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Mid-Life Oasis Ch. 01

By: meddlesome



From a sexual perspective, what follows is a rags to riches story. My name is Mike Lewis. I'm a forty five year old recently divorced retiree. It's a mouthful isn't it? I'm sure to a lot of men my age, that description sounds pretty good. And heck, by the time I actually fit that description, my life was already on the rise.

Two years ago, my Wife, Naomi, went crazy on me and tried to take everything I had, including custody of my then sixteen year old Daughter, Karen. Until this time, my life was rather typical. I was unhappily married but I stayed with my Wife because I promised to on my wedding day and because I wanted a stable home for Karen, who was and is the most important thing in my life.

My marriage wasn't always terrible. I loved Naomi for a long time, but she started to change after we married. She got a little more unhappy every year it seemed. I'm not sure what the problem was, though she claimed it was me. It certainly wasn't stress. I made a ton of money, which she spent liberally. Naomi loved to spend my money, but she also loved to complain about how much time I spent away from home. 

Pretty fair, huh?

True, I did travel an awful lot, but sales numbers don't just happen on their own. Getting face-to-face with customers is the only way to stay on top of your business and in control of your destiny. 

I used to tell Naomi that if she was happy with a typical six figure income and a smaller home, that I'd be more than happy to change jobs. However, if she wanted the house help, summer homes, ski houses, cars, country clubs, walk-in closets and clothes to fill them, either I would need to work very hard or we would both have to work. She never seemed to accept this reality and she had no interest in working. Naomi had an MBA and was quite capable of earning a substantial income on her own. With the benefit of hindsight, I think she was just lazy and liked to bust balls. 

By the time I had reached forty, my marriage was pretty much passionless. What happened to her I have no clue. Our sex was still good, but she just wasn't the same. She never initiated. She acted like she was giving to the needy if she went down on me. All this was very strange to me as this was not the way she'd been for the first eighteen years of our relationship.

She was cold when I tried to talk about it and I did try. I think she felt boxed in and blamed me for her lack of options. The life that she thought she wanted was given to her. I was up to my ass in work so I could sustain it for her. Living in luxury wasn't enough. I was supposed to guide her path to self actualization too? And again, maybe I would have if she'd helped me to understand. That conversation never took place. 

Karen was still going to be home for another four years and I wasn't going anywhere until she was at college. In my mind, my Wife had four years to get with it or I was gone.

It never came to that.

A few years back, she started up an affair during one of my longer trips abroad. I was in South America for three weeks and she used her loneliness as an excuse to start an affair, which was easy for her, since she is drop dead gorgeous. Lucky for me, she was totally unaware of the ultra high-tech security system that I had installed a few months prior to her affair.

When I came home from my trip, my Wife seemed a bit out of sorts and she was clearly distant. I'm pretty sure this was her first affair, and she probably wasn't prepared for the guilt she'd saddled herself with. I asked Karen if she knew what was wrong with her Mother and she had no idea, though she did spill one little nugget. Mom had some people over on Saturday night and Karen slept out at her friend's house.

Instinctively, I smelled a rat. I went and reviewed all of the digital recorders that archived the goings on at my home. They are motion sensitive, so I figured this wouldn't be too hard to find. I had this system installed to keep track of my daughter and her friends when we were not around on weekends and to monitor the estate staff and the estate in general. Naomi would not have approved of the snooping, so I never told her. There were three separate cameras for our pool area and that's where my Wife entertained her guests on the evening in question.

It was a small party as my daughter described and when things broke up, one man stayed behind. He and Naomi sat there for a while and had a few more glasses of wine. There was no audio, so I don't know what initiated it, but after a spell, my Wife went over and got down on her knees in front of this guy and gave him a porn-quality blowjob. It lasted about ten minutes and when he came, she swallowed it all like she used to do for me.

I never said the woman had no redeeming qualities.

After the blowjob, they went into our bedroom and had sex several times. Further review found five other instances of sex in my house with this same guy while I was gone. The fact that I had not felt love for her in some time made things much easier to take and emotion was not clouding my judgment. My ego was certainly bruised, but I was ok. Deep inside, I had wanted out for some time. The only issue was how to go about dissolving my marriage to my maximum benefit.

I decided to toy with her a little and I was hoping I could continue to gather evidence showing that she was the one ruining the marriage and that she was unfit to take care of my daughter, who had her current semester plus another full school year before college.

I resolved to keep all my knowledge to myself for the time being and to push my Wife with my behavior. I was never kind to her again unless Karen was around. I was gruff and disinterested in talking to her and when she pressed me, I just said that work was hard and that all she did was spend money. In truth, it wasn't a lie, but I was no longer being nice about it and I left out the part about her being an ungrateful cheating bitch.

I figured that by mistreating her in this somewhat subtle way, I would lessen her guilt about cheating and that she would keep it up. 

Boy, was I right. 

Not only did I find fifteen more instances of infidelity, but I also found the crème de la crème. Her new man was apparently pretty wild and she allowed him to bring a friend with him to one of their sessions. They double-fucked my Wife in broad daylight out by our pool. It was pretty hot actually, though I doubt it was worth it for Naomi as I used it to take her to the cleaners in divorce court. I can't lie though. I beat off to her double penetration several times. The part where the two men both cum in her face at the same time is just priceless. If Naomi had been that much fun as my Wife, we'd never have drifted apart, but that's just spilt pussy and ass at this point.

I intensified my antisocial behavior and a month after her pool side DP and cum shower, she filed for divorce citing irreconcilable differences. 

Ya think?

I told her that she wasn't getting a penny and that I was taking custody of Karen and she laughed in my face. Well, you should have seen the look on her face when we played her highlight reel at the deposition. 

My attorney slaughtered hers and I made out like a bandit in the settlement. Out of the goodness of my heart, I agreed to alimony for one year and I gave her use of our Winter home in Vermont for the same time period. She had some time to find another sugar daddy, but I was free and clear and I got everything I wanted, including my daughter.

My Wife left in utter shame and Karen would not even speak to her. She still hasn't and it's been two years now. And no, she never saw the video.

Karen and I had a good year as she finished high school. I worked my tail off and made sure she had a good home. It was easy to work long hours without a nagging wife. I had no relations with any women during that year. I gave all my free time to my daughter, who was pretty devastated after the divorce. 

She was accepted into most of the schools she applied to and she decided that she was going to attend UVM. I gave her the house in Vermont as a graduation present. She took great pleasure in evicting her Mother when her year was up. The house was on Lake Champlain and was about thirty-five minutes from Burlington. I told her that I'd be happy to get her a dorm room too, so she had a place on campus. I didn't want her drinking and driving in the new car I bought her.

Yeah, you could say Karen loved her Dad.

After she moved to Vermont, I retired and sold the estate on Long Island. Even with the depressed housing market, I netted 3.8 mil. I also cashed in all my company stock and got a sweet retirement package. I left a large booming client list with them, but it was worth it. I got a ton of cash and they will save huge on commissions over the long haul.

I had well over 6 million dollars in the bank and a solid portfolio on top of that. I decided to move down to South Carolina and live in our huge beach house in Hilton Head that looked out over Port Royal Sound. I bought it years ago and rarely used the place. I had a travel agent who'd been renting it out for me, and the place had been a money-maker, but now it would be my new home.

It was a strange transition. After a year with no sex life, I was ready to spread my wings again though I was very opposed to any serious relationships. I got lucky in one divorce. I wasn't going to push it.

I was living full-time in a resort town, so it was easy to find a party, but you mostly met folks that were there for a week or two or maybe for the season. Still, my first six months were quite enjoyable. I had a few hookups, but I met no compelling women. There were plenty of gold digging divorcees and the ones who knew about my net worth wanted to get to know me for sure, but I was not at all interested in what I'd already experienced. I'd be better off taking Naomi back.

Shudders.

I was a UNC grad and a few of my good college friends had settled in Charleston, which was a short drive away. Once I was living in Hilton Head, they took every chance they could to visit and enjoy my pad, which boasted seven bedrooms and five baths, plus a pool, a Jacuzzi and a huge wraparound porch with great views of the water. I also had two boats. A large fishing-equipped yacht and a smaller fishing boat that I used when I was fishing alone. I kept both of them in a private boat house that was about eighty yards from my back door.

I had weekend guests down from Charleston at least once a month and that always made me feel good. Save for loneliness, I did not have a care in the world. I got myself into great shape and I played golf or fished almost every day.

Like I said, it was a beach house, and I shared a good-sized private beach with six other homes. The beach was more than big enough to handle a hundred people, so it was never crowded unless somebody was throwing a party. Karen was really looking forward to coming down for the Summer and I was really looking forward to being a family again. Unfortunately, she got a great work opportunity and decided to stay in Vermont. Maybe giving her a house was a bad idea.

I was pretty down about not having her for her break. Being alone suddenly hurt a lot more. Maybe it was having such a huge house and using so little of it. The house had an attached one bedroom apartment on the basement level. It was right under the porch and had great views of the ocean. I knew that if I put it up for rent, I would have it filled almost instantly. It was never used, so I figured what the heck. Why not improve my monthly cash flow.

I posted it in a few places and got a ton of e-mails. Being the devil that I am, I only returned e-mails that were sent by women. I figured I might as well get something that's nice to look at.

I had a few ladies come over to look, but they were all annoying. I gave them a price that only a loon would pay and they all went away. I was ready to drop the price considerably if the right leseee came calling.

She did.

The tenth person that came to see the place was a 26-year old beauty named Jill, that had just graduated from Duke with a masters degree in ocean sciences. She had a six month gig on Hilton Head and needed a place to stay.

