Luckiest Guy I Know Ch. 02

Story Info
With the help of my girlfriend, I score my step-mom.
8.5k words
4.73
134k
171

Part 2 of the 2 part series

Updated 06/08/2023
Created 10/10/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Luckiest Guy I Know Ch. 02 – With the help of my girlfriend, I score my step-mom.

Thank you for your interest in the first chapter of this story. I do not have any present plans for additional chapter(s), but am always open to returning to it. Your thoughts or suggestions are welcome; it is hard to underestimate how valuable your comments can be.

I am working on several stories at this time, none near complete.

As always, all story characters engaged in sexual activities are eighteen years of age or older.

* * * * *

During the summer I worked at the coffee shop and Viki, who shared a small off-campus apartment with three girls, became a regular presence at our house. I'd return from work to find her and Mom by the pool, cooking, or changing after a pilates or steps class. And when Mom headed for the shop, Viki and I headed for my bedroom. The only problem was keeping a ready supply of clean sheets, for Mom and I had adopted an unspoken protocol: she pretended not to know Viki and I were sleeping together at the house and I did my best to hide it from her.

The only cloud in my world was my upcoming trip to Dad's. As part of the divorce settlement I spent time with Dad each summer and although, consumed by his job and often on the road, he'd never shown much interest in me when I was there, it was his right to see me and dad-gum-it, he wanted his rights.

And so Mom was at the shop and I in bed with Viki bemoaning the time I'd be with Dad for the who knows how many time when she said, "I've been thinking about that. I know how to make your trip more interesting and a lot more fun. Seduce Sandy."

"What?"

"Y'know, Sandy, your step-mother."

"Yes, I know Sandy, are you nuts?"

"Don't you think she's pretty?"

"Yeah, I mean yeah, but I date you and she's my stepmother."

"It's sweet of you to be faithful, but it's not cheating if I say its okay and I think you should. Sandy and I spent that time together when your Dad was here for graduation, got along great, now we're always texting. She's like your mom, lonely and unappreciated in her marriage and while she comes across as sweet and innocent, there's a tigress in there."

"Viki!"

"Hear me out. As to the stepmother part, what could be better? Your Dad fucked around on your Mom, now you do his wife."

I said she was crazy, wondered whether this was some bizarre test of my fidelity, but Viki kept bringing it up and I eventually became convinced she meant it, but still said, "No," until one day, in frustration with her refusal to accept my "No's," I said, "How?"

"Glad you asked. I have a plan."

She outlined it for me. I told her she was nuts all over again. She said she'd handle phase one, I could decide whether to move on from there.

* * * * *

Distracted and angry, Sandy turned on the computer in the home office. Even though her husband was out of town and neither father nor son had any real interest in seeing each other, he'd insisted on Gabriel's visit. She was already teaching a summer school course at her high school, she barely knew the kid, what would she do with him?

Something else was bothering her. Sandy had found in Viki a sensitive and discerning ear and in their e-mails and texts had become increasingly forthright about her frustrations with her marriage, something she preferred her step-son not know. Had Viki told Gabriel about any of it, or about the afternoon of his graduation. God, the women had been magnificent; Sandy understood Gabriel's reluctance to leave her. No, Viki was a free spirit, but she was smart and discreet, Sandy trusted her judgment.

Turning her focus back to the computer Sandy made sure the flight was on-time, then

checked for messages from her students. There was only one. She opened it, read it, gasped:

"My mother did business with your husband, saw the picture of my favorite teacher in his office, mentioned it to me. I asked her to describe him. Then I understood. The first time I sat before you, you were vivacious, energetic, optimistic, dynamic, eager, positive, happy, full of life. And you've never disappointed, every day in every class you've been wonderful. Your energy's contagious, you spread it throughout the room, invest it in each of us.

"But I've also watched you in your unguarded moments, sitting by yourself at the end of the day, walking to and from your car. That's where I saw the change. At first the vitality you showed in class was omnipresent, but recently, in those unguarded moments, I've watched the joy drain from your face. The word is you married well, but I wondered, were you happy?

"The man my mother described was so unlike you. You exude life and energy, he is by the numbers, by the book, life taking second place to figures and columns. There is nothing wrong with his life, his way of being, but it must be hard on you. You are supple and flexible, he rigid and unbending. He'll never change and it must wear on you; not to celebrate the wonderful and unexpected the world can bring, not to treasure the joy our minds and bodies can bring. Instead to be with someone whose concern is not what it is, but what it costs, who measures success not by who he helped, but by who he hurt.

