A gay story: Visiting the Ceo
I arrived to work with a minute to spare. I didn’t get home until late last night and collapsed on my bed. I hit the snooze alarm twice before dragging my ass out of bed and into the shower. I had a powdered shake for breakfast. Thank god that I remembered to buy some more the last time I was at the store.
I sat down at my desk. I work in an office with about 20 other people. We all have our own little cubicle. The first thing on the agenda is to review my emails. Just some of the normal b.s. that I have to read through every day. Heaven help me if I should miss some obscure point in an email from the VP in charge of fuck ups. I normally work from 8 until 4:30. It was going to be a long day.
My name is Jack. I’m 24 and have been out of college for a couple of years now. After working a dead end job for a year and a half, I found a job with this company about 7 months ago. As much as I am complaining about it this morning, I actually enjoyed working here. My complaints have a lot more to do with how tired I was from last night as anything else.
I had gone to a party last night. Well, maybe a party isn’t the right term. I went to meet up with a couple of guys, Al and Dave, that I had been with before. I met Dave at a bar a few months ago and wound up going with him to his apartment.
My girlfriend, Kim, left me about a year ago after being together for a couple of years. She was the only girl that I had ever slept with more than once. I suspected that I knew why I had such little luck with women. My cock, when it was at full staff, never got to 5 inches. My girlfriend taught me how to get her off with my tongue. Not only did she enjoy it (at least I thought that she did), I enjoyed it. I even went down on her after cumming inside her. Our sex life became a routine where I would bring her off orally, then fuck her, then she would feed me my cum until she came again.
I saw a picture of her with her new boyfriend on a social post. They were at a pool party. She was in a bikini, and he was wearing board shorts. He was bigger than me in every way. Well, in my paranoid state, I assumed in every way. I couldn’t see under those board shorts.
I am 5’8″ and weigh in at 135 pounds. I have hair around my dick and some under my arms. Like my head, it was blonde. When I looked at myself in the mirror, sometimes it was difficult to see the hair.
I was having a beer with a friend, Ken. I was really down. Ken was a coworker in that dead end job.
“I know its rough, Jack, but you’ve got to move past this. Have you asked any other women out since she left?”
I had. A couple, but had been shot down both times. Since Kim left, I had been reduced to jacking off to porn, and lately the ladies in porn have been resembling Kim. The men she was with, were always bigger than me. And since it was porn, I can tell you that they were bigger under the board shorts as well.
“I’ve asked a couple of girls out, but I’ve had no luck.”
There was no comment from Ken for about a minute. “Have you ever tried a guy?”
I stopped in the middle of drinking my beer and looked at him. “No.” I hoped that I said it in such a way to let Ken know that I would never try a guy either.
Ken set his beer down after taking another drink. “Do you miss the sex?’
I looked around to see if anyone could hear our conversation. I couldn’t believe that I was having it. “Come on Ken. I don’t think that I want to talk about this, especially not here.”
Ken finished his beer and waved the bartender over to close out our bill. “Ok. Let’s talk about it at my place.”
Shit. I didn’t want to talk about it at all, but right now, I felt that Ken was about my only friend. The friends that Kim and I had, had stayed with her. That’s what happens in a break up. When I thought about it, they were always more her friends, than mine. My choices were to go with Ken to his place, or go home and jack off to “Kim” porn. Ken and I lived in the same apartment complex, but at different ends. When I pulled in the main entrance, if I went left, I was heading to Ken’s place. If I went right, I was going home to jack off. I turned left.
Ken was already home and answered the door with a beer in his hand. He handed it to me and suggested that I take a seat on the sofa.
He already had a beer for himself there. After we sat down, Ken told me that he had been in my place a couple of years ago. Ken was 26. He stood about 6 feet and was 170 pounds. He was handsome for a guy. “I tried singles bars, online dating, blind dates set up for me by family. None of that was getting me laid. I was desperate enough that I was willing to take a blow job from a guy.”
I hadn’t taken a swallow of my beer yet. As I digested this information, I took a swallow. “Are you telling me that you’re gay?”
“No. That’s not what I’m saying. Look. I went to a gay bar one night to see if I could find a guy to give me a blow job, and on the first try, I did. I didn’t have to buy dinner or a movie. I struck up a conversation with a guy at the bar, and an hour later I was at his place. He gave me a great blow job.”
