Jessicas Downfall

Jen

=====

Best Valentine Ever!

I thought, gazing deeply into my husband's eyes.

My handsome, and decidedly sexy husband and I were enjoying a romantic dinner date at Oriole, one of only three restaurants in Chicago to boast two Michelin stars. The food was divine and, despite being married for fourteen years, Dave was flirting with me as if it were our first date.

All's well in the world,

I told myself. I have a career that is flourishing, I'm well on my way to achieving a partner position and, although I'll turn forty in just a few weeks, I was feeling radiant in the short, sparkly cocktail dress that I'd purchased especially for tonight's date. Best of all, I have two beautiful daughters at home who mean more to me than anything else in this world.

As usual, Jessica, my friend Rachel's daughter, was sitting for them, as she had since age fourteen. I've watched her blossom from a gawky teenager into a beautiful and poised young lady. She's a good Catholic girl, attending church weekly, and I trust her implicitly with the girls. She'll be a college freshman after the summer, which means not only will there be a string of broken hearts at Duke, where she has a scholarship to study pre-law, but that I will, unfortunately, need to find a new sitter for the girls.

Returning to the moment, I flashed my sexiest smile at Dave and brushed my hand across his lap, lingering just long enough to feel the first stirrings of his delicious manhood.

"Thank you for tonight, babe. It's been wonderful! Let's have dessert at home. I have something special for you." I said, once again looking into his dazzling blue eyes.

He grinned back, like an eager puppy dog, and signed the check with a flourish.

"Ready when you are, Jen. Happy Valentine's," he said, leaning over to kiss me.

The 'something special' I had for him was a very sheer black baby doll, decorated with emerald green lace, that came with a matching green and black thong. The plan that had been budding in my brain was that, while he drove Jessica home, I'd change into the baby doll, pour him a glass of his favorite malt whisky (Laphroaig, for those of you who are connoisseurs), and arrange myself artfully on our bed to await his return. I'm pretty sure that you can figure out just how I intended my best ever valentine's evening to end.

Unfortunately, it wasn't to be!

I was more than a little disturbed that Jessica wasn't watching Netflix in the family room as usual, when we got home. When there was no response to calling her name, I rushed upstairs, alarmed, to the girls' bedrooms. To my relief, they were both fine, curled up under their comforters, sleeping like two angelic cherubs.

I was flummoxed! What had happened to Jessica? Surely she wouldn't have gone home and left the girls sleeping! Right then, Dave bellowed from downstairs.

"Jen! Where are you? What's going on?"

I hurried back downstairs. He was standing at the bottom, pointing towards our master bedroom.

"You better check on Jessica."

"What? What do you mean?" I responded quizzically. "What's Jessica doing in our bedroom?"

"Just go check on her, babe. Make sure she is ok."

The scene confronting me when I walked into the bedroom can only be described as surreal, way beyond anything my imagination could ever conjure up. Jessica was asleep, or at least I prayed that she was simply asleep, on our bed. She was naked from the waist down, a thin yellow thong dangling from one ankle. Beside her, still clasped in the fingers of her right hand, was my Hitachi wand. Now, I have to tell you that I would be more than happy to own that wand solely for the body massage that it gives. When Dave uses it on my neck, shoulders, even my lower back, all of my tension and knots seem to melt away so easily. However, when he, or I, use it on my clit it never fails to deliver an explosive orgasm in a matter of minutes.

It was obvious that Jessica had been experimenting with the wand after settling the girls in bed. Her pussy lips were red and puffy and I surmised that it hadn't been too long since she'd brought herself to an intense, mind-blowing, and probably very noisy orgasm.

As my eyes surveyed the room they landed on the empty vodka bottle that sat on the nightstand next to a heavy crystal glass.

Oh, Jessica, I thought to myself, what have you done!

Shaking my head slowly, I took a blanket from the closet and laid it softly over Jessica's inert body. Dave was looking pensive and sipping on a glass of whisky when I returned to the family room.

"Is she ok?" he asked, anxiously.

I held up the empty vodka bottle. "She's fine, I think. I suspect she's sleeping it off!"

"Ummmm, she was naked, Jen. I didn't hang around but I did see she had no panties on."

I laughed, shaking my head slowly. "Yeah, seems like the little slut discovered my wand and was having herself a little fun. Looks like the vodka got the better of her and she fell asleep on the bed."

