Now, I was poised on the threshold of her big oak door (unlocked as she assured me it would be), about to step into what I was hoping was another full trio, which would make her count now an impressive 15 men in just about 12 months. My friends should be teaching a course in sexual technique in school, and not taking the math major courses she seemed to breeze through!
Her front entranceway was dark but I clicked my way down the deep wood floor of the hallway, and found Andrea standing before three naked guys (one of which I think was in a history course I had audited). She saw their eyes flash when I came into view though she wouldn’t have heard their exclamations, stuffed as their mouths were with an apple each. She turned, smiling at me. It was then that I realized she was topless.
This was a detail Andrea had not told me when she described this scene. And, here I thought all I was going to see was her giving quick blow jobs, and maybe an ass beating. When in Rome, I thought, and, as I returned her smile, I undressed completely.
“Plop,” I heard, and looked up as Andrea turned to a lanky guy looking down to his cock as much to the apple he had just let fall from his mouth. I assumed a flattered stance, with hands on hips, front heel set, and my button-down and short skirt splayed on the floor around me.
“Well, we see who the losers are,” Andrea said, bending to throw two sets of clothes to the men flanking the guy who had just dropped the apple.
As she had told me, when Andrea revealed that those who had not dropped the apples were losers, she grew as wet from the confusion that passed across her men’s faces as she did with what she got into later, slicing her belt across bare, suffering flanks. The guys grumbled past me, the taller of the two swinging such a tree-trunk-log-of-a-cock I almost ran after him.
“Sue, say hi to Steve,” Andrea said, holding out her hand for me to step closer. She kissed me heavy on the mouth, and pressed her cool body into mine. My big tits smothered her smaller ones and I had to stop myself from just pushing her to the floor.
“Niiiice,” Steve snickered, and took a step to us as Andrea and I released, and turned to him fully.
“Now, let’s just see what trouble we can get into, shall we?” Andrea said. Stepping up to the guy, she reached down to his bare cock. I guess I had interrupted the usual full test as I just realized none of the crew had been outfitted with condoms yet. Just as Steve leaned into her tickling his balls, Andrea spun the man with her free hand, and smacked his right cheek hard.
I jumped as Steve did.
“He who loses the apple pays a heavy price,” she said as Steve stiffened. And, tonight, my man, you get two for the price of one.”
Billy Getting Exactly What He Wants
by Ralph Greco, Jr.
Playing along as if I had no idea what Nikki and her friend were going on about, I offered after a long chew and swallow of quiche, “Pegging, what is that?”
The two brunettes literally plucked a snippet of quiche in unison as Carol pushed the woman’s magazine over to me. There was no way the duo didn’t want me to ask, of course.
I had been friends with this pair for 25 years. During these weekly lunches, we had all managed a goodly amount of naughty talk, usually centered around, "Well, someday if we all ever get the courage to’s."
Or, Carol’s quick quips of, “We never really did get 'round to that huh, Billy?”
I certainly liked being the only cock in the henhouse these afternoons, thought both women attractive, would have loved to get a gander at Carol’s firm 36D’s, and had harbored not a fair amount of naughty little fantasies about Nikki, as I'm sure she well knew. When any idea popped up here between the two friends, I always flashed enough baby blues to let them know that, hell, if this was the time, if they were actually doing more than just talking, I was game.
Not that they needed me to say this, of course.
I knew what pegging was, having enjoyed a few strap-on dildos up my ass in my 38 years, and would have loved nothing better than to have this pair engage in the practice with me. Unfortunately, while Nikki all but flirted to a razor’s edge, I knew Carol was mainly talk with anything truly kinky. But, the lunches here were always a good gossip fest. Nikki was a great cook and even if, like now, I wouldn’t see much more than these two teasing me (though I knew they teased themselves just as much), I liked being in their company.
“Wow,” I said, pretending to read the magazine, “Mmm, um, ouch maybe?”
I looked up as Nikki went back to her piece of quiche and Carol leveled me with her little brown eyes.
“We’d be gentle.”
