My Bondage, part 3 by Sir Richard

My Bondage
by Sir Richard
Part 3

Chapter 3 – Games

F/m, F/mff
Freedom
A couple of days after our terrible punishment Janice and I were again alone on the lawn as she brought me lunch. Trying to mask our actions to avoid further brutal punishment, I lifted the sandwich in front of my mouth and said, “I want to apologize for getting you into trouble and whipped like that. I had no idea of what she would do.”
Janice surprised me when, with her back to the house to avoid detection, she responded, “Forget it. You have nothing to be sorry about. In fact I ought to be thanking you for what you gave me.”
I was delighted to hear her response but couldn’t resist joking, “I didn’t think it was that good an orgasm.”
Janice looked at me the way a teacher might look at a particularly stupid pupil. She said, “Not the orgasm. Oh that was very nice too but I am talking about the freedom.”
My face must have looked puzzled because she continued, “Don’t you get it? For a brief while there we were doing what we wanted, not what that bitch wanted. My pussy was still chained and your cock was still locked in a tube but for six or seven minutes we were free and able to do just what we pleased. That’s a precious gift and why I want to thank you. Now, we have fooled around long enough, finish the water and let me get back to the house.”
I couldn’t help admiring this woman who wanted even a bit of freedom so much she was able to suffer brutal punishment and look upon it as worth the price. I imagined she must be of the same character as the patriots that founded our nation. Plus the fact that she was damn sexy. Well, I am a guy you know.
I handed her the empty water bottle and she deliberately fumbled it. She dropped to one knee to retrieve it and, still shielding her actions with her body gave me a quick kiss on my thigh. Then with a smile and a wink she turned and set off for the house. I watched and noticed that she was walking on the balls of her feet and swinging one foot in front of the other. Of course this firmed and shaped her calves and imparted a sexy sway to her ass. The little minx was teasing me.
By the way, the stories about keeping the penis in a bent tube are misleading. Sure I wanted to get hard and have sex, or even just masturbate. The thing is though that when you penis can’t get an erection the frustration, at least the physical sensations, are pretty much not there. I wanted sex but it was more in my mind than in my groin.
It would have been much more effective if the chastity device was a larger diameter, longer straight tube. That would have allowed me to get an erection but have prevented me from doing anything with it. I am certain that sort of design would have been much more frustrating.
Then I gave myself a mental head slap. Was I really thinking of how to make a more frustrating male chastity device? While what I was wearing didn’t allow me to get all horny and physically frustrated, it was bad enough, thank you very much. I could only put that line of thought down to how sexy Janice looked as she flounced her way back to the house.
As I thought about it I wondered if it was sex I wanted or the freedom to have sex. Janice was a smart woman and I think it was then that I realized I was in the process of falling, or perhaps had already fallen, in love with her. Whatever the case was, I hardened my resolve to somehow find freedom for both of us, no matter what the risks were.
The Sex Toys
None of my brief experience as Diane’ slave prepared me for what she called ‘a night with her sex toys.’ The first hint I had was when, after dinner and the clean up, I was led into my cell. Lying on top of the bed were the usual four cuffs. I was made to lie on the bed and the cuffs were attached to my wrists and ankles and instead of the loose face up position in which I normally slept, I was pulled tight. I was really stretched out.
When I was immovably stretched, Diane produced keys and gave them to Pillar who removed my chastity device and both her and Janice’s pussy lacings. The key was returned and both slave girls removed the Chinese balls. At Diane’ direction Janice cleaned the balls and set them aside while Pillar, who, you will remember, preferred women, was made to fondle and suck me to an erection. While Pillar wasn’t particularly enthusiastic or skilled at this, as you might imagine it didn’t take long at all for me to be fully stiff.
Then Diane produced a wire tie and a slotted bead. She slid the bead onto the wire tie and had Pillar fasten it tightly around the base of my erect penis with the bead at what would be the bottom crushing the internal tube through which my ejaculate fluids would normally flow. Diane smiled at me as this was being done and said, “This will keep the blood in your cock so it can’t get soft and at the same time crush the tube that carries sperm from you balls so that you won’t be able to cum.”
