Autumn

It’s autumn, which means all across America college boys will be locking up their dicklettes again. “Locktober” and “no nut November” have been big events on campus both of Colin’s first two years as a student. He almost made it all the way through October last year wearing the cage, but he broke down and begged his keyholder RA to let him cum on October 24th. 

This year he is determined to make it. He started practicing by locking during the week while on campus starting just after Labor Day. He read somewhere that playing with his ass could cause a prostate orgasm, which he hoped he could teach himself to do before October 1 so he went out and bought a huge dildo. 

Now instead of jerking off every night, he’s pussy fucking himself all the time. It was on the third night riding that dildo he realized he had a pussy, it was a real revelation. He hasn’t taught himself to cum hands-free yet. But he’s finding out more and more that he doesn’t mind wearing the cage as long as he gets to fuck himself all the time.

Colin hasn't thought about his poor limp neglected in days instead he sees the next two months as solely pussy time, connecting to his femininity, and the need he has in being fucked. So much so that he's asked all his top friends to fuck him regularly, and his bottom friends now come to his place for pegging parties.

It's Time

"You see how good that makes you feel. See how Daddy's fingers make your little hole squeeze over and over? That means your ready for Daddy to give you a proper pussy."

Stuart said this as he massaged his fingers in and out of his mewling boy. This entire moment happened because Stuart had grown tired of hearing how much his son's back hurt. So he had talked Simon into a massage to relieve the pain. Naturally, he had other things in mind. However, sonny-boy was clueless as to what was to happen. His son thought a regular massage would happen as his dad ran a successful massage side hustle.

What Simon didn't know was that his father's massage business had a ninety-eight percent gay male, sexually passive clientele. Or that his father fucked and bred his clients. His father also had popped his fair share of cherry's.

It all started with, "up on the table. Face in the cradle and I'll focus on your back like usual." Nothing out of the ordinary if you asked Simon. Dribbling lavender oil Simon's father began knowing his son required firm rough pressure to relieve anything. 

"Oh god, Dad.... ummmmffffppphhhh. Lighten up just a little bit."

"Remember to breathe through it, that way the pain and tension will release and you'll feel better." His father's hand moved to where the arch of Simon's ass and his hands began moving lower. "Arch your back some, it will release the knotting going on. I'm going to massage really deep when you do. So breathe really deep." 

Simon did as he was told, again questioning nothing, but the towel drooped toward his waist as his ass went up and, Stuart, his father saw his son's hairless pink starfished shaped pucker. Simon's father openly stared knowing his son was unaware he was exposed this way, he thought to himself as he licked his lips.

"OOOOOwwww Dad not so deep with the force of your hand on my back." Stuart let up and his son's butt popped up more, the towel was around his waist. Simon was nearly on all fours, although his arms stayed on the table his ass was that high. With his ass so far in the air, his pucker was fully exposed. If I didn't know any better I think he loves exposing his cunt to me. Or is he in heat? Either way, he could stay like this for me forever. When a client does this it means he wants his pussy played with.

"Here let's remove the towel, baby boi," Stuart said rubbing his son's back. Stuart's hands moved to the globes of his son's hairless bubble butt. Stuart dribbled lavender oil on his son's ass. "Stay arched up," as he began working Simon's glutes. Stuart also dropped his shorts and was like his son, naked. His erection grew because Simon's twat was still fully exposed.

Having always been locked in chastity, this was the only sexual pleasure Simon would know. Chastity came about because Stuart, a few months back, late at night discovered by accident that his son was riding a huge dildo. Stuart got out of bed that night, nude. It was after all like 2 AM and he and his son lived alone knowing Simon was asleep, and walked to the bathroom, which was past Simon's room. Simon's door was wide open and Stuart swore he heard mewling before he got to Simon's bedroom. 

"I think it is time baby girl. Time for Daddy to show you what he made you for."

The man lined his cock up to the quivering pucker. The tip of his angry cock ached to pierce into the virgin flesh. He pushed slowly, savoring every sensation. His son gripped the sheets as he felt his very maker enter him.

"Fuck... Good girl..."

Waited Long Enough

Turning his son to his side on his bed, and spreading his ass open Gerald said, "This is an important moment son..." His father said as he looked upon his son's virgin hairless hole before him. Gerald had put this moment off for far too long in his opinion. His son had come out as gay months ago when he first started college. 

