Guilty Pleasures Ch. 10

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"Who's Jill?" I found myself asking, though I said it to myself.

"And I nearly allowed that to happen as well, even though I knew it wasn't right. I allowed my own curiosity and temptation to get in the way of my reasoning, something I should never have ever done. I'm just glad it never went quite that far for one thing, because I now know, it can't and never will."

"I know that now too," Jared told her. "Like I said...I think just because Jill reminded me so much of you, which is the reason why I even began thinking about it in the first place."

"Ok, sorry for interrupting, but who is this Jill person anyway?"

"Jill Welsh, she was Jared's first true love, and not just a passing fancy at the time either. They had known one another for years, they'd literally grown up together as kids. Bill and I seriously thought one day they would actually get married, when the time came."

"But I screwed that one up too," Jared said butting in. "We broke up my junior year of high school, which was again my own damn fault. I'd been pressuring Jill into having sex with me, something she had repeatedly told me she wasn't ready for yet. We'd done other things of course by then, but mostly just mild petting, nothing serious. She wanted to wait, asked me to do the same. But I kept pressuring her more and more until she finally couldn't handle the pressure any more, and broke up with me. Shortly after that, her parents transferred her to another high school, and then a short time after that, they even found a new place and moved away. I never saw, or spoke to her again after that. Anyway, I now know, because Jill did remind me so much of you, that not having her around anymore, I quite naturally began looking at you, as Jill."

"Well, that explains a few things anyway," I stated.

"So you see mom, this still didn't have anything to do with anything you did...not really. I'd been dealing with my own guilt for a long time, thinking about you in ways that I shouldn't have been in the first place. But now I know the reason why. So I've come to terms with that, and accepted that now. You see...when I saw you sitting in the chair, saw the tears in your eyes falling, yet the love you still had for me as you did, as you sat there humiliating yourself in front of me. I saw not your face, but Jill's. It was the same look she gave me just before we broke up. And then I realized, I was about to lose you...as my mother, the same way I lost her. Because of my own foolish pride, stupid illogical reasoning. And I knew then, in that moment...I had made a horrible, horrible mistake. And so again...for that, I am truly, truly sorry."

"Well I'm just glad that we've somehow managed to make it here," Susan told him. "But...there's no need for you to do anything rash, certainly not move out of the house, unless that's something you still wish to do. Just do it for your own reasons, and not for the reasons you indicated earlier. I'd prefer it if you continued to live at home, at least for a while Jared. You'll be moving out on your own soon enough as it is anyway."

"So you don't hate me then? Either of you?"

"Of course not," Susan and I said almost simultaneously. "Believe it or not Jared, we both love you. "Maybe things happened that now shouldn't have, but the fact they did cannot change the way I now feel about you. But I for one, am glad that we've all come to our senses about this. You need to make your own decisions, have your own choices and not have anything forced upon you, no more than you tried to force yourself later upon us. In that...we were all wrong. But now hopefully, we've been given a new chance to set things right again. So, can we all agree on that? Forgive and forget as it were?"

"I can...if you guys will," Jared stated, and then received a hug and a kiss from Susan in response to that, and then from me. "Well, I still think I'm going to be heading back. I've already ruined apart of your weekend as it is. Maybe at least you can salvage the rest of it, still have a little fun together."

I saw Susan's eyes rise in surprise upon hearing that. "You're ok with that? Still? After all this?"

Jared laughed. "Oh mom, give me a little credit anyway. You guys are friends, albeit close friends," he snickered. "No...the thought of that doesn't bother me at all, and frankly I'm glad that you can, that you do. But you are adults, responsible for yourselves, just as I now know that I am. So no, I say have fun, enjoy yourselves and quit worrying about what I think one way or the other about it, but more importantly, quit worrying about me. My time will come when it's supposed to, and not before then."

Jared stood up, preparing to leave. He glanced out across the pool area, and then froze. He looked as though he'd seen a ghost. And in a way...he had.

"What?" I said looking over in the direction he was, but didn't comprehend what it was he was looking at. Though Susan did.

"Oh my god!" She exclaimed suddenly sitting up, as Jared all but collapsed back down into his seat, his face having lost all color.

"What?" I repeated again.

"See that young attractive little blonde just sitting down in the lounge chair over there?"

"Yeah?"

"That's Jill!" Susan said sounding almost out of breath.

"Well I'll be damned," I exclaimed just under my breath as I sat there looking at what appeared to be a younger image of my very best friend. "No wonder."

**

We all sat there in silence watching the young woman as she spread out a towel on one of the pool lounge chairs preparing to lay back and catch some sun. I was a bit surprised when she reached back around behind herself, undoing the clasp on her top, letting it fall. Unlike Susan, her breasts appeared more similar to my own in their size and shape, a nice full perky "B" cup, and perhaps a bit fuller than my own. But it was obvious that Jared was surprised when she did that, let alone surprised at just seeing her there after all this time.

