Blackmailed: Cheerleader's Mom

"Sorry," I shrugged, "I was just pointing out your obvious similarities. With training, she's come to enjoy a cock inside her ass more than inside her cunt."

"Please stop," she pleaded.

I obliged... kinda... by pulling my finger out of her cunt and progressing to her virgin ass.

"Please no," she begged.

"That's a rather humorous oxymoron," I quipped, my finger teasing her puckered bud.

"I'll do anything else, just please not that," she begged, her assertive personality having fled and gone.

"Agreed," I said, then paused just long enough for her to think I was agreeing with her, before I pushed my finger even further inside her and added, "Yes, I agree that you'll do anything to prevent your slutty daughter's porn scene from going public. And to be clear, I'm not calling her a slut as an insult; she always loves when I call her that."

"Aaaaah," she whimpered from my penetration of her ass. "Please... stop!"

Ignoring her pleas, I pushed my forefinger deeper inside. "Sweetheart, trust me when I say you want me to do this."

"I'll never want it," she whimpered, grimacing.

I laughed, "You want it because if I don't loosen your ass like this first, then the pain when my cock slides inside will be excruciating."

"Then please just fuck me?" she begged. "In my pussy?"

I smiled to myself at her begging me to fuck her cunt. I wiggled my finger inside her ass, working the slow gaping process. "Oh don't worry, I plan to fuck you in all your holes. Maybe not tonight, but soon."

"You're such a sick bastard," she whimpered through clenched teeth.

"That's what my exes usually told me," I smirked, "but eventually they all came back for another go at my cock," I replied, recalling Jessie, who called me up just last month, two years after we broke up, just to get laid again.

I pulled out my finger and warned her, "This next stage may sting a bit, but not for long." I added a second finger and slowly pushed both of them in. She tightened her ass muscles, so I recommended, "I wouldn't do that if I were you. It only makes it worse. Now just relax and trust me."

"Trust you? You're raping me!" she snapped.

Deciding to play her game, I pulled out my fingers and said, "I'm not raping you. Did I force you into my office?"

"No, but...."

I cut her explanation short. "Did I force you to bend over my desk?"

"Well no, but...."

"But nothing," I snapped. "You chose to bend over my desk like some cheap whore. If you want to blame anyone, blame yourself. You're also the mother who allowed your daughter to become such a bitch that she needed to be disciplined. All I did was the job you didn't." I knew this was cold, considering she was a widow, and Dallas's loss of her father figure wasn't Devon's fault.

I went around and sat down at my desk, now facing her. Tears were once again welling in her eyes.

Sticking with my coldness, I asked, "Weren't you about to leave?"

"Do you mean you're giving me the DVD after all?" she asked, a glimmer of hope in her eyes.

"Certainly not. We made a deal about that, and you haven't fulfilled your side of our arrangement," I answered, struggling not to smirk at my own cleverness.

"But I really need that disc," she said, her eyes begging.

"I'd love to help you with that, but I refuse to rape you," I answered. "That would be insufferably rude of me."

"Sorry I misunderstood," she whispered, avoiding eye contact. "Then please fuck me."

"If that's what you really want, I'll be happy to oblige. So to be clear: exactly where do you want me to fuck you?" I asked, forcing her to say the words.

"In my ass," she admitted, although her tone was screaming the opposite... she'd clearly prefer to have her pussy filled.

"Then beg for it," I ordered, standing back up, my erect cock staring directly into her face.

The sight of my cock seemed to encourage her, and I even saw a glimmer of lust awakening inside her. His time her voice was more believable when she begged, "Please, Mr. Stanford, fuck my ass."

"Gladly," I agreed. "But first, would you be so kind as to strip naked for me? I'd love to see if your body is as spectacular as your daughter's, which I suspect it is."

"Well, since we're about to have sex... and at my request... then I guess I really should," she agreed with a sensual smile.

And then she did, and her naked body was almost identical to her daughter's, and just as sexy.

"You're absolutely gorgeous," I told her sincerely. "And now there's an upcoming duty for my cock to perform, so next you should get it rock hard, slut," I ordered, shoving it into her mouth.

She bobbed on it awkwardly for a minute or two, before I pulled out and returned to prepping her fine ass.

