Chapter One

I peeked through the tiny slit in the cracked bathroom door. I won’t try to justify my actions—there was no justification. Spying on a naked woman was wrong, but what can I say? I was a horny eighteen-year-old boy. Walking through my neighbor’s house while she was getting out of the shower with the door partially open was like baiting the hook and dangling it in front of me.

Ms. Bennet had been my curvy neighbor all my life. A pleasant woman who lived alone in the house beside my parents and never caused any problems. She was a middle school teacher at a private school, so I never had her as my teacher, but we had kept up with one another over the years. During my youngest years, she taught a bible study group with all the kids in the neighborhood; then, as I aged and entered my entrepreneurial years, Ms. Bennet became my first customer for cutting grass.

Over the years, my services expanded and grew to include mulch, weeding, gardening, and power washing to the point now, as I am on the verge of graduating high school, I didn’t have to go to college if I didn’t want to. I was already making a livable wage with over a hundred clients. However, with the money I saved up throughout middle school and high school, I decided to put myself through college and business school. I’d still keep my business going, but I would be starting fresh with new clients a hundred miles away near the University of Tennessee. After six years of handling her lawn, today was my last cut.

Last weekend was my graduation, and tonight, after I went home and showered, I was moving to my apartment to get a head start on building a client base over the summer before school began. So when I came into her house to say goodbye and thanks, I guess I didn’t really expect to find Ms. Bennet here. I shouldn’t have peeked a look. I shouldn’t have kept looking after peeking; I knew this. But there was something captivating about seeing her step out of the shower. She had been my friendly neighbor and mother-like figure for so long that it was like I was just seeing her as a woman for the first time.

A curvy, sexy woman… I thought. Her long brunette hair clung to her back as she reached for a towel and got to work drying her body off. Her plump breasts were scarred with stretch marks and swayed with her every turn. She had more padding, as most women did in their forties, but carried it well. Adjusting my jeans, I felt my cock continue to grow and harden at the sight. I swear I was just about to look away and leave when I was spotted. It was as if Ms. Bennet had a sixth sense that just kicked in. Without warning, her eyes snapped to the mirror from which I had been watching her reflection, and shock washed over her face.

Backing away from the bathroom door was futile now, but the juvenile portion of my brain took over and did it anyway. I was caught with my hand in the cookie jar. I looked for the exit and started running. The thing that stopped me was the sharp and swift shriek of Ms. Bennet’s voice halted me in my tracks and sent my mind reeling back a decade to bible study school. She’d use the same voice then to chastise me for playing in the back of class rather than paying attention.

“Ben!” her voice was wrought with unstable emotions. “You turn around and look at me.”

Turning around like a whipped dog, I squinted through winced eyes up at Ms. Bennet. She stood in the doorway to her bathroom with a towel clenched around her body and over her bountiful breasts. The surprise in her wide eyes hurt almost as much as the fear in her tight grip on her towel as if I would try to take it from her or do anything else that was unconscionable to think.

“And what were you doing, mister?” she asked, cocking her head to the side. Her wet hair that wasn’t clung to her back dangled with the direction of motion.

“I—I’m sorry, Ms. Bennet,” I stuttered and looked away to hide my embarrassment. While I had always had an unparalleled work ethic and drive when it came to business and school, my confidence was constantly lacking when it came to social situations—especially women. I had a feeling this interaction wasn’t going to improve that. “I finished your lawn and just came in to say goodbye because, you know, I—I was leaving for college, so I wanted to say bye, and I heard the shower running, but…” The staccato and stutters of my words became so much that I simply slumped where I stood and sighed. “I’m sorry I spied on you. Please don’t tell my parents.”

Ms. Bennet huffed a sigh and made a face as she tilted her head back the other way. The stiff lines of the stern, middle-aged teacher softened as her shoulders fell before she made an apologetic face.

“I—I’ll just go,” I said in a hurry to leave the increasingly awkward moment. “Sorry, again.”

“Wait, wait,” Ms. Bennet said with a final exasperated sigh. “I’m not gonna let you leave on a bad note. Not after so many years of you being a good young man. Come in over here to the living room. Have a seat.”

I winced again, preferring to just leave on a bad, awkward note than prolong this moment, but she was already walking to the living room, so I followed.

