Naughty Time Ch. 01

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Kyle meets a very special woman on line.
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Part 1 of the 4 part series

Updated 10/19/2022
Created 02/08/2010
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Many Feathers
Many Feathers
10,461 Followers

As I'd been prone to do lately, I was up late again surfing the web, enjoying a few of my favorite erotic web sites. I'd just finished my quarterly exams and was looking forward to Spring Break, though unlike a lot of my college buddies, I couldn't afford to go anywhere. Still, it meant a bit of time off to sit back, relax...even sleep in. Which was one of the reasons I happened to be up this late.

It was naughty time.

I glanced at the clock on the wall in my bedroom, it was just then 10:50 p.m.

"Ten more minutes and she should be on line," I said to myself, already becoming aroused just thinking about it. About her.

Though I still lived at home, primarily for financial reasons, my parents had basically created an apartment of my own downstairs. I had a small kitchenette, though I rarely if ever used it. My own fairly large bedroom with a small sitting room within. I of course had my own shower as well, and all the amenities that made it feel just like an apartment. Even mom and dad knocked on the downstairs door waiting to be invited in before actually doing so. For the time being at least, I had plenty of privacy and space to spread out in. After I graduated, a year or so from now, I hoped that with a decent paying job that I'd finally get out and move into a place of my own.

But for now, I paid my folks rent, which they were most grateful for, and it didn't cost me an arm and a leg doing that, and putting myself through school either.

The one really downside to all of this had been the fact I didn't have a decent set of wheels at the time. Close enough to the University, I took other transportation, rode my old bike, or occasionally borrowed mom and dad's car whenever they didn't need to use it. Unfortunately, it was a luxury I couldn't afford at the moment, though that too I was working towards. But...not having transportation also made dating a lot harder to do to. And that was one of the main reasons I currently wasn't seeing or dating anyone, besides my own hand.

And it's not like I was a nerdy, or a geeky looking guy either. Reasonably attractive, or so I'd been told anyway. Though I certainly wasn't a jock, or worked out every day either. Still, I'd had my fair share of attractive women myself, and until lately anyway, I hadn't had any complaints in the bedroom department either.

But the fact was, because of all this, I had turned towards the Internet for my sexual release and amusement. And it had been while doing that, that I'd signed onto a website were couples met, chatted, got to know one another (very often intimately) and on occasion, sometimes even met. So far, nothing like that had been offered up, but I had been enjoying a few steamy chat-room sessions with what I knew to be an older woman. The only name I knew her by was her sign-on, which happened to be "Naughty Time".

Yeah, now I know...I'd heard it all before. That maybe some of these people claiming to be women, were in fact actually men. And in the beginning, I'd been nervous about that a little. But over time, several weeks now in fact, after getting to know "her" and some of the things we'd discussed, shared, I was ninety-nine percent sure she was in fact who she said she was. And as such, had begun loosening myself up a little. It had been a very slow and gradual thing with us too, another reason I was fairly confident that it really was a she, and not a he. Had it been otherwise, I seriously doubted it would have taken us this long to actually start talking about, or discussing sex. Something we'd only just really gotten into doing, not counting last night of course. Our last chat in fact the night before had gotten pretty hot and steamy. So much so, I had actually jerked off while talking to her, and according to what she'd shared and told me, so had she. Needless to say I was looking forward to another hot "naughty" erotic session with her again tonight.

I had already logged on to the website, just waiting. In the meantime browsing a few other websites, looking at porn, watching a few videos, and arousing myself. Mom and dad had retired to bed quite some time ago, so I knew there was virtually no chance either one of them would find any reason to come downstairs and disturb me. As such, I was now sitting there naked, stroking and fondling my hard cock in anticipation of her soon signing on. When I heard the "ping" of an instant message waiting for me, I immediately brought it up in order to read it. Sure enough...it was her.

Naughty time: "I'm horny....you?"

My online screen name was "Home Alone," maybe it wasn't too sexy, or very original, but it was the best I'd been able to come up with on short notice when I'd signed on the first time.

Home Alone: "Very. Hard as a rock now!"

She responded back with an LOL, along with an EWG, then adding..."Wish I could see that."

I did have a web cam, and wondered if she did. So I sent her the message telling her I had one, and that if she really did want to see me, I'd turn it on for her. Her response back wasn't nearly as quick as they usually were, and I wondered for a moment if maybe I'd been wrong about her all along. Maybe "she" wasn't a she at all...but really a guy after all. To my relief however, she responded back moments later.

