I Shouldn't Have... But I Did


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.


"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.

.... There is more of this story ...

The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account