The Ruination of Randy (F/M Intense)

“EEEE-EEEE-EEEEEEEEK!!!” Randy squealed, lifting his bare behind from the mattress and wiggling it frenetically. “STOP it! Don’t fucking DO that—!”

“Now don’t be such a SISSY!” Gwen admonished him. “It’s just a little TEASE!”

“But you’ll make me CUM!” Randy cried.

“Oh, I don’t THINK so!” Gwen chortled. “That would be a terrible SIN, wouldn’t it? You’re my STEPBROTHER, for heaven’s sake!”

“GRRRRUUUUMP!!!” Randy grunted as her clever, sharp-nailed fingertips stroked the head of his tumid boy toy. “OMYGAAAAW-HAAAAW-HAAAAWD—!!!”

He jerked his arms and legs in a desperate attempt to slip the bonds that secured his wrists and ankles to the corner posts of the bed. But it was no use! The bitch had used plenty of duct tape and there was no escape from her perverted ministrations! He was naked—he was spread-eagled—and he was completely fucking DEFENSELESS—!

“Better not lose control of your emotions…” Gwen cooed. “If you make a mess, Randy-candy, I’ll have to give you an extra-special punishment…”

She punctuated this threat by stroking his pee hole—which sent a thrill through Randy’s body that made him whine and writhe!

“Naughty boys DO make excellent tickle toys!” Gwen snickered. “Especially handsome college jocks who have desperate CRUSHES on their STEPSISTERS!”

It was his own stupid fault, Randy told himself as he struggled to stave off the orgasm that his sexy stepsister was coaxing out of him. Gwen was a hot blonde, nineteen years old—leggy, curvy and a more than a bit of a tease. She’d come into his life a year ago when his mother remarried, and it hadn’t taken her long to notice that that he’d developed a bad case of the hots for her. Randy had tried to be good—he’d tried to resist temptation—but Gwen hadn’t made that easy, the bitch! She took sadistic pleasure in flirting with him, showing off her legs and cleavage, making suggestive little comments. Finally, one weekend when he was home from Unknown University, he’d snuck into her room—where she’d busted him jerking off while wearing a pair of her panties!

The choice he’d been offered was stark: “You can accept my punishment, Randy-candy, and the whole thing will remain our little secret. Or I can have a chat with the parentals about this. Your choice…”

That was no choice at all and so here he was, alone with Gwen in the bedroom of her father’s lakeside summer cottage, being subjected to this unthinkable humiliation!

Kneeling by the side of the bed, the leggy blonde toyed with his rigidly erect penis until Randy squeezed out a clear, tiny drop of pre-cum. “Uh-oh! I think somebody’s betting CLOSE!” she exclaimed.

“Oh FUCK!” Randy cried. “Oh SHIT! Oh FUCKING shit! Oh PLEASE don’t STOP—!”

“But you said you didn’t want to commit such a heinous SIN!” Gwen reminded him.

“Gwen PLEASE!” he cried. “I’ve learned my LESSON! Just let me GO—!”

“Hmph!” she snorted. “A second ago you were begging me to bring you OFF! So which is it, Randy-candy? Release or…release…?”

“Oh my dear sweet GOD!” the naked jock whined. “I’m so CONFUSED—!”

“I can easily unconfuse you, sweet cheeks,” Gwen whispered, placing a hand on his thigh. “But that would mean extra punishment, of course…”

Randy moaned. Her hand felt very soft and warm on his thigh and he longed for her to move it higher…to caress the most precious and sensitive portions of his masculine anatomy…to grant him the favor that despite his guilty conscience he so ardently craved…

“Hmmm, but you might actually enjoy my punishments…” she went on. “Yes, Randy-candy, I think that you like being tortured by your sexy stepsister…”

“NO! I do—”


“—NOT!” Randy cried. But Gwen could tell that he was lying.

She’d been pleased to discover that her new stepbrother was a good-looking brown-eyed brunette, well built, hirsute of limb and torso. And she’d been absolutely DELIGHTED when he’d developed a desperate crush on her! But alas, Randy proved to be a bit of a prude. She’d teased him mercilessly and it was rather amusing to see him squirm and blush, but had never been able to entice him into a compromising position of the kind that would infallibly enslave him to her will.

“So how about it?” she whispered, moving her hand a trifle higher. “Are you ready to cum for me, Randy-candy? Ready to make a mess and accept your punishment…?”

“Oh Gwen PLEASE—!”

“Just let me get comfortable,” she said with a wink. The leggy blonde was clad in a halter top and shorts. With brisk efficiency she stripped them off, exposing scarlet silk panties and firm, ample breasts that swayed ever so slightly as she moved.

“Recognize these?” Gwen inquired, indicating the panties. “That’s right, sweet cheeks, they’re the same ones you were wearing when I caught you masturbating in my room. I thought it might be fun to wear them myself while I played with you…”

“HEEEEEEEE!!!” Randy squealed as she dug her nails into his thigh. “Oh SHIT! That TICKLES—!”

“Does it? How interesting!” She dug in again, this time flexing her fingers.

