A series of dirty dares that went way too far [Mf, humiliation, masturbation, oral]

Been chatting with this super cute girl in my college class. Her name is Liz. Turns out she’s kind of a massive perv… We’ve been flirting through text for a couple of weeks now. The plan was to finally ask her out next time I saw her but… tonight I just got a bit too thirsty and ended up taking a stupid risk. Because right in the middle of a flirty text conversation, she suddenly brought up underwear;

*”- Omg I was an idiot and impulse bought a pair of see-through panties at the mall today”*

Immediately after she sent another text justifying herself as if she was embarrassed;

*”The girls totally pressured me into doing it! They know I’m not slutty enough for something like that”*

I could feel myself getting excited reading her texts. Surely she would not be bringing this up unless she was trying to get me to make a move? Like an idiot, I used it as an opportunity to bait some sexy picture from her:

*”- You sure you’re not at least a little slutty? If you showed me how you look in them I could give you a rating, might not be that bad!”*

I got the checkmark next to my message that showed she read it. I sat in anticipation waiting for her to respond… But she wasn’t even writing anything. Immediate regret. Fuck! I’m an idiot, I should’ve just been respectful and waited to ask her out instead of making it apparent what a fucking sleezebag I am.

The painful silence went on for a couple of minutes. Then I started thinking about what I should send as an apology for making her uncomfortable. Just as I started writing my message an image appeared in the chat.

It was her, standing in front of the mirror in just her panties and a shirt, with the phone hiding her embarrassed smile. Her long red hair which is usually curly was wet as if she’d just been in the shower, her legs flawlessly spotless and smooth – resting the other hand on her juicy thighs, only a pair of red panties hiding her treasure from me. I could see her shaved crotch through them. Her tits pushed up her shirt a little which made some of her belly show.

I bit my lips and stared at her amazing body intensely. I couldn’t believe I’d gotten such a sexy, dirty girl to be into me this way. I imagined all the fun we could have together… but *fun* was not the right word for the path she was going to lead me down. This picture is how it all started, and how I eventually would end up doing something really fucked up. But I didn’t know that yet She sent her next message;

*”- So what’s your rating? There may be more to see… I lied you know – I’m actually a MASSIVE slut and a perv. You gotta prove to me you’re commited enough to deserve more”*

My heart thumping excitedly as I read, I typed quickly;

*”- What do you have in bind?*” typing so hurridly I didn’t notice the typo –

*”Whoops. Mind**”

She responded;

*”- Haha, slow down. I want you to undress and stand in front of your window… so anyone in your neighborhood could see you. Send a pic of you from behind so I can see you exposing yourself to everyone. If you’re lucky no one will see!”*

“*- What the fuck? That’s so much crazier than what you sent me. I may do it on one condition. You have to do something crazy too*”

“*- Whatever you say… But I don’t think you’ll dare to do it anyway*”

My mind was making up fantasies about the dirty things I could make her do… I pulled my pants down and threw my shirt off. Stood in front of the window and looked out… Only a lady walking her dog outside, looking the other direction. My dick was making a little tent in my underwear. I heard a *buzz buzz* from my phone;

“*Come on, no waiting for the right moment, be quick*”

I made sure the lady was looking the other way and quickly pulled down my underwear, standing completely nude in my room for the whole neighborhood. I opened the camera app on my phone and awkwardly tried to find the right angle to get a full-body pic from behind. It was difficult, I was shaking from excitement and embarrassment, my dick standing rock hard despite that. The lady looked my way – I quickly snapped a picture – before I could look I heard a *THUMP THUMP THUMP* –

“*- Hey are you home?? Do you have the vacuum cleaner in there??*”

The door started to open. No time to put my clothes on. I leaped into bed full panic mode and got under the cover.

It was my sister, Claire. She gave me a weird look.

