Cougar Diaries: In the Game

Maria and Her Boys. Jilted wife relives her youth.

In 2 parts, by mjar65 . Listen to the Podcast at Steamy Stories.

This story is about an older woman, a woman in her middle forties, who has sex with different men. Mostly she has sex with men who are younger than her – much younger.

This story is about me – Maria. I am happy and fulfilled and satisfied. I am loving life more than I have done for years. And I am making sure it stays that way.

Although I have sex with different men, you might want to know that most men I choose for my bed are in their early twenties. They are “barely men”, in their youth and ripe for the picking.

You might wonder why I do this. The simple truth is that for an “older woman” there is nothing to match the feeling and the sight of a young man between her legs. Having a much younger man makes me feel youthful as well. These are the type of boys who first introduced me to sex, who took my virginity and taught me the pleasures of the flesh. I have never forgotten those years and those wonderful experiences as I first explored the world of sex. For so long I dreamt of those times and those experiences and wished I could revisit my youth. Now I get that chance on a regular basis and it is simply wonderful.

Guys that age, the age I like to choose them, are always so eager to please, to do a good job for me. Their bodies are always hard and taut and I can feel their desire for me through their skin. They are so sweet the way they get nervous the first time they touch me and kiss me and fuck me. Sometimes its like I cannot get enough of them.

A young man’s penis is guaranteed to bring me pleasure. Older guys might be more experienced but they do not throb and explode like my younger ones. Boys at that age are so virile. Their cocks are things of wonder, the way they swell and pulsate. In my hand and in my mouth and especially in my vagina. Their cocks feel as if they are alive all on their own. When I have a young guy, a boy old enough to be my son, on top of me or entering me from behind, his cock always feels harder and closer to bursting than any man my own age ever could.

I get fascinated with their balls. I crave to fondle those hard, little eggs, to cup them in my hand and stroke them with my fingers. I delight in their big loads of semen. I like to imagine how virile are my young lovers, their balls holding so much powerful “baby making stuff”. Younger guys produce impressive amounts of semen, even when cumming the second or third time. There is no better feeling for a woman “my age” than to make it shoot from a young cock. The way it gushes, into my mouth or my vagina, and fills me up always gives me a powerful feeling of validation.

No so long ago, I had a “normal” life – married and happy. I had only slept with three boyfriends before I met my husband. I would say I was inexperienced sexually and somewhat lacking in confidence. We got married and had a beautiful daughter. He forged a successful career and I started my own business. It made sense to describe myself as happy.

Somehow, I knew the sex was not all it could be. Yes, I was inexperienced but I always felt that our sex life could be more exciting – more satisfying. But my husband never seemed to mind. Even when, a few years ago, I tried to spice things up with lingerie and mention of different positions, nothing changed.

I tried not to think about it too much because I felt in love and loved in return. As a result, I never really worried he would chase his pleasure elsewhere. So it was a shock a couple of years ago to realise he had his eye on a younger woman.

At first, I was crushed. Then I took action. I changed my eating habits to lose some weight. I started going to the gym and did thousands of squats to improve my butt. Then I even went overseas to have my breasts “fixed”. Mostly I wanted to correct the effects of gravity but I went a little bigger as well – between a ‘B’ and a 'C’-cup.

Our sex life stayed the same and then my husband left me for his younger model. After everything I had done. I was crushed all over again. Until two girlfriends took me to lunch and told me the “cure”.

“Just go out and have lots of sex,” they told me, looking half serious. That was their solution - have lots of sex with as many guys as I could! Right then, I scoffed at the idea. But they were adamant.

“What you need is to find a man, or a few of them, and then fuck the shit out of them.”

I managed to have a laugh with them. Part of me wanted it to be true. I was a “free” woman now, I could do whatever I wanted with whoever I wanted.

I just didn’t know how to go about getting all that. At my age, with a marriage behind me, I was not feeling very brave.

To help pass the time and overcome my sexual frustration, I bought myself two vibrators on the internet – my first time ever. One of them was especially effective and on the first weekend I took to bed and gave myself more than a dozen orgasms before I finally decided I should stop! I figured that was my future sex life but that was OK – I had our house to myself since our daughter spent most of her spare time with her father. He always had time for her whereas I was still trying to run my business.

