Monogamish - Realizing Her MILFdom

"Good to meet you Greg," Todd said in his heartiest voice, giving him an appraising look. "Although it might just be only today, since I hear that we are losing you and Roxy next weekend. We will be sorry to see her go."

"Not as sorry as she is," Greg said with a slowly nervous smile. Todd just laughed.

"Well, you got here just before I left," he went on, indicating his ridiculous-looking golf pants. "I'm off for 18, 27 if we can get them in. Please don't injure yourself and bleed all over my hedges, okay?"

Then he turned back toward me. "You are dressed to work in the garden too, I see," he added, as if he had not happily watched me getting dressed, something he took time out to do often--a happy lesson from an earlier Hall Pass.

I was wearing... not exactly practical gardening attire. Daisy Duke jeans shorts and a U2 tour teeshirt that had been purposefully bought five years ago at a size too small. It was still only one size too small, thank you.

#SmugAndIKnowIt

Greg was having a hard time keeping his eyes off me as I kissed my husband goodbye, with a gentle peck on the cheek, as opposed to the way I would usually climb down his throat at a time like this, to make him regret deciding not to stay home for an easy hole-in-one.

Today, I settled for the listless peck.

As Todd drove away to actually play golf, I led Greg out into the backyard.

"You know much about pruning?" I asked him, the homeowner in me hoping for a yes.

"Yes, ma'am," he said, looking around where all I was indicating. "At our old house, we had a lot of shrubs and a high hedge like this."

"Then have fun!" I said with a hopefully dazzling, friendly smile.

"You aren't going to direct me?"

"Greg," I said conspiratorially. "There is no way I'm going to actually do any work out here while Todd is off sneaking up on dimpled, defenseless, little white balls. This is the first really hot day of the year. I am going to get some sun and read my book, and occasionally watch you work. How's that?"

"You're the boss," he smiled.

"And?" I prompted.

"And there is no need to mention any of that to Mr. M when he gets home?"

"Exactly," I said with a wink. "Though there is no way in hell he will be home before you are gone for today anyway. That really only applies if you see him tomorrow." I punched him on the shoulder very lightly, to emphasize our relative sizes.

If I wanted to, I'm pretty sure I could have made the boy take a knee with one punch or kick. The bad Hall Pass had left me with an affinity for martial arts.

With that, I pointed out the electric trimmer and the big shears lying next to it, and turned to sashay my way over to the big chaise we had in the back yard. It was deeply cushioned and oversized in width, with enough room for the boys to both sleep on it at once when they were younger... and for Todd and I to enjoy other activities thereon. I turned sideways, seeing that Greg's eyes had yet to let his feet move, and without looking at him, tugged the U2 shirt off over my head.

Underneath I had on a plain blue bikini top, one that was a size too large, in contrast with the tour shirt. I was quite confident that my breasts did not need a tight bikini top to look enticing, and this one could be easily made to gape in various ways. I had actually gone out and just bought it that week. I had not actually bought a bikini top, only bottoms, ever since I went on my first Hall Pass. I had one-piece suits for when the boys and their friends were around.

I let him actually get stuck into the work for about 45 minutes, which also confirmed in my mind that all I had was about two or three hours worth of actual work for him, and two days for him to do it. Then I got up and wandered inside. I know how to sway my backside with some skill when I walk, and I employed that skill.

I went to the kitchen and grabbed two cans of passionfruit seltzer water, which would make a good double-entendre if it came up, but which was otherwise my favorite anyway, and went back outside.

Greg was trimming away with his back turned to me, and as I got near, I called out his name. He turned to see me approaching, with my tits about to fall out, and a can of the cold seltzer pressed against my already slightly glistening neck. "I was just thirsty, and figured you would be too," I said, lifting the can before I got to him. "Want a seltzer?"

"Um, I'm not twenty-o..." he began to stammer.

"It's not hard seltzer!" I exclaimed sternly. "I'd never! This is just flavored seltzer. It is refreshing, not sweet, and has zero calories, which I think looks best on me," I said, leaving the 'don't you?' left unspoken, but not unheard. I leaned forward and up to hand him the can, and if I didn't give him at least a hint of some nipple, I'm not a judge of men's faces.

Greg took the can, looked at it, and muttered, "Passionfruit?"

