Holiday Story 2: Jeremy Dooley & The Dildo

Jeremy’s package finally came in the mail. He ran to his mail cubby in the rooster teeth office after he got the email that the item was delivered. Rushing through the halls, people would notice, but paid no mind after they saw who it was. Figuring it could be another video or what not. Once Jeremy ripped into the mail room, he grabbed the padded envelope bag that stuck out of his box and continued to walk fast, so nobody asked what he had gotten. He made it into the bathrooms and made sure no one was in there by checking each stall. Jeremy had gone to a bathroom in the back of the warehouse where not too many people ventured. He knew from since he ordered the package he watched which place he could…use his new toy. Once he made sure the full bathroom was empty he opened up the last door of the row of stalls and locked it behind him. The room was very clean which made Jeremy pretty happy, although he would’ve seen what he could do if it wasn’t, he really just needed this.

Lately Jeremy had been getting rather…adventurous. Specifically in the ass region. While he was getting a blowjob he’d ask for a finger or some kind of anal stimulation. It just started feeling right and sooner than later, Jeremy would have 3 of his own fingers buried in his tight channel when he’d touch himself on weeks when his wife was gone. Face down on the bed, arm reaching back trying to get that stretch that he learned to love so fucking much. He’d come practically buckets more than when he had just regular sex. His ass was becoming something of a necessity to get off in general. So when he had thought the stretch was too hard to achieve with all of his fingers, he ran to what he knew would help him. The internet. More specifically, porn shops of the internet. He scrolled for a little while, getting hard at his home desk, looking up “beginner’s toys” and “anal trainers”. He settled on a nice 7” dildo that suctioned and had apparently realistic veins? Not too expensive and it was on it’s way.

Jeremy had opened the bag fast, loud plastic sounds filling the silence. He got the shell casing out and pulled his knife as he ran his thumb up the cock that was incased in plastic. Jeremy cut open the package and was happy that he cut himself. Just running out for help with a dildo in its casing still behind him would not be the way he’d want people to find him. He tugged the rubbery cock out of the case and threw the remnants onto the floor. Jeremy held the fake cock in his hands. He stroked the cock as if it was his own, or like he was trying to pleasure another man. He didn’t know what he was doing anymore, just pure lust and want spreading through his body. Making him hot in more than a couple places. He brought the dick closer to himself and looked to see how big it really was, holding it to his groin like it was his cock. Thinking it was shorter, yeah, so accurate 7”. But the girth was, well, it was a true beer can cock. His fingers just reaching each other if he chocked down on the cock and his hands were pretty beefy. 

He brought the cock towards his face. A gentle swipe of his tongue glided across the head and slit. Jeremy bit his lip produced a look that was a mix between confusion, determined, and wanton. He quickly placed the whole head inside his mouth, his lips stretched thin around the crown. Jeremy’s tongue lapping and cheeks sucking in. He pulled off with an audible pop. A sound that made him groan. The groan itself shocking the presumed straight man. “Well, bought you for my ass, and my mouth ends up liking you.” Jeremy talked to the inanimate object. He shook his head, and turned it around to lick the suction cup, then pushed it down onto the closed toilet seat. After he released the thing, it bobbed back and forth. Almost inviting Jeremy, pulling him closer as he got down to his knees and reached forward and grasped the length. He pulled his hand back and spit in his palm to the reach back and glide up and down the dick. Stroking the cock felt right? Another feeling that he never thought he’d have, the thought bringing him back to the need he felt in his ass. He stood up and looked for the packaging, inside being a small tube of lube - Jeremy thought ahead. He pulled the lube bottle out and opened the cap. He tilted the bottle over the top of the dildo and watched as the clear fluid rolled down the already slick cock. He pulled back when half the bottle was empty and sat it down behind the dildo. 