Naughty Time: "I have one too. But to be honest, I've never used it," she told me. "I have to be careful...can't show you my face. Sorry. But if you can accept that...then I'll turn it on for you."

I felt genuinely relieved. If she was willing to do that at least, then she really was for real. I responded back.

"Agreed. No faces...just naughty bits, how's that sound?"

"Sounds perfect, I'm looking forward to it," and then, "Wait one."

Seconds later I got a prompt from her, inviting me to view her web cam. I likewise connected, doing the same, turning my own web-cam on, quickly adjusting it so that it was totally focused on my hard erect cock. Which is about all she could see as it basically filled the screen.

"Wow! You're big!" she typed, as the image of her came up, likewise filling in the view I now had of her, which was two fairly good-sized breasts sitting there staring at me, which is about all I could see of her too. But it was good enough in anyone's book. She had great looking tits, and especially as she was obviously much older than I. No, they weren't firm perky breasts of some twenty-something, but that wasn't what I was interested in either. I'd always been partial to older women for some odd reason. So seeing these mature full breasts that tended to rest against her ribcage a bit more than they might on a much younger woman, was still more alluring to me and sensual than anyone else's I had seen. It was also the main reason I tended to browse the "older mature" photo and video sites, not to mention setting up the filter on the website when I joined, inviting mature older women who'd like to chat to contact me as opposed to letting just any woman at any age do so.

"I love your 'tits'," I typed, remembering. She had told me a few days ago, she liked the more obscene, decadent sounding words whenever she was aroused. "Breasts where what woman called one another's," she'd told me. "But tits...was a naughty word, which she preferred using whenever discussing them, or talking about sexual matters regarding them. Boobs was for young girls, tits were for mature, horny women.

"I like your prick," she'd responded back. She liked the word cock too, but she said it was almost used too much, and thus had slightly lessened the erotic sensuality of describing a man's member, though she liked that word too, over cock. Penis of course was too clinical, whereas prick at least, had a naughty feel and sound to it, according to her anyway.

"I'd like my prick between your tits," I had typed back. "I bet it would feel heavenly, fucking them, squirting my juice between them."

"It would feel heavenly for me, jacking you off with them too," she responded back, and then adding. "I am so fucking wet just thinking about it. Wish you could hear the sounds my fingers are making inside my pussy while I'm sitting here playing with myself."

Maybe I couldn't hear her, but I could sure see how wet she was. And she could likewise see how juicy I was getting too as I squeezed my dick, a fat juicy dollop of precum oozing out of the tip which I quickly gathered up with my finger, smearing it around the head of my cock.

"Oh, I wish I was doing that," she said, the camera now pointing further down at her pussy, showing me a nice close up of her cunt, her lips glistening with juice, her fingers now taunting her hard extended little clit as she captured it, pinching it and showing it to me.

"I wish I was licking you too," I told her. I'd love to be sucking that hard amazing clit of yours," I said stroking my cock for her, showing her just how fucking hard I really was.

"I want to watch you cum, see you squirt," she told me. "Will you do that for me baby? Cum for me? Cum hard? Give me a big messy, juicy squirt?"

Just watching her as she fingered herself, playing with her clit, suddenly slapping it a bit with her hand was enough to get me off. I quickly typed "soon" that was all, and then sat back away from the keyboard just enough so she could watch it, watch me, without squirting all over my monitor or keyboard. I then watched as she did the same, giving me more of an exceptional view of her magnificent tits, and pussy at the same time. The moment she did that, I felt the tightening in my balls, the churning surge as my come raced up the length of my shaft. I quit stroking it, though only long enough to momentarily fight against the onslaught, forcing it to erupt by itself, making the orgasm even more intense before helping it along.

"Oh fuck!" I cried out, wishing she could hear it, hear me crying out my pleasure, my joy...my excitement. But I did see it.

Staring at my monitor, I watched her as well. Watched her hand as it came up to clasp one of her breasts. Her fingers forcefully pulling on her nipple now, stretching it out, thus lifting her breast as she did. Her other hand a blur on screen, almost too fast for the web-cam to capture as she obviously frigged her own clit violently. It was a pure joy to watch, watching her cum, seconds later a surge of clear juice emerging from her cunt, surprising me a little, yet exciting me beyond measure.