"My favorite," I said blandly, and turned to walk back to my book, still walking at ass factor nine.

This was almost too easy. I could fuck this delicious boy today, without breaking a sweat. But if I did, what would I do with my tomorrow? Both Todd and I had done multi-day Hall Passes, and we had both sometimes hit it off with more than one person during those passes. But they had been away from home, and it had never, never been with the same person on multiple days. This whole enterprise was too close to the edge already, so I was not about to try to add a second helping from the same dish.

I could have my fun today and be done, but I kind of felt like I wanted to really get Greg's motor running hard. Leaving him to stew over me and what my intentions might be for a night might be just the ticket to complete my scenario perfectly.

Of course, something might happen, and if I didn't fuck him today, I might never get the chance tomorrow. He might even grow a spine or some morals and not return!

I laughed at that last to myself. I had never known any nineteen year-old guys in my time who had many morals when it came to a piece of fantasy candy, to my frequent pleasure back at that age.

I would torture him today, and reward him on Sunday. And myself.

But first, I was going to get a good dose of showing off, my first in a while.

With a dose of humorous fantasy thrown in.

I settled in and ran through my options. Nothing slutty or too blatant... today. After a slow and thorough sun-screening of myself--a process that dragged Greg's eyes from the back hedge a gratifying amount, I settled in for a chapter of my book.

After another few minutes, I reached behind my head and untied the bikini top behind my neck. Greg had moved to one of the shrubs, a boxwood clump that had gone crazy with sprouts shooting out all over the place across its fine compact shape, and he was facing my way.

I'd have hated to have him fall over backward or injure himself with trimmer.

I slowly pulled the straps of the bikini down off my shoulders and tucked them fastidiously into the oversized cups of my top, then tucked the tops of those cups, one at at time, inside as well, leaving my nipples just barely covered... unless you were standing over me, in which case a significant crescent of my pink aureoles would be visible.

"Greg!" I called, beckoning.

He came over dutifully, his eyes having a very hard time staying off my half-removed top. When he reached and stood over me, it was as I had postulated, he had an impossible time looking away.

"Get me another passionfruit, would you?" I asked absently, not looking up at him so he could get his eyeful without being nervous about looking into my eyes.

"Sure," he stuttered, and went into my house.

He was back swiftly, with two fresh cans. He cleverly approached me from over my shoulder, giving him the best view yet... especially since, while he was inside, I had pushed the cups of my bikini even farther free. He saw nipple this time. I made sure of it.

I cracked open my can, leaving Greg to wander bemusedly back to work.

After rolling the cold can around in my cleavage a little, I went back to reading. It was a good book.

By the time Greg was half done, I estimated he could have finished, had I not been distracting as hard as I could without making it obvious. I sat up noisily, tied my top behind my head again and went inside.

This was fun. I had almost felt his eyes on my body like a massage. A really nice massage. I considered asking him to sunscreen my back, but no. That was for tomorrow, when he would be sunscreening a lot more than my back.

I went back outside with a fresh can of spray-on sunscreen in hand. To my delight, Greg had moved on to the shrubs along the left fence, which gave him a delightful view of the chaise from the side.

Ignoring him, as far as he knew, I went to my chaise and lay down on my chest, setting my book clearly aside for later. Once on my chest, I reached back and undid my top, both behind my neck, and in the small of my back. I deliberately lay the straps of both to the side, leaving my back utterly bare, and the bikini completely removed beneath me. A quick spray over my shoulder put a fig leaf on the fact that my back already had a deep tan laid in.

I actually took a brief nap. It was wonderful. Naps had been a joy I had recently rediscovered after the intervening years since I was four.

Twenty-somethings: Naps fucking rock. Look into them.

My nap was not long, especially since the minute I dropped off, my groin went into overdrive, rampaging through my dreams.

I awoke, with my crotch feeling very fine, and realized that I had rolled a quarter turn to the side, leaving a huge scoop of side-boob showing right in Greg's direction. I swiftly decided that that was just great, and pretended to continue to nap, rolling an eight of a turn back and forth. He always was presented with some of my tit, it was just variable how much.

