A Stimulating Life Ch. 06

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Anal penetration and other humiliations for Scott.
9k words
4.53
22.2k
21
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Part 6 of the 9 part series

Updated 06/09/2023
Created 01/28/2020
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On the morning of February, the 1st, Mrs. Canalis announced that she had planned an amazing day for me.

She refused to share any of the details for my "amazing day' with me and instead handed me over to one of the maids so that I could be properly prepared.

I soon discovered that preparing me meant the maid brushing my teeth, giving me an enema, washing me thoroughly and shaving me into prepubescence. After she was finished grooming me, I assumed that I was prepared for my "amazing day", however, I soon discovered that I was wrong.

The maid grabbed me by the arm, escorted me down to the foyer and told me to place my arms behind my back so she could tie them. Then she opened a drawer and produced enough ropes to make me helpless.

Another maid ambled into the foyer while I was being tied. The ropes went tightly around my wrists and elbows, immobilizing my arms in a box tie. Her skill and efficiency at tying my arms was such that I knew she must have tied people like this before.

"He looks so much sexier all tied up and helpless," said the maid who had watched from a distance, "Would it be okay if I spanked him?"

"Mrs. Canalis gave me permission to spank him," said the one who had tied me.

The two maids argued heatedly over who should be allowed to spank me until Mrs. Canalis came storming into the room, glared at both maids and snapped, "There will be no more shouting in my house! Anna don't be greedy! Share the slave with Daria!"

Grudgingly, the maid named Anna followed orders and allowed the other maid to abuse my poor bottom. There were two chairs in the foyer. Daria sat down in one of them and pulled me down on top of her until I was arranged to her satisfaction over her lap. My arms were bound in such a way that I was unable to protect my backside no matter how hard I tried. That meant that my naked, innocent buttocks were available for whatever torments Daria had in mind.

Of the two maids, Daria looked to be the least imposing. She was about two inches shorter than Anna and was almost anorexically skinny. Her arms were slender and by the look of her I didn't think she would be able to spank me awfully hard.

Of course, appearances can be deceiving.

Daria was a lot stronger than she looked and I ended up gasping in pain at the first stinging blow. The smacking of her hand on my bare ass reverberated loudly in the foyer and I kicked and squirmed as Daria reddened naked buttocks.

When my eyes were welled up with tears and bottom was on fire, Daria lifted me to my feet then turned me so Mrs. Canalis and Anna could have a good look at my reddened ass..

"How's that?" Daria asked, "Did I do better than Anna?"

"It's not a competition," Mrs. Canalis replied, "You made his ass red and tender. That's all that's important."

She was right about my ass being tender. I had been spanked until my skin was raw, and while the women in the foyer were mostly focusing on the redness of my poor bottom, Daria was eying my cock, which was hard and embarrassingly erect. It was in my nature now to become sexually aroused from corporal punishments and the spanking Daria had delivered left my cock predictably hard and throbbing.

Daria stared at my swollen manhood and opened her mouth as if to make an astute observation, but then her mouth snapped shut again. She continued to stare at my cock, but she seemed at a loss for words. I think she was shocked that a man could be in so much pain and still have an erection.

"I've invited guests over for today's festivities," Mrs. Canalis informed me, "You'll wait for them in the back yard."

I was led out into the back yard. I was naked, my hands behind my back, a collar around my throat and pulled forward by a leash. One of the maids held my leash and compelled me to follow her. I was led to a verdant section of the yard with two pillories. Each pillory looked primitive and ancient and seemed out of place on a twenty-first century estate, but I kept my opinion to myself.

I stood timidly by one of the pillories as my collar was removed from my neck and my hands were briefly given their freedom. Another servant raised up the upper yoke of the pillory and beckoned me to rest my wrists and neck on the lower part. I bent over at the wait and the upper yoke came down with a wooden "thunk". A heavy lock secured the two halves together and I became a helpless prisoner once again.

"Mrs. Canalis needs to go and greet her guests when they arrive," one of the servants told me, "We'll keep an eye on you until she returns."

While Mrs. Canalis was gone the servants took the opportunity to examine my naked body. They ran their hands all over my abused hindquarters, stroked the smooth flesh of my perineum, cupped my balls and even pried my buttocks apart and gently stroked the soft flesh of my anus.

