Journey of Punishment...

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Woman who likes sexual punishments...
1.7k words
4.12
76.7k
25

Part 1 of the 2 part series

Updated 06/08/2023
Created 07/01/2017
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Fiction Experiment Chapter 1

She had tried the online spanking personals but found only a lot of men interested in imposing their own (usually physically improbable) fantasy. What she wanted - needed - was erotic punishment and the humiliation of it being witnessed, critiqued ... and added to. She needed her limits pushed and exceeded.

So she decided to embark on a journey of tantalizing and painful auto eroticism, increasing the pleasure through pain and releasing the long long past through accepted punishment. Pleasure and pain are two sides of the same coin.

Chapter one; it begins.

She sat down to write, naked, rubbing her smooth breasts still bruised from yesterday's tit whipping and clipping. So that she wouldn't come before the chapter was finished, she ripped off two pieces of duct tape and white trash chastity-belted her pussy. She was already throbbing and electrified but resolved not to come until the chapter was done. That was part of the punishment.

Day 1: Journal.

Today I conducted Anal Training and Punishment. Stopped at a rest area to insert a butt plug. Tried all positions, including kneeling with my pants below my knees on the floor to force my tight ass to take it. The only way I could slide it past the painful bulge was to sit on it and press my ass down upon it. It slid through my protesting sphincter with a burning sensation. It turned me on to be violating tight exit hole in a rest stop trail head with a compost toilet.

Since I was already at a trail head, I went out on the trail and ran around a little. The butt plug filled me up and twitched a little. I taped it in with a strip of duct tape. Then the punishment began in earnest. I hiked about a mile and a half, climbing hills and running, with each cheek shoving it harder into my ass as my legs moved. I ensured when I got back in the car to sit down straight on it, so that anything that my punished ass had pushed out was forced back in. While driving, I rhythmically clenched the painful piece of plastic, and I occasionally rocked myself up and down, back and forth, essentially fucking myself in the ass. It turned me on to punish myself and receive pleasure at the same time. The last half a mile was a boardwalk with signs. I did 20 push-ups and 20 deep squats at each sign, while quizzing myself on aspen and coyotes. After a total of 100 each, and a mile and a half of walking, jogging, each cheek forcing the 5.75 " intruder into me, my sore and punished asshole began to squeeze it out. In full view of any cars that might be passing, I reached behind and gave myself four hard thrusts, deliciously pulling out the bulge only to ram it back in. Sore and now limping, I returned to the car and kept it in while I masturbated. I told myself, "you are a bad slut, and you will only come with something or someone fucking that tight little ass." Afterward, I practiced clenching my asshole back to its tightness, for more pain and so that an eventual cock will find it tight, and I will groan and maybe scream as my most private hole is dilated by a throbbing cock.

Afterwards, my asshole burning but recovering, the tit punishment. I hate them for being huge, so they must be punished. I pulled up my bra and shirt, whipping each sensitive nipple and aureole with the two ends of an USB cord. Each exposed tit got 150. Then to give me something to think about, I clamped each nipple and left my huge, nasty, porny breasts exposed while I drove. If I can't find anyone else to issue my hard punishment, I'll do it to myself. Maybe eventually I'll have a man who will treat me the way Jack used to use and punish me.

Interlude: the past

Get naked and get on the bed. Elbows and knees. Arch that heart-shaped slut ass in the air. Do you hear that? Yeah, you hear that, that's my belt coming out of the loops. You're going to get it hard, you little bitch. Start counting.

My ass was pointed up. The doubled-over belt slapped first from side to side, ten on each cheek, then vertically up to punish the tender flesh where my thighs met the curve of my ass. I moaned and pointed my ass higher up. The belt came down harder and harder, and I rocked back and forth on my elbows and knees.

Please stop. Please. My ass can't take it anymore.

Your SLUT ass. That's five more. Each side.

My slut ass. I'm sorry.

Let's have some more descriptions for that slut ass.

My slutty, nasty ass that needs punishing. My dirty ass that needs a belt on it and to be bruised and spanked daily.

It was like the burning pain on my belted ass cheeks was making me enjoy saying this. I could feel the bottom of my gut begin to warm with pleasure, and my pussy lips were plumpening.

Why are we doing this? Why are you here with your ass in the air getting whipped with my belt? Here's a few more to help you think.