I continued to spurt, though the orgasm itself was now lessening. No longer the ropes of sperm shooting out of the end of my prick, but continuing to ooze, running down the sides of my shaft and onto my hands where I continued to milk my prick, forcing out each and every last drop of my spending.

"God I wish I could clean you off, lick it all up...suck you down," she typed. "That felt so good...watching you, watching you cum just as I did."

"That really was amazing, seeing you cum too, actually seeing you. Do you always squirt like that?" I had to ask.

She gave me another LOL. "Not always, but usually when I am exceedingly horny, like I was tonight," she said.

"Do you enjoy being horny?" I now asked. "I mean...do you enjoy arousing yourself during the day?"

"Sometimes," she confessed. "I do...why?"

"Because I'd love it if you'd do something for me," I asked her.

"What?"

"Do you own a vibrator?"

"No, I don't. My husband, or rather my ex-husband I mean, would have killed me if he ever caught me using one," she said. "So I never did bother to get one, even now," she added. I had wondered about that, an inadvertent slip perhaps...but I didn't pursue it. "I have used other things though," she said giving me another LOL. "Why do you ask?"

The thought of that gave me another idea, even more wicked than the one I'd been toying with.

"Ever used a banana? Cucumber? Zucchini?"

"Naughty boy," she then said. And then said, "Yes. What do you want me to do?"

"Wear it...all day if you can, put one of those up inside yourself, hold it in with a pair of panties...and then tomorrow night, sitting here, show me...use it on yourself and come for me with it."

"OMG!" She responded back...hesitating for a moment while she thought about it before typing anything more. "OK, I will...but then, you're going to have to do something special for me too!" She said.

"I will, I promise," I told her.

We signed off after that, it was late, now nearing one in the morning. At least I could sleep in a little, though I did have plans to go grocery shopping sometime during the day. Beyond that, I only had time to myself. Time to fantasize, time to imagine...and time to wonder what "Naughty Time" was feeling while doing all that.

I was already anxious for tomorrow night.

**

When I finally got up and came upstairs, mom had just gotten home from dropping dad off at the airport. He'd be out of town on business for a few days, or so he said anyway. For several years now their marriage had been one of convenience more than anything I think. I couldn't even for the life of me imagine them still having sex either, though they still must have from time to time, whenever dad got horny...or wasn't scheduled to be out of town. And I honestly felt sorry for her, it wasn't like mom still wasn't attractive, because she was. Sure, she wasn't exactly svelte, had put on a few more pounds than she would have liked, and even had a bit of grey hair now intermingled with her reddish brown. But all in all...I still found her to be an attractive woman, even if she was my own mother, and had told her so.

She blushed at the comment, trying to pass it off, ignoring me. "Sit down...eat, and don't dawdle too long doing it. I need to get to the grocery store, we're just about out of everything."

I had assumed we'd be going later, but now she seemed to be in a bit of a rush, so I hurriedly ate, and then ran back downstairs to dress. She was waiting for me almost impatiently at the door when I came back up, but at least she was smiling at me when I arrived.

The moment we got to the store, she headed over to the produce aisle. A bit out of the norm perhaps, as usually we started at the other end, and then ended up there. But today obviously she'd decided to go there first, so I followed her, pushing along with the cart. I stood patiently waiting while she picked up a bunch of semi-ripened bananas, tossing them into the cart before moving along, next stopping where the cucumbers were displayed. She picked several examining them putting a couple of them back, picking others, finally selecting two. She then moved on, locating the Zucchini, where the entire process was repeated again.

"What are we having for dinner?" I asked.

"Oh, I thought perhaps we'd have a nice tossed green salad tonight. It would be nice not having to cook a big meal for a change. Been a while since we've had something good and wholesome don't you think?" She was right about that. Dad had always been a meat and potatoes kind of guy, so it was rare that we had anything much different than that. Admittedly, I was now sort of looking forward to that myself.

"I'll help you cut everything up later, maybe we can relax, have a glass of wine, maybe even watch a movie together," I suggested.

"I'd like that, but...the fact of the matter is, your aunts coming over pretty soon. She's planning on having dinner with us. She knows Harold will be out of town for a few days, and you know how much she dislikes visiting whenever he's here. Hope you don't mind," she told me.

