Midnight Tryst

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This is my first submission for this category. It’s a fun arousing short story. If you’re looking for a long winding epic erotic yarn, this is not it. I would like to thank Shyone245 for editing and helping me flesh it out.


It’s a Sunday night, after 10:30 pm. I’m sitting on my bed, bored and unable to sleep. I look at the door that connects my room to my brother’s room, maybe I’ll go over and talk to him. We do this frequently, late night conversations about life, the universe, and everything that we can think.

Our parents had that door locked some time ago, but I figured out how to unlock it and keep it unlocked. I don’t know what the big deal is to them, about it being open in the first place. Besides, I love chatting with my brother at night. He helps me with problems and to keep me from going insane.

I should probably introduce myself, my name is Anna, I’m a 20 year old student at the local community college. 5’8″, 135lbs, auburn hair, green eyes. My brother John, is 19, about 6′ tall, 170 ish pounds. He’s not really jacked, but he is fit.

Anyway, it was probably mid-July, our parents were in their room sleeping. I sat on my bed, pondering the universe, and watching the clock. At 11:00 I was thinking that I would go in and talk with my brother. He’s leaving for college in a few weeks, and I won’t see him much anymore, so I want to spend as much time with him as I can.

I never thought of my brother in any other way than him as my brother. He was my brother, a part of me, maybe that is why I am going to miss him so much when he leaves.

I crept over to the door and put my ear against it. I could hear him moving, but I couldn’t hear what he was doing. Slowly I turned the knob and pulled it open just enough to see inside. He was sitting on his bed, facing away from me.

I could see he wasn’t wearing a shirt or anything. The light from the moon filtered through the shades and illuminated him, I could see the muscles in his back flexing a little bit. Maybe I should go back to my room because he seems to be pretty into whatever he is doing, but curiosity gets the better of me.

Risking discovery, I opened the door a bit more. I looked down and realized the lights were on in my room as there was a beam of the light shining through on the floor. ‘Shit, Anna.’ I cursed myself.

I looked up and John was looking at me. “I’m sorry, bro. I couldn’t sleep and was wondering if you were still up.”

“Yeah, it’s all good, Anna.” He pulls the comforter up to him, looking a bit awkward. With the comforter pulled around him and as if to hide something.

“I couldn’t sleep and figured I’d come over and chat with you.”

“Ah, okay. What’s up?” He was sitting on his bed, comforter covering him to his waist. No shirt on, I could see his chest had some hair on it, the light from my room casting a glow over him.

“Mind if I come over and sit next to you?” This caused him to stare a bit and worry.

“Um, that’s fine.” He shifted slightly, pulling the comforter a bit tighter around him.

“I can come back if it’s a bad time.” I turn to go, hoping he would stop me.

“No, it’s alright. I’m leaving in a couple weeks and we won’t see each other much, so come on over. Besides, I was just thinking about you.”

“Really? What were you thinking about?” I ask him as I walk barefoot over to his bed. I’m wearing sweat pants and a baggy t-shirt, nothing else. I’m guessing he’s not wearing anything at all and that’s why he keeps fidgeting with the comforter.

“I, um, yeah, I was thinking about how I’m going to miss my sister when I leave.” He awkwardly replies, I suddenly feel very powerful and push on.

“Yeah, okay.” I give him a playful tap on the shoulder as I sit down next to him. “And I’m the Queen of England.”

“Pleased to meet you, your Majesty.” He says, bowing as best he can from a sitting position.

“You’re such an asshole, you know that?” I laugh. “How come you don’t have a girlfriend?”

“Wow, um, well, I’m going away, so I didn’t want to bother with a long distance relationship or anything. Figured I’d meet someone at school. What about you? You broke up with what’s his name, and I don’t think you’ve seen anyone since then.”

My brother has always cares about me no matter what happens. “Yeah, Steven. He was a jerk. I’m better off without him.”

“Yes, you are, Anna.” He looks at me with a sparkle in his eye. I get this sudden urge to change the subject to something a bit more sexual.

“So, tell me. What do you do for relief?” I don’t know why I ask him this but the urge pushes me on, he’s sitting in front of me barely covered.I’m pretty sure he was waxing his carrot, but maybe I’m wrong.

“What do you mean?” His eyes are big, I guess he can’t believe what I’m asking. But I think deep down he wants me too.

“You know, like sexual relief. You’re 19, I know you’re probably horny as fuck. What do you do?”

“What do you think?” He asks me very sarcastically with a interesting look on his face, a look izmir escort bayan I haven’t seen before.