Jeremy opened the door to the stall and looked out to make sure no one had entered and once he saw the coast was clear, locked the door again and started unbuttoning his pants. He thought to leave most his clothes on so if he had to quick and hide everything, he could get dressed quickly. He rucked his jeans and boxers down past his knees and reached back to tug his cheeks apart, liking the stretch. He used the rest of the lube to oil his fingers as he pushed two immediately into himself. A moan pushed out and while he already had two fingers in his ass, he pushed back to feel the touch of the head of the cock. Eager, Jeremy pried his hole and entered a third finger. Pulled out quick and reached back under himself to re-insert the three fingers. He pushed his lips together as the fingers spread and spread his hole. His ass almost understanding how quick he needed to prepare. The hole giving way and accepting the fingers as he pushed the tip of a fourth in there. He figured he needed a little more to ensure he didn’t hurt himself, still wanted the stretch, but the thought again of having to run out hurt made sure he prepared himself enough. Once he felt he was prepped, Jeremy pulled the fingers out and looked back to make sure the lube was still coating the dildo. Jeremy reached behind and pulled apart his ass cheeks as he tried to sit on the cock. The silicone moving back and forth getting his ass a little more wet than what he wanted. Jeremy determined, finally made contact with his hole and started pushing back. The hole truly now giving away to the hard object. 

Definitely glad he stretched with the fourth finger. The burn was almost too much, but once the longer than normal head sucked through, it was just the right amount of pressure. Jeremy only had the bulbous head in himself, but his cock was already weeping, precum ran down his throbbing cock. Jeremy thought the head was hardest part, but the shaft was still just as thick if not a tad bit wider around the middle. His hands shot out to the walls to his sides as he sat further down. His mouth now open and gasping, the slow push opening him deep. Jeremy kept pushing back, his face stuck in an orgasmic bliss kind of look. He paused a second because it was almost too much all at once. He rested waiting for his hole to accommodate. He reached back to see how close he was to the bottom, he had to have been pretty close, he thought. He reached back and felt that he was barely half way down the length. He gasped and looked confused as he felt the length and where it met his ass to make sure, but he was nowhere near taking the full length. “Holy shit” Jeremy exclaimed silently. Jeremy looking determined pushed down harder while pushing himself with his arms back on the walls. He made another good portion shoot up into himself, which hit a special spot that Jeremy had been trying to reach these last few months. 

Right then when the cock his his prostate, Jeremy’s ass opened more and allowed him to take most of the length. He paused again, another wanton gasp and mouth open look appeared, eyes wide open and more precum running down his balls. “That’s it” He moaned to himself as he started a wild bounce that pushed the length in and out at a rapid speed. The hole widening and shrinking back with every thrust. He bounced as fast as he could. He reached back and placed his hands on the water tank above the seat. Giving the dildo a new angle that rubbed his prostate with every single move. His hard dick smacked back and forth hitting his stomach. Precum flying and hitting him in the face as well as splattering around the stall. The dildo kept hitting exactly where he wanted inside his ass and oh did he wish it would cum inside of him. As the thought of the warmth that would fill him took over, his release did as well. Not stopping his thrusting, just like the pre, his jizz shot everywhere. His face, small spots on his chest, the wall behind him, the stall door, the floor in front of him, to then finish itself and flow down his cock and balls. Jeremy stood and pulled himself off the dildo. The same audible pop came from his hole still trying to grasp at the dildo that his mouth did earlier. 

Jeremy in need to get back to the main office for work started cleaning up quickly. Pulling his pants back up and making sure his shirt was clean as it could get. Once the stall was clean and the package wrapping thrown away, he realized he would still need to somehow get the dildo out of here. If he put it back in the package, it was too ripped to have it fully conceal the dick. He looked around for any kind of box, paper towels maybe. All things that he would end up getting questioned about. Finally a lightbulb clicked above his head. Even though he couldn’t take the full length before, he was going to have to now. He pulled down his pants and sat back on the dildo, really forcing it up his recently opened ass. Jeremy after a minute of continuous pushing, sat completely on the suction cup, his ass never felt so full. His underwear acting as a tight sleeve to hold the dildo inside himself. He pulled up his pants and started making his way out to his car so he could hide the dildo, when he got a wicked thought from his twitching cock.

Jeremy walked back into his office with the rest of the guys, pulling back his chair and started sitting. The feeling of the dildo making itself known obviously as he ground himself in the chair, trying his hardest to not make a sound of face. He looked around, no one noticed. He’ll just leave this in till he has time to run out to the car. The next couple days are going to be very fun.