Jessica's Downfall

"Jessica, stop!" she said, a note of warning in her voice. "Struggling like that is only going to make it worse."

I sobbed and settled myself on her lap once again, resigned to the fact that she intended to show Mr. and Mrs. Allen just what a tough disciplinarian she could be. With that, her hand continued to work its way up and down my bare bottom without respite. I was sobbing loudly, asking for forgiveness and for it to be over.

"Oh God, please, mom! That's enough! I've learned my lesson!'

Suddenly she stopped and I lay on Mom's lap panting and sobbing softly as she gently rubbed my ass.

"I love you, Jessica," she said, her hand continuing to rub.

I sobbed and sniffled my response, "Love you too, Mom."

I was embarrassed that Dave and Jen had seen me kicking and sobbing across Mom's knee. I kept my eyes fixed firmly to the floor, unable to meet theirs. Thankfully, the spanking wasn't quite as hard as some I've had in the past. In particular, I recalled the one she had given me for stealing a magazine from a newsagent when I was thirteen. Now that one had hurt!

I was just beginning to think there was a possibility that she wasn't going to follow through with Mr. Whippy when I heard the dreaded words.

"Jessica, go get Mr. Whippy," she said, a snap in her voice.

"Please Mom, please no," I pleaded.

"Now young lady, or it will be even worse. Also, it's time to strip off that skirt of yours," she said with a smirk.

I stood up, and as ordered slowly unzipped my skirt, allowing it to fall to the floor, baring myself to the Allen's. I looked up shyly and as I expected, Mr. Allen couldn't stop leering at my young body. To my surprise, I detected a look of desire on Jen's face too!

Oh my God, I thought to myself, I wonder if she is bi?

Now a little bit about Mr. Whippy. Unfortunately, he's been in our family for ages and I'm rather well acquainted with him. He's almost three feet long, looks like a long conductor's wand, and is extremely flexible yet very sturdy. If I'm honest, he's my worst nightmare and I have always cringed when Mom tells me to retrieve him from her closet.

Mom and Mr. Allen were conversing lightly, almost flirting, when I returned. Mom pointed to the arm of the sofa. It was thickly padded, approximately thirty-six inches off the floor, and I'm sure, to Mom, appeared to be the perfect spanking spot!

"Over the arm of the sofa, Jessica," Mom commanded.

I handed Mr. Whippy to Dave, sticking my tongue out at him as I turned away from Mom and laid myself over the arm. I was totally embarrassed at having my bare pussy on such wanton display, especially since I was well aware that my lips were puffy, red, and glinting with the slick juices that were dripping from me.

Disbelief flooded through me as Mom gave Mr. Allen what sounded like some sort of tutorial in the art of spanking.

"David, the key to Mr. Whippy is in how you flick your wrist."

She demonstrated, waving Mr. Whippy through the air. I shuddered at the high-pitched whizz of the cane as it cut through the air.

"Mr. Whippy has been in our family for generations. My mother used it on me and her mother used it on her," she said quietly, looking at me bent over the arm of the sofa. "Unfortunately no one has experienced Mr. Whippy more than Jessica. Not surprising really, as she is such a strong-headed young lady."

I gasped as the tip of Mr. Whippy slid over my bare swollen lips while Mom conversed nonchalantly with Mr. Allen. Then, all of a sudden, with no warning and the merest flick of the wrist, Mr. Whippy whooshed through the air and slashed across my bare, vulnerable ass.

"Owwieeeeeeee, fuck!!!", I screamed, my entire body recoiling into the arm of the sofa.

"Jessica Grace!!!! Language!!!!" My mom chided as a warm, stinging pain spread across my buttocks.

She smiled as she continued, "Did you see her reaction, David?" That's why Mr. Whippy is so effective for a headstrong young lady like Jessica. But he's also extremely effective across the thighs, like this!"

With just another flick of the wrist, she slashed the cane across my bare thighs.

"Jesus Mom! Please! it hurts!" I cried, my body once again recoiling from the pain and plowing against the sofa.

My pleas were however studiously ignored as she continued the tutorial. "Now those are two very effective spots but the most effective place is right between those two areas, for very obvious reasons".

She smiled teasingly at Mr. Allen as she expertly tapped Mr. Whippy on the exact spot that she was referring to. I groaned softly, knowing that the next stinging blow would not only be across my ass but would likely get my very sensitive bare swollen lips as well.

"Ohhhhhh goddddddd, nooooooo", I moaned, even as the sturdy stick whizzed through the air, landing on my ass with a resounding snap.