She then produced two collars with two short chains and cuffs attached. At first I was perplexed by these but I soon realized that even when Diane gave her slaves relief she did it in the most frustrating and humiliating way. The chains were long enough so that Pillar and Janice could play with their own breasts but couldn’t get their hands anywhere near their pussies. There would be no clitoral stimulation to help the vaginal penetration for either woman.
Since Pillar didn’t like men, it was predictable that Diane had Pillar mount my rigid penis. While I was hard and ready Pillar had trouble getting me into her and Janice had to lean over me and use her chained hands to guide me into Pillar. With some encouragement from Dianne, Pillar began to ride me. I had a brief glimpse of Pillar rising up and down while squeezing her breasts and tugging at her nipples.
The view was brief because Janice was now told to sit on me with her pussy over my mouth. Suitably encouraged with Diane’ riding crop I licked Janice to two orgasms while Pillar rode me to what sounded like a very satisfactory orgasm of her own.
I think the idea was to humiliate me but I enjoy eating pussy and wasn’t bothered by that at all. The sensations from my groin however were another matter entirely. At first it was very nice, just like normal female superior position sex. As time went on however first my testicles and later my penis began to protest. The signals indicated ejaculation but the wire tie and carefully positioned bead prevented relief.
After Pillar had cum, rather noisily, Diane ordered them to change positions. Now things really began to be painful. My jaw and tongue were aching from the exercise with Janice and my penis, despite the adequate natural lubrication that the women were providing, was beginning to grow sore and overly sensitive from the constant rubbing. Then too, Janice had just had two orgasms and it took a really long time to produce a further one.
As if that weren’t enough, Pillar decided to express her displeasure by moving far enough up my face that her slit was covering my nose. I thought that might have been an accident but when she smothered me three times relenting only when I was on the verge of passing out from asphyxiation I decided to object. I mean, perhaps I wasn’t Pillar’s preferred sex but her orgasm had sounded pretty good. I mean, what was the woman’s problem? At least she was getting to cum. The next time she covered my nose I nipped her labia. It wasn’t a real bite but it was enough of a nip that she got the idea and stopped playing nasty.
When both women had cum several times, at least twice on my mouth and once on my poor sore penis, Diane ordered them off and told them to clean me up. This was apparently to be an oral exercise because both women leaned over my face and licked me free of the copious deposits of female fluid that had accumulated. When they finished with my face they moved down my body to my groin. Now normally that would have been very pleasant but, as I said, by this time my penis was overly sensitive and each stroke with a tongue was actually painful. The pain was made worse by the ache in my testicles that were desperately trying to respond to the signals they were getting to ejaculate.
I had hoped the evening was drawing to a close when they finished the clean up chores or even that I was to be given some relief but I soon learned that this was to be all about pleasing the women and causing frustration and pain for the lone male. Diane produced a ball gag attached to a flat leather strip that covered the mouth and which had a dildo attached to the outside. I was forced to wear this and this initiated a new round of Janice and Pillar riding both the dildo and my poor over abused penis to one last orgasm. Actually I should say to two last orgasms as they each rode my penis to one and the dildo to one.
At that point Janice removed the gag and cleaned it while Pillar had the task of cleaning my groin. I tried to beg Diane for relief but hadn’t gotten two words out when she commanded me to silence, emphasizing her command with a vicious slash of her riding crop. Pillar’s cleaning of my penis was done with a rough wash rag and, though she was more or less gentle, by that time it felt as though she was using sandpaper. When they were done Diane had them reinsert the Chinese balls and re-lace their pussies shut. After applying the locks they were led away to their beds to prepare for the night.
I thought that I was going to be left with my aching testicles and sore penis for the night but I had forgotten that Diane, the mistress of ceremonies (pun intended), hadn’t gotten any relief herself. After the female slaves were locked away for the night Diane returned with a blindfold which she slipped over me. Apparently, as a mere slave, I wasn’t to be allowed to gaze upon my owner’s nude body. I know it was a nude body because in a few moments I felt a nude woman climb over me and settle her pussy on my mouth. I knew it wasn’t either of the girls because both of them were locked down on their beds for the night.
