"Despite the rumors, this is my story, and like all tragic love stories, it begins with a man…"
"One… Ugh! Two… mmm!" a woman cried out lustily, shuddering. "Forty-three… Uh! Forty-four! Forty-five! Forty-six! Fuck! Forty-seven… Uh!"
"Quiet! I don't want to hear another word out of you except counting," Master commanded huskily.
Not this man. This man is the Sir before…
"Forty-eight… Forty-nine… argh. Fifty!" the woman shouts, falling forward limply, beads of sweat dripping down her face and hair, her sex, slick with arousal, her ass stinging from the blows of her Master's hairbrush.
He pulls her face roughly toward his crotch. Her lips open and he shoves his cock into her mouth, fucking it, holding her head as she sucked him off.
"Take this cock, Lee-Lee! Don't gag. Suck it down. French kiss the tip. Yeah… like that. That's my good girl. Suck it down like the naughty slut you are. Yeah. Uh. Mmm. Yeah. It's good and hard now. Bend over and assume the position."
Lee-Lee falls to her hands and knees, placing her head and chest flush against the bed, arching her lower back, causing her shoulders to dip with her ass riding high, thighs open wide, presenting herself to her Master.
Master blindfolded her with a long, wide strip of black silk. His rough hands grasped each breast in turn, twisting her nipples, attaching weighted clamps to the erect flesh. He places himself firmly behind her, reaching between her legs to attach the clitoral clamp, forming a harness.
Master took a plaited leather crop with small wooden beads, lightly smacking her over-sensitized flesh. Using lighter strokes along her thighs, reaching to place a light tap on her swollen clit, massaging the stiffened leather between the dripping lips of her cunt, pantomiming frottage. He then dragged the saturated end between her ass cheeks, teasing her rosebud. Lee-Lee trembled from the sensations wracking her body.
Master's footsteps retreated. He returned with a jar, opening it, releasing a minty aroma. Lube, she guessed. A slurping sound as he dipped his fingers in the water-based ointment, gathering a liberal amount on his fingertips, slathering it between her cheeks, across her rosebud, pressing against the resistant flesh, massaging two, then three, fingers inside her tight orifice.
"Have you been preparing my ass for me, Lee-Lee?" he demanded gruffly in a tight, husky voice.
"Yes, Master. This girl has prepared Sir's ass," she replied softly.
"Good girl," he responded with a slap to her clit, causing the weighted clamp to shake, sending a delicious thrill up her spine, reverberating within her heated core.
Master began to slowly press his largest butt plug into her ass, Lee-Lee squirming at the pressure of insertion, her flesh opened obscenely wide, displaying the ring, pink and pouting, stretched to the max. He pressed a button, causing the plug to vibrate, causing her to tremble and moan softly. Master reached between her legs, yanking the clamp harness harshly, causing the rounded, blunt teeth to dig into her sensitive flesh, quieting her after a brief hiss of agony.
An alert sounded. Master quickly mounted his girl, slamming his cock deep into her wet pussy, his balls slapping wildly against her clit, sending her nerves into overdrive. She fruitlessly attempted to push her ass into him to deepen his stroke, but he held onto her hair with one hand, and pushed her back down firmly, foiling her efforts. Juddering with the beginnings of orgasm, she almost huffed in annoyance as he released his hand from her hair, touching her inner thighs, motioning for her to widen them further.
The vibrating plug continued pulsing maddeningly within her bowels as he slowly pulled his cock from her pussy, quickly replacing it with a very thick, extra-long silicone vibrator. She felt so full, penetrated in both orifices. Master smacked the butt-plug over and over, jolted her body, before swiftly extracting it and stuffing his cock inside before her sphincter could collapse, sealing him out.
Though I knew from the beginning that Sir was somewhat of a BDSM dabbler at best, he was kind to me, and charming in his own way. Very thoughtful, since the very beginning. We both realize he's practically old enough to be my father, but he takes very good care of himself and me. Older men seem to know how to take care of their women, even if they don't love them. I know he's in it mostly for anal sex, something most men can't get at home. Say whatever you like. Older men can afford the best toys.
