Cougar and her Five Virginal Cubs Ch. 08

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All that's left are sexy memories of Mom, Sis, and Kathleen.
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Part 8 of the 19 part series

Updated 10/30/2022
Created 06/30/2012
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Chapter Eight - Reliving the Memory

It was late, early evening, and I had been at Kathleen's place several hours for an unbelievable day of painting and screwing. Well, certainly, the screwing was the unbelievable part of the day but, then again, the painting wasn't so bad either because of everything that led up to the painting preparation, the actual painting, and the cleanup of the mess that I made. It was because of the painting and the errant doors that I got to see Kathleen's little striptease show, when she changed into her overalls in front of me. Never having experienced a woman removing her clothes in front of me, a gross understatement, bit of exhibitionism was as shocking as it was exciting.

Truth be told and I'm as embarrassed as I am excited to admit this, but except for my mother and older sister, I've never seen a naked woman before, never mind a woman in her panties and bra. Other than mere photographs in Playboy, again, other than my mother and sister, Kathleen was my first woman that I saw naked, up close and personal. Just as I couldn't believe my eyes, when she unbuttoned and removed her blouse in front of me, I couldn't believe my eyes, when she unzipped and removed her skirt and stood in front of me in her panties and bra, albeit with her back to me. With sexy lingerie being my favorite outfit of choice, looking so much better than even a woman standing there naked, Kathleen was sexy and sensual decked out in her panty and bra. Then, when she reached behind her back to unhook her bra, when she flashed me the entire side of her breast, while stooping to pull up her overalls, having never seen such an erotically exciting naked sight, I thought I'd cum in my pants.

She had big tits, C cuppers that looked even bigger because she was tall and slender, albeit shapely. She stood 5'7" and appeared to have weighed no more than 125 pounds, so thin for a man, but oh, so shapely for a woman, she had an incredible body. The narrowness of her waist made her breasts appear so much fuller, rounder, and bigger, and with her hips curving out to her ass, so round and so shapely, her naked body was akin to a long, winding, banked curve on a racetrack. With my pulse racing, my heart pumping, and my engine revving, I couldn't wait to run my hands along the full length of her. I couldn't wait to touch her, while negotiating all of her dangerous curves. I couldn't wait to feel her naked, sexy body and in my arms. Relegated to just watching her, I could only imagine how she'd feel

While she undressed, just as she removed her bra, I wished I had the nerve to walk around her and see her tits, in the way she walked around me and saw me standing there in my underwear with my cock pitching a huge tent. I wish I had the nerve to spin her around and kiss her, while she was topless. I wish I could have touched and felt her C cup breasts, while sucking her nipples and reaching down her panties to finger her pussy but, never having done that with any woman before, not even one my own age and especially one her age, I was afraid. So sexually unsophisticated, so naively virginal, I was so afraid to make the first move on her.

I was afraid she'd take my intentions wrong because I misread her intentions. I was afraid I'd ruin everything, before it even started. If I touched her, if I felt her, if I took her in my arms and kissed her, I was afraid she'd scream rape and demand that I leave or she'd call the police. She wasn't just any Italian woman from the neighborhood. She was an older woman, an Irish woman, and with my lack of experience with any woman, Italian or Irish, holding me back and stopping me in my tracks, I was scared into inaction.

When I removed my jeans with my back to her and she walked around me on the pretense of getting empty coffee cans under that sink to collect the paint, she stared at my erection that tented my underwear. Embarrassing and exciting at the same time, I wanted to show her my cock but, again, I was afraid. Clearly, with my erect cock so stiffly hard, she could see the side of my exposed prick through the pee hole in my underwear. Clearly she could see my balls and my pubic hair that were exposed from the underwear being pulled away from my body by my erection.

Except for those times, when my mother walked in on me naked and except for those times, when my older sister caught me masturbating, no woman has ever seen my cock before. Even then, hoping they did, I couldn't tell if my mother and/or sister liked seeing my cock. Any time they walked in on me with me being so exposed, it all happened so fast that I couldn't tell if they were excited, embarrassed, or disgusted by the sight of my prick. I only knew that they looked. I only knew that they saw my erect prick. Other than that, I only knew how I felt, excited that they saw my cock and wishing they'd stayed, so that I could show them more.

