After the Windfall: 'Mother'

My plan is to make this the first of several stories following Walter Winthrop as explores the world of sex and himself, but I can't promise anything. I hope you enjoy it. Warning: It contains some incest role-play, but no actual incest.

I looked gobsmacked, I'm sure.

"You look gobsmacked," Trilby Archer said to me with a wry smile.

My family's attorney had just informed me that I was a millionaire, potentially.

It had been two weeks since I arrived home to discover part of our home in flames. It was almost 10 p.m. and I was finishing my commute from my job as a computer technician and member of the Nerd Herd, a service offered by my employer whom I will call Optimal Purchase.

I was gobsmacked then, too. Firefighters were crawling all over grounds and structure. Hoses were everywhere. A patrol car with lights flashing had closed the road. Neighbors were gathered on their lawns to watch. I parked my car curbside and proceeded to the patrol car.

Zombie-like, I walked toward the house, probably slack-jawed. A police officer put his hand on my chest to stop me. I guess I hadn't heard him. The contact jolted me out of my stupor.

"That's my fucking house!" I shouted in alarm. "Is my mother OK?!"

He sighed, walked me to his patrol car, opened the back door and seated me facing out.

"Are you Walter Winthrop?" he asked. I acknowledged my identity with a nod.

"Mr. Winthrop, I'm very sorry to inform you that your mother is dead."

I must have looked ready to faint because he reached out to steady me.

To say my mother and I had a tense and troubled relationship would be an understatement. Gwen Winthrop was a 60-year-old former dancer and golddigger turned reclusive alcoholic. At his own death 10 years before, my much older father, a decrepit playboy who had spent what remained of the family fortune, had left us nothing, acorrding to my mother. That's why my mother had refused to pay for college and was charging me rent to live at home. Now, Trilby Archer, our very preppy lawyer, was telling me facts that contradicted some of that narrative.

Despite living as a virtual pauper, my mother had left liquid assets of more than $900,000 and benefits from an insurance policy almost equal to that same amount. Next, I learned that in addition to those sums, I was acquiring ownership of the Frank Lloyd Wright-designed home we had lived in for decades. It was now damaged but still salvageable.

Trilby continued, "The last bit of business involving the settlement of your mother's estate are the paintings — the two Matisses and the Picasso."

I smiled.

"They're good reproductions, Mr. Archer, but I doubt they're worth much and now probably fire damaged as well."

"No, I mean the ones in storage."

I asked him what he was talking about.

"She really did tell you nothing at all, did she?" Trilby said with a weary shake of his head. "Those reproductions are so good because the artist your father hired was working from the originals. The originals are in super-secure storage in a fine-art storage facility out west, and they belong to you now."

This is the part where I got smacked by gob, so to speak.

"An estimate for insurance purposes a few years ago valued them collectively at a total of almost $100 million. That was a conservative estimate made at a low point in the high-art market."

My head was spinning.

"They are not insured for their full value. Your father only could afford policies that covered much less than that, and he only agreed to buy that insurance because the Vault required it. That's what people call the place out west."

"Wow," I said. "What do we do?"

Over the course of the next few months, we did what Trilby suggested. The paintings were sold at auction, the house was sold to a well-heeled neighbor who had lusted after it for years. When all was said and done and taxes paid, Trilby collected a handsome fee, and I was worth more than $60 million. It was good to be 27 and a millionaire in reasonably good health. I half felt I had earned it for putting up with my parents' lives and a lot of other bullshit.

In the interim, while the house was being repaired and restored by its new owner and before the final settlement of the estate, I moved into an apartment in Cliffside. It was on the edge of "Edgetown." If you don't know Central City, it's in the quote-unquote bad part of town at the south end of downtown and between Cadron Boulevard and the Cadron River. Once it had been home to working and middle class folks-- downtown shopkeepers, employees in the railyard and factory workers. Now it was peopled by a mix of working poor, immigrants, criminals and low lifes.

My apartment was in a restored hotel just off Cadron. Trilby was one of its owners, along with some partners. They'd bought it in the aftermath of the Great Recession. Finished what little remained of its renovation and started renting units. The area of Edgetown I was in had been in the early stages of redevelopment when the downturn happened. It was starting to pick up again and I liked being walking distance to downtown. My fellow tenants were single men and women my age who were starting careers at Central City banks, law firms and companies in inner Central City. That and some newly married professional types. The building was quiet and about half occupied.