“Were you rubbing one out when I came in?” I start to get some courage from the urges inside of me.

“Maybe.” He blushes slightly, but I see it, so being the great sister I am, I ask just in case he doesn’t want to continue.

“Does it bother you that I’m asking these questions? They’re pretty personal, I guess.”

“It’s alright, we share pretty much everything anyway. I guess this is fine.” That’s true, so I have been granted permission.

“That’s good.” I lean my head against his shoulder. “If you tell me what you do, I’ll tell you what I do. Sound like a deal?”

“Um, sure. That sounds fair.” He says that with a hint of shyness.

“So, tell me brother of mine, what do you do to relieve that tension?” I look at his face, waiting for the answer.

“Well, mostly I just masturbate.” Here we go on the plan that has been laying deep inside me for some reason…

“Oh, just masturbate. What do you think of when you touch yourself?”

“Girls. Doing things with girls.” He seems a bit embarrassed, but I want to press on, I want to see what he wants.

“I masturbate too. I can’t go without getting off every so often. What kinds of things do you think about?” I think about all the lovely orgasms I’ve had lately.

“Sex.” One word answer? Really? Time to turn this conversation up.

“Like, blowjobs? Do you imagine a girl sucking on your cock?” I ask bluntly to get right to the point.

“Wow, you’re pretty blunt tonight. I do, that and other things.” He’s still avoiding my conversation.

“I like to imagine that a handsome guy is thrusting his cock into my pussy when I masturbate.” I’m enjoying talking dirty to my brother, making him uncomfortable. I feel very powerful…

Serves him right for leaving me behind in this one horse town, I think to myself about all the things I’m going to miss.

This conversation is getting me aroused, I can feel the heat between my legs, the familiar tingle, my pussy begging for attention. It seems to be making John even more uncomfortable though, so I’ll deal with it, even though him uncomfortable is making me feel dominant.

“That’s kind of hot. I sometimes imagine that I’m fucking a girl. Like going to town.” Yes I’m pulling you into my trap, I think to myself.

“Who do you think about? Come on I told you mine, now tell me yours” I want to know, I need to know your desires big brother.

“I’m not telling.” He shifts about, crossing his legs under the blankets, his hands in his lap, as if to hide something. Maybe how much this talking has aroused him too.

I attempt something that I would have never thought I’d ever say to MY brother. “I think about all different guys, but sometimes I imagine you’re the one fucking me. I cream harder when I masturbate while thinking about you.”

I see his hand slip under the blanket, fidgeting with something. It has worked, I have him!

“Are you touching yourself now, brother? I know you were thinking about me when I came in, so I guess you think about me too when you jack off.”

“I was, I couldn’t help myself.” He finally admits to me, and he hangs his head, but keeps moving his hand under the blankets.

Feeling emboldened, I reach a hand into my sweatpants and touch my pussy. It’s slick with my natural lubricant. I start rubbing up and down my slit. John looks over at me to see what I’m doing. An idea forms in my head, I decide to take charge of this situation even more.

“I have an idea. Since we both think about each other when we get ourselves off, why don’t we do it here next to each other?” I ask very bravely.

“Um, w-what do y-you mean?” He asks nervously, his hand stops moving, as if he’s shocked.

“Keep stroking yourself, I didn’t say to stop.” I tell him, my more dominant side coming out, I slip a finger into myself. “We won’t touch each other, just masturbate next to each other.”

“Okay, that doesn’t sound so bad.” His hand starts moving again. I can hear my fingers slipping over my pussy, I bet he can hear it too.

“You know, you don’t have a shirt on.” I point out, looking at his chest. Knowing where I want this to go, but I can’t!

“I know.” Pointing out the obvious.

“Maybe I should take mine off as well, do you want me to? I want to. I want you to see my breasts as you jerk yourself.”

Without waiting for a reply, I pull my shirt off and toss it on the floor. I turn so I’m facing him, my breasts exposed. My nipples are hard at the thought that my brother is rubbing one out while looking at my tits.

“Wow, they’re nice.” He says as he stares at my tits. I use my free hand to pinch and twist a nipple.

“Thanks. You know what I’m doing now, John?” I continue rubbing myself, paying some extra attention to my clit. I still have my hand on my nipple.

“Touching yourself?” He says carefully as he is still stroking his cock.

“Rubbing my clit. It’s nice and hard and my escort izmir pussy is nice and wet too, cos I’m so fucking horny right now.” I watch his reaction, he strokes himself a little faster.

