Anniversary Assignment: Riding The Horse Part Two

Riding The Horse
Assigned by Mistress Kari

Part Two

02/25/11

In my present state, with sore cunt, the last thing I wanted was Robert’s still ENLARGED and SWOLLEN cock inside my pussy. I lifted my head, shaking it, protesting, but then Kari was kissing me, sticking her tongue in my mouth, her fingers squeezing my only recently released nipples. I cried out, my back arching and then I felt the bed compress at the bottom. There was movement between my legs and I felt Robert’s knees against my thighs. I shuddered against Kari’s kiss, her fingers and then Robert’s cock was pressing against my bruised petals. I lifted my hips, trying to twist away but he moved against me, pinning me, spreading my labia open with his bulging tip, plunging his massive vacuum altered shaft into me. It went deep, impaling me while his hips pressed against mine. I convulsed down there, as if I had a hundred debilitating cramps all at the same time. Agony poured up from my pussy, all the while I felt the sudden rush of sexual intoxication from my libido. Robert moved up, replacing Kari and his mouth was sucking on my nipples, drawing the crushed nub inward while a female hand continued to play with the other one. Then I felt Kari on the bed next to us, her fingers caressing me, my head, my shoulder, my neck, tickling my ear even as her fingers moved between us. She actually touched Robert’s cock as it slid in and out of me and when I felt her fingertips on my clit, I cried out in sexual exhilaration.

After spending almost an hour on the wooden horse, having sex immediately after getting off was not exactly recuperative. My brain was fighting a losing battle with the flood of hormones and chemicals flashing through my bloodstream with only my emotions being any kind of help. My brain was saying “now wait a moment. Her body was just propped up on a fucking wooden pony and there was quite a bit of bruising on that part down there. Not to mention her nipples were clamped and weighted, and frankly I don’t think that she’s in any condition to be fu…acchheedd.” That last part is where my brain was throttled by my libido, who was repeating “Oh fuck yeah!” over and over.

So as you can imagine, Robert’s “fuck her until you cum” was a rather brutal opening of my bruised nether regions. But to his credit, Robert moved slowly. That helped. Of course on the flip side, he was thorough as well, moving his swollen shaft all the way in and as deeply as possible. Since he was now about three inches in diameter instead of the typical two inches, it was like fucking my Core Driller dildo. He also picked up the pace as he started to cum and the next thing I knew his shaft was throbbing inside me, filling the extra large condom Kari had slipped over his cock to the max.

He collapsed on top of me with a sigh of relief and despite the fact that I was still hurting I couldn’t help wondering how long it had been since Robert had felt release. I heard a sharp smack and Robert grunted. Kari had hit him on the bottom.

“Okay, get off her.”

I blinked as Robert rolled off me. Kari was standing there. She had changed out of the pajama top she was wearing earlier and was now dressed in black leather boy shorts and a brazier that emphasized her top. A set of incredible strap high heels were on her feet and she looked like a sex goddess. I would have fallen to my knees to worship her had I not been already bound and spread on her alter like some sort of sacrifice.

Kari was also wearing one other item, but it was something I hadn’t seen before. It covered her right hand and I realized that it was a glove. She moved close even as Robert vacated both the space above me and the space inside me. She crawled up onto the bed and moved close to me.

“And how is our little doe doing now? Feeling the need?” she asked.

I didn’t reply. I knew the question was rhetorical. Besides, while I was still horny, I wasn’t anywhere close to orgasm. Fucking Robert had been both excruciating and wanton, but it wasn’t enough to get me going. Not yet at least. Kari stroked my cheek with her left hand and let the finger slide down my throat and to my breasts. She circled the nipple lightly which caused me to shiver. The pain from the clamping was almost gone, but for some reason my nipple stiffened as she ran her finger over it.

Then Kari lifted her gloved right hand, holding it up in front of my face, palm forward. I blinked, then gasped. The fingers of her glove were covered with short, sharp, pins. In the space of a heartbeat my breathing became labored and I was pulling against the bondage holding me down as Kari waved her pin covered fingers in front of me. I’m not sure why, but she started off by using just one finger and touching my chin. I felt the little sharp pin pricks, but they weren’t deep, just there, like one of those medical pinwheel toys with the sharp pins.



She lifted her hand again and this time I watched as she moved it over my right breast. She spread her fingers and then lowered her hand down until my entire nipple was centered in her palm and her fingers curled around into my cleavage. Almost immediately I felt the sharp tacks touching me and it was like I was wearing those silly tack pads in my bra. Kari began moving her fingers up and down, like playing a piano arpeggio and then moved her hand around. My breast felt like a pin cushion and my nipple stiffened even more, the raised flesh prickling deeply as it rose into the pins of my best friend’s glove.