She was a bubbly young thing and she loved the apartment. The thought of her tight little body living under my roof was delicious. She was a brunette and her hair was shoulder length. She had a nice tan on her smooth skin, but you could tell she had to work for it. Her breasts were average size but very firm and she had smoldering blue eyes that made my cock jump the first time we made eye contact.

I was totally smitten. Anybody would have been. I hadn't had that kind of immediate attraction to a woman in years.

Sadly, when I told her the rent, she almost fell over. The number was a thousand lower than what I'd been offering the place for, but was still more than double what she could afford. I could tell she was devastated. The money meant nothing to me and I was very much into having this incredibly sexy creature living on the premises. I tried to play it cool and told her that I had some people who already wanted the place. I also told her in a casual tone that she was the nicest person so far and that, since I want a person I am comfortable with, I would knock her rent down by twenty-five percent. That still left her significantly short on a monthly basis.

Then, she took the bait.

"Mr Lewis, I really love this place. I love the ocean and I love the idea of going to sleep to the sound of crashing waves. My job is only four days a week. Is there any way I could work off some of the other money on Fridays through Sundays? I am good around the house and I can cook."

I told her that I already had a maid service and she seemed to deflate. Then I told her that we could give it a go on a trial basis. She could stay for the next month and take over my housecleaning and we'd see how things work out.

She was giddy and she moved in the next day. She had a few bags and no furniture, but the place was already fully furnished, so she was going to be fine down there. Jill worked Monday through Thursday and we agreed that she would clean my house on Friday and Saturday mornings while I was golfing. She did a good job, but it's not like I made much of a mess. After the first month, I agreed to extend her stay to the full six months.

Jill was a very nice girl. Very enjoyable to be around. That said, it was her incredible beauty that punched her ticket for the last five months.

A few weeks after extending her stay, I came home from golf a little earlier than normal. I found Jill sunning on my porch with her ipod on and nothing else. 

Now, based on my usual timing, she still had forty-five minutes left. I had gotten an early tee time that day, but she did not know about that. I just hadn't thought to tell her.

She was on a lounger and she had it down flat. Her eyes were closed and she'd have had a tough time seeing me anyway with the Sun's glare off of the glass windows on the sliding doors.

There she was. 

I just had to get a better look. 

I crept a bit closer and my breath was taken away. She was just amazing. Her dark little nipples stood out proudly and looked like candy. Her pussy was shaved, but she had a nice cropped patch of black hair up top. She had a sexy tummy and a cute little diamond belly ring. Her body was even tighter than I had gathered. Though I knew she was hot, I didn't realize just how hot until that moment. Even her shoulders and arms were sexy. Jill had an athletic build, but she also had a little extra padding where it really counted. She had phenomenal hips and a little perceptible bubble shape to her butt. She was absolutely fucking perfect.

Me and my raging hard-on backed away and went back out to my car and left. I came back an hour later to find her finishing up the house with clothes on. I figured that this was her routine. 

When I moved in full-time, I decided to set up a high-end surveillance system like the one I finished my Wife with. At that moment, I was very happy about my decision.

I had twenty hidden cameras installed. They were all in my part of the house. There were none in the apartment.

The cameras revealed little more than expected at first, but she did get more and more daring as time went on. After a month went by, she was doing everything in the nude and throwing her clothes on right before I got home. She obviously loved being naked and her total lack of tan lines attested to this.

The girl also liked to touch herself. She usually made herself cum at least once when she was sunbathing and it was always extremely hot to watch. 

Jill had exquisite orgasms.

I now had a plan and it was time to push the envelope a bit. I set up an early tee time that Friday and came home a full hour early. I checked the deck as I drove up and it looked empty. I closed the car door gently so as not to alert her to my presence and I walked right in on her vacuuming my living room with nothing on.

She jumped about ten feet in the air when she saw me and she hid behind the sofa as she apologized profusely. 

I didn't give her anything to read. I was nearly expressionless as she went on and on about how sorry she was and how embarrassed she was.

"Jill, do you always clean my house in the nude?"

"No, sir. Well, sometimes."

"Sometimes?"

"Well, I like to tan in the nude and since I can't do that at the beach, I've been using the deck while you are golfing. I hate tan lines and I love the sun's warmth on my body. I'm so sorry, Sir. I didn't think there was any harm. Please don't kick me out. I love it here so much!"

I had the upper hand. The salesman inside me kicked in. I wanted to play this just right.

"Well, Jill, I guess there's no harm. I mean, we're both adults."

"Yes, Sir."

Then, in a very light joking tone, I threw out a test balloon.

"Heck, you sexy little thing. If I'd known you liked to clean in the buff, I'd have had you to do your cleaning while I was home!"

I laughed as if I'd just told the funniest joke ever.

She laughed too, but I could tell she was actively thinking. She was still behind my lounge chair and it really didn't cover much.

"Ok, you poor girl. Let me get out of here so you can get decent. My show's over."

I turned and started off towards the open stairway to the bedrooms. 

"Uh, Mike?"

I turned around and she was standing there totally exposed.

"Uhhh, Yes, Jill."

"If you like what you see, I'd be really into showing it off."

She put nice emphasis on the word really.

"Jill, I'm not sure that's appropriate. I'm your landlord."

"No really, I actually prefer being naked and being seen really turns me on. I'm a bit of an exhibitionist. You've been so nice letting me stay here and I know my two days of dusting and vacuuming plus my rent don't add up what my apartment is worth. Not even close. I'd love to entertain you and I'm sure I would be very entertaining."

She put a very sexy emphasis on the word very.

"I'm sure you would, Jill, but this is not at all necessary. A deal is a deal. I'm not some middle-aged creep who asks young ladies to undress for me for money. I respect you."

"I know your not asking, Sir. I'm offering."

Now she had a very naughty smile on her sexy face.

"Jill, I'm not comprising your integrity so I can get off. It's wrong and you are too sweet a girl."

"Mike, I'm just asking you if I can be naked when I'm in your house and we're alone. I know I don't have to. I know it isn't for rent. I don't think you're at all creepy. I think you are a very sexy older guy and I want to be naked for you."

I was quiet -- letting her words hang in the air for a few seconds.

"Well, maybe we can make a little deal. It would be pointless for me to lie about how sexy you are. I could look at you all day. How about this. From now on, you clean when I am home. And, when you do clean, wear something sexy or wear nothing at all. In return for this, I will give you total access to the outside of the home and not just the beach. You can use my hot tub naked and you may sun nude on the porch any time you want. Basically, save for the beach, which I share with neighbors, you can be naked any time you want. If you'll enjoy showing yourself to me, I guess there's no reason for me not to enjoy the view."


Mid-Life Oasis Ch. 01



"So, it's the same deal as we had before, but now I'm cleaning in a sexy outfit or naked? That's all?"

"That's all."

"Ok, Sir, you have a deal."

I bought her a skimpy French maid's outfit with stockings but no underwear. For a month, she cleaned and I watched. Every time she bent over, I got a clean look at her hairless pussy and ass. I also saw her naked walking around on my porch or in my hot tub. She was a vision and the vision was all mine.

My rate of self-gratification was through the roof.

As the days passed, she cleaned more and more until she was cleaning every day without fail.

I obviously wasn't the only one having fun. She really seemed to get off on cleaning for me and showing me everything. She would bend over any time she got the chance. She also bought a bra to wear with the outfit that pushed her tits up but left the nipples uncovered. She showed up in it and asked me if I liked it.

I said that I did, but that I was already having trouble waiting for her to leave before I masturbated as it was. This would only make things worse I told her, with a bit of humor in my tone.

"You really have to do that because of me?"

Is this girl serious? She was probably the sexiest creature I had ever seen. Nobody could survive the show I was privy to without substantive release.

"Well, I don't have to," I said, "but I'll have a serious case of blue balls if I don't."

Then the little minx had an idea.

"Well, if it helps, you can do that right now. Why should you have to wait?"

"Oh dear, I think we've already pushed the bounds of our relationship pretty far, haven't we? I already see you naked all the time!"

"Exactly! You see me nude everyday and I now know you beat yourself off after I leave. Why should you have to wait? I want this to be fun for you."

This was going almost too perfectly.

"Jill, you are as hot as a woman can be, but I just don't feel right about it. I feel like I'm taking advantage of you."

"Nonsense! I'm a grown woman and I have seen a penis before. Besides, I think it's hot!"

She left without a word and went to my downstairs bathroom and returned with some lotion.

"Here!"

She tossed me the bottle.

"Let's see you take care of yourself while I do some sexy posing for you. Come on. How do you want me? Should I just take it all off?"

"Jill..."

"Come on. Are you afraid? Is it small?"

She was really teasing me now and she was obviously enjoying being the aggressor. Jill was far naughtier than I had expected.

"Small? Um, no...."

I dropped my shorts and boxers and revealed my rock hard nine plus inches. She gasped.

"...not small."

"Um yeah! That is the longest cock I've ever seen and the fattest too!"

I started to rub it out and I was about to open the lotion when she stepped in and grabbed my cock with both hands. Now we were both holding my big tool and I was going to be dumping a huge load very soon one way or another.

"Can I please suck you big cock, Sir? Please! I really want it, Sir. Don't deny me."

She said it so sexy and she looked at me with her big innocent wanting eyes. I just fell back into my lounge chair and Jill dropped to her knees in front of me. She didn't suck my cock. No. She worshiped my cock. I had never had such great head.

Her body was as sexy as you could possibly imagine. Lithe and supple. She was extended towards me with her back arched and her ass forming a heart shape from my angle. The muscles in her slender back twitched as she worked on my cock.

Better times have never been had.

She took as much as she could and then moaned on my shaft when she reached her throat's limit. She was taking me pretty deep and using her tongue on the underside of my shaft. Between her great skills and the vibrations from her moans, I didn't last long.

