position in involuntary reaction. Janice looked horrified and said almost reflexively, “Sorry.”

Diane pounced on Janice and said, “Did you speak without permission Janice? We will see to your punishment later. For now get him into the stocks.”

The Pillory

Once on my feet I noticed that the room we were in had three concrete walls and a fourth wall of bars like one might find in an old fashioned jail. I noted a number of rings on the floor and ceiling, a drain and a strange lower half of what appeared to be a pillory. It was a large wood beam mounted horizontally on top of a post set in the floor. The beam had semicircular depressions for the neck and wrists but there was no apparent top. I was led toward this device and halted. Diane, or Mistress as I was told to call her, told me to spread my legs. I must have hesitated because I got a nasty swipe with her riding crop. I saw no point in earning another and obediently spread my legs. Pillar and Janice dropped down and tied my ankles to two of the rings in the floor. With no hands and Diane behind me with that damn crop, I didn’t give them any trouble.

Any guy can tell you standing nude with you legs spread leaves you feeling quite exposed. With my ankles secured I was doubly aware of my vulnerability and just how exposed I was with all my dangly bits swinging in the wind.

Diane looked at Janice and said “Neck!”

Janice grabbed me by the hair, pulled my head forward and down so that I found my neck resting in the beam’s center depression. She reached down and grabbed a large block of wood with two flat metal straps bolted to it. Janice passed the block to someone, presumably Pillar, behind me. As the block passed back I saw that it had a half circle cut out of the bottom between the two straps. I couldn’t see but felt Pillar (I guess) settle the block over the back of my neck. Of course I couldn’t see what happened next but I now know Pillar pushed two bolts through holes in the metal straps that mated up with holes in the lower beam.

Once the metal bolts secured the top of the neck piece in place Janice released my hair. Of course the bolts made it impossible to lift the upper block and held me securely bent over at the waist. Janice ensured that the bolts would remain in place by spinning butterfly nuts over the end of the bolts. She didn’t bother tightening them. There was no need.

I felt some one working to remove the rope holding my elbows so tightly behind my back. That rope was then looped around the links of my handcuffs and around my stomach. Then the handcuff on my left wrist was opened. Pillar took my left wrist towards the appropriate cutout on the beam. I guess I instinctively tried to pull my arm back because Diane used the riding crop again. This time she brought it sharply up between my legs.

I didn’t fight after that. Pillar placed my left wrist in the cut out. Janice placed another block with straps over it. Pillar inserted the bolts and Janice twirled on the butterfly nuts. My right wrist followed, the rope around my stomach was removed along with the now empty handcuffs, and I was fully secured.

I am certain you can guess what came next. A nozzle was pushed into my all ready pumped up butt plug, and I was given an enema. It was a very large and very violent enema and it lasted a long time. I don’t know what was in it but I knew I had to go in a couple of minutes. This was not to be however as, at mistress’ order Janice set a timer for 15 minutes and set it on the floor in front of me.

After the liquid had flowed into me I felt some one nuzzle up to my rear end. I couldn’t see but ropes or perhaps straps secured this person’s thighs to mine. Then I felt the person behind me bend forward and her breasts press into my back. Her arms wrapped around my chest and were secured, probably with the handcuffs that had just been removed from me.

I heard Diane say, “You ought to know better than to talk without permission, Janice. I think that ought to be good for six.”

I heard the crop impact and felt the person on my back lurch six times and realized that Janice was being whipped, or at least cropped, for her involuntary expression of sympathy. I guess the cropping was pretty severe because I could feel what must have been tears on my upper back. After six slashes Janice was released from my back.

I was in too much pain by this time to really be aware of what was going on but I do remember something like a tape measure being wrapped tightly around my waist. In any event it was a long 15 minutes before the butt plug/nozzle was released and I was allowed to expel the enema along with whatever else was inside me. Afterward I learned the reason for the drain as Janice hosed down both the excrement and my rear, with cold water washing both my legs and the floor.

After the enema had been expelled Diane told Pillar to prepare dinner. Then she instructed Janice to shave me. I expected Janice to lather my face but instead Janice began to spread something, which I later realized must have been shaving cream, over my groin. Of course with gentle hands working over my testicles and the crack of my ass I grew a sizable hard on. Janice more or less ignored that, except that as she maneuvered it right or left to clear her razor she occasionally managed a frustrating pump.

All of which seemed to amuse Diane who told me, “I like to keep my slaves horny and frustrated. The girls have Benewah balls under their chastity chains but I don’t think I am going to have a problem with you. With all this female flesh in display I think you will be frustrated just fine.

"Now listen up because this is important. There are three simple rules you must live by. If you do you may enjoy life as a slave, or at least find it tolerable. If you don’t I will make your life a living hell.

"First slaves never speak except to answer a question. You saw what Janice got for forgetting that rule.

"Secondly, when you do speak you must always respond respectfully addressing me as Mistress or Miss Diane. Occasionally I may have guests. If they ask you a question you will address them as sir or madam.

"Finally and most importantly if I tell you to do something you will do it immediately and without hesitation. I don’t care what a slave likes or dislikes or what he or she wants to do. Your function, like that of the other slaves, is simply to obey.

Do you understand these rules?”

Still gagged and held in the pillory the best I could do was nod slightly but this was apparently acceptable to Diane as I didn’t feel the riding crop again. By this time Janice had finished her task and was wiping away the excess shaving cream and I was, predictably, rock hard.