“EEEEEE-HEE-HEE-EEEEEE-HEE-HEE!!!” the naked jock howled, squirming to and fro on the bed. “IT TICK-HICK-HICKLES MEEEEEE-EEEEEE-HEE-HEE!!!”

“So I see!” Gwen chortled. “And how about your BELLY, Randy-candy? Is THAT ticklish too?”

“GAAAAAA-HAA-HAA-AAAAH-HAA-AAAAH-HAA-HAA-AAAAH-HAA-HAA-HAA!!!” he screamed as her well-honed nails stroked his drum-tight abdomen.

“Goodness!” Gwen exclaimed. “For such a masculine jock, you’re very SENSITIVE, aren’t you?”

“HIIIIEEEE-HEE-EEEEEE-HEE-HEE-HEE-HEE!!!”

“Let’s try this,” the leggy blonde suggested, sticking a finger into Randy’s belly button.

“EEEEEEYAAAAAAR-HAR-HAR-AAAAAAR-HAR-HAR-HAR!!!”

Gwen tormented her writhing stepbrother’s midsection for five solid minutes, until Randy’s face was bright pink and his body was bathed in a delicate sweat. Then she let him gasp for air for a while as she pondered her next move.

The leggy blonde was interested to note that Randy’s cock was still standing tall. Perhaps, she reflected, there had been some truth in her insinuation that he enjoyed her tortures. But that mattered less than the fact that SHE enjoyed inflicting them on her handsome, helpless stepbrother! Gwen sighed with pleasure. Things had worked out after all. She now had Randy by the balls…and she intended to take full advantage of the situation…

“Well,” she cooed, running her fingers through the naked jock’s chest hair, “now that we’ve discovered your weakness, sweet cheeks, let’s test your limits, shall we?”

“Omygod!” Randy blubbered. “What are you going to DO to me—?!”

“Hmmm, good question…” She stroked a nipple until it stiffened. Then—

“AAAAAARRRRRRGH!!!” Rand bellowed as his nipple was smartly tweaked. “You’re HURTING me—!”

“But Randy-candy you—”


“—LIKE the way I hurt you! Isn’t that RIGHT?” Gwen demanded, tweaking again.

“EEEEEEYAAAAAAR!!!” Randy screeched as a jolt of pain—curiously pleasurable pain—shot through his body. And he realized that the sadistic bitch was right—he DID like what she was doing to him! It made him fell all LOOSE and GREASY, deep down INSIDE at the bottom of his BELLY—!

“Dear me!” the leggy blonde remarked with mock disapproval as she began teasing his other nipple. "Is that a drop of pre-cum, sweet cheeks? Am I getting you all EXCITED?”

“HIIIIIIEEEEEE!!!” Randy shrieked as she tweaked again. He squeezed out more pre-cum.

Each nipple received half a dozen tweaks before Gwen relented and moved her hand down his torso. The naked jock moaned as her fingers closed around his upright organ. He wiggled his hips, mutely begging to be stroked. But the fucking bitch’s hand remained still!

“I bet that if I teased your precious PENIS, Randy-candy, you’d come all the fuck OVER yourself in about thirty seconds!” She put on a rueful expression and shook her head. “But you wouldn’t want to disgrace yourself in that manner, would you? No, sweet cheeks, you’d rather be TICKLED, isn’t that right?”

“Gwen—PLEASE! I don’t think I could TAKE it!” Randy’s arms and legs jerked in another futile attempt to escape the duct tape. “I’ll do ANYTHING! Just let me GO—!”

“That’s right, Randy-candy,” the leggy blonde nodded. “You WILL do anything—anything I say! Because if you don’t, well, then I’d have to have that chat with the parentals concerning your shocking behavior.”

“I’ll fucking DENY it—!”

“I took a couple of pictures with my phone.”

Randy begged and pleaded, but Gwen was implacable. “You’re my slave now,” she sneered, “and my slaves do as I say! Right now, I want my slave to LAUGH for me!”

So saying, Gwen moved to the foot of the bed. A shock of horror shot through Randy’s nervous system as he realized what her shift in position portended.

“Don’t you DARE!” the naked jock screamed. “Leave my feet ALONE—!”

But Gwen merely smiled as she—


—knelt and for a long moment contemplated her helpless stepbrother’s bare, wiggling feet. She licked her lips. One hand stole to her breast and began stroking its erect nipple…

“Oh PLEASE!!” Randy cried. “Not my fucking FEEEEEE-EEEEEE-HEE-HEE-HEE-HEEEEEET!!!”

“Now don’t be such a SISSY!” Gwen admonished him as she stroked the sole of his right foot with her sharp nails. His response to her ministrations was most gratifying—the naked jock pitched an absolute HISSY fit! He writhed and struggled with desperate energy, causing the frame of the bed to creak. And he laughed! Oh, how he laughed! He laughed like a fucking LOONY bird—and it was music to Gwen’s ears!

“Tickle, tickle, TICKLE!” she chanted, bringing her other hand into play. “Randy-candy likes being TICKLED!”

“OH-HO-HO-OH-NO-OH-HO-HO-OH-HO-HO-HO!!!” he bellowed. “GET OFF MY FUUUUK-HUCK-HUCKING FEEEEEE-HEE-HEE-HIIIIEEEE-HEE-HEEEEEET!!!”