*”- Oh hey, yeah I forgot to take it back it’s standing right there.”*

*”- Uhhh why are you in bed without clothes on. Were you literally jerking off just now??”*

*”- What? No! I’m just getting some rest, you know how college is.”*

Neither of us said anything, I just laid there feeling awkward – hiding my giant boner. She took the vacuum cleaner and closed the door behind her quickly. I heard the *buzz buzz* from my phone;

*”- Hellooooo?”*

I looked at the picture I had taken. It wasn’t great, the light from the window had blended the camera a little. But you could clearly see my full body looking out of it, my asscheeks and back clearly visible on the picture. I tapped send. It took a while again before she wrote her next message;

*”- Damn! You actually did it, haha”*

*”- My sister almost walked in on me…”*

*”- OMG LOL. Poor Claire!”*

*”- We rent a student apartment together… Oh right you guys are friends. That’s even more awkward”*

*”- Yeah Claire is a real cutie. Bet she doesn’t have the ass her brother has though!”*

I scrolled back up to look at my picture exposing my ass. Not enough that I went through with showing it to her, now she’s teasing me about it too.

*”Well I guess now it’s my turn to do something crazy for you… What do you have in mind? I bet you can’t come up with something as creative as me!”*

I already knew what I wanted her to do, but I strongly doubted she would go through with it;

“*- Since you’re not slutty enough for those panties anyway, I know a way you can dispose of them… Take them off now, and put them in your neighbor’s mailbox. Don’t wash them or anything, just go through with it now and send a picture as proof. If you’re lucky they won’t guess they’re yours*”

Silence for a while. Then a *buzz buzz*. A picture of the very same panties I just saw on her stuffed in a mailbox. Wow, she really is crazy…

*”- That was easy. My turn!”*

And that’s how we went on for days.

She made me put my balls in a glass of ice water, I made her grope an old man on the metro.

She made me upload an image of myself in lipstick to Facebook, I made her come to college in a short skirt with no panties underneath the next day.

She made me write her name on my chest with my own cum, I made her fuck herself to orgasm with her family’s TV remote (it somehow still worked afterward, just smelled weird…)

She made me run a lap around my local blocks naked in the middle of the night, I made her go skinny dipping with me.

We were crazy. But it was so fucking sexy – seeing how far we would go for each other, not thinking about the consequences, just having fun together.

Then I got the last dare I would get from her. The one that finally took it too far;

*”- I got a real crazy one for you this time… I don’t think you’re gonna be able to do this one”*

*”- Fine. But know that if I do this one, you have to go on a date with me. A hot date. Like, hot as in I fuck your brains out for the entire weekend afterward”*

*”- Hmm… It’s a deal. But you’re never gonna get to do that anyway. Because my next dare is…”*

She started typing for a long time, her “… is typing” notification disappearing several times to show that she was going back and erasing things. Maybe her initial idea was too crazy and she was trying to make it fair? At last she dropped her message;

*”I want you to hide out in Claire’s room. I want you to get a pic of her completely undressed…”*

What the fuck? That’s not fair! My sister doesn’t have anything to do with this. She quickly sent another message;

*”Don’t worry, we’ll delete the pic directly afterward. I just want it as proof. Claire and I are friends lol it’s nothing I haven’t seen before”*

I started justifying it in my head. I guess it’s not that weird, I thought. I’d seen my sister naked a few times through our teens. It’s just bound to happen when you’re growing up together. And she wouldn’t even know about it this time. If it’s all I need to do for a girl I really like I’m sure Claire would understand… Right? Yeah. It’s not weird.

*”- You’re the cutest girl in class but you’re also weird as fuck. I’m gonna do all kinds of crazy stuff to you after this you know”*

She sent back a winky smiley;

*”- I guess you must really like me to go through will all this huh… I think you’re really cute too”*

*”- Save it for the weekend when you’re begging for my mercy”*

*”- Okay… Are you sure you wanna do this though?”*

*”- Yeah it won’t be weird, and she won’t even know a thing. Right?”*

*”- Right”*

*”- Okay so… Imma wait for her to get in the shower. I’ll text you when I’m done”*

She read my message but didn’t respond. And then I waited, scrolling up and looking at our texting history the past few days… We’d done so many crazy things, but now it was all going to pay off. I got the feeling that she really liked me. Between our dirty dares, we’d had so many fun conversations. It wasn’t just that she was a hot, dirty girl. I hoped we could be together for a long time.

