A Penny for Your Thoughts

byMany Feathers©


Once Gayleen had unbuttoned her blouse, she leaned forward reaching around behind herself, unclasping her bra. It fell away, slithering down her arms like a sensual serpent. She then removed it, along with her blouse, now sitting there topless. Her breasts indeed weren't overly large by any means, but certainly more than a simple handful. One thing I loved seeing almost immediately however, was just how large her nipples were. Areolas a nice rosy-color, sitting atop each breast like a small pancake. Nipples capping each, thick...invitingly hard and erect, just begging for attention. As much as I wanted to reach over and touch one, I refrained however. That may perhaps...come in time. Right now, I knew it was best to simply follow her lead.

She again paused only briefly, allowing me this intermittent look. I ensured that the look of surprise, and then pleasure on my face had registered with her as she then reached down unbuttoning her fly, unzipping her jeans.

"Well? You going to join me, or just sit there with your tongue hanging out?"

I grinned at her, trying hard not to leer, and then unbuckled my own jeans, slipping them down around my ankles, just as she did. The two of us now sitting there looking at one another, albeit a bit awkwardly, nervously at first. My hard cock throbbing however, dancing all on its own accord as she lowered her gaze away from my face, now focusing on that more directly. She sighed, a small moan escaping her lips. One hand almost automatically coming up to capture her breast, watching her do that, wishing it was my own as she began fingering it, toying with her nipple. Her other hand now down between her legs, the tip of one finger slowly drawing itself upwards through her hairless little groove. I fisted myself, squeezing, producing a nice fat dollop of precum smearing it about the head of my dick, thus further stimulating myself in doing so.

"God you're hard!" She exclaimed suddenly, finally breaking the momentary silence that had fallen between us.

"And horny, but you look pretty hard too," I motioned, looking at her thick fat nipples as she continued playing with them, teasing each back and forth. "I take it...they're pretty sensitive then? You enjoy having them played with?" I asked, my tone of voice a bit deeper now, more husky.

"Oh yes...yes I do," she groaned back, playing with them even more noticeably now. Actually pulling on one of them, stretching it out a bit, lifting her soft firm breast in the process before letting go, and then doing it all over again. "I've always enjoyed having my tits played with...you, you can touch them if you'd like," she then informed me.

I reached over, again glad I had waited for the invitation, now fondling her neglected nipple and breast as she continued playing with the other one, still fingering her pussy, toying with her clit as she now rubbed that hard little knob with gentle teasing motions. She too was wet, very wet. Applying a bit of her own special sauce to her clit, just as I was doing to myself. We could each hear the slickness of our own juices as we sat there. Mine, a squishy slick sound as I slowly pumped my prick up and down, taking time in doing it, not yet ready to stroke it as urgently as I might.

"I love the way that sounds," she told me. "I like hearing it, feeling it...making it do that," she added.

"Feel free," I then said. "But don't feel like you have to or anything, only if you want to."

Gayleen licked her lips, and then withdrew her hand from between her legs, now reaching over. I felt the softness of her small delicate hand wrapping itself around my stiff, turgid member, once again squeezing it, producing another nice bubble of pearly liquid. She now took that, smearing it about my shaft just as I had done. She pressed, the squish sound produced, giggling as she did it, doing it again.

"God that sounds naughty."

"Yes it does, just as naughty as your pussy sounds when you were fingering yourself," I added to that.

"I like naughty."

"So do I."

"Finger me. Finger-fuck my pussy...my cunt!" She said hotly. "Go on Brian, finger my fucking cunt!"

We sat side-by-side there on the front seat of my car, not only watching one another masturbate, but masturbating each other! It was more than I had honestly hoped for or expected. But it had proven to me, that with a little concentration, patience, and a willingness to simply direct things, most of the time, people did...and would. It would be far easier now of course to continue more of this in the evenings with Gayleen, which I certainly planned on doing. But now, even as I fingered her to a nice little climax, and as I likewise sat back, enjoying the pleasure she gave me as she stroked me off, purposely drenching her cute gorgeous tits with my semen a short time later, I was already planning another test. And this one a bit more risky perhaps. A subject who I knew would be a lot harder to control, to manipulate, or get them to let their guard down more likely. Even as I sat there squirting all over Gayleen's boobs, I was already planning my next conquest.