Gwen’s nostril’s flared. His musky scent—an amalgam of sweat and sexual arousal— perfumed the air of the bedroom. The leggy blonde realized that her panties were becoming damp. One of her hands left off tickling and insinuated itself into the panties, to pet her curl-covered mound…but just for a moment, she admonished herself…just for a moment…

She made Randy howl with laughter for many minutes, not relenting until a deliciously pleasurable thrill gripped her loins and pulsed through her body. Only then did Gwen awake to the fact that the hand she’d plunged into her panties was still there…

“Mmmm…” she sighed, moving back to the side of the bed. “I have a feeling, Randy-candy, that I enjoyed that more than you did…”

The naked jock didn’t reply. He was too busy gasping desperately for breath.

“So, Randy-candy,” the leggy blonde continued as she wiggled out of her panties. “I think that at this point we should discuss our future relationship.”

“Gaaaa…gaaaa…gaaaa…” the naked jock gasped in reply.

“The way I see it, sweet cheeks, I have you by the balls.” And suiting the action to the word Gwen grabbed her stepbrother’s scrotum. She dug in with her nails, smiling with satisfaction as Randy squealed and squirmed. “In fact, I’d say that these balls and their contents are MY property!”

“W-w-w-what do you mean…?” he stammered.

“I mean that from this day forward, you can regard yourself as my SLAVE, Randy-candy!” She gave his balls another sharp-nailed squeeze. “Get the picture?”

“Omygod—!”

“You’ve been a good boy for me today, sweet cheeks, so I’m going to give you your REWARD now!” Gwen’s hand moved to Randy’s tumid tool—


—and began to stroke! Randy arched his back and gyrated his hips in a mute plea for release! The touch of Gwen’s hand swept all thoughts of shame and humiliation from his mind! He didn’t fucking CARE that she’d tortured him by tickling! He didn’t care that she was a sadistic BITCH who was promising to make his life HELL! No! the only thing he fucking cared about was her hand—how it moved up and down—but too slowly—oh why couldn’t she go fucking FAST—?!

“Tell me when you’re getting close…” Gwen whispered. She put her other hand on his chest and began running her nails over his torso. And it fucking TICKLED—oh, yes—but in SUCH a sexy WAY—!

“UGH!” Randy grunted. “UGH! UGH! GRRRRRRUUUUUUGH!!!”

And oh, he could feel it coming on—the sweet sensation was beginning to build in his balls—and every muscle of his body was tense with anticipation—and a plague of goose bumps was roughening his skin—and she was stroking with her thumb and forefinger now—up and down—over the swollen head of his yearning penis—and it was going to happen any MOMENT now—!

“Omygod I’m cumming NOW—!” Randy cried.

And instantly, Gwen plucked her hand away!

The naked jock arched his back again—this time in response to the orgasmic wave that flooded over him as be began to empty his balls. But where was her HAND?! Tears of frustration stood in Randy’s eyes as he squirted himself from neck to groin while Gwen knelt there with a snide smile plastered all over her beautiful face!

“Yuck, you really DID make a mess!” the leggy blonde snickered. “And I guess I kind of ruined your orgasm, didn’t I?”

“Oh Jesus GOD!” Randy blubbered.

“But I’ll make it up to you!” she giggled, grabbing his still-erect boy toy.

“YAAAAAARRRRRRGH!!!” Randy screamed as an unbearably potent sensation convulsed his body. “DOOOON’T—!”

“A little SENSITIVE, is it?”

“EEEE-EEEE-EEEEEEEEK!!!”

“Okay then, Randy-candy, how about more TICKLING?” Gwen climbed aboard the bed to kneel between his legs.

“YAAAAAA-HAA-HAA-HAA-AAAAH-HAA-HAA-HAA!!!” he screamed as her sharp nails probed his armpits.

“THAT’S right, you dirty fucking little boy! LAUGH for me!” She sank her nails into his ribs. “Laugh your handsome HEAD off for me! Laugh your sexy ASS off for me—!”


Three hours later, Randy was treated to a second ruined orgasm at the hands of his sexy, sadistic stepsister. By then he’d been thoroughly tutored in his duties as Gwen’s slave and poodle boy. The thought of the abuse to which she’s subjected him made the naked jock cringe with shame…and excitement. Had he actually begged on his knees for permission to worship her feet…and her pink places…and her brown ones? Yes, he had…and he would again…

Gwen, lounging on the bed while her handsome, servile stepbrother pampered her feet, sighed with satisfaction. It would be so nice to have him at her beck and call. Already she was planning their first weekend together…when the parentals would be out of town…and he could go naked for her the whole time…

“Just remember, Randy-candy!” she commanded. “I don’t want you masturbating! You only get to cum by MY hand!”

“Yes, Mistress,” he replied.

But the leggy blonde knew he couldn’t be trusted to behave himself back at U.U., where she wouldn’t be around to supervise him. So…

“Tell me, sweet cheeks,” she purred. “Have you ever heard of chastity…?”

Wonderful story!