Empty Nester - The Awakening

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A beautiful MILF grows sexually as an empty nester.
9.5k words
4.56
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Part 1 of the 7 part series

Updated 04/04/2025
Created 01/27/2025
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Empty Nester - The Awakening

Author's note: This story is relatively long and takes some time to develop, so if you are looking for instant gratification, this might not be for you. All characters are fictional, and this story is a complete figment of my imagination.

...

Hi, my name is Jodi. I am, or I guess was, just a normal boring housewife that was hit hard by empty nester syndrome. It all happened so quickly. My life changed in ways I could never have imagined. I can't believe I am actually writing my story. If it weren't for a little encouragement from my best friend Marcy, I am one hundred percent sure you would not be reading this.

We had a great life; myself, my husband George and our baby Jackie. Well, not technically a baby I guess since she was just about to head off to college. God how did that happen so fast. It seems like only yesterday that I was pushing her out of my tight little vagina. I was so naïve back then. Obviously, I knew enough to get pregnant, but in actuality knew very little about my own sexuality. To be honest, I couldn't even bring myself to say the word vagina back then. There I was, twenty-three years old, spread eagle with everyone staring at my crotch waiting for a baby to pop out. I don't think most young girls really think this through completely, but all sense of modesty quickly goes out the window as, what seems like a room full of strangers coax a baby out of your most intimate and private place before poking, prodding, and wiping everything down there. Unfortunately, that experience only served to further deteriorate my sexual self esteem. After giving birth, I could barely disrobe long enough to shower, and intimacy only served to remind me of the whole ordeal. Sex became a chore that was reserved for the darkness of our bedroom, and only under the cover of thick blankets. As far as I was concerned, no one, including my own husband ever needed to see what was hiding between my thighs ever again.

Needless to say, our mediocre sex life became even less momentous after Jackie arrived. I know George wanted more. He made a point of scheduling a date night at least once a month that generally ended in some fairly energetic lovemaking, by our standards at least. At best, intercourse happened a couple times a month. I always felt bad when I would detect the bed moving next to me while I pretended to sleep. It seemed to happen a couple times a week, and I just knew that George was masturbating to some unknown fantasy that most likely didn't include me. I just couldn't seem to find a way to enjoy sex. To be honest, I never had much of a libido. Sex just seemed like a messy necessity, something that a good wife was expected to do.

...

"Hey mom," Jackie's voice interrupted my early morning slumber. "Wanna help me pack?"

I let out a deep sigh as I rolled out of bed and slipped into my bathrobe. I had been very depressed for the past couple of weeks, dreading the day that Jackie would leave for college. Well, it was happening, so I needed to make the most of our last day together.

"Sure," I replied.

I was a little taken aback when I pushed her bedroom door open and saw all of her tiny little bras and panties spread across her bed. It is not like I hadn't seen her underwear before, I did do the laundry after all. They just seemed so skimpy laid out on the bed. I spotted one lacy little thong that I had never seen before. It appeared to be new. I picked it up and unconsciously slid my fingers over the tiny silky gusset. An uninvited image of my innocent little Jackie wearing these suddenly flooded my mind. Did she keep herself trimmed down there? OMG, did she wax? I could feel my face blushing. I felt an embarrassing and unexpected tingling sensation deep inside me that I hadn't felt in a long time.

"Mom!" Jackie's voice interrupted as she snatched the panties from me. "What is up with you? Why are you blushing?"

"Sorry," I responded, trying to shrink into my bathrobe. "I guess I was just imagining what it would feel like to wear something like that."

"Hmmm," Jackie pondered with a cute little giggle. "I think you would have to do a little landscaping first. Do you still have that massive bush?"

I just gave her the best version of the mom eye I could muster in the moment. "Are you, ummm, you know?" My eyes drifting downward on her body.

"Bare?" Jackie interrupted. "I've been waxing for a few years mom. Everyone does it. You should try it before judging."

"Doesn't it hurt?" The words just came out before I had time to think. Did I really want to have this conversation with my daughter?

"Fuck yes," Jackie blurted out. "Oh, sorry. I didn't mean to use that word."

"It's okay, I know you and your friends use that kind of language." I paused for a minute, pondered what the process must entail. I couldn't imagine a more intimately invasive procedure aside from childbirth. It must be humiliating. "Is it worth all the pain and embarrassment?"

