“Oh come on! It can’t be that bad!” Amy chuckled to herself in front of the glow of her computer screen. “There is no way on earth that I would sleep with a 50 year old pervert just to get my share of the rent together.” Sarah had argued for the past ten minutes with her roommate about the dangers of using Craigslist to make money, but as always with Amy, she had to feeling she was fighting a losing battle.
“You don’t have to sleep with someone, you can just do what I do. Go out for dinner or let them take you shopping. It’s good money.” Amy was a typical ditzy blonde and Sarah couldn’t help but think to herself that she couldn’t put on the always smiling, innocent and flirty act as easily as Amy could if she was sat opposite a guy who was paying her $100 just to cope with a meal together. “What about this one?” Amy turned the laptop screen to show Sarah yet another advert. “It’s only modelling for an hour or so and at the end of it you get $350! Plus you’ve done modelling before.”
It was true, Sarah had on occasion done some modelling shoots, but she doubted that one found on Craigslist would have much in common with the times spent with a professional photographer. For a start, she just knew it would probably take place in some sleazy hotel room or in some newly divorcee’s messy apartment. Nonetheless, modelling was something she could do. And at 22 years of age she still managed to easily maintain her swimsuit body, a pretty face, beautiful brown hair and smouldering blue eyes. Her sun kissed skin and rounded ass capped it off for most men and her 34B breasts might not have been as big as she would have wanted, but fit her slender frame perfectly. In fact, if it wasn’t for her petite five foot four height, so always felt that she might have given modelling a stronger go. Despite Amy’s girl next door cuteness, there was no denying that if you had to label one of the two friends as sexy, it would go to Sarah every time.
“$350 for an hour modelling? So where’s the catch? If he is paying that much he must be a creep.” Sarah said furrowing her brow. “Why can’t someone just be nice in your books?” Amy exclaimed while reading ahead in the advert, before her face dropped. “It’s lingerie modelling and the guy is in his 40s… but it won’t be published. I think he is just lonely and wants to have something to look at when he is lonely.” Amy sympathized. “Does lonely in your world mean jerking off over pictures of exploited girls in your books?” Sarah laughed, but she couldn’t deny that despite the creepiness of it all, if she get paid $350 just for standing in front of a camera in lingerie, she would allow the guy to jerk off to her pictures for the rest of his life as it meant she could cover this month’s rent. “Oh come on Sarah! It isn’t that creepy. It’s over in an hour. Then after that rent is covered for this month. I got mine together by going out with one of these so called ‘creepy’ guys last night and had a lovely time.” Amy pleaded.
Sarah thought for a minute. She couldn’t think of another way of easing their financial troubles, and an hour of her time for $350 was good money. “Ok, but if I don’t have a pleasant experience, then you have to drop the issue of craigslist.” Amy gleefully clapped her hands together and went back to her laptop to begin forming a response to the man. “I’m serious Amy! If he makes even one creepy remark, I don’t want you to be trying to convince me to do it again this time next month.” Sarah felt that her words of warning fell on deaf ears however as she watched Amy tap away on her laptop keys…
Sarah stretched out her arm and knocked firmly on the black, wooden door. “Sarah? Come in, I’m Simon.” The man opening the door said, stretching out his hand which Sarah shook while stepping out from his porch and of the dark night and into the bright and warm entrance of his Simon’s house. Although it was only a condo as she expected, it was tidier, trendier and in a nicer and quieter neighborhood than she had imagined. Simon himself looked to be in his mid to late 40s. He was short at probably five foot eight inches, had short receding black hair and had a bit of a protruding belly, but his teeth were immaculate and all his own and Sarah noted that he may have been reasonably attractive in his younger years.
