Seven Tails: Tail 02

Being bound seemed to give him a measure of comfort, letting him justify in his mind that he had no choice even though he had agreed to this thing willingly. Plus we were all coming to the realization that being tied up turned him on. I was more than willing to accommodate that. Sarabeth always submitted to being bound in various ways because she knew it pleased me even though the act itself did little for her. The turn on for her was submitting to and pleasing me, not necessarily the bondage.

I had purposefully set the hassock down over a length of rope which I now brought up and tied securely across his shoulders, holding him down. Using her hands and knees, Sarabeth had him spread his legs apart until each knee was on either side of the hassock. I loosely tied a loop around one leg right above the knee, then pulled the rope around the front of the hassock and secured it to the other leg and tied it off, keeping his knees bent and his legs spread wide with his cock hanging down the back, brushing against the leather. He wiggled a little and made small sighs. One of my hands went to the back of his neck and caressed him gently.

"One last question, Nathan. Do you want me or Sarabeth to give you your tail?"

"Y-you p-please, Master."

"Very well, then." Sarabeth and I changed places, swapping one end for the other. She immediately put her hands back on his shoulders, her strong nimble fingers digging in to his tensed muscles while she bent her head and whispered softly into his ear. I couldn't hear what she was saying but I could see some of the whiteness leaking away from the knuckles of his clenched fists. I just sat there for a moment, drinking in the sight of Nathans rear end sticking out there so conveniently. The strong fine legs which were becoming more defined by the day. Those tight cute ass cheeks, so firm and so full. His heavy ball sack dangling like a fresh fruit, hanging in front of that fine thick cock of his that was halfway hard and twitching in anticipation even through his nervousness.

And right there between those heavenly ass cheeks was the prize I had been seeking. That tight virginal little ass. Reportedly unpenetrated by anyone or anything ever. Not even his doctor had been there. And I was going to be his first. Well, if you didn't count the tip of Sarabeth's tongue, that is.

I was going to deliver his first fingering and after that the first of many butt plugs to come. And later on this evening I was going to introduce his virgin hole to it's very first cock. Even if it would be a bit on the painful side for him at first, I had a feeling he was going to end up loving it in the end.

No pun intended, of course.

My excitement didn't all revolve around him being a virgin. Or even completely was it about fucking him, though I was going to enjoy it immensely tonight and for many nights to come. No, most of my joy came from the fact of him submitting himself to me. He'd already taken the collar and the leash and the harness. He already performed for me in the ring. But from now on he was going to wear my tail and show not only me but any who saw him that he belong totally to me, mind, body and soul. After tonight he would be more thoroughly united with me..... With both Sarabeth and I, than after any sort of mundane marriage ceremony. He was going to become one of us forever.

On the other hand, I wanted Nathan in my bed so bad it felt like I had been waiting an eternity. He was so pretty I had wanted to fuck him the first time I laid eyes on him and the waiting was driving me crazy. But now the waiting was almost over and serenity and joy washed over me like a cool shower. Though while I was cooling off on the outside, my inside fires were stoking up and getting near the boiling point. This was going to be a night that we remembered for a long time.

Reaching up, I took both of his hands in mine, my palms wrapping around his clenched fists and started rubbing them slowly, my thumbs probing in between his palm and little finger, trying to get him to relax his hands. Slowly and almost reluctantly his hands open and I clasped them in mine finally and squeezed his hands in what I hoped was a reassuring manner. Nathan took a few more deep breaths and squeezed back and more of the tension leaked out of him. Sarabeth was still caressing him and whispering in his ear softly. Occasionally she would kiss the back of his neck or rub her lips along his shoulder and the side of his neck, making him moan and shiver just a little.

Gradually, I pulled my hands from his and worked my way down his spine, my thumbs and fingers massaging as I went. Rather than work my way down his buttocks I went to the side down his hips and ran my hands up and down his thighs. Only after he was used to me being back there and touching him did I work my way up to his ass cheeks, shivering a little myself as I reveled in the feel of his firm bottom and thinking of the joys to come from there.

