Mid-Life Oasis Ch. 02

"Yes, it is. Is there more?"

"Oh yes, Master. They really abuse me once they stop playing. They do things to me that I wouldn't want anybody to do under normal circumstances, but since I am there to fulfill their kinks and wants, I manage to get off on it. They fuck my pussy with a beer bottle. They fuck my ass with no lube. Eventually they cum in my ass a few times and that helps. Eventually, they start fucking me in the ass and pussy at the same time. They are all incredibly well hung and they take me right to the edge of the mother of all orgasms and then I wake up right before it hits."

"That's quite a fantasy, Jill."

"Well, Master, that's my dream. My fantasy is a little different."

"That's very interesting, Jill. Tell me more."

"Well, in my dream, I face the men I turned down. I didn't really like them and they were boys who barely understood what they were doing. Sure, in my dream, the sex is magic, but it's a dream."

"I see. Go on, Jill."

"My fantasy is to have a group of experienced men use me for their pleasure. I want men who have had the time to figure out what they really want and I want to give it to them. I want to be their pliable cumslut who follows orders and makes dreams come true. In the dream, I am passed around a poker table, but poker is not a requirement in the fantasy though it'd be great if it worked out that way."

"Ok, Jill. Before you move out, we are going to fulfill your fantasy. You will be used by a group of men and you will follow orders and be a total cumslut. Now I want you to stand and then turn away from me with your legs spread."

She complied instantly.

"Good girl. Now bend over and grab your ankles so I can use you comfortably."

"Yes, Master."

I was too hot to be denied at that point.

She's very flexible and she bent over so far that I saw her upside down face looking up at me and my cock as I stuffed her pussy. She was soaked and I got more than half of cock inside her on the first stroke. I started to fuck her as I held her hips. Her pussy was hot and tight. This was going to end quickly.

I lasted about a minute before I announced my load and pulled out.

Jill sucked the cum right out of my tool and swallowed it all. Then she cleaned me without having to be told.

I was living out almost every man's fantasy and the only fear I had at that point was never seeing Jill again after her six months were up. When she finished, I had praise for her.

"Jill, you have done very well so far. Please clean up the kitchen, but when you finish, I want you to take the rest of the afternoon off and work on your tan or whatever you feel like doing. You've earned it."

She was giddy.

"Thank you, Master!"

"Your welcome, Jill. And, Jill, since our time is short, I think we will just go ahead and move you into the main house. I want you in my bed tonight and every night going forward."

"Oh thank you, Master! Thank you!"

I could see how happy this made her and she gave me a huge hug. My hands went to her incredible ass and caressed it. No way was this body sleeping anywhere other than next to me.

"Your welcome, Jill. Now don't make me regret it. Finish your work and clean up."

She bounced off to do her chores with a huge smile. I retired to my study to put all the pieces in place for Jill's fantasy. Two of my frat brothers are extremely well hung and they already made frequent trips down from NC. I was going to start with myself and them and I'd invite a few more frat brothers to fly down as well. The brothers were a perfect solution as they have group experience and are a lock to never utter a word to anybody about Jill. We are an extremely tight and loyal group. Additionally, the guys in her dream were all fraternity brothers, so it played well all around.

My basic plan was to get five of us and Jill and to take my large fishing yacht out for a weekend cruise. The key ingredient would be finding a guy I could trust to captain the ship for the weekend. I didn't want to be bothered with Captain's duties on this trip, though I normally enjoy it.

My boat was an extravagance that my ex insisted on if we were going to buy the house. All I wanted was the small fishing boat. Naomi needed to show off.

The behemoth cost well over a million brand new, but I got mine used for $800,000, which was a steal. It slept eight comfortably with two staterooms plus two more bedrooms as long as you were willing to give up the living room on the lower level. We had plenty of space for all.

There were several great places on-board where we could stage parts of my little sub's fantasies. I was going to do the poker thing for sure, but I also envisioned some fishing games and perhaps some bedroom hopping.

