A fun little weekend

I was totally stunned, as I swiped my thumb across my step-sisters Iphone revealing yet another nude selfie. This one was from above as she held her blonde hair up and pouted in that stupid duck-face way that teenage girl do these days. There was even one in a mirror. She was on all fours and had pulled her bikini bottom aside. Freaking breathtaking

Gina was three years younger than me. She was 22 and she was the biggest pain in my ass you could imagine. She was the ‘it’ girl at our small Uni and she walked around like the world owed her a fucking debt of gratitude, while I was already out in the working world and was only here to get the last of my things, having moved into a new place.

Don’t get me wrong, I understood why she acted like this, she was hot, sexy actually but wow did she know it! She treated me like shit, always whining at me when she decided that it was her turn to watch TV or screaming through the bathroom door when it was her turn to use the shower.

BITCHY STEP-DAUGHTER TAMED

It was serendipity, really. A confluence of things that happens every once-in-a-while that leaves you breathless. If you stop to question or ask why, you miss the opportunity. When it happened to me, I never considered asking, I just went with it. One of the best decisions I ever made.

About a week before, I had placed discreetly placed one of those traffic cams in the car we let my spoiled rude-as-hell step daughter Kaitlyn drive. In her early 20’s and just drop-dead gorgeous, she really understood that fact and used it to her advantage, being a total bitch, all the time. She also really disliked me, never accepting that I had married her mother. I knew it because she had told me so more than once.

So when I reviewed the footage, expecting to see her driving like an idiot, I was but for a moment floored at the sight of my wife’s adult child doing coke, discussing on her mobile moving drugs, and giving some guy a hand-job in exchange for drugs. Yep, serendipity, chance, whatever you call it, it had just smiled on me, and I intended to use it.

MY FIRST SUGAR-BABY

COMMENT AND LET ME KNOW IF THIS SHOULD CONTINUE!

Sometimes I get the strangest fleeting memories. This ever happen to you? I mean, take right now. Antionette, this absolutely gorgeous ebony beauty 20+ years my junior is on her knees, grinning as she tugs down my boxers. As she takes my full caucasian cock in her hands I’m reminded of how I very unexpectedly became a “Sugar Daddy”.

I groan as as my fully erect penis probed it’s way into the back of this gorgeous woman’s throat. I glance over to the three sided mirror and enjoyed ‘the look of her bare, dark-skinned breasts as the move and sway to her head bobbing. this is supposed to be a ‘quickie,’ but I love the feeling of being treated this way so much that to stave off the inevitable, my mind goes back to the beginning,,,

***

Step Sister Dilemma

I was taking an unexpected day off mid week. I had been in an electrician apprenticeship for nearly two years and finally, I was at a point that was really kicking it. I had been paying mom & dad rent for the last 6 months, and had just recently received my second bonus. The owner was also giving me a few days off as a way of saying thanks during this intense wave of heat.

I had been chilling in my room over the garage, binging on Netflix, when I saw an odd car pull into the drive. Out hopped a young man I had never seen before, but he walked up the drive like he’d been here before, and in he walked. I was more interested in the show than that guy, figuring it was someone from my step-step-sister’s classes. I was right, but not at all in the way I had pictured.

My step-step-sister is Arielle Wilder, and unlike myself, she had chosen to go to our local university and major in Art. When we would argue she would point out that she was engaged & her fiancé was quite well off, so it wasn’t like she would ever have a care, and to that point, Arielle was completely correct.

ASHLEY’S INTRODUCTION, PT.1

(a young lady is introduced to the BDSM lifestyle by a much older man from her innocent past)

(note that this is a work of total fiction and the names and locations are slightly changed to protect the not-so-innocent)

I was in Orlando to see a client when I somehow found myself in that obnoxiously loud bar; it was seriously not my scene. So in case you were wondering, I’m Johnathan Roberts (see my other stories for this character) & I am one of the most upwardly mobile lawyers in North Florida, at least according to Esquire magazine. I stand a bit over 6ft, am slim yet athletic from swimming and biking and am too close to 50 to tell my age

But tonight was about schmoozing a client, and that brought me here. So as you can imagine, I was thankful my client left after only a short time and it was only while cursing the Droning from the stage and paying the tab that my luck changed, much for the better.

“Mister Robert’s?” An oddly familiar voice called “Johnathan Roberts!” Up strolled one Ashley Brooke West and she locked on to me with a grand hug. Hell, I could feel her chest pushed into me

ASHLEY’S INTRODUCTION, PT.2

(a young lady is introduced to the BDSM lifestyle by a much older man from her innocent past)

I was laying in bed with the incredibly sexy Ashley Brooke West. We had, for a time, simply lay there enjoying each other’s nakedness. I had worked very hard to stay in shape; bicycling & swimming were a passion. So I was comfortable beside this 21 year old woman.