"Oh god, here it comes."

I shot off an enormous load and she didn't pull off. She held my cock-head just inside her mouth and took my entire nut and swallowed it down. Jill then took me deep again. She didn't stop sucking me. She just kept going at me hard and never let me go. She kept my cock at full staff. I could barely take the pleasure Jill was dishing out and I was almost relieved when she finally took her mouth off of my cock.

"Sir, will you please fuck me now? My little pussy is just aching for your oversized cock."

She didn't waste any time waiting for my answer. She climbed up, straddled me, and she slid down my pole. Now, under normal circumstances, I could never have kept an erection after an orgasm. 

This was far from normal. 

This woman was getting sexier by the minute. Her little pussy was tight as a vise as she rode me.

"Oh yes! Fuck my little pussy. Oh my god you're so huge!"

I held her hips and she rode my cock. She was soon taking the entire length and I was harder than I'd been since I was a teenager. It went on for about five minutes and we were locked in a deep kiss with our tongues entwined the entire time. It was amazing. She started to convulse and I felt her tighten further in orgasm, which set me off. I sent spurt after spurt into her tight little pussy as we kept kissing deeply. 

It was our first time and we came together. She broke the kiss.

"Oh my god! That was the best sex I have ever had in my life." 

She immediately went back down on me and cleansed my cock for me. Then she slid back up with a huge smile on her face.

"The royal penis is clean, your highness."

It was a joke from an Eddie Murphy movie and I laughed. She put her arms around me and kissed me some more before asking a really dumb question.

"Did you enjoy me, Sir?"

"Yes, Jill -- and I'm glad you enjoyed it too. Though I am not very proud of my behavior. Nor do I know how we can go on from here."

She was immediately concerned.

"Did I do something wrong?"

"No, Jill. You are an amazing woman. I wish we could do that all day every day."

"We can, Sir!"

"Jill, I really don't feel comfortable having sex with a young girl who calls me Sir."

"Oh, I'm so sorry. It's just that I am a little on the submissive side. I like doing what I'm told and I like to be extra respectful. It gets me off, so I just sort of do it all the time."

Oh brother. 

Where did this woman come from? What next? I continued to play it cool, knowing that I had her.

"Jill, like I said, I could have sex with you every day for the rest of my life, but I just don't know if it's cool for us to be together. I'm freshly divorced and I don't want a relationship. And, based on the sex we just had, we will end up in a relationship if we aren't careful. The French Maid thing was cute and harmless by comparison."

"Mr. Lewis, I am a grown woman. I can have sex with anybody I choose. I'm not all that experienced, but you are not the first older man that I've been with. I'm twenty six! And, I swear I don't want a relationship with you. I'm only here for six months!"

"Well, I still don't see how this is going to work."

She was well prepared for this.

"How about this, when I am at work, I am on my own time. But, when I am off work, I am all yours. Yours to have when, where and how you wish. I've always wanted a Master, but I've never met anybody I trusted enough or who I thought deserved me. But, with you, Sir, I feel like giving up control and being what you want me to be. Maybe you and I can use the next three and half months to fulfill some fantasies for both of us? No strings!"

I had her. And, I had her in a way that I'd never even contemplated.

"And you'd be totally comfortable with this?"

"Oh yes, Master! More than comfortable. I want it!"

"Well, I have never been a "Master" before, so I may not make you happy. I think I may lack the proclivities needed to satisfy a submissive like yourself."

"But you're willing to try?"

"I guess so, but should we establish some ground rules? Is there anything you want that I should know about? I'm not entirely sure how to proceed as a Master."

"It's pretty easy I think. Respect my limitations. Try not to leave any permanent marks on my body. Don't injure me. I just want to be your little sex slave, Master. I want you to use me as you want and I want that big cock stretching me and making me cum. Use me to fulfill your fantasies! I've never been in a threesome and with you, I'd be more than willing to try one. I will do anything you say."

Oh my. Once again, I let her words hang for a few seconds.

"Ok, Jill, you win. Let's give this a shot."

"Yay!"

She hugged me and then I told her to finish her cleaning and that I'd have more orders for her when she was finished. 

"Yes, Master."

She got right to work with my load running down her inner thighs and I went to my office and looked up "sexual submission" on Google. I was going to need to be a quick study on this stuff. I really wanted to get this right. Jill was the most amazing woman I'd ever met and I wanted to make her want me not just for the next few months, but for as long as I could have her.

About and hour later, I had learned some things. It was mostly basic psychology, but I still had a lot to learn. About this time, her nude form appeared in my office doorway.

"I'm done with my chores, Master. What can I do for you now?"

I decided to buy myself some time. I figured the less said that day the better. I hid my burning desire and played things cool and cold.

"That will do for now, Jill. I may require your services later and I may not. Please stay in your apartment and wait in case I need you. Oh, and you only wear what I tell you to wear from now on. For now, let's just stick to nothing at all."

"Yes, Master."

"Tomorrow, we will sit down and go over the ground rules for how you will be expected to behave."

'Yes, Master"

She left and I sensed that she was a little off-balance. I had no experience at this, but neither did she. She was in a very wild situation and I was the cat who ate the canary. This was going to be a lot of fun.

To be continued...



Mid-Life Oasis Ch. 02



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."




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. 




Mid-Life Oasis Ch. 02



I guess even paradise has its little problems.

I decided that, until we had the gangbang, I would need to be more dominant. We were on a trajectory to be in-love too soon and that was a potential problem. She wanted discipline and I figured this was a good time to push that envelope a bit and to hopefully keep love on the back burner.

I decided to spend more time on the details of her fantasy and see what that might lead to. 

"Jill, tell me more about your fantasy. How do you envision it playing out. How do the men treat you?"

She didn't hesitate.

"They treat me like a slut, Master. They treat me like their property."

"And, that is what you want?"

"Yes, Master."

"Jill, tell me again why do want to be treated like a slut. Be totally honest."

"Because I am a slut, Master. I may act like a good girl, but deep down inside, I am a dirty girl."

"Then, why do you act like a good girl?"

"Because being a slut is no way to live, Master. A woman is not accepted unless she behaves like a lady. I want a career and I need to maintain my reputation. I can't have pictures of me on the net or whatever and that's what happens to girls who are reckless and who give it out all the time."

"So, if you could get away with it, you would be a slut all the time?"

"I don't know. Maybe. I do like being a good girl too. Maybe I'm just sick of all the men that I'm with treating me like a goddess or whatever, when what I really want is to be fucked. I love sex, Master, and I love getting fucked. Every guy I have been with except for Kyle, has wanted me for a Wife. Guys fall in love with me too easily and guys don't like to fuck the shit out of the love of their life. They want to protect me and respect me. I don't want their respect and protection if that means a spineless sex life. Men are too linear when it comes to love and sex. At least that's the way it seems to me. It's what I've experienced so far."

This was one unique woman.

"Wow. That's quite enlightening. In your fantasy, what are the men saying as they fuck you?"

"They call me dirty names like whore and slut. They tell me that I'm nothing but a cum bucket and that they are going to use me until they are satisfied. I really get off on it too. I'm always on the verge of the biggest climax ever when I wake up."

"Jill, did you have the dream last night?"

"Yes, Master."

"Jill, the next time you wake up after having the dream, I want you to tell me every detail that you can remember. Wake me up if you have to, Ok?"

"Yes, Master."

"Ok then. It's time for you to get to work. Get your chores done and when you are satisfied with your work, I want you to work on your tan until it's time to cook dinner. I'll be in my study."

"Yes, Master."

She cleaned the house with her usual zeal and cooked a great dinner that night. We had more intense sex before bed and she came like crazy. When I awoke the next morning, Jill was awake and looking at me with her big blue eyes. I felt blood rushing to my cock. 

Jill told me that she'd just had the dream again. I told her to recount the most vivid part or parts.

"Master, after they finish the card game, they penetrate me in both my holes at once and it really hurts."

"Is that pain part of the dream Jill or is part of the fantasy?"

"Both, Master."

"You want to be in pain?"

"Yes. Well, sort of."

"Please explain, Jill."

"It's sort of like you taking my ass. There's pain at first, but the pain is something that I overcome. A few minutes later, the pain has turned to intense pleasure and as the men are calling me their whore and their cumslut, I begin to shake and as I am about to explode in orgasm, my eyes fly open and I am unsatisfied. That was just a few minutes ago, Master."

"You always mention your failure to finish. This has to be a big key. Part of you fantasy is just to finish? To find out how that orgasm feels in real life?"

"Yes, Master. Very much so."

"Ok, Jill. I think we are getting somewhere now. The only issue I see is that if the men are only using you for their pleasure, will you get that big climax? I think we might have to blur that line. At least at the end we will. Does that make sense, Jill?"

"Yes, Master."

"Good girl. Why don't you go fix breakfast and then get to work on your chores. There's a shopping list on the kitchen table. Please get to the store today."

"Yes, Master."

While Jill shopped that afternoon, I made some on-line purchases. I got her a pair of Ben Wa Balls to help her enjoy her cleaning a little more.

I also bought some restraints just in case I ended up wanting some during our trip. They were padded, but they were steel on the inside, so I knew they'd get the job done if I needed them. The thought of chaining Jill somewhere on-board so the guys could just use her at their whim was pretty hot and I knew she'd love it. I also bought a long chain and collar for her so we could move her around in the kind of demeaning fashion that she craved. The last two things I bought were a blindfold and a ball gag.

