Eight Days in a Binding Contract

Sir Michael and I have discussed our individual sex activities for years. I know that at times with his friends he has dabbled in bondage, but it's not really his thing. He's claustrophobic. I have heard numerous times about his sling in his garage and his escapades using it. Lots of stories of gang bangs here too. But not so much about activities with bondage furniture though, so I was curious of why he had such a well-equipped dungeon. I know it wasn't for his massage clients. He must have been reading my mind. He told me as we were finishing up the tour of the room that many of the pieces of furniture were not his. He had borrowed them from some of his friends who are more into the bondage scene. He said they had offered him advice on my training and envied the opportunity he was going to have with me. I got a twinge of anxiousness with the thought that these practiced bondage friends could be potential guests. Sir Michael then indicates the level of effort he had to extend to insure all the toys and furniture were clean and sterile per our contract and I should expect significant punishments throughout the week to make up for his efforts to outfit the room and then to make it clean just for me. Now I'm even more anxious as Sir seems to be aroused by the punishment aspects of my ordeal. Me, I like the bondage and restraints the most, I think. Well, maybe I need not worry, he's just showing he will try to fulfil my wants. I see that my mind will have as much of a workout as will my body. Who would have thought?

The atrium was nice. It was between the dungeon and master bedroom. The three places I would likely be spending most of my time are all connected. It had a wood deck floor made of smooth 3-inch-wide fine teakwood boards stained red, bordered by nice flowerbeds. Large flowerpots and patio style chairs adorned the deck. The atrium has four enclosed walls, the bedroom wall, the garage wall, the wall of the garage of the adjacent condo, and an outside wall that faces the street. This wall was lower than the other three and allowed for the sloping mostly open roof which was comprised of open 2x8s and a center heavy wood beam. I told Sir that the space was nicely decorated. He obviously had pride in the space, and I was told it also had accent lighting that would make evening sessions with me very nice for 'him'. The space was isolated from view, but the light road traffic and pedestrians could be heard. I was warned that when playing out here any outburst from me might be heard and that I would be severely punished if it happened. He also stated that I should expect to be gagged if I was secured there. He had a reputation and a business to protect.

He then added there was no time like the present to see if I would control myself. He told me to undress in the bedroom. Leave my clothes on his bed. I was then to report back to the atrium. I did so quickly. When I got there, Sir had a power drill in his hand and the Home Depot bag. He then indicated that outside bondage was at my request so I should install my own securing hooks and chains here. He showed me where he wanted the eye hooks installed so that they would be hidden, and I completed the task along with attaching the six-foot chains to them. It felt weird as this was the first time I had ever completed a drill project stark naked, and while not visible, still outside to boot. That is, naked other than the chastity device which was still in place. Sir Michael then had me move some of the chairs and flowerpots to the side, making for a completely clear space in the center of the deck. The moment I was done, Sir pulled on the chains to see that they were indeed secure then told me to lay down spread eagle on the deck. I complied immediately thinking I wish I had been able to take a pee first. Not wanting to add potential discipline I ignored the desire. Sir Michael retrieved four leather cuffs from the shelf in the garage and placed them on my ankles and wrists. He then placed miniature locks on each of the cuffs so that the cuffs were not removable; not that I could have gotten them off anyway. He then maneuvered me around so that I was evenly space between the chains that extended from the four corners of the deck. These were then secured to the cuffs with full sized keyed padlocks. As he attached me to the chains, he made sure each of my limbs were as taught as he could get them, limiting most, if not all, of the movement of my limbs. He then said; "FYI, the little cuff locks are not keyed the same, but they are marked. The padlocks are all keyed the same. Just following the rules, I expect you to do the same. Always. Now how do you get that chastity thing off?"

"You have the key, Sir. Just unlock the lock, then the parts will easily disassemble." And off it came, a little sticky, pre-cum I guess. He stepped away into the garage and came back with a narrow blade riding crop. "Take a deep breath" and in a split second I am rapidly hit three times by the crop, twice in the ball sack and once on my shaft, both of which in my current predicament are fully exposed and unprotected. "Now, try to remember not to put that damn thing on without permission." "Yes sir" I meekly responded, still catching my breath. "Did you bring a gag?" "Yes sir, different kinds. They are in the yellow tool bag in my suitcase." I had brought a ball gag, two ring gags, a penis gag and a piece of cut sponge for filling my mouth if stuffing it was the master's pleasure. Also in the bag, were two hoods, one a lighter style leather hood with zipped eye holes and mouth hole that secures by laces up the back, and a severe hood with no openings other than two small 1/4 inch grommeted holes by the nose. It also laces up the back but in addition has three 1-inch leather straps that tightened around the neck, over the chin and across the eyes, making it very tight and restrictive around the face and head. It feels great when on if you have that kink, I do, but it's not for the claustrophobic. Very tight and restrictive, evil looking too. I also brought my two favorite Lovense programmable butt plugs, my favorite leather wrist and ankle cuffs, a set of four hospital style cuffs and companion restraint straps, a leather padded blindfold, a large neck collar with attachment rings, a dog collar and two leather riding crops, one of which along with the wrist cuffs had been previous gifts from Sir Michael. There were some other toys including my two Wartenberg wheels, a leather ball stretcher and a pair of nipple clamps.

