Shepherd’s Pie
By Earth Angel
It all started when I was 10 years old, the year my parents got divorced, a normal age for a lanky, soft-spoken only child to have his obsession with Grand Theft Auto blindsided by his first crush.
I had just started junior high, where they made us read boring stuff like Romeo & Juliet, though I was too young to understand the dangers of forbidden lust, yet old enough to notice how my mother would often do the sexiest things without knowing it.
Things might have been different had my mother been more willing to let me out of her sight. Instead, I was treated more like a pet, expected to literally follow at her heels everywhere she went. Naturally, by forcing me to spend all my free time with her, it wasn’t long before I started observing some of her more peculiar tendencies.
She had an extensive shoe collection, most of which were high heels. She loved wearing heels so much that even when she took them off, I’d often catch her walking around on her tiptoes, like she was purposely training her leg muscles around the house, by practicing in invisible stilettos.
No matter what she was doing, she always seemed to need something inside her mouth. When we went out to eat, she couldn’t drink anything without a straw. If she was sitting at home grading papers, she’d sit there for hours sucking on the end of a pen. She watched football every Sunday, though she knew almost nothing about sports. She just enjoyed wearing her fitted jersey and a pair of tights, rooting for whichever team had the cutest quarterback.
Whenever I got lint in my eye, she would lean down, pout her lips together and gently blow until it was gone. The feeling excited me so much that I eventually found myself actually looking forward to it.
By the time I finished high school, I was so used to being by my mother’s side that leaving for college less than an hour away filled me with highly mixed emotions due to all the amazing memories left behind.
By my third year at Emerson, the novelty of living away from home had worn off almost completely. With each passing day, I was growing more lonely and homesick, with no girls and only a few male friends to help kill the boredom.
One dreary afternoon, my mother called me completely out of the blue, with the radical idea of finding a new apartment for us to live together.
Even at 42, my mother was still an incredibly striking woman, with long, flowing, chestnut brown hair, hazel eyes, flat cheeks and skinny lips set between her oval chin and the downward tip of her nose.
At 5’6”, 120 lbs., she’d fully outgrown the red leotards from her glory days of high school gymnastics, where she’d collected multiple trophies, mostly for balance beam. Still, she kept her body in tremendous shape, wearing trendy outfits that proudly displayed her pert breasts, tight ass, and best of all, her long, head-turning legs.
To put it bluntly, in my own personal opinion, my mother was the hottest woman I’d ever seen. I jerked off thinking about her so much that it soon developed into a full blown obsession. I tried my best to keep her from catching on to how often I fantasized about her. Yet, over the years, she started to worry that I seemed to have no interest in other girls.
I had just started college two years earlier, so the thought of moving back in with my mother initially felt like a step backwards. Admittedly, I was living in a small, dumpy apartment. My roommate was a total slob. Yet, in spite of the headaches, and as much as I missed seeing her every day, I’d still managed to survive on my own and part of me had gotten used to fending for myself.
At 19, I was eager to spend my junior year getting hammered every night and screwing as many co-eds as possible. At least, that’s what I’d always imagined college would be like. Though in reality, I was still the same skinny kid from Rhode Island, with a tendency to fidget and make awkward jokes around girls my own age, to the point where even the ugly ones started avoiding me.
The day Mom called I was in lying in bed going through my favorite pictures of her on my cell phone. I never knew when I might get the sudden urge to rub one out and nothing made me cum faster than looking at pictures of my gorgeous mom, even fully clothed.
For as long as I could remember I had always been captivated by my mother’s legs. When Dad left, because of all the travel, she gave up event planning to teach marketing at a nearby community college where the women on staff often wore pantyhose under their skirts. By that time, for all I knew, Mom had been wearing pantyhose for many years. Yet, it wasn’t until she started teaching that I really began noticing how this basic element of her daily business attire distinctly brought out the remarkable beauty and dimension of her long, sinuous legs.
Maybe it was genetic, or perhaps it was just puberty, but around that time, I became so fixated on my mother’s legs that I started to question why I was so helplessly drawn to them in the first place. As flawless as they looked by themselves, their hypnotic effect immediately doubled whenever I saw her in pantyhose.
It was as if this ordinary undergarment was imbued with extraordinary powers luring my eyes to linger over the supple tone of her lean, slender calves, moving up to the meaty flesh of her firm sculpted thighs, where her long, shapely legs gradually expanded leading to the fullness of her hips, topped by a set of luscious round asscheeks beautifully encased under sheer, shimmering threads of nylon.
Though I’d long forgotten the very first time that I noticed Mom wearing hose, the one thing that never left me was an urgent impulse to look down and gaze over the dazzling aura emanating from her legs. From the bottom of all her short skirts, down to the tips of her toes, each pair she wore had the power to enthrall me with its own seductive sparkle.
Not a single day went by where I wasn’t sitting at home waiting for her to walk in and kick off her sexy heels. My dreamy eyes followed as she tiptoed around the house, lost in the warm glow of her lustrous pantyhose, completely spellbound. The longer I stared, the more I became desperate to feed my growing obsession at all cost.
Growing up, Mom and I traveled quite a bit. Wherever we were, it wasn’t unusual for me to pull out my camera and get her to pose for me out in public. She’d always been the type of mother who gladly encouraged any hobby I developed, especially my growing interest in photography. Eventually, I managed to collect dozen of pictures, all of which focused on her long, gorgeous legs. I was certain she never suspected what I actually did with her pictures after she went to bed, considering I was so young, not to mention being her son.
My favorite pictures for jerking off were the ones that involved Mom sitting down and crossing her legs. Before teaching, working in corporate America had given her many years to develop this particular skill. As a trained professional, she was far too elegant to take one leg and carelessly flop it over the other.
