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This is a work of fiction, and any resemblance to real persons or events is unintended and purely accidental. Intended for mature (50+) audiences. All characters are over 55. This story contains scenes of incest.

This story is part 3 of a series. If you haven’t already done so, it is best to read Chapters 1 and 2 first to familiarize yourself with the characters. As there is no story category for bisexual male/MMF, it is here in the Gay section. Hope you enjoy.


Chapter 3

Journal Entry Sunday, May 2, 2010

What a great day the first of May was for us yesterday, followed up with the finale to end all finales this morning.

We set aside the whole afternoon to have some fun with my wife’s younger brother Kenny, who brought and made lunch for us. It was great – none of us felt rushed to get into anything, and we talked a lot about our individual fantasies. He also brought along his sidekick, ‘Moby Dick’, the large and apparently very expensive life-like phallus supposedly modelled after some porn star I wouldn’t want to meet in a dark alley.

Well, maybe I would like to, but I digress..

I knew damn well that I was going to lose my anal virginity that day to Kenny, one way or the other, so I had prepared accordingly. And that is the first thing that came up in our afternoon agenda after the lunch dishes were cleared.

Kat took the floor, vocalizing her wishes right off the bat.

“I’ve been so looking forward to watching you getting your ass properly fucked, mister macho man,” she said, looking right at me.

I, like so many other married men out there, had often lobbied to do just that to Kat’s pretty little ass, but she was understandably reluctant to go there.

“Hey, I’m man enough to admit I would love that too,” I snapped back. “But how about you? What can we do for you that you’re in the mood for today?”

Kat had been using some really expensive cream prescribed by her doctor to try and revitalize things ‘down there’, and with success, I might add. With Katy pushing sixty, and Kenny and I not far behind, we need all the help we can get.

“I just want to watch . . for now anyway. Maybe later, I’ll see if Moby over there will fit in my strap-on harness. How about you, Kenny? You looking for anything special?”

“Your hubby’s ass! And if that dick fits .. maybe I can find a place for you to put it.”

We all seemed to agree on the number one priority of the day.

“I’ll see if I can find that harness,” Kat replied exuberantly, before disappearing into our bedroom.

“You still sure you want to go through with this bro?” Ken asked, suggestively stroking himself through his shorts.

“You’ll have to take it easy on me Kenny, I’ve never had anything much bigger than a dill pickle up there.”

“Don’t you worry about a thing. I’ve got a plan,” he said, placing his hand on my shoulder.

“Man with a plan! That’s my bro!” Kat exclaimed, returning with her dick belt securely fastened and adorned in her powder-blue baby-doll lingerie. She grabbed Moby, and sure enough, it did fit in her harness.

“Put it on sis!”

“Ok, I’m working on it.”

The thing was so heavy, it hung down obscenely between her legs.

“Wow, I don’t know how you guys can walk around with these things,” she astutely observed.

“Our cross to bear,” I replied sarcastically.

“OK, who wants it first?” She said, waving it at both of us.

“Get away from me with that thing!” I hollered.

“Maybe you can take me after I take your hubby,” Ken suggested.

“Well what are we waiting for?”

“Lube, that’s what. And lots of it!”

“Got that too,” Ken said, pulling it out of his sack. “Let’s get this show on the road, shall we?”

“Follow me,” said Kat, leading us back into our bedroom, Ken and I shedding our clothes along the way. Her seductive appearance, dressed so sexy but adorned with that extra equipment dangling from her crotch, gave both Kenny and I instant hard-ons.

Kat took charge immediately.

“Lay down on your stomach, just like Kenny did.”

I eagerly complied, making myself comfortable and placing a pillow under my hips, to elevate my ass and make it more accessible to any and all takers.

“You know what to do,” she said, looking at her brother, while she stroked her ever-hard Moby Dick like it was her own flesh and blood.

And Ken sure did. For the first time in my life, I felt lips and tongue working their way into my hole. It was more sensuous, more stimulating that I had ever imagined it would be. We have so many nerve endings there; what a great place to practice the art of loving. It almost tickled, but in a very good way. I could feel the arousal in my hardening member, albeit jammed into the pillow beneath me.

Ken spread me with his fingers, and pushed his tongue into me as far as he could. I pushed back, trying to open up more for his probing efforts. Meanwhile, Kat slapped that big dick of hers on my neck and shoulders, Demetevler Escort maneuvering her way up to the head of the bed.