Simon ushered Sarah into the room adjacent to the entrance hall, where she found a lounge area with a three person black leather sofa backed up against the wall facing a matching armchair at the far side of the room. In between was a large area of thick white carpet. In the corner of the room was a television sex which had been moved to make room. A tripod stood with a camera and a long lens stood giving a side view of the room, the sofa and the chair. On the couch lay a smaller and less expensive camera. “Would you like a glass of wine before we get started?” Simon asked as Sarah surveyed the scene. “I’d rather just get it over and done with if it is all the same to you.” Sarah nervously chuckled. “That’s fine. You’ll find the bathroom just through there if you would like to change into the first outfit. I’ll just set up my gear.” Simon pointed towards a door next to the couch and Sarah shuffled through the room and into a bedroom with even thicker and luxurious cream carpets and a king sized bed with expensive looking linen sheets.
At the far side of the room was a door slightly ajar with a bright light beaming out of it. She stepped through and into a small, but clean and tidy bathroom. On a chair in front of the sink sat a chair with three different sets of lingerie folded into a pile. Sarah slipped her coat off and folded it up and placed it on the windowsill. She placed her handbag down, opened to clasp and took out her mascara and lip stick, before heading over towards the mirror by the sink. She applied the dark black mascara to her eye lashes and then smothered her lips in the deep red lipstick. She removed her shoes, her jeans and her t-shirt before placing them on top of her coat. Sarah surveyed the room one last time for any hidden cameras then, happy with no discoveries, removed her bra and panties and stepped in front of the mirror once again.
Sarah grabs the thick black bra at the stop of the pile and straps it on before straightening the shoulder straps up. Although finding it tight and quite uncomfortable, she had to admire the way it pushed her breasts up, making them look much bigger than a 34B. The lacy bra is matched by a pair of lace black panties and transparent black hold ups with a pair of six inch heels. Once she straightened up, Sarah can’t help but admire how classy she looked in the mirror. She expected to be made up a bit sluttier, but thought that Simon might like something perhaps a bit more up market.
Leaving the bathroom and through the bedroom, she now walks into the lounge again to find the lights are dimmed. “Wow, you look amazing!” Simon remarks while holding his camera. “Where do you want me?” Sarah asks and Simon responds pointing over to the chair. *Click* Sarah turns her head to the camera on the tripod. “Don’t worry about that, that is just set to go off every 30 seconds, but you’ll mainly be posing for this camera that I have here.” Simon then proceed to raise the camera in his hands to his face, look through the lens and then take a photo of Sarah front on. The second was from the side, and the third from behind, before he instructed her to sit on the armchair and pose for another couple of photos. When it was over, Simon peeked up from his camera. “That’s great, if you would like to go put the second pair on now and we can get on with it. You never know, we might be done before the hour mark.”
Sarah returned to the bathroom, pleased and slightly relieved that it was working out much better and faster than she had anticipated. The next outfit was a much thinner and better fitting. It consisted of a purple bra and panty set, but this time without any shoes or stockings. The panties were tight around her buttocks and showed off just a slight bit of both cheeks at the bottom. She re-enters once dressed and Simon asks her to pose in a similar fashion, again ending sat on the chair. “Can I make a request?” Simon asks from behind his camera nervously. “Sure, what you want?” Sarah asks. “I need something a bit different and perhaps a bit sexier this time. Would you bend over the chair for me?” Sarah thought it was going so well that she wouldn’t put up a fight and in fact was feeling slightly sexy in the lingerie, so climbed up onto her knees, leaned over the chair and stuck her ass out for the camera. The fabric tightened around her bum and clung to her cheeks even more as she gives Simon a look over her shoulder while he is snapping pictures off rather quicker than before.
