Cougar Italiano

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me.

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Finding a small gap at the bar, I squeezed my way in and ordered another beer. The fact that I didn't order a bottle of mass-produced domestic swill attracted the attention of the woman I had squeezed in next to and she asked me about the type of beer I had ordered. She was a very attractive older woman who, although she had aged quite well, must have been an absolute goddess in her younger days. She looked very Italian to me, with thick, dark hair and a slight olive tinge to her complexion. I managed to keep from tripping over my tongue as we started talking about good beer and, because she had a glass of red wine in front of her, good wine. I completely forgot about the friends I'd been hanging out with the longer I talked with this stunning older woman who must have been at least twice my age, though I was only in my early twenties at the time. I managed to teach her a little bit about good beer while she taught me a little bit about good wine, especially good Italian wine since both of her parents had been immigrants.

The conversation went so swimmingly that we eventually ended up leaving the bar together to go to her place for some of that good Italian wine. We caught a cab the short distance and, as she led me up the steps, I admired her ass wrapped in a short, tight skirt. The high heels didn't hurt the way her legs and ass looked either. I was glad she hadn't worn a low-cut top because I never would have been able to keep my eyes off her cleavage at the bar, though I did notice that her tits were quite substantial. Inside her apartment, she selected a bottle from the small wine rack on the top of her refrigerator while I continue to admire her ass. She had me open the bottle as she found a couple of wine glasses with broad bowls, pouring immediately as she explained that she didn't believe that letting the wine breathe would improve the flavor that much. Glasses in hand, she led me to her living room and we sat on the couch, chatting again as we sipped our wine, but eventually kissing and, after setting our glasses on the coffee table, making out.

My hand naturally ended up on her tits as I felt a lacy texture to her bra through her top as well as a couple of very stiff nipples. Her hand moved from my thigh up to massage the bulge in my pants until she finally said that she was going to suck my cock. I asked her if she would strip down to her lingerie first and blow me wearing only that. She was game and stood before me to strip down as I watched attentively. She peeled off her top to reveal her succulent breasts encased in an extremely sexy, lacy bra that revealed plenty of cleavage. While my eyes were glued to her tits, she reached back to unfasten and unzip her short skirt, then shimmied it over her hips, making her tits jiggle, and let it drop to her ankles. I was ready to blow a load in my pants as I admired a very fine, though by no means perfect, physique that would have made women half her age jealous. She graciously turned to show me that she was wearing thong panties, which looked outstanding on her ass.

Once she felt she'd modeled for long enough and that I was sufficiently impressed, she knelt between my legs and started to unfasten my belt. My attention was between her hands at work getting my pants opened up and her cleavage but hers was on the bulge in my briefs as she got my pants open. She ran her hand over it before grasping the waistband of my briefs as I raised my ass up off the couch. My pants and briefs were quickly at my ankles and my cock standing straight up as she worked my pants and briefs completely off. That done, she grasped my cock in one hand and ran her tongue up the shaft and around the head several times before wrapping her lips around it. I moaned as she slid her hot mouth down my tool, then back up again, pausing briefly before she started to suck my cock in earnest. I just watched, running my fingers lightly through her long hair, as my cock disappeared between her lips repeatedly.

She was pumping the base of my shaft as she was sucking and would pump the full shaft when she paused to lick my balls. I had been completely worked up before she'd even undressed, so I was feeling an intense orgasm beginning to build from the moment she first slipped my cock into her mouth. She was definitely talented, probably more so than anyone I'd ever experienced up to that point in my life, and was able to prolong my pleasure much longer than I ever would have thought possible given my state of arousal. She also appeared to be enjoying having my cock in her mouth as much as I enjoyed having her mouth on my cock. When my cock wasn't in her mouth, she was breathing as hard as I was, as if she was building toward her own climax.

She seemed to know when I was at the point where I desperately needed to blow my load and that she should stop trying to draw out my climax. She changed her technique enough to allow my orgasm to build up, my cock swelling even more, until I exploded with a moan of pleasure into her hot mouth. She continued sucking, swallowing every drop of my cum, until I was completely spent, then continued to gently nurse my tool until it started to soften. She let it fall from her mouth and looked up at me, smiling, and actually thanked me. I told her that she was the one who had earned the thanks and that I wanted to show my appreciation by returning the favor. She didn't argue and downed the rest of her wine as we swapped places.

As I knelt before her, we made out again as I fondled her tits before reaching behind her to unfasten her bra. I had to back up slightly as I started to slide her bra off so that I could get a good look at her succulent tits. They were absolutely luscious, with large, dark pink areolas and hard, thick nipples, so I immediately lowered my head and started to lick and suck her nipples. She ran her fingers through my hair and moaned as I lavished attention on both of them. I could have spent hours enjoying them but I knew that her pussy must be dripping by this point, so I start kissing my way southward over her stomach to the elastic of her thong panties. Her legs were spread wide, so I kissed her inner thighs before pulling her panties aside to expose a shaved pussy topped with a narrowly groomed dark brown bush. I started lapping up her juices, running my tongue up her slit, then licked and sucked her clit at I slipped first one, then a second finger into her hot, slippery pussy.