Instead, with her head up and her perky breasts pointed straight out, she’d gracefully sit down, sweep her hands under her skirt, then with full extension, flick out one leg, flexing the tip of her shoe, as she leisurely elevated her long, silky stem, the lush contours visible though the pantyhose, as she draped it ever so gently across her lower thigh, all this in one rousingly fluid motion, seamlessly merging her firm shapely calves in deliciously perfect alignment, as I stood there completely riveted, listening as one leg brushed up against the other, sweeping against the grain, a thrilling sound that instantly made my dick throb hearing that subtle swish.
Deep down, I knew it was wrong. Still, I often tried to convince myself that it wasn’t so unusual to see my mother as the hottest woman on Earth. Her voice alone sent chills down my spine, with the perfect diction and dignified restraint of a well-trained, highly confident educator, with only the slightest trace of a typical New England accent.
Despite being over forty, her nutritious diet and friendly demeanor gave her a youthful glow. She barely ate more than two bites of anything, loved yoga, and jogged two miles every morning. While it was clearly a positive thing, her healthy lifestyle only encouraged my physical attraction to continue building and become more powerful each day.
Her bra size was an average 34-B. Yet, her modest chest proudly stood out in contrast with her petite waistline, jutting from the flimsy material of her tight blouses and low-cut tops.
Despite being a hard-working single mom, I had to imagine she still had needs. Yet, to my limited knowledge, after the divorce, she had no men in her life. Perhaps, if she hadn’t spent so much time worrying if I was getting laid, she might have had time to date. She should have had offers lined up considering how hot she was. But then again, I might have been somewhat biased by my own forbidden infatuation and my ever increasing lust for pantyhose.
I had already started loosening my belt, as I lied in bed, eager to stroke my cock. My phone started buzzing and Mom’s cell number flashed up across the screen. The timing was terrible as I’d just settled on one of her better pictures, taken in Times Square. She had on this beautiful, wine-colored blouse, with a black miniskirt, black pumps, and a radiant pair of suntan pantyhose gleaming in broad daylight.
I snapped the picture just as Mom walked over to pose next to a tall New York streetlight. It was like she could read my thoughts as she suddenly stepped over and purposely draped her arm around it. Her face was only half visible under her long hair, as she leaned forward and pressed her forehead against the rusty pole. She rotated just enough to smile toward the camera, flexing her left knee behind her back. She stood there holding the pose for several seconds, with one shoe playfully lifted off the ground and a smile on her face as bright as the pantyhose on her legs.
“Hey Mom,” I said, holding the phone up to my ear, as I leaned back hoping her well-trained hearing had failed to detect the noisy jangle of belt, which I’d tried to unbuckle as quietly as I could.
“Hey Chris, got a minute?” she said quickly. “There’s something important I need to ask you.”
There was something urgent in her voice that told me it must be serious. Still, I’d just spent the last five minutes drooling over her sexy photos. I’d even pulled out a pair of pantyhose I’d recently stolen from her dresser on my last trip home. She had over a dozen. So I easily convinced myself that she wouldn’t notice if I only took one. My dick was already throbbing. All I could think about was taking her pantyhose, sliding them over my hand, then taking my silky fingers and wrapping them gently around my cock. Naturally, the more she talked, the quicker I found myself doing just that.
“My lease is up in two months,” she said. “I just got a letter that my rent is increasing by almost 200 dollars. There’s no way I can afford that.”
“Okay,” I answered, trying to refocus, as I slowly began stroking myself with her stolen hose.
“No, it’s really not okay,” she said. “I’m going to have to move out. I was actually wondering how you’d feel if I moved up to Boston.”
At that particular moment, I probably should have been listening more carefully, but her pantyhose felt so good around my cock that I almost blurted out yes without thinking, just for the chance to be up close and personal with her amazing legs again.
“I understand if you need to think about it,” Mom continued. “I’ve barely given it much thought myself. I’m just not sure what else I can do.”
Again, my mind drifted off. I lied there trying to imagine what she was wearing. I purposely asked her a random question hoping to get a clearer picture.
“So, um, where are you?”
“In the teacher’s lounge,” she said. “I’m on my lunch break. Why?”
“No reason,” I said, smiling to myself, as I pictured the image of her sitting there with her legs crossed, knowing the way she typically dangled one shoe off her foot, especially when she was stressed.
“You seem distracted,” she said. “Is everything all right?”
“Yeah, everything’s fine,” I said. “I was just thinking that living up here would be even more expensive. How would that make things easier?”
“You’re right,” she said. “That’s actually the real reason why I called. I know how you feel about your roommate. And I’ve never been crazy about the neighborhood you live in. So I was actually thinking of finding a nice place for the two of us.”
It took me another moment to respond. I was still lying there quietly teasing myself with the smooth velvety texture of the nylon. My hose-covered fingers were gently grazing up and down the length of my shaft.
“Oh, umm, yeah, that’s an idea.”
By then, I could barely concentrate. I was too busy wondering what her free hand was doing as she sat there with one hand holding the phone. Was she gently rubbing her fingers over the nylon like I’d caught her doing so many times at home? Was she dipping one foot in and out of her shoe, or wiggling her hose-covered toes? There was no way to know for sure. Still, I pictured her doing all three, right there in the teacher’s lounge, in full view of anyone walking by.
“Come on,” Mom continued. “It’ll be just like old times. I can always find work at another campus. Plus we can find a place with more space for your camera equipment. I’ll even do all the cooking.”
There was a thought, Mom in the kitchen, bending over to reach inside the oven. I could already see her skirt riding up, framing her heart-shaped ass, with just a hint of her pantyhose gusset peeking out between her legs.
“Hmm, I don’t know,” I said, trying to keep myself from breathing too heavily while I kept beating off. “I’ll have to talk to Jimmy about this,” I said, knowing that I couldn’t just bail on my roommate, even if our lease was month to month. “Plus, we’ll have to lay down some ground rules,” I added, when I started to realize the freedoms I’d be giving up purely to see her legs every day.