Then I heard my sister finally get out of her room and into the shower down the hall. I took my phone with me and snuck into her room when I started hearing the water running.

Her room was quite messy, just like my own. Clothes on the floor, a plate of food from yesterday, and on her bed was her laptop which had an essay she was writing open on it. On her drawer was a lit scented candle, making the room smell of some kind of flower.

I awkwardly crawled under her bed, where it was dark. There was no way she would see me here. I waited, though there was a weird smell bothering me. I looked to my side and saw a pair of her used panties laying there in the dark next to my head. Gross! The irony that they were red and see-through was lost on me. I couldn’t push them very far from me, they had to stay under the bed so she wouldn’t suspect anything.

Then she got out of the bathroom. I heard her walking down the hall. I got out my phone and got ready to snap a picture of her, feeling nervous but weirdly excited in anticipation. But instead of coming into her room, I heard her knocking on the door of *my* room instead.

“*Hello?? Are you home?*”

I took a deep breath. I couldn’t respond. When she got no response she came into her room instead. She threw off her towel on the floor, and there she was. I could see her full body, naked and wet. Her short blonde hair was dripping. Her tits had gotten so big the last few years, I hadn’t even thought about it until now. She turned around and bent down to get a hair drier from her drawer, exposing a full view of her curvy asscheeks, asshole, and her slightly hairy pussy. Holy fuck, I thought. What am I doing. This is so wrong. My poor sister. The fact that I had a huge boner just made the shame even worse. She stood straight again, her asscheeks wiggling as she blew her hair dry. I decided to not take a picture of her. It’s not right to do it without her consent or knowledge. I will wait this out instead and explain it to Liz later. I’m sure she’ll still go out with me, I know by now that she likes me.

Now she’ll get dressed and go to the kitchen to make dinner, I thought. That’s her routine.

But… seeing as she thought I was not home it seemed she decided to do something else. She hopped in bed, the underside of it squishing my face from the force. It remained tight to my face as I heard her getting on her laptop, making a few clicks, and then… moaning. Was she watching… porn? Is this what she does when I’m not home?? The bed started pushing against my face again, to the motions of… her humping against her own fingers.

*Oh god, why now! This was not my intention at all! This was not my fault, I didn’t plan this! This is her fault for being disgusting, I am the victim here, she’s the one doing something risky. I never knew my sister watched porn, she’s just as perverted and disgusting as me. She probably deserves something embarrassing like this happening to her.*

Angry and disgusted at her, angry and ashamed at myself, I silently unzipped my pants and stroked my cock to the motions of the bed squishing my face. *It’ll all be over soon*. I heard her quietly moaning and speeding up her humping. *She’ll never know a thing.* I stroked my cock faster too. I thought about how I’d just seen her beautiful curvy ass wiggling just a few inches from me. I could hear her thighs clapping together as she was going faster and faster, I could feel the cum building up in me. If I went any faster I wouldn’t be able to stop myself from cumming. But I couldn’t stop either.

And then I heard my sister’s sexy voice make a series of gasps and moans as the whole bed was shaking. My cock burst out a violent explosion of cum that covered my whole shirt, I didn’t care. And then, silence as we both laid still. I felt a wave of horrible shame wash over me. It’s okay, she’ll go and make dinner now and then I can sneak away.

And then…

*Buzz buzz…*

I froze. Fuck. My phone. Maybe she didn’t –

I felt my sister turn to her side and bend down to see me, a shocked disgusted face as she saw my panicked expression, cum covered shirt, and throbbing cock.