All my stuff was either smoke damaged or not worth saving from the house. As executor, Trilby was able to advance me about $40,000 on the estate to give me something to live on until the settlement. In actual fact, the insurance paid up sooner than expected, long before the $40,000 had run out. So, I started buying new clothes, a good bed, a new laptop, a computer desk and a couch and TV. I wasn't sure what I was going to do with my life now, so I was reluctant to buy more right away. I used a folding card table for eating meals.

Just so you don't think I'm a complete coldfish, I'll say that yes, I did have some bad days. Although our relationship was not ideal, she still was my mother and my only living relative. I think she had some cousins in Nebraska, but I'd never met them. At times, I was lonely. At other times, I was lonely and mourning. Still, I never let myself brood or mope for more than a few hours before I would force myself out the door to shop or grab lunch or do whatever. Of course, I quit my job, which I retrospect might have provided a helpful distraction until the settlement. My other focus was on getting laid.

I was a 27-year-old male with limited sexual experience. I'd had some drunken sex with girls in college, but it was vague and dim in my memory. I was and in many ways still am a classic geek--- bachelor's in computer science, Star Wars nerd, comic book collector. I was terribly shy around women--- not quite Raj in "Big Bang Theory" but close. With enough beer or liquor, I could be brave and seduce a young woman who was equally drunk. That same inebriation robbed me of the experience though. I decided I would use my free time to end that cycle. Maybe it even would alleviate some of my loneliness emotionally. I didn't want any more drunken sex. I wanted to feel and experience everything about it. I'm not sure what my motivation was other than the usual primal ones, but maybe it was the death of my mother. Suddenly, I didn't want to waste any more time. She certainly had.

Now that I had more free time, I started hitting the gym daily. I just had to walk a few blocks over on Cadron to get to a downtown gym that catered to the business crowd and folks who lived over in the Yard. I became quite pleased with my new toned look. I've always been slender but now I looked really fit-- no six-pack but tight. I took photos of my physique wearing Speedos and from the neck down. Despite the upgrade, I still was shy. I offered face shots on request in my online ads-- CraigsList, Tindr, et cetera.

Most of the responses I did get came from gay and bi dudes, even though it was in the hetero section. I was upfront about the virgin thing. Maybe that's what drew the guys, or my photo. I'll admit that I was a bit bi-curious but I wanted to give straight a try first. So, I didn't get the responses I wanted and continued to use porn and such as an outlet. After a month of junk and two failed meet-ups with women, I took my ads down. I waited a week before getting up the nerve to post a new personal with a face shot. I just listed my interests and desire for companionship basically.

Three days in, Valerie responded.

XXXXXXXXX

Valerie said she was bank executive, 45, who worked downtown. She had divorced about three years ago and had an adult daughter who was married a career Army officer and relocated to Europe. "I guess we both are empty nesters," she wrote.

Valerie said after her divorce she had coped by burying herself in work, winning a promotion that actually allowed her more free time. Extra time also meant less distraction and more loneliness. Our situations were similar that way too. Both of us were looking for more, and while definitely not a virgin, she admitted her dating skills were rusty. My lack of experience made me less scary to her.

It's funny even writing that now because Valerie exudes confidence and somehow manages to walk the line between strength and bitch professionally. On an interpersonal level at that point in time, she felt more vulnerable though and I appreciated her honesty. It helped relieve some of my performance anxiety. Her other big secret was that she was a Star Wars fan. We laughed about it. Princess Leia was an important role model growing up. Oddly, she was not much of science fiction geek, just had the Star Wars bug.

That gave us a common topic for that always awkward first meeting-- coffee at Starbucks on a Thursday after work. We shared our excitement about the new movie and managed to talk about other things too -- family, other interests, even religion.

"Look, what do you think about me now that we've met?" she asked near the end of our visit. "Am I too old, Walter?"

I laughed and said, "No, not at all, you're hot."

I immediately blushed but she gave me a big smile.

"Well, I think you're cute, too. I'd like to take you to dinner tomorrow night."

"Oh," I said. I was taken aback that she was asking me out.

"Is that a bad day? I know it's short notice."

"No, no, I'm flattered. ... Uh, sure. What time?"

