The Do-Over

The Do-Over

By Stephanie Gilbert

Copyright 2024 Stephanie Gilbert ©

All characters in this story are totally fictional and over the age of eighteen. No A.I. was used in creating this story.

The beginning or the end

The sea was getting very rough, so I went to the Captain's cabin. I was being tossed from one side of the tiny passageway to the other, bumping off the bulkheads like a ping-pong ball. I pounded on the hatch twice, before opening it to find the Captain's back to me.

"It's pretty rough out there, Cap," I yelled, but got no response.

I shook his shoulder, and an empty bottle of rum fell to the deck, rolling to my feet before being sucked under the bunk, by the pitching boat.

"Get the fuck up!" I yelled into his ear, at the top of my voice.

He grumbled and tried to pull the covers over his head, but I was much quicker. "I need you at the helm."

I half pushed, and half lifted him through the short passageway to the bottom of the ladder and up into the wheelhouse. When we got to the top, his eyes opened wide. "Fuck!"

It had worsened in the minutes I took to get the Captain. The waves lashed the deck, and the wipers struggled to clear the screens. "Get the life jackets from under my bed," he ordered.

This wasn't good, and I rushed back down the stairs as he turned us into the waves. I heard the crash as a wave pounded the bow and began pulling the best life jackets from the storage under the Captain's bunk. That's when the lights dimmed for a second, then blinked twice before everything went black. It was like being in a washing machine as the top became the bottom, then the top again. Things hit me from all sides, as I was crushed against the roof with the mattress.

Then it went quiet, only the sound of the creaking hull. Fuck, this was it. We were under the waves, sinking to the bottom. I pulled out my phone and turned on the light. I could feel the water coming in around my feet. I pushed myself out from under the mattress. I crawled upward to the boat's bow. I felt the bump when we hit the bottom, than everything was still. The water rose until it was at my waist, then slowed to a trickle.

"Fuck." I yelled, then punched the hull, but it was as solid as a rock, only hurting my hand.

"Maybe this is what I deserve," I thought to myself. I had wasted my life worrying about all the wrong shit and working my ass off almost every waking hour. And what did it get me? Divorced and broke, estranged from my family. What a fucking mess. It's Christmas Eve, all I want to do is go back and hug my Mum, one more time. She died a year ago, so I heard, but I hadn't seen her in many years.

Then it hit me; no one will give a shit that I've gone. There will be no grieving; my wife hates me, and I don't blame her. I was never there. But fuck it, I still love her after thirty years of marriage! The water was at my chest, and I was finding it hard to draw breath. I had a few minutes of battery life on my phone, so I typed a message in case anyone found it.

"There have been a thousand decisions in my life, and I think I made every one of them the wrong way. Except marrying Dianne and having our children. If you find this, know I regretted all the others." I typed, as the water reached my chin.

I was so cold that even the shivering had stopped. I was at peace as my body surrendered to the water.

1969 again

I was sitting in the chair at the end of the kitchen counter, with my coco pops crackling away in my bowl. Mum was on the other side of the counter, washing the breakfast dishes. I had seen this scene before, it was a fleeting memory. Mum came around to help me off the chair, but I held out my arms, and the hug felt just like I remember, warm and soft as I snuggled into her neck. "I love you, Mum."

"Oh, I love you too, Honey," Mum said, a little taken aback by my words, as I vowed to say them more often.

My little Sister was crying in her bouncer. She did that a lot. I remember it pissing me off the first time around, but then I looked at Mum's face and saw the effect it had on her. Mum picked Sandy up and sat in the chair, and as she tried to get her to settle, I put my hand on her arm. "It's alright, Mum, she's only crying."

By the time Sandy was walking, her crying was a thing of the past, mostly, and Mum's post partum depression had passed with it. I hope I helped, rather than added to it, like last time. I had little control over my life, which would remain that way, while I lived under my parents' roof. I tried harder at school but stopped myself from jumping ahead. I didn't want to change where I ended up too drastically, as the people I met and the friendships I developed would eventually lead me to Dianna.

I spotted Mum looking out the window as Sandy was screaming. I stood back with my arms folded as Mum opened the back door. "Mum, he hit me." She shrieked, and even had real tears in her eyes.

