tagAnalMid-Life Oasis Ch. 02

Mid-Life Oasis Ch. 02

bymeddlesome©

After sending Jill to her quarters, I thought long and hard about how to move forward. This was an entirely new paradigm for both of us. Of course, she wanted to follow me, which meant that I was to lead and leading was going to be a challenge. As much as I liked to see myself as a person of substance, I had been buying my way through sexual relationships for a long time. My Wife loved me at one point, but in the end, she was all about what I could give her. I adapted myself to this and eventually, I valued myself the same way.

Now, I had a woman who wanted me to explore her sexuality with her and to lead her to her own light. No amount of money could quench the thirst she shared with me. In truth, this is exactly what I wanted for a long time. Not the opportunity to dominate another, but to be in a relationship about sharing–about openness and a total lack of judging.

Of course, as much as I wanted it, it was going to take some getting used to. I had been cold and closed for some time. Clearly, Naomi had done more damage to my psyche that I was originally willing to admit.

I had been at my PC for over two hours now and I just couldn't get Jill's perfect body out of my mind. I had a raging erection that wouldn't quit. I thought about going down to her apartment so she could take care of it. I decided to have dinner instead and to try and clear my head.

I hoped to take a somewhat conservative approach with Jill in the early going. I thought this would limit my mistakes of inexperience. Since I had never been a Dom before, I figured it best to wade into the water a little--to do less while I knew less.

I was trying to be duly respectful of the trust Jill had placed in my hands. She had wanted someone to dominate her for years. Yet, she never allowed anybody to do it until now. The significance of this was not lost on me. I was going to do my very best to fulfill all of her fantasies. I was determined to make sure she never regretted choosing me.

I went downstairs at 9pm and knocked on Jill's door with the honest intention of giving her the rest of the night off.

"Come in!"

I opened the door and there she was--naked and on her knees just to the left of the doorway. This was obviously her submissive way of greeting me with due deference. I felt blood rushing to my cock as she began to speak.

"Greetings, Master. I am ready to serve you."

I reached down and patted her head gently as I told her she was a very good girl. I decided at that moment, that having her service my needs was appropriate. Conservatism would just have to wait.

"Jill, you are going to suck my cock now. You will swallow all of my cum and leave my cock clean when you are done. Is that understood?"

"Yes, Master. I am here to serve you."

"Good girl."

She reached out and took my cock out of my pants. She started to give me more of the great head I had received that afternoon. I had already cum twice during our earlier session, so this was going to take some time. I decided that a little endurance test was also quite appropriate. I was going to let her suck me for as long as it took.

I grasped her head with each hand and pulled her off of my cock. I led her to the sofa and I sat down. She knew where she was supposed to be and dropped to her knees in front of me and got back to work. She sucked on my tool with genuine passion. Jill either loved sucking cock or was hell-bent on making sure I thought she did. Either way, her sense of purpose was a turn on for sure.

Don't forget, I went over a decade having to beg for a decent blowjob.

I laid my head back and let Jill do her magic. She sucked and licked and took good care of my balls with both her mouth and hands. The girl was very thorough and she kept her hands and mouth in synch with each other. She had talent for sure. I stayed a little bit detached mentally, to avoid cumming quickly, but she just went on and on with sexed-up vigor and never relented. I continued to keep myself in a non-orgasmic mental state, but her skills were a tough match. I used every trick in the book, including thinking about baseball.

Once she had been sucking my cock for about a half hour, I could tell she was getting a little discouraged. Perhaps Jill was beginning to doubt she could get me off. I sensed that she might make a move and try to switch to sex in order to get my load. I told her preemptively, that we weren't done until she swallowed my cum.

She turned up the heat a little. She was now really sucking the top half of my cock hard and she was pumping the bottom just right. To top it off, she was moaning in very sexy tones. The moaning also added some nice vibrations. She kept this up for a few minutes and I must say I was pretty damn impressed. This girl had heart to go with the looks and the talent.

I decided to engage fully and to help her out.

I began to rock my hips a bit in-time with her strokes. Then I started to shorten my breathing and really concentrate on what she was doing to me. We were now in-synch with each other and my balls slowly began to boil.

