Shepherd's Pie Ch. 04

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Chris seeks professional help for his Mommy issues,
14.4k words
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Part 4 of the 7 part series

Updated 10/06/2022
Created 08/20/2013
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Rite of Passage

(Part 4 of "Shepherd's Pie")

Sunday morning, after spending the night alone in our empty house, haunted by lingering thoughts of Cynthia, struggling to escape the memory of her begging me to cum inside her, I jumped out of bed and frantically started cleaning every corner of the house, partly to keep from sitting still, but largely also to ease my guilty conscience.

The day before, I'd not only fucked my landlord without a condom, I'd also fallen for one of the oldest tricks in the book, letting her convince me she was on birth control, easily my worst decision ever, beyond reckless, completely inexcusable, yet also impossible to take back.

To make matters worse, Mom called from New York on Saturday night, asking how I was doing, and then making some cryptic comment about meeting some really great guy whom she couldn't wait to tell me all about.

After two hours dusting, mopping, and scrubbing every surface in sight, I turned my attention to Mom's closet, spending at least thirty minutes organizing all of her shoes, pleased to discover out of 26 pairs that 23 of them were high heels.

Admittedly, the simple task of organizing Mom's shoe collection should have taken no more than ten minutes, if only I hadn't stopped so often, smelling them one at a time, hoping her fragrant aroma would hold me over just a few more hours until she got home.

By noon, I was so looking forward to Mom's return that I lost count of how often I checked the time. The house was spotless. Still, I couldn't just sit there. So I took Mom's car and quickly sped off to the gym, hoping to burn off my nervous energy with a long, strenuous workout.

Shirtless in the locker room, standing in front of a mirror, it was easy to see how six months of rigorous training had really paid off, having slimmed down to almost zero body fat on my hard, lean, wiry frame.

My abs looked completely shredded, as I stood there admiring my well-earned six-pack, a testament to eating mainly fish, chicken, and protein shakes, along with a whole ton of raw fruit and vegetables. In addition, for increased stamina, my trainer started me on daily regimen of vitamins and supplements, including testosterone, all of which had a visceral effect on my volatile teenage hormones, to the point where a stiff breeze in the right direction could easily produce a massive erection, rivaling the might of any towering skyscraper in the city.

Around 3 PM, I hit the showers in order to meet Mom at Logan by 4:15. Once dressed, I walked to the car, where I sat in the parking lot, casually rolling a blunt, hoping to calm myself down, as I quietly proceeded to sit there and smoke the whole thing. I rolled down the windows to let in some fresh autumn air, feeling no less anxious, not when I knew how good Mom was at telling when something was clearly on my mind.

Around quarter to four, I started making my way through Boston traffic, which thankfully wasn't too bad, reaching the terminal just as Mom texted me from baggage claim.

She walked out rolling her Gucci carry-on, in full make-up, hair down as usual, in a black leather, waist-length jacket, over a thin, white, pullover sweater, with sandy brown riding pants, so tight I could see her cameltoe as she stood there waving from the curb in sexy, brown, spiked-heel boots.

On a 45-minute flight from LaGuardia, she had no reason to look so incredibly hot. Yet, that's just who she was. After helping her put her bag in the trunk, she hopped in, leaned over and gave me a kiss, moaning while greeting me with her soft lips, reaching down, sliding her hand between my legs, making my balls tingle as she lovingly squeezed my cock.

"Mmm, I missed you," she whispered under her breath, as I sat there enjoying the floral scent of her perfume. "Did you want me to drive?" she asked curiously, as I turned and gave her a puzzled look.

She'd always been sensitive about her car, especially when I was driving, which only made me feel more agitated than I already was.

"I'm good," I answered through a half-hearted smile. "How was New York?"

She leaned back in the passenger's seat, voice pitching with teenage enthusiasm. "New York was uh-ma-zing," she said, drawing out each syllable. "Of course, it would have been better if you were there, but I still had a really great time."

"Cool," I said, pulling off, headed toward the expressway, when I bluntly decided to ask her the one question stuck in my head. "So who is the guy you met? Tell me about him."

"His name is Doug Vincent," she said glowingly. "I met him at the conference. He was one of the guest speakers. He's from Albany, also divorced. He started his own chain of department stores than sold them to Macy's for a small fortune. He lives in Manhattan now, makes most of his money on investments. He's only 45, very smart, really funny too."

