Friends with Benefits

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Jack finds the best friend ever.
12.2k words
4.68
58.4k
25

Part 2 of the 2 part series

Updated 09/22/2022
Created 06/27/2006
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Many Feathers
Many Feathers
10,461 Followers

I had gotten divorced several years ago, and since then had preferred remaining single living alone. Although I was in my early fifties, I was still in pretty good shape and had been told I had "bed-room" eyes, whatever that meant. I had certainly enjoyed the occasional fling here and there, but had shied away from anything long-term, which had severely limited my options. I was almost content to remain far more intimate with my own hand, until the perfect woman came along. And to top things off, she'd been living next door to me for several years now.

I had guessed Jocelyn (though she preferred being called Joy) to be in either her late thirties, or early forties, though I had of course never asked. They had lived there next to me for several years, Joy and her husband Dave, along with their two daughters Amy and Rebecca. Ironically, my ex-wife and Joy had become fairly good friends, though I hadn't much cared for Dave since the day I had first met him. He was an alcoholic for one thing, but he was also fairly abusive to his wife, and most likely the girls as well. I had felt bad for what I knew was going on, but there was little that we could do about it, except to be there for them in support. Or... if things got even more abusive than we suspected, to step in if necessary. Thankfully, that never happened. Ironically, other things did.

In time, I think I became better friends with Joy than my own wife was. After she had kicked Dave out of the house, I'd begun doing more and more to help out whenever I could. Something that Joy and the girls had very much appreciated. Like I said, we'd eventually gotten to the point where we could sit down and have a cup of coffee and discuss just about anything. I'd come to respect and appreciate Joy's honesty, and openness with me, which is maybe why things had become a bit strained between Cindy and me. I had a much better relationship with the next door neighbor than I had with my own wife. And oddly enough...there wasn't a damn thing going on between us, not even once hinted at.

And to be honest, maybe it was because of that, that I didn't see things coming, or what was happening in front of my own face. But Joy had. And eventually it reached the point where she felt it was necessary to open my eyes a little, as hard as that was for her to do. I had just finished mowing her lawn and had stepped over to accept a glass of fresh lemonade from her when she asked me to take a seat at her patio table. I could see by the look on her face that she was troubled, especially by the way she seemed to fidget around in her seat, even spinning her own glass of lemonade around in circles, trying to find the courage to say whatever she was going to say perhaps.

"What is it Joy? What's wrong?" I finally asked, forcing the issue. She took a sip of her drink, and then set it down, trying to steady herself.

"I've really struggled with this for a long time now," she began, looking even more nervous and confused.

"Go on," I said steeling myself, though again...some deep-down part of me already knew where this was headed.

"I didn't want to say anything to you, until I was sure. After everything you've done for us...the way you've been there for us, and the good friend you've become to me after Dave finally left. The last thing I ever wanted was to say or do anything to hurt you, or cause you pain. Until now."

Now it was my turn to sit back, and spin my glass in circles waiting for her to continue.

I can honestly say I really had few vices, save for one perhaps. I loved to golf on Sundays. I made a good living, enough so, that Cindy had whatever she wanted, whenever she wanted it. Maybe it was my way of trying to keep things even between us, since I felt that I did more than my fair-share, not only with work...but around the house too. So spending half the day golfing with my friends on Sunday's didn't seem like a whole lot to ask. And Joy of course knew all that.

"At first, I didn't really think too much of things..." she began again. "Sometimes I would see you leave in the morning to go golfing. And then not ten or fifteen minutes later I'd see Cindy leave. I figured back then, that maybe she had something going with a group of friends, though I found it a bit odd she never mentioned anything to me about that as close as the two of us supposedly were. The thing is, I began to take a closer notice of it. Always on Sunday, shortly after you left, she would. And then she'd return in a couple of hours, long before you did. I began to notice subtle things when she did. And I hate to say that because by now I was actually spying on her, that those subtle things included her obvious dishevelment whenever she came home. Like she'd been ridden hard, and put away wet...so to speak."

As hard as this was to hear, I sat quietly, patiently, taking a sip of my drink again as though some sort of signal for Joy to continue. Which she did.