The hardest thing I had to do was share my little prize, but with all she was giving me, this was the least I could do. I could feel myself getting attached to her and I figured the sooner the better with the fantasy. I could at least minimize my attachment angst that way.

I shot out a group e-mail to my top four candidates and told them they were all invited down two weeks from that day and that it was a male-only event that would feature serious sex for all on my yacht with a red hot submissive. I went on to describe Jill and her assets.

I got four "yes" responses in five minutes. The game was on.

I sent a confirmation e-mail and the date was set. I was going to hold off on telling Jill as I thought I might just surprise her. For now at least, I would hold my cards.

Jill spent the entire afternoon tanning and she looked incredible as she cooked our dinner in the nude. I opened a nice bottle of wine and we ate a delicious chicken stir fry with it. Oh yeah, as it turns out, Jill can really cook.

I was on a fucking roll.

We shared another bottle after dinner and we retired to my bedroom early at around 9pm.

I ordered Jill to get on her knees and suck my cock. I told her to give me the best head she could give and I told her to swallow my whole nut. It was a little strange ordering her as I did, but boy did my cock spring to life when she did as she was told!

She was really into this whole thing and she went after my cock like she was possessed. She gave even better head than she did the first two times. The only way it could have been any better would be if she could take all of me. Not once in my life had a woman taken my cock balls deep while giving head. It occurred to me that this was probably as good a chance as I would ever get.

"Jill, I want you to do your very best to deep throat me. Work on controlling your gag reflex and start taking more of my cock in your throat. I fully expect you to be deep-throating me within the week. Jill, tell me what you are going to do."

She took her mouth off of my cock.

"I am going to suck your whole cock, Master. I am going to learn to take it all until my nose is touching your balls or pubes and I am going to love it."

"That's a good girl."

She went right back to work, blowing me as I stood there. No way was I going to last much longer. Jill is just so hot when she sucks cock. Just watching her work on me is enough to get me off, but when you combine her brimming sexuality with the sensations from her mouth and tongue, you are going to cum and cum soon.

She was moaning and taking me deeper than she had before. Then she was sucking the top of my shaft and jacking the lower half with her hand. I was close and I grabbed her head and help it in place as I shot off about ten huge spurts of thick cum. She gulped it down as it came out and she cleaned me up when I finally stopped.

"That was a wonderful blowjob, Jill. Now I want to taste you. Get on the bed and spread yourself as far open as you can get."

She smiled a big smile and did as she was told. She looked amazing with her all-over tan. She was all spread open on my bed. I lavished her bald pussy with my tongue and I used a steady rhythm to bring to the edge of her climax, but I backed off a bit to make it last. I tongue-fucked her little pussy for a while and then I told her to get on her knees with her ass in the air. She complied instantly and as she did, it began to hit me as to why people were so into dominance and submission. It takes all of the awkward communication out of sex. It was an amazing change for me and I was really enjoying it, but not for the reasons one might expect.

The simplified and streamlined communication allowed for more complex sex. Complexity through pure compliance. I mean, is there anything worse for an erection than sexual negotiations? Until Jill, I'd never really given the matter much thought. Going back to a normal relationship was not going to be easy when my little sub left.

Jill had her ass sticking straight up and I started to tongue her little rosebud. As I did that, I worked two and then three fingers into her pussy and put some very firm pressure on her g-spot. Her moans were deep and soulful.

"Ohhh Master. You are making feel so good. I love this so much. Ohhhh..."

I worked her insides deliberately for a good ten minutes -- applying firm steady pressure on her g-spot. She had an internal orgasm and I kept it up. A minute later she had another. I just kept up my slow rhythm and allowed her to roll through a series of absolutely stunning climaxes. She was shaking now and I ordered her on her back.

I went after her clit and nibbled it for a bit before settling into a front-of-the-tongue-back-of- the-tongue stroking (like a paintbrush) where I never lost contact with her clit but also stayed in a steady rhythmic motion. After about a minute of that, she erupted in a huge screaming clitoral orgasm.

I got up and we embraced and got into a long deep passionate kiss. When we finally separated, she told me that she had never experienced orgasms like the ones she was having with me. I told her that it was only going to get better.