"You know how soft and smooth your legs feel after shaving, right?" Jackie responded with a smile. "Well just imagine how silky smooth your pussy lips would feel, especially if you were wearing this." Jackie held up the silky thong as her fingertips slipped seductively inside the tiny little crotch panel. "I love it when a guy kisses my bare pussy," Jackie added, knowing how squeamish I would get with such a graphic sexual reference.

"Do you think your dad would like it?" I retorted with the hopes of turning the tide of embarrassment. As soon as the words left my mouth I panicked. "On me, I mean, oh damn, I mean.. you know, if I did it." My hand covered my eyes as my face turned all shades of red.

Jackie smiled slyly. "He would fucking love it," she blurted out. "OMG, he would so go down on you. I was planning to get a little touchup before heading off to college. Wanna come with me, you know, a little mother daughter bonding time before I leave?"

I could feel the flush spread from my face down my neck and over my chest. That tingling feeling intensified as I imagined George's lips gently kissing a newfound silky bareness down there. He had hinted many times over the years that he wanted to kiss me down there, but I was always just so hairy and couldn't possibly imagine letting him do that to me. My breathing was becoming irregular as the inappropriate fantasy dominated my consciousness.

"Earth to mom," Jackie joked. "Thinking about dad going down on you, aren't you. Maybe you need a little alone time. Wanna borrow my vibrator?"

I took a deep breath and shook off the fantasy. "OMG Jackie, that is disgusting. I am just having a hard time wrapping my head around your leaving for college."

"Yea right!" Jackie retorted. "Pretty sure you were thinking about wrapping around something hard but probably not so much about me leaving."

"Jackie!" I reprimanded as tears started streaming down my cheeks.

"Sorry mom," Jackie whispered as she wrapped her arms around me and gave me a big hug. "I know this has to be hard, no pun intended, especially since dad just started his new job and all."

Jackie was right. George's company shut down six months earlier and he decided to go to truck driving school. We thought he would be able to find a job driving locally but ended up signing on as a long-haul driver. He had departed on his first trip two weeks earlier and wouldn't be back home for several more days. I had never spent a single night home alone, ever. Jackie would be leaving in the morning, and I was terrified.

There was a brief pause in our conversation. I was simply too embarrassed to speak and Jackie seemed to be pondering a question that she wasn't sure how to ask.

"Don't you masturbate?" Jackie suddenly questioned cautiously. "I guess I've never actually heard you and dad having sex, but just figured you took care of your own needs. Especially now that dad will be gone for weeks at a time."

I took a deep breath, paused before responding. My eyes stared a hole in the bedspread, not wanting, or perhaps able to make contact with hers. "I grew up in a different time Jackie. Girls weren't supposed to do that kind of thing. I wouldn't even know how to do it."

"Come on mom," Jackie's surprised voice questioned. "Are you honestly going to tell me that you have never touched yourself? I suppose the next thing you will tell me is that you have never had an orgasm. It's not rocket science. Besides, my Gyno told me it is healthy to get to know your own body. I do it all the time, it feels incredible." Jackie giggled and blushed. "Don't you remember a few months ago when you walked into my bedroom unannounced because you heard a strange noise? Yup, busted."

I tried hard to shake off that vivid image. "I'm not completely incompetent sexually," I countered defensively. "I am pretty sure I've had an orgasm or two in my life. We did manage to make you after all."

"An orgasm or two?" Jackie shrieked. "Damn mom, you need this way more than me."

Jackie reached into one of the pockets of her suitcase and pulled out a small, sealed box. She tore the plastic off the outside and pulled out a slim pink vibrator. She plugged the cord into her phone charger and set it on the bedside table to charge.

"I picked this one up for college," Jackie announced proudly. "My old one still works just fine so you should have this. It has variable speeds, so start out on low and see how it feels. All I do is touch it to my clit to get started, then just use my imagination."

I was thoroughly embarrassed as my daughter schooled her old mom on the proper way to masturbate. Just exactly when did it become okay for women to do that kind of thing? What was this world coming too?

Jackie picked up the pink toy, flipped it on and touched it to the end of my nose. "This should get you off," she said with a smile. "You can use it on those too," Jackie said with a smile as she motioned the vibrator towards my breasts.