Kari moved to the other breast and repeated the same process. Then she cupped my sex, applying various degrees of pressure. It wasn’t exactly erotic in the sense that I wanted to cum, but it brought my thoughts directly to the spots she touched, emphasizing them, making me want more. After she completely circled me once, spending five or so minutes on each breast and even my pussy, she returned to my right breast and then snapped at Robert.

“Bring a vibrator over and touch her where ever I just did.” Kari ordered. As soon as she was done with my right breast, plumping it and squeezing it with pin covered fingers, Robert moved in and touched my nipple with a purple covered plastic vibrator. Kari moved to my left breast, once more grabbing hold of the entire mound and squeezing. Sharp prickles were like little bits of electricity sparking against my nipple. And over on my right side I was suddenly feeling the intense and direct vibrations against my nub.

By the time Kari was cupping my pussy again I was starting to get really excited and the pins were starting to feel good. Kari finally moved back and Robert did my clit, eliciting a cry of desperation out of me. My breasts sported tiny dots all over where Kari had squeezed tightly. Then Kari nodded at Robert and the two of them began releasing my arms and legs.

I stretched, trying out my new freedom and I wondered what they were going to do to me next. I was pulled up right as Kari left the room and the Robert was giving me a quick massage. It was a muscle rub, focusing on my legs, back and then shoulders. It was fast and a little rough, but I just enjoyed having him touch me. Then when he was done, he helped me to my feet and pulled me back out into the living room.

That was when I realized what was coming next.

The wooden pony had been reset. The two stools were in place, as was the spreader bar. Kari suddenly appeared from the kitchen holding a glass of water. I took the proffered drink and drained the glass, even as I felt my heart flutter at the thought of riding the horse again. When I finished I handed the glass back to Kari and Robert moved me toward the horse.

Climbing those stools was so hard. But I did it.

“Robert! Don’t forget the vibroballs!” Kari shouted from the kitchen. Robert looked a little sheepish but quickly left me standing there on the stool while he retrieved the vibroballs. When he returned I lifted one leg, placed an arm on his shoulder, and let him insert them. He wasn’t as rough as Kari had been the first time, instead making sure I was capable of taking the vibroballs. Once stuffed, he turned them on and I moaned as the waves rolled over me.

Robert spent a moment locking my arms to the sides of the bondage collar, which was quite different from the behind the back position I had first ridden the wooden horse in. I liked it, though it did choke me a bit. Now my elbows were sticking out to my sides and ironically they ended up helping me keep my balance. Robert helped me swing one leg over the horse and then went about getting the spreader bar attached. This time I stayed on the stool, putting all my weight on the right foot. It was an awkward and uncomfortable position, but it was better than sitting on the damn horse early. By the time my legs were locked open, Kari had returned. The glove was still on her right hand, but something more frightening was in her left.

On the previous Wednesday, Master Barrett had given me a rather specific assignment. I had been directed to go to the hardware store and have a chit chat with Mike, the store manager. Master Barrett had felt that I needed another insert, similar to the ones Mike had made for my bra. Despite his concerns, Mike had made me something appropriate, using a oval cut piece of ¼ inch rubber and a handful of stainless steel tacks, each about a ¼ inch long. He had cut a small grove down the center of the rubber, basically allowing it to be folded easily and then nailed the tacks down to either side of that groove. What I ended up with was a pliable rubber pad that was foldable in the center and that would bend in a gentle curve outward. We tested it that afternoon and let me tell you, slipping that tack pad into my pussy, feeling the pins along my inner and outer labia, was about as scary and sexually erotica as I have ever felt. Mike also gave me a lot of instructions about how not to use the pad, how to clean it, and offered to make me something a little less dangerous. I drove home with the thing embedded in my pussy and let me tell you, I came hard.

And Mike got to butt fuck me too, so he was rewarded for his work.

It was this little rubber pad that Kari was now holding. It had been in my bag and I had been instructed to bring it, but I had thought it was just to SHOW Kari. I now understood the pin glove. With one leg forced up and my pussy fully on display, Kari moved over to me and reached down with her right hand. Pins pressed sharply against my labia as she spread my petals.

“Please! Kari, no!” I begged, shaking my head. Kari gave me one of those looks that told me I needed to shut up or this would hurt a lot more. I closed my mouth even as my chest started to heave in silent sobs. Tears poured down my face as she folded the tack pad and stuck in up into my pussy.

