tagFirst TimeMy Best Friend's Mother

My Best Friend's Mother

byMany Feathers©

Danny would kill me if he ever knew, ever found out...I had watched his mom pleasure herself. Bad enough that, but that I had in turn, jerked off watching her do that, though of course no one would ever know. Certainly never my best friend Danny, though we had years ago sworn to one another as kids growing up together, we'd never lie to one another, or keep any secrets.

Up until now.

And it's not like I was looking for it, or expected it to happen. It just did. But once it did, once it had, I couldn't keep the image of it out of my mind, no matter how hard I tried. And worse...going over there which I so often did, now speaking to her as I also always did...there was that secret hidden longing deep down in my gut that wouldn't go away. Even seeing her dressed, in things I'd never thought or considered her sexy in, now were. But even more surprising, I could see her as though she didn't have a stitch on. Busily in the kitchen baking cookies, or ironing as she watched her soaps on TV, naked...always naked. I could see her soft mature breasts dangling so provocatively on her chest as she smoothed the iron along one of her blouses, or one of Danny's shirts. Her nipples hard and erect, just the way I'd seen them, begging to be kissed, sucked and fingered. That small tuft of hair between her legs, not shaved like so many women were wearing it these days, not quite as unruly either as some of the women I'd seen in that stash of 70's porn I'd stumbled into in my father's closet. No...not quite like that either. Trimmed, cropped...sort of secret like, and yet...hiding the passage to her desires like a door that could only be opened with a special key. A very special "clit" key as I now called it, remembering that moment and that day, just days ago now.

Danny had gone to spend two weeks with his father as his mom and dad had gotten divorced two years previously. It meant a semi-lonely period of time for me while he was away, few others our age living close by, and especially with the two of us having recently graduated from high school, it meant a lot of free time on my hands with nothing much to do. Though I did work part-time, and supplemented that with doing odd jobs around the neighborhood, I missed the evenings when we'd usually go out and hang out together.

And at the moment, I didn't have a girlfriend either, making it even more boring for me.

I had gone up to my bedroom to spend some time amusing myself, browsing a few websites. Most of which were adult in nature, and of those...most all of which were MILF sites, as I had a secret thing for older women. Especially one in particular, though again, I had never acted on it, or ever intended to. Beverly Mason, though everyone simply called her "Bev", was after all, my best friend's mother.

After browsing a few sites, I was now horny and bored. I walked over to the bedroom window standing there glancing down and about. Normally, I didn't usually see much of anything, a single lone window facing me from my friend's place that gave me an angled view down into their family den. Tonight however, I got a brief glimpse of something that would forever change my life. For the briefest of moments, I saw Beverly cross the room holding a glass of wine in her hand, and then lean over in front of the TV, obviously putting in a DVD into the player. The thing about this was, she was naked when she did that. The view of her lovely heart-shaped ass, nearly stopped my own as I stood there holding my breath. It was only seconds as she then turned heading off towards the couch. Once she had, she was completely out of sight. But what I now saw there on the TV, even at this distance, was what was obviously some sort of porn movie. And that was a surprise in and of itself. Danny and I had certainly looked for "stuff" to amuse ourselves with, but never figured his mom would have anything like that hidden away at their place. Most of what we'd found and discovered had come from my dad's stash of X-rated stuff.

"What the hell?" I thought to myself. "Danny's mom's watching porn?"

I knew that there was one for sure way I could see more, especially now knowing she was naked, though I hadn't gotten that good of a look. And having seen what I had seen, I now knew I had to see more, risky as it might be. This was plain and simply too good of an opportunity to pass up.

I was scared shitless as I made my way downstairs, informing mom and dad I was heading off to meet up with some friends. Now that I had graduated, coming and going as I pretty much pleased, especially working and for the most part paying my own way, gave me a lot of unsupervised freedom and flexibility.

The moment I stepped outside through the backdoor, I immediately hopped over the fence after first ensuring no one was around, or would have been able to see me do that when I did. With plenty of coverage from the high fence and bushes running around their yard, I cautiously and quietly made my way over towards the back of the house where the patio was. I knew from having been there countless times before where my best vantage point would be in having any hope of seeing her. The risk of course being caught as a Peeping Tom, a sexual pervert no doubt if I was, but the thought of actually getting to see the object of so many secret fantasies was a temptation simply too great to ignore.