I didn't need to look down. I could feel how hard my nipples had become, and knew they were on full display through the layers of concealment. I let out a sigh.

Jackie and I spent the next few hours laughing and crying as we talked, reminisced, and packed. She wasn't kidding about having more than one vibrator either. I guess we never really had the "talk", yet she seemed so sexually astute. In hindsight, I learned a lot from her that day. Who knew guys really liked to kiss girls down there. God I was naïve.

...

As I prepared for bed that evening, my conversation with Jackie was weighing heavily on my mind. Was I the prude my daughter seemed to think I was? I looked at my long thick nightgown and wondered why I felt the need for such extreme coverage while I slept. It wasn't like anyone was going to walk in on me while I was sleeping, and the many layers of blankets would sufficiently shield me if someone did. I took a deep breath and reached to the back of the bottom drawer of my dresser. I pulled out a short thin little nightgown that George had gifted me many years ago and held it up. It's not like it was overtly sexy or sheer, but it would do little to conceal my physique. "Fuck it," I whispered to myself before checking in the mirror to make sure little devil horns didn't suddenly appear on my head.

As I slipped the nightgown over my naked body, the thin silky material sensually tickled my sensitive nipples. When I checked myself out in the mirror, my butt was barely covered, and those pesky nipples were on high beam. Instinctively, I covered myself by cupping my breasts with my hands as I climbed into bed. I looked over at the bedroom door to make sure it was closed tightly before pulling the blankets up snuggly around my chin. I felt so naughty, so rebellious. My heartbeat was slightly elevated, an energy flowed through my body. Every time I closed my eyes, I conjured images of vibrators and sweet little Jacki's smooth hairless vulva. Very carefully, almost as if I were trying to conceal my motions from some non-existent onlooker, my hand slid down my side and pulled the thin nightgown up to my waist. My fingers crept across my thigh and came to rest on my curly bush. I glanced at the door again before allowing my legs to gently part. I took a deep raged breath and let out a sigh.

As my fingers toyed and twisted in the long curly locks, I couldn't help but wonder what it would feel like with no hair down there. My fingers carefully traced the outer perimeter of my vulva, focusing on that sensitive crease between thigh and vulva where no hair grew. The skin was so soft and smooth. My other hand joined in on the action. I fantasized that George was beneath the covers with his head nestled between my legs, his hands gently pulling my thighs apart. As my own fingers kneaded and pulled the soft flesh of my thighs, I could feel myself gently open. In my fantasy, George was kissing the tender flesh of my thighs, his lips so dangerously close that I could feel his breath tickle the silky fine hairs that guarded my pink opening. I could feel something cautiously exploring, circling, carefully penetrating. In my fantasy, it was George's tongue. In reality, it was my own fingertip.

The combination of fantasy and my own touch had me breathing heavily. My legs widened as my knees lifted and separated. I could feel, no hear my heartbeat. I pushed the heavy blankets down until the cool night air licked at my thinly veiled breasts. The sensation only adding to the heat that was building between my thighs. The exploring fingertip slid deeper into the moist crevasse as my pelvis rocked seductively. My head pressed back into the pillow as that naughty little finger teased deeper, pushed past the outer barrier. Sensing imminent invasion, my pelvic muscles tightened ever so gently causing the moist flesh to tightly hug the invading finger.

"God that must feel nice on a penis," I thought as my curious little finger explored my own intimacy for the first time. A warm wet slipperiness signaled approval to enter as the finger pushed deeper. A soft moan escaped my lips. My free hand slid up my torso, its fingertips trailed across the sensitive underside of my full breasts. My stomach filled with butterflies as the anticipation grew. I was going to do this; I was officially masturbating. A gentle peace set over my otherwise sexually tense body. My vagina hugged and comforted that adventurous finger, nourished it with nectar. I was in heaven.

