I had just graduated high school and was looking to earn some money for my up coming departure for college. One of the first things I did for work was to put up a flyer in a few of the local stores advertising myself as a handyman. I was not the biggest guy at 5'8" and 150 lbs but if there was something I could not do I would tell the prospective client. I also made sure to include my picture on the flyer so everyone could see I was the boy next door.
I was getting a few calls from older folks who wanted some yard work done or things moved in their houses or apartments. I was making a few dollars and was happy to be helping people.
One day I got a call from a guy named Christopher. He said he had seen my flyer at the store and wanted me to do some things around his place for him. I made an appointment and went by his place at 3:00 on a Wednesday afternoon. His place was beautiful, it was an old Victorian with a manicured lawn and some really nice gardening. I went up to ring the bell and noticed a note telling me to go around back, and meet him by the pool. I found the gate and wound my way down a path to his very nice backyard. I saw a guy floating on a raft in the middle of the pool so I walked over and said hello. He said he was Christopher and he swam over to the side of the pool, and got out wearing a very small bathing suit. He got out and shook my hand while apologizing for being in the pool. My first thought was that he was obviously gay. He was fairly effeminate in his mannerisms and was obvious about it.
He was around 40 or so. He was taller then me by a head, I would say he was 6'3" tall and he was very thin, but defined. He looked like he swam a lot of laps in his pool. He had pierced ears, and very blonde hair, he also had a very bushy mustache that covered his lip. I also noticed that the front of his bathing suit was straining to hold in his cock and balls. He looked to be hung like a horse.
He asked me to sit at a table under an umbrella while he put a robe on. He came over and offered me some iced tea, I said sure and he went to get it. He returned with the tea and with his robe done up. I guess he thought he was making me uncomfortable. He sat down and lit a cigarette and made his proposal. He said his pool company was very unreliable and he wanted to make a change. He took a drag of the cigarette and went on. He wanted to know if I would like to take care of his pool for him. He said he would pay me $100 cash a week to vacuum it and keep it clean. All in all he thought I would spend about 1 hour a day there. I said yes immediately. To know I was starting out each week at $100 was a big win for me. He said great and asked me to start the next day. He showed me where the equipment was and how to use it. Then we shook hands and off I went.
I got to his place at around 3 the next day, he had asked me to do the work in the afternoons as this was the best time to see things in the very shady yard. I had done all the work in the pool area when Christopher walked out of the house is his robe with a glass of iced tea again. He left it on the table and said he was going swimming. Again he had on a very revealing bathing suit, and again his cock and balls were barely being contained in the fabric of the suit.
I sat down and drank my iced tea while he expertly swam so laps. He was obviously a very good swimmer as he cut through the water with ease. He got out just as I was finishing my tea and came over to the table. This time he did not put his robe on....he sat down next to me and grabbed my empty glass and sucked on an ice cube. I looked away a little embarrassed at the provocative nature of that. He took out a cigarette and asked me for a light. I said I did not have any matches but he pointed to some on the table. I got a match lit and held it out. He leaned in and grabbed my hand and lit his smoke. I could not help myself and looked down at his suit and could definitely make out his cock through the thin fabric. He blew the smoke up into the air and lamented his bad habit. He said he wished he could quit but he still liked the little rush it gave him. Plus he said he thought it made him look sexy. To prove that point he took a very flamboyant drag and release. I laughed and excused myself, saying I had to be somewhere.
Christopher continued to be friendly to me but I had not spent any time talking to him in a couple of weeks. There was always a glass of water or iced tea waiting for me but he maintained his distance. I think he thought I did not like the way he acted. In truth I had found him as sexy as he thought. I had not done anything with any other guys yet, but I had found myself thinking about it even before I met Christopher. I had even found myself thinking about the huge cock he hid in his bathing suit.
