This is Part Two of a series. For part one, see The Airplane
The first thing Rick did when he landed in Seattle was message Pauline, saying he got back safely and that it was so nice to meet her. Her response was simply one word: Good. He waited a couple of days and tried messaging again, asking how she was, and again got just one word back: Good. He asked if everything was ok and if she had regrets.
“Look, Rick. There’s just no way this is going to go anywhere. We’re so far apart. Unless…”
“Unless?”
“The website with the dares. You said you would catch up and we’d keep eachother honest.”
“Oh yeah. I wasn’t sure you were actually on board with that. You said you’d think about it.”
“You join the site and catch up to me, and then we can talk. But I want proof.”
Pauline sent Rick a link to the site. He opened it and, without thinking too hard, created an account. A few seconds later he thought using his regular Google account was probably a bad idea, but he couldn’t be bothered to make a second account. Anyway there was an email with instructions:
DARE: ask a random person on the street to take your photo, fully clothed. Your face and body must be clearly visible, and it must be clear that you are on a street. Send the photo to _____@____.com to receive the next dare.
Well, this seemed easy enough. Rick walked down the street towards a local park. He saw a young woman jogging and approached her, jogging in place at a red light. “Excuse me,” Rick said. “Could you please take a photo of me?”
The woman huffed and puffed. She didn’t stop jogging in place. “A photo of you? Here? That’s random.”
“Yeah, I just need a photo of myself in the street. It’s for some dumb website.”
“Sure, no problem,” the woman smiled, took his phone and caught her breath. Rick noticed that she was quite stunning, dressed in a tight grey tank top and short black shorts. She was gleaming with a tiny layer of sweat. He realised that if it weren’t for this strange website, he would never have had the balls or the reason to approach this woman. Maybe there is something to this confidence thing after all.
The woman took a few photos from different angles and handed the phone back. “Any of those ok?”
“Yeah, the first one’s great. Thanks!”
“No problem,” she smiled and jogged across the street.
Rick immediately emailed the photo to the address from the site and waited impatiently for a response. He walked home, constantly refreshing. Five minutes later there was an email in his inbox:
DARE: take a photo of yourself in just a bathing suit. Your face and body must be clearly visible. Send the photo to _____@____.com to receive the next dare.
Again, not a big deal. Maybe even easier, as he could do this one himself. He quickly got changed into board shorts, set his phone camera to a timer and propped it up. Done.
After a few more fairly tame dares, there came the one that he was expecting.
DARE: take a photo of yourself fully nude, but covering yourself with your hands. Your face and body must be clearly visible and it must be obvious that you are nude. Send the photo to _____@____.com to receive the next dare.
Rick hesitated, wondering if it was ok to use the photo from the airplane. Did they care about timestamps and the order the photos were taken? He guessed it was probably fine, scrolled back in his photos and sent it. As he waited for the response, he noticed that he was actually getting quite a kick out of this. It seemed subversive and a bit thrilling, wondering ordu escort what would come next.
DARE: take a photo of yourself fully nude from behind, outdoors. Your whole body must be clearly visible and unobscured, from feet (no shoes!) to head (no hats!) Send the photo to _____@____.com to receive the next dare.
At first he started trying to think how he was going to pull this off without being caught. But then he remembered Pauline. He was all caught up. She would talk to him again. He sent her a message:
“Ok, I’m all caught up.”
“Where’s the proof?”
He sent her screenshots of the emails with the photos.
“Ok, we’re even. BTW in the future you can just cc me the emails you send. My address is _____@____.co.uk.”
“I’m ____@____.com. Did you do the next one yet, Pauline?”
“Honestly, I didn’t even look at the email yet. I’m a tad nervous about how this is going to escalate.”
“Can we do video? What time is it there?” It was 10 am on a Saturday in Seattle.
“6 pm. Yeah, one sec.”
There was an incoming video call. Rick answered immediately. “Hey! How’ve you been, Pauline?”
“Good good. And you? You look well.”
“Yep.” There was no denying this was awkward for both of them.