I was not thinking about young men right then. But I resolved to keep myself at my best so I was still going to the gym regularly, still doing those squats.

One night I was doing some regular training with weights and I noticed a group of boys. They were around twenty years of age and talking and laughing a lot. Several of them seemed to glance over at me and I was convinced they were having a laugh at my expense. I was furious but I tried to ignore them and finish my workout. On the way out, I was still upset when I saw one of the group loitering near the entrance.

Well, my temper got the better of when he stepped towards me, obviously wanting to talk to me. I assumed it was another joke at my expense. “Hello. You had a good workout,” he managed to say.

“I did. With no help from you lot making fun of me.” He looked surprised to hear that.

“No, we weren’t looking at you. Well,” he stumbled, “I was looking but the other guys weren’t.”

Now I was a little confused. I could see this young man was keen on talking to me and I’d not had that experience for almost twenty years. And he was tall, over six foot beside my five feet five inches. I was trying to stay angry and to give him my best “death stare” but it wasn’t working. He looked so taut and trim. I couldn’t stop thinking about how much he reminded me of the boys I had desired before I got married.

He was trying to talk to me but I wasn’t really listening. I was thinking about my boring sex life with my husband. I was daydreaming about those boys from my youth and wondering whether they’d have been better lovers.

Then I heard a voice say, “If you want to talk, why don’t you invite me for a drink?”

Yes, that was my voice. I was shocked at myself. He managed to mumble a reply and suddenly I felt something happening to me. I felt in control – I felt in charge. This nervous young man wanted to please me and I had the upper hand. I had never in my whole life felt like that in front of a man.

He just wanted to talk, to get the attention of a nice woman. But something clicked in my head. It was like there was some connection between my vagina and my brain. My anger had turned into action, my humiliation into desire. I had sorely missed younger males with their lean bodies and their enormous libido. Yes, I wanted to have sex with a man and here was one standing right in front of me. He was about the same age as my daughter but that hardly registered with me. I could feel the power I had over this guy. I wasn’t concerned about the age difference. I just wanted to take advantage.

“You can come to my place if you want,” I told him in an even voice. “But that’s the only offer I’m making.” He just stared at me for a few seconds. I guessed his mind was reeling almost as much as mine.

“What’s your name?” I demanded to know.

“Ryan,” he managed to mumble.

I told him the name of my street. “Follow the black Beamer,” I told him and walked off.

Inside my car, I could suddenly breath again. But driving was a problem. What was I doing? This young stranger was obviously keen on me and I’d just invited him to drive to my house at night. I felt something like revenge – against my husband or against this silly young guy who had let his friends laugh at me? I didn’t want to think about it because not far from there was the thought of “revenge sex”. Was I really that desperate for a fuck? That was preposterous. But where had this craziness come from? How could I even contemplate what I was about to do?

I remember thinking again of how his body reminded me of the guys I had dated, or wanted to date, in my younger years. I still found that very sexy. I could have that now, couldn’t I? He’d meekly followed my instructions. I had power and I could use it any way I wished. I’d missed out for all those years and now I had the chance to do something about that.

At my house, I waited for him to cross the street, still in his gym gear. My heart was thumping in my chest. I had wanted to feel brave. Was this brave? I was banking on this young man’s libido to make him do anything I wished.

“How old are you?” I demanded to know. With a pause, he said he was twenty-four but I was sure that was a lie. Ryan looked no more than twenty-one. That was OK by me because later he asked my age and I lowered it by ten years – he’d never know the difference. Part of me knew it was wrong. But what I really cared about was that I didn’t have to be frustrated or denied any more. I’d been angry but now I could take charge and make sure I got what I wanted. I could have what I’d missed out on for so many years.

I let this young man inside my house, staring at him, thinking that he should be dating teenagers and that, instead, he was going to climb into my bed. He made a clumsy grab for me, trying to put his arm around me or touch my breasts. I don’t know which.

He was even less experienced than I was. It was not too late to change my mind. I could have sent him away. But I’d given about as many signals as a woman can. There was no doubting his enthusiasm but, after all, he was a younger man. He was turned on and totally focused on having sex – with me!

