Fiftyandclueless, Author at NSFW story — Page 5 of 8

Upstairs, Part IV – Emily Gets Her Freak On

By J. K. Jones

Friday afternoon my cell phone buzzed with a text. I was sitting out on the porch of my fraternity house, basking in the sun, reading some literature, wondering what kind of games Emily might have in mind for the weekend.

Last week, after giving me a loving kiss goodbye at the door at 6:30 in the morning, after the insane debauchery that had occurred with her and her two slutty friends Jane and Jasmine, Emily told me. “Don’t make plans for next weekend, okay?” Her eyes had twinkled mischeviously as she nipped at my lip. “Please?” Grinning like an idiot, I gave her ass a squeeze, and then hopped on my bicycle, waving good bye to her. Inside her house, her 9 year old son Jacob was still asleep, but it was about time to get up to start getting ready for school. Read more »

College Babysitter Blowjob

By Rodney Robertsen

Clark smiled at Ginger as he reached for his wallet. The pretty blonde college student was standing in front of him, her long pale hair swept back over her shoulders, her pert 19-year old breasts jutting out of a tight grey sweater which didn’t come down far enough to cover her skinny tanned midriff with a cute orange belly button piercing. Her shapely calves were bare, small feet in flip flops, and her slender thighs poked out of blue jean cut-offs.

Clark’s wife Betty was already upstairs and in bed. The two had gotten home from an exhausting company party, and Betty had given him a peck on the cheek as they walked up the stairs, her ample ass moving in her long dress. “Can you go pay Ginger and drive her home if she needs it? I’m tired. I’ll peek on the kids, and then I’m hitting the hay. I assume you’re going to unwind on a game or something?” Clark told her “Yep,” and came back downstairs, where Ginger was waiting. Read more »

Helping my Cousin Perfect her Stripper Dancing [dancing; incest]

By Rodney Robertsen

I was lounging around the living room of my parents’ house one afternoon, a little sweaty from just having mowed the lawn in the sun, thinking about a shower, but not quite motivated yet to do it. At the prime age of 19, I still lived with my parents; this made sense, because I was enrolled full time at the local community college, getting some of my basic credits in on the cheap. Mom and Dad didn’t charge me rent, and in return I kept the lawn and gardens crisp and clean, the windows washed, the garbage taken out, and any other random chores that Mom was fond of assigning me. All in all, it was a sweet deal for me, since I had my own room in an otherwise unoccupied basement, and could study, game, or fuck to my heart’s content.

Speaking of fucking, I hadn’t done a lot of that for a few weeks, ever since my now-ex-girlfriend Tiffany had dropped the boom on me, calling me a loser and breaking up with me. “You might have a big cock,” she said, “but you’re boring and unmotivated. Community college? For fucks sake.” Then she promptly started dating some greasy auto mechanic. You know, whatever. Read more »

Upstairs –A MILF Fantasy – Part III – “Emily and her Friends”

By J.K. Jones

At the tender age of 19, I’d had a few sexual encounters with girls my age or just a bit younger, and had even gotten a hand job from a teacher’s aide, a 24 year old grad student named Sheila, one day after class in her tiny office. Long story, and one that involved three hours of flirting over coffee, and a wager, but I’ll tell that one another time. My point is that I had so far had some mild level of sexual adventure by my junior year in college. I was tall, not bad looking, had a body hardened by bicycling and tennis, a good-sized cock that was always popping up and out. I had straight teeth, (thanks to braces in middle school) an agile mind, and because I liked people I tended to talk to them. One secret that many kids my age hadn’t yet figured out, but I had, was that if you spend some time and effort talking to a lot of females, you are going to end up fucking some of them. Read more »

Upstairs – A MILF Fantasy – Part II – “Serious Fucking” (Part I was posted earlier today).

By J.K. Jones

Emily’s hand in mine was smooth, slim and warm, and pulsing with life as she almost dragged me up the stairs to the second floor of her house. Her sexy ass was bouncing right in front of me, her legs long, smooth, naked. I could smell the heady aroma of a turned on woman, with a tinge of alcohol. Her hair was long, thick, and showed signs of recent brushing, less wild than ten minutes ago when she had come rolling in drunk and disheveled from a night of drinking with girlfriends and fending off creeps.

Emily turned her face as we arrived at her bedroom door, and her beautiful large brown hazel eyes flashed with lust and urgency. Pragmatically, I noticed that during the five minutes she had been upstairs, she had touched up her make up. So the act of letting her robe slide to the door to show me her fine, naked, aerobics-built ass and legs, and asking me if I wanted to go upstairs with her, as spontaneous as it had seemed, was probably something of a planned seduction. However, it had worked with acute efficiency. Read more »

Upstairs – a filthy MILF fantasy (Part 1 of 5) – [the build up and seduction]

“Well,” she asked, looking over her shoulder at me. “You coming upstairs?”

