My Journey of Discovery Ch. 03

He placed the ring in my mouth and fastened the strap around my head, buckling it in the back. I quickly realized the ring would not allow me to close my mouth, making it difficult to swallow. Try it sometime. Keep your mouth open and try to swallow. Closing your lips creates a seal and allows the tongue to reach the roof of your mouth, making it easier to push things down your throat. If your mouth is open, your saliva may still go down your throat, but it will trickle down. I think it's why the dentist makes you spit instead of swallow when he's got your mouth open. Plus, I could see the open ring would allow him to put his cock through it, into my mouth. Given the diameter of the ring, his prick couldn't be thick, though it might be long. The only problem; I was fastened against the board in an upright position. He either had the longest dick in the world, or he would need to stand on a chair.

How wrong could I be? He kicked a pin at the bottom of the board and it pivoted around a center point until he lowered it to his crotch. I could not see his face, but I heard him chuckle. He popped the snaps on his pants and his prick fell out, somewhat stiff, but not fully hard yet. In my mouth it went. I used my tongue as best I could, but I was unable to suck. How was I supposed to satisfy him without sucking? I didn't realize it then, but he didn't care.

"Take this, slave. Take it now!"

Saliva was forming in my mouth now. His cock ensured that. Stuff goes in your mouth, saliva forms, the first step of the digestive process. It had no where to go but to run down his dick. To him, the warmth and wetness were enough to stimulate his desire and his dick swelled in my mouth, getting longer, going deeper. It reached the back of my throat and I gagged. Master Jack did not care. I think his cock expanded more as he made me choke and he pulled my head farther on his prick. Drool was running freely out of my mouth and down his shaft; rivulets of the stuff, soaking his balls and dripping on the floor forming a pool. I could not withdraw or spit his cock out and he would not. I gagged harder, gurgling around his organ. His cock went deeper. I was breathing through my nose, my throat closed off where his cock choked it. My lungs burned. I was getting some air, but not enough. I got ready to slap the board but he lifted me up at the last minute and I gasped for breath, sucking oxygen while thick strings of drool dripped to the floor in long trails.

When I thought my breathing was close to normal, he lowered my head again and his cock pushed deeper down my throat, right past the initial gag reflex. What had Dina said? Everything before ten minutes ago seemed fuzzy. Swallow! Swallow, that was it. It was hard. With my mouth open, it was hard. I told you before. My tongue was nearly useless, everything else was flowing the opposite way, but my throat muscles could still move, so I did the best I could. I swallowed. It was like my throat opened and his meaty stalk could slide right in. I felt his balls slap against my chin and his pubic hairs tickling my nose. As soon as he was all in, he started thrusting. No more than an inch or so, but he did not need much, my throat muscles massaging his cock all he needed for his stimulation. I couldn't breathe, but he realized and pulled me off him before I would pass out. As soon as I took a couple gulps of air past his dick, in it went again.

Just like that, it was okay. His cock would disappear down the back of my throat like it was a tunnel. My breathing would stop as he thrust for half minute. Out he would go, breathe, boom, in my throat. My vision narrowed down to one thing; his balls when I could see them, looking for any sign of his pending release, and the gray peppered pubes over his shaft when he was buried in me. I could not see anymore. Sounds were distant, like faint echoes. The only other sensations were his hand on my head, twisted in my hair, so he could guide it up and down, and the ropes around my breast. Out, breathe fast, in, thrusting, repeat pattern. Time lost meaning. I was nothing but a receptacle for his need. We were nearing the end of another cycle. I was expecting to breath shortly when I felt his cock swell in my throat and warm fluid shooting from the end of his cock. I did not care; I only wanted my next breath. I could not swallow it, so it leaked out around the edges of my throat/cock seal and leaked out to join the puddles on the floor. With one last tiny thrust to pump the last few drops of his seed in me, his dick suddenly fell away and I could breathe again.

"Not bad. Most women fight it longer. You did okay," Master Jack said.

I said nothing; I could not with the ring gag. I was still gulping down air, drool and cum leaking out in the opposite direction. Sights and sounds started to return. My throat felt raw. Master Jack released the buckle at the back of my head and pulled the ring from my mouth. I worked my jaw, making sure it still worked. He raised the board, restoring me to an upright position. Removing the ropes first, Master Jack freed my breasts, tingling as full blood flow was restored, thankful to be loosed, the rope marks clear. Off came the straps and I could finally stand, though I felt wobbly. He steadied me so I remained upright.