And I was feeling incredibly horny myself. Masturbation was not enough. And besides, if my husband could choose a younger model then I knew I could do the same. It had been years since I’d had a man so young and I was not going to stop now.

“Shower first,” I warned him, pushing him away. I showed him to the downstairs bathroom. “Just put a towel on when you’re finished and come upstairs.”

I almost ran to my bedroom and jumped into the shower. I had to be ready before he was. I needed to be in control. This was all so totally insane. I was fully intending to have sex with a new man for the first time in twenty-something years and this particular man was not even born when I met my husband. I tied my long brown hair out of the way and took a quick look in the mirror. “Not bad,” I thought to myself and decided not to wonder whether Ryan would like it as well. This was my last chance to call the whole thing off. I paused for a second and walked into the bedroom.

I was wearing a silk robe when he came in. I hadn’t bothered to tie it and my new breasts were holding it open nicely so he could see all my “treasures”. My confidence was not that great and I dared not let Ryan get cold feet.

This time I allowed him to slip his hands up my body to my boobs. They are high and firm again, the nipples pointed slightly upwards. These were the boobs I’d bought for my husband but instead it was a horny, young guy groping them, fumbling in his excitement. Just the touch of his soft hands on my flesh almost made my heart jump out of my chest. I was no longer thinking about anything apart from my own lusty needs.

Maybe I should mention right here that his touch felt electric. Standing there, practically naked and being felt up, I was losing control of my body, if not my mind. It wasn’t him so much – it was the whole experience of being wanted by a man, being touched with real passion and lust. My girlfriends were totally right - the “cure” was lots of sex.

Ryan had the towel wrapped around his body, making him look even more beautiful. I saw his cock making a healthy bulge in the front. I couldn’t take my eyes off it. That was all the courage I needed. This young guy really wanted me, my body, and I was saying “yes”.

As he really started to grope my breasts, I dragged the towel away so that he was totally naked. Ryan looked just like the young guys I remembered from university. It was a heady experience. I had almost forgotten the virility of the younger male – his cock was a very admirable size and I saw how it was standing almost vertical. When he bent forward and started sucking on my tits his cock just grew bigger and harder. I wanted to be fucked so badly.

“You have great breasts,” he said and I smiled with relief. I wrapped my hand around his shaft and it was practically throbbing. I heard him moan and I knew he had no chance of escape.

There was one small detail to attend to. “If you cum, can you get hard again?” He nodded mutely and I smiled at him. Aah yes - the prowess of the younger male, the ability to shoot his load and then be ready for action again. This was crazy but I was determined to get my fill.

Soon we were on the bed, both of us naked, and Ryan was sucking on my boobs as I carefully stroked his wonderful young cock. How hard he was, so keen for this older woman. His body felt so amazingly good, so much better than the podgy middle-aged man I’d slept with for years. He was fit and lean and so responsive to me.

Ryan proved his own desire for sex by going down on me right then. It was something my husband had rarely ever done. His lips and his tongue flicked over my clitoris and my wet vagina and I felt my back arch off the bed. He wanted me, he was horny for me, and I was ready to give him everything. I didn’t even care about his technique. I climaxed anyway, so horny and so wild at the sensation of a man who was eager for my body and desperate to pleasure me. Here was the sex I’d been missing so badly - and with a young man to make it real.

“Put it in me,” I whispered, imagining myself still in my university days. I was losing all self-control as Ryan climbed on top of me. This was almost a moment of truth. God, he was so young but right then I could think only of how much I wanted his rampant cock. I reached between my legs and held his member – I remember how excited I was to feel him in my fingers as he got ready to penetrate me.

Gently, I guided him to my vagina and Ryan did the rest. I just moaned, “oh yes.”

Later I would tell myself it was depraved, but I almost came from guiding his hard, young cock into me. I felt like I deserved it after so many years of boring sex. He would do whatever I wanted and I was eager to receive it. So I encouraged that young guy, the age of my daughter, to lie on top of me and put his penis inside me.