I told Jill that my load was on the way.

She clamped down on the end of my cock and sucked my nut right out of me. Once my load was in her belly, Jill started to lick me clean.

I patted her head as she finished up and told her she was a good little cocksucker. I also told her that she should get a good night's sleep as she had a big day ahead of her. She nodded as she cleaned my cock.

I gave explicit instructions, that when she awoke, I expected her to come upstairs and make coffee and breakfast. Once she was done, she was to start cleaning the kitchen and living room until I was satisfied with her work.

With downcast eyes, she said "yes, Master" and my erection returned with a vengeance. Jill looked at me with her big eye lashes batting as if to say "I'll do it all again right now, Master", but I laughed and said that I was finished for the night.

I brought her up to me and gave her a nice deep kiss and told her she had done well. I left her room and went back to my study. I stayed up half the night reading about submissives and their controllers. It certainly wasn't the kind of thing you just learn cold in a matter of hours, but I did my best to get a better grip on the fundamentals. I wanted to have a lot of fun with Jill but I also wanted her to have a great experience. As I mentioned earlier, I knew she was putting a lot of trust in me, so I took her submission seriously.

I finally hit the sack at about 1am -- feeling pretty beat. I now had some more ideas as to how to proceed with my sexy little submissive.

I awoke at about 8am and I headed downstairs. Jill was cleaning in the nude.

Seeing her bent over cleaning the lower track of the sliding doors was a wonderful way to start my day. The coffee was ready and so was breakfast.

She heard me coming down and she greeted me enthusiastically.

"Good morning, Master! Your coffee is ready and there are some freshly baked muffins on the table. Would you like me to fix you something else?"

"No, Jill. This is fine. And a good morning to you as well."

"Should I continue my cleaning, Master?"

"Yes. Finish up what you are doing with the sliding doors and report to me when you are done."

"Yes, Master."

Geez... I was hard before I even had a sip of coffee. I ate a few muffins, drank my coffee and watched Jill's ass spread wide open as she cleaned on her hands and knees with a bubbly energy that would seemingly belie her situation.

I sat, ate and contemplated what her giddiness implied. I was happy she was happy, but was she too care free? Was I supposed to have her more on-edge than this? The counter-intuitive nature of my charge sank in a bit further.

Once she finished, she came over and got on her knees next to me.

"Is there anything else, Master?"

Jill had this slightly left-of-center look to her gaze, but she also seemed very content. She was obviously comfortable kneeling and that moved me to get her up to my level.

"Yes, Jill. Please sit down at the table."

She sat down and looked at me attentively and respectfully.

"Jill, I think it's time we go over the rules that you will need to abide by if this is going to work. Do you understand the need to do this?"

"Yes, Master. You are in charge and I am at your service. I want my new rules to live by, Master. Tell me how I can best serve you."

"Good girl. Jill, there are a few key things that you absolutely must do if this is going to work. The first thing is that you must be one hundred percent honest with me at all times. I want truthful answers to all of my questions. Do not search your mind for the answers you think I want to hear. Let me repeat that part, Jill. Do not search your mind for the answer you think I want to hear. Doing so will pollute our relationship and, more importantly, it will damage and corrupt your growth. So, rule number one is total honesty. To this you must submit completely. There can be no part of your inner or outer self that you are unwilling to share with me in full and without equivocation. Is that understood?"

"Yes, Master."

This was clearly making her hot. I could hear significant shakiness in her voice.

"Good girl. Rule number two is that your submission is not to be shared with anybody unless I expressly allow it. This is only between you and me. I am more than happy to indulge your desires, but it's not something we can take public as I will be living here more than your six months or what's left of them. When we are around other people, you are to act as my girlfriend and not my submissive. Is that understood?"

"Yes, Master."

"Lastly, for now anyways, though I will follow the limits you laid out yesterday, there will be punishments if you make mistakes. This is fair warning. I will follow my instincts as far as how to discipline you, but there will be consequences for mistakes or non-compliance. Do you understand?"

"Yes, Master."

She was now blushing and breathing heavier. This was really exciting her.

"Good. So we have the three tenets of our new relationship. You will be completely honest and forthcoming. You will curb your overt submission when we are in a public setting. Lastly, you will be punished for non-compliance."