When my mother and sister burst in my room, while I was standing there naked, it happened so unexpectedly fast that I didn't even have the time enough to react to put a hand down to cover myself. Whenever one or the other caught me masturbating, usually my sister, even though I was so embarrassed, once I composed myself, I wished they'd stay to watch me cum. As if they were deer caught in headlights, both my sister and mother looked down at my cock and stood there staring longer than they should have, before turning to leave and closing the door behind them.

Always so horny, I always had an erection, back then, and whenever they entered my room unannounced they saw my cock at my fullest extension. Maybe, that's why they looked longer at me because my cock was erect and so big. I don't know. A time when neither my mother and sister were having sex, maybe they liked what they saw. Maybe they were just horny for a cock, any cock, even my cock. I don't know that either.

So surreal, as if it all happened in slow motion, my mother and my sister both stared at my cock, at least, I think they did and I masturbated over them staring at my cock for months. Actually, while fantasizing about them touching me, I masturbated over my mother and my sister seeing me naked for years. Only, I never told my friends about my mother and sister seeing me naked. I never told them about my mother and sister staring at my cock. In the way they thought about the forbidden, incestuous relationship that Joey had with his mother, they'd really think me perverted, if I told them that I got off having my mother and my sister seeing me naked.

With my horniness escalating with my hormones raging out of control, if it wasn't for Kathleen releasing the sexual tension that I had, I probably would have flashed my mother and sister on purpose. Who knows? Maybe I would have tried something with my sister and/or my mother. Maybe I would have touched them and felt them inappropriately. Maybe, I would have tried to have sex with them. I wonder if my mother or sister would have taken me up on my offer to have sex with me. If I had to pick one, I'd pick my sister but, back then, because my Mom was so young, she was hot, too. Moreover, there was more lust in my eyes, whenever she saw me naked and, especially, when I saw her naked. She was never as shy as my sister was about sex, especially incestuous sex.

Whenever my sister caught me masturbating, she'd stare at my cock, before calling me a pervert and slamming shut my bedroom door. Minding my own business in my own room with the door closed, she's the one who opened my door without knocking. She's the one, who barged in my room, while I was masturbating and stood there staring at my exposed prick, yet, I'm the pervert. Why is that? Why does she get a free look at my manhood, when she denies me so much as a down blouse and/or up skirt, most times. What the Hell did I do, other than to answer my personal need to ejaculate in the privacy of my own room?

After that incident, it was as if she went out of her way to catch me masturbating and she caught me several times more, once just as I exploded cum all over my stomach, chest, and thighs. Right at the very height of my sexual excitement, I didn't care if she was standing there staring at me explode a volume of cum. Matter of fact, I was even more sexually excited knowing that she was there watching me cum. That day, while my cock continued oozing cum, she closed my bedroom door behind her and stood in my room staring at my prick, as I wiped cum from my stomach, chest, and thighs with toilet tissue. Even though, obviously, she enjoyed the free masturbation show, she lambasted me with foul names for having caught me pleasuring myself.

With my cock still in my hand, just as it excited me to have her still standing their staring at me, while calling me names, it excited me for my sister to see my naked cock so big and so hard, just as it exploded cum. It took all the control that I had not to ask her if she wanted to touch me, stroke me, and masturbate me. It took all the control that I had not to ask her, if she wanted to take me in her mouth and lick me clean, while I was still cumming. Always so terribly horny, not that I'd do that to them or ever want them to do that to me, but I always fantasized about my mother, especially my mother, or my sister, jerking me off, blowing me, and/or fucking me.

I used to wonder, back then, if I was perverted or just normal. With so much testosterone flowing through my 18-years-old veins, with the ever present thoughts of incest crossing the line and distorting my sexual excitement, my definition of perversion was as twisted, as it was normal among my peers. At that age, all of us so very hormonal, whether man or women, especially man, we're all perverted.

Then, thinking back so very long ago, there was that one time that I opened my mother's bedroom door and saw her standing by her dresser naked. Turning to face me, as if confronting my horniness with her immodesty, she gave me a full frontal view of her naked body. Standing there with her hands on her hips, while looking at me looking at her, I memorized every detail of her naked body. Motionless, with incest heating my desire for my own mother, I couldn't move. There just a few feet away from me was my mother's big tits and her bushy, dark brown pussy.