“You’re so bad, stroking your cock while your sister talks dirty to you.” This is making me so hot, it’s so enjoyable.

“I can’t help myself, I just want to come.” He says to me while having a hint of urgency. He cannot come without my permission…

“Oh, but you can’t yet. Not til I tell you to come. Can you handle that?” This is starting to cause something deep inside to stir and make me more powerful.

“I think I can, but what if I can’t hold or stop my orgasm?” Mmmm, not going to work.

“You wouldn’t want to find out. Now stop stroking yourself.” He keeps going, so I slap him lightly but hard enough for him to feel, his hand stops moving. I like this feeling of being in charge of my brother’s pleasure.

“If you don’t listen to me, I’ll go back to my room and frig myself there where you can’t see or hear me. Do you want that?” Knowing he won’t let me go, I dare him.

“No no no, I’m sorry, I’ll be a good boy” he has a very lusty look in his eyes.

“It’s alright. Now, do you want to see how excited I am?”

“But, you’re my sister.” He looks very worried but still interested.

“It’s alright so long as we don’t actually do anything more than look. So, do you want to see?” I keep rubbing circles around my nub.

“Can I? Pretty please?” He begs me and I enjoy it very much.

“Since you asked so nicely, I’ll let you see my cunt.” I remove my hand from my pants and get off the bed. I reach over and turn on the lamp that’s on the bedside table.

“I want you to see how wet my pussy is.” I pull my sweatpants down very slowly to tease him and step out of them. My labia are swollen from the excitement, my clit sticks out a bit from under it’s hood. I move closer to the bed so he can get a good look.

“Wow, that’s beautiful.”

“I’m glad you like it. You can start jerking off again, but only til I tell you to stop.” I watch as his hand dives back under the blanket to touch himself.

“Can you smell how horny I am?” I reach between my legs and start stroking myself, I can feel my juices run down my thighs. I move a little closer to the bed.

“Lay down, put your head on the pillow.” Obediently, he does. Like the good submissive he is.

I step up next to the bed, my sopping wet pussy inches from his face. “Do you like looking at me? Looking at how wet I am?” Bossing him around is thrilling.

And him doing what I tell him makes me even hornier. I decide to push things a bit further.”Oh god, that’s so amazing.” He stares at my pussy, so I take both hands and part the lips so he can get a real good view of it.

I notice he starts stroking himself even faster. “Are you gonna cum?” I ask knowing he’s already on the edge.

“I feel like I’m getting close.” He says, still stroking his cock at a fast pace.

“Stop! You can’t cum until I do, from now on I’m going to call you my slave, because you are a submissive.” I tell him, he pulls his hand away very reluctantly and I can see the sheet bulging where his erect member is.

Holding my pussy open with one hand, I slip a finger into it. “Watch me, watch what your slutty sister does.”

I slide my finger in and out, my fluids glistening in the light, I feel how hot and how horny I am. “That’s so hot, Anna.”

“You like it my slave? You like when your sister finger fucks herself in front of you?” This is turning me on so much, I am feeling live a real mistress.

“Yes, I like it.” I slip another finger inside, going at it furiously with two fingers. I stop abruptly, pulling my fingers away, to give my willing slave a treat.

“Open your mouth, and call me mistress from now on, okay?” I tell him. I wasn’t going to go this far, but I’m so horny right now, I don’t care. He opens his mouth, his eyes on my wet fingers.

“Okay, hold still. I’m going to give you a taste of my cunt.” I put my two fingers into his mouth. He sucks the juices off, licking my fingers to get all the evidence of my nectar.

I can feel myself getting even wetter. I pull my fingers away from him. “You like the taste? You like tasting your mistress’s cunt?”

“You taste so good, m-mistress.” He answers me very carefully and his eyes seek approval.

“Good, you can start stroking yourself again, very slowly though.” His hand goes back under the blankets, I can see them rising and falling as he rubs up and down his shaft very slowly, as instructed.

“I want to see what you’re doing there. Show me your cock. “He pulls the blankets down, exposing his hardon to me. His hand sliding up and down it, over and over.

“Oh my slave, that’s a beautiful cock. Your mistress likes watching you stroke your cock.” I start rubbing myself again. I’m really enjoying this, I’ve never been more excited in my life. I get the feeling that John is equally excited.

“Are you imagining that your cock izmir escort is pounding my pussy? Cos that’s what I’m imagining. My brother’s hard cock slamming into my wet cunt.” He lets out a loud moan.

“Oh god, that would be so awesome.” I know this is wrong, but I am in charge now.