The way he was tied down to the hassock with his legs on either side left his butt spread slightly open anyway so I didn't have to fight his urge to clench his butt cheeks together, which was good. Right before I started to delve inside I reached over and grabbed the bottle of lube and stuck it between my own thighs to keep it warm. My thumbs lightly rubbed up and down his perineum area, watching his ball sack retract with each touch. And each time I got closer and closer to the entrance to his anus which was contracting in spasms in expectation of being penetrated.

Right before I actually zeroed in on his entrance, I reached down and got a good dollop of lube on my forefinger then rubbed it in smaller and smaller circles around his hole until the tip of my finger rested there and just pressed gently, not seeking entrance, just letting him know I was there. He gasped and wiggled at the touch. His legs flexed the little bit he could against the ropes. Sarabeth lifted his head and brought her lips down to his and kissed him long and hard. While he was distracted I dripped some more lube onto my finger and pressed slowly forward. Nathan moaned into Sarabeths mouth and the ring of muscle guarding his entrance went into spasms trying to prevent my intrusion. But each time it relaxed just a little I gained more ground, my finger slipping deeper and deeper inside of him until it was buried in his butt all the way. Giving him just a moment to get used to the feeling, I slid my finger almost all the way out then back up inside of his ass again, making him squirm some more. Since he was turned the right way occasionally I would curl my finger downward and graze across his prostate gland which would make him press his bottom back at me the best he could and made his now hard prick thump against the leather side of the hassock. A small evil grin on my face, I reached up with my other hand and grabbed his prick and squeezed it. He tore his mouth away from Sarabeth and moaned aloud and said "Oh.... Oh my god... what are you doing to me?" I released my hold on his cock and patted him on the bottom and said "Relax, boy. Just trying to make you feel good. Show you it's not as bad as you feared it would be." I drizzled more lube on his hole and on my fingers. "Now I'm going to try two fingers. Open you up a little more. It will feel even better, I promise."

"Oh god....."

It took a little patience on my part and some more moaning and gasping and wriggling on his but I finally had two fingers buried all the way up his ass, stretching his tight hole open. I started slowly twisting them back and forth stretching the muscles and massaging his insides with my fingertips. The lad was covered in sweat and goose bumps and he was alternately holding his breath and gasping while I worked my fingers in and out of his bottom.

Since the tail he had chosen wasn't much larger than my two fingers, I decided against trying a third. He was becoming accustomed to the feeling of being full and I thought it was time for the next step. I slowed my movements inside him and held my fingers still. "Nathan. Are you ready for your tail, now?"

"Unhhh... I.... think so, Master. Unhhh..."

I curled my fingers down and rubbed them against his prostate making him moan and press back into me. "Yes or no, Nathan. Are you ready for your tail now?"

"Ohhh... god. Yes, Master! Please!"

"Good boy. Sarabeth? I need a hand."

"Of course, Master." She came around and as I held up his tail she shot a generous blob of lube on the tip of it and a small line up the shaft. I slowly removed my fingers and before his body could react and clench back up again, I pressed the tip of the plug to his slightly gaped open hole and pressed forward slowly but firmly. He gasped and wiggled and squeaked and whined a little as it spread him open even further than my fingers had and his toes curled up hard. We all held our breath and I fed more and more of the plug up his ass until with a mutual sigh, it reached the narrower portion and allowed his ring of muscle to close on it and hold it in place.

I patted him on the ass cheek again and said "Congratulations, Nathan. You are now a full fledged pony." He just lay there over the hassock panting "Oh my god... Oooh... Oh my god..." over and over again.

And as I predicted, I absolutely loved seeing my tail poking out of those awesome ass cheeks. The sight made me flush with desire.

Working slowly and deliberately, Sarabeth and I undid the ropes holding him down, saving those on his wrists for last. As his hands came free we each put a hand under his arms and lifted him and rolled him backwards saying "Easy... easy... we got you.. Just lay back..." until he laid on his back on the rug. Of course I forgot to take into account that his butt would hit the ground first, driving the plug deeper into his ass. He groaned deep in his chest and his hips flexed and thrust upwards and he said "Oh shit! Oh my god...."