I went down to the marina and talked to a few candidates for captaining my ship for the big weekend. I met a guy named Bill and I told him that we had a bachelor party scenario and that we'd be banging a hot submissive for about 48 hours. We needed a guy who could handle the ship and also use proper discretion once the weekend was over. Bill told me that he was only here for another three weeks and that he was moving back to San Diego after that. He said that he'd be fine with the bachelor thing and that he'd keep everything he saw to himself.

I told him that he was hired and that the gig would pay five times his normal rate. He liked that a lot. We had our Skipper.

After I left the marina, I hit the butcher shop and put in an advance order for a weekend's worth of steak, chops, sausage and plenty of marinated chicken tenders. I kept the boat well stocked with booze, but I went out and bought ten cases of various beers and a case of wine and champagne too. Better safe than sorry.

I also placed an order for fresh breads and produce to be delivered the day we left and the stage was all set in terms of prep. Everything we needed would be there and Jill would be cooking when she wasn't satisfying us. She was going to be a slave for five men and she was going to love it. I was determined to bring Jill's dreams to life for her.

I just hoped that my dreams weren't squashed in the process.

To be continued...



Mid-Life Oasis Ch. 03



Jill's big weekend had come and we were set to leave early Saturday morning as soon as all the guests arrived. 

After she had cleaned up the kitchen following breakfast, I ordered my little submissive to the boat. She was to go to her bedroom and wait for me to summon her. Jill was officially on-duty. For the next 36 hours or so, she was a whore to be used for pleasure.

I did my level best to eradicate all of the affection from my voice, but it wasn't easy. 

"Go now, slut" I said firmly and flatly.

"Yes, Master."

She was definitely in the zone. Her tone was meek and her eyes were downcast. She was ready to serve.

Once my college buds arrived, I went over the rules with them. I told them that they were not to show Jill overt kindness or sympathy. She was to be used like a slut and spoken to like one. They all understood. All the men I enlisted were sexually confident and were all well hung. 

Including me, Jill had five very large cocks to deal with and hopefully to enjoy. 

I explained that things would begin as soon as we were at sea. Jill was already naked and she would remain that way. We were going out to deep water where there would be scant boat traffic if any. We had a very solid weather report and the captain was going to keep us in calm waters for the bulk of the weekend. The stage was set and Jill was ready to take as much cock as we could give her. All her holes were on the menu and the menus were now on the table.

The men were all ready for action and they had all abstained from sex for a few days. They would have big loads to kick things off during the opening round of blowjobs.

We hit the boat and Captain Bill took us out to sea. We opened up with a round of tequila shots and then cracked open some beers. One of the guys lit a joint and that went around so everybody could get a little taste.

Once we had a nice buzz going and once the mainland was no longer in sight, I went downstairs to get Jill. When I went to her room, she was by the door, eyes down and on her knees waiting--like an obedient dog.

"Slut, are you ready to be used?"

"Yes, Master. I am your horny cumslut and I follow all orders."

"Good girl. Now we are going to go upstairs and you are going to meet my friends. After I introduce you to a man, you will ask him if he wants his cock sucked. Is that understood?"

"Yes, Master."

"If he says yes, I will hand your leash to him."

I then took out a collar and put it around her neck. I took the long leash and hooked it to the collar.

"And, slut, don't let me see you walking without explicit permission. On your hands and knees all weekend unless I say otherwise. Is that understood?"

"Yes, Master."

Whoa. She was suddenly even meeker. This got me thinking. I turned up the heat a little more.

"You are here for our enjoyment, slut. Don't allow your pleasure to get in the way of your Master's pleasure. Your pleasure is only a bonus. Job one is satisfying your Masters. Don't you dare allow a cock to leave any of your orifices without being thoroughly cleaned. You are going to be degraded and treated like a whore and you will thank your Masters for this. Do you understand, slut?" 

"Yes, Master."

She was now barely audible.

I led her to the back deck. The men were all blown away by Jill's beauty. 

Despite my assurances that she was a hot little innocent, they expected a trashy chick and trashy was about the last thing that anybody would ever say about Jill, especially at first glance. She just had a pure look--like she had been living under glass her whole life.

There were leather bench seats that went around three of the four sides of the back of the ship. The fourth side was open to the sea and allowed for a good fishing set up. The men were all seated and there was plenty of space between each person. The area can seat about twelve people comfortably. The first guy was Lou and I introduced him to Jill. I pulled Jill's leash upward and told her to stand for her introductions.

"Lou, I'd like you meet Jill. She is going to be our cumslut this weekend."

She did a little bow curtsey kind of thing as she began to speak.

"Very nice to meet you, Master Lou. Would you like me to suck your cock?"

"Very nice to meet you too, slut. Go right ahead. Suck my cock and swallow my load."

"Yes, Master Lou."

Jill handed Lou her leash which he accepted with a sardonic grin.

She dropped to her knees between his legs and fished his huge tool out of his pants. He was already on his way to erect and Jill sucked his head with her usual zeal. After a few minutes, she had him at full staff and he was impressive.

Jill began working his lower shaft with both hands as she bobbed on the top half. Then she slathered him with saliva from top to bottom and jacked him with two hands as she licked and sucked on his big balls. 

"That's right. Suck my balls you little cumslut. I'm gonna feed you my nut and you are gonna swallow it all. You hear me, slut?"

Jill moaned her approval and gave a few subtle nods as she continued to suck on his balls with a fervor I was slowly growing accustomed to. She was getting to Lou and after a few minutes she sensed he was close and attacked his cock with her mouth. She took him as deep in her mouth as he'd go and then started to force her throat down on him. She gagged a few times but kept trying. She had a few inches in her throat when Lou grabbed her by both sides of her head and dumped his wad right down her esophagus as he let out a moan of satisfaction that any man would envy. He pulled out of her throat and he looked like he gave her a little more sperm to taste. Jill cleaned him thoroughly and when she finally took her mouth off of his cock, she gave him a huge smile that was obviously genuine.

The other men were staring in awe at what was going down. 

As I said, I had gone on about her sex appeal when I told them about her, but they were now realizing just how serious I was. Jill turned to me on her knees, unsure of how to proceed. Lou handed me her leash and gave me a huge shit-eating grin as if to say "man were you right." I stood her up and pulled her to Rob, who was seated directly opposite of Lou on the starboard side.

"Jill, this is my good friend, Rob. Rob, this is Jill and she will be your slut this weekend."

"Nice to meet you, Slut."

"The pleasure is all mine, Master Rob. Would you like me to suck you cock?"

"After what I just saw, you bet."

Jill gave him the leather handle to her leash.

He took the leash and pulled his trunks off and sat back as Jill knelt between his legs. He was big, but he was a ways from full staff. She licked and sucked him as he grew.

Here we were... miles and miles from shore on an absolutely gorgeous Saturday morning--partying on a huge luxury yacht. We were all getting blowjobs from a woman that was so hot she makes Katy Perry look fat and ugly.

I never envisioned my retirement being this good.

I did a good job hooking my girl up too. All of my buddies kept themselves in great shape. She didn't have any fat bald middle aged guys to deal with. I could tell she was very happy with the sexual hand she'd been dealt. 

Jill was now going to town on Rob, who was not going to last very long. Her oral skills were just too good and combined with the scene and the vibe, we were all going to be quick the first time.

She was cupping his balls with her hands as she took two thirds of his cock with her mouth. Rob announced his nut.

"Get ready you little slut. Here it comes!"

He started bucking his hips and cumming in her mouth. I never saw a drop as she swallowed it all down and proceeded to suck him nice and clean as he degraded her.

"That's a good slut. Yeah, that's it. Clean my rod. Good girl."

Jill finished up and thanked Rob for his cum.

Rob handed me her leash and I brought her over to Marc, who had gotten ready. He was sitting down but his massive tool was standing at attention. 

"Jill, this is Marc and Marc's big cock."

"Hello, Master Marc. Would you like me to suck that for you?"

"Will you swallow my nut, little slut?"

"Oh yes, Master Marc. Every drop."

"Get down on your knees then."

She did and I handed the leash to Marc. She performed another amazing act of oral that had Marc dumping his seed in no time. She swallowed everything just as she promised and she worked his manhood until is was nice and clean as he patted her on the head and told her what a dirty slut she was.

Once he was clean, she got to her feet and took another submissive bow. I took her leash from Marc and brought her over to her last new cock. 

"Jill, this is John William Jacobs the Third, but you can call him Trip."

Trip had also disrobed and he was sitting holding his huge rod. Trip was more than ready after watching his friends get blown so vigorously. 

"Hi, Master Trip, would you like a blowjob?"

"Nice to meet you too, Jill. Are you ready to be my little cockslut?"

"Oh yes. Can I swallow all your cum?"

"We'll see if you can handle it."

"Every drop, Master. I promise."

I gave Trip the leash and he leaned back in his seat.

She got down on her knees and went to work. Trip's cock was big like the rest but what stood out was his cock's head. It was freaking enormous.

Jill was having some trouble taking it into her throat and she rightfully gave up and started to work his whole cock using her hands and mouth in tandem. She did that with sublime rhythm and she just kept it up and Trip's moans of pleasure let her know she had him. His breath shortened and he announced his eruption.

"Open up, Slut. Here comes my nut!"

She covered the tip with her little mouth and she was swallowing a second later. She kept stroking and he kept spurting. After about a minute, she licked the whole monster clean and Trip was patting her head and calling her a good little slut over and over as his head rolled around in agonizing pleasure. Jill was clearly loving it.

It was now my turn and I was going to enjoy her. I had sat down after bringing her to Trip. I was by the back of the boat on the port side. I shed my trunks and spread my legs. Trip released her leash and I told Jill to come to me.

Jill stayed on her knees and crawled over to me with the leash dragging behind her. 

"May I please enjoy your cock, Master?"

"Yes, slut. Take all of me in front of everybody. Show them what you can do. It's time to deep-throat. You're ready now. Take me all the way you little cumslut."