“Did you have to suck him in return?”
“No. That was understood going into it. After giving me the blowjob, and swallowing it, he asked me if I wanted to fuck him?”
“Did you?”
“Not that night, but the following week I was back. He had me fuck him on his back and asked me to jack him off at the same time. I had never touched another guy’s dick, but I did it. And I’ve got to tell you that helping him cum as I was fucking his ass was exciting. I wanted to do it again. I’ll admit. He was sexy and had a good size cock. As I was stroking him, I wondered what it might feel like to have him fucking me.”
“Did you let him?”
“Not that night, but after cumming, we rested and had a drink, then we got into a 69.”
“So you sucked his cock. Did he cum in your mouth? Did you swallow?” This conversation was having an effect on me and I was getting hard.
“Yes and yes, and the following week he fucked me after I fucked him.”
“You were wearing condoms, yes?”
“Yes, but since then, I’ve gone on PREP. I have a few fuckbuddies, including him, that I do bareback with.”
“Bareback? You mean you don’t use condoms?”
“It depends on the guy and the situation.”
“Do you still fuck women?”
“I have, but its been almost a year now. If I found the right woman, I would consider limiting myself to one or two guy friends.”
“Ok. Before we go too far down that road, why did you invite me here? Are you offering me a blowjob?”
“If you would like one, yes. Look. Your right hand isn’t the answer to the problem.”
I used my left hand, but I understood what he was saying. “Would I have to suck you in return?”
“Tonight, no. But if you want it again, that would be the deal. A suck for a suck.”
I took another drink of my beer. “Do you have any pot?”
Ken went to a drawer in his TV stand. He pulled out a tray. There was a pipe and a jar of weed, already ground up and ready for the bowl. He packed the bowl, lit the pipe and passed it to me.
“Would it help if I turned on some porn?”
I took a second hit and after I exhaled I asked if it was gay porn?
“Your choice. I can play either gay or straight.”
The porn that I had been watching all had “Kim” hooking up with guys with big cocks. Some of them were black. I spent a lot of time watching my make believe Kims swallowing big cocks before watching those cocks fuck her in various positions, even occasionally in the ass. “Have you got anything with bi?”
“I stream my porn Jack. I can get anything you like.” He took another pull off the pipe and handed it to me and proceeded to load something on the TV. It took two more tokes from each of us before the porn was playing on his big screen. Ken jumped up and returned with a big towel. He asked me to stand up and take off my clothes. He spread the towel on the couch and had me sit down while he disrobed. Why did he need to take his clothes off if he was just giving me a blowjob.
He took another drink from his beer and sat down next to me. He suggested that we just stroke ourselves for a moment and watch the action on the screen. There were two guys and a girl. She had a nice set of tits. At one point, she was sucking a cock and went to lick the side of it. The other guy leaned over and started licking the other side. After 15 or 20 seconds of this, she started kissing up the body of the first guy, leaving guy #2 to suck the cock.
Ken reached over and took my cock in his hand. I had seen Ken’s cock when he had taken his clothes off, but now I looked at it again. He had 7 inches above a smooth body. I assumed that he shaved. He started to stroke my cock and I laid my head back and closed my eyes. I noticed a change in what I heard from the TV. When I opened my eyes, guy #2 was now performing oral on the girl and he was being fucked by guy #1. I looked at Ken’s cock again, and reached for it. We stroked each other until the video ended. The site cycled to another video, also bi.
Ken took his hand off my cock and stood up. That removed my hand from his cock. He pushed the coffee table away from the couch and knelt down between my legs. He leaned forward and took my cock into his mouth. Kim had given me blowjobs, but it had been over a year since she had done so. I laid my head back again and let Ken do his work. He started by licking my balls, then licking up to the top of my cock. He took me all in one downward stroke. He held his mouth there for a moment while he swirled his tongue around my cock.
Then Ken started going up and down on my cock as he fondled my balls. I felt a finger working its way from my balls towards my ass. Ken pulled my body towards him so that my ass was near the edge of the couch. This allowed that finger to get to my ass. I looked up at the TV. This time a guy was fucking another guy in the missionary position while the girl held his legs up. She was sitting on the face of the bottom guy. I assumed he was busy with his tongue. The top guy was stroking the bottom’s cock and kissing the girl. The bottom started to cum, spraying his load over his abdomen and chest.