Emily had slipped the fuzzy robe off of her shoulders, and as it slid to her ankles, it revealed a tall, fit middle aged brunette woman, her skin toned dark from the shadows of the stairwell that she stood within, her legs tall and slender, her lovely ass even more shadowed and mysterious. Her hair was dark, and her eyes glinted in the low light. I noticed her tongue lightly emerging and licking her upper lip as she grinned at me.
I stood up, in shock. Definitely not what I was expecting.
Working my way through college, I had accepted a few babysitting gigs here and there, mostly from members of a community writing club that I had joined down at the YMCA, and from a few other couples that saw my advertisement, placed on the bulletin board in the YMCA lobby. I know it sounds a little odd for a 19 year old college junior, a male, with classes, intermural sports, fraternity hazing, campus parties, and all of the other distractions of collegiate life, to make some extra scratch as a babysitter. However, it was a good gig for me, since I usually could count on the last few hours to do homework, and didn’t mind if things went late. That endeared me with several couples who appreciated a sitter that didn’t turn into a pumpkin at 11. Hey, ten bucks and hour, and feel free to stay out all night while your kids sleep and I plug away at homework. Talk about a win/win. Read more »

Can’t Resist My Step Mother’s Huge Jugs [incest, cheating]

Our family was going on vacation together to Hawaii. We were flying together from Seattle, but my father was on a business trip in the Midwest. My stepmother Jennifer and I flew to Seattle and were planning to rendezvous with Dad in the morning, meeting him as he flew in from Omaha, and then the three of us would hop on the plane to Kona.

Jennifer and I arrived in Seattle midafternoon the day before, and both of us noticed the crowds at the airport. “Holidays, I guess,” my stepmother said, shrugging her shoulders and grinning at me. She was a short, curvy lady of vaguely 40 years, with long flowing brown hair, flashing blue eyes, and a wicked smile that hinted of things that I never allowed myself to think about. She was dressed in comfortable travelling clothes- yoga pants over her shapely legs, and a t shirt and hoody that didn’t do much to conceal her very large breasts. In fact, sitting beside her in the cramped airplane on the flight in, her boob kept pressing into my arm as we flew, pretty much any time either of us moved. It felt nice, but I made a show of moving away from her the first time it happened. She sighed and looked at me. “Sorry I keep touching you. Dangers of flying. Better you than him.” And she rolled her eyes at the guy on the other side of her seat, so obese fat fuck. She leaned in to me and whispered. “So just expect me to be half in your seat the whole trip, love. I really don’t want to touch that guy.” I grinned and nodded, and she leaned into me unabashedly, her breast smashing around my arm. “You do feel nice.” Jennifer whispered. “Strong young muscles. I wish your father had those.” I chuckled, flexed my arm a little so she could feel it, then went back to my book. Read more »

Free Use Family, Part I

By Rodney Robertsen

I imagine my family is a little different from you. I have a brother and two sisters, all older than me. My Aunt Sandy lives with us, and her daughter Harriet as well. Mom and Dad are old hippies that used to live in a commune in Bend, Oregon, back in the day. They cleaned up and got professional, and when we were little kids they were working their asses off, and now are pretty much retired in their late 40’s. A decade ago they purchased a huge Scooby Doo mansion in a small town off of I-5 (I’m not going to say which one, but I’ll say its north of the California border.) Read more »

Cupping Therapy and Tentacle Marks [bondage, anal play, cupping, body art]

By J.K. Jones

My wife Zara was a little restless last Sunday afternoon. I was sitting back on our bed, propped up and half reading a garbage Tom Clancy novel, and half watching some awful movie on Youtube, when Zara came walking into the bedroom and hopped onto the bed beside me. There was a flashing gleam of mischievousness in her dark brown eyes, and as she pushed aside her long black hair, she smiled, and set down a large black rectangular case, on the bed between us.

I raised an eyebrow at her. Read more »

Raunchy Road Trip with Emily and Jane – a MILF Fantasy (Part V)

By J.K. Jones

As Emily’s sleek blue sports car purred under us, I navigated through the empty streets of Lincoln City, Oregon, keeping one eye on the clean streets and wide sidewalks in front of us, and the other on the rear view mirror, which revealed Emily and Jane reclining in the back seat, sun dresses up to their waists, legs splayed wide, a hand from each slowly and casually stroking the pussy of the other. The two gals were gently touching each other, their eyes focused out the windows, taking in the gorgeous ocean vista off to the right in the background. My two gorgeous milf friends had been having sex in the back seat for the last hour and a half as I drove west toward the setting sun. We had reservations at a motel down near the beach, and I was headed there with the two gals, and a car trunk full of sex toys.

“Hope you two aren’t worn out,” I said. “Because I’m ready to bust a nut.”

“Don’t be crass, young man,” laughed Jane. Both ladies had pretty, tanned faces, long wavy brunette hair, and the vestiges of sundresses, pulled up at the waist to reveal juicy swollen pussies, and the tops pulled open to expose hard-nippled tits. Read more »