The longer she spoke, the more my temper slowly kicked in. It was only supposed to be a weekend business trip, not an excuse to go out and meet other guys. What happened to all her talk about being my new, live-in girlfriend? Was it all bullshit? By then, I was so pissed I had no idea how fast I was driving.

"Slow down, sweetheart," she said, touching my arm. "You're making me nervous."

"Don't worry," I said, snapping at her. "I know what I'm doing. I'm not going to wreck your precious car."

"Excuse me?" she said, clearly displeased with my tone. "I think you know better than to speak to me that way. Nothing happened between us, if that's what you're worried about. We had some drinks. We talked for a while. He took me dancing, and that's it."

"He took you dancing?" I said, raising my voice. "Then what, did you go out to the parking lot and jerk him off like that other guy?"

As soon as it happened, I instantly knew I'd fucked up. Nothing was said for several seconds, as my hands tightened around the steering wheel, eyes staring through the windshield, as Mom turned, voice incredulous, holding back imminent rage.

"Um, I'm sorry...what guy?" she said. "What are you talking about?"

Swallowing hard, I paused for a moment, bracing myself for the shit storm sure to follow my confession.

"The one I read about in your journal," I said, letting the statement hang there for a moment, fearful of saying more.

"So that's what this all about?" my mother eventually responded, as I felt my heart pounding in my chest. "You read my journal behind my back. Do you have any idea how hurtful that is?" she asked, voice cracking a bit. "Why would you do such a thing?"

I knew how badly I'd betrayed her trust, not only by reading her journal, but worse yet, fucking Cynthia too. My mother had always been a forgiving person, but not with people who were blatantly dishonest. That was the main reason she'd left my father, not because he'd cheated on her, but mainly because he'd lied about it for so long.

Still staring straight ahead, avoiding the shameful look I knew she was giving me, I answered weakly, slowly shaking my head.

"I don't know. It's hard to explain," I said.

"Well, you'd better come up with something in the next ten minutes," Mom threatened, "or I may have to reconsider this whole arrangement."

Since our first memorable encounter in the living room, I'd feared hearing her say something like that. I needed a way to defend my reckless behavior, but how could I possibly justify committing such a thoughtless and humiliating violation?

"To be honest, I don't have a good excuse," I said, hoping she'd sense that there was no malicious intent behind my actions. "I found it when we moved in. Lately, I've grown so attached you, sexually, that is...I just couldn't help myself."

The sincerity with which I tried to account for my regrettable behavior seemed to produce the desired effect as Mom gradually began calming down, gently setting her hand against my upper thigh, then slowly rubbing back and forth, voice filled with a healing tenderness normally reserved just for me.

"Sweetheart, it's not like I haven't noticed that. By now, you should know that I feel the same way. I'd never let anyone come between us. You know that, right?"

"Then what about this new guy?" I asked directly. "What does he want?"

"Doug just likes me, that's all," she answered with a shrug. "I like him too. He makes good money and has lots of connections in New York. He even said he could help you find work when you graduate, maybe even an internship with one of those men's magazine you love so much. I'm just saying...this could be good for both of us."

"Oh," I said, nodding my head. "So, you're just using him...is that it?"

"No," she pronounced quickly. "It's not like that at all. He's just a very generous person. He likes helping people. We actually talked about you quite a bit. He's eager to meet you."

"Really," I said sarcastically, taking the exit near our street. "And what happens when he finds out about our so-called 'arrangement'"?

"Why would he?" Mom answered. "You obviously know how good I am at keeping secrets. I think you should just give him a chance. You might like him. His daughter goes to school here too. Her name is Mia. He even mentioned us all getting together for Thanksgiving."

"And you're okay with that?" I said, frowning at her. "You hardly know this guy!"

Before answering, Mom took a deep breath, obviously weary of the whole topic, as I swiftly turned onto our quiet street, moments away from home.

"Look, I get that you're upset," Mom said, as I pulled up in front of the house. "Let's just go in, okay?" she added, changing the subject. "I bought some new pantyhose from Wolford's while I was there. I'm sure I can find some way to get your mind off this..."

