THE DARE, AND THE UNEXPECTED NIGHT
“Send him a text,” I said, setting up the dare. “Just type, ‘which body part?’ and see what he says.”
“I know what you want him to say, and I think I know what you are going to ask me to do,” she smirked. “He’s my coworker, dammit.”
“He’s got three chances, ok? I guarantee you his first reply won’t be naughty.”
“Fine.”
She types:
* w h i … ch bo…dy p art?
Moments later:
* ???? ankles?
“Ha, alright, take a pic of your ankles and send it to him, then ask the same thing again.”
She does.
* whic … h b … ody par … t?
“I wonder why he thinks I’m asking.”
“Maybe he thinks you are a serial killer asking which part to chop off next.”
Almost immediately, he responds:
* belly button
“He’s getting closer,” I said, a smile of anticipation as she snaps a pic of her belly and hits send.
* beautiful belly button!!! i love the piercing
“This time, say ‘last one, which body part?'”
“And what if he says ‘hands’ this time?”
“I guarantee you he won’t. He knows where this is headed.”
She sends the text.
The reply comes quickly:
* breasts?
She smiled, “He said ‘breasts’ but with a question mark.”
“Heh, ‘breasts.’ He’s either shy or being polite! But there you go, hot tits it is. Take a pic and send it!”
She makes an exaggerates sigh, but her mouth smiles with it, removes her shirt and bra, and gives her breasts a quick once over with her hands.
“Alright. I said I would. This is kind of crazy. You want to take it?”
“Nah, it’s better if you take it. Hot selfies, and all.”
She holds out her hand, snaps a few.
“Ugh, you can see my bra lines.”
“That makes it even hotter, shows you just undressed specifically for this.”
She swipes through the boob pics, selects the best one, attaches and sends.
“Fucking awesome,” I say, pleased.
He responds with my own words:
* omg fucking awesome!
* is that you????
We both laugh.
He texts:
* you are so fucking hot
She writes:
* that’s all for now, enjoy. ;)
I ask her to screenshot that conversation and send it to me.
“I’ll be getting off to that later,” I say.
A week later, I ask if he has said anything else about it or asked for more.
“No. He seemed a little awkward at work, but he didn’t say anything, probably because we weren’t alone.”
“Hmmm. Well, we can fix that. I’ve got another one for you. You game?”
“Maybe,” she said, slowly.
“Ok, this one’s for money. But you will kinda need to be there alone with him.”
“Uh oh… I’m scared of what’s coming,” she says. “So, what is it?”
“Fifty bucks if you take a pic undressed in his apartment.”
“How am I going to do that?”
“Uh, you go over for whatever reason you think of, take off your clothes and take a pic. Then send it to me right away.”
“That’s a little weird, don’t you think? Just pull off my clothes and start taking pics?”
“It’ll be unexpected and hot! You can give him a little warning first if you want. Say, ‘Hey, I lost a bet and have to do something,” then just do it.
“Fifty bucks?”
“Yeah, and I’ll throw in another twenty if he’s in the shot, too.”
“We’ll see. I don’t know about this one.”
I shrug, but really, I’m already aroused thinking about it. It will happen, I think.
The week leading up to her planned rendezvous, I’d already jerked off to the idea. Finally, Thursday, she texted me:
* Heading over there soon.
I responded:
* :) text the pic as soon as you take it. don’t forget, bonus dollahs
* oh god. we’ll see. later.
A few hours later, my phone buzzes. A pic of her topless in an apartment I didn’t recognize. Yes, she did it. Immediate hard-on.
Before I can text back, another pic shows up. She’s topless, a sultry expression, and a male hand in the frame, cupping her left breast.
Followed by another, his fingers pinching her nipple, and she’s fully naked, bush and all.
Fuck! I’m already out of my pants, getting off to this when I think to text back, one hand on my cock, pecking out the letters with one finger:
* so hot $$$
I finish on the floor, and after cleaning up, I text:
* me and the floor babies thank you ;)
An hour, two, more go by and she hasn’t texted back yet. Not unlike her though; she isn’t attached to her phone.
I imagine the way it played out, thinking to myself that it is probably hotter in my mind than the way it’s happening.
I scroll through the pics again and shortly, the phone buzzes.
Another pic.
It’s her, laying back in a bed, topless, hair askew, with a look on her face and something about her eyes.
I know that look. And as soon as I think it, she texts:
* fun night. talk to you tomorrow ;) :)
Holy fuck! Wow! And, though I didn’t even realize it, I was already stroking, making more floor babies to this wonderfully hot turn of events.
I fantasize about this for the rest of the night, jerking off once more before finally being able to sleep.
The next day, she walks into my place, a slight smile as she takes off her sunglasses. Without a word, I hand her ninety in cash.
“And,” I say, “I do believe you have a story to tell.”
