Watershed Moment

My story begins pretty much now. Actually, as far as I'm concerned, my real life didn't begin until two weeks ago, when I turned 18. Nothing before that really counts in the grand scheme of things--at least as far as I'm concerned. But I guess you do need a little background to put everything into perspective.

We are a close family--just the three of us: Mom, who tells everyone she is "29 forever," but who is actually three years short of 40; my sister, Valerie, a year older than me (19) and almost sexy enough to be a cheerleader, and me. Everyone calls me "Twerp" (a nickname started by my sister) and I was probably the only male virgin in my graduating class last year. (That's not something I'm particularly proud of, but just letting you know for the record.) Of course, we do have a father, but he and Mom never got married and Mom kicked him out three years ago when he knocked up the woman next door. He hasn't married her yet, either, but he lives with the other woman now (Glenda) and their baby turned out to be the cutest set of twins imaginable. He seems to have settled down a bit, but Mom claims he is completely irresponsible when it comes to keeping his dick in his pants and I blame him for my life being so fucked up. Because it really is.

You see, I don't really want to be like him. According to Mom, he's a good provider (after all, he's supporting two families), but he's not much of a lover. Her words, not mine. I want to love, admire (I think a naked female is the prettiest thing imaginable), and respect them--not just use them like my father does, as well as most of the guys I know at school. ("Fuck 'em and forget 'em" is a term I often hear but find particularly offensive.)

And that's my problem. I'm not interested in the busty, brazen, cheerleader types (except for my sister and her friends, but I'm inclined toward the quiet, reserved, modest-figured, goody-two-shoes type--the girls I think too highly of to try to seduce. As a result, I come off as kind of stuffy and shy--the kind of guy no girl in her right mind would be interested in. Mom says I'm just the opposite of my father, which is just fine with me.

Well, I think that's enough background for now. It was kind of embarrassing to put down on paper, and even more-so to read, but it's all the god-honest truth! Transparency is what it's all about nowadays, isn't it?

So my story begins late last night, or early this morning if you prefer, shortly after midnight. I had just finished my regular porn session (a couple of hours each night). Our nightly routine seldom varies. After dinner, Mom, my sister, and I, do the dishes together and clean up the kitchen, then settle down in the living room to watch TV. Our sofa just fits the three of us and I have to admit that I feel kind of special in the middle with my two favorite ladies on either side of me. Did I mention that we're a pretty close family? If I didn't, we are.

Our evening starts with the PBS NewsHour, followed by a Hallmark Romance movie at eight. At ten, I say good night, depart the ladies, and head upstairs to my bedroom to finish up my night with entertainment a little more risqué. With a large screen computer monitor mounted on my bedroom wall and my laptop close at hand, I strip down and stretch out naked on my bed for a couple of hours of uninterrupted porn. Most evenings I can knock out two or three good orgasms before drifting off to sleep around midnight with my cock still in hand.

Often, though, I have to pee before turning in for the night. Such was the case last night. When I went to the closet for my robe, it wasn't there--or anyplace else to be found. My Mom has the irritating habit of removing clothes from my closet to be washed and taking a long time replacing them.

Damn! I really didn't want to slip on a pair of pajamas. I opened my bedroom door just a crack and peeked out into the hall. As I expected, all was quiet. Only the low hum of the air conditioner working in the background broke the silence. Mom and Sis usually turned in around eleven, so they were probably both asleep by now. My bedroom was at the end of the hall, and their bedrooms on opposite sides of the hall stood between me and the bathroom at the head of the stairs. Did I dare risk it?

What the hell! No guts; no glory. I cautiously stepped out into the hallway. My bare feet immediately detected the difference in texture between my bedroom rug and the carpeting in the hall, making me keenly aware of the chance I was taking as I ventured into the dark hallway. A single night-light mounted near the baseboard in the middle of the hallway did not detract from its late-night cavernous appearance. I felt like an interloper as I snuck past the bedrooms. My heart was pounding a mile a minute by the time I reached the bathroom door. I would have collapsed to the floor, I swear, and died right there had the room been occupied, but it wasn't.

Blinded by the light when I flipped the switch, I stumbled in and sank back against the sink. The feel of the porcelain, cold against my bare butt, assured me that I had done it--perhaps the dumbest and most daring venture in my entire life! Maybe not brave like Katniss and Peeta in the Hunger Games, but brave for a guy like me in real life.

