I Shouldn't Have... But I Did

by Thesandman

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, First, Oral Sex, Masturbation, Petting, Squirting, Voyeurism, .

Desc: Sex Story: An older woman finds passion and lust with a much younger man.

It had been months since my divorce, and though I had recently started dating again, I was more than just a bit gun-shy about some of the men my best friend and sister had been trying to hook me up with. Only one of which I had actually had sex with, primarily because he had been good looking ... and I had been horny.

But that too had been a mistake. He was lousy in bed, looking out only for himself.

Like I had been doing, I then swore another oath of chastity on myself (at least through a minimum of six dates) before allowing so much as a titty fondle. So far, I'd managed to go the distance of three dates with the men Joyce, my sister had sent my way. Either they were in too big a hurry to take me to bed, or I knew at the end of three dates we simply weren't compatible.

"I don't know what I'm going to do about you," she had told me one morning. "I mean I'm glad to see you're at least going out once in a while, but you're getting more and more moody with each passing day too," she then added. Which was true ... I had been.

Going without sexual release just simply wasn't normal for me. Not that I didn't masturbate, because I did. Every single day, and sometimes twice. But that was more like a stress-relief kind of an orgasm, and not a pleasurable "felt like I'd died and gone to heaven," kind of a climax. That kind I hadn't had for longer than I cared to think about.

"Yeah, I know ... just not easy these days," I told her. "I'm nearing forty, and at the moment most of the good ones are already taken. Seems like all I'm getting are the ones more like my ex, who's now out doing what they are. Looking for an easy score, fresh new pussy, and no commitment."

"Well? Maybe that's what you should be doing right now. Just relax, enjoy yourself. The right man will come along when it's time Debra. Until he does, quit insisting on that silly six date rule of yours."

I laughed at that. "Oh? And what's so silly about that? If you remember correctly in the beginning, I was more than willing to just be my old horny self, even if that made it look like I was easy or something. And then the very first guy I end up going to bed with since my divorce, pops off in less than fifteen seconds. Next thing I know he's laying next to me, snoring away in my bed. Damned if I'm ever going to let that happen again!" I responded back.

I had no sooner said that, than the sound of a lawn mower starting up in my sister's back yard startled me, not to mention making it slightly noisier inside my sister's kitchen. On most Saturdays, I had gotten in the habit of driving over to my sister's house for an early morning cup of coffee and weekly gossip. Having been doing so for so long, and since she lived less than a mile away from my house, I'd gotten in the habit of just driving over, usually in nothing more than a wife-beater tee shirt, panties, and if I even remembered to grab it, my robe. This was one of those days when I hadn't even bothered to bring that as warm as it already was. I glanced up at the clock on my sister's wall, it was barely past seven.

"Isn't that a little early to be mowing the lawn?" I asked standing up as though to freshen my coffee though I was curious to see who'd be mowing my sister's yard at this god-forsaken hour of the morning. I stood looking out the window.

"That's probably Peter," Joyce said now standing, walking over to join me as the two of us stood looking out the window together. "As hot as it's been getting lately, he likes to get an earlier start before it gets too unbearably hot to mow the lawn." She paused for just a moment, adding. "Cute butt on him isn't it?" She now asked.

He was obviously young, but very handsome and good looking for his age. "How'd you end up with a hottie like that mowing your yard for you?" I asked still glaring out the window at him.

Peter, as she had referred to him was a tall, well toned without being overly muscled young man. Though she later confirmed it, I had guessed him to be eighteen or nineteen, with sun bleached hair and a light tan as he began mowing her yard wearing nothing more than a cut off pair of Levi jeans.

"Julie's boy," she told me, referring to their next door neighbor. "Peter just graduated high school a couple of months ago, and will soon be heading off into the Navy. Just waiting for his papers to go through I guess. Too bad too, he's been nice to look at when he's come over to mow the lawn. Sometimes his younger brother Dave does it, but I get guilty every time I look at him, two years younger than his brother is, but just as good looking."

I caught my breath just then still looking out, I had seen Peter nonchalantly reach down and scratch his groin as he pushed the mower. That simple innocent act sending a wickedly erotic jolt of pleasure down between my legs. For the briefest of moments, I'd actually imagined him taking his cock out in order to stroke it. Talk about instantaneous unexpected fantasies!

"Get a grip girl!" I told myself and finally stepped away from the window. "He's way too damn young!"

As I turned my sister was sitting there at her kitchen table grinning at me.

"What?"

