Eight Days in a Binding Contract

I felt him behind me as he put his hand on my back and then squirted lube in my hole and smeared it around my crack. He went to work with his fingers, first one, then two, then three, in and out, swirling and probing just like he did the night before. He worked the prostrate which made my dick a little hard which Sir immediately noticed and made comment, then with his lube coated hand added my dick to his fingering rotation making the butt stretching a bit less tedious. He switched to using an assortment of dildoes, three by my count, one a vibrator, increasing the size of them till my body baulked. I was worked side to side and around as he pushed them in and out.

He then announced he was going to open me up wider medically. What the hell did that mean? Medically? I'm now nervous as I can't move, and I can't see to protect myself. I feel his two fingers enter me again and come out, then something cold slides into my anal cavity. I have no idea what it is. He seems to be fiddling with it. Then slowly I feel something pressing against the upper and lower walls of my inter butt. It feels like my hole is expanding, wider and wider. Now I am experiencing some minor stretch pains just like when a butt plug is being forced in, but it is easily bearable. It is somewhat of a slow process whatever he is doing.

Finally he announces, "Great, it is fully open. Good boy. By the way, the toy in your ass is a speculum, a medium size one. You took it all, it is fully expanded, I'm pleased. I have a large one too. You take that and a couple of bigger dongs I have here and by tomorrow you'll be ready for the real thing." Now I know what a speculum is. Gynecologists use them to open a woman's vagina when they are examined. Never thought of one in the butt hole. You could probably look right in. I see why he wanted a second cleaning. These gay guys are inventive. He says "I'm going to leave it there to help you stretch wide. I want you to squeeze down on it like you're trying to go, then release and then try to make your muscle relax, then again squeeze and then relax. Do it repeatedly while I work your oral cavity."

About a minute later I felt him pulling open the zipper over my mouth, then adjusting the hood so my lips are fully exposed. "Open your mouth, stick out your tongue, not too far and keep it that way until I tell you otherwise." I do as I am told. Swiftly something is push across my tongue into my mouth; not too far in and withdrawn. In it comes again and it registers in my brain via the feel on my tongue that this is a dildo. One that is of the type that is a facsimile of a real dick. Out it goes, then back in a little deeper, out, back in deeper, out and back in and I gag. It is quickly pulled out; a short pause is taken and it is reinserted and the in and out is repeated till I gag again. And again, and again. Now I am told to close my lips around it without biting the shaft. I comply. In and out, in and out deeper till I gag. When I do, I immediately open my mouth. Sir Michael pulls out the dildo and a few seconds later, WACK, my butt is smack with what I think is a paddle. It smarts, it wasn't a love smack. "Don't open your lips unless you are told" I am scolded. Then it is back to "open your mouth." The dildo is inserted. "Close" And the in and out, ever deeper till the gag reflex occurs again. This time I resist the opening of my mouth, but it's hard. I choke a bit, but the fake dick has been pulled back and I recover. This goes on for a while. There is a dildo change, maybe a tad bigger, but not a problem. The only issue is when it goes in too far and I gag. "You must learn to control your gag reflex. Your mind can do it. It takes time. I can swallow a dong much deeper than that. Come on, you have seen hundreds of videos of girls blowing guys with huge dicks. Try arching you neck back a little, it will help." He is trying to help. He is in a teaching mode. And again, we try, and I started to do a little better. I am then told to work on rubbing my tongue on the shaft as it moves in and out. I've done that with my penis gag before so with this I'm a fast learner.

Sir Micheal gives me a break from my oral lesson and returns to my butt hole. Out comes one speculum and in goes another. The new speculum's clappers feel wider than its predecessor. I soon found out that it expands further too. Because Sir has opened the spreader slowly there was minimal stretching pain, but I feel someone could now drive a truck into my ass. Of course, the plan is to drive something in there. That's what I'm being trained to allow.

It back to my mouth and throat. We practice. I gag regularly, but I feel I'm doing better. Apparently not well enough, as halfway through my butt is redden by two more hard strokes of the paddle. After about 15 minutes an exchange of ends again occurs. The speculum is removed, I am lubed, and a new dildo is pushed in. This one is different. It feels like a stack of steel balls that are getting progressively larger. I guess steel because they are cold. First one slides in easily, the second is not so bad but by the time we hit the third there is a bit of pain as it slides by my door. I get to experience those shots of paint numerous times as Sir Michael is pulling the toy in and out of my rectum entry. As soon as he is satisfied that this size ball passes the door we move to the forth. Same drill, this hurts more. I'm arching my back, pulling my butt forward to little avail as I am tied tight to the bench, a bench designed for just such an assault. I must be resisting because I get a "Relax, let it in" command. I try but I am still arching up trying to pull away.