“Well,” said Pauline, “I guess we’re doing this. Alright, let me read that email for the next dare.” Rick watched as Pauline poked at her phone, and knew the moment she saw the dare because she turned bright red. “I don’t know about this, Rick. Is this really about confidence? Or is it just an excuse to get people to create amateur porn? I don’t know if I can do this.”
Rick didn’t know how to respond. He wanted to reassure her and convince her, but not be a dick about it. “Well,” he said, “you already got me hooked. I’m going to continue. But it sure would be more fun to do it together.”
“How are we going to do it together? We’re oceans apart. The time difference alone is killer.”
“We can scope out locations on video chat, and when we each have one ready we can try to be on location at the same time. Then we get off the video, each of us takes a photo and when we’re both ready, we send them to each other simultaneously. Saturday and Sunday mornings are good for me. Would around this time work for you?”
“Yeah, I suppose. Ok, I’ll give it a go.” She giggled nervously. “I think my balcony will work for this one. That counts as outdoors, doesn’t it?”
“I think it does. I don’t have a balcony myself, so I’ll have to find a quiet place on the street. There’s a little park nearby that’s kind of rundown and not too popular. Maybe that will work.”
“Ok, Rick. You go scope it out and ring me back.”
Rick hung up and hurried out the door. He was excited. He couldn’t be sure which part excited him more, what he was about to do or what Pauline was about to do. He got to the park and scoped it out. It was small with a few leafy trees and some strewn garbage. Nobody there. There were however several buildings nearby that had windows overlooking it, and a fairly major street on one side. He hesitated, trying to find at least some reasonable amount of cover. There was one spot right beside a large tree that was mostly obscured by the other trees. This might work, but he would have to be quick. There was a direct line of sight from a small part of the sidewalk of the major street. If anyone happened to be standing there looking his way, he would be totally visible.
The next challenge was where to put his phone to get a decent shot. He tried propping it osmaniye escort up against some small rocks but it kept falling down. The other trees were too far away. Eventually he dug a small hole in the soft ground and shoved the bottom of his phone into it, checking the angle for where he planned to stand. Then there was the question of what to do with his clothes. He hadn’t brought a bag or anything. Mental note: next time, come prepared. Oh well, no backing down now. He picked up his phone and video called Pauline.
“I’m ready,” he said. “Not the most private location, so I’ll have to be quick.” He gave her a little video tour of the surroundings. “You ready?”
Pauline was standing on a small balcony, the sun highlighting her light brown hair. “As long as my neighbour opposite doesn’t come to the window, yes.”
“Ok. Video off so we can take the pictures. I suppose we can stay on audio. Does that work for you, Pauline?”
She seemed hesitant. Nervous. She bit her lip, looking around. “I suppose.” She switched to audio only. “Here goes!”
Rick took one look around, especially at the street, and then pulled his t-shirt off and took down his jean shorts. It probably would have been smarter to take the sneakers off first. He sat down in his underwear and yanked at the shoes, looking around nervously. He nearly jumped when he heard a loud hoot, before he realised it was Pauline on the phone. “Oh my God, I can’t believe I did that!” she chuckled on the speaker phone.
“Hold on, I’m not done,” said Rick. He got back to his feet, shoved his clothes out of the way and propped up the phone in the hole he had prepared, then set the ten second timer, stood up and moved to his spot, almost forgetting he was still in his underwear. He quickly pulled them off and threw them out of the shot as he heard the click.
Turning back, he instinctively grabbed his phone and checked what the photo looked like. Not the best photo, but it satisfied the requirements. His underwear was mid-air. The lighting and angle were crap. But you could see that he was naked and outdoors. A second later he realised that. He was naked. And outdoors. He shot a quick glance to the street, and saw an elderly couple walking slowly by. If they glanced this way in the five seconds it took to get past, they would have clearly seen him naked. He crouched down, nervously, and grabbed for his clothes. “Done!” he chuckled as he crab-walked over to where his underwear had fallen and started getting dressed. His clothes were quite dusty and some twigs had gotten in everywhere, but he didn’t care.