Sir Michael returned with a selected gag and my blindfold, fastening the ball gag in my mouth much deeper and tighter than I do when I play self-bondage at home. Then on went the blindfold. "My inspection this morning found you a little pale. I assume that's common to you Easterners. I'll let you catch a little sun here, then if the mood strikes me, maybe I'll apply some suntan lotion on you. Enjoy." And I believe he went into his bedroom as I heard the screen close, but not the sliding door. My first thought was he was supposed to stay within view if I was gagged. Certainly, possible from the bedroom but I didn't know. I was going to call out, but then thought, No Fool, that's punishment for sure as I had been firmly warned.

And there I laid. In mid-May it is warm, no make that it is hot in San Diego. Sir Michael has a chiming mantle clock in his bedroom so although blindfolded I could somewhat keep track of time. About an hour into the ordeal Sir Michael called out, "I'm going to look for that Suntan lotion." Good, I thought I'm certainly perspiring here, and I think I'm starting to burn. Listening to the clock it was more than fifteen minutes to get the lotion. I must admit, though, so far, I was really enjoying just lying there outside tightly spread eagle. My neck was sore as I had no pillow, and my head was sore too from where it was resting. Otherwise, I was fine.

I was squirted with the lotion, an unexpected shock. The spreading of the lotion showed both that, yes, he is a professional masseuse, and that, yes, he is gay. The lotion was applied everywhere he could reach. And I was made hard, although no further action was taken. Then without a word, solitude again.

I was in deep thought when I heard the phone ring and a few minutes later Sir Michael returned to advise he had a customer coming over in about 30 minutes. He could let me up and put me in the garage or leave me here. While I couldn't see him, I knew he was thinking it through. "I must do a little prep before the client gets here, plus I have to stow your luggage that YOU didn't put away. We will revisit that later. So there really isn't time to properly resecure you elsewhere. So, I've decided to simply leave you here. Nod your head if you don't think you can make it. It's a half hour till he comes then about an hour and a half till he is done and gone. Before he gets here, I'll come remove the gag because I must close the drapes and I then won't be able to see you. Our agreement is you are within view when gagged."

I nodded in agreement, relieved that he did remember that safety precaution and had been watching me, besides there was not much else I could do, and at least for now I was OK. About twenty minutes later he did come back and removed the gag, which really felt good. I wasn't use to one being in so tight, although I did like the sensation. He then pulled my head up and said drink some water. I got most of it in from the water bottle, some dribbled down my neck. He then asked if I needed anything else. Risking possible punishment, I said "Yellow, could I have a towel or pillow for under my neck and head?" Into the house he went and then quickly back. I now had two towels, one rolled up under my neck and one cushioning my head. He may be playing the Dominant role but he is being compassionate and isn't brutalizing me, at least not yet. A second sip of water and he was gone again. I heard the door shut and lock.

Wish I had some music. I listen to the street traffic, which is minimal, Sir Michael's home is on a Cul-de-Sac. You do hear nature scurrying around and birds tweeting. I get the willies thinking of the possibility of insects crawling on me but then that is part of the mystique of being bound outdoors. I couldn't hear the clock anymore. Time passes slowly. I really needed to pee. That water was a blessing and a curse. This is probably the longest I have ever been bound in one position in a long time. At least the bondage is comfortable, although my shoulders are starting to ache. I have minimal movement, but enough to keep from cramping. Sun is still warm but has lessened, it doesn't seem to be beating down on me anymore. It must be getting late. I'm hungry, sure, of course, I didn't have lunch.

Finally, I hear the door open. "Hey Bitch, you had enough for a while? Let's eat, you're going to have a busy evening."

Chapter 4 The First Evening and Night in Bondage

Friday evening. "Go take a quick shower and wash out your butt hole. You know how? I told you to look it up online last week. There is a clean shower douche wand on the toilet. And put on your chastity thing and then give me the key. Jeans and a tee shirt, no underwear. Hurry it up." he commands. To save time I pee in the shower, what a relief.

