Thanks for reading. All characters are 18 or over, and this work is purely fictional. It involves brother/step-sister incest. If that is not your thing, feel free to click away! I wrote this story for myself, but hope you enjoy.
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It was tough not to thrust my hips some more and dump my goo in Ashlynn Luker, one of the damn-sexiest pieces of ass I'd ever had, and the fact I was paying for that ass made it somehow even MORE erotic, stepsister be damned!
Now, I knew Ashlynn was not dumb. She knew the deal, knew what was expected, and I figured she was okay with it. Her willingness told me she felt safe to do this. As long as I went slow, it should work juuust fine. "Okay, sweet, I'm going to go slow here," I said. I slid the 'mighty mushroom' down, between those cheeks, and feeling it nudge against that cinnamon ring, I applied just a bit of pressure.
"Oh-Oooooh.." Ashlynn said. Her ass was straight up, but she was bent over, and looking back at me. She nodded encouragingly.
With my left hand, I held her left ass cheek, and pulled out just a bit, while the right hand was palm down at the bottom of her spine. Steady but slow, I pushed, and felt her anal ring give.
"Ooo-OOH!" Ashlynn said. She looked back, remained still for a moment, and again she nodded.
I was absolutely okay with letting her think she was in control of this. The idea I had planted in her head was going to make this possible; I was sure, so again, I pushed forward. I felt her lower back push against my palm, as her face reddened a bit and her brow furrowed, but I held her still. 'The door to the club' was opening, and with a final 'pop' of sorts, the old mushroom head popped right in.
"Ah--AHH!" Ashlyn called out. I'm sure it hurt, but she remembered to push back like she needed to poop. She did that and finally, that dick she liked so much, was in a new place. She held her hand up for a moment, thankful that her 'benefactor', as she preferred to think of him, held still. It felt like more than just the head was in, so Ashlynn concentrated on allowing her asshole to accommodate him.
She was breathing heavier now, partly from the pain. It's not like she made a habit of putting anything in her ass, much less a thick dick like mine. She had to know I wouldn't stay still for long, so I liked that she reached down and began to stimulate her clit using her fingers. It must have felt good because she picked it up, and I took that as my cue to move.
I had not quite half of me buried in Ashlynn Luker's gorgeous, bought ass. Slowly, I began to p-u-m-p, moving back, then in...back and then in. My woman was doing her best to take it, and after just a bit, I was up to the really thick part of my shaft, but I could tell it hurt.
Ashlynn held her hand back to tap my hip, saying "Oh-Gah Bae...slow...easy, Bae...."
I was ready for this. I knew the Anal-Ease would only do so much. Stopping, I reached over--causing her to utter a satisfying grunt--and from under the pillow I pulled out 'our little friend', Mr. Hitachi. Ashlynn looked back at me and smiled, as she flipped it on and put it to work.
Ashlynn looked like she was trying her best to like taking it in the ass. I was sure that part of her liked submitting like this, but the pain would be the deciding factor. The Hitachi was doing its thing, and when applied to her clit, it was like science or something, because I could tell the wave was building.
"Ba-Bae? I...I thi--Think..." she was trying to tell her man that she could cum, but the real truth was she was stuck somewhere in between the pleasure being applied to her clit, and the fucking city bus working its way deeper and deeper into her ass.
I was at least three-quarters of the way in now. Ashlynn had gone from pain, to moaning like an orgasm, to somewhere in between. It was good for me, too. I knew I wouldn't be able to do much more. Her colon was like a silky glove, and it gripped me, TIGHT. Each time she gasped, it squeezed me and were it not for that tight ring gripping my base, I would likely have shot my goo long ago.
It wasn't that I was in love with Ashlynn, no. But I did care for her deeply; it's hard not to, for someone like this, bought or not. And now, I could feel the need to dump my goo. That urge was taking over, so I began to thrust into her harder. I cared bery much for this woman that was going to let me shoot my load in her ass--plain and simple.
I told her, "Cum" --pump-- "for me," --pump-- "Bae..." --pump-- "Cum..." I was absolutely balls deep at long last.
"I-I...I'm try...I'm...Ahhhhh," Ashlynn answered. Then all at once, I could tell she let her final guard down, and bus in her ass or not, the wave was released. "I -- AHHHHH!!!" she screamed.
When Ashlynn finally orgasmed with me in her ass, her butthole and whole rectum, started tensing on me so hard; it was like her ass was giving me a hand-job. I heard someone making a high-pitched little-girl scream...Oh shit, it was ME!
When I realized that, I was too far gone, and I proceeded to cum so hard, MY butthole tightened up, and I dumped every single thing I had in me into her. I orgasmed so hard, the lines on the bottom of my feet went smooth, and had it not been for her butthole clutching, I would have popped out and fallen over.
Afterward, I collapsed on the bed, and Ashlynn fell over beside me. We just lay there wheeze-panting loudly, both of us staring at the ceiling. I finally managed to speak with a quiet, "Holy shit!"
Ashlynn chuckled and responded with, "I think you broke my asshole, John."
We both lay there together, laughing hysterically, enjoying the moment of the shared incredible orgasm and just being together.
***
For the next two weeks and then some, I was tied up in court and with general work, and was not getting back over to St. Georgina. On a Thursday, I sent Ashlynn a text, "Check your Cash App, sent you a bit just for 'cause I can."
Ashlynn understood the relationship and where it was going, but at the same time, she appreciated that he thought of her like that. She was in her room with the baby, and trying to get her to lay down. Once she had her settled, she cooed quietly, "I'm not going anywhere, rest."
With the kid's eyes closed, Ashlynn dropped her shorts to just under her butt, and leaned forward. Looking back at the mirror, she got a pic of her thong disappearing in her fanny crack. You could see her dark pussy in the light-colored panties, and she texted it to Johnathan, with the caption 'something misses you.' Then, she, too, settled in for a short morning nap.
Ashlynn and the baby met Clara for lunch over at The Parrot, it being 'the spot'--actually the only one of consequence on such a small island. Ashlynn started the conversation. "So, Clara, how has the arrangement site been working? Or should I ask, 'How's business?'"
"It's been okay," Clara commented. "Here, it's mostly old fat guys or middle-aged pervs cheating on wives with quickies, but recently, I've done a lot better where the population is, well, a bit larger."
"Oh?" Ashlynn asked, her suspicion raised, "do tell."
"Well let's just say that lately, I've been able to meet with this one john that really knows how to push a girl's buttons. Tips well, too. Like REALLY well."
"Up in Tally, or over in PCB?" Ashlynn asked, now more interested than ever.
"Hey girl, not giving up my find here," Clara responded. "Besides, from what I've seen, you have either landed one big whale, or two smaller ones."
Ashlynn smirked, "Oh, I've got a tiger by the tail all right," she responded, "just hoping it holds up a little longer until I'm off to school...and mine's nearby."
