The night started off with Gwen telling me she wanted to play. She told me that she was going to make me cum in ways I've never dreamed of. As a sadistic switch, I have begged her for years to truly test me. She had never been comfortable truly pushing my limits though. As I would find out later, tonight was going to be the night that changed!

"The Ritual that you so elegantly laid out for me to follow is yours to follow tonight!" She said as I was walking to the bathroom. "Also, I want you to edge yourself before coming to the bedroom. Don't cum. Period. If you do, there'll be hell to pay. If you walk in here with a soft dick, you won't get more than a chaste peck on the cheek for a month!"

After my enema, I got in the shower. As I was lathering everything up to shave, my mind wandered and I envisioned so many different scenarios that could be coming up. The thought of her pussy grinding into my face, the softness of her hands on my cock, the intrusion of one of our toys into my ass.... Mmmm.... so many possibilities!

I shaved around my asshole, my balls, around my cock, my face and head, and trimmed the hair that was left. As I was moving things around to shave, my cock was throbbing because of the scenarios going through my mind.

I wrapped my hand around my erection and started to stroke, imagining myself tied to the bed while she stroked me. As I got closer, I imagined her sitting on my face, holding my breath like she was cutting off my air, my pace got faster, my orgasm building inside me. Every stroke led me closer to the line she demanded that I not cross. As I felt the point of no return coming at me like a truck screaming down the freeway, I willed my hand to stop. I barely stopped in time, I was so turned on, so lost in fantasy, that I very nearly sealed my fate with one last stroke.

Getting out of the shower, I was incredibly horny and very frustrated. To say that I got close would be the understatement of the week. My cock was throbbing and angry at the interruption of my orgasm, and my mind was in a really raunchy place.

DING! My text notification went off. "Did you get lost? Hurry up! I want your tongue between my legs in 5 minutes. If not, you will regret it!"

Fuck! I still have to brush my teeth, towel off, put my cuffs on, and install the plug that is normally reserved for her!

After I brushed my teeth and put on my cuffs, I struggled with the plug. It's not that it is that large, it's just hard with no warmup. I'm not that experienced back there, so it took a few extra minutes. That is the point that the night went awry for me.

I walked in 5 minutes and 14 seconds after the text came in. At least that's what Gwen said. As I looked at her in her stunning skirt suit, she glared at me like I'd just farted at a dinner party. I knew better than ask to see the timer just from the look in her eyes. "Knees, NOW!" She commanded, and I knew I was well and truly fucked.

"Eat. Now, slave!" She commanded as she slammed her crotch into my face. Her slit was already wet and fragrant, her folds absolutely delicious under my tongue. Her greedy hands pulled at the back of my head, grinding my face into her cunt. Her legs were closed, and with her pulling my head forward, just breathing was a challenge. Effectively satisfying her was going to be impossible in this position, but then, I have a feeling that was by design.

"That was the most pathetic attempt at eating pussy you've ever given me. You need some practice, and you're going to get it tonight." "Stand the fuck up!" As soon as I had complied, a riding crop that I somehow hadn't seen slammed into my cock. "FUCK!!!!" I nearly yelled. I wasn't braced for it, prepared for it, or expecting it, when the impact traveled up my spine and down into my balls. Pain exploded in my eyes a second time just before she told me that I had 28 of those coming, and that it would've only been 26 if I'd counted the first two. "Furthermore, I'm about to tie you up, and if you yell, you'll wake the baby. If he wakes up while you're tied up, you're getting a prostate vibe shoved in you and being left stuffed and miserable while I go tend him, so I'd shut the fuck up if I were you."

