Guilty Pleasures
Chapter 2

Copyright© 2009 by Thesandman

Erotica Sex Story: Chapter 2 - Best friends begin with sharing common interests

Caution: This Erotica Sex Story contains strong sexual content, including Reluctant   First   Safe Sex   Oral Sex   Masturbation   Sex Toys   Squirting   Cream Pie   Spitting   Exhibitionism   Voyeurism  

I honestly didn't believe I had heard her correctly, so I asked her again.

"What did you just say?"

This time she didn't hesitate. "I asked you, if you'd like to fuck my son," she said simply ... even more importantly, seriously. And quite naturally, I said,

"You can't be serious!"

"Oh but honey. I am. I've even talked to Bill about it, and he agrees with me."

"You what?"

"Yes, we talked about it, spoke a great deal in length about it, and came to the exact same conclusion about it. We really think that you should. Even Bill said he now wishes that his parents had done something like that for him when he'd reached the age of consent. Would have saved him a whole lot of trouble with all the misconceptions he'd been forced to live with after that. All the mistakes, the ungrounded fears, not to mention the guilt he had endured afterwards because of it. Always wondering if he could have done better, been better at it. Learning from someone with actual experience who knew what they were doing as opposed to the blind leading the blind as it were."

"So get him a hooker!" I said disbelief clearly being revealed in the tone of my voice.

"Yeah, we talked about that as an option," she actually admitted. "But then decided against it. As Bill reminded me, and I him ... part of that first time experience is doing it with someone you really care about. Obviously Honey ... Jared really cares about you. I think he's made that quite clear, so sending him to a hooker wouldn't actually be in his best interests.

"What about mine? What about MY interests? Or my husband's?" I asked beginning to sound hysteric.

I finally calmed however having vented, collecting my senses along with my breath.

"If you're finished ranting and raving?" Susan asked.

I said nothing on my end of the line, waiting for what I knew was coming.

"We agree with you on that too. And because of that, because of our friendship with one another, we wouldn't expect you to go behind Rob's back. This is something he would likewise have to be in agreement with before we'd ever consider actually pursuing it. So ... what we'd like to propose is to perhaps come over this evening, maybe even have a little barbeque or something, and then lay it all out for him. See what he has to say, at least explain our reasoning's to him personally ourselves, to both of you. Then ... later on, after the two of you have had a chance to think about it and discuss it, you can tell us what your final decision is. How's that sound?"

The fact that I actually agreed to hearing them out was one thing. Actually going through with it even after we did, was something else. Though I was also in agreement not to even mention we'd talked about it this much until they came over later on that evening and spoke with the two of us together. At least that way, I could pretend to be hearing it for the first time too, and then gage my husband's reaction and similarly react the same way that he no doubt would. I was fairly confident he'd laugh it off as more of a joke than anything, and then that would be that.

Or so I hoped anyway.

Susan and Bill arrived later on that evening. We'd enjoyed a nice quiet little barbeque. Almost too quiet as Rob periodically glanced towards me, his eyes raised in question. Obviously he knew there was another purpose behind our friends visit though he was patient enough to wait it out and see what it was.

I was nervous as hell, sitting on pins and needles and half hoping they had changed their minds and not even bring the subject up. I should have known better, especially when Rob decided to open the door to whatever it was they had come here to really ask us about.

"So, as much as I enjoy having you guys over, you're not acting like your usual naughty selves ... what's up?"

It was all the opening the two of them needed, though it was Susan of course who finally broached the subject.

Though Susan told the entire story from start to finish, which she'd told me she'd do. I was grateful at least that she did it in such a way, that it appeared I was just then hearing about her son's conversation with his friend at the same time Rob now was. When she and Bill finally got to the reason and purpose of their visit having said all that, I found I was holding my breath. I continued to hold it as Rob sat back in his chair digesting what Susan had told him, exactly the same way she had said it to me. For a moment, his facial expression gave absolutely nothing away, one way or the other, and I nearly screamed out at him to say something as it was driving me nuts. When he did, I still sat there looking at him with a stupefied expression on my face.

