The Seductive Seed of a Tranny MILF

"You were scared when you first brought up the idea to me of selling my spunk. You were scared when you drank it for the first time. You were scared to use your hands on me and then your mouth. Each time you did it and you're glad you did, aren't you?"

Jackson nodded affirmatively, staring like a puppy dog up into Martha's big, twinkling eyes.

"And I've been there every step of the way to help steer you along, haven't I? This time'll be no different, honey. Won't you let me share in some more of the fun with you?" Her voice had a smooth, soothing quality that stirred a sense of comfort and security inside Jackson.

He thought about it and then he said, "We can do it, on one condition."

Martha's smile stretched across the entirety of her face. "Name it! Anything."

"You never threaten to give me up and go back to your socks again." He returned her smile and coiled his small hand around her still-stiffened member.

"I accept your condition," she said with a wink before swooping down and kissing him eagerly. Her hands were all over him in a flash, groping his body and removing his clothes with passionate precision. Martha stripped him just as naked as she was and pulled his little body into hers while their tongues wrestled. Her hands reached around him and kneaded his smooth, bubbly ass cheeks.

Jackson listened to Martha and did what she told him to. It was a different experience than any of the others. Oddly, even when he'd been pleasuring her cock with his mouth, part of him felt like he was still the one in control. She didn't grab him by the hair and fuck his throat. She let him take the initiative, he played and experimented and went at his own pace. Now as he climbed into her bed and bent down on all fours, his chubby, little ass aimed toward her, she was the one firmly in control.

Martha groped his butt and spread the hairless, little cheeks as a fiery smile twisted its way onto her face. "We're gonna do just fine together, you and me," she said, staring eagerly at his tiny, quivering asshole. She pounced on Jackson and bit playfully into one of his soft cheeks. He yelped and pulled away, out of surprise rather than pain. Martha chuckled, admiring the little love mark she'd left on him.

"Relax," she told him.

"You've done this before, right?" Jackson asked softly.

"Of course."

"And you've had it done to you?"

"Sure. Remember I had a dildo eight inches deep before you got here today, honey." Her fingertips grazed his lightly-trembling cheeks.

"Did it hurt the first time?" he asked finally.

"Yep, it hurt at first. And it felt good. It felt both ways at the same time until eventually the pleasure drowned out the pain. Some things are worth a little pain, sometimes those are the best things. The things you're most glad you did." Her hands stroked his hairless butt and thighs reassuringly as she spoke.

Jackson seemed comforted for the moment but jumped when she opened a bottle of lube from off the dresser behind him. Martha put the bottle back down for the time being and gently laid down on top of him, her heavy tits squashing against his back and hard cock lodging harmlessly between his thighs.

She kissed his neck and took his earlobe into her hot mouth before whispering in his ear, "Listen to me when I tell you to relax. Don't tighten up. Loosen yourself from within. Nothing bad's gonna happen to you. I've got you and I'll take care of you."

She squeezed his arm and then lifted off him. Martha dropped her head and planted a loving kiss on his butt right below where she'd left the little mark with her teeth. She grabbed the lube again and held it over him.

Her cock ached and strained desperately for the pleasures of his little ass. "Are you ready? If you need to, you can still say no."

"Do it. I want you to."

Martha sighed with relief. Both of their hearts were beating out of their chests as she drizzled the oil onto his wincing pucker. She squirted some onto her hand and after a few strokes had thoroughly covered her impressive length in the greasy lube, paying special attention to make sure the swollen tip was thickly-coated.

"It's coming at you. Don't tense up. Don't get scared. Let it in." Martha spread his cheeks and brought the fat, spongy helmet to the mouth of his asshole, letting it nestle comfortably there, she basked in the first sparks of pleasure that coursed through her horny, mature body.

"I forget just how big it is sometimes," Jackson said, ready to grit his teeth if need be, trying to keep his breathing steady and his body calm.

"When it's knocking on the door of your little rose for the first time, of course it feels big. You're gonna do okay. Think loose thoughts. You can't fight it. It's gonna go where it's gonna go. Do not clench. It's just me. I'm knocking on your door. Let me in. All I want to do is shoot my cum up your ass instead of in your belly for a change. You may like it just as much this way."

Martha's massive tip had started to work against his natural defenses, sawing its way inside, while she spoke to him soothingly, hoping to preoccupy his mind and pacify his nervous body. She was halfway through his hot, clutching sphincter and leaking pre-cum like a sieve before he knew what had happened. Jackson grunted and pushed gently around it, opening the way as best he could for its grand entrance. He winced with tremors of sharp pain but he forced his muscles gradually to ease as she wrestled all the way through his sphincter into the moist, trembling cavity of his ass.

