Pleasures with Guilt – 3



We both heard the mad-dash scramble coming from below us, the sudden silence of the TV as it was switched off, just as Sophia called out again. “Jared? Are you here?” More movement, and then the sound of steps in the hallway just below the stairs.

“Yeah mom, I’m here,” Jared called up. “Just taking a break,” he then added. “I’ll be up to finish the lawn in a few here,” he then assured her.

“I bet he’s standing there naked with a woody,” Sophia whispered looking at me. “Perfect,” she grinned further. Once again calling back to him. “Ok, just wanted you to know that Jennifer’s here with me, she’s going to be borrowing your dads workspace again for the next several days, so we’ll be in his den if you need us,” she finished calling down to him. Once again there was scurrying below as Sophia and I headed into the house down the hall and away from the kitchen. We’d barely entered Bill’s office when Jared stood there in the doorway, poking his head in.

Sure enough, all he had on was a tight, form fitting pair of swim trunks that he’d obviously been wearing while out mowing the yard. The fact he must have recently been playing with himself was likewise almost as obvious. He had just enough of a tell-tale bulge remaining in his tight-fitting shorts as he stood off to one side of the doorway, trying to conceal it, to confirm what it was he’d been up to.

“So, you’re gonna be working here for the next few days huh?” He asked a bit too curiously as Sophia shot me a quick knowing look.

“Yep! Sure am!” I said, smiling at him.

“Cool!” He again answered a bit too quickly, casting a worried look over towards his mother, though she didn’t respond. “I won’t get in your way though,” he added. “You won’t even know that I’m here.”

That one she did respond to. “Actually Jared, I’d appreciate it, and so would Jennifer, if you would drop in on her from time to time while she’s working. Make sure she has something to drink, or munch on while she’s working so that she doesn’t have to worry about getting up in the middle of something and getting it herself. I mean don’t bug her all the time, but…if you’d at least stop in and ask her if she needs anything every hour or so, that would be great,” she told him.

“Yes Jared, I’d appreciate that very much myself,” I added to that, seeing the delight in his eyes as I smiled at him.

“Sure thing! Well…guess I’d better get the yard done before dad gets home,” he then said and hurried out the door before the obvious became even more noticeable than it already was.

“So…did he?” Sophia asked after he’d left.

“I think so, yes. Sort of hard to tell though, he was pretty good about keeping himself hidden behind the door, but looked to me like he did.” Sophia grinned, taking me by the hand and led me back out of the room towards her bedroom and then over to the window looking down into the yard below. We stood just well enough back behind the somewhat transparent curtain looking down. Just then Jared came out into the yard. He quickly looked about, and then shoved his hand down the front of his swim-trunks adjusting himself. Even doing that, it was noticeable from Sophia’s bedroom that he had an obvious erection.

“Looks like all systems are gone,” she giggled looking down at her son as he fired up the mower, though once again he looked down at himself as though checking to see if he was presentable enough.”

“Looks like,” I commented back, giggling as well, surprised that I could find myself becoming as aroused as I was so soon after our little episode at the restaurant. But here I was, nearly as horny now as I had been then.

“I wonder what he was watching,” Sophia mused, and nodded towards the door. “Come on, let’s go see. I bet he didn’t have time to put everything back the way it should be,” she told me.

Bill had always been meticulous about his stuff. His books, CD’s, even his DVD’s were always in perfect alphabetical order. Up until a year ago or so, he’d kept his X-rated movies under lock and key, but ever since Jared had turned eighteen, he was no longer worried about Jared watching some of them from time to time. Though even then…he kept them in perfect order on the shelf. Sophia walked over towards the cabinet, sure enough, Jared had hurriedly returned them out of order. She pulled three he’d obviously been looking at. Even by the names on two of them I was surprised Bill had them to begin with.

“Hmmm, Hot naughty MILF’s and young men,” Sophia said reading the first. “Not surprised at this one, it really is pretty good. Bill and I have watched it a few times together, and even I’ll admit, I’d do some of the women myself…not to mention the young men!”

She then pulled the other one glancing at its title. By the look on her face I could see she was surprised by that one.

“What?”