That did it for me. I started cumming in Ken’s mouth. I never even thought about warning him. I hoped he wouldn’t be angry. Ken swallowed it all, gave a final lick to my dick and my balls, then lifted my legs and gave me a couple of licks on my ass before lowering my legs again. I enjoyed those few licks on my ass.
Ken got up and asked me if I would like another beer? I asked if he had a bottle of water. When he walked away, he headed towards his bedroom. He was wearing gym shorts when he returned. He went in his fridge and returned with a water and a beer. He turned the TV off and sat down next to me. He handed me the water. “Well. What do you think?”
I looked at his smooth chest and saw that he still had a bulge in his shorts. I wasn’t sure if I could reciprocate. I took a swig of the water and told him that I hadn’t had a blowjob in a long time. “And while I don’t have a lot to compare it to, that was the best that I’ve had.”
“Thank you. I enjoyed giving it to you. Most girls don’t enjoy giving them. Most bi and gay guys love giving them. If you like blowjobs, that is another thing to consider.”
“I think that I have a lot of things to think about. Do you mind if I take the water with me?”
“Not at all.” I got up and got dressed and Ken showed me to the door. “See you tomorrow at work”, he said as he opened the door for me.
“Thank you. I liked this.” Two days later, I had returned and we got into a 69. I wound up swallowing someone else’s cum for the first time. We did this in Ken’s bedroom. When we were done, Ken put on his gym shorts and handed me a towel to wrap around myself. We went out to have a beer. Ken turned on some gay porn.
On the screen, the action quickly got to a guy eating a second guy’s ass. I remembered when Ken did that to me for a little bit two days prior. “I liked that when you did it to me” pointing at the screen with my beer bottle.
“That is a special feeling. I enjoy both giving and receiving that.”
Ken took another drink of his beer. “Would you like a smoke?”
“I thought that you would never ask. Yes. Thank you.” Ken walked over and grabbed the pipe and a lighter out of the drawer. It was already loaded. He took his toke and he walked back and handed the pipe to me. We passed it back and forth a couple of times. The action on the screen had gotten to the point where the bottom was lowering himself onto the cock of the top.
Ken took a drink of his beer. “I’ve got to tell you Jack. I would like to fuck you.”
I could barely get his cock in my mouth. I didn’t think I could take it in the ass. “Would I get to fuck you as well?”
“Definitely. I love to flip.” I didn’t know what flip meant, but I liked the “definitely”.
At our next meeting, we flipped. We were relaxing afterwards and Ken suggested that he take me to the gay bar. If I was interested in more, I could find a lot at that place. Which brings us full circle to where I met Dave.
After Ken brought me to that bar a couple of times, I started visiting on my own. I met a few guys there and had fun with them. I fucked a couple and got fucked by them all. I found that I was enjoying the feeling of a big cock entering my ass. But, I hadn’t really experienced a big cock yet.
One night, I met a guy by the name of Mike. Mike was 6’3 and towered over me. Mike asked me to go home with him. He was the typical guy that “my Kim” would attract in the pornos that I used to watch. I followed him to his place. When we got down to business, Mike dropped his shorts, and I was in the presence of the biggest cock I had ever seen. It was already twice my size, and it was still hanging soft. Mike had me disrobe and get on my knees. “Get me hard Jack.”
I took him in my mouth. He had to remind me to watch my teeth. As he got hard, I was having a difficult time keeping him in my mouth, because it was so strong, it kept popping out. Mike lifted me up (yes, he lifted me) and placed me on his bed with my head at the edge. He then pulled me back so that my head wasn’t supported. He brought his cock forward and I opened my mouth again. Once again, he had to warn me about my teeth. He started working his cock in and out. Once he was hard, it wound up being 10 inches and thick. When he got to my throat, he pressed forward. Backed off and pressed again. He did this several times.
“Try swallowing Jack. Relax that throat for me.”
The next time he pressed, I swallowed. I felt it slip in a little before I pressed his hips and he pulled out.
“You almost got it Jack. I’ll give you a moment and then we can try again.”
