Guilty Pleasures Ch. 04

Story Info
Jennifer puts her plan into action.
5.4k words
4.63
42.3k
8
Story does not have any tags

Part 4 of the 10 part series

Updated 10/23/2022
Created 08/07/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Many Feathers
Many Feathers
10,462 Followers

I'd actually been working on the manuscript for the better part of an hour, surprised that Jared hadn't come back and peeked his head inside the door, asking me if I wanted or needed anything. And to make matters worse, I really was horny too. The story was indeed erotic, parts of which I'd read and found myself flushed in the face after reading them. And then having to go back and read them again as an editor and not some horny young woman. I had to laugh at myself however still thinking about Jared. No doubt the thing he needed to see to had been what was sticking up between his legs. Having done that, I was reasonably sure he'd taken the edge off and for a while at least, would no longer be horny.

Though I'd been a reasonably horny teenage girl at one point, teenage boys at that age were something entirely different. I should have remembered that. Needing to pee, and honestly wanting another cup of coffee, thus deciding to go and get it myself rather than wait for Jared, I stood up and quietly left the room. Oddly enough, I couldn't hear anything, wondering where Jared had gone off to, and then actually convinced myself that he might have actually left for a while.

Passing by Susan and Bill's bedroom, I decided to use her bathroom rather than go all the way downstairs in order to use the "guest" one as they called it. But Susan had already told me before hand that I was certainly free to do so. Feeling like I was alone, I entered their room, walked around the bed and entered the bath. I had just sat down on the toilet in order to pee when I heard footsteps coming up the stairs. Having not bothered to close the bathroom door, I wasn't about to get up and do so now, figuring that Jared would simply pass by their room anyway on his way in to finally check on me. Which is when I figured that he'd soon after discover I wasn't there, and most likely come looking for me. Even if he did, I still wasn't sure he'd consider the fact I might be using his mom and dad's bathroom, especially with the door open. But that's when I came up with what I thought was a rather naughty idea.

I'd be busy taking a "break". A rather naughty one, and pretend like I wasn't aware of his presence when he came in and found me, unless he made an issue of it. Even then, I quickly rehearsed a few possible scenarios in my mind just in case. Adapting to whichever one seemed more appropriate...if and when he came in to look for me.

Sure enough, seeing the door to his father's room open, and me no longer at the desk, I again heard his feet turning around coming once again back down the hallway. I was almost holding my breath with anticipation, and then moment's later disappointment as I heard him pass by the open doorway of his parent's room. That was one I hadn't planned anything around, and nearly stood up flushing the toilet and then head downstairs after him. About that time I heard footsteps returning, they hesitated briefly in the doorway, and then quietly padded into the room. Hurriedly I lifted my tee shirt up and over my breasts. I figured if he came in and saw those, along with my hand down between my legs there was no way he could deny what it appeared I was doing. I closed my eyes, tilted my head back, and then slipped my finger deeply inside my very wet pussy.

"Oh my god! I'm sorry!"

Jared had indeed stepped into the bathroom. With the door open, I had hoped he would still be curious enough to at least look inside, which he'd done. Sitting the way I was however had caught him totally off guard. He had immediately backed up through the door as I called out to him saying his name twice. But this was one I had prepared myself to react to if he did.

"Jared? Jared!"

I knew he hadn't left his parents room, and figured he was just standing outside the door. He was.

"Jared? It's ok...really." I made no effort to pull down my tee top however remaining as I was with my bare breasts fully exposed. I was hoping that small bit of vulnerability would be enough to put him at ease to some extent. I waited for what I knew was only a few moments when he once again poked his head around the corner of the bathroom door looking at me.

I smiled when he did that. "I told you I might need to take a little break," I said grinning trying to keep it light between us in having said that. "And there's nothing to be embarrassed or ashamed about either," I further added, though truth be told, I was a bit embarrassed as he continued to stand there halfway looking at me though he said nothing.

Finally he did however as I re-straightened my tank top pulling it down over my breasts once again. It was now time to reverse direction slightly.

"I'm still sorry, I should have ah... knocked first or something."

"It's my fault, the door was open. But there's still no reason to be sorry Jared, I'm the one who was caught masturbating!"