She drops the cash in her purse, sits, and says, “Well, that was certainly not the night he expected.” Her smile shows teeth, she looks away, and I think, God, she is so fucking hot.
She tells me all about the night before.
“So, when I got there, we talked for a bit, and then I just asked, ‘So, did you enjoy our game last week?’ That’s when he told me he’d been fantasizing about me since we first met.”
“I figured,” I say.
“I was trying to think how to segue into your newest request, so I told him the game was kind of a dare — ‘I lost a bet.'”
“Heh.”
“So, anyway, I said, ‘While we are on that subject, there’s something else I have to do.’ And I tell him I have to take another pic and that it has to be in someone’s apartment, not mine. I don’t think he quite got what I was suggesting, though. He was just like, ‘Oh?'”
“Did you just rip off your shirt and bust out those titties?” My heart was beating harder, and my hands were starting to get shaky.
“I asked him if that was ok, and he was just super polite, saying, ‘Yeah, um,’ and stuttering a bit. Honestly, it was kinda awkward!”
“Funny.”
“Yeah, but then I did it. I took a couple from different angles, and then figured what the hell, and asked him to come over, and I took his hand and put it on my boob and took a couple more. I think he was in shock. I did get his face in one or two, but didn’t send that. But I can show you.”
She pulls out her phone, opens the gallery, and I see there are a handful of pics with both of them in there, one being with both of them smiling into the camera, almost a normal selfie except she was topless.
“Ahhh, yes. You. You know my fantasies about you being naked around guys. You should send me that.”
She swiped through more pics, and I was shaking more, excitedly.
“I could see he was turned on when he was touching me.”
“Yeah? Were you?”
“I was.”
“So then what?”
“He kissed me!”
“Whoa!”
“Yeah, I was surprised. Well, kinda, a little.”
“And you kissed him back?”
“Yeah, it was good.”
“Was he still touching your tits?”
“He was. And I put my hand on his crotch, felt that he was indeed hard.”
“I don’t know why I’m shaking, I’m loving this.”
“Oh, I know you are, and it gets better. He goes, ‘should we behave?’ and then says, “or, no strings attached?'”
“You looked great in the pictures, I’m sure you’d be hard to resist.”
“I did look good. All part of the plan.”
“You are sly.”
“So, he’s saying all these things, and we sit on his couch, and he’s touching my legs and all, and he puts my hand back down on his hard-on, so I’m rubbing that.”
“I am so turned on right now.”
“He’s saying how badly he wants me. It’s getting pretty hot. We’re kissing. I’m massaging his cock through his pants.”
“This is his sign, the okay he needed?”
“Yeah, so I start to unbutton his pants, unzip him, and slide my hand onto him, and he helps pull his pants off.”
“You are committed to it at this point. How’s his cock?”
“Nice! Not huge, but nice.”
“Did you put your mouth on it?”
“Yes, I started giving him a blowjob. He was totally loving this.”
“Fuck…”
“Then he pushes me off him, and pulls off my leggings and panties.”
“I might start jerking off right here in front of you!”
“He starts licking me…”
“Mmmmmm…”
“I pull him up, and grab his cock, and we go to the bedroom, and I guide him into me.”
“I need details, positions, everything.”
“Dude, he fucked me every which way.”
“How long?”
“I have no idea, but it felt so good.”
“Did you come?”
“Yes.”
“Did he come inside you?”
“I wanted him to, but he pulled out just as he came. It just shot right out of him. Like up my stomach and all the way up to my chin!”
“Oh, man, I’d love to see a pic of you with someone’s cum on you.”
“I took that last pic and sent it to you right after, when he went into the bathroom to get me a towel. I think you can see the cum on my chin.”
“Really, I didn’t notice that!” She pulls up the photo and zooms in, and sure enough, now I can see a spot glistening just under the piercing below her lip. “Oh fuck, that is just too hot.”
“There’s some on my chest too, between my boobs.”
“I see that now! Oh my god, as if that photo could get any hotter.”
“Glad you liked that. The post sex selfie was a spur of the moment thing, but I thought you’d enjoy that.”
“Fuck yes.”
“I have something else for you.”
I cocked my head as if to ask what.
She reaches into her bag and pulls out a little ziplock bag and hands it to me.
“I figured you would appreciate this. They still smell like sex.”
Inside the bag were her panties.
After she left, I pulled up the photos, cast them to the TV so I could have the pleasure of a slide-show on the big screen. I removed the panties from the bag, and put them to my face, inhaling deeply as I jerked off twice in a row. I even licked at the fabric, tasting her pussy and the sex.
Later, I texted her:
* this is the hottest thing you’ve done for me yet. i love you.
She typed back:
* i know ;)
THE END
Source: reddit.com/r/sexystories/comments/m65u5h/the_dare_and_the_unexpected_night_fm