The Late Night Conversation

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Amateur

This story is dedicated to my pet.

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[Are you awake?]

I saw the message appear in my inbox and I can feel the bone weariness in my entire body and for a moment I think about ignoring it. But I can’t, it’s from her. I have never been able to ignore a message from her, even at work.

So, although all my body wants to do is sleep, I pick up my phone and reply.

[Yes Mistress.]

Two simple words. I don’t feel the need to say more. I feel like there’s a pretty strong connection between us and just those two words will be enough.

Sure enough, her reply comes quickly.

[I’m having trouble sleeping. Can you stay up a little longer to talk?]

My eyes rake over the clock on my dresser. It’s nearly two o’clock in the morning. I shouldn’t even be awake now since I have to be up in four hours to get ready for work. The only reason I am is because I was dealing with family drama until about ten minutes ago. I was just about to lay down. But… I sigh and slide out of bed.

[For you Mistress, I would do anything.]

It must be my sleep deprived brain that compels me to word it like that. I didn’t really think through the consequences of that broad statement, as I soon realize by her reply.

[Really? Then can we actually talk?]

I know what she means by that immediately and my body stiffens. I’ve heard her voice before and she’s definitely heard mine, sometimes in very compromising positions. I’ve recorded myself in such vulnerable times, she has heard me orgasm before, heard me give myself three back to back ruined orgasms, heard me whine and plead for release. But it’s always been recordings. We’ve never talked live together. She’s suggested it before. I’ve always beat around the bush or changed the subject every time it came up. When entering into this relationship I set some boundaries for myself. Boundaries I promised myself I wouldn’t cross for my own good. One of those boundaries is to keep this relationship solely text based. Part of me has to admit I’ve already gone and blown that one since we have exchanged voice recordings.

Still, when I record my voice there’s always that disconnect that allows me to tell myself that I haven’t crossed that line.

My phone chimes with a new email from her.

[Okay. Nevermind. Forget that I asked.]

Clearly she picked up on my reluctance. I’ve been sitting here debating this so long that she assumed my answer was no and that I was too cowardly to answer her. The thing that stings most about that is that it’s true. I am a coward. I love my Mistress. I didn’t want to hurt her by saying no and now I don’t have to because she’s withdrawn the question.

So why do I feel even worse that I didn’t answer? I know her message came through solely as a text message but I could practically hear the hurt in it and it acted like a hot poker through my heart.

I close my eyes and feel myself walking through the house and out into the garage. I’ve got a three car garage and the third one has been transformed into a sort of indoor work station complete with bench and a chair.

I sit down on the chair and reach into my pocket to pull out my pack of cigarettes. Bad habit, I know. I only picked it back up recently due to all the stress. I quit nearly twenty years ago but with everything that’s been happening these last few months, and the fact that I’ve been around smokers lately, I fell back into the nasty habit of destroying my lungs with nicotine infused smoke.

Right now I’m hating myself for a number of reasons. I set the cigarette between my lips and pull my phone out again, staring at the on screen keyboard as I try to mersin escort decide what to say. What can I say after something like that?

Before I can write anuthing, another email comes through from her.

[Well I guess you don’t actually want to talk. Goodnight.]

Her brisk words drive another dagger through my heart. I hate feeling like I’ve disappointed her and now I’ve done it twice in one night! I need to do something to make amends.

Before I can change my mind, I log into Discord. I made an account a few months ago, the last time my Mistress mentioned wanting to be able to talk. She told me Discord allows you to make internet calls without revealing a personal phone number. That’s also been one of my hang ups. A major one. That is a hard boundary I told myself I would never cross with anyone online – Do Not Divulge Personal Contact Information. I already feel like I dipped a toe over that line by telling her my real first name. I could have lied, she would never know, but I told her my real first name.

I stare at my Discord app and realize I have no contacts. She’s the one that suggested Discord and I just now realized I don’t even know her Discord handle.

Frowning a bit, I lick my lips and then bring up a web browser on my phone. I navigate to the website where we first connected and find her profile. I breathe a sigh of relief when I see she has her Discord listed.

I copy and paste her handle into Discord and only then realize that now I’ve made the conscious choice to cross one of my boundaries. And I’m okay with it.

I send her a friend’s request through Discord and wait. And wait.