He left me a message saying he was going to be out of town for a few days and to continue the work. If I wanted to jump in the pool when I was done go ahead. I did jump in once and it was nice, it was so private you thought you were miles from your nearest neighbor, when in reality they were right next door. So since I was all alone I took off my shorts and jumped in naked. I swam around for about 10 minutes enjoying the feeling of freedom swimming around in the buff. I got out and sat at the table. I noticed he had left his cigarettes on the table so I helped myself to one. I had not smoked before though and coughed when I tried, so I put it out. Between the skinny dip and the attempt at smoking I found myself pretty turned on. So I looked around and knowing no one could see me, I jerked off. I was thinking about Christopher when I did it, and I shot a huge load when I came, it felt great. I cleaned up my spunk and left.
Christopher called and said he was back in town, and that I had done a great job while he was gone. I thanked him and said I had gone swimming once. He said he knew that, he had a security system that recorded everything in the backyard. I was speechless. He laughed and asked me if I was still there. I said yes and apologized profusely. He told me not to worry, my secret was safe with him, and he told me he had watched a few times himself before he erased it. I said sorry again and thanked him for erasing it. No problem he told me. He was having some company over the next few days so please make sure I kept up on things.
I showed up at 3 the next day. This was my usual time. Remembering that Christopher had company I knocked on the door. There was no answer so I walked around back. As I reached the gate I heard two people talking. I did not want to interrupt the conversation so I quietly retrieved the equipment behind the pool house. As I rounded the corner to begin my work I saw something incredible. There was Christopher standing on the side of the pool, and in front of him was a guy sucking his cock. Christopher had his hands on his hips and was slamming his cock into the guys mouth. I could not believe what I was seeing. Christopher's cock was huge, and every time he thrust into the guys mouth his balls swung like a pendulum. The guy on his knees obviously knew what he was doing. Christopher was now literally fucking his mouth. I could hear him trying to keep up with the pace Christopher was setting when all of a sudden Christopher pulled out and shot rope after rope of cum onto the guys face. The guy was doing everything he could to keep up with the huge load being shot on his face and into his mouth. I was furiously rubbing my own cock through my shorts at this point.
Finally it subsided. Christopher walked over to the table and sat down. He lit a cigarette and the guy who had blown him walked over and put his semi hard cock in his mouth and continued to suck it. He was paying special attention to the tip. I noticed Christopher was uncircumcised and the guy obviously enjoying finishing his work. He was jerking on a pretty big cock himself, and he shot his load all over the ground in front of Christopher. All the time Christopher just sat there playing with the guys hair, just letting him service his huge appendage.
Finally they finished and they both jumped into the pool. At that point I pretended to arrive at the house. I thought to myself that what I had seen was no accident. He knew what time I came each day, that was all for me. I walked out with the equipment and pretended to be surprised that there were people in the pool. What was even more surprising was they were in the middle of an embrace when I turned the corner, and the were both still naked.
Christopher quickly broke the embrace and apologized for what I had seen. He climbed out of the pool and walked to get his robe. His ponderous cock swinging in front of him. He smiled at me and said they would go inside while I did my work. He put his robe on and he called his friend out of the pool. He walked out naked and went over to get his towel. It was then that I noticed how much the guy looked like me. He stopped on the way to the table and introduced himself to me as Edward. He stood there naked and said in a very surprised voice why we could be brothers. He wrapped his towel around his waist and semi hard cock and walked hand in hand inside. I looked at the pavement on the side of the
Pool and I could see where Christopher's cum had overflowed Edwards mouth. I also saw the puddle of cum where Edward had cum while he was sucking Christopher's cock.
I was just finishing up, and was putting the equipment away when Christopher called to me. I put everything away and met him at the table. I had hosed away the cum that was on the side of the pool as well as doing the rest of my work. Christopher had a glass of water for me. He had put on a t shirt and sweat pants, I could make out his huge cock through the pants. He definitely saw me glancing at the front of his pants.
He lit a cigarette and pushed the pack towards me. I said no thanks. He took a drag and blew the smoke at me. I kind of inhaled a bit as the cloud passed me. He apologized for me walking in on them. He then told me what Edward had said about us looking alike. I said it was true. We did look alike. He agreed and said I was definitely his type. That was why he called my number when he saw the flyer. He was not sure how it would turn out, but I was a good worker so it did not matter to him. But he had noticed a few things, I was always trying to get a look at his bulge. I tried to deny this, but he just laughed and blew some more smoke at me. He also said it seemed I was attracted to him. He asked if I was. I said I was confused. I was appreciative of him for the job, I felt I owed him an honest answer. I said I was not sure, I told him I had some feelings for him but I was scared by them. I told him I did not think I was gay, but I had watched him get his cock sucked. I also told him it was him I was thinking about when I jerked off while he was away. More then anything I told him I was confused.
