Guilty Pleasures
Chapter 1

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

Desc: Sex Story: Chapter 1 - Best friends begin with sharing common interests

It was a beautiful Saturday morning as I stepped outside the door of our home. As I'd been doing now for the past two years, I was off to visit my best friend Susan who lived just a short three blocks away. We usually traded off weeks, me going there, her coming here. It was my turn to walk over and spend the morning with her, sipping coffee and enjoying our weekly gossip sessions with one another. During the time we had come to know one another, our husbands had quickly become best friends as well. Like us, they usually went out golfing together at least every other weekend, which gave us more than enough reason to spend the better part of our mornings together.

And I didn't mind getting up early in order to do that either. It was my favorite time of day. The quaint little neighborhood we lived in was always so peaceful and serene. Most people not quite up yet, still sleeping in with very little traffic on the road, only the occasional jogger running by, people out walking their dogs enjoying the same calm and quiet of the morning that I was.

Susan was already standing in her front door waiting for me, a cup of fresh hot coffee in her hand which she extended towards me even before I'd left the sidewalk walking up their drive towards her.

Aside from one brief curious fling with my college roommate years ago, I had never entertained nor ventured again down that particular path. I'd have made another exception for Susan. She reminded me of Christy in so many ways, though ironically they didn't even look like one another at all. It was however her bubbly personality, her enthusiasm for adventure, and her uninhibited thinking that had first attracted her to me as a friend, and later, on some few occasions, becoming the object of the rare fantasy where I once again entertained private thoughts. Thoughts which I had never acted upon, or felt like I ever really would as tempting as they actually were.

Susan was around the same height that I was, around five and a half feet. Though a blonde, she certainly wasn't dumb, actually having an IQ somewhere around genius level, though you wouldn't have known that in simply speaking with her. She never lorded her intelligence over me, or anyone else for that matter. But she could if necessary provide statistics, logic and somehow manage to conclusively support whatever discussion she might be involved in. But like I said, on top of all that, she was attractive, if not downright sexy as hell, and she knew it too, though once again, she never really used that to her advantage either. Well ... most of the time anyway.

Susan loved to flirt, not only with my own husband, but very often with me as well. It was the kind of fun sexy flirtation that was more innocent than serious, but it never failed to ignite my husband Rob's ardor, and very often even my own.

Susan wore her hair short in a very sassy, again flirtatious sort of way, where I on the other hand wore my dark brown hair long, usually in a ponytail most of the time. She'd been after me to cut it, wearing it as short as she did, but with a much more rounded face than she had, I just couldn't see getting away with the same sort of look.

Susan had another thing going for her as well, though at times I think she considered it to be more of a detriment as opposed to being an attribute. She had fairly large breasts, easily a D cup, if not a double D, as opposed to me being more of a large sized B, or small C if that. But in that too we tended to disagree. Susan was always telling me how she wished she had breasts more like my size, but that her husband Bill would kill her if she ever seriously considered having them reduced. Though I might have wished for larger breasts myself, I'd never once considered having them enlarged, perfectly content with them the way they were, as my own husband Robert so often told me he was.

As usual, Susan stood in her front door holding open the screen, coffee in hand, one for her, one for me. Her robe open. I don't know if she actually had a sash for it or not. I'd never seen it if she did. Never seen her wearing it tied together, yet when she did have a free hand, she very often walked with it clasping her robe closed. I'd even once commented on why she did that. She'd mentioned she had it around somewhere and perhaps should try and find it, though she also said, she enjoyed teasing her husband by not keeping it closed. And more importantly, he loved it whenever she did that, very often flashing him one thing or another without her ever realizing that she had. In that, she almost did play the dumb-blonde role, but I couldn't help but wonder if that wasn't deviously planned as well. She seemed to enjoy teasing her husband constantly, and loved how he appeared to be constantly aroused, constantly horny whenever he was around her. I knew from our conversations, they had a very satisfying and enjoyable sex-life. Once again, because of her perhaps, mine too had slowly gotten to be more and more like that with Rob.

But that was indeed my very dear and best friend Susan. The way she wore, or almost didn't wear that silly robe of hers was more along the lines of Susan's personality. I never saw her with her robe closed again after that.

"Morning sweetie!" She called out upon seeing me. "Beautiful day isn't it?"