I sat down on a loveseat and expected her to sit in the chair beside it, but instead, she sat next to me. Immediately, I locked my neck and stared as high on her face as possible as she was still naked except for the beige towel she had wrapped around her. When she sat down, the towel slipped up, revealing the length of her thick thighs and her creamy skin that led all the way to her shaved pussy that I spied on earlier. It was like a magnet that pulled on my sight down with a tractor beam, but I resisted.

“I’m a forgiving woman, and I know ‘boys will be boys,’ so I won’t hold it against you, but just know, you should only look on a lady who is naked if you asked permission first, okay?” she said in a voice I thought only teachers had mastered.

“Yes, of course,” I mumbled, though in the back of my head, I wondered what would happen if I asked for permission right then and there.

“Good,” Ms. Bennet said with a proud smile. “Now I just wanted to say I’m so happy to see you going to college. I remember when you were a little tike in my Sunday school. Now look at you. The only problem is you’ve been doing my lawn so long, I don’t know if I can do it myself.” She laughed and patted my shoulder as I joined in. “Well, I hope you enjoy your time there, have lots of experiences, and learn lots, okay?”

“Yes—yeah, I’ll do my best,” I said.

“Now, let me go find my wallet. I want to give you a little something extra since it’s your last—oh!” Ms. Bennet patted my lap as she stood, but she wasn’t prepared—and I hadn’t realized—the erection standing tall in my jeans poked down at an odd angle and wrote where she touched.

As shock over came her Ms. Bennet’s face as her hand recoiled, horror drowned my face. I didn’t think there was a lower level of shame I could possibly stoop to but somehow I found it.

“Oh God, I’m—I’m so sorry, I—I didn’t know,” I blurted out and moved to stand, but Ms. Bennet stopped and quieted me.

“It’s okay, dear. It’s okay. It’s my fault; I shouldn’t have touched you so recently after… seeing those things,” she said hesitantly. A smile was stuck in the corner of her lips, and she pursed her lips as she looked down on it with pity. “It’s not the first penis I’ve seen, and I’m sure it's not the first time that’s happened to you.”

“In public, it is,” I admitted. “God, this is so embarrassing. I didn’t even realize—I’m sorry…”

Ms. Bennet laughed a light giggle and petted my shoulder this time, “Stop apologizing, Ben. You did nothing wrong. Honestly, it’s kind of flattering. I didn’t think a young man like you could even possibly still find me attractive.”

“Are you kidding?” I blurted out. The smile on her face deepened, and a slight pink hue warmed her cheek.

“Well… I am over twice your age, so…” she said, pulling her wet hair over one shoulder distractedly.

“That—” I started but hesitated as I didn’t want to dig myself a deeper hole but then looked back down at my raging boner pressing through my jeans and realized I was already at the bottom. “Well, that doesn’t bother me.”

 “Oh, you’re too kind, Ben. You definitely got the butterflies airborne in this old gal’s belly.” Ms. Bennet laughed, trying to break the tension as the pink of her cheeks turned ruby red.

There were several seconds that followed her laughter, which was filled with awkward silence. Had I not already been immune to the discomfort in the air, they might have killed me, but then Ms. Bennet did something so surprising that it caught me off guard.

In a sudden burst of motion, she pulled her towel down, flashing me with her massive breasts, and quickly covered them again. A devious grin and giggle consumed her as she hid her face and nuclear red cheeks with a hand. “Ah! I can’t believe I did that!”

“Can I touch them? I’ve never…”

Ms. Bennet’s eyebrows went high with shock. “You mean you never… you’re a virgin?” she asked, blinked, and suddenly realized the forwardness of her words when she saw the hurt in my reaction. “I’m sorry to sound so… I just… you’re a handsome young man and always seem so popular. I just thought…”

I was so caught up in the moment that I didn’t realize what I was admitting to until it was too late. Now I was afraid to say anything else and was afraid of divulging even more. This conversation just went from one of the most embarrassing of my life to the most insulting.

“I have just always been busy, you know, with school or the business…” my words trailed off as I hung my head.

“Hey…” Ms. Bennet whispered and scooted an inch closer to me as she rested a hand on my knee. “Don’t be embarrassed. It’s a good thing. It means you have discipline and character. You’re going off to college; you have plenty of time for all that. Trust me,” she said with a small chuckle at the end. Pursing her lips, she looked around her living room as if people might have magically appeared without her knowing, then loosened her towel. “Here… just don’t let your parents know, okay?”