As Sarabeth pulled his legs apart and knelt between his thighs, I lay down beside him and slipped the blindfold off of his eyes so that my face was the first thing that he saw. One hand stayed on his cheek and turned his face towards mine as I gazed into his eyes with a smile.

"You did it, Nathan. You took your first tail. I am so proud of you. Now you are my pony forever." As my lips closed on his, Nathans hands came up, one on my back and the other caressing my shoulder as his mouth opened to mine. I gestured to Sarabeth and she wrapped her hands around the shaft of his prick as it stood straight up from his crotch and began stroking him. He moaned against my mouth and his whole body writhed in pleasure.

I pulled back just a little and spoke right against his lips. "Does that feel good, boy?"

"Oooohhh.... Yes, Master!"

"Do you want her to suck your cock, Nathan?"

"Oh god yes, please, Master! Please let Sarabeth suck my cock, Master! Oooohhh... I want to come so bad...."

I stroked his cheek with my fingers. "I have so many things planned for you tonight. This is going to be a night none of us will forget. But I think you deserve a small reward." Looking down I said "Sarabeth? Do you think you can make him come?" She gave me a happy smile.

"I have no doubt about that, Master!"

"Then lets make my pony boy happy, shall we?"

"Of course, Master!" With a well practiced move, she flipped her pony tail to one side and, tugging back his foreskin, leaned over and took the head of his cock deep into her mouth.

As he moaned and lifted his hips to thrust his cock up into her mouth, Sarabeth slipped a hand underneath his butt and cupped her hand around the base of his tail, pressing it firmly into his backside. He gasped and shuddered and made articulate noises. Nathans toes curled up so hard I heard the joints pop and his whole body stiffened like he'd been hit with electricity. He convulsed a couple of times then stiffened again and howled and started coming in her mouth harder and faster than I had ever seen him do before. His hand tightened on my bicep so hard it was almost painful as he shook and shuddered through his orgasm. It's suddenness and ferocity were a little starting to all of us. Being the true artist that she was, Sarabeth kept up the stimulation with her hands and her mouth and manipulating the plug in his butt bringing him to peak after peak until she finally slowed to a halt. Nathans hand fell from my arm and his eyes closed and he went completely limp, his hand bouncing off the rug as it dropped.

Startled, Sarabeth let his prick slip from her mouth and fall back on his belly. "Oh my god! Is he okay?" I smiled.

"He just fainted, love. He'll be all right in a moment."

Twelve

Outside the storm was still raging in direct opposition to the peace that was reigning inside the house. Despite being in the dark we were all in a bit of a celebratory mood. Giving Nathan his first tail was a huge milestone and I felt like a huge weight had been lifted from my shoulders. And I burned to begin the final phase of his initiation. Taking him to my bed.

But he needed time to get used to having that tail in his bottom so I calmed myself and waited. It would come soon enough. This very evening, as a matter of fact. What helped me considerably was watching him come to terms with the new experience. For one thing the hairs on the tail kept brushing against his legs and startling him. He was constantly jumping and brushing the backs of his legs.

"I don't know if I can get used to this thing touching me."

"You will, Nathan." said Sarabeth wisely. "Once you get used to the idea of looking at it differently. That isn't just a thing sticking out of your butt. It's your tail. It's Masters tail. It's your symbol of pride. It's your symbol of submission. Of ownership. Even more than his mark on your neck. It shows the whole world that you belong to Master Max Rambeaux and that you are proud to be his pony." She put a hand on her own butt and smiled and her nipples hardened into little points. "Once you get that, then feeling it touch you and feeling it inside of you is a constant reminder that Master loves and desires you above all other things. It's like a wedding ring. It symbolizes your love for Master and his love for you."

Sometimes that girl made me so proud I could burst.

"Besides," she added "These look way cooler than those other ponies that just wear tails strapped to their hips or hanging from their harness. We aren't just fetish freaks. We're real proud ponies."

The other thing that kept me distracted and amused was the fact that having that plug in his butt kept him constantly aroused. It moved around inside of him when he walked and he couldn't take more than a few steps without having to stop and shiver, his erection pointing the way wherever he went. And being the evil bastard that I was I made sure he walked around as much as possible. In a way he was relieved to be standing up, as he was discovering that it took a whole new set of positions to be able to sit down. He couldn't sit cross legged on the floor as he had when we played chess. The tail forced him to sit on his haunches or recline on his side.