"Damn, I've never really even seen her boobs before," he said still in somewhat of a state of shock. "Now suddenly, there she is...after all this time, just lying there..."

"Maybe you should go over and say hi to her," I suggested. Jared looked at me like I was insane. "Why not Jared? What have you got to lose? What's she going to do? Make a scene? And even if she does...which I'm willing to bet she won't, what's the worst that can happen anyway? Ask you to leave? If she does...then leave. But you won't know one way or the other unless you go over there."

"She's right Jared. If you don't do it, you'll never forgive yourself. There's no way you can just up and go home now, not after seeing her again. And not until you've at least made some attempt to speak to her. If nothing else...just go over, tell her you've missed her, you're sorry, and then see what she has to say about all that. If she still has feelings for you too, you'll know it. If she doesn't...well, then you'll know that too. But you won't know anything one way or the other, unless you go over there and find out."

Still weak in the knees, Jared did stand, holding briefly onto the table for support, screwing up his courage. "Well...if she does hit me, I hope she hits me hard enough for all three of you...because I'll certainly deserve it," he stated, and then finding his legs, he slowly began making his way around the long end of the pool slowly approaching her.

It was like watching it all in slow motion. No one else around the pool area even seemed to exist anymore, somehow fading away. I glanced first towards Jared as he rounded the diving board heading directly towards her at the far opposite end. She was by now applying a bit of sunscreen to herself, glancing about as she did, and then as though sensing something...looking over in his direction. Her hand froze on her flesh, her hand suddenly coming up to shield her eyes. She sat straight up in her chair then, and I half expected her to reach for either her top or the towel beneath her, but she did neither. Jared had stopped midway towards her, hesitating, gauging her next reaction perhaps. Which when it came, was totally unexpected, for everyone.

As quickly as she had sat up, she now stood. She made for neither her top, nor her towel in order to cover herself with. In the next instant she had closed the gap between them before Jared could even react to it. So unprepared for it, when she reached him running at nearly full speed, Jared lost his balance, and together the two of them fell sideways into the pool, clinging to one another as they did.

"Now that's what I call a welcome!" Susan laughed, as I sat there and joined her, totally surprised by what we'd just witnessed.

**

We sat watching them thrash about wildly in the water for a few moments. Curious onlookers sitting nearby, temporarily watching them as well, wondering what all the sudden fuss and laughter was about. Finally, Jared managed to say something to her, now pointing in our direction. I saw Jill wave, as Susan waved back, and then we watched her sprint the short distance across the pool as she swam towards us, soon after getting out, Jared following behind. She arrived moments after that at our table, dripping wet, bare breasted, and obviously not the least bit embarrassed at being so, though amusingly, Jared was.

"Well, well Jill. Been a long time, nice to see you again," Susan told her. "I've...we've missed you," she then added and stood up giving the young woman an affectionate hug as Jill all but clung to her, hugging her back excitedly, just as Jared only then reached us...smiling. "So...what are you doing here anyway?" Susan asked.

"As a matter of fact, I just moved back a few days ago, got a place of my own, plan on starting school again in the fall. Thought after all that, I'd come up here, spend a few days relaxing, gathering my courage...and then see if I could find Jared, see if there was anything worth salvaging between us. Low and behold...guess who finds me instead? What do you call that anyway?" She said suddenly pressing herself against Jared kissing him deeply right there in front of us, with poor Jared not at all sure at the moment where to put his hands.

"Perfect timing?" I suggested, and then burst out laughing as Jared finally gave up worrying about it, and embraced her as everyone about us stood there looking on.

**

The pool waiter came over and took new drink orders from us, this time ordering Jared as well as Jill a non virginal drink. I liked the fact that she wasn't at all shy or inhibited about sitting there bare breasted while we did so, though of all people, it was Jared who seemed the most perplexed and confused by her newfound boldness.

"Want me to go over and get your uh...towel or something?" He'd asked her.

"Why? You embarrassed about seeing my boobs? I thought you always wanted to, and now...here you are trying to cover them up instead. Though if you are uncomfortable, I guess I will if that's what you really want."

"I didn't say that...it's just that, well....um ah....seeing you, I mean, like this, suddenly..."

"Jared? Relax, enjoy your drink," I told him, and then removed my own top, just as Susan did.

"See? Now we're all relaxed and equal here, though some more than others," I said once again looking at Susan's much larger breasts. This time however, Jared didn't even bother noticing, his eyes glued on Jill at the moment.

"So, what are you doing up here anyway?" She now asked the rest of us. For a moment, Jared had a worried look in his eyes.

"Same as you...just getting away for the weekend, trying to relax, though Jared here just mentioned the fact he was thinking about heading back, rather than staying."

