Chapter 1

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Heterosexual, Mother, Son, Brother, Sister, .

Desc: Sex Story: Chapter 1 - There's something about fucking a girl who's recently given birth to a baby. Being in a vagina that had served an entirely different purpose. If she's still nursing, all the better. But what I like most is sweet-talking her into bed while she's still in the first blush of motherly love. And has just given her husband the greatest gift a couple can produce. New-mother fucking is a kink, I'm very aware of that. But seducing a woman who is even more in love with her husband than ever ...

Winston:

Does anyone grow up 'normally?' White picket fence normal? Stay-at-home mom? Apple pie in the oven? A firm, but wise father? An understanding and indulgent older sister? A spirited, but good-natured younger brother?

Not many, would be my guess. And certainly not in NYC.

On the other hand, I would imagine that most of us think we're more interesting, more unique, than we really are. That our inner fantasies, our darkest dreams, reveal a singular soul, unmatched in the annals of history. (In my current state, it's an infatuation with new mothers. Sexual infatuation.)

I'm like most people -- wanting to be exceptional, if not extraordinary, but mired in the familiar daily routines that get us through ... well, through the day.

Name: Winston. Age: almost 23. Occupations: gopher for a top ASID (American Society of Interior Designers) superstar. Art gallery assistant. Waiter. Deli delivery boy. Design student.

Pathetic for a Williams grad? In a way. But I'm gaining work experience and professional credits to become a licensed interior designer. It's years away, but I'm on the path I want to be on. Working in a Chelsea art gallery adds to my postgrad street creds.

One cliche I've avoided is boomeranging back to live with my parents on Central Park South. My independence didn't take me far, however. I moved in with my sister Pamela (never Pam) when she kicked out her roommate.

Pamela explained it to Mom and me, "Deirdre was a slut and a slob. I could take the slut side, but I got sick and tired of cleaning out the bedroom, bath, and kitchen after her whirlwind visits."

Thus, I was invited to move into Pamela's 1200 square foot (minimum size in SoHo to obtain a Certificate of Occupancy) Prince Street loft. Pamela said, "Mom, as long as Winnie doesn't jack off in front of my friends, I'll put up with the perv. At least he's a neatnik."

Mom's answer: "It's better for him than living in Queens."

Pamela and I almost always got along pretty well. She's two years older and cool, even though she's a techno nerd. She's a freelance IT consultant, is a fanatical gamer, and hauls in major bank.

She doesn't mind when I bring home a waitress, a gallery customer, a casual girlfriend for the night. And she's introduced me to a new guy a time or two at breakfast. Well, more than a time or two.

Pamela got her looks from Mom. Both are tall, around 5' 9." They have similar slender bods with perky boobs. Not that I ever noticed. Pamela wears her dark brown hair in short, shag cut. No muss, no fuss.

Both of the principal females in my family have vivid green eyes. And a spirited outlook on life. They are quick witted and sharp tongued. I'm glad they're on my side.

Despite my latest fixation on married mothers, I didn't lust after Mom all that much. Well, not at first. It eventually dawned on me, from my friends' reactions to her, that she was hot. I did go through a sneak and peek period, but outgrew it. Mostly. Mom wasn't upset with me, she probably figured it for what it was -- adolescent growing pains.

Pamela was another matter. Along with being killer smart, she has an extraordinary awareness of everyone and everything around her. It took her about two seconds to understand the effect she had on me once Mr. Puberty had knocked at my door.

To say my older sister played into my sudden fascination with sex would be an overstatement. But, when she was in a certain mood, she didn't mind steaming up the home front atmosphere. Wearing only a towel, strolling by in panties and bra. Brushing her hair without the bra. Pamela knew exactly what she was doing.

However she was more than a tease, she was a pal. Educated me, as much as an 14-year old can be educated, on the fairer sex. When I started dating, Pamela asked detailed questions, gave me detailed advice, and probably was more responsible for the awkward, groping, successes I had than anything I did or said with girls on my own.

