Seven Tails: Tail 02

"Now the first thing you have to know about anal sex is that it is not 'nasty' or 'dirty' or anything like that. As far as 'perverted' goes, it's just a matter of taste. Simple cleanliness and maybe the occasional enema to clean yourself out if you want makes it just as clean as any other body part." His eyes were wide as we slid his fingers up and down her crack. "The next thing you have to remember is it is very important to have your partner just as relaxed as possible." I smiled. "Of course if Sarabeth was any more relaxed right now she would just seep into the cushions and turn into a puddle. She's a good girl and willing to do anything to please her Master. She knows that giving up her little bottom to me makes me happy so she does it whenever I want her to. It wasn't quite so easy the first time, though."

"I thought you were going to kill me that first time." She said, tensing up her ass cheeks just a little at the memory. "But once I realized how good that feels it got much better." She hummed a little in the back of her throat and swirled her hips against our combined touch. "Much, much better! Mmmmm......" With my finger on top of his, I moved his fingertip around and around her tight little ring of muscle guarding her entrance. "Feel how it moves." I whispered. "Contracting and expanding. She wants to let you in, but her body's natural reaction is to keep anything out. Or in, as the case may be. It takes a conscious effort to relax those muscles enough and let something in. You have to work them slowly.... Helping them to relax and allow you inside...." Our combined fingers moved around and around the little rosette of her anus while she sighed and hummed. Nathans eyes were wide and his mouth hung open. I could see a flush of desire spreading down his neck and chest and his prick was stiffening and bumping against the side of the table.

My other hand grabbed the bottle of lubricant and squirted some down just above our hands and let it run down her crack. The massage oil was slippery, but not generally slippery enough for actual penetration. I pulled his finger up to get it well saturated with the lube then brought it back down to press gently at her entrance. Sarabeth groaned lightly and pressed her hips backward, taking a deep breath to loosen up the muscles there and grant him entrance.

"Once you've got her relaxed enough, just press forward gently and slowly. My good girl will let you in. Stop when she tightens up and slide in deeper when she relaxes." Sarabeth opened her mouth and made a small "Oh..." as his finger slipped into her ass and then "Mmmm...." as he slid all the way up inside of her.

"Oh my god!" he breathed. "That feels awesome!"

I held up my index finger for him to see and moved it in a little circle. "Now try this."

Sarabeth said "Ahhh...."

"Use the web of your finger and the knuckle to put a little more pressure on the muscles. Back and forth just a little bit. Stretch them open a little more and get them ready for the next phase."

She said "Mmmm.... Ooohh... That feels so good, Nathan!"

"And once you have her good and receptive, get a little more lube, like so..." I squirted a bit more above his buried finger. "Then pull slowly out and try two fingers. Just like that. Slowly and gently. Let her open up to you." Sarabeth clutched the edge of the table, breathing through her mouth as his fingers opened her up and slid inside. Her hips came up off the table and she pulled her legs up and wide to ease his entry. His prick was so hard if I had reached over and grabbed hold of it he would have shot his come all over her hip. Mine was in no better shape either. Seeing Sarabeth holding that delicious butt up in the air made me want to climb up on the table, yank his fingers out of the way and drive right in there myself.

I could have. I was the Master, after all. But this was about Nathan and not about me. Well, not directly, anyway. The whole point of this exercise was to get him used to the idea that I was going to be the first man to fuck him and that it was going to happen tonight. The thought of that made me shiver with anticipation.

Sarabeths moans brought my attention back to the present. Nathan was working his fingers in and out of her bottom and she was hunching her butt higher and higher off of the table. I patted her bottom and said "Love, are you ready?"

"Mmmm.... Yes, Master!" I reached between her thighs and grabbed his ring finger and brought it up right between her pussy lips and slid it inside her and straightened out his pinkie so that it rubbed directly on her clit. "Short strokes, Nathan. Slow at first. Speed up as you think necessary. I'm sure you'll know when." Sarabeth began holding her breath and letting it out in gasps and bucking her hips back against his hand, her pelvis moving in circles. Her whole body was tightening up and starting to move back down onto the table. I put one hand on her shoulder and the other hand over Nathans, loving the feeling of holding his hand as he made my pony girl feel so good.

