Author: writercat67

BUYING MY STEP-SISTER, Pt.1

(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!)

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(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. Read more »

BUYING MY STEP-SISTER, Pt.2

(Ashlynn’s plans for ‘fast money’ escorting take an unexpected turn, but she begins to think the deal might not be so bad after all…)

2

When Ashlynn was naked, it was quite a sight, as her body was petite and lithe, except for her near-PAWG ass, damn thing was like a shelf! She moved to the bed, down on her back, “This is too weird!” she said, and held a hand up where she didn’t have to look at me

I pulled her to the edge of the bed and looked at her nice little pussy. The lips were pink and a bit swollen, and she had a large patch of dark pubic air above it. I touched it and rubbed it several times as she stared at the ceiling, having moved her hand away. Ashlynn’s breathing had deepened a little, so I dropped down to my knees and gave that pretty pussy a long, firm lick.

“What are you doing?” She asked, “I thought you wanted to fuck me?”

“I’m going to take my time and enjoy it,” I told her, adding “You are going to be worth every penny, Ashlynn Luker, because I am very much going to enjoy this.” and started running my tongue up and down her slit, giving her clit a small kiss each time. Read more »

BUYING MY STEP-SISTER, Pt.3

(Ashlynn finds she enjoys having her step-brother be her ‘John’, getting much more than she ever hoped for)

3

I had the corner room up on top, their so-called “Presidential Suite” really it wasn’t all that impressive. In reality it was a one bedroom walk-up apartment on the corner of the L-shaped building. Nothing that special, just standard Hotel furniture, but it was new furniture, clean, and it had a small view. I heard Ashlynn coming up the steps so I went ahead and opened the door.

“I thought you had that little separate Cabana-house down there?” She asked.

“It’s being renovated and not ready yet,” I replied. With Ashlynn in, I handed her the envelope as last time.

“what did you mean by ‘and then some?” she asked, raising her eyebrows at the cash.

“Well, let’s see if you wore what I requested, then we’ll talk” I replied.

Good girl Ashlynn was, under her t-shirt and short-shorts was the bright yellow, skimpy bikini secured via ties that was in one of her profile pics. Unlike our last meet, Ashlynn was a bit more like an escort this time, modeling her bikini in an almost lap-dance ,showing me her boobs and rubbing her ass on my tented pants Read more »

BUYING MY STEP-SISTER, Pt.4

(Ashlynn accepts her step-brother as not only her lover, but also as her primary ‘John’. I am ok with it too)

4

At Dad’s I hung out with Dad & my brother David at the grill. I saw Ashlynn arrive, but we both kept our distance. At dinner, Gina mentioned that she was happy that Ashlynn was getting additional call in work and some ‘bonuses.’ Ashlynn just shrugged, but she did give me that ‘lingering eye’ for a moment, and I understood. In-fact it made me smirk.

I was helping David put some things in his car before he left. As we were carrying it out, he asked, “Hey Big-Bro, why no arm candy? Thought a successful lawyer like you would be ‘pulling it’ and have someone for Gina to meet, and Dad & I to drool over.”

“Sorry to disappoint you, but being a lawyer isn’t all courtrooms, suits, and blondes you know.” I replied, and then added, “From what I hear, you’ve had something going with some chick on your street, or was it your neighbor?” Read more »

BUYING MY STEP-SISTER, Pt.5

(Ashlynn and I are really enjoy our time together, both accepting the odd relationship and going with it)

5

Ashlynn Luker was lying there, taking every bit of my dick. “Pinch your nipples” I told her, as I pumped steadily away.

“UH-h-hh!” She moaned out loud, as she was pounded into again and again. Ashlynn was tugging her nipples as told, looking at me with a slightly glassy look, mouth open. She was all but being bred, used as her buyer intended her to be, and it was apparent she liked it. A lot.