Then a pause, and SMACK, SMACK, SMACK, SMACK. Four rapped blows, two each to each cheek of my butt. "That will take your mind off your butt hole." And back the in and out of the intruder goes. He's right, my smarting butt cheeks are a diversion, and we are onto the fifth ball. Now I have two sharp pains, at my butt door and internally deep. We are now at a length that my rectum is fighting. Sir Micheal is proceeding slowly at this point, rotating the tool, moving it side to side, extracting then inching forward again till this ball is swallowed up like the ones in front of it. This one hurt bad as it passed through. Once it is in it is abandoned in place, at least for a while.

We our back to oral drills again. I do better. I'm actually having a little fun as Sir Michael has started to add commentary to the in and out dildo entries into my mouth. "Oh, that feels good, suck it Cunt, oh you love it don't you Cunt, lick me boy, Take it all Cunt, I'm going to cum in your mouth you filthy bitch, you take me all Cunt, you better swallow every drop you pussy," and so on he goes. If he knows how I am enjoying the banter, I'd likely be smacked again.

He pauses with the latest dildo that he is using, a moderately sized unit, not to long as it hasn't been gagging me unless driven way in, but probably thicker and longer than my real one is. But it is out now. A few minutes passed when again he says open, wide this time and I do. Something new slides into my mouth and in an instant, I know it is him. I pull my head back, which I can do because I am only secured up to the top of my chest. I have enough movement to escape and close my mouth. I expect immediate punishment, but it doesn't happen. Instead, I hear "I thought you were ready mentally." And I instantly feel regrets.

Sir Michael really was trying to train me for what I professed I wanted. And here I am bound and blindfolded, wanting to be forced, all my fantasy requirements met and yet, I rejected my own wishes. My reflection let me push through and try again. I slowly opened my mouth and put out my tongue. "You OK?" I'm asked. "Green" is the reply. "Want to be punished first?" I'm asked. "Green." I'm expecting is another series of smacks, what I get instead is the metal plug in my anal cavity gripped and pulled out quickly, pushed back in and out again twice to what I think was the third, maybe the forth ball, then reinserted all the way back to where my butt swallows the fifth ball, which hurts like hell when it pushes past my sphincter this time without tenderness. This final hole stretching aches and spasms for a minute until my butt hole settles back down. This is a true meaning of the pain-pleasure experience. As some of the smaller balls slide by sphincter and up and down the canal they caused very pleasant stimulating feelings, the larger balls stretched me well beyond my pre-violation normal and caused pain, but together it was enjoyable.

Sir Michael is again back in front of me. "Open" I comply, and his dick is slid into my mouth. This time with one hand guiding his member and the other firmly at the back of my neck. I can tell he is hard. He must have been stroking himself. I'm instructed to close my lips around him. He is not deep in my mouth, but my mouth feels full. Much more than any of the dildos did. He doesn't move in and out, he just rests. Move your tongue around me. That's difficult to do with a mouth full of dick, but I try. He is smooth and hard. Actually, he tastes better that the dildoes did. There's a hint on coconut taste too, and from the back of my thoughts I recall he uses coconut cream as a lube when he jerks himself off. "Yeah, that's good Cunt. Try to tickle my slit, good, lick under my head. Yeah, that's right."

He now grips my head with two hands and he slowly pulls back just a bit, than slides back in. Then back out and back in. I only have his dick head and a little bit of his shaft in my mouth. I feel him pull my head towards him then slides it back. He keeps his dick still and is providing the stimulation up and down his shaft by moving my head. I am just traveling about an inch each way. It is not nearing my throat. I'm instructed to press my tongue tight to the underside of the shaft and I comply. "That feels good, you're learning fast my little Bitch.

