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Debbie was the cougar everyone wanted.
My entire routine had changed as well as my sex life. I had recently moved back from my hiatus out of state so that meant adapting to a different life style as well as a new routine. Not that I cared that things weren’t as comfortable as they used to be, I actually embraced it. I’m the kind of guy that likes change, who welcomes change, so that’s why it was easier for me to adapt to a different culture.

Of course the culture was something I was used to – I used to live here, after all. It’s not like I was stepping into the twilight zone where everything was flipped on its head, I was stepping back into my old stomping grounds. I wasn’t sure what would be here waiting for me, but I knew it wouldn’t be the same as I left it. After all, the only constant thing in this world is change itself.

“Hey, man, we’re playing poker tonight if you wanna join us,” Aaron said from the cab of his truck as I walked by towards my car.

“Right on, when?” I asked, stopping at the open window of his truck.

“I don’t know, probably around seven or eight. You in?”

“Yeah, don’t see why not,” I shrugged, before continuing the short trip to my car.

“Cool, see ya then.”


I had been warned that Debbie was pretty good looking for an older woman; I just didn’t realize she looked as good as they were saying. I figured they were just messing with me since I had been so gullible to believe just about anything they would say in the past. I had learned a lot in my time away, so they weren’t going to pull one on me so easily this time.

“Dude, you’re so full of shit!”

“I promise, Mike. She’s pretty hot, but I know she’s not easy. Simon tried to get with her, but failed miserably,” he added with a laugh.

Simon was, by most standards, a pretty good looking guy that really didn’t have a problem picking up a girl when we’d go out. Being good at getting girls our age was his specialty; getting older women, not so much. He didn’t know how to talk to the cougar like he did with the younger girl. He didn’t how to be blunt and unabashed. That’s where my skill set came in.

“Damn, that’s pretty crazy,” I lied, acting surprised before taking another drink of my beer.

“Yup, so good luck if you decide to go after her.”

Challenge accepted.

They knew my preferences for older women so it really wasn’t a surprise that they made the effort to get me to notice her. When she walked into Nate’s garage, I looked up expecting to see an older woman that may not have exactly been appealing to the eyes. Instead, I looked up to see a bomb shell of a red head. They weren’t fucking with me and, for once, I looked like the ass.

“Told you so,” Aaron said after seeing the shocked look on my face.

Fuck me running…

“Yeah, not bad,” I replied, still looking at her.

We continued playing poker with Debbie there. She’s friends with both Nate and Aaron’s wives so she came over to hang out with them. Naturally that meant she had to come into the garage to say hi to the rest of the guys there since she was freshly single and no restrictions were on her. Sometimes she could be a distraction since some of the single guys couldn’t keep their eyes off her, me included. I couldn’t blame them, I was right there with the gawking, but it was also a little irritating having to yell at someone to either make a move or fold their hand because of Debbie’s hot ass lingering in the garage.

“I don’t think I’ve seen you around here before,” Debbie said as she followed me to the fridge that was located in the other room so I could grab another beer.

“I actually just moved back here from Wyoming. I was there for three years,” I replied, hanging out in the lobby of the garage just to have some alone time with her.

“Oh, nice. So how do you know all these guys?”

“I went to high school with Aaron and Austin. I was down last year for Aaron’s bachelor party and that’s how I met Will, Nate and Charles,” I replied, taking a swig of my drink.

“Well, that’s cool,” she began with a smile, “what’s your name?”

“Mike. And you’re Debbie, correct?”

“Yes. How’d you know?” She asked.

“I heard about the Simon debacle,” I said with a wink and a smile. I wasn’t too sure how that would boil over with her, but I felt it was necessary to show her that I wasn’t afraid to poke fun at anyone, including her. Sometimes it got me into trouble, but I wasn’t worried about it that night. I knew the pool of women here was much deeper than it was in Wyoming.

“Oh? And what did you hear?” she asked, clearly puzzled that I knew something about her.

“That he tried to get you to hook up with him, but it ended badly.”

“Yeah, I guess you could say that. It’s kind of awkward with him here. I know I should go inside the house, but it is kinda fun seeing him squirm every time I look at him,” she said with a grin before adding a wink.