The tacks were much more wildly spaced than the pins on Kari’s glove. But they were also sharper too and more likely to penetrate skin. The thought of having to sit on this, on a wooden horse, suddenly was too much and I turned to Kari.

“This is in violation of my limits! It will cut me! I can’t!” It was about as close to panic as I’ve ever come. Robert had to hold me in place or I would have fallen off the stool. That would have been bad since I was now technically bound around the wooden horse. Kari listened to my protests for just a second and then placed the forefinger of her right hand against my lips. Pins locked my mouth closed and I shook, scared of what she was going to say.

“Hush,” Kari said softly. “I would never do anything to you that violates your limits. This will not. You will ride it for ten minutes and then we will lift you from it, remove it, and you will continue your horse ride. But I will not waste the efforts of either your Master Barrett or your handy man. You WILL ride with this saddle and you will suffer.” Then she gave me a smile. “Cumming is up to you.”

And Robert picked me up and set me on the edge of the horse.

Pain flooded up through my groin and exploded skyward, overwhelming everything in its rush to get to my brain. Between my legs I felt something much different than the first time I had rode the wooden horse. First of all, the edge was no longer this painful crushing sensation between my legs. Ironically, the rubber was protecting me from the solid wood and cushioning me slightly. On the flip side I could feel the tiny exposed tips of the tacks digging into my labia. I adjusted my position and tried to get comfortable. After all, I only had to handle it for ten minutes, right?

Kari looked at Robert. “Sit on the couch and make yourself ready.” Robert nodded and immediately moved to the sofa in front of me and began rubbing his still soft cock, watching me suffer in front of him. Evidently I must have been particularly sexy, because it wasn’t that long before he was starting to get hard.

While Robert was rubbing himself, Kari had lifted her right hand and once again started squeezing my breasts. The tiny pin pricks were enough to attract my attention, sending little shocks of pain through my nipples. She moved rapidly, squeezing here and then there. Then she smacked me lightly on the bottom. This resulted in my gasp and a hip jerk forward. I cried out as the tiny tacks in my saddle dug in deeper. Pain was radiating up from between my legs, despite the rubber mat stuck up my pussy and I began rocking back and forth, trying to relieve the pressure.

A pinprick pinch on my nipple made my eyes open and Kari was right there, grinning.

“You like it don’t you, little slut?” she asked. “You like being hurt?”

I nodded, the pain melding with the pinches and the vibrations of the vibroballs in my pussy. Kari’s left hand went down to the saddle and I felt her bare fingers touching my clit. I gasped, nodding.

“Oh yes! Please hurt me!” I said, my body trembling.

“How much do you want it to hurt?” She asked, lips at my ear. I could feel the warmth of her breath.

“Badly! Please! As much as you can, Kari!” I practically shouted.

“What are you?”

“A Nympho Humiliation Pain Slut,” I cried out.

“And you want me to hurt you?”

“YES!” Now I was bucking. Her finger was working my clit in circles while the pin covered fingers switched from one nipple to the other, crushing and perforating the little nubs. Robert watched, his fingers moving up and down his oiled and now straight cock.

“How long do you want to ride the horse?” Kari demanded.

I was getting worked up. The orgasm was getting close. “Forever!” I said strongly, with a bit of helpless desperation in my voice. At that moment I was totally honest. I WANTED to ride the horse, with the spikes and everything, forever.

I grit my teeth as I felt the orgasm build and threatened to overwhelm me. But then Kari pushed me backward, rolling me so that the pressure of the horse was now on my tailbone and not my pussy. I felt the rubber pad extracted from between my labia and Kari quickly checked me to see if I was damaged. Evidently I wasn’t because she then tipped me forward and I was treated once more to the sex bruising hardness of the wooden horse, pressing against my pin pricked labia, clit, and perineum.

And I was once more back in sexual hell.

Kari bent down and put the heavy sand filled jugs on the spreader bar, increasing the weight and pulling me down even more. I gasped as I tried to adjust to the additional pressure between my legs.

You know, pain is sort of a weird thing, isn’t it? I mean, right now, while I’m writing this, I’m having a hard time REMEMBERING how much it hurt. I mean I know it did. I can REMEMBER it hurting, but I can’t remember how much. Strange, isn’t it?

So while I sat there, rocking back and forth, humping the wooden horse, my clit going down to be pinched with each forward movement, Kari moved toward the sofa. I watched as she ordered Robert to kneel on the sofa while she sat down to Robert’s left. She asked him to face her, rather than me, and I suddenly saw Robert in profile, his hard cock his normal size, but sticking straight out at attention. I bit my lip as the combined sensations of pressure, the vibrations of the vibroballs, and my tenderized labia sent some interesting messages up to my brain. Seeing Robert in all his oiled glory didn’t help either.