Regardless, despite her efforts, the rest of our evening didn't go well at all. For once, I was actually not in the mood, as she sat on the sofa in a white, fitted, Tom Brady jersey, with nothing below but a sexy pair of blue opaque tights, legs stretched across my lap, as she kindly offered to give me another footjob, hoping to make me feel better. Instead, I told her I needed to finish writing my Psych paper and get some sleep. Then I stood up and left her there by herself, quietly heading up to my room.

* * *

Monday morning, lying in bed, naked and half asleep, before opening my eyes, my nose sharply detected the familiar fragrance of Estee Lauder perfume. The smell of fresh orange blossoms lulled me from my peaceful slumber, upon which I felt a sudden chill. Slowly, it hit me that Mom must have quietly entered my room, carefully peeling back the covers, thus leading to the rapid drop in temperature around my cock.

Though she'd never been the mischievous type, clearly she was up to something. Nonetheless, I remained still, never peeking, as I felt her crawling over the foot of my bed.

I knew it was coming. Still, my eyes instantly popped open as I felt the warmth of her steaming crotch softly descending over my morning wood. The room was cold, yet my hard-on wasn't for long, as I felt the light pressure of Mom straddling me below the waist, blanketing my penis with the downy fabric of warm, velvety soft pantyhose.

Waking with double vision, I squinted at dual images of Mom smiling down over me, hair matted, fresh from the shower, water dripping from her tits.

With no hesitation, I reached down, returning her smile, sweeping my fingers over the lush, comforting fibers clinging to her silky thighs. The texture delighted me as I lingered over the smooth nylon seemingly waiting to be touched. I reveled in the moment, choosing to remain silent, as Mom wisely followed suit, both of us choosing to avoid talking about the previous night.

Her eyelids fluttered in response to my leisurely caress, encouraging my hands to venture further, freely exploring her lower body, sliding my fingers where the nylon molded the curves of her jutting hips, never expecting her stirring reaction as she slowly began writhing on top of me, rolling her hips in slow, circular motion, curling her lips with killer intentions, like a kitten waiting to pounce.

Her hips temptingly rocked back and forth as she looked down and warmly whispered, "Good morning, Mr. Shepherd."

For a moment, I had to remind myself that this stunning, fair-skinned, hazel-eyed seductress was the same woman who'd carried me in her womb for nine months, the same woman who'd taught me the alphabet, fed me chicken soup when I was sick, and beautifully sang 'Happy Birthday' to me every year.

Still, as I looked up into her beaming face, feeling the smooth texture of pantyhose over her naked skin, I couldn't help wondering if she'd purposely planned this in advance. Though I admitted reading her journal was wrong. Perhaps, after sleeping on it, she'd come to realize how much she'd also let me down, knowing how much she'd made me believe that the future was all about me and her. By then, I wasn't sure what to believe. Not to mention completely guilt-ridden that another woman, the one who conveniently owned our house, was most likely pregnant with my unborn child.

Clearly, the stress was getting to me, even as Mom did her best to distract me in the hottest way possible.

Slowly, she reached down and slid her cold hands over my naked chest. Then leaned over, pressing her tits against me, grazing my sensitive skin with her raised nipples, sweeping her moist hair across my face, as I went up to kiss her, deeply inhaling her fruity scent.

As our lips parted, I could almost taste the hunger inside her, tongues swirling and worming in each other's mouths, as a breathless series of moaning and spit swapping ensued, feverishly trading our shared DNA, sealing the bonds of our unspeakable relationship with a long, steamy, French kiss.

Reluctant to pull away, our lips briefly pulled back, leaving threads of spittle bridging the gap between them, only to reunite and feast on each other once more.

After several minutes, our intense make-out session left us completely breathless. Though I didn't want to be late for school, the conflict swirling inside me left me with no desire to get up and face the world. By then, my dick was hard enough to cut glass. I needed to get off, for no other reason than to ease the tension mounting between us with each passing moment.

"Hmm," I moaned, stretching my arms. "Now that's how I like to be woken up."

Mom smiled at my warm reception. I watched as she slowly sat up, fluffing her fingers through her limp brown hair. Her high-wasted pantyhose covered most of her stomach as she reached down and snapped the waistband against her skin.

