First attempt at writing a story. Feel free to make suggestions on improvements. Thanks for reading.
Part one: John
John had bought a house a few years back in a college town and had decided to rent out his spare room this year for some extra cash and to have some more company around. Most of the applications he'd received were from undergrad students and after a few interviews he'd been disabused of the notion of having a nice respectful roommate. He was ready to give up on the idea when he received a last minute application from a 25 year old graduate student a week before the semester was supposed to start.
Jessica was a stunning woman, standing at 5'5'' with a slender toned build. She carried herself with an air of confidence. Her 34C breasts were perfectly proportioned to her frame and she liked to wear yoga pants or booty shorts to show off her powerful glutes from back when she was on the college gymnast team. She had a coral pink pixie cut that framed her face with a touch of playfulness. Her piercing blue eyes held a hint of mischief, adding to her overall allure. Jessica's appearance was a perfect balance of seductive and approachable, immediately capturing John's attention. John wouldn't admit it but his attraction toward her played a big part in why he said yes to such a last minute request. Jessica obviously knew the effect she had on John and would wear progressively scantier attire in the house and got a kick out of seeing Johns face turn red when she caught him looking. John had just turned 30 and wasn't bad looking himself at 5'10" with a toned swimmers build, but he was a bit of an introvert and hadn't ever built up much confidence with the ladies.
Jessica and John meshed well as roommates and fell into a comfortable routine. Their schedules were fairly well aligned and the two were typically home at the same time. They would often end up watching different shows together and sharing dinner together. Despite their friendly rapport John never got the vibe that Jessica was really into him. Jessica thought John was cute enough but preferred a more confident and dominant man.
Jessica was a very sexually free person and wasn't ever embarrassed to talk about sex with her friends when John was around. He had begun experimenting with anal play recently after overhearing Jessica's friend talk about how much her boyfriend enjoyed it. He'd been playing with a medium sized inflatable buttplug he'd bought at a local sex shop and was making decent progress at stretching his asshole wider and wider. He had fallen down the rabbit hole of anal stretching and huge anal insertion porn and had finally ordered a horse shaped cock called Chance from a brand called BadDragon. His anticipation was high but the ship time was crazy and it wouldn't be there for a few weeks.
Jessica had recently started bringing a new FWB home named Jared. Jared was a tall black man who seemed to be very well hung from the comments and noises Jessica made after she would lead him into her bedroom. The few times John had talked to Jared he had exuded a confident air that John envied. Jared was also quite a bit bigger than John at 6'2" with a strong muscular build from being a professional trainer. Initially, John felt somewhat annoyed by the interruptions to his time with Jessica, but he eventually began to appreciate the occasions when Jared would visit. In the beginning, John would either retreat to his room or sit in the living room watching TV. Despite this, he could still hear them engaging in intense and passionate sex. After the 2nd or third time Jessica asked John if they were being too loud and bothering him, but John acted oblivious and said he hadn't heard a thing.
This was obviously a lie but Jessica played along, getting an extra thrill from the exhibitionism. As time went on John couldn't stop himself from being drawn to the sounds of pleasure coming from Jessica's room. The first time he snuck up to her door to listen his heart was racing and he was shaking with nerves and arousal. He quickly grew confident that he wouldn't be caught and began to listen intently at her bedroom door any chance he got, trying to catch every sound of their passionate encounters. They were very vocal and John learned a lot about their sexual proclivities from their dirty talk. Jessica was a big fan of anal and could apparently take Jared's entire 9" BBC in all of her holes. It was common to hear her demanding he go deeper in her pussy followed by the sloppy sounds of her eagerly sucking his cock clean and the 'glug glug' sounds of his cock going deep into her throat. On a few occasions he even heard Jared demand she clean off his cock after he had fucked her ass. John wasn't a prude by any means but thought ass to mouth was a little gross and unclean.
Normally John would have his inflatable buttplug up his ass while listening and would make it a game to choose a different word each night to inflate it too. Some nights it was when Jessica would moan "harder" and others when she would mention how big Jared's cock was. John would inflate it each time until he could barely take the pressure and then try and slowly pull it out, stretching his anal rings further and further imagining Jared's BBC sliding in and out of Jessica's ass or pussy. It was almost always too big to actually pull out so he would slowly deflate the plug while pulling it until it popped out. He also started to record the sounds of their fuck sessions, putting his phone to the crack at the bottom of the door, and would masturbate to them on the nights Jared didn't come over.
Jared was a very dominant lover and it was obvious from the sounds that they engaged in BDSM play and had a Dom/Sub type relationship where Jessica was a bratty type sub. John started to tailor his porn selection around interracial and BDSM porn, searching for tags like MMF, Femdom and forced anal. He would download different videos and edit them together into compilations that he could watch while playing with his ass and fantasizing about getting dominated by Jessica and Jared. He also started overlaying the audio from the recordings over the compilations, matching up what Jessica and Jared were doing with the different scenes.