"Oh oh oh! Oooohhh...!" Those long slim legs came back together and she slid down onto the table. I held onto her shoulder to keep her from going headfirst onto the floor.

"Oh god oh god oh god...... Oooooooooooooo.......!" Her little ass cheeks clamped down on his hand and she started humping her ass up and down hard and she gave a little yip and shivered hard all over as she came. Nathans eyes were still wide with wonder and surprise as her inner muscles clamped down around his fingers. I held his hand and kept him in slow motion as she bucked and cried out and came over and over again.

Finally I had him hold still and Sarabeth lay still on the table and panted. I held one finger to my lips and grinned at him and held up my other hand and wiggled my fingers slightly. Caught by surprise by the sensation, Sarabeth jumped and cried out again, her butt clamping down hard again and shivering all over, goose bumps ran up and down her back in waves. Nathans eyebrows went up and he grinned back at me. A whole new world was opening up to him right before his eyes.

Slowly I had him pull his hand back as Sarabeth moaned and panted and she said "Oooohhh.... Yes......" as he finally slipped out from between her cheeks. I sent him in to wash his hands and patted her on the bottom. "You okay, love?"

"Mmmm Hmmm...." She gave a happy sigh. "Was that okay, Master?" I patted her bottom again affectionately.

"That was just perfect, baby girl. Just perfect."

Fourteen

We let Sarabeth relax on the table for about fifteen minutes, the rosy glow slowly fading from her skin. Nathan had gone and got us glasses of ice water and he put a straw in hers and held it up now and then so she could sip. And he had thought of that and done it without being asked. Despite his earlier denials, he was turning into a perfect submissive. Thinking of others pleasure before his own. That suited me just fine, as he was going to be my pony boy for a good long time.

When we finally got him up on the table Sarabeth and I spent a good long time working over every single muscle that we could reach as he lay face down, groaning with pleasure and occasionally letting out a little "eek!" as one or the other of us dug a little too deep into a tight spot. It was just such a pleasure to be able to have my hands all over that sweet body without having to fight him or tie him down.

Not that I had anything against tying him down, mind you. I liked that a lot and I was pretty sure that being bound excited him too, from his reactions. That just made him even more perfect in my eyes.

As he and Sarabeth had traded places, I thought it was only fitting that she move him into the next phase herself, as he had done to her. Even though he had wanted me to give him his very first anal penetration when I gave him his tail, I let Sarabeth take the lead this time. He didn't seem to mind it too much, groaning and sighing happily as she rubbed and teased his tight semi-virginal backdoor with the tips of her fingers. The only difference in the proposed program was that I didn't want her to bring him to orgasm. I told her to go slow and steady and to back off if he seemed to be getting too close. I wanted him hard and wanting and slightly frustrated and begging for release when I took him to bed for the first time.

He'd had his head laying on the end of the table, resting his chin on the soft mat and his hands gently gripping the edge. When her finger finally pressed up inside his butt for the first time his head came up, eyes closed and mouth open and his fingers tightened their grip. He said "Aaaaaaahhhhhhh....... Oooohhh....." and I could see his whole body writhing and fighting to relax into the intrusion. With his head up and mouth open like that I really had to fight the urge to just walk around and stick my cock in his mouth. But I didn't want to come just yet and it would have been difficult to pull myself away from those wonderful lips in time. I'd been hard for well over an hour in anticipation of what was going to come next and my balls ached with the need for release. It was going to happen soon, though.

I did the next best thing, though. I teased him with it. Stepping around the end of the table, I wrapped my fingers in his hair and pulled his head back just a little more. Nathans eyes flew open to see the head of my prick bobbing right in front of his face, only inches away. He said "Ah!" and shivered hard. I could see his mouth close slightly and his adams apple bob in his throat as he gulped. One hand came up to reach for me and I pressed it back down to the table. His tongue came out and licked his lips. His whole body was in slight motion as Sarabeth worked her finger in and out of his tight ass.

"Please let me suck your cock, Master."

"Not yet, boy. Not yet. The next time my cock finds it's way inside you is going to be in your ass."

Nathan made a little strangled noise in the back of his throat. "Oooohhh..... God."

