Cougar and her Five Virginal Cubs Ch. 05
Tem 29, 2022 // By:analsex // No Comment
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Chapter Five – The Seduction
Cougar strips naked in front of her cub.
I followed Kathleen to her apartment. Her place was nice but in disarray because of her painting project. Just a one bedroom flat with an eat-in kitchen, a living room, and a bathroom, her apartment was small but plenty big enough for just her and her little dog. Looking out her windows was a whole another perspective from my house. A layout so different than my parents apartment, it was weird seeing the cemetery from her bedroom windows, the park from her living room windows, and the Boston Harbor from her kitchen windows.
Moreover, a dog that barks at everything and everyone, it was weird that Barky didn’t bark at me, even when I first walked in her place. I figured he would, as soon as I opened her downstairs front door. He always barked. Ignoring him to stare at Kathleen, while waiting for him to come to me, instead of me going to him, maybe because he sensed that I liked dogs and wasn’t a threat to him was the reason why he didn’t bark. Maybe because he already had my scent in his nose from me hiding behind the wall with the rest of my friends, while watching her climb the cemetery fence and watching her flash us her panties. Anyway, we got along fine and without incident.
“Here,” she said, as soon as she entered the apartment and closed the front door behind me. She handed me this folded, white piece of material that I figured was a drop cloth, until I unfolded it.
“Painter’s overalls,” she said. “Put them on so you don’t get paint on your clothes.”
I wiggled my foot in but my shoe got stuck in the pant leg.
“Take off your shoes,” she said laughing. She had a nice laugh and a pretty smile. She looked even prettier, when she smiled and younger, too. Actually, before I knew her age, if I had to guess her age, I would have guessed that she was in her mid-twenties. I was floored, when she told me she was 32-years-old. “You never wore overalls before?”
“No,” I said prying my foot out with great difficulty and removing my shoe this time, before sticking my big foot back in the pant leg. I’m a big guy and these overalls were just too small. There was no way that I could squeeze them over my bulky clothes. “These overalls are way too small,” I said ready to give up, forget about earning twenty dollars, and go home.
“They won’t fit over your clothes, silly,” she said laughing. “You have to remove your clothes and put them on over your underwear.” She looked down at the bulge my cock made in my Wranglers. “You are wearing underwear, aren’t you?”
In the way she looked at me with a look of lusty hunger, when she asked me if I was wearing underwear, she suddenly made me feel a little uncomfortable, sort of like that time, when Father O’Malley touched me in my private place.
“Yeah, I’m wearing underwear,” I said insulted that she suggested that I was a pervert, which I was. “Who the Hell walks around not wearing any underwear under their clothes?”
“Those flashers who just wear a raincoat and who are naked underneath,” she said laughing.
“Well, I’m no flasher and I’m not wearing a raincoat,” I said returning her laugh without totally understanding her joke.
Whether I understood her more mature humor or not, with the both of us sharing a laugh, immediately, I got over the awkwardness and felt at ease in being alone with her. She was a good looking woman and unlike the uptight older woman in the neighborhood, she was no Nun. She was fun. She was funny. I liked her and I had an erection just thinking about being in her apartment in my underwear, while thinking of her flashing me her panties, every time she climbed over the cemetery fence.
Except for the front door, the weird thing was that she had no doors in her place. There was no bedroom, closet or bathroom doors. I stood in her kitchen looking around for a place to change out of my clothes and into these overalls, a uniform that looked so much like the white suit that the ice cream man wore in his ice cream truck.
“Well,” she said looking at me, while raising her eyebrows with her shoulders and hands, “what are you waiting for an invitation?”
“Where can I change? You have no doors.”
“Oh, sorry, I removed the doors to strip off the paint,” she said pointing to the doors leaning against the far wall. “There were layers of paint on the doors and the wood veneers underneath are beautiful. I’m going to restore them,” she said with a smile. “You can change right here in the living room. I’ll turn my back to give you privacy. I won’t look. I promise,” she said with a sexy smile that made me think that she’d look.
