Caught in the Office

Jason pulled down his pants. He was in his usual office fit, blue button down and khaki chino pants. His pants bunched up at his ankles with his ridiculously expensive lululemon underwear and his belt made a "clink" on the floor tiles. His work look was so unsuspecting that nobody would imagine all the kinky shit that him and his girlfriend April got up to.

He had already pulled out the dildo out of his bag and fixed it to the center of his desk. The suction cup held firmly to the glass top of the desk about an inch in from the edge. He has removed his laptop and all the paper and other junk and had a clear surface to get to work.

April had slipped the dildo in Jason's laptop bag with a note as a surprise. It was a shock to Jason when he got to work that morning and saw the pale flesh colored thing at the bottom of his bag. He quickly pulled out his laptop and hid the bag under his desk. It wasn't until most people had left for lunch that he pulled it back out and read the note:

"Did you like your surprise sweetheart? I didn't mean to scare you. I knew you'd be working late today anyway so I thought I'd back you a nice treat. Be a good boy for me and use it at your desk. Send me a video so I know you completed your task."

-xoxo April

Jason got red hot and excitement started swelling in his crotch. April wanted him to use it here? She was right he would be working late, often times he was the last to leave the office, but dam it still felt risky. He also couldn't believe how big the dildo was. It was an inch longer then his cock and much thicker. It had a fat flesh colored head and life like veins up and down the sides. At the base the suction cup set beneath a bulging pair of balls. Jason was a little annoyed she packed such a life like dildo it would really be like he was getting "fucked."

While April had played with his ass before it was never with anything like this. Only with her fingers or a prostate massager. She would make a whole show of it though. Make him present his ass to her for her to play with. She would slap his balls and spank him, make him beg to be "fucked." She convinced him that he needed to be trained to take it up the ass like a professional.

Jason slipped the note back in the bag and felt his hard-on flex in his pants. It was resolved, he would do it.

So there he was that evening, looking at the set up on his desk with his pants around his ankles. There the big dildo sat in front of him ready and waiting. He wondered if he would even be able to take it. There was no going back now he thought. Using the lube April also slipped in the bag he squirted a hefty amount on the top of the dildo and rubbed it around. It felt like he was jerking the thing off. Next he put a similar amount on his fingers and reached around and rubbed it around his hole. The excitement of having his pants down in the office was already getting him hard but feeling the cool lube around his hole got him really excited. Ok he really wanted this. Oh shit he thought to himself, almost saying it out loud, he forgot to set up his phone to record. He shuffled to the other side of the desk with his pants still around his ankles and propped up his phone and started recording.

He shuffled back over to the dildo, thought "fuck it" to himself and turned around. Thankfully he was tall enough that he could lower himself onto the dilos standing up. It took a second to line up the head with his asshole but once he was in the right position Jason began to push down. It hurt like a bitch opening his ass up for the plastic cock. Jason felt like his ass hole was burning, being ripped open by the fat dildo. He slowly pushed down the shaft, groaning in pain. Jason made the mistake of flexing has asshole, tightening around the dildo, this sent a jolt of pain shooting through his body. He realized he needed to really relax and release the tension in his ass. This dilos was so much bigger then anything he had taken before. As he began to release he felt the dildo slide up into him a little bit quicker. After about a minute he felt it bottom out. He couldn't believe it he had taken the whole thing, April would be so proud of him.

The pain of taking the dildo had made him go soft but as Jason sat there feeling the full extent of the thing inside of him he realized it felt kind of good. He adjusted himself leaning forward a bit so had more control of his movement. He now had both feet flat on the floor instead of the tippy toes needed to slower himself on the dildo. In this position he could move back and fourth, bounce on it, and fuck himself. This maneuvering brought new sensations and he let out a slight "ughhhhhh." God he felt dirty doing this in the office. He slowly because lowering himself up and down, working the dildo. Only a few inches at a time at first but soon his pace quickened and the strokes were longer. In a couple of minutes he was full on fucking himself.

Jason looked over at the camera. In profile you could see the base of the dildo and a section of the shaft disappear in and out of his muscular ass cheeks. His blue dress shirt was hiked up around his waist and his slim but muscular runners thighs flexed as he worked. His cock stuck out hard as a rock in front of him. Seeing his rock hard cock in the camera he began stroking himself and moaning, loud, for the camera and ultimately to show April back home.

