Ouch My Assbywhooper©
My name is Bob. I have never considered myself to be gay at all. However, I would occasionally glance at other guys and wonder. Well, one day I found out what it was like to be gay. I am about 5'9" brown hair, green eyes and 31 years old. My dick is about 8" long, 3 inches wide and I have a strong sex drive. I had been eyeing my boss for a while, his name was Jay. Jay is about 24 years old but looks no more than 18 years old. Jay has boyish good looks, a little shorter than me and about 20 pounds lighter than me, which would make him about 130 pounds. Jay also has blonde hair blue eyes and a very good since of humor.
One day I told him to come by after work, my wife had left me and I needed someone to talk to. Well, he came by and we started talking. I asked him why he made a lot of gay jokes and why they were always aimed at me. He assured me that I was taking him too serious. Then I decided screw it lets take this farther. I told him that I was curious about homo sex and asked if I could suck his dick. He protested, telling me to stay away from him, that I was a fag. I explained I was just curious about gay sex and that there was no better to find out than try it. He protested saying that there was no way he was sucking my dick. I assured Jay that I wanted to try it that he didn't have to participate. I also said "I tell you what, let me suck your dick, you get a nut no strings or obligation. And that if he could hold out for 10 minutes I wouldn't expect him to return any favors. But if he blew his load before the 10 minutes was up, he had to get me off also. He said ok but that he wasn't going to touch my dick and that he had enough stamina to hold out for 10 minutes.
Jay pulled down his pants and to my surprise, he was a boyish guy with a man dick! His dick was 10 inches long and almost as big around a coke can! And fully erect. Yeah, he didn't want me to touch him….right. I but my hand around his dick and drew it into my mouth, the taste of is smooth soft dick was better than I ever expected. I had never been this turned on. I didn't think I could get the thing in my mouth, but the first insertion I took about 5 inch in and started to pull back off of it. I was stopped by his hands behind my head. His dick was touching the back of my throat as it was and he wanted me to take it all? How? He held his dick in my mouth for a minutes and I eventually had to swallow saliva around his massive tool. When I did, he forced the rest of his cock down my throat gagging me, I could hardly breathe.
Then for the next few minutes he face fucked me like a wet pussy. His dick tasted better than any candy I had ever tasted. He eventually blew his load down my throat and kept pumping for a few more seconds, not even going limp. My first taste of cum was not disappointing it was think sweet liquid and I think I am addicted now. But he screwed up! He forgot about the clock and at the 8 minute marker he blew his load! NOW HE HAD TO GET ME OFF! When I told him it was my turn he said there was no way in hell he was putting his hands or mouth on my dick…that I would have to fuck him in the ass. My mouth hit the floor! He told me to make it fast and quick, that he had never been fucked in the ass and that he knew it was going to hurt but that he could take the pain if I would hurry and blow my load.
I reached into the nightstand and pulled out some lotion…applied it to my dick and put my dick to his hole. I pushed forward and nothing…it wouldn't go in. I continued for about 5 minutes to try and get my dick to go in and finally I penetrated his ring…he screamed like a little bitch! And I was only about 2 inches in him….he pleaded for me to wait a second. So, I gave him about one minute to adjust to my dick then slammed the other 6 inches in and held it there for a second, the hold time he was screaming! I told him scream all he wanted but to put his head in the pillow and I would be as quick as I could. I started fucking his ass like a madman! It grabbed my dick so tight, I wanted this to last forever. I guess he had got used to my dick because now instead of screaming he was moaning and pushing back to meet my thrusts, making our balls touch a bit with each thrust! I reached around as I pumped his ass to find that the dick that had been limp from the pain was now raging and thicker than when it was in my mouth! WOW! Jay's ass was clinching my as so hard I didn't last much longer and I blew my load deep in his bowels.
Jay said, now I want to fuck you! Jay demanded for me to lay on my stomach. I hesitated because his dick was much longer and thicker than mine…and my ass was a virgin too. I lay there on my stomach scared as hell that he would rip my poor ass ring apart! But that isn't what happened. After a lot of lube and some quick hard pokes his purple headed read skinned cock made it thru the ring of my ass. It hurt like hell! He pushed a little of his dick in waited for me to adjust and did this about 5 times, every time plunging a little further into my virgin ass. I was wondering how much longer it was going to take for him to be fully inserted into my ass…. I thought he was never going to run out of dick. I asked how much was in me and he replied that only half of his dick was in me. I started to panic, I already felt like a telephone pole was up my ass. I told him just to get it over with. He then pushed with all his weight slapping his nuts up against my ass. Jay was finally completely balls deep into my ass, AND IT HURT!
Jay started to pump my ass like there was no tomorrow. IN , out , IN , out. Having already blown his load once jay was working my ass like there was no tomorrow, moaning, but showed no signs of letting up. Then the weirdest thing happened, all the pain turned into pleasure….making my cock pulse , as it was pinned between my stomach and the sheets. I blew 2 loads while he pounded my ass for almost 2 hours. He fucked like a stallion for the complete time, never letting up. I was about to cum again when he blew his load deep in my ass, but he pulled out with a slurping plop and just layed there for a second. I complained that damn it , I was about to come again. Jay smiled , leaned over and took my cock in his mouth. Here I was getting blown by my boss! That was the best blow Job I had ever had! He stayed a while and blew him a few more times.
The next day at work was hilarious, I could barely walk, and he was walking a little funny himself. =) Later that day I let him bend me over a stack of milk crates in the back, yet again pumping his 10 inch fuck stick all the way up my soar ass. And then later I gave him a blowjob in his office! He pumped my face hard and strong hurrying so not to get caught. I didn't care, I loved that sweet liquid. I ended up jacking off in the bathroom after each encounter. Needless to say I am the bosses favorite employee. And he is my favorite boss!