Without warning, my thighs slammed together, trapping the invading digit between the soft warm folds deep between my legs. I scrambled to pull the covers up with my free hand in an attempt to hide the indecent activities below. It was a sound, the sound of Jackie's bedroom door opening. I held the covers tightly around my neck as my body trembled, badly needing more attention while at the same time frozen in fear. I could hear footsteps in the hallway. For what seemed like an eternity, I lay there helpless, my heart pounding. I listened intently. I could hear the flush of a toilet, footsteps, the closing of a door. I took a breath, continued to listen. It was over. I adjusted my nightgown and closed my eyes. The combination of embarrassment and relief caused me to chuckle nervously. That special moment was over. A sense of shame replaced the sexual tension. The faint scent on my sticky finger was the only evidence remaining.

I tossed and turned all night. The burning sensation deep in my loins and tension between my legs never fully subsided. My dreams were vivid, raw, and wet. I woke with a silky dampness between my thighs as I tried unsuccessfully to recall the details of my dreams. "Women don't have wet dreams," I whispered to myself. The slippery mess between my legs told a different story.

...

I held my bathrobe closed tightly as I waved goodbye to Jackie from the front door. A heavy weight settled in my chest. I was alone for the first time in my life. As much as I wanted to crawl back into bed and have a good cry, I decided I should jump in the shower before getting busy clearing out Jackie's bedroom. George and I had decided that we would convert it into an office after she left for college. A little physical labor right now would help get my mind off the embarrassing conversation from the previous day and the vivid dreams that resulted. First though, I needed to take care of that sticky little mess between my legs. My whole body seemed overly sensitive. That nagging tingly sensation was back. A cold shower would do me good.

As I stepped out of the shower and dried myself, it quickly became apparent that the cold shower wasn't completely successful. The soft towel on my sensitive skin brought that tingling sensation back. I could feel butterflies in my stomach as I gently patted myself dry. I started to reach for my bathrobe when it occurred to me that I was alone in the house. For the first time in my life, I walked out of the bathroom completely naked. It was terrifying, but somehow tantalizing. I strolled over to my dresser, my breasts swaying freely with each step. I felt a sense of empowerment. I bent to reach for my underwear drawer and caught sight of my nakedness in the dresser mirror. The fullness of my breasts, the hardness of my nipples on full display. As I pulled the drawer open, I immediately spotted the pink vibrator. I had declined Jackie's offer the previous day, but apparently, she thought I really needed it. I took a deep breath, picked it up and sat back on the bed. I flipped the switch and felt the tingling buzz in my hand.

I just stared at the smooth humming plastic as a feeling of doubt creeped into my mind. How could I cheat on George like this? This wasn't right, I couldn't do this. My mind and body were at odds. That tingling sensation deep within me grew more intense. A naughty voice in my head begged me to satisfy my cravings. I wanted so badly to slip the vibrator between my thighs, touch it to my eager clit for the first time. I could feel my nipples grow longer and harder, begging for attention. I had always been embarrassed by my breasts. Their full teardrop shaped D cups with long thick nipples. I always hated the stares I got when my nipples suddenly decided to push through the thick padding of my bra, those obscene protrusions that always drew eyes downward. Now they were begging for attention as well.

From my position on the bed, I could see a beautiful naked woman in the dresser mirror. The thick patch of hair protruding from between her thighs, large full breasts with long hard nipples crying for attention. I studied the reflected image, that of a woman whose hands would surely disobey her mind. While the reflection looked like me, it couldn't be me. This sensual, beautiful woman was in need of sexual gratification, and she would have it.

The pink vibrator moved closer to her left breast; the woman pressed the humming vibrator to its nipple. A sudden burst of energy, a shock if you will, seemed to engulf her nipple sending a magical sensation through her body and deep into her loins. Her vagina clenched tightly. Her free hand instinctively moved to her right breast as the little buzzing magic wand pressed and rolled over the subservient nipple of the left. My eyes stared into the mirror; my mind could no longer differentiate between fantasy and reality. I could hear a soft moan. Was that her or me?

I closed my eyes and took in a deep breath as I lay back on the bed. My legs parted slightly as the buzzing vibrator slipped cautiously down my torso and through my thick curly muff. My hand trembled as the magic wand slid ever closer to its goal. It carefully pressed into the soft flesh of my mons, the vibrations gently ringing outward in every direction, tickling at the thin covering of my little clit. I could feel it grow, tingle. It pleaded for more direct attention. My entire vulva grew warm to the touch, engorged, cried for attention. I could feel my lips gently part, begging to be fed, ready to swallow.