“Oh yes, certainly,” Nikki said after a quick swallow…still looking down at her plate.
“Wow,” I said, sliding the magazine between them again.
As had always been my play here—though granted it had never born me any fruit—I was acting more sub, or at least taken-aback, ‘welI-I-never!’ with the pair. You don’t grow through nearly three decades knowing people without realizing a thing or two about their personalities. I prided myself in this perception, even beyond these friends, with how I dealt with most of the women in my life. I hadn’t gotten to this age, still single and never without the attention of some woman, or even a few, because I didn’t know my way round the old feminine brain. I'd had quite my share of kinky dalliances in my day, almost all with me playing the sub role, and it wasn’t simply because I dated only women who liked to play dominant in bed. It was also because I knew how to exploit even a hint of a woman wanting to lead or control, and could play into it exactly the way she wanted me to.
With Carol, and especially Nikki, I couldn’t ever have just come out and said: ‘Yes, I want to have both of you truss me up against Nikki’s kids’ jungle gym there in the backyard, strip me, and have at my ass with switches from the perimeter of trees. No, I had to swallow any of Carol’s suggestions with a fair amount of surprise, and be able to play the whole thing off if I overstepped and Nikki got cold feet, as had happened on a few occasions already.
Carol had turned me over her lap in front of her friend on my 35th birthday and, while all in seeming good fun, Nikki couldn’t bring herself to spank me as her friend asked her to…and I was clothed the whole time! Or another occasion, when Nikki had actually posed the age-old question of boxers or briefs, I stood in her brightly lit kitchen, and peeled my pants down but she literally ran from the room in faux shock…while Carol stayed to watch me pull my pants back up.
Pegging was certainly something that I wouldn’t think Nikki would ever entertain witnessing, let alone participating in. Carol lived to shock her friend, I knew, but really lubing my ass, and fucking it with a dildo she wore or wielded, did seem beyond anything she might want to try, with or without Nikki by her side. Still, the wide-hipped 40-year-old had brought the magazine and I was playing my part for them both.
“That would take some lube,” I quipped, finishing my lunch.
“Think I don’t have any?” Nikki spat, stood from the table, and look down at us both.
“Give me five, then meet me in my room,” she said, picking up the empty plates in front of us.
“Are you serious?” I said to Carol, watching Nikki walk through her living room and her kitchen beyond.
“She’s had a strap-on for years,” Carol said, looking long and deep at me across the yellow table top.
I sat back, and let the sunshine hit my face.
Careful what you wish for indeed, I thought.
Legacy of a Slightly Dom, Widowed MILF
by Jeanie
Grabbing her big tits, riding either one of her dildos (in her ass or pussy), Dolly masturbated nightly to the image of some sweet college boy standing before her, and dropping his pants for her inspection. Then another and yet another guy, faceless studs, would walk past her mind’s eye, all no more than 25 years old, parading through her daydream as she’d come not just once, but twice, sometimes three times, thinking about the wide range of cock she wanted to stare at, touch, and lick, if just the right si
ze, like that fairy tale character with the porridge that was ‘just right’.
The bop-haired blonde woman might have been actually considered a ‘size queen’ if she could really reign over any cock but, as it was presently, sitting just this side of her "late 40’s" (she was actually 52), all Dolly did was dream, whack-off, and while away her hours visiting friends.
Arnold had been a wonderful man, three years older than Dolly, and hung pretty much like a horse. Dolly knew she’d never find another man as kind and as fulfilling as Arnold. But, considering that her semi-divorced, unhappily married, and even one older spinster friend were constantly reminding Dolly that she was indeed now two years widowed, and pretty much a MILF by any stretch of the definition of that word, Dolly could feel her courage rising.