"Yes, Master. Thank you for being clear with me."

"Good girl. Should we begin then?"

"Oh yes, Master! I'm ready!"

She wasn't kidding either. You could just see her whole body brimming with endorphins. She was amped to be under my control.

"Good girl, Jill. Ok, then. I want you to go out on the porch and get some sun in the nude, but I want to spice it up a bit. Jill, do you own any sex toys?"

"Yes, Master. I do."

"Good, Girl. How many do you have and what type?"

"Master, I have a vibrator and two dildos. One of the dildos is for the shower and it has a suction cup."

"Good girl. Go get the regular dildo and bring it with you to the porch."

"Yes, Master."

"Go now, Jill."

She left to get her dildo and she wasn't gone long. She returned with a large red rubber dildo that looked like it was about eight inches long. We went out to the big deck, which has outstanding privacy and I told her to get comfortable and to use the dildo on herself as she would if I was not there.

"Remember, Jill... Honesty. Use the dildo as you would if you were alone. Use it for your pleasure and do not try to entertain me."

As if I didn't find her pleasure entertaining.

She lay back on the lounge chair and placed the dildo on her tummy. She spread her legs and started to rub her pussy with her fingers until her wetness was spread around. Then she picked up the faux phallus and started to rub it up and down her pussy vertically for a minute or two as she began to get hot. When it crossed over her clit, you could hear her react a little.

Then she grasped it at the bottom and began to fill herself with the dildo. She was taking most of the big cock after a few pushes. Jill fucked herself with long strokes as she rolled her hips against the big dildo.

I was getting so hard that I thought I might blast off without being touched. It was that hot. She was making these little squeals on the in-stroke that were so freaking sexy. The woman was driving me crazy.

"Jill, I want you keep going, but answer my questions while you masturbate. Do not stop. Understood?"

She was very excited, but she managed a very breathy "yes, Master."

"Good girl. Jill, can you make yourself cum for me?"

"Yes, Master."

"Excellent. Do it now. I want to see you orgasm. Get yourself off as quickly as you can. Show Master how you make yourself cum."

The girl did not hesitate. She got up and held the dildo inside of her as she straddled and squatted over the wooden lounge chair. She slowly lowered herself down onto the dildo until it was almost all inside of her. Then she started to rub her clit furiously for about ten seconds until she started spasming. She bucked and moaned and fell forward with the dildo sticking obscenely out of her pussy as she was rocked by her climax.

As her orgasm slowed, she rolled over and started to fuck herself again.

"Jill, did you cum?"

She was randy now and was not speaking that clearly.

"Yesss, Masssterrr."

"Good girl. Now lay on your back and use the dildo to make yourself feel good. I am going to ask you questions and I expect honest answers. Keep working the dildo and don't think too hard, Jill. Give me the first answer that pops into your head."

"Yesss, Master. I promise."

She was now pumping herself deeply and slowly.

"Jill, now that submitting yourself to another is a reality, I want you to tell me about your hottest unfulfilled fantasy. The fantasy you want more than anything else. It doesn't matter if you think it will happen or if you ever intended to pursue it. Tell me about a fantasy that makes you all wet when you think about it. Start now."

"Oh my God. I can't believe I'm saying this... I have a secret fantasy about being a slut for a group of men. Men who don't care about my pleasure."

Wow, talk about homering in your first at bat.

"Tell me more, Jill."

She was still pumping the cock in and out of her pussy.

"I want to be passed around from one man to another and used for pleasure like a slut."

"Why do you want this, Jill?"

"I ...ahhh... I always have."

"Always?"

"Well, since I started having fantasies."

"Why, Jill? Why do you fantasize about being used like a slut?"

"Because... (she was panting) I have always been a good girl. I've always done the right thing in public. My dirty side has only been revealed in private and not very often with anybody other than myself."

"And what gave you the idea of being used by a group of men?"

"I...well..."

"Tell me, Jill. Remember the tenets of our relationship."

"Yes, Master."

She gathered herself and continued.

"I had a boyfriend my last year in college when I was twenty two. He asked me to be a slut for him and his friends at a poker party and I declined."