Get ready, I'm going in deeper. He does this by moving his Dick forward along with pulling on my head towards him. It's not much, maybe just another inch, he is still not reached the back of my throat, but I think he's getting close to gagging me. Instinctively I pull my head backwards, but he has a firm grip and I go nowhere. I'm still OK, he doesn't change the depth of each penetration, but he picks up the speed of his thrusts in and out. Five, eight, ten thrusts, is this going to count as my first blowjob? Fifteen thrusts and then he pushes in further and I gag, big time. He quickly pulls out. I recovery relatively quickly due to my previous dildo induced gag control practice.

"Open." I open my mouth and insertion is again made by Sir Michael. The same steps, cadence and thrust sets occur and eventually again I gag, and he retreats. We do this maybe six or seven times, each ending in a gag reflex, some violent, then recovery and reinsertion. The last two maybe three times he pulls back but keeps his head in my mouth so I can't close my mouth, which hinders my recovery a bit, I think by design. "Bitch, I'm only about halfway in when you gag. You are going to have to train your throat to open itself up and accept something passing by it. You swallow food every day, use the same muscles and swallow the dick. That action is what makes deep throating feel so good. I know your own dick is shorter than mine but by your own description of your wife doing you, she takes it all."

My bride does give amazing blowjobs, only to me, mind you. My dick is nothing in size like Sir Michael, but I'm not that short especially when full erect. I can pull her face tight against my groin while thrusting and she takes it all and I go nuts. Sadly, while she enjoys the taste of precum, she finds the taste cum itself revolting so I must pull before I shoot my load. If I would cum in her mouth it would be the absolute end of that pleasure. But she is proof to me that I can learn to do this. I just don't know if I can do it this week and there won't be another chance. It's just that he's so wide. The dildoes he's been trying to push down my throat surely went in further. I think at least some of them were as long as his, but just not as wide. I swear must be his thickness that is getting me.

He pushes his dick back against my lips and I let him enter, really no choice. This time he's just trying to get some minimal pleasure for himself. He provides tonguing instruction for working his head over as he strokes his shaft with his hand. I feel his hand movement against my face. He withdrawals from me and a few moments later I feel his presence in front of me again. I also pick up the scent of coconut. He is satisfying himself. The student has failed. A few minutes pass and he seems to move away. Shortly later I hear a distinctive groan and I feel my butt near my crack hit be three shots of cum.

I hear the shower running. It's a while till Sir Michael returns. The straps on the pegging bench continue to their job, I stay secured where he left me. It's a good time to reflect on my first kind of a blow job. Not sure if I'm credited with it as I didn't make master cum. He had to do that on his own. I'm both surprised and glad that he shot his load on my butt and not in my mouth. With my face covered in leather it probably made no sense to shoot it at my face.

I ponder on the toys I sucked and the ones in my butt and how I had no say in the matter, bound to a bench and punishment always lurking around the corner. And about the punishments, while they hurt, the paddle strike stinging heightened my awareness and alertness. Pain that quickly changes to a pleasure as it dissipates. My mind wonders to the bench. How effective it is in holding me tight. That it is comfortable. That it is set up to put both my oral and anal cavities in the perfect positions to be used and abused. I wonder how much time this week will be spent secured here as there are so many other devices and places to be bound to at this place.

Sir Micheal is back and says "Let's finish up here. Your butt shows more progress than your mouth. With a bit more work tonight and some tomorrow you may be able to use that hole for some good. Not yet with me, but you could please others." And with that, I feel a tug and I am released from the ball stack shove up my ass. What a strange and enjoyable feeling as it is slowly twisted and pulled from my hole. One ball at a time, the door opens wide then narrows back tight to the staff as each ball slips through.

I feel Sir Michael start to push something back into me. It's cold like the speculum but this is solid, feels round like a big ball, it doesn't take much wiggling by Sir when it pushes through and into my now stretched out asshole. It feels like a ball, a big ball on a stick, whatever is protruding from my butt is laid down against my crack. I then feel him fiddling with it. Then it is pull and I feel tension on it. He's now playing with the top of my hood and before long I feel my head being pulled back and pressure from the device pulling my hole upward and toward my head. My butt hole and head have now been tied together, a bit strange and bit uncomfortable with both my neck and hole stretched together. I am familiar with bondage toys, so I am able to figure out quickly that I have an anal ball-hook inserted into me and it's been stretched to the tie off ring on the top of my hood. I'm in a very odd hogtie like position. I know the anal hooks come with different size balls and apparently this one has a large one. It did not slip in easily and I don't think Sir has to worry about it slipping out without help. It sure is holding the rope pulling hard on my hood fast.