Ashley did have just a touch of ‘phat’ but I really thought it just made her even sexier. I think the term is ‘THICC’ but I’m nearly a boomer, so what do I know. Her breasts were quite full so I rolled a bit closer and, giving her breast a squeeze I also took that incredible tasting nipple in my mouth and used my tongue to fondle it.

I did this while toying with her bellybutton. Ashley lightly moaned. She liked it, but I was getting the ‘talk’ vibe. I moved up and accepted a kiss, then listened.

“Johnathan,” she said, “I have to say, I am TOTALLY impressed. You are…well…-“

CONSEQUENCES, Pt.1

I smiled as I saw my childhood pal Don Heaton drive past, going to his evening part-time job, just as he should be. I checked the tablet I had with me again. Yep, my little video was still there. The other day I saw Don’s mom, Amanda Nicole Heaton was at home, and the man I got her kissing at the front and going down on, complete with tits out, was NOT the man she lived with, of that I was sure. Amanda Nicole Heaton’s common-law ‘husband’ worked 2nd shift he wouldn’t be home until midnight, and her child, Don, would not be home until about 9:30PM. PERFECT.

I mostly hung out with Don thru high-school because had a big house, generous ‘parents’, & his Mom was utterly gorgeous. Some of the guys say his mom was 15 or so when she had Don, so Mrs. Amanda Nicole Heaton couldn’t be over 40. We were 18 now, so my personal bet in our cash pool for her was age 34. She was maybe an inch shorter than my 5ft. 8”/173cm frame in those heels she always wore, with dirty-blonde hair, big breasts, thicc hips and a flat tummy. Amanda Nicole Heaton had a sexy MILF body I intended to enjoy.

CONSEQUENCES, Pt.2

2

“well based on the lingerie I see, you and the hubby certainly have an active sex life.” I said with a lewd grin. Amanda Nicole Heaton was topless but still wearing her yoga pants. “Oh look, wet spot.” I said, pointing at her crotch. My prey blushed, so I tossed the satin and lace Cami PJ’s I dug out on the bed between us and said “Change into those, I want a little fashion show.” And moved the chair over, having a seat.

If Amanda Nicole Heaton didn’t feel embarrassed and humiliated before, she certainly felt it now. After all this, she was being made to parade in front of her torturer like some damn piece of meat. But again, she knew she had little choice. The Cami PJ’s were skimpy and she be blushed as she stood, twirled, and bent over in front of naked torturer. She noticed that his dick was getting erect again, and that could only mean one thing.

Seeing the MILF pose for me in lingerie was nice. She was currently bent over the bed, one foot on the floor, one knee on the bed, looking back at me. I stepped over, and tugging on the bottoms I said “let’s keep the top, but trust me you won’t be needing these…”

CONSEQUENCES, Pt.3

3

I woke up Wednesday with a severe boner, apparently from anticipation. Noting that it was nearly 10AM, I texted “Clear your late afternoon, you’ll be busy after 4” and then sat down to a leisurely breakfast.

Sarah was thankful her phone was on silent, as she had been enjoying having her man spooned up to her, and it wasn’t until he got up to make breakfast for her that she saw the text, spoiling her mood. She decided she was going to enjoy her day and deal with that later, damn him, and deleted the text.

I figured on no response, so I sent another that I knew would get at least a reaction. “Something in a box for you on back porch. You’ll be wearing it later.” I had spent the day off doing more than making her send pics, as Sarah Connor was about to discover.

Sarah Connor almost exclaimed “Oh Shit!” aloud before catching herself. Thankfully the BF was not in the room. She made an excuse to keep the shades closed, and after an admittedly great breakfast of eggs and bacon, she was just able to see thru the window the corner flap of a box.

CONSEQUENCES, Pt.4

4

It was nearly 10PM and I was finishing up some online school work and a university app when I got the text. ‘Danny…this has to stop.’ It read. ‘when did u plan 2 stop with lover-boy?’ I sent back.

Amanda Nicole sighed. Don was in his room, doing schoolwork, and her boyfriend wouldn’t be home for another hour. “Danny, please,” she texted, “You know this must end, I’m begging you.”

Acknowledging she was right would give her power, and that wasn’t going to happen, yet I knew I had to give her a glimmer of hope, because she was getting very desperate. ‘tomorrow’ I simply texted, and tossed the phone aside.

***

Amanda Nicole’s boyfriend gave her a quick kiss and was out the door. He was off to the gym for a morning workout with his guys, and he would meet her for lunch. She was having real pangs of guilt as of late. It was one thing to be forced to give up her body as she was doing, but it was something altogether worse to be enjoying it. She hadn’t offered herself to him for more than a week, and it was all due to her own personal greed. But she kept a good face for him, letting him squeeze her butt and breasts before he left.