one-lucky-sumbitch
TABOO SEX STORIES

One Lucky Sumbitch

One Lucky Sumbitch

by vividlyyours
19 min read
4.59 (14200 views)
adultfiction
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This work is complete fantasy, a fictional composition about a man and the women in his family, with lots of love and a bunch of sex. It's not a quick stroke piece. Any resemblance to anyone living or dead is purely coincidental.

Please enjoy it for what it is. If it suits your fancy, good. If it does not, please just leave it for others to enjoy.

All active and named characters are over 18 years of age.

************

It was all too much.

Too much shapely ass.

Too much firm boob.

Too much long, shapely leg.

Too much long, beautiful hair.

Too much skin.

Too much of everything.

Too much.

My immediate family was enjoying its annual ritual of a week by the beach, sharing an enormous vacation rental less than a block off the sand. Expensive, but when the cost was split six ways it became quite reasonable for each of us.

What does that have to do with "too much?"

Allow me to explain.

Besides me, my immediate family included my mother Janice, at seventy years old still a head turner with a classic hourglass figure and a mane of silver hair. A lifetime of good eating and exercise had delivered her into her dotage as a true GILF, and she even turns the heads of guys younger than -my own thirty years. Dad had died ten years previously from not-so-good eating habits and a faulty ticker. We missed him, but time had taken the edge off the pain.

Then there were my sisters Terri and Sharon, aged 45 and 40. If the term SILF ever enters the lexicon, my siblings will be the picture next to the words in the dictionary. Holy mama, these two.

Yowza.

We are a tall family in general, so Terri is five-nine and Sharon is five-seven. As if that doesn't attract enough attention, their genetics and their own eating and exercise habits kept them in remarkable shape, long and lean and shapely with curves in exactly the right places and figures that were the envy of every doughy, middle aged matron.

Terri and Sharon were also blessed with faces that could grace the cover of Elle or Cosmo. It was like the face designer on duty that day had taken the best from Cindy Crawford, Julia Roberts, and Helen Mirren, and combined them into something superior to all of them. They were and are total babes. Terri was an OR nurse and Sharon a teacher, and they were both single moms, with Terri divorced and Sharon abandoned by the baby daddy before the little one came.

The gene fairy was very, very good to the women in my family. Very good indeed.

About Sharon's little one. She had produced a daughter, Wendy, when I was only eight years old, putting me closer in age to my niece than to my sibling.

Wendy and I spent a lot time together as she was growing, and she always told me that I was her favorite uncle. Whenever I pointed out that I was her ONLY uncle, she would say, "I don't care, you're still my favorite." With my agreement, she never used the title when addressing me as we were too close in age and personality.

As a toddler, she was my shadow at family events, following me around with her arms extended as if to demand I hold her. I gladly did that.

As she grew I still provided a lot of attention to her, playing games with her and generally keeping her occupied. I was happy to do it; being so much younger than my siblings put me in a different generation, and as a preteen boy I felt a closer kinship with my young niece than I did with my sisters, my boring old parents, and their families.

Even as a teenager I maintained a close relationship with Wendy. We would have long, deep conversations and she treated me like her closest confidant, which I guess I was. As she hit puberty and beyond I was the one who provided an ear or a shoulder as necessary. I honestly enjoyed her company and she enjoyed mine and I was quite attached to her.

I watched her blossom into adulthood and I like to think that I helped her become who she is, a smart, well adjusted, happy woman who will conquer the world.

Like her mother, Wendy grew into a stunning beauty. It was the crowning glory, the denouement, the delicious cherry atop the most decadent sundae imaginable.

Cripes, was she hot.

Taller than most women at five-nine, she was striking enough, but with her absolutely gorgeous oval-shaped face, curly brown hair halfway down her back, and a body do die for, she was a fucking goddess. Long and lean, she nonetheless sports large, full breasts, only 34s because of her wiry frame but easily c-cups in size.

She was and is a stone fox, ain't no doubt about it.

And remember, I'm her favorite uncle.

But even all that wasn't enough to trigger my dilemma, oh no.

You see, Wendy had not only joined the rest of the family for a week at a beach house, but had brought her friend Kate along, another brunette who was every bit as lovely as Wendy.

Do you see where I'm going with this? Thank you.