Diane had chosen to mount me facing toward my feet which not only made it harder to lick her pussy, it also allowed her to suffocate me simply by sitting up enough to encase my nose between the cheeks of her butt. She did this several time apparently enjoying it when I was thrashing about as much as my bondage allowed and gasping for air. Unlike Pillar, I had little opportunity to nip back and, frankly, given her riding crop I am not certain I would have taken the opportunity had it arisen.
Dianne encouraged me to keep my tongue busy by the simple expedient of reaching down and crushing my testicles whenever she felt I wasn’t sufficiently enthusiastic, generally when I was gasping for air. As if that wasn’t bad enough she jacked (jilled?) me off the entire time with some rough surfaced glove. I later learned it was a velvet glove but at that time it felt like a thousand needles jabbing into my poor sore penis.
It was in that manner that I brought Diane off to two orgasms. When she had enough (and I had more than enough) she climbed off and forced a bit gag into my mouth. I guess that Janice and Pillar had been similarly gagged as I heard nothing from them that night. Then she mounted my poor abused penis and rode it to another orgasm while I suffered in the blindfolded darkness. Somehow being blindfolded concentrated all of my senses on the pain from my groin making it an even worse torment.
While I couldn’t see past the blindfold there was enough light at the bottom, that I knew when Diane finally left and turned off the lights. I remained blindfolded, gagged, locked firmly in bed with a firm but very sore penis and aching testicles. It wasn’t my best night’s sleep.
The next morning I was marched to the pillory where with my wrists and neck locked in place and my legs spread and tied, Janice was allowed to remove the blindfold and my control belt. While she administered the inflatable butt plug and an enema, Diane crushed my testicles until the pain reduced my penis from its rock hard erection to stiff, putty like, half staff. At this softened condition Pillar was able to painfully, with some accidental jabs, at least I think they were accidental, work one blade of a scissors under the wire tie. She then twisted the scissors and snipped through the plastic tie freeing my penis. The renewed flow of blood created a terribly painful pins and needles sensation.
Pillar was then sent to make breakfast while Janice was required to get me erect with her mouth. Given all the pain I had this wasn’t quick or easy but Diane encouraged her with the damn riding crop and eventually I was erect again. Janice then milked me into a glass jar using both her mouth and her hands. Janice was wonderfully skilled with her mouth and the milking would have been very enjoyable if I hadn’t been suffering cramps from the enema while she was taking care of me.
The milking was followed by Diane crushing my testicles yet again; presumably to speed the softening of my much abused penis, and Janice installing my now flaccid organ into the chastity device. Janice then shaved me and, deflating the butt plug cleaned up the mess from my enema.
We had these sex toy nights about twice a week as it struck Diane’s fancy. They followed a similar pattern of multiple orgasms for all of the women and painful frustration for me. Of course they weren’t all exactly the same. Sometimes my knees would be drawn up, the control belt removed and one of the women would ream my ass with a strap on while rubbing my erect and tied penis with the now familiar velvet glove. The torments were many and varied but always consisted of satisfying both slaves and later Diane while causing me pain and sexual frustration. They always ended with the slaves locked down and me blindfolded serving Diane followed by a painful night and an even more painful milking the next morning.
My escape
Although the women had advised me against trying to escape, I was determined to at least try to get away. As I mowed, I had found that the property was surrounded by a rough stone wall about ten feet tall topped with broken glass set in cement to discourage climbing. There were also some electrical boxes near the top that looked like they would trip an alarm if the beam between the boxes was broken but that didn’t worry me. If I got over the wall I didn’t care if Diane knew I had made it. How foolish I was.
I figured I could hide out somewhere in the woods until I saw someone hanging out washing. Then I could steal enough clothing to allow me to mingle with the crowds. While the local police might be on Mistress’ payroll, once I was dressed and made it to some town, I didn’t think they would be much of a problem. I was pretty certain I could make my way to our Consulate and get my own government to bring pressure on the locals. If they were forced to look into Diane’s slavery, I would be able to free Janice and perhaps Pillar as well. My biggest concern was how to get over the wall while chained to a lawn mower and how to swiftly get across the broken glass without getting all cut up.
I thought I had a chance when I finished the mowing and was going to be sent out with the light weight edge trimmer. Unfortunately Mistress had anticipated me and I found the six foot chain attached to my chastity device was now locked to the heavy metal lawn roller. The six feet gave me a reasonable amount of movement but then I had to put down the trimmer and use both hands to drag the roller to a new position. Clearly there was no way I could climb the wall without using both hands and that was out of the question with 60 or 70 pounds of weight dangling from my scrotum. I had already experienced what would happen if I was caught with an empty roller.