I 'awoke' and shook my head, pressing my chest down against the chaise. I looked around, pretending not to register Greg's attempted subtle ogling of me. Then I pressed up onto my forearms, letting my tits dangle completely free in the air over my top, which of course just lay there on the chaise. I shoved things around for comfort, and settled back down again. I may have actually napped a little more. It was hardly the sleep of the just. Greg had gotten quite the view of me.

When I went for a second time, I made sure to watch him closely out of the corner of my eye. This time, I was looking for when he was inattentive, paying his mind to unimportant things like my hedges. When he was looking away, I 'reawoke' and pushed up, dangling my tits even more in the clear. I shoved my towel around under me, then, when his eyes had shot back to my body, I pretended to realize what I was doing, and rather than look his way, I twisted away, clutching my top. I made a big deal of subtly slipping it back on. When I finally furtively looked around, Greg was turned away and trimming the back edges of my hedge. The edge that didn't need trimming.

I quickly put my top back on, as if embarrassed, and deliberately did a bad job of settling the ill-fitting top back in place. I looked at my watch. It was a little earlier than I had planned for him to leave today, but I needed to make sure there was plenty left to do the next day, and my last little display, followed by my alleged embarrassment, was the perfect note to leave the boy hanging.

I got up hesitantly to my feet, then strode over to him confidently. I was pretty sure that I had nailed the way just a crescent of pink aureole peeked out of my top.

"Greg, I don't think you can get all this stuff finished today, so why don't you knock off now, and be back about one tomorrow?"

"I might could finish before dark," he began.

"No, don't worry. Tomorrow will be fine," I said, resting my hand briefly on his arm. He jumped, whether from my sudden touch or the way a little more of my aureole came free with the gesture, I did not know. Nor did I care.

"Okay, Mrs. M," he said, and headed off. I indulged myself in watching his sweet, muscular ass flex as he left my yard.

God bless the high privacy hedge all the way around the back. Tomorrow was going to be a very good day.

ME: He's gone for the day.

TODD: Mission accomplished?

ME: Today's mission. I have him thoroughly tortured.

TODD: Heh

ME: So you can come home whenever

TODD: Sorry. We really are going for 27 holes.

ME: Jerk!

TODD: Be dressed for dinner when I get home, how's that? I'll take you Prime Meats.

ME: Marginally less of a jerk

I had so much enjoyed torturing Greg this afternoon. I was going to torture Todd tonight, I mused, mentally going through my wardrobe. I know I can be cruel, but I was going to pay off both guys, in spades, so what was the harm?

The gold dress, with the extra cleavage. That would do for tonight. I'd torture the wait staff too.

Bless Hall Passes, I might never have realized how fun it was to make men bite themselves...

*

I awoke early Sunday, feeling quite satisfied with Todd's and my dessert the night before. But also quite hungry for my Hall Pass experience.

"Morning, MILFy," Todd said with a smile. He reached out for my breast, but I slipped out of bed.

"Ah, ah!" I giggled. "I need to be fresh today. Tonight you can defile me to my heart's content." He just smiled and I stopped to enjoy the sight of him, sitting up with his lovely chest bare, and the simple sheet covering what was mercifully not a full erection. I might not have been able to resist.

When Greg arrived at one, I was dressed what I hoped would be disappointingly, with simple slacks and a blouse. The blouse did show some cleavage. MILFs always show cleavage, right?

When Todd once more showed Greg through the house, I greeted him absently. His face did flash a brief sag of disappointment. Perfect!

Todd went out to the backyard with Greg and proceeded to talk his ear off back there. I waited for a while, then came out myself, holding two glasses of lemonade... not passionfruit seltzer. "Thirsty, guys?" I asked, approaching with an ordinary walk. "Todd, if you are going to be out here, you could actually lift those shears and, you know, help."

"Can't," Todd said to Greg, not me. "I'd have to change clothes. And I need to be ready to go play poker this afternoon, in..." he looked at his watch. "Shit. Now. Sorry Greg, I have to ghost. Love you babe," he added absently, barely missing landing a kiss on my cheek as he headed out the door. "I'll bring back Mikey and Junior on the way home late tonight," he called on his way out the door.

I watched him go, then turned to Greg and handed him a glass. "Cheers," I shrugged, and we clinked glasses. I waited by him, implying I wanted the glass when he finished, so he dutifully drank it down. He even dribbled just little down his chin. That was sexy.