I invented chores for him to do just to get him used to walking around wearing my tail. Plus I couldn't get enough of the sight of that tail poking out of that fine firm bottom and what that represented. I was constantly aroused myself in anticipation of taking him to bed and fucking him for the very first time. I was all for drawing out the anticipation and denying him any release until he gave himself to me. But I had a feeling that Master was going to need some relief fairly soon. My balls were starting to ache with my need.

My two ponies had been sent into my bedroom to change out my sheets and get the bed ready for the evenings festivities. I'd told them to strip the bed and just put on a fresh bottom sheet, leaving the top sheet and blankets folded up on the chair for later. They were to have a supply of fresh towels within arms reach and make sure that the bottle of lube was full and in the warmer. Seeing the flush of anticipation and trepidation on Nathans face made me add an admonition that they were to keep their hands off of each other and off of themselves while they were in there. Then I watched those two switching tails as they scurried off to do my bidding. It was sight I was sure I would never tire of.

While they were so occupied I pulled on a pair of sweat pants and a t-shirt and went out into the covered sun room to look at the storm outside. It was completely enclosed with large windows and in temperate weather it was good place to just sit and relax. I didn't really use the room all that much, preferring to be actually outside with my pets when we weren't inside cuddled up in bed. But there were some mornings when Sarabeth and I had eaten breakfast out there or just curled up in a chair together with the windows open enjoying the summer breezes, just relaxing and content for the moment that we were together and happy.

Being shut off from the main house meant the room was pretty chilly. It was a big drop in temperature from the cozy warm wood heat of the house and I shivered as I looked out the windows. There had been a small break in the storm but I could see more flashes of lightning on the horizon no too far away and dark threatening black clouds moving back in. Rain water stood in deep puddles and rivulets all over my property and there were numerous tree branches on the ground all over the place. We had quite a bit of cleanup to do in the next couple of days. Fortunately from what I could see there didn't seem to be any roof damage or broken windows in the stables or the arena. That was good. I didn't want to spend too much time away from our training schedule and I didn't want to have to bring strangers onto my property to repair anything I didn't know how to do myself.

Being so jealous of my privacy had forced me to learn how to do many things I had never done before. It was a small price to pay.

There was a small noise behind me and as I turned to look over my shoulder two naked ponies walked into the room and each one stepped up to my side as I raised my arms. They cuddled in under my arms and I could feel goose bumps raise up on their bare skin under my fingers. My palms slid down over two strong backs and I cupped a naked buttock in each hand. I could feel each of them tighten up under my grasp and they both snuggled in a little tighter.

"It just looks nasty out there." Sarabeth said.

"I'm glad we're inside today." Said Nathan. "And glad we got a fireplace. Otherwise we would be freezing." I could feel his prick twitching against my leg as he plastered his body next to mine for warmth. I laughed and patted his bottom.

"We could always just use body heat. I'm sure the three of us could manage to keep warm together." I squeezed his butt again and kissed him quickly. I could feel myself getting hard again being surrounded by so much naked flesh.

"Let's go inside. I have something I need, Nathan. And I think you can help me out. Another lesson in Pleasing master 101."

"Oh god...."

I lay back on the rug in front of the fireplace with my head on a small pillow. Naked once again and soaking up the glorious warmth from not only the fireplace but the two warm bodies laying on either side of me. Both of my pets lay with their feet up by my head, leaning together over my crotch while Sarabeth resumed her lecture on the Care and Feeding of Masters Cock. My forearms were between their thighs and I held a warm firm ass cheek in each palm which I patted and squeezed softly, just enjoying the feeling.

Nathan was nervous and I could feel him tremble now and then. He knew what I wanted and he knew what was going to happen, both now and later on this evening and he was trying hard not to lose his nerve. And Sarabeth was doing her best to both bolster and distract him, touching him and interspersing her lessons with long lingering kisses with their lips meeting right above my hard upstanding prick. Both of their hands were wrapped around the shaft of my cock, stroking me slowly.