"What are we going to do? I can't take her home in that condition. Rachel will freak if she finds out what Jessica has been doing tonight. You know how uptight and straitlaced she can be."

"I know. But we trusted her with the girls, babe. I'm not sure I can let her behavior pass without there being any consequences. What if one of the girls had woken up and found her in that state? Honestly, she deserves a good spanking!"

"Probably so but you know we can't do that. Not only is she not our daughter but she's eighteen and past the point of being spanked, even by her parents. Look, why don't you put her to bed upstairs and we can talk to her in the morning when she's a little more with it."

It was past ten the following morning before Jessica, rather sheepishly, walked into the kitchen. She remained silent when I opened the refrigerator and handed her a bottle of chilled water.

Finally, she spoke. "Good morning," she said quietly, refusing to look either of us in the face. "I'm...ummm, well, I'm sorry about last night. I got kind of carried away and...well I know I shouldn't have done what I did. I'm really sorry. I hope you won't tell my Mom."

I looked at Dave, took a deep breath and let loose.

"What were you thinking, Jessica! Drinking and...well, doing things that young women of your age shouldn't be doing. Do you realize just how much time, effort, and money your parents have invested in raising you to be a proper young lady? Of course we're going to tell your parents about your behavior.

She looked up at me, rolling her eyes.

"Oh, for fucks sake! Do you have any idea how hard it is to live with their expectations of how I ought to behave? I'm eighteen for God's sake. Yes, I'm young but that doesn't mean I don't have needs and desires just like every other woman in the world. Yeah, so guilty as charged," she said, holding her hand up, "I used your wand to get off last night. Isn't that what you use it for too, Jen?"

A sly grin covered her face as she stared at me, laughing in my face which was rapidly blushing a deep shade of red.

"And guess what? I was imagining that it was Dave who was fucking me while I did it! Does that surprise you?"

"Jessica! Oh my God, you can't say that!"

Now it was Dave's turn to blush.

"Why not, it's the truth! Hasn't my dear pious Mom raised me to always tell the truth? Well, the truth is that I was imagining your husband's big fat cock pounding me while I played with my pussy last night. So there!"

"Jessica! Really! I am taking you home this minute and I'm going to tell your mother everything that happened last night. She can figure out what to do with you but if it were me I know what I'd do. You'd be over my knee, receiving a good hard spanking!"

"Yeah, well you're not my Mom, so hard luck on that one," she retorted sharply. "Look, really it's no biggie! So I got a little drunk and got off imagining being fucked by an older guy. Doesn't every eighteen-year-old girl do that? No need to tell my Mom, right Dave?"

Dave shook his head slowly.

"If it were down to me," he said, "we'd simply have this conversation and put it in the past, Jessica. But Jen is worried about you. She thinks your Mom and Dad need to know so they can help sort you out before you go off to college."

"Help sort me out! What does that mean?

'Jessica, you aren't old enough to drink and you know that good Catholic girls don't have sex before marriage. What were you thinking?'

Seriously? Is that going to sort me out?"

Jessica

======

Despite my bravado, I really didn't want Jen to read Mom into what had happened the night before. It was embarrassing enough to know that both Jen and Dave had seen me semi-naked but having Mom know that I was masturbating about Dave, with a vibrator no less, was something to be avoided at all costs.

"Seriously, Jen, please don't tell Mom. I'll do anything you want. I'll babysit for free from now on."

"I'm worried about you, Jessica. You shouldn't be getting drunk and fantasizing about older men like Dave. You should be having fun with boys your own age."

"Guys my age are so immature. All they want is to get into my panties, Jen."

I looked at the two of them pleadingly, hoping that the sad little girl look that works so often with my father might get me out of this hole.

"Don't give me that look. Your Mom is going to hear about your behavior and that's final!" Jen said.

I pouted and sent one last zinger her way.

"Well at least let me fuck your husband before you condemn me to a life of penance!"

Half an hour later I was standing in front of my mom, looking woefully at the floor as Jen recounted the events of the previous evening and the conversation she'd had with me this morning.

"I hope you understand why I'm sharing this with you, Rachel. It's not that we want Jessica punished for her behavior, though I did tell her that she deserved a good spanking. We're worried about her. It's not right that she should be drinking and having sordid thoughts at her age."

