5 comments/ 65375 views/ 45 favorites Milking Grandma's Preemie By: milfleglover I puttered around the house, starting my fall ritual of putting stuff in the attic, clothing, seasonal knick-knacks and the like, a task that used to be easier when I was younger, and my husband was alive. But as I'm pushing 65 and though still in great shape, going to the gym and running regularly, it is a little more tiring than before. So I rely on the help of my grandchildren, such as this day when 19-year-old Bradley came by to assist me. Ah, Bradley. I noticed a change in him in recent years, a strapping young lad, college athlete, quite the hit with the ladies, a change that had him looking at me oddly from time to time, particularly when I was dressed for warmer weather. Like today. I had slipped into a pair of mid-thigh satiny white running shorts and a tight white top to hit the gym and left it on when I got home and Bradley pulled into the driveway. I couldn't help the feeling he was checking me out, a sensation that first left me aghast, but as time wore on, more than a bit flattered. Being the object of prurient attention by one so young couldn't help but make me feel better, but at the same time leaving me ashamed for it. The boy would check out his silver-haired granny when I wasn't totally covered in clothing, and then make an excuse to dart off to the bathroom, where, I imagined, he was relieving himself in more ways than the usual. Still, I shook those thoughts away, deeming them unpleasant and immoral, fighting the ones that were quite the opposite. This day, the two of us hauled boxes to the attic, taking turns, me getting that unmistakable feeling of being watched whenever I'd bend over to pick something up, on more than one occasion hearing the boy moan almost imperceptibly behind me as I did. Once, I heard a more frantic moan, a desperate moan and then him gulping, as if fighting something. 'Good lord,' I thought. 'Is he...is he about to..cum in his pants?' I turned and saw him, red-faced and uncertain, and covering his groin with his hands, scurrying to lift a box for me, figuring I caught it just in time. A sly smile crossed my lips, the reason why filling me with shame and her own uncertainty. "Uh, Bradley, we're almost done here, just one last thing," I said. "There's a light bulb over in the kitchen that needs changing, it's pretty high up. Can you get the closet stepladder for me?" "Sure thing, Grandma," he said, happy for the diversion. He set the ladder up, light bulb in hand, as I stood before him. "You go up, you're younger than I am!" I said brightly. "I'll make sure you don't fall." "OK, Grandma," he said, walking up the ladder to the top rung where he froze the instant I put my hands high up the backs of his thighs to hold him steady. "You OK, Bradley?" I asked, knowing full well he wasn't as I felt the heat from my hands through his jeans. "Uh, yeah, yeah, fine, fine," he stammered, probably glad he was facing away so I wouldn't see the bulge in his pants I assumed he had brought on by my hands on his thighs and more than likely hoping against hope he wouldn't pop a load! He struggled with the light, a tight recessed fit, but at least it took his mind off the sexual rush that I assumed was overcoming him. I wanted to stop, thought about stopping, but couldn't. His thighs were trembling in my hands and I found myself gently needing his steely young muscles, making him groan a bit more loudly. "Uh, better let me up, Bradley, I have pretty skinny hands and fingers, probably work better," I said, impulsively patting his fanny playfully. "You...you sure?" he squeaked, no doubt realizing that in my sexy little shorts, getting behind me would mean looking up underneath them. "I'm sure," I said, tugging at his belt to pull him down the ladder. I was right. Moments later, as I stood on the ladder, I knew his gaze was going directly up the backs of my wrinkled yet sexy thighs to the little sweep of my butt visible in my white panties, offset in its paleness by the long tanned legs below. He moaned again, more desperately now and I fully imagined he was about to shoot a load in his pants! It felt so wrong, so perverted, so immoral – and so hot. I couldn't help myself and pushed the sexual envelope further. "Uh, Bradley, hold me would you please?" I said over my shoulder, knowing the effect it would have on the boy putting his hands on the legs I knew he was staring at. "Uh...ok...Grandma," he stuttered, closing his eyes and his hands around my amazingly solid calves, getting more solid