Each day of slavery followed the pattern of the first. First into the pillory, have the belt removed and suffer through an enema. While this was going on recharged batteries were put into the shock belt. Of course the battery compartment was only accessible from the inside of the belt when it had been removed. Then it would be install the shock belt and off to breakfast and then work. Each day Janice coated me with suntan lotion creating an uncomfortable case of blue balls. Then the mistress assigned that day’s labors and left me to get on with them.
It wasn’t until the fourth or fifth day, when I had finished the edging work and was pruning the shrubs that I had an idea. The metal belt around my waist was tight but not so tight that I couldn’t pass a link of the chain between the belt and my body. I made certain that I was out of sight and let the water out of the roller. Then I worked the chain through the belt, up under my chest and then over my shoulder, around the back of my neck and down the other side of my chest, tying it off at the belt. It wasn’t perfect. The still heavy roller hung from my shoulders but at least it didn’t drag on my genitals. It awkwardly banged against my knees as I made my way from the shed to the most secluded part of the wall with the two towels I had stolen to protect my hands.
When I got to the spot I had chosen I gripped the towels in my teeth and began the climb. It was awkward with the damn roller but I was nearly to the top. I paused to flip the towels over the jagged top. I knew that once the towel broke the beam I would have to move fast, so I worked my feet as high as I could, sort of crouching. Then I flipped the towel over the wall.
As soon as the towels were over the glass I climbed over the wall and dropped down on the other side. I set off at a trot to find some place to hide and eventually some clothes to steal. Perhaps I could use a rock to break the padlock and get rid of the damn roller as it would make me stand out like the proverbial sore thumb.
I don’t think I had gotten more than a mile from Diane’s estate when a police jeep caught up to me. I was caught so I reluctantly raised my hand as two cops climbed out. I tried to ask for help in Spanish but the cops didn’t even bother responding as the approached me. They had both drawn wooden police clubs but I thought that was just a precaution and I raised my tired arms further over my head.
The younger cop just rammed his club into my stomach. Of course I doubled over and the older cop took advantage of my position to club me on the back of the head. I don’t remember the exact sequence of blows after that but they rained down on me fast and furious. I tried to cover my head with my arms but it didn’t do much good. I was driven to the ground and one of the cops pinned me there with his boot while the other one hand cuffed my hands behind my back.
I was then hauled to my feet and half marched, half dragged to the jeep where I was pushed face down on the floor in front of the rear seat. My ankles were forced up and then handcuffed on either side of the roll bar ensuring that I couldn’t get up or even roll over. Hand cuffs have a circular opening and ankles are oval. It isn’t a good fit and the metal dug painfully into my ankles as the jeep bounced along.
At that point I still harbored some hope that, despite the rough treatment I had received, I might wind up in a police station where someone might listen to my pleas for help. That hope disappeared as we drove through the gate back to the familiar lawn of Diane’s estate.
Dianne met the jeep and watched as the cops removed the leg cuffs and then the hand cuffs dumping my battered body on the lawn. Urged by Diane’s riding crop and threatened by the terrible remote control I was taken back the pillory and fastened by the neck and wrists with my legs spread and tied to rings in the floor.
Punishment
They say that criminals are not deterred by the thought of punishment because they never think they will be caught in the first place. I don’t know if that is true or not but I certainly hadn’t considered what might happen if my attempt to escape from Mistress failed. What followed was long and brutal. It was bad while she was hurting me and worse when she left me.
Let me explain that. Diane directed me into the large room with the drain and put me in the pillory. I spent the next two days with my legs spread apart locked into that damn device. The thing with a pillory is that you can neither straighten up nor kneel down. Any change of position causes a terrible strain on your neck that is held rigidly parallel to the floor. Your back aches, your shoulders ache, your legs cramp and twitch but you just can’t move. The human body just isn’t designed to hold the same position over long periods. Then to, there is the intense fatigue. Every time you start to drift off to sleep your body tries to relax and change the angle of your neck to the floor. Of course this is impossible and the pain on your neck snaps you back to full wakefulness and forces you back into position.
