Milking Grandma’s Preemie Ch. 02

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It was eating at me, what I’d done with my grandson. But I couldn’t stop doing it. I didn’t want to. And neither did he.

Bradley, a dear boy of 19 and always helpful to his old granny, had come to my house one day to assist in putting away seasonal things in my attic. I’d felt for awhile he was fascinated with me, having what I guessed you could call a crush on me. I enjoyed it, secretly, seeing nothing but innocent fascination.

But I never thought it would come to this: Having sex with my grandson.

His increasing fascination was noticeable, particularly when I was dressed in somewhat revealing attire in warm weather. To be immodest, I couldn’t say I blamed him. I’m 64, with silver hair but take care of myself and have pride in my body, tall, lean, even muscular.

Especially in the legs. Which is where it all started.

I’d asked him to change a light bulb in the kitchen for me, steadying him on a step ladder. Instantly, I felt his nervousness as he stood, my hands on his legs, then his hard young butt, as he struggled to change it.

I got him down and went up myself, feeling naughty in knowing that in my tiny running shorts, he’d have a clear view of my long, strong legs and butt beneath those shorts.

I was right. As he held me, his trembling hands on my thighs and cupping my ass, I could feel his undeniable sexual tension and knew he was hard, and worse, seemingly about to cum in his pants from the barely perceptible groans he made.

So I decided to put an end to it – but not before I staggered back from the ladder, perhaps subconsciously willing it to happen, and ended up astride his shoulders, my lean legs clamped on his neck and ears.

We’d both stumbled around the kitchen and in my efforts to keep from falling, had accidentally – or not – spun around so my crotch was in his face, my thighs scissored securely around his head, and his dick seemingly about to explode.

And then it did. We fell to the floor, me astride his shocked face, shorts and panty pulled aside in the fall, and he shot his load the instant his handsome young face contacted my rather hairy pussy.

Awkward doesn’t begin to describe that moment. Humiliating was more like it, more for poor Bradley than me. For a very long moment that seemed forever, we stared at one another, his face pressed between my thighs for longer than I should have allowed.

But I couldn’t move. When I finally regained my composure and slid off him, I slipped back to sit on his crotch – which was soaked with cum, his pants front warm and sticky.

I apologized profusely, aghast I’d done this to him, made him ejaculate in his pants, yet secretly delighting in the fact I had. Forbidden fruit, after all, is the sweetest.

But I calmed down, took control, easing his fears, telling him what had happened was perfectly natural. Then I did something perfectly unnatural.

I seduced my grandson.

It felt so wrong yet so right all at once. Quite simply, I blew him and fucked him, wrenching three more orgasms from the virile young stud, promising him to do the same any time he had a date coming up and feared his biggest problem: Premature ejaculation. Poor boy would cum just kissing girls, he said, and my mind rationalized I was just helping him out.

And I did, over and over. He’d come back several more times, eager for his granny’s special loving, even when he didn’t have a date.

And all of it was eating at me like a raw nerve, it went beyond lust and satisfaction into depravity – which I could not stop.

I hadn’t told a soul. Until the day my best gal pal, Tobey Wolfsen, a 61-year-old gym rat like me, stopped by for an early-afternoon cocktail. Tobey, a gorgeous tall blonde, is a true liberal spirit, and an old, trusted friend. If I could confide in anyone, it would be her; I had in the past, and she was always accepting, gracious, non-judgmental.

And as we sat around my swimming pool sipping wine, the need to confess threatened to overcome me.

I hid it, as best I could, but our conversation, as it often did, veered into the sexual. Both of us were single, long complaining to each other about the adequate stock of suitable men out there, often joking that we should perhaps set our sights on much younger partners.

Tobey, in fact, had dated men 30 years her junior, and often urged me to do the same. As she was doing now.

“You know, girlfriend, it wouldn’t hurt you to put your toe in younger waters,” she laughed, swirling her wine glass and sipping. “Nothing like a younger man, I tell ya…”

“Yes, so I’ve heard,” I said, apparently somewhat wistfully, something Tobey picked up on because Tobey always could read me like a book even when I didn’t think it was open.

She looked at me, head cocked, her long, pretty face slowly breaking into a smile.

“Lannie Markum, you’re getting some, aren’t you?” she laughed.

My face dropped. I shook my head.

“No, no I’m not, whatever are you talking about?” I said, feeling myself blush. “God, Tobey, sex is all you think izmir escort bayan about, I swear!”

She leaned forward over the glass table we sat at, putting her hand on mine. She felt it tremble, and her smile widened.

“Thought so,” she grinned. “Now don’t bullshit me: Who’s the lucky young stud and how good is he? From your reaction, I’d say pretty damned good!”