The towel fell to her lap and I was able to truly appreciate the beauty of Ms. Bennet’s figure. The curve of her large, round natural breasts as they hung from her chest. The circle of pink areola surrounding the hard nub of a nipple.

She smiled and giggled a little at my face of wonder, “Well, go on.”

Raising my palms to her breasts, I couldn’t help but feel astonished at how soft her skin was. Compared to my coarse and calloused hands from years of strenuous labor, slipping my hands over, around, and under her breasts felt like massaging silk pillows. I don’t know how long my hands were on her while stuck in my trance, but when I finally looked up at Ms. Bennet, I saw her eyes were closed, and her lips parted in a silent gasp.

She’s enjoying my touch, I realized with bubbling excitement. My cock flexed, trying its hardest to rip through my jeans. When her eyes flicked open, I returned my gaze to her breasts and pretended to have not noticed.

My touch changed from one of exploration to one with a purpose. I had a goal now. Gently, I pressed my palms into her nipples and rubbed in outward circles, my strong fingers groping her thickness with every motion. I noticed her chest rise and fall with greater speed, and the sound of her breath grew louder. When I moved my thumbs to her nipples and started to circle them, Ms. Bennet pushed a hand down to the couch cushion to steady herself, but while doing so, she knocked part of the towel from her lap. I could almost see what lay between her legs.

In my distraction, my hands moved on their own, rolling her nipples between my fingers, flicking her aching nipples with the pads of my thumbs, and squeezing and mashing her heavy breasts with a stronger grip now. Ms. Bennet’s brow was knitted, and her forehead creased as she screamed in silence. I bit my lip and read her body’s cues, continuing to molest her breasts and nipples in whatever way caused the older woman the most agony until it happened.

Jutting out a hand, Ms. Bennet gripped my strong biceps. At first, I thought she tried to stop me, but then I felt her pull me closer as she leaned forward. Pressing her thighs together, she heaved and gasped until a stuttered moan escaped her lips as she rocked forward and back. With eyes closed, I don’t think she realized how close she came to kissing me in one motion, then nearly putting her head in my lap in the next. I smelled the fruity odor of her hair conditioner and the familiar spice of the perfume she had been lightly using for decades now. My cock flexed so hard in my jeans, for a moment, I wondered if I just came accidentally.

Chapter Two

When the moment passed, Ms. Bennet sucked in a deep breath and exhaled, shuttering. Opening her eyes, it was as if she just remembered where she was and who she was as she quickly leaned back and covered her breasts with one arm while the other hand searched for the towel.

“Sorry,” I mumbled as I retracted, wondering if I crossed a line.

“Oh, um, don’t be. No, dear. You did nothing wrong,” Ms. Bennet said, licking her lips. “It’s um, it’s just I haven’t been touched like that in quite some time. My body just isn’t used to it is all. Maybe it’s best if you head on home.”

“Okay,” I said and stood. Ms. Bennet and I froze at the same time with our eyes locked on my crotch. If my hard-on was a small tent before, it had now turned my pants into a triangle. At the tip of my tent, a small round wet spot formed on the crotch of my jeans. If the pre-cum made it that far, I couldn’t even imagine the mess in my boxers. “Oh, sorry, I—I don’t think I can,” I sighed, humiliated. “Can I just wait here for a few minutes? Let it go down before going back home.”

“Uh, sure. Yeah, of course,” she said. “I’m… just going to get my robe.”

When Ms. Bennet left for the bathroom, I spent the next several minutes trying to calm down and relax, but nothing made it budge. It got to the point that I was even getting concerned; normally, they went away after a minute or two. Ten minutes later, Ms. Bennet returned with drier hair, a layer of makeup applied, and wearing a black silk robe, which wasn’t helping anything. The robe was thin and hugged her hips and breasts. Her nipples showed through the fabric as if it was see-through mesh.

“No, luck?” she said, looking down at the growing stain on my jeans.

“No, sorry. Um, you think I could use your bathroom… um, for a few minutes?” I asked, tossing another shovel full of embarrassment out of the hole I was digging.

Ms. Bennet flattened her lips disapprovingly and rubbed a hand on her forehead, expressing her dismay at their strange situation.