I laughed out loud good naturedly. "Beautiful view too!" I called back as I began the short walk up the driveway towards her. "I'm sure Mr. Edwards across the street thinks so too," I added as I'd seen him step outside his front door briefly, leaning over to pick up his morning newspaper before disappearing back inside. But not before he'd taken a good long look at my best friend, one breast clearly in evidence as she held up my coffee in offering to me.

She glanced over towards his house, but he'd already gone back inside. I half wondered as she did if he wasn't still standing back in the shadows beyond the window looking out at the two of us as I reached her, embracing her, and then just for fun, mauling her exposed breast briefly.

"That should make his day alright!" Susan squealed and then stepped back letting me inside. "You're in a naughty bit of a mood aren't you?" She then asked. "If I didn't know better, I might think you're just horny enough to take me to bed and have your way with me!"

"Damn near," I told her, half considering it. "Rob was almost late picking up your husband for their golf game!" I said grinning at her. I woke up to the alarm, as well as his very hard cock poking me in the back. Decided to do something about it before he left. Unfortunately, he got his jollies well enough, but left me even more aroused and horny than I already was. I guess the good thing is, he's promised to make up for it later on this evening, so I guess the extended arousal I'm in while waiting for that will be worth it."

"I could help you take the edge off," she quipped. And once again, I wasn't at all sure if she was just being her usual self, joking around, or might actually be suggesting it for real. I just smiled at her without saying anything. "Or ... you could go into the bedroom and try out that new vibrator I just got and told you about. I love it, and I know you would too!" She told me.

I did actually own one, but it wasn't anything too terribly complicated or elaborate. Just a simple slim, silver vibrating device, much like the way they were in the beginning before they started getting all the new whistles and bells attached to them.

"I think I'll wait until that toy party of yours you invited me to," I told her. "Maybe then, I might actually get something different," I told her. Oddly, I really did now wish to change the subject before my panties got any wetter than they were already beginning to be. The likelihood of that happening remote however, as usually our early morning discussions centered around sex most of the time anyway, that and the latest gossip we sometimes shared, which usually did too.

"So ... how's Jared doing anyway?" I asked attempting to change the subject. I should have known better.

That was another difference between us. Susan and Bill had a teenage son, about to graduate soon, though his plans were of course to eventually move out and head off to college. Rob and I had never had any children of our own, I couldn't for several reasons, though we'd once considered actually adopting a few years back. Our jobs, new careers had of course given us the excuse to never really pursue it. And though we sometimes still talked about it, it's about all we ever really did. I was only a couple of years younger than Susan was, though neither one of us really looked our age. At thirty-five, I knew I could easily pass for someone in my late twenties, and Susan easily doing that herself.

"He's fine, doing well ... though lately I think he's been having girlfriend problems, if you know what I mean," she snickered. "He got in really late last night and headed straight up to bed. He tried to hide it, but I could tell he was sporting an erection. No doubt he struck out once again with his new girlfriend Stacy. She's a cock-tease if I've ever seen one!"

I was used to her uninhibited way of thinking of course, that was Susan. But hearing her talking about her son's sex-life on such a personal level still tended to throw me a little whenever she did that.

"You don't have any concerns, fears about your son having sex at this age?" I asked curiously, already knowing the answer.

"Of course not, why should I? I certainly had by the time I was his age, as long as he's responsible for himself and his partner, shows maturity with regards to it and respects her, why should I? Frankly honey ... I'm actually surprised he's still a virgin!"

"He is?" I said surprised to be hearing that. I'd actually assumed he wasn't. "How on earth do you know that?"

"Because he told me, and I believe him," she responded back easily.

I'd often wondered if there was any truth behind the old adage about feeling your ears tickling if someone was talking about you. As though to support that, seconds later I heard a door opening and then closing a bit back further into the house.

"Speak of the devil," Susan giggled. "Sounds like Jared's up." I noticed that she reached up closing the front of her robe with her hand, though as usual, she didn't do anything more than that, still sipping her coffee when he came walking in.

"Morning honey," she said as he did so, lifting her cheek in order to receive an affectionate morning kiss from him as he leaned over towards her, though eying me. Seeing me shouldn't have been much of a surprise either, I very often was on Saturdays when he'd gotten up before. But for some reason I noticed an odd expression on his face as he glanced over towards me, smiling quickly however acknowledging my presence.