Returning back to the bathroom, Sarah feels even more confident and relaxed and thinks to herself that she better make this last one worth it. Removing her bra, she looks at her now hard nipples in the mirror. Then taking off her panties, notices the dampness of the gusset, moistened by her own excitement. Somehow, feeling so sexy and wanted had turned her on. She picked up the final outfit and to her shock found it to be much more risqué than the others. The bra was white and sheer and her pointed nipples were clearly visible through it. The panties this time a matching white thong that rode right up her ass and made her cheeks fully visible. Sarah wondered if it was too late to back out, but still get paid, but thinking that it would only be an extra five or ten minutes and only for Simon’s private collection, walked out to Simon with his draw dropped. He took more photos this time, obviously focused on both the front view in which her nipples could be seen and the back in which her ass cheeks were hanging out. Sarah felt a tingle of excitement as she climbed onto her knees on the arm chair again and peered back to see Simon, slightly hunched to try to hide the bulge in his pants. “Ok, could you pull your thong down ever so slightly for me?” Sarah reached back and placed her thumb under the waist band of her thong and pulled it down and to the side ever so slightly. *Snap* “A little bit more” *Snap* “And a bit more” *Snap* “Come on Sarah, don’t be shy!” Sarah now pulled the elastic and slipped it down. *Snap* The camera caught the perfect moment of Sarah’s slip and the other side of her panties slipped down and she felt the cool breeze of her now exposed asshole.
“Wow! I guess you aren’t shy after all.” Simon remarked as Sarah pulled the thong back up and turned around, letting out an awkward giggle before sitting on the chair. “We still have some time before the hour up if you would like to make a bit more money?” Simon asked sitting down on the couch behind him. “More money?” Sarah said intrigued. “Yeah, you clearly have a nice body and you’re not shy about it, and seeing as it is only for my private collection and that outfit doesn’t leave much to the imagination, how about bumping your pay up to $600 for a few naked snaps?” Simon calmly asked, his heart racing 100 miles an hour. Sarah had to admit to herself the $600 sounded like a good deal for photos that nobody else would see, and felt more and more suggestible and comfortable around Simon as her arousal at the situation increased. Sarah stood to her feet calmly, then reached behind her back with both hands and nervously fumbled off the clasp and dropped her bra to the floor, revealing her perky breasts and her already hardening nipples to Simon’s gaze and the cool air of the room. Simon was quiet and mesmerized as Sarah reached down to her panties, hooking her thumbs into the elastic waistline and pushing them down her long, smooth and slender legs and onto the floor bellow. Standing straight she now gave Simon a completely naked view of herself. Her pussy was smooth and shaved and glistened with dampness in the light.
After what felt like an eternity of Sarah watching Simon look up and down her naked body, Simon raised the camera to his face, and snapped a picture of her now naked form. Much like before, Simon took pictures of her from the front and back, before getting her to lean over the chair again. Sarah stuck her ass out towards the camera, feeling more exposed than she had ever done before. Simon flashed more and more pictures off of her exposed holes. “Ca…Can I ask if you can do something to make this look really sexy?” Simon spluttered and looked up to a curious Sarah turning her head, but slowly nodding it. “Can you reach underneath your legs and put your hand on your vagina? You don’t need to do anything with it, but in the photo it will look so sexy and like you’re masturbating.” Sarah’s heart rate increased as she reached under her legs and up into the pose Simon had described. She placed her hand over her damp pussy and pressed in slightly, feeling just how excited by the situation she really was.
“Thanks! That’s going to look so unbelievably hot! Hey, if you didn’t mind doing that last pose, how about I give you $1000 instead of $600 and we can make it look even naughtier? We wouldn’t actually be doing it, but I could make it look like we are playing together.” Sarah didn’t have to think about it for long. $1000 would ease her money problems and give her a bit extra, and it was clear from the way her groin was reacting, she was enjoying herself. “Ok, how do we do it?” Simon instructed Sarah to sit down on the chair and place her feet on the arms of it. He snapped another picture of her with her legs spread, before getting down on her knees in front of her and placing his hand on her pussy. Sarah flinched, but didn’t say anything as he took a photo of his hand placed over her pussy, having to admit to herself that it felt kind of nice to be touched after feeling horny for so long. Simon then slipped his middle inside of her wet hole, feeling the warmth inside. He went up to his knuckle before taking a picture and withdrawing it and presenting it to Sarah’s lips. She placed the finger in her mouth, tasting her juices as Simon took another picture. Simon, then leans down to her pussy as if to eat it out, but stops just before putting his mouth to it. As they waited for the camera in the corner to snap a side angle shot of the pose, Sarah could feel Simon’s heavy breath on her sensitive opening, internally willing him to just stick his tongue out and lick it. However, he doesn’t and when the picture is taken he stands back up and starts to undo his belt. Sarah’s eyes widen, now in panic mode and disbelief of how she got herself in this situation. Simon unzips his flies and takes out his already hard dick. Although only average in length at about six inches, Sarah noticed that it was fairly thick, circumcised and clean looking.
