Empty Nester 04 - Conflicted
A loving MILF can't decide between the hard love of a man and the soft love of a woman
Author's note: This story is the fourth in a series titled "Empty Nester." The first story set the stage for all the remaining chapters of this adventure. All future stories will continue to chronicle the events of these three lovers. It would be best to read them in order. All characters are fictional, consenting, and over the age of 18. This story is a complete figment of my imagination and not based on any real events or characters. I love to read comments as long as they are constructive.
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"What the fuck am I doing?" I questioned myself silently as my mind grappled with what had transpired in the truck's sleeper unit with Charlie, the stark contrast to what was happening in that very moment. I had just officially cheated on my husband, crossed a line that should never be crossed. Sure I had the hall pass, but that didn't excuse the fact that I was solely responsible for causing an orgasm in another human being, a woman, a total stranger. Worse yet, I allowed her to do the same for me.
I should feel guilty my mind reasoned. I should feel ashamed. I should be begging my husband for forgiveness. Instead, I was lewdly positioned in the front seat of this beautiful stranger's big rig truck, masturbating. Oh, and not just good old fingers strumming my clit masturbation. Not even full on finger fuck penetration masturbation. No, I was fucking my nasty little cunt with a foreign object. A foreign object that was so realistic looking with its spongy bulbous head, thick veiny shaft, and natural curve. I was masturbating with a cock, a hard, cold, lifeless cock.
I was feeling very conflicted. I had just experienced the most sensual, gentle experience of my life. Charlie's body was so warm and delicate, so pleasurable. Yet, for some unknown reason, I was now forcing my body to accept a cold, hard, demanding replica of a man's genitalia. The ultimate source of male love. The contrast was so completely undeniable.
Every woman I know claims to enjoy making love to a man. Marcy always speaks so highly of her sexual rendezvouses with men, how much she enjoys a hard cock deep inside her precious body. Romance novels always seem to praise and worship men, their hardness. Why was I so different? Why did I find it so difficult to truly enjoy the love of a man?
When George made love to me in the truck for the first time, it was so raw, so primal, so unscripted. Yet, the very thought of that same beautiful man penetrating me somehow seems repulsive. When Charlie asked what it was like to make love to a man, I described the sensual feeling of his warm thick cum coating my insides, yet the very thought of it now seemed to make me nauseous. My mind seemed to be lying to me, deceiving me.
If I was ever going to truly love my husband again, I had to find a way to enjoy this thing between my legs. I closed my eyes tightly, let my negative thoughts disappear. My mind conjured up a complete stranger, a beautiful handsome stranger. A fantasy lover whose sole purpose was to teach me to love and respect his hardness. He was inside me, gently stroking my depths. I was completely lost in my fantasy.
My lover's progression paused momentarily allowing my body time to adjust to his girth, for my vagina to carefully study every detail of his shape. My beautiful lover seemed so cold and callous when he first entered my warmth. He had warmed since first penetrating, melded with my core temperature. I had hopes that he would feel more natural. Maybe even a little more personal.
We hit what seemed like an especially rough patch in the road. I could feel the jarring in my bare feet, the rattle of the loose objects on the dashboard. The truck was big and demanding, cold and hard. In my mind the truck was representative of a man.
No matter how rough the road however, I could barely feel it on my butt. Instead, the plush seat just raised and lowered on the air suspension. With my eyes closed, it felt much like riding a gentle horse on a carrousel. All I could feel was the fluid up and down motion as the seat absorbed all of the trauma of the road. The seat was gentle and caring, comforting and soft. In my mind that seat was representative of a woman.
Somehow, in that very moment, I found clarity. I wasn't masturbating with a dildo for pleasure. No, that rubbery phallic symbol in my pussy was a key, a key that would help unlock the deeply personal truths that had been safely archived in the farthest recesses of my mind.