“Let’s see you suck on this thing, slut-boy.”

Well, I could barely get the head of it in my mouth, but I gave it my best, as Ken’s fingers started working their way into me. He had obviously spread lube over me while I was preoccupied, as it was beginning to feel quite slick back there.

Suddenly, he hit ‘the spot’ that made me jump – it was my prostate, and he was massaging it, with lord knows how many fingers inside me.

Kat had my head in her hands and was forcing even more of that monster into my mouth, and I truly felt like a slut. I wanted even more, but that thing seriously would not fit without splitting my lips at the seams.

Kat must have felt my pain, as she withdrew it from me and moved back to the foot of the bed.

“How is slut boy doing there – opening up nicely for you?”

“Mmm, sure is,” Ken replied. “I think he’s almost ready for a hard cock.”

“Get up on your knees, baby. Your time has come,” she ordered me. I complied without hesitation, sticking my rump up in the air.

I heard Kat sucking and spitting on him, getting him stiff and slick.

“Tell me you want it Jimmy boy.”

“Fuck yeah, I want your cock up my ass. NOW.”

“Just relax and breath. And push out when I say.”

Then I could feel the warmth of his shaft run up and down over me. I don’t think I ever wanted anything so bad as I did just then.

“Do it Kenny. Please.”

“Here it comes, bro.”

I stopped breathing for a few moments as he gently pushed, and I could feel the head of his penis just breach the first ring. I moaned like a twenty dollar whore in heat.

“OK, now, push against me,” he said.

I knew exactly what he meant, as I had felt him do that when roles were reversed earlier. But it felt so good with him there like that, I hesitated.

“Just give me a moment,” I begged.

“Of course. We’ve got all the time in the world,” he said.

After about ten seconds, I pushed back, and his cock was in. But oh, what a stretch I felt.

I panicked a bit, but Kenny kept me cool.

“Breathe, bro. Deep breaths. I’m not going to move until you tell me.”

Kat affectionately stroked the sweat from my face, and laid down by me. We kissed for a while, as I relaxed into it more.

“You ready for more?” Ken asked.

“Slow, nice and slow,” I replied.

Gently, he eased into me the rest of the way, until I felt his balls touch mine. He was all the way in – and it felt amazing! A fullness I had never experienced, but knew from that moment forward, I would forever crave.

“FUCK .. you feel so good in my ass, Kenny!”

In and out, slowly at first but gradually picking up speed, I felt every vein in his shaft massage my anal walls. His warm, wonderful, loving dick stroking me, fucking me, throbbing inside me; I could even feel his heart beating through my anal wall as he made love to me as no other had before.

So self-absorbed was I that I lost all track of where Kat was or what she was doing. Kenny had picked up the pace, and I could feel my prostate throb each time he bottomed out in me. I wish I could say that it lasted longer, but after five or ten minutes Ken was almost at the end of his rope.

“Oh fuck, I’m gonna blow . . I’m gonna fill your ass with cum bro!”


That was when I felt the warmth of his seed fill me, tingling inside me like a thousand microscopic fingers. I felt him spasm several times, then his fullness inside me receding. We were both panting and sweating profusely.

In a few more moments, he slipped out of me, and excused himself to the shower. I just remained as I was, laying on my stomach, enjoying the afterglow of losing my virginity, yet at the same time regretting that the time had been so short. It was as though I just got used to him, and then he was gone.

Kat was stroking my back and ass, her presence suddenly becoming evident behind me in my altered state of euphoria.

“You look so happy there, baby, but his cum is leaking out of your ass and onto your pillow.”

It was then that I felt her fingers – and that big dick she was wearing – pushing Ken’s creamy load back inside me. I thought to myself that I could never take anything as big as that monster dick inside me.

“Fuck, baby, I don’t know if I can ..”

Kat interrupted my pleas with yet another, firmer push into my gaping hole.

“OH..” I involuntarily blurted in reply to Kat’s bold intrusion. She had broken through my first line of defence, the outer sphincter, and was drilling for more. And now that she was part way inside, I wanted more.

Ken emerged from the shower, and chortled at the sight.

“I knew you could take it, bro. Give it to him Katy. And try and stay hard for me later!”

“I can stay this Otele gelen escort hard all day long,” she replied sarcastically, rocking her hips just a bit.