under the tanned, wrinkled skin as I moved about, tensing them as I maintained my balance. "Don't be shy, Bradley, higher, put your hands on my thighs, the way I did to you, it's safer!" I said, suddenly, shamefully feeling my pussy moisten beneath the matted fur gone damp in my panties, knowing full well what I was doing and not wanting to, but unable to stop. "I won't bite!" I heard him gulp as he slipped up my sculpted calves to the firm lower thighs and beyond, finally cupping around my taut hamstrings, the flesh saggy and wrinkled but hard beneath, the sinewy muscles flowing hot in his hands. I know he was looking up as I leaned up to work the light bulb loose, my shorts riding high, my legs flexing hard, and I felt my butt being exposed as my panties scooted into my saggy ass cheeks! So wrong, I knew it, but with that white flesh of my butt so close to him, I couldn't help myself and I swear I heard him sniffing, his face inches from my ass, seeking my scent. His hands trembled and I knew his cock, his lovely, young cock, was mere seconds away from betraying his incestuous lust! "Are...are you almost done, Grandma?" he said in a near whisper, no doubt looking at the tufts of hair peeking out from my panties, his hands quivering as he tried not to massage and caress them, and probably fighting the urge to plunge his face deep into my ass cleavage for a good, deep whiff. "Are you?" "Almost there," I said, amused by the irony of the statement since I knew by his weak voice he was almost there himself. That's as far as I was going to take it, I'd convinced herself, just letting the boy ejaculate in his pants and being flattered by it. But now my sense of balance betrayed me as I suddenly wiggled back and forth on the ladder, and felt Bradley's hands slip involuntarily upward, cupping fully the thick flesh of my ass as he tried to steady me. I gasped, fearful of falling, but did so, backwards, where Bradley's head was tilted down, and as I opened my legs for balance and fell, they went directly around my grandson's skull and in a flash, I found myself sitting astride his strong young shoulders, my pussy pushed up against the back of his head which I intuitively gripped with both hands, still fearing I'd fall, and wrapping my fleshy sexy old thighs around it, locking my ankles together. "Bradley, don't let go, don't let go!" I screamed, genuinely fearful of falling. In this rather awkward position, Bradley stumbled backwards, bouncing off the kitchen island, with his screaming grandmother securely attached to his head with her thighs! I screamed in fear as the boy, blinded with my supple old thighs folded like a meaty scissor around his head and face, couldn't see, and staggered toward the living room, his hands pulling at the old legs crushing his head. "Grandma, leggo, leggo!" he hollered, hands cupped around my solid, squeezing thighs. "Oh dear!" I yelled, slipping and twisting until, to both our horror, I slid around on his shoulders so my crotch was right at his face, my hands now cupping the back of his head, pushing my pussy into him, thighs still strapped to his ears as I tried to stay aloft. "Mmmgplffff!" Bradley yelled, his voice muffled in the suffocating grip of his my crotch. As he fell to his knees in the living room with me still frantically attached to his face, I heard his most desperate grunting yet and knew full well his dick was exploding! I could almost smell the sweaty scent of my pussy that I knew was enveloping his face and probably a huge reason why he was shooting his load in his pants, as well as the sight of my pussy as my short legs rode up completely and my panties shifted, putting his face in full contact with my hairy lips! He moaned as he shot his wad, his hands no longer pulling at my clutching thighs but mauling them, caressing them, feeling their sexy, squeezing power as they clamped around his cheeks and ears. He fell to his back, thrusting his hips into the air as I came to settle atop his face, legs now unlocked and knees splayed wide, my exposed, hairy pussy enveloping his nose and mouth. I looked down between my tanned thighs, the look of shock on my face matching the one on his. Our eyes locked, and both knew exactly what had happened. A very long moment passed when thoughts consumed us both, and I found myself sitting on Bradley's face far longer than I should have before I regained my composure and slid back to sit sheepishly on his chest, looking down at the panting boy, and pulling my shorts legs back down as well as adjusting my panties over my