The Finer Points of Sheila Ch. 01

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High school senior discovers his best friend's mother.
6.9k words
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Part 1 of the 5 part series

Updated 10/16/2022
Created 10/28/2006
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bluefox07
bluefox07
472 Followers

"The Beginning..."

EDITED BY:

Miriam Belle

CREATIVE CONSULTANT:

Simply_Cyn

Author's Note:

"For me, this story is the most personal. A lot of this story is based in truth from my own life, so it really has a special place. When it first posted 2 years ago, the reader response was overwhelming. I thought about making changes to it for this reposting, but I decided against it. So, here you go. Cheers!"

***

My senior year of high school was probably the best of my life, if not the most eventful.

This was the year that I finally came into my own as a person and started really exploring what life had to offer. I was never what one would call a jock, or a nerd, or geek or even popular. I was one of those guys who cruised in that moderate gray area, not really ambitious enough to strive for that ever-elusive and sadly-finite title of "Popular," nor did find myself labeled with the far more common and unfortunately for most long lasting brand "Loser." I was just myself.

I played football (not very well, mind you, but I could plow people over with the best of them), I worked as hard on my studies as I guess any average senior does and I was stupid enough to start smoking, but smart enough to avoid the pitfall of serious drug addiction.

My best friend Elle was my right-hand woman, my partner through thick and thin since we were six years old. She was a great girl and she had really blossomed starting our freshman year from the beanpole I had know and loved for years to a fully rounded young woman that I lusted after. I guess we both liked each other a lot, but we knew our friendship wouldn't survive it. I had been through seven different girlfriends during the last four years (typical of the high school mentality) and she had been experimenting with her sexuality with a number of different guys. Our relationships never lasted longer than a roll of Mentos, and we cared too much about each other to screw up our friendship with sex.

Elle was 6 foot even with long mahogany hair that hung from her head like shiny silk, all the way to her shoulders. She was a little on the heavy side, but it wasn't grotesque or anything. She just had the right amount of meat on her hourglass frame, with the biggest set of tits in the senior class. She was a healthy 40DD, and the other girls despised her over her natural bustiness. She had large brown eyes that really told you everything you would ever need to know about her. She tended to wear her emotions on her sleeve, which was both good and bad depending on the situation, but for the most part she was a loose cannon.

And it worked for her.

Her parents had been going through another dive in their marriage that year. Her dad, Tom, and her mother, Sheila, had known me since I was a kid and had always been friends with my family. My mom and Sheila had gone to school together and once it became clear that they would never get out of this one-stoplight town, they resigned themselves to a life of marriage and children.

I'm not saying that my mom or Sheila regretted getting married or having kids (well, maybe my mom does, at least the marriage part), I just know from talking to Sheila that they both had some pretty upper-end goals for their lives. Instead of becoming a doctor, Sheila settled on becoming a real estate agent and marrying Tom.

I guess we all knew Tom stepped out on her, which blew my mind because Sheila was everything her daughter was, only with bigger tits if you can imagine. I had always meant to sneak a peek at one of her bras throughout my adolescence, but never got an opportunity. I figured that they were at 42DD, if not bigger. I had lusted after Elle to be sure, but Sheila was my secret obsession and the golden standard that not many women could ever really meet. Why in the world Tom would cheat on her was beyond me.

Unbeknownst to Elle, her father had dealt with the guilt over his infidelity by turning all of his attention to her when he was home. She had been daddy's girl all her life, and their relationship was strong and clearly meant to isolate Sheila from the family. I think, even now, that Tom was trying force Sheila to leave or cheat on him so he could be justified in his lifestyle. The hundreds of times I had been over there hanging out with Elle allowed me to witness his mind games, and his total hold over his daughter. It could be simple shit like what to do about dinner, and Sheila would suggest making her homemade pizza (which was fabulous and way better than even Round Table, I might add) while Tom complained that he wanted Chinese.

Elle would follow suit and finally, Sheila would give in and start to order the Chinese food. Tom would then say he didn't want it if she was going to be a bitch about it, and that they should just have the pizza if it was going to be such a big deal. Sheila was at a breaking point after eighteen years of this, and to her credit, would be as gracious as she could be and offer to make the pizza again rather than argue. Tom would make some smart-ass comment and she would crack. An argument would ensue, and somehow Sheila came off as the villain through the process of Tom's lawyer-esque argument tactics.