“Here, lube that thing up some more. Remember, this morning he was a virgin.”

The sensation I was feeling was like someone trying to shove a greased baseball bat up the wha-who. But my ass was indeed surprisingly game for the challenge. The veiny protrusions were even more pronounced with Moby; while Ken’s penis was pliable and alive, this thing gave no quarter.

Now I could feel the stretch even more, and started moaning loudly as Kat, and her coach Ken, worked that thing up and into me even further, breaking through my second sphincter. Their chattering was almost foreign to me, I was so concentrated on the feelings of being stretched beyond any previously known limit.

“OK, in and out slowly now,” Ken urged his sister.

I almost dared not look back, but relented to my curiosity as I became more accustomed to my anal intruder. Ken was standing behind Kat and they were joined at the lips. He appeared to have his hands on her appendage, working it in and out of me with increasing depth and frequency.

I placed a clump of pillowcase in my mouth to muffle my loud groans and moans; I really couldn’t help myself as they worked that dick in and out.

“I’m gonna need a break soon,” Kat declared. She was obviously not used to ‘topping’ like this for any extended period.

Ken offered to take over, slipping Moby from Kat’s harness, and, grasping it by the suction cup end, began thrusting it in and out and moving it around. It actually felt better that way, as he varied the angle to find where it provided the most stimulation for me.

“This is how you do it,” he said, demonstrating to Kat the finer art of sodomizing a man.

“Are you guys having as much fun as I am?” I asked rhetorically.

“Oh yeah, I’m getting the hang of this now, no pun intended,” chuckled Kat. “Be a good bitch and take that dick, baby,” she added with confidence, being more forceful in her thrusts now, and using the large tool at her disposal with more confidence and assertiveness now.

Leaving his sister to her own devices behind me, Ken crawled onto the bed and slid underneath me in a sixty-nine; I welcomed him by burying my face in his crotch. He must have propped his head up on a pillow, as I now felt my balls engulfed in his mouth.

Talk about over-stimulation! The scent and taste of Ken, his long dick plunged down my throat, him doing likewise to me, and a monster cock plunging in and out of my super-dilated ass. I couldn’t even warn him when I released my seed into his mouth. Shortly after, he too finished in my mouth, and I drank him down as fast as he could feed it to me.

Ken took hold of Moby from Kat, and held it all the way inside me, as we slumped to our sides on the bed.

“Remember bro, you still got my first load up your ass.”

With some degree of difficulty, I maneuvered my way off the bed and into the shower, holding the rather large appendage inside me along the way so as not to leak cum and heaven knows what else onto the floor.

I succeeded, and got myself and my attachment all cleaned up. I was gaped enough to almost put my whole hand up my ass, I remember thinking, as I stood beneath the warm shower spray soaping myself up.

Kat and Ken had relocated to the kitchen and were enjoying a large glass of her home made lemonade when I emerged. I felt sorry that Kat had been sort of ‘left out’, and told her so.

“What do you mean? Of course I came – while I was watching you get fucked!” She replied.

“Oh, well shit, I guess I must have missed it,” I thought, scratching my head.

“You were a little preoccupied, slut boy. You were groaning so loud you probably never even heard me.”

~ ~ ~

We sat around and rehydrated for a couple of hours, yakking about life in general and our plans for the rest of the weekend, as we would have otherwise done in our ‘normal’ day-to-day lives. When the four o’clock hour rolled around, we each cracked a beer and began discussing our sexual bucket lists.

It wasn’t long before Kenny reminded us of how much he would love to get fucked before he left. My loins were stirring again, so I was about to make him an offer, when Kat piped up.

“Why don’t hubby and I take turns on you?” Kat suggested. “I kind of like my new equipment, now that I know how to use it.”

Well, you never saw a pair of pants come down so fast in your life.

“Who want a piece of me first!” Ken cried.

“Let me open you up first,” I recommended.

“The voice of experience?” Ken smirked. “Give me ten minutes in your shower first, then you can take turns on me.”

Kat propped up pillows and laid out towels on the bed while I assembled the goods – the lube, the harness, and of course good old Moby Dick.

When Ken emerged all squeaky clean, Kat took charge. Balgat Escort

“Lay here, with your legs off the edge. That way we can take you standing up. My knees can’t take much more.”

I helped Kat into her gear, then gave Ken a good smack on his right butt cheek.