"Maybe ... you should throw Peter a going away fuck," she laughed.

"Yeah right, don't be ridicules Joyce!" I admonished her, yet my pussy was thinking the very same thing. Already I could feel the sudden appearance of moisture beginning to seep into my crotch, and now wished for the first time I'd actually brought my robe over with me. I hurriedly sat down at the table, but I'd forgotten about the other telltale signs, which my sister immediately picked up on.

"Oh I am, am I? Then why is it if the thought isn't already running around inside that wicked little head of yours, that you're sitting there with your high-beams on honey?"

I looked down at myself. Sure enough, my nipples were rock hard, pressing against the thin material of the white wife-beater I had on. It couldn't be any more noticeable. Which is when I then realized the mower had stopped somewhere along the way, and the sound of someone knocking on her kitchen screen door made me jump.

"Mrs. Jackson?" Peter asked peering through the door at us as we sat at her table. "Your mowers out of gas, and there wasn't any more in the gas can either. I'd offer to go and get some myself, but I happen to be without any transportation at the moment."

"Come in Peter!" Joyce called out to him as I sat glaring at her. Had she forgotten I was sitting there half naked? Then I realized ... she hadn't. Before I could even begin to react, Peter stepped inside.

"Debra? This is Peter, Peter ... my sister Debra," she said introducing us. Though I noticed as he stepped over to take my hand, his eyes had already locked onto my chest, though he quickly looked up upon realizing that, his face reddening.

"Pleased to meet you," he said taking his hand back, though for a moment I'd almost wished he hadn't.

"Unfortunately, Ted's at the golf course, so he has our car," she told him. "Would you mind taking him to get some gas?" Joyce turned asking me.

"I'm ah ... not exactly dressed for that you know," I said once again glaring at her, though she found it obviously amusing, as I again turned seeing Peter's eyes once more locked on my nipples, which felt like they had turned to petrified stone at this point, and looked like it too.

"I guess you can take my car," I then stated, forgetting myself for a moment as I stood to grab my purse. It was no more than two, perhaps three feet away on the counter, but plenty of time for me to realize my mistake, though it was already far too late for that. I now stood there in my sister's kitchen in nothing more than a white pair of cotton panties, and my wife-beater with my full breasts looking like they'd been painted on, my nipples all swollen and hard as rocks pressing against it. All I could think of to do was fish inside my purse for the keys, and hand them to him. Pretending as I did so, that my attire, such as it was ... was perfectly natural for me to be standing there in.

The problem was, I could still feel the wetness between my legs, but I sure as hell wasn't about to look down either and draw any more attention than I already was.

"You know sis, your lawn could use a good mowing too. How longs it been? Two? Three weeks?"

Now I felt my face beginning to flush. One, because I was dressed the way that I was with a sopping wet crotch. And two, because I was actually embarrassed that I'd been neglecting my own yard work, something which I truly hated doing.

"I'd be glad to come over and mow it for you, just as soon as I'm finished here," Peter told me.

"There, problem solved!" Joyce said speaking up before I could, "provided your mower still works of course," she had to add.

Peter had already turned having taken my keys and headed out before I could respond to that one way or the other.

"What the hell are you up to?" I found myself asking my sister instead. But all she did was smile at me and laugh.

"Nothing besides getting your lawn mowed," she grinned wickedly. "Which reminds me, when was the last time you got it mowed anyway?" She now asked.

I knew damn well she wasn't talking about my lawn either. Truth was, I had always kept my pussy bare, nice and smooth. And had in fact just shaved it again last night before slipping into bed. But again, that still wasn't what she had meant either.

"You really are incorrigible, you know that?" I answered. "Now, before he gets back, how about you lend me something to wear?" I asked.


At least Joyce was kind enough to lend me a pair of decent shorts to wear home, though I was still a bit self-conscious about the wife-beater and no bra. Peter had finished her lawn in short order shortly after his return. Just long enough for another cup of coffee and some catching up gossip, though for the most part my sister kept teasing me about tossing Peter a "sweet friendly fuck," as she called it. "Better than an extra tip," she had added.

I stuck my tongue out at her as Peter and I left. I had no intention of doing anything even remotely like that of course, but I still couldn't help fantasizing about it anyway as we made the quick trip back to my place.

"Can I say something and not mean any offense by it?" Peter stated as we drove the short distance home. I smiled, holding my own nervousness, and curiosity in check.

"Sure, go ahead," I said smiling demurely, trying to look something less than the cat who had swallowed the canary, though I'd already caught myself thinking about swallowing something else.