"I will be the one free you. For reasons you won't discern you'll know, and you'll prepare yourself, wear a short dress and heels that show off your delicate curves and killer legs, let me hold your body against mine.

"You'll know it's forbidden, but that will only make it hotter, make you crave it more. How long has it been since you embraced the forbidden, since you celebrated the uninhibited joy of your body? Together we'll demolish the walls of your silent prison and, best of all, he'll never have the imagination to suspect we're lovers.

"So you'll say yes, not at first in words, but by pressing your breasts, filled with blood, nipples hard, to my body. My hand will slip under your dress, cover your panties. My mouth will be on yours; you'll welcome my tongue.

"Your sex is wet and itchy, your nipples ache; I slide a finger inside you, my thumb covers your clit. You'll remember how you love a man's body, love a hard dick spreading the soft lips of your sex, spearing inside you; love the way sex smells, sounds, tastes, love a man focused on your pleasure and you on his.

"You rock your hips on my hand, moan, bend over your desk, thrust your hips into me as I enter you. You're seeing all this in your mind's eye, right now aren't you? Your sex is on fire; you know it will come true.

"You need to be fucked. Your hot pussy needs hard cock. You're husband won't do it, can't do it. I'll be the one. I'll fuck you silly, fuck you til the sun comes up, fuck you the way you need to be fucked. And when I do you'll know why it had to be me."

* * * * *

I was horrified when Viki showed me the e-mail, made her explain why it couldn't be traced back to her, made her explain it again, but finally, rationalizing that I couldn't stop her, assented to her sending it.

Then Viki suggested a new role play. I'd be me, she'd be Sandy, and I'd seduce her. It was fricking amazing, each and every time.

* * * * *

Sandy checked the message, no name, no return address. Who sent it? She pictured her students, one-by-one: who had she taught two years ago, who had parents who might know her husband? She started to forward the e-mail to the principal, stopped. Whoever sent it had sensed her inner feelings, things she kept hidden. Did she want the principal to know any of this? Would the e-mail become public? What would her husband think? She turned off her computer, she needed to think this through.

Driving to the airport, replaying the e-mail in her mind, Sandy was imagining wearing a short dress, a hand running down her body, across her thighs, a dick, hard and hungry, pressed to her. She'd turn her face to her lover, flatten her breasts on his chest, his mouth would cover hers, she'd welcome his tongue.

At a stop light Sandy, pussy spasming, rolled a hard nipple between thumb and index finger, ground her sex on her fist. She told herself to calm down, this was no time to be playing with herself.

She arrived at the cell phone lot early – traffic had been light – parked in the back, brought herself off, then, lingering in post-orgasmic bliss, wondered again, who sent the e-mail? He said he was safe. What student could be safe? Her phone pinged; it was Gabriel; she turned on the ignition.

* * * * *

I texted Sandy, then Viki and Mom to let them know I was okay, then wondered, had Sandy seen Viki's message? If so was she angry, fearful, or was Viki right, was she aroused? My phone pinged. Viki was asking me call her as soon as Sandy checked her computer.

Sandy pulled up, got out of the car, greeted me with a hug. Her eyes were dilated and her skin, normally a light pink, flush. I got in; the car smelled of sex. I looked at Sandy. I'd always thought her more pretty than sexy, but now, as I pictured her fingering herself at a sop light, I saw a sexy wanton edge.

* * * * *

Sandy showed me the guest bedroom, then said, "If you'll excuse me, I need to check for messages on my computer, for school."

"Okay, I'm going to call Viki."

Sandy's face perked up.

"I really liked her. We had the best time while you and your Dad were at that father-son thing. We've kept in touch."

"She told me. And yeah, she's a force of nature, but I'm holding on as best I can. She said the same about you, said she had a great time, asked me to...," what was a synonym for seduce you, "say hello."

* * * * *

"Hey babe."

"Hey, how long?"

"How long what?"

"How long after you guys got back did she check her computer."

"Right after she showed me my room, maybe three minutes."

"Excellent. Is she looking at the e-mail?"

"I don't know."

"Well, go look."

"I can't do that."

"Yes you can."

It wasn't much of an argument, but I had no retort, and glancing through an office door helpfully left ajar I saw Sandy read Viki's message, wet her hips, absent-mindedly touch her breast, read it again. I returned to the kitchen and called Viki.