At forty-three years of age, I was just now beginning to understand myself, my truth. My mind replayed the events that had transpired mere hours earlier. My lovemaking session with Charlie was so pure and innocent, so soft and gentle. I fast forwarded that vivid mental recording to the moment when Charlie pressed the cold, lifeless dildo to my warm and inviting body. The vivid replay now in slow motion, I could feel every detail, every emotion as the pink rubbery head of the dildo parted my tender lips, pushed against the tightness of my vagina, eased slowly inside. I could feel the stretching sensation that I had always associated with lovemaking. I could feel my love muscle hug and embrace the strange foreign object. More importantly, I could feel myself reject it, try and expel it. For some reason that pink phallic impersonator felt so completely repulsive to me.
The jarring of the truck reminded me of the obscene position my body was currently in. I didn't need to open my eyes to fully understand what a sight I must have been. My knees were parted wide, my bare feet planted firmly on the dash, and "
he"
was inside me. "He" was pink and hard. "He" was warm, but not from his own internal heat source. No, he was only warm because my body provided the heat, that intimate warmth that only exists deep inside a woman.
I could sense that my pussy was moist and tolerant of the pink cock, but not overly wet and slippery like it had been with Charlie's fingers. I thought for a moment about her long slim fingers, the way they gently toyed and caressed deep inside my pussy. The mere recollection of those loving fingers caused a gentle flutter inside me as a silky wetness coated the pink cock. It wasn't the cock that was responsible for the warmth and wetness. No, it was my brain, the memory of a woman loving me so tenderly.
I was certainly no expert on female masturbation let alone masturbation with a dildo. One would think that a dildo would be pleasurable, serve as an aide to the ultimate end game. For some reason, my pussy didn't seem to like it. I felt the need to better understand why.
Using two fingers at the base, I pushed the phallic impersonator deep into myself. Once fully seated, I tightened my pelvic muscles, forced my pussy to hug it tightly, show it love. I removed my fingers and could immediately feel it slip. I tried with all my might to hold the rubbery object inside my body without the aid of my fingers. My attempts were futile. It slowly creeped outward, slithered from my grasp. No matter how badly I wanted to keep it inside, I couldn't hold it in my grasp. I couldn't love it.
Over and over, I pressed the dildo deep into my pussy and removed my fingers. Each time it slithered out leaving me feeling empty and sad. I could feel my eyes start to well up as a deep sadness spread throughout my very being. This wasn't about a rubber toy, it wasn't about masturbation, this was much deeper than that. Tears started rolling down my cheeks.
"Ya'all doin alright over there?" Charlie's soft tone barely audible over the loud roar of the engine. "That's not the face I would expect to see on someone with a big hard cock slip'n in and out of that pretty little pussy. What's wrong?"
I let out a deep sigh as I finally let the dildo drop into my hand. It was clear that my body was rejecting it. Perhaps, more accurately, my mind was rejecting it. Maybe, I just wasn't capable of being loved, of loving.
"Ya'all need a little help with that?" Charlie asked in a tender caring voice.
"No," I politely responded. "You need to keep your eyes on the road."
"It ain't my eyes that'd be doing the work. Shoot, I used to use that thing on Cassie all the time as I drove," Charlie replied with a naughty little chuckle. "Makes the long days go by much quicker."
Charlie reached into a seat pocket and tossed me a folded hand towel. "Slip out of them undies and put that under your butt. Don't wanna be staining the seats."
I just smiled and chuckled. I slapped the base of the glistening sticky dildo against the metal dash of the truck. The suction cup on the bottom held it firmly in place. Charlie and I giggled like school girls as we watched the pink cock sway and bob obscenely with each bump in the road.
I lifted my butt and slid the soft cotton panties past my hips and down to my ankles. I carefully folded them and set them on the mattress in the sleeper. I spun my butt around in the plush seat until I was facing Charlie, then slipped the towel under it. Charlie just watched silently with a big beautiful smile on her face.