“Tobey, honestly…it’s nothing…I mean, no one…really,” I said quite nervously.

She leaned forward, her face, smiling, inches from mine. I thought she was about to kiss me. Which truth be told, I would not have minded. I’d had encounters with females many, many years ago, and so had Tobey. We just never acted on it with each other, both thinking what’s past was past, we’d gotten mature, married, had children, grandchildren.

We never talked about the possibility of us getting together, but now, along with my incestuous relationship with my grandson, it was the secondary elephant in the room.

And as her face, so beautiful, almost equine with its sharp, exquisitely handsome features, got closer, I wanted more than anything for her to kiss me.

“Don’t lie, girlfriend,” she hissed, eyes on mine. “Tell me….”

“Well….” I said softly. “It’s like this…”

And I told her. Just like that. In slow, lurid detail, looking into her brown eyes, captivated by them, drawn into the telling, feeling relieved, alive, ashamed. Slowly, very slowly, she sat back, stunned, mouth agape, eyes wide. She was scarcely breathing and finally let out a long exhalation.

“Holy….shit…” she said when the tale was told, and I sat back on the lounger by the pool, Tobey leaning on the other arm. “Wow…Bradley, huh?”

“Yes, Bradley, I’m so ashamed!” I suddenly blurted out, putting my glass down and leaning into my hands, sobbing.

“Honey, honey, it’s ok, it’s ok!” Tobey cried, shuffling over to put her arms around me, hugging me close and comforting me. “It’s love, right? You love him, he loves you, it’s ok, really!”

“You…you think?” I said between sobs, turning to face her, her fingers coming up to wipe the tears from my eyes.

“Of course, honey, of course,” she said soothingly, hugging me tightly.

“Have you…I mean, with…”

“My grandsons? No, no, but that’s not to say I haven’t thought about it, lord they are good-looking young studs, that’s for sure,” she laughed. “Maybe I should have them both come by and change my light bulbs for me!”

We roared with laughter, easily and freely. Tobey was so good like that, able to defuse any tense situation, as old friends tend to.

“You know, Lannie…I gotta say, that’s pretty hot, you…you blowing, fucking Bradley,” she said softly.

“Really?” I sighed. “Well honestly, sex with him is the best sex I’ve ever had, he’s just so eager to please, ya know? He did things….no one else ever has, it was amazing…”

“Do tell, girl, do tell!”

“Well,” I said slowly. “He…he was not at all shy about kissing me…you know, after…well, after I blew him…”

“Get the fuck out, I’ve never met any man who’d do that!” Tobey laughed, slapping her leg. “That’s great, just great!”

“And he isn’t shy know, licking me…down there, after we make love,” I sighed.

Now THAT is amazing. I had to lock him in down there with my legs to get him to do it at first, but he really did enjoy it..and still does!”

“You never cease to amaze me, Lannie, you never do,” Tobey sighed, getting up to get us more wine, pouring it into our glasses, and clinking hers to mine. “Here’s to old sexy babes and horny young…grandsons!”

We chatted away, and I looked at my watch. It was after 4, and Bradley was coming by to, well, prepare for a date later. As always, Tobey read my mind.

“Your little cum-slurping slave boy’s due here soon, isn’t he?” she asked, making me laugh with her straightforward train of thought.

“Well…yeah, he has a date for real tonight, and…you know…I’ll, uh, take the preemie edge off for him..”

“I do know,” she laughed. “And I do know I wouldn’t mind getting in on this action…with your permission, of course.”

I looked at her, astonished but amused.

“You are such a horny bitch, you know that?”

“Oh hell, I do know that, too!” she laughed, edging closer, that pretty, elegant face inches from mine again. “And I know I’ve had just enough to drink to do this….”

She kissed me. It was that simple, though not a simple kiss, not a gentle peck on the lips. She melted to me, me to her, and we sighed, bodies trembling, lips pressed against each other’s for a full second or two but which felt like a lifetime.

She broke, sitting up, smiling.

“I’ve always wanted to do that,” she sighed. “Ya know?”

“And..I’ve always wanted you to,” I whispered. “Ya know?”

We stared at one another for a moment before Tobey giggled and said, “Well, it’s certainly been a day of revelation hasn’t it? As far as we go…we’ll get into that later perhaps, but for now….”

She escort izmir stood, taking my hand, which felt warm, comforting, and escorted me back inside, turning to face me. Her hands held my shoulders and she smiled a loving smile.

“Let’s talk about a plan for young Bradley, shall we?” she said.

“Well,” I responded, taking a deep breath and letting out a long sigh. “Why the hell not?”