But then, to my horror, Kari grabbed his cock. With her right hand. The hand covered with the pin glove. I saw Robert’s eyes widen, but he stared stoically ahead and didn’t say anything. Kari didn’t even look at him. She was looking at me. Her crystal blue eyes seemed to sparkle with evil design and she squeezed his cock hard. I could tell because Robert’s expression changed a smidgen and I could see him having trouble staying still.




“If you cum I’ll stop,” she said, still looking straight at me. Then she squeezed him again.

I can’t really imagine what it felt like. I know a man’s penis is delicate and very sensitive. Hell, that’s why Kari and I would find a gullible but handsome hunk every few days, invite him to our place on a Saturday or Sunday morning, tie him to the bed, and milk him until his cock was nothing more than a sore tenderized, raw piece of meat. Granted, we never actually fucked a guy until he bled, but I know that we came close a couple of times. I remember one black guy we had down and he ALMOST ripped his arm out of its socket trying to get free. He ended up bending the bed frame though.

Kari shifted her grip so that more of her palm was now over Robert’s tip. She squeezed again. Words of protest formed on my mouth as Robert winced, a look of real pain, but they died when I realized that nothing I said short of “Oh God! I’m cumming!” would actually make Kari stop. And it had to be a real orgasm.

I was under a lot of pressure at that moment. Sure, I was hot and bothered, and even half was up the ladder to the impending orgasm, but there were some serious issues at play. First of all, if I orgasmed so soon, then my tolerance for the wooden pony would be seriously diminished until I could get myself worked back up. I wanted to do another hour too, just like last time. So no matter what I was looking at some pretty agonizing moments. Second of all, forcing an orgasm out while riding a pony, I mean ACTIVELY working myself to orgasm, meant inflicting some rather pernicious discomfort to certain parts of my anatomy. It wasn’t like I could reach down and finger myself until I came. It meant I’d have to really RIDE the horse, and not a walk or even a cantor. I’m talking about humping the wooden horse at a gallop. Then there was the torture being applied to Robert. Obviously he wasn’t used to being a pin cushion, but there was no guarantee that immediately after I came and Kari took her hand off his cock, she wouldn’t just wait a few minutes and then put it right back on. Or worse, right?

She shifted her grip again, this time moving her fingers downward so that most of Robert’s shaft was covered from the base to the now exposed tip. I imagined I could see the little red pin holes as she gave him another hard squeeze. He groaned and I could see his jaw set as Kari began pulsing her hand in rapid little movements. God, that had to have hurt.

And so I began pumping my hips, thrusting my body along the spine of the horse in wet painful glides. My clit was dragged down underneath, pinned between my pubis and the wood. I’m not an expert… okay maybe I am, but I can say that crushing your clitoris between your entire torso and a sort of sharp wooden point IS a decent way to push yourself to orgasm. I rocked back and forth, my arms sort of flapping like wings to the sides of me as my movements set the milk jugs hanging from my feet swinging. Kari watched me, my face heating up, my chest heaving, and my body tensing. I could feel the buildup inside me. She gave me another wicked look, let go of Robert’s cock, and grabbed hold of his balls.

Ooohhhh….



I hate to say this, but while I wanted to end Robert’s torment, it sure was turning me on! The thought of all those pins against his scrotum was just… hot. I’m not so sure he thought so, because his face had one of those “Oh Shit!” expressions followed by a rather ginger wincing as Kari began kneading his testicles. I bucked like mad, working myself as hard and as fast as I could. Kari continued for another twenty or thirty seconds and then let go. Then she grabbed his tip between two pin covered fingers and began tweaking, hard.

“OH GOD! I’M CUMMING!” I shouted. And I was. Wetly. I could feel the juices streaming from my pussy and for a second, down my thigh. I wasn’t so much rocking along the spine of the horse now, I was sliding, back and forth in this ludicrous and totally lewd maneuver that would look pretty awesome if it had been caught on video. I was so far gone too. My eyes were rolling and fluttering, my heart was racing, I felt like I had just been injected with stimulants, and my entire body felt light for a moment.

Then that feeling ebbed and I was dropped down several stories onto that wooden horse with no padding and nothing to slow me down. Ow.

At least Kari had let go of Robert though. As I groaned and started whimpering from the pain shooting up through my groin, Kari got up and moved back over to me. Her pin covered glove found its way to my breasts, squeezing each in turn, playing with the nipples, and generally hurting me. Her left hand once again found my clit and began rubbing it, using my own juice to lubricate the tiny nodule of flesh. I started shaking uncontrollably even as the arousal started to bubble through the layer of pain. Kari didn’t waste a moment and I thought I’d go nuts when she switched hands and my clit was suddenly pinched.

