(hello to all! this is my own personal fave here, I REALLY enjoyed writing this! Please read and enjoy, and if you don’t mind, please tell me if I should continue with these two, and where you think it should go! Always interested in constructive criticism!)
(Ashlynn decides to try escorting, and finds her new customer is someone completely unexpected!)
1
Mom died when David &I were very young, and Dad had basically raised me & my brother by himself. A few years ago though, with my younger brother & I busy in our careers, Dad remarried. I personally like the new wife, Gina. She wasn’t a gold digger, and was very caring and sweet to my Dad. But I have to admit, what impressed me more was my new ‘step-sister,’ Ashlynn Luker.
5ft. /160cm at her tallest, with dirty-blonde, perfectly straight hair below her shoulders and a petite frame, weighing maybe 100-103lbs/45-46kg, Ashlynn’s mom Gina was Asian, & some of those looks had transferred over, especially in the shape of the eyes and the petite body.
Ashlynn was a single mom, & they and her mother had come from much more modest means than she was used to, so she had a hard time balancing out her newer surroundings. They were now in Dad’s large multi-level home in a posh, gated community on an island in the panhandle, replete with house cleaners and screened in pool. Gina (Ashlynn’s mom) was, as typical with most Asian Moms, super-strict on her. This was both because she did not want Ashlynn becoming a spoiled brat, or just as importantly not doing anything to get in the middle of her relationship with dad. Dad was happy, so it worked for me.
So one Friday night when I had come in for the weekend, I was looking for some printer paper for this project I’d been working on at work. I knocked on Ashlynn’s door and then heard her shower running. I went in and dug through her desk and found the paper. I was about to leave when I saw her cell phone laying there and picked it up.
it was too easy, because Ashlynn had left her phone fully unlocked, and she had the screen time set for a very long time, leaving it open to me. Hey, I know I shouldn’t have, but my curiosity got the better of me,& really I didn’t even think about the fact I was invading her privacy. Hey, she shouldn’t have left it unlocked.
Being a total snoop, I read through some of her text to her ex-boyfriend/baby-daddy, and then some others to her friend Clara, and THAT was so good, it made me drop the phone! Scooping it backup, I saw something in there about the two of them both escorting? I was quick to send myself screenshots, and had just enough time to go to her email and forward her log in info from the app, plus some rather risqué pics. I locked her phone, and left the room as fast as I could when I heard her shower turn off.
As soon as I got back to my room, I spent the rest of the evening looking through her pictures. Ashlynn was thin sweet and petite, her B+ or maybe C cup tits looked yummy! Like two grapefruits, round and firm, with nice perky nipples that made my mouth water, and her ass was super large for her frame. Damn thing was like a shelf.
There was a really good one with a skimpy pink bikini, but my favorite was a selfie taken in her bathroom mirror, only just obscuring her face. I was over the shoulder, and Ashlynn was showing her pert ass and major side boob. Her ass was seeming to ‘eat’ that bikini bottom, and the nipple was poking out the top, wheat little did cover her. It made my cock hard just looking at them!
It suddenly hit me that I could use her pictures to get what I wanted, but I would need to be sly about it. The texts told me that Clara had been doing this for some time, and Ashlynn was only just getting started, and in fact was only about to post her profile when I discovered all this. I should feel guilty about it, but at that time, the little head was doing the thinking, and all I could think of was how badly I wanted to fuck that ass, and next thing you know, I found myself signing up at this “arrangement Sugar-Daddy App.’ I called myself Steve, and waited.
It had barely been an hour since I had signed up, and was binge-watching Netflix, when the ‘new arrangement in your area’ notification at the app lit up. Popping on, there it was. She didn’t have her face, calling herself ‘Annie’, but I knew from the tatt that Ashlynn was so careful to hide around her mom it was her.
I had spent the last year+ working with a trainer, getting ready for local level iron-man competitions, when Covid hit. I had not let myself go, and was still “living it,” so I was solid, lean muscle. Bad part was, that plus being very successful at work meant no time to play. I was careful in my posting to use only oblique shots of myself, and had a grainy pic of an older gym mate in there, so I felt secure in answering the ad.
Two old sayings that were ringing true in my business were “You get what you pay for” and “Go cheap and go empty-handed” so I made my offer a quite generous one, and it did not take long for “Annie” to answer my ad. My plan was to ‘hold’ what I have described so far to use for blackmail as I needed, but the cash offer was a real one. Relative or no, Ashlynn was hot, and I wanted to hit that pussy, and was willing to pay to keep it all quiet.
It was barely an hour when I got my chance. Gina and Dad went shopping over at Panama Beach for the afternoon, and Ashlynn was home, down in her room. I happened to be driving over to see a bud when I got the message notification, so I had simply pulled over in a parking space downtown in order to respond properly (and safely) Ashlynn had send a message via the app, wanting more information, and introducing herself.