Sure, the idea of fucking some young stud did excite her. But, as of late, Dolly had been imagining how grand it might be just to lure some unsuspecting young dude to her well-appointed Tudor for just the sheer thrill of getting the guy erect and pounding, and convincing him to let her see, and then subsequently measure, his cock. With her quiet home life, Dolly could pretty much entertain whomever she wanted. So, why not entertain a parade of willing, hard dicks? And, while her girlfriends would see Dolly’s interest as a definite quirk (if they could even consider it at all without keeling over), the truth was that Dolly was older then these guys she wanted, and that a younger man would probably be more apt to shuck down his pants to show the ‘old lady’ what she obviously just had to be yearning for. What better way was there to control a man than to request to see his cock, which all of them wanted to show off anyway?
Dolly did not particularly consider herself a dominant personality but, the more she thought about her plan, the more she considered that, yes, maybe in fact the way to keep these potential encounters to her liking was to lead young men into her trap very much like the older, mysterious woman she could easily play.
So, on that Thursday, in a long and loose flower print skirt and tight blue sweater outlining her still-full 38C's, Dolly sauntered to the biggest bar in the tri-county where she knew pretty much men and women of all ages mingled for local camaraderie and beers. She was even known in the place, having enjoyed darts with her hubby and another couple during tournaments. Not being a woman afraid to drink alone, and knowing she’d find plenty of locals she knew, Dolly wasn’t in Jake’s 20 minutes before she was invited over to 2 separate tables. As she sat at the second invite, she found herself being entertained by two brothers who had both kissed her cheeks hello in recognition. She had known their mother for years.
‘Well, at least one of you would suffice,’ Dolly snickered to herself, and was soon in a dart match with the taller of the two, Kevin.
She knew if she did not take this opportunity right now, she might never muster the courage again. On their second pass of darts, with the sandy haired 20-year-old, not as of yet looking at his cell phone nor even hinting at wanting their gaming to end, Dolly threw out the biggest volley of her life to the lanky guy.
“I have a very specific request, Kevin, but stop me if I overstep, okay?”
“Sure, sure,” the guy said, throwing a dart, then fixing his baby blues on Dolly.
“I know I am probably older than your mother.”
“So?”
So far so good, Dolly thought as she managed to arch her back just enough so Kevin’s eyes actually flicked down for a millimeter-of-a-second peek.
“Okay, here goes,” she said, threw her dart, and wiggled closer to the young man, “If I were to leave right now, could you meet me at my house later? As soon as you could actually.”
“You wanna fuck?”
Dolly tried not to rock back on her heels. She smiled, and rose her hand to pat the young man’s soft cheek, hoping no one in the bar saw her.
“Naughty boy,” she giggled, as did Kevin.
“Maybe…but not tonight,” she sighed, and handed her darts to Kevin who, still smiling wide, took them from her. "But, I did have something naughty in mind. Do you know where I live?”
“Yes,” he said, his eyes ablaze. Hook, line and sinker. Maybe Dolly really was a MILF, she suddenly realized.
“Stop over when you leave here,” she said.
“Definitely,” Kevin said, reaching out his hand, and touching Dolly’s. That sudden electric contact alone made her yearn for her dildo right then.
* * *
The allure of the wait was something Dolly could never have counted on. But, only an hour later, she saw the headlights of what she assumed was Kevin’s car cutting across the high tress in her cul-de-sac, then light in her driveway as the young man bounced his car up it.
“Not here for a fuck. So, what could it be?” the curly haired man said the second Dolly opened her door to him.
“Get in here this instant, you bad boy,” Dolly said, laughing as Kevin followed her into her front landing, then to her spacious green and brown living room just off to the right.
Sitting quickly to as much hide her nervousness as to bade the man into the room, Dolly was actually face to crotch with the young man as he didn’t do much more then step right in front of her.
He looked down and just “hmm, hmm'd” with that hubris that Dolly had imagined all attractive young men might muster in the presence of an old woman they thought wanton…and wanting.
She’d quell this bravado but quick, she reasoned, by the very one—and maybe the only—thing she wanted from this guy and, in a quick show of the dominance, Dolly even then felt roiling to the fore.
“Drop your pants and underwear, and get as hard as you can for me,” she said, not even looking up at the man, “I want to inspect the goods before I even consider anything further.”