“Um, sure, yeah. I suppose it’s fine. Kind of a strange situation we’re in, huh?” she giggled and led me to the bathroom.

Ms. Bennet had a water closet-style bathroom with a toilet and shower in a separate room within the bathroom. Stepping into the toilet room, I felt a flush of heat hit my face as I closed the door. Ms. Bennet awkwardly turned to the mirror over the sink and went back to applying her makeup.

Removing my jeans and boxers, I found a mess of pre-cum covering my shaft that protruded like a kickstand. As soon as I started stroking, logic and reason diminished in my mind until they were forgotten concepts. I couldn’t believe I was jacking off alone in front of this toilet when there was this curvy cougar who had already come from me, touching her breasts on the other side of this door. Twisting the doorknob carefully with my free hand, I pulled it open a few millimeters until I could see through the sliver of a crack.

Ms. Bennet flicked on eye shadow and mascara while leaning over her sink. The bulge of her fat ass stuck through her robe. When she leaned back to search through her tray of makeup, I could see the flaps of her robe had loosened, and her breasts were visibly shaking as she moved about. Seconds went by as I jerked off when, to my surprise, she undid her robe entirely. The black silk hugged the outside of her breasts and thighs like it was begging to fall off completely. I bit my lip as she reached for something close to the door, moving closer. I could see the small mound of blonde hair between her legs, and my cock throbbed.

I relived a familiar startle when Ms. Bennet finished applying her lipstick and pushed her nearest hand slowly through the cracked door.

She knows! I thought, and my heart dropped on my stomach.

I was preparing my next in a series of apologies when her hand continued in until it bumped against the side of my cock. Immediately, her delicate fingers slipped around my shaft and began to stroke me. The sound that escaped my lips was something between a gasp and a groan, but it was the first time another person had touched me there—let alone an attractive woman over twice my age who used to read to me in Sunday school.

With her whole arm in the toilet room with me, she pumped my shaft, making a wet gooey sound as she spread my juices along my cock. She faced forward, staring at herself in the mirror, and watched her breasts jiggle uncontrollably as her robe slipped down her shoulders. It was like she was trying to hide that she was giving me a hand job even though there was no one here to hide it from. My breathing increased to a pant as I leaned forward, catching myself with a hand on the wall as she sapped the strength from me with every stroke. The girth of my cock flexed against her grip, and she squeezed back with every stroke. Ms. Bennet was panting now nearly as hard as she was before when she came. Her teeth clenched; I could feel her hand willing me to cum. With one final hard flex, I shot my load, spilling over the toilet seat and tank as she continued to stroke me until the last dribble fell from my tip.

Chapter Three

When the waves of euphoria finally dissipated, I opened my eyes to see the mess I had made. Thick, smokey white cum covered the toilet, and logic, reason, and embarrassment reappeared in my mind. Ms. Bennet stuck her head inside to observe me and the mess. Before I could apologize, she was waving me away and using a small bottle of cleaner and toilet paper to wipe up my mess. For a moment, with her on her bent over wiping, she looked over at my softening cock a few inches from her face. I held my breath, but the moment passed, and she finished cleaning before straightening to look at me. There was a mixed bag of emotions cluttering her face. Apologies, admonishments, and arousal all competed for dominance.

The moment grew too much for me and my shrinking cock. I reached down for my jeans, and Ms. Bennet held up a hand.

“Wait. Wait…” she said, then sighed, making an uncomfortable face. “Come here.”

Taking me by the hand like a Sunday school teacher would, she led me out of the bathroom, down the hall, and into her bedroom. It was modestly decorated in grays, whites, and soft blues. In the center against the wall was her king-sized bed, which had a dozen square pillows covering it. Standing in front of her bed, I was in a daze. It was like being walked through one of my dreams. Letting her robe fall to the floor, she grabbed the tail of my shirt and pulled it off so that I was as naked as she was.

Ms. Bennet teethed on the corner of her lip, a sign that she was as nervous as I was, which oddly gave me a jolt of confidence. Stepping forward, I kissed her, and she kissed me back. Her warm lips were soft and wet. When her tongue swirled against mine, a crash of vertigo nearly knocked me off my feet. While my hands cupped her hips and slowly inched over her ass in ever-expanding circles, Ms. Bennet’s hands seemed content with rubbing over every hard muscle and divot on my chest, shoulders, and arms.