Kate was like a reflection of Wendy in many respects. Kate was an inch taller, bringing her within four inches of my own six-two. Also long and lean, she had the longest, straightest, smoothest brown hair of anyone I knew, framing a longish face reminiscent of Celine Dion but without the hard edges. She had this disconcerting habit of standing very close when engaged in conversation, sometimes within less than six inches, and her height put our eyes at almost the same level.

Oh, those eyes. As brown as her hair, they were deep pools of wonder, sparkling with wit and intelligence and inviting anyone looking into them to just dive in and drown.

Wendy and Kate had been classmates and college roommates and I had known her since she was twelve. I was quite fond of her and truly enjoyed her company.

Two quite lovely women in their early twenties, freshly graduated from college and anxious to take on the world. A den of foxes. Vixens?

Thus my dilemma.

I mean, picture the scene. We were all staying in a large house in a popular beach resort town in the middle of a hot summer. How do people dress at places like that?

Skimpily. Shorts are

de rigueur

as people want as much skin as possible exposed to the sun. T-shirts and tanks are the universal tops for men, while women wear what they can get away with. For pretty twentysomethings that was usually crop tops, often worn braless, and of course bikinis.

Oh man, those bikinis.

I was surrounded by acres of beautiful flesh at every turn.

The struggle was real.

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Terri's son Dylan was a surly, perpetual loser in a hoodie who lived with his loser of a father and preferred video gaming to spending a week at the beach, so it was just me and a houseful of world-class beauties. A smorgasbord of boobs and butts and skin and the absolute best that Mother Nature had to offer.

I will admit that I am an unashamed horndog. I love women and love everything about them. Their look, their smell, their eyes, their brains, every single part of who they are fascinates me. And that applies to my family.

Including my sisters, my niece, and her friend.

It's a dirty job, but someone had to do it.

My name is Jack.

I won't express any false modesty; I'm no Adonis and you'll never see me as the male half of one of those beautiful, vaguely Italian couples in fragrance ads, but I'm actually not that bad. Thirty years old, six-two, 195 pounds, tight core, good arms and shoulders. Brown hair tastefully tousled, fashionable stubble, brown eyes like the rest of the family. Permanent tan from lots of outdoor activities. I don't turn heads, but then I've never been kicked out of bed, either. A real everyman.

About that: I had enjoyed a couple of serious long-term relationships, but for whatever reason they never reached the "can't live without each other" stage and kind of just petered out. Despite my horndoggedness, I am not always on the prowl and only occasionally hook up. Honestly, I'm quite content with being alone much of the time and actually savor it. As a cybersecurity guy working remotely I make close to two hundred large every year and work at whatever time of day I chose, requiring only a secure internet connection.

In the intense summer heat, all the women except our mother spent most days in a bikini, with maybe a colorful wrap around the bottom when strolling the sidewalks or slipping on shirts and maybe shorts to eat in restaurants.

The bikinis were of a more traditional variety, not the three-tiny-triangles-and-butt-floss models featured in so many Literotica stories. Brief and tight, but no nip slips and at least half of each butt cheek covered. Nonetheless, there was little left to the imagination.

We all enjoyed our time together, sunning and beaching and cruising the streets as a large group most of the time. I got more than a few smiles, nods, and thumbs up hand signs from passing men.

I was in horndog heaven.

Life was good.

But back to our tale.

************

Day 1

It wasn't flirting per se, but man, did it get me going.

First night in our rental, the day having been spent mostly at the beach. We were sunned out and sitting around the large central room sharing pizza and drinking beer and wine and already feeling a bit buzzed. Four beauties are arrayed around me, the younger ones in shortie PJs, my sisters in long Ts and panties, not a bra anywhere. Mom was already reading in bed.

Kate spoke up. "Do you dress like this around Jack all the time?"

"What do you mean?" Terri asked.

"In just panties and a T."

Terri glanced quickly at her sister. "Well, yeah. Is it a problem?"

"Not at all. My parents never let me show that much skin around my brothers, but you guys seem to be very comfortable with it."

Terri laughed. "We are. We didn't have a large house growing up, so it would have been hard to say covered from head to toe all the time. We all saw each other in various stages of undress a lot, and I guess that habit remained even after we all grew up and left home. Jack was so much younger than us anyway. I was gone by the time he started school."