"You were right, she's reading your e-mail."

"Good, tomorrow, while she's at school, check her computer, let me know how many times she's viewed it, whether she forwarded it to anyone."

"Viki, I can't look on her computer, it's private."

Viki laughed. "First of all, it's my message, not hers, if it's private, it's private for me and you have my permission. And honey, be serious, soon you'll be between her sheets, between her legs. Privacy is not an issue here."

I said, "Viki, I am..."

"Hey Gabriel. Oh, sorry, I didn't realize you were on the phone."

Viki said, "Is that Sandy?"

"Yes."

"Good, please give her the phone, I'd like to talk to her."

I handed Sandy the phone, who, talking animatedly to Viki, wandered off.

* * * * *

The next morning, Sandy at school, I was sitting before Sandy's computer – I found the password was in the top desk drawer – and phone tucked under my chin, said, "Okay Viki, I'm in. She opened the message ten minutes after you sent it, it must have been right before she left for the airport, then four times last night, three times this morning."

"Did she forward it to anyone?"

I checked. "No."

"Excellent, now she can't, she'd have to explain why it took her so long. Is our girl's libido on the war path?"

"Best I can tell, yeah. I'm pretty sure she masturbated on the way to the airport yesterday and I heard her last night. She also dawdled in the shower this morning."

"Most excellent. Time to put our plan into place."

"Viki, we don't have a plan, you have a plan. I haven't said I would, even if I could."

"You'll come around. Think about it: you'll get to show off all the things I've taught you to a wonderful new lover. It will turn me on; when you get back I'll be on fire. I know, I'm always on fire, but we're talking five-alarm-stuff. And that's not the best part. The best part is that it's your Dad's wife, it's the ultimate revenge for his screwing around on your mother. What do you know about jazz?"

Bewildered by the sudden turn in our conversation, I said, "Not much."

"In the living room you'll find a bunch of jazz records, original vinyl, classic stuff. Sandy collected them, but your Dad, as Sandy described it, gets passive-aggressive when she talks about it or plays it, calls it jungle music, so she's pretty much stopped.

"Find the records, play them. When she comes home be interested. I didn't say act interested, I said be interested. I'm like you, I don't know much about jazz, but when she talks about it she gets absolutely transported. It's a vital music you and I know nothing about. I know you, you've got enough intellectual curiosity to get interested."

"And this will help me seduce her?"

"Of course, and what else do you have planned?"

Good question. I was in a low-key suburb where I knew no one, ostensibly visiting my father, who wasn't there.

"Nothing."

"Good, let me know how it goes."

* * * * *

When Sandy got home Louis Armstrong was playing on the stereo and I was chopping the ingredients for shrimp etouffee in the kitchen.

"Hey Gabe, whatcha doing?"

"I hope you don't mind. I saw these records in the living room, put some on. When I found the Louis Armstrong records I thought about New Orleans, which made me think about this shrimp etouffee Mom taught me to make. I ran down to the store for the fixings, figured I'd cook us dinner. You game?"

"You're sweet, I didn't know you liked jazz."

"I don't know if I do either. I'm not really familiar with it, although I recognized some of the names."

Looking wistful, Sandy said, "I love it, don't play it much anymore, but when I do I'm always reminded why. I'll put my things in my office, then give you a hand."

And, after enough time to read Viki's e-mail several times, she did.

* * * * *

Sandy and I fixed dinner, discussed her, her day. Viki was right, as I focused the conversation on Sandy, a rare event in her Dad-centric world, she blossomed. We ate dinner in the living room as she played record after record and, as Viki predicted, I was captivated by the music and her enthusiasm for it. It was close to 11:00 before, noting the time, she said, "Oh, sorry, it's getting late."

We packed up the records, then she went to her office, re-read Viki's e-mail, and wondered again, who sent it.

* * * * *

I came downstairs to the smell of coffee and Sandy wearing a floral dress and a bright smile. I kissed her cheek. She smelled good.

"Good morning Gabe. I made coffee, help yourself. I wanted to let you know how much I enjoyed dinner and our conversation last night."

"Thanks, I had a great time. If it's okay, I'd like to play some of the albums you talked about."

"Of course, music is meant to be heard and shared. I'd love to know what you think."

Her phone rang.

"It's your father. I'll take it in the car."

Sandy hadn't driven two miles when my phone rang.

"Hey son, my stay here has been extended. I just talked to Sandy; she's not happy. Do me a favor, take her to dinner tonight, on me, her favorite place is the Versailles House."