"Please knock the next time," she said without cowering and/or making any move to cover her nakedness. "Now get out of my room, please, so that I may get dressed." When I didn't move fast enough, couldn't move fast enough, she walked to me and pushed me out of her bedroom. "Get out," she screamed slamming shut her door.

I so wanted to reach out and cup her big breast. I so wanted to finger her dark brown nipple. I so wanted to finger my mother's pussy to see what it felt like to feel a woman and to feel the place where she birth me. Had she given me any encouragement at all, I would have pushed her back on her bed and mounted her. Had she given me any encouragement at all, I would have pulled out my cock, pushed her down to her knees, and had her suck me. Yet, as excited as I was seeing my mother naked, I was guilt ridden for having incestuous desires for my mother and for my sister.

Needing to get laid, probably, no doubt, she was always so angry, but why was she so angry? Was she angry because I saw her naked? Was she angry because she purposely flashed her naked body to me and because I didn't make a move to touch her, feel her, and grope her? Maybe she wanted me to push her back on the bed and force myself on her. Maybe she needed me to make the first move, so that she'd always have me to blame and to feel guilty that I fucked my mother. Maybe, unable to bring herself to cheat on my Dad, she felt safe cheating on him with me. I don't know. I'll never know.

Why didn't she try covering herself with her hands and/or her forearms. She could have pulled the bedspread from the bed to put over her nakedness, if she was so embarrassed. She could have grabbed a pillow. The pillow would have hidden her tits and pussy from my horny eyes, but she didn't shield herself from my sexual stares. Yet, she made no attempt to preserve her modesty and we never had a conversation about all that I saw of her that day.

Thinking back on that fateful day, I couldn't help but wonder if she was angry at herself because she was driven to show me her naked body. I couldn't help but wonder, if she was angry at herself for being sexually excited showing me her naked body, as I was excited seeing her naked body. Nonetheless her anger, the reason for her anger, and for my obvious sexual, albeit incestuous excitement, I didn't dare make a move. I stood there and stared.

Over the years, I can't even count how many times I masturbated over seeing my mother's naked body. Over the years, forget about my sister for a moment, I can't even count how many times I fantasized about having sex with my mother. Back then, incest was something that only happened behind closed doors and to those ignorant people who lived a solitary life in the woods. Incest was something that no one even dared whisper about doing or wanted to do. Yet, so many men had sex with their sister, mothers, daughters, aunts, and cousins. Most times, it was only a problem, if they became pregnant.

The first time I saw my sister naked, an explosion of sexual emotion, I was so embarrassed and so excited. Yet, always, after getting a good look of her ass, tits, and/or pussy, I was always so horny afterward that I couldn't control myself from trying to time opening her bedroom door perfectly and without knocking, when she was changing out of her clothes, for me to get another look of sister naked. Never did I catch her again, when she was naked, but I caught her plenty of times in her panty and bra. It's funny how her reaction to me seeing her in her panty in bra was even more violent than me seeing her naked. Always, she threw whatever was handy, a book or a shoe, at my head. Now, that I think back about it, I was more successful at catching my mother naked than catching my sister naked.

Now, that I think back about it, hoping that she was to save me from feeling so guilty, I wonder if my mother was standing there naked waiting for me to open her bedroom door. Now, that I think more about it, even after I opened her door unannounced several times, she never locked her bedroom door and she never told my father that I saw her naked or in all manner of undress. Now that I think more about it, with my father sleeping, when not working, and drunk the rest of the time, I imagine my mother's sexual life was non-existent.

It would be sadly funny, if my mother had been just as horny as I was. Maybe my mother was thinking of me in the way that I thought about her. Maybe, had I stepped in her room and held her in my arms and kissed her, while touching her, feeling her, and groping her, she may have liked the sexual attention that only a son could pay his mother. Only, a line I never could cross, seeing and showing was one thing, but touching was a whole different matter.