Though Jerry and I had remained good friends throughout the years of course, with the passage of time he'd eventually gone on his own way. He was currently attending University out of state, and had been for almost a year now, though it had been almost two years since the last time we'd even hung out together. I still saw his mom from time to time however, always asking her how he was doing, what he was up to, things like that. I'd always considered Jerry's mom an attractive woman, though she certainly didn't dress the part. Not exactly prudish perhaps, but certainly conservative. She went to church every Sunday, but I'd been around her enough to know she wasn't overly religious either. She cursed on occasion, though always apologizing for having done so immediately afterwards. Though even her curse words were the mild ones, never once an "F" bomb, though I could say pretty much the same thing for my mother too.

But I had picked out Jerry's mom, Carol, as my next unsuspecting target.

Carol was perhaps in her late forties to early fifties even, though I had never asked. Either way, she certainly didn't look it. She had dark brown hair, shoulder length, and a reasonably nice figure, from what you could make of it. Most of the time, as I said, she dressed conservatively. I don't recall a single time when I'd seen even a hint of cleavage in anything she'd worn. And yet she had large breasts, easily a C or even a D cup. The fact I had very often hung around her, talking to her while waiting on Jerry to either finish up with some chore, or even get home from practice after school, gave us some history and background together. In many ways, she had treated me from that time on almost as though I was another child of hers. Not that I minded. Like I said, even back then I was starting to appreciate the MILF thing, even though no one had called it that yet.

Now all I had to do was come up with a good enough reason for going over there, and visiting with her for a bit. That...and do it when I knew she and I would be all alone. Jenny, my boyhood sweetheart, well sort of anyway...was still in high school and a member of the cheerleading squad. I knew from my own past experiences there, she had practice three days a week. Today was a Friday, so I knew for sure she did, if not actually a game even though I'd lost track of following any of that. Either way, I felt sure we'd be alone. As far as Jerry's dad went, that was a no brainer now either. Like a lot of people perhaps, Carol and Mike had gone through a rather messy divorce nearly three years ago now. I had to wonder, reconsidering Carol if she hadn't inadvertently contributed to that. Mike had been having an affair with a woman half his age, and once discovered, it was over with. Just like that. Jerry's dad had moved out, and they all got on with their lives as best as they knew how to. Including Carol, who'd now gone back to using her maiden name, though I honestly had no idea what that was. But that too, gave me something else I might be able to use on her as I sat there thinking about what I was going to attempt to do.

Needless to say, it would be a tough one, given I only had the fifteen, maybe twenty minutes I had to work with here. I'd not flicked my Bic for the full twenty four hours needed so to speak, and then grabbed one of my many "Magic Pennies" as I still called them out of the jar in my room, just in case. I didn't recall seeing Carol very often wearing jeans, let alone anything else that might have copper in it, so if nothing else, then the penny would have to do. I then called her, surprising her perhaps, but laid out a story about possibly going to the same university Jerry was attending, or maybe even the one I know she had gone to, graduating from UCLA as Jerry had once told me. I had in fact been working towards doing that, earning the extra money I'd need, saving up for it with the intention of enrolling in the fall. As I'd hoped, Carol was excited, anxious to see me, so I promised to come over that Friday, sit down and visit with her.

As she usually did of course, she met me at the door with a big hug and a kiss. A chaste one of course, usually on the cheek. She invited me inside for a glass of lemonade to go along with our chat of course, and then took our glasses into her informal little sitting area just off the kitchen area where she preferred entertaining. I knew for a fact that Carol didn't do a whole lot of entertaining these days, wondering how long it actually had been for her, since she'd entertained much of anything.

"So...Mrs, Ms...gee, what do I call you these days anyway?" I asked trying to sound innocent about it. Jerry told me you'd taken back your maiden name, but I'm not sure he ever told me what that was."

