Mom died when my brother and I were very young, and Dad had basically raised us by himself. A few years ago though, with my younger brother and I, busy in our careers, Dad remarried. I personally liked his 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 stepsister, Ashlynn.
Standing at five foot three inches at her tallest, with dirty-blonde, perfectly-straight hair to just below her shoulders, carried by a petite frame, weighing maybe a hundred pounds, Ashlynn Luker was her full name. Ashlynn's mom was Asian, and some of those looks had been passed down to her, especially in the shape of her eyes and the petite body. No way around it, my younger stepsister was drop-dead sexy as hell.
Ashlynn was also single mom with a baby daughter, and they with her mother had come from much more modest means than they found themselves in, so she had a hard time balancing out her newer surroundings. They were now in Dad's large, multi-level, lifted beachfront home in a posh, gated community on St. Georgina Island, off the coast our state's panhandle, replete with house cleaners, a gorgeous beach not hundred yards from our door, and screened-in pool. Gina was, as is typical with most Asian moms, super-strict with her, as this was both because she did not want Ashlynn becoming a spoiled brat, and, just as importantly, not wanting her doing anything to get in the middle of her relationship with my father. 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 I needed for an upcoming deposition/trial I was working on. The ground-level room which used to be mine was Ashlynn's, where I thought the paper was kept. I knocked on Ashlynn's door and heard nothing. Thinking she was upstairs, I went in and dug through my old 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, since Ashlynn had left her phone fully unlocked, and she had the screen time set for a very long time, leaving it open to me. I know I shouldn't have, but my curiosity got the better of me, and I really didn't even think about the fact, that I was invading her privacy--hey, she shouldn't have left it unlocked.
Being a total snoop, I read through some of her texts 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 back up, 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 site, plus some rather risqué pics. I locked her phone, and left the room as fast as I could, before she came back.
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. Her ass was heart-shaped goodness on her frame, ready for a stout pounding, and her excellent lingerie choice in a few of those pics, REALLY accentuated that.
There was a really good one with her in a skimpy, high-cut thong, but my favorite was a selfie taken in front of her bathroom mirror, only just obscuring her face. It was an over-the-shoulder pic, with Ashlynn showing her pert ass and major side boob. Her ass was seeming to 'eat' those panties, and her nipple was poking out of the cover-up, what little it did cover. 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 'escorting' for some time, and Ashlynn was only just getting started, and in fact, had only recently posted her profile when I discovered all of this. I should should have 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' site. I called myself Steve, and waited.
It had barely been an hour since I had signed up, and was finishing my work--a lawyer's work is never done, when the 'new arrangement in your area' notification from the site lit up. Popping on, there it was. She didn't have her face revealed, calling herself 'Annie', but I knew from the tattoo, that Ashlynn was so careful to hide around her mom, that it was her.
I had spent the last year and a bit, working with a trainer, getting ready for local-level Ironman competitions, when Covid hit. I had not let myself go, and was still 'living it,' so I was solid, lean muscle; not too shabby for a guy in his 40s. The bad part was, being very successful at work, meant no time to play. I was careful in my posting to use only oblique shots of myself, and I had a grainy pic of an older gym mate in there, so I felt secure in answering the ad.
Two old sayings that rang 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. It did not take long for 'Annie' to answer me. My plan was to 'hold' what information I had so far, to use for blackmail as I needed to, but the cash offer was a real one. Relative or not, Ashlynn was hot--and I wanted to POUND that pussy, and was willing to pay well to keep it all quiet.
It was the next afternoon 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 simply pulled over in a parking space downtown, in order to respond properly and safely. Ashlynn had sent a message via the site, introducing herself, and wanting more information.
I responded, confirming that the offer as stated was real, and asked if we could meet this afternoon, and offered the nearby Coombs Inn B&B. I smiled because I knew that it was not only one of the only nice places in our little town, but I also knew the owners well, and in return for bringing a steady stream of business to them, they were prepping a small separate cabana for me. I got a text from Ashlynn, asking where I was. I grinned and responded that I was busy all day with work, and would see her 'after a while.'
Moments later, I got an 'OK' and an address. Bold girl, 'Annie' was--it was Dad's house I grinned, and as I turned the car around, I used the Bluetooth and called my bud and told 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 that it was pretty soundproof. I'd snuck a few girlfriends in my bed a few times back in high school, and even a MILF neighbor once--okay, 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-tag stickers from a conference that said, "Hello, my name is ____" and so, at a red 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.