Simon then takes Sarah’s hand and guides her to wrap it around his thick dick, which she limply clings on to as he takes another snap. “Open your mouth” Simon requests, before taking Sarah’s hand off his cock and guiding it forward. Sarah watched it oncoming, but before it reaches her open mouth, he veers to the right of her and places the warm and pulsating member on her cheek, giving the impression that a blowjob is being given from the view of the side camera. She closes her mouth in slight disappointment at not being able to feel his dick in her throat after the picture is taken, but doesn’t have long to feel bad about it as he places it over her chin and lips, lying it along her face and up to her nose before taking another picture. Simon then grips the base of his dick and takes it off of Sarah’s face. “Stick your tongue out for me” Simon told Sarah, which she obliges to. He then places the tip of his dick on to her tongue and holds it while he takes a pic. Sarah can taste a mixture of cleanness and soap alongside the salty, musky taste of Simon’s pre-cum which is leaking out of the tip of his dick and onto her tongue.
Simon then placed his hand on the back of Sarah’s head and forces more of his shaft inside her eager mouth. Sarah pulled her tongue back into her mouth and wrapped her lips around Simon’s cock, now engulfing the head completely. Simon is now eagerly snapping off pictures as Sarah slowly slips her mouth down Simon’s shaft, trying hard not to gag as she buries her nose in his trimmed pubic hair. As Simon let out a moan from behind his camera, Sarah resisted the urge to suck on or flick her tongue against the pole that was filling her mouth. When Simon was satisfied he had enough pictures, he removed his now wet dick which glistened from Sarah salivating over it and there was smudges of her red lipstick up the shaft. “Ok, get on all fours looking at the camera over there.” Simon pointed to the camera still snapping in the corner and Sarah got down on all fours onto the thick carpet as Simon completely undressed behind her. She felt Simon place his penis underneath her and his hands on her hips, and felt his cock pushing up against her lower stomach, giving the illusion he was inside her to the camera. After a few pictures, Simon then picks up his handheld camera and places his dick at the entrance of Sarah’s now soaked pussy and takes an aerial shot of his cock placed against her opening. Sarah resists the urge to push her ass back and feel Simon’s dick become engulfed as it slips inside her.
“Can I get a video of me inside of you on the couch?” Sarah’s heart skipped a beat at the request, eager to feel something inside of her before she leaves this evening. “Ok, that’s fine.” She said nervously. They both got up and Simon positions the tripod in the corner to look directly at the couch before flicking the camera onto record mode, hitting record and then sitting himself down on the leather couch and grabbing hold of Sarah’s hips and guiding her to sit on top of him. As she straddled him, he placed his dick at her warm and damp entrance and felt her pussy lips wrap around the head. Sarah pushed down and felt the dick slip inside her with no resistance. When she hit the bottom, she let out a gasp of pleasure, thankful to finally feel something as thick as Simon’s cock inside of her. She then slipped up the length of his shaft and back down again, before picking up the pace and riding Simon hard. It was a good couple of minutes of intense pleasure before Sarah realized the words and moans that were coming out of her mouth. “Oh fuck! You feel so nice inside my pussy Simon!” Before she can reach orgasm though, Simon grabs her hips and stops her from bouncing on him any further. “Stop! You don’t want me to finish already do you? We need to really make this complete. I want to fuck you in the ass.”
