Eight Days in a Binding Contract

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.

“Where is your chastity belt? Go pee, then put it on. I follow my directions and give Sir the key. It’s bedtime for you. I look at the clock and see it’s a little past 11:00, 2:00 in the morning East Coast time. I’m beat, it’s been a long day. I foolishly think I’ll be getting a good night’s sleep. I see Sir has my leather hospital style waist restrain belt and two cuffs in his hands. He beckons me over and puts cuffs on each of my wrists. He threads the belt through the cuff anchors and secures the belt around my waist. He engages the built-in slip lock. My hands are now secure to my sides until he sees fit to release me. He has the key on a string around his neck like a necklace. I am naked other than my chastity and restraint.

I’m directed to the bathroom. Master’s bathroom has a forward area with double sinks and counters on one side, sliding door closets on the other. Then there is a second smaller room to the rear housing the toilet and walk-in shower. It has a door that can be closed for privacy. He points to the walk-in shower stall and says laydown there. I follow his direction, though it’s a little tough with my arms at my side. The tile floors and walls are cold. Real cold, a little wet too by the drain. I am shocked and shivered as I lay down on the floor. He steps away and returns with a throw pillow and wool blanket. Wool! “Our agreement was sleep where I say, with a blanket and pillow. I have fulfilled our agreement, my little Bitch. Remember, this is your fantasy, not mine, I’m just making it happen,” Sir says in a sarcastic tone. He turns, shuts off the light, leaves pulling the door closed behind him.

Total darkness. He’s correct, this is mostly of my doing. And, yes, while I am suffering, this is what I asked for and this is just the end of day one. I do my best to get the scratchy wool blanket both under and over me to shield me from the tile. I try to get comfortable and fall asleep. It is a bit of a struggle; my hands secured to my waist on a hard tile floor, naked, wrapped in wool, overly tired. I slip in and out of sleep, not knowing when the morning sunrise has come while lying in this darkened windowless bathroom.

I am woken twice from sleep during the night as Sir Michael comes in to take a piss. I’m thankful he doesn’t just turn and unload on me. After hearing him go the second time, I too, get an uncontrollable urge to go and therefore must struggle to rise from the floor and use the toilet. Peeing through the slit of my chastity device is strange, but I have done it before, never, however, without use of my hands to direct the angle of the device and in complete darkness.  Directing it to the bowl will be a challenge, just finding the bowl was a challenge. I decide to just try to take a sit-down pee. I back up to the toilet and sit down, a mistake, as the seat is up from Sir Michaels recent deposit. I must have been an interesting sight.

I just say to hell with it, with my butt stuck down in the cold rim of the porcelain bowl, I began to pee. I can’t touch my encased member and I pee through the opening in the cover provided for just this use. I cannot see it or for that matter anything in the darkness. I bend over as far as I can to make sure my stream is in the toilet and not running down the front of the bowl, a likely criminal offence to Sir Michael. Finished, I struggle up, fumble around with what little movement I have with my hands to flush and I shuffle back to my blanketed floor, with my butt a little moist and some urine dribbling down my leg as I have no ability to shake my dick dry.