"Tell your Mistress you took a seven inch cock," he said.

"I will. Thank you, Master Jack," I rasped, still raw and out of breath.

He handed me a water bottle. "Drink this. It will help." I gratefully accepted and took several long sips. While I drank, he wiped the drool and cum off my body where it dripped off my chin with a towel.

"Your Mistress mentioned you had other tasks to perform. What do you need to do next?" He asked, still wiping me down.

"I'm to find Master Gregory," I said between drinks.

"You're first anal?"

"Except for plugs, Master Jack."

He stood up and nodded. "He's the best to see for anal newbies. Won't ruin it for you your first time."

Master Jack bent down and kissed me gently on the lips. "Remember what you learned. You don't want to go through this again."

Hell, no. "I will, Master Jack." Or give up my crazy idea of studying submission by immersing myself in it, I thought. I won't go through that again. No wonder Dina looked at me funny. She knew what I would experience. Had she gone through it herself, or seen it happen to others. Given her distaste, I suspected the former. "Can you tell me where to find Master Gregory?"

"I'll lead you to him."

"Thank you, Master Jack."

He brought me to a corner I had paid little attention to on my tour. Master Gregory was giving another female a set of butt plugs in a box with increasingly graduated sizes.

"Start with the smallest one," he said. "Use the next largest size every day and return here to see me next Friday." Much like Mistress had done for me, though she changed them every half day.

"I'm so excited," she replied. "My boyfriend has been begging me to do anal for months. He'll be so happy when I let him take my ass."

Apparently, Master Gregory was performing a community service. I wondered how many of the boyfriends or husbands realized their sweeties were getting their asses broken in by another person before they shared their booty. None of my business, really. I was getting mine broken in for another person, I hoped. If he was looking for an experienced submissive, I had to at least know what it involved.

After she left, Master Jack introduced me to Master Gregory. Master Gregory had me turn around and I imagined him to be studying and appraising my derriere. He was about to sample the goods, after all.

"She is absolutely superb," Master Gregory said. "I've been waiting for her. Thanks for bringing her over, Jack."

"Let me know how she does. I'd like to fuck her ass myself, if there's time tonight. She's got perfect booty."

"I'm surprised you noticed."

"How can you not?"

So men appreciated my ass. My boyfriends said they liked it, but they had to compliment me if they expected to get any. These men could have it anyway, whether I liked it or not, so their opinion held more weight to me somehow.

Master Jack left and Master Gregory asked, "You've been cleansed?"

"Mistress took care of that this morning, Master."

"Excellent. Come here, please."

"Yes, Master." This was it. My anal virginity was about to take a hike.

Master Gregory had me straddle a wide, rounded, padded horse, not dissimilar to a pommel horse in gymnastics, without the pommels, but maybe thicker. He adjusted me so my ass was hanging over the end, the edge just catching my clit. My wrists were slipped into cuffs and drawn tight around the horse so I couldn't move too much. My legs were drawn forward and secured under the horse. I probably looked like a jockey in the Kentucky Derby except the horses ass was not behind mine; nothing but air and Master Gregory. My bum looked to be the same height as his cock would be when he took me. I trembled a bit.

"Are you frightened?" He asked.

"A little," I admitted, "Master."

"You needn't be. It's my job to ensure you enjoy the experience and I'm good at my job."

"Will it hurt, Master?"

"You've had plugs installed the last several days, haven't you?"

"Yes, Master."

"They weren't painful, were they?"

"No. Well sometimes to get them in, but the pain ended," I said, "but I'm told this is different."

"Not so different. Relax and you'll enjoy it. I expect the most you'll feel is a little discomfort."

"Yes, Master."

I closed my eyes and tried to relax. I heard him moving behind me, getting things. I hoped lube was included on that list. I heard a chair scrape the floor behind me and his left hand touched my cheek. I tightened up.

"We're not starting yet. Relax. I promise I will make you cum."

"Yes, Master." I took a few deep breaths and felt myself relax some.

