The following weekend jewel came over looking visibly distraught. "Oh, Master I am so sorry! I was so looking forward to being with you today, but when I woke up this morning my once-a-month visitor had come to see me! I am sorry, but I had to wear panties today because I didn't want to make a mess!" she said.

"That's okay jewel, this happens. We will just work around it, that's all."

"I tried to call and ask permission to wear panties, but I couldn't get you on the phone. Please forgive me, Master, I know that I'm not supposed to wear panties but..."

I cut her off mid-sentence with a kiss–she was so afraid that I would be angry, I figured that kissing her would solve both problems simultaneously. When she realized I wasn't mad at her she put her arms around my neck and returned my kiss passionately moaning into my mouth her thank you.

When our kiss broke jewel gasped. "Oh Master, thank you for understanding. You are a wonderful Master!"

"Are you ready to play, slut?" I asked.

"But how Master? My... I can't!" she said confused.

"My dear, you have three holes. I'm sure one of them is functional. And since I own all three, we can still do something I'm sure!"

"Well, Master I was thinking about that all morning and on the bus ride over here. There IS one hole you haven't tried yet... the only thing is, no one has ever been there. I am a virgin back there." she said.

"I see. Well, I will leave it up to you then. If you wish me to take your anal cherry today, I will. Eventually, I will be using your ass, but because you are not yourself today, I will let you decide if today is the day. 

"You can also wait and just use your mouth to pleasure me–you are good at that. Either way, you will be of use to me and you will have served me as you are supposed to... as you want to."

"You want to be my first... back there I mean?" she asked, somewhat stunned I would offer to be her first anal experience. "Really, Master?"

"Do I not own every part of you? Mind, body, and heart... and every hole?

"Yes, Master, of course," she said sheepishly. "I would love for you to be my first, Master... I would love to give you the gift of my anal cherry!"

"Then I shall."

"But Master... what about the mess? I mean..."

"Don't worry about that. The bed in the guest room is designed for... messes. I have a plastic mattress cover under the sheets and the sheets are old ones so it doesn't matter if they get soiled." I said.

"Oh, Master, you are so smart!" 

"Well, it pays to be prepared," I said.

I went into the kitchen and got us each a cup of coffee and brought them out to the living room. While we drank our coffee we talked some. "So tell me about your monthly visitor... is he regular–I mean predictable? Do you know when he's coming usually?" I asked.

"Most of the time yes, he's usually pretty prompt. But things have been kind of a mess at work lately. With the government budget cuts it's been pretty stressful and because of the uncertainty... well he moved his visit up, I guess!" she said.

"I'm sorry that things have been so stressful but that's what this weekend is for–to give you a chance to de-stress and focus your mind on one thing only. Me. 

"You see that is why a lot of women find submission so attractive. All day long at work, you are pulled in a dozen different directions. If it isn't your boss wanting something, it's a colleague or co-worker or one of your employees wanting something. HR called they need this, the customer has changed his mind and wants that. 

"You have to juggle work, home life, the kid's soccer practice, Sally's school project, etc, etc. It's enough to drive anyone insane sometimes. I know–I've heard it all before from other women. But here with me, you can get rid of all that. 

"Because for this weekend all you have to think about, all you have to do, is please and pleasure me. Your whole focus and energy can be channeled towards pleasing me. And mine will be in rewarding you–very well–for doing that."

"Mmm... Oh Master that sounds so nice!" she said. 

"A good Master makes all the noise in his submissives head go away so she can concentrate on him. I will quiet your mind and help you relax and be at peace here."

"Please Master... I want the peace you talk about. I want to be able to focus on pleasing and pleasuring you."

"And I want you at peace and focusing on me too because that's the best way you can fulfill your role as my submissive. The role you want to play. The role you need to play. I want you to be successful because your success benefits us both," I said.

"Master I have to tell you, when I first came to you I was afraid that you would not accept me as your submissive. Then, when you did, I was scared I would not be able to meet your standards. I had overheard you talking at the munch and you sounded so smart and so... professional. I was afraid that I would not be able to live up to what someone of your skill and experience would want. 