Just when the kissing was beginning to turn into something else, Ms. Bennet pulled away with a smile on the corner of her lips. “Here, lay down.”

I did and tried to focus on memorizing the sight of Ms. Bennet crawling on all fours toward me on her bed, her breasts bouncing between her arms as she neared. Sidling beside me, she licked her lips as she propped herself up on her pillows and fed one of her breasts to me.

“Come here, baby,” she whispered.

Without hesitation, my lips parted, and I accepted her nipple into my mouth. My hands cupped her chest as I licked and kissed her nipple. The soft moans that slowly grew louder egged me on to suck on her nipple.

“Oh, God, yes, honey,” she rasped, her fingers combing through my hair. “It’s okay, sweety. Y—you can be a little rough with them. Ahmm… I don’t mind.”

Eyeing her face, I began to teeth on her nipple as I saw the shock mix with pleasure in her eyes. “Oh my God, honey, I’m so sensitive,” she panted.

My rough hands explored her body, rubbing every inch I could reach until they brushed the start of her pubic hair and hesitated. Ms. Bennet’s hand found mine and guided it down between her thighs until the hairs I felt were wet. She pressed my fingers down on her clit and made slow, repetitive circles. Instantly, she reacted.

“Oh my God,” she trembled, her other hand holding me tighter to her breast. “Oh, honey—sweety, don’t stop.”

Switching to her other breast, my lips clamped down on her nipple and began sucking hard immediately. Ms. Bennet bent forward and cried out as her legs clamped around my hand, and her entire body began to tremble.

“Keep going, keep going, keeping, honey—oh… God…” she whispered into the top of my head as I sped my fingers up on her clit. When I bit her nipple, she let out a loud scream and cursed for the time I had ever heard. “Oh shhhiiit, God!”

My hand slipped off her clit when a splash squirted from her pussy, and her flexed thighs quivered. I had seen women squirt in porn before, but I had always thought it was made up and not a real thing. Touching her clit again, I was able to make one circle on her clit before she jolted back on her hand and grabbed mine, pulling it away from her.

“I… I…” she panted, still trying to catch her breath as she giggled. “I need a second—oh God…” her eyes rolled back as every muscle in her body appeared to tense and loosen sporadically. “It’s been so long since I—I orgasmed like that… God…”

“Are you okay?” I asked, frozen, worried I had done something wrong.

She smiled down at me like I was an adorable pet. Her body finally began to relax, and her panting slowed slightly.

“Come here,” she whispered, though I didn’t even have to move. Ms. Bennet rolled over on top of me. Her lips covered mine as her breasts mashed into my chest. It was her turn to rub a hand down my chest to the half-mast cock between my legs. She hummed a note of approval at its touch and pumped it erect with a few strokes. “Oh, God, honey… you’re so hard…”

Inching one leg over my hips while we kissed, after several minutes, Ms. Bennet was very nearly completely mounted on top of me when I felt her pussy hairs brush the tip of my cock.

“We… we don’t have to do this…” Ms. Bennet whispered suddenly. Her cheek pressed against mine as we broke briefly from our wild make-out session. Our hot breath bathed each other as we panted and groaned for another. “I don’t—maybe your first time should be, mmm, with someone—someone your own age.”

“No,” I protested, one hand rubbing over her fat ass cheeks and squeezing. This caused Ms. Bennet to cry out and inch her pussy nearer to the tip of my cock. “I want you.” I groaned the first thing that came to mind. “Your body, your lips, God… you have me so turned on. I want you so bad.”

Surprise sprouted on Ms. Bennet’s face and voice, “You do?”

“God, yes. You have no idea how many times I’ve thought about you,” I admitted.

A fire ignited in Ms. Bennet’s eyes that I had never seen before. It was a hunger of insatiability and full of excitement. Her hands cupped my cheeks as she kissed me hard and deep as she lowered her pussy onto my shaft. My hands gripped her fat ass cheeks as I willed her to move quicker, but she refused, savoring the moment as the tip of my cock pierced the tender flesh of her pussy lips.

Breaking the kiss, Ms. Bennet gasped when I was halfway in. The surprise swirled with pleasure on her face as she squinted and moaned. Her tight moist pussy walls squeezed on me as I flexed inside her.