Totally opposite of my mother. My sister was a whole different animal. Where my mother was revealing, albeit angry being seen naked, my sister was a psycho. I never knew which way the wind was blowing, whenever I saw something of her that I shouldn't see. Whereas, my mother would never mention that I caught her naked or in her underwear again, threatening to tell my friends, my sister would call me names and hold the fact that I was an incestuous pervert against me to get whatever from me that she wanted.

Something she never did before, always covered up in a bathrobe, after all those times my sister caught me masturbating, after all those times she saw my cock, she started walking around in just a towel for an extended period, after her bath. Now, I wonder if seeing my cock made her horny, not so much for me, her brother, but for a cock. Now, I wonder if she got off showing me bits and pieces of her naked body, as fodder for her masturbation, as well as my masturbation, too. Created from the same genes, maybe my sister was just as horny as I was.

Then, whether accidentally or on purpose, I really couldn't tell which, it was then that she started flashing me her pussy and her ass in up towel and up nightgown views and her tits in down towel and down nightgown views. On the pretense of painting her toes, always sitting across from me with her legs open enough to give me a good view or her panties or her naked pussy, she knew I was always looking. Only, every time I got a glimpse of her forbidden body parts, always with a yell followed by a barrage of name calling, she ended her naked flash with a slap, a pinch, a punch, and/or a kick. As obviously was my mother, with me being her punching bag, maybe my sister was angry at herself for being so incestuously attracted to me and for being so perversely perverted and horny that she'd flash me, her own brother, her ass, tits, and pussy. She was such a teasing bitch anyway, but it was worth whatever punishment she doled out to me for me to see some part of her naked body that I wasn't supposed to see.

Now, that I think of it, I wonder if my mother and sister were just as perverted as I was. Who knows? Why not? We all had the same genetic makeup. Once, after my sister slapped me, tired of her physically abusing me, I pulled the towel off of her and she chased me in my room naked. Wishing I was naked, too, we wrestled on my bed, while she beat the crap out of me, and even though she kneed me in the balls and slapped me across the face, it was worth the pain to get some cheap feels of my sister's naked ass and tits.

Only, fast forwarding to my sexual experiences with Kathleen, just like my mother and sister, was Kathleen really staring at my cock? I didn't know. I couldn't tell. It sure looked as if she was. Yet, did she really want me or was it all so innocent? Was it my twisted mind and dirty thoughts that created the hope in my horny imagination that revved me up on testosterone overdrive?

I was so young. I was so naïve. I was so horny. Between being young, naïve, and horny, I wasn't thinking straight. Not sexually experienced to know, there was just no way that I could tell if Kathleen was coming on to me or not, even after she stripped naked to use her bathroom without a door to pee.

All the while we painted her walls, with me on the ladder and her doing the trim on her knees, I stole perverted peeks down her overalls at her tits and panties. I did more peeking than I did painting and come to think of it, knowing I was looking, she never admonished me for peeking more than painting. Did she not know that I could see, as much as I saw. Did she know that I could see her tits down her top? Did she not know that I could see most of her panties down the sides of her open overalls?

On the pretense of painting, was her flashing me the reason why I was there? How could she not know all that she was showing and all that I was seeing? After undressing in front of me, knowing that I was peeking, maybe she didn't care what I saw of her tits and her panties. Was she flashing me on purpose? I didn't know. For sure, after we had sex, I knew she had been flashing me purposely. After we had sex, in the way that Mrs. Robinson seduced Benjamin in the movie, the Graduate, and in the way that Jennifer O'Neal, as Dorothy, seduced Hermie in the Summer of '42, I knew that Kathleen had seduced me.

It was as sexually arousing to play our mutual game of voyeurism and exhibitionism and touchy feely, as it was to finally strip off our clothes and have sex. Even more arousing than the actually sexual act, the teasing, the foreplay, and the seduction is what stayed with me all these years and is what I remember and masturbate to now, when I'm lonely and horny. The culmination of the sexual act, in the way of fireworks exploding in the finale and disappearing in a smoke filled sky, wasn't as everlasting as the excitement received from extended foreplay. The chase is always better than the capture. That first look, the first touch, and the first kiss, are things that I more remember than my first sexual encounter. It's always the buildup, before the storm, that's so exciting.

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