Learning to Beg

It was an accident. You never intentionally decided to end up here. It started out as a mild curiosity. A small voice of questioning that you decided to explore. And it ended with countless nights with your hand on your cock muttering nonsensical pleas into the space of your bedroom. You were embarrassed. Even when you learned this was a secret desire for many men, you were still embarrassed. To be frank, you are not an open person. You're quiet. And reserved. And you suppose it's true what they say about people who are quiet...and reserved. Because currently it's 2 am. Your hand is on your cock again. Watching things you'd never want your mother to find. And it isn't enough. It's never enough. Well, of course, it's enough to finish, you suppose. But not enough to satisfy for long periods of time.

Something tells you to look. Look for someone to help you at 2 am. Usually, you don't listen to these passing thoughts, but logic does not exist on the same plane as desperation. You remember seeing an ad. A chatroom. For desperate filthy people like you. You find yourself typing the address. You find yourself pressing enter. You also find yourself wondering if it's too late. And of course, in theory, it isn't. At any time you could close this tab and pretend tonight didn't happen. But you know yourself. You know even if you are scared you won't want to turn back.

You begin a chat. A stranger is typing on the other line. She says something much too intense for your liking. You end the chat. It continues on like this. You have several awkward encounters with men like you. Each one says a shy hello and a quick goodbye. Then she types.

'How is my good boy tonight?'

You swallow thickly. You read the words again. And then again. And yet, you still don't know what exactly to say.

'Please, don't be shy with me. I know you're there.'

You take in a sharp breath.

'Hello' is all you can manage to say.

'There's my sweet pet...' Something inside you clenches.

'What brings you here so late.' You're sure she knows exactly what brings men like you on sites like this at this ungodly hour. But regardless you feel this aching need to open yourself to her. And you do. You tell her exactly why you are here at 2 am on a Tuesday night. You tell her about the girlfriend you had back in high school and how she jokingly called you a good boy and how you came all over your hand in the bathroom stall right after. You tell her about the first time you found dominatrix porn and how you finished in 2 minutes. You tell her about the dream you had where you were bound and spanked by your history professor. And you stop for a moment, because it seems like you've said too much.

She's typing. And then she pauses. You wait for her to call you disgusting. To tell you to see a therapist. She doesn't. She sends her number. She tells you to call her. Your hands are shaking for a moment. You contemplate whether you really ought to be doing this. You ask yourself if you really can go through with this. You decide that yes, you can go through with it. Your cellphone is on the desk in front of you. You take a breath and pick it up. The number is dialed, it's ringing now. She picks up.

"Hello?" Her voice has the same smoothness of high class southern women. It's slow but deliberate. Calm and yet demanding.

"This must be my shy little boy hmm?" You realize you haven't said hello yet, but you can't bring yourself to speak.

"Tell Mistress your name pet.." You breathy is shaky.

"Mason.."

"My sweet little Mason. You have the most delightful voice."

"Thank you.." You take in a breath.

"So tell me, Mason, what do you need from me tonight?.." Before you can think you're answering.

"Mistress I need to come." Your voice is more unsure than you intend.

"That's really what you want pet?"

"Y-yes"

"Yes what baby?" You hesitate.

"Yes Mistress please.."

"Such a good boy.." You moan without warning.

"And eager as well." You can hear the amusement in her voice.

"Now... Do exactly as I tell you."

"Ok..."

"That's not how I taught you."

"Yes Mistress." This time you don't hesitate.

"Take your cock in your hand." The sheer touch itself bring you back to life. You let out a whimper. That's the only way to describe it. A meek shaky whimper.

"Now baby, stroke yourself."

"Yes mistress" You voice is hush and yearning. You take your hand up your shaft slowly as instructed. You repeat the movement closing your eyes.

"Pretend that's my hand baby. Imagine me touching you."

"Fuck.."

"Hmm we don't use such foul language. Next you will be swiftly punished" You hold back a moan.

"Oh my.. You like that sort of thing don't you?.. You enjoy being punished? You want to feel a heavy hand on you behind don't you?" You don't know what to say. You can only accelerate the past of your hand.

"I do hope you have not increased the speed of your touching without my permission." You slow down immediately, but you're aching already to go faster.

"Mistress I want to go faster."

"That isn't how we ask pet." You let out a soft groan.

"Please.."

"My, hasn't anyone taught you how to beg like a proper slut? 'Please?' You think that's sufficient? For your sake I hope not." Your face is burning.

"Please Mistress.. I need more. Please Mistress I promise I'll be good i want more I-" You cut yourself off with a loud whine. You've never quite yearned to come like this.

"Hmm I didn't realize I was harboring such a needy little boy." She is pondering whether she'll let you continue. You can hear it in the silence.

"Very well. Continue." You moan.

"Thank you mistress." You're fucking your hand. Every time you think of her hearing you it inspires you to moan louder. It forces you to move faster. Because you want to come for her so badly. And you realize that this may very well happen in not too long.

"Mistress I'm close."

"Stop."

"What?"

"I said stop."

"But Mistress I-"

"Orgasms are earned Mason." Something about hearing her say your name makes you melt.

"Beg. Tell me why I should let you finish tonight." You start without hesitation.

"Please Mistress I need to come. I need to finish. I need you to hear me finish. I need it so bad. I want it Mistress please-"

"Then come for me slut." And you do. You jerk yourself fast letting out long erotic moans followed by streams of white. You thank her. You can't seem to stop thanking her because you've never felt quite this good. Nothing, no one, has ever made you feel quite this good.

"It doesn't have to end here." You are thrilled by this proposition.

"Meet me tomorrow. I'll send you my address."

"Yes Mistress."