The Finer Points of Sheila

"The Inevitability Of It All..."

EDITED BY:

Miriam Belle

CREATIVE CONSULTANT:

Simply_Cyn

Author's Note:

"When they have you by the balls, they really know how to squeeze..."

***

It was around one in the morning when I opened my eyes. At first, I was a little confused as I slowly focused on the strange room around me. I felt a brief moment of panic as I registered I was not in my own room. Then I felt a hand on my shoulder, and I remembered where I was. Sheila was spooned behind me, her thighs tucked up behind mine as she caressed my shoulder. Her breath was hot and wonderful on the back of my neck. The combination of her exotic perfume and the scent of her hair made me feel so content as I smiled in the dim light of our room at the Freeling Hotel.

"You're cute when you sleep," she said into my ear.

"I thought I was cute all the time?" I said with a mock hurt.

"No," she kissed the back of neck, her body so soft against mine, "You're irresistible all the time."

"Now is no time to suck up," I said, never before having been so genuinely flattered. It was amazing and strange at the same time, being here with a woman who was not only the most attractive I had ever seen, and maybe the end all be all of lovers for me at the age of eighteen, but also the mother of my best friend.

Sheila was quiet for a moment. "It's wrong what we're doing, you know."

"All four times tonight?" I asked, "Should I have done the swirly thing with my tongue when I went down on you that last time?"

"No," she laughed, hugging me close, "I mean this...us... right now I feel like this is like being in bed with Dustin Hoffman."

"Which movie was that?" I smiled to myself, "Uh, 'Rain Man', right?"

"No," she grinned.

"Hook?"

"What?" she laughed again.

"Oh wait, I know this one. It's a classic," I said as I rubbed her thigh, "Marathon Man?"

"You're a geek."

"Here's to you, Mrs. Robinson," I said as I reached over to the nightstand and took a drink of water.

"Can you be serious for a minute?" she kissed my shoulder, "Please?"

"Absolutely," I smiled, although I didn't really want to see where this was going if she was going to start feeling guilty.

"Doug, I feel like I'm fucking you over."

"Well, you sort of are... four times tonight so far..."

She smiled despite herself. "You know what I mean. You're eighteen years old, and I'm old enough to be your mother. I'm forty-five. If anyone ever found out..."

"No one is going to find out," I reassured her, pulling her close to me as I turned to face her. She rested her head on my chest as we settled and got comfortable.

"How can you be so sure?"

"Do you think anyone here recognized us? Do you think anyone here even cares? We're an hour away from everyone and everything we know. I think we're safe."

There was a moment of silence between us.

"I just don't want you to regret any of this," she said softly, her vulnerability thick like a heavy smoke, encircling her.

"Sheila," I said, trying to pick just the right words, "This is the best thing that's ever happened to me. The only thing I regret is that it didn't happen sooner."

Sheila chuckled. "Any sooner, and it would've been considered an expression of pedophilia."

I felt her body shift against me, the heat of her leg draped across mine, the warm wetness of her crotch against my skin and the pressure of her large, perfect breasts. It was a feeling that years later I would look back on as being the first time I ever felt really secure. I felt safe with her, free of doubts or inhibitions about myself. Sheila made me feel confident and sexy, she made me feel like I was someone special and she did it all without even knowing she was doing it. It was like a second nature to her.

"Tom isn't coming back," she said bluntly, and I could feel her physically wince as she said his name, as if the words were razor blades tearing her throat apart as they left her mouth. "He packed up all his things and was gone by Wednesday evening. Elle took it really hard. She hasn't said a word to me since."

I frowned. "She hasn't said anything to me about it, either. You'd think being her best friend would count against keeping secrets."

Sheila looked at me slyly. "Do you tell Elle everything?"

"Touché."

"I don't know what to do," Sheila sighed, "Everything is falling apart."

"You can't look at it that way," I said as I ran my fingers through her silky, bronze hair, "Tom's a prick, and we all know it. He's been stepping out on you for awhile now, and he's tired of being sneaky about it."

"Sneaky?" she asked, "You know how many times I've found lipstick or perfume that's not mine on his shirts... and his underwear?"

"Shit, he wanted you to know."

"You think?"

"It's so obvious. He wants you to leave him, to get mad and walk out that way he doesn't have to initiate anything. Did he say he wanted a divorce before he left?"