"You've got really amazing boobs!" He said startling, and surprising me with his boldness. Now I did laugh, unable to help myself.

Not wanting to embarrass him, nor myself any more than I already was, I tried keeping it light, a bit flirty perhaps ... but friendly.

"I bet you say that to all the girls."

He actually looked surprised at that, his eyes wide as he responded back to me. "No, I don't ... never have in fact, you're the first. But ... I've only seen one other girl naked anyway, my ex girlfriend, and she didn't have boobs anywhere's near as big, or as pretty as yours are!"

It was a strange compliment to have received, especially the way I'd received it, and with Peter sitting next to me in the car actually staring at my tits. Though had I of been in his shoes, I probably would have too. Just innocent, and naive enough not to know better. But then again, I only had myself to blame for looking the way I now looked too.

"Thank you," I said simply not knowing exactly what else to say, though my mind jumped out ahead of me like it quite often did whenever I became aroused. "I take it she was your first then?"

"First?" He said in that same naive way, and then realized what I'd meant by that. "Oh no ... we ah, we ah never did that," he said blushing. "In fact, well ... I'm still a virgin," he all but blurted, though continuing. "And I'm actually nervous about that too, you know ... going in the Navy here soon and all, can only imagine what the other guys will think, or even do to me maybe, once they find out."

I did laugh openly, embarrassing him a little perhaps though I had tried very hard not to. "I'm sorry," I said still trying to control my giggling. "But it's just that I'm actually surprised. As good looking a boy as you are, and knowing how kids are these days, it's just surprising to find one as attractive as you are ... to still be a virgin!"

Now he laughed too, once again easing the tension. "Not like I haven't tried," he explained. "But the one girl, not even my ex ... that I thought about doing something like that with, wanted to wait until we were married. And I wasn't exactly in the marrying frame of mind at the time. I've always wanted to see a little bit of the world first before settling down, and I thought that joining the Navy for a few years, and doing that would be the most opportune way. Unfortunately, most of the girls I've known didn't see it that way. Hence me still being a virgin."

We had just reached my street and was about to pull up into the driveway. "Tell you what, after you've finished mowing my ... forest," I amended. "Come inside and we'll finish this conversation we're having," I told him, though again for the life of me ... I didn't know why I had said that. I knew damn well I was teasing myself in a way, and perhaps him a little too. But I'd enjoyed talking to him, and if anything, wasn't quite ready to shoo him back home again too soon either.

I quickly showed him where my own mower was, and then left him to his work while I went inside to once again change my clothes into something a bit more appropriate perhaps than what I'd been wearing. It was already getting warm however as I stood there in my bedroom, now naked trying to figure out what exactly it was I could wear without looking too obvious about it.

"Obvious about what?" I asked myself. "It's not like you're actually planning on fucking the poor boy now are you?" I once again asked silently. "Or was I?"

The truth was, I now found myself thinking about it, wondering. Wondering if in fact he actually might be interested. "Chasing Cougars?" Wasn't that the term I'd been hearing lately. "Was I? Would Peter see me in that light? Would he even be interested? Admiring my boobs was one thing. Giving his virginity away to a woman he'd most likely never see again was something else entirely. Especially when I was almost twice his age.

I put another tight fitting red blouse on. No bra. And a matching pair of red shorts to go with it. No panties. And then I traipsed back down to the kitchen area to make up a batch of iced tea for when Peter was finished with the lawn.


Half an hour later he was standing at my back door. I waved at him, motioning for him to come in. "I made some iced-tea," I said pleasantly, though his look told me upon hearing that he didn't really care for it.

"Thanks, but I'd really prefer a beer if you have any," he said walking over to stand next to my kitchen counter. It was just noon, but I figured one beer wasn't going to hurt this early. It just so happened that I had a few Corona's in the refrigerator so I pulled two of them out. "You have any limes?" he now asked.

I did, but I almost told him I didn't, starting to get just a little irritated with his sudden brashness the way I saw it. But once again my own horniness and my odd attraction to this young man both physically as well as towards this somewhat bold attitude caused me to do otherwise. I quickly retrieved a lime and began cutting it up for our beers.

He stood still leaning against the counter as I strolled over towards the kitchen table preparing to sit down, knowing as I did so he was staring at me, no doubt admiring my tight fitting red outfit.

"I liked the other shirt you had on better," I heard him suddenly saying.