"You are aware than in a few minutes I am going to carry you to my bed. And not very long after that I am going to be the very first man to fuck you." I gave Sarabeth a little nod and she backed out and slid a second finger up inside of him, stretching him open even further.

"Oh! Oooohhh god.... Y-yes Master!!"

"Do you want me to fuck you, Nathan?"

"I...... Mmmmm.... I....." he was pushing his hips back into her invading fingers as they swirled and twisted around inside his bottom. I held up a hand and she stopped. He gave a little frustrated moan and tried to push himself back into her but I kept my grip on his hair to keep him from moving around too much.

"Do you want me to fuck you, Nathan? Do you want my cock in your tight little pony boy ass?"

"Unhhh.... P-please, Master!" I leaned down and looked him in the eyes.

"Please what?"

"P-please fuck me, Master!" I waved a finger and the little blond started thrusting slowly into him again and he moaned and shivered.

"Please put your cock in my little ponyboy ass, Master." As the words left his lips I leaned even closer and kissed his open mouth hard, my tongue sliding into his throat. My hand gripped the hair on the back of his head hard and he moaned into my mouth and panted through his nose. I'm afraid my hand gripped his hair a little tighter than I intended and I growled into his mouth as a wave of lust washed over my body. I had been waiting so long for this moment that I refused to wait a second longer than I had to.

It was time for two things. One, to take Nathans anal cherry. And two, to fuck my first captive pony boy. This was going to be a night I was going to remember for a long time. And I suspected it was going to loom large in Nathans memories as well.

I pulled back from his mouth and stood up, motioning to Sarabeth. She slowly pulled her fingers out of his ass while he wiggled and reached a hand behind him, trying to keep her inside. I stepped around to the side of the table as she stepped away and flipped Nathan over on his back then slid my arms underneath him and lifted, one arm under his knees and the other behind his back. I shifted his weight higher and his arms went reflexively around my neck. Being as small as he was, he was no great burden. Besides, I didn't have to carry him that far. As I walked, he just looked up at me, his eyes wide. I could feel him shiver now and then. And I looked down at him and smiled.

"I told you this was going to happen, Nathan." I rolled my eyes up in thought for a moment. "Let's see... twelve days ago. Our hardest day ever. Right after you got stupid and I had to beat your ass. I told you that one day very soon you were going to beg me to fuck you. I'm just sorry it took so long."

"Me too, Master. I.... think, anyway."

"I've seen how you reacted, Nathan. I watched you when Sarabeth stuck her tongue in your ass. I was right back there looking at how hard you got when I slipped your tail up inside you and how hard and how fast you came afterward. And just a minute ago how excited you got with her fingers moving in and out of your butt." I knelt up on the bed and leaned over and placed him down in the center of the mattress.

"Face it, Nathan. You were born to be a pony. You are a natural born submissive." I reached down and grabbed hold of his prick, which was standing up hard and tall. He gasped and moaned and his hips bucked upwards into my grip. "Your body wants me to fuck you, even if your mind hasn't fully grasped it yet. We just have to get you past your fears and lay them to rest. Then you will learn to be a happy and contented pony. And we are going to do that right now."

"Oh..... God."

Sarabeth crawled up on the other side and I started to recline on one elbow next to him, making a little sandwich out of his body. Nathans eyes rolled back and forth and his hands suddenly came up, palms out and he stuttered "W-wait! M-master, please!"

"What is it, Nathan?" His mouth opened and nothing more than a breath came out. Then he brought his hands up over his head and crossed his wrists. His eyes looked at me pleadingly and he trembled.

"It's like that, is it?"

"P-please, Master!" I leaned over his body and looked down into his eyes.

"This is just like when you accepted your tail, Nathan. From now on I won't tie you down and force you. It has to be freely given. You have to ask me." I leaned closer and put a finger against his chin. "Tell me what you want."

Nathans jaw worked a few times like he was trying to force the words out of his mouth. Then he whispered "P-please tie my hands, Master."

"And?" I just couldn't resist dragging it all out of him.

"T-take me." he whispered. "M-make me yours." His whole body trembled hard and he flushed a deep red before he could add "F-fuck me in my ass, M-master." I leaned down and kissed him quickly and when I looked up again, Sarabeth already had a chunk of rope from my stash on the headboard and was putting it in my hand. I crawled up on my knees and leaned over to tie his hands together above his head, my hard prick bobbing in the air inches away from Nathans face. His eyes locked on to the sight of my meat hanging there and he trembled hard again and said "Oh god...."

