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

by Nika Bella Dea

  Deanna looked around to see what she could use on the ass sticking so invitingly into the air. As well as an array of whips and paddles, there were also some butt plugs and strap-ons for pegging, as well as what appeared to be an electronic probe. “What does that do?” she asked K.

  “Push it in, and turn it on. You will see,” she said with a mischievous smile.

  Deanna pushed it into the slave’s ass, and then flicked the switch. He immediately began to twitch with the peculiar sensations roaming through his body so Deanna turned up the power. She noticed the slave was getting hard without permission so she stopped the stimulation immediately. “I never gave you permission for that kind of behavior,” she snarled and, drawing her hand back, slapped him hard across the face. He moaned and his cock twitched.

  “You want me to be harsh with you, don’t you?” Deanna said. “Well, I will show you what happens to slaves who do not take notice of what their Mistresses say.” She switched on the power again, turning it up to full, and reached for a whip. She began to crack it over his butt cheeks, hard and fast. He was jumping about as far as his restraints would allow, his hard cock was twitching, and pre-cum was seeping out of the end. Deanna was aware of this so she brought the whip down harshly onto his cock.

  He screamed aloud and his erection immediately disappeared.

  “Please, Mistress,” he begged. “Allow me to have some release, please.”

  “When I decide that you may,” she answered, picking up a piece of rope, and tightly binding his cock and balls together. Soon, he was bright red and blood engorged and his face was twisted in agony. “I think you should stay like that until I decide otherwise,” she said.

  “Shall we go to the bar, K? I’m in need of a drink after that exertion.”

  They started to walk away and Deanna turned back to the slave for one last vicious slap. “I will be back,” she warned, walking to the bar. “And, then you will be sorry.”

  Feminizing Barry

  by Carter

  Sandra held tight to Barry but he was doing his best to keep a distance from her, while still being locked hard and tight there beside her. The thin, curly-haired guy was literally as far from his head as he could be, like those people who astral project out of their bodies, Barry felt a goodly amount of his awareness was up high, over this scene, looking down at the man he did not now recognize. The woman was squirming in her stilettos next to him. She knew Barry was struggling with the reflection that stared back at them both from the hotel bathroom mirror.

  Sandra had begun by spreading a bright, fire-red lipstick across her boyfriend’s ample lips. Barry pursed his smile in the mirror, giggling at the sudden odd brashness of Sandra. But, that smile had receded as he realized his girlfriend was growing ever-more-interested in applying more make-up to his square face.

  Returning the lipstick to the counter before them, Sandra helped Barry to strip his underwear down as she flicked off her bra and panties. Turning to his girlfriend then, he figured he’d wipe the lipstick off across Sandra’s 36D’s in what was probably going to be a quick fuck here in the tiny bathroom. But, she had stopped him, turned him fully to the mirror, and continued to apply make-up on him.

  What had seemed to be chance meeting in the hotel bathroom, with Barry literally happening across his girlfriend while she was dressing, had quickly turned into something else entirely.

  “Babe, what are you…? Sandra, okay, enough already. Um, is this something you wanted to do all along?" Barry had offered during the five minutes of Sandra clucking her tongue, stepping round him, applying mascara to his already long lashes, and rouge to his cheeks. At the sight of his Cuban beauty in any stage of undress, and suddenly naked as Sandra was then, Barry was, of course, stilled and excited at the same time. In fact, as long as he got to stare at his wide-hipped girl in the mirror, could spy her high, wide ass and her bouncing breasts as she shucked this way and that, he decided she could flitter and tap make-up across his high cheekbones and eyelids all she liked. He and Sandra had taken the weekend to enjoy two days at this country casino. Why not have a little playtime?

  But, as Barry floated there then, seeming to observe the scene from afar, he now found himself dressed in his girlfriend’s panties and bra. He couldn’t exactly reason how the dressing-up had taken this serious turn, and why he hadn’t put a stop to it…and why, right even then, he couldn’t.