I rolled my eyes at Jen's mention of sordid thoughts.

After all, I'm not the one that owns a Hitachi wand, am I? And it sure as hell isn't just for massaging your neck,

I thought to myself.

"Of course not. I can hardly believe that what you just described came from our Jessica. We've raised her to be better than that. Father McPherson will be so disappointed when he hears about this."

I couldn't believe my ears! Father McPherson? What did it have to do with him?

"Mom, seriously! What's it got to do with him? He's just an old goat that likes to ogle the young girls at church!"

"Jessica Grace! You will apologize to Ms. Allen for your behavior this minute! And the next time you take confession with Father McPherson you'll ask forgiveness for your sins and apologize personally for spreading such vile rumors about him."

A wave of relief washed over me as I listened to Mom's lecture. Apologizing to Jen and having to go to confession with Father McPherson was a small price to pay considering I had been expecting much worse. However, the ax soon fell, dragging away any hope I had of getting off so easily.

"What's more, young lady, you're going to be punished severely for your sins. Tomorrow afternoon you are going over my knee for a hard, bare bottom, spanking. You may be eighteen but no daughter of mine is going to act like a slut in front of my friends and not suffer the consequences."

"Mom, no! Please I'm too old for that!."

"You're never too old, and what's more, Mr. and Ms. Allen are going to watch! And Mr. Allen is going to give you six strokes of Mr. Whippy!"

"Oh my God, Mom. You can't. Please, that'll be so embarrassing!"

"Really, Rachel. There's no need," Jen interjected. "Dave and I just wanted to let you know so you could talk with Jessica."

"Oh, there's every need, Jen. Jessica's behavior was extraordinary and as a result, extraordinary discipline is necessary. Otherwise, there won't be any change in her behavior. Tell Ms. Allen who Mr. Whippy is, Jessica."

I looked down at my feet and mumbled a response.

"He's Mom's favorite cane. Only brought out for particularly egregious misbehavior. Please, Mom, you can't have Mr. Allen spank me with Mr. Whippy. It would be so embarrassing for him to see me naked."

"Well, young lady, from what I've heard you were perfectly happy to think of him seeing you naked last night! Tomorrow you're going to get your wish. Just not necessarily in the way that you imagined."

She turned to Jen.

"If it's alright with you, Jessica and I will come by at two o'clock tomorrow afternoon. Since Jessica prefers to behave like a schoolgirl rather than an adult, I'll have her dress in her school uniform. That'll give easy access when it comes to baring her bottom!"

I was mortified! Mom was going to make me dress as a schoolgirl before baring my bottom in front of Jen and Dave. Never mind the spanking that Mom was planning on giving me, I'd die of embarrassment right there!

Dave

====

True to her word, Rachel and Jessica were at our house promptly at two the next afternoon. I opened the door to them rather solemnly, not quite knowing what to expect. As advertised, Jessica was dressed in her school uniform; a short green and black plaid skirt and white blouse which, stretched tightly across her young breasts, made her look anything but a schoolgirl. In her hand, she was carrying a long, thin cane which she handed me without comment.

"Rachel, Jessica. Nice to see you both, though I wish it were under different circumstances," I offered sadly.

"Don't worry," Rachel responded, "we'll get this done and everything will be fine."

I've always found Rachel to be an attractive, if somewhat uptight, woman, and today she had made an effort to ensure that she looked especially good. She was wearing a classic black skirt, paired with a mustard-colored silk blouse that draped sexily across her large breasts.

She may be the mother of an eighteen-year-old

,

but she's certainly still hot and fuckable,

I thought, showing them to the family room

.

Rachel and Jessica sat together on the sofa. Jessica looked distinctly uncomfortable as Jen tried one last time to stave off the embarrassing punishment that Rachel had decreed.

"You know, Rachel, there's really no reason to punish Jessica like this. I'm sure she's sorry and repentant by now. Perhaps if she simply apologizes to Dave and I, we can put everything behind us."

A sly smile crept across Jessica's face at Jen's statement. I'm pretty sure she was thinking that, just maybe, there was hope of escaping punishment after all.

"Oh, She'll apologize for sure, Jen. But both her father and I agree that it's important that we follow through with this punishment. Now shall we get on with things?"