"On the bed! Hurry up if you want to be able to sit down tomorrow!" She said as the crop bit into my ass. I thought to myself that she was brutal with that crop as I crawled up on the bed. As soon as I was on the bed, she positioned me to lay with a bar behind my back and sticking out of both sides around the level of my nipples. She quickly fastened my arms to the wood and ran a rope between my cuffs and tied them tightly in front of me. My arms inescapably secured, she told me to pull my legs up and secured my thighs to the wood too, holding my legs back like I was the missionary's wife waiting for a hard cock. My mind couldn't help but think about seeing her splayed out just like I am now, although that particular vision soon fell victim to her asshole lowering directly over my mouth and her cunt sealing off my nose. "You better start eating, slave, you have to earn your air after that pathetic attempt at eating pussy earlier!" As my tongue lapped at her asshole, she ground her wet pussy into my nose so hard that it was painful. Relief coursed through me when she lifted herself enough for me to get a breath, and was just as quickly dashed as she slammed into my face just as quickly as it had lifted a moment before. My heart raced and my lungs burned as she ground against me. My tongue danced across and delved into her ass like it was the last thing I'd ever taste. Her muffled groans grew, and just as I was thinking I couldn't keep going, she lifted again. This happened more times than I could keep up with until she made me start to panic before she lifted back up. My lungs were screaming in agony before she lifted her ass off me.

This time, she didn't crash back down on me. Instead she knelt beside me on the bed and explained what was going to happen. I was to be punished for two things, then the retribution for our last few play times would begin. She went on to explain that while she had gotten off on (a mild understatement if I say so myself) my exploration of my sadistic side, she felt that I should be on the receiving end of the abuses I put her through. I was to be punished for being late, which would consist of 2 lashes on my cock per second that I was late, and my failure to perform to her standards in eating her pussy, which was to consist of her withholding any kind of pleasure to my cock for the first hour of playtime and I was going to eat her ass and pussy until HER tongue gets tired.

"There are no yellow safe words. Your only safe word is red, and if you say it, we stop. Period. I won't touch your cock for a month if you use it and I DAMNED sure won't finish you off tonight."

I thought to myself that this shit just got REAL. I know she can go a month without fucking me just because of all the toys in our stash. And if she says something, she fucking means it. I'll just have to tough up!

"Now, for your first punishment, I think I need something aside from the crop!" My mind races, the crop is bad on my dick, but I don't think we have anything else that's really gonna work well... That's when I saw the applewood switch she cut from the back yard. Oh. Fuck. This is going to..... "FUCK!!!!" pain explodes again, the first lick hurts so bad I forget to count. "I'm only going to warn you once, if you don't count, they don't count! Now, let's try again!" The second blow, officially number one lands, and my God it hurts. "Two Ma'am!" White heat sears across my cock as the next 9 blows rain down, I gasp out the count with every scorching blow. My cock is rapidly softening to the point that it isn't a good enough target for her, so she stops for a minute. "You seem to not be that horny, slave, don't you like what you see?" She purrs to me as I hold back tears.

"Let's give your cock a break and show your asshole some love, shall we?" She says as she pulls on a pair of black rubber gloves. The plug pops out of my ass with a firm pull from her, and is almost immediately replaced by two well lubricated fingers. She works them in all the way to her knuckles and starts dancing them across my prostate. Holy fuck, that feels so fucking good. I'd give my right nut to have her mouth on my cock right now, but I'm not saying anything for fear of her taking me up on that! A few hard strokes against my prostate and she forces a third finger inside me. Three fingers is as big as we've ever gone and that was after a lot of warmup. This wasn't slow, loving, or tender, this was fast paced, punishing, and painful. She was trying to hurt me, which considering how roughly I used her ass the last time, I guess I earned it. The third finger stretched me out, my asshole screaming to my brain that it was too much, but my cock screamed just as loud to shut up before I said the safe word. The fourth finger was very nearly the end of me, my asshole felt like it was being torn apart and my cock throbbed like it was possessed. I bit off the screams when she started fucking my ass with nearly her whole hand, but the tears would not be stopped.

