Rewind Railing

Hey, Pink Fairy. I’m 30 now and sometimes I worry that I didn’t have enough fun when I was younger. Can you do something for me? I want it to be my 21st birthday every night! And I wanna be ready to party!

Story Request by @derekwilliams

This is a rewrite of a request previously received and responded to on Tumblr.

You wake up one day, feeling rather strange as the sunlight streaming through the windows shines straight into your face. You groan, stretching your arms over your head.

You roll over onto your back and yawn. You still like sex, now that you’re older and wiser, but not as much as you used to. The burning libido of your prime years has gradually mellowed out, lustful thoughts taking up less of your mind than in the past.

Today is different, though. Your body seems to disagree that you’re not as horny as you used to be. Your cock is rock hard and the way that it throbs so insistently makes it impossible to ignore.

The light blanket draped over your naked body is tented out obscenely between your legs. A small wet spot grows at the tip of your cock. The feeling of the fabric rubbing against your cock head makes your body shiver with delight.

In the back of your mind is the faint recollection of a dream you had last night. It is already fading, but you still have the image of a sex shop that shouldn’t exist in your mind.

Vaguely, you’re aware that you’ve made some sort of deal with a strange cosmic force of some description. However, you can scarcely remember the nature of this entity, much less the details of the deal.

Thinking too much about it gives you a headache so you set it aside. As soon as you let the matter go, you promptly forget about it. No matter. Something else demands your attention, anyway.

You grab your cock. It throbs at your touch. You’re more sensitive than you remember ever being but you can’t complain. It feels so good.

You’re tempted to do the usual, perfunctory stroking that masturbation has become for you, now that you’re older but as you approach the edge you feel a sudden urge to enjoy the feeling. You take yourself as close as you can, pinching a nipple between the thumb and forefinger of your free hand.

Your cock throbs as you approach the edge, but you stop just short of spilling. You stroke yourself faster and harder, holding back from your climax to bask in the feeling of riding the edge.

You’re not sure how much time you lose to edging, but it doesn’t matter. It feels so good. You haven’t been so horny in a while and you want to savor it.

Still, your stamina is not infinite. After what feels like an eternity and yet altogether too short still, you come. You blow a massive load all over your stomach, chest, and face.

You lie there for a second—thick ropes of cum cooling on your chest and stomach. It was an intense jerk-off session, but you can’t spend all day basking in the afterglow. You slip out of bed, swinging your legs over the side. It’s time to get on with your day.

The haze of arousal around your mind doesn’t dissipate one whit, making it difficult to think, to process what’s going on. Somehow, you manage to make it to work, but the guys seem to be acting rather differently toward you.

It’s strange. You don’t head toward the office you’ve been working from for the past half-decade. Instead, you make your way to a cubicle. The same one you were assigned on your first day on the job ten years ago.

One of your colleagues, who looks strangely younger and as attractive as ever, even makes a pass at you. There’s a hesitation, in the back of your mind, because you just know that he’s spoken for. And yet, somehow, you also remember that he’s quite single and more than ready for some fun.

Needless to say, one thing leads to another and when he heads to one of the bathrooms, he conveniently forgets to lock the door. You follow, of course, some minutes later, having also conveniently forgotten that the particular bathroom is occupied.

Your co-worker gives your hole a good workout. When you first see his big dick, you’re afraid it won’t fit, but all such reservations evaporate the moment he pushes you up against the door and slides his meat between your ass cheeks.

He fits with ease and slides into you in one smooth stroke with no pain other than the burn of feeling your hole stretch around him. The sounds he extracts from you could have made a whore blush, and the way he grabs your hair and pulls your head back while slamming you against the door with his hips makes sure that your desperate cries are heard by the rest of the floor.

By the time you emerge from the bathroom, you look utterly disheveled and your hole has been brutally ravaged. You feel his cum dribbling down your legs, and can’t help but flush at the knowing looks shot your way by your coworkers.

The rest of the day passes by in a blur. You head to the bathroom again a few times—occasionally with a friend to keep you company. On one occasion you happen to glance in a mirror and are shocked to see how young you look. Unfortunately, the cock pounding your prostate leaves you without the opportunity to process this information.