Anyway, I peed, washed my hands, and steeled myself for my exit and return trip. The worst part was over, from here on it was a piece of cake. At least, so I thought. I hadn't taken ten steps before my sister's bedroom door opened and, the light being dim, I barreled right into her.

"Watch it, Twerp!"

I backed away in horror. " Sorry, Sis," I murmured, dropping one hand to hide my privates. "I wasn't expecting you."

"Obviously! What are you doing prowling around this time of night?"

"I had to pee."

"How come you're naked?"

"Mom stole my robe."

"Mom didn't steal your robe, Jack. She did a huge load of laundry today. And you know Mom. Your robe is probably sitting in the laundry basket downstairs right now and won't show up in your closet for another day or two. You can always get it yourself. That's what I always do."

"Maybe I will. Tomorrow." I tried to slip around her, but she kept purposely blocking me. "The bathroom's all yours."

"I don't need the bathroom. Not now, anyway. I can't sleep and I'm going down for a cup of hot chocolate. Why don't you join me?"

"Ahhh," I glanced down at the hand clutching my cock and balls. So did she. "I need to put something on."

She grasped my arm. "Oh, come on! Too late to close that barn door. You've been busted!" She tittered, amused by my predicament. " Might as well come down as you are."

Shit! Why the hell not? I gave in and followed her. At least my dick hadn't added to my embarrassment by hardening. It swung freely from side-to-side as we descended the stairs. For some reason, it seemed perfectly natural to be walking barefoot and naked through the house. And I have to admit, a bit exciting, too. Isn't that weird? With my sister by my side? But the harsh reality set in when we entered the kitchen and a moment later were suddenly flooded with fluorescent brightness.

When my eyes adjusted to the lighting, I realized Valerie was staring at me, openly inspecting my bare body from top to bottom and everywhere in between.

"You don't have to gawk!"

"I'm not gawking, just checking you out. Pull your hand away," she said with a wave of her fingers.

I heaved a sigh of exasperation, but felt a little thrill as I did as she suggested, fully exposing myself. "Wh-what do you think?"

She bit her lip and narrowed her eyes in thought before answering. With a grin and a little wink, she said, "Actually, you look pretty good for a twerp, Bro." Turning, she set two mugs on the kitchen counter and reached up for the Swiss Miss. "I've seen worse," she threw back over her shoulder with a giggle.

Pretty good? My cock twitched at the compliment.

Ohmigod! I had just walked through the house without a stitch of clothing on, along with my sister--and her, not even batting an eye! Now, I was naked in the kitchen and, surprisingly, not the least bit embarrassed or ashamed. And, I looked pretty good! Damn if I wasn't a changed man! I would never again consider myself a twerp again!

"Watch the water on the stove," Val said as she stepped back from the counter.

"Turn it off before it starts to whistle. We don't want to disturb Mom. I need to get something. I'll be back in a minute."

Then, she rushed off.

Have you ever waited for water to boil? I tried my best for a minute or two, pacing back forth in the kitchen, my toes curling as they reacted to the coolness of the tile floor while my mind wandered, picturing myself walking naked down a deserted nighttime street, moving in and out of the shadows cast by trees swishing in a gentle breeze that teased my bare flesh. Then, the scene segued into a sun-bright, grassy meadow; the six-inch blades of greenery tickling my toes as I ran chasing a naked, white-assed waif with flowing blonde hair, while birds sang in the distance--

"Jack!"

"Huh?"

"Turn off that water before we wake mother!"

"Oh, yeah!" I quickly removed the chirping kettle and looked up at my sister.

Her face was partially hidden by her cellphone. "That's it! Give me a smile--"

"What the hell?"

"Good job, Bro! Now, one more--perfect." She lowered the phone and started thumbing through the pictures she had just taken. "Oh my God! Your expression--" she chuckled. "Just precious."

"What do you plan to do with that pic?" I was looking over her shoulder.

"Do?" She pushed a button and looked up at me with s grin. "It's already done."

I straightened in anger. "You've sent it to someone?"

"Just Tamara."

"Tamara? Geez, Sis, you should never do something like that without someone's permission."

"Would you have said yes?"

"No!

"That's what I thought." She teased me with a grin that made my dick wiggle. "It would have been useless to ask."

I winced. "That's a feeble excuse, Val."

"I owed her, Jack."

"Owed her for what?"

"She shared me a dick pic a couple of days ago. Wanna see it?"