After a couple of minutes, the pressure, the fullness, and the constant playing with my prostate was feeling amazing, good enough that the residual pain didn't matter. When she unceremoniously pulled her fingers out of me, I could feel my asshole gaping open, empty, wanting something in it. "Tell me what you want me to do with your ass, slave!" I'm almost ashamed of the words that came out of my mouth at that point. "Please Mistress, PLEASE fill my ass. I'll do anything!

It took me less than half a minute to regret that plea. Her second largest vibrator probed against my asshole, and was slid deep inside me. This thing was bigger than my cock, both in length and girth. It was by far the biggest thing she'd ever put in me. It went in easily because of her stretching me out, but it went deep. It hurt as it pushed deep inside me. When she turned the vibrator on, the pain faded into a mind numbing wave of pleasure as the vibrations hit my prostate.

Playing the sadistic bitch roll ever so well, she turned off the vibrator off and proceeded to fuck my ass like she was angry with it. Out until there was barely the tip in me, slammed back deep inside, out, back in. It felt like my guts were being rearranged every time she slammed into me. The pain was back with a vengeance when she suddenly pulled the vibrator out of me.

"Well, you wanted your ass full, so let's fill it up!" She said with an evil grin. The largest toy in her collection is a 9" curved g spot vibe that is porn star thick. When she held it up, I begged her not to. I begged her to beat my cock again instead. I begged her to spank me instead. Anything but that! "Oh, don't worry, I'm going to do all of that too, but not until your asshole is full!" The pain as she stretched my ass with the vibrator was very close to bringing the tears back. Full doesn't begin to touch how my ass felt, and without her touching my cock to distract me, my mind just couldn't let go of the violation that was happening. "Please ma'am, please take it out! I'm begging you!" As I begged for mercy, she just smiled at me. "Do you want it out? All you have to do is say one little word and I'll take it out. You can end this so easily, but I don't think you will!" The glee in her voice told me that unless I said my safe word, this was only going to get worse, but I couldn't bear the thought of going to bed unfulfilled after bearing this much. I had to stick it out!

"Are you sure you don't want to stop?" she said as she smiled wickedly at me. "I'll take it out and untie you if you say the word!" she taunted as she started fucking my ass slowly with the vibrator. The pressure was enormous, and my cock took on a mind of its own as it pulsed and twitched with every thrust. The pain was receding again when out of nowhere the switch crashed down on my cock again. Before I could get the count together and out of my mouth, another blow rained down on my cock. "Eleven, Mistress!" The pain was blinding, the count near a scream. The switch was thin and supple, it wrapped around my cock with every blow. Tears were falling as she fucked my ass and landed nine more blows across my cock. "I think you can handle the other eight now, your cock isn't showing any signs of going down!" The next eight lashes were rained down with more intensity. Each lash wrapping around at least one fresh welt. My cock looked like it had grill burns crisscrossing it by the time she was done.

After the whipping was done, she turned the vibrator on and started absolutely pounding my prostate. My cock, marks and all, twitched harder, and pulsed like it was possessed while precum started to leak out of it. I begged her to touch my cock, to absolutely no avail. My mind was nothing but a ball of frustration, need, and agony. Tears of frustration and pain ran down my face as she ravaged my asshole with a toy that took her a lot of lube and mild discomfort to fit in her pussy, much less my ass. The pain in my guts slowly receded as my need for orgasm grew closer, with her skilled hands finding my prostate with every stroke of the intruding shaft in my ass.

A timer went off that I hadn't noticed before. "That's the 45 minute mark, slave. I think we'll change things up a bit!" She pressed the vibe deep inside me as she tied paracord around my balls, being careful to not touch my twitching, leaking cock. As soon as she had them wrapped, stretched, and separated, she tied the cord securely around the base of the vibe. She then pulled the tails to each side of the arm bindings to press the shaft deep inside me. No rocking, squirming, or pushing was going to do anything but make it stretch me more.