"But you make it so easy to serve, Master. I don't feel pressured or like too much is demanded of me. If anything, I want to give more of myself. I don't really know how to explain it... it's certainly not what I expected. 

"I am happy here Master... probably happier than I have ever been. I feel complete with you. I don't feel like a poor blind girl being pitied. I feel like I am an equal, like my opinion and my feelings matter. Thank you for that, Master. It's a rare thing for me these days."

jewel took my hand and brought it to her lips and kissed my palm. Then without speaking, she stood up and, looking down at me with her soft brown eyes, she began slipping out of her dress.

jewel's LBD slid softly and silently off her smooth brown body to pool around her ankles and the four-inch heels she wore. She hadn't worn a bra and her magnificent 34C's stood tall and proud with nipples that seem to call to me to come suck on them. 

Standing there in front of me in panties and heels she was truly an incredible sight and I could feel my cock trying to tear its way out of the confines of my pants.

"Master, please, let this girl be of service to you. Use this body as you wish to give you pleasure."

It was an offer even a fool wouldn't turn down.

"You know where the guest bedroom is, don't you? Go in there and wait for me beside the bed. I have to get a couple of things then I will be in."

She smiled and with a "Yes, Master." she turned to leave. I noticed that as she walked, her tight apple ass shimmied seductively–whether it was intentional or not I don't know, but it had an undeniable effect on me! 

I walked several steps behind her, stopping at the end of the hallway and watching as she walked down the hallway and turned into the guest bedroom. She trailed her fingers along the wall to guide her and let her know when she reached the doorway.

Once she was safely in the guest bedroom I went to get the necessary items for our play. When I had gathered what I needed I went to the guest room. I opened the door and my caramel fucktoy was standing there waiting for me.

She heard the door close and the latch click loudly. She shuddered and a soft gasp came from her lips. I walked up to her "Put your hands behind your back slut," I commanded her. Instantly she obeyed putting her hands behind her back and clasping them together. 

Using my index finger I trailed it lightly across her jawline then down the front of her throat to her suprasternal notch (where her collarbones meet in the front). From there I ran my finger down her sternum and between her amazing tits. 

I circled left, going under and around her left tit until I was back on top. Then I crossed over and circled around her right tit. I could feel her lift her chest as I circled her tits–she wanted me to play with her tits and nipples.

"What do you want my little fucktoy?" I asked.

"To be of use, Master," she moaned softly.

"NO!" I said, slapping her tit. "Why did you come here today?" I asked again.

"I don't understand the question Master!" she said, fearfully.

"Did you not tell me you wanted me to introduce you to anal sex? Did you not ask me to take your anal cherry?"

"Yes Master," she said.

"Well, a good submissive knows she has to beg for what she wants from her Master. Do you want to be a good submissive, slut?"

"Yes, Master. Please, Master, please take my anal cherry. Please, I want you to be my first. I want to give you my virgin ass. Please, Master, honor me with your cock," she pleaded.

"That's better. Now take off those panties and let's see that ass. I like to know what I'm being given."

She slid her thumbs under the waistband of her panties and slid them slowly down her long lean legs, stretching down and grabbing her ankles as she showed me her ass. 

And it was quite an ass too; tight, apple-shaped, and firm, it would be so much fun to play with, to spank... and to fuck. 

But before we got to that, I would have to get her to relax and let me open her ass up a bit. Assholes and pussies, like the women they belong to, need to be wooed, need to be seduced, and made to want to open up to you. 

Sure you can just shove your way in by brute force, but that is akin to assault and certainly not the way to insure a return visit. 

Since I wanted to take care of my submissive as well as get another opportunity to visit her ass, I wanted to ease into this coaxing her to give herself rather than taking her. There would be time for "forced anal" games once she had a few anal sex experiences. 

But this was her first experience with anal sex and I wanted it to be enjoyable and fun for her. Something she would remember fondly, not fearfully.