"Six o'clock. I'll meet you here, and we'll grab an early bite and continue the conversation."

She didn't seem unsure of herself like she seemed in her emails.

"That sounds good," I said.

As she got up, I again took in her chic business attire. She was a tall five-eleven compared to my five-eight. Valerie loomed over me in my seat with her three-inch heels, and looked down at me, smiling.

"See you about this time tomorrow then," she said turned and exited the store.

That's when the thunderbolt struck. Her black stockings got me. Valerie also cuts quite a figure, noticeable breasts more commendable for their round fullness and shape than enormous size. She had curves in her hour glass, too. Her straight black hair, face and glasses gave her a bit of a Tina Fey look that I found sexy.

XXXXX

While our relative age difference gave Valerie a confidence boost, the two cocktails made her positively bold. For the reasons previously stated, I stayed 100 percent sober. Dinner at Lush Life was fun. The food and drinks were fantastic. I'd never had antelope steak before, but it was delicious.

"Where do you want to go next, Walt? You pick."

I thought for a minute. Lush Life was a place she knew well but I had never been to before. I tried to think of something different.

She already had told me at Starbuck she had never been to a hookah bar, and and I guess she might like an after-dinner smoke.

"How about Hookah on the Corner?"

She laughed.

"I'm not a hookah! Are you going to try to pimp me out or should I pimp you, Walt?"

A bad pun, but we both laughed and got up to walk the six blocks to the hookah bar.

They'd only been open since 5 p.m. and it was still quiet. In my experience, the place never got busy until 8 or 9.

We settled into a sectional, and I ordered a mint shisha.

As we sat down, she patted the cushion next to her and said, "Come sit next to, mama."

I'd never harbored the slightest erotic thought for my own mother, but somehow this excited me.

Most of the next few minutes was taken up by me explaining hookah to Valerie. We relaxed into a silent rhythm of smoking that almost seemed erotic. Flirting occurred with the eyes, a touch, holding hands.

"I never had a son," Valerie said outloud but in a whisper, almost as though she was speaking to herself.

"I no longer have a mother," I whispered in reply.

I must have sounded sad because she looked at me very warmly, very motherly, then Valerie took my face in her hands and said, "Mama is going to kiss you and make you feel better."

She kissed me on the lips then slightly parted them. I felt her tongue lick at mine, and I instinctively opened my mouth. Our tongues danced around each other, but she was more aggressive. I moaned low, involuntarily, and she pulled away.

Her hand dipped down and she copped a feel of my dick, which was fully erect.

Valerie looked surprised.

"Wow, Walter, how big are you?" she asked in a low voice.

"Average."

"You don't feel 'average.'"

"I think maybe I'm thicker than normal."

"I think maybe you are, too. I'm going to measure you."

Again, in a whisper, "Let's go back to your apartment, Walt. Your new pretend mom wants to teach you some things."

We both got up and made our exit, holding hands.

No one was nearby. It still was that early evening moment after rush hour and before busy night life activity.

"Have you ever gone down on a woman, Walter?"

"No," I said sheepishly.

"Do you want to learn?"

"Sure"

"Good, it's never wrong to lick a woman before you fuck."

I was a little taken aback by her frank language but said nothing.

"Are you kinky? Do you have kinky fantasies, Walt?"

I nodded shyly.

"Are you open to some roleplay? I guarantee you that you'll get some fucking in tonight."

I told her I had an open mind.

"Good."

We finished the walk in silence, stepped into the building elevator and went up to the seventh floor to my place.

Once inside, Valerie kissed me deeply again.

"Get a tape measure and take off all your clothes for mama."

I couldn't find a tape measure, so I brought her a string and a ruler. I stripped.

When I came back, I was surprised to find Valerie was fully dressed and seated at my card table.

"Come here," she said.

"Yes, mama," I replied.

It was the first time I had used the word 'mama' with her. She uttered a throaty chuckle and smiled wickedly.

"Such a good boy," Valerie said as she put her hand around my cock. "Jesus, you're thick."

She put the string around my shaft and then pinched the string to mark the place where it met. Next, she measured it against the ruler.

"Wow, almost six inches around. Average is about four."

"How do you know that, mama?"

"Because I love cock," she laughed. "I've made a study of it, even read a book or two. Now, let me measure the rest."

Valerie put the ruler next to my dick.