In the end he provoked his wife to such angry extremes that Sheila had finally had enough. She slapped the shit of Tom one night, in front of Elle and me, and sent the man to the floor, breaking a lamp. It was no easy feat, as Tom is well over 215 lbs and no slouch when it comes to strength. We were all dead quiet as he stood up, dusted himself off and calmly said, as though he had been rehearsing it, "You know, Sheila, I've fucking had it with you. You're a self-centered bitch who never thinks about anyone but herself, and now you've taken our bullshit and put it out in front our daughter and her friend. It's over."

With that, Tom stormed out confident in his self-nurtured righteousness and made for his truck in the driveway, and Elle got up to follow.

"Sit down, Elle," Sheila said, her eyes on the floor.

"No," Elle said as she knocked over her chair and scooted the table into me, "He's right, you always do this!"

Sheila looked at her, her eyes filled with tears and said, "Do you think I want this? He wants me to leave, don't you understand? He's turned you against me!"

"If you had been a good wife, maybe it wouldn't be that way!" she yelled.

"Elle," I said quietly as I stood up, putting a hand on her shoulder, "You're not being fair."

"You stay out of this," she fired at me. I had never experienced her directing her rage towards me, even for a second in all the time I had known her. I stepped back, my eyes wide as I put my hands up inoffensively.

"Elle, do not go out that door," Sheila said, her voice clearly not kidding as the truck outside started up with a roar. Elle looked at her for a moment, and then left. We stood there for a moment as we heard the truck door slam and then the whine of the tires as Tom pulled out of the driveway and drove off. Even after the squeal of the tires had faded, I could still hear the spiteful words Elle had spat at her mother hanging in the air. Sheila leaned against the kitchen counter, and then slid down the front of it, crying as she went.

"Jesus, Sheila," I said as I sat down beside her and put my arm around her. Her shoulders were shaking violently as she wept, and I couldn't blame her. Tom had fucked her over, and just for standing up for herself, she was being crucified by her own daughter. I said, "She didn't meant that, any of what she said... and Tom is full shit, Sheila."

"Don't talk like that," she said as she regained her composure.

"No," I said, feeling that I had to speak my mind, that maybe if I did, it might help her, "I've seen this shit going on now for a long time, and it isn't fair. He's been turning her against you, and I see it and you see it. I know I have no right to be saying anything, but you and Elle are so close to me, I don't want to see either of you hurt."

"That's sweet Doug," she smiled and looked at me, her eyes puffy and red and yet, looking so reflectively radiant that I felt my heart start thudding in my chest and an erection begin swelling in my pants. "But this is just the way it has to be."

"Why?" I asked, "Why does he get to do this to you? You had every right to slap his sorry ass to the floor, which by the way, was the coolest fucking thing I've ever seen."

Sheila laughed. "Really?"

"Hell yes," I smiled, squeezing her shoulder, "It was like one of those big payoff moments in a movie that everyone has been waiting for, and then it finally comes. If I could have, I would have given you a standing ovation."

"It's really been that apparent?" she asked quietly.

"Yeah," I nodded my head.

"He's been cheating on me," she looked at the floor, more tears spilling out as she spoke, her voice trembling as she fought back her inevitable break down, "He's been cheating and I let it go. I ignore it. He says these horrible things to me and I let it go. He sets me up and tricks me into arguments and I let it go. He turns my own daughter against me, and I let it go...no, I let it happen. I let it all fucking happen."

She began sobbing again, and I felt my heart break for her. I pulled her close and held her in silence for the next hour. I worried Elle and her father might come back, but they didn't. In fact, even after I had walked Sheila up to her bed around 9 that night, they still had not returned. Sheila took off her flannel, and the undershirt she was wearing revealed that not only was I right about her tits being in the double D section, but that she was also not wearing a bra. Her nipples looked huge as they strained against the thin fabric, and I had to not stare as she sat down on the bed, flipped her legs up and under the blankets. Thank God she kept her jeans on. I might have creamed myself right there, just looking at her.

"Thank you, Doug," she said as she propped her head up with three of the fluffy pillows, "You're right about everything."