"Damn, I wish my parents had done that for me!"


I'm fairly certain by the look on my face as Rob finally turned to look at me that he backtracked a little, hesitating. It's not like I was opposed to the idea emotionally, or that I had any real reservations about actually doing it. Though obviously there were some. But it was the fact I'd at least expected him to look a bit more shocked perhaps, or even offer up some sort of initial reservations about it. Which he did, but only after he'd seen my face.

"I think, we'll need to give this some thought and discuss it," he finally added. "Obviously Jen's the one that has to make the ultimate decision for herself, but I think my own personal concern would be, not wanting this to affect our relationship with the two of you. To be honest, when you came over tonight, I was actually concerned, well worried ... that you guys were moving away or something and had come over to tell us that. As you well know, Jen and I are very fond of you two, hell ... I'll come right out and say that we even love you guys, a lot! So I'm actually relieved that wasn't what you came here to tell us. But ... I'll be the first to admit, this was a bit of a surprise."

"We figured it would be," Bill finally said jumping in after being silent most of the evening. "But Susan and I have talked about it at length, and came to the same conclusion about it. But we did so for the very reasons you just mentioned. Because we love you guys too, and wouldn't have asked this of you otherwise, if we didn't. But you're right, it is something you should probably discuss and consider privately. Especially as Jen's the primary individual involved here. Though there is a bit of another caveat we'd like to discuss, if and when you agree to do this for us."

"Oh? And what's that?" I now said finding my own voice. Whatever this was, was new, and not something that Susan had obviously chosen to share with me yet, which I could see was the case by the expression on her face. She didn't blush very damn often, and now she was.

When we'd begun talking, we had moved from the patio table where we'd eaten our dinner together. Susan and I now sitting down on the patio swing where we still were. Rob and Bill had each taken one of our cushioned lounge chairs, sitting down on those, drinks in hand. Susan now turned towards me, sitting a bit sideways in the swing, taking my hands in hers as she spoke.

"If you do decide to do this," she began. "And I honestly hope that you will, what Bill and I would also like, and appreciate, is if you'd take the time to let Jared attempt to seduce you himself. That way ... it won't appear as though we actually set him up. Not only do we think his first experience should be with someone he truly cares about, but that he also have a good memory from it to keep with him always. I think that in his knowing it was mommy and daddy that had fixed up his first time, he might have reservations about it later on. And that would of course go against part of the reason for doing this in the first place."

"You're telling me, that if I do decide to actually go through with this, that you want it to be Jared's idea, or at least let him believe that it is, and allow him in time, to eventually seduce me?"

"In a nutshell, yes."

This time Rob really did have some reservations about it, which I was a little relieved to hear him respond to.

"I'm not sure that I'm really comfortable with that," he told our friends. "I mean, it's one thing for Jen to sleep with Jared, taking his virginity and all that. Something else entirely for him to think he's having some sort of an affair with her, or hoping to."

Susan answered. "We actually both agree with you on that point as well," she began. "Which is why we think it could be handled in such a way that Jared would eventually know it was a onetime only thing when it finally did happen. We're both fairly certain that in time, Jared would eventually reveal to Jennefer he was a virgin. When he does that, after he's enjoyed the thrill of having tried to seduce her, that would be when her resolve would finally melt and that she'd actually consider sleeping with him. But that would also be the time when she'd let him know in no uncertain terms that it was a onetime thing, and would never, ever happen again after that. I think under the circumstances, faced with sleeping with you, or not sleeping with you at all, especially for his very first time, he'd opt for the opportunity at least of doing so."