He groaned at the tightness of her ass. Anal sex was sublime. His tight-ass, bitch of a wife wouldn't let him ass-fuck her and he didn't want the hassle of hiring escorts. BDSM solved the conundrum. He wasn't paying for sex, he was enabling his sub to cede control. It wasn't prostitution, it was a mutually beneficial arrangement. Thus, he wasn't paying her for her service, he was facilitating a reciprocal experience.
And it would be over all too soon, he thought mournfully as he pounded relentlessly into Lee-Lee's ass. Once again, his wife had 'caught' him. Every year or so, she would become suspicious and check all of the accounts, ask for his calendar to 'coordinate' with hers or track his mileage and GPS to determine his whereabouts. Before, he had had a string of discreet affairs, but the fallout was usually messy and hard to contain. But his wife had the instincts of a bloodhound. Sometimes he wondered if she'd had his cock was lo-jacked. And in three hours, his arrangement with Lee-Lee would be no more. Bitter anguish caused him to increase the intensity of his strokes. God, he would miss the fuck out of this ass!
His cellphone rang, knocking him slightly off his stride, yet he continued to slowly fuck her ass as he commanded her to make no sounds. He began gyrating his hips as he reached to pick up. Fuck, it was his daughter! What the hell did she want now? He slid into a seated position, pulling Lee-Lee onto his lap, motioning her to ride his cock with her ass. If he didn't have this ass to keep him calm, he would've exploded with rage when his daughter proceeded to inform him of the trouble she'd gotten up to in college.
His daughter, though, was a piece of work. He got a call almost every other session, usually demanding something or other guaranteed to drive his blood pressure up, the little veins in his forehead and neck pulsating with rage… The spoiled 'heiress' to a business neither she nor her brother will inherit.
It wasn't like she was a fucking Rhodes scholar. She was attending the equivalent of a community college, but her grades had slipped. Again. She should've been able to get into a more competitive, higher-rated institution, but her reputation preceded her. Thank fuck for her roommate who had injected a modicum of sense into her with her down-home values or else he could imagine the hijinks that his slut of a daughter could get up to.
"Daddy, I need help. My ethics teacher is going to fail me!" she whined. "This is so unfair! She's only putting so much pressure on me because I'm your daughter!" she complained.
"Why is she gonna fail you? Did you not hand in assignments or flunk a test?" I inquired, grateful that Lee-Lee had reached her arms between her legs and begun massaging my balls with purpose. Damn, the woman had arms like an orangutan. She kept fucking hard on her downstrokes, too. She was a machine.
"Well, she had a problem with my midterm paper. She claimed I didn't adequately cite my sources. As if!" she sniffed. "Now she wants me to re-do the works cited page for 10 percent less credit!"
"Her demand sounds reasonable. She's most likely already graded everyone else's paper. Your mishap is going to cost her more work."
"But Daddy, what about Spring Break?" she whined.
I wondered why she didn't just fuck the boys at her college. Did they look better in Miami or something when she's playing peek-a-boo with the directors of Girls Gone Wild? Her roommate seems to do most of the heavy-lifting. I don't think the girl's typed a single paper since school began…
"Then I'd suggest you get to work!"
"I knew I should've called Mom. You have absolutely no compassion for the pressure I'm under."
If my cock could deflate, invoking her mother would've killed my hard-on, but thanks to my blue pill, I still had a couple hours to spare. I leaned forward, pushing Lee-Lee back on all fours as I attempted to pile drive the lining of her ass into her uterus.
"Listen, honey. I'm always concerned for your welfare, but if you want that internship, ya gotta buckle down, put your nose to grindstone and do the fucking work!"
"Thanks for nothing!" she yelled, hanging up the phone.
"Fuck!" I exclaimed in disgust. My spirits rose a notch as I began to caress Lee-Lee's body, slick with sweat. The evidence of our silent endeavors had soaked into the sheet. Grateful for the waterproof mattress cover beneath it, I slid out of her ass and pulled her into the en-suite where we would enjoy an invigorating shower.