crotch. "Uh, Bradley, I'm..I'm...so sorry!" I said, hands over my eyes as Bradley struggled to sit up and in the process knocking me back where I settled directly on his cum-soaked crotch. "Oh...my...GOD! Did...did I do that...did I do that to you????" I knew I had, of course, but played it like I didn't know, not wanting him to realize his premature ejaculation was something I wanted to bring about, ashamed to have done it but at this moment, feeling his wet heat in his pants, so glad I did. I rolled off him and looked down at the spreading wetness in my grandson's crotch, wide-eyed, ashamed and electrified, all at once. He lay there, covering his eyes, humiliated. "Grandma, I'm so sorry, please...I just couldn't...that always happens...it's just..." he babbled. "Shh, shh, shh, Bradley," I said soothingly, scooting up close to caress his face as I knelt beside him, looking down at his wet crotch where his cock was fully erect still. "I understand, young men...sometimes...they..." I couldn't stop myself, reaching for his cock with my bony old hand and watching him jump when I made contact, my fingers closing around it. "Grandma, what????" he said, eyes open and full of tears. "Shh, shh, Bradley," I said in a husky voice that took me by surprise as I watched my hand leave his cock only to undo his pants and slip them down over his thighs, Bradley offering only token resistance. "We've...we've, uh, gotta take care of you, we have work to do, and don't need, well, any distractions...." His eyes went wider still as I encircled his gorgeous young cock, hard as stone and a good seven inches long and wonderfully thick, in my fingers, stroking it, the cum already there acting as a lubricant, the squishy sounds sexual and obscene, causing me to stroke him faster and faster, my own eyes half lidded as I felt the smoldering desire well up in my own crotch as I jerked him off. "But...but...but..." he moaned, succumbing to me, relaxing back on the floor as I stroked his cock faster and faster, using my other hand to squeeze his beautiful, hairless balls, eager to milk them dry. "Oh, God, Bradley, oh God," I moaned. Within a minute of stroking his dick, and only a few minutes after he'd cum in his pants with my pussy in his face, he came again, the first rope of sperm shooting two feet in the air and striping across my shocked face. Instinctively I popped my mouth over the jetting head and felt the scorching heat of several more thick jolts of his cream fill my cheeks, as I used both hands now to stroke him, twisting them back and forth, up and down, the poor boy screaming in pleasure and uncertainty as he filled his grandmother's sucking mouth with his wonderfully tasty, gooey seed. I swallowed down quickly, the load seemingly never ending until he finally settled back down to the floor and I continued to stroke his cock into my mouth, my pussy absolutely soaked in my panties as I was wonderfully close to orgasm myself. I finally popped my mouth off his dick, squeezing the last drop out with my hand and lapping it off. I sat back, smiling, wiping the cum from my face off with my fingers and slowly sucking them clean. "My, my, my, Bradley, you young ones deliver SO much!" I laughed, leaning forward to kiss his trembling lips and shooting my tongue inside his mouth to let him taste his sperm. "And really, you're STILL hard!" We both looked down to that impossibly erect dick, slick with his juice and my saliva, bobbing up full. He smiled sheepishly at me and then looked on incredulously as I slipped off my shirt and bra, my saggy white tits bouncing free, and then my shorts and panties, kneeling before him only in socks and sneakers. Astonished, he watched as I climbed atop him, gasping as I fisted his stiff young dick and fit it to my hairy hole. "Grandma! No! This is...so wrong...oh..my..GOD!" he moaned. I smiled at him as I settled down fully, taking his long, thick shaft inside me, feeling it fill my pussy in a way no man had ever done before. I felt his hot nuts brush my ass and I moaned in pleasure as I leaned forward on his chest, pumping up and down slowly, feeling his fullness enter and leave me with each delicious stroke up and down, my tits swinging at his wide-eyed face. "It's been soooooo long, Bradley, so terribly long," I hissed, leaning further down, holding my wrinkled tits in my hands, offering him the thick brown nipples that he anxiously sought out with his mouth, suckling at me, nursing me like a baby at his mother's teats. "Oh, God, Grandma," he moaned, eyes closed, that hot tongue washing over