"Oh no, not at all, I like Aunt Kathy, she reminds me of you a lot," I said. "Too bad the two of you don't spend a lot more time together as it is."

"Besides, wouldn't you rather be going out...with a girl perhaps, instead of hanging around here all evening with two old ladies?"

"For one, you two aren't old, Kathy's what, one? Two years older than you?"

"Yeah, but she looks ten years younger than I do!" Mom quipped.

"No she doesn't. But she's also a lot more independent and outgoing that you are too mom. Ever since she left Uncle Fred years ago, she's been much happier, far more content, just like you used to be. Maybe, some of that will rub off on you," I hinted without coming right out and saying it. But I could see by the look in mom's eyes, she got my meaning.

"Never mind that, we need to finish up here and get home again. I still have a few more chores to do!"

We soon after finished our shopping, and then rolled out several bags of groceries out to the car. "Here, you put these in the trunk, she said handing me the keys to open it, taking a few of the smaller bags, mostly the fruits and vegetables we had purchased, and began putting those into the back seat. As she leaned in doing that, just as I began lifting out the other bags, I caught a nice view of her legs. It wasn't often than mom actually wore a dress, or even a skirt, but she was doing so today, and once again it reminded me of how nice she looked.

"You know mom, you really should wear a dress more often, you really do have great legs you know!"

"Thank you," she blushed. "I'm glad you still think so, not sure your father does, he rarely even notices me anymore," she said looking a bit sad-eyed.

"Yeah, I know," I offered turning to put away the rest of the groceries as she all but climbed in to the back seat for a moment, before reemerging to sit back up in front with me as we drove home in order to put everything away.

We soon after began doing that, standing side by side in the kitchen while mom handed me stuff, which I then put away. Including the somewhat green bananas that I placed in the bowl on the kitchen table.

"Wasn't there five of these?" I then asked, seeing that one of them appeared to be missing.

"No...I don't think so, I'm pretty sure I only purchased four," she told me. "Or perhaps, one of them broke off and dropped someplace."

"Maybe in the car, in the back seat," I suggested. "I'll go out and look for it later just in case it did."

Mom just smiled at me nodding her head, and then informed me she had other things to do, and that I could run along back to my room if I wanted to. Which I was grateful to do, wanting to spend some more alone time, browsing the net, getting myself good and aroused for this evening, just as I hoped "Naughty Time" would be doing.

**

I'd gotten so involved in browsing the net, in particular one site where all the women posting personal photos on it were considered "mature", that I didn't hear the quick brief knock on my door for a second. By then, my Aunt Kathy having made her presence known, simply opened the door walking in.

Unlike mom and dad, she didn't stand there and wait to be invited inside, especially as I hadn't locked the door. Thank god I wasn't naked. Bad enough I had to hurriedly shut down the screen. Worse, that I was sitting there with an erection, having to wait just for a second as she closed the distance between us coming over to give me a hug. Only then did I stand when she was close enough that she wouldn't have seen the tent I'd created in my jeans. I hugged her, bowing in the middle just a bit to ensure that I wasn't pressing anything against her that would give away my predicament.

"Studying?" She asked.

I doubt she had seen anything, though I know I looked flush in the face by the time she had reached me. I could feel it.

"No, not really. Spring break," I said lamely sitting down again, inviting her to do so as well, though she sat down on the corner of my bed when she did.

"And you're spending it here?" She asked surprised that I would be. "You should be out chasing a few bikini clad girls rather than wasting your time hanging around here!" She said exasperatedly.

I don't know why I said it, but I did. Maybe it was because I was after all still damn fucking horny sitting there. But my Aunt Kathy, ever since her divorce, had tended to wear somewhat revealing clothing. She might have been sixty-one, but I'm here to tell you, she looked a hell of a lot sexier than most women my age did. Like mom, she too had a nice set of breasts, though she tended to let them "hint" at you a bit more than mom ever would. Even now, the blouse she was wearing had one more button undone on it than most women would feel appropriate wearing that way. As such, when she leaned forward even a little bit, you caught a glimpse of her well rounded, smooth orbs peeking out at you, along with a bit of lacy edge to her bra as she also tended to wear far more sexier one's than was also otherwise normal. I'd even seen her go without one before when she'd worn cashmere pullover sweaters and such in times past.

Many Feathers
Many Feathers
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