I could see the confidence she had about her, like she didn’t give a fuck if anyone liked her or not. She was a woman who knew what she wanted and knew how to get it. She just went through a divorce with her husband of eighteen years who was as controlling and possessive as someone can get. He always questioned her whenever she came home from work, the gym or even from a night out with her friends. The clamps on her took their toll, but she finally had enough and ended what had been eighteen long years that produced two daughters and a lot of heartache.

“Yeah,” I said with a laugh, “he told me you were hot, but definitely not easy to crack.”

“Well, he was talking all this shit saying how easy it would be for him to get into my pants. I just wanted to make him feel like a little boy and that his game wasn’t as great as he thought it was. Don’t get me wrong, he’s a good looking guy, but not a guy I’d ever do anything with.”

“That’s good, but I do have to agree with him to an extent – you are hot,” I added with a wink.

“To an extent? You think I’m hot, but what don’t you agree with him about?” She looked confused which indicated to me that what I said went right over her head.

“Yeah, I think you’re hot, but I don’t think you’re impossible to crack.”

The expression on her face almost turned to anger as she thought about what I said. “Do you think I’m easy? You don’t even know me and you already think I’ll let just anyone in my pants?”

“No! I don’t think you’re easy, I just don’t think you’re as difficult as he makes you out to be.”

“I look at it this way, if a guy is interested in me and plays his cards right, he has a pretty good shot at getting with me,” she said, her expression changing.

“Ah, I’ll keep that in mind. But, if you don’t mind, I need to get back to the table before they fold my hand for me. I have some cards I need to play,” I shot at her with a wink before walking back to the table.

The poker game continued for the next couple of hours even though I wasn’t really focused on it because of Debbie’s lingering presence. Even though she was there, I did my best to try and ignore her to see how she was going to react to my lack of attention to her even after the conversation we had in the other room. She didn’t seem too effected by it at first, but the more I ignored her, the more she tried to get my attention. She even went as far as sitting next to Simon and starting a conversation, hoping that would make me pay more attention to her. I smiled to myself knowing that he didn’t have a snowball chance in hell, but I wasn’t going to break my resolve.

I made eye contact with her throughout the night, but didn’t say much to her unless she asked me a question or made a comment about the hand I played. I think the other guys caught on to what was taking place between us but no one said anything to me even though there were plenty of chances to when she would get up and get me a new beer without me asking for one.

The poker game finally wrapped up and everyone left except for Simon, Debbie and I. The three of us sat in the garage and talked while Nate went inside and everyone else went home. I was staying with Aaron at the time, which was convenient because he lived next door to Nate. I was literally steps away from the back door that he always kept unlocked.

Simon’s new interest in Debbie became overwhelmingly obvious as well as irritating. I didn’t want to step on his toes and build a wall between us since we just met, but I didn’t want him to ruin whatever chances I may have had with Debbie if he was to step in and take her that night. I wasn’t cool with double dipping into something that a friend, or potential friend, had already dipped into. That’s not how I rolled.

Oh geez, Simon. Go home already. You’re drunk and making yourself look like a total ass!

“Simon! Go home, you’re drunk!” Debbie said to him with a little sternness behind her words as if she heard what I was thinking.

“I’m not that drunk, woman!” he shot back, clearly not wanting to go home without getting a piece of her pussy first. “What’s wrong with you, anyways? Why don’t you want me?”

“I don’t want you because you’re an arrogant ass who thinks you can get with any girl you want. I’m a grown ass woman who doesn’t fall for the shit like little girls do. That’s what’s wrong with me,” she said, causing me to feel kind of bad for the guy even though he brought it upon himself.

“Wow, you’re a bitch,” he said before getting up and walking out of the garage.

“Well, that was interesting,” I said after Simon had drove off.

“You’re telling me,” she replied before going to the refrigerator to get us another round of beers.

I’m not sure how things proceeded after Simon left, but I do remember that we kept drinking in the garage and our conversation gradually became sexual. It all began innocently enough, like most conversations do, but the more we drank, the more I didn’t care. I knew from past experience that older women usually only want one thing – sex.

Most of the time cougars are looking for something with no strings attached. They’ve already been through the rigmaroles of marriage and have dealt with the bullshit that comes along with it. Usually they’re not interested in getting into any type of relationship unless it’s beneficial. It’s like the song title goes: girls just wanna have fun.

And that definitely applied to Debbie. She was more of the free spirit type of woman and was at the point in her life where a relationship simply wasn’t on the books any time soon. She was perfectly suited for me because, at the time, I wasn’t interested in any sort of relationship. I was interested in the same thing she was – to shamelessly get off with no strings attached.