“Oh, I see,” she said. “So you want to make the rules now, huh? Okay. Like what?”
“Nothing major,” I explained. “I’m just not a kid anymore. I want to be sure we’ll respect each other’s privacy. That’s all”
“I get that,” Mom said. “But it’s not like I’m bringing guys home or anything. There hasn’t been anyone since your father. You won’t have to worry about that.”
My rhythm was getting faster as the conversation went on. My grip was tight, but thankfully her pantyhose provided a smoother, more delicate friction to my teasing hand strokes.
“I know. It’s not that,” I said, clenching my fist. “I’m talking about respecting each other’s space.”
“Oh, I see,” Mom answered. “Like giving you space to smoke weed and play with yourself all day. You think I don’t know about all the porn you have on your computer? You’re my son, Chris. There’s nothing you can hide from me.”
“Mom, what the hell,” I said, voicing my annoyance. “Have you been checking up on me?”
Clearly, I wasn’t amused. Yet, her first reaction was to giggle. Then, she started to explain, parsing her words carefully.
“Let’s just say I’ve poked around a little bit,” she said. “And if you don’t mind me saying so, you really should get out more. You’re very handsome. It doesn’t make sense that you’d rather sit at home surfing for hot MILFs online, when there’s plenty of real women out there.”
“Great,” I replied. “So you’ve checked out my history too? Jesus, Mom. What else did you see on there?”
“Enough,” she said, in a sobering tone that made me a wee bit nervous. “I never knew you had such a thing for older women,” she continued. “Maybe I should introduce you to some of the teachers here.”
“Yeah, maybe you should,” I said, playing along. As mad as I was at the thought of her checking my computer behind my back, by then my head was literally spinning as I jerked off more vigorously.
“So,” I asked, switching the subject to something more stimulating. “Did you like the new shoes I sent you?”
Mom paused for a second, as I lied there waiting for her answer. The lift in her voice told me she was smiling on the other end.
“You must have been reading my mind,” she said. “I’m wearing them right now. I’ve had nothing but compliments all day. It was nice telling everyone my son picked them out.”
“Cool,” I said, picturing her in the five-inch black strappy sandals I ordered from Amazon. “I can’t wait to see how they look.”
“Well, you’re in luck,” she said cheerfully. “You can see them tomorrow if you want. I’m driving up to look at places in the morning. You should come with me.”
“Mmm, I’d love to come,” I said, catching myself. “I mean, that sounds good. It’s supposed to be cool tomorrow. You might want to wear something warm.”
“Oh, I’ll be fine,” she said. “I normally wear pantyhose under my jeans. That usually helps. Though I seem to be a missing a pair,” she added surprisingly. Naturally, I avoided the subject.
“Really,” I said. “Pantyhose under your jeans,” I repeated, resisting the urge to moan. “I guess that would probably help.”
“Yeah, it really does,” she said. “But anyway, sorry for rambling, I’m sure you’re not interested in that.”
“Oh, it’s fine,” I said, knowing it would only be another minute or so before I exploded all over my hand. “So, about tomorrow,” I said, holding it together, “were you thinking of swinging by here first?”
“Yeah,” Mom said. “I should be there around nine. Just make sure you tell Jimmy to wear some pants this time. It’s a little awkward seeing your roommate with an erection.”
“Yeah, sorry about that,” I answered, stroking like a fiend. “But then again, you can’t really blame him. That skirt you had on was pretty short.”
“Oh, you think so?” Mom said, scoffing a bit. “It was normal length. The skirt I’m wearing today is shorter than that.”
“Well that explains all the compliments,” I said. “How do you keep your students from hitting on you?”
“Never said I did,” she answered. “It’s kind of flattering honestly, especially at my age.”
“Stop it, Mom. You look great. You know you do.”
“Why thank you,” she said. “But I’m just like any other woman. We all like to hear it.”
“Well, it’s true,” I told her. “I think you’re beautiful. In fact, if you weren’t my mother, I’d probably…um, nevermind,” I said, stopping myself. Who knows what I was thinking. By then, my penis was doing all the talking.
“No, go on,” she said. “If I wasn’t your mother, you’d probably what?”
That was the pivotal moment. In 19 years, my mother had never asked me a question as directly sexual as that. My balls were practically about to burst. My fist was pumping non-stop. Yet, even then, I still couldn’t bring myself to voice my unnatural desire to run my hands over her soft silky pantyhose and cum all over her sexy legs. Still, I somehow managed to respond with an answer intended to hide my true feelings.
“Wow,” I said, rubbing my forehead. “This is starting to take a weird turn. I really don’t think we should go there, do you?”
“You brought it up,” Mom answered bluntly. “Go on, tell me,” she added, with a boldness I found intimidating, yet highly erotic at the same time. “Seriously, I want to know,” she pressed, as I held back what felt like a massive eruption. “Do you think I’m a MILF…like the ones you look at on those dirty websites?”
My body trembled. I honestly couldn’t tell whether she wanted the truth, or whether she was just testing me.
“Really Mom, stop,” I said, assuming the latter. “I don’t think we should talk about this anymore.”
“Okay, fine,” she said. “I wasn’t trying to make you uncomfortable. Just tell me one thing. Which part of a woman’s body do you like most? Wait, let me guess, you’re a leg man, right?”
Now she was pushing it. My best option was to push back.
“Yes, Mom, I’m a leg man,” I answered flatly. “There, I said it. Can we drop it now?”
To my amazement, she didn’t stop there.
“With or without pantyhose?” she said, pushing me to my wit’s end. By then, I was jerking off so hard if she hadn’t already gathered the state I was in, she was only seconds from figuring it out.
“Definitely with pantyhose,” I said. “Now seriously, stop it. I can’t take this anymore.”
“So you’re really into pantyhose,” she said. “I guess that makes sense, considering how often I wear them. I suppose it’s good that I found out. Maybe we should reconsider this whole idea. It’s bad enough you can’t find a girlfriend. I’d hate to do anything that makes you feel even more frustrated.”