I had been doing this to her long enough, so I changed it up. Going ‘all in’, I held, knowing she would expect me to begin to grind as I have done before. Instead, I let go of her ankles, shifting her ankles to my shoulders. It was now MY turn to grasp those taught little pencil-erasers on each breast. And then, I shifted myself up…a little adjustment…THERE.

I could now feel my uncircumcised mushroom head pushing on what could only be Ashlynn’s cervix. Rather than pump, I began to make tiny circular ‘tuck’ movements with my hips. I knew that I would now be rubbing her G-spot, and I also knew that the end result would be explosive. It was. Read more »

BUYING MY STEP-SISTER, Pt.6

(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. Read more »

BUYING MY STEP-SISTER, Pt.7

(Despite Ashlynn’s reservations, she decides to just go in the moment, and enjoy her time with Johnathan)

7

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 it’s a fucking dredge, normally I work 12-16 hour days. Can’t blame a guy for taking the edge off a time or two.” 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 some humiliation mixed in, and none of that is you.” Read more »

BUYING MY STEP-SISTER, Pt.8

(Fun with Clara is certainly a different kind of fun, but with her here, I intended to make the most of it.)

8

As any gentleman would, I held the car door for Clara Dandra. Clara stood an easy 5ft. 9/175cm if not a bit more. She was partly Italian or less possibly Hispanic, with that olive skin, & also more voluptuous, being about 125 pounds/57kg I guess. Clara had much larger breasts, and a more rounded face framed by short black hair. Clara’s ass was even larger than Ashlynn’s.

This late afternoon, Clara was dressed in a very short denim skirt, with a tight sleeveless top. She was wearing a bra (likely a skimpy set in satin, because I told her I wanted her that way), and it’s lines were distinctly shown by the tight top

Once in, I shut the door, and handed Clara that traditional envelope, and asked “Why are you here, Clara?”

“I thought-“ she tried to reply.

“You didn’t THINK, you acted Clara. Now tell me WHY.”

Clara remained silent for a log moment, looking at the floor. She traced her foot in a circle and meekly said “I…I…” Read more »

BUYING MY STEP-SISTER, Pt.9

(Clara continues to show her worth; Both girls get an offer…but can they refuse?)

9

When I returned the lotion to the night stand, I was careful to flip the switch on my other two test cameras at the head board and the footboard. They had about 45 minutes run time, and that should be plenty. “Now Sweet,” I told her, “If you like this cock like you claim, I want you to get it hard, then I want you to ride me, starting reverse cowgirl, ok?”

Being her ever submissive self, Clara said “Oh Yes Sir!” and sliding down a bit as I relaxed, she enthusiastically bent to her task, giving my dick some solid hand-job attention, adding in some first-class tongue action on its mushroom head, complete with wonderful slurpy-noises.

Different positions are like different moods and different women. With Clara I mostly enjoyed really dominating her, and that meant being on top. But I had to say, this pretty lady on top of me, working those hips while she faced away was quite nice. The icing on this cake was that I could still top her from underneath. Read more »

BUYING MY STEP-SISTER, Pt.10

(It’s decision time for the girls. Johnathan gets to see if he can tick one off his bucket list)

10

It was Clara that first took an envelope. With a large and audible gulp, Ashlynn picked up the other one, again repeating “I’m not into girls, “ then adding “we stop if I say stop, right?”

I nodded, and smiled. “Yes, certainly. I can work with that. Now before I undress both of you, I want you to each step over to the side of the bed, and face the two large mirrors.” I had managed to discreetly flip my newly-installed switch by the door, (Need to change that though, I thought) then I enjoyed peeling each one of these lovely young ladies out of their respective clothes.

“now ladies,” I said, as I stood between them and had them face the large mirror oppoappside of the bed, “You are both incredibly sexy in your own way. I mean, look at yourselves, can you blame me for not partaking in an opportunity with you both?’’ I gestured towards the mirror. Ashlynn’s initial shyness was mostly gone, and she did smirk, as Clara outright beamed at the positive reference to her. Read more »