“Oh my God, honey,” she gasped, her eyes flirting with the ceiling as she bit her lip.

Ms. Bennet leaned back, and my cock slipped all the way inside her, and her eyes locked with mine. They were squinted and focused as she gasped for each breath.

“It’s—it’s been so—so many years since I’ve had such a—a hard cock inside me,” she whispered and squealed. My cock throbbed, and she groped her own breasts as she cooed.

Slowly, she started to rock on top of me. The last inches of my cock slipped in and out of her slippery pussy with ease as she mouthed a silent moan with every insertion. The tease wasn’t enough for me. I wanted more.

Gripping Ms. Bennet’s ass with both my fists, I pushed up on my feet and began pumping my cock inside her.

“Oh, lord!” Ms. Bennet yelped and fell forward, catching herself on her hands on either side of my face. Her long blonde hair, still damp from her shower, dangled over my face.

My strong legs and muscular core flexed as I rammed my cock up and into my neighbor’s pussy as I pulled down on her ass. Her swaying tits clapped and made circled above my chest as the older woman squinted and arched her back.

“Yes, yes! Oh God, Ben—yes! Take me!” she cried as the sound of my cock thumping inside her grew louder.

Looking up at this gorgeous, mature, naked woman made my hard cock throb as Ms. Bennet began to ride me more aggressively. The whole bed shook and creaked as her hips moved in unison with my thrusts. I moved my hands up her body and cupped her bouncing breasts in my warm, rough palms. Lifting my head, I fed one of the nipples into my mouth—sucking, tonguing, and biting it before switching to the other.

“Ahh! Ben!” was all she shrieked before her thighs locked around my hips and her pussy tightened around my cock. It was like her body had become a giant hand that clenched around me. Flicking her hair to one side, she wrapped her arms around my shoulders and neck and forced her lips on mine. Kissing me hard and with a passion I didn’t think I would ever know again, Ms. Bennet hummed a note of pleasure.

Despite her shuddering body clamped down on mine, my warm palms slipped down her tender ribs, around the small of her back, and pressed down on her ass as I forced my cock up and into her. Ms. Bennet’s eyebrow went high during the kiss, and she moaned a squeal that I swallowed. Continuing my short, hard thrusts, Ms. Bennet finally broke the kiss as the pleasure became too much, and she released a guttural moan, her hot breath bathing my chin and neck. A violent quiver shuddered through her body, and I felt this mature cougar’s pussy flex and squirt on my cock. She tensed again and released a louder moan and a smaller squirt of juices on my cock.

I was so close to cumming myself that I couldn’t stop. Pressing down on her ass with every hard buck into her turned Ms. Bennet’s face more innocent. Her wide eyes and gaping mouth hovered over me with almost a look of betrayal with every thrust.

“Oh… oh, honey, oh God, yes! Keep going!” she cried. “Let it go. Let it go inside me, honey—ugh… sweety, yes! Give it to me!”

 With a final thrust inside her, my cock flexed and filled her with spurts of warm semen. Her slippery lips milked my shaft as my balls emptied inside her. Ms. Bennet leaned forward, kissing me deeply. Her breasts mashed against my chest, and her hair draped around my face like a curtain that shut out the entire world from our moment. The euphoria lasted forever, and still, it didn’t feel long enough. After several minutes of making out, my neighbor pulled away from the kiss that I didn’t want to end.

As she stood and put her robe back on, I did my best to savor the sight of her deliciously curvy body, as this was probably the only time I’d see her like this. While I was dressed, Ms. Bennet asked me about my classes and if I was nervous. Suddenly, she was my neighbor again.

“I’m leaving tonight, but plan on coming back for Christmas or Spring Break,” I said. “Maybe we’ll see each other then?” my breath baited with hope.

Ms. Bennet smiled coyly, “I’d like that.” She said.

Walking me to the door, we said our goodbyes, and then, without warning, she pulled me back inside for one final lingering kiss. My neighbor giggled afterward.

“Just needed one more from you,” she admitted.

“I’m going to need more than one from you the next time I see you,” I smiled. Leaving her freshly mowed lawn for the last time, I felt a seed of confidence planted in me that I didn’t have before. I wasn’t a virgin anymore, and I wasn’t a boy anymore. I was a man and ready to start my life, thanks to my neighborly cougar.