Try again? You already got it in once! I couldn’t say these things out loud because his cock was still stuffed in my mouth.
He pressed forward again after a few seconds and I felt it slip in again. “That’s it Jack. Let it in.”
He never got it in all the way. I was panicking about getting air.
He withdrew and then flipped me around so that he could start eating my ass. I had taken a couple of 8 inch cocks over the past few weeks or months, but I never had one this thick up my ass. The thing is, if someone eats my ass, I am willing to let them do just about anything to me. I think that Mike knew that he had a newbie to his size, so he took his time. He worked his dick in gradually, and eventually bottomed out. “Are you ready Jack? I’m going to try and blow your mind.”
I had heard about orgasms from anal penetration only, but up until that day, I had never experienced one. Afterwards, I had recognized that I had been close a few times before, but I had blocked it. I couldn’t block it this time, and I was glad that I didn’t. The orgasm that I had that night was the single best orgasm of my life.
From that point on, my major goal was to cum from anal stimulation only. A lot of guys got me close, but with most of them, I had to manually stimulate myself or have them stroke me to achieve that orgasm. I found only a couple of guys that could cause it without manual stimulation. Mike had a regular boy friend, so he wasn’t able to scratch my itch regularly. Then I met Dave.
I had moved jobs by this time. I was no longer working with Ken, but I was still in touch with him. I was in the bar one night on my own, and Dave came up and started talking with me. One thing led to another and I was at his apartment. It was a nice loft in the downtown area, not far from my new office. Dave was only the third guy to help me achieve that anal orgasm.
I would meet up with Dave every other week or so, and one day he had a friend with him by the name of Al. Al was staying with him for the week. Al fucked me and I got to my orgasm with the help of stimulation. Then Dave fucked me and thirty minutes later I was able to attain an anal orgasm, again, this time without stimulation.
My thoughts about Kim had long since vanished. I tried to control my urges, only going out once during the week and on Friday and Saturday nights. Dave wasn’t around a lot, so I hooked up with other guys if I could. Most nights, I was being fucked in my bed or their’s. I wasn’t doing any fucking anymore. I hadn’t received a blowjob to completion for several months. Yes. A lot of times they would start by sucking me, but once I put their dick in my mouth, it progressed to my ass. I was using condoms with everybody, everybody but Dave.
Dave showed me a negative test for HIV and a bottle of PREP pills. I was already on PREP. He said that he wanted to take me bare. I can’t tell you how much better that fuck felt. Dave had fucked me six or seven times by then, and Al twice. Al visited often. Al showed me the same data and he became the second guy that was fucking me bare.
I got a message from Dave yesterday morning. Al is in town for the night. Can you come over?
I had to work the next day, and I had been out last night. But I enjoyed the times that I was with Dave. I replied: What time?
I arrived at 8. I was able to get home, clean up and out and take a 30 minute nap. Dave met me at the door with a joint in his right hand and a vodka and tonic (for me) in his left. Al was on the sofa with a porn playing on the TV. He was still wearing his boxer briefs, but nothing else.
Shortly after I started at the new job, someone pointed out the CEO walking through the office. His name is Mr. Roberts. He was walking with his personal assistant, Jeff. When they got to their office, Mr. Roberts asked Jeff who the new guy was? “His name is Jack Wilson.” Jeff explained my qualifications and work history. That was all fine and dandy, but Mr. Roberts had seen me before. He occasionally went to that bar that I had been introduced to.
Mr. Roberts suspected that I was gay. After all, why would I be at that bar? He had a nephew by the name of Dave. He told Dave to look me up at the bar some night. He had Jeff print up a picture of me from my personnel file, and he passed it along to Dave. “Check him out and let me know.”
I received an email from Jeff just before 2 asking me to work late, probably only until 5 or 5:30. By 4:30, the office was empty except for me. I had no idea why I was asked to work late, but I had plenty of work to do, so I just kept doing it. If last night hadn’t been so long, it wouldn’t have been a big deal.
At 5, Jeff was at my desk and asked me to follow him. He escorted me to Mr. Roberts office. I had met him before and even shook his hand once. Mr. Roberts asked me to take a seat. Jeff took the other seat.
Once we were settled, Mr. Roberts told me that I had received an email earlier today from an outside address.