“Look Mom, for the last time,” I said, starting to lose it. “If I really wanted a girlfriend, I’d get one.”
“Oh, really?” she said. “And when will that be? When I’ve already got one foot in the grave? Seriously, Chris, I’m worried about you, especially with this pantyhose fetish I’m just now hearing about. You know I wear them all the time. I certainly don’t want you having sexual thoughts about me. Surely, I don’t have to tell you how inappropriate that would be.”
Of course she didn’t. I’d known all along how inappropriate it was. In that moment, I honestly didn’t care. By then, I was pummeling my cock with a vengeance, bent on ruining her pantyhose no matter what, dying to soak every thread with a massive wad of thick greasy spunk, purely out of spite.
I closed my eyes, instantly reliving the indelible memories that triggered my fetish in the first place.
I vividly pictured Mom strolling through the house wearing see-through pantyhose with no skirt on. I could see her returning from work in her black fuck-me pumps, the stale odor of damp, sweaty nylon spreading through the air as she took off her shoes and asked me to rub her swollen feet. I could even picture the way she smiled as she walked down the street, hips switching from side to side, pretending not to love how men spun toward the sound of her spiked heels clicking on the sidewalk, only to come home, peel off her pantyhose and carelessly toss them in the hamper, leaving them for me to salvage, as I secretly pulled them out, slid my tongue over the wet spot, and deeply inhaled her strong, musky scent.
My lurid memories pushed me right over the edge. With each violent spurt, I was forced to stifle my urge to groan, watching jets of semen blast into the air, surging from the head of my cock, splattering down, drenching the nylon around my hand, while my mother patiently waited on the other end, with no idea what was happening as I lied there shamelessly enjoying my reckless act, her pantyhose swimming in a pool of cum.
Finally, I managed to collect myself, leading with a heavy sigh.
“Look Mom, I’m sorry,” I answered wearily. “You asked me to be honest. I wasn’t trying to upset you. Maybe we should just hang up now.”
“No,” she said, softening her tone. “Don’t hang up. I know you were just being honest. I realize that’s how I raised you. But before we make such an important decision, I think you should tell me everything. Tell me the truth, Chris. Have you ever fantasized about me?”
As soon as she asked, I instantly knew that I was stuck. On the one hand, by saying no, she’d most likely sense that I was lying, which would only make her angry and potentially spoil any chance of us moving back in together. On the other hand, telling the truth would most likely freak her out so much that she might not speak to me again for months, and that was even worse.
Normally, in situations like this, where I wasn’t exactly sure what to do, the first thing I usually did was try to imagine what Mom would do if she was in my position. That’s when it hit me that the best way to answer her question was to turn it around and ask her a question of my own.
“I’ll be honest,” I said, pausing before slyly attempting to redirect. “But first I’d like to hear what you think?”
“What I think?” she said, pausing for a short breath. “I think that all that porn you’ve been watching is starting to mess with your head. I think if we’re going to live together, then you have to promise to find a girlfriend and start living in the real world. Can you do that?”
“Sure Mom, I can do that.”
“Good,” she said. “I’ll see you in the morning. And don’t forget to bring back my pantyhose.”
* * *
The next morning, Mom showed up right on schedule, in a form-fitting, black, V-neck sweater, fairly low cut, with her first initial, L for Lauren, dangling from a silver necklace which failed to keep me from noticing the cleavage swelling over her plunging neckline. Her blue skinny jeans sat low on her shapely hips, hugging every curve under skin-tight denim, leading down, just as promised, to her brand new, high-heeled, black leather sandals, with thin straps spanning over her naked feet.
Looking down at the cuff of her jeans, the first thing I noticed was the disturbing absence of pantyhose I’d been expecting. Naturally, I was disappointed, especially after spending my whole night tossing and turning in anticipation of seeing them the next morning.
My first instinct was to say something about it. Then, I remembered how concerned she was talking about my fetish. So the last thing I wanted to do was call any undue attention to it right away.
We stood there enjoying a warm hug, when my roommate, Jimmy, promptly emerged from his room. The grin on his face told me he liked what he saw, as Mom reached over and greeted him with a polite handshake. For a few minutes, she and Jimmy stood there making small talk, until Mom finally excused herself, turning to ask if she could speak to me in my room.
I led her back to my bedroom and there she explained that she’d accidentally put a run in her last pair of pantyhose with a sheer heel and toe. Fortunately, I’d remembered to rinse out the pair I’d taken from her dresser. So I promptly fished them from the pile of laundry thrown on my bed and handed them right over. She then asked if I would give her a moment to put them on. So I quickly stepped out and waited for her out in the hallway.
She must have been hurrying too much to realize that I’d purposely left the door slightly ajar. I stood there peering through the narrow crack, knowing it was wrong, yet still unable to tear my eyes from watching her undress.
With her back turned, I stood there watching as she reached down and pulled off one shoe at a time, enjoying the lovely sight of denim smothering her tight round butt. I then heard the sound as she yanked down her zipper, then continued watching as her hands went up to her sides. She hooked her thumbs into the narrow waistband and promptly began squirming and wiggling her hips side to side. I fully expected to see panties, or at least a G-string, resisting the urge to gasp as she peeled down the jeans, revealing her naked ass. My dick instantly started to swell. Then she bent over, folding at the waist, presenting me with a clear view of her outer pussy lips, smooth, pink, and fully-shaved.
I worried that Jimmy would walk by and see me standing there at any moment. Still, my incredible fortune was too good to pass up, as I stood there watching and waiting to see even more.