As soon as she had me securely plugged, she straddled my face again. "I'm going to let you eat my cunt this time, slave. Do it right this time or it's back to eating ass for you. You're not to touch my clit unless I tell you. I don't want to cum too fast!" Her cunt slammed down on my face. It was slick wet, pungently horny, and gaping open like it was begging for cock. I plunged my tongue into her folds like a man possessed as she ground her asshole to my nose. I could breathe a little, she made sure of this, after sitting down. The problem with being able to breathe is that she saw no reason to lift up. I knew better than to stop without her taking her pussy away from me, so I kept at it as long as I could. She ground into me, and I felt her putting the wand against her clit. The vibrations were definitely helping her along, but they were making my jaw go numb and my tongue was getting weak. When I started to slow down, pain bit into my inner thigh. The switch made its mark again. "That's ten licks. I don't expect you to count, but if you stop or slow down again before I say to, it'll be 20 next time! The pain swelled away from each lick. Radiating towards my very tired asshole and very sore and frustrated cock and balls. I did my best to maintain a steady rhythm as she rained 10 licks onto me. Almost immediately after the blows, I felt her orgasm growing. Her lips swelled into my face, her juices flowed more easily. Her asshole started to twitch against my nose, and suddenly she sealed off my mouth mid inhale. She bucked against my mouth, preventing my breath. Her orgasm pounded over us both like crashing wave after crashing wave. I could not even begin to breathe as she continued to buck against me. My lungs heaved, they burned, I started to panic as her juices flooded my mouth. Suddenly, she lifted. I swallowed what I could quickly and breathed in. She let me breathe for a couple of minutes while her orgasms wound down, both of our breathing ragged and deep.

"Would you look at that!" She exclaimed, "your hour is up! Would you like for me to touch you?" I groaned yes, and started to beg, plead, promise things there was no way I could give I'd do anything for her to touch my cock. To provide some relief to my aching cock.

"You'll have to earn it! You ate my pussy right this time, so you won't be punished, but now you have to earn a blow job." She kneeled back over my face and I could see her asshole coming towards my mouth. "Tongue fuck my ass. I am going to let you watch me fuck it, so warm it up for me." She put her asshole against my lips and clamped my nipples. She clamped down hard enough that I cried out against her ass. She pulled them up and commanded me to eat. Trying to get her to ease my suffering, I licked her with a fervor that I didn't realize I was capable of. My tongue danced across her rim, plunging in and out of her hole. Her hips started to rock against me, her moans became insistent as she pressed her ass against my face. The pain in my ass and nipples combined with the persistent tremors against my prostate had me bucking my hips against empty air. Suddenly she lifted and I could see her dripping slit with two fingers buried deep inside.

When she slowly stroked my foreskin with a single fingernail, the groan that left my throats was urgent, needy, primal to its very core. The electricity that seemed to flow from her into my throbbing member bit deep into my balls, accentuating an ache that had been drowned out by so many other sensations of pain and suffering. The ache was persistent and suddenly became my single focus. The deep throbbing in my ass, the sharp bite of the clover clamps on my nipples, the still stinging welts on my cock and thighs, they were all distant annoyances compared to the pressure in my tightly bound balls. She wrapped her index finger and thumb around me and slowly stroked my shaft with just enough pressure to move my foreskin a little bit. The torturously slow up and down strokes were driving everything in my mind away except the need to be in her. I tried to buck my hips, but the way I was bound made the movements ineffective at best. Finally, she roughly pulled my foreskin back and just held it. She gripped my cock painfully tight, and told me she would let me cum right now, but she wouldn't move her hand to make it happen. I bucked, I pulled, I twisted, and all I gained from it was more soreness in my balls and ass.