"A dick pic? No!"

But she had already found the photo she was looking for. "Here!" she said pushing her phone in front of my face.

"Sheesh, Sis! Who is that?"

"Hank."

"Her brother?"

"Nice dick, don't you think?"

"I'm not a judge of dicks."

"How about this?" She found a different pic, one more to my liking: a selfie of Tamara, herself, with a teasing smile, apparently naked. Since it was a bathroom mirror view, only her top part was visible. But that was plenty.

"You like her tits, don't you?"

"Ah, yeah."

"I can tell," she said, glancing downward. My dick had began a slow rise. She tittered. "Guys are so transparent."

"I can't help it," I murmured apologetically.

"How about this one?"

"Yeah, that one's better." This time, it was a full-frontal. Definitely better. "Who took it?

"Probably Hank--don't be so shocked," she said, noticing my expression. "They're not like us. They do things like that."

"Like what? Take nude pics of each other?"

"And other things."

I raised my eyebrows. "What other things?"

"They fuck--"

"Each other?"

She gave a slight shrug. "And others."

]

"My God, Val! That's incest."

"Not unless you get pregnant."

"Sis," I said with a patronizing look, "that's not the way it works."

"Bullshit, Jack. Everyone's doing it. Three of my friends are fucking their brothers regularly--probably even as we speak!"

Obviously, she was lying. I crossed by arms over my bare chest, stared her right in the eye, and called her bluff. "Name one."

"Shit, Bro, I'll name three." She started counting on her fingers. "There's Linda and her brother, Matt--"

That pair only confirmed suspicions I already had.

"--Jean and Troy, she continued, "who actually isn't such a bad fuck--"

"You know that for a fact?

"I know that for a fact."

I rolled my eyes, feigning disbelief. It would appear as though my sister was not what I always thought she was--still perfect, perhaps, but not so innocent as I held her up to be. The pedestal had started to crumble, bringing her down to eye-level.

"And Floss and Josh--although he hardly counts because he's just starting out and has a lot to learn, kinda like you."

"Geez, Val, you know that, too, as a fact?"

"Not the way you think, but because Flossie told me, and I believe my friends."

"Do you girls tell each other everything?"

She grinned at me. "Whisper something in a girl's ear at night, and it'll be viral by morning."

"Fuck!" I murmured. Then, "Who haven't you fucked?"

"Let's see...Linda is pretty possessive, so I haven't done Matt yet. I'll probably get to Hank this weekend. That's why he had Tamara send the dick pic--advance foreplay." She giggled.

"Shit! If you've been getting around that much, how come we've never been

getting it on?"

Looking up at me with a teasing grin, she wrapped her fingers around the tip of my now-freestanding dick and gave the end a gentle stroke. "Why don't you tell me?"

A sudden distraction interrupted us. "Good heavens! What's is going on down here?"

We both stiffened, and Valerie cinched her robe up tight. Our mother stood in the doorway, staring at us, her hands on her hips. She was dressed for bed in a pink flannel nightshirt that fell loosely around her body, stopping just short of her knees, and the fluffy bunny slippers Val and I had given her for Easter. I was at a loss for words, but Val came to our rescue. "We were both having trouble sleeping, so we decided to come down for hot chocolate."

"Both of you? Together?"

"Separately. Would you like to join us?" She already had Mom's cup on the counter and was spooning in a measure of Swiss Miss.

"Yes, please." She combed her fingers through her bedroom-mussed hair, pushing it back from her eyes, "How come you're naked, Jack?"

I glanced downward. I had all but forgotten my illicit exposure. Thank goodness, my cock had settled down again, drooping to insignificance in my thick, black tangle of pubic curls. "Ah, it's a long story--"

"He couldn't find his robe," Valerie explained, handing Mom her mug.

"Oh. It's in the laundry room. I didn't get everything put away. I'll get it--"

"No, Mom." I touched her arm, holding her back. "Not now. I'm okay."

"Are you sure?" She gave me a skeptical once-over. "It looks like you--"

"I think he's an exhibitionist, Mom," Valerie said, laughing. " I found him wandering in the hallway like that.

"Naked?"

"--as a baby."

"Good Lord!" She let out a sigh of resignation and took a sip of her hot chocolate. "My son, an exhibitionist. I suppose it's not the worse trouble he could get into. Well, no sense in standing around like this in the kitchen. Let's go into the living room and get comfortable."