She made love to my cock with her mouth for about five minutes. She was intense and focused and she did all the tricks that she always does. I was percolating for sure. Then I took her by the sides of her skull and started working my tool into her depths. She adjusted her angle and relaxed her throat as I kept working my way in. Suddenly her throat stopped resisting and I slid into her completely. 

Wow.

This was better than any porno you have ever seen. Nobody there will ever forget it. I know I won't. For the first time in my life, my cock had been taken to the root.

What a scene... clear blue skies on an almost still sea, and this girl has almost ten inches of cock in her mouth with a group of men watching. Jill told me later that she was so turned on by what she'd done that she almost came without being touched.

Well, I was being touched in an amazing way. And, after about three small strokes in and out of her throat, I made a massive deposit that she never even tasted. It went directly to her belly. I pulled my cock out and she caught her breath audibly. Then my little slut cleaned up my cock.

Once she was done, I told her to get on her feet and fetch us a round of beers. She did, and each guy gave her pats on the ass as she served them. "This is the hottest fucking thing I will ever experience", I kept thinking to myself. 

She was so willing and so hot for the fantasy. It was just incredible.

I sent Jill to her room to clean herself up. I gave her clear orders to not make herself cum and told her that she'd be summoned in a little while. 

She looked great and had performed incredibly well in round one, but I wanted some time to talk to the guys without her around. She crawled off to her room dragging her leash behind her as the men stared in total disbelief. 

My buds were all astounded at what they had fallen into. They all wanted to do Jill in every imaginable way and I assured them that they would get ample opportunity. 

I told the guys about her secret desire to be passed around. I wanted to give her the exact experience. My idea was to pass her around for as long as we could as we fucked her standing up. 

Eventually, when we started to get tired, we would DP her and that way she'd only weigh half as much or thereabouts with two men supporting her weight.

Her feet were not to hit the floor once we started fucking her. We were going to literally pass her around for an hour and fuck the shit out of both her holes while calling her names and listening to her sounds of ecstasy.

It was a lay-up as long as we worked together. 

As it worked out, we all had cocks that were in the 9-10 inch area and we were all about six foot or thereabouts. Keeping her even and balanced and not having our cocks slip out was going to be easy once we had her on two cocks. But before that, we would pass her around from guy to guy. Given her fantasy, it was going to be really erotic.

I decided to keep her alone and horny for a while. It was a little after 11am and I figured I'd bring her back in time to make us all lunch. After lunch we'd hit the mid-deck area, which is by far the nicest area topside and we would pass her around in the afternoon sun.

I reminded all the guys to keep calling her names but to make it genuine and not forced. I also reminded them all to use lube before fucking her ass. Another joint was going around and I went for another round of beers.

At 11:45 I went and got Jill. She was kneeling at the door naked with her head down and her leash on. She was really into this.

"Jill, it's time to get lunch ready. I'm going grill steaks and lobster tails up top and I want you to fix the pasta salad and put the vegetable skewers together. Bring me the skewers when they are ready. You will eat a light meal by yourself in the kitchen."

"Yes, Master."

"Good girl."

I walked away and grabbed all the meats to be grilled before heading up top. We had a great lunch and we all had a nice even buzz going into the afternoon. 

Once we had a little time to digest, I called Jill up top and told her to start working on our cocks as we sat. I told her that we were going to fuck her now and that she had better be ready to get all of her holes taken deeply and repeatedly. She said she was ready to be used for our pleasure and that we should treat her like a dirty slut.

She dropped down in front of Marc, he was just left of the door she entered through.

"Ok, guys. Don't cum in the slut's mouth. Save it for later. She's just here to get us all hard."

Marc pulled her off and she moved to Trip for a bit and then to Rob. As she sucked Rob, we all closed around her in a circle and got our cocks in her face. She went from cock to cock for about ten minutes as we all enjoyed her wanton display of servitude.

Eventually, I told her it was time to get fucked. She stood with a big smile as I told her to come to me. I had her jump up and get her legs around my waist and I fucked her standing up. She held on to me with her arms around my neck.

She was completely soaked and I bottomed out in her pussy on the first stroke of my big cock. I bounced her up and down for a bit as everybody watched. She was cumming in less than a minute and her screams were exquisite. I kept fucking her deeply right through the climax and as she settled, I walked her over to Marc, who grabbed her from behind with her legs spread so I could pull out of her.

Marc held her there so Trip could push into her pussy. Jill gasped as his big head breached her womanhood for the first time. She threw her arms around his neck and got her legs around his waist and the transition was complete. She rode Trip as we all watched and told her what a slut she was. She had another huge orgasm and Trip passed her to me and I held her so Rob could get into her pussy and get a hold of her. 

She rode cock number three for a few minutes and Rob was tickling her depths as he thrust his ten inch monster up inside her. Jill's body was writhing in ecstasy as Rob moved her up and down on his big pole. I told him to fuck her faster and to make her cum. Rob started to really bounce her up and down and giving her the whole length. After a minute of that, Jill cried out in orgasm and she started to shake and buck. Rob was losing his grip on her as she orgasmed out of control.

Lou stepped in from behind and held her up as both men got a grip on her. Rob pulled out and Lou held her as Marc stepped up and pushed his cock into her. She wrapped her arms around his neck and rode him as she had ridden the rest of us. After a few minutes, I held her again so Lou could get a turn.

She hopped up and down on his incredibly thick root and you could tell she liked it. She was bringing herself down really hard and Lou was loving it.

"Yeah. That's it. Take my whole cock you fucking slut."

Jill started to moan really loud as Lou talked to her.

"Yeah, baby. That's it. You really love being degraded don't you? Ride my dick you dirty little cock-whore."

Lou's manhood was extremely thick at the base and she had tears in her eyes as she bounced up and down on him, but the sounds she was making told us that she was loving it. Eventually, her cries increased in intensity and she started to shake in orgasm. 

Jill made all kinds of whimpers and moans as she came all over Lou's big monster. Now I was ready to take things up a notch. I had already poured lube into my hand and I went right to her ass and lubed up her little starfish as she orgasmed. This unexpected jolt made her transition or something and she started to quiver and her legs opened even farther.

Jill was one wild fuck. That was for damn sure.

I kept rubbing the lube into her ass as she came and came and I kept rubbing it in as she slowly calmed down.

"Jill. Tell me what you want right now."

"I want two cocks, Master! Please do it to me! I want to be a whore for my Masters!"

I stepped in and held her ass as I pushed my length into her. She screamed as soon as I forced the tip in. She made a half moan half grunt kind of sound each time I pushed more cock into her, until both Lou and I were both balls deep.

We bounced Jill up and down on our two cocks for a long while as she just went for the ride. She'd cum so many times that she was having a long ride without orgasm, but she was still loving it. 

"Are you enjoying your DP, my little slut?"

"Ohhhh yes. Thank you Master. I love it. Treat me like the dirty whore that I am!"

She went right back to moaning and groaning and listening the men who continued to make crude remarks and encouraged us to "keep pounding the little whore."

I was getting close to orgasm and I told Rob to take my spot. Lou held her as I pulled out. Marc pushed into her ass and they got back into a rhythm. After a minute, Lou told Trip to take his place in her pussy and Rob held her open so they could make the transition.

Trip had a little trouble getting that big old head into her when she was already stuffed with ten inches in her ass. He put some lube on the head and forced it into her.

Jill gasped as he forced it into her and she closed her eyes as he started pushing his big cock into her depths.

"Do you want all of it, you little whore?"

"Oh yes, Master Trip. Fill up my little pussy. Use me for your pleasure, Master Trip! Make me your whore!"




Mid-Life Oasis Ch. 03



She had her eyes closed and she moaned the words as much as she spoke them. She was now really enjoying herself as that big head was scraping her insides and rubbing on her g-spot each time it passed by.

Rob and Trip bounced her all the way up and down their two big cocks in perfect unison. They had the best synchronization so far and they kept that up for about tens minutes as Jill's intensity slowly increased until she was perched on the edge of something really big.

Sensing this, the men tightened their grip on her waist and hips and became more forceful as they moved her up and down on their massive shafts. She started making involuntary noises and thrashing her head around. 

In her dream, this is probably where she would wake up. Instead, she started cumming at the top of her lungs.

"Oh my god! Oh my god! Hold me! Ahhhhhhhhhhhhhhh!"

Jill started twitching and convulsing and was letting out long moans. Then she went stiff as a board and let out a scream that echoed out across the sea as the two guys held onto her precariously.

I spread a towel across the floor of the open area and the men dropped her down.

"Get ready to take our loads slut. On your knees with your head up. Get your mouth and eyes open too you little cumbucket."

She complied instantly. We encircled her and stroked our cocks as we readied to drench Jill in sperm. She got into perfect position and we all aimed for her open mouth.

Trip shot off first and Lou was right behind him. They blasted her from opposite sides and both had thick white loads. Most of it went right into her mouth, but there was also some on her chin. She gulped the mixed load and got her mouth back open just in time for Marc to blast her face. He got her right on the tip of the nose and it went everywhere. The next three spurts landed right on her extended tongue and she swallowed it immediately and kept her mouth open as she did so.

She had a little jizz in both eyes, but she dealt with it. She was really into this and was serious about following directions. She kept her body position and was ready for Rob and I to finish her off. I asked her what she wanted and Jill didn't hesitate.

"I want to be your cum whore. I want to be abused. I want more cum and more cock in all my holes."

Seeing a girl that hot, naked and cum slathered--begging for you to give her more was just too much for Rob and I. We both started dumping big loads on her and we managed to get most of it into her open mouth.

She drank it like is was an elixir and was panting when she finished.