Again, I cannot describe how it felt to have that young, taut body on top of mine and to feel his thrusting into my vagina. Luckily for me, he was not a virgin. All I could think about was his passion for me and the way my body reacted to the pent-up lust and his youthful fumblings. I let him thrust inside me and marvelled at how fantastic it was to have such a virile shaft filling me up. Free from a boring husband, I could concentrate on my pleasure and I felt so good I even tweaked my own nipples for extra stimulation.

“Don’t cum inside me,” I warned him. Then I let myself go and allowed a string of incredible orgasms to surge through my body. I could not recall when a man had made me cum like that.

We fucked for – I don’t know how long. Then he brought me back to the present.

“I’m really close,” he said in a strangled voice. It was the sexiest thing he could have said. But that wasn’t what I wanted – not yet.

Reluctantly, I guided Ryan off me and onto his back. I lay next to him, still panting, and placed my head on his hip. With one hand, I reached down and massaged his balls. They felt better than I can describe, so hard inside their soft pouch. A man’s balls are his most precious thing and we women are cautioned about how we touch them. But now I had power and I could hold them and fondle them and imagine them so full of semen and tiny little sperm.

Then another thought jumped into my head. It was really crazy but I wanted to do something my husband had not let me do for some years. Being so young, I knew Ryan would have had very little experience of women letting him cum in their mouth – but right then I could think of nothing I wanted to do more for this wonderful boy.

I still had the knack, I am happy to say, and could almost cup his balls and stroke his shaft with one hand. It was easy to move a little closer and take the head of his cock into my mouth. He tasted of my vagina and that made me feel even hotter. I remembered from my own youth that he’d last only seconds.

I felt so incredibly alive, so intensely sexual. Ryan came beautifully. I was delighted by the heat and the salty taste of his stuff as he gushed into my mouth. He bucked and swore as I milked him, sucking all I could from his impressive cock. I swallowed him, of course, just as I had wanted for years to do for a man who would appreciate it. I was so “in the moment”, amazed at how intense the whole experience could be.

“You are so sexy,” he told me soon after. “You have a really great body.” I assumed it was what any boy would say to a woman who’d just given him a first-class cock sucking.

Ryan did not have big muscles - he was still too young for that. But he did have the early signs of a six-pack. I took my time to enjoy him and run my hands over his hard, lean shape. Yes, young men still felt the same as I had remembered them. If only I’d married a body like his.

After a time, he wanted to play with my boobs some more. I soon pulled him in close so he could suck them again. At his tender age, of course he was obsessed with my breasts. It was fantastic to feel so desirable to a guy so young. And I have to admit, Ryan seemed to know how to handle them. What was more important was that it did the trick and I could feel his organ getting hard and ready for more action.

I was still horny. There was something delicious about having a naked twenty-something man in my bed. I could be his teacher – I could have been his mother! It was taboo but that only made me want him more.

There was something else I’d not done in years and this was my chance.

“I want to do something,” I told him.

“Yes,” he said with a look of lust. “Do whatever you want.”

I rolled Ryan onto his back and his superb young penis was hard and upright. So I climbed on top. I knew Ryan wouldn’t judge me. The look on his face said it all and I felt so wicked as I held him in position and lowered myself onto that pulsating young shaft. I let him fill me up completely. It was quite easy for my vagina to swallow his young cock because I was suddenly wetter than I could ever remember.

“You have great breasts,” he said again.

I am proud of my new boobs – I really enjoyed the way they sat up nicely and bounced as I rode my young lover. My nipples pointed upwards again. Ryan took advantage, too, reaching up to play with them. I definitely was enjoying the attention from Ryan and I moaned loudly as he squeezed and massaged my tits. I rode him as if he was a new sex toy, cumming again and again till I was too tired to stay up there. Just as I’d hoped, he now had the stamina to give me a proper seeing-to.

We swapped places and once again Ryan made a good effort at screwing this older woman. He was more than twenty years younger, so much less experienced, and yet I could lie back and enjoy myself as his unquenchable libido allowed him so easily to mount me and fuck me. I have to say again – it was incredible to have a man so hungry for me. His young cock stayed so hard and he thrust so deep into me. I felt like a woman for the first time in ages.

“Can I cum this time?” he asked at long last.

It was so sexy to hear him ask me that. I felt his young, slender body thrusting into me and thought about the contents of his balls. I wanted him to erupt inside me!