"That's enough touching for your cock for right now. I want you to watch this with your undivided attention!" She then proceeded to straddle my face again, but bent over so I couldn't touch. She reached back and dipped a well lubed finger inside her ass, slowly swirling around her rim, then sliding in and out of her hole. Her finger sank deep inside, she wiggled it a little then pulled it back out. She fucked herself with just one finger for a couple of minutes before she asked what I'd give for a blowjob. I foolishly replied "Anything!" and as she sank her mouth onto my cock, I swear I heard a laugh. My mind fogged up to the point I could only see her ass with two fingers now playing with it and feeling only her glorious mouth wrapped around my cock.

Her mouth worked like she was trying to suck my soul out through my cock. She licked, sucked, bobbed and swirled until I felt the first tremors of an enormous orgasm start up. She must have felt them too, because she lifted her mouth back off my cock before I could cum. I begged her to please don't stop, but she laughed at me and said "You begged for a blow job, not an orgasm. You don't get to cum yet!" With that, her cunt slammed back down on my mouth, sealing it off to prevent any more begging. As I watched her still busy fingers, she started playing with my balls. As tight, sore, and swollen as they were before the blowjob, they felt as if they would burst now. Her musky slit surrounded my tongue as I worked it in and out of her. Her juices soaked my beard and mustache as she ground into me. At least this time I could breathe, so I could somewhat focus on doing a proper job of eating her.

"I know how much you like seeing me with something in my ass, so watch closely!" she said as she pulled her fingers from her ass. Her hand disappeared and came back with a vibrator that was about the same size of my cock. The thing about it is that I generally use anal sex on her as a punishment, as she doesn't typically enjoy it that much. The only reason she was doing this was to torture me. To let me know that something was in her ass that I didn't put there and she knew it drove me nuts. The vibe slowly slid inside her, deeper and deeper until she reached the flared base.

When her lips wrapped back around my cock, I thought I would die of heart failure. She slowly took my cock deep into her mouth. As she was sucking me, the dildo right in front of my eyes stretched her ass. I could see her hole sucking in as it went deep, pulling out as she slid it back. I could see her run quiver around the ridges as they passed by it. Her mouth worked feverishly on my cock, sucking, swirling, licking, until finally, my orgasm reached critical mass again. Instead of pulling away, she bit down on my cock, just below the head until I was screaming into her cunt. The pain drove the orgasm back just as effectively as her stopping had before. As I screamed into her, she ground against me even harder, her own orgasm building past the point of no return, finally crashing over her. The sight of her ass quivering around the vibrator combined with the taste of her juices combined to give me a euphoric feeling as her orgasm crashed over me as well.

As she was coming down, she removed the vibrator from her ass. The gape drew closed as I watched, her inviting, beautiful asshole closing around nothing but air. "Now, what would you give for your orgasm? You've given me a great orgasm and you got two very close edgings for your blowjob. How about a spanking? Would you take a HARD spanking?" The look in her eyes showed absolutely no room for bargaining, no space for mercy, just the desire to inflict more pain and suffering on her slave. "Mistress, I will gladly take whatever you believe to be fair retribution for my orgasm." My exhaustion was such that I couldn't think enough to say anything else. My ass was cramping around the now dead vibrator, my balls felt like they were in a vice, and my cock would have broken stone. I would happily give or take ANYTHING just to have her make me cum.

When she started to untie the vibrator in my ass, relief flooded through me. The thought of having it out of me was heavenly to say the least. I was so sore from its excessive girth and writhing around it, that when it slid out, I nearly screamed. She replaced it with a much smaller plug much to my relief, but that didn't last, for as soon as it was firmly seated, she started inflating it. She pumped it up until I felt like I was stretched paper thin. At least this didn't go as deep though, so there is that!

"Open your mouth. Now." And she forced a pair of her panties that she had wiped her pussy off with into my mouth. This was quickly followed be a ball gag that was tightly put around my head.