Have you ever heard the expression “I felt pins and needles”? Well, I have. On my clitoris. Imagine your most sensitive spot being pinched with a mass of pins and needles. Sharp ones. I’m not sure how it could have been worse, or more erotic. I gasped and was instantly catapulted upward into this spiral of mixed pain and pleasure. And Kari didn’t stop either. She kept moving from one breast to the other to my clit and the followed it all up with one or two smacks to my ass. Then we started again. In short order I was humping the horse, sliding my pussy along. Except now I was so wet, and the wood was drenched, that there wasn’t any friction, so no moving forward to drag my clit under. Just the inexorable pressure downward along with the torments inflicted upon me by Kari.

When we passed the forty five minute mark I was really close to my third orgasm. Kari was playing me like a violin, keeping me vibrating just below the point where I could push myself over. It was agony and ecstasy all in one blow. The jugs on my legs swung violently back and forth as I did the twist, my legs parted wide, all while balanced on the edge of a wooden horse.

I didn’t make it to an hour, in fact I didn’t make it past my previous fifty four minutes, but I got close! At fifty one minutes, after my third orgasm the pain was too much and I turned toward Kari who was still pinching my right nipple.

“Anniversary” I whispered, to tired to shout it.

“Robert!” Kari said sharply. He jumped off the couch even as Kari was bending down and freeing one ankle from the spreader bar. Thank God it came loose with a simple metal clip. Seconds later Robert was picking me up by the waist, lifting me away from that god awful torture machine.

Kari removed the spreader bar from my other ankle while Robert turned off the vibroballs and I was once again carried to the master bedroom. I was sobbing, or at least crying pretty hard. My pussy hurt, but I also felt light headed from the sexual explosion and despite the fact my wrists were still stuck to my collar, I laid my head on Roberts shoulder and just tried to pretend I didn’t exist.

He laid me down softly on the sheets. I could smell them, not the sheets, but Robert and Kari’s scent on the 500 count Egyptian Cotton. It was both masculine and feminine all at the same time, with hints of Kari’s vanilla perfume and a little bit of Old Spice. And there was the smell of sex, that musky flavor that comes only from a woman’s orgasm. Of course it could have been me. It wasn’t like I hadn’t cum in that bed before. In fact, unless Kari has bought a new one (which IS possible), it’s likely I have cum in that bed more often than Robert has!

I was laid on my stomach this time, which was a blessing considering what Kari had only recently done to my breasts. I felt two sets of hands rubbing me, massaging my legs, my still bound arms, my back, even my ass. Then Kari left the room and it was only Robert touching me, gently trying to pull all of the pain out of me.

“Thank you,” he whispered in my ear. I couldn’t help but to smile. His words were soft and filled with appreciation and love. “You didn’t have to do that for me.” I turned my head and looked at his brown eyes.

“Yes I did,” I replied. He smiled, then leaned forward and kissed my forehead. He jumped back to work on my shoulder and upper arm as Kari returned.

I felt the bed depress down by my ankles as Kari climbed up onto the mattress with me. Her knees widened and I felt my own legs parting a bit and I hissed as aches went shooting up my calves and into my crotch. I felt a tug and then Kari was pulling the two vibroballs out of my pussy. I groaned, wincing as the two ovoid objects pressed against my bruised and now swollen labia. It hurt.

Kari got up off the bed and I heard the dresser door slide open. That got my attention. When we were living together, the top dresser door was where she kept…

Oh my God… no!

She returned to the bed holding the wooden paddle. It was thick, drilled with holes, and I knew from experience, very painful. I clenched my ass even as I started to turn over. Kari put one hand down on my rump, pushing me back down.

“Stay still!” she demanded. My heart thumped as the words “Oh God Please NO!” went rapidly through my mind over and over. Kari held up the paddle and looked at Robert over my back.

“How many thrusts will it take for you to cum, Robert? Right now the cost is two thrusts per stroke. If you run out and have to use more, the cost will be one thrust per stroke. Oh, and if you cum BEFORE you use all your purchased thrusts, the unused thrusts come back at two strokes a thrust. So use your brain instead of just your dick.”

I looked at Robert and he looked at me, and I knew I was about to get seriously paddled.

Part Three will continue to be available at Michael Alexander’s BDSM Blog for free! If you enjoy Breanne’s antics, feel free to catch up with her daily assignments! You can also read all of Breanne’s previous year’s assignments at the Michael Alexander Stories VIP Lounge! Join today! It’s worth it!