“Okay,” Kevin said, and Dolly looked up at him then as a cast of nervousness crossed his angular face. He took a step back, and began to unbutton his jeans. For her part, Dolly stayed stock still, fixed Kevin with a raised right eyebrow, and rolled her rump to the edge of the couch.
“I can’t believe I am doing this,” Kevin said, peeling his zipper down.
‘Neither can I,’ Dolly thought, but instead said, “I do hope I am not disappointed. I’d hate to think the price you’re going to have to pay if I am.”
Of course, she had no idea what, if any, price she’d make Kevin pay. Dolly was simply working through the dominant mindset here, stretching this scene for every erotic morsel she could before she was shown…
Kevin was bare suddenly from the waist down. The sight of his pants and boxers pooled in a hammock mid-knee was nearly as erotic to her as the fact that she was facing the man’s tightly manscaped balls, and semi-erection.
She immediately stood, and click-clocked her short heels into her kitchen as she caught a peripheral view of Kevin starting to handle his cock.
“Dolly!” Kevin called after her, but she was back in the room in half a minute, her cloth tape measure in hand.
“Fuck….you weren’t kidding!”
“No, I wasn’t,” Dolly said to the masturbating man standing still at her couch. She got a good, long gander at Kevin’s smooth, tight ass, and suddenly realized there was lots more to see on a young man than just his cock. But, for right then, she had to keep to the matter at hand.
“Getting’ there, huh?” she said, reclaiming her seat as Kevin manipulated what was appearing to be a long, yet thin cock to full erection.
“You young men are supposed to be ever on the ready,” she lightly scolded, reaching over, and tickling Kevin’s tight, smooth ball sack. He got up on tiptoes instantly as Dolly watched his cock literally jump in his fingers.
“Mmm, I’d say we are pretty much near," she added.
“Dolly…I…” Kevin moaned as he let go of his dick and it wagged hard and out in Dolly’s face.
“Now, let’s just see,” she said, and took to measuring Kevin’s erection, from base to tip, and even lifting it for a second, longer length measure, where she as much jerked the man as measured him. All t
hrough this treatment, Kevin moaned, rolled back and forth on his heels, and closed his eyes to this wonderful woman’s warm game under him. Dolly willed herself not to lean forward, and take the man in her mouth.
“Hmmm,” Dolly said, making a big show of examining the cloth ruler where it lay between her two fingers. “Mmmm.”
Kevin looked down at the second ‘mmm’ and Dolly grabbed his balls again, looking up to speak to him with as level a tone as she could.
“Time for you to be on your way, dear.”
“Dolly, I…Dolly.”
“It’s okay. All young men want to measure up." Here, she made a big flourish of twirling the loose end of the ruler in her fingers. “But, not everyone does.”
Dolly stood, pulled up Kevin’s underwear and pants as he reached for them, than kissed the man on his lips hard.
“Maybe some other time,” she said, and smiled after releasing their lip lock. “I do have others to measure.”
As if leading a zombie to her front door, Dolly walked a silent, fumbling Kevin up and out of her sunken living room, down her hallway, and to her door.
She heard his car leave a prompt two minutes after she shut the door on the man’s firm behind. Three minutes after that, Dolly had the measuring tape in one hand, and was rummaging through the top dresser draw in her bedroom for her dildo. If she could manage to scour the entire tri-town area at this particular enterprise, she would not only measure a copious amount of cock, she reasoned, but leave a good portion of the male populace confused and sufficiently blue-balled as well.
Now what could be a better legacy for a slightly dom, widowed MILF?
Part I - Deanna’s Dominant Day
by Krystal Kourtesan
Deanna and Nick Jefferson were a happily-married couple in their early 30s who had been together for 15 years. They had always enjoyed a fulfilling sex-life but, as is normal with a large number of married couples, things had gotten a little stale lately. Deanna was sometimes more adventurous than Nick and she was eager to try new things. The only problem was encouraging Nick to try also.
69 SHADES OF RED: Femdom Stories of Spankings and Other Sexual Punishments - Bend Over! You Know You Deserve It! Volume 2 of the WellHeeledDominatrix.com Collection Page 5