Mom settled herself in her knitting chair, kitty-cornered from the sofa where Valerie and I took took opposite ends with our hot chocolate close at hand on the adjoining end tables. Or rather, I squeezed into one end and my sister took up the rest of the sofa. Her robe fell open completing exposing her legs from her toes to her crotch as she pushed her feet into my lap. She was wearing panties; I was not.

"You don't have a foot fetish, do you?" she teased with a girlish giggle as she wiggled her foot in my lap.

"I didn't think so," I said, using my hand to help guide the sole of her foot to the comfort of my my cock. "Until now." Her foot was just the right size to cuddle my cock.

"What are you kids up to?"

"Just fiddling around," I said.

"Couldn't sleep?" Val asked Mom, directing the conversation to a safer path while pressing both feet around my dick.

"Heavens, no! I haven't had a decent sleep since your asshole dad moved in with that bitch next door. I'm so used to having a bed partner to wrap my arms around that I haven't had a decent sleep in years.

"What did you do before you got married?"

"Your Uncle Jim and I shared a bed all our lives."

"Really, Mom!" I said, totally surprised by this admission, following right on top of my sister's revelations.

"Didn't that get a little awkward once you got of age?" my sister asked.

"Oh, no! That's when the fun began." She looked around to make sure no one was lurking in the corner eavesdropping, leaned forward, and whispered, "This is just between the three of us--even your asshole father doesn't know." Another glance around, and then, "Your Uncle Jim taught me everything I know about sex."

My eyes widened and my jaw dropped. Well, fuck!,Welcome to the world of adults, Jack! It's not Disneyland.

Val lowered her voice to match her mother's "Was he--"

"My first?" Mom sat back in her chair and smiled. "Yes, honey, my brother got my virginity."

'He seduced you?"

She chuckled. "It was more the other way around." With her secret out, she seemed relieved.

"As you have probably noticed, we still get together three or four times a year. Asshole next next door has never even noticed. Your Uncle Jim was my first, and he'll probably be my last," she said, visibly saddened.

"Oh, Mom, don't say that." Her daughter reached for her hands. "You're still young. Still beautiful--"

"--with years of good fucking--I mean sex, still ahead of you", I added.

"Hardly," she said. "I'm almost 40, kids. Past my prime. No young man would want me--and I'm certainly not looking for a pot-bellied, middle-aged, secondhand asshole who's trying to recover from a marriage he probably screwed up himself. Nope, the good ones are already taken." She sighed, "I'm just going to have to settle for a heavy duty vibrator with a 10 or 15-year warranty."

"Don't be so negative." Val caught my attention by squeezing my dick between her feet. "She's a MILF, don't you think, Bro?"

"A MILF?" My butt arched upward as her toes wiggled against the tip of my dick. Apparently, it had recovered from its late evening workout and was readying again for action. "Oh, yeah!"

"What's a MILF?"

"A 'Mom I'd Like to Fuck," Sis supplied vacantly, her attention elsewhere.

"And I'm a MILF?"

"Hell, I'd fuck you, Mom--I mean, if you weren't my mother."

Val suddenly pulled her feet from my lap, leaving my upward reaching cock embarrassingly exposed, and sat up. "You know what Mom?" she said excitedly, "I might have the solution to your problem. I was just reading something the other day--"she reached down to the shelf under the end table and brought up a magazine "--here, in First for Women--" She flipped rapidly through the pages, found what she was after, settled back, and started reading:

Sex has its perks, but a new study...reveals that cuddling may have more. In the study...researchers found that type of intimate activity, including close touch, was associated with both physical and psychological benefits, improving the quality of life. But older women who reported a higher frequency of kissing and loving touch also reported higher levels of life enjoyment and emotional closeness--whether they were having sex or not. More good news. Subjects who spent time cuddling enjoyed sex more than those who didn't cuddle.

She looked at us both with a gleam in her eye. Her attention settled on me. "You think something like that might work?"

I shrugged. "Cuddling? Sure, that's a no-brainer."

Mom nodded in agreement. "Yes, that's what I need: a little kissing and cuddling. First, I had my brother; then, your father."

"How about if Jack or me cuddles up with you for a while when you go to bed. Do you think that might help you get to sleep?"

"Oh, my! Yes! I never thought about something like that. That would be so sweet of you. That would keep me from feeling so lonesome in that big bed all by myself and maybe start me thinking of all the good things that have happened to me instead of the bad."