Monogamish - Realizing Her MILFdom

He got most of my back swiftly, but was being hesitant at the margins. Tut tut.

"Could you make sure you get under my arms along the side?" I asked sleepily, lifting my arms to cross under my head. "Careful though," I added with a giggle, leaving my eyes closed, looking a vulnerable as I could.

If I thought his fingers had trembled before, they were little vibrating points as he rubbed under my arms, smoothing their way tantalizingly close to the edges of my breasts. Tantalizingly close for both of us.

Just as he finished, I swept my arms down and tucked my bikini bottom's waist down just a fraction of an inch. "Don't miss right along there," I murmured. Then I hummed appreciatively again as his fingertips stroked me so close to my glutes. When he finished, I primly pulled the bottom back up.

"All good?" Greg asked briskly, starting to rise.

"Could you get the legs too?" I asked. "Save me the trouble?"

Greg strangled the cutest little moan of fear, and gargled, "Um, sure."

I heard him almost drop the lotion bottle, then felt the cool liquid trickle up first one leg, then the other. Now I was trembling just a little.

"You okay?" Greg asked, his voice a little higher than usual.

"Hmm? Oh yeah. Just tingling at the cold lotion on my skin," I said, relaxing once more.

And his hands grabbed my feet, massaging the lotion in all over. Then he started moving upward, one hand remaining on each leg as he rubbed along.

I didn't know about him, though I had my very good guesses, but I for one was horny as fuck by this point. I could feel everything swelling down here between my legs, and my nipples were almost achingly hard. We were at a point where the kid might just try to make a move of some kind. If he did, he was going to be rewarded.

But I didn't think he would. I hoped he didn't. There were still one or two more things I wanted to happen and to do to make the little fantasy of mine complete.

Yes, I like a little porn. Todd and I like watching it when the mood strikes. What, beside me telling you earlier, gave you the clue?

Greg did not, in fact, make any kind of move, but he obviously couldn't keep his hands to himself, as he rubbed the lotion into the backs of my legs, going higher. As he passed my knees, he was reluctant to really work the inner curves of my thighs, and more and more, the higher he got, he kept his fingers outward, with just his thumbs rubbing the lotion down between my legs.

"Mmmm, Greg," I muttered, quietly enough to make him really pay attention to hear. "That's a not bad massage you are throwing in for good measure."

He almost panicked again, but kept going.

It got very interesting as he reached the last few inches from where my legs met. If he kept going, he would be making a move whether he meant to or not. But he slowed down and was suddenly very tentative.

I took 'mercy' on him and cleared my throat. "Thank you, but I think maybe I'll get the last bits, if you'd rather?"

I felt him sag in relief. Then, in the first really proactive thing I'd felt him do, he didn't completely stop but slid his hands out wide, away from my crotch, and took advantage of that apparent timidity to slide his hands all the way up the outside to my bottom, allowing him a good caress of the outsides of both my glutes.

I pretended not to notice.

But I noticed.

I let him finish coating me across my butt before I rolled up on my side, but facing away from him. He was now confronted with my upright naked back, knowing that my tits were just dangling there in the open, maddeningly out of his sight. I took the bottle from where he had set it on the ground. In that process, he might have caught just the glimpse of a nipple from his angle. I hoped he had. He had certainly gotten a good dose of side-boob.

I squirted a nice dollop of the stuff into my palm, and proceeded, while he was still standing there, to coat the tops of my thighs between my legs, then reached around to rub a little on the inner cheeks of my ass where he had not had the guts to go. There was hopefully more side-boob in that process.

Then I set down the bottle, and quite carefully lay back down on my front, making great efforts to preserve my modesty and his innocence as I did so... as if I had not just all but flashed him several times.

"Thanks, Greg. You're a lifesaver," I murmured, snuggling down and closing my eyes.

"Uh. Yeah. Sure."

"You are getting close to done, right?" I asked idly.

"Yeah... yes ma'am," he said. "Um, yeah. I'll get back to it. Shouldn't be but maybe another half an hour." And he retreated hastily to the safety of the remaining overgrown bushes.

Perfect.

I let him go about fifteen minutes. Then I clutched my bikini top to my chest and sat back up. I held the top in place, poorly, with one hand, while I popped the backrest of the chaise up once more. I settled in against it, arranging my top to be discrete, for some ranges of value of the word discrete.