"Even with my suspicions, I didn't want to say anything. Not unless I was one hundred percent sure. Even then, I hesitated Jack. We've become good friends, and I didn't want to lose that, or do anything that would jeopardize the friendship we did have. Until the day came that she didn't leave after you left. Instead...he did. As far as I was concerned, though maybe it shouldn't have been my concern, the moment I saw him sneak up into the house shortly after you'd left was the last straw for me. I knew then, I had to tell you at least this much, and then let you decide for yourself how you wanted to handle it. I just hope...this doesn't destroy our friendship," she smiled worriedly. I stood up, walked over...and kissed her on the forehead.

"Thank you," I said softly. And then turned and left for home. It was the hardest week of my entire life. Trying to pretend everything was normal. The following Sunday, I left to play golf as usual, though I'd already told my friends well ahead of time that I wouldn't be able to make it as I had business out of town. The only person I had told about what was going on was my best friend Roger, also a golf buddy, and someone that Cindy had never met. We hurriedly switched cars (and clubs) and then I parked a short distance away from the house...waiting. I figured if she left, I could easily follow her. Or...if he showed up at my place instead, then well...though I had all sorts of thoughts and scenarios racing around inside my head when she actually came out. So...I followed.

To make a long story short here, I basically caught her with her pants down so to speak. I followed her to a nearby hotel. Saw her get out of the car and walk up to a particular room where she was met and quickly ushered inside. A hundred bucks, and verification of my ID to the nervous looking desk clerk, finally convinced him to run me a key. After assuring him I wasn't there to cause any trouble...and wouldn't, I took my digital camera with me, put it on video and started recording. I stood listening outside the door for a moment until I was reasonably sure they were already at it. After all, time was precious here. Seconds later I was standing in the doorway recording everything I needed to confirm what I already knew. What I hadn't known until now, was the guy she was with...a married man himself, and someone she worked with, happened to be her lover. So in the long run...I knew this would really turn out well for me if I played my cards right.

On Monday, I filed for divorce, with very specific stipulations. Yeah, in a way I guess you could say it was blackmail. Unless Cindy walked...and I mean walked...I threatened to expose her affair and who she'd been having it with where she worked. Needless to say, they both caved in at that imploring me to not say anything to anyone...though I kept my little video as insurance against that until after the divorce was final.

Six month's passed, and I had quickly gotten over all this. Though I was a bit gun-shy about really getting serious with anyone again. The occasional overnighter with someone was fine with me, though there were aspects of that, which I did miss.

And then low and behold...the solution to all this, which had been living next door to me all this time, suddenly became readily apparent. Though even then, I hadn't been looking for it...or expecting it, when it happened. Neither of us had been.

Rebecca had moved out and gone onto college shortly before all this had happened. Now it was Amy's turn to do so within the next week or so. Both girls attending the same University, out of state...which would leave Joy home alone for the very first time really. It was something we talked about, though I had ensured her of course I would always be there for her, and that she could certainly call on me, even if it was just for a little company and someone to talk to. And at first, that was pretty much the way it remained for the next month or so, until circumstance, or fate perhaps stepped in.

I had kept up my weekly golf outing with the guys. Something I looked forward to, and which helped to keep me sane. As we'd discussed, my plans were to golf, come back in the afternoon, and then spread and pour some mulch I had gotten for Joy's back yard flower beds. We'd even planned a semi-cozy little barbeque dinner with one another for later on that evening. Something else I was again looking forward to. And then fate, for whatever reason seemed to step in and take over at that point.

I had actually waved good-bye to Joy as she stood outside watering her front garden when I left. A short time later I arrived at the course, only to discover that a tournament was going on. Stupid me. I had lost track of the dates, only then realizing I thought the tournament was to be held the following week. Getting back into my car, I headed home again, surprisingly not at all disappointed at the turn of events. If anything, I was looking forward to spending even more time visiting with my dear friend Joy. I even thought about surprising her perhaps. Getting her back gardens filled in and spread with mulch before she even knew I was there. I'd begun doing just that, when by chance I happened to look up and in to what I knew was her bedroom area. I had no intention of spying on her, or doing anything like that. Nor did I expect to see what I was seeing, when I did either.