"What a fine ass you have my little fucktoy... I'm going enjoy taking your ass and making it mine!" I said as I caressed the warm brown globes.

"Ohhh Master..." she moaned as she swayed, her ass enjoying my hands on it.

"Okay, now up on the bed. I want you on your hands and knees," I said with a playful pat on her ass. She immediately moved into position in the middle of the bed. I fine-tuned her position, pushing her head and chest down onto the bed which caused her ass to raise a bit higher. Then I spread her knees further apart, giving me access to her pussy should I want it.

I wanted to take her from behind, mounting her doggy style. It is a good position for those who are just starting with anal sex and a position that is very dominant for me and one that makes her submissive, even a bit humiliated. It allows me to spank her while I fuck her, I can reach around and play with or punish her tits, and I can finger her pussy or clit if I choose. 

It is also a position that gives me a wonderful view of her ass. I absolutely love looking down on my girl from this position, her ass sticking up in the air so invitingly, just waiting for me to enter her. I love the way her ass cheeks spread apart a little, giving me a view of her cute brown rose. 

And the sight of my cock, slowly disappearing into her tight ass... oh, I can't even begin to tell you what wonderful a sight that is, watching my cock slide back and forth between her ass cheeks, then tilting it a bit and pushing into her, opening her tight anal ring and slowly penetrating her, knowing my full length is filling her ass.

With her now in the position I wanted her in, I climbed up behind her, a brand new tube of K-Y in my hand. As I opened the box the K-Y came in, I moved forward until my hard cock slipped between her legs, brushing against her thighs and teasing her pussy lips. 

As I worked to open the box and pierce the tube of K-Y getting it ready for use, I began sliding my cock back and forth across her slit, teasing her pussy lips and clit and letting my hips smack lightly against her ass.

"Ohhh Master... ohhh..." she moaned, her hips starting to gyrate in time to my movements. I have been told by other women I've had that being "in season" makes them exceptionally horny. This was certainly true of jewel, she was riding my cock like it was a coin-operated drug-store rocking horse. 

I let her ride my cock for a few moments–I wanted her to get a little warmed up and aroused. It would make the next phase easier and she'd be more receptive to it. When I started feeling her dampness on my cock I knew she was ready.

"Okay slut, since this is your first time at this I brought a couple of items in with me. I have some lube here to make things easier for you and I also have a little friend that will get you used to having something back there."

"A little friend, Master?"

"Yes, it's a slim dildo, specially designed for anal use. It will get you used to having something back there and once you are comfortable with that we can move to something bigger."

"May I see it, Master?" she asked. I handed the dildo to her and she ran her hand over it, feeling its size and smoothness. "Oh, it's shaped just like real cock! It has a head and everything!" she said.

"Yes, it's just like a regular dildo only slimmer. It will be a good starter to get you ready for my cock."

"Yes, Master you are quite a bit bigger!" she giggled. "But thank you for taking your time and making sure I am ready for you." 

"Now I am going to tell you everything I do before I do it so you can be ready. I don't want you to have any surprises and I want you to know what's happening. This is the trust I was talking about. 

"I want you to be able to trust me and trust that I will always take care of you. You are my most precious possession... my jewel. And I never want to do anything to break the tremendous trust you put in me.

"Thank you, Master. I do trust you."

"I'm glad for that. Now the first thing I'm going to do is try to get you to relax a bit. You are far too tense, my little fucktoy," I said.

"But, Master I am relaxed. I'm always relaxed when... Oh my God! Master, what are you doing?" jewel had definitely noticed the attention I was giving her ass! 

"I'm rimming your ass. I wanted to taste it before I started with the lube. I like the taste... you taste quite delicious my pet."

"Oh. Okay," she said. 

"Besides this will help you to relax that sphincter muscle so it's easier for me to enter you. Do you want me to stop?" 

"No, Master," she paused, "please keep going... it feels really nice."