I felt a finger pushing into me and I gasped. I was already naked, bent over with my wrists and throat bound. I felt helpless enough without being anally raped.

"He's awfully tight for a slave," one of the servants commented as she wriggled a finger inside of me, "You'd think a slave would have been used so much by now that I could fit my whole fist up there."

The finger was withdrawn from my rectum and there was an intense discussion about how wide a phallus could be forced into my ass if they used enough lubricant. During this entire conversation I just remained bent over and helpless, feeling vulnerable to impalement upon whatever sort of thing they decided to thrust into me next.

Luckily before they could find something massive to spear my anus, Mrs. Canalis returned. She had changed her clothes and was now wearing a black two-piece swimsuit. Locked in the pillory I couldn't get a good look at her, but I did see that she had beautiful legs, tight abs, and a toned ass. She was in great shape for a woman in her forties.

"We're going to leave you in that pillory for a while," Mrs. Canalis explained, "however, I thought I'd have my guests say hello before we go for a swim."

Mrs. Canalis stepped back and urged her guests to step forward. Christopher was the first one to step into my line of sight. He was wearing black swim briefs that did little to conceal the shapely curves of his ass. The next person walk up to me was a young man named David. He was a slender youth with an athletic build and a cute, boyish face. He was also wearing black swim trunks that left little to the imagination.

"And last but not least," Mrs. Canalis said, "We have David's slave."

I was told that David had purchased his slave at the same auction where Mrs. Canalis had purchased me. I briefly considered the possibility that I might have met David's slave while I was going through my slave-training at the Vineyard, and then David's slave stepped forward where I could get a good look at him.

"Nari," I exclaimed as he walked into view. He had blonde hair, blue eyes, a slender waist, beautiful pecs, reddish-pink nipples, and perfect dancer's body. Then he got down on his knees so that his face was level with mine. I couldn't touch him, but just seeing him made me happier.

"Nari was easily the most beautiful slave sold at the auction that day," David told me as I looked into Nari's boyish eyes, "I had no idea that my slave and you had a sexual relationship. That was just good luck on my part."

"It creates possibilities for all sorts of sexual entertainments," Mrs. Canalis added.

"We've already planned some of them out," Christopher commented.

Like me, Nari was naked and his cock was conspicuously erect. And then Nari's situation became even more like mine as he was locked in the pillory beside mine. Christopher spent several minutes fondling my naked body before moving away from me and then I heard Nari gasp as Christopher presumably ran his hands all over Nari's naked body as well.

"There's something about punishing naked slaves together that creates a sense of solidarity," David explained, so, I decided that Nari and Scott should be whipped side by side."

David whipped Nari while Mrs. Canalis whipped me. I couldn't see what sort of whip she was using, but I could certainly feel the sting of leather every time she used it on my bare skin. Leather cracked across my naked ass, scorching pain into my innocent flesh and making me howl in helpless agony.

I reflexively stamped my bare feet as if that might somehow negate some of the agony being inflicted on my backside. It didn't work, but I was naked and locked in a pillory. What else could I do other than stamp my feet and scream in helpless torment?

I was whipped perhaps ten times or more across the backs of my legs. I yelled from the pain each time the leather scalded my naked skin. I struggled against my bondage, but the wooden pillory easily defeated my most frantic squirming.

By the time Mrs. Canalis was done, my backside was throbbing in agony and I was panting and gasping for breath. Christopher came around and gently whipped tears away from my face and then Nari's.

"I don't know which of you is more beautiful," Christopher said, "I think I've got a crush on you both."

As Christopher, David and Mrs. Canalis walked off towards the pool, I heard Nari say, "Oh, this is going to make my life more complicated."

I agreed. Christopher was our friend and ostensibly straight. It was weird having him ogle and fondle our naked bodies. It seemed wrong somehow, but I reminded myself that everything was out of my control. I was a naked slave locked in a pillory. Until I got my freedom back, nothing that happened was my responsibility.

Embracing helplessness when you're naked and locked in a pillory is easier than I realized. I felt foolish with most of my body hidden where I couldn't even see it. And yet those parts of my body could be abused or molested in dozens of ways by anyone who happened to wander in my general direction.