Soaping eachother's bodies, I rubbed my cock against her asshole again. I was still sporting a hard-on that wouldn't quit. She cooperated by bending over slightly, pressing her hands against the wall, allowing me easy access. I briefly dipped my wick into her honeypot, stirring her up and lubing my cock before reaching around to quickly snatch off her harness and shove my cock in her ass as she began to orgasm, as cum poured out of her pulsating snatch.
"Ugh! Oh! So fucking good, Lee-Lee. Such a good fucking girl. Ahh… Fuck! Fuck! Ahh!" I cried out as my cum started shooting deep inside, painting her hot, tight walls. I began to furiously massage her clit in tight circles as I wanted to feel her writhe and quiver against me as I fucked the rest of the cum out of my body, down to the very last drop. Had to make it count. I didn't know when I'd get high-quality ass like this again.
We finished after she had another very powerful orgasm. Not many women come during anal, so she was a queen amongst women. She liked the pain and strain of a hard fuck. You could ride her like a fucking horse and she'd beg for the crop. I wish we could've made this a long-term arrangement, but seven months was a good run. But it's not like she didn't know I had a wife and family prior to the contract. Besides, we both knew I wasn't the kind of Dom she signed on for. I'm a dabbler at best. I just wasn't into all the kink and pain shit she wanted. I just wanted to fuck a frequently forbidden hole without getting anyone's dander up. If I just wanted pussy, I could fuck my wife.
I dried her off carefully, but roughly dragged the towel across my body. I wanted to be in this moment. Her long, dark hair, soulful brown eyes, soft skin and small frame. For a moment as she turned, I caught her in profile with the light angled just so, and fuck if she didn't look like my daughter's fucking roommate! Fuck, that was a disgusting realization! Ana is like another daughter to me. Well, that helped deflate my cock a tad. I suddenly felt much better about ending the contract.
We dressed, her slowly, seductively. I, hastily, jerking my clothes on and covering myself like a Regency maiden protecting her virtue. I wanted to be anywhere but here. She must've felt me mentally pulling away because she smiled tentatively at me, a question in her eyes. Then I said the most ominous fucking words ever formed into a sentence: "We need to talk."
She looked wounded. I guess she had some expectations as we had just renewed our contract last month. "I'm sorry. My wife, she found out about us, so I have to let you go."
She smiled wryly and said, "So this is it, huh?"
"Yes, I'm sorry it has to be this way. I've enjoyed our time together very, very much, but I can't leave my wife," I said.
"Can't or won't?" she inquired.
"Look. Deny all you like, but we both understood this was a possibility considering my circumstances. But haven't I been good to you?" I asked patiently. Despite her age, she seemed rather innocent. Then again, so do praying mantises before they devour their mates. "I took the liberty of looking into some of the art programs you've mentioned over the last few months. I can get you into one of these three institutions," I explained, pulling out a few brochures for her perusal. Her eyes lit up. In the end, it's all about the money. The course fees, letter of reference from someone else of course, and a cashier's check for twenty five large and we went our separate ways. C'est la vie.
Another Master has left me. I'm a great sub. Everyone tells me so, yet none of them want to keep me. I have practically no limits, and I'm very good looking. I keep myself supple, and well-groomed. I even have an interest in the fine arts which makes me appear 'cultured'. I'm quiet, unobtrusive. I like to blend in. Usually, if people don't notice you, they don't send you away. Nobody would ever guess I was the product of trailer trash before I was adopted by the Williams. It was a very private, closed adoption. My birth parents' names aren't even on my original (and only) birth certificate. My adoptive parents weren't rich by any stretch, but they had access to the right people at the right time and ta-da! Newborn!
I need to call Mistress. She likes bad news immediately. Hopefully, she'll assign me another Dom soon. I'm due for a wax anyway. Ah! I contacted Mistress. She explained that I was in luck. There's a Dom that she's looking to match and if I get my health screening, she can introduce us in a month. She was able to give me a brief sketch of his requirements: pale, petite and brunette is his preference. He also like various implements and very rough sex. So far, this sounds like kismet. If I had remained under contract with Master Kavanagh, this narrow window of opportunity would've closed.