"That's it, honey. You're doing great. Laying that tight, little red carpet out for me. I know it hurts, it's going to get easier. Just hang in there." Martha held him by the hips in her strong hands and began with deliberate slowness and steadiness to feed her pulsing meat into his tiny, twitching passage.

"It's so tight," Martha cooed. "Like my cock is being smothered. God, I could get used to this."

Jackson clenched his eyes shut and waited for the worst of it to be over. Behind the pain he could already sense something else lurking there deep within; a nugget of pleasure. Every time he reached for it he couldn't quite grab it, but no matter how much hurt her intruding member inflicted on his poor ass, that shiny, promising spark of hiding gratification was always there. All he had to do was catch it.

The greasy inches of her fat prick disappeared until there was none left outside his pucker and their bodies fully met. "That's all of it. You did great! How's it feel in there, everything all right?" Martha's words were coming out slightly slurred due to the immense pleasure she was reaping from him tender, throbbing insides.

Jackson mewled out an incomprehensible reply, but he didn't tell her to stop and he wasn't crying in pain. Martha took that as a cue to keep going, her fingernails dug into his warm butt cheeks as she slowly withdrew just a couple inches, curling her toes when his hole contracted around her girth.

At a pace similar to how she first had penetrated him, Martha eased those veiny inches back inside him. Jackson groaned and clutched the bed sheets beneath him. "So deep," he muttered.

"Don't listen to the pain, listen to me. I know what you're going through and I'm right here." Martha wrapped one hand around his body and grabbed hold of his fully hard cock. "Someone's stiff," she said, chuckling. She massaged his straining pole as she withdrew a few more inches from within him and then gently slid them back in.

"Still so tight. You sure are a gripper, honey. Bad for you right now, good for me because it feels so fucking fantastic. You've had the worst of it already. Loosen this booty up for me and I can really start to lay the wood on you." She continued to stroke his manhood, pulling her hips back in one long motion until just the engorged tip remained jammed within his pucker.

Martha relished taking her young lover's virginity, reveling in the intense pleasures of his tight clutches. Soon she could drop her responsible demeanor and do some real fucking. Jackson had the kind of ass that begged with all its little trembles and squeezing kisses to be ridden for real by a woman like Martha with her size and stamina. She put her hands back on his hips in pursuit of more control for what was soon to come.

She pressed back inside him until about the halfway point, looking down between their bodies at the fat inches she knew were up his ass, being gripped and massaged by his hot, moist anal muscles, and the inches just outside, throbbing, desperately eager to join their brothers deep within his utopian opening. Martha could never deny her cock what it wanted. She went balls deep inside Jackson with one steady push that was faster and more powerful than anything she'd done so far.

"Uhhmmghhm... fuck..." Jackson whimpered loudly, finding his voice.

"Too much? Is the pain very bad?" Martha asked, caressing the butt cheek she'd left the lightest of bites on.

"It feels... it feels... kind of good? Do more. Ohh, I feel something... way deep in there. Fuck! Don't stop, it, it's making me shiver, making me feel weird all over... I, I like it!" The pain was dulling for Jackson, transforming slowly into a tolerable ache that radiated through his ass while a dark, forbidden pleasure began to sweep throughout his entire body.

Martha felt similar elation. She'd been given the license she needed to enjoy the incredible pleasures of his tiny, clutching hole without worrying about the pain it was causing him. She extracted a few inches of her hard cock only to bury it back inside him. Martha did this a few more times, finally developing the sort of rhythm, though still slow and relatively gentle, that made it feel like real sex. It was glorious.

"Yes, ughh, fuck, ohhhh, fuck... yes!" Jackson moaned. "This, this is why people love getting fucked. I, I didn't know! Didn't know what it felt like!" His back arched and he could feel his toes flex stiff then bend tight.

"It's the greatest feeling in the world, honey. And this is why you love getting fucked. There's no one else here but you and me. One little hole and one big, fat cock." Martha's breath was coming out heavily now. "You're doing so good. You're an amazing first-timer and I'm so lucky to be the woman doing it."

After a string of unyielding thrusts inside her boy Martha was beginning to sweat. She listened to his soft moans and the slapping together of their bodies. They really did make beautiful music together. She wouldn't let herself think about how it would have to come to an end before too long. She wanted to stay buried inside him forever, luxuriating within the hot, delicate delights of his slippery insides.