I inserted two fingers to continue the gaping process, while my other hand began playing with her pussy. I explained, "You see Devon, your ass was made for fucking, but first it needs to be properly prepped before you can enjoy it. And then once you've experienced how overwhelmingly good it is, you'll start craving it as much as your daughter does, and you'll be begging me for anal over and over."

She tried to pay attention to my words, but I could tell she was distracted by her enjoyment of my fingers on her pussy and the burn in her behind. Her breathing began deepening. Once both of my fingers were deep inside her rectum, I began slowly twisting my hand right and then left. More whimpers escaped the increasingly horny MILF's mouth. I explained, "As you can see Devon, or rather feel, your ass is getting accustomed to being penetrated. It doesn't hurt as much now, does it?"

"It still hurts," she said.

"But as much as before?" I asked.

"No," she admitted, "now it's more of a burn."

"Good," I said, "Because believe it or not, I really do want you to enjoy your first ass fucking." My fingers lingering at her pussy, I slipped them inside to distract her from the other fingers in her ass.

Again her breathing increased as she attempted to respond, still defiant till the bitter end. "I will never, never, ever enjoy such a... such a... such a wretched penetration."

"Never say never," I replied. "Your daughter once said those exact same words, and now she's addicted to getting reamed from behind."

"Oohoohoo," she whimpered as both of my hands played her like an instrument I was fine tuning.

"Your ass is adjusting itself to being filled. So the pain is dulling now, and a new pleasure you've never experienced before is building slowly," I explained, my fingers continuing to gape her virgin ass, preparing it for my cock.

Her breathing was slowly deepening, and her earlier objections had ceased as she moaned quietly, just passively allowing me to play with her two holes. My cock, now rock hard, was begging for action, and after another minute of gaping her ass, I decided it was time to step things up. By now she was obviously horny, and an orgasm couldn't be too far behind.

I pulled my fingers out of both her cunt and ass, and as I expected from a slut (although she was dressed as a professional), she moaned, "Nooooooo!"

"No what?" I asked, my cock now positioned between her snow-white ass cheeks.

Realizing the time had come for me to fuck her ass, she begged, "My pussy, please fuck my pussy."

Deciding to give her some false hope, but also to see how good a fuck she was, I sat down in my desk chair and ordered calmly, "Come here and straddle me, Devon."

Given her desire to come, and I imagine her hope that she'd get me off with just her cunt, she quickly stood up and backed up to me. Straddling my legs, her red cheeks and stiff nipples betraying her excitement, she slowly lowered herself onto my erect missile. I watched my cock slowly disappearing into her cunt, and leaned way back in my chair, watching her riding my cock. It was easily the best vaginal fuck I'd ever had. She rode me recklessly, her pussy muscles able to grip my cock in ways I can't describe, but which had me in ecstasy.

Her words and moans increased as well, as she got more and more animated. "Fuck, does your cock feel good in my cunt. Your big cock is filling me up so completely." Her breathing increased, and knowing she was close to an orgasm, I lifted her up and sat her onto my desk, my cock still inside her.

As I began fucking her ever harder, any hint of propriety she'd had disappeared as she screamed, "Fuck yes, fuck me, harder, harder, fuck yes."

Knowing she was seconds away, I pulled out and demanded, "Now beg me to fuck your ass."

"No, my cunt, fuck my cunt, shove that big snake in my cunt," she whined, her desperation to come obvious.

I gave her one final hard thrust into her cunt, and then backed out. She moaned like a bitch in heat. "Yeeees...noooo."

I smiled to myself, knowing I was seconds away from getting what I wanted, this sexy MILF begging me to fuck her ass.

"Oh please," she whined.

"Please what?" I asked, my cock sliding up and down her ass crack.

"Please, I need it so bad," she moaned, her ass attempting to pull my cock back inside her, her face that of a woman desperate to come.

"Exactly what do you need?" I pushed.

"I need to come, dammit," she answered, her frustration growing. One thing I've learned about women over the years is that when they're close to orgasm, most of them will do things they'd never do just a few moments sooner.

"No problem! I'll make you come like you've never come before... right after you beg me to fuck your ass," I promised, my confidence brimming over.

"Fuck, dammit, fine then, please fuck my ass!" she begged, giving me permission to deflower her ass, her desire for an orgasm overriding her stubbornness.

The instant she said the words I'd been dying to hear, I pushed forward and said, "Glad to hear it, baby. Now just relax; my cock is bigger than two fingers, so for your own comfort, it's important that you relax."