We concocted a plan, two old friends perhaps a little buzzed by the wine, but purposeful. She’d change into one of my bathing suits, since we’re about the same size and have always shared clothes, and lounge by the pool. Waiting for Bradley. I’d make up some excuse to be gone, and then let Tobey work her sexual magic.

And I’d come back and secretly watch from the pantry window overlooking the pool.

“Wow, this is nice, is it new?” Tobey said as we were in my room, showing her my bathing suits with one, a rather revealing bright yellow modest two piece catching her attention. “I love it.”

“It’s yours…for the moment!” I laughed. “Go on, try it on.”

She stripped quickly, standing naked before me, unashamed. Her body was spectacular, muscular and lean like mine, legs a bit longer, the flesh tighter, tanned and taut. Her tits were tiny, practically nothing more than little silky puffs of flesh, centered by long, luscious nipples. Between her luscious thighs was a big thatch of neatly trimmed dark hair. She caught me looking.

“I don’t shave,” she shrugged, looking down at it. “The boys seem to like it, it’s so…retro, I guess!”

“Throwback pussy!” I added, and we both roared.

She slipped into it and she looked fabulous, good enough to eat, those long nipples poking through the top. As if everything that happened so far wasn’t making my mind race, the thought of me suckling those tiny little tits just added to my sexual fog.

“OK, let’s do this, baby,” she said, slapping my ass as we walked out, adding a squeeze at the same time. “God, you have a great ass, you know that?”

“So I’ve been told,” I cooed playfully, slapping hers in return.

“By Bradley, no doubt, with his face buried inside it!”

We went by the pool, Tobey lying on a lounger just as the doorbell rang. She reached up and grabbed my blouse, pulling me in for a quick, lovely kiss.

“Here we go, girlfriend,” she snarled. “Bring the boy to me!”

“You’re incorrigible, you know that?” I laughed, walking away and yelping as Tobey pinched my ass through my shorts.

I opened the door, and my dear grandson stood, smiling, then looking back at the car in the drive.


“Oh, that’s an old friend of mine, Mrs. Wolfsen, Tobey, Tobey Wolfsen,” I said, bringing him inside, delighting in his eyeing me up and down, as always. “You know her, I’m sure you’ve met her once or twice over the years…”

“But Grandma, I thought,” he said, looking nervously at his watch.

“Yes, yes, of course, we’ll have OUR time, Bradley,” I said, slowly slipping my hand down his shorts and making him gasp as it encircled his hard, ever-eager cock. “We have a couple hours, more or less, right? She just stopped by for a visit, a quick drink. And besides, I have to run out for a bit, half hour or so, deliver some paperwork to my office.”

I stroked him, pressing him against the wall, kissing him, getting him worked up and smiling at the sticky result as his cock oozed precum all over my clutching fingers.

“Why don’t you just go relax by the pool, with Mrs. Wolfsen,” I said, pulling my hand out of his shorts and slipping my juicy fingers into his mouth, which he sucked clean, eyes open and locked onto mine. “I’ll take care of you later – I promise!”

“Oh…OK…” he warbled weakly, obediently following me, eyes watching my muscular legs flex as I walked.

“Tobey, this is Bradley, my dear grandson,” I said, walking us to the pool where Tobey lay looking exquisite in her clingy one piece. “Do you remember him?”

“Of course I do!” she said, jumping up and hugging him, the poor boy holding back a bit to hide the obvious aroused state I’d put him in, exacerbated by the sight of the gorgeous older woman by the pool. “It’s been awhile. My God, look at you, all grown up, so handsome, such….a young stud!”

Bradley blushed, smiling nervously as Tobey sat back down, eye level to his crotch. He quickly covered it with his hands, backing away.

“I have to go out for a bit, 30 minutes maybe, you two chat, OK? Catch up?” I said, walking away.

“We’ll be fine, Lannie, just fine,” Tobey called out in sing song voice, winking at me as I turned to wave goodbye.

I raced down to my car, jumped in and drove away, circling the block slowly, nervous with anticipation. I drove back, inching into my driveway and creeping inside.

I looked out through the sliding glass dor and saw Tobey on her belly, Bradley kneeling by her, trembling hands applying suntan lotion to her slender, smooth back. Quickly, I made my way to the pantry, peering out the window there for a mun clearer view.

“Oh, izmir escort that’s nice, very nice, Bradley, thanks so much for doing this,” Tobey sighed as his fingers worked the cream into her silky flesh.

“My…” he coughed nervously, “uh, my pleasure…Mrs. Wolfsen…”

“Indeed,” Tobey giggled. “Now…my legs, would you, squirt some of that cream onto my legs, my calves and thighs, and work it in good?”