When I (finally!) lost my cherry at 14, it was to one of Pamela's girlfriends. I still try to tell myself that it wasn't a mercy fuck. Although Melody didn't ask for an encore performance.

But before that particular night of bliss (for me, anyway) Pamela started giving me an occasional hand job. Not often, and never when I begged. But still.

Our father, also named Winston, has always been a hard charger. He and Mom (Sophia, but everyone calls her Satin) were both fifth generation New Yorkers. Dad works hard and plays hard. He bought out his two partners in a boutique venture capital firm and moved the company into high tech a year or so behind Silicon Valley but a couple of years ahead of most of New York.

Pamela inherited his tech savvy. I didn't.

But Dad has never been all work, despite his travel schedule. Our family skis, kayaks, skeets ... well, work hard, play hard. He still plays a few chukkers at his club down in Wellington. Dad isn't Triple Corona class, but he's damned good for an American part-timer.

I did inherit his height, I'm just under 6'2". We both weigh in around 180-185.

So, Winston V and Satin uptown on Central Park South. Pamela and Winston VI downtown on Prince. Close, actually, in terms of miles. But worlds apart so far as culture and attitudes.

Neither Pamela nor I is big on cooking. Fortunately you can live for years in New York without turning on your stove. Working in restaurants or that deli, I usually was able to forage. My sister and I ate street quite often. And the takeout and delivery options were legion.

Pamela's attitude -- living alone with me, as opposed to when we were at mom and dad's -- toward clothes became more and more casual. She didn't loll around in the nude, but it wasn't unusual for me to catch sight of her dressing or undressing, getting ready for her treasured bubble baths, etc.

I'm no exhibitionist, at least not much of one, but I certainly didn't mind when Pamela came into my tiny bedroom and talked with me when I was naked. Sometimes she watched me finish jacking off.

Eventually, after a long day at work for both of us, we fell into a pattern of my sitting on the bathroom chair while Pamela lounged in the tub, covered with bubbles up to her chin.

So, we were pals. And she still gave me the occasional hand job. Didn't make a big deal out of it, but it wasn't a brisk, let's-get-this-out-of-the-way deal either. She sometimes grinned at me and drew it out, able to sense when I was on the verge and pull back until the moment passed. Those were my favorite times.

Jessica (writing as Pamela):

(If Jimmy thinks changing his name and marrying me off, fools anyone but himself, I did an even poorer job of raising him than I thought. Goofball.)

Pamela thought, "I may as well suck him off, Winnie's a pretty good kid."

I never knock at Winnie's door, never have. He's younger than I am and has fewer privileges. He was sitting at his laptop, nude as usual, but he wasn't surfing porn for a change.

I tugged his soft cock -- he's so proud of how fat it is -- typical boy. I led him to his bed, pushed him back, got on my knees and took him in my mouth. No objections from Winnie.

I didn't say a word, just sucked him off. In the future I'd take more time, tease him, keep him panting. But I wanted to get this first one out of the way. I'm good at sucking cock because I like doing it. Mom told me she's the same. The string of men who call her when Daddy's at work back her up.

Plus I have eyewitness evidence which I'll discuss later.

But Winnie's first blow job from me wasn't methodical. I added some flourishes that I've picked up on the dozens of cocks I've been sucking since middle school. I was lucky to come of age in the hookup era. My girlfriends and I would cheerfully suck cute boys off just for the fun of it.

Almost no one in school -- middle school through high school dated. We just roamed all over the city in packs. If a guy was feeling a little down, flunked at test, got grounded, anything ... there were any number of us who would suck him off,

Fucking was a little different. Most of my friends and I put out for a lot of the guys, but we usually had to feel something for them. Like them a little, if not a lot. But a blow job? Before school, during school, after school, on weekends.

Of course there were exceptions to our fucking standards. A really hot guy, or one with a terrific line of patter or ... when we just wanted to.

I could tell Winnie was about to cum even before he moaned.

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Story tagged with:
Ma/Fa / Heterosexual / Mother / Son / Brother / Sister /