"Kkkkk," she grimaced as my cock slowly broke through her final wall of resistance.

"Rub your clit, baby, it'll distract you from the burning," I suggested.

She obeyed immediately, her left hand shooting to her pussy.

I gradually soldiered on, my cock slowly venturing into this beautiful woman's ass. Her whimpers became moans as she masturbated herself.

"Don't come yet, sexy," I ordered, "the orgasm will be much more powerful if you can hold it back for a while."

"Kkkk," she moaned, asking tensely, "are you all the way inside yet?"

"Six inches," I answered, "which is all an anal virgin like you should be able to handle."

I hadn't meant that as a challenge, it was just the truth; but she took it as one and ordered, surprising me, "Then keep going, stud. I want it all."

"You're sure?" I asked, surprised by her sudden eagerness.

She asked, "Can Dallas take all of it?"

"Yes, easily," I admitted, "but for her first time, I prepped her ass more thoroughly than I did yours just now."

"Then go for it," she demanded, removing the hand from between her legs to grip the desk firmly.

"OK," I said, greatly turned on by this hot, suddenly eager, nympho-MILF. I explained, "My cock is longer than my fingers, so I'll be penetrating some unconquered territory."

"I know," she answered, now displaying a sexy mix of nervousness and eagerness through her gritted teeth as she prepared herself for the pain she anticipated.

"I'll do this slowly, my sexy pet," I explained, as I began slowly fucking her ass.

"Oh God," she moaned, the instant my cock began pumping back and forth.

"'Oh God' good... or 'oh God' bad?" I asked, unsure of the answer myself.

"Good, it's fucking good," she moaned as I continued my short strokes into her ass, each going slightly deeper than the prior one.

The next couple minutes were more of the same. Her moans increasing as my penetration into her ass continued drilling into new depths. Until finally all nine inches of my cock were buried inside her ass.

I said, impressed, "Wow, even though you kept begging me not to fuck your ass at all, you've officially taken all of me inside you."

"Good! Now fuck it, fuck my ass, make me into an ass-slut just like my daughter is," she demanded, her words a desperate plea to make her come.

My balls ready to burst, I answered her plea, shifting from slow strokes into long, hard ones.

My first hard thrust slammed into her ass, once again reaching uncharted territory; and she screamed, "Oh my fucking God, it hurts so fucking good!"

"I could fuck your ass forever, beautiful," I grunted, her tightness milking my cock like nothing I'd ever felt.

Her hand returned to her pussy, and she frantically frigged herself as I continued pounding her ass.

She was insatiable as she begged, "Harder, ream my ass harder. I'm so fucking close!"

I tried to go faster, but I was already at warp speed, sweat dripping off my forehead.

Her moans increased, and her orgasm was the fuck heard around the world. "Oh Jesus Christ, oh fuck, oh God, yes, yes, yes, fuuuuuuuuuuuuuuuuuk!"

The last syllable echoed through my office, ricocheting off of each wall. I continued my assault on her ass while her orgasm pulsed through her. Unable to hold back any longer, my balls burst and I, for the second time today, came inside the ass of an Allen woman. My cum shot out of me like a rocket, and the most exhilarating orgasm of my life electrified my very being! I collapsed on top of her until, both of us spent, I reluctantly pulled out of her perfect ass and fell back into my chair.

Except for her deep gasps for air, Devon didn't move a muscle at first, still in full recovery mode, and I had a perfect view of her gaping, just fucked ass, with my cum leaking out of it in slow, thin drips. They say a picture is worth a thousand words, so I reached slyly to my cell on the corner of my desk, and filched a few quick pictures.

Eventually mobile, she stood up, turned around, and surprised me by bending down and kissing me. When she finally broke the kiss, she smiled for the first time since my blackmail had started and said, "That was fucking amazing!"

"Agreed," I replied. I hated to break this intimate moment, but glancing at the clock, I freaked. We'd been at this for an hour. "Shit, time really flies when you're fucking a beautiful woman."

Her wit apparent, she quipped flirtatiously, "So now I'm a beautiful woman instead of a slut?"

"Can't you be both?" I countered. "I far prefer beautiful, sophisticated women who can also perform as wondrous fucking sluts."

"Aww, I bet you say that to all the mothers you fuck," she teased, her hand slowly stroking my cock.