"And good morning to you too Jen," he said shortening my own name with equal affection. The only other person who ever called me that had been Rob. Even Bill called me Jennefer, as did Susan, though usually I was always Sweetie or Honey whenever she spoke to me. But again, it was an odd look that I had received from him there for a moment before he moved further into the kitchen, pouring himself a cup of coffee and then returning back towards his own room.

I didn't even ask Susan the question, merely looking at her with a curious expression on my face perhaps. She had obviously seen it too. We waited until we'd both heard his bedroom door closing again before I finally spoke.

"He really doesn't seem like his usual self, did you see the way he looked at me?" I asked wondering why he had. Susan giggled and then purposely looked down at my chest.

"Maybe that had something to do with it," she then said.

I looked down at myself, totally oblivious, and then saw what they both had. My nipples were rock hard, sticking well out of the thin tight man's sleeveless tee shirt I had on. I hadn't worn a bra, though I usually didn't a great deal of the time either. Like I said, I had smaller than average breasts and usually didn't worry about wearing one unless I was going out for one reason or another. Making the walk over to visit with Susan didn't constitute the requirement of having to wear one. My mistake. I was also wearing a lightweight floral print blouse over that, but it wasn't buttoned hanging fashionably open. I hadn't even thought about it when I had gotten dressed and walked over. Now I wish I had.

Once again Susan laughed seeing my face turning beet red.

"Honey, don't worry about it. Yours certainly aren't the first tits he's ever looked at, probably even felt, and they sure as hell won't be the last. I'm sure he's just a bit over stimulated at the moment after his frustrating night last night. You know, having a severe case of blue-balls as it were?" she said joking around about it. "And it's not the first time I've caught him looking at your boob's either, or mine for that matter either," she then added. "So ... don't let it get to you. Jared's a normal average American boy whose hormones are currently running rampant at the moment. I should know, I've changed enough soiled sheets lately, not to mention finding an inordinate amount of dirty hankies as well. And never once have I seen Jared running around blowing his nose. Like I said earlier, Frankly, I wish he'd find someone and take care of his virginity issue, all this laundry I'm doing is starting to get expensive!"

That honestly did make me laugh, and I felt a little better. Though I felt something else in addition to that, which didn't. My panties were once again starting to feel a bit sticky, though I blamed my own hormonal needs left unsatisfied due to my husband's fault, which still didn't help my current problem. I stood up, excusing myself.

"Potty time," I told her. "All that coffee we're drinking, like usual, has run right through me."

"Speaking of which, I'll start up another pot while you're doing that. When you come back, I'll tell you about what Doris Jackson told me she saw yesterday afternoon!"

Doris was another friend of Susan's, not a close one, not the way we were of course, and certainly no real close friend of mine either, more passing acquaintances than anything. But she never failed to have a bit of gossip about one person or another, which very often proved to be true, so it was interesting to hear from Susan what the latest bit of news was. Getting the "Doris Report" as we jokingly referred to it, had become a natural part of our weekly get-togethers.

"Hold that thought," I said as I hurriedly retreated down the hallway towards the bathroom. I knew I'd be passing by Jared's room on my way there, which I had so often done in the past. The exception was, this time I happened to notice that his door hadn't been closed all the way. It was only open just a crack, but enough so that I caught movement coming from within his room as I started to walk by. The fleeting image of what I then saw stopping me cold, backing me up. I knew I shouldn't, and had I thought about it before then, wouldn't have. Logic and reasoning making more sense. Unfortunately at the moment, I wasn't thinking quite as clearly as I should have been. Aroused, with a very wet pussy driving my emotions had caught me off guard, as had Jared.

I found myself holding my breath as I realized what he was lying there doing. Even though the guilt of actually standing there peeking at him was already beginning to worm its way into my thoughts, I managed to hold it off for a moment more, still looking before finally giving in to it, and then hurriedly entering the bathroom. I basically collapsed down onto the toilet, only then daring to breathe, fearful that he might have heard me coming. ("Cumming?") I actually found myself thinking, realizing I was horny as hell.

For a boy ... well, a man boy anyway, he had a sizeable cock, one that appeared to be considerably larger than even my husband's was. But the fact he was lying there on his bed, stroking it, furiously in fact ... had taken me by surprise to say the least, and I found myself wondering what he might be laying there thinking about while he pleasured himself, and briefly wondered, entertaining the thought, "Had it been me?"