“*- What are you -*”

She gagged and gasped for air.

“*What are you – what… WHAT THE FUCK IS WRONG WITH YOU??*”

“*- I can – I can explain – THIS WASN’T MY FAULT IT WAS YOU WHO- just wait I can ex-*”

She ran out of the room, panicked and confused. She slammed the bathroom door behind her… I could hear her crying in there as I got out from under the bed and ran into my room. I curled up into a ball on my bed, shaking, my cum-covered shirt still on me, making that sour-sweet smell. I didn’t think about it right now. I was desperately trying to come up with an excuse for my sister in my head. But no… there is no way she will ever look at me the same again. My relationship with her was over… all for a stupid dare with this FUCKING WHORE LIZ. WHAT KIND OF FREAK IS SHE THAT SHE WOULD MAKE ME DO THIS. I’M GONNA TELL MY SISTER IT WAS HER FRIEND THAT MADE ME DO THIS. I’M GONNA DESTROY HER-

*Buzz buzz…*

It was my phone again. I picked it up and looked at my last two messages… It was Liz.

Sent 10 minutes ago:

*- “I’m calling it off! I thought about it, I just can’t do it to Claire. I don’t know why I came up with that weird idea, I just got caught up in our little game. DO NOT do the dare please! You don’t have to put yourself through that to be with me because I’m pretty sure that I’m falling in love with you anyway”*

Sent 30 seconds ago:

*”Hello?? Are you there?? DO NOT DO THE DARE!!!”*

I threw off my disgusting shirt and started crying. It was too much. Too many emotions. She said she’s *falling in love with me*? How could anyone love me after what I-

My sister stomped into the room.

“*- I’m moving out. I can’t stay here anymore. You’re a fucking creep. I hate you.*”

I sat there, crying pathetically without a shirt.

“*- Okay… I hate myself too.*”

She didn’t say anything. She just looked at me with complete despair and disgust in her eyes and closed the door, leaving me alone in my dark room.

A few hours later Liz received a text from me in the middle of the night, after not hearing from me since this afternoon.

*”- Hey you’re still living with your parents right…? I think Claire is moving out so… there’s a room available here if you want it.”*

She didn’t have any questions. She knew what had happened. All she replied with was;

*”- I’m so, so sorry. Please forgive me. Please do not hate me. I love you”*

I couldn’t think of anything to respond with. I can’t say I felt any love in my heart right then. She sent another text;

“*I’ll explain to Claire that it was my idea and that I made you do it. She’s gonna hate me too but it wouldn’t be fair otherwise*”

A week passed. Claire didn’t talk to me, and I couldn’t bring myself to talk to her. Some of her friends came over to help her move, they all looked at me with disgust when I opened the door for them. None of them said anything. Claire left without saying goodbye to me. And then I was alone in the apartment. I walked into her empty room, which still smelled like some kind of flower. It was empty and clean. The only thing left was the bed which she just a week ago had caught me under. I cried. I already missed her.

Another week passed. I was in my apartment, fresh out of the shower. I looked at myself in the mirror. For the first time in 2 weeks, I didn’t feel appalled by my own image. I stood there looking as sexy as I could naked, sprayed myself with deodorant, and brushed my teeth. Then I walked out completely bare naked and into Claire’s old room, which now had furniture in it again. There, on that very bed, laid Liz in a seductive position, naked and biting her lips. She was so beautiful. She spread her legs for me, invitingly showing her wet pussy and smiling at me.

*”- I dare you to…”* was all she said.

I just laughed as I rolled on a condom on my throbbing cock. I crawled into bed and put her legs around me. She embraced me and pulled my lips to hers, our tongues reaching out to each other. I dug my hands into her beautiful red hair, pushed my cock against her crotch, grinding against her impatient clit.

*”Don’t tease me like this… Fuck my brains out, please. I’m begging you.”*

I pushed the tip against her warm entrance.

*”- I love you too…”* was all I said.