“Yes, please,” I whispered to him.

It was only moments later that he unleashed a second flood of semen, this time deep into my body. He groaned in a very satisfactory way as I felt him pulse so powerfully with each spurt. And I was captivated by the look on his face as he shot his load for a second time. I had forgotten the gratitude of younger men.

“Good boy,” I whispered as he finished.

I have no idea why I said that but I suppose his eruption was the final proof of how sexy an “older woman” could be. “Good boy,” I told him again as he finished pumping into me.

When we were finished, and his stuff was still leaking from my vagina, I found an old shirt of my husband’s to send him home in. There was just one more thing.

“Do you have a girlfriend?” I asked him. I didn’t care about her – I know that is wrong. There was something else on my mind. He told me that he didn’t have a girl.

“You’d better not tell your damn friends about me,” I said sternly. “If my husband finds out he will cut your balls off.”

It was a silly thing to say but I was so new at this and I felt I needed to protect myself. The look on his face assured me that I was safe and would not find a sniggering group of boys on my next visit to the gym.

For the next few days I was on cloud nine. I found myself thinking again and again how easy it had been. And about how right my girlfriends had been – the “cure” was to have lots of sex. Mind you, I could never tell them about Ryan. What would they think of me? - a mere boy, less than half my age. But I never once felt guilty about what I’d done with Ryan. In fact, it was quite the opposite. I knew I hadn’t been wrong – I had found passionate, intense sex with a man who became highly aroused by me. Now I was wondering how I could find another man to do those things with.

I had to take care of some business. Changing my gym nights was first. Next I made an appointment to have my vagina waxed – it was a little embarrassing but I guess younger women still do that. Lastly, I called my doctor for an appointment. Thank God, I was still using contraception before I let Ryan fill me with his virile, youthful sperm. Apart from that, I enjoyed the memory of an amazing night with a much younger man in my bed. I had no real plans except to find more sex.

A week later I was at the gym, in a class, when I saw Ryan. He didn’t see me in the middle of a big group. He was alone and I could see he was working hard on his beautiful, young body. He was quite a distraction. At that point I had not made any decisions about Ryan. I was not even avoiding him. Changing my nights had just felt safer and gave me some space.

In the end, I couldn’t help myself. I made a decision on the spur of the moment and this time it was me waiting in the carpark. This was the freedom I told myself I could enjoy now. I was liberated and ready for anything. And it was incredibly erotic to be the person in control and getting exactly what I wanted.

Ryan saw me and came over. It was a brief conversation as I was feeling rather giddy.

“Would you come to my house again if I want you? Good, here’s the address. Tomorrow night. And my phone is on there as well – don’t call me unless you have a reason for not coming.”

Shit – it was that easy to command a young guy to come over and have sex with me!I had not forgotten the difference in our ages. Yes, I felt a little foolish propositioning a man so young in the car park. I suppose my justification is that sex is a primal act and that good sex, not age, is the key. I was more than twenty years older than Ryan but still wanting the best sex I could find. And his sweet, young body had fired something in me. Once upon a time I had loved young men. Now this young man with his magnificent penis was available to me. I was getting aroused just talking to him.

That night also brought home to me the advantages of my daughter moving out and spending more time with her father. We had the place to ourselves, my young man and I. When Ryan arrived, I was wearing nothing but my silk robe – this time tied around as I opened the door to him. Of course, he was randy and it didn’t take long before we were in the bedroom, me kissing him deeply and him grabbing at my boobs and my bum. I felt those same tingles of electricity again. “You really have a great body.” He murmured into my mouth. I knew he meant to say “for an old woman” but at least those squats had paid off.

I undressed Ryan, letting my hands wander slowly over his gorgeous young body.

“You have a beautiful body,” I said softly and it was no lie. I enjoyed the shape and feel of his limbs and his muscles. I loved his hard butt. I enjoyed the way his young cock stood so hard and straight, pointing at the ceiling. I know young guys do that without even thinking but I felt so fabulous knowing he was hard because of me.

And I especially enjoyed the feeling of his balls in my hand. Their weight sat snugly in my palm as I curled my fingers around them and stroked his curly pubes.