She was moaning and writhing as I devoured her pussy, my fingers sloshing in her dripping depths. As I gazed up past her looming breasts to the look of raw passion on her lovely face, I could feel the blood already trying to return to my spent cock. I resolved to give her an incredible orgasm and be ready to fuck her by the time she'd recovered. Her reaction gave me confidence that I was doing a good job, which I only would have questioned because I expected that she was much more experienced than I was. Since she was clearly well on her way, I continued what I was doing with even more enthusiasm, which resulted in an even more enthusiastic response from her. I didn't have any tricks up my sleeve to draw out the pleasure she was experiencing as she had for me, but I got the sense that she wouldn't have any complaints about that.

She started getting louder while writhing faster as I felt her pussy getting even juicier. I was really enjoying going down on her because she wasn't afraid to be very responsive to what she was feeling. I felt her starting to tense up as she held my head in place and knew that she was just about there. While I wasn't disappointed that I had managed to provide her with so much pleasure, I felt as though I could have camped out between her spread thighs for a lot longer. Her low moans had gotten higher in pitch the more she tensed up but when she suddenly went limp and her body shuddered, the moans were much lower again. I continued to lick and finger her as her body shook and only raised my head when she relaxed her grip enough to allow me to do so. I slipped my fingers from her pussy directly into my mouth to suck off her pungent nectar as I watched her chest heaving while she caught her breath.

I reached over for my wineglass and downed the rest of my red while my eyes traveled over her nearly naked figure and my cock continued to grow stiffer. Her legs were still spread and her panties askew so I was admiring her trim little bush and her smooth pussy lips. My gaze traveled up over her stomach to her heaving breasts and the hard nipples topping them. By the time my eyes rested on her face, my cock was nearly rigid again and her eyes were beginning to open. She beckoned me closer so I set my wineglass down and leaned in so that we could make out again as I guided my stiff cock to her pussy. Placing the head between her slippery lips, I eased it in, feeling the warmth and slickness along the entire length of my shaft. She moaned into my mouth as I fully embedded myself and slowly started to fuck her.

While her pussy wasn't the tightest one I had ever fucked, it was so hot and so wet that it really didn't occur to me as I was sliding my cock in and out of her. We continued making out and she reached around to grip my ass while I brought a hand up to fondle her luscious tits. I kept up with the leisurely pace, relishing the feel of her pussy on my cock, her tongue in my mouth and her nipples against my palm. Eventually, when a change of position seemed warranted, I moved back and slipped out of her while suggesting that she turn around and kneel in front of me. She joined me on the floor and leaned on the seat of the couch while I admired her ass and ran my hands over it before sliding her panties off and guiding my cock back into her. In this position, I started out holding her by the hips as I was bouncing my own hips against her ass, but soon moved my hands up to cup her breasts, hefting their weight as her hard nipples brushed against my palms.

As I was enjoying her breasts while giving her a good fucking, she reached a hand down and started to stimulate her clit. It didn't take long before her heavy breathing turned into soft moaning as she started pushing back against my incoming thrusts. Incredibly, her pussy was feeling even hotter and more slippery the longer I fucked her and I could feel my second orgasm beginning to slowly build. I tried to maintain the slow and steady pace, but as she was pushing back against me and her pussy was feeling so good, I couldn't help but gradually fuck her harder and faster. Her soft moaning had become louder and longer as she pushed back harder and her pussy continued to become more engorged. My orgasm was building faster but still not fast enough to beat her to the punch. She finally pushed back against me and let out a cry of pleasure while I felt her trembling as she came again.

When she finished cumming, she pulled away and straightened up, then moved away from the couch and lay on her back on the floor with her legs splayed wide. Still on my knees, I moved over to her with my cock, shiny with her juices, bobbing in front of me. I had to admire her physique again and remind myself that this was the body of somebody likely in her fifties. I couldn't believe how lucky I was to be there with her and decided not to waste any more time that I could be spending deep inside her hot pussy. I did tell her, though, as I guided my cock back into her how incredibly hot she was. She thanked me for saying so before she stuck her tongue back in my mouth. I supported myself over her, feeling her breasts against my chest, as I was thrusting in and out of her, now in pursuit of my own orgasm. She brought her feet up off the floor and rested her heels on the small of my back as I pushed into her as deeply as I could.

My orgasm was slightly delayed by our change of position, but it didn't take much time of fucking her hard on her living room floor before it was building quickly again. I savored the pleasure I was feeling as well as the somewhat unique situation of fucking a fifty-something hottie on her floor, not knowing at that point whether this would be a one time occurrence. My cock began to swell even more as I got closer to cumming and I just kept fucking her harder and faster until I finally exploded with a grunt, spewing deep into her hot pussy. I continued thrusting with each spurt until I was spent then pulled out and collapsed next to her. We both lay there catching our breath for a few minutes, then smiled at each other and kissed tenderly, agreeing that it had been friggin' hot.