Almost crawling on my belly now, I made it all the way over to the sliding glass doors before even daring to look up and into the room. A small step gave me minor concealment, but I knew that once I was there, I'd be able to see into the den easily. Like I said before, I knew the layout, and had a pretty good idea where she would be sitting, watching the TV. Sure enough, she was, and what I now saw blew me away!

Bev was lying on the couch facing towards the TV, though where I crouched it was sitting sideways to me, so I couldn't see it. But...I could certainly see her well enough. And to my relief, I now realized she would have to actually look up and turn her head back in my direction if she were to inadvertently see me. A small advantage then, as any motion on her part to climb off the couch, positioned as she was, would give me plenty of warning.

The thing was, she was so lost in what she was doing at the moment, I think a bomb could have gone off, and she'd never have been aware of it. And that meant, I could sit there unobserved (somewhat in a state of shock) and take in something that I never thought in a million years I would ever be privileged in seeing.

Up until now at least, I'd only gotten a few subtle hints at to what her boobs might look like, but the surprise there was, they were a bit larger than I'd even imagined, though they had flattened out a bit as she lay on her back, indicating their fullness. Even more remarkably however, was the fact she was at the moment wearing nipple clamps. Both of her dark pink nipples clearly pinched, or being pinched at the moment anyway. Two thick fat eraser like nubs sandwiched in between, hard and stiff and proud looking. Bev's shoulder length dark hair spread out sensually on the pillow she was resting on, one leg casually thrown up over the head rest of the couch, the other bent at the knee off one side resting on the floor. It was evident she was sliding something in and out of herself as she lay there watching the TV. And then she took it out for a moment, actually sucking and licking it, licking her own juices off what I now realized was a glass dildo. Seeing her do that, made me realize just how fucking hard I was, wishing it was my cock she was doing that too.

Setting the glass dildo off to one side, she now reached down grabbing something else that had been hidden from view. That one I recognized having seen plenty of them in movies and magazines, and certainly off the Internet. She now held a long slim silver colored vibrator in her hand, which she turned on. And though I couldn't hear it, it was obvious by the way she now closed her eyes, gently running it around and over herself between her legs, she could certainly feel it.

A bit more relaxed and less fearful at being discovered, I moved up into more of a crouching position, still easily able to duck off and away to one side should I feel it necessary to do so. I unzipped, reached in, and withdrew my own very hard needful cock, and then began stroking it as I watched Bev continue to tease herself with the toy. As hot as this all was however, and exciting as it was for me to be sitting there watching it all, it got even better seconds later. Much to my surprise, I now watched as Bev again reached down beside the couch, this time lifting up what appeared to be a hand-held mirror. I couldn't believe what I was seeing, it was horny, naughty, and hot as hell. Bev was now watching herself as she placed the tip of the vibrating toy directly against her clit, holding it there. And then that's when she picked up the glass dildo, and slid that one deep inside that wet looking passage just beneath. Once she had slipped it inside her as far as she could, she went back to teasing the area around her clit with the other one. I watched all this, watching her do this only a few short feet away, close enough to pick out quite a bit of detail as she did so, furiously pumping my prick up and down the entire time.

When she came, it startled me, mainly because it was the first real sound I could easily hear. Obviously loud enough to have made it's way through the glass doors to me. The thing was, I jumped a little in surprise, lost my balance, and toppled over sideways off the step into the bushes off to one side of the door. I rolled, jumping up, and sprinted off like a man possessed easily clearing the fence separating our two yards from one another. Hunched down on the other side, I peered through one of the knotholes looking back. Sure enough, I saw the sliding doors open, as she peered out into her backyard, though she was now wearing a robe, holding it closed together in front with her hands.

Skate, their cat...like a godsend, just then came bounding across the yard, chasing insects perhaps. Though spotting Bev, stopped and came strolling over towards her.