The pain, this time, was excruciating and I buried my head in the sofa pillows, sobbing loudly, as my body spasmed. Eventually, the stinging began to subside and I looked back over my shoulder to check on what might be coming next. I was dumbfounded to see Mom take Mr. Allen's hand in hers and guide it between my thighs.

"See David," she explained, "you can tell just how effective Mr. Whippy is on Jessica by feeling here".

She pressed his hand into my soaking mound, drawing a soft moan from me.

"Feel how wet and swollen she is."

She guided his hand forward and backward over my bare pussy and my moans only increased in intensity when she slid his finger over my hard, swollen clit. My legs spread involuntarily when she pushed his middle finger through my wet, pink folds into my tight, eighteen-year-old sex.

"Oh god!" I moaned softly, "please don't stop!"

Abruptly, she pulled his wet hand away, causing me to groan.

"David, would you like to take a turn with Mr. Whippy?"

"Of course Rachel, it would be my pleasure", I heard him reply, smiling at my Mom.

I mentally braced myself for a hard, stinging strike but before it could arrive, Mom interjected.

"Oh, David, look at you!" she exclaimed. "This won't do, not at all."

Dave froze in mid-strike as he looked at Mom.

"Your shorts, David. Look at them. Much too constraining!"

I watched, shocked as my mother focussed her gaze on the large bulge that tented Mr. Allen's shorts and could only gasp when, with a lewd smile, her fingers fumbled with his belt and buttons.

"Let's get you out of these", she giggled, sliding his pants down to his ankles. "Much better", she purred, her hand gently squeezing him through his boxers. I was astonished! What had happened to my god-fearing, church-going, Catholic mother!

"Now you can continue, David. Doesn't it feel better to be unfettered?".

He responded with a soft groan as my mom continued to rub and squeeze his hard dick. Just a few seconds later, my body jolted as, with a flick of his wrist, he landed Mr. Whippy on the exact spot my mom's last strike had found. I squealed as the stinging pain seared my buttocks.

"Mmmmm very well done David", my mom cooed while I sobbed into the cushions.

Almost instantly, another blow landed in that most embarrassing spot.

"Holyyyyy fuckkkkkk!!!" I screamed as the shock of the strike pulsed through my body.

"You are a natural, David!" My mom cried, with a degree of glee that to my mind was completely unwarranted. "Now you need to inspect Jessica to ensure you've achieved the desired response."

I was panting and sobbing, dancing from foot to foot, as the pain from Mr. Whippy coursed through my body. I couldn't help but moan, however, when Mr. Allen's fingers once again slid through my now, very sensitive pussy. Instinctively, my legs spread as his fingers probed and caressed my soaking lips. Looking back over my shoulder I was shocked to find that mom now had Mr. Allen's cock free, her hand sliding up and down his rock-hard shaft.

"Can you feel how incredibly wet she is, David? Push your finger inside her and feel just how tight she is."

I moaned again, louder this time, as two of his fingers pushed deep inside my wanting entrance. I rose up on my toes as he fingered my wet pussy, curling his fingers against my walls before slowly withdrawing them.

My Mom was on her knees now, stroking Mr. Allen's thick cock with her fingers.

"Can you imagine how exquisite it will feel to have your cock inside that young swollen tight pussy?" She said, her hand moving up and down his thick shaft.

From her knees, my mom looked at me lewdly.

"Jessica, please go sit with Ms. Allen. I have another place that I think David will enjoy being inside."

Jen

====

Wait, what! How on earth did we get here, my brain screamed.

I couldn't believe what I was seeing and hearing! Not only had my husband, under the direction of Rachel, just fingered Jessica's pussy but now it seemed very much like she wanted him to fuck her!

"Rachel," I squawked, "what do you think you are doing?"

Her head swiveled as she got up from the floor, her face flushed and her breathing a little heavy.

"Sorry, Jen. I kind of got carried away." She looked pointedly at Dave's very hard cock which was bobbing and weaving as he watched Jessica's naked body pad to the sofa. "God forgive me, but I'm so hot I want that cock inside me," she said, shaking her head slowly.

Dave chose that moment to be the archetypal man, looking around the room at each of us in turn. "Look, I don't care which of you I fuck. All I know is that I have a cock that is about to explode and needs the comfort of a warm pussy right now."

His gaze returned to mine.

"Jen, we've come this far," he said. "We can finish this now if you want but there will be a whole bunch of sexually frustrated folks. Or I can sink my cock in your delicious pussy, right here, right now. I know it must be wet and ready. Or, you can watch while I fuck Rachel's brains out, baby. Wouldn't that be hot? You've always talked about how hot it would be to see me fuck another woman. Well here's our chance!"