Sharon piped up. "We've been doing this for years and it's never been an issue. Jack, does it bother you to see us like this?"

I took another sip of my beer and considered my words carefully. "Not at all, in fact far from it. I mean, aside from the fact that you're all supermodel beautiful, it's really about how close we all are. You're my sisters and I love you."

Both of them smiled. "We have just the best little brother anywhere," Terri said.

Sharon addressed Kate. "Does it make you uncomfortable to see us like this?"

"No, no, not at all. I guess I'm just a little jealous that you can all be so comfortable with it. My family is very conservative and modesty is pretty strictly enforced. It's one of the reasons I went so far away for college and have no intention of ever living at home again."

Wendy chuckled. "Yeah, you really busted that rule. You had no problem walking around our dorm room with your boobs out."

The whole room laughed, including Kate. "Well, yeah. Our room was my safe space. Most of the guys around us were so creepy, and it felt good to just let loose. Plus bras are so damn uncomfortable and I like giving the girls a little air."

It's starting. I'm sitting here with these gorgeous women, and they're talking about boobs. Alrighty then.

"I'll second that," Sharon said. "Guys can go anywhere wearing just enough to cover their junk, but we girls have to bind ourselves up so the jiggling and pokies don't distract them." Another laugh from the room.

"Jiggling and pokies?" Oh my, yes.

Wendy addressed me. "Look at Jack over there, listening to us talk about our tits. You must be loving this."

I grinned. "Far be it from me to interrupt such an erudite discussion of the female anatomy." Everyone gave a big laugh.

"I think our Jack may be a breast man," Terri opined. "You like boobs, Jack?"

Careful, boy. The ice is getting thin.

"Of course I do, I'm just a red blooded American male. But they're not all I see in a woman."

"Pffft. Yeah, right. I'll bet if one of us flashed you right now you wouldn't be able to tear your eyes away from them."

"I dare you," Wendy said.

"Dare me to what?"

"Show Jack your boobs. I dare you to flash him for five seconds."

Terri stared at her niece and I wasn't sure if I was seeing anger or acceptance.

Acceptance it was. "Ya know, I've had just enough to drink to take that dare." Sitting forward on the couch, Terri turned to face me. Looking straight at me, she grabbed the bottom of her t-shirt and lifted it above her breasts, staring defiantly at me.

Oh holy fucking mama. She did it. Those are my beautiful sister's tits. Her very naked, very beautiful tits.

Remember, Terri is my oldest sib, 45 years old. By that age, so many women are already well on their way to being shapeless blobs, carrying 50 or 100 extra pounds and a couple of extra chins.

Not my Terri, oh no. She was as fit as she had been thirty years earlier, but with the curvier shape and mature boobs of a real woman who had given birth. Hers were perfectly shaped C-cups of delight, firm and full, with just the right amount of sag to give them that classic teardrop shape.

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The skin of each one was of course paler than the surrounding flesh, and her silver dollar sized areoles were significantly darker, with a large, erect nub in the center of each. Delicious titty sundaes.

Lord have mercy, they are perfection.

She held her shirt up for what seemed like an eternity before lowering it and sitting back. She reached for her wine glass and took a long swig.

Everyone in the room looked from Terri to me and back. It felt like everyone was holding their breath at once.

"Holy shit, I can't believe you did that," Wendy said.

"Neither can I," Terri answered as the room erupted in loud laughter.

"Did you see Jack's face?" Sharon said. "Jack, you were mesmerized. Terri was right." I could feel my face flushing.

The girls were laughing so hard that a couple of them were wiping tears from their eyes. "Oh Jack, that was priceless," Sharon told me.

"So what did you think, Jack?" Terri asked. "Were you able to see anything but my boobs?"

In for a dime, in for a dollar. Two can play this game.

"When they are as perfect as yours, then no, dear sister. I couldn't see anything else."

Another round of laughter from the room, but Terri looked at me seriously. "You think my tits are perfect?"

"Terri, they are the definition of perfect. If you look up the word 'boobs' in the dictionary, it is illustrated with a picture of yours." I gave her my best loving little brother smile as she blushed bright red.

"I have to admit, Terri, your tits are about the best I've ever seen," declared Wendy. "I hope mine are as good as yours when I'm 45."

Terri laughed with the rest of us. "Listen to you, Miss Perky Titties. Broads my age can only look and you and Kate and try to remember when."