Now that would be torture enough but not for that bitch Diane. First she caned me. Twenty five lashes spaced from just below my waist to the top of my thighs. Each stroke delivered after a pause to allow the pain of the prior stroke to spread and radiate through my body. Then, splat, the next one was delivered. Every stroke was administered by an expert arm with the full force of her body powering the swing. She left me un-gagged so that she could hear me scream and believe me, I did.
After a pause during which Janice was sent to bring her a glass of something cool, she came at my back with a flogger. It wasn’t quite like the royal navy cat-o-nine tails. Those things ripped backs down to the bone. Still, she managed to cause plenty of pain. She started out with light strokes to, as she explained, wake up the nerves. Then when my back was raw and fully sensitive she began the heavy flogging. My back felt as though it was on fire by the time she stopped. The thing is, it kept burning even after she had stopped. It felt like a very bad burn, perhaps the worst case of sunburn you could imagine.
While she refreshed herself she had Pillar butt fuck me with a strap on dildo. Just to be particularly nasty she tied some weights to my scrotum and then had Pillar lube the strap on with heat generating muscle cream. Of course the inside of my rectum soon felt as though it was on fire and the constant banging against my rear did nothing to sooth my buttocks. Further, as Pillar thrust forward she banged my butt causing the weights on my scrotum to swing back and forth tugging my testicles. At mistress’s direction, Pillar continued to ream me until she, Pillar, had an orgasm.
I had hoped we were done when Janice was sent off to clean up the strap on and Pillar was sent off to prepare dinner. That proved to be overly optimistic as Mistress returned with the flogger, aiming at my thighs and dangling testicles this time. Again she demonstrated her expertise leaving me on the verge of collapse but forced to remain fully awake by the constraints of the pillory around my neck.
I was left in this condition overnight with my body burning in pain and unable to move. Hunger and thirst added to my discomfort.
Apparently I must have looked as bad as I felt because Janice was allowed to feed me dry toast and water the next morning. This was done awkwardly as I was still locked into the pillory. Apparently Mistress didn’t want me dead. That would have lost her the time and money she had invested in capturing me. Instead I had a relatively quiet morning enlivened by another flogging from neck down to my knees. Then it was Janice’s turn to ream me with the muscle cream coated strap on. Apparently Mistress didn’t find her energetic enough because I heard several commands of ‘harder’ and ‘faster’, each accompanied by the sound of a crop or a cane striking Janice on the butt.
After Janice had her orgasm, Diane went back to flogging me so that my back and legs were once again burning with pain. It wasn’t until after another sleepless night and uncomfortable morning that I was finally released. Diane reinstalled the electric butt plug and control belt and let me down from the pillory. While I had no doubt she was had enjoyed my painful cries while she was punishing me, she also wanted work from her male slave.
She solved the wall climbing by leaving off the heavy lawn roller but keeping me chained to the lawnmower. While it was slightly lighter than the full roller, the lawnmower was bulky and awkward to lift or carry. It would be impossible to climb a wall while chained to it. In addition she doubled the chain so that I was only 3 feet from the machine instead of the previous six feet. There was no way to loop this shortened chain over my shoulder to take the strain off my groin.
Other Sex Games
While I have described our sex toy nights, Diane didn’t restrict her orgasms to those infrequent evenings. While it didn’t involve me at first, I learned that most afternoons were also time for the mistress to play. Generally Janice’s chores were completed by early afternoon and once Pillar had cleaned up from lunch she generally had time before beginning to prepare Diane’s dinner (the slaves’ dinner only required microwaving three bowls of canned stew so little or no preparation time was required).
Generally these play times would be on the back deck around the swimming pool. They would vary depending on the Diane’s mood. Most frequently one slave would be tied on her back to a lounge, while the other woman, generally with her hand bound behind her, licked Diane to several orgasms. When Diane was satiated she would force the more or less free woman to tease and arouse the tied woman by licking her nipples while Diane would ‘encourage’ her efforts with occasional use of the riding crop.
