Buying My Step-Sister Ch. 06

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."

"Well I've been enjoying my time in PCB," Clara said, "he's been good for an older guy."

Right then, Ashlynn knew Clara was lying. Clara's ex lived over in Panama City. He was so violent she had a restraining order against him, and there was no amount of money that could get her over there, so that meant, she was sure, of just one thing.

Ashlynn knew the deal between them, but at the same time, she needed to know. So with only a little prompting, she got her mother to agree to keep the baby that evening and the next day. This time, she didn't grab a small bag of anything; she headed northeast on coastal highway I-98, straight to the capital, and straight to the apartment.

***

I was expecting a relaxing evening, but instead, Ashlynn appeared on my doorstep. She hadn't made an arrangement through the site; plus, she seemed to have a bit of an attitude as well, so I figured something was up--and I also had a pretty good idea what it was.

"Have you been fucking Clara?" Ashlynn asked, with an irritated tone.

"I didn't think what you and I have been doing was considered exclusive," I replied. "In fact, I told you to be evasive, but not exclusive."

Ashlynn turned her head and looked away.

"So besides today, and the time you surprised me, that would be the only two times you have even been in this town." I then added, "I seem to recall your ex being here and that was a major reason you don't come up here."

"Well, that is true," she admitted, quietly, "but, you gave me good reason to drive up here."

"Well, I didn't know you'd take that risk, so I used someone from the same site I found you on; it just happened to be Clara." I knew that sounded pretty innocent, and the fact she didn't slap me made me think she accepted it. "Also, one of us is about to go off to school."

"Also true," she said again, "but, so will Clara."

"Okay, but look Ashlynn, you're not being replaced or anything, I thought the deal we have had has worked very well, so let's not go goofing it up. Are you okay with that?"

Ashlynn nodded, and went to the bathroom. While she was in there, I sent her a meeting request through the site.

Ashlynn came out of the bathroom, and said, "Well, someone sure thinks a lot of themselves."

"Hey, I figure I'm here, you're here, my boner's here, so why not?"

Ashlynn shook her head, as she felt him step in close. She knew where I stood on this, and from her reaction, appeared to be good with it. In fact, I was sure she knew I was right, and that wasn't a bad thing, was it?

I stepped in close, and gave the hem of Ashlynn's shirt a tug. She slapped my hand away.

"How do I know you haven't already gotten some from Clara?"

"Because up here, work is a fucking dredge. I normally work twelve to sixteen-hour days. Can't blame a guy for taking the edge off," I said, as my tug brought success, and Ashlynn pulled the shirt off.

I reached for her bra again, and again, she slapped my hands away.

"I can't help but compare myself," Ashlynn said, "I've known Clara since we were kids, but that doesn't mean she's a BFF or anything, not by a long shot."

"Look because you're asking, I'll tell you. Clara is 'different'. Fun in a certain way, but not my normal thing. And before you ask, let's just say she REALLY likes being submissive, even enjoys it with some humiliation mixed in, and none of that is you."

I reached for the middle of her bra again, and Ashlynn leaned back on her hands and let me unsnap it. It was a nice, little baby-blue number with white lace, and latched at in the front, so it flew open, and I started to fondle her nice breasts. Ashlynn's mouth dropped open, as I gave that pert little nipple a twist.

"I have to say, you do have a certain way..." Ashlynn said, with a light moan in there, as well.

I sucked that nipple and teased it a bit, before tasting the other one. I pulled off of 'em when they were sticking out nice and hard. Her eyes were closed. I wanted to kiss her, but decided to go with something else.

I had the right motivation, so I stepped right out of my pants, and in peeling off Ashlynn's pants, I also took the waistband of her panties and pulled them down to her ankles. She lifted first one foot and the other, as I was on my knees on the tile in front of her, her back against the marble counter.

Her pussy was right in front of my face, and so I gave it a big wet kiss. Damn it smelled good and tasted sweet.

I heard her inhale sharply when I did, so I ran my tongue up her slit to her clit. I started flicking my tongue on it, just as fast as I could.

"Unhhhh!" Ashlynn croaked softly, "Uh...you do have that way....!"

I enjoyed licking every inch of her pussy. It wasn't too long before she had a hand in my hair, mashing my face to her twat, soaking my goatee in her juices. I lifted her by the hips and sat her on the low part of the marble counter in front of me. She let me push her legs apart and put her feet on the counter, so she was wide open leaning back on her arms with this glassy look in her eyes.

"I think you like my cock."

Ashlynn bit her lip as she nodded emphatically. Her look was glassy eyed, but excited. As I rubbed my dick on her clit, she moaned and tried to push it down, but it was my turn to slap her hands away.

"Tell how much you like this cock," I said, and continued to rub it on her slit.

"I've -- oooh -- I've always liked how it feels, as it goes -- ahhh -- inside m-me..." she said, and reached for it.