my nipples, sucking one then the other into his mouth, then slurping over the creamy white flesh around them as his hands, trembling, closed over my saggy old ass that was pounding up and down around his cock with mounting frenzy. We locked into a rhythm of long-time lovers, he thrusting up, me thrusting down, my ass meat jiggling and quaking in his hands that cupped and caressed the flailing flesh, for long, sweet minutes. He continued to suckle at my old breasts and I wrapped my arms around his head, cupping his face to my tits, smiling over the top of his head, as he ran his tongue into the deeply wrinkled flesh of my cleavage and to my neck, madly suckling the creased flesh of it, flesh I hated for the way it sagged but loving the attention the dear boy was paying to it now, mouthing it to hold in his lips and running his tongue over the salty meat. I was completely lost in the shameful sensation, the forbidden lust consuming me as I came, again and again and again, huge, quivering orgasms followed by smaller ones, a nonstop parade of pleasure I had never felt before. I pulled back and off him suddenly, smiling at his surprised look, then turned to face away from him, fitting him back inside me, affording him the view of my wrinkled ass around his cock as I leaned forward on my hands and humped him madly, on my knees, the flesh of my butt quivering and quaking as I slammed up and down on his beautiful young cock. "You like that view, Bradley?" I found myself asking, looking over my shoulder at his face staring at my wrinkled ass in a quivering frenzy around his prick. "You seemed to like the view of my butt when I was on the ladder, you must love this!" He moaned reaching out to gently hold my hips as they continued to pound up and down, my butt shaking and jiggling around his dick. "God, Grandma...damn...gonna...you're gonna make me....." he moaned as I slammed up and down harder, my pussy flooded with my own orgasmic juices, the sloshing sounds wet and wonderfully obscene filling the air around his moans. "Cum, boy, give Grandma your hot, sweet cum!" I growled. His third load filled me, not as large as the last two but still larger than anything my late husband ever gave me and I felt its forbidden heat overwhelm me as Bradley's sperm barrel into my milking womb. I screamed in orgasm as he did in his, until we both finally stopped, me leaning forward on his trembling legs, he laying back, both of us sweat soaked and panting for air. I was overcome with desire, still, and slowly, very slowly, pulled off his stiff dick and inched my way back, feeling his eyes on my ass and gaping pussy and the thick well of his hot cum that was poised inside, dripping slowly down my hairy lips. "One more time, Bradley, one more time," I hissed, feeling him tense up at the sight of that cum-filled granny pussy making its way toward his face. "Lick me, boy, lick your grandmother's hot, filthy, cummy cunt!" These were words I never imagined myself saying but I was too far gone to stop now and even as he protested, I pushed back, planting my dripping hole on his face, pulling it deep inside my wrinkled ass flesh and feeling the cum squirt into his sputtering mouth. "Grandma, no, no, no..mgmpflff!" he said before I scooped his face deeper into my cummy hole with my hand, clamped my muscular old thighs around his face and secured it by folding one calf across the back of his neck, hooking that foot under the other leg, a figure-four scissor that completely buried his mouth to my dripping sex. "Lick, lick it, suck your hot load and make me cum again!" I heard myself screaming, squeezing his head in my thighs, taking that protesting face deeper still, the hot cum flooding out and filling his mouth where I heard him desperately swallowing, gulping it down, his chin on my clit that I banged into with my humping hips. "FUCK!!!!" As I came, I looked at his stiff dick that was again ready to burst and slipped my sucking mouth over the thick cap, jerking him in both hands, corkscrewing that slick meat into my lips, moaning as I did, my pussy continuing to drench his scissored face in our combined fluids. In less than a minute, my blowjob forced Bradley's fourth load of the last half hour or so from his tireless balls and cock, his load seeping into my mouth, again filling my cheeks as I moaned and thrust my cummy pussy harder and harder into his lips, feeling the last drops of his last load ooze into his gulping mouth. I finally stopped sucking him and released his face from my scissoring legs, turning to lay next to