When Kyle came out he started going to an all-gay male salon for their waxing services as he knew when he was going to have sex for the first time he was going to be the bottom. Kyle also knew good bottom bitches waxed, especially their pussies. He had been reading the "Size Kings" series, after all, by non-binary author P.B. Breckinridge and what it took to be good pussy for men. The opportunity though to be actual pussy for men though had yet to happen.

"What do you mean dad?" His son asked. It started simply because Kyle had developed a severe Charlie horse in his upper calf and his father had offered to massage it out for him. How he ended up in his father's bed completely naked however was a blur. Not that Kyle was complaining. His father was smoking hot.

"You and I are going to do something very extraordinary. Something extremely beautiful." As he spoke he brushed the head of his erect dick against the innocent exposed and lubed pucker. Granted it was just baby oil, that lubed Kyle's pucker, but it was enough. When his father's oily hand had accidentally brushed against Kyle's pucker it had winked at Gerald. Maybe it was just a reflex of being touched, or maybe just maybe Kyle did it on purpose. Either way, Gerald could no longer resist.

He continued. "We are going make you into a girl. Actually, MY girl if I'm honest with you."

The boy started to look flustered, confused, and unsure of everything.

"Shh shh now sweet thing, Daddy loves you." With that, the father sank his dick into the squirming boy. "Ohh that's it, squeeze that pussy for Daddy like a good princess."

"But are you even sure I am a princess?"

"Hmmm? Let's see... ur in my bed completely naked, ass up & my dick up ur waxed hairless cunt. You're a princess!"

"I thought a princess meant you got bred."

"Oh, you'll be bred, baby girl, and a lot." Kyle's father was balls deep.

"MMMMppppphhhhhttt your so fucking big! Damn!"

Gerald slapped Kyle's bubble butt. "Come on cuntboi, open up! Relax that pussy.

Fully Letting Go

He kept hitting right into the boy's princess spot. He watched the boy try to hold on and not dribble cum or to ejaculate hands free. Trying to keep hold of himself and not lose himself to the feminine pleasure he was feeling from getting his cunt worked over.

Over and over the boy could feel himself being spread open again and again accepting the full length of the man's powerful thrusts. His dick was so deep.

And between his legs was a soft little nub, shuddering in the open air. The man never touched it, the boy had surrendered his virginity not even knowing of the cost. Now, at any moment, the little nub will lose to the pulses of pleasure from deep inside, feeling truly opened and used.

The man felt the hard little spot swell against his dick. It pushed him over the edge. As he began to orgasm, he saw the boy become something beautiful on his cock.

He watched the boy's eyes gloss over, his body started to convulse, and he began to moan in a higher and higher voice. He could feel the pink hole spasm on him over and over as it became a full and beautiful pussy. The pulses of his orgasm were in sync with the pussy now milking the cum from his cock.

Then he watched the little nub. It didn't even swell. It didn't pulse or jump. It seemed to shrink even tighter and tremble. Then at the peek of his pussygasm, he witnessed it finally happen.

The boy exhausted released a breathe and let go. The little nub started to softly dribble a clear fluid. It was not explosive or even that much. It was the death gasp of the boyhood and it was adorable. The little clit looked so innocent and scared, he would keep it nice and safe. Protected and pure, it would stay as innocent as it looked. As the last little drop oozed out, the man watched his good girl struggle in her first hands-free ejaculation, fully letting go and letting the feminine pleasure destroy her masculinity. She was now a beautiful princess wrapped around a man's cock.

Devotion

This is your Dad. He's a nice guy and a big cuddly bear, but you wouldn't want to cross him. When he says "suck my dick", you suck his dick. When he wants you to stand on his hips and squat, you do it. You want to impress him, so you ride his big dick like a whore, or try to. You whine "It's too big". You squeal, he laughs. He grabs your butt and pulls you down.

'Come on boy, get down on that big dick,' he commands.

You start whining.