I gulped with anticipation as she wisely removed the jewelry from her fingers, then reached over and lifted her pantyhose off the bed. Within seconds, her nimble fingers rolled up the first leg. She then lifted her left foot, then reached down and slid the ring of nylon over her sharply pointed toes. She then carefully slid the delicate fabric up to her slightly bended knee. She set down her left foot, then steadily raised the other, pointing her toes once again as she slowly eased her right foot inside the opposite sleeve, leaving me breathless as she patiently slid the pantyhose over her knees, drawing the nylon inch by inch over her supple thighs, and finally squirming to squeeze her shapely hips under the straining waistband, making one final adjustment to line up the stitching along her narrow butt crack, where her high-toned asscheeks, under a wondrous layer of tan, glossy, sheer-to-waist pantyhose, shimmered like a pair of half-moons.
I could have stood there watching forever, but my instincts told me to quit while I was ahead, knowing she could turn around and catch me at any moment.
I went back to the living room to find Jimmy rolling a joint, which I’d come to expect as part of his morning routine. The night before, he and I had sat down for a long talk where I’d delicately broken the news to him that I was moving out. To my surprise, Jimmy took it in stride, explaining that he had already been planning to move in with his girlfriend in a few weeks anyway. Fortunately, there were no hard feelings between us, especially when I stopped to consider who my new roommate was soon to be.
Moments later, my lovely mother finally returned from my room, smiling cheerfully, as I looked down grinning over the sight of pantyhose covering her pretty feet. I promptly turned and hurried toward the door, hoping to shield my raging hard-on from her view. We left my apartment and set out to find our new place, quickly escaping so Mom could avoid Jimmy staring at her ass, and practically cumming in his pants.
We made our way down to the car, where Mom got in behind the wheel and turned on the local eighties station. The song on the radio thankfully managed to calm my erection as I road beside her, shifting my focus toward the highly ironic lyrics.
“Every little thing she does is a magic. Everything she do just turns me on…”
We then proceeded to spend the next couple of hours going from one ugly, over-priced apartment to another, before finally stopping at a newly-renovated, second floor walk-up, on a quiet, tree-lined street in Roslindale.
The house was owned by a young, newlywed couple named Joel and Cynthia, who conveniently lived on the first floor. Joel was a successful contractor in the city. Cynthia was a former nurse turned stay-at-home mom who’d recently given birth to their first child. Looking at Cynthia, it was pretty obvious she’d just had a baby, judging by the size of her enormous tits which seemed to account for nearly half her body weight, especially considering how short she was. If I had to guess, I would have said she was easily a G-cup…With a capital G, as in “Goddamn, those are some big tits!”
Compared to Mom, Cynthia was easily three or four inches shorter, as I stood at Mom’s side and watched them converse with each other, instantly hitting it off, smiling and hugging like long lost friends when they quickly discovered that Cynthia had graduated from the same high school as my mother, only eight years later.
Cynthia led us up to see the apartment and we couldn’t believe our eyes. The place had literally everything we wanted, high ceilings, hardwood floors, with tons of space, including a large eat-in kitchen. As we walked in, on the left was a combination dining and living room area, divided by sliding double doors. On the right was a small office, a small guest bathroom, then the kitchen, followed by a small storage space, with a door to the back porch, and stairs leading up to the attic. The attic had been completely remodeled for new tenants, with two bedrooms, and a large master bath.
Mom and I signed the lease in a matter of days, agreeing to move in by October 1st.
The move itself went fairly smooth. Mom hired movers to handle all the big furniture. Then, on Sunday the 30th, we rented a U-Haul, loaded up everything else, and got it all moved in within a few hours. Sometime around noon, Mom figured I was probably hungry and realized we had no food. I offered to start unpacking while she went out and got us some lunch.
I headed back down to the truck and pulled out a box labeled “Mom’s bedroom.” I carried the box upstairs, setting it down in her room, where I opened it and start removing the items inside. It was mostly packed with old books and photo albums, until I noticed something buried underneath.
Curiously, I reached down and pulled out an old, dusty, leather-bound journal which I’d never seen before. I stood there alone in the empty room and quietly cracked open the first page.
The first entry was dated November 7th, 2003. If memory served me correctly, it was only six months after my parents’ divorce.
The first few entries weren’t particularly interesting. She started off talking about leaving the old marketing firm she’d worked at during her marriage. She’d already completed her teaching certification and put in her two-weeks notice. She was clearly still hurting over Dad leaving her for someone else, blaming it mostly on her own ambition when all Dad wanted was someone more traditional and submissive. Personally, I never understood why he felt that way. Still, he did seem much happier with his new trophy wife. So there really was nothing else for Mom to do except move on.
I read through the first five or six pages, when things started to pick up a bit.
November 13, 2003
Something crazy happened today. I made out with Mike Sullivan in the stairwell over by his office. I’m not even sure why I did it. He’s almost 10 years younger than me. Plus he’s so full of himself, really not my type. He hasn’t stop flirting with me ever since he heard I was back on the market, as he put it. It’s not like I did anything to encourage him. It wasn’t my decision to move the copier outside his office. I love how he always comes over and drops his pen on the floor. It used to make me uncomfortable, but now I just play along. At first, he would drop it and pick it right back up. Now he likes to linger down there and stare at my legs for a while. It’s pretty funny to watch. Chris doesn’t know it, but I’ve actually caught him doing the same thing. He must really like my legs. I know he’s my son and I should probably say something to him, but he’s been through enough lately. The last thing I want to do is embarrass him. I guess he’s just at that age. Anyway, I’m not sure what to do about Mike. Kelly and Robin are throwing a goodbye party for me tomorrow night. Mike said he’d be there. I really liked kissing him. I could tell he liked it too. His dick got really hard when he rubbed it against my leg. It felt pretty big too. No wonder he’s fucked half the women in the office. He probably thinks I’m next. It’s tempting, but I don’t know. We’ll see…
November 15, 2003
I can’t believe I spent $80 dollars on a brand new party dress and that son of a bitch didn’t even show up. Oh well, his loss I guess. God knows there were plenty of other guys there who liked it. Never thought I could pull off zebra print. Maybe I’ll wear it again next week. It was kind of odd being the center of attention, but I think I could get used to it. I know Robin was pretty jealous. I told her to stop buying me shots. Besides, no one puts stripper poles in a bar full of drunken women expecting nobody to use them. It’s not like I was up there flashing my pussy for everyone. I did wear pantyhose. I’m sure Mike would have loved that. I wore them just for him. God, I can’t stop thinking about his cock. I really need to get fucked. I should probably invest in a good vibrator. I would have bought one months ago, but I’m just afraid Chris would find it. He’s always sneaking into my room. I’m not sure what he’s looking for. I hope he’s not going through my panty drawer. I’m sure he’s learned how to masturbate by now. The last thing I want to find is a huge cum stain on one of my satin thongs. I guess at some point I’ll have a talk with him. I just don’t enjoy thinking about my son’s penis. I really wish his father were here…
I would have kept reading but I knew Mom was on her way back. So I packed everything back inside the box and quietly left the room. I headed back downstairs trying to process all the twisted thoughts scrambling through my mind. Clearly, my mother wasn’t as clueless or innocent as I’d always believed. She seemed to enjoy getting attention from younger men. She also knew way more about me than I’d ever realized. The thought of Mom willingly behaving like a slut really got me excited. I stepped out onto the back porch, where I lit up a cigarette, trying to calm myself down.