I was dumb-founded to say the least. And a bit stupid too perhaps, but I was frozen with indecision just long enough to complicate the situation even more so. Joy was naked, laying in the middle of her bed, which faced towards me. On her back, her legs spread and bent at the knee, she was currently thrusting what appeared to be a rather large-sized vibrating dildo of some sort, in and out of her pussy. I must have caught her right at the perfect (or imperfect moment depending upon how you looked at it) moment...as she began to climax. As she did, she sort of sat up, the convulsions no doubt intense and pleasurable, which is the first look I saw on her face, followed almost instantaneously by the second one...which was pure unadulterated shock. About all I could do was turn and head sheepishly back towards my own place, leaving shovel, rake and mulch behind in my wake.

I sat at my kitchen table, the image of what I'd just seen and witnessed firmly etched inside my head. I was certainly at a loss for words, or action...in what I should say, or even could say...when the phone rang. Quite naturally I jumped. And a quick glance at the caller ID told me who was calling me too. I picked up, but before I could even say anything, I heard Joy's voice coming through on the other end.

"Jack? I think we need to talk. I'll pour a coffee for you. Please come back over as soon as you can...ok?" And with that, she hung up without waiting for a response. I sat there looking around the kitchen like I'd find some sort of answer waiting for me there, or at least something to bring over. I know...I know. I grabbed a partially opened bag of Oreo cookies, and took them with me as though needing something...anything. Joy met me at the back door. Thankfully she was dressed, well sort of anyway. She had a bathrobe on, but I wasn't about to entertain any thoughts about what she either did have, or didn't have on beneath it.

My first words as I stepped inside the door. "Joy, I'm so sorry...I hope..." but she waved me off with her hand, pushing a freshly poured cup of coffee towards me, and then actually laughing as she took the half open bag of cookies from me setting them down.

"There's nothing to be sorry for Jack. And you need to know that. Now...let me ask you something." I took a swallow, and not of coffee either, nodding my head towards her, prepared to answer anything at this point. "Tell me Jack...do you enjoy masturbating?"

You could have knocked me over with a feather. It was probably the last thing in the world I expected to hear coming out of her mouth. Though I found myself again nodding my head yes.

"So do I," she smiled somewhat demurely. "Let's face it Jack, and be honest with one another. After all, we always have been haven't we?" Again I nodded. "I know you weren't pulling a Peeping Tom on me. I know it was purely by accident that you saw what you did. But I'm also not going to sit here and tell you that I'm ashamed that I do, or anything like that. In fact Jack, I happen to masturbate a lot. So it's perhaps even more of a surprise that you haven't caught me until now. The number of times I've sat out back in one of the lounge chairs enjoying myself, well..."

Now I had another image which was permanently stored. I had seen her before of course, but I had never not once stood there and spied down on her, hoping to catch anything.

She had continued...but I'd had a momentary black out as my memory seemed to pause for a moment with that image of her laying on her back again.

"I mean look at us Jack. Look how long it's been for both of us. I know in the little bit we have discussed, that we're both pretty open-minded about things. So either one of us feeling guilty, or even embarrassed about this, doesn't make any sense." She was certainly right about that. We had had some pretty interesting conversations in the past, and I had gone home more than once needing a bit of relief afterwards. Apparently, so had she.

"And just who and what do you think I have very often fantasized about when I have anyway?" She asked. Though I think I was still trying to convince myself that it wasn't me she was talking about. Until she actually came right out and said it. "Would you like to take a guess as to who I was thinking about when I was climaxing a few moments ago?" She grinned somewhat wickedly.

"Me?" I asked stupidly.

And now she did laugh, though reaching for a cookie. She dipped it in her coffee, and then lifted it towards her mouth. Only the soft mushy edge disappeared as she removed it again. It was the most sensual thing I had ever seen her do. Aside from well, you know.

"It's almost funny in a way. Perhaps even poetic."

"Yeah? And how's that?"