"Fuck, fuck, fuck me! I'm all yours, Martha! I love the way you do me. Don't stop. Don't ever stop!" Jackson cried, beginning to jerk his cock and moaning into the mattress.

Martha buried her throbbing prick to the hilt inside him at the end of every thrust, digging her sharp fingernails into the soft meat of his ass more ferociously. It was too hot inside him. Too tight. No one could hold out against the unyielding grip of his quivering pucker. Martha knew her eruption was fast approaching and she was determined to savor every moment until then.

"You're the tightest I've ever had, the absolute best ass out there, Jackson. Keep clutching my pole like that and I'm gonna stuff your little butt so full with cream!"

Martha drilled his hole with forceful thrusts as his anal muscles wound even tighter around her girth and squeezed the semen up from her depths. Martha's big ass bounced with each snap of her wide hips. She felt pleasure-filled shivers run up and down her spine and the hair on the back of her neck stand straight.

"Do it," Jackson urged her, biting down on his knuckles, cum boiling through his shaft. "Shoot your delicious seed deep inside me! Fill me with it! Drown me in it! Make me yours for good!" he cried, shooting his load into the mattress.

It was during his orgasm that his ass violently seized around Martha's throbbing cock, sending her finally over the edge and into new, uncharted pleasures. Stars shone in her twinkling eyes as she slammed her fat meat as deep as it would go inside Jackson's quaking asshole and erupted with a triumphant, thunderous cry.

"I'M CUMMING, I'M CUMMING! Fuck, ahhhhh, yes-yes-yesss!" Martha's swollen prick lurched with each hot gush of thick syrup inside him. Their sweaty bodies trembled together as she crammed her sticky load all the way up his ass, shooting him full with rope after rope of boiling sperm. Martha grunted and groaned like a wild beast as her balls emptied deep within his tender, convulsing passage.

"I feel it all, fuck! I feel every shot. So much, there's so much!" Jackson panted, loving the way it splattered everywhere and coated his insides.

Martha's shaking legs gave out beneath her and she collapsed down on top of him, mashing her sweaty tits into his back, while her hard slab continued to blast, coating him in love goo. Time slowed down, she kissed the back of his head frantically, spewing everything she had inside him, squeezing out every last drop she could give.

They laid like that for a few moments, perhaps a few minutes. Neither of them was counting. Martha's big, sweating body seemed to wrap around him so perfectly. She didn't want to speak yet and break the mood, preferring instead to smell his hair and nibble at his neck. Her cock remained inside his aching channel, being massaged lovingly by his exhausted anal muscles. Jackson took her hand closest to his face and placed dozens of slow, gentle kisses on it.

Eventually she had to get off him. Martha carefully withdrew her shrinking prick from the depths of dripping hole and rolled over next to him. They turned toward each other, she brushed the hair out of his face as their eyes connected.

"I'm cold now that you're not on top of me," he said, smiling.

"You won't have to put up with that too much. I'm going to spend a lot of time on top of you from now on," she replied, smiling back. Martha took the blanket that was next to her and draped it over his soft, beautiful body.

"So I guess we won't be going into business selling my spunk, huh?" She chuckled.

"No, I want it all for myself." Suddenly he remembered something. "Did... did you want to eat the cum from my ass?"

"No. What do you think I am? Some kind of sissy?" she said with a wicked grin before catching on her finger a freshly-formed pearl of cum from the tip of her cock and bringing it up to his mouth.

Jackson got over his sudden shock at her ribbing when he saw the beautiful pearl shimmering there for him. "Being a sissy has its perks," he said, the smile returning to his face. He engulfed her finger between his greedy lips and sucked it clean. Martha's eyes twinkled when she saw his shut as he savored her taste.

"What I will take is half that blanket and a kiss," she said, snuggling closer to him and pulling it over her big body.

"You're going to need more than half."

"How dare you." She caressed his cheek.

"You started it with that sissy talk," he said, beaming at her.

"Next time you make a comment like that I'll throw you out of my bed." Martha winked at him, taking his hand and placing it on her breasts.

Jackson began to squeeze and play with them as he spoke. "I'd like to see you try. I wouldn't make it to the door before you saw the cum dripping from my asshole and begged me to come back for another round."

"You're right... smart-ass."

"It's sore-ass now after what you just put me through."

Martha chuckled, her smile broadened as she brought her face nearer to his. "Better watch out or I'll do it again."

"Yes, please." Jackson bit his bottom lip.

"Now who's begging?" she asked, reaching over to pinch his butt.

"I am. So kiss me already."

The conversation ended as their lips met.