"No."

"Well there you go. Then he can look like a victim..."

Sheila sighed. "I hate him, Doug. I hate him for what he's put me through. And he has the balls to accuse me of being the problem?"

"The guy's a fuck," I laughed as I squeezed her to me.

"A lousy fuck, in more ways than one."

"That's the spirit," I said, deciding to change the subject, "Now, its time for a exercise in self-esteem."

"Excuse me?" she looked at me.

"Your ego has been wrecked by that guy for years. Now repeat after me..."

"Oh my God," she giggled.

"This only works if you repeat everything I say and mean it."

"Okay," she rested her chin on my chest.

"Say, 'I, Sheila Crane, am without a doubt the sexiest woman over forty in the world, even sexier than Raquel Welch'."

"I, Sheila Crane, am without a doubt the sexiest woman over forty in the world, even sexier than Raquel Welch."

I nodded. "I have a beautiful smile..."

"I have a beautiful smile," she repeated through a laugh, proving to me just how right I was about that smile.

"My eyes are mysterious, my ass is round and firm and my breasts gleefully defy gravity..."

She laughed and hugged me.

"And say that I, Doug, am the best lover you're ever had. That my modestly large penis is the pinnacle of male achievement in a world of phallic obsession."

"Now whose ego are we building?" she asked, her hand sliding down my chest, under the sheets and to my semi-erect cock. She began stroking me, her thumb rubbing over my glans and making my balls tingle.

"I just thought I'd slip that in there."

"Well," she kissed my neck as she stroked my slowly hardening cock, "You are on your way to being the best lover I've ever had, Doug. That's no lie. And your cock is something special..."

"Oh go on," I rolled my eyes, enjoying the feeling of her hand job, "No really, go on. Keep going."

Sheila smiled. "You make me happy Doug, happier than I've been in a long time."

"That's what friends are for," I smiled, her fingers caressing my scrotum.

"You sure you're only eighteen?"

I nodded as she stroked my shaft to a healthy erection. As I lay there, I began to consider the very real possibility that Sheila was becoming more than just a friend to me. It was crazy; the very idea of our age difference would be laughed at and ridiculed if we ever took it beyond this. Maybe she was rebounding from her failed marriage? I figured maybe I was just caught up in the heat of our passion, carried away from common sense by our mutual attraction. But how could I help not being carried away by her? She was gorgeous, kind, smart and so damned sexy it could be considered a crime.

But something had happened to me between the drive to this hotel and found fruitition the moment we began dancing only a few hours ago. When she put her hands on me, under that intense light and the beat of the music dictating our direction and pace, I let go of all control over myself. I was simply with her, both of us an extension of the other, moving together toward something much bigger than ourselves. I knew that I didn't know jack shit about the real world, and I knew even less about what a real relationship was, or what it even entailed. The only thing I knew for certain was she touched me and so precisely stimulated me that I was already missing her before she was gone.

I ached for her when she wasn't there.

"Penny for your thoughts?"

"Oh," I laughed, "I was just thinking about you."

"And what were thinking?" she purred as she kissed my neck, her hands warm and tight around my thick shaft, slowly pumping up and down.

"That you're amazing," I murmured as she slid her body on top of mine, my hands caressing her ass as the sheets pulled down. Her pussy was clean-shaven and smooth against me. Her wet lips pressed against me as she necked on me.

"Keep going," I felt her smile against my neck as she moved a little more and positioned her pussy on my shaft, grinding herself against me. I massaged her breasts slowly as we rubbed against each other. She was deft in every move, her every lick and touch a perfectly targeted erotic missile setting me on fire.

"I've never wanted anyone more than I want you."

"Mmmm, nice," she raised a brow and grinned wickedly at me as she began kissing her way down my chest, running her tongue over my pecs and nipples. As she went down, her breasts dragged on me and sent a shiver through my body. She stopped when her tits reached my cock, their silky smoothness against my shaft a sensation unlike any I had ever known before.

"Here Doug," she said as she sat up on her knees, her body absolutely glowing in the pale lighting of the room, "Let me lay down, and you just straddle me."

As we switched positions, I stupidly asked, "Why?"

She regarded me with a hint of playful sarcasm. "You do know how to tit-fuck?"