He was right. He and I had often talked about just how erotic it would be to have another woman as part of our sex life. But that was just pillow talk, wasn't it?. Now, confronted with the opportunity, I was frozen, my mind in frantic overdrive as I tried to parse what we were doing and the impact it might have on our relationship in the future.

"Please, Jen. I need his cock in me, I'm so horny right now," Rachel said in a small, plaintive voice as a naked Jessica climbed onto my lap, sniffling quietly.

I snuggled her head against my shoulder and stroked her hair softly as I worked through the possible options and outcomes.

"Don't ever make me regret this, David Allen," I said, looking my husband straight in the eye. "And this is a one-time thing, right? You fuck Rachel now, but never again. Understood?"

His face broke into a bright smile and he quickly crossed to the sofa, tilted my head up with his fingers, and kissed me lovingly. Next was a deep kiss for Jessica, whose fingers I could feel squeezing my arm as Dave kissed her longingly.

Dave

====

I couldn't believe it. A beautiful naked, eighteen-year-old woman was sitting on my wife's lap and Jen had just given me permission to fuck her mother who, at this very moment, was bent over the arm of the sofa awaiting my throbbing cock.

For a moment I thought this must be a dream, that I was laying in bed next to my wife of fourteen years after our Valentine's date while my mind conjured up this weird but very sexy scenario. I closed my eyes tightly, held them shut for a few seconds, and snapped them open again, fully expecting Rachel and her delectable daughter to have disappeared. But no, Rachel's trim, tight ass continued to stare back at me from the sofa and, when I turned my head to check on Jen, she was in the middle of a deep, passionate kiss with our young babysitter.

No further encouragement was necessary and I quickly crossed the gap to where Rachel waited for me, a knowing smile covering her face.

"God forgive me, David for this is a sin against the church and my husband but I need you to fill my pussy with your beautiful cock."

I positioned myself behind her, groaning as I ran my hands across her soft ass.

"Rachel, Rachel," I said softly, gazing longingly at the puffy red lips lightly covered with jet black downy hair that were on display between her thighs.

Grasping my rock-hard shaft, I ran the full length along her slick lips, luxuriating in the warmth of her soft lips sliding along my cock. She moaned softly and spread her legs a little further apart.

"Oh Dave, that feels so good. Please...please let me feel your cock inside me."

My cock suitably lubricated, I lined it up on the entry to Rachel's alluring pussy and, my hands holding her hips, slowly pushed forward, sinking the first two inches of my throbbing manhood into her.

"Oh God, Oh my God," she moaned, rising to her toes and pushing back hard against me.

The pleasure of her pussy enveloping my hard shaft was heavenly and it took everything I have to stop from simply plunging myself into her depths. Instead, I eased my aching cock into her warm, wet depths slowly, relishing every moment of filling her. Finally, I luxuriated balls deep for a few moments before, agonizingly pulling my cock from her delicious warmth, causing her to whimper quietly.

"Fuck, Rachel, you feel so good," I gasped, landing a stinging spank to her ass as I thrust into her hard.

"Oh my God, yessssssss," she moaned as I worked her pussy. "Fuck me harder."

I held her hips and complied, pounding her hard, my heavy balls slapping against her clit each time I bottomed out in her. Rachel's fingers grabbed at the sofa cushions as I fucked her and she began to emit a series of high-pitched squeals as intense pleasure flowed through her body. I reached forward, curling her flowing locks in my fist, and pulled her head back. The sight of her back arched, thigh muscles taut and stretched, was exquisite and it was hard for me to focus. Thankfully, fucking a beautiful woman is instinctual for most men and, despite my inability to focus, I continued to work her welcoming pussy at a furious pace.

"Oh, oh, God forgive me!" Rachel squealed, "I'm going to cum!"

Her entire body shook as the sexual tension that had been building for so long released like water bursting through a dam. The walls of her pussy convulsed around my thick cock, gripping it tightly, while I continued to fuck her through the orgasm.

"Rachel, Rachel, that feels so good," I panted, breathlessly as my own orgasm barreled relentlessly toward me.

She was spent, laying listlessly across the arm of the sofa as I used her warm, wet pussy for my gratification.

"Fuck, yeeesssssssss," I grunted as cum erupted from my balls and began to fill Rachel's sweet pussy. I held my cock deep in her warmth, groaning, as rope after rope of cum jetted into her.

Slowly my senses returned and I looked around warily, recognizing that I'd just fucked my wife's best friend in front of her. I needn't have worried, however, as Jen was lost in a deep kiss, two of her fingers buried in Jessica's mound.

A few seconds later she broke the kiss and, looking across the room at me said, "Now it's my turn for some fun, babe!"