"From over there?"

"Yes, he ran over here, hit me... then ran back." She said, stopping to think mid-lie.

"Come over here," Mum said sternly, and Sandy smiled.

"No, you."

When Sandy finally approached, she got a quick swat on the bottom and was sent back to the sandpit, crying. "Next time, I will really give you something to cry about, if you lie to me again!" Mum said, going back to her housework.

Dad, as it was in those days, came home from work via the pub. He would be a little tipsy and cuddle Mum and squeeze her bottom while Mum tried to get his dinner from the oven. Then he would chase us around the lounge and dining room, trying to tickle us. His prickly chin scratched our bellies, as he blew bubbles.

His job was to tuck us in at bedtime, and it was just as I remember. The bear of a man carrying my limp body over his shoulder, throwing me into the bed and pulling the covers up under my chin. "I love you, Dad," I said through my yawn.

"I love you too, little man."

1980's

The last days of school were a struggle, just like the last time. The school was trying to keep a lid on things, but the eighteen-year-olds, that most of us were by then, could drink, smoke, and drive a car; but still had to take orders from teachers that we had come to realise, were as fucked up as we were.

Sister Mona was the worst! She had hated me from the Mument she first laid eyes on me. I had tried to rationalise her actions, but she was just a bitch; and there was next to nothing I could do about it. I decided to give it one more try, before I left. Her status as the assistant principal gave her authority over all the students, and she used it to instill fear into everyone.

I only felt pity. The first time I thought she was ancient, but she was really only in her late thirties and had never had a good fuck. Frustration was her problem, I surmised, and I would try to solve that for her. I had one chance coming up as, from memory, I would be dragged through the empty halls of the nunnery to do some painting, as penance for an outburst in class. I think most of the maintenance and gardening got done that way.

As predicted, she had me in the hallway across from her small brick bedroom, painting the kickboard, as she folded her delicates. "You get to have sex before you enter the convent, Sister?" I asked, still painting.

I heard her gasp and stop her folding. Then she fumbled around for a Mument, before answering. "No, I would never."

"Don't you wonder what it would be like to have a man hold your naked body against his?" I said, and I saw, from the look in her eyes, that it was exactly what she dreamed about.

"That's enough!" She said, with some conviction.

"You have the same bits under that habit as every other woman. You have desires and longings like the rest of us. I bet you play with your clit and dream about having a cock inside your pussy just as much as the rest of humanity. No, more; because you have never had it."

"Stop it this instant."

"I could lick your clit, while I put one finger in your pussy and one in your ass. I could give you the best orgasm of your life right here, right now, and no one will ever find out. All you have to do is ask." I said, looking her in the eyes.

She huffed, her stare hard as she tried to remain as cold as I remember. "The whole school would know by lunchtime."

"Have you ever heard even a whisper about any of my girlfriends? Loose lips sink ships." I said, taking a chance, dropping the paintbrush, and crossing the hall to her doorway.

"I..."

I reached out and cupped her breast through the stiff fabric and felt her warm flesh beneath. Her posture softened, and I knew we had passed a hurdle. "The Convent is empty. It's just us. Take this scratchy shit off."

She took hold of the sash around her waist but stalled for a second, so I began unbuttoning from the top. This was enough urging for her to continue. I helped push the top to reveal the most unflattering bra I had ever seen; even Mum's were more delicate than this. I reached behind her and deftly undid her bra strap, and she looked at me, shocked.

"Where did you learn that?"

"A gentleman never tells," I answered, but silenced her by cupping her bare breast and pulling on her nipple.

I took control from there, pushing her back on the bed and pulling the habit down her legs and off her feet. Her body was surprisingly nice under all the clothes. Her legs were long and slender, and her pussy hair flattened to her mound. I pushed her knees back to her chest and then to each side to reveal her.

"I don't think..." She started, but I kissed her clit, and her words died in her throat.

She was wet. My finger slid into her pussy with no effort and then a second, as I licked circles around her clit. She let out a sigh when I flattened my tongue and lapped at her nub. She was mine for the taking; I had her body quaking at my touch. I should pull away now and leave her hanging, wondering for eternity how my cock would have felt.