"Of course," I replied as she settled in on the mattress. Her hair splayed out from her head like a dark shiny fan, her eyes looking at me expectantly as she cupped her breasts and squeezed them together. Her nipples poked out from between her fingers as I put one leg over her and straddled her torso. My balls rested against her smooth skin as I lowered my painfully throbbing seven and half inch cock between her tits. She pushed them together and I shuddered as their warmth enveloped me. I looked down and saw the head of my cock just barely peeking out of her cleavage, a shiny droplet of anticipatory pre-cum oozing out.

I began to slowly thrust against her tits, being careful not to crush her rib cage as I went. With each thrust, my cock would emerge from the crevasse of her breasts and she would quickly suck on me before I pulled back. The contrast of my swollen, almost purple head against her milky white flesh burned into my memory as the mixture of my pre-cum and her saliva lubed up my passage. Her tits seemed to roll and jiggle with every movement, her nipples erect like two dark rocks on twin white sand dunes.

"Yes baby, just like that," she smiled as I started thrusting a little faster.

"Oh Sheila," I managed as I felt my body preparing for the inevitable conclusion.

"I want you to cum for me, Doug," she whispered, her eyes burning into mine.

"Yes," I whispered.

"I want you to cum on my tits," she breathed, and just hearing her say that made me kick up my pace a notch. I had seen a lot of porn flicks where women moaned that phrase to men, and it was always a superficial turn on. But this was different. There was emotion behind the words, powered by passion and need. When Sheila said the words, with her sultry voice and the lust I felt behind her words, it was irresistible. She licked my head quickly again and said, "Cum on my face, Doug. I know you want to."

"Yes," I moaned, unable to think of any other reply as her words began to carry me away.

"Cum for me Doug," she moaned.

I tried to yell out as I came, my fifth one for the night, but the combination of a slight rawness to my cock and the tingling of the orgasm only allowed for a gasp of air. My semen exploded across her neck and chin in a long, white rope of cum. I spurted again and again, releasing only a fraction of what I had done earlier, but still soaking her enough to make a mess.

"I don't know how much more I can take," I huffed as I began to lose my erection between her tits.

"Now Doug," she ran her hand up my stomach lovingly, "You're not winded are you?"

"No," I collapsed on the bed, settling in close to her, and then added, "Yes."

"I'll bet I can get you up for another round."

"Oh yeah?"

"Yeah?"

"How?" I asked. I opened my eyes as she propped herself up on one arm. With her free index finger, she wiped up some of my cum off her neck, raised it to her lips as licked it off. She let me see my cum on her tongue for a moment before she swallowed it, and I felt my cock twitch. She then took her finger and scooped more of it off her neck and chin, and then rubbed it over her nipple. She began teasing the nipple between her thumb and forefinger, rolling the wet nub back and forth.

"I want you to make love to me, Doug," she whispered, her honesty and need so apparent that it made my heart break. It was the first heartbreak I'd ever known that hurt in a good way.

I kissed her without a word, and when my cock was ready, I entered her again and lost myself willingly to her once more.

***

A week later, Tom still hadn't called Sheila to let her know where he was, and Elle still hadn't said a word. I made it a point to be over at Sheila's as much as I could, and as my final weeks of high school grinded out, I found myself less focused on my college endeavors. As a protest to the break-up, Elle had taken to staying with friends and pretty much telling her mom to fuck off, sometimes literally. And because she was eighteen, Sheila couldn't do much about it. I got the impression that Sheila had reached a point where she felt she shouldn't do anything about it. I could see the beginnings of a depression hanging over her head, the first warning signs appearing when we left the hotel and said our good-byes for the day.

So I did my best to cheer her up as much as I could. With the house being empty in the evenings, we made in love in almost every room. We re-christened the kitchen the day after our return from them city and made sure not to destroy the new table she had just bought to replace the old one. Over the next few days, we made a mess of the bathroom, bounced on every step of the staircase, tested every spring in every bed and managed to make our way from the living room to the garage. We must have used over twenty condoms that week, which to me was a world record.

That next Sunday, I got a call from her around six in the evening as my mother washed the dishes and my father watched the evening news.

"What's up, Sheila?" I asked, standing close enough to be within in earshot of my mother, "How's it going?"

"Is your mom nearby?" she asked.

"Yep," I said.

"Okay," she said, "How are you?"

"I'm fine."

"How's your cock doing?"