him, his arm around me and mine draped over his sweat chest. I giggled like a schoolgirl and licked his cum and mine from his face, then planted my lips on his, making out with a young man, my sexy, young grandson nearly 50 years my junior, our tongues doing battle with each other. We stopped, then stared into each other's eyes. "Ah, my little preemie, how was that?" I laughed, leaning to nibble at one of his nipples. "Un...unreal, Grandma...just unbelievable..." he smiled. "Do you have this...uh, problem with cumming quickly with your young girlfriends?" I asked. "Always," he said, shyly, blushing and turning his face away from me. "I mean I...I cum in my pants just kissing them! It's awful..." I turned his face back to mine, kissing him. "Never again, boy," I smiled. "Any time, any time at all, when you're going on a date, you just come visit your old granny....I'll take the edge of for you..." "Really?" he said with eyes wide and a beaming smile on his face. "Well...I, uh, actually have a date tonight..." "Not a problem," I sighed, slipping to lay on him face to face, gripping that only slightly flagging cock in my thighs and work it toward my hungry pussy. "Not a problem...." Milking Grandma's Preemie Ch. 02 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 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 about..you 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 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. "Who..." "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, 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. "But..." "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. "Oh...my...GOD!" 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. Milking Grandma's Preemie Ch. 02 She took all of it, every thick, roping jet, swallowing – and looking sidelong at me in the window, my own face a mask of orgasmic delight. The dear boy was writhing in pure pleasure, hips twisting as he unloaded into her, and finally looked down as she cupped his huge smooth balls in one hand and twisted the other around his shaft, slowly popping her pretty mouth of it. Her cheeks bulged with the last of his cum. She stood, putting her arms on the boy's trembling shoulder and pulled him in for a kiss. He didn't resist a whit, and their lips met, Tobey groaning and pushing close to him, his hard cock knifing between her oily thighs as she shot the cream into Bradley's accepting mouth. She squeezed his cock, the top of it brushing her pussy through the bottom of her bathing suit, slowly stroking it as she lashed her tongue into his mouth, scooping out some cum to swallow. "Well now, that was quick and should take the edge off for you," she smiled, pulling her cum-shiny lips from his as she quivered her clutching thighs around his dick, which showed no signs of going soft. "Or perhaps you're in need of a little more..." She backed away and for his pleasure, slowly peeled out of her suit. His eyes, as well as mine, were riveted to those fantastic little titties and those long, strong legs and that furry thatch between them. She dropped the suit, smiled at him and walked to the pool, curling a finger at him. His eyes were fixed on Tobey's beautiful ass, the meat if it jiggling, the tight muscles beneath the silky dimpled skin dancing. "Let's have a quick swim, Bradley," she said. "Lose the clothes." She jumped in as my grandson hurriedly tore the off his t-shirt and leaped in beside her. They played like two long-time lovers, splashing water on each other and swimming toward the deep end. Tobey reached up for the diving board, grabbing it. Bradley swam near her and instantly she snaked her beautiful legs out to scissor his slim waist, squeezing him to her. He grabbed the board as well and they were face to face now, kissing, groaning, loving. "Fuck me!" she hissed, moving her hips to take him into her, the boy gasping loudly as he felt his cock plunge through the cool water into her superheated pussy. "Hurry, before Grandma gets back!" "Oh god oh god oh god!" the boy groaned, holding the board and thrusting into my friend's gripping pussy. He fucked her, the water sloshing around them, bending his head down to suckle those enormous, long nipples, gnawing on them. Tobey tilted her head back to give him room, peering over her shoulder where I stood in the window, transfixed. She winked again. "Hurry, Bradley, hurry!" she cried out. "Fuck me, cum in me, it's ok, cum in me, quickly, before your grandmother comes back!" He'd been fucking her for less than a minute when true to his premature