  It might have been how Sandra had turned to his side, snaking her right leg across and up over his hip. While smiling at her completed masterpiece of Barry’s pretty face, she had literally rubbed her pussy into the side of his thigh. Or, the fact that Sandra had made sure that, with every cosmetic she placed back on the counter, she had reached down to give Barry's thick hard-on a good long tug and squeeze. Or, it might have been how brazen the woman was to have stepped out of the bathroom suddenly, and then back in three-inch heels, making her taller than Barry. Or, that Sandra had knelt to the bathroom floor, took Barry in her mouth, sucked his dick to just about the point of his all-too-quick explosion, then popped his cock free, and went about wiggling her panties up Barry’s legs.

  “I usually hate it that you’re skinnier then me,” the woman said, standing back up as she pulled her pink, high-thigh cut undies between the crack of her boyfriend’s ass, pushing his balls and cock so up high that Barry’s dick was pushed tight to his stomach, the head peeking from the top of the elastic pink band of Sandra’s panties.

  Somehow, when he looked at himself in the mirror, Barry couldn’t seem to find words. The makeup on his face looked more than a little garish but Sandra had outlined his lips perfectly, lips he ached to kiss with. And, when he looked down his washboard abs at the sight of his red cock head sneaking northward, cut across with that tight panty-top, this made him hornier still.

  It was then that the girl to his side had flicked, flipped, retrieved, and then began to put her big boulder-holder bra around his skinny back and shoulders.

  And, Barry had allowed it all. Now, he stood facing the mirror as his busty, semi-brown skinned girl wiggled into him, clicking her heels across the tile floor, and smiling, as Barry did, the couple acknowledging his quick first, but certainly not only, brush with feminization. With neither speaking, Sandra snaked her hand down the front of his panties. Folding the front of the panty off her man’s dick, holding that elastic right under the root of his cock to seriously pinch back his ball sack, Sandra at once jerked the thick cock in her hand as she leaned into Barry while he watched in the mirror.

  “You like the way you look?”

  “Sa…” Barry said, his full consciousness now back in his body as he stared at this suddenly dangerous woman holding his cock, and seething into him. Who were these women who stared back at him? He didn’t know Sandra right then any better than he did his made-up self.

  “Tell me you like it,” Sandra said, looking deep into the mirror as Barry looked at himself hard.

  “I like it, baby,” he moaned as Sandra all but laid into him, pushing her weight up on her heeled toes, and smacking the side of her man’s leg with what Barry could feel was a dripping pussy.

  Just before he came, Barry puckered his lips. Sandra squealed and this brand new couple came in unison.

  Keeping Secrets

  by Gayle

  "Sit down," I said to Ben’s wide, white smile as he came from around my kitchen wall.

  Keeping my firm legs crossed pinpoint on high knees, bouncing my lower left high heel on the wooden floor, I looked from under my bangs as he took the rocker opposite. If I hadn’t been so nervous, I would have delighted in watching my best friend’s almond-shaped eyes run up and over me, from the tight sweater, down my oh-so-short skirt, down to my bare, taut gams, to my three-inch pumps. Ben had seen me dressed up plenty of times, including weekends like this. We usually ran over to the local tavern for a few cocktails, or to a movie at the very least.

  Later, lighting the condo with candles was usual for me. But, this was one of my shortest sk
irts. I was wearing no stockings with these high heels and the very scented air between this handsome man and me was charged with what was about to happen…at least it was for me.

  "You're late," I said smiling.

  I hadn’t expected, or counted on, Ben being a couple minutes late but the fact that he was helped. In the few seconds it took him to digest my soft scolding, I re-crossed my legs, right knee over left. I could almost hear the tumblers a tumblin' in his crafty little brain. Ben’s a quick guy, probably one of the smartest I know, and we both remembered speaking about this very scenario two nights before.

  Not that in his wildest dreams he would have thought that I would be the one to surprise him with it.

  “It's not so bad, really...” I continued, smiling still at Ben’s now open mouth.

  “I'll only punish you a little for that. But, you’re gonna really get it for taking seven years to tell me your fantasy."