Then, when she turned her back to me to undress to change in her overalls, I was stunned. I was shocked. I was surprised. Without the privacy of a curtain or a door, suffice to say my stunned, shocked surprise was an understatement to the sudden sexual excitement that I felt, when she was undressing just behind casino siteleri my back. Even though she said that she wouldn’t look, I made no such promise. I didn’t say any such thing about me not watching her undress.
I turned my head and watched her, as she slowly unbuttoned her blouse. It was then, when she turned suddenly and revealed her side profile to me that she jogged my memory of who it was she looked like. As if I was watching a scene in a movie that I had seen a dozen times before, I recognized her. That’s who she looks like and that’s who she reminds me of, Maureen fucking O’Hara. Oh, my God. I’m watching Maureen O’Hara unbutton her blouse. I couldn’t believe I was watching a younger and prettier look-a-like version of Maureen O’Hara undressing.
I couldn’t believe it. I just couldn’t believe it. Consumed by sexual excitement, I froze. Here’s a woman, an older woman, an attractive woman that I’ve seen around the neighborhood, but have never seen up close, haven’t formally met, and/or spoken with, that is, until today, and she’s undressing in front of me, actually behind me. With my head cocked to one side and my eyes bulging out of my head, I couldn’t believe my eyes, when she removed her blouse and stood there with her back to me. I couldn’t help myself from staring at the back of her bra. Other than on my mother and sister, I had never seen a bra that was on a woman before.
I stared at her curly auburn hair flowing over her shoulders and at her shapely and defined muscled back. Guzzling and memorizing the image of her to save for my masturbation session later, I took her bra straps and the back of her bra all in, as if she was a cold beer on a hot day. I couldn’t wait to tell my friends that she removed her blouse in front of me, albeit with her back turned to me. Hers was the first bra that I had seen that wasn’t in a dirty magazine, on a display mannequin in a department store, on a counter in a lingerie department, or that belonged to my mother and sister in the dirty laundry basket. Then, when she turned slightly to the side to hang her blouse over the kitchen chair, I saw the side of her bra cup.
Oh, my God, she has big tits, bigger tits than my mother’s and sister’s tits. When her blouse slid from the chair and onto the floor, she gave me a good look of most of her bra when she leaned down to retrieve her blouse and to hang back on the chair. My heart was pounding, my pulse was racing, and my blood was pumping everywhere, especially below my belt.
Frozen in place holding the overalls she gave me in my horny hands, I watched her, as she unzipped her short skirt and allowed it to slowly fall to the floor and collect around her ankles. As if imagining this, unbelievably, it was as if I was having a sexual fantasy, while jerking off about her. I couldn’t have picked a better sexual fantasy to have, only this was no fantasy. This was real. This was really happening now. She was stripping off her clothes right there in front of me, actually, right behind me. Having never seen a woman undress before, it took all the self-control that I possessed not to turn around and stare, while watching her undress.
There she was in her white bra and white panties, the same white panties that all of us had snuck a peek at so many times before, whenever she climbed over the fence with her little dog tucked under her arm. I remember thinking that she had a nice round ass. I remember wanting to reach out my hand and feel her ass through her panty, but I didn’t dare touch her or even have her catch me looking. Filled with guilt that she’d catch me looking, filled with sexual excitement of all that I wanted to see, I didn’t know what to do.
Except for a few flashing incident with my mother and my sister, never have I seen a woman in her panties before. I looked down at her legs and they were shapely, too. She didn’t have any of that cottage cheese stuff on the back of her thighs nor did she have those saddlebags that so many women have on the sides of their thighs. The sight of her legs made me wish that I could run my hands along the length of them, while pausing to pay homage to what was between them.
Eager to tell my horny friends every raunchy detail of all what happened. I couldn’t wait to tell my friends all that I saw. They’d never believe me that she removed her blouse and her short skirt, while she stood behind me. The guys will never believe me, I thought. I could just hear Stephen’s voice.
“Fuck you! No way! She changed out of her clothes in front of you? Get outta here. You’re lying. She wouldn’t do that. She looks like a nice woman and not a whore. Only a whore would change out of her clothes in front of you, a horny teenager.”
I heard of older women picking up younger guys and doing them, if that was what she was doing and was about to happen, or were we just getting ready to paint? Then, I remembered that rumor about her being kicked out of Charlestown because she was caught having güvenilir casino sex with a bunch of younger men. Yet, after meeting her and seeing how nice she was, I’d never believe she was that type of woman. For sure, she was no whore.