“What would, my dear slave? Tell me what would be so awesome?”

“Fucking you.” I can tell he’s really getting into it and needs to cool off for a minute, because his face is going red.

“Stop jacking yourself. Stop right now.” He pulls his hand away and lets out a low whine, and looks at me with begging eyes.

“Oh god, I need to cum, please mistress.” I lean over him, my face next to his.

“I know you do. But what did I tell you, you bad boy?” I whisper in his ear.

“I don’t remember.” He looks scared of what I might do to him, that look sends a bolt of energy to my pussy.

“Do I have to spank you?” The thought sends a second shot of tingles through me.

“Huh?” I can feel myself getting close, so I force myself to stop stroking my sensitive clit. I slap my pussy, not too hard, but enough to hurt a bit. Wincing in pain, I need to stay in control of the situation here.

“Get up. Get up and stand over there by that chair.” I tell him. He obeys, walking over next to the chair by his desk.

“Okay, now I want you to bend over, your hands on the chair.” I instruct him. He pauses a moment. Frightened by the reality of this.

“Now!” John bends over as I told him to, his ass pointing at me. I can see his hard cock swaying between his legs, a drop of precum drips from the tip onto the floor. Holy shit, he’s really aroused.

I’m surprised he didn’t tell me to piss off so he could finish himself off. Maybe he’s enjoying this as much as me, this is why he will be a great submissive.

Taking a deep breath, I walk over to him as calmly as I can. I reach out and rub his right ass cheek, then I pull my hand back and slap him. CRACK! He flinches, but otherwise doesn’t move.

I rub his left ass cheek, then slap it. CRACK! He doesn’t flinch this time. My heart is pounding, I can feel my pussy throbbing with excitement.

“Does my slave remember now?”

“Yes.” He quickly answers but has forgotten something.

“My slave, have you forgotten something in that sentence.”

“Yes, M-mistress.” He whines.

“Well, do you remember now or must I remind you again?” I caress his left ass cheek.

“You cum first, then I get to cum.” He says softly. I can see his cock twitching in the light of his desk lamp.

“I want you to sit on this chair, put your hands under you.”

“Yes, Mistress.” He does as I told him. His cock ramrod straight. I take a moment to admire it, it’s only about 6 inches, but kind of thick, a nice mushroom head. I bet it would feel like heaven inside me.

Taking a deep breath to calm myself, I look him in the eye.

“If you cannot follow directions, Slave, then you don’t get to cum. And I can tell you want to cum so very bad, don’t you, Slave?” I ask him, disdain in my voice.

“I’ll behave, Mistress.” He looks to me telling me that he is desperate need to come.

“Good, now let’s continue. Pull that chair closer to your bed.” He does obediently. Such a good little Slave brother, I think to myself. Maybe I should really have some fun with him.

I sit on the edge of the bed facing him. I look him up and down, he really is quite attractive. I don’t know how I never noticed before. I stare at his swollen cock, licking my lips.

Oh god, I want to, but I know I can’t. That would be going down the rabbit hole. I take a deep breath, clear my head, then look at his face.

“Okay, so I want you to do something for me.”

“Anything, Mistress.” Nice. I put my feet in his lap, right next to his cock, but not touching it.

“I want you to suck on my toes.” I tell him. I wonder if he really will, then takes my right foot in his hands, caresses it, brings it to his mouth and starts kissing my toes.

“I said suck them, Slave.” He takes my second toe into his mouth, his tongue flicking over the tip of it as he gently sucks on it. A pulse of energy goes through my body, I can feel my pussy leaking onto his bed.

Fuck, that’s so hot, the sight of my brother sucking on my toes, the feeling of them in his mouth. After a couple minutes, he takes them from his mouth and puts my foot back down.

He then does the same to my left foot. I can feel an immense pleasure inside me at the feeling of his tongue on my toes. I think I might cum just from this. “Keep sucking those toes.” I tell him, my voice husky.

I begin rubbing circles around my clit. I’m so sensitive right now, I have to go easy so I don’t cum right away. With my other hand, I put two fingers in my pussy and begin fucking myself with my fingers as I stimulate my clit.

I watch John’s cock bobbing as I pleasure myself while he continues sucking on my toes. I see that he is watching me pleasure myself as well. “You can stop sucking now, Slave.”

He puts my foot down. “Such a good Slave, I think I’ll give you a treat.” He looks at me eagerly. I can feel an orgasm coming on and, oh boy, is it gonna be a doozy. I get to my feet, a bit unsteady, as I feel it building.

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