"6.5, almost seven, you are a big boy, and definitely above average. Average is between five and six." she said with pleasure. Valerie licked a drop of precum from the tip of my cock and I shivered in response.

"Yum."

"I've been eating pineapple."

"Good boy. Let's move to the sofa."

Valerie sat down and told me to kneel. She reached out and caressed my face.

"I'm going to show you how to lick Mama's pussy," she said. "Every son should thank his mother and his mother's pussy for giving birth to him. Every son needs to give his mama as much pleasure as his birth took in pain. Don't you think?"

"Yes, mama."

She caressed my face.

"That's a good boy."

With both hands grasping my head, she pulled my face toward her pussy, hiking up her skirt. I found that she had removed her panties while I was in the other room.

I could smell her arousal and feel the heat of her body, especially her thighs, as my mouth and chin descended. Under her skirt, I discovered a thick thatch of dark hair, trimmed and not unruly and then that first taste as I kissed and she gasped. Valerie pushed me away slightly.

"Start on my thighs like a good boy. Take it slow. It's important to give a woman time. You'll never regret it."

I planted kisses on the soft skin of her inner thighs, along with feather licks. I worked my way up and then started on her other leg. Valerie's legs were beautiful, long and well-shaped. My breath wafted toward her pussy, warming the air beneath her skirt even more.

Finally, I was back where I started, intimidated by a new experience but wanting to explore. Her scent was salty and warm, enticing. My first kiss pressed through her pubic hair, and I could feel the lips of her cunt against my mouth. My lips had met hers. I kissed everywhere lightly and elicited soft, little moans from her. Her flavor was like her scent. Hot and savory. I wanted more. My licks became wetter and all were on the surface from top almost to her asshole, and then back again.

Near the opening of her vaginal tunnel, I began licking deeper. Her inner pussy was wet, almost dripping, and licked up that moisture.

"There, Walt, yes. Take it slow, up and then down. I'll show you my special places."

With her fingers, she opened herself and pointed to a spot just below her clit and another just above her hole. I licked and ate her. I worshipped, and she let me. Her moans and whimpers became more frequent and louder.

"Maybe it's beginner's luck, but mama likes what you're doing. You're a good boy, a good son."

I brought her to her first orgasm and she pushed me away.

Valerie smiled down at me as she breathed heavily.

"That was great for a first time, Walt. It's important that mothers show their sons how to please a woman. We owe that to our future daughters in law. I'm not sure how much time we have left though. Do you know when your papa gets home? I can't remember."

It took me a second to remember we were in a roleplay. My cock was hard as steel and was something of a distraction.

"Uh, he said he had a business dinner and won't be home until after 9 p.m."

"Oh, good," mama smiled back at me again.

She stood and slowly stripped. Valerie's breasts were large and only showed a slight sag. Her nipples were rosy against her pale skin.

"Let's try again, Walt," mama stood over me, completely naked with her arms akimbo. Her feet on either side of my chest. "Do you want to make mama happy?"

"Yes, mama."

Good, her tone and demeanor became more stern.

"Good, I want you to make mama feel like a queen. You are going to be my throne, Walt."

She turned around and pointed her ass toward my face as she squatted above me. Her ass and pussy soon encompassed my entire field of vision as it descended to my face. Although Valerie supported the bulk of her weight on her knees and legs folded under her and to the sides of my head, I felt like her throne. Her ass was clean, having freshened herself up before we began having sex, but I drew her scent even deeper into my lungs and perception. I licked hungrily at her juicy quim and I was rewarded with a steady stream of her essence.

Valerie seemed even more into it. Her commands became nonverbal--- a shift of her weight and position to direct my tongue, a grunt or a moan when I was doing well and silence when I wasn't. Her pussy and ass were my world, and the sensations of my licking were hers. My tongue dipped into her hot, wet hole and swirled. She shuddered and moaned louder. Soon, much to her delight, I was tongue fucking her. Her motions became more frantic and her pressure heavier-- legs tighter around me, humping more energetic on my tongue and mouth. I began to fear for the well-being of my jaw when the vise reached its peak. A guttural, primal moan, loud and uninhibited, escaped her throat. A brief squirt of pussy juice drenched my face. My cock was so incredibly hard now that I ejaculated without any contact. It was a tiny squirt into the air, and it landed on Valerie's thigh, jolting her back to reality.