I was so naïve and a woman would have to hit me over the head with a baseball bat to get my attention. Yet, her baseball bat was her sexy body and her grand slam homerun was when she started to remove her clothes. If only I knew then, that I was about to round all the bases and score, I would have been more prepared for what was to happen. Knowing what I know now, albeit glad to play the game, I was just a spectator in her little ballgame.
“Batter up! Play ball!”
Every day, my horny friends and I lined up behind the wall to watch her scale the fence in hopes of seeing a bit of her panty and, now, here she is standing behind me so exposed in her bra and panty. When she climbed over the fence was one thing, lifting her leg and raising her skirt high enough to clear the rod iron fence in her miniskirt, but now here she is showing me the entire back side of her panty clad, round ass and her bra adorned back. Stunned into inaction, I couldn’t believe my eyes. Too sexually inexperienced to wrap my arm around her and kiss her, while touching her, all I could do was stare.
Bending at the waist and staying in that position longer than necessary, she picked up her skirt, folded it, and placed it on the kitchen chair. With her standing there in her sexy lingerie, I couldn’t believe that I was witness to a striptease show and that I was seeing Kathleen in her panties and bra. Shapely in the way of Ann Margret, she had a nice body, an understatement. I so wanted to wrap my arms around her waist, pull her closer, and hump her from behind, as my hand reached up and felt her tits through her bra. Only, it was one thing to think that and another thing to do that. Being more of a gentleman than that, I’d never do that.
When she turned to place her skirt on the chair, my eyes were transfixed on her crotch and I could see her dark patch of reddish brown pubic hair with some red pussy hairs sticking out the sides of her panties. Women back then didn’t shave or trim their pussies in the way they do today. Then, when she reached around herself and unhooked her bra, slowly removed the straps from her shoulders, and tossed her bra on the kitchen chair, holding my breath, while watching her remove her bra out of the corner of my eye, I thought I was going to have a heart attack. Afraid to turn to look but needing to take a peek, so that I didn’t regret for the rest of my life not looking, she was topless. Knowing all I had to do was to turn my head to see, her tits were on display for my horny eyes to see.
My mouth fell open, when she removed her bra. I couldn’t believe she removed her bra. She was topless, but with her back turned to me. I thought I was going to faint, if I saw any part of her naked breast. Then, with her back turned away from me but now turning slightly my way to dress, I turned my head slightly to watch her, as she bent forward and stepped in her overalls. Now, I could clearly see her ass crack through her sheer panty and the entire side of her left breast, when her breast fell forward, as she bent forward to pull the overalls up past her knees. Oh, my God. Oh, my God. Oh, my God. I was so sexually excited.
I would’ve given my right nut to see her nipples. From what I saw of the side of her tit, as big breasted as Anna from the neighborhood, she was definitely a full C cup, maybe even a small D cup. She had a nice, full set of round, shapely tits, not that I was a breast expert, but I’ve seen enough Playboy pictorials to know what a tit should look like and, from what I briefly saw of her naked breast, her tit looked just like the picture in the centerfold.
Actually, her tit was the first naked tit that I had ever seen, albeit only one side of one breast, it took all the control that I had not to step around her and take a good look of her tits. I wanted to twirl her around, take her in my big arms, and kiss her, while feeling her big, Maureen O’Hara like tits. I so wanted to see her areolas and her nipples. Except for all those women in Playboy, I had never seen a woman’s nipples in person.
With my head slightly turned her way, while watching her out of the corner of my eye, I’d be so embarrassed if she caught me peeping. Little did I know, back then, that she was hoping I’d look. Little did I know, back then, that she was teasing me and seducing me. She turned to face me as she slipped the overall straps over her shoulders giving me a nice shot of her abundant cleavage and the side of her right breast.
“Well,” she said.
“Oh, sorry,” I said turning my back to her, kicking off my other shoe, unzipping, pulling down, and stepping out of my jeans, and unbuttoning my shirt.