"Oh? And now that you've found out I'm staying here? Is that something you're still considering on doing?"

"Well no...I guess not, not now anyway. But...I did sort of crash my parent's weekend, so if they don't mind letting me stay in the extra room."

I could just see the look on our husband's faces when we told them that Jared had decided to stay with us for the remainder of the weekend. Until Jill once again surprised us all...and I do mean everyone.

"You can always stay with me in my room Jared, I am sleeping alone you know."

Susan and I both watched Jared's eyes light up with delight upon hearing that, as he stood there grinning at his mother and I sheepishly.

"You and I have a lot of catching up to do...in more ways than one," she added. "I think we need to sit down and have a long talk first though...before we do that," she then said as Jared frowned a little upon hearing that. She then leaned over, whispering into his ear. He listened, his eyes growing wide, his face suddenly blushing a little as she stood.

"Well, I think I'll go gather up my things and head back to my room for a bit. When you're ready to come see me Jared, I'm in bungalow 37. Oh, I understand they're having an outdoor pool party and barbeque tonight for dinner, you guys planning on being there?" She asked.

"Wouldn't miss it for the world!" Susan and I both told her, and then watched her as she scampered off, her cute little boobs bouncing up and down suggestively as she did so.

"So Jared...what did she just tell you?" Susan asked, once again seeing him blush upon being asked that.

"She said she was still a virgin...but that hopefully after tonight...she won't be."

Susan laughed at that. "Isn't that a case of the blind leading the blind?" She teased.

"Except, he's not quite as blind as he once was," I reminded her. "And because of that, I don't think it will be quite as awkward for either of them as it might have been back then. And besides...something tells me that Jill's not as blind as we might believe her to be either. I have a feeling, she's honed up on her brail techniques. But, what you Jared, need to get straight in your mind, is if you can accept that. So...can you?"

He thought about that only briefly, and only for a moment, and then stood.

"Who the hell am I to judge? I'm the one who chased her away in the first place. I'm the one who nearly lost her because of it, who nearly lost what I now have with the two of you, and more so...with my own mother!"

It was nice finely hearing him say that, and I gave him an affectionate kiss of my own. He looked at me then, winking.

"I don't mind telling you Jennefer, especially now. I still wouldn't mind being with you one day, you know...sort of finishing what it was we started and never really got around too?"

"I'll tell you what Jared, see how things go with you and Jill, see how your relationship with her goes first. Work on that...work on yourselves. Perhaps for your birthday maybe."

"My birthday? Shit! That's less than two months from now!" He said grinning at me.

I laughed. "I didn't say 'which' birthday, and I also said...maybe."

Jared moaned, nodded his head smiling. "Yeah...maybe, maybe then." He then kissed his mom, told her how much he truly did love her, and then dashed off in the direction of Jill's room.

Susan and I held up our drinks, clinking them together, smiling once again.

"Hey, you know what I could really use?" Susan asked me.

"No. What?"

"A really nice massage!"

"Think we can still call and get an appointment this late in the day?" I wondered.

"To hell with that," Susan said standing. "I was thinking more along the lines of you doing me...and me doing you."

"Even better," I told her standing up taking her hand in mine. "Lead the way sweetie...lead the way."

**

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AnonymousAnonymousabout 3 years ago
Very good story

I was a little worried there for awhile, last chapter, but it turned out well. Another good story.

RanDog025RanDog025about 6 years ago
WONDERFUL STORY

IT DID HOWEVER REMIND ME OF HOW BIZARRE MY NOW "EX" COULD BE. GIVE AN INCH AND BEHIND YOUR BACK THEY'RE GOING FOR THE MILE. YOU JUST CAN'T TRUST A WOMAN, SO STAY SINGLE AND STAY AWAY FROM MARRIED WOMEN.

BogartsBossBogartsBossabout 13 years ago

Well written. As usual. I want to know more-and yet this feels like a good place to step away from Jen and her friends.

digdaddyrichdigdaddyrichover 14 years ago
I didn't get the the point of the story

First of all, I can't see a young man 18 years old ever passing up some mature sexy MILF, just because he wanted to save himself for the perfect mate, unless he wants to be a fucking MONK. Normally the guy would only think with his dick head, and would have fucked her the first chance he had.

I didn't understand all of the humiliation that he was putting the two women through either. I would have thought he would have considered himself lucky that they would even care enough about him to help with his sexual hang ups.

It's a shame that Jen didn't get her pussy filled with the young studs cock, but I guess he was in fact too immature to know that he had the sexy woman any time he wanted her.

What a waste, it would have been so sweet to read that Jen actually got to feel a young lover.

pouyqwertpouyqwertover 14 years ago
Nice recovery

Nice Recovery.

I think there should be a two more chapters.

1. The evening with Jared and Jill

2. The birthday surprise for Jared.

I look forward to other stories also, I enjoy reading your stuff.

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