I pulled my fingers from her wet opening and spread them, slipping one into her tight ass and the other back into her pussy. She bucked up to my mouth, her pussy pressing to my tongue. I reached across her body with my free hand and pinched her nipple, rolling it between my fingers and thumb.

She was writhing under my assault. Her body rolled and shook, as she got close to her orgasm. I tempered my caresses and held her close to the edge, slipping a second finger into her dripping pussy, to keep her rocking. She looked down her body in frustration and locked her eyes on mine as I licked and sucked her clit. I drove my fingers hard into her body and concentrated on her clit, pushing her over the edge.

She stiffened and grunted, as her climax crashed through her body in waves. Her ass and pussy contracted around my fingers as she gripped my hair, pushing me tightly to her spasming pussy. "Aaarrrraarrrr," She moaned, as her orgasm ripped through her, finally releasing my head, as my breath was running out.

I pulled out my fingers and moved up over her body, pressing my hard bulge to her pussy, as I kissed her with my pussy juice-covered mouth. As expected, she began to protest, pushing me to the side as she looked at the lump in my pants. "What have I done?"

"You had an orgasm, a big one," I said, undoing my belt.

"This was a mistake. I can't have sex with you."

"You already have."

"That wasn't..."

"Well, it was sexual relations..." I started, but realised that Clinton hadn't been elected yet. "This was very natural and incredibly good. You had a huge orgasm that your body needed. The thing, about nuns and priests not having sex, didn't come about until over a thousand years after Christ died. You guys made that shit up later, to make you all look more holy or something. Trust me; this will cause more problems for the church in the future."

She was stunned by my counter to her argument and hadn't even noticed that I still had hold of her nipple. "Now, are you going to return the favour or let me use this condom in my pocket?"

"I've never."

"Your hymen is gone, so it won't hurt." I offered, and she glanced at her hairbrush.

I took her hand and placed it on the front of my pants, giving her permission to explore if she wished. She didn't move for some time but continued to argue that this was somehow wrong. "You can't tell me you didn't need that orgasm. You almost chewed my fingers off with your pussy and ass," I said, and she stopped complaining.

I kissed her again, my pussy breath ignored this time, as my tongue searched for hers. When she stopped resisting, I felt her hand move and unzip my fly. She groaned into my mouth when she felt my warm erection in her hand. "Will it really fit in there?"

"Why don't we find out."

"O...K."

I kicked off my pants and got between her legs, rolling on the condom as I did. I paused Mumentarily, looking down at a woman I had despised for most of my life, now seeing her in a totally different light. She looked up at me with a worried expression, but I kissed her lips as I pressed my cock to her opening. "Just relax and enjoy."

One long slow stroke, and I was halfway in, and as I took the next two, I was bottoming out in her pussy. She was watching me intently, as if deciding what she should be doing. "Play with your tits, Sister. And rock your hips. We are making love here, not me fucking you."

"Don't call me that while we are doing this."

"Fuck me back, Mona. Use that beautiful body to please me." I said, and she came to life.

She was hunching back at my thrust while running her hands over my ass and pulling me in. She wrapped her long legs around my hips and dragged them down the back of my legs, her passions ignited. I wasn't going to last, but that might be a good thing, as I was getting worried about one of the staff coming to find us.

"I'm going to come," I said, and she redoubled her efforts.

Her expression was priceless as I began to fill the condom and grind my pelvis against her clit. She rocked her hips when she picked up on my motions and rubbed herself to a second climax. I rolled to the side and pulled off the condom, before taking her hand and pouring some into her palm.

"What am I going to do with this?" She asked, looking down at her pussy.

"Not in there. That would be a mistake. Feel it and smell it, even taste it if you like. There is nothing to be afraid of." I said, and she tentatively dabbed her finger into the puddle. I started to dress and picked up the used condom and packet, placing them in some tissues from her nightstand and tucking them into my pocket. It wouldn't be good for someone to find them in her trash.

"Sister, have a great life. And if you ever find the right guy, don't hesitate to grab onto that love with both hands. It will give you more joy and satisfaction than anything this life will give you." I said, knowing in a few years, that's precisely what would happen with a priest from the next parish she is sent to.

