Empty Nester 04 - Conflicted

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.

...

"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.

"Eyes on the road," I scolded. "Jesus, the last thing I need right now is for us to get in an accident."

I carefully placed my left foot in Charlie's lap and pressed the heel into the crotch of her jeans. I stretched the other leg out and planted it on the dash just inches from the obscene flailing dildo. As I settled my back against the door, I scooted my butt towards Charlie and pushed both knees out wide. I was so completely exposed, so vulnerable.

"Oh my," Charlie's voice shrieked. "I knew ya'all were bare down there, but the light was so dim in the sleeper, I never got a good look. Them little lips are really cute."

"The road," I reminded with a nervous chuckle. "Do you like it?"

"I'm kinda partial to the bush," Charlie responded hesitantly. "But damn, you can sure see every detail."

"Me too," I replied. "I really miss the hair. I feel really exposed without it. This was just one of those spur of the moment things that happened while I was drunk. I have already decided that I'm going to let it grow back."

Charlie let out a deep chuckle. "Spur of the moment like ya'all two fillies forgetting to pack any clothing?"

"Something like that."

I gently slid my hands over my widespread thighs, my index fingers both gently caressing my swollen vulva. I pulled outward on my thighs. I could feel my moist lips part. The cool breeze from the truck's air conditioner tickled over my sensitive pussy, the contrast between hot and cold sent shivers up my spine.

"I need you Charlie," I pleaded as I allowed my eyes to open slightly. I could see her dainty hand reach for the pink dildo. "No Charlie," I said quietly. "I need you, your loving touch."

I reached over and took her hand into mine, pressed it into a fist leaving her two middle fingers extended. Her hand felt so soft and smooth as I gently stroked her extended fingers. As I pulled them close to my crotch, the anticipation seemed unbearable. I guided her slender fingers to my entrance, gripped her wrist and pushed them deep inside. I didn't want foreplay. I didn't want teasing. I just wanted her inside me.

I inhaled sharply, held my breath. The sensation felt incredibly personal. I carefully pushed and pulled on Charlie's hand, pistoning her long fingers in and out of my wet hungry pussy, stroked my love tunnel.

"Let me," Charlie said in a warm sensual voice.

I released my grip on her hand, slipped my hands under the T-shirt and gently cupped and caressed my sensitive breasts. My eyes were closed tightly, I could feel every intimate detail of her fingers inside my trembling pussy.

"Let it go," a soft caring voice said. I wasn't sure if I had imagined it, or if that was Charlie's voice I heard. The most peaceful feeling settled over me. "Let it go," the soft voice repeated.

I could feel tears begin to stream down my cheeks. I could feel a fluttering sensation deep inside my womb. I could feel Charlie's loving fingers. My body wasn't trying to reject these loving fingers like it did the dildo. It was pulling them deeper, holding them tightly.

I took a deep breath, let it out slowly. "Oooooooohhhhhhhhhhhhhhhhhh," was the sound that escaped my lips over and over as wave after wave of pure pleasure surged through my fragile body.

When it was over, her fingers stopped moving, remained deep inside. I had never felt so completely at peace with myself, the world around me. I pictured my beautiful daughter Jackie, my loving husband George, our perfect little family. I began to weep uncontrollably.

An embarrassment suddenly set over me. I tried to conceal my nakedness as I slid back in the seat, causing Charlie's fingers to slip from my body. I cleaned myself with the towel and slipped the panties back on. As I made my way to the sleeper, leaned over and kissed the beautiful truck driver.

"Can you call George and see if it would be okay if we stopped at the next rest area?" I whispered in her ear. "I really need to see him."

"Absolutely," Charlie responded.

Charlie never questioned my tears, my reaction. It was like she could read my thoughts and emotions. Oh, how intuitive and understanding women are.

...

I was laying in the sleeper, curled in the fetal position gently cradling and rocking my body when I felt the truck begin to slow and stop. I draped the robe over my T-shirt and panty clad body and climbed out of the sleeper. I cradled Charlie's lovely face in my hands and kissed her pretty lips.

"Thank You," I whispered. "I really needed that."

I ran over to George's truck. Marcy was just climbing out of the passenger seat and down the step of the truck. I wrapped my arms tightly around her body and kissed her sweet lips. I pulled back, locked eyes with her, and said, "I want you Marcy. I need you to make love to me, tender passionate love. Our lips met again. Our tongues explored as we held each other tightly.

"I know," Marcy whispered. "But not here. Not like this. I want to make love to you in the comfort of your bed, beneath the silky soft sheets."