There I was standing in my briefs and t-shirt with my back to her, while fumbling with canlı casino the overalls, when, suddenly, she walked around me to grab some empty coffee cans from under the kitchen sink. After she walked around me like that, I wished I had done the same to her and walked around her, when she was standing their topless with her back to me.
Embarrassed by my erection, quickly covering it with my hand, and excited at the same time by all that I saw of her and, now, all that she was seeing of me, I couldn’t stop staring at her. When she squatted down her overall top fell forward and I could clearly see most of her tits down her overall top. Oh, my God. I could have sworn I saw part of her nipples. Definitely, I saw part of her areola, I think or did I imagine that I saw? No matter, she was showing me more of her tits than I’ve ever seen on a woman not in a magazine.
Then, when she turned and caught me staring. I was mortified. I was humiliated. I was so embarrassed. I could feel myself turning a bright red. I didn’t know what to say.
“You’re going to have to do something about that?”
“What?” I was so embarrassed that she caught me staring down her overall top at her tits. I was so embarrassed that she was admonishing me for looking and for the pervert that I am. I wanted to flee from there and run home to masturbate over all that I saw of her. “I’m so sorry,” I said with a stutter. “I didn’t mean to stare.”
I figured she was scolding me for looking down her overall top and staring at her tits. What the Hell did she expect? I’m human. I’m a horny teenager and she was standing there topless albeit with her back to me and now she was squatting down in front of me braless and with her top falling forward and opened enough for me to see most of her breasts. Being able to look down her overall top in this way was better than what Joey imagined he saw at the supermarket, when he imagined seeing a braless woman with an unbuttoned blouse reaching for the cheese in the dairy case. Definitely, I was seeing the real thing, instead of what Anthony imagined he saw, when he sat on the ledge and he assured us that she was parading in front of her window naked.
She looked down and straight ahead and I looked down to see what she was staring at. When I moved my hand away, my cock was at a 45 degree angle and pitching a huge tent in my cotton briefs. My cock was so erect that the section where I reach in my briefs to pull out my cock to pee was pulled forward and the entire side of my cock was exposed to her. Moreover, my entire underwear was pulled forward due to my massive erection exposing part of my balls and pubic hair to her.
“That won’t fit in your overalls like that. Seriously,” she said again, while still staring at my erection, “you’re going to have to do something about that.”
“Sorry,” I said turning the other way and quickly wiggling in the overalls. Still, even to this day, having heard her say it twice, while staring straight at my erect cock, I wondered what she meant by saying that, ‘you’re going to have to do something about that’. What did she expect me to do? Did she want me or expect me to pull out my cock and jerk off in front of her? Now wondering if I should have, I always regretted that I hadn’t.
“Stupid ass, you should have pulled your cock out and masturbated in front of her,” I imagined hearing Stephen’s voice in my head berating me for not giving her a masturbation show. “She practically invited you to do just that, you stupid ass. You’re such a stupid ass, you stupid ass,” I imagined him continuing to berate me.
I did have the urge to reach inside, pull out my cock, and jerk off in front of her, but I wasn’t that perverted. I wasn’t that depraved. I was so young and she was such a nice, pretty lady. Things, especially regarding sex, were different back then, not to mention that I was an innocent, virginal eighteen-year-old in the apartment of a woman old enough to be my aunt.
I wonder what she would have done had I pulled out my cock in front of her and started stroking myself. Would she have screamed? Would she have called my parents? Would she have reported me to the police? Or would she have watched me masturbate and cum for her? I read about women in Playboy who got off watching a man jerk off. Only, I couldn’t do it. With no one knowing I masturbated, that is, except for my mother and sister, not even my friends, I always denied masturbating, even though we all masturbated. Nonetheless, I didn’t want to be deemed a pervert, especially if that’s not what she meant by me doing something about my erection and masturbating in front of her.
Even for me to see the back of her panty and bra, along with the side of her breast, enough for her to see my bulge tenting my underwear, I was so horny that I thought I would cum right there. Back then, I jerked off a lot, always twice a day, once in the morning and once at night. On those days that I was really horny, such as that day, I’d masturbate three and sometimes four times a day. For some reason, I hadn’t jerked off yet that day, which made me even hornier. I so wanted to jerk off now, especially after all that I saw of her bra, her panties, and a good portion of her tits and all that she saw of me.
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