I felt both his hands on me, but all he did was rub; massaging the globes of my ass and I felt myself loosen more and more, the tension leaving my body. It was like a back massage except he concentrated exclusively on my butt cheeks. He had to have a bird's eye view of my rectum and pussy and I felt myself getting wet there. His finger made a light trail up my crack from my pussy to my tail bone, passing Go, but not collecting $200 dollars. I momentarily clenched, but loosened again as soon as I knew he was not lingering there. His hands would return more frequently, a finger lightly brushing, but each time, I reacted less and soon, I made no response at all when he brushed across my rosebud. Sneaky devil.

The next time, it was not a finger brushing up my crease, but his tongue. The wetness added a new dimension, but not enough to tighten again. I actually moaned, it felt so good. Master Gregory had not lied to me so far. I was starting to turn limp.

The next time, his tongue did not sweep my crinkled sphincter and pass by, it loitered in the area right by the No Trespassing sign. It was angelic. My cunt was leaking profusely now. Master Gregory possessed a gifted tongue with the only proviso being it was working my asshole and not my clit, but right now, I did not care. Just when I thought it could not get any better, it did. I felt his tongue poking at, then through the muscular defender of my anal virtue. No wonder he wanted his first timers cleansed. I could not imagine what it would be like if I was not.

His tongue kept stabbing into my rectum like a little finger, except it was wetter and slicker. I started to pant; it felt seriously good. He kept it up for several minutes and my toes were curling it felt so exquisite. I whimpered piteously when his tongue left me.

"You're ready now," he said.

He was right. I wanted something back in my ass and I wanted it now. "Yes," I said, "fuck my ass now."

I felt some drops of lube drip on my rosebud, warm and slick. His finger rubbed it around and I could feel my rectum pulsing open and closed, seeking something to fill it. His finger left me and I felt something bigger, something velvet smooth touch me. He rubbed his cock in the lubricant, dripping more to make me wetter. The head of his cock planted itself at the entrance to my ass and began to exert pressure. I felt myself giving way before the onslaught, parting around his cock like the Red Sea, surrendering. I did not see how big his cock was before he started putting it in me, but it felt thick and firm. I grunted a little. I felt a pop and the head was in. No worse than a plug, softer even, at least until he decided to move. Fortunately, he was giving me time.

Slowly, so slow, he pushed in, a millimeter at a time. Steady girl, I told myself, you can do this. It feels okay. It was so odd, the sensation of something coming in instead of passing out. I squeezed down, like it was going to help push it out and Master Gregory gave a little gasp. Of pleasure? Or had it hurt him? It did not stop his slow inexorable march into my bottom, so if it hurt, it was not much. He kept feeding me a little more, and I felt it, a delicious pressure and fullness. Suddenly, I felt his balls dangling against my cunt. Had I taken it all? How much cock was in me right now?

"How do you feel?" Master Gregory asked. "Any pain?"

"No, Master. It feels good," I replied. "Is it all the way in?"

He laughed, a deep pleasant laugh that shook his cock and vibrated in pleasant ways deep in my guts. "All the way," he said. "You're so tight. This feels fantastic."

"I hate to admit it's on the fantastic side for me as well. Do we stay like this or are you supposed to move or something."

"Just giving you some time to adjust. Do you want me to move?"

"Yes, Master. I believe I'm ready."

He started to pull out, almost as slow as he pushed in. I felt the flange of his crown tugging at my opening on the inside before he pushed back in, faster now. Back out, push in. He found a rhythm pleasing to us both, and I started to feel the build up toward a climax, though it seemed to center in my ass instead of my cunt, though even there, it felt good. My clit was rubbing on the edge of the horse and it helped to increase the pleasure.

"How can this feel so good?" I panted, wanting to rear back against him, unable to due to my bondage on the horse.

Master Gregory replied, "The anus contains almost as many nerve endings as your clitoris. That can make it hurt more if I were to abuse it, or feel better if I'm gentle. Since this is your first time and I don't want to hurt you, it feels better than you think it would."

"You can go faster now, Master" I said. "If I weren't tied down, I'd be fucking you back."

He didn't reply, just sped up and I moaned. Soon, I thought, soon. I'm going to cum from being fucked in the ass. Building, building and then it was on me and I gave a little scream which I attempted to bury in the leather of the horse. My muscles were contracting, I bounced up and down on the edge of the horse, pounding my clit and riding it for all I was worth. Master did not stop. He rode out the pulsing in my ass and kept pushing me higher and higher until I screamed my pleasure to the world, much to my dismay and astonishment.