With her permission now, I resumed licking and tonguing her puckered little brown flower. jewel began to get into it right away too, she laid her head down on the bed and I had her moaning and wriggling her ass in only a few moments.

"Oh, God, Master... please, yes. Ohh, lick my asshole, yes, just like that. Lick it, lick it, oh fuck, that feels soo good... Please don't stop please..." she moaned as she twisted and writhed under me.

Up to this point, I had been holding her ass cheeks apart as I ate her asshole, but I needed the use of my hands for this next part.

"Reach back and hold your ass open for me," I told her. She did as I said and reached back pulling her ass cheeks far apart for me. 

Such a good girl! I rewarded her eager obedience with a long, slow lick from the bottom of her pussy slit around and past her cute asshole. 

"Ohhh fuuuck, Mmmassterrr," she groaned as she felt my tongue caressing her perineum and asshole. 

I smiled to myself knowing that if she liked that she was going to love what I had in mind next!

I sat up on my heels behind her and placed my hand on the small of her back right at the top of her asscrack. My other hand went under her and I could feel her dripping wet pussy under her. She was very turned on! I slipped two fingers into that wet slippery hole and began gently fingerfucking her slowly, not going too deep at first but just letting her feel my fingers inside her.

"Oh Master, I can't-I'm on my..." she started to protest. But as quickly as she got those few words out my thumb found her anus and I pressed against the puckered opening just enough to show her I was there.

"Oh GOD!" she squeaked as my thumb pressed against her virginal area. She was caught between my finger inside her pussy and the one knocking on her backdoor!

"Shhh... quiet my sweet slut. I know about your condition. Just relax and enjoy this," I said calmly.

After that, she just laid her head back and relaxed letting me do what I wanted to her with no further complaint. And as my fingers slowly worked her pussy, my thumb began massaging her tight little opening, coaxing it too to relax and yield to me.

"I'm just going to play with your ass for a while, if that's all right with you," I said, not really asking more than I was informing. I had every intention of toying with her ass, I just wanted her to know what I was doing.

"Ohh, that sounds wonderful to me, Master..." jewel moaned as she pushed her ass back at my hands, letting me know I can go harder.  I increased both the speed and the depth my finger went in and out of her pussy. Gently at first, then harder and harder. Her pussy was slobbering happily as I raised her arousal level higher and higher. 

"Does that feel good, fucktoy?" I asked.

"Oh God yes, it does... Please keep doing that, Master. Please don't stop. Oh fuck, Master, that feels sooo good... Where did you learn how to do that?" she moaned, wriggling her ass harder and digging her fingers deep into her assflesh as she tried to concentrate on holding herself open for me.

I could feel her sphincter muscle relaxing and I could slip my thumb easily inside her up to the first knuckle. Her gasp and moan told me she liked it. It was time for the main event to begin...

"Okay jewel I think you are relaxed enough now that we can begin. Like I told you before, I won't do anything without telling you in advance but I want you to trust me, okay? 

"I have done this a number of times with women who had never done anal sex before or who were resistant at first to try it. I haven't had anyone come back saying they regretted the experience. And you won't either, I promise."

"Yes, Master I trust you. I know that you are a skilled and caring Master and you would never do anything to hurt me."

"That's right. You are more precious to me than you can know and I will care for you above all else. Now I am going to squirt a little of this K-Y lube on your ass," I said.

"OH! You're right, that is cold!" she gasped as the lube hit her asshole. But as soon as I started rubbing it around it warmed up and the slickness made her mewl and begin to slowly grind against my finger. I spread this first bit of lube around in a circle about three inches in diameter with her asshole in the center. When that circle was well lubed, I put another glob right on her pucker. 

"I have to lube your asshole now and make it slick so the dildo can slide in easily. I'm going to use my finger to spread the lube though so I can feel how you are doing. But if it gets too hard, you remember your safe word right?" I asked.

"Yes Master... it's Eve, my name."

"That's right. Or you can use the "red light" version too if you want. I will respond to either one," I said.

"Yes, Master. I will use it if I need it. But I don't think I will need to."