"Did you like getting double penetrated, slut?" I asked.

"Yes, Master."

"Do you want us to keep stuffing two cocks into you?"

"Master, I want as much cock as you can give me. I want to be a good really slut for you and your brothers."

"Good girl. Go back to your room and clean yourself up. We will need your holes again later on."

"Yes, Master."

She crawled off to her room with her leash dragging behind her.

It was Saturday afternoon and we'd all cum on or in Jill twice. I asked the guys if they wanted to fish and nobody had even remote interest. Things were just too good to distract ourselves from the hot slut we were inexplicably in total control of.

I asked the guys if they had ideas of how we could humiliate her without going over the line. Paul asked where the line was.

"Nothing too disrespectful. So far everything we've done to her is what she asked for. Heck, we've probably been nicer than she's looking for. She wants to be treated like a whore both physically, which we are doing, but also mentally. But as far as limits go, we should not hurt her. No marks that don't go away quickly. And, obviously, if she does say no to anything, we must respect that. The thing is, I think she's past the point of saying no, so we need to make sure we don't abuse the license we've been given.

So, if you have alone time with her, don't do any kink stuff like golden showers or worse. Keep it sexual. She wants to be a cum dumpster, but not a toilet. 

For the most part, let's make sure she can enjoy it. She's being too awesome for us to not at least try to make this a great thing for her too. Besides, if we take good enough care of her, she might let us take her out again in the future. I'd hate to kill the golden goose."

I got nods all the way through my speech. The guys got it. I had selected well.

I had an idea for how to abuse Jill on Sunday and I explained it to the guys. We were going to have mostly smooth sailing and our Skipper had assured me he would keep us away from other vessels. My idea was to tie Jill up and have us all take her over and over. I knew that being restrained was part of her fantasy, but just tying her up was too bland. My idea was to tie her very securely to the pulpit up on the bow of the ship. It extended out past the body of the vessel and I was going to tie her so that she would be hanging out face down over the water with her ass and pussy spread open to be taken by us at will.

The guys all loved the idea and since Trip, Skip and myself were all good with rope, we figured we could secure her pretty well. Plus, we had the cuffs and we could lock them to the railings for extra security.

The idea was that we'd leave her strapped to the bow for as long as we enjoyed fucking her that way. Probably for a few hours. Of course, if I got the idea that she was suffering up there, I'd get her down. Jill had been on a lot of boats, so I figured she'd be fine. Her biggest love was the ocean and I thought getting royally fucked with dolphins jumping nearby would be pretty hot for her.

I went down below and grabbed the rib eyes and some more lobster tails. I stopped by to tell Jill that it was time to cook dinner and that we expected to be served in one hour. 

"Yes, Master."

"Good, slut."

She was all cleaned up and kneeling naked by the door. I wondered how long she'd been there.

I walked away and I couldn't help but notice that she seemed a little more "tranced" than usual. She had a kind of stepford tone or vibe and I figured that could be good bad or nothing at all, so I let it go. I was going to avoid asking questions unless I had real concerns.

There'd be a time to discuss all this in more depth when the weekend was over.

I went up top and grilled and shot the bull with my brothers. Jill brought up fresh vegetable skewers and told me that the salad and potatoes would be ready on time.

"Good girl, now get back below deck."

"Yes, Master."

She did a little bow and left.

I looked at the guys and they were all a little mystified. Trip spoke up.

"Dude, what in god's name did you do to that girl? She should she be on a catwalk somewhere and she's our little private whore. How much are you paying for this?"

"Trip, this isn't costing me a dime save for all the food and drink and what I shelled out for Captain Bill."

"So, you're telling me that this was really her idea?"

"Just like I've been telling you all along."

"I feel like I am living inside one of my favorite dreams," said Marc.

"Marc, the amazing thing is, Jill most likely feels exactly the same way. We are helping her to fulfill her darkest fantasy that she never thought she'd get to act out. On top of that, she knows that you guys are trustworthy and we are out at sea where nobody will ever know. She didn't have to leave a bar with us. Nobody in the world has a clue what we are doing. Trust me, the person having the most fun is Jill. I just hope that we show her such a good time that we get to do it again some time."

The guys were all on-board with the program. They understood that she was our whore for now, but that she wasn't really a whore. This was all suspended reality and we were all lucky to be here.

I told them that we'd be fulfilling her poker party fantasy tonight and that she would fellate the winner until the stakes were raised and then she would sit on the winner's lap and ride him until the hand was over.

Not surprisingly, this worked for everybody.

We enjoyed an awesome steak dinner and we summoned Jill for poker at 8pm. I gave her a pair of knee pads. I told her to put them on, get under the table and to wait. The winner of a hand would spread his knees apart and that would let her know who she should be sucking.

"Yes, Master."

Lou won the first hand and he spread his legs for her. A few seconds later, he had a big smile on his face. We played for two hours with Jill crawling around under the table sucking the winner's cock. I had only planned on doing blowjobs for a while, but she was sucking us so enthusiastically, that I decided to let her keep going. The guys were all having a blast drinking and smoking and playing Hold 'Em while getting blown.

Rob won three hands in a row, and as we were in the middle of the next hand, he leaned back, put both hands on Jill's head and pumped a load into her mouth.

"Sorry Bro, she's just too good too hold off that long."

He patted her head and told her she was a great little cockslut and told her to keep sucking him.

Lou won the next hand and she switched over to him. Then I announced that Jill would ride the next winner and that the blinds were being raised to fifty and twenty five dollars.

Trip won the next hand. Jill came out from under and climbed into his lap. Then she got herself onto Trips big monster. She lowered herself down and she was whimpering as she rode his huge cock.

"Wow, look at that little slut ride that big cock," said Lou.

"Yeah, this little cockwhore was born for big dick. Look at her, she's loving it!" said Marc.

She really was too. You could see all of her muscles working hard as she bounced herself on Trip's pole. We all enjoyed her moans and she came very quickly once he had himself fully buried in her. I won the next hand and she was drenched in her own juices when she climbed onto my johnson.

We passed her around the table and never let her feet hit the floor. She's a little pixie, so it was easy to just pass her from man to man. She had several orgasms and she was clearly enjoying being passed around and being called a slut and a whore as she rode our cocks.

At midnight, we all adjourned to the big stateroom to finish her off. I had Trip lie down so Jill could mount his big tool. Once they had established a nice deep position, I had Lou force himself into her ass. I told them to take turns in all of "the slut's" holes and that I'd be back in a while.

When I left, she was getting double-stuffed by Trip and Lou while alternately rooting Marc and Rob's cocks. She was learning how to be a whore very quickly.

I went up to give the Skipper a break. When he returned he told me that he was very impressed with Jill and I told him that he could have a few turns if he wanted as long as he wore a rubber. He said that he was so horny after to listening and watching all day, that he would love some release. I told him that I would send Jill up to take care of him.

I went back downstairs and Jill was now on her knees being spit-roasted between Marc and Rob. After a few minutes, Marc grabbed her head with both hands and dumped his load. I could see Jill's throat swallowing it all down as Marc's eyes rolled back in his head. He held her head and called her a good little slut as she cleaned his cock.

When he was done, I took his place and Rob and I pushed her back and forth between us. After a few minutes, we switched ends. Jill then proceeded to deep-throat Rob and basically steal his load. Once she had her nose in his pubes, he blasted off helplessly with a huge groan. Jill pulled off him for some air and then cleaned his tool for him.

The men were all sated and they patted Jill's head and ass as they left for their bedrooms and told her she was a good little cumslut.

Once they were gone, I told Jill that she needed to take a condom up to the Captain's deck and let the Skipper fuck her. When she was done, I wanted her to come back to bed and take care of me.

"Now go. I want you to suck him hard until he's ready for the rubber. Then you will roll it onto his cock and bend over to offer him his choice of holes."

"Yes, Master."

She was only gone for ten minutes.

"Which hole did the Skipper fuck you in?"

"He took my ass, Master."

"That's my good little slut. Now get ready for some more. Get on all fours for me."

She did and I lubed my big cock and fucked her ass deeply until I lost my load deep inside her rear.

"Ok, slut, clean up my cock."

"Yes, Master."

She cleaned me to my satisfaction and then I told her to go wash herself up in the shower.

"Yes, Master."

While she was gone, I changed the sheets on the bed and climbed in. Jill crawled in beside me and whispered "thank you, Master" into my ear. We slept like rocks on the surprisingly calm ocean.

I awoke to the now very common feeling of Jill's mouth on my cock. I relaxed and then wondered if I really wanted to dump a load so early. Her ministrations were just too good to put a stop to and I lay back and enjoyed a wonderful twenty minute blowjob that ended with me blasting off into her mouth as it closed around the head of my cock.

She sucked me dry and clean and then she came out from under the sheets with a big and extremely content smile.

"You are the best Master than any girl could ever have."

She cuddled up next to me and we both fell back to sleep. When I awoke, she was gone and the smell of bacon was in the air. I went out to the kitchen and found that I was the last man to wake. The guys were all seated drinking their coffee and enjoying Jill's naked body as it moved around the kitchen.

No matter what the guys said, she just thanked them. 

"Jill, you are one hot slut. I can't wait get my cock back in your ass."

"Thank you, Master Lou."

"Yeah, Jill, you give better head than any cockslut I ever saw. You better swallow all of my jizz again today you little whore."

"Yes Sir, Master Marc. Thank you."

She was still in her zone. This was some kind of internal game and I could tell she was winning. Jill made an amazing breakfast with Portuguese sausage to go with the bacon, eggs, bagels and hash browns.