He told me it was natural to be confused about what I was feeling. He said he had felt the same way I had when he was younger. He told me an older man had brought him home one day and had relived his stress about his sexuality. He told me if I wanted anything from him to let him know. He put out his cigarette and went inside.
He called me the next day and asked if I was alright. I said yes, then told him I had actually seen him and Edward doing a lot more then simply embracing, I had seen the blow job. He told me he knew that. He had purposely set it up so I would see that. So I would see him with another man. So I would know what would happen if I wanted to continue. He said he had wanted me from the first time he had seen me. If he had his way he knew he wanted me, it was just a question of if I wanted him. He said he liked younger guys, he also asked me if I liked older guys. He pointed out that he was twice as old as I was.
I told him I really had not thought that much about men until I met him. He had somehow managed to get me think of another guy in ways I really never had before. He then said something that rang very true. He told me he had seduced me.
That had a very sexual undertone to it. Yet I knew it was true. He had seduced me. Now he said it was up to me. If I wanted to pursue it he would love to be the first. If not he was content just being friends.
I asked for a couple of days to think about it. I continued to work at the house. I hoped I would see him at the pool or elsewhere but he was not around. I think it was to give me space to make my decision. There was always a glass of water at the table but I did not see him. Yet he was all I could think about.
Finally I went to clean the pool on an overcast day. I had decided that he was the one. As I arrived he was sitting up on the deck away from the pool. He was smoking a cigarette and drinking a glass of wine. I put down my equipment and walked towards him he looked at me with a question in eyes. I walked up to him and leaned over and kissed him on the mouth. I could taste both the wine and the cigarette as he gently pushed his tongue into my mouth. I was being kissed by another man, a man who admitted to trying to seduce me since the first time he had seen me. He pulled me onto his lap and continued kissing me, he was very gentle with me but there was a definite passion in him as well. I on the other hand was starting to enjoy myself. I think he was going slowly to let me acclimate myself to everything. I think he purposely went slowly so as not to scare me off .
I suddenly realized how strong he was. He pulled my mouth onto his and began to aggressively kiss me. I was beginning to get caught up in the moment. I returned his kisses with the intensity he was giving me. I could feel his huge cock starting to stir under my ass he suggested we go inside.
We made our way to his bedroom. It was large with a huge bed set in the middle of the room. There were silk ties attached to the posts and several large dildos on the night table. He turned me around as we walked into his room. He was a bit different now that I was inside. He again kissed me, this time he shoved his tongue into my throat and he growled in his throat, his thick mustache was rough on my lips and face. He licked my face and sucked on my neck. He wrapped his arms around me and pulled me into him. I was enjoying the fact that he was taller then me, I enjoyed looking up at him when we kissed. I could feel his cock as well. This was something I had thought about for a long time. I snaked a hand down between us and ran it down his length. It was soft and big, it was probably already bigger then my 6 inches and thick as a large keilbasa.
He walked me over and sat me on the edge of his bed. He stepped back and kicked off his shoes. He was wearing a pair of linen pants that were tenting due to his cock. They had a draw string which he undid. He slowly lowered the pants to the ground. I was stunned. His cock was absolutely huge. It was semi hard but was nestled over his huge ball sack. I could see his foreskin gathered up at the tip of his cock and it looked an inch long. He took off his shirt and stood in front of me. I knew he was doing it so I would either stay or go. The literal enormity of what I was about to do was 2 feet in front of me. I slowly reached out both of my hands and lifted his cock off his balls. It was heavy in my hands. I gently pulled back his skin and exposed the huge cock head. I loved the way his skin slid so smoothly over and off his cock. I moved my left hand under his cock and hefted his huge balls. The had to be as big as eggs, and his sack let them hang low. They were covered in a light blonde fur, the same fur that ran from his pubic area up to his belly button.