And again, I am left alone. I guess the large ball hook needs time to complete its stretching duties. I hear the porn sounds from master's computers change, so I assume he's watching, surfing the channels. Not sure how long I've been hogtied, it's been a while. I don't mind the solitude, but I've been tied to the bench a long time now and I starting to get uncomfortable, especially with my neck pulled back. My thoughts of my existing discomfort are interrupted by a new sudden pain. There is a sharp moving pain in my ball bag, and I realize instantly what it is. Sir Michael discuss the toys I would bring, and two from my list that he wanted to come were my single-wheel and five-wheel Wartenberg pinwheels. The five wheel is taking a trip down my bag. These wheels are a great pain-pleasure deviant device. They are deviant in that it is the operator's choice as to which side of the pain-pleasure equation the victim will fall. Either Sir is just inexperience, or he wants me to feel pain. The pricks of the wheel are typically most sensitive when ran over the nipple, a woman's pussy lips and clit and a man's bag. The next move tells me Sir knows how to use this because as I react and try to move away, which by my bounds is limited. He grabs my balls, pulls down stretching the bag taut and running the pinwheels across the balls now bulging from the sack. I'm feeling it. Nothing jumps to mine why I'm given this punishment. There certainly must be an infraction for which I am paying, or he may simply be amusing himself with the toys I brought. He's allowed, I've read the contract. He stops working the bag, switches to my single wheel and starts running up and down my crack, circling round and round the hook protruding from my hole. Oh boy does it hurt as he goes over the nerve clusters at the sphincter. He tires quickly of particular abuse on my anus or maybe is sympathetic to my bucking butt and instead, starts five-wheel journeys down my butt, upper and lower legs continuing onto the soles of my feet and then making return trips. These round trips excursions down and up both legs put me back in the mid-line of pain-pleasure. After a couple of trips it is onto my inter-thighs racing up to where my privates connect. All this stimulation actually makes me a little hard. Sir must have noticed because my dick head is grab, the dick pulled downward and the single wheel explores all side of the shaft, then the top of the head and slit are visited, and we are back to the pain side with me bucking hard to no avail with my dick still held fast in his hand. And then he abruptly stops his skin torture and says, "Let's go to bed." And he wonders away.

I wait and wait, there of course is no other options. Am I to sleep here like this? I'll never be able to tolerate it. I'm tied chest down in a squat with my head pulled back and tied to a hook planted in my butthole. I wait but not patiently (yes, the reactions of an impertinent slave, I should confess and be punished), I'm ready to yell Yellow, no this would be Red. But I'm all excited about nothing. Sir just went to take a piss and get himself a snack. He's back, untying my hood from the hook. The hook is then unceremoniously popped out from my hole. He wanders away again, and I hear the sound of the hook being dropped in his bathroom sink. He's back, undoing my chest straps, then legs and finally my arms. "Get up Bitch, you have toys to clean and take that hood off. When you finish your chores get ready for bed, put down your bedding, lock up that sorry dick of yours and bring me your cuffs." I climb down from the bench. I am bent over and stiff. My morning stretches are a long time in the past. I struggled a bit to untie the string at the base of my hood but eventually get it. Good thing or I would have been wearing it all night. Help wasn't coming for it elsewhere. I stretch out the laces and pull the hood off.

I went immediately to the bathroom sink and find all the butt toys that were used to stretch me tonight in it. With soap and hot water, then chlorine wipes I thoroughly clean the toys. Surprising to me there is very little butt residue to remove. It's mainly just lube, if anything. I'm fascinated by the stacked ball dildo. It's glass, not steel, with five graduated bulbs expanding in size and then after the last it narrows to a neck that allowed my muscles to wrap around and hold it in between my cheeks. Well, that was true up until I was punished with it. I am stunned that my sphincter let the last ball through. That bottom ball is the biggest of all the toys I took in. I can't believe it passed by my sphincter without ripping me. I reach under my legs and feel just to make sure. I'm not torn, but my finger easily slips into my hole as I feel around there. I wash my hands. I now understand my pain and why childbirth causes so much agony. The two speculums are intriguing too. I operate the larger speculum's slide and spreader mechanisms and I was amazed at what it could and did do to my hole. The size of the ball on the hook is big compared to ones I have seen in online adult toy stores.