Variations on this theme occurred as Diane’s moods dictated. She might, for example, remove Janice’s crotch chains and Benewah balls while keeping her hands secured behind her. Then she would have Janice mount the prone Pillar and have Pillar give her an orgasm. Equally she might stop Pillar just when Janice was about to orgasm. Of course some days the positions would be reversed and Pillar might either have an orgasm or be held on the edge at Diane’s whim. The only constant in these games was that Diane always had two and sometimes three orgasms.
When I was first put to work the grass was long and the plants overgrown and there was a backlog of handyman chores to be finished. I worked from breakfast until dinner. As I got the lawn cut short, rolled, and trimmed my workload decreased. Similarly the ‘to do’ list of minor repairs was cleared up item by item. After several weeks my work schedule changed and I worked only in the mornings, being summoned back to the house for lunch (inevitably a sandwich and bottle of water, but at least we could sit on the floor and eat with our hands).
Actually I viewed this as a mixed blessing because it gave me less opportunity for those hasty whispered talks with Janice. The reduction in work load also meant that I was available for the afternoon play times.
Generally my participation was to lick and suckle the nipples of the woman that was tied down while the other one ate Diane’s pussy. As a practical matter that generally meant I was playing with a bound Pillar, who didn’t like men while Janice, who preferred men, was busy licking Diane.
I found being required to arouse a woman who didn’t like men was something of a challenge. Pillar’s body responded to the physical stimulus as I played with her breasts but I found it an opportunity to vary my approach to see what brought her nipples to the most turgid in the least time.
Surprisingly I found that just licking and suckling, which had generally been my approach, was considerably less effective that just using my tongue to lightly circle her nipples. Most effective of all was using the very tip of my tongue to barely make contact with the very tip of the nipple. I tried to be as light and as fleeting as the kiss of a butterfly. This light but repetitive touch not only raised her nipples more rapidly than anything else I had tried, it also wrung moans from the reluctant Pillar.
Of course sometime I was tied and Pillar worked on arousing me, both by playing with my pierced nipples and licking and sucking on my scrotum. At first she played games with my scrotum by nipping a bit but she found that I could reciprocate the next time I had her nipple in my mouth and soon decided that trying to arouse and frustrate me was a better game. I have to say that she did a pretty good job.
Occasionally Diane decided to play other games with her slaves. My favorite was the ‘69’ game where both women had their hands tied behind their backs. Then I got to remove the crotch chains and gently pull out the Benewah balls and fastened the women together face to groin. They were tied at the waist and thighs with Pillar’s thighs holding Janice’s head in her groin and visa versa. At a signal both women would begin to lick the other. The objective of the game was to bring your opponent to orgasm before you came.
Both women had the Benewah balls reinserted and their pussies once again chained, a task which I rather enjoyed performing. The looser of the game was then spanked by the winner. This was particularly hard on Pillar when she lost as it turned out that she was a mild pain freak and was aroused by being spanked by Janice.
My least favorite, but I suspect Pillar’s favorite, game was ‘dunk the boy.’ In this my wrists and elbows were tightly tied, my ankles were tied to my thighs and a line was passed across my chest, under my arms and tied behind my back. Then I was lowered into the pool, towed to under the diving board and fastened to the underside of the diving board, so that my mouth was just above the water line.
Then all three of the women went diving and swimming. As you might imagine each dive required several up and down jumps on the edge of the diving board which caused me to submerge. How deep I went depended on how hard the jumps were but even the slightest of jumps put my mouth and nose below water while some harder jumps managed to dunk even my eyes.
Of course, under the board I had no way of knowing when someone was coming and had to guess as to when to breathe and when to try and hold my breath. I usually got it wrong and wound up gasping for breath having only seconds between the first jump and the second to grab some air. I guess I was never in any real danger of drowning but all three of the women, yes even Janice, thought it was a great game. Add to that, sometimes Janice would swim underwater and use my scrotum as a lever to pull her to the surface. I would have been angry with her but she generally used it as an occasion to give me a quick kiss, so I couldn’t really get mad.
I more or less got my own back on those few occasions when Pillar was eating Diane and my job was to tease and arouse Janice. I found that Janice had very sensitive nipples and that I could manage a bit of rubbing over her chained but still sensitive labia. I also managed, while Diane was otherwise occupied, to steal some kisses which Janice reciprocated very ardently.

End of part 3

Copyright© 2014 by Sir Richard. All rights reserved.