While he was mesmerized by the sight of my cock hanging there in front of his face (and no doubt envisioning it driving into his ass) Sarabeth patted him on the thigh and said "Lift your hips, Nathan." He did so and she slipped a small firm pillow up under his butt to raise his pelvis a few inches off of the mattress. That way I didn't have to bend him quite so far to get into a good position. I wanted him to be as comfortable as possible this first time. It was probably going to be a trial getting him relaxed enough to take my prick.

The rope snugged into the metal eye on the headboard with a final tug, making sure he wouldn't be going anywhere until I wanted him to. Sarabeth placed a hand against the nervous lads cheek and turned his face towards hers. Her soft lips were millimeters away from his and she made him look into her eyes.

"Look at me, Nathan." she breathed into his lips. "Just look at me and relax. Don't think of anything else. Now.." One slim hand went to the center of his chest and she said "Take a deep slow breath. In....." She gently blew against his lips as he breathed in. "Deeper... deeper.... All the way in..... And out, nice and slow... Very good...... Now, again, lover. In......"

While she had him distracted I nudged his thighs apart with my knees and slid between his legs. Moving slowly, I brought his knees up and then grabbed his ankles and brought them up even further and crossed them over each other on my chest just below my breastbone. That held his legs up and spread and kept my hands free for the moment, which was what I wanted.

Actually what I wanted was to flip him over on his face with that delicious ass up in the air and work my cock up into him from behind. That was one of my favorite positions. I just loved watching my prick slipping inside a tight pony ass while they squealed and wriggled.

But this way had him spread open wider with less leverage to tense up or pull away and it gave Sarabeth a better opportunity to keep him distracted and relaxed. Which was infinitely preferable to having him tense and fighting me all the way. If I had tried this without Sarabeth it would have been much more difficult.

She shifted positions, moving up above his head with those sweet warm little titties of hers on either side of his face. She put her hand under his chin and tilted his head back into her chest so he would look up at her and she continued helping him to breath slowly and deeply. Not only was it helping him relax and keep him distracted I'm sure the change in breathing was giving him a slight buzz, which would help enhance the experience.

One hand worked the pump on the bottle and got a big dollop of warm lube on two of my fingers. The other hand slid down his thigh and cupped a warm ass cheek in my palm, squeezing it gently. When I slipped my lubed fingers between his cheeks, Nathan twitched and made a small sound. Sarabeth squeezed his head between her tits and said "Ssshh.... It's okay, Nathan. Master isn't going to hurt you. Just breathe and look at me...." She ran one finger over his lips and leaned down even closer. "And after tonight maybe Master will let you fuck me in my ass!" She purred and her tongue flicked out and licked the end of his nose. "I can't wait to feel that big pretty cock of yours in my ass, Nathan. Mmmmm.... I want you to fuck me long and hard and make me come and come and come..."

I waited until he was at the deepest point of an inward breath then slowly pressed one finger to the entrance to his rectal channel. The ring of muscle twitched and spasmed and slowly opened to my intrusion and my finger slipped up inside of him. Nathans mouth opened and he breathed "Aaaaaaahhhhhhh....... Mmmmm...." and his hips moved a little in pleasure. The pad of my finger grazed over his prostate which made him groan and his prick, which had flagged a bit with his nerves sprang back to life, full and hard.

I didn't give him long to enjoy the sensation. Since he had already taken his tail and worn it for several hours he was already fairly used to being stretched open at least that far. Besides, I was desperate to fuck him for the first time and I wanted to move things in that direction as quickly as I could without panicking or hurting him. After only a few moments I pulled back a little, added more lube and slid a second finger up inside his tight ass.

"Oooohhh.... God...I.....Oooohhh......That...Mmmm..."

I really wanted to talk to him, like I did with Sarabeth while I was making love to her. It was part of my kink, I guess. Interacting verbally with my partners. I wanted to ask him if it felt good having me stretch his asshole open before I fucked him for the very first time. I wanted to tell him how proud and excited I was to be the very first man to fuck him and what a wonderful pony he was going to be.