He took the cock from my hand and stepped towards me. He put the tip on my lips. I hesitantly put out my tongue and licked his gathered foreskin. He moaned and continued to hold himself in front of my mouth.
"Open your mouth," he told me.
I did and after pulling back his skin he pushed his cock head into my mouth. I had to stretch my jaws around it, as it was starting to get hard. He pushed into my mouth a few times. The taste was hard to describe. There was a definite tang, I think from being uncut, but there was also the musty manly smell one has around their cock and balls. He told me to go slow. There was plenty of time. He put his hand on the back of my head and shoved that cock into my mouth again. I gagged as it closed off my airway. He pulled it out and held it out and told me to lick it. I started up by his sparse pubic patch and worked my way up and down his length. All the time he kept telling me to look at him. So my tongue was working his foreskin inside and out as I looked into his eyes. He reached forward and gently pinched my right nipple. I was surprised at how good that felt. He continued to work on my nipples as I learned my way around his bull cock. He then removed it from my mouth and pulled my face into his balls. My nose was right between the pair as I stuck my tongue out and started to luck them. The light hair was almost invisible but I could feel it under my tongue as I got his ball sack coated with my spit. He obviously enjoyed this because his cock had reached scary proportions. At this point it had to 10" long and was so thick I was barely able to get my hand around it, it was also hard as a rock.
He told me to get up and when I did he again gave me some very passionate kisses. I could tell he liked kissing, he was very good at it and I could feel my cock in my pants. He sat down on the bed and ordered me to get undressed. I did as I was told. First I took off my shirt, when I did he pulled me over to him and began to work over my nipples. I could not believe how good it felt. He stared licking them, then graduated to nibbling on them. Always moving between the two. Then he bit them harder, I gasped but he continued. It hurt but it had also started to feel good. He looked ip at me and asked if it hurt. I said yes but I kind of liked it. He smiled and said alot of what we are going to do tonight is going to both hurt you and feel good, the question is can you get through the pain and reach the pleasure. I was starting to realize what he talking about. He told me to continue getting undressed. I took off my shorts and he reached out and stroked my rock hard cock.
" I think you are enjoying yourself", he said.
Then he leaned forward and engulfed my cock in one movement. I almost passed out. He had taken my whole cock down his throat in one shot. I told him I was going to cum but he just sucked harder. Then I came like I never had before. I thought I was going to fall down my knees got so weak. He continued to suck my cock until it was done leaking. I was in heaven. He had given me the best blowjob I had ever had, there were only 2 before that.
He said now that we have that out of the way we an really start to try things out.
I took the lead at that point. I got on my knees in front of him and slowly started to try to suck his huge cock. He was giving me instructions on how he liked it. He did not like me to use my hands at all. He said he wanted to see my mouth stretched around his cock. I tried to get as much of it into my mouth as I could but I kept gagging. He was starting to talk dirty to me, and I could tell he was getting off on it.
"Suck that fucking cock boy. You like that big cock don't you boy. Lick my fucking balls boy."
His cock was hard as a rock, he stood up and started to really fuck my face. I was only getting about a third of it in my mouth but it was huge progress from where we started. He would pull out every now and then and tell me to suck his skin. I would gather his fore up and suck on it. He definitely enjoyed that. Suddenly he told me to get on the bed. I laid my head up by the pillows as he walked over to the nightstand and picked up a dildo. It was large. Not as large as him but still. It was long and black. He told me to roll on to my stomach. I was very nervous with him back there and told him so. He told me to remember what he had said about pleasure and pain. I did remember. He turned my face towards him and gave me another one of his kisses. Then he disappeared from my view.
When I came over to Christopher's I knew what could have happened. Things were definitely moving quicker then I had anticipated. I was about to tell him to stop when I felt him blow on my asshole. It was just him blowing some air on my ass but I gasped. Then I felt him spread my ass cheeks and kiss my hole. He mumbled something and then he started to lick my crack, still only blowing on my hole. He licked everywhere around it. It was driving me nuts. I could feel hit spit running down my ass crack and onto my balls. Finally when I thought I could not take it any more he lightly brushed my asshole with his tongue. I moaned as loud as I ever have. He then started to work my asshole over with his mouth. He was kissing it, and licking it, and shoving his tongue up me. I could feel that my cock was as hard as a rock again as he ravaged my asshole with his mouth.