"I wish I weren't" I shook my head, "You and Elle deserve better."

She looked at me for a moment and then said, "You love Elle?"

I smiled, feeling a little embarrassed. "Uh, yeah I guess I do," I said, "But not like that, you know? She's been my best friend for a long time and I just don't want to lose that. I just see so many friends cross that line and after they realize they can't handle it, they lose what they had."

"That's very observant."

"I think so," I said, "I mean, Elle is a knockout, don't get me wrong and a great catch. The only catch better than her in this town is you, Sheila. Considering she gets what she has from you, that's a pretty good place to be in, right?"

Shelia smiled, a blush coloring her beautiful, flawless skin. "You are a charmer."

"I just call it like I see it. Here's my cell phone number if you need anything, okay?" I said as I wrote the number down on a receipt I had in my pocket.

"Thank you Doug," she smiled again, and put the number in her nightstand.

I got up to leave and turned off her bedroom light. As the room fell into deep blue shadows, I said, "You know Sheila, you deserve much better than this. Elle is a good girl, and it isn't because of Tom."

I couldn't see her face very well, but I think I heard her beginning to cry again.

"Good night, Doug."

I wanted to say more, but in the end I didn't.

"Night Sheila."

***

That next afternoon, I bumped into Elle at the mall. She looked tired, but beautiful as always. We walked together for a while, talking about inconsequential bullshit and everything but the incident last night. Her eyes were puffy and red, reminding me of Sheila just before I had left her. I was dying to know what had happened after she and her father got home, but I held off until she was ready to talk. It wasn't until we sat down for dinner at the Taco Hut at the far corner of the food court that she addressed the issue.

"I'm sorry for the way I yelled at you last night," she apologized as she stirred her ice tea with her straw, "That's not how I wanted to spend the evening."

"No, it's alright," I lied, still angry for her ignorance of the truth about her dad, "I just thought it was harsh the way you bailed on your mom."

Elle rolled her eyes. "I know she looks like a victim, Doug. But she's not. You ever wonder why dad acts that way towards her? He's put up with too much of her bullshit over the years, and he's had it. That's why I don't blame him for..."

"... for cheating on her?" I finished, knowing I was either going to get slapped or rewarded for my bold comment.

Elle looked at me, her eyes unreadable as she stirred her tea, her mouth twisted into a tight grimace. She finally said, "Yeah, for cheating on her. Would you put up with that?"

"Elle," I said, feeling more and more uncomfortable, "I've been hanging with you since we were little, and I have never seen your mom do anything to him to justify what he does or says. It's common knowledge what he does behind her back, and I gotta be honest, most people don't see it the way he does."

"Really? What people?"

"Jesus Elle," I sighed as I poked at my taco salad, "It doesn't matter. What does matter is that right now your parents are in a bad way, and they both need you. To be fair, they BOTH need you."

"I'm there for my dad," she eyed me, "but mom can just go to hell."

"Elle..." I began, but she cut me off with her finger over my lips.

"Doug, you're a nice guy, a smart guy," she said softly, "But you are blind to a lot of things. This is one of them. Just let it go."

I considered that hard for a minute as my mind raced. I wanted to defend Sheila, I wanted to make Elle see what that fuck Tom was doing to her family and expose him for the sleazing shit-head he really was. But, I also loved my friend. And I could see that I was going to make it worse if I butted in and made it my problem. She was warning me to stay out of it, and despite what I knew and the injustice of it all, I did just that.

"Okay," I said against her index finger, "Okay."

"Good," Elle smiled and picked at her nachos, "You going to the party tonight?"

"Yeah, I think so."

"Good, you can be my date."

"No," I corrected her, "I'll be your designated driver when you finally slip into an alcohol induced coma."

"That's love, isn't it?"

I laughed, "Sure."

***

It was a little after one in the morning when I pulled up to Elle's house. Tom's truck was gone, and I thanked God for small favors. I didn't need him breathing down my neck and asking questions. I got out, opened the passenger side door and lifted Elle out of the car. She was passed out from her merrymaking and on her way to having the worst hangover in the history of bottle tipping. She also had fucked three guys at the party from what I understood, and if she didn't wind up pregnant she would be lucky. As I carried her, her shirt opened up and I could see she had lost her bra.