We stayed in bed and watched some trash TV until we were recharged. After an hour of Fringe, I told Jill that it was time for her to get back to making me happy.

"Yes, Master."

She started to give me outstanding head and as soon as my cock was at its best, I told her to get on her knees with her ass in the air. I got behind her and I ate her pussy until she was close to orgasm and then I gave her ass a soft tongue bath and then went back to her pussy until she was randy as can be.

"What do you want, Jill?"

"Master, I want you to fuck me as hard as you can."

I leaned into her and it only took me three strokes to hit bottom. I had her stuffed with cock and she was cumming in no time. I banged away at her with full strokes and in just a few minutes, I shot my wad into her deepest places. Jill cleaned me without being told and we went to sleep in each other's arms.

The next morning, I awoke to the smell of coffee and french toast. I went downstairs and was greeted by Jill wearing nothing but a great tan.

Somebody up there likes me.

I sat down and ate as I enjoyed checking out Jill. I told her to eat with me, because otherwise the little sub might not have fed herself at all. As we ate, we talked about things and she confided that she was happier than she had ever been and that the sex so far had been incredibly fulfilling.

We talked about the things she liked and it occurred to me that anal sex was something we could try together. I'd rarely gotten the chance to bang my Wife in the ass and girls weren't at all into it back when I was in college.

I asked Jill if she had ever had anal and she said that she hadn't. I asked her if she wanted to try it with me and, without hesitation, she said she was ready to try anything and everything with me.

I decided that there was no time like the present, but I also wanted to add a bit of drama, so I told her that her anal training would begin after breakfast. I told her that if she performed satisfactorily in her training sessions, that I would allow her to have my cock in her ass.

"Thank you, Master."

After eating, we took a nice long shower together. I washed her thoroughly and paid special attention to her cute little back door. It was going to be a tight fit for sure. We dried each other off and went back to the bedroom. I told her to get on her knees with her ass in the air. She complied instantly with a youthful bounce. Jill's body was insanely tight and with a deep tan she was pure perfection. I was in sexual overdrive just being near her.

This was going to be great for me. That much I knew. I was going to take my time and help her enjoy it too.

I dove right into her crack with my tongue leading the way. I licked her pussy and her rosebud for a long while and I led her to a pair of big orgasms. She was panting now and she couldn't take any more direct stimulation on her clit. I moved back to her little bud and worked her ass sensuously but firmly until she was moaning and asking for my cock.

"Please fuck me, Master. Please give me your big cock. Please, Master!"

I wanted her focused on the task, but she was blindly rushing for the finish line. I could have let it go, but I wanted her to be more compliant and aware.

"Slut, you are not yet ready to make my cock happy. Don't go writing checks that your ass can't cash. Do as you are told and take your anal training like a good slut. In the future, you will exert more patience. There is no pleading during training. Is that understood?"

"Yes, Master. I won't do it again."

For the first time, there was meekness in her tone, which is what I wanted. She was where she wanted to be now and her training was ready for the next step.

"That's better. Now stay as you are."

I got up and put some lube on my hand and rubbed it into her ass. She was purring and enjoying it. After she was lubricated to my satisfaction, I pushed my index finger into her ass. She clenched up a bit, but did not complain.

I worked the finger for a few minutes and she heated up. Then I added a second finger and worked her the same way. After a few minutes, I had her roll onto her back and I ate her pussy as I stroked her ass with my fingers. She came in no time and I told her that the session was over and that, apart from her inappropriate pleading, she did very well.

For her one indiscretion, I had her scrub the deck and deck furniture while I watched. It wasn't too bad, as she got plenty of sun on her nude frame, but the message was sent. The possibility of punishment was real.

The next evening, we repeated our training session and I probed her a little deeper and added a third finger. She took it all and did not complain or plead for release. She was now ready to be taken. I told her that I would take her cherry in our next session.

That session occurred the next morning after breakfast. I told Jill to soak in a warm bath for thirty minutes and to meet me in my room when she was done. She came in naked and she looked incredible. Knowing that I was going to take her ass was a serious turn-on. I had her lay down on her tummy with her legs spread and told her to relax.