"Naughty cat!" She laughed. "You scared the hell out of me!" She said chastising him and then letting him inside. "For a moment there, I thought we had visitors!"

I managed to swallow the lump in my throat, and then made my way back inside the house with my heart beating a hundred miles and hour.

**

I stayed away for three days, not daring to even accidentally bump into her, just in case she'd been wondering and not actually blaming the cat. And besides, I had no excuse for going over there anyway, not with Danny gone. But come Saturday, I did. On Saturdays I always mowed their lawn by way of picking up a little extra spending money. So, as I always did, I went over needing to get the key from the shed in order to use their mower. I stood on the back porch, knocked and then waited only for a moment when Bev finally came out to invite me in.

"Been a while since I've seen you last, how've you been doing?"

"Fine, thank you," I responded back. "How's Danny?"

"Talked to him this morning in fact, he's doing fine...told me to tell you hello next time I saw you, which I figured I'd do today if you came over to mow the lawn."

I had a hard time keeping my eyes off her breasts, even though she was dressed, I could still see them as clearly as I had then. With one more button undone than perhaps she should have, it was hard not to, taking a quick peak down her blouse as she moved about, leaning forward briefly as she sat down at the kitchen table sitting across from me.

"By the way...I just put come cookies in the oven to bake, when you're done with the lawn, perhaps you'd like a couple, along with a glass of milk."

"I'd actually prefer coffee," I told her, which I did prefer, but which I also hoped would let her know I was a bit more grown up, way past the glass of milk and cookies stage. She did smile at that, nodding her head.

"Yeah, me too," she replied actually winking at me.

I finished the lawn up in short order, coming back inside just as she placed the fresh-baked cookies on a plate, and then on a tray, along with two steaming hot cups of coffee for each of us.

To my surprise, she then led me into the den where we could sit more comfortably. "Have a seat," she stated indicating the couch, taking a chair across from me, the coffee table between us where she placed the tray down. "How do you like it?"

I was looking at the couch, my thoughts elsewhere. "I'm sorry...what?"

"How do you like it? Cream? Sugar? Black?"

What I wanted to say, was I liked it if she'd get on her back...with lots of cream. "Black," I said instead, accepting the cup along with a cookie, which she held out to me as I sat back on the couch. Doing that however, I felt something dig into my bare leg as I was wearing cut-off shorts. I reached down towards, and in between the cushions where I'd felt the small stab into the back of my thigh. I came away with what I knew now...was one of her nipple clamps. It took me a moment to realize what I was holding as I held it up. It took Bev two seconds after that to likewise comprehend what I was sitting there dangling in front of her. Her face turned scarlet, her mouth open, though no words came out.

"Here," I said blushing. "This must have fallen off the other night."

The moment I had said that, I knew I was dead-meat.

"So it wasn't Skate after all...it was you!" She declared glaring at me. I didn't know what the hell to do, or say...feeling glued to my seat on the one hand, but wishing I could simply turn invisible and then simply disappear. "Oh my!" She then added seconds after that, her face turning crimson, as she must have then realized what I had seen.

"I'm...oh god, Mrs. Mason, I'm sorry...I didn't mean..."

She sat there staring at me as I tried to stammer out some sort of an apology.

"Yes you did," she said simply sitting back in her chair. "Obviously you knew...saw me, and came over to peer through the doors at me, while I...while I touched myself," she said her voice taking on this weird little edge to it. An edge that could easily cut either way, and one in which had me wondering which way it would cut. I could just see her picking up the phone, calling my folks. But she didn't. Instead, she reached up, undoing another button on her blouse. Talk about confusing! "And just what did you see...exactly?" She asked. "And more importantly, what were you doing while you did?"

I was honestly speechless, caught betwixt and between here. "Where you jerking off?" She demanded. "Come on Robbie...tell me, where you?"

"Yes, yes I was!" I finally blurted out, shame-faced, disgusted with myself.

"I see," she said sitting back in her chair again, staring at me, though still fingering that damn button on her blouse as she did that. Several long moments passed without a single word between us, and then she spoke again. "So...what do you think we should do about this?" She now asked as she popped the button free, revealing the contours of the lacy bra she was wearing as I sat staring at her chest now.

