(Ashlynn lets me go where few have gone before. Someone else enters the picture?)
6
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, step-sister be damned!
Ashlynn was not dumb. She knew the deal, knew what was expected, and was OK with it. Ashlyn Luker had long ago decided that it was part of being bought, but even more so she felt safe to do this. As long as Johnathan Roberts (me!) went slow, she felt like it would go OK.
“Ok 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 anal 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 OK with letting her think she was in control of this. That 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 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. It HURT. 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 an allowing her asshole to accommodate him.
She was breathing heavier now, partly from pain. It’s not like she made a habit of putting anything in her ass, must less a thick dick like her benefactor’s. She knew he wouldn’t stay still for long, so reaching down, she began to stimulate her clit using her fingers. That felt good, and she picked it up as she felt him begin to move.
I had not quite half of me buried in Ashlynn Luker’s PAWG ass. Slowly, I began to p-u-m-p, moving back, then in…back and then in. My bought ass was doing her best to take it though, 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 her benefactor, 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 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 was trying her best to like taking it in the ass, but so far, it was not for her. Part of her liked submitting like this, but the pain? DAMN it HURT! The Hitachi was doing it’s thing, and applied to her clit, it was like science of something, because she could feel the wave 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 phone pole working its way deeper and deeper into her ass.
I was at least three-fourths the way in now. Ashlynn had gone from pain, to moaning like an orgasm, to somewhere in between. It was good to 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 deeply, it’s hard not to for someone like this, bought or not. But now, I could fill the need to dump my goo. That urge was taking over, so I began to thrust into her harder. I cared for Ashlynn, really, but I was going to shoot my load in her ass, plain and simple.
“Cum for me, Bae…” I told her. (pump-pump-pump) “Cum…” I was absolutely balls deep at long last.
“i-I…I’m try…I’m….AHHhhhhhh” Ashlynn answered. Then all at once, she let final guard down, and pole in her ass or not, the wave was released. “I – AHHHHHHHHHH!!!!!!!” she screamed.
When Ashlynn finally orgasmed with me in her ass, Her butthole and entire rectum started tensing on me so hard, it was like her ass was giving me a hand-job. I heard someone making a high-pierced little-girl scream…Oh shit, that’s ME!
I realized that and was far too gone, and I preceded 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 & 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 general work, and was not getting back over to St. Georgina. ON 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 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 & the baby met Clara for lunch over at The Parrot, ‘the’ spot (actually the only one of consequence on such a small island). “So Clara, how has the arrangement app been working? Or should I ask, How’s business?”
“It’s been OK,” 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 in 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’ll hold 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 PCB, or Panama City beach. 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, Ashlynn was sure, just one thing.
Ashlynn knew the deal between her & Johnathan Roberts, but at the same time, she needed to know. So with only a little prompting she got her mother to agree keep the baby that evening & the next day. This item she didn’t grab a small bag of anything, she headed North East on coastal Hwy. 98, straight to the capital.
**
I was expecting a relaxing evening, but instead, Ashlynn appeared at my doorstep. She made no arrangement thru the app, plus she seemed to have a bit of attitude as well, so I figured something was up.
“Have you been fucking Clara?” Ashlynn asked, with an irritated tone.
“I didn’t think what you & I have been doing was considered exclusive,” I replied.
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
“So I used someone from the same app where I found you, it just happened to be Clara.” (I knew who it was but wasn’t about to admit it). “Also, one of the two of us is about to go off to school.”
“Also true.” She said again, “but so will Clara”
“OK 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 OK with that?”
Ashlynn nodded, and went to the restroom. While she was in there, I sent her a meeting request thru the app.
Ashlynn came out of the restroom 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 he stood on this, & the strange part was, she was pretty sure her Benefactor was right, & that wasn’t a bad thing, was it?
Source: reddit.com/r/eroticliterature/comments/m2zwwx/buying_my_stepsister_pt6