This is getting very interesting, yes it is.

"Are you calling me 'perky?'" Wendy replied, lifting her own shirt and exposing her glorious pair, which were indeed quite perky. Standing tall and proud, they needed no artificial support, their pale skin crowned by nipples only slightly darker than the surrounding flesh but still quite delicious looking.

Holy shit. Oh, fuck me sideways.

"Wendy!" her mother cried. "What are you doing? Put those away!"

Wendy glanced over at me and smiled. "Jack? Do you think I have perky titties?"

"I plead the fifth," I said, fascinated by the sight before me. This was truly unbelievable. Wendy lowered her shirt with a mock pout.

The repeated displays of beautiful boobs was having an effect. Yes, I was blood related to most of them, and yes, I loved them like a brother and uncle should, but goddam, I'm a man, yes I am and I can't help but...

My body was reacting just as you would expect a horndog's body to react.

Get your wits about you, boy. This is no time to let your little head take over.

"Oh no, you can't get away with that." Wendy declared. "Perky or no?"

"Of course they are," I carefully said. "Let's be clear - every single breast in this room is perfect in every way. And I thank you all for giving me the opportunity to reach that conclusion through personal observation."

The ladies all laughed. "You are one diplomatic son of a bitch, Jack," Sharon said. "You should be in the State Department with that smooth tongue of yours." Her double entendre elicited more alcohol-fueled giggling around the room.

"I don't think we're drunk enough to go there just yet," intoned Terri. "Maybe tomorrow." More laughter.

"Okay, I think I'm done in," Sharon said. "My pillow is calling my name. Night, all." As she rose the rest of the women followed suit and trooped one by one up the stairs to their bedrooms. As the only guy I was relegated to a futon in the living room, which I didn't mind a bit because I woke up earlier than everyone else. Kate was the last to go, deliberately holding back for a few seconds.

Just before she reached the base of the stairs, she turned to me and said in a whisper, "You ain't seen nothing yet, Jack," then whipped her short pajama shirt up and off, leaving her topless. She ran her hands enticingly over her nicely rounded and now very naked hemispheres, a firm and fair pair mounted high on her chest, then turned to walk upstairs. I watched her as she climbed, and just before she passed out of sight she turned to me and blew an air kiss in my direction.

Fuck me, I am going straight to hell.

.

I turned off all the lights and unfolded the futon, then grabbed the folded sheet behind it and spread it over the bed. Dropping my shorts, I laid down on the sheet and stared into the darkness. I had a lot to think about.

As close as we all were, this was uncharted territory for me. Sure, I was used to hanging out here with my sisters wearing close to nothing, but the titty show I had just witnessed had taken things in a whole new direction. I had always admired the breathtaking beauty of my sisters and niece, but I had never really thought of them sexually.

Until now.

Damnation

.

Just as sleep was about to overtake me, I heard light footsteps on the stairs. Whoever it was padded across the floor to where I was lying on top of the sheet in my boxer briefs. In the dim reflected light from outside I saw that Terri had come down to talk to me.

"Jack? You awake?"

"Very much so, Terri. You OK?"

"That's what I wanted to ask you," she replied. "I wanted to make sure you were all right with everything that happened tonight. I didn't want to embarrass you." She sat on the edge of the futon, her hip against my leg.

"Embarrass me? My otherworldly big sis flashing her boobs at me? Any other man would sacrifice a limb to see what I saw tonight. No, not embarrassed at all."

I could see her smile in the near darkness. "I'm glad. You know we all love you so much."

"And I love you, Terri. I'm glad you all felt safe enough around me to do what you did."

She looked at my face for a long moment. "Safe. Yeah, that's a good word to use. We all feel safe with you." Leaning toward my face she gave me a soft kiss right on the lips, a kiss that lasted a couple of seconds longer than a sister/brother kiss would normally last. No tongue, but such sweet lips.

"Thank you, Jack. We are so lucky to have you as a brother." She ran her hand lightly across my cheek while looking into my eyes, sending an electric current up my spine. All I could do was smile, fighting the urge to wrap my arms around her and pull her to me.

"I'm the lucky one, babe. Thank you for being who you are."

She took another long look at me before speaking softly. "I swear, Jack, if you weren't my brother..."

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