We ate well. Once we had finished I told Jill to go get cleaned up and come back up top. She had a long day ahead of her. She came crawling back twenty minutes later with her leash dragging behind her. I took the leash and led her like a dog up above board to the pulpit. Trip and the Skipper were waiting for us and I wondered what Jill was thinking.

The guys had done good work lashing some floating seat cushions to the top of the bars where the bulk of her body weight would be resting. She was going to be pretty comfortable up there. For a little while anyway. Definitely better than just putting her on the bare bars, I thought.

We got her on top of the pulpit and secured Jill's hands and feet with the soft cuffs. This guaranteed that she would not end up in the drink under any circumstances.

We then used rope to secure her at the key contact points. Jill was lying face down with her head and the tips of her shoulders out over the water. Her hands and feet were fastened to the metal railing which had a curve to it which is easy to imagine if you've ever been at the tip of a boat. It bends into a thin walkway that extends past the tip of the ship. Her legs spread open right at the point where the pulpit widens. It worked even better than I had hoped.

She was in a perfect position and at a perfect height to take our cocks in either hole.

I whispered into her ear so only she could hear and asked Jill what she thought, just to gauge where she was at. 

She whispered back.

"It's wonderful, Master, but I don't know how long I will last if the water gets rough."

"Ok," I said and then I surprised her with a special toy I'd bought specifically for her fantasy. It was a very large anal plug with long hair sticking out of the end. It looked like she had a horse's tail when fully inserted.

I lubed her ass up and started to push the big toy inside her. She gasped and tried to relax as I tried to get the widest part past her sphincter. It took some extra lube and a few forceful pushes, but I finally got the massive thing into her ass. 

So nasty, I thought, and it looked awesome. Bill and Skip were both making comments of amazement and of degradation.

"Wow, that is one of the hottest things I have ever seen. I can't wait to pull on the slut's tail as I stuff her pussy," said Trip.

"Yeah," said Bill, "I am going to enjoy watching her getting abused with that tail whipping around in the wind."

Now I spoke at full volume so all could hear.

"Can you take that thing plus a big cock, you little slut?"

"Yes, Master."

"Good girl."

Jill was looking down at the water. She would not be able to hear or see any of us as we approached her from behind. And, as I said, her pussy and ass were both at a great height for us to bang away at. She was tied down very securely and she wasn't going to move much at all, which would help when somebody was grinding into her.

The game was on. This was going to be good.

"Goodbye Slut. We'll be coming up one at a time to fuck you in both of your dirty holes."

"Thank you, Master."

Before we left Jill, I reminded her that Captain Bill would be watching her make a complete whore of herself as he steered the ship. That made her even hotter.

I went down to the back of the boat where the guys were fishing. Trip and I explained the dos and don'ts as far as the way she was tied up. Under no circumstances should anybody untie anything or try to get their cock in position for head. It sounds obvious, but with all the drinking were going to be doing, who knows.

I also told them to remove her tail if they wanted to fuck her ass. And, if they did remove the tail, they should put it back when they were done.

It was up to the individual if they wanted to let Jill know their identity. There was no way she could look back given the way we had her restrained. Even if she could, she was told not to. 

I had already cum, but I wanted to make sure everything worked right, so I told Lou to come with me. I brought him up and I grabbed a deck seat to watch. As Lou stepped up behind her and lubed his prodigious tool, Captain Bill got the boat moving at a nice steadt clip that worked for the fisherman too. It was a clear day with calm water and we glided along smoothly.

Lou waited to get used to the speed a bit and then he moved in and lined up his big cock with her pussy. The lube allowed him to push in balls deep. You could see a jolt go through Jill's restrained body as she was effectively double penetrated with no warning. 

She was obviously shocked and her gasp was audible even from where I sat.

Lou long-dicked her pussy with big powerful thrusts and was talking dirty to her as he fucked her. Every now and then I heard the word slut. And I'm sure she came at some point, but her noises were intermittent with the wind and the moving boat. He pulled out, as I had asked all the guys to do, and blew a huge load up her back and into her hair. 

Very nice work, actually.

I told Lou to send up someone else and he was off. While he was gone, I made sure she was ok. She said that it was awesome and we left it at that. 

Marc came up and removed Jill's tail. Then he lubed up his manhood and proceeded to push into Jill's back door. I heard a little whimper as he entered her. He pounded Jill's ass for about 20 minutes as he talked dirty to her. When he came, he shot it up her back just like Lou. I told Marc to send up a new cock for the slut and he was off. I went back to Jill and checked her restraints and she was fine. Captain Bill had done an outstanding job. Then I picked up the tail and pushed it back into her and she moaned as it stretched her. 




Mid-Life Oasis Ch. 03



I left without saying anything and went down to fish. I passed Trip on the way and told him to have fun and to remember to replace her tail if he removed it.

Everybody, including the Captain, got a turn with Jill and she was still hanging in there. I decided a change was in order and I asked the guys if they minded taking a break from fishing. We hadn't caught squat and nobody really cared much anyway. Jill was far more interesting than anything we were going to catch.

We all went topside and set up some chairs on the deck about ten feet behind Jill. This was closer than I was sitting before, so we could hear her noises much better. I decided that it would be fun to take turns pounding her and to keep a fresh man in the saddle as much as possible. It was decided that we would all fuck her relentlessly and "tag out" like a tag team wrestler when we needed a break.

I told the Captain to take us up a few knots as trolling for fish was no longer a concern. I wanted things to get a little more intense and I figured that the scenery moving faster would speed her up inside. Now we were cruising at four or five knots, which was a big step up from the slow trolling were doing most of the morning. We were in better position to find some dolphins now too.

We each went after her in three-to-five minute spurts of pure aggression. I went first and after working my cock all the way in, I began to simply deep-shag the living shit out of her pussy. She was so tight. Her insides were swollen and her ass was stuffed with the toy. It was intense. I pulled out after a few minutes and blew my load up her back. For a man my age, three wads before lunch is pretty amazing, but that's how sexy Jill is.

Trip was right there to take over for me. He lubed his monster of a cock and shoved it all the way into her pussy on the first thrust. He proceeded to bang her with full strokes for about five minutes and it was pure animal sex. Trip held onto the horizontal bars that connected the rail to the hull and was able to pound Jill with one mighty thrust after another. Her wails were easily heard through the wind and over the engines. 

It sounded like she was feeling both pain and pleasure and that made sense given the double stretching she was getting. 

Trip kept slamming into her without letting up. You could really hear her now. There was agony in her voice as she screamed "oh my god" over and over again. Trip upped the ante and increased his intensity to full throttle and her screams continued. After about a minute of giving her every ounce of effort in his body, we saw Trip's hand go up. He was done. Fresh horses were needed. 

Marc sprang to his feet and told Trip to vacate. Marc slid his big dick right up into Jill and started to pound away at her for all he was worth. He kept this up for a few minutes and then he began to spank her ass and call her names.

"Take my cock, bitch. You are a such a dirty whore. You love this don't you."

"Yes, Master! Oh my god yes! You're so fucking deep!"

He was making big vocal grunts every time he bottomed out in her and he just kept talking to her and degrading her. Jill had adjusted to things at this point and she was now just screaming "thank you, master" and "fuck me harder" at the top of her lungs. 

Suddenly, the boat pitched and we turned starboard and picked up speed a little bit. I looked back and up to the Captain and he pointed out to sea. There were some dolphins and we were closing in on them.

Jill's reaction to Marc sent him over the top and he pulled out just in time to blast his load all over Jill's back and into the ocean.

Lou got up quickly and took his place. As he forced his big tool into her we made it to the school of dolphins. They were jumping all around her and they began to swim with us. Lou started pounding her with massive strokes and once he had a good rhythm going, he grabbed her tail and started giving it small tugs. This had the effect of moving the toy inside her ass without dislodging it. Jill has a very positive reaction to all of this and we could hear her screaming "oh my god" over and over at the top of her lungs. After a few minutes, the "oh my god" turned to "yes!" and we knew she was cumming. Lou confirmed this and told us that her pussy had gotten even tighter around his monster cock even though she was cumming all over him.

She later told me that it was perhaps the most amazing thing she had ever experienced–having a big climax with dolphins all around her.

The new snugness around his cock and Jill's wails were too much for Lou, who blasted off all over Jill's back. He swore that he got some on the dolphins too, but that's unconfirmed.

Rob was up in a flash and he was already hard. He pushed his big tool into Jill and started banging away with all the strength he could muster. 

What a sight she was seeing and hearing Jill getting royally fucked with the toy's tail hanging out of her and blowing around in the wind. A sense of accomplishment surged through me. I had managed to keep my attachment in check and we had given her all of her fantasy and more. The dolphins added an element that I hadn't planned and it was like the cherry on top of the sundae.

Rob was getting close. You could see it in his intensity and the tone in his voice and then in the content of his words...

"You dirty fucking slut! You are going to make me cum!"

I yelled out that he could cum anywhere he wanted and that apparently gave him an idea. 

"Are you ready for my nut, slut?"

"Oh yes, Master! Cum on me!"

Rob had other ideas. He pushed himself in to the root and held himself there. Then he grabbed Jill's tail and used it to pull the toy out of her ass. Once her back door was vacated, he pulled out of her pussy and forced himself into her ass. He wasn't gentle and he soon had himself buried.

Then he took the toy and reached forward and told her to hold it in her mouth and not to drop it. He was fucking her ass with slow deep thrusts and once he had his hands free, he leaned forward and used both hands on Jill's pussy. He held her womanhood open with one hand and worked her clit aggressively with the other. 

Jill was being fucked in the ass and there were dolphins everywhere now. The scene, plus the clitoral stimulation sent her flying back over the edge of climax and we all heard her mewling with the toy in her mouth as she came. It was cathartic and emotional and you could hear it in her muffled tones. It was also too much for Rob, who pushed all the way into Jill's ass and dumped his load.