“How old are you?” Debbie asked.

“Twenty-three,” I hesitated, hoping she may or may not have second thoughts about me.

“Wow, you’re not too much older than my daughter,” she said. “I’m old enough to be your mother.”

“Yeah, you are… That’s pretty crazy…”

I looked at her to gauge her interest level after learning how old I was. I didn’t think it would be a deal breaker, but there was still a part of me that was screaming to tread with caution in case my age bothered her.

She laughed. “You’re just a baby,” she added with a wink.

“I may be young, but I know what I’m doing,” I said sternly, making sure to get my point across.

“I don’t see any proof of this,” she said, trying to call my bluff.



“Okay,” I said before getting up and pulling my cock out of my pants. I walked over to her, already hard, before making eye contact, making sure she could see the lust in my eyes.

“Wh…what do you think you’re doing…?” she asked, completely taken aback by my blunt actions.

“Well,” I began before looking down at my cock, “it’s not gonna suck itself,” I added.

“Oh? And you think I’m gonna suck it?” she asked, trying to hide her own arousal.

“Yes, you are,” I replied bluntly, moving closer until the head of my cock was brushing her lips.

She didn’t say a word. She opened her mouth, letting me push my cock past her full lips, before closing them around the head as my length disappeared into her mouth. I gripped her hair before plunging my cock down her throat, causing her to gag and sputter before I pulled back. She gripped my cock with her small hand before taking control and bobbing her head up and down the length of my spit-soaked dick.

“Oh, fuck,” I moaned out as she released my dick from her mouth before stroking it with her lithe hand.

She definitely knew what she was doing as she worked my cock with her expert mouth. She had the right combination of using her mouth and hand while she continued to suck my dick like it was something that she loved doing, like it was something she needed to do. She kept sucking away, trying to milk the cum from my balls, before she abruptly stopped.

“Sit down,” she said, indicating towards the chair that was right behind me.

I sat down in the chair before she moved between my legs, but she didn’t resume sucking my cock like I thought she would.

“I feel kind of guilty,” she said, looking up at me with a bit of hurt in her eyes.


“To be honest, this is the first time I’ve been with another man in about ten years.”

“Ten years? Weren’t you married longer than that?”

“Yeah, but I slept with one of Dave’s friends about ten years ago. It was a drunken mistake but he doesn’t know about it. I feel guilty because I just got divorced and it’s weird not doing this with him.”

I could see the guilt and trepidation in her eyes as she confessed to how she was really feeling. I was led to believe that she was just another divorced woman only looking to have fun since she spent a good portion of her life tied down to a man who wanted to control every facet of her life. I felt kind of bad for her at the time, but I also had my own desires that needed to be released – pun intended.

“I didn’t know that. I mean, we don’t have to do this if you don’t want to,” I said, some of that being genuine.

“Don’t get me wrong, I want to do this, but I feel bad about doing this to my ex-husband,” she said as she stared at my dick before wrapping her slender fingers around my shaft and slowly stroking it.

“For someone who feels so…guilty, your hand is wrapped around my dick…”

She looked up at me before freeing my dick from her grasp. I thought it was over until she surprised me by turning around, dropping her pants and lining my dick with her wet entrance. With one quick and fluid motion, she had my dick lodged into the opening of cervix, eliciting sweet moans from her pretty mouth. She began moving her hips as she moaned out her pleasure for me.

Even though she said she felt bad, I wasn’t quite buying it. The way she was riding my dick showed me that she was into getting her own just as much as I was. She could try to deny it as much as she wanted to, but, since she was moaning like a bitch in heat, I wasn’t going to believe that she wasn’t into it like she might’ve tried to indicate earlier.

“Oh, fuck your pussy feels amazing,” I moaned out, trying to spur on some sort of dirty talk from her.

“Mmmmmm,” was all I could get out of her other than the moans that were spilling from her mouth as she moved up and down on my fuck stick.

Debbie kept riding away at my dick even though she wouldn’t say anything to me. It was a little frustrating because I wanted to know what she was feeling and how she was enjoying things, but she wouldn’t say a fucking thing. I could only get moans out of her which was still enough to keep me hard and interested, but I wanted more. I wanted to know what she thought about the way my dick felt inside her, how it felt to bounce off her cervix every time she came crashing down on it.