Now clean inside and out, chastity belt on and locked, dressed, and ready to go, we head out to P.F. Chang's for a nice meal. While out, conversation is normal. I don't get dessert as I am worried about the possibility of another weigh-in. Sir orders some butter almond ice cream with chocolate syrup for himself, something he's been getting since college days, I see normality as a blessing for me. I paid the check, and we went. It's now dark out. As we get to the car, Sir Michael says "Stop, put your hands behind your back." And then, snap, click-click, snap click-click my wrists are handcuffed together. Discreetly standing between me and the Jeep, blocking the general view, he then tells me to open my mouth and he slips in the penis gag I had brought from my collection, buckling it tightly behind my head. I think he's gotten it to the last buckle hole. Both the selection and the application surprised me. It's a little larger than the ball gag from earlier. This one fills my mouth more, it rests on my tongue which can stroke it. It has a large leather front piece that holds the penis to the straps. It is one of my more favorite choices when I am doing self-bondage as I like to run my tongue around it when it's in my mouth. The penis shape is not very long, but it is pretty authentic. My oral familiarity with it is one of the reasons I think I'll be able to potentially bare having a real one in my mouth this week. But of course, that is someone else's prerogative. I just don't usually have it strapped as tightly as Sir Michael has just done. I keep it loose for safety reasons when I am alone. I can usually push it out with my tough when needed. Not this time. The car door is opened, and I'm pushed in. He sits me upright and buckles my seatbelt. We drive home. This treatment is kind of exciting. Out and about driving cuffed, secured, and gagged. Tightly gagged. I think please drive safely; we don't want to be pulled over by the cops.

It's a short ten to fifteen-minute drive. We get home, and he helps me get out of the car and then I am marched into the house with him securely holding my cuffed hands. I am taken directly to the bedroom and ordered to kick off my shoes and drop my pants. I had a small struggle with my hands being cuff but having a straight waist I quickly get it done. I am put in front of the pegging bench and told to climb up. It too is difficult to get on with my hands cuffed behind my back, but a manage. Sir Michael straps my legs to the leg rests and pulls off my socks. I'm told to sit upright, and my handcuffs are released. I am then told to pull off my T-shirt and lay back down on the chest and arm rests. My arms and body are then promptly and firmly secured to the bench. A blindfold is applied. The bench is kind of comfortable. I wait. I hear Sir fiddling around the room, then I hear sex sounds, groans, sound of ecstasy. Seems like he's watching porn. About a half hour seems to pass, when suddenly and without warning SMACK. My butt has been wacked. It stings, but the unexpected shock of being stuck overwhelms any real initial pain. I hear "One" announced. Now I begin to feel it, my right butt cheek is smarting. Then a hard smack on my left cheek. 'Two". Then my right again. "Three." Then its "Four." "Five." "Six." "Seven." "Eight." "Nine." "Ten." With a matching strike coming before each number. Intense and not rushed. I am so glad I have the penis gag in my mouth as I am biting down hard doing all I can to not shout out. Then there is a pause. I feel my blindfold being lifted and I am shown the weapon just used on me. It was my 26-inch-long leather riding crop with a 1 1/2-inch-wide tip that I had brought. My wife had used it on me a few years ago. Maybe two of three taps on my butt and member and it never hurt like this. Master must have used full swings on the crop, these were no love taps. I think to myself, hey, I did this to myself, so bare it. My blindfold is pulled back down and then nothing. He must be watching porn again.

Maybe fifteen minutes have passed, my butt stinging has dissipated, and I then feel a cold ooze run down the center crack of my butt checks. Then insertion. There is a finger in my butt hole. "Eck, oooh" Unexpected, yes, but keep your mouth shut, stay under control. Finger in, finger out. Finger in, finger out. Finger in pretty deep, finger out. Finger swirling around, in and out. "Owww" Two fingers in. Stay quiet, this isn't too bad. He's being gentle. He knows I'm new to this. Two in, two out. Now three, no please no. He must feel my tensing up and withdrawals. Now I feel vibration. Vibration and penetration. A vibrator is being inserted. Not bad, he's going easy. He's training me to take this. If he plans to screw me with his big dick I'm going to have to take much more than this. He works the vibrator in and out for a short while then withdrawals. A moment or two later, more lube is applied, and I go another round of one, two, three fingers and a vibrating dildo. Out they come, then another plug, this one, non-vibrating is pushed in. This feels like a traditional plug that is wider in the middle than at the tip and then decreases so the butt hole closes around it and holds it when it fully pushed in. It is not small. "Take it Bitch, relax, open up your hole" he scolds. I don't have any choice in the matter, all I can do is take it. Sir Michael, obviously an expert, works the plug with finesse and sets it in place. The sharp pain caused when my rectum was forced over the widest section quickly subsides when the port closes around the throat base. I feel full, a little uncomfortable, but okay.