And. Wait.

After fifteen minutes I fear that she has already gone to sleep. I’ve written, erased and rewritten an email to her a half dozen times before I get a notification that she accepted my friend request.

[Hello. Do I know you?]

Her message comes through on Discord and I smile. I used one of my old handles, one she hasn’t seen before. I should have used something more obvious but for some reason my whole body is thrumming with energy. This is fun.

I don’t reply to her question, instead I send a request for a phone call.

She rejects it.

[Sorry. I don’t do phone calls with people I don’t know. How did you get this account name?]

Well, at least she’s not stupid. I think for a moment. I want to surprise her with this. I don’t reply and just send another phone call request.

Again she rejects it.

[Tell me who you are or I will block you.]

Forceful and direct. I feel my cock twitch at her command. Why the fuck does this stir me? Probably because I’ve preconditioned myself to respond to her every whim for three and a half years now. It could also be that my cock is eager for attention. I was finally able to cum this week after my longest ever chastity. I was trying to prove to my Mistress what a good pet I could be and wanted to set a new record. And I did. 69 days.

She finally gave me permission to cum a few days ago but currently I’m under ‘no cum’ rules and it’s only been a few days but I want to cum again so badly.

Finally I give up on playing coy. I don’t reply through Discord. Instead I send her an email.

[Do you still want to really talk?]

I send the email then return to Discord and send a third voice call request.

This time it rings and rings and rings. I hear a click and the ringing stop and immediately think she’s rejected it a third time. I sigh and fish a lighter from my pocket.

“Hello?” Her voice, her beautiful voice that makes my cock hard, that’s coaxed me to more kocaeli escort than one climax over the past few years, comes through the phone loud and clear. I am so surprised by it that I drop my lighter.

“Hello Mistress.” I say on instinct and bring the phone to me ear.

“Well this is a pleasant surprise.” Her voice is warm and happy. Hearing it brings a smile to my lips.

“Yeah.” I say stupidly, a dumb smile on my face.

“How are you doing? Is your cock, sorry, my bad. I meant to say my cock. Is my cock all hard and achy?”

“Fuck.” The word slips from my mouth as an involuntary reaction and my cock twitches harder in my cotton briefs. “Yes Mistress.”

“Mmm, just hearing my voice gets you hard, doesn’t it?” She purrs, pure feminine sexuality dripping from every word.

“Yes Mistress.” I repeat lamely.

“Mm, you know, eventually you’ll have to say something other than Yes Mistress. It’s sexy as all hell but I’ll grow bored.”

“I understand Mistress.” I paused then stumble boldly onward. “I’ve never really done this before so I’m not sure what to say.” I admit.

“Aww.” She cooes. “It’s okay my pet. I’ll do the talking, you just listen.”

“Yes Mistress.” It’s second nature for me to reply to her like this even though this is the first time hearing her voice live.

“And no touching yourself!” She says so suddenly that I jump and immediately pull my hand away from my crotch. Yep, I had been touching. She giggles. “You were touching weren’t you?”

Red faced, I instantly reply with yet another, “Yes Mistress.” Which just makes her giggle again. God, her giggling is so hot.

“So, I am home alone tonight.” She says and I shift a little, glancing down at my crotch with my hardon pressing against my briefs harder than ever. There’s a damp spot forming over the tip, which is saying something since I’m wearing briefs and pajama bottoms.

“I am wearing my penguin pajamas. You know the ones.” I most certainly do. She’s sent me more than one picture of them and I close my eyes to imagine them. Baby blue with a pattern of penguins this way and that all over them. The words ‘Baby it’s Cold Outside’ scrawled across her beautiful, full bosom.

“I’m feeling pretty horny so I’ve just picked up one of my vibrators and slipped it under the elastic waist and of my bottoms and into my panties, which, by the way, are Completely. Soaked.” She puts emphasis on the last two words and I actually whimper out loud, rolling my hips a little. My noise makes her giggle and I can hear a faint rumbling noise in the background – the vibrator.

“Oh God…” I mutter under my breath, drawing another giggle from her.

“Around, and around, and around my clit it goes…” She moans breathing heavy and I’m sure she can pick up on my deepening breath. I’m so hard it’s almost painful not to touch it.