Nari had a look on his face that suggested he was swimming in feelings of helplessness as well. His face was still beautiful, even streaked with tears. He had the most beautiful lips. They were so full and sensual. And I knew from experience that he could do amazing things with that mouth. I wanted to kiss him, but that wasn't possible with both of us locked up like this.

While I was locked in the pillory, one of the servants rubbed medicinal gel into my wounded backside. Mostly it was rubbed into my buttocks and my thighs. However, the person who applied the gel to my poor, abused buttocks also smeared gel all over my cock and rubbed it in until I was on the verge of orgasm, leaving me in sexual frustration.

Nari was subjected to the same treatment and then the servants proceeded to grease my anus up with anal lube. I could feel them working a cold glob of grease into me and then twisting their fingers around inside of me. My interior was fully explored while I was bent over and my ass vulnerable. Nari gasped as his anus was impaled and copiously lubricated as well. These actions strongly suggested that Mrs. Canalis's guests would be coming by to fuck us later. We were helpless, naked, bent over and lubricated for anal rape. It didn't take a genius to guess what was planned.

I nervously shifted my weight from one bare foot to another as I awaited my fate. The servants didn't seem to mind if Nari and I conversed while we waited, so we attempted to catch each other up while we were bound, naked and waiting to be sexually abused.

Nari told me about his slave-training at the Vineyard. It was very similar to my own training. He had been ruthlessly trained in slave positions, spanked, whipped and chained up in the shower room so he could be raped by prospective buyers.

"The worst part of the training was the libidol," Nari confided, "My cock was constantly hard and erect but the drug made it impossible to have even one orgasm the whole time I was in training. I'm a very sexual person, I need my sexual release."

I agreed with Nari. Libidol was the worst part of slave training. On libidol my cock would be hard all the time, so hard and swollen that it ached, but no matter how much my cock was sucked, oiled, squeezed, twisted, or pulled, achieving orgasm was never possible. It was a form of sexual torture.

And while Nari and I were discussing our slave-training, Christopher and the others returned from their swim. When they got close, the three of them began to peel off their clothes. Christopher's cock was instantly hard and impressively large. David's cock wasn't quite as impressive, however, it was big enough to be intimidating. I was suddenly grateful for how through the servants had been in lubricating me for anal penetration.

"He has dancer's legs and a perfect ass," Christopher said as his hands explored my body, "and yet the whole time we lived in the same apartment together we never fooled around."

"Well, you'd best make up for lost time then," David suggested. And then I felt Christopher's hands tracing the welts on my buttocks. He caressed my naked curves while Mrs. Canalis stood in front of me and forced her crotch into my face.

"Christopher can't be the only one who has fun with you," she insisted, "Lick me."

I licked at her swollen pink slit and worked my tongue into the gap between her labia. I was confident of the job I was doing as her hips swayed and she began to make soft moaning sounds. And while I probed her vagina with my tongue, Christopher stood behind me and pried my buttocks apart. I could feel the head of his hard cock as he pressed it against the delicate flesh of my anus. I whimpered as he forced open my sphincter muscle and then the shaft of his cock was slipped firmly into me.

I gasped as he penetrated deeper and deeper into me. I made sounds of helplessness as my ass was roughly used, however, my sounds were muffled as my tongue was deep inside my mistress's wet sex.

Christopher rammed his shaft into me again and again. The more he thrust himself into me, the more I moaned. His cock was thick and being impaled on it made me feel helpless and controlled. I slipped into a mindless state, where I became nothing but a naked slave to be punished and possessed and objectified. As Christopher's thick shaft thrust deep inside me over and over again, I gasped and panted and accepted that he owned me and could use my naked body in any way he desired.

When I became physically and emotionally overwhelmed by all of this, Christopher pulled out of my ass, slapped my tender buttocks vigorously a half dozen times with his hand and then forced his cock once again into my lubricated anus.

I grunted and panted and somehow continued to probe Mrs. Canalis's pink slit with my tongue while my ass was being raped. I felt Christopher spasm inside of me as he let out several large gasps. David climaxed at almost the same time as Christopher. It took a little bit longer for Mrs. Canalis to reach orgasm, although when her orgasm hit, it lasted longer and sounded much more intense.