Ow ow ow... ow. Ok, please stop, I'm such a bitch and I'm sorry. I told you your job was shit, I didn't care how much money you made.

So you bought the beer tonight, didn't you? Yes? And you didn't even notice that I left one on the nightstand. You lazy little fucker, you can't even clean up after me like I told you to.

SMACK SMACK SMACK.

I'm sorry, I said I was sorry.

You're going to be more sorry. Have the last sip of that beer. Get your lips around the bottle. Great, it's nice and wet. Now fuck your slut ass with it. That's right, squeeze it in there and start fucking your ass.

I try to relax, I tell myself this is well-deserved, and I force the cool lip of the IPA bottle into my clenched asshole. Once it's inside and still, it's actually not that bad. But more was to come.

Push it in to the neck. I'd make you take the whole thing but I want that behind tight. Now pull it out, all the way. Take it out and push it back in again. No, you aren't going to just wiggle it and pretend that's a beer bottle ass fucking. You're giving yourself the real thing. All the way out, all the way in. Keep doing it.

The lip of the beer bottle violated my ass ring with every shove. But the more I relaxed and accepted the punishment, the less it hurt. I told myself, yes, I was a little shit, I yelled at him and hurt his feelings. The least I can do is sodomize myself as if I mean it. At least my burning ass cheeks get a rest.

That's good. Your ass is going to hurt tonight. Faster. As fast as you can. Rear up to get a better angle. Do it faster or you're going to take the thick end. Awesome. Just like that. Shit, you got it past the neck. In further. OK, that's enough. You're shaking. Wow. You aren't done being punished yet, but you're going to get points for good behavior. Take it out. Nice, dilated.

Please, I said I was sorry. Can it be over? I'll suck your dick. I'll take it down my throat. You can come in my mouth or on my tits, whatever you want.

If you're that sorry, it's time to beg for anal.

No, please, I'm sore. Can I blow you? I'll suck your huge dick so hard.

I felt a tooth last time you sucked my cock. I'm not risking it. But I'll make a deal. You can suck me to get me wet. That's all the lube you're getting, so make it sloppy. But you only get to suck it first if you beg for anal real good. Otherwise it goes in dry.

Please put it in my slut ass. I'm such a little bitch. I deserve a hard cock punishing my slut ass. I want you in me, driving in me, opening my ass up. Your dick is huge. My pussy doesn't deserve it. I need it to punish my beaten slut ass. Please, please put it in my ass.

Well since you asked nicely. And because you took your ass whipping and got so enthusiastic about a beer bottle in your back door, you fucking dirty porn queen, we'll do this. Rub yourself while I ass fuck you. I want you to come, then I'll fill that ass up with my come. Then we're done for the night.

I arched up even higher, rearranging my knees on the comforter so I could spread further and reach my pussy. My ass was burning and sore in the cold air. I would have bruises tomorrow. Thankfully I had given him the deep and sloppy blow job he requested, so he wasn't dry. His cockhead pressed on me, popped into me slicky but still with pain. I fingered my clit to mix the pain with pleasure. My pussy was sopping. Popping my anal cherry with his cockhead wasn't the worst. He pushed it in almost balls deep. That hurt but was OK, but then he stared moving. It expanded my surprised and shocked walls. I rubbed my clit harder, dipping my fingers into my pussy. He told me to come, and I did. It was amazing. My entire anal tract contracted around his cock ... and then came the final punishment of the evening. When he came, he throbbed and squirted, pushing my ass past its limits.

It hurts, take it out, it hurts so much.

Shut up you little bitch, you know you came. You know you enjoy this. My cum is up your bruised ass. You know you like it.

Despite everything ... She had enjoyed it. She lay there panting with a throbbing ass, inside and out, as he cockslapped both her cheeks.

Next up ... Chapter Two, more masochistic auto-eroticism, and more reminiscences. How do you think this naughty girl should be punished? What should she do to herself next?

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3 Comments
AnonymousAnonymousabout 4 years ago
Hot

That was so hot...can't wait to try it out.

AnonymousAnonymousover 6 years ago
Wow!

So much pleasure and pain....mmmm

AnonymousAnonymousover 6 years ago
i love buttsluts

Take her shopping with a buttplug in her asshole. Have a string tied to the buttplug with a bell on the end that hangs below the hem of her skirt so with every step everybody within earshot know her butthole if filled

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