All of a sudden, she got off my cock before turning to face me. I looked up at her to see the same guilty look on her face. It was a little disconcerting because I didn’t want her to feel like she had to do something she didn’t want to do.

“Fuck me.”

“How do you want me to fuck you?”

“Get up,” she ordered, making sure to avoid eye contact as I stood up. She bent over the chair, bracing herself on the arm rest, before wriggling her ass at me as if to tempt me to take her however I pleased.

I moved in behind her, taking in the heart shaped look of her ass, before running my hands over her tight cheeks. Debbie was fucking sexy – even sexier from behind, which made it easier to line my dick up with her already fucked hole without feeling bad for doing so. I wanted to fuck her tight pussy from the moment I saw her and I wasn’t planning on wavering from that thought with her sweet ass present in front of me at that moment.

I gripped her hips before plunging deep inside her tight cunt. I held on tight as she moved back into me, working her hips to get more of my length as deep as it could go before she let go of the inhibitions of her ex-husband that kept a tight hold on her, that wouldn’t allow her to have fun and enjoy herself. She finally began to loosen up and let what was happening between us to consume her.

I fucked her pussy hard from behind; doing what I could to make her forget about her ex-husband and to just enjoy the moment that she was in. I was enjoying the feel of her pussy tightly clenching my cock as much as I was hoping she was enjoying being fucked. I wanted her to know that it was alright to enjoy the pleasures of another man, even if it was for one night.

And, even though it was that particular night, I wanted her to know how much I was enjoying myself. I loved the way her tight pussy gripped my rigid cock as I sawed in and out of her hole, willing both of us to an orgasm.

“Fuck…your pussy makes me want to cum deep inside it,” I finally said, breaking the lack of words spoken between us other than the moans that were still spewing out of her mouth as I fucked her hard and deep.

“Then do it.”

That was music to my ears. I gripped her hips even tighter as I dug in deep, concentrating on that looming orgasm only so I could fill her sweet pussy full of my nectar. I didn’t know if she was protected or not, but, at the moment, I didn’t give a shit. I was doing what I could to make sure my cum was deposited into the deepest depths of her willing and wanton hole, no matter what the consequences were going to be. I flat out didn’t care, didn’t give a flying fuck if something came from this or not. I wanted to get my own and wanted it to be as deep as humanly possible.

“Oh, fuckkkkk,” I cried out as my seed filled her waiting pussy, the walls of her cunt contracting around my jerking cock, milking my sack of the potent liquid that was contained within.

I held deep without either of us saying a word to each other as the rest of my cum emptied deep inside her. The reality of what took place hit me full force. I was thrilled that I fucked the shit out of her, but I was also highly nervous that I may have fucked up by not pulling out. I didn’t know if she was on any sort of protection even though she let me know it was okay to unload inside her. Logic was telling me that if she didn’t want a surprise popping up, she would’ve had me pull out and possibly coat her face with what I have to offer.

Chill the fuck, you’re overreacting.

I slowly pulled out before pulling my pants up and taking a seat in the chair next to the one I fucked her over. She stood up and pulled her pants up before sitting down and looking over at me.

“Wow…” was all she could say even though I saw more than just a content look on her face. Under the orgasm she had, she still had the same guilty look on her face.

“That was amazing, Debbie,” I reassured her with a smile, hoping that would sneak a smile on her face.

“Thank you,” she said with a smile, “it was really good, but we shouldn’t have done that…”


“Because of David. I know we’re divorced, but it still felt like I cheated on him.”

“I understand how you feel. You spent so much of your life with him that it feels so weird to be with anyone but him. I get it, but you also need to get over that. If you want to enjoy your new life, you need to let your failed marriage go and enjoy yourself like you did for the most part tonight.”

“I know and I’m so sorry for that. To be honest, I really liked the way you fucked me…I haven’t been fucked like that since…” she trailed off.

Your husband’s best friend…


We hooked up plenty of times since then, but those experiences are another story in themselves. I’ll say this though – she became more lax and actually enjoyed the fucking I gave her. I went to her house plenty of times with her older daughter under the same roof. I’m pretty sure her daughter heard us a few times, but she never let on to what was happening when I was around Debbie. Of course, when Hailey and I were alone, things were different. But, of course, that means writing another story.

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