It was clear that there was to be no reprieve for Jessica or, for that matter, me. Last night, when Jen and I were talking before sleep, she told me about Jessica's punishment and that Rachel wanted me to use Mr. Whippy on Jessica after she was spanked over Rachel's knee. I wasn't sure I could do it. Sure, I spank Jen's pretty ass now and then when we're doing doggy but those are love taps given in the throes of passion, simply communicating to her that, in the moment, she is mine. I'd certainly never spanked her for discipline, not even with my hand, never mind the long, whippy cane that presently stood against the wall by the front door.

"Jessica, go and fetch a chair from the dining room and set it just there, in the middle of the rug," Rachel said, pointing to the middle of the room. "Then you can get yourself ready and apologize to Mr. and Ms. Allen."

Jessica stood and, looking at both Jen and I pleadingly, quietly made her way to the dining room. She was back a moment later, carrying one of our straight-backed dining room chairs which, as instructed, she placed in the middle of the room.

"Mom...please! Please don't make me do this. It's, well it's so embarrassing! I'll never do it again, I promise," she wheedled.

She was trembling but Rachel was unmoved. "Jessica, you know what to do."

Reluctantly she began to unbutton her blouse, her hands shaking as they moved slowly from button to button. Beneath she wore a white lace bra that showcased her young breasts perfectly. Pulling the blouse from her skirt, she slid it off her shoulders and folded it neatly before placing it on the chair. Her face was bright red and my cock stirred at the sight of the young, beautiful, and very vulnerable woman standing in front of us.

"Your bra, Jessica," Rachel said after a minute or two.

"Mom...please!"

Jessica's hands reached behind her back and, a moment later, she shrugged her chest forward, allowing the bra to drop from her shoulders. Two firm, perky breasts, adorned with long, pink, and very stiff nipples were now on display. I blushed and rearranged myself on the sofa as Rachel stepped slowly to the center of the room.

Jessica

======

It all felt so unreal. One minute I was being lectured by Mom and the next I was standing, almost naked in front of Jen and Dave. To say I was conflicted by my predicament would be an understatement. My pussy was flooding at the desire I could clearly see etched in Dave's eyes and the large bulge that had formed in his shorts. Yet, pleasurable as it was to know that he wanted me, I was keenly aware that the imminent spanking from Mom and Mr. Whippy was likely to be a very painful experience.

"Over my knee, Jessica. You know the position by now," Mom said quietly, disturbing the myriad thoughts that were racing through my brain.

Reluctantly I arranged myself on my mother's lap, acutely aware that the position afforded Dave and Jen an unrestricted view of my ass and pussy. I shuffled in her lap; she liked to have my bottom perfectly placed in the center with my arms outstretched, touching the floor. My face colored a deep red when she flicked the plaid skirt up, exposing my panty-clad bottom to Mr. and Mrs. Allen. It seemed funny, but right then I could no longer think of them as Jen and Dave.

"Lift, young lady," Mom's voice commanded.

Dutifully, I lifted my hips from her lap, groaning as she deftly pulled my white panties to my knees. My ass and bare, pink pussy were now fully on display and I blushed furiously at the thought. Mom's hand ran softly across my milky cheeks as she told me that she'd never imagined having to do this at my age.

Although, truth be told, the way that her hand moved across my ass it indicated that she might actually be enjoying my predicament!

I mean, did I really just feel her hand "accidentally " slide between my 18-year-old thighs? Did I actually feel her fingers flutter across my wetness? Oh my god! Was I really this wet? Of course, I was, how could I not be?

She started slowly; a soft smack to the top of my right cheek, followed by a similar one to the left. Her left hand pushed into the small of my back, holding me in position, as she gradually worked her hand down my ass and onto the top of my thighs.

"Ouch! Ouch! Mom, stop." I cried, twisting and squirming on her lap in a futile attempt to escape her steadily increasing blows.

Of course, she simply ignored my pleas for mercy and continued to spank my quickly reddening skin, working her way back up to the top of my ass. She gave me a moment of respite when she reached the top, rubbing my warm, pink skin before starting again with increased vigor.

"Jesus, that hurts, Mom! Really, it hurts, please stop!" I cried, kicking my feet and lower limbs in complaint.

This simply seemed to inflame her, and the pace and force of her blows increased, causing me to flail on her lap.