Rob then took the toy out of Jill's mouth and used it to keep his nut locked deep inside her ass. Once he had her plugged back up, he stepped away and sat down exhausted.

Trip was now rejuvenated and he got back between Jill's legs and pushed his huge cock in to the hilt. He fucked her slow and deep and had a lot of fun talking to her.

"Are you enjoying this, slut?"

"Yes, Master," she said between grunts.

"Do you think I care if you are enjoying this, slut?"

"Mmmph! No, Master. I'm just a whore. My pleasure is unimportant. I am unimportant. Only my Masters matter."

"That's a good little whore. I'm going to fill your pussy with cum now. Here it comes you dirty slut. Ahhhh!"

Trip pumped a big load up into Jill and when he pulled out, a ton of jizz poured out of her pussy onto the deck.

Jill had now made all of us cum twice since being tied up plus the one go with the Captain. I summoned Bill and took over the ship as he took a final turn with our submissive. He told me that, to keep us with the dolphins, I should hold the same course and that I should not turn unless I had to. 

Bill rolled on a rubber and fucked Jill's pussy with vigor. After all he'd seen, he was blasting off in a few minutes. Before he left, he told her that she was a good little slut.

He came back and thanked me as he resumed his duties.

I climbed back down to the deck and walked up to her. I leaned in close and asked her how she was. She told me was sore but that she was cumming so often she had lost count of her orgasms.

I decided to give her a g-spot massage before taking her down. I stood behind her and lubed up two fingers and pushed them into her with my palm facing down. I found her spot and worked it hard by curling my fingers as I stroked her. After a few minutes of this, Jill went rigid, screamed and squirted into the sea and onto the deck. I went back at her for another minute or two and she clenched up again, screamed and released another stream of cum.

She was now panting and totally limp with her head rolling from side to side.

We cut her down and I helped her to our stateroom. 

I helped her take a shower and told her to rest up for a few hours. She was really stiff from being in one position for so long.

It was 2pm when I left her sleeping and I didn't go down to wake her until it was time for dinner. She was actually awake when I came in. She gave me her usual big smile as she rolled up onto a seated position on the bed.

"Jill, dinner is going to be ready in a few minutes. We can be done for the weekend now if you want or you can keep taking care of the guys. You've already gone beyond my wildest expectations, so feel free to throw some clothes on and come up as yourself and not as our sex slave."

"What does my Master want?"

"Your Master is completely satisfied, but only you know how the fantasy should end."

"Thank you, Master."

"You are a very good girl and a very good slut. You have made your Master very proud. I'll see you up on deck. We'll be home in about two hours."

I left and headed upstairs. The guys had dinner ready to go and I opened a nice bottle of white wine for Jill. 

A few minutes later, she came crawling up the stairs wearing nothing but her collar, leash and tail. What a vision of perversion she was.

"Master told me that I can keep fucking you studs until we get home."

Hoots and hollers came from all around as even a depleted man would be nuts to pass up a chance with Jill. She came over to me and crawled into my lap. 

"Master, is it ok if I skip dinner? I'd rather suck cock."

She wore an amazing devilish grin as she said this.

"Get to work you little cockwhore."

She retrieved her knee pads and crawled under the table. I saw all the guys trying to drop their shorts as they sat. Wiggling everywhere.

From under the table, we all heard Jill say "ok, who's ready?"

I'd already blown three loads including my morning blowjob and I planned on blowing one more right before I went to sleep later that night. She could suck me, but she wouldn't get my nut.

Marc started moaning and we all knew who she chose. She was obviously doing good work as he looked down at her and gave her the degrading talk she loved.

"That's it. Yeah, suck my cock you fucking slut. That's it. That's it. Take it deep you little whore. Oh yeah. You are such a dirty little slut. Keep it deep. Keep it deep. That's it. Yeah. Work for my nut you little cumslut."

Jill was moaning louder and louder as her degraded her. There was a desperation in her tones. She was really putting on a show or maybe it was genuine. Either way it was insanely erotic listening to her.

After another five minutes of great head, Marc put both his hands on Jill's skull and held her on his cock as he unleashed his final wad of the weekend.

"Yeah, swallow it all, slut. That's a good girl. Now clean me up you dirty cumbucket."

She was moaning sexy moans as she finished him and Marc was rolling his head as he could barely take the post-nut stimulation.

A minute later, Lou started moaning and we knew she had switched cocks. Lou is a fucking character and he just kept eating as Jill sucked his big cock. He was talking to her with his mouth full and that seemed to add a air of condescension somehow. 

"That's it, slut. Yeah, suck my tool while I eat my fucking steak. Does my meat taste good, bitch?"

Jill's moans of affirmation could be heard but she never took her mouth off his cock to answer.

"Yeah, you sure do suck a good cock don't you, slut? Yeah, keep it up and don't stop. I'll give you my nut when I'm good and ready. You hear me, slut?"

More affirmative moans.

We all sat and talked about how much fun we had fucking Jill and the guys were very descriptive as to what they enjoyed the most. We knew she could hear us, so we made sure to talk about her like she was just a whore. Her continuing moans told us that she loved what she was hearing.

After about twenty minutes of head, Lou grasped Jill's skull and unloaded without warning. She swallowed it and Lou complimented her and patted her head as she made sure he was clean before she went to the next cock.

"That's a good little slut. Goooooood little slut."

Everybody had finished dinner, so I said we should take our party up top. Once we got settled, I told Jill to get up on my lap and ride my cock. She did and I had no trouble getting hard. I told her to do all the work and we all watched as she used her leg muscles to ride my big tool. She was really something to watch. From the guy's perspective, she was back-lit by the sun as it started to set on the clear horizon. 

She rode me like her life depended on it and we were all a bit maudlin a minute later when we saw land in the distance.

We were now fifteen to twenty minutes from home. I yelled up to the Captain to slow down and buy us some time and a few seconds later the boat slowed perceptibly.

I stood with Jill still on my cock and told Rob to hold her open for Trip. We passed her from me to Rob and finally to Trip as he entered her and took possession. Then we passed her back and forth for a while and moved her from cock to cock. She rode each of us four or five times and then I told Trip and Rob to DP her and to fill her holes with their seed.

They moved to the middle of the deck and Rob moved in behind Jill and pushed his big cock into her ass. They power-fucked my little sub with long hard deliberate strokes until she started to buck, convulse and whimper as an enormous orgasm overtook her. Both men pushed in balls deep and pumped their loads into her orifices as she continued to whimper and moan.

They dropped her to the floor with care and then she cleaned all of our cocks. I was still saving my last load for later on.

"Jill, your weekend as our whore is now over. I think we'd all like to thank you for being a simply amazing submissive for all of us these last two days."

All the men loudly agreed and she was given a round of applause. I told her she could go clean up if she wished and that she should probably wear clothes when we walked home from the boat house.

She crawled out of sight and returned ten minutes later on her feet with a tank top and bikini bottoms on.

Captain Bill was getting paid to break down all the equipment and I gave him a generous tip which he tried to give back. He felt that his three turns with Jill was more than enough as far as a tip was concerned. I told him that, though he was right, he was still getting the tip.

I gave him an extra grand for all he did. The man only slept about three hours over the two days. He earned his money and he was worth every penny.

We all walked up to the house and headed over to the garage, which was located below the part of the deck that wrapped around front. The guys were all going to hit the road as they still had significant travel ahead of them. 

My driveway is very private once you get to the parking area, so at my suggesting, Jill wiggled out of her bikini bottoms and tank top to say her goodbyes. She gave each of them a hug and a kiss. They all gave her a squeeze or two and told her how special she was and how much they wished they could do this all the time.

Lou whispered something in hear ear before kissing her cheek and driving off. I asked what he said after they had all left and she was hesitant to answer. I gave her a look that reminded her of her place in our current relationship.

"Master, Lou told me that you and I are the perfect couple and that he wanted me to take good care of you. He said he thinks we'd be great for each other."

Now I realized why she didn't want to divulge the content of his words. This was the first truly awkward moment in our offbeat union. The deepening bond between us was like the elephant in the corner of our relationship. 

I knew I was in love with her already. 

It was love that made me allow her the fantasy we'd all just experienced. As much as it felt weird to watch her get fucked, I understood the context of the event. Now that it was over, I wanted to give voice to my true feelings and Lou had left me an opening.

The fear of rejection was palpable and I did not want to risk the last few months that she already promised to me. If I professed my love, it might go unrequited and that imbalance would surely kill the golden goose.

This was suddenly one of the bigger moments in my life and my breath was uneven as I struggled for adequate words. 

Jill spoke and she saved me.

"Master, don't say it. You don't have to. We both know something's happened and for now we should enjoy this great relationship and keep things as is. We have plenty of time to contemplate our future, but let's not mess with the present. I'm enjoying being your submissive too much right now to be anything else."

I was astonished that she, as usual, seemed a step ahead of me. I went with it.

"Good enough, Jill. I think I'm going to get a shower. You should do the same. And hurry. I want you naked in my bed when I get out. And wear your tail you dirty little cumslut."

"Yes, Master."

When I came out of my shower and entered the bedroom, the first thing I saw was her ass and tail. I lubed up my tool and took her pussy, which was tight as all hell with that big toy stuffed up her ass.

I fucked her hard and deep and tried to get myself off for the fourth time in fifteen hours. Jill knew my dilemma. She reached back and gently fondled my balls as I slammed in and out of her.

"Fuck me, Master. I love your big cock so much! Make me your whore and fill me with your seed!"

That did it. I thrust in to the hilt and sprayed her insides with my load. We fell asleep together.

More to come...