'Focus boy! Don't give me half-assed service. Give me your all,'

You blink back tears, and you slide down further down. The tight ring of your pussy is halfway down his shaft... You feel that big hard dick deep inside you, pushing at your second internal pussy ring, and through it. A new level of penetration, that sent shivers through you with each bob. Your knees hurt, but you keep bobbing your butt up and down, and look into your Dad's face, hoping to see him pleased. But he's not, he's scowling, and gruff.

'Please, I'm trying, I'm trying,' you whine.

He reminds you who the boss is. Domination activates your genes, and your cunt seems to open wider of its own accord, taking the paternal rod so deep that you felt its tip soar through that second sphincter and up to the third. As you pushed yourself down, you felt your third pussy be breached. Ecstasy washed over you, as you realized that all the space inside of you belongs to him. At the lowest squat you could manage, you feel his pubic hairs on your taint. Up and down you go. 

Dad's eyes were fire, commanding your service. Each of your three cunts was breached again and again, creating rising pussy-gasams, that tortured you with ever-rising but never resolving pleasure.

Suddenly, it became unbearable for Dad, and his eyes flashed: 'Time to show you who's boss,' he said.

With one motion, he rose to his feet and embraced you in his strong arms. Tiny compared to him, he carried you with as much ease, it was as if you weighed nothing. Still inserted into you he crushed you against his chest, and your legs spread up on either side. Grasped your entire body as if you were a fleshlight and forced his cock deeper. You learned then, that you had not in fact, got all of his dick all the way in you, there was at least one more inch. One inch deeper, beyond your third pussy. Suspended in the air, he fucked his full length into you. It felt as if each pussy-ring was being punched open, to your very core, much faster than was comfortable. 

Squeezed so tight, you couldn't speak, you could hardly breathe. A helpless toy. You couldn't say if it was joy, pleasure, or love. He fucked you beyond the threshold and your deep pussygasm exploded. You struggled futilely against his grip, as your cunts dilated and clenched involuntarily in a way that only encouraged and serviced his dick more. The rush caused increased internal lubrication and sweat. He wasn't even slowing down. It only encouraged him. He wasn't letting you go until he forced another load in you. Your brain was in total devotion and submission, as you transformed into a cum dump for the man who created you. 

Spinning

His brain was spinning. He felt full in a way he never thought possible as his pink lil pussy spasmed on the big dick sheathed inside of him. His cunt had never been looser, but than again he had been getting cunted for over an hour already. It was sheer and utter heaven.

All because he had gone to that new bar on Lexington dressed like a whore, picked up instantly by the couple he now was with.  Bryce still buried in his way

Then Cody began to line up his even bigger dick to enter his stretched-out gash. His eyes went wide and he threw his head back as he prepared himself for the experience of absolute and utter submission. Snorting the poppers he had on him when he left the house he began to relax even more as his head swam. His pussy growing even hungrier.

His soft clit leaking, knowing he had already given up his manhood. The whole world was about to be reduced to the joy and pain his pussy was feeling. God he loved being a girl.

Keep On Trying

So close yet so far. You can feel your whole body tingling. You've been there before, many times, but you never managed to quite get yourself to shoot your load like this -- locked and not touching your clitty. 

You had been playing around with chastity for some time and always looking for new challenges. After a while, nothing quite seemed challenging enough anymore. That was until your new, kinky boyfriend -- finally somebody who understood why you wanted to lock your dicklette -- suggested locking your dicklette until you managed to cum from pussy stimulation alone. He, of course, would hold on to the key. After all, it's not really chastity if you can just unlock in a weak moment. 

This was such a hot challenge, but there were just two problems: 

1) You had never even gotten close to getting a hands-free orgasm before and even now, months into the challenge, you always fall frustratingly short. You're just not convinced you'll ever manage. 

2) You're pretty sure that if and when you do manage to cum this way, he'll just say: "See! Now, there's no need to ever unlock you again!" 

Every day, every week, that goes by without being unlocked, you're starting to accept more and more that he's just decided to keep you locked permanently regardless of the outcome of this challenge. All the more reason to train yourself desperately to cum like a good little girl!

You were always meant to be locked permanently.  This is his way of giving you more motivation to learn to squirt.  A responsible Daddy works to improve a girl's threshold for pleasure as well, teaching her how to find all the ways that sex can be enjoyable.  But it's up to you to learn it.  Daddy's going to cum either way.

Submit and Obey