She looked me in the eyes with a surprised, happy expression. And then I thrust into her, turning her expression into one big gasp of long-awaited ecstasy. I pushed as deep into her as I could, finally feeding my cock which she had teased so long with her amazing inside that I could feel pulsating against my shaft, squeezing it as she was adjusting to my throbbing cock. But I didn’t give her any time to adjust. I started making powerful slams against her crotch, using my hands on her head to push her down into my cock with each one. Loud moans from us both. The smell of sweat and genitals building up.

*”- Oh my god you’re so brutal”* she moaned, *”How did you guess I would like that?”*

I didn’t say anything. I just fucked her faster, grabbing her jaw and pushing my tongue into her. She was lost in senseless pleasure, not even keeping up with what I was doing, struggling to feed me back with her tongue. Faster and harder. I put one of my hands on her thigh to help me push her up and down faster. She tried to say something and just ended up blowing a big chunk of her air into my own mouth. She pushed me away from her tongue and through her mindless panting and moaning screamed

*”OH MY GOD I’M GONNA CUM”*

She shook uncontrollably, her eyes rolling back into her head. She started hitting my back to make me stop thrusting. I kept going, feeling my own orgasm building up. Her insides were convulsing violently and she was just screaming *OH GOD YES*. But my orgasm was still building up. I kept thrusting my cock into her after her orgasm was over. It became easier as our bodies became more and more slippery from all the sweat. I felt amazing for the first time in so long. This felt so right. I didn’t think. There was nothing but my cock relentlessly fucking her for what felt like an hour. After I came I switched condoms and kept going. I had so much built up in me, I hadn’t jerked off for two weeks. She came two more times, and when I came the second time she moaned *”I need- I need water…”*

I realized I was thirsty too. I pulled myself out of her and we both gasped for air. I threw my condom on the floor next to the other one filled with cum.

*”- Okay… I’ll go get us some”* I went and got some water in the kitchen, sweat running down my naked body. After I got back we just sat there looking at each other happily for a while in silence as we were each sipping a glass of water. I finished my glass and went to put my arms around her. I wanted to embrace and cuddle her all night. I was so happy in this moment.

*”- No, there’s time for that later”* she said.

She turned to look at me with a dumb, shameless smile on her perverted face, mindlessly sighing *”I want more cock”* before dropping her head to my crotch and devouring my entire throbbing cock into her throat in one go. Her red, curly hair was spread out around her and tickled my thighs as she fucked me with her mouth. Her slimy saliva dripping from my balls and running down between my asscheeks. She was got her hand between her legs and was just rubbing her pussy as she kept gagging on my cock. Without thinking, I pushed her head down and blew a big load of hot cum straight into her throat. She immediately pulled herself away from me and started coughing out cum.

*”- Fuck I’m sorry, I didn’t think! Are you okay?”*

She just looked at me with her naughty eyes and licked her lips as if she’d just enjoyed a fine meal. Then she turned around, and pushed her ass and dripping pussy in my face. I started eating her out without hesitation, bathing my tongue in her delicious pussy-juice. She shoved my cock down her throat, laying one me in a “sixty-nine” position. And this is how we kept going without pause, through multiple explosive orgasms, until sunrise. My balls completely drained of anything, she stopped when she noticed I was almost falling asleep with her ass in my face. She rolled off me and turned herself around to face me, putting my arms around her and resting her head on my chest.

“*- Hope you’re prepared for this every night now that I live here*”

Oh my god. This is a dream. She is the perfect girl. Just as crazy and disgusting as me. Thinking about spending the next couple of years together in this little apartment was the only thing that could make my cock rock hard again.

*”I take it you’re prepared then”* she said laughing.

She grasped my cock with her warm hand and just slowly stroked me as we both fell asleep entangled together.

And that’s the story of how I lost my sister and found my soulmate.

Source: reddit.com/r/sexystories/comments/eqoi8i/a_series_of_dirty_dares_that_went_way_too_far_mf