Laughing, I admitted, "Actually, you're my first MILF."

"Really?" she asked, surprised. "Then I guess I should be honored."

We got dressed in silence, and once we were once again looking respectable I asked, "So this may be in very bad taste right after I've blackmailed you into having sex with me, but would you like to go out sometime?"

She responded, her face suddenly cold and her tone colder, and her volume a long crescendo until by the end she was bellowing, "Let me get this straight. First you blackmailed my daughter, then you used her for your personal fuck-toy for the past few months, then you blackmailed, and then you humiliated and violated me in ways I can't believe I even allowed you to do, and now you're asking me out on a fucking date. Is that about right?"

I shrunk completely, suddenly feeling horrible for how I'd manipulated her into fucking me. "Well, when you put it that way, it sounds really bad."

Her glare was so cold it would freeze fire, although her volume was soft again, just making it scarier. "So you'd agree that sounds awful?"

I was silent, realizing I had nothing to say.

Suddenly she broke out in laughter. "Fuck, are you gullible!" Corralling me like the seductress she was well accustomed to being, she whispered, her voice sultry sweet, "Here's the deal, mister. You're taking me out for a drink or three once this prom is over. It's the least you can do for me after coming in my ass, don't you think?"

Playing along, my heart beating a mile a minute, "Yes, it certainly is the least I can do for such a wonderfully accommodating lady."

"And then," she added, going to my office door, "Dallas will be spending the all-nighter tonight with Markus, so I'll be home alone, and I hate being home alone."

Before I could formulate a reply, she was gone; but my cock was still responding, swelling quickly back to action size.

I returned to the dance and scanned the crowd, which was now much smaller. I caught Dallas' eye at the punch bowl, and she sauntered over to me with a knowing grin on her face.

"Did you fuck her?" she asked directly.

"I don't fuck and tell," I countered.

"Tell that to your face and your hair. You look like you just ran a marathon," she observed correctly.

"Maybe I did," I replied vaguely.

"You're a terrible liar, so there's no doubt that you fucked her," she said confidently, adding with a quizzical look, "so the only remaining question is, did you fuck her in the ass?"

I said nothing, but my face apparently spoke volumes

"You did! You fucked my Mom's ass, you dirty devil! I really hoped you two would hit it off," she said, throwing me for a loop.

"You wanted me to get together with your Mom?" I asked, stunned, realizing the player had just been played.

"Of course, that's why I talked her into signing up to be a chaperone tonight. Although she just thought she'd be supervising. And then... great minds think alike... you wanted to fuck her even before I introduced you, which was perfect. She needs a good man, and despite your blackmailing me and ass-fucking me over and over and over and over and over and over and over...."

"OK, OK, point made," I said, interrupting her endless commentary.

"But seriously, she needs a man who can look after her now that I'm leaving for Harvard, and you need a woman to replace me, and who better than my Mom, who looks just like me," she explained.

"No arguments here," I said, just as Devon joined us.

Dallas smiled at her, "I hear you two hit it off."

Mom replied cautiously, unsure of what her daughter knew, "I guess you could say that."

Dallas, guaranteeing that her Mom knew that she knew all about her, added, "I understand he also explained about my after-school program... very thoroughly."

Devon blushed at her daughter's frankness, and looked a question at me.

I shrugged, "Dallas has very keen journalistic instincts, and not many secrets ever get past her. I wonder where she got that from?"

Devon returned to addressing her daughter, now switching to mother mode. "Yes, and he showed me a video of you being... shall we say... overly scholastic. So you and I will discuss your after-school activities later, and I promise not to yell at you... much. Now go and enjoy the rest of the prom."

Dallas nodded and turned to leave, but she then turned back to her mother and advised her, "Don't worry Mom, you'll get used to it. As a matter if fact, I quite like it."

"I'll get used to what?" the beautiful mother asked, falling hook, line and sinker for the set-up.

"Walking around with hot, sticky, cum leaking out of your ass." Dallas snickered, before turning and leaving her mother standing motionless, her jaw fallen open.

Once Dallas was gone, I quipped slyly, "Like mother, like daughter."

With a laugh, Devon countered, "I think in this case it's more like daughter, like mother. After all, she fucked you before I did."

I laughed back, as my hand slyly grabbed hers.

Epilogue:

They say love can come when you least expect it, it and for Devon and me, that was definitely the case.