"Yes!" I rejoiced. "Me too. First though, I need to talk to George. Would it be okay if you rode with Charlie the rest of the way?"

"Of course," Marcy responded.

...

"I love you so much George," I said as we got back on the road. "I don't think any other man would have been so patient with me or allowed me the freedom to truly find myself. My real self, I mean. I think I had an epiphany when I was with Charlie. I think I now understand why I have struggled with love since Jackie was born."

George just looked over at me, his smile so warm and genuine. "Tell me about it."

"Do you remember how depressed I was when we got home from the hospital after giving birth? How I couldn't even bear to look at our beautiful little baby let alone hold her in my arms? God, I felt like such a failure, such a pathetic excuse for a mother."

George reached his hand over and took hold of mine. "Postpartum depression, according to the doctors. I remember it well. You seemed to get past that after a couple weeks though," George reminded.

"But I didn't George. I just buried those awful feelings, internalized everything including my hatred for you."

George suddenly pulled his hand back, a serious look covered his face.

"It wasn't that I hated you George," I said as I reached for his hand and squeezed it tightly. "I hated the idea that you were the root cause of my deep depression. In fact, it wasn't even you, but rather your cock. That was the thing that impregnated me, put me through the pain of childbirth. It was the thing that always wanted attention, stretched me to the breaking point, pumped me full of its seed. When we had sex, I didn't feel love, but rather fear. I was so afraid of getting pregnant again. Sure, I was on the pill. That didn't seem to stop the fear."

George gently squeezed my hand, pulled it close to his face and kissed it. "Why didn't you tell me," he asked.

"Because I didn't know George. I didn't understand those feelings. I was numb. I wanted so badly to have a happy family, a peaceful existence. I really do love you George. With all my heart. I just need some time to forgive that big cock of yours."

George just chuckled. "And how exactly does that work? The two of you kiss and make up?"

It will take time, but it will happen. Unfortunately, I can't take care of your needs for a while. I can't make love to you until I figure out how to move forward."

George let out a long sigh. "So, are we talking separation? Divorce? I just can't imagine a life without you. I love you so much. I love calling you my wife. God, what would that do to Jackie?

"I have a better idea," I interjected. "Just hear me out please."

George nodded, listened attentively.

"That beautiful cowgirl up there in that big truck in front of us, she needs a man. She will turn thirty next month, and is desperately wanting to start a family. We had a very intimate conversation, and she asked about you. She asked if maybe, you could be the man to love her for the first time, make her a mother."

I paused for a moment to let the idea settle into George's mind. I knew his first reaction would be no, but I needed him to think before responding.

"I know you always wanted more children George. I know that Jackie always wanted a baby sister. I can't give that to you, I just can't. As much as I want to give you more babies, I just can't bear the thought of going through that again. Charlie can give that to you. You can give that to her."

I paused again, let George think for a minute.

"So, what exactly would that look like," George questioned after a couple minutes. "You and Marcy move in together and Charlie and I live somewhere else?"

"No silly," I responded with a chuckle, trying to lighten the conversation a little. "There is no way I am going to let that little cowgirl ride off into the sunset with you. Not a chance buddy. Don't forget, I want you in my life. I want your cock in my pussy. Just not right now."

"Okay?" George said in a questioning tone.

"So," I continued. "Charlie is about to lose her truck to the bank. Without a co-driver she can't make the payments. I am proposing that we mortgage our house and pay off her loan. The two of you can roam the country and make a baby in that oversized sleeper while Marcy and I make love in a real bed."

George chuckled, a smile appeared on his face. "Damn, that does sound kind of fun."

"Oh, it gets better," I assured. "Marcy has been looking for an investment opportunity for that chunk of cash she got after her great aunt died a while back. I think she might be willing to buy a second truck."

George's smile turned into a question mark again. "Wait, I thought I would get to team up with Charlie. Why a second truck?"

"For Marcy and I silly. Well actually, for which ever couple is fucking each other at the time. We are all girls you know, and we all still get our periods every month. You can team up with Charlie when she is fertile, and Marcy and I will team up. When Charlie is on her period, you can team up with Marcy, and I will team up with Charlie. Sounds like a win win for all of us."

George seemed dumbfounded. He just sat there shaking his head.

"I still need to talk to the girls of course. I am just spitballing right now. So what do you think?"

George didn't respond. Instead, he reached over to his phone and pressed redial.

"Hello," a husky southern accent answered. "What can I do for ya'all."

"What does your schedule look like after your Dallas drop?" George asked.

"Still trying to find a new load," Charlie responded. She giggled as she continued, "I was hoping to find a really big load, something that would fill me to full capacity, something I could ride all across this beautiful country."