The view from the back porch overlooked the garden in the backyard. I stood there leaning over the railing, as I looked down and noticed that the curtains were drawn on our new landlord’s bedroom window downstairs. In the corner of the room, I spotted an empty rocking chair, next to what looked like the railings on a baby’s crib. I flicked my cigarette, then looked back again, when Cynthia appeared carrying the baby in her arms. Even from such a high angle, it was virtually impossible to look down and see anything other than her humongous tits. The image reminded me of those IMAX movies where they show you the Earth from space and you can still see the Himalayas only because they’re so fucking big.
I couldn’t help grinning at the light blue button up sweater she was wearing. The fabric was stretched out so much it looked like she bought it from Baby Gap. I took another drag of my Marlboro Light, watching as she sat down, only to gasp in disbelief when she started unbuttoning her top.
By then, I was already horny as fuck, as I watched Cynthia reach up and unsnap her bra from the front, letting her left breast flop through the opening of her sweater, before lifting it up and pressing her baby’s mouth over her swollen nipple. My whole life I’d never seen anything like it, as she sat there rocking back and forth. I’ve always preferred legs, but there was no denying the beauty of Cynthia’s phenomenal jugs. The size of her breasts reminded me of my days back at the pizza shop, where we laid out the dough until it rose into soft, round, flesh-colored mounds. The longer I watched, the more I found myself jealous of her little boy and the blissful look on his face as he eagerly suckled his mother’s tit.
Just when my dick couldn’t possibly get any harder, Mom finally returned as I heard her opening the front door. I wasn’t about to let her see what I was doing, so I quickly hustled back inside.
I met her in the kitchen where I found her wearing a short, heather gray, New England Patriots T-shirt, with black spandex yoga pants, and a pair of brown fur-lined boots. Her hair was tied back in a ponytail, with no make-up, yet I still wanted to bend her over and completely fuck her brains out.
“How’s it going?” she said. “Get much done?”
“Umm, not really,” I said. “Went out for a smoke. Figured I’d wait for you.”
“That’s fine. You must be starving,” she said. “I brought you a turkey sandwich, no tomatoes.”
“Thanks,” I said, looking around at the piles of junk everywhere. “Where should we sit?”
Mom looked around as well. There was only one chair in the kitchen. The rest were all stacked in the dining room.
“Good question,” she said. “Why don’t you sit here? If I get tired of standing, I can always sit on your lap.”
Assuming she was just kidding, I grabbed my sandwich and took a seat, while Mom leaned against the counter and started to eat.
After one bite, she strolled over toward me, walking around in front of the chair, where she then settled down, with one arm draped around my neck and her legs stretched out across my lap.
“So,” she said. “This is it. This is our new home. Are you excited?”
I would have answered, if only she hadn’t chosen that exact moment to set her ass on top of my groin. The frown on her face instantly told me she could feel how hard I was. I expected her to jump right up. Instead, she just sat there for a second, looking at me with this tortured look on her face like I’d murdered someone.
Finally, she whispered softly, with this cold, distant look in her eyes.
“Uh, Chris…is that what I think it is?”
It was just like the phone call over again. Only this time, there was no clever way for me to spin it. I was far too humiliated to look her directly in the face. Instead, I quietly looked down and slowly nodded my head. I wanted to say something, but all I could focus on was the smoothness of her leggings as she pressed her ass firmly against my cock.
Intended for yoga, the leggings felt more like velvety tights, not sheer like pantyhose, yet every bit as soft to the touch. On the plus side, the fabric was made from Lycra spandex, which visibly made them fit like a glove.
Finally, Mom pulled her arm away and slowly stood up, folding her arms in front of her.
“Maybe you should tell me what you were really doing while I was gone,” she said in an accusing tone.
Still unable to face her, I lifted my sweaty palms and started to rub them against my shorts.
“I wasn’t doing anything,” I answered meekly. “Sometimes it just happens. I’m only 19.”
“I see,” Mom said, nodding her head. “Look, I understand that you’re young and you need sex. But I can’t have you walking around the house like that. We talked about this once already. I hope you remember what you promised me.”
“Yes, I remember. But finding a girlfriend isn’t that easy. It takes time.”
“Okay, maybe you’re right,” she said. “So in the meantime, what should we do?”
“I don’t know,” I said, shrugging it off. “I’ll just have to deal with it on my own.”
“Fine,” Mom said. “Why don’t you go ahead and do that so we can get back to work.”