You have more than a few loads leaking out of your abused hole by the time the workday is over. Just as you’re preparing to leave, a few of the guys come up to you and tell you they’re looking forward to your party tonight.

You’re confused for a moment. Not for long. You quickly recall that it’s your 21st birthday tonight, even though you’re pretty sure that you’re pushing 30.

Nevertheless, you can’t help but giggle. You can’t believe you forgot such a basic fact. You apologize for being such an airhead but one of the guys comes up behind you, gropes your ass, and calls you babe.

You’re in the middle of the office floor but no one seems to complain as he slides his hands down the back of your pants. His finger slips into your hole and you can’t help but buck your hips against him. You fuck yourself on his fingers as he churns the loads you’ve gotten fucked up your chute through the day.

The way home is also a bit different. You were so out of it earlier in the day that you didn’t notice but now it’s impossible to miss. You’re pretty sure that you’ve managed to secure a comfortable, decently-sized apartment for yourself but the home you return to is quite tiny.

It’s not a surprise, though. You’re not sure how you got it in your head that you could afford anything substantially bigger than the tiny apartment you currently have. You’re fresh out of college, after all. You don’t have the career prospects to afford more—even if you do badly want a larger apartment.

The end of the workday is always nice, though. It’s a good time to unwind and relax from all the not-work that you did at work today.

You throw yourself down on the couch and lean back to take a moment. As you do, the haze of arousal in your head gets thicker. It gets worse with every moment that passes.

It gets more and more difficult to think until you eventually don’t want to think at all. You giggle to yourself and strip off your clothes, spreading your legs to idly finger your hole.

It feels good.

So good.

Shortly thereafter, your friends come by. They have a spare key so they invite themselves in. They’ve come with drinks, condoms, and lube.

Suffice to say, they’re ready to party and you’re the main attraction—even if it is your birthday. Not that you mind. There’s little else you can think of wanting to do at the moment, anyway.

You practically start drooling the moment they shuck off their pants. What remains of your older self is shocked. Your 21st birthday 10 years ago, the one you faintly remember in the back of your mind, had not been anywhere near as exciting as this one.

Not that you’re complaining.

Definitely not.

By the end of the night, you’ve been reduced to little more than a blubbering mess. Fucked every which way up and down your little living room and your nearby bedroom. Cocks up your ass and down your throat. Cum plastered all over your cute face.

You’ve been called slut and whore and bitch so many times through the night that you don’t really remember your own name. As you wind down from the high of a birthday night well spent, your exhaustion catches up to you and you pass out.


You wake up feeling somewhat strange the next morning. You had the weirdest dream last night. You were young again. And infinitely more slutty than you remember being.

Your cock is hard. Harder than it’s been in a while. All you can do while you reach down to stroke yourself is wish that tonight will be as fun as the night in your dreams.

As you blow a load all over your stomach, chest, and face, you realize with a start that you’re in the tiny apartment from your dreams. Your body is crusted with dry cum, in addition to the fresh load you’ve just spilled all over yourself.

Your hole is not so much sore as it is well-used. Loads from last night are still trickling out of you onto the sheets.

You glance at the calendar-clock by your bedside and realize with a start that the date is the same. It’s your 21st birthday again, and somehow that knowledge makes you even hornier.

The haze of arousal descends upon your mind once more, making it more and more difficult to think about anything other than sex. The last thought you have, before it’s scattered to the aether, is that it seems you’re living in your very own, very horny, very sexy version of Groundhog Day.

You don’t think you’ve ever been more excited in your life.

Your wish has been granted. Tonight will be just as fun as last night.

Tonight.

Tomorrow night.

Every night.

From now until eternity.

It’s a unique kind of hell, but you’re sure it’s a torment that you’ll enjoy. It’s not like you’ll ever know better. Getting hornier and dumber with every loop of the day until you’re no longer even aware that you’re trapped in a sensual prison of your own making.

Then again, you can’t really be trapped if you’re willingly submitting yourself to your bondage. In any case, there are worse ways to spend eternity.

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