I sat looking at my husband, who of course sat looking towards me. I was as yet undecided about all this, though oddly enough, I was aroused too. Just talking about this the way we had been had had a profound effect on me in ways I could never have imagined. As I suddenly now noticed with Rob. Even sitting down in the lounge chair, I could see he had an erection. It became clear to me he'd become aroused by all of this, sitting there thinking about it, as I'd been. And I also know, it was because of his own horniness perhaps that he jokingly said what he said next, not really meaning it perhaps as we discussed later. And it wasn't at all out of character for either one of us to have done either, as we'd joked around, flirting around before on previous occasions.

"So ... if Jen does decide to go through with this, what's in it for me?" He quipped trying to make light of things. "I mean after all, I'm the one that has to look the other way and pretend I don't know what's really going on. Do I at least get a handjob, or a blowjob out of this?" He chuckled, "Or even better, finally get to see Susan and Jen going down on one another?" He said laughing again, honestly joking around, as he'd said this before when we'd gotten together, hinting at the fact this was, and had been one of his own personal life-long fantasies he'd enjoy seeing. Only back then, we'd all laughed it off as a bit of naughty playfulness, suggesting that perhaps "one day" it might actually happen, and then very often leaving it at that.

As I said, it's not the first time he'd jokingly hinted at something like this, so had Bill. And even I had on some few occasions indicated that if Rob and I ever did do anything with anyone else, the only two people we'd ever consider doing something like that with, would be the two of them. Susan had herself on numerous occasions come right out and freely admitted that she'd love going down on me, even if I wasn't comfortable in reciprocating the same back for her. Which she now knew, after my admission to her earlier about Christy wasn't as much of a concern as she at first thought it might be. I had simply not encouraged her too seriously, not because I didn't want to, but because I was sorely tempted. It had even been one of Rob and I's dirty "pillow-talk" discussions on more than a few evenings. Each of us knowing that with only a little persuasion on my part, that Susan would no doubt seriously jump at the chance. And that Bill had basically already given his blessings to her if something like that should ever happen. Though so had Rob, a long, long time ago.

Susan was still holding my hands in hers as she looked at me, all of us having just heard Rob's comment.

"Well, if it would help, if it would make the two of you feel a little more relaxed at doing something like that for us, for Jared..." she added looking into my eyes, "I think that if the four of us were to also become a bit more intimate than we already are now, it might in fact make the rest of this far more accepting for all of us in the long run. So ... to answer your question Rob, if she'd let me, I'd love to lick her pussy right now. Right this very moment in fact."

I still thought she was joking around as she slid off the swing down to her knees in front of me. She had done that before too. A little over a year ago when we'd gone on vacation together over to the Islands. We'd been laying on a secluded section of beach, once again the topic of sex coming up where she'd actually rolled over, repositioning herself between my legs. She had hinted then at actually doing it, her face only inches away from my bikini covered pussy. She had even run her tongue briefly between my legs, though my bottoms had been the only barrier existing between her tongue and my pussy at the time. Once again, Rob had been sitting there next to me with a massive erection, just like he had now, half wishing she was serious. As I actually found myself wishing at the time as horny as I was. But even with the stretch of beach we were on being as secluded as it was, there was still too many other's within looking distance to have noticed her actually doing so. Her look however as she finally rolled away, laughing and once again sitting up, was the exact same one I was seeing now.

We had in fact fucked side by side in the same room we shared later on that evening, watching one another doing so in fact. But it was as close as we'd ever come to doing anything else. Even I had to admit, that night, and the two successive nights afterwards when we did, were amongst the most erotic that Rob and I had ever shared together.

Now I sat there looking down at her as she looked up towards me. That same look, that hungry, wanton expression on her face. I felt the heat in my own face as I sat there, expecting her to sit up, once again laughing it off as just another one of her teasing little adventures.

"Yeah right ... you'd do that right here," I finally said calling what I thought was her bluff.

"Right here, right now," she said leaning forward a bit more. Close enough I could now feel her breath against my skin as I nervously laughed looking up. Both Rob and Bill seemed transfixed, frozen in time, drinks in hand, hard cocks readily apparent as they had both sat up hopefully, expectantly ... though neither one of them moved, nor even appeared to be breathing.

 
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