form, he grunted and came, as I could tell by his groans and body language, holding tight to Tobey's writhing body and emptying his balls again. She let him stay inside her, holding him, her thighs still wrapped around his sides, before releasing him from her leggy grip and kissing him gently. "Now, hurry, over here, Grandma's due back shortly, we haven't much time!" she said, swimming over to the edge of the pool and pulling herself up onto the lip, legs spread. "Time for...for what?" Bradley asked, swimming to her, facing that hairy, dripping chasm. "For this," Tobey snarled, pointing at her cunt. "Clean me up, honey, quickly, I can't be leaking your hot cum into your grandma's bathing suit I borrowed, can I? Hurry, she'll be back any second!" I couldn't see anything but the Tobey's sleek, tight back as she reached out with her incredible legs to scoop my grandson's head into them, thighs clamping shut around his face. I heard his groans and then hers and knew he was slurping his sperm from her well-fucked pussy as his hands cupped around Tobey's slick, sleek thighs, the sheen of water accentuating every sexy muscular furrow and pulsating sinew. "Oh, shit, that's right, that's right, clean up your cummy mess AND make me cum, baby, make me cum!" she screamed loudly, more for my benefit than the boy scissored between her churning thighs. She came against his face, snapping her slim hips, grinding against him and finally letting his head slip from her crushing thighs. She stood on the pool's edge, smiling down into his smiling face slick with their juices. "C'mon, hurry, get dressed, it's been almost a half hour!" she said, rushing to her crumpled suit on the pool deck, looking at me in the window with a huge smile. I took the cue and left the pantry, giving them a few minutes to gather themselves. When I walked out, I had to stop myself from visibly shaking. "Well now, you two been getting along?" I smiled, standing between their lounge chairs, Tobey looking serene, Bradley slightly edgy and nervous. "Famously, just famously," Tobey sighed, stretching out those long gorgeous gams that had just been locked around my grandson's ribs and neck. "Like old friends..." "Yeah, yeah, it was great," Bradley added. "Very glad to hear that," I said, looking at the boy. "Hon, can you come inside for a minute, there's something I need you to do." "Uh...ok, sure, Grandma," he said, standing up. "Anything I can help with?" Tobey said, smiling up at me. "Happy to lend a hand!" I almost burst out laughing, knowing what she meant. "No, no, you've done enough...entertaining this young man while I was gone!" I said. "You just lay here, enjoy the rest of the sun, OK?" "Sure thing, Lannie, I'm all for that," Tobey sighed, hands behind her head and wriggling that fine ass into the lounge chair. Bradley and I walked inside, through the dining area to my kitchen. In the wall separating the two areas is a large cutout that allows a clear view of the pool – and my relaxing friend. "Now then," I hissed, taking my grandson into my arms and nailing him with a long, sloppy wet kiss, grinding my crotch into his, cupping his ass in my hands. "Let's get you ready for your date tonight, shall we?" He kissed me and I felt his cock grow against my crotch – but not as fully as it had always done. I knew – and loved – the reason why. "Is everything OK, honey?" I asked, pulling his lips to my neck and holding his head, letting him suckle the salty warm wrinkles as I put my hand into his shorts to stroke his nearly hard cock. "Yeah, Grandma, yeah," he groaned, pumping into my hand, sucking my throat wetly. "It's just that...she..Mrs. Wolfsen...right there..." "Yes, sexy isn't it?" I giggled. "Now you just stand there, keep an eye out on the lovely Mrs. Wolfsen..." I knelt down as he stood, facing the pool, his eyes fixed on Tobey lying there. I pulled his shorts down, freeing his luscious cock, and slurping it into my mouth, savoring the oozing precum that bubbled from it. I wasted no time, attaching both hands to that handsome prick, twisting my fingers around it, stroking it in and out of my mouth, my head bobbing back and forth. I felt him tense in my mouth, his cock fully hard now. I blew him for a few minutes, far longer than it should have taken had not my friend extracted two loads from him moments earlier. I popped his cock out of my mouth and jerked it with one hand rapidly, holding the thick tip against my pursed lips, lashing it with my tongue. "You haven't cum yet, honey, aren't I doing it right?" I teased as I jerked