"Greg!" I called. He stalled the trimmer and listened. "You are cool, right?" I asked.

"I... I guess... I mean, I..." he trailed off and shrugged.

"I think you are," I said with an innocent smile. "But do you mind?"

"Sure! I mean, no! I certainly don't mind," he bumbled into it like the dear, sweet, polite, stupid boy he was. "Wait, mind what?" he added too late.

"Thanks," I said, and peeled off the top and dropped it on the patio.

I am fairly certain I heard him say, "Oh fuck!" But it was very quiet. The noise of the trimmer was not in evidence.

I lifted my ass and pushed down the bikini bottom as well, kicking it away from the chaise. I stretched to give him a good look at what he'd been fantasizing about for 24 hours. Then I grabbed the lotion and gave a slow, circling pass over my nipples and breasts, then another languorous set of passes over the areas around my mound. I made sure to twist enough that he could see I was clean-shaven everywhere.

Then I settled back in all my glory and sighed happily. Then I rolled my head toward him and smiled calmly.

He jumped to see my gaze on him, and he tried to look away to restart the trimming.

Enough of that shit. There was maybe five minutes of work left for Todd to finish off later in the week. And I didn't want Greg to fuck up my hedge at the last minute. This MILF wanted that boy, and she was going to have him. Now.

"Greg, come back here," I said, beckoning sultrily now.

Almost hypnotized by this point, he approached carefully to stand over me. His khaki cargo pants were baggy, but he was clearly packing an interesting erection inside them.

"What do you want, Greg?" I asked, my voice soft.

"Ooohhhh," he moaned in uncertainty. We both knew exactly what he wanted, but he was terrified. "I... um..." he trailed off, actually trembling a little.

"Well, I know what I want," I said, sitting up to sit on the edge of the chaise, directly facing him. I kept my legs together lightly, and tilted them slightly to his left. I looked up at him and breathed deeply. I reached out slowly to the front of his pants. "I hope you still won't mind," I breathed as my fingers went to the snap above his fly.

He mewled again, frozen in fear, but beating his instinct for flight to death with a bat inside his head. He stayed right in front of me. I undid the snap, and reached for his zipper.

And his hands grabbed mine in a fearful grip, but a strong one.

"Wait... Mrs. M," he said in anguish. "Mr. M is really cool, or... or Roxy says he is anyway. I don't want... to... ohhhhh," he trailed off miserably. He wanted very much to. He just wasn't sure exactly what.

"Greg," I said seriously. "You are so sweet, and so damned good, it makes you even more delicious. Do you know what is happening in Todd's and my marriage?"

"Uh, no."

"Of course not. No one ever does. You are not going to hurt Todd, and I swear he won't hurt you. First, he is never going to find out what we do here." Not in exact detail anyway. "And second, if he were to... we would be fine. That is all you need to know, but I'm glad you were strong enough to ask that. Okay?" He nodded almost involuntarily. But his hands still held mine in an unconscious grip.

"Good," I went on. "Now will you please let go of my hands, so I can suck your cock for a while?" I asked sweetly.

His grip did not so much release as it melted away, and his eyes grew to almost cartoonish, anime size. I tugged the zipper down, and found a pair of astoundingly boring boxers, with a definitely non-boring tent in front. I tugged them free as well and a beautiful, young, throbbing cock bobbed free. I may have sighed a little at how much it rose to my expectations and hopes.

Then I shoved his pants down to his ankles and held them there, instructing him to kick free of them and his shoes. Then, without another word, I gently clasped the base of his really very attractive cock and took several inches into my mouth.

"Oh my God," Greg moaned instantly.

Don't go off instantly, kid. It wouldn't be the worst thing in the world, but it might get into your head.

He didn't. His whole body trembled, but he didn't do anything like come. Instead, I felt his body slump and give into what I was doing to him. Holy fuck was that hot.

I relaxed, confident that the initial crisis had passed. As I bobbed slowly up and down on him, tongue ravishing him with each pass, I tugged fleetingly at the tails of his shirt. He got the message, and ditched it too.

That was better. We were both totally naked, as we should be for this.

I slipped him from my lips and looked up at his face, now rubbing his cock over my lips and cheeks. "Greg, I need you to pay attention to detail here," I whispered at him. "Take in every detail of what I am going to do to you, so you can get all the girls who are sucking this splendid beast to take care of you like this."