With my back still towards him I set my beer down on the kitchen table. Surprised unexpected anger, a bit of irritation with this young man caused me to do something that had I taken a moment more to think about, I probably wouldn't have done. Grabbing the bottom of my tank top, I suddenly yanked it up and over my head, turning, grabbing my beer as I did so. Tossing my top onto the table, I finished the turn lifting my beer up to my mouth sipping from it. I noticed as I did so, Peter had been in the process of sipping on his too, and now held it against his mouth, though he didn't drink. The surprise at my sudden action catching him totally off guard. His eyes were wide, as I stood there in front of him, my bare breasts both clearly revealed.

"That better?" I asked.

"Damn!" He finally said lowering his bottle without having taken a drink from it, drawing out the single word as though it were a sentence all by itself. I couldn't help but smile, his obvious appreciation was disarming as he stood there staring at my tits. As he did, I felt my nipples immediately begin to stiffen, my rather large areola's crinkling up excitedly. And then my own eyes wandered. Still leaning against my kitchen counter, it was nigh impossible not to notice the sudden growing bulge between his legs. The tight fitting Levi shorts he had on, simply not able to contain the press of his rapidly growing prick as he stood there. A fact that he became immediately aware of as it became quickly uncomfortable.

Once again I put my beer down on the table and sauntered over towards him, my full breasts jutting out enticingly as I approached.

"I hope you don't mind my asking..." he began. "But are those real?"

Peter was so innocent, so naive, that I'd quickly come to the conclusion he was simply being himself, speaking his mind, putting words to his thoughts before actually thinking them through. I laughed.

"See for yourself," I told him as I stepped up to stand there in front of him, only inches separating the two of us. I hadn't had children, nor would I ever do so. Something I had learned several years back. Though in a way I was now glad I hadn't, my almost forty-year old breasts looking as good as any woman's might half my age, especially as big and full as they were, though they did rest against my ribcage a bit heavier than they once had.

Peter didn't need to be invited, or asked twice however as his hands immediately came up to surround, and almost immediately begin kneading my aroused flesh like a contented kitten.

"Damn," he said again speaking his one word long drawn out sentence.

"You like huh?" I purred back, enjoying the feel as he continued to squeeze, press and now palm my hard erect nipples, rubbing them in small gentle circles, which had the effect of releasing a driblet of arousal between my legs. Much more of that, because I hadn't worn any panties, I knew I'd be soaking my crotch in no time. My own newfound boldness took over as well as I softly reached out, fingers easily locating the firmness pressed against his pants. I allowed my fingernail to teasingly begin carving out an outline around his rock hard shaft.

"Ohh!" he moaned, shivering uncontrollably as I did that.

"You like that too huh?" I grinned continuing to do so.

"Oh fuck yeah," he said pinching one nipple a bit too firmly, but I accepted the sweet momentary pain as being a sign of his ever-growing need and lust as we stood there.

Reaching over with my other hand, I quickly popped the button on his jeans and then likewise began lowering the zipper on them too. "So Peter, have any of your ex-girlfriends given you a blowjob at least?"

"Yeah, a couple of times, one did anyway ... well, sort of."

I looked him in the eye, eyebrows raised in question. "What do you mean by sort of?"

"Well you know ... she sucked on it a little, for a while. But then she took it out just before I came, didn't want to ... well, you know. But ... she DID let me shoot all over her breasts, that was nice!" He grinned remembering.

I could tell by the expression on his face that even that had to have been a major turning point in his life. I rather enjoyed the feel of that myself on occasion, but as he'd already experienced that, I thought I'd give him something else even more pleasurable to remember. Wordlessly, I finished unzipping his shorts. The moment I had they came loose falling all the way down to his ankles. I had already half suspected, and now confirmed, he hadn't been wearing anything beneath them. His young very aroused prick stood up thick and straight, not overly huge by any means, but certainly well above the norm. I held it briefly in my hand, feeling the heat and throb of it as I caressed him from prick tip to his balls, gently caressing them as we stood there. I was enjoying the catch in his breath each and every time I slowly stroked down, watching his shinny hard prick-tip unsheathe itself. Even better, a nice pearly droplet of precum suddenly oozing from the tiny eye-slit when I did.

It was then that I dropped down onto my knees before he knew what I was about. My mouth suddenly surrounding the spear-like tip of his shaft, his smooth head sliding in as my lips surrounded it, sucking it, teasing it with the tip of my tongue.

"Oh fuck ... that's nice," he again drawled out the words, rolling them over with his tongue as the excitement of the sensation became clearly evidenced in the way he had spoken them.

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