"I kind of figured you might enjoy it," she said, with a playful wink. "I'm wearing new pantyhose today," she added, sliding her fingers between her legs. "Notice the seamless crotch," she said, leading my eyes down to a patch of brown pubic hair, neatly trimmed and plainly visible through the sheer, flesh-colored hose.

I listened as Mom continued talking, voice dripping with affection, as she held her legs open, shamelessly rubbing her clit on top of me. "There a little pricey," she explained, fingers massaging up and down. "Mmm, but they're so worth it," she added, rolling her eyes orgasmically, squeezing her pussy above my lap.

"Very nice," I said, blinking in disbelief. "Are you wearing those to work?"

"Oh, absolutely," she said, twitching her eyebrows. "It'll give you something to think about until I get home, assuming you can wait that long."

"I see," I said, responding to her challenge. "So you're saying I can't go a whole day without jerking off?"

"No, I'm not saying that at all," she said. "But maybe you'll get another visit from Cynthia. Maybe this time she'll want a little more. You may think it's just business. But I know women. And it's pretty obvious she wants more than that."

"So," I answered defensively. "What would I want with her when I already have you?"

"My point exactly," she said. "Like I told you last week, from now on we're not only mother and son. We're a couple. The connection we have goes way beyond family. I've seen how you look at me. I know what goes on inside your head. I've known it for a long time. What I couldn't face until recently is how much I secretly wanted the same thing. Not until we moved here. But now you know. And now we're free to enjoy each other as much as we want. And because I'm your mother, I know that no other woman can fulfill your fantasies like I can."

Her speech ended as she reached down and took my penis softly in hand. Her eyes pierced deeply into mine as she gently cradled the shaft between her fingers, slowly beginning to stroke.

"Don't you have to finish getting ready?" I said, though all I wanted was to lean back and let her jerk me off.

"We have time," she said. "I was thinking maybe I should drain you before I go, you know, to help you focus."

By then, I could barely focus on anything besides her hand. At first, she started off teasing my cock with long, delicate strokes. Then she slid her hand down to the base and slowly began rubbing it against the hose, brushing my rigid shaft against the nylon, back and forth, back and forth.

I lay there squirming under the weight of my mother's legs, covered in pantyhose, soft and light as a feather, with sheer, luxurious, finely-woven threads sending a tingling sensation through my hard, sensitive prick, down to the tips of my toes.

"Does this bother you?" she whispered, seeming to notice my disadvantage, as she playfully smiled and continued grazing my penis over her pantyhose. "If it does, I'll stop," she said, sweeping her hand up to the head, then slowly dragging it back and down. "Otherwise, you do have another option," she said, piquing my interest. "That is, if you feel like sending me to work with a fresh cum stain under my skirt. I've always wanted to show up at work with a huge load splattered all over my pantyhose, just to see if anyone would notice," she added, head dipping, dribbling saliva from her lips, slowly letting it string down, moistening the head of my cock. "Can you see me sitting in front of my students, slowly crossing my legs, wondering who'd be the first to notice the crusty blotches all up and down my pantyhose. Doesn't that sound hot?"

As she painted her vivid picture, her curled fingers firmly enveloped my shaft, gradually sliding them down toward the base. Using gentle pressure, with a light twisting motion, making me shiver as her clenched fist slowly slid up to the head. "Normally, I sit on my desk a lot," she continued, "but the guys up front would probably notice the cum on my legs pretty quickly, don't you think? Especially if I just happened to spread my legs," she said, demonstrating on top of me. "Not on purpose, of course," she promptly added, with a devilish grin, "but it might get a little distracting to sit there with all that cum stuck to my legs, constantly reminding me that only my son could produce such a giant load, making me remember how hot it was jerking you off this morning, dripping from overexcitement, with no cotton panel to soak up all of Mommy's juices in these seamless pantyhose," she breathlessly whispered, drunk off her own words. "And I do have to say, young man," she continued, churning her moist fingers around my throbbing erection. "I'm not sure what you've been eating lately, but I've never seen anyone cum as much you do. It's rather amazing," she told me, "not to mention quite tasty," she added, ending with a wink.

Certainly, hearing my mother talk dirty was incredibly hot. Yet, the thought of her flaunting herself wantonly in front of her students didn't excite me as much as she probably intended. In fact, I was starting to feel a little jealous, even somewhat angry, unable cut off my increasing need for an explanation of why she had chosen to date someone else.