On the bed, we kissed some more. Once again, I had an amazing feeling of electricity as his hands roamed over my body. He was as eager as our first time and I was responding accordingly. I knew we were going to fuck again and that I was going to enjoy it very much. Right then I knew I was hooked on sex with younger males. Yes, it’s a forbidden passion but I wanted more.

Struggling to control his lust, Ryan quickly moved to my tits and then to my vagina. The newly bare skin was a nice surprise for him and he gave me a big grin.

“Is that special for me?” he asked. I just smiled back at him.

“You were such a good boy last time,” I said to him, wanting his mouth so badly. And, wow, was I glad about the waxing as I was so much more sensitive as he used his lips and tongue on me.

I am sure not all young men are such considerate lovers but Ryan was already outdoing my husband. He had me cumming in just minutes. I was just taking it all, gently running my fingers through his long, brown hair as he worked on my vagina. But I needed more.

“I need you inside me,” I said, trying to order him but instead sounding desperate.

Just like the younger men I’d remembered, he got straight down to business. This time he needed no help piercing my opening and quickly had me filled up with his fantastic, hard member. He felt even better on this second night and he’d seemingly gained more confidence in this thrusting. I knew my next orgasm was close. When I exploded I could even feel my vagina in spasms, squeezing and gripping his cock as he fucked me so well. I wrapped my legs around that tall, slender body and he actually moaned in response.

Ryan only knew one way of screwing because he is a young guy. He went deeper and faster until I was cumming for him like a train. I know his idea was to cum as quickly as he could but he managed to last a good while. Finally, he had “that look” on his face and I knew he was close.

“Don’t cum yet,” I told him.

Now he was looking desperate. But with a signal I got him off me and on his back. His cock was so big and so hard and it was all mine at that moment. Once again I finished him using my hand and my mouth.

I still remember clearly the first time I ever had a boy cum in my mouth. He was nineteen and it was his idea. But I said yes because I wanted that too. I was so nervous because I had no idea of what to do. But, with him in my mouth, nature took its course and I remember the huge pulse in his penis before his first spurt. It was an incredible buzz to feel his balls emptying into my mouth and I recall it felt so natural to just swallow him. For a teenaged girl, its so amazing to feel you have that much power over a guy and his penis.

The sensations of Ryan erupting in my mouth took me back to that first time. I just loved the warm taste and the thick consistency of his stuff. I cannot say that semen tastes delicious but, to be honest, I was excited to swallow all that youthful sperm. It was such a “wild” thing to do. The best part was that I did not need “permission” to perform such a natural act.

We talked a little as we recovered. I used the time to explore his body, stroking his arms, his chest and his butt. I even slipped my hand between his thighs and gently played with his balls and stroked a finger along his perineum. I even let my finger slip down to his “back door” a few times. I guess I was testing him, or teasing him, but the slow touching was another form of intimacy I’d missed for so long.

Later I couldn’t resist sucking his beautiful cock back to its full hardness and then lay down so he could enter me again. It was a little bit obscene given that he was over twenty years younger than me but, you know what, that only made the act even more enjoyable for me.

We had another glorious fuck and I could not have cared less if anyone thought I was doing the wrong thing. I came over and over again as his youthful body humped on top of me and then I suddenly got another idea. I wanted to try sex in a different position. I knew Ryan had little experience and it felt so wicked to be the older woman who could teach him about sex.

I told Ryan “from behind… go from behind” and, just like that, I got onto all fours in front of him.

With a little fumbling he got his dick inside me again. Only a young guy can feel the way Ryan did as he shoved his big poker back inside my vagina. I watched in the mirror as this handsome young man resumed his animal-like thrusting. It was an incredible turn-on watching us fuck like that, Ryan’s hips moving faster and making my tits bounce with each thrust. I could not remember sex like this with my husband. Again my vagina was spasming around him – I just couldn’t help myself – and I was too far gone to even try counting my orgasms.

For the second time, I let Ryan empty his sperm into me. It felt delicious to have a virile young man, at the height of his powers, shoot his baby-making stuff into me.

I kissed him gently before he got dressed.

“Thank you,” I said honestly. “You are a very good man.”

He grinned and told me, “you’re a totally sexy woman.”

To be continued in part 2, by mjar65 for Literotica