I responded, confirming that the offer as stated was real, and asked if we could meet this afternoon, and offered the nearby Gilbert Inn B&B. I smiled, because I knew that it was not only one of the only nice places in our little town, Ashlynn knew the owners from previous employment. At that moment, I got a text from Ashlynn, asking where I was, so I grinned and responded that I was busy all day, and would see her ‘after while’
Moments later I got an OK and an address. I grinned, and as I turned the car around, I used the Bluetooth to call my bud and tell him I couldn’t make it, as it looked like “my whole afternoon was screwed.”
Ashlynn’s room used to be mine, and I missed it. Mainly because it had its own bathroom, and was pretty soundproof. I’d snuck a few girlfriends in my bed once or twice back in High School, even a local MILF’y neighbor once (OK, twice) and fucked them without anyone even knowing about it. This would come in handy, should the parents come home early. On the way home, I remembered that I had a roll of those name-stickers from a conference that said “Hello, my name is ____” and so at a light I grabbed them and wrote STEVE on one in big bold letters.
When I pulled in I started walking towards the separate door for Ashlynn’s room, and she came bolting out with a totally shocked look on her face. Ashlynn was right in the middle of “Johnathan! You can’t be here, I–…” and then her face went white in shock and horror when she saw the nametag.
I walked right past her and into her room, saying, “Hey Sis, I’m Steve!, let’s talk.” I rolled right over, and had a seat in her glider rocker, and then Ashlynn followed and sat, totally passive, looking like she’d just been caught for murder or something. Ashlynn was smart and knew the gig was up, the only question was, what was I going to do about it.
“Where’s the baby?”
“Clara has her. What are you going to tell mom?”
“Here’s $50 for Clara taking care of the baby,” I replied, then slid over it, with an envelope with the remainder. Ashlynn looked down at it, total confused. “The offer was real” I said,
“But what are you going to tell mom?”
“Depends on what YOU tell her,” I reply, adding “I’m a lawyer and good one at that. I know how to keep my mouth shut. Now in front of you is payment for services, including a sitter, but they didn’t include sitting here and staring at each other.”
Ashlynn’s mouth dropped open. “You can’t be fucking serious, you’re my brother!”
“STEP brother, and does this look serious?” I said, gesturing towards my tented shorts. As if to emphasize it, I dropped them to reveal my big boy doubled-over in my boxer briefs.
“What, you can’t get any on your own, so you have to blackmail me?” She looked really pissed, “That’s fucking sick!”
“I can get it anytime I want,” I told her, “But right now I want you. Face it, Ashlynn, it’s not blackmail. What you were going to do here is prostitution, and I am a paying customer. As long as we keep it between us, I think you’ll find I’m a rather-well paying customer.”
“And what if I don’t keep it between us?” Ashlynn blurted out.
“Well then, I’d get in trouble for sure, but I have screenshots of your posting on the app, plus some other things. Be a real shame for all your MOM, your new Dad, your friends, coworkers, and school mates to know how you support yourself. Bet the baby-daddy might have something to say as well.”
Ashlynn looked at me for almost a half-minute without a word, then her eyes shifted over to the $50 on the envelope. “So it’s all there then?”
“As I said, I am well-paying, so let’s make this a mutually beneficial time together, hmm? Now why not step over here,” I told her, indicating the floor just in front of my chair, “I’d like to start with you blowing me, so take that top off.”
Ashlynn looked disgusted, “Really! I have to strip for you too?”
“You know, I think you need to improve your customer service if you expect a decent review” I replied
Ashlynn looked disgusted but pulled her T-shirt over her head and tossed it on the bed. She was wearing a nice little lacy-white bra underneath. She unhooked her bra, and I got my first real view of her breasts. Despite having a child, they were still pert, and the nipples small, looking like pencil erasers. Also, based on them poking out as they were, I figured she was liking this more than she let on.
“Happy now?” She grumbled and stepped forward, reaching in my shorts and taking hold of my dick.
“Those look nice.” I told her and touched both breasts, then her nipples,& then began to fondle them “I might suck them later.”
Ashlynn knelt, pulling my boxers off, then slid over and looked at my dick in front of her face. She reached for it and put her hand around it, “This is a lot bigger than I had ever thought” She told me as she started stroking it, then added “But this is too weird.”
Ashlynn opened her mouth and took my hard cock in while I watched. It felt great and looked even better, but truth was she really wasn’t doing much, just keeping it in her mouth.
“Come on. You can do better than that. I thought all hookers knew how to suck dick.”
She pulled her mouth off my cock and looked up at me, “Really! I just put my step-brother’s dick in my mouth, and you’re going to insult me too? I’m not a damn hooker!”
“Ok, ESCORT” I replied, sarcastically.
“Fuck you, Johnathan!” She replied but started to suck me again. But the second time it was much better. She was using her tongue now, and even let me get all the way back in throat. Ashlynn was pretty submissive it seemed, because she was OK with me pumping away, and & I kept at it for some time, working from her cheek to her throat.
She finally pulled off me. “Are you ever going to cum?” She asked, “My mouth is tired.”
“I’m not one of those two pump chumps you date,” I told her, “And the agreement was for two hours or two orgasms, so I guess you better get those shorts off.”
Source: reddit.com/r/eroticliterature/comments/m30381/buying_my_stepsister_pt1
A little bit short but definitely hot???