“You ready there, sport?” I asked.

“Oh yeah. Give it to me good.”

I leaned down, just as I had before, and slurped away at his rosebud. It was almost second nature to me now. I probed with my tongue, then added fingers, and was amazed at how quickly he just seemed to open up.

Kat seemed mildly interested, and moved in closer to watch me. That made me wonder . .

I turned to face her and mumbled something about being a messy eater, and she planted her lips right on mine, sharing the taste of her brother’s ass on my mouth.

“He tastes good, doesn’t he,” I said, breaking off the lip-lock.

She looked at her brother’s pucker, then back at me, smiling.

“Mind if I try too?” She asked.

“Be my guest,” I said, pulling out the three fingers I had buried in him.

Well, she took to it like a poodle on a pork chop, burying her tongue inside him then licking all around his puckered star. I stood up and held my semi-hard penis close to the action, and she took the bait, going back and forth between the two of us. Ken just kept moaning into his pillow, oblivious as to who was doing what, only knowing how good it all felt.

Kat finally let me have the last licks at him before I finished prying his hole sufficiently open to receive his due.

“You must have taken a lot of Moby up here,” I commented, surprised at how big his asshole really was.

“I think I am gonna need to upsize Moby soon,” he replied.

That gave me an idea that I filed for later.

Now fully engorged again, I got the lube and Kat helped spread it on both of us, while I took care of slicking down her appendage.

“Say AAAHH” I quipped, just as I pressed against his opening. I slid in with no resistance. In fact, it was like he swallowed me up. I glided in and out of him with relative ease, and his ass muscles felt good on my cock, expanding and contracting in rhythm with my thrusts.

Kat watched intently, seemingly mesmerized by the sight of the two men closest to her engaged in such debauchery. This was the second time I had fucked Kenny, and it seemed to go much easier this time, as we read each other’s body language. I instinctively knew when he wanted more, and conversely, when he needed me to slow down.

We were getting rather good at this!

Wanting to get Kat in on the act, I reluctantly withdrew and motioned her closer.

“Your turn!”

I moved just off to the side, and watched her push her way in. And what an erotic sight it was. That thing looked so damned real, hanging off my lovely wife.

“I think he could take both of us up there,” I joked, slapping his ass again.

“Fuck . . YEAH . .” Ken moaned, seemingly off in another world.

Kat went at him rather briskly, probably payback from some long-ago brother-sister feud. But he took it well, and actually asked her to fuck him even harder if that were possible, which she did her best to do. After a couple of minutes, I could see her slowing down though.

“Time to switch!” I said, right there to take her place. I knew she was getting tired.

Now, I’ve done a lot of fucking in my life, and these hips were built for hard thrusting. So I gave it my all and gave him a real good pounding. He muffled his now more intense groans into a pillow but never asked me to even slow down, let alone stop. I’d already cum once, so my staying power allowed me to go at him for quite a while before I ultimately succumbed to the feeling.

“Gonna fill you up, bro!”

“DO IT!” He cried, clamping down even harder on me.

That did it, and I exploded inside him, painting his throbbing bowels with my hot seed.

I slumped down on top of his back, panting, not wanting to withdraw from him. But it was not long before nature took its course, and I unceremoniously popped out.

Kat had pulled Moby from her harness and handed it to me.

“Maybe you should plug him with this, so he can get to the shower.”

I took it from her and shoved it home.

“Maybe you both need a shower,” she astutely observed, as I dripped a mixture of lube and cum onto the towel below.

“I think maybe you’re right..”

~ ~ ~

Ken and I helped each other clean up, then I took a load of bedding down to the laundry room in the basement and started it up while the other two headed for the kitchen for a beer.

When I returned, they were talking about poor Kat being the odd one out again.

“Hey, I’m happy, I got my wish. And I know you guys are pretty well fucked out for today. But I have a proposition for you, if you’re interested.”

Kenny and I were all ears.

“Tomorrow, I want to be pampered, then I want to try to take both of you at once.”

“Wow, Kat, that’s a big step. But if you think you’re ready, I am sure we can make that happen. How about you, Kenny, you into it?”

“You just tell me what time to be here, and I’ll be here with bells on.”

~ ~ ~

The ‘pampering’ Kat referred to was to sleep in, have a nice breakfast, followed by a warm bath, with two gentlemen to cater to her every wish.

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