As I'd hoped, the word "caught" seemed to act like a trigger for him, the movie he'd been watching the day before centering around that very theme. He stepped more fully into the room as I stood up having pulled my thong and shorts back up once again covering myself completely.

"I know your surprised, but for your information Jared, women do masturbate just as often as most men do, especially if we've been reading hot erotic stories like the one I've been working on," I said continuing to smile.

"You do?"

"Oh hell yes!" I laughed. "And especially after working on and reading through the particular scene in the book I was at the time, which finally got to me."

I could see he was curious as to what that might have been, and decided it was time to entice him further if I could, especially as he now questioned me.

"What were you reading?" He asked inquisitively. I had briefly glanced down at his groin, only then realizing he had in fact changed out of his flannel pajama bottoms, now wearing a pair of tight fitting cutoff Levi jeans instead. It was hard to tell if he had a partial erection, or that his package was simply that size all the time.

"Glad you asked that," I said reaching down taking his hand as I led him back through his parent's bedroom down the hall and back to his father's study. "Perhaps you can actually help me out with something," I continued "From a man's perspective."

Rather than taking my seat behind the desk, I had led him over to the small comfortable little couch in the room. Sitting down still holding his hand I pulled him down to sit beside me before letting go. As I did, he slid over just slightly ensuring there was still comfortable distance between us on the couch. Almost too much.

"You see Jared, I'm at a part in the book where the main character is lying down on his bed masturbating when the maid walks in and catches him doing so. He's not even aware that she's there, so naturally he continues. Fascinated, she remains there watching him, slowly becoming aroused herself. Minutes later she is standing there touching herself. Eventually of course he realizes she is, though he doesn't let on that he knows. He proceeds to get even more aroused, playing with himself quite openly, which he hopes will excite her into even doing more herself. It does, as she finally succumbs to the intensity of her desire, fingering herself openly now when he looks over towards her smiling. Both now aware of one another, they continue, just watching one another pleasuring themselves."

"Wow," Jared moaned obviously now aroused himself. "So...what did you mean by needing a man's perspective on this?" He now asked, which I was hoping he would do.

"Well you see Jared, I'm having trouble with the emotional aspect of what the woman was feeling, sensing as she saw him touching himself. As strange as this may sound, I've actually never watched a man masturbating, you know...start to finish. Even Rob hasn't done that for me. I mean sure, I've seen him stroke it a little, just in an effort to get himself aroused prior to doing anything else. But obviously, that's not quite the same."

"Obviously," Jared agreed nodding his head.

"So in trying to understand the emotions and the intensity of the scene as it's been written, I was trying to picture myself as the maid in that situation, but surprisingly enough, I'm finding it a bit more difficult to do so than I first imagined, especially since I've never really seen a man doing that, purposely pleasuring himself so openly and so candidly in that way before. So...I was sort of wondering..."

I saw Jared's eyebrows lift. "You...you're asking me if I would?" He stammered.

"Yes Jared, it would help me out a lot. I'm sort of stuck trying to reason it all out, so it would help me yes, a great deal in fact if I could get a greater sense of what she was thinking, feeling as she stood there watching him."

"Geeze, I don't know," Jared said obviously nervous even shaking a little as he said that. "Can I think about it?" He then said surprising me as he stood up.

"Ah, sure Jared...of course," I responded slightly disappointed. I had actually thought that with his having schemed into getting me to see him, even if it was meant to appear as an accident when I did, would have been sufficient for him to do so for me now. Obviously I had missed something in my way of thinking. Perhaps he felt threatened by me as opposed to being aroused enough to want to do it now being confronted directly with it. I continued to sit there as Jared walked back towards the door.

"Oh, I originally came up to see if you...ah needed anything...to drink!" He quickly added.

"Any more coffee?" I asked dejectedly. He nodded his head yes and said he'd be right back with it.

Still shaking my own head in wonder, I crossed back over towards the desk sitting down. I began wondering what it was going to take, likewise realizing this might in fact never actually happen. I didn't know whether to laugh or to cry at the moment. It was turning out to be a much more difficult task than I'd originally thought.

Jared returned several minutes later with a fresh cup of coffee for me, along with a decanter, which he had also filled. I almost frowned upon seeing that. He'd obviously ensured I'd have no reason for needing him to check in on me again anytime soon.