Sarah’s eyes widened. “No way! I’ve never done anal before and you’re lucky to have even got this far with it.” Simon frowned and looked up at her with puppy dog eyes. “But, I wanted to get a quick video of me fucking your ass. That’s what I thought about when I offered you the $1000, I’m afraid I can’t give you the full amount if you don’t give me what I wanted. Ok, how about a compromise. I’ll give you the full $1000 if you let me take a picture of just the head inside your ass.” Sarah was now panicking, not wanting to have come this far and get conned out of what Simon owed her. How bad can it be if it is just the head, she thought to herself. “Ok, but just the head!” She said, causing Simon to beam up at her. Sarah climbed off of Simon’s pole and sits herself down on the sofa, reclining back and bringing her legs up to her side. Simon got up and left the room for the bedroom as Sarah reached under her knees and spread her ass cheeks, exposing her virgin hole to the still recording camera in front of her. Simon returned with a short tube of lube and sprayed it all over his dick, before positioning himself on the floor in front of the sofa. Simon then squirted a generous onto his middle finger and placed it at the entrance of are ass. Sarah flinched at the cold liquid being applied and felt more and more of it leave the tube as Simon slowly wormed her finger inside of her butt. He placed his other hand over her pussy and began to rub her clit with his thumb as he attempted to insert a second finger into her anus. Sarah felt uncomfortable as Simon began to finger fuck her freshly opened ass, but didn’t want him to stop due to the pleasure he was giving to her clit, so she instead tilted her head back and closed her eyes. Sarah then felt both of Simon’s hands leave her body, before feeling the warm head of his dick placed at the entrance of her ass and the unmistakable snap of a picture being taken. Without thinking, so reached her hand forward the wear Simon’s thumb had been and began to rub her clit to get the sensation back. She gritted her teeth as she felt Simon push harder and harder against her ass, trying to impale her against some resistance. She lets out a whimper of pain as her ass finally gives way and Simon manages to slip his head inside her. Feeling relieved that the head is now in, she hears another click of the camera, but is alarmed when she feels Simon push more and more of his shaft inside her. “OW! The heads inside, just take the picture!” She demands. “The head isn’t fully in yet, it won’t look right.” Simon responds. Simon continues and gets another inch inside of her before Sarah opens her eyes and stops rubbing herself, placing her hand on his stomach and stopping him from getting any further inside. Simon the takes Sarah’s hand away and snapped a picture of half his cock buried inside Sarah’s ass. He places the camera down on the floor and looks up, still inside of her to see Sarah staring into his eyes. They look intensely at each other for a minute in silence, before they lean in and lock lips. Sarah can feel Simon push further inside of her as their tongues dance around in each other’s mouths.
As Simon breaks off the passionate kiss and slips the last few centimeters inside her Sarah gasps, as if she had been winded. Simon picked up his camera again and takes a couple of photos of her ass engulfing his thick cock as it completely stretches around his shaft. Sarah could feel every millimeter of his six inches as he slowly slid it back out and forcing it back into her. Stride after stride her ass stopped resisting and in turn hurting as it got used to the intruder it was swallowing. She began to play with herself again as Simon used her backside to pleasure himself. As his strokes got firmer and faster, Sarah’s fingers rubbed harder and deeper, occasionally slipping one inside her. She felt the familiar feeling in her loins building up. Soon she was oblivious to everything else that was happening and could only think about the sensation of her clitoris. Her legs straightened stiff as she reached climax. She was breathless for about ten seconds until she suddenly realized the sensation in her ass, now feeling tighter than ever before.
The sensation for Simon was too much, feeling her anus squeeze around his cock while Sarah squirmed herself through an intense orgasm. With some reluctance he pulled himself out of her backside, still trying to swallow and suck him in. “Got on your knees!” Simon urgently shouted. Sarah threw herself down on her knees in front of the camera, just in time to catch the first spurt as Simon jerked himself over her face. The first rope of jizz splashed diagonally across her lips and onto her far cheek. Sarah, with her eyes tightly fastened felt the warm sensation as it hit and couldn’t help flick her tongue out to her lower lip, taking in a thick, creamy glob of his salty sperm and tasting it. The next jet hit right over her closed right eye and into her fringe. The third and fourth streams landed right across her nose and onto her other cheek. A fifth was more runny and splashed on Sarah’s chin and dribbled onto her bare breasts below and Simon squeezed out the last few drops onto her pretty face. Sarah’s face felt completely warm and covered as she heard Simon move about and then the distinct sound of him taking pictures of her cum splattered face. “You may want to clean that off in the bathroom” Simon said as Sarah slowly peered out of her one capable eye. She got to her feet and stumble through the bedroom and once again into the bright light of the bathroom, grabbed a hand towel and wiped away a thick strand of semen covering an eye so she could once again open it and peer out. Standing in front of the mirror, she peers at her cum soaked face, now dribbling down her chin and neck and onto her body, before wiping it off and washing her face in the sink.