I quickly convinced myself no. Even though the last thing he'd seen before returning to his own room had been my tits ... my rock hard nipples, which as I now looked down again at, were even harder than they had been. The image of his boy-prick as he lay there fisting it. I shook the thought from my head, which immediately came back as I finally took off my shorts, lowering my thong in an effort to finally pee. I touched my clit, touched it again, felt the electrical shock of doing so overwhelming as I continued to do so.

In all the years that Susan and I had been friends, I had never once masturbated in her home, let alone anywhere else for that matter, not counting the one time I had at the office I worked in. But never in Susan's home, nor anyone else's home except for my own. The fact I was doing so now, surprised me, even shocked me a little, though I simply couldn't help it as I sat there playing with myself. I came with such a rush, trying to stifle my cry of pleasure, fearful that Jared might have overheard me, even though I was still a good distance down the hallway from his room when I did. Even so, I took an inordinate amount of time to collect myself, finally peeing, and then washing my hands before re-emerging.

His door was now closed as I walked by again heading back into the kitchen area.

"Jesus Jennefer. I was about to send out a search and rescue team for you," Susan laughed upon seeing me. "What else were you doing in there besides peeing anyway?" she joked not really meaning anything, but the look on my face must have spoken volumes as she stood there looking at me. "My God! You did didn't you?"

I never had been able to lie to her. Sure ... I'd sometimes gotten away with not revealing the truth about something, though usually because her attention had been drawn elsewhere, or I'd somehow gotten lucky and changed the subject. But not this time. And to make matters worse, Susan wasn't about to let up either, not until she'd rung out the reasoning behind the fact that I actually had either. It would have been like getting involved in a really good book, and then putting it down just before reaching the ending. Wasn't going to happen.

The bottom line was, I was embarrassed however, my face having turned scarlet, though I also imagined I was still a bit flushed from the rather intense little orgasm I'd just given myself in addition to that.

I swear, Susan had a nose, or some sort of sixth sense or something when it came to anything sexual too. Like a bloodhound, she sat there sniffing me out. I half expected her to get down on all fours and come over and smell me personally herself. She just sat there waiting, smiling at me. She'd have stayed that way too ... forever, for as long as it took until I finally said something. I know. Because she'd done it before. Thank god, that she was my dearest and very best friend. I knew I could tell her anything without judgment or recrimination, though even this, was perhaps borderline in doing that.

I did however, finally find my courage. "I just ... I ah, just saw ... Jared, um ah ... jerking off."


For the first time since we'd known one another, I think I had actually taken her by surprise.

"You did what?" she asked again. At least she didn't look angry or anything. Just surprised, though I was pleased to see the sudden upturn of her lips a moment or two later when she spoke once more. "How?"

I sat in my chair feeling like I was on the witness stand. Susan now standing in front of me, though thank god she at least had a fresh cup of coffee in her hand. Though even then I felt like she was the bailiff, soon to be the prosecuting attorney as she swore me in.

"Do you swear to tell the truth? And nothing but the truth? So help you God?"

"I do Susan, I do." Though we never said any of that of course, even though I was thinking it. But I then did tell her what had happened ... and exactly how it had happened, and then of course confessed to her what I had done. She sat in silence for a moment thinking it over, and then burst out laughing.

"Jesus Jen," she said shortening my name, something she rarely if ever did. "Even I've never caught him doing that. All I ever get is the aftermath!" She was still chuckling as I sat there growing redder and redder by the minute.

"So ... tell me, just how big IS my son's dick anyway?"

Somehow we managed to get through the rest of the morning without discussing it further, though we'd forgotten all about the "Doris Report", and had in fact headed off into our own childhood explorations and discoveries. So perhaps in a way ... we still were. I'd even found myself telling her all about my brief little fling with Christy, but all that seemed to do was fire her up even more. Before I knew it, she was pressing me for specific intimate details, a blow-by-blow of our encounters, obviously fascinated to be hearing it, not to mention being aroused. I didn't make an issue out of it, nor even let on that I knew what it was she was doing. But there was no denying the fact that her robe was fully open, and that her hand was moving quite noticeably down between her legs as she sat across from me at the kitchen table.

Had I not been dressed. Had I not been worried about Jared suddenly coming out of his room again, I might actually have joined her. If I thought I was horny and aroused before, I was even more so now. Even walking home shortly after I'd sat there and looked into my friends eyes as she came, I was still thinking about everything that had happened, the moisture pooling between my pussy lips as I walked home on very unsteady feet, my head swimming, my emotions raw.