He moaned in distress at that.

Yep.

This cock was not getting sucked right and left by the girls at school. They were idiots. I hoped this would give Greg the confidence that the girls living wherever his family moved to would smell, and fix that issue. This cock was wonderful, and needed attention. Girls out there were in need of giving a cock like this attention.

Convinced I now had his attention at least, I really went to work.

There is an incredible, indescribable feeling you get when blowing a guy well. He is your utter thrall. Even if he is some kind of wanna-be alpha jerk, he is your bitch while you give him great head.

Some guys shake it off and think that the act means that they own you. They are the ones you immediately make available to the market... along with some one-star reviews for good measure.

The rest? The good ones? They are the ones that shit gets real good with. I've been with plenty of both when I was young. I know.

Never settle.

I was not settling here.

My only complaint with this lovely man-child was that he was petrified. I mean, his cock was pure stone, and that was great, but the rest of him was in shivering paralysis.

I let him slip from my lips here and there, So I could gasp out instructions. Hold my hair. Tickle my ears. Pump into my mouth slowly. He was so very accommodating. And his eyes were clear, he was taking notes.

Good boy.

I am not really one to have my face genuinely fucked. Not my favorite method of operations. But I had him nicely, considerately, thrusting carefully in my mouth, not throat. It was divine.

I was not going for anything fancy, I just wanted to kick this off for him with a nice, orally delivered orgasm, and that is what I concentrated on.

Greg eventually settled back in to a sexual lethargy, letting me work, and I did so. He did a lot of murmuring and moaning, and far too much thanking. I would have to warn him on that. A cock you are sucking needs to be at least a little dominant. Fortunately for me, his hips and hands did the job, even if his words did not.

Meanwhile, I did my job. Gleefully.

"Oh fuck, oh fuck, oh fuck," Greg began to moan, then repeated that soliloquy at an increasing rate. His shaft throbbed and his balls tensed. I sucked him deep, to the entrance to my throat, and my hands cradled his shaft while my pinkies tickled his scrotum.

As simple cry of, "Ohhh!" escaped his lips, and a flood of extraordinarily delicious cum flowed into my mouth. I'm not kidding, this was some one-percenter jizz. I swallowed it greedily and suckled for more. He gave it to me a few more times before I felt him fire dry, followed by a nearly total collapse of his legs.

I hopped up for air and caught him, helping him sag to the chaise beside me. Fuck yeah. I had wrecked this boy... and I had only just begun.

Mentally, I took a step back. This was a goddamned power trip for me, I suddenly realized. Fuck, it was good, but I needed to make sure I didn't ruin him. I had no worries about making his year.

I pulled his shaking, weak body against me and whispered in his ears, "Grab my breasts! Easy! We have so much left to do!" His hands fumbled hungrily against my breasts, and I kissed him gently. We went on like that for a while, trading soft kisses with very little tongue, while I softly whispered instructions to him for his hands. His instincts were good there, his grasp soft, his body language gratifyingly grateful, and I could have left him to go with his instincts, but there was a thing or two I wanted him to do, ways I wanted my nipples played with, that I led him to.

Finally, I felt energy flowing once more in his body, and blood flowing once more in one particular place. He actually pulled away from the soft kisses so he could look at me, his eyes wandering over my chest, what he could see of it that wasn't covered by his own eager hands. His eyes drank in the sight of my hard nipples being rolled between his first and middle fingers as I had instructed.

I saw him unconsciously lick his lips as he shivered with pleasurable restraint.

The sight of his tongue gave me some very definite ideas, but I had my own impatience, and by this point I wanted his dick in me more than his tongue. I wanted that very badly.

I pulled gently away from him and rose to my feet, deliberately standing before him in display. "I have to go get something to drink from the kitchen. We both need it," I said. As I turned, I looked back over my shoulder and winked, "Be sure to keep an eye on me so I don't get lost!" Then I headed off to the kitchen, taking my time to let him drink in the way I was moving my ass.

I returned a few moment later, carrying a bottle of water in each hand, with a condom packet sticking out obviously from two grasping fingertips. His eyes watched my breasts bobble as I approached and I saw his fingers twitch. When I got close, he spied the condom pack and his eyes widened.