“My other hand just reached up into my top. I’m not wearing a bra, by the way.”

“Fuck… Mistress, please may I touch myself?” I beg, practically whimpering.

“Not yet.” Her voice is firm, commanding. I do whimper this time, shifting in my chair and biting my lip. My noise makes her laugh, which causes my cock to twitch yet again. It’s a vicious cycle!

“As I was saying, my hand reaches up into my shirt and I begin to play with my full breasts, teasing my nipples…” Her voice has reached that low, seductive tone that makes my heart race.

“I wish I could touch them…” I whisper without even thinking about it.

She laughs and says, “I bet you do. Would you like a picture?”

“Yes please!” I say instantly.

There is a moment samsun escort of silence then I get a new email. I open it to find a picture of her, exactly how she described herself. She’s lying in bed, her beautiful brown hair splayed out in a halo around her head while her hand is up her shirt. She’s not wearing makeup but she’s one of those women that looks better without it. The skin of her cheeks is smooth and glistens with arousal. No torso skin is revealed but it is still one of the sexiest things I have ever seen. I’m salivating just looking at her!

“Now I want you to touch yourself. Through your pants.” She tells me and my hand instantly goes to my crotch.

“Yes Mistress, thank you!” I say honestly, thankful for the chance to rub myself even if through my pajamas. My hand begins stroking up and down my shaft and I close my eyes as I listen to her.

“You’re not allowed to stop stroking unless I say so. You may slow but not stop.”

I whimper, that’s always so difficult for me. She never gave me permission to cum either and my current orders are no cumming, so that means I have to keep stroking, no matter how close I get and I have to try to hold back. “Yes Mistress.”

“I’ve just slid my toy inside of myself. It’s humming away inside while my fingers play with my clit…” Her voice is dripping with arousal.

I run my tongue over my lip and gently stroke my cock, up and down in slow strokes. Touching myself through my pants certainly helps me hold back.

“I’m imagining that my hand is wrapped around your cock…” She says and my cock twitches in excitement.

“Oh God.”

“I’m using the head of your cock to pleasure myself. Can you feel that?”

“Fuck, yes Mistress.” I whimper, imagining the hot warmth of her pussy on just the tip of my swollen cock.

“Pull it out of your pants.” She orders and I don’t hesitate. “Keep stroking.”

The moment my hand wraps around my cock and I feel the skin to skin contact, I know I’m in trouble. I’m getting so close.

“I’m running the head of your cock over my clit… At the same time I lift up my shirt. You can see my bare breasts but you’re tied in place so there’s nothing you can do. You can’t reach my breasts or stop me from tormenting your – I mean my cock. I keep the head pressed to the heat of my cunt while my hand begins to stroke up and down, faster and fas-“

“Red!” I cry out in alarm, feeling myself oh so close to the edge.

“-ter. I drag your cock up along the inside of my pussy lips.” She keeps talking as though she didn’t hear me and I start to panic.

“Red! Fuck, red, red, red! Please Mistress!”

“Cum for me, pet.” Those words come so suddenly that I’m stunned and stop stroking for just a second.

“Do… Do I have permission?”

“No.” She says and my eyes grow wide. It’s a trap. There’s no way to win. I let myself cum and I disobey my order to not cum, I stop stroking and I disobey my orders not to, I hold back and I disobey her purred request for me to cum.

“Mistress Please… I… I don’t know what to do!” I cry in desperation. “I’m so… So fucking close. Please may I cum?”

To my surprise, she doesn’t answer me. Instead she starts to moan and groan. It takes me a minute to realize she’s getting off on hearing my plight. That’s so hot.

“Mistress…” I moan, knowing it turns her on. I can’t ignore the fact that my own orgasm is dangerously close. My breathing is heavy.

“Oh fuck… That was…” She says, her voice breathy in pleasure. “You may stop stroking now.

I stop, pulling my hand away. It’s a blissful sort of torture. “Fuuuck.” I moan in a drawn out tone, using all my willpower not to cum.

“I think I can sleep now. Thank you my pet. Goodnight.”

An agonized noise escapes my lips before I say, “Thank you, Mistress. Goodnight. Sleep well.”

She ends the call and I sit there in my garage, my hard cock aching for release, the sounds of my Mistress’s pleasure still echoing in my ears…

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