him, looking up at his face. "No, no, it's great, Grandma...but Mrs. Wolfsen...God, she's like right there!" "Can you see her?" "Yes, of course, she's right there!" "She's just lying there, she's not getting up or anything?" "No!" "Then enjoy the view, darling," I groaned, stroking him even faster now. "Watch her as I suck...you...off....look at her, Bradley, she's quite beautiful, isn't she? Such a gorgeous woman, that strong, lean body....those legs, goodness, she has fantastic legs, doesn't she?" "Oh my God, Grandma!" he groaned, eyes fixed at Tobey. "I think her legs are incredible....God, can you imagine them wrapped around YOU, honey? Can ya?" He stiffened more in my pumping hand, the wet stroking sounds filling the kitchen. "Does she turn you on, Bradley? It's OK, tell me: Does Mrs. Wolfsen turn you on?" "Oh...oh, GOD, Grandma!" he moaned. "Yes! Yes, she does!" "Wanna know a secret?" I teased, lapping the precum oozing out of his cock as I jerked it. He looked at me. "What?" "She turns ME on, too!" His eyes could not have opened wider as he looked into mine, astonished. "That's right, baby, that beautiful old woman out there turns me on! Oh, we haven't done...you know, anything, but in my past...a long time ago, I had enjoyed...the company of other girls..." His cock thickened under my strokes. I ran my other hand to his nuts, drawing my nails over them, making him jump. "And I liked it, Bradley, I liked it a lot...being with a girl...so much fun..." I jerked him faster, holding his dripping tip to my lips, tongue tickling it. "Cum for me baby, cum for Grandma, as we watch our lovely friend out there....look at her baby...look at that beautiful woman...." "OH SHIT!" The first spurt splashed into my face, hitting me in the forehead and running in a thick, lumpy sheet down over my eyes and nose, over my lips. I quickly popped the head into my mouth, stroking him with furious deliberation, my hand flying up and down the shaft, coaxing the rest of his spunk out of his beautiful balls, thick, surprisingly copious strands of it given what Tobey had milked from him not long ago. He finally stopped cumming and I swallowed every drop, eagerly, smacking my lips as I let his wilting cock slip from my hand. I looked up through the cum dripping over my eyes, wiping it off with my fingers. He stood, looking down at me, mouth morphing into a smile. "It took you longer than usual, maybe our training is paying off!" I laughed, standing. He took me into his arms and lovingly began to lick his cream from my face, lapping it off my forehead, down over my cheeks and nose, slurping it from my chin where it hung in goopy strands and finally kissing me. We shot his spunk back and forth between our mouths, his cock, now half hard, pushing into my crotch. "Wow, this is unusual," I laughed, stroking his wet dick, making him wince as my fingers pumped around the slick, sensitive head. "It's almost soft..." I suddenly felt playful, dominant. I grabbed his softening cock shaft in one hand and with the other ran my thumb in agonizing circles around the underside near the top, where the post-orgasmic sensitivity is the strongest. He squirmed in my grip, which I tightened around his cock base, not letting him get away, my thumb pressing harder and faster in cruising laps around the tip. "Grandma...please...it tickles...it hurts!" he groaned. "Tell me, Bradley, did you cum while I was gone?" I asked sternly, looking into his eyes. "What? No..no, of course not, how..." "Perhaps just looking at my friend? You know, you always cum so very quickly for me, perhaps just looking at Mrs. Wolfsen's luscious body...those long legs...those little titties...maybe you came already, that why it took you so long to cum for my mouth, hmm? That why you're so soft now? Answer me boy or I won't stop!" "Ohhhh...oh, God...no, Grandma...I swear...I didn't cum...in my pants!" Which, of course, was the truth. He'd cum in Tobey's mouth and pussy. I laughed thinking about it, relishing his trembling as I continued to work over his super-sensitive cock tip before stopping. "Very well, I believe you," I sighed, kissing him. He quickly bent to pull his shorts back up as I walked away, to the pool deck where Tobey looked up at me. "Got a little on ya, baby," she giggled, pointing to my chin. I wiped off the dollop and extended the finger to her mouth. She lustily sucked it off, tongue running over it. "Tasty little boy, isn't he?" she laughed. She got up and we both walked inside where Bradley now stood at the far side of the large kitchen counter. She