“Not one I’ve seen before,” she told me. “Must be a new one, though Bill never mentioned this one to me.” I looked at the title then too.

“Maybe it’s not even one of his?” I suggested, which was entirely possible. It wasn’t anywhere near where it should be if it was, and not something I would have expected to find Bill interested in either.

“Young men were caught masturbating by their mothers,” it said.

“You don’t think he…”

“You never know,” I laughed in response. “I think most young men do from time to time engage in fantasies of that sort, and you are after all, an attractive looking “MILF”, I said, spelling the word out purposely, teasing her as I did. “Not to mention…being a pretty nasty mother on top of all that.”

Sophia shot me a derogatory look, but then grinned. “Yeah well, while you’re at this, see if you can discover just what his thoughts are towards that?” She suggested.

“I will Sue, but only if Jared doesn’t swear me to secrecy or something. The one thing I will never do, is betray his confidence unless it was a life threatening situation or something. If he asks me to promise him not to tell you something, outside of what I’ve already promised you I would, then I can’t. Simple as that, so don’t ask me. If I should learn about something, or it comes up and I’m not having to stand there and cross my heart and hope to die over it…then I will. But otherwise…no.”

“Fair enough,” Sue said. “In the meantime, I’m still fucking horny, care to share the other side of my new double dildo?”

I grinned back at her, chasing her back upstairs towards her bedroom. “Thought you’d never ask!”

**

As I’d already been there that afternoon, it was far more natural for me to show up in the morning with all my work stuff, doing so long after Sophia and Bill had left for work. I was still setting up when Jared poked his head inside the door.

“Morning Jen, can I get you anything he asked?”

I had purposely worn the exact same skin-tight shirt I had worn the other day when I’d caught him staring at my nipples. I figured that might be a rather nice reminder, and though they weren’t poking through my shirt now like they were then, I knew that later on after the air-conditioning kicked in as the day heated up, that they would. In addition to that, I’d also worn a pair of already too short shorts, about my only pair really,

and had in fact rolled the cuff on them, making them even shorter. I knew damn well that the lower portion of my ass cheeks would be sticking out, which is what I now presented to him as I leaned over sitting two boxes of the rather large manuscript I’d be working on down on the floor. I took a bit more time bent over that way as I pretended to arrange things.

“I’d love it if your mom left me a cup of coffee,” I responded, still bent over at the waist rummaging through the box. I smiled inwardly when it took him a moment longer than normal to answer me back.

“Sure, uh…she did. Be right back!”

I was sitting behind the desk in Bill’s chair looking at my computer screen when Jared returned. Almost immediately he walked over behind me, setting down my fresh hot cup of coffee, peering over my shoulder as he did. Normally, something like that might have irritated me, but not today.

“So…what are you working on this time?” He curiously asked.

I’d been hoping he would eventually, as it now gave me the perfect opportunity to sort of set the tone and mood while I’d be here.

“Actually, it’s an erotic novel,” I told him. “Written by a much older man now, who has put together his memoirs of his early life growing up as a young man. His sexual exploits, adventures, that sort of thing.”

“Wow,” Jared said, perhaps surprised I would share that with him, but I wanted him to feel like I was treating him like an adult, and thus speaking to him as one, albeit him being still a young one. “You mean, you’ll actually be reading about all the stuff he’s ever done…with women? Stuff like that?” He asked an obvious excited edge to his tone of voice.

“Yes I will,” I said, sipping my coffee, glancing sideways towards him. It was early in the morning, not even 7:30 yet when I’d come over. Jared was wearing what appeared to be a pair of flannel pajama bottoms and nothing else. I’d obviously begun to notice his firm physique, his wiry muscled frame, but once again I noticed something else as he stood there next to me, the ever growing bulge in his loose-fitting bottoms. Though at the moment, he didn’t seem to notice it was, or that he would soon be standing there next to me with a full-blown erection either.

“Ah, um…can I ask you sort of a personal question?” Only then did he seem to realize he’d soon be in a bad sort of way as he scooted around the desk taking a seat in front of me, and thus hiding for the moment at least his rapidly growing dick.

“Sure, go ahead, feel free,” I told him. “We’ve known one another long enough that neither one of us should feel uncomfortable around one another, so ask me whatever you’d like!”