"I don't know," I responded back, though by the look on her face, that wasn't the answer she expected to hear from me. "What can I do to make it right?" I then added, to which she smiled...slightly.

"Take off your clothes."

"I'm sorry...what?"

"You heard me, take off your clothes. You saw me vulnerable, naked...being intimate with myself. And for that, now you'll feel what it's like having someone looking at you while you do that."

"I can't!" I said shaking my head. There was no fucking way!

"You can...and you will, unless you want Danny to find out his best friend spied on his best friend's mother, jerking off while he did."

I was about to call her bluff, stand up and leave...but then I saw the look in her eyes, she was serious, she would tell him I had. She wasn't bluffing! And that would be the end of our friendship, forever! I did stand up then, but I undid the belt on my cutoffs, likewise popping the button on them, releasing them. They fell down around my ankles.

"Everything," she said with that same fierce look in her eyes. I pulled the tee shirt I had on up and over my head likewise kicking off my shoes. All I had on now was my briefs and a pair of socks. But I knew I wasn't getting out of this either. I was embarrassed as hell, but in a really strange way. Not so much for being naked in front of her, because I knew I would be in a moment. But because I was limp, flaccid as hell, and worried now of all things that she would see me, and treat me like that same little boy she used to know.

All I could do now was grin and bear it. I slipped off my briefs, and then my socks, now standing there facing her directly, eyes closed. I stood in complete silence, not daring to even open them, certainly not to look at her directly.

"Sit down," she now said, which I did almost gratefully...now given the opportunity at least to partially cover myself. "Stroke it...make it hard."

"Jesus! Bev, Ms. Mason," I corrected, shocked at what I'd heard. "You can't mean that!"

"I most certainly do! Now do it! Find out what it feels like to have someone else watching you, watching you while you pleasure yourself, see how it feels...see how I felt, how I feel now," she said sternly.

This wasn't for fun...this was payback. Her eyes told me so, as did the tone of her voice. If jerking myself off in front of her was the only way I was going to get out of this mess I'd put myself into, then I was sure as hell going to do it. I began stroking my prick. It took a moment...lots of moments in fact, but finally it began stiffening as Bev sat back in her chair a bit more comfortably, sipping her coffee, watching me.

"For how long?" I eventually asked, wondering if she wanted me to go all the way with this.

"Until I say otherwise," she said simply. "Let me see it," she said suddenly standing up walking over.

"Surely you can get harder than that, you're young, virile, and you're supposed to get steely hard. Fuck, even Jeffry could get harder than you are," she said referring to Danny's dad, her ex-husband. But it was hearing her say the word "fuck" that really surprised me, and oddly enough, sent a renewed bolt of unexpected desire, and now want...surging up my cock. It stiffened a bit more, but even that didn't seem to appease or please her much. But it was a war of nerves and anxiety for me, sitting there stroking my dick in front of her, and yet...scared shitless and still too damn embarrassed the entire time.

"Here, will this help?" She asked, and then sat down next to me, though hugging one end of the couch. As she did, she finished unbuttoning her blouse entirely, removing it, and then reaching behind unclasping her bra. It fell away, her gorgeous...and I mean gorgeous bare breasts suddenly confronting me.

"Holy shit! Wow!" I exclaimed without thinking. "You really do have fabulous tits!" I stated without hearing my own words as I said that. What happened then, was amazing. She laughed. Laughed out loud and hard.

"Oh they are, are they?" She asked suddenly filling her hands with them, lifting them up pressed together. "Not too saggy? Too floppy for an old lady like me?"

"You're not old...and they're sure as hell not saggy...or floppy, they're beautiful!" I exclaimed again, though I didn't have the heart to tell her I was actually staring at the first pair of real-live boobs I'd ever seen either. Up until now...all I'd ever managed was to feel up Christine Johnson's tits, and that was in the dark in the front seat of my car, through the sweater she was wearing. So far...that was the extent of my on-hands experience. I was still...a virgin.

I was still staring at them, not even realizing I was still slowly stroking my cock up and down as I did that. But one thing was for damn sure...I was rock hard solid now. And she saw that I was too!

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