John loved the sexual energy in the house but was easily flustered by the confident pair. Jared would catch John staring at the outline of his bulge and always got a kick out of the attention. He normally liked to wear jeans to be more discreet in public but started going commando and wearing sweats or athletic shorts that would outline his 6" soft cock when visiting Jessica. John found himself adding more BBC content to his compilations. Jessica had always been pretty brazen and comfortable with her attire but kicked it up a notch and started to walk between her room and the bathroom in her bra and panties or nearly see through nightgowns. This provided John with ample opportunities to catch a glimpse, as the living room had a direct line of sight into the bedroom and bathroom hallway.
About two months into this cycle John heard them talking about how popular their new Onlyfans page was getting. Jared was saying that a lot of the comments mentioned that they needed better lighting and angles and he was going to buy some equipment online to up their production value. John immediately tried to find their OF page but quickly realized how impossible that would be. After several weeks, his curiosity was reaching a fever pitch, and he was growing increasingly desperate to see their sexual escapades. So far, he had managed to resist the temptation to invade Jessica's privacy, but the allure of witnessing their passionate encounters was gradually overpowering his better judgment and moral compass.
When Jessica told him she would be gone this coming Saturday for a day trip to the local hot springs his willpower broke and he knew that he was going to take the opportunity to snoop around her room. He had also received an email that the dildo he'd ordered was supposed to be arriving on Saturday. His excitement was so intense that/Thrilled with expectation/ he chose not to climax for several days, with the goal of having a massive orgasm on Saturday.
On Friday evening, John seemed quite anxious, and his obvious fidgeting prompted Jessica to ask if he was feeling well while they were watching TV together. His brief, guilty glance piqued her interest, but he reassured her that he was alright. They watched one more episode and then both retired to their bedrooms fairly early. Saturday morning Marisa and one of her other friends swung by and picked Jessica up.
John waited 30 minutes after Jessica left to make sure she hadn't forgotten anything before he approached her room. It was fairly large and had a king size bed with a heavy wooden headboard and footboard. The bed was situated sideways to the door against the left wall and had a nightstand on each side. On the opposite wall was a dresser with a 65" tv on top and a door to the walk in closet. Another dresser and computer table with a swiveling work chair took up the back wall. In the corner next to the bed along the front wall was an armless accent chair.
John entered the room with some trepidation but quickly got down to business. Jessica's laptop was on top of the desk and was the most obvious first place to check. With low expectations John opened the laptop and was greeted with the login screen. He checked around the desk to see if there was anything with a password written on it but wasn't surprised when he didn't find anything. Next he checked the desk for any type of external harddrive or USB drive. After finding a USB drive in one of the drawers he ran back to his room to grab his laptop. He searched through the folders on the drive but only found school related files and some older platonic pictures and videos. He made sure to check for any hidden folders but didn't have any luck.
After going through the dressers, being careful not to disturb anything, and not having any luck, John was getting sad about his prospects and turned to the closet as the last place to look. Inside the closet was Jessica's clothes hamper which was half full. John spotted a pair of sexy green lace panties and was temporarily distracted from his search. Pulling the panties out he inspected the crotch and saw the white sticky stain of leftover grool. They must have been the panties Jessica changed out of that morning as they were still damp. Bringing them up to his face he took a tentative smell and was pleasantly surprised by the musky sensual aroma. John's cock twitched with arousal and grew to half its 6.5" length.
After sniffing the panties a few more times John tossed them back into the hamper and continued his search of the closet. Ignoring the many sexy outfits and lingerie sets John spotted some lighting equipment in the corner and a small black bag behind them. Pulling it out John finally started to get excited as he opened the bag to find a DSLR camera. This must be the equipment that Jarred had mentioned for their Onlyfans account! As John turned on the camera his heart began to beat faster and his palms grew sweaty.
And there on the screen was exactly what John had been looking for, small thumbnails of the bedroom he was in with the camera pointing at the bed. John quickly powered off the camera and removed the SD card and brought it over to his laptop. There were around 15 videos ranging from 5 minutes all the way up to an hour and a half and a few hundred pictures. He quickly transferred them onto his laptop and put the SD card back into the camera.
While he was replacing the camera in the closet John noticed two boxes next to the lighting equipment and something else with a towel draped over it next to them. John opened the top box and was happily surprised to see an assortment of BDSM equipment. There were whips, flogs, a thin cane, a ball gag, an open mouth gag and an assortment of restraints. John moved the box aside and opened the bottom box. Inside was an impressive collection of sex toys and one in particular caught his eye. It was black and had a tip shaped like a buttplug that tapered down before expanding again in a cone shape with ribbed rings that got slightly bigger till the base. It looked like it was about 10" long and had to be over 3" in diameter at the base.