walked over and sat down beside him, smiling. "Grandma says you have a date soon, that right?" "Uh...uh yeah, I probably should be going, you know, gotta get ready..." he said nervously. "Oh, just relax for a bit, you've got time," I said, sitting at the small table in a tiny space just off the kitchen where I did my work, opening my laptop. "Just got a couple emails to catch up on..." There was a mirror on the other wall there, which gave me a clear view of the two of them, Bradley leaning over the countertop facing away from me, Tobey seated beside him – looking right into the mirror, smiling at me. She slowly ran a hand up the back of Bradley's thighs, under his shorts, cupping his ass. I saw his face turn to the side, looking at her, shaking his head. She said something to him, apparently calming his fears. I pretended to be typing, my eyes on the mirror, as she worked his ass, massaging it under his shorts. Her eyes on me, she pulled her hand out for a moment, ran her fingers under her bathing suit top and coating them with suntan oil. She pulled down his shorts, his head frantically shaking side to side, but couldn't stop her. His shorts were now down just enough to reveal his fantastic young ass, milky white. I couldn't believe what she was doing as I watched in the mirror. She slipped her oily fingers into his crack and very slowly, ran one into his rosebud asshole! I thought he'd scream, but she stifled it with her other hand, cupping it over his mouth. "How are you two doing in there?" I called out, typing away, eyes fixed on the mirror watching my best friend finger fuck my grandson's asshole. "Oh, just talking about his date tonight, you know, finding out about the lucky girl!" Tobey said loudly, winking at me in the mirror as her muscular forearm flexed with sinew as she pumped her finger into his butt. "You just take your time, honey, we're just fine...aren't we Bradley?" "Oh..oh yes, Grandma, fine!" he said in a forced, hoarse whisper, giving into her plunging fingers, two of them now sawing deep into his ass. I knew what she was doing, burrowing both fingers into his butt, holding them there, wiggling the tips against his prostate. I saw his back arch, head back, mouth open in a silent scream of pleasure. He was cumming, my best friend was fingering my grandson's asshole until he came, and now I saw her put her other hand before him, presumably catching his flow in her cupped palm as those sexy forearms sinews flowed under the silky, tanned skin. And I came again as he did, now running my fingers into my slit under my shorts, stroking my clit to a quick, very satisfying orgasm, watching them. It was surreal, incredible and over far too quickly. I watched in the mirror as with her eyes fixed on mine in the mirror, she lifted her gooey palm up to Bradley's face tipping it and letting the smallish pearly stream of cum collected there drip in a silvery strand into his waiting mouth. She smiled broadly at me as the boy ate his cum from her hand, then attached his mouth to it as she smeared it into his lips, lapping the rest of it clean. She finally pulled her fingers from his asshole, tugging his pants up over his hips, rubbing her palm on the front of her bathing suit – my bathing suit, actually – and then sitting back on the stool as if nothing had happened. I closed my laptop, took a deep breath and came back into the kitchen. "Well, Bradley, you must be going, right?" I said, giving him a hug, feeling his body tremble as he stood next to Tobey. "Get ready for the big date!" she laughed. "Hope you're not too tired from all this time you spent with two old ladies this afternoon!" "No, no, it was ...great...nice seeing you again, uh, Mrs. Wolfsen..." he mumbled, walking toward the door. "See you soon, I hope," Tobey said, waving goodbye as I walked him down the hall to the door. In the alcove, I swept him into my arms, kissing him, tasting the cum still on his lips, palming his crotch. "Hope you can still perform tonight, young man, you seem a little soft right now," I laughed into his mouth. "Come back later, if your little girlfriend isn't enough for ya...." "Thanks Grandma," he said quietly, kissing me back. "You're the best..." I walked back into the kitchen, shaking my head at the smiling Tobey. She stood to face me, holding up her shiny palm between us. I held it in my hand, eyes on hers, as I ran my tongue up and down it, tasting Bradley's residual sperm. "Well now," Tobey hissed, licking her palm with me and then to my lips, kissing me deeply and wetly. "Where were we...."