"What did he want you to do, Jill?"

"He wanted me to do a striptease for him and his fraternity brothers and then he wanted me to have sex with all of them. He said that it would be fun and that they would all keep quiet about it. He said that the idea of me satisfying other men turned him on."

"But you didn't do it?"

"No, Master."

"Why not?"

"I was scared. I broke up with him soon after. But..."

She went quiet again.

"But what, Jill?"

"But I regretted it."

"Why did you regret it, Jill?"

"Because I ended up fantasizing about it after he propositioned me. It became a dream that I would have almost every night. I'm serving drinks to him and these guys and when I am told to disrobe, I do it. Then they order me around and tell me what to do and with who and I do everything they say. I fuck all of them in all kinds of ways. I do things that I've never done and I love it, but I always wake up right before the biggest orgasm hits me. The dream always ends in frustration."

"I see. Jill, when was the last time you had the dream?"

"Last night, Master."

"Really?"

"Yes, Master."

"How often would you say you have the dream?"

"Every few days."

"I see. Jill, do you want me to help you with your fantasy?"

"Yes, Master."

"Jill, sometimes our fantasies are better off remaining fantasies. Sometimes when we crack the seal, the contents aren't the real deal. Are you sure, Jill?"

"Yes, Master."

"Then consider it a fantasy in progress. Tell me all the details of your dream and what it is that gets you the most excited."

She was increasing the speed with the dildo now and she looked like she might cum again.

"Jill, before you answer, why don't you give yourself another orgasm."

"Yes, Master."

Once again, she got up above the dildo and secured it with one hand as she sank down fully and fiercely rubbed her clit with her free hand. She came hard and a loud scream escaped her lips as she went over the top. God was this girl sexy.

"I'm sorry, Master. Did I make too much noise?"

"No my dear. It was exquisite. You are stunning when you climax. You may stop with the dildo if you wish, but you may also continue."

"Thank you, Master."

Jill laid back to the position she was in before mounting the dildo and kept the phallus buried in her pussy, which surprised me. I suspected that she was trying to impress me and that was almost tantamount to dishonesty, but I said nothing. She was moving the dildo with tiny little strokes and at a very slow pace, but she kept it in motion.

"Now, my dear, you will tell me all the details in your fantasy. Remember, honesty."

"Yes, Master. I promise to be forthcoming. My dream is almost always the same. I'm in my room. The guys are all downstairs. I can hear them yelling and acting like drunk guys and I want to go down and give myself up to their sexual whims and wants."

"Go on, Jill. Honesty."

"Yes, Master. For some strange reason, the dream has me in my apartment and not my boyfriend's."

"You apartment had two floors?"

"Yes, but it was a cottage with a loft. I lived their with no roommate my last year of school. I found the place online. It was cheaper than a dorm. There were strict rules on having people visit. No parties and all that as it was on the edge of this woman's property. She was a really nice widow and she liked me, so she gave me the apartment cheap."

"That sounds familiar. You didn't become her submissive did you?"

"Oh heavens no."

She was laughing as she said it.

"She was older and I think she liked having a young woman living on her property versus some man."

"That makes sense. Go on about the fantasy."

"Yes, Master. I'm in my room and I want them to take me. I decide to give Kyle what he asked for and I put on my sexiest thong. Then I put a bikini over the thong with a plaid skirt on top and a white button down shirt. I look really hot in the dream."

"I bet you do. Go on."

"In my dream, I have incredible confidence. I go downstairs and I serve them and every time I get a beer for somebody, I take off something. In less then ten minutes, I am completely naked. They decide that I should fellate the winner of each hand and they make me get under the table on my knees. I move from man to man under the table and suck their huge cocks for the next hour and I swallow a lot of cum. After about ten hands, they decide that it's time to fuck me, so the game continues with the same rules, but now I am above the table and I ride the winner of the hand until the subsequent hand is won. When it's time for me to switch, the man inside of me gets up and brings me to the next man and puts me down on his cock. I get passed from guy to guy for the next two hours until it's midnight. The only time I am not riding cock is when I drop to my knees to take a load or for a second or two when I am passed from one man to another. It's incredibly erotic."

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