Granted, the logical thing to do in that situation would have probably been to stand up and go to my room. Instead of doing that, I chose to make light of the situation, hoping to cut the tension by seeing if Mom was willing to have a sense of humor about the whole thing.
“So what,” I said, staring back defiantly, “should I just whip it out right here?”
She had already started to turn away. Then she slowly twisted her head back, arms folded as she glared at me through the narrow slits of her eyes.
“You haven’t got the balls to try anything like that.”
Her response hit me like a punch in the gut. My whole adolescence was littered with people calling me a wimp. I’d never been good at sports. In school, I got picked on for being the skinniest boy in class. Girls pointed and laughed at my scrawny build, knowing I was too chicken to fight back. I’d been putting up with bullies for as long as I could remember. I wasn’t about to sit there and get bullied by my own mother.
Instead of looking down, I looked Mom square in the eye, as I jerked down my zipper, reached in and promptly pulled out my cock.
“Okay, time out,” Mom said, putting her hands up. “This has gone far enough. Put your dick back in your pants, right now. I’m not joking.”
“Neither am I,” I said, pointing the tip straight at her. “You told me I needed to cum. So that’s what I’m going to do. If you don’t like it, don’t watch.”
“Don’t watch?” she said, raising an eyebrow, with a mild laugh and an obvious smirk on her face. “So you just expect me to ignore you while you sit there touching yourself? You want me to act like this is normal?”
“Sure,” I said, “as long as you stay where I can see you.”
“Wow, you’ve got some nerve,” Mom said, dropping her head to her chest, before wearily rubbing her forehead. After a brief moment, she slowly raised her head up, responding with a short nod, as she quietly answered. “Fine, do what you want. I can’t stop you. But don’t even think about trying this again. Once you get off, we will never mention this again.”
Admittedly, it would have been easy to stop right there. I could have easily controlled myself, if only Mom had done something besides walk over, snatch my cigarettes, and light one up right in front of me. She wasn’t a smoker and she’d obviously chosen to ignore her own rule about smoking inside the house. Still, after clearing a space for herself on the table, she propped herself up, then slowly inhaled, with an air of sophistication that only made my dick harder as she gracefully crossed her legs in black spandex.
“Don’t take all day,” she snapped over a puff of smoke. “You’re lucky I’m allowing this at all.”
I wasn’t expecting any sympathy, yet I still felt compelled to explain why it was taking so long.
“Sorry, my hand’s pretty dry,” I said.
She sat there thinking for a second, startling me as she sprang up, with cigarette in hand, as she marched back over toward the counter. She flicked her cigarette, tossing it down the sink, then reached over and opened her purse, pulling out a small plastic bottle. She screwed off the cap, then boldly walked over and stood above the chair where I was sitting. Bottle in hand, she leaned over the head of my cock, squirting out a generous glob of creamy lotion, which dribbled down all over my shaft.
“Will that help?” she said, with a grin on her face which I instantly read as mild amusement.
“Very much,” I said, gripping my penis around the base, making her watch as I slid my balled fist up to the head, spreading the lotion over my veiny foreskin, making it glisten from all sides, enabling me to enjoy the feeling of my own slippery hand, rising and falling around my rigid shaft, as I sat in front of her and boldly continued to jerk off.
I sat there hoping she would study my technique, imagining one day to feel her hand instead of my own. The look on her face lacked any form of expression, as if to prevent me from noticing any signs of interest in her cold, lifeless eyes.
“Um, we should really speed this up,” she said, dropping her hands to her hips. “Is there something else I can do?”
“Sure,” I said, hoping to push this even further. “You could turn around and show me your butt.”
“Oh, I could, huh?” she said. “Will that get you off…if I turn around and show you my ass?”
“Mmm, yes please.”
“Oh,” she said, smiling openly. “I like it when you say please. Go on, little boy. Say ‘please Mom, may I look at your ass?’”
Hearing her sexy, commanding voice, with its air of implicit power, prompted the increased rhythm of my hand, as I looked up, begging with enthusiasm.
“Please, Mom,” I said earnestly. “Please, may I look at your beautiful ass?”
“Hmm,” she said with a snicker. “You did that very well,” she added, slowly turning around. She arched her back slightly, with her ass sticking out less than three inches from my face.
“How’s that?” she said, poking it out. “Tell me how good it looks.”
“Mmm, so good,” I answered quickly. “Your ass is perfect. Really, it’s perfect.”
My mouth watered at the sight of her black leggings stretched taut over the curve of her firm shapely rump. She kept her feet together, accentuating the slope where the small of her back arched over and her asscheeks strained under the tight fabric, so amazingly round and full, I could barely hold back from reaching up and squeezing that plump, sumptuous bubble.
“I’m glad you approve,” she said. “Now hurry up and cum before I lose my patience.”
“I’m getting close,” I said. “Just bend over a little further.”
“Oh, I don’t think so,” she said. “I’m not taking any more orders from you today. You’ll cum when I tell you. Understood?”
“Okay,” I whispered, losing my breath. “I’ll do anything you want.”
“That’s better,” she said. “Now I want you to stand up. We’re trading places.”
With no hesitation, I jumped out of my seat, expecting my mother to turn around and slowly sit down. Instead, she held out her index finger, directing me to stand in front of the chair. Then I watched as she set her knees down on the wooden seat, keeping her legs together as she slowly leaned forward, her ass pointed back towards me.
“Is this where you’d like to cum,” she asked, flexing her tight glutes, “right here, all over your mother’s ass?”
“Oh, fuck yeah,” I moaned, stroking intently. “You have no idea.”
“Then show me,” she said. “Show me how horny you are right now. Let me feel it. Let me feel that hot load all over my ass. Go on, Chris, cum for me.”
My knees buckled as the sound of her voice nearly caused me to pass out from overexcitement. I had never imagined that my mother was even capable of acting this way, let alone seeing it first-hand.
Was she really begging me to jerk off in our brand new kitchen? Was she actually ordering me to cum all over her black yoga pants?