“Ok,” said Pauline, starting up the video again. She was sitting in what must be her living room, wearing a nice green blouse, smiling from ear to ear, still giggling. “Let’s send them in and to each other at the same time. I’m ready. You?”
“Just a minute,” said Rick as he typed while walking back to the street. “Ok, three two one, sending!”
Rick refreshed and refreshed his email while he walked. Then he saw it. An email from Pauline to the website address, cced to him. He opened the photo. He realised this was the first time he’d seen Pauline really nude in good lighting. She was standing serenely at the railing of her balcony, looking off into the distance. Her light brown hair fell in soft waves over her creamy shoulders. Her slender back and cute little round butt shone in the sunlight. She was on tiptoes, presumably to make her butt stick out more. “Wow! That’s a stunning shot!” he exclaimed. “Now I’m really embarrassed sinop escort about mine.”
Pauline giggled. “Well, yours might have been more challenging. It’s kind of fun. There’s action to it.”
“I guess. I might have to invest in some better equipment,” he joked.
“Or hire a staff,” she laughed. “Wow, that was just so invigorating! I must admit I’m really turned on. Do you want to see?”
Rick, still walking, looked straight at his phone. “Oh?”
Pauline slowly panned the angle down to reveal that aside from her blouse, she hadn’t put anything else back on. She held the phone up with one hand and caressed her thighs with the other one, then she spread her legs and pulled her blouse up from where it had bunched, revealing her slightly-engorged pink-brown pussy and the bottoms of her breasts.
“Oh!” said Rick, picking up his pace as he approached his building. Without taking his eyes off her, he fumbled with his keys and ran up the stairs, nearly running right into an elderly neighbour. By the time he got into his apartment, Pauline had removed the blouse entirely and was playing with her left nipple. Rick ripped off his clothes and sat back on the couch, careful to put his underwear underneath him. He was already rock hard.
“Oh!” said Pauline when she saw what he was packing. “Looks like you’re all caught up.” She fumbled with her phone for a bit, leaning it against something so that she could free up her other hand. Rick did the same.
“I wish you were here to do this to me,” said Pauline as she licked her middle finger and inserted it slowly in her pussy.
“I’m here for you,” said Rick. Instantly thinking that line was too cheezy. But it didn’t matter. Pauline was already moaning and thrusting against her left hand, while occasionally tugging at her nipples with her right. Rick began to stroke his bulging dick, trying to match Pauline’s timing. He looked around for some tissue and, not finding any, grabbed his shirt.
“Mmmm,” moaned Pauline. “Don’t wait for me. I might take a while.”
“It’s ok,” said Rick. He was already doing mathematics in his head as a delay tactic. He moaned too.
Pauline picked up the pace, stroking her wet clit in circular motions as she clutched at her right breast. She stared at the phone and Rick tried to meet her gaze, which was impossible with the awkward angles of the phones.
A minute later they both jumped. There was a bing and then a little jingle as they each received an email. “Don’t stop, I’m almost there!” said Pauline. The excitement of what might be in that email was pushing them both to the edge. Rick started cumming loudly. He grabbed his shirt to try to collect the spurts as best he could without obscuring Pauline’s view. He was certainly going to have to do some cleanup today. And laundry.
Pauline’s moans got louder and more frantic as she moved her hand rapidly, arching her back as she came as well.
“Well, that’s two things today that I’d never done before,” laughed Rick as he sopped up some drops with his shirt. “I guess three if you count the shirt!”
Pauline wasn’t wasting any time. She already had her phone in her right hand as she licked her left clean. “Aren’t you curious what’s next?” she said. Then she stared at the phone and gasped. “Oh my God! I don’t know if I can do this one.”
“What is it?” Paul was intrigued and maybe a little scared as he grabbed his own phone and switched to the email.
DARE: take a photo of yourself fully nude, but with someone else’s hands covering you with their hands. Their face doesn’t have to be visible, but your face and full body must be fully visible (aside from what’s obscured by their hands). The other person can be clothed or nude, a stranger or someone close to you. They can be touching you or not. Send the photo to _____@____.com to receive the next dare.