The door was unlocked and I managed to open it. I quietly went upstairs as the staircase creaked louder that I had ever heard in all the time I had known this family. I had just made it to the top when the light came on suddenly, and I almost dropped Elle. Sheila was in the hall, in her nightgown and robe and looking at me.

"What happened?" she asked, her eyes wide.

"She had a little too much fun with Jacky D. and the Captain," I grunted as I moved towards her bedroom. Shelia came to help me as we got her into the room and plopped her on her bed. Elle only mumbled and then began snoring loudly. I sighed, my arms screaming as they recovered from carrying her weight. In the transfer, her shirt opened all the way, revealing her huge tits. There were hickies all over them and her stomach, up her neck and on her shoulders.

Sheila looked at me. "Did you?"

"No," I said, realizing how bad this must have looked, "No, I was her driver tonight."

"Why didn't you stop her?" Sheila asked incredulously and covered her daughter up, "You're supposed to protect her, and she's your best friend!"

"Hey," I snapped, angry for a moment and then calming down, "She does what she wants and there isn't jack shit I can do to stop her. You don't think I've warned her, Sheila?"

Sheila stood back and glanced down at her unconscious daughter. She shook her head and then smiled apologetically. "I'm sorry, Doug," she said genuinely as she hugged me. Her body felt so good against mine. The sensation of her huge tits against my chest while sliding in the fabric of her silky nightgown made me feel dizzy. God, she even smelled good, like lavender, as she held me tightly against her. I returned the embrace. She added, "I know that you did what you could. Thank you for bringing her home."

Sheila covered her up and we went down stairs to the kitchen. As we got into the good light, Sheila noticed my eye.

"Jesus Doug, what happened?" she asked as she tilted my face towards her.

"Elle punched me right before she dropped," I said and winced as she touched the bruised skin at the corner of my eyelid, "She really didn't want to come home yet."

"Let me get some ice for that," she said as went to the freezer. I sat down in the chair that Elle had knocked over the night before, watching Sheila's ass flex and un-flex as she walked, the silky fabric at the mercy of her perfectly round ass.

"I am so sorry for her behavior," Sheila said with a frown as she opened the freezer door and grabbed a handful of crushed ice. She opened one of the nearby counter drawers and pulled out a zip lock sandwich baggie and began filling it with the ice.

"Where's Tom at?" I asked bluntly and looked around.

"He's gone for a few days," she said as she zipped up the plastic bag and massaged the ice around inside. She came over to me and applied the ice pack to my eye as she added, "Hunting."

"Hunting," I repeated, the ice wickedly cold against my skin.

"Yeah," she said with a doubtfully sarcastic look, "A man who won't even go camping without a hotel and room service."

"So that's why you guys never went camping," I smiled. I noticed that she was still holding the ice pack to my head, and her breasts were blatantly eye level in a tantalizing jiggle.

"When you're paying off your deadbeat husband's gambling debts and supporting a growing daughter, with rent and bills on the side, well, camping is a luxury."

"I love camping," I said as the sting of the ice faded and then began to soothe, "Maybe I'll take you some time."

There was a moment of silence between us as I realized my words had taken our thinking beyond the mere relationship of mother and daughter's friend. My lust for her, and my concern for her, and I guess my true feelings about her had surfaced and leaked as the words came out, suggesting that I thought we could be more than just our longtime status quo. Sheila looked at me, her eyebrow cocked.

"I'm old enough to be your mother," she smiled maternally, "In fact, I'm best friends with your mother and you know it could never happen."

"I know, " I conceded, but was amazed that we actually knew what we were both talking about, that she had actually had the same thoughts I had. Her words "... and you know it could never happen..." said volumes to me. As much as I had slipped up in letting on that I'd gladly take this married woman camping, she had slipped and let it out that she had already come to the conclusion that we could never happen. And that meant she had thought about being with me at least once before now...

But if she was truly convinced that she wouldn't ever see me that way, it didn't show as she moved, her braless tits swinging for a moment inches from my face.

"Tom and I are divorcing," she said plainly as she sat down in the other chair across for me. "It's been coming for a while now, and I finally gave him a reason."

bluefox07
bluefox07
472 Followers
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