"Hard," I smiled, "But most graduation preparation is."

"Would you let me suck it later on tonight?"

"Oh absolutely."

"God, you are good for the ego," she smiled, "Listen, I just got a call from Tom..."

"Oh no," I frowned, "You got rats?"

"A big one," she laughed, "He's shacked up in the city with an old girlfriend, and he wants to talk to me."

"Don't be intimidated by rats."

"No, I'll be okay," she said, "I just need you to come over and keep an eye on the plumber, make sure he doesn't smell my underwear or steal anything."

"Will I get paid for this?"

"Of course you will," she said knowingly.

"I'll be right over."

I excused myself and drove the Sheila's house. When I arrived, there was a large white plumbers van in the driveway, still brilliantly white as dusk settled. I parked on the corner and hurried up the walkway, dressed in shorts, a t-shirt and sandals. I took a deep drag on my smoke and then crushed it out on the sidewalk. Sheila was inside, wearing her gorgeous yellow sundress with her hair pulled up and back.

"Hey you," she smiled as she led me through the kitchen and into the garage. Once the door had shut, she put her arms around me and we began kissing feverishly. My hands cupped her ass as our tongues rolled and caressed with each other.

"So what does Fuck Face want?" I asked, still holding her.

"He wants to discuss Elle," she shook her head as we kissed.

"Any word from her?"

Sheila broke the kiss.

"No," she lowered her eyes quickly, trying to hide the glassy sadness that was welling up at their corners.

"I've seen her at school at a few times, but she's been distant."

"I don't know what to do, Doug."

"Hey, just keep doing what you're doing right now. She'll come around. You want me to talk to her, loosen her up for you?"

"Can you even find her?"

"If I can't, then Brett will. Okay?"

She smiled, a fat teardrop running down her cheek. "Okay."

"Now, go and see what asshole wants and come home quick."

"Keep the plumber away from my panties."

"How can he get your panties when I'm smelling them all simultaneously?

"Good point," she laughed and then ran her hand over my crotch, "When I get back, I'll pay you for services rendered."

"I expect interest..."

"I can handle that."

We kissed briefly, and then she left. I spent the next two hours on the couch, watching the television and getting hornier by the minute as I fantasized about Sheila. The plumber left around 8:30 that night, and as I watched him drive away, I felt relieved. It meant that when Sheila got back, we wouldn't have to wait. I took the paper work he had filled out for her and put it in the kitchen. As I poured myself a glass of milk, I heard the door open.

"Is that you?" I called, taking a long chug from the glass.

"Doug, what are you doing here?" Elle asked me, standing in the entry between the kitchen and living room. She was dressed as I was, in a t-shirt and shorts, but a t-shirt on her was a like a t-shirt on her mother. Even at a large size, it was still stretched out from her huge tits, and I found myself gawking for a moment. Coupled with the shock of her showing up suddenly, I simply looked at her dumbfounded for a moment.

"I'm-" I began as I set the glass down, thankful I hadn't assumed it was Sheila and said something I would have regretted, "I'm here to talk to you."

"You could have talked to me at school," she said, still uncertain of my presence in the house with no one home.

"Yeah, you're right," I nodded, "But I wanted to catch you here."

"I haven't been here in over a week, and you just happened to be here when I show up?"

"Your mom asked me to talk to you," I said, gesturing for her to sit down at the table, "She had a plumber working on the upstairs bathroom and needed someone to watch the guy while she ran out real quick. So here I am."

"What did she want you to say to me?" Elle asked as she sat down. It amazed me how much she looked like Sheila, their faces perfectly matched and her hair almost identical to her mother's bronzed strands.

"She's worried about you," I said as I pulled out one of my smokes, "Is it cool if I smoke in the house?"

"Dad always did, why can't you?"

I lit my cigarette and continued, "She hasn't told me all the details of what has happened, which is fine by me. But she has said how she wishes you wouldn't be mad."

"You and mom are chums all of a sudden?"

For a moment, I felt like there was a load of subtext to her question, but I played it off. "No, she just wanted to me to try and explain that she loves you very much, and misses you."

"Doug, you don't know shit about this situation, okay? And she should fucking know better than to involve my friends as pawns in this."

"I'm not a pawn, okay?" I said, "You're both my friends... I can't just watch you two lose each other because of your father."