Then abandonment again. Maybe another ten minutes of just being secured to the bench, blindfolded, gagged and plugged. Then out of nowhere, TWANG. I jump but go nowhere as I am tightly secure to the bench. My right ball has been stung. "Eleven". Then the left ball. "Twelve." Right ball. "Thirteen." Left ball, right ball, then my dick head, back to the balls, right, left and again the dick head "Fourteen, fifteen, sixteen seventeen, eighteen, nineteen." Then the center of my bag is struck. "Twenty." Oh my God, oh my God, oh my God, AHHHH. Thank goodness for the gag or I am sure there would be more administered for losing control. Damn my balls are stinging. The dick not as much. Down again comes the blindfold. What weapon had he used? What is that? Oh geez, chopsticks from P.F. Chang's. And I paid the check for this dinner experience. He bends back the stick with one hand while firmly holding the base with his other hand and twangs my face cheek. Ouch. How resourceful, cunning, and skillful; my old friend has become quite the Devil. He is playing this Dominant role well. And back on goes the blindfold.

Twenty? OK this must be the overweight punishment. Three pounds over the limit. That means ten more to go. And I wait. I wait for a punishment I agreed to and now do not really want. I'm not sure I could explain to others why this is a fantasy I dreamed of and set in motion. But here I am, bound, blindfolded, gagged, plugged and still stinging. I feel tugging at my butt. Master is pulling out my plug, it's coming out easier than it went in. Pop, it's out. It does feel better out than in. A moment passes then, whiff, yeech, the plug is dabbed under my nose. My upper lip is wet. "You did a poor job of cleaning yourself out, I'll remember this Cunt." He wonders away and returns a few minutes later with more lube, fingers in me again, starting right away with two, in and out twirling, then its three. His hands feel like they have gloves on. He must really be unhappy with my cleanliness. I'll pay, I know. Now, a bumpy dildo is being inserted. It feels like a stacked column of round balls. Ahhh, this is hard, oh, too deep, too deep! It's long, with rounded bumps that continue till it reaches its base. As it is push along each bump seems to stretch my hole, closes, and then stretches again. Sir Michael is slower to react to my tensing up this time, less merciful. "Relax, relax" he commands. I do all I can to accept the intrusion. "Enjoy this, it's what you asked for." He lets up a little but keeps pushing it further into me. He seems to be done now, I don't feel his touch anymore, but he has left the long dong in me. I have no idea how long it really is, but I feel pressure and discomfort deep inside me, painful, but it is bearable. I do not need to call out my yellow safe word. I rest, as time goes by, there is no more discomfort. He must be watching porn again. He seems to have turned up the volume on whatever he is watching. Sounds like someone is getting a great blow job. It must be at least a half hour since I've been touched. I keep listing for the clock chimes, but my mind is wondering, and I lose track of the chimes. Then without warning SWAT. Ouch! "Twenty-one." I can tell this is a paddle. Feels like leather. Must be the one I saw in the Dungeon. Left butt cheek three times in a row, then three on the right. Two left and two right, these last four are a little lower and a bit harder. Stingers by the end. "Thirty." My butt must surely be bright red. It's a spanking I'll remember. "Now never show up fat when you promise to be fit." This was said to me calmly, in an even, non-angry tone. He is coaching, teaching his new submissive in how he is to be serve. Punishment for the transgression has been paid. A lesson learned and reenforced. I pray he doesn't plan a daily weigh-in and I am punished after each. The dong is extracted, and I feel gloved fingers once again entering my anal cavity. One, two, three fingers, probing, flexing, twirling, in, out, in out. This actually feels good. It seems easier to take. "Do you feel that? Good, isn't it? I'm messaging your prostrate. Anal play feels good when you accept it and stay loose. I could make you come this way." He continues his probing while addressing me. "I've stretched you. That's good. If we do this a few more times and you'll be capable of accepting dicks without tearing. You've done well, Bitch, I'm both pleased with your progress as well as your acceptance of your punishment." He withdrawals and I hear the gloves coming off. Soon the straps are being released and I'm told to climb down from the bench. I'm a little weak kneed. I rub my butt, it's tender. My balls have seemed to recover from their ordeal. I'm told to remove my blindfold and gag and I do. It seems I may be done for the evening.