His smile was one of relief, yet at the same time one of obvious joy as well as pleasure at having heard that.

“Cool, well in that case, I was sort of wondering…” though he again paused.

“Wondering what?” I said looking back, sitting back in my chair as I now knew my nipples had stiffened considerably. In doing that, I knew damn well I was putting them at direct eye-level as I sat there across from him. When I saw him looking directly at me there, still speaking, I smiled into the side of my coffee cup as I sat sipping it.

“Well, reading stuff like that, doesn’t it sort of work…you know…” He was blushing as I straightened myself up a bit more, answering his question boldly.

“Make me horny? Of course it does! I’m only human after all. But it’s my job too, and since they pay me fairly well to read manuscripts, even manuscripts like this one, it’s just one of the hazards of the job so to speak. Especially when they get as erotic as this one’s been,” I said, sharing with him. “The guys had quite a bit of experience with the ladies. I think he’s even done things I never thought possible,” I told Jared, seeing the somewhat shocked, though equally excited expression on his face when I said that.

“Wow, so, ah…so what happens if you do? I mean, you know…do you have to get up and take a break or something?”

“Or something,” I smiled back, looking at him over my cup, only then setting it down. Once again he said “Wow”, and then standing, his face clearly flushed as he did. And then as he did, he looked down at himself, saw his erection which had of course drawn my eyes towards it as well, and then excused himself as he turned his back quickly towards me as he walked hurriedly towards the door.

“I’ll ah…I’ll be back in a little while to check on you, see if they’re anything that you need. I ah…there’s ah…some stuff I need to do myself, so…I’d ah, you know…best get at it.”

He was gone before I could even respond, closing the door behind him as he left. I could feel the wetness already pooling between my legs as I stared at the now closed door. I smiled inwardly. It was going to be a very interesting day.I met Sophia for lunch the following day at a favorite little restaurant of ours. As we usually did, we asked for our favorite table, which was off to one side and a bit out of the normal flow of traffic.

In the beginning our waiters and waitresses weren’t too pleased by our request. But now being “regulars” as we were, and tipping very well for the additional privacy so we could often chat without being overheard, we were only met with smiles and better than average service after that.

I knew this little meet would center around Jared. I was more than a bit nervous even now as we met up, sitting down to discuss it. And though I had in the heat of passion agreed to do this, after Sophia and Bill had left, Rob and I had sat down and discussed it at length after that once again. My first concern was for him, and had he had any reservations about it whatsoever afterwards, I’d have gladly declined, calling up our friends and reneging on my agreement to go through with all of this.

Rob didn’t, aside from getting my assurance that once Jared and I had in fact slept together, it wouldn’t continue. (Unless he was there to see it of course and be involved afterwards). I didn’t take his comment seriously, not even being able to imagine it myself, but after what we’d now experienced with our friends (discussing that in detail as well) I no longer believed that even that wasn’t possible.

The biggest obstacle of course in pursuing this, was in doing it in such a way that Jared could enjoy the thrill of the chase prior to our ending up in bed together, and me taking his virginity. We all knew going in that it wasn’t likely to happen overnight, and that in the beginning, Jared might in fact not even be self confident enough to go through with it himself when push came to shove so to speak.

I’d agreed to keep everyone informed of course as to any progress, and what all might transpire over the days, or even weeks ahead if it were to take that long. Interestingly enough, my husband as well as our friends had found the aspect of that arousing. But then…so did I. I’d already imagined myself a few silly scenarios as to how things might progress, what might happen, and then later on sharing the details with everyone in explicit detail. I had in fact masturbated that very morning prior to dressing and leaving to meet Sophia while imagining just that.

If anything, Sophia was even more nervous and excited than I was. If she’d been a pot of water, she’d have already boiled over as we slid into our cozy, somewhat private little booth together sharing the same bench seat.

“So…you and Rob discuss things after we left?” She asked. I told her we had, and that it was still on, though I was curious as to how we were going to go about setting this up so that Jared had some way of screwing up enough courage to approach me, and very possibly try and seduce me. I wasn’t at all surprised to hear that Sophia had already come up with an answer to that.

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