Once we recovered, she invited me to join her in bed and spend the night. We left our clothes and wineglasses behind and, with very little in the way of ablutions or other preparations, fell into her comfy bed and slept naked in each other's arms. I don't know what woke me first the next morning, the sound of the front door closing, the loud voice yelling "Ma?" or Gina jumping out of bed. She was grabbing her robe off the back of the door while gesturing for me to remain quiet then left the bedroom, closing the door behind her. This being a typical New York apartment, I could hear everything that went on outside of the bedroom about as clearly as if I was standing right there. Apparently her daughter had showed up unannounced along with her own two daughters who both wanted to know why there were clothes all over Grandma's living room. I guess her daughter noticed that some of the clothes were men's and that there were two wineglasses and put two and two together. Sounding a bit put off, she gathered up her little ones and explained that Grandma wasn't quite out of bed yet, so they'd have to come back later.

It was a couple of minutes after I heard the door chain, which we'd apparently missed the previous night, before Gina came back into the bedroom. She looked a little sheepish, but I was glad that she wasn't suddenly ready for me to get the hell out of there. She apologized and I told her not to worry about it and that they could have arrived at a much worse time. She went wide-eyed as she agreed with me then asked if I was weirded out to know that she had grandchildren. I told her that I had never knowingly fucked a grandmother before and found the idea strangely arousing, then flipped back the covers to show her that I was completely rigid. She looked pleasantly surprised, then quickly shed her robe and straddled me, guiding my tool between her lips and lowering herself onto it.

She moaned and a shiver passed through her as she sat there for a moment just feeling my girth inside her. Slowly, she started to ride me, her pussy again feeling totally hot and slippery, though my focus was on her tits bouncing in front of me. I reached up to fondle them as she rode me, running my hands over the smooth skin and lightly caressing her hard nipples. She dropped a hand down to caress her clit as she rode me, her pace gradually increasing as I continued to fondle her bouncing tits. The bed was squeaking and I was glad once again that we hadn't been doing this when her daughter had showed up. She kept getting louder and riding me harder and eventually leaned forward, propping herself up on her arms which were planted on either side of my head. I let go of her tits, feeling them brush against my chest as they swayed back and forth, and ran my hands around to grip her ass.

I wasn't surprised that she was getting close to cumming already because she clearly knew her body very well and knew how to get the maximum pleasure while riding me. I could feel the beginning of my own orgasm but felt confident that she'd be cumming before I did. I pushed up into her each time she came down on me, hoping to give her even just a bit more pleasure as her orgasm got closer. Her tits were really swinging, the harder and faster she rode me, while her moaning got louder until she slammed herself down and shuddered as she came again. I lay there watching and feeling the muscles inside her pussy working until she opened her eyes and looked down at me, breathing hard. I suggested that she roll over onto her back.

She climbed off my cock and was lying on her back as I was getting up off of mine. She spread her legs, but that wasn't my destination; I straddled her and lay my cock between her luscious tits. She squeezed them together for me and I started to fuck them. I was holding onto her headboard as I slid my throbbing cock between her soft, smooth tits and felt the orgasm that was beginning to build continue to do so. Gina watched the head of my cock as it popped out of her cleavage, holding her tits together to provide the pleasurable friction. Seeing her pretty face staring intently at my cock and her tits squeezed together around it aroused me to incredible levels on top of the feel of actually sliding my cock between her tits. I was fucking them slowly, enjoying the pleasure of the gradual build, but as it got closer, I was fucking a bit faster.

My breathing was a bit harder as my cock started to swell with my impending orgasm and, when I finally started shooting my load onto her chest, I let out a moan of relief. Gina's eyes were wide and she jutted out her tongue but wasn't able to catch my weak load. Once I was spent and had started to move off of her, she cleaned up my cum with her finger and licked it off while I watched. We were just lying there when her phone rang and, after looking over at the caller ID, she decided she'd better take it because it was her daughter. I lay there for a few minutes listening to one side of the conversation, the gist of which was that Angela was aghast that her mom had a man in her bedroom and that Gina had no intention of moping around for the rest of her life just because her husband had died. I got up and went to use the bathroom while the conversation continued, then headed to the living room for my clothes.

I was just starting to get dressed when Gina came out wearing her robe again. She asked if I was running off and I just said that I thought I shouldn't be there when Angela came back. Gina assured me that Angela wouldn't be coming by without calling for a while and said that she wasn't letting me leave without breakfast; I'm sure she didn't mean that to sound as maternal as it did. I agreed to stay but continued to get dressed then did what I could to help her. The apartment smelled great with the combination of the cooking food and the brewing coffee and I couldn't resist wrapping my arms around Gina from behind as she cooked. I thanked her for having me over as I squeezed her and she turned to kiss me before telling me that it was her pleasure and that she hoped it wouldn't be the last time. I got a sense that this was almost an inquiry so I slipped my hands into her robe to cup her breasts as I told her that even Angela wouldn't be able to keep me from coming back.

As we ate, she assured me that Angela would never feel good about her being with somebody other than Angela's late father, so we would be better off being as discreet and careful as possible. I told her that we might be safer if she just came to my apartment and asked if she wanted to come over and watch the Giants on Sunday Night Football that night. Her response left no question about how she felt: "You're a Giants fan? As if there wasn't already enough about you to like."