I was in heaven when he slipped his first finger into me. I was surprised but he had loosened me up with his tongue so it was not at all unpleasant. He continued to work my hole with his tongue as he slowly started to finger fuck my tight ass. Then he put another finger in, now it was a bit uncomfortable. He could no longer get his mouth on my hole so he slowly stretched me out with his 2 fingers. I felt him pull them out slowly and he again started on my ass with his mouth. I could feel his tongue in a bit deeper then before so I guess his fingers had done the trick.
I had my face on the pillow when he pushed the big black dildo in my face and told me to suck it. I was at the point where I would do anything he asked me to so I gave that big black dildo the best blow job I could. All the while he continued to work over my ass. I had gotten the dildo soaked with my saliva when he pulled it away from me. He came up next to me and gently rubbed my back. I felt the tip of the dildo push against my asshole. The pressure was severe. He slowly worked in the head till it got past my ring. I was in alot of pain. He never stopped moving the dildo though. I had tears running down my face as he ever so slowly worked more and more of the black plastic Dick into my ass. He would get it further in and then work it in and out from there. It took a while but at last I could feel his fingers where they held the dildo. I was not enjoying myself at that point. He slowly started to work the dildo in and out of my ass more and more each time. He was also increasing the intensity of it. He told me to roll onto my back at that point. He had me grab my ankles as I laid on my back. He then started to slam the dildo into my ass. It hurt like hell, but he did not stop. My cock was rock hard again as I watched the dildo sliding in and out of me. Then he pulled out and put the tip of his cock on my ass and shoved in. I screamed in pain. It was only the tip but it was definitely much bigger then the dildo. He told me to relax and started to move into me. He went slowly and every time I thought I was used to him he would put more in, and I would be in agony all over again. He was leaning over me and kissing me intensely. It was definitely making everything easier. Then he pulled me over to the edge of the bed. He stood up and I looked down. He had gotten himself about halfway in. I could not believe it, he had been fucking me for about 20 minutes and he was only half way in. He took out a tube of lube and squirted some more on his dick. And a bit onto my hole. Then he started to go in and out. Till then it had been him slowly introducing his cock into my ass, now he was starting to fuck me. I was in alot of pain but he was getting deeper and deeper. He told me he could not believe how much of his cock I had taken, as he worked more and more into me. In and out. He again leaned in and started kissing me. He was covered in a light layer of sweat which I licked off his chest. I then reached up and pinched his nipples. He went crazy. He slammed the last bit of his cock into me, I felt his huge balls against my ass as he gyrated that Monster into my guts. I had my hands on his hips trying to push him out. Then he told me he was going to fuck me now. He started pulling out and slamming back in. I tried to get him to stop but that only made him go harder. I was in tears begging him to stop as he fucked me as hard as he could. I do not know at what point it happened but it did not hurt as much. I felt myself starting to rise to meet him on his strokes. I could feel his huge balls actually bouncing off my ass. He was going into me like a piston. He told me he was going to cum...he completely removed his cock from my ass in one shot and pulled my face up. He put the tip of his cock into my mouth and shot load after load of cum all over my face. It was in my mouth my nose my eyes my hair. I reached my fingers up and gathered it everywhere and licked it off my fingers. I then put his semi hard dick in my mouth and drained the rest of him and his fore. He stood there smiling and sweating as I licked his cock and balls. He leaned in and gave me another kiss, this one was the best yet, it was slow and sexy, as he licked whatever of his cum I missed and passed it to me with is mouth.
He reached into his drawer and took out a cigarette. He lit it and drew a hit of smoke. He blew it to the ceiling and then he put it in my mouth and I did the same. I could feel how stretched out my ass was. I asked him if he would fuck me again before I went home for the night. He kissed me on the mouth and said of course I will fuck you again you little fag.