Despite feeling very sore, she managed to slowly get back into the clothes that she came in, before limping slightly into the front room to see Simon sat, now dressed again on the couch with his laptop in front of him. “You will find the money on the chair. I’ve called for a cab to pick you up. It won’t be long.” Sarah picked up a brown envelope on the armchair and peered inside to see a bundle of $20 bills. She placed it safely in her handbag, before gingerly sitting on the couch next to Simon. Despite her ass feeling sore, she was made to feel even more uncomfortable by the fact the Simon was now watching the recording of what had just happened on his laptop. It began to sink in what she had actually done and could only wish to herself that Simon kept his promise and kept it for his own viewing alone.
They both spoke very little in the ten minute wait, until the cab finally arrived. As if they were business partners, they shook hands at the door as Simon shook Sarah’s hand. She didn’t know whether to laugh or cry on the cab ride home, but knew she was glad to be sitting there with $1000 in her purse. The walk up the stairs to her apartment was painful, and she was glad to get her key into the lock and slip inside the comfort and safety of her home. Amy came rushing to great her with her characteristically wide grin. “How did it go? Was it as creepy as you thought? Did you enjoy it?” She was sure that Amy had hundreds of questions, but Sarah just shrugged them off and said “Yes, it was ok. Pretty boring stuff really. I am tired now though so think I’ll go to bed.” She smiled back at Amy, hoping to not give her any reason to be concerned. In bed, Sarah’s mind was racing. She thought, as she couldn’t piece together what exactly to make of the night’s events, she should just lock them away and never think of them again. Slowly her mind slowed as she fell further and further into a deep sleep.
ONE MONTH LATER
Sarah opened up her email inbox to find she had a new message. Her heart starts to race as she sees the sender “Simon” and the email subject “Craigslist”. She had tried to block that night from her memory, but the $1000 sitting in her bag was too much of a reminder. Opening up the message, she read the contents:
“Hey! Thanks for a wonderful night together. I don’t think I’ve ever had anyone as successful as you.
P.S. Thanks for telling your roommate that you had a good time!”
Sarah’s heart skipped faster and faster. Had he been in touch with Amy? All that she had said was that it went ok. Underneath the message she found a link to a website she had never heard of before. She reluctantly clicked on the link and a new window opened up the page of a porn site. The main part of the page is a picture of a pretty little blonde naked on her knees, beaming up to the camera with her face completely plastered in cum. Behind her is a black leather couch and thick white carpets underneath her. It was unmistakable to Sarah that it was a picture of her roommate Amy, sat in Simon’s house. Scrolling down the page, she discovers it was uploaded by a user calling himself “craigslist_creep” and opens the link to the member’s profile. A series of galleries of different girls appear on the right hand side of the screen and sure enough at the top is a gallery labelled “Amy”. Three galleries down though, Sarah gets a sinking feeling in her stomach as she notices one labelled “Sarah”. She clicks the link to open up of gallery with all the pictures and videos that Simon had taken of her last night and to her horror sees that the view count on each is in the thousands and the user comments are in the hundreds. She navigates to the comments section to see “Hottest one yet!”, “How do you get to be so lucky craigslist_creep?” and “Damn! I can’t stop jerking over this one! Thanks!”
Sarah lay on her bed in silence and shock, reading a barrage of comments. She slowly reached down under her covers, sliding her hand onto her panties, to feel the dampness of her pussy seeping through the cloth…
Source: reddit.com/r/eroticliterature/comments/e5kh5m/picture_perfect