I saw Bradley’s eyelids flutter and knew he was about to cum in his pants! He obeyed, dutifully squirting the lotion onto Tobey’s slim, muscular thighs and calves, lacing each with a long stripe of white, snapping the bottle shut and nervously rubbing the cream in. I could almost hear his moans over Tobey’s voice.

“Oh, that’s nice, VERY nice, Bradley!” she hissed. “God, lovely, just lovely…yes, massage them, too, you may as well, rub my old calves, really rub ’em….just like that, that’s right…now up, up my thighs, go on, massage my thighs! Don’t be afraid, boy, I won’t bite!”

“Yes, Mrs…Wolfsen…” he squeaked, his voice cracking as he gulped.

I groaned myself, catching it, quieting it, but at the same time sneaking a hand into my shorts and playing with my clit. Tobey’s legs were magnificent, muscular, lean and sinewy, all the more lovely gleaming with suntan lotion. This was the most erotic thing I’d ever seen – and it could only get better.

“Uh…if you don’t mind, Bradley?” I heard her say.

She reached back, slipping her bottom up between her cheeks. We both gasped, Bradley’s audible, mine silent, as Tobey’s luscious, fleshy white ass quivered into view, her fingers releasing the fabric to snap against the succulent meaty butt.

“Are…you….” he groaned.

“Oh, yes, I’m sure,” she said softly but forcefully. “I don’t usually tan my bum, but I like to…when it’s appropriate…go on, put some cream on and rub it in!”

I didn’t know who’d cum first, Bradley or me, as I fingered myself faster, watching my grandson’s strong, nervous hands knead my best friend’s gorgeous ass. His eyes were rolling over in the sockets, and I knew he was very close to popping his load.

Tobey sensed it, smiling, turning her head to face the window. Bradley’s back was to me, and she saw my face in the window. She smiled. And winked.

“Now then,” she said, suddenly twisting around to sit up, forcing Bradley to his feet.

And as she sat, her face was again level with his crotch – which was clearly showing that beautiful young, hard cock, sticking up like a tent pole before he could cover up.

“Oh my goodness!” she cried out with mock shock, covering her mouth with her hands.

“OH MY GOD!” Bradley cried out, staggering back and falling to his ass, rolling over in shame on the pool deck. “I’M SO SORRY!”

Tobey didn’t say a word. Slowly, very, very slowly she stood, walking over to him, standing on spread feet, hands on her hips.

“Bradley,” she said with a near growl, looking at my face in the window and smiling. “Are you…aroused? Is…is that what I just saw…poking up in your shorts? Hmmm?”

He didn’t move, frozen in fear, huddled into a ball. She knelt by him, putting a gentle hand on his back. He shivered at her touch.

“It’s OK, Bradley, really it is,” she said gently, rubbing his back. “I understand…”

He turned his head to look up at her.

“You…you do?”

“Of course, you’re a normal young man with normal…reactions, to what I guess you find an attractive woman! I’m flattered!”

“You…you are?”

She very slowly took his arm, twisting him to a sitting position.

“Did you….I mean, have you….oh, hell, why beat around the bush,” she laughed. “Did you cum in your shorts massaging my legs?”

His eyes widened, his head shaking side to side.

“But you were about to, right?”

His head nodded.

“Well, that’s sweet,” she smiled. “You have a date, I think right? Your grandmother said something about a date?”

He nodded again.

“Well heavens, we can’t have you going out all hot and bothered now, can we,” she sighed, standing, offering him a hand. “I did this to you, it’s my responsibility to fix it.”

His eyes nearly fell out of his head as very reluctantly he stood, hunched over a bit.


“No buts…well, not yet,” Tobey giggled. “But this is very important…”

She knelt before him, smiling up, her hands on his shorts, slowly unsnapping and unzipping them, Bradley watching raptly.

“Not a WORD to your grandmother about this, OK?”

His head was a blur as he frantically nodded, then gasped as Tobey yanked his shorts down to his ankles, his beautiful, hard young cock bobbing up and nearly hitting her in the face.

“Nice, nice, VERY nice!” she exclaimed.


I fingered myself watching Tobey’s beautiful mouth open and with excruciating slowness, encircle my grandson’s cock tip, and then just as slowly working down the shaft, inch by delicious inch, the lips puckering down it like a fish mouth until she reached the base.

At which point Bradley came – and I as well.

“SHIIIIIT!” the boy screamed, head back, howling, eyes scrunched shut as he delivered what I presumed to be a huge load down my best friend’s gulping gullet.

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