After I did, I felt his cock pulse in my rectum and liquid warmth spread like a soothing balm in my ass. Master Gregory gave a few shudders and grunts and I felt him straining to empty his sack, little jerky thrusts in my butt. I felt him start to shrink. A couple squeezes by me and I felt his cock fall out, followed by a small amount of his cream, dripping out of my ass as my sphincter slowly realized it's emptiness and started to close.

"Thank you, Master Gregory. It was indeed a wonderful fuck. Much better than I'd hoped for. Thank you for taking care of me."

"Mistress L said you are still finding your limits. I have to ask if you want to suck my cock?"

Given my cleansing, I was more inclined to be open minded about the subject than when it was broached a couple days before. Master Gregory's cock appeared to be smeared with cum and nothing more. On the other hand, he was not my Master and just introducing me to anal sex. I did not feel I owed him more than I had already given.

"I would have to call 'Poughkeepsie' on that," I said. "This is still too new to me."

"I'm sorry to hear that. I would have enjoyed sampling your new cock sucking skills. Which is the third thing you must accomplish today?" Master Gregory asked. "Mistress L said there were three."

"Mistress wants me to seek out Master Lamar."

"Not for your ass, surely," Master Gregory said. "We've just started to break you in."

"No, Mistress wanted his thickness in my cunt and the volume of cum, plus my first black man. She wants me to return home with sperm dripping out of my body, both holes."

"Lamar is definitely good for that," Master said. "But you may need more in your ass. I was pretty well drained today."

"What would you suggest?"

"How does your ass feel?"

"I know it's been used, but it's not sore. Why do you ask"

"Jack wanted to fuck your ass. He's not too broad. He'd be willing to do a double with Lamar."

"A double?" I asked.

"A double penetration. Lamar in your cunt and Jack in your ass."

"Mistress did not tell me to get a double penetration. Would she be angry if I did?"

"I'd tell you to text her and ask, but I know you don't have your phone. If you're willing, go for it. I will notify Mistress L it was at my direction."

I thought about it. Master Jack had scared me some; I thought he might asphyxiate me, but he did not, and was kind enough afterward. My ass was not abused, and felt as if it could accept another cock and Jack's was on the thin side. Better a thin one now than fatter one later. While Mistress had not directed a double penetration, perhaps she felt I was unready for such an undertaking. I was sure they were in her plans for me at some point.

"It was bound to happen sometime. I suppose now is as good a time as any," I said. "I won't be as afraid today as some other time. Lead the way to Master Lamar and let Master Jack know where I am."

He agreed and led me to Master Lamar. He had a white woman tied to a post and was laying a five stranded whip on her back and buttocks. I might have been a little concerned, but Master Gregory told me she was his devoted pain slut and would be upset if I interrupted Lamar now. Her back and buns turned a lobster red before he stopped. He did not seem to restrain himself using the whip. I'm glad all I had to do was fuck him. Master Lamar was a coal black shade of dark, seeming not even to reflect light. He was over six foot and heavily muscled. Bald or shaved on top, his head seemed to have muscles as well. His pants were similar to Master Jack's. A flap over his crotch with a couple snaps for easy access.

Master Lamar was sitting, catching his breath when Master Gregory introduced us.

"Mistress L would like you to fuck her slave silly, Lamar."

"She sent word. This the gash she talking about?"

"Yes."

"Nice!" He exclaimed. "I wouldn't mind sinking my cock into this slit."

"Lamar," the pain slut complained. "You know how much I need your cock right now."

He gave her a solid thwack between her legs onto her cunt. I flinched more than she did. "Shut up, bitch. I'm doing a solid for another Domme. You want me to send you to fucking machines right now. I'll crank it up and leave you on it til this place closes down. I don't need your lip. And don't call me Lamar" He sent another blow between her legs. I think she climaxed the way she was twisting and moaning.

He waited for a response. "You want another one?"

"No, Master. I'll behave."

"Damn right you will."

"Would you be willing to do a double with Jack? Mistress L wants her dripping cum when she leaves."

"Sure. Be happy to double team this bitch with Jack. Where is he?"