* * * * *

I found the Versailles House on-line: expensive, formal, heavy food encased in heavy sauces. I looked at the reviews, obsequious service, food palatable if over-priced. This did not look like Sandy's favorite place.

I called Viki, filled her in. Making no effort to disguise her glee she said, "Excellent, your Dad, thoughtful man that he is, has provided us the perfect opportunity. We must make sure to thank him. Sandy once texted me about a soul food place. What was the name, let me check, what was the name, what was the name, found it, the Praline Connection."

"Spell Praline."

"P-R-A-L-I-N-E."

I googled the name. "Got it."

"Okay Gabe, make reservations for tonight. Hot music, spicy food, steamy dancing, by the time you get home she'll be putty in your hands."

"Viki, are you sure you're okay with this? You're asking me to cheat on you."

"Like I said, it's not cheating if I say it's okay and I say it's okay. And I promise, when you get back the sex here will be hotter and crazier than ever."

I was a teen-aged boy; there could be no argument more convincing.

* * * * *

I sent Sandy a text: "Is Versailles House really your favorite restaurant?"

"LOL, no it's your Dad's. Place is stuffy as heck. Why do you ask? Did you talk to him?"

"Yeah, he told me he's delayed again and you're pissed. He wants me to take you to the Versailles House to mollify you. I looked it up, it didn't seem like you. You know a place called the Praline Connection?"

"Yeah, I haven't been there since I married your father, love it."

"Well honey, got a date tonight, cause if not I'm looking for one."

"My dance card is wide open."

"Great, we'll get dressed up, make it a special evening."

* * * * *

Wearing the one nice set of clothes I'd brought, the ones Viki has selected, the ones she insisted I pack, I watched Sandy come down the stairs dressed in the manner described in Viki's e-mail, dress not skin-tight, but tight enough to show off her curves and short enough to show off her legs, heels high but suitable for dancing, earrings long and dangling, hair in a ponytail. She was ready for a good time.

"Damn, showing off the gams."

"You don't think it's too short and I haven't heard 'gams' in years."

"That's a heck no and I've read Raymond Chandler."

"I love Raymond Chandler."

Viki had suggested him, I'd read him on the plane. I don't think it was a coincidence. By the way, I recommend him, great stuff.

* * * * *

The Praline Connection was everything advertised. Food good, music hot, and Sandy and I danced. After the past months with Viki I'd gotten pretty good at it and, as we did, I understood what Viki saw in Sandy. She was pretty and blonde and cute and sweet, you couldn't miss that, but now I was seeing an underlying sexiness, not Viki's can't-miss-it sexiness, but something more subtle, sexier because it was hidden, sexier because it was blossoming before me.

* * * * *

Later, her hand in mine, I walked Sandy to the car. My phone rang, but I ignored it, instead I held her door open, helped her in, then walked around the car, got behind the wheel, and checked my phone.

"That was Dad. Do you want to talk to him?"

"Heck no, he'll just bring me down."

Sandy pulled the tie from her pony tail, shook her head, letting her hair down, and lowered the visor to re-do her lipstick while I put the key in the ignition, preparing to back up, when my phone pinged. It was a text from Dad: "Gabriel call, it's important."

I showed it to Sandy who smacked her lips together and said, "I guess you better."

I said, "Maybe we'll get lucky, maybe he's delayed again."

She said, "You're a bad boy."

I said, "We'll see."

"Hey Dad."

"You alone."

"Yeah, getting ready to drive to the store, Sandy asked me to pick something up."

"This late, that's nice of you son. How did it go tonight?"

"You mean with Sandy?"

An impatient, "Yes."

"Versailles House was booked, so I took her to the Praline Connection."

"Never heard of it. Did you mention my name to the Versailles?"

"No."

"Next time do so, they'll find a place, they love me."

I said, "Will do."

"How is she?"

Looking at Sandy I said, "I did my best to charm her into forgiving you."

She shook her head in the negative, extended her lower lip in a pout.

"But I'm not sure I made much progress."

"You need to keep trying, I'm going to be out here another couple of days."

There were voices in the background, Dad, only paying half-attention to me, spoke to someone.

Naughty grin on my face I hit the speaker button, looked at Sandy, and said, "Really Dad, delayed another couple of days. I'll do the best I can with Sandy, but I don't know how she's going to react. Can I do whatever it takes to make her happy, anything at all?"