Little did Jason know there was another camera filming the action. The custodian, Victor, had heard the commotion and ran over to see who was still in the office. To his surprise he stumbled upon Jason with his pants down and a fat dildo in front of him. Victor wasn't going to miss the opportunity to watch what was about to go down, now and at any later date he choose, so he pulled out his phone and quietly began recording himself. He positioned him self peeking around a cubicle so it would be hard for Jason to spot him. And it worked Jason was too distracted by his dildo to notice Victor. Victor's own cock started growing in his pants. It was sexy watching Jason's pale Yuppie ass take the dildo. Victor had definitely noticed him before and relished watching his muscular body take it. His own video was just as good as the one Jason was taking for April.

Jason's pace quickened even more. Now he was really enjoying himself. He fucked him self furiously on the dildo, jerking himself off while he did it. The combination was taking him too new sexual heights. He may have found his new hobby he thought to himself. He was already close to cumming. The simulation on his prostate was almost too much to bear. He jerked himself even harder and boom, his massive load shot out from his cock and sprayed the floor in front of him, the wall, and a couple other items. Damm April was going to enjoy this video.

Jason dislodged himself from the dildo, stopped the recording, and accessed the damage done. There was cum everywhere. He turned around and what he saw stopped him in his tracks. There was the Janitor, Victor, smirking at him.

"Don't look so surprised buddy. You've been very naughty." He jeered at him.

"I'm so sorry, I swear, I didn't know you were here" Jason responded terrified. His nervous facial expression made Victor giggle. He loved having this white boy scared.

"It's ok baby, you can do it anytime I'm here just clean up after yourself" Victor said throwing a towel at Jason. Not missing a beat Jason kneeled down and then got on all fours wiping up his cum. His pants were still around his ankles so Victor got a peek at Jason's asshole. It was glistening with lube and gaping slightly from the massive tool. He look delisted like that with his pussy presented for him.

"In fact you don't even need the dildo baby, you can just use mine."

Jason was too scared to turn around and look at Victor. He just kept cleaning. If we did he would have saw Victor pawing his crotch.

"I'm sorry I'm straight Sir." Jason responded unsure why he was using "Sir," the office setting must have been coming back to him.

Victor cackled. "You're straight and you're fucking yourself?... Fucking yourself with that?"

"Yeah man I was filming myself for my girlfriend." Jason responded on the verge of tears at the humiliation.

"Dammmm baby she has you trained well." Victor said still pawing his crotch.

"Yes Sir. I like letting her be in charge." Jason was unsure why he was giving all this information away.

Victor cackled "I am sure you do baby, that's ass was made for fucking. Let me give you the real thing."

Jason couldn't even respond just kept cleaning up his load.

Finishing up he stood back up and pulled up his pants. In his embarrassment he had forgotten they were down.

"Awww the shows over." Victor said again laughing.

Jason finally got the chance to look at him. Victor had a slight beer belly, a mustache, and a sloppy unshaven face. He was dressed in a company polo, jeans, and work boots. Jason honestly hadn't really noticed him much before this.

"Again I'm really sorry man I didn't mean for you to see that." Jason said meekly strapping his belt.

"Are you kidding that was the most fun I've had at work in years buddy."

Jason giggled, unsure what had come over him.

"Go home buddy it's late."

That is a good idea Jason thought to himself.

"Just know you're going to be doing it for me again buddy. Know I can show my video to anyone here and get you fired."

"Yes Sir" Jason responded. Still shocked by his own compliance.

"Give me your number baby."

...

Jason sat in his car and thought about what just went down. He had just taken a real dildo for the first time, used it to fuck himself a shoot one of the biggest loads of his life, and then got caught in the act. He had to admit his asshole was sore but he was honestly ready to do it again.

He pulled out his phone and sent the video to April. This would give her enough time to watch it while he commuted home. Following the video he texted her: "How did I do Mistress?"

He wasn't going to tell her what happened with Victor, too embarrassing. Plus he was still he was still worried about what could happen. The guy now had a lot of leverage over him.

Before he pulled out of his spot he got a text from an unknown number. It was Victor. "You did a good job today boy but we are just getting started." Jason put his phone down, sighed, and backed out. He was fucked.