Christopher, David, and the woman who owned me were all spent and riding a wave of post-orgasmic bliss. I assumed that meant that the festivities were over, however that assumption was wrong.

"David was terribly excited when he learned that the two of us had purchased slaves who were already involved in a sexual relationship," Mrs. Canalis explained, "It's very rare that slave owners end up with slaves who know each other so well."

"And now that we've brought the two of you together..."

"We're going to have the two of you have sex while David and the rest of us watch."

Nari and I were both unlocked from our pillories and I slowly stood up. Nari was moving gracefully, but cautiously as he got up and took a few tentative steps towards me. If anything, Nari was even more beautiful than I remembered.

He still had a tiny waist and shapely legs, but his already tight abs looked more amazing than ever. There was sexy, sculpted muscle just underneath the skin. His calf muscles looked more developed too. Slavery certainly agreed with Nari. He seemed sexier now than when I first fell in love with him. And unless I was delicious, his cock had somehow gotten bigger. I mean, Nari had always been well-endowed, but his cock seemed to have increased in both length and girth. How was that even possible?

David gave Nari and I a few minutes to touch each other and engage in foreplay before we got pornographic. Nari's ass that was so beautiful it was mesmerizing. I literally had trouble looking away it, it was bewitching in its beauty. Of course, his ass had become reddened from his recent whipping, but the whip marks just seemed to make his ass even more beautiful.

Nari assured me that my ass and the backs of my thighs were just as reddened as his own. He complimented me on my legs and my body in general. I was a professional ballet dancer, so it was my job to stay in excellent physical condition. Still, when someone like Nari told me that my body looked amazing, I could eat up those compliments with a spoon.

With Mrs. Canalis and her guests watching, Nari gave me a lustful look, took my face between his hands, and brushed his lips against mine. An instant later I was melting into a passionate kiss. Nari kisses better than any man or woman that I know of. The kiss was hot, intimate, and triggered a delicious tingling sensation that resonated through most of my body.

As we kissed, my hands explored Nari's naked body. His skin was soft, and feverishly hot. His lips were surprisingly soft for a male, something about that excited me and I kissed him back with even greater intensity. And when Nari's tongue tried to enter my mouth, I widened the opening between my lips, making it easy for his tongue to invade.

Nari kissed me hungrily, like a man who had been denied pleasure for months. I wondered just how badly he'd been treated as David's slave. From my perspective it seemed as if Nari had been denied physical affection and now that he had me, he was going to use me to satisfy all the desires that had been starving for. Nari's tongue did battle with mine, running up against it, wearing it down, pinning it down, and then retreating before brushing up against it again.

Nari moaned into my mouth as his hands explored my naked body, cupping my sore buttocks, caressing the small of my back, tracing his fingertips across my shoulder blades and the vertebrae of my spine. It seemed as if he intended to touch every inch of my naked body while we kissed.

Of course, my hands weren't exactly idle. While Nari ran his hands up and down my body. I took hold of his abused buttocks in my hands. His ass was amazing, and I savored the feel of Nari's firm gluteal muscles covered in soft, smooth skin. I kneaded his lovely buttocks with my hands, relishing the feel of his boyish derriere as much as I relished the feel of his tongue in my mouth.

As much as Nari enjoyed making out, there came a point where we had to do more than just kiss and grope each other. It was at that point that I ended up down on my knees, kneeling in the grass in front of Nari's hard cock.

I placed my hands on his hips and inched my face towards his swollen erection. His cock was so engorged with blood that the shaft had become dark pink, while the head of his cock was almost strawberry red, and a thick dollop of milky-white semen had seeped out from the tip.

I cupped Nari's balls with one hand and found them to be heavy. I wondered how long it had been since he last had an orgasm. Judging by the size and weight of his scrotum, it had been quite a while. His balls seemed quite full.

Nari's penis seemed to be both longer and wider than I remembered. His cock was swollen and throbbing no doubt due to constant stimulation and orgasm denial. I hypothesized that a man's cock could become larger if he was kept constantly hard but never allowed any orgasmic relief.