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...