  "Ga...Gayle."

  Poor guy, what could he say? I was ambushing Ben with the one sexual fantasy he said he wanted above all others, the one thing he thought of most when he masturbated, the one kink he had never been able to get his nerve up to tell any of his past lovers.

  Though this guy and I had shared plenty of secrets, two nights ago Ben and I were being ardently forthright and he let spill one particular ache…and ache was the word he had used. It was the kind of detailed scenario you only ever revealed during a drunken night of pillow talk (Ben didn’t drink, though), or maybe to that very best friend you’ve always held a secret, burning physical attraction for.

  "I hope you're ready," I whispered, questioning myself more than Ben.

  Though best friends for nine years, Ben and I had kept our obvious mutual attraction at bay all that time. To be sure, I was dying right then, deeply turned-on, wondering if I could steel my nerve enough to lead Ben in the next few minutes. But, it was entirely possible Ben’s fantasy wouldn’t work with me in the starring role. We might just get to the precipice here, not that we weren’t pretty damn close right then. Either he or I might simply halt the proceedings when I got in position and he began to disrobe, two things that had to happen if we were to make his fantasy real.

  This guy and I knew each other so well, and saw each other so often, that we didn’t even kiss hello anymore. We acted in many ways more like a brother and sister to one another than we ever did romantic partners. Would it be possible for us to get up close as we would have to here, to have Ben see me contrary to how I usually acted around him, and for him to submit the way he would have to now?

  What I was hoping here—and the only reason I even really put this plan into action—was that, since this was a specific kinky scenario of Ben’s I was birthing, the unusual and precise nature of what we’d be playacting would undercut that sticky no man’s land close friends cross when entering into a physical relationship. I wasn’t sure Ben and I could survive a classic and cliché friends-with-benefits pact. Of course, for that, I’d have to get naked myself and I planned on staying within the letter of Ben’s fantasy by remaining completely dressed throughout the next half hour. Not knowing the answers to the riddles above added to the heat I felt between my long legs.

  “Are you sure?” Ben asked.

  I stood and my skirt whispered an inch down my smooth mid thighs. Offering Ben my hand, he stood and I led us down my dark hallway, my heels “click-a-clicking” across the wooden floor as we walked the ten steps to my bedroom. Here, too, I had candles as the only light source and, following what Ben told me about his fantasy, had placed my wire and wicker vanity seat dead center of my peach and tan room. It was obvious what was about to happen.

  “Well…” I said, crossing to the vanity seat, sitting, and then looking up at Ben. "You did say on the bare,” I added as Ben reluctantly began to unsnap his tight jeans.

  I was silently aching to see Ben naked, having dreamed about his thick body on many occasions. I wanted to shift or shuck so I could bring some relief to my throbbing but I didn’t dare take my eyes off the man, or halt my movements. For him, and for me, I had to appear confident, cool, and collected as he stripped not more than two feet from me.

  “Fuck, Gayle,” he sighed, grabbing his zipper with his long fingers. Ben quickly opened and then rolled his black jeans down his thin thighs.

  I swallowed the lump in my throat, trying to avert my eyes from the obvious lump in Ben’s underwear. He stood fully as I tried with all my might to keep my eyes up on his, but there was no ignoring Ben’s powerful, slightly hairy legs, and the thick erection tenting his tight, white briefs.

  “Go ahead,” I assured him and Ben smiled slightly as I sighed.

  Another silent moment of hesitation fell between us as Ben bent with a shot, peeled down his underwear, and then stood back up to present himself proudly to me.

  I ran my eyes to the very bottom of his tight, hairy belly, judiciously exposed under his slightly scrunched-up shirt, then down to his popping cock. Thick and olive-toned, like the rest of the man’s color. It was all I could do not to reach out, and take Ben in my hands…at the very least. The heat coming off my best friend, his close proximity, and his thickness were all making my head spin.

  “Turn around,” I said.