I was slightly surprised when he sat back down on the couch again as opposed to taking one of the two desk chairs in front of me.

"Ok, so what do I need to do?" He asked softly. I tried to hold back a delighted laugh, seeing the somewhat serious expression on his face. I changed tactics, deciding to approach this almost clinically, as though doing research. I realized at that very moment, that Jared truly did want to be the one to seduce me, and not visa versa. Having reversed the rolls even to the small extent that I had, had thrown him. It was time to switch things around again in the other direction.

"Well, like I said Jared, I'm trying to get a feel for how the maid felt, to more fully understand what seeing him doing that felt like for her, especially as I've never seen that myself. So...even if you sort of only pretend perhaps for a few moments for me, right there on the couch even, it might give me a much better idea as to how she really did feel before I go making any changes to the book that might hurt it as opposed to helping that particular scene."

"Ok," he said once again looking a little embarrassed, but I was pleased when he stood, his hands coming up to undo the button on his jeans. I turned my head purposely looking away, and then stood up myself.

"In fact...what I'd like to do, is sort of recreate the scene. I'll leave the room stand outside for a moment, give you a chance to get a bit more comfortable with yourself while you do this. Then I'll silently open the door and look in. How's that sound?" I asked.

It was evident that he liked the idea, waiting for me to leave before completely pulling off his jeans. I hurriedly stepped outside the door softly closing it and then began counting to fifty.

It was strange. I knew what I would no doubt be seeing when I reentered the room. So I felt prepared for it when I did. I wasn't. It was as though I had actually walked in, catching him. I actually found myself catching my breath, totally unprepared for what I was seeing, looking at as Jared lay there on his father's couch. He was completely naked for one. The fact he'd only been wearing cutoff jeans previously shouldn't have had the impact on me that seeing him entirely naked did. But it did. The lean lines of his magnificently sculpted body as he stretched out there on the couch, the tautness of his tight firm little ass pressed deeply into the seat. I stood there literally holding my breath taking it all in. I hadn't even as yet focused in on the obvious as he lay there eyes closed, slowly fisting his hard erect prick. When I did, I nearly gasped in surprise. I knew from the little I had seen, and in the short time I had actually seen it, he was big. But for some reason as I stood there looking at him now, he seemed even more so, and perhaps was for all I knew. His cock appeared to be even more purplish than I remembered it, far more angry looking in appearance, the fat spongy head of his prick likewise more swollen as he slowly lay there stroking himself.

I quietly stepped further into the room. As I did, I felt the trickle of moisture between my own legs, amazed at how rapidly I'd become aroused, though I'd certainly been earlier. Even so, the sudden onrush of additional liquid had surprised me. I could feel the sudden escalation of my heart beating deep inside my chest. Jared continued to lay there, pretending to be unaware of my presence though I stepped in even closer, as quietly as I could. I could now hear the squishy, erotic, highly sensual lubrications of his cock as his hand continued to pump it, though again slowly up and down his shaft. It glistened as he did so, further intensifying my own senses. I didn't even realize at first that I had slipped my own hand beneath the waistband of my shorts in an effort to seek relief. I now stood there, frustratingly touching myself indirectly, still watching him, once again gathering in the entire picture of his long lean form, his toes almost pointed at the end of the couch, the flare of his nostrils as he breathed, the rigidity of his enormously hard cock. I was now breathing hard. So much so that it was easily heard. As though part of the story, realistically anyway, Jared opened his eyes only then looking over. He stopped stroking his cock, now staring at me. It was my turn to feel slightly embarrassed at having walked in, catching him playing with himself.

Like I said, it actually felt that way. Like I had. It was erotic as hell.

"Is this what you had in mind? Is it helping?" Jared now asked.

God I wish he hadn't said that. At least not like that. I didn't want to turn this into a clinical observation, not now.

I decided then not to respond back in the same manner, letting my true feelings and emotions speak for me instead.