She laughed at that, blushing just a little. "Oh for heaven's sakes Brian, the days of you calling me Mrs. Davis, or now...Ms. Peterson, are long gone. Just call me Carol, I think we're way past formality now, don't you?" I smiled at her nodding my head.

"I'd like to think so," I assured her.

"Now, what can I help you with?" She asked curiously. And of course I then told her I was as yet undecided as to which school I might want to attend, my choices now pared down to where Jerry was going, along with UCLA, where she had herself graduated from, and one other, a bit more Midwest, though that was a long shot the more I'd been thinking about it.

"So...what was it like going to UCLA anyway?" I asked. "I've heard...it's quite the party school," I stated shyly. "Which surprises me, as to why you went there," I then added as I began setting things up. I hadn't as yet "flicked my Bic" of course, not wanting to waste any precious time here, getting the chit-chat out of the way first, setting up the direction I hoped we'd soon be taking before doing that. My Penny, already handy and available for when the time was needed. I had already noticed she wasn't wearing anything with copper in it, so the penny would have to do.

"Well believe it or not Brian, back in my college days, I was actually a bit of a party girl back then. Did some things I'm not exactly proud of now, got into a little trouble for it in fact, nearly getting expelled even. But...I soon after got my act together, changed my ways, buckled down and graduated. And stupidly...got married," she'd added taking a breath, and then looking flustered. "Not that I have any misgivings about getting pregnant, giving birth to Jerry, and later Jenny. Not that...just that, well...you know how it is," she left off saying.

"Yeah I know, and I'm sorry about that. But you Carol? A party girl? I'm having trouble seeing that," I laughed just a little. But she was already lost in thought perhaps, remembering back now.

It was time to flick my Bic. I'd been holding the penny in my hands, and now charged it. I pretended to reach into my pocket as though getting it, and then held out my hand to her. She looked at me.

"Here, open your hand." She did so. I dropped the penny into it, she looked at it, and then at me. "Penny for your thoughts?" I asked.

Almost immediately I got a sense of embarrassment and shame even. Brief fleeting images, a drunken party perhaps, plenty of nude men and women running about, squealing, chasing one another. And then this image of Carol, a much younger Carol, the way she saw herself perhaps, remembering, though even that image tended to flicker back and forth between that one, and the way she actually looked now. She finally snickered a bit. "Oh Brian, I dare not tell you those thoughts," she stated moving about in her chair as though suddenly uncomfortable. "Like I said, I was a different woman...a different girl back then. I did things, like I said, that I shouldn't have." I sat listening, or appearing to however, now slowly worming my way into her thoughts, like a shadow in the back of your mind, whispering to her, using what I saw, what I felt, what I sensed to draw her out more and more.

"It still excites you to think about though," I told her. "Things you did, the pleasures you felt, so long ago now. How long has it really been Carol? Since you've allowed yourself to feel that way again? To experience that kind of exquisite, joyful pleasure? How long? Certainly what you did wasn't that bad now was it? Haven't you made more of it than what it actually was? When are you finally going to let go of that, quit brow-beating yourself with it?" I pressed, now seeing the struggle, sensing the emotions as memories of that time came flooding back to her.

"Oh come on Carol, it can't be that bad. Can't be any worse than some of the things I've done myself, now can it? Doesn't everyone experiment in one way or the other? Try things? Do things? Some of which we may latter regret yes, but isn't that how we learn who we are? I'm sure, knowing you...it isn't half as bad as your making it out to be."

"Oh Brian, seriously honey...you have no idea. I really did do a few things that I regret. Not all of them of course, but some. And yes, you're right, I do sometimes think about those times fondly," she stopped herself looking at me. "You...you did ask me that right?" She suddenly questioned, not at all sure now if I had asked, or if she'd just offered something she shouldn't have.

Like I said, this could get interesting, but I needed to tread carefully here, and we were still on borrowed time as well. I knew then, this might take more than one session to make any real progress with. It might be better to take it slow and easy with her as opposed to trying to force anything too quickly. Though I did decide right there and then to try and plant the suggestion, along with the determination to tell me what happened, seeing me as a friend, someone she could trust, share this long held secret with.