I should have accepted it for the privilege that it was. Instead, I got greedy, giving her no chance to react, as I lunged forward and slammed my cock smack up against her butt, a forceful collision softened by the leggings and the meaty flesh underneath, the perfect cushion for my throbbing penis to grind against her smooth, velvety rump.
She let out a terrified shriek, as I grabbed her by the waist, ignoring her vocal protest as I violently started thrusting my hips back and forth, viciously humping her from behind.
“No, Chris don’t!” Mom cried. “Chris, stop! Oh my God! Please don’t do that!”
Of course, I could hear her. But I wasn’t about to stop, not for anything.
“You told me to cum on your ass. You said it Mom. I heard you say it!”
She said nothing in return. Yet, her ass clearly pushed back against my cock. Her voice was raspy and out of breath, with her head forward, hair swinging all over.
“Oh, God,” she moaned. “God, your dick is so hard. Oh my God, don’t stop. Yes baby, I said it. I want you to cum. I want you to cum sweetie. Please let me feel your cum!”
In 19 years, I’d never felt an orgasm quite like that, let alone seen so much spunk come gushing out of my cock like a broken water main. The force of each spasm was so violent that I stumbled over and collapsed on top of her as my legs gave out. My face was buried in her hair as I felt Mom trembling beneath me. Even then, with our bodies mashed together, the lingering sensation of her soft cheeks pressed up against my cock milked out the remaining semen flowing from my aching balls.
As I looked down and slowly rose to my feet, the black leggings spread over Mom’s ass were completely coated under a thick layer of white creamy foam, rolling down the black spandex, then pooling in the crack of her ass, before slowly dripping down to the cleft of her moist pussy.
Covered in sweat, I quietly zipped up, lost for words as I stood there scratching the top of my head.
“Umm, maybe you should go change,” I said, clearing my throat.
For a second, Mom remained quiet. I watched as she reached back, sliding her fingers through my creamy sperm.
“Yeah, good idea,” she said, slowly rising to her feet. “Just try to avoid getting another hard-on in the next ten minutes, okay?”
* * *
For the rest of that afternoon, Mom and I barely spoke. I could only assume she needed as much time to process what had just happened as I did. We spent the rest of the day quietly arranging furniture and unpacking most of our things. Mom spent most of her time in the kitchen, while I worked in the living room hooking up our television and stereo. We ordered pizza for dinner. Then sat on the couch and quietly watched football. Around nine o’clock, I went out to meet some friends from school who were hanging out downtown. By the time I got home, Mom had already gone to bed.
The next morning, I woke up and walked downstairs to an empty house. It was Monday and Mom had apparently already left for work. I’d woken up with barely enough time to grab a quick shower, throw on some clothes and race off to get to my morning class. It wasn’t like her to leave without waking me up. I started to worry that my foolish actions had managed to ruin everything on our first day. Before leaving, I’d noticed a note with a list of things Joel needed to fix, written in Mom’s handwriting on the fridge.
When I finally made it to class, the fear of Mom telling me to move out made it virtually impossible to focus on anything else. I stared off into space, tapping my pencil against the desk, dreading the thought of going home, certain of what was destined to come.
My final class ended at noon. Fortunately, before moving out, Jimmy had kindly given me two ounces of Blue Dream. So I figured the best thing to do was go home, smoke a bowl and have a couple beers, just to prepare myself for the foul mood my mother was sure to be in when she got home.
The moment I walked in the house, I instantly remembered my mother’s journal, as I headed up to her room and luckily found it in the same box where I’d left it, right at the foot of Mom’s bed. I opened it up and thumbed through a few pages, stopping at a passage that instantly caught my eye.
December 10th, 2003
Today I caught this guy following me around the mall. I was kind of scared at first, but he looked fairly harmless so I chose to ignore it rather than causing a scene. He was well dressed for a younger guy with a nice business suit like he could have been a lawyer or something. I needed some coffee so I went into Starbucks where I saw him sitting by himself. There weren’t many tables as I took my seat, which ended up facing him directly. From the moment I sat down, I could instantly feel him watching, as I looked over and caught him peeking at my legs. I could have got up and found another seat, but he wasn’t being terribly obvious about it. So I sat there and kept my legs crossed, waiting to see if he’d move on. After a minute, I realized he wasn’t leaving. So I glanced over and looked him straight in the eye thinking he’d take the hint and go away. He must have thought I was flirting when he looked up and smiled back at me. For a moment, I was expecting him to walk over and say something. But the longer he waited, the more I realized how nervous he was to approach me. I was kind of insulted, but then I figured if all he wanted was a show then why not give him one just to fuck with his head. When he looked over again, I picked up my coffee, turned my hips toward him, and slowly uncrossed my legs. I paused for a moment, holding them open to show him the black thong I’d worn under my pantyhose. I did this three or four times, crossing my legs back and forth. Each time, I held my legs open for a second, letting him see up my skirt. Finally, I stood up and quietly went on my way, never thinking he’d actually have the nerve to follow me down to the shoe store.
I’d found a great deal on a black pair of Jimmy Choo’s with a peep-toe and a nice glossy finish. I sat down to try them on when I looked up and saw him watching me through the window. The bench was so low that sitting down opened my skirt up even more, exposing not only my black thong, but most of the pantyhose covering my legs as well. Still, I wasn’t about to let some pervert keep me from buying shoes. So I sat there on the bench thanking myself for wearing underwear, with my legs open and my skirt up around hips, working my feet into the shoes. When I looked up again, I couldn’t believe he was still standing there trying to play innocent with his back turned. At that point, I probably should have confronted him. Instead, I just paid for the shoes and walked out, thinking he’d never follow me outside.
I reached the exit and turned around to see if he was still behind me. Sure enough, he walked out with a smile on his face like he hadn’t done anything wrong. By then, I was so irritated that I walked over and asked if I could help with