"You are good with direction for today, right?" I asked. He nodded. "Then carry on, Greg," I said and walked back inside. Ass factor nine was back in my stride. The slacks I wore were not that slack, especially across my backside.

I shot up to our room, and stripped out of my housewife garb in a flash. I picked up the other new bikini I had bought--the expensive designer one that fit me like I was in a magazine advertisement. I slid on the bottoms, and chuckled as I straightened up the top before donning it. It really was a waste, given my bikini-wearing habits, to have even bought it. Today would likely be the only time I ever wore the top. And it would not be for long...

I slipped it on and looked at myself in the mirror.

Yessss. I might wear this top a few more times...

I grabbed a nice, wide-brimmed sun hat, and a bottle of sunscreen. Not the aerosol from yesterday, but a nice, viscous, white lotion.

I picked up my book and swayed out of the house.

The noise of the trimmer stopped as I let the door slam loudly behind me. I looked over to see Greg staring. Perfect. "Hi Greg!" I said. "I'm just going to get some more sun this afternoon, do you mind?"

"Me? Uh, yeah... no. No, I don't mind," the boy said.

"Like my new bikini?" I asked almost absently as I swayed my hips over toward the chaise.

"It's uh, great," Greg said, on autopilot. "It fits really well. Better than..." He tried to shut himself up.

I just chuckled. "Yeah the one yesterday is a loss. I've already waited too long to return it, though. The bottom always fit perfectly from the start, but I never needed the top. When I finally put it on, it was too late to return it," I said regretfully. I never looked his way, but I could sense that that little speech had his attention even more, if that were possible.

I got out the sunscreen lotion and began to slather it on myself, taking my time and rubbing in everywhere, including tucking my fingertips underneath the waistband and leg holes of my bottom from one side to the other. Ordinarily, I do my legs in short, circular motions, but this day, I coated them with long strokes of my fingertips, running up from my toes all the way to the bikini, and then back down.

I left the back of my legs alone for now...

Covering my torso was even more fun, rubbing gooey white stuff into my skin, tracing the still flat flesh of my belly, and pressing into my cleavage. I made sure to move the top around a lot as I got all around the edges. My throat was covered swiftly, with my head thrown back. I had done my face ages ago with a different product. I lay back and read my book.

While I had been putting on that show, the sound of the trimmer had been sporadic at best. It was better that way. I neither wanted the boy to hurt himself, nor did I want him to scalp my hedge. If he ended up doing the latter... I'd live with it.

After he finally got back into a rhythm, I gave him five minutes to make some good progress, then I stood up and bent over to mess with the chaise, giving him a really good view. My bikini bottom was in no way a thong, but it wasn't like the thin, perfectly fitting fabric was much good at concealing even the parts of my ass it did cover.

I laid the chaise out flat now, and I spread out a towel on it fussily. Then I finally lay down on my front. I rustled around a bit more. There were once again very sporadic trimmer noises. They stopped entirely when I reached back and unhooked both top and bottom straps off the top. I laid the straps out to the sides and lay there for a second, my back completely bare. Then I pushed up my torso just far enough to not let my tits actually hang free in plain sight, but enough to give a good dangly side-boob show. I reached for the sunscreen and settled back down. Then I fiddled with the lotion. Even if I did not have an obvious plan, I could not have gotten my back well, if at all.

"Greg!" I called, turning to look his way. I tilted my torso a bit, but kept my tit from showing itself by bunching up the towel against it.

He waited to see what I wanted, but when I said nothing else, he approached hesitantly.

I grimaced in embarrassment. "I know it's a pain, but I don't want to get any tan lines started on my back," I explained, leaving out that I had no tan lines on my front, and no intention of developing any there either, thank you. "Do you suppose you could put some sunscreen on for me? I just can't reach." I extended the bottle toward him, making a show of keeping that tit covered by the towel.

When he took the bottle wordlessly, I smiled, thanked him and settled back down on the chaise, flashing him pretty fully while I straightened out the very towel I had been concealing myself from him with. It looked completely, absent-mindedly accidental.

I relaxed almost as soon has the boy squirted the first lotion on my back, then began to smear it around. His hands trembled wonderfully, and he clearly did not know much about putting suntan lotion on someone else. I still loved the sensation and murmured just a little, approvingly.