Had a good dream last night. Some of it is based on true events about myself.
I am currently looking for a new place to live as I am recently separated from my wife (true).
Since most of my money is wrapped up in our house I am cash strapped. Its not easy to find something in the northern VA area these day, so I’m starting to get desperate. I go to work and I ask around if anyone knows anyone looking for a roommate or a basement to rent. I’m in my mid 50’s and look like most guys my age. This one day would change everything and then some. I’m in my office when we get word the CEO (John) is arriving. He is some billionaire who is in his late 70’s, bald and short. Nothing to look at.
The day goes on and I get a message to come to the office he’s in. I’m worried why the hell he would want to see me. I go in and he smiles. “A little birdy tells me you’re looking for a place to live.†I was perplexed and just answered “yeah it’s been a tough one on the personal side, but it’s not affecting my job. In fact I am working harder than everâ€. I am not sure why I added the last part. He nods his head. “I get it divorces are hard and I had two myselfâ€. He laughs. “I think I can help you out, I have a pool house and I need someone to watch the main house while I’m away traveling the world for work. Interestedâ€?
“Heck yeah, that would be awesomeâ€. I said without hesitating. I knew he lived in a huge property and the pool house is better than a basement. “Great, can you drop by tonight, and I can show you aroundâ€? I quickly said “yesâ€. The day flew by, I drove to the house and saw a fountain in the front that was bigger than my living room. The John met me at the door. “Come in, come in. Let me introduce my wife Cindyâ€. Cindy was mid 60’s very thin with a very toned body and graying dark hair.†Cindy had a laptop in her hand as she walked over. “Ah he’s here great so did you ask him yetâ€? I jumped in “about watching the houseâ€? I smiled. John laughed “oh no, about how and what you are going to do to keep your jobâ€? I was shocked. John opened the laptop and turned it so I can see, and there in front of me was my profile on AFF. “So you are looking to try anything and do anything? You love oral? Well let’s see if you will do what it takes. Now come back here after work on Friday and we will see. Now get the FUCK outâ€. In a panic I just left. “What will he want me to do? Oh shit is he going to fuck me? Or piss on me or anything elseâ€?
Friday at work I was very worried. I drove to the house and knocked on the door. John opened the door. “Well you did show up, you must want to keep your jobâ€. “I will do whatever it takesâ€. I said back. John escorted me to a large study five older men were there in bathrobes. “Well boys the fluffer is here. Treat him nicely he has never done this beforeâ€. My mind raced. John sat in a chair in the middle of the room and Cindy came in completely Naked. She looked amazing. “Ok your job is to get all my buddies hard. They are going to fuck my wife and while they wait their turns you will suck them off. Simple enoughâ€. I nodded, The men took off their bathrobes and surrounded me. Some had very small cocks some had big cocks. I have never sucked a cock before so I was very nervous. I got on my knees and reached out slowly towards the first one right in front of me. I must have been going to slow. “Come one suck our cocks bitch†One of the men said I could not tell who, as another grabbed my head and shoved his cock in my mouth. I started sucking and licking it when another guy forced his cock in my mouth and laughing pushed the other guy away. I grabbed two other cocks and was trying to jerk them off while sucking every cock I could. Cindy was lubing up when John spoke up. “ok boys she has holes to be filled let’s get this party startedâ€. One guy with a small dick bent Cindy over and started fucking her pussy while a guy with a small dick took her mouth. I in the meantime was sucking off the other three, just trying to do it right. John came ver to me. “lets go suck mine now and lick my balls†I did what my CEO told me. His cock was also very small but I did my best to get him hard. “I want two in my pussy, and one in my ass boys, lets go†Cindy yelled out. John looked at me â€Enough. Take a break and enjoy the show. If anyone starts go get soft get in there and suckâ€. John then watched and the men took her every way possible. She even had two cocks up her ass while sucking another off. John just masturbated and smiled. I have no idea how long they went at it. Soon the moans started and the “I’m cumming!†was being yelled out. I just watched as each of the five men came inside of Cindy and she was laughing. After blowing their loads the men put on their robes and hi fived John. “Next week we are still on†one asked john who nodded. On guy looked at me “next time I’m going to bend you over and fuck your virgin assâ€. I was tired and my jaw was hurting. “Ok now your reward. Clean up my wife. Lick up all the cum from her, let’s go hop to it. Swallow all those loads of cumâ€. Cindy spread her legs wide open, “hope you’re hungryâ€? I licked and licked, and swallowed all the cum I could see. It wasn’t that bad. “Good boy, now one more load. Open your mouth I want to cum inside your mouth, no spitting it outâ€. I started to suck john off and within a minute he came in my mouth. I felt so humiliated. “Great job tonight†he said there is envelope with $5000 in it and the key to the boat house. “Thank you†I said meekly. “Now this is how it will work, you will keep your current job with a nice raise and you can stay here for free. My wife loves to fuck more than I can give her. You will do anything she wants. If she wants to be with ten guys you are to clean up after her. If she wants to peg your ass you let her. If she was to piss all over you, you let her whatever she wants†Cindy interrupted “And If I want you to fuck me you will fuck meâ€. I thanked them and I woke up with a massive hardon.