"Oh wow," he said softly.

"Oh yes," I said, handing him the bottle of water held in the hand that didn't have the condom. He fumbled at it, then drank greedily. I took a long pull of my own, working my lips suggestively on its neck. Given what I had just done to the boy, it was a helluva suggestion.

I set down my bottle, but not the condom, and pushed him back to lie on the chaise, with his shoulders supported by the slightly raised headrest, and climbed on to straddle him. I let my pussy press along his prick, feeling the wonderful sensation of him groaning and involuntarily working his hips, moving his cock along my slit.

Then I pushed myself backwards a little, so his dick was free and clear. Holding up the condom packet, I asked, "Have you used a lot of condoms, Greg?"

"N... No. Not many," he answered.

I was by now increasingly clear that he had probably never used a single condom, nor had sex without one. That might have even been his first blowjob. I again considered whether I should teach him cunnilingus first, and again discarded the notion. Let him learn a few things at least on his own.

And my pussy ached to just slide forward and impale itself on that cock.

"Well, then you know they can be tricky. Let me put this one on. That's kind of fun if you do it right," I said, acting as if his 'not many' had meant something other than 'none'. Then I tore the package open carefully, and extracted the cover. I took forever to get it on him, explaining each little detail of how to get a good fit, and a secure one, without tearing anything, and the importance of making sure of that before using.

"Now," I said at last, massaging the cock with both hands softly. "Now that we have this beautiful cock all wrapped up like a present, what say we fuck my brains out with it, hmmm?"

"Ohhhh... fuuuuck," he said, eyes wide with almost animal desire lurking beneath the anxiety.

I slid forward once more, up on my knees, and lifted his dick upward, presenting the tip toward me. I pressed my hips downward. My opening pressed perfectly against him, and I kept my grip on his dick as I felt him begin to penetrate me.

As the head separated my lips, molding my body around it, he was shaking like a leaf. Had I not just blown him so thoroughly, I was sure he would have lost it. Damn, he felt good going in, going a kind of place where he had never gone before. As I sank, I lifted free my hands and wrapped them behind my head. His hands went swiftly to my hips, holding them desperately. I came to a rest on his thighs, filled nicely by that rod of youthful steel.

Not every cock gets rock hard, at any age. Some always remain a little spongy. I was always a little disappointed by that back in my days of sampling. Some cocks remain a little springy. That was fun sometimes. But stiff as a board always feels the most affirming.

And this kid was making me and my body feel very affirmed.

And I rode him, up and down, in slow, wonderful movements that sent shivers of pleasure through both our bodies, without crazily ramping up the stimulation in a way that might end it for either of us. His hands left my hips and went back to playing with my tits. I was a proud teacher to see him immediately remembering my instructions on how I liked him to do that. Even the skin of his fingertips felt soft and youthful.

And as I rode, I told him what I was doing, why I was moving my hips as I was, how that was making him hit my g-spot, making sure he knew how to find it again.

"Hold on, Greg," I said. "I think... you're going to make me... come just a little... a little bit here. Don't... ohhhh, let yourself go yet, please, but... ooohhhh," I sort of babbled. Then I crooned loudly. It was a little orgasm, one I could not avoid after showing him for so long how to bang my buttons. I did not let it stop my rise and fall on him. I kept going until my vision cleared, and I smiled down at him. "Thank you," I whispered.

He just looked up at me in amazement.

Then I did slide free of him, distracting his disappointment by pointing out how to check the condom after every extraction, and the importance of that.

I would have loved to ridden the kid into the oblivion of his release, but he deserved to feel his first orgasm inside a woman from on top. He leaned forward as I lowered the back of the chaise, though not all the way, and lay down beside him on it. Then I pulled him over on top of me. He kissed me, and I let him have just a little tongue.

"Put it in me, Greg," I whispered in his ear, and bit the lobe gently. He moaned again happily. He swung his cock against my groin, and fumbled just a little until he found his way. It was my turn to moan as he eagerly sank his whole length back into me in a single, swift stroke.

His instincts took over and I let myself simply enjoy his eager, aimless thrusting for a bit. But then I whispered again, "That is so good, Greg! But remember what I told you about what I was doing with my hips before? To make you find my sweet spots? I can't control that as much beneath you. It is your responsibility when doing it like this."