Rob never knew what hit him the moment he got home from golfing. Not that he minded. But even that had barely taken the edge off.

Sunday afternoon I was outside in the garden doing a bit of weeding when my cell phone rang. I knew immediately that it was Susan. She had a while back taken my phone, programmed her song on it for me. I had nearly killed her because of it. Now every time I heard the song, I couldn't help but laugh. Once again, another Susanism. Hearing "I touch myself" never failed to cause me to giggle, though there had been frantic moments out in public or at work where I'd dived into my purse to answer my phone. Even then, I'd usually got more than just a few curious looks at hearing the tune. I quit worrying about it so much however when I realized just how many people had heard the song, and obviously enjoyed it by the smiles on their faces.

"Susan? What's up?" I answered glad to be taking a breather for a moment as I stepped back into the shade sitting down at our patio table.

"You sitting down?"

I laughed. "Just," I answered back. "I'm outside weeding." She didn't immediately speak, so I asked her again. "Why? What's up Susan?" I now asked a bit more curiously.

I heard a nervous giggle in her tone of voice. "I just overheard Jared speaking to one of his friends," she told me.

"About what?"

"About you!"

"Me? Why? What about?" I now asked sitting up straight in my chair. "Oh my God Susan, he didn't see me standing there behind his door did he?"

That made her laugh, and gave me a little relief at the same time when she did.

"No, at least I don't think so, he never mentioned that to his friend, but I did overhear him saying something else about you."


"You want the Readers Digest condensed version? Or the entire story?"

At least she was teasing me, so that was a good thing. Not something Apocalyptic or earth shattering ... at first.

"Since I really am sitting down, how about you give me the long version?" I asked now quite curious as to what Jared had told his friend.

"Got batteries for your vibrator?"

"Susan!" I now spat into the phone actually getting irritated with her.

"Ok, ok ... but even I have to admit, it was pretty horny hearing what he said to his friend about you."

"Which was?" I said still sounding a bit put out, but likewise, too curious and just a little worried as to what it was he had said to remain totally angry with my best friend. Especially as she was the one about to tell me what it was her own son had actually said about me.

"Ok, word for word then ... the long version."

I sighed on my end of the line ... waiting.

"I heard him telling Peter, his best friend what he'd seen yesterday morning when he came into the kitchen."

I didn't say it, but I was thinking it. "So what ... he saw my hard nipples, what men wouldn't look if given the chance if they were to walk in on a woman who did?"

She had continued on however, and it took me a moment to catch up to her, stopping her when I realized what she said.

"He said what again?"

I heard Susan snicker. "He told Peter, that he wished he could squirt his cum all over your hard stiff nipples, and then eat you out while waiting for himself to become hard again, and then have you be the one to take his virginity after that."

"He said that? He actually said that to his friend?"

"Not only that honey ... but he also said he was laying in his bed, masturbating while thinking about you. He'd even left his door open a little, hoping you might walk by, look in and see what he was doing. If you had of, he'd have pretended not to notice you were standing there, and he'd have kept jerking himself off until he came, just so you could watch it."

"Oh my God! Then that means..."

"Yeah, he had actually hoped that you would. Obviously he must have known you did pass by his room, though I'm not sure he ever knew if you ever peeked in and actually saw him. But he was certainly hoping that you would."

"Jesus Susan! I'm not sure what to say, what to think about this. Fuck, what can I say except to say I'm sorry!"

"About what? About being the focus of my son's fantasy? Why should you be sorry about that? He's only human ... and like anyone else, has and entertains his own thoughts."

"Yeah, but if I hadn't been sitting there with my tits poking out..."

Once again Susan laughed. "Oh honey ... get real. I have a sneaking suspicion this has been going on a hell of a lot longer than either one of us has even realized. I am quite sure he's had a crush on you for a lot longer than this, and has no doubt shot several of those wads of his I've been forced to wash, just thinking about you. Which reminds me. I guess that means that you're actually responsible for all that additional laundry I've been having to do lately. Maybe I should bring over all his cum-hankies and let you wash them up for him instead!"

"You know Susan, you can really be a little shit when you want to be, you know that?"

Once again she laughed, but then so did I.

"Anyway, that brings me to the real point of this call."

"Which is?"

Once again she paused. And this time she didn't giggle, serious when she spoke.

"How'd you like to fuck my son?"

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