  I was more than happy when Ben turned so I could steal a moment out from under his gaze, and stop staring at his erection. But, of course, seeing Ben’s bare ass, the amazing, high, round work of art that I always spied it to be, made me so heated I had to roll forward on my little chair.

  "Okay..." I said standing…nearly swaying, actually. Adjusting my short skirt so it rode as far down as possible, I sat once again on my vanity chair, pressed my legs tightly together, and said, "Over my lap..."

  Ben laid across my lap with his sculpted ass positioned at the dead-center. I ran my fingertips over his bottom, gently tracing its curves. His massive erection fit neatly between my bare inner thighs. His manhood was now literally an inch from my bare, swollen labia.

  I felt trembling in my legs. I couldn’t tell if the shaking was from me or him.

  The wooden hairbrush lay on the table next to the chair. It was a family heirloom, inlayed with ivory that gave its backside a surface of random textures. The brush was my great-grandmother’s, passed down through the generations to me. I wondered briefly if it had ever been used this way before.

  The trembling was definitely coming from Ben. He must have been shaking from a combination of excitement and fear from the anticipation of what was next. Secretly, I was, too. At this point, I had no idea how this would play out.

  I placed my left hand slowly, but firmly, on the back of Ben’s neck. I wanted to convey a non-verbal sense of authority. I brought my brush hand back, and then squarely down on Ben’s naked ass.

  THWACK…

  Brian’s Ass Worship

  by Claire

  As my plane tickled the tarmac that Friday night, I found myself all but squirming in my seat, aching to get out of the plane. I was pretty wet thinking about the new wrinkle I’d be introducing into what was turning out to be quite the intense game. It was a game I thought about a lot during the weekends I wasn’t up here in Massachusetts.

  Leaving Friday afternoon, I had come to stay at Brian’s condo for my one-weekend-a-month business trip. His place is a mere ten minutes from Quincy, and close to the Monday morning work pow-wows. Brian was my best friend and he and I had stumbled across a desire I always knew he had, and one I suddenly found I could indulge, given this latest work schedule.

  A trust built from 25 years of friendship enabled my interest and arousal, all with me still maintaining a level of propriety where my marriage was concerned. It quickly became a balance beam of Brian working through a sub quality we both knew he courted, and a dominant tendency that had always been evident in me.

  What had gotten us to this point was that Saturday afternoon of my third weekend staying with Brian. He happened to walk in on me naked in his bathroom, putting on make-up. I can’t blame him, real
ly, as my lanky best friend and I had agreed it was best for me to come and go as I pleased, and to make myself at home. This particular early Saturday afternoon, Brian had simply woken from a nap, sauntered down his hallway and, with sleep evidently clouding his brain, hadn’t realized I had entered the condo already, showered, and was in his bathroom, readying myself to go out yet again to visit some old friends.

  By the time the shock registered for both of us, I was jumping to cover my big tits with the side of my arm and Brian was backing out of the bathroom. We were then both chuckling on either side of the closed door. Seeing as I was bent over his sink, and putting on mascara, what he spied of me was really just the side of my body and he had all but jumped back into the hallway in seconds.

  “You always put on make-up naked?” he asked through the door.

  “Yeah…I mean…geez, didn’t you hear me come in?”

  “Dana, you know I sleep like the dead.”

  That was true, he did.

  “Still, I am staying here this weekend, dummy.”

  “Both our faults,” he said and I sensed him moving away from the closed door.

  “Wait, wait,” I said, and popped the door a crack. "You can come in.”

  “Dana,” Brian said, smiling one of five killer grins he kept in his arsenal when something randy might be happening around him. I had known this guy a good many years and, though he and I had managed never to date, we did hold a certain attraction and, on more than one occasion, I had flashed my friend here one of my ample-sized tits.

  If I was going to be staying at his place now once a month, taking showers, putting on make-up, and shimmying my little booty in and out of the futon he had in his spare room, sooner or later we’d be sure to come across a moment of either of us being in our underwear, or wearing even less.

  “What’s the big deal, really?" I said, opening the door wide, and continuing to apply my make-up. “Get a good peek!”