I moved in from behind and gently spread her legs farther apart. She opened up and arched her back. I slipped a pillow under her hips and had access to both of her holes. I tongues her everywhere and I took my time. After about fifteen minutes of oral, she had an orgasm as I was working her clit. I let her ride it out to completion keeping pressure on her clit, which she likes. As she started to come down a bit, I moved back to her little rosebud and worked it softly for another minute or so until she couldn't take it anymore. Since this wasn't training anymore, she was free to beg all she wanted and I told her so.

"Please fuck me, Master. Please give me your big cock. Please, Master!"

She was saying it in this soft pleading moan and it had me hard as a rock.

"Where do you want my cock, slut. Tell me now."

"Oh Master, I want you to take my little ass. It's never been fucked and it wants you to be the first. Please fill my little ass with your huge cock."

"Will you take everything?"

"Ohh yes, Master. Please make me take everything. Be as forceful as you need to be. My only purpose is to satisfy you. Make me your slut."

Wow. She was whimpering as she said it. She was in the zone now. She was obviously very comfortable in her submission.

I raised up and grabbed some lube. I rubbed some into her sphincter. Then I greased my raging cock and placed the head at her opening.

"Tell me what you want, slut."

"Please push your big cock it into my ass, Master."

I leaned into her slowly and her ass resisted though she was not tense. I continued to apply steady pressure and waited for her ass to give way. After a few more seconds, the head of my cock slipped in and she gasped and squeaked a little.

I then began to use small thrusts to increase my depth as she moaned and whimpered. I dripped some more lube on my tool as I worked it into her. I had about six inches inside and I was hitting some resistance. I increased my angle and was able to get the last three plus inches into her ass.

Once I hit bottom, I did a grind into her depths and she was gasping, yelping, moaning and whimpering in no particular order.

"Jill, you may tell me if you are in pain."

She sobbed as she spoke.

"No Master, I love your big cock in my ass. I want you to fuck me this way every day. I feel so full. Fuck me hard, Master. Own my ass. Fuck it however you want. Its your ass."

She was clearly doing ok, but I wondered if she was trying to impress me. I started to take longer strokes, but I didn't just start pounding away. I gradually worked up to long strokes where only and inch or two remained inside. Then I started to increase the speed and she took it well. The sounds of pain were gone. She was gasping as I pulled out and I could hear air being forced out of her lungs when I pushed all the way in.

There is no doubt whatsoever, that this was the best sex I had ever had.

Jill's tail was exquisitely tight and watching my cock take her ass was almost as great as the physical sensations her ass provided. I knew I only had a little time and I enjoyed every second of it. Luckily, her ass was now mine whenever I wanted it. No need to try and make it last this time.

Jill was really into it now. She was thrashing her head about and whipping her shoulder length brunette mane from side to side. I couldn't take the visual and pushed my cock all the way into her and dumped a huge load. She ground onto my cock until she was sure I was done. I pulled out and she cleaned me like a pro without being asked.

As Jill cleaned my cock, I thought about how my sex life was blooming at light speed--like a flower in time-lapse photography. I was in sexual paradise.

When she was done, we rested and talked about how much we loved sex with one another. I was glad to hear that she really enjoyed having her ass fucked and that she wanted more. I told her that we would explore it together. She was a great girl and I knew deep inside that I was falling for her. It had been over twenty years since I felt the stirring that I was feeling at that time.

On some level, I was feeling regret for promising to have her shared by a group. I was beginning to wonder if I could handle it. Fulfilling her fantasy would be challenging enough, but watching her get abused was going to be tough, and it was abuse that she desired as much if not more than the sex itself.

I steeled myself to make sure she got her fantasy, but I couldn't deny that I had become perhaps the biggest complexity in-play. My friends would play their part well and without complaint. Jill was going to get what she wanted. I was the one that I had to be concerned about. It was important that I kept myself from being possessive and I knew I had to stay aware of that once the cum started flying.