She leaned forward, getting ready to dip her cookie again, though this time I noticed her robe had parted just a little. Not a lot mind you, not enough to be overly suggestive or anything, but enough to hint at the fact, Joy really did have a nice pair of breasts.

"What I was actually fantasizing about, when you saw me...was just that. Walking in and catching me, seeing me like that. Pretty wild huh?" She asked.

"So you weren't mad then?"

"Mad? Are you crazy? Didn't you hear what I just said? If anything I was a little shocked and surprised yes...I mean after all Jack, the very thing I happened to be thinking about, had just happened. Had you not turned and walked away when you did...you'd have seen me continue...certainly that. Which I was quite disappointed in when you actually left. And I knew then I had to call. That we had to fix this before it got all blown out proportion and ruined everything else that we have."

"I'm really glad you did," I said taking a cookie, dipping it. Though it mostly fell off and into my cup. It was a nice ice-breaker, especially for what came next.

"Yeah, me too. But I still have another question to ask Jack, and you still haven't really answered my previous question either."

I thought back...only then realizing. "Which one do you want me to answer first?" She again laughed, tossing her head back a little, causing her robe to open even more. I now had a pretty good side-view of her left breast, just short of the hidden nipple beneath the cloth.

"Do you enjoy masturbating Jack? And how often? And what do you like to think about when you do?" She asked.

"Well, for starters...that's three questions," I grinned back at her, though answering the first two. "Yes I do...and perhaps even more so these days," I think I actually blushed. "And maybe once a day, or every other day at least," I confessed. Though I temporarily held off on answering her third question. I wasn't sure she was ready to hear about how often I had in fact thought about her, even in the simplest of ways.

"Do you...sometimes, think about me?" She asked, and then I noticed her hands coming up, the sash on her robe undone. It fell apart, fully. Both breasts now totally and fully revealed to me. I sucked in my breath and slowly let it out, my eyes still feasting on her.

"Often," I said softly almost in a whisper. "I think about you very...often."

She stood up, though scooting her chair off to one side before sitting down again. Though her robe, if anything, remained fully open as she did. I could now see a small dark tuft of hair just above her mound as she sat down again, though this time spreading her legs. Almost obscenely as she did. I was mesmerized...hypnotized by it. By her.

"Will you watch me...Jack?" She asked, her fingers slowly sliding down between her legs. One hand now spreading her swollen, glistening lips apart. The other, teasingly, tenderly even, skimming the hard shiny surface of her tiny protruding clit. "Will you let me do what I was doing? Only just fantasizing and thinking about earlier? Only this time...for real?"

I took another deep cleansing breath again, realizing as I did that my prick was hard, swollen, and now straining uncomfortably against the press of my jeans. Perhaps my glance down briefly gave that away. Though I now heard Joy's intake of breath as I glanced back at her. One hand now pinching on a hard delicate nipple, tweaking it. The other, still thumbing, strumming that precious naughty nub between her lips.

"Are you hard Jack? Are you getting hard thinking about this? About watching me? I would love to see your cock Jack. You know I would. I always have I would love to watch you stroking it, while you're watching me. Would you like that Jack? Would you like to really jerk off, actually seeing me instead of just fantasizing about it?"

I had learned early on in our relationship that Joy was one that always spoke her mind when she felt like it. I had thought then that perhaps sometimes she had divulged, or shared too much. But then I realized, she wasn't that way with everybody. Usually only with me, though I had learned she did have one other girlfriend who she had very often confided in as well. So hearing her now, hearing her allowing herself this uninhibited, unbridled discussion of her feelings and desires, wasn't all that surprising. This was Joy...this was how she truly was. And frankly, I found it refreshing. In comparison, I'm not sure I even heard Cindy say fuck...except towards the end there. And then it didn't really have the same effect as I might have liked. Or maybe...it did.

In answer to her question, I stood up, unbuckling my jeans, and then kicking them off before sitting down again. And just as she'd done, scooting my own chair out and away from the table, now sitting across from her. My proud prick standing hard and full at attention.

Many Feathers
Many Feathers
10,461 Followers