Again I slapped her hand away. "Is that all?" I asked, continuing my fun.

"I REALLY want that cock, Bae..." Ashlynn cooed, "I love the way it fills me up, come on..." and as she pushed it down, Ashlynn shifted her ass. It was like an unstoppable force, that pussy, and it sucked my cock right in.

As soon as it was in, I started pumping that pussy, and I pumped it HARD. With the wonderful 'schlack, schlack, schlack' sound of my dick going in and out of her.

"Unnhhhhhh!" Ashlynn moaned, and both legs went up in the air around me.

"Yep, I knew you liked it."

This position made Ashlynn's pussy feel even better than ever, and I wanted it to last. So, I slowed to a stop, looked her in the eye as her mouth hung open, and then I started to hump her nice and slow.

"Oh, ohhhh, unhhh!" Ashlynn groaned, as she shook her head, and her legs wrapped around my waist. I could feel her bare heels as she crossed her feet and locked them tightly around me, like I was going to go anywhere except where I was fucking her.

I kept my hands under the small of Ashlynn's back, on the counter and loved how tight her pussy felt on my mushroom head and shaft, when it was all the way inside her. Ashlynn's head went back and bumped when she hit the cabinet. Ashlynn grinned, and she put her arms around my neck to hold herself in position. Her face was just inches away from mine. Ashlynn's eyes were closed, and she was moaning softly with her mouth part way open.

"Ashlynn your pussy feels so fucking good!" I whispered, and pushed my cock all the way in again.

Ashlynn's head dipped back, and she let out a long moan. I couldn't take it -- I started to pump her harder because my balls were starting to get that tight feeling before orgasm.

The room echoed with the 'schlack, schlack, schlack' sound of my balls smacking her wet pussy, and from the groans coming from both of us.

"Dammit...I'm gonna cum!" I moaned.

Ashlynn's eyes popped open, and I got a real surprise. She grabbed my hair and pulled my head down to her lips and gave me a hot, wet, open-mouthed kiss, sticking her tongue in my mouth and moaning at the same time. We were still kissing like that, when my dick exploded deep in her pussy.

Ashlynn broke the kiss, and her head went back. "OH GOD!" she moaned out again, and I felt her pussy tightening up around my cock, as it started jerking as she orgasmed in time with me.

***

We were both sitting on the floor, naked, eating Chinese takeout that we had delivered. It was a woman who delivered our order, and Ashlynn answered the door clad only in a long shirt, much to the delivery girl's smiling shock.

"You should be ashamed, embarrassing that sweet little delivery girl like that," I said, with a wry grin.

"I have to admit I enjoyed that," Ashlynn replied. Looking at her phone, she added, "Ah, thanks for the payment via Cash App."

"Yep, but there is something 'naughty' about the envelope; I just don't carry cash unless I'm on the way to see you, and I like seeing you" I said.

"After we get done here, I'm gonna wash my man. I think of you as my 'benefactor', and I want my benefactor-man clean, but then I have to go." Ashlynn said.

By what she said and her manner, it was apparent she felt good about herself, and where this was. And she was not alone.

***

Later the following week, again, Cara and Ashlynn had met to hang out, this time at Lighthouse Park, mostly so the baby could play.

"I'm betting I know your new 'heavy-tipper,'" Ashlynn told Clara.

Clara's face flushed and she said, "Look, I know he's your stepbrother now, but I have to say, he tips well. I didn't want you to know because I didn't want you upset with me."

'Or you didn't want me to know you're stealing him,' Ashlynn thought, but then responded, "Look, Clara, it's business, and that is how you and I have to look at it. This part of Florida is small, so you have to figure sooner or later, we're going to get the same john."

"You're right," Clara said, "but, well...my profile is decidedly different from yours, so I'm actually surprised he's into that...it IS fun." And she grinned.

"Not my bag," Ashlynn answered, but it made her think. Part of her had never cared for Clara, and now she was having to share the best fuck she'd ever had with her, and she wasn't sure how she felt about that, and that got her mind churning.

***

"Just one more day, then back to the beach," I told myself, as I walked from the courthouse to the Porsche. Just then, I got that low 'bleep', the one from the arrangement site. I smiled, knowing it could only be one person. In the car, I acknowledged the request, and smiled. It HAD been a frustrating day after all, and the workout Clara wanted, beat going to the gym any day.

A block from the apartment, I pulled briefly into a lot, where a heavily-tinted Nissan sat. I blinked my lights.

"Is this girl wearing what I like?" I texted.

"You know I am, Sir. I feel so submissive." Came the reply.

"You will be, little girl." I sent back. The Nissan returned the blink of lights, and then followed me as I drove to the apartment.

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Hey everyone, and thanks for reading! this is one part of a multi-chapter story, so please give me your votes and constructive criticism, any suggestions as to storyline appreciated!

Special thanks to Kenji Sato for this editing help. Without him this would not have been possible!