Dianne handed something to Janice and I felt her moving under me. The pillory beam blocked my vision, of course so I couldn’t see what was happening, but I felt something cold on my chest. Then there was a tug, followed by a sharp pain and then a stinging sensation. This all happened a second time. Finally the stinging settled down to a dull ache. At the time I thought they had given me some sort of injections.

My attention was distracted as Diane instructed Janice to get the control belt first and then the chastity device

The Control Belt

Janice came in front of me to show me a metal belt similar to the one she was wearing. There was a single chain from the middle of the rear of the belt. Dangling from that chain was what appeared to be a large butt plug. The plug was out of some plastic or hard rubber material but had two metal strips at the extreme end. Janice lubed the plug and went around behind me to my still sore sphincter.

She slid the butt plug into me and held it deep within me as Diana pulled the chain taunt and wrapped the waist belt around me and locked it in place. It fit very snugly around my waist and the chain prevented me from expelling the plug. It was uncomfortable but not as big as the inflatable plug I had worn during the journey and I didn’t understand how it was supposed to control me.

Chastity device

Next Diana grabbed my testicles and squeezed. The pain was incredible. I wanted to curl up in a ball but, of course, being held rigidly in the pillory prevented that. Of course the pain over rode my arousal and my penis shriveled.

“I had to get you soft for this next part.” Diane said in a disgustingly cheery voice. Well of course she was cheerful. No one had just given her a pain in the groin. My testicles were still protesting the pain of having been crushed.

‘This next part’ was even more depressing. Mistress slipped a noose of string around the head of my now shrunken member, dropped the tail of the string through a curved metal tube and proceeded to pull my penis into and through the tube. The tube had two little ears or lobes with holes or more accurately slits. These were at the base where it was pressed against my groin. She held up a U shaped device of thin metal with two holes at the tips of the top of the U. A chain dangled from the center of the U. The U shape went under my scrotum up through the slits tightly holding the tube to my body. The chastity device was secured with a padlock through the holes. The narrow gap between the U shape and the base of the tube prevented any possibility of removing the device without either cutting off my testicles or first removing the padlock and the U shaped part.

While this was new to me, I had read about this sort of device. In addition to the discomfort caused by the weight of the device and the lock, the curved tube would make it both impossible to become erect and painful to even attempt an erection. At the same time I would be able to urinate freely though I would have to squat or sit if I didn’t want to wet my legs.

Standing at the foot of the table Mistress gave a slight tug at the chain which, of course pulled at my already painful balls. She instructed Janice to, “Let him stand up and release his feet. It must be about dinner time.”

Obediently Janice undid the butterfly nuts reached under the pillory to remove the bolts and then removed the three blocks of wood that had imprisoned my neck and wrists. Then she moved over to untie my ankles. I stood up and flexed my arms for a few seconds and then unbuckled the gag strap. Even with the strap unbuckled the gag was too large to remove from my mouth.

I glanced downward and found I had good news and bad news. The good news, I now realized, was that the pain on my chest wasn’t an injection. The bad news was that they had pierced me through each nipple. Both nipples now sported large nipple rings similar to the ones Pillar and Janice had. I had no problem with nipple rings. In fact I thought they looked kind of sexy on a woman. I did not want them on me. It looked as though I had no choice in the matter. Oh great, this was becoming crazier and crazier.

I waited until my feet were free and then pointed to the gag. Janice looked toward Diane and, apparently having received a nod, did something that let the bladder or balloon deflate. I pulled out the gag and turned towards Diane. I realized that for the first time since she had shocked me I was free.

“Now look…” I began. I say I began because at that moment a pain blossomed. No it didn’t blossom, it exploded deep within me and I dropped to the floor curled in a fetal position and momentarily out of breath. It wasn’t like the taser she had used in the hotel room. My arms and legs weren’t twitching and my jaw wasn’t hanging open but the pain was terrible. Actually it was too bad that my jaw was still working because as I started to get up I tried again, saying, “What…” The result was the same. Another explosion of pain and there I was curled up on the floor in agony.

Diane stood above me with some sort of remote control device that looked like a garage door opener. She said, “Come on! Get up and bend over the stocks. I told you not to speak unless spoken to and you better keep my instructions in mind or you are going to get shocked quite a bit. I hope you are a fast learner because I don’t know what long term effect there would be from many repeated shocks. Right now you spoke twice and are going to get a dozen lashes with my crop. ”

Shocks! That was mind numbing pain. Surely there was a better word, a more frightful, horrifying word than shocks for that terrible pain. Still I levered myself to my knees and then shakily to my feet and bent over to let my neck and wrists be refastened in the pillory. I realized that the belt around my waist somehow delivered an electric charge to the butt plug inside my colon, of such intensity that all my muscles collapsed. I understood then why Janice and Pillar were so obedient and, while I still wanted to escape and regain my freedom, I silently vowed to myself that I would do everything I could to avoid that dreadful pain.

The vicious beating began and eventually worked up to 12 strokes with the riding crop. My ass felt like it was on fire but the humiliation of standing helplessly nude before a fully clothed Diane to be punished as though I was a small child was almost worse than the beating itself.

End of part 1

Copyright© 2014 by Sir Richard. All rights reserved.