As soon as it was in place, she told me that I didn't need to count. She was going to spank me until she got tired of the noises I was making. The fear that went through me when I saw the new paddle I had used on her shortly before this was absolutely electric. The paddle had a thick fiberglass rod for a spine covered with a one and a half inch wide leather sheath. I knew what kind of damage it could deal out, as her ass was sore for a few days after I worked her over with it. She'd actually called yellow that time, and she's only done that 3 times since we started playing.

"Thud!!!" I tried to scream. The first blow was vicious, jarring me deep inside. The next few hits blurred together in sync with my muffled screams. The blows became a cacophony of misery and pain, yet the vibrating plug in my ass kept my mind on my cock just enough to keep it hard and needy. The shocking hits came at random. Sometimes alternating from one side to the other, other times hitting the same spot multiple times until I though I'd pass out. Screams and tears were flowing from me freely, my ass on fire and my cock and balls needy as ever. The ever present vibrations were causing my cock to leak almost continuously now. By the time the last blow landed I was nearly delirious with pain and need.

"I think you have earned your orgasm now, don't you think? I won't edge you anymore, if you cum, you cum, but if you do it before I tell you to, you'll pay dearly for it!" The gleam in her eyes said that I would never match the demand she just put on me, no matter how hard I tried.

She sat on my cock, reverse cowgirl style except with my legs pulled back she had extra support and could easily get to my balls. Her hot, wet, smooth cunt felt like heaven sliding over my cock. I wanted to buck to her, but I knew I could move hardly at all. As she slipped onto me agonizingly slowly, she pulled the cord attached to my balls. The pain from her pulling was delicious as her pussy swallowed me to the hilt. As she started fucking herself with my cock, she would rhythmically pull the rope. My orgasm started to build in seconds. I needed to cum so badly, yet I feared what punishment I might receive for not waiting. I tried, I yanked my thoughts to anything I could to stop the freight train of an orgasm that was barreling down on me. "Not yet slave! Don't you fucking do it!" I could hear the smile in her voice as she said it. She wanted me to cum. She wanted her last bit of punishment to mete out. I screamed into the gag as my orgasm pummeled me. I thrashed against my bonds, shooting what seemed like gallons of cum into her hungry cunt. My ecstasy soon turned to agony as she kept riding my now over sensitized cock until my erection fell enough she could not stay on it.

"I warned you not to cum yet. I fucking told you, but you have no self control." She said as she was removing the gag from my mouth. "I need to cum a couple more times. I wasn't done with that cock, so you're going to make me cum." She must have seen the realization flash across my eyes because she looked at me and told me that all those times I'd jammed my cock in her throats after she'd cum all over it had earned this for me.

I hadn't even processed everything fully as I was still riding the high of my orgasm when she told me to take a deep breath and her cunt, full and oozing my cum, slammed down on my mouth. The taste wasn't as horrible as I'd imagined, although being forced to eat my own cum was humiliating. As she rode my face, she wrapped her lips around my cock and sucked me. I was so incredibly sensitive that it was absolute torture. She sucked and rode, only lifting her pussy enough for me to breathe occasionally until all my cum had drained down my throat and my cock was hard again. I writhed underneath her until she suddenly lifted up and grabbed a very strict cock ring. Placing it around my cock, she started sucking again for all she was worth. When I saw the tube of stay-hard, I knew I wouldn't be cumming this time. The two thick, ribbed condoms ensured that I wouldn't feel enough to get off while she used my cock.

As soon as my cock was covered, she slid her box back over my again and started riding my cock like it was the only to save her soul. She bounced on me, pulling my balls, turning the plug back on, pumping it up even more, until she collapsed as a wave of orgasms hit her one after the other. I have no clue how many she had, but when they hit her, she nearly tore my cock off at the root. After she was done, she straddled my face yet again and told me to lick her pussy and ass clean, but don't touch her clit. I complied without arguments, as I knew I wasn't getting loose until I did it. I tasted myself very faintly under her own juices, but I didn't care. I was where I belonged, worshipping the pussy and ass of the most gorgeous woman in the world.