I couldn't help smiling at Sister Mona across the assembly the next day, as we were sent out into the world.

****

I already had my first job lined up before leaving school and was on my way. I did take a few shortcuts before finding the right job for me, making sure to keep the ones that lead to something important, like meeting my wife for the first time, while skipping the ones I hated, like the night cleaning job. My Sister graduated from high school and was on her way to college, but was tossing up whether to continue, after some lonely months away from home.

I picked up the phone on one of my last days at home, before I moved into my little flat at the other end of town. "Hi, Sis, how's Uni going," I asked and heard a sniff.

"You alright?" I asked, and she blubbered something incoherent.

"You lonely? Want a visit from your big brother?" I said, teasing a little.

"Yes, please." She answered, she must be bad if she wanted me to visit.

"I'll come up this weekend; we can go dancing," I said, wondering if I might meet some hot Uni chick.

I moved out of home, taking my bed and all my clothes, but buying an old couch from a second-hand shop. It was nothing flashy, but it would serve me well for what I had coming up in my life. I did make a few changes. The biggest one was not spending every cent I earned on crap, banking it instead.

The following weekend, I drove three hours, arriving at my sister's shared accommodation just off campus, and knocked on the door. My Sister appeared at the door and threw herself into my arms. "Hi, Sandy."

"I missed you," she said, holding me tightly.

"Good to hear."

I dropped my bag in her room, and she dragged me back out the door. Her flat mate had friends over, and for some reason, Sandy didn't seem to want me mingling. I pulled my keys out of my pocket, but she waved at me to follow on foot. We crossed the road and cut through a vacant block before emerging next to the pub.

"They have a five-dollar salad bar," Sandy said, as we waited to be seated.

"My shout. We're having steaks," I said, waving away her protests.

I could tell she had lost some weight, and she was already on the thin side. She ordered coke and then pulled a vodka bottle from her bag. "It's my shout. Save that for when we get back to your place."

"Are you sure?"

"I'm not going to get kicked out of a Uni bar on my first night in town," I said, as she put the bottle back in her bag.

We ate the food and had a few drinks at the bar, until the music started. Sandy was getting hit on pretty hard, and I couldn't fault that. She was the best-looking Shela in the place. "Dance with me. It might keep the flies away." She said, pulling me by the cuff.

I have never liked dancing, probably because I have two left feet; but my Sister persisted and slowly taught me some nifty moves. The music was mostly rock, as that's what you play in a Uni pub. I would have never done this in my previous life, but I needed to do something differently this time. And bugger me, if I didn't enjoy myself.

We left the bar at one in the morning and leaned on each other as we crossed the empty block. I had to catch her a couple of times, my hands ending up in all the wrong places. Sandy didn't complain, only snuggling in under my arm. The apartment was empty when we finally got the keys to work, and Sandy's housemate was nowhere to be seen.

"Vodka?" Sandy announced, and I was drunk enough to accept.

"One more."

She poured the vodka into two glasses, with some juice from the fridge. I think it must have been some mango crap, but I was too far gone to complain. Sandy flopped down on the couch beside me, looking deeply into my eyes. "Thank you for coming, I needed this so badly."

"It's fun, hanging out with my beautiful little sister." I blurted out, as I took a pull on the strong drink.

"You think I'm beautiful?" She asked, with a shocked expression, and I thought she was mocking me, but her expression didn't break.

"You do know that you are the most beautiful girl I know, right?" I asked, looking into her aqua-blue eyes as her bottom lids began to fill.

She didn't answer, only tucking her head into my chest to hide. I wrapped my arm around her body with my hand, ending up cupping the side of her breast. I went to pull away, but she dropped her elbow and trapped my hand in place. "I love you, Jamie."

"I love you too," I said, her head rose from my chest, and she kissed me on the lips.

It was an intense, few Muments, as her hand grasped my bulge through my pants, and I slipped mine under her skirt. She was wet enough to feel it through her panties as she spread her legs for me. I worked her gusset aside and slipped one finger into her tight pussy, as her hand worked its way down the front of my pants.