“Yes sir. I did, but I didn’t open it.”
“There was an attachment to that email.”
I looked at Jeff. “I noticed the attachment Sir, but I didn’t open the email or the attachment. I would never do that on a company email (or on a personal one either if it was someone I didn’t know).”
Mr. Roberts hit a button on a remote and pointed towards the 50 inch TV in his office. “We opened that email and the attachment.”
I saw Dave and Al on the screen, with a guy on his knees giving Al a blowjob. The guys face was blocked, but I knew who it was. When the guy moved from one cock to the other, the face came in plain view. It was me. Mr. Roberts paused the video.
I looked at him. “I didn’t know that was being taped.”
“There is more Jack.”
I know there is more. There is a lot more. The video shifted so that I was being fucked by Al and was blowing Dave. By this time, the blindfold had been put on me.
Dave and Al had me wear a blindfold once before. I loved not knowing what was coming next, so I had no problem when they handed it to me this time.
While Al had cum in me, he hadn’t brought me off. That was left for Dave. The next clip showed Dave fucking me and the video zoomed in when I started cumming over my abdomen.
I was worried. Were they going to fire me over this? I not only liked this job, I needed it. “Sir. Really. I didn’t know this was being taped, and I didn’t open that email.”
“There is more Jack.” He pointed at the screen. He didn’t have to tell me. I knew there was more. If the video had ended here, I wouldn’t have been concerned about it.
The next clip had another guy there. He must’ve been wearing a camera on his head, because all that you could see was his cock and abs as he fucked me. His cock was easily as big as Dave’s. He fucked me until I came again. The clip showed that.
Then I got a question from last night answered. I wasn’t sure who had done it, but the next clip showed the mystery man working his fist into my ass. I had never had that happen before, so it took almost 45 minutes for my ass to relax enough. Dave was talking me through it. I don’t know if the clip was of the first penetration, but when I saw the fist go in, I remembered that first penetration. I squirmed in my seat. I thought that I heard Jeff snicker.
I looked down at my lap. Mr. Roberts called my attention to the screen. “There’s a little more Jack.”
I looked up. My face was pointed up, still with the blindfold on, and there were 3 cocks being stroked above my face. I couldn’t tell who came first, but over the next few seconds I had 3 loads on my face. Somebody had done some pretty good editing, because in reality it had taken the 3rd guy a good 4 or 5 minutes to complete. I hadn’t left Dave’s until 11:30 last night. So what took 3 hours in real time had been condensed down to a 2 minute video. The final scene of the video was frozen on the screen. My cum covered face, and I was smiling.
Mr. Roberts got my attention. “We can’t have stuff like this coming into our email system Jack.”
“I understand that Sir. That is why I won’t open any videos that I don’t know the senders.”
“So. You’re saying that you don’t know this guy that sent it? You obviously know the guys in the video.”
“Yes sir. I know them slightly.”
“Slightly? This is how you act with guys you know slightly? Did you know the third guy at all?”
“No sir”
“So you let 2 guys that you slightly know, film you, fuck you, blindfold you, and then hand you off to another guy that you don’t know at all, and he fucks you, then fists you. On a work night. My god, what do you get up to on the weekend?”
Nothing like this. I’m not sure what got into me last night. I wasn’t high. I don’t think they drugged me. I was just incredibly horny and agreed to some things early on. I did not “not enjoy” anything that happened to me last night, with the exception of maybe the fisting … maybe. Being fucked by an anonymous stranger has been a fantasy since I’ve been fucking guys. Last night was the first time that’s happened. I wasn’t going to let it stop last night, and if the situation came up again, I may not stop it again.
“Is this going to affect my job Sir?
“No. This has nothing to do with your job.”
“Thank you Sir.”
Mr. Roberts handed me a piece of paper. On it, was typed an address. “Jack. I’d like you to be at that address tomorrow night at 7.”
I looked at the paper. Tomorrow was Saturday. I would be able to sleep in and relax before going to this address. I had a feeling that I was going to need the rest.
“Yes Sir. May I go now?”
“Certainly Jack. I want to thank you for staying late.”
After I left the office, Mr. Roberts sent a text to Dave: Everything went well. See you again tomorrow night.