"Go ahead Carol, you can tell him. He'll listen, he'll understand, and he won't judge you, or think ill of you for sharing something with him, something a bit naughty, a bit dirty...about your past. It's ok, he's old enough now, far more mature than his age even. He's always liked you, admired you. Hell, you know deep down inside, he's even been a little bit attracted to you, sometimes hanging around, flirting with you in that little boy way of his he once did. He's your friend...go ahead, tell him. Tell him what you did that you think was so bad. He'll listen, he won't judge. If anything, he'll think it's way cool that you did that."

It was like watching her talking to herself, only it was listening to me, she continued to struggle a bit, weighing the consequences perhaps, and finally...finally...accepting it.

"I can't believe I'm actually going to tell you this Brian, but I think you're old enough now to hear it and not judge me for one thing. But for another, there's no one else I can possibly even image telling this. It's something I've held onto for years, struggled with. But maybe, maybe telling you...telling someone about it, will help me see it in another light."

I sat back, pleased with the progress I had made, though having less than half the time left before the Penny wore out. The penny she still held in her hand like some sort of amulet. Which in a way, it was. But maybe, just maybe...it would be enough. One more prod. "Go ahead Carol, tell him, and don't hold back. Tell him everything, spit it out, don't be afraid. He will understand."

She seemed to settle into it then, finally having made up her mind, with some encouragement from me of course, and began, relaxing in her seat after taking a sip of her lemonade. "Believe it or not Brian, I once belonged to a rather prestigious Sorority. I won't give you the name, as I don't wish to blemish them further with my own wrong doings. But needless to say, it was shortly after my...my misfortune, that I was asked to leave. Something that I have had to live with to this very day."

"Go ahead Carol, tell him. Spit it out, tell him everything, all the gory details. It won't shock him, offend him...you can do it, spill it, you'll feel better." I could feel the energy starting to weaken. The link between us not quite as strong. I relaxed it a little, buying a bit more time, something I'd recently learned how to do. Just barely holding on, no longer able to suggest anything anymore. But perhaps I had done just enough. I could still hear her thoughts, which might help me in redirecting our conversation if I had to.

"I'm not sure you'll want to hear this..."

"I do. No matter what it is you have to say or tell me. I really, really do Carol. I can see that it's something that's been bothering you for quite some time now. Listen, we're friends, just not neighbor's, and least I'd like to think of us as being that. Good friends, close friends, someone you can share a secret with, say something to, and know they won't go out and tell anyone else about it. I'll promise you this Carol, you share yours with me, and I'll tell you a secret I've never told anyone else!"

She actually smiled at that, now grinning, nodding her head. "Ok, just remember I warned you, but I'm going to hold you to your promise to tell me what your secret is afterwards," she stated.

"I promise Carol. I will."

"Still can't believe I'm actually going to tell you this, but ok...here it is Brian. Like I said, back then, I really was a bit of a party girl. Some people might even call me easy, though I'd still like to think it wasn't like that. But I did enjoy doing certain things, admittedly. And I didn't see that as being much worse than anything any of the other girls were doing back then either. So it's not like it was all that bad, even now...I still don't see it as such. Only what happened, what I got more or less trapped into doing, all because of a stupid bet. A bet I lost, and out of some sort of twisted, false pride and vanity perhaps. It was a bet I felt I had to honor and live up to."

"Which was?"

"That I had to blow every single guy in the Fraternity we were associated with, or at least those who were willing to go along with it anyway. Blindfolded mind you, so I wouldn't ever really know who I had...or hadn't. But I did Brian. And I'm ashamed to say it now, but I enjoyed it. I enjoyed every moment of it. Kneeling there naked in this little room, hands tied behind my back. One guy after another coming into the room, the sensation of a different dick perhaps, each one fucking my face." She stopped, obviously surprised with herself, her face deepening in color, even more embarrassed now, realizing she'd just dropped the "F" bomb in front of me. "Oh my god Brian! I got carried away there for a moment, I shouldn't have said that."

"What? Fuck? I happen to like the word, and not in a mean way either. I think it's sexy personally, I like hearing it, saying it...especially when I'm horny. Don't you?"

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