"That is fucking hot," which it was, I replied lustfully, now more purposely fingering myself, though again failing to make better contact than I needed to, wanted to. I removed my hand, quickly undoing the button on my waistband, almost as hurriedly undoing my zipper. I saw Jared's eyes light up as he lay there looking at me, almost yelling out at him not to move as he swung his feet around on the couch now sitting up. As he did, my shorts fell down around my ankles, I stepped out of them and then slithered my thong down my legs as well stepping out of those. I now stood before him almost as naked as he was, my fingers quickly finding my slit, spreading my labia apart for him to look at, which he was. I now tenderly touched my clit, flicking it with my finger as his hand once again slid down his enormous cock all the way to his balls, cupping them and toying with them briefly before sliding upwards once more. I watched his hand as it slid over the top of his prick, gathering even more moisture, which had oozed from the tip. He palmed it, smearing his fresh slick essence over the head of his dick, and then down his shaft once more, wetting it, slicking it, and now stroking it firmly up and down.

I groaned.

Jared stood suddenly. And as he did, I watched an enormous streamer of spunk suddenly fly from the end of his dick. His eyes looked wild as he did so, almost surprised. I stood there unmoving, my own fingers suddenly paralyzed, yet embedded deeply inside myself. I too had been taken by surprise, watching him as he jettisoned another, and then another thick streamer of sperm towards me, but not quite reaching me where I stood. Within moments he had plastered the floor with his thick sticky cream, one long streamer of it now lying only inches away from my foot.

"Fuck!" he cried out looking down at the mess. "I better get something, dad will kill me if this stains the carpet!" As though a whirlwind, Jared shot past me running down the stairs, his previously discarded Levi jeans clasped in his hand as he did. I could only stand there in shock, not yet comprehending what had just happened until the reality of it hit me.

Once again, I didn't know whether to laugh or to cry.

**

By the time he returned carrying a wet towel and carpet cleaner in his hands, once again dressed when he did, so was I. I'd been half tempted to remain as I was, but seeing the look of relief on his face when he came back into the room, I knew I had made the best choice. As he knelt down on the floor spraying the carpet with the bottle, I spoke.

"Thank you Jared, that really was wonderful you know, and helped me a lot," I told him trying to ease his sudden self consciousness at how quickly everything had happened. It was obvious he wasn't real pleased with himself however, almost angry when he answered me back.

"Glad I could help," he said simply, somewhat sarcastically. "Damn, I hope this comes out."

I wanted to walk over and shake him, but I didn't, sitting down instead at the desk, waiting patiently for him to finish and look up at me before speaking again. When he was finally satisfied, and more than a little relieved to see that everything looked perfectly normal, perfect again, only then did he look up towards me and actually smile. Though there was still a red tint to his cheeks as he did so.

"Sorry," he said once again. "I wasn't quite expecting that."

"Don't worry about it, I wasn't either...but I don't mind telling you Jared, it really was damn fucking hot, watching you...squirting like that," I said trying to reignite the moment. And for a moment, it nearly did. Which is when the phone rang downstairs. He turned heading towards the door speaking as he ran off.

"I'll come check on you again later," he said. And was gone.

True to his word, he did. Around lunchtime. He came into the room carrying a tray full of food. A tuna salad sandwich, some chips, an apple along with a lemonade, which he'd, made for me. He was also dressed. Jared now wore a pair of long legged jeans, tee shirt and sneakers, so I knew he was going out.

"My friend Bob called," he informed me. "Meeting him at the movies. There's plenty more lemonade down in the fridge if you want more," he then told me, and then with that smiled, though he turned and once again headed out through the door.

I ate what he'd fixed for me, saved out what work I had actually done, and then drove myself home.

**

I was more confused than pleased with everything that had happened, though I did see it as having made some progress. And the honest truth of the matter was, I still highly aroused myself, the image of Jared lying there on the couch stroking his cock was one that would remain with me for some time to come. I did realize though as I thought about it, this really wasn't going to be as easy as I'd first imagined, if in fact it actually did happen at all. Jared was indeed still a boy in so many ways, and lacking in self confidence perhaps, or in being brave enough to actually approach me, wasn't something that was going to just happen overnight. I wasn't prepared to let it go on forever either, deciding that if we truly hadn't accomplished anything by the time I'd finished editing the novel I was working on, that it wasn't going to after that either.

Many Feathers
Many Feathers
10,462 Followers
12