My story which will start off true in first couple of chapters then will continue with some of my darkest fantasies
My story starts around 15 years ago as a young man living in suburban Sydney. I was 18 years old and still a virgin, although I was desperate for that to change I had major confidence issues.
My problem was I was chubby short received no attention from any girls and knew my cock was small. Even if I could get a woman interested I was sure she would burst out laughing once I dropped my pants. So I was stuck reading adult stories and watching porn wishing I could experience something.
Our next door neighbour for the last few years was a big man called Bill. He was well over 6ft tall, barrel chest, a big stomach and massive hairy arms. We always got along well and I used to be in awe, he seemed to be everything I wasn't. Often I'd see ladies go to his house in the evening. One of those times I was letting the dog out at night and heard some noises. I had watched enough porn to know what I was hearing and stood next to the fence pulled my cock out and came almost instantly. After that I tried to catch him again and did succeed a couple of times. I had no thoughts about Bill, it was always his women I thought about and fantasised it was me making them feel like that.
Everything changed one day when I helped him assemble a pool table he had bought. He had a big room out the back he had converted into a bar. The table was up and I was reaching across the couch when I felt a hand grab my side. I jumped so high I must have nearly hit the roof. I turned to see Bill laughing at me. I was laughing too but said stop that. He asked me why and if someone was ticklish. I tried to deny it but he just held his fingers up and started wiggling them. I burst out laughing and tried to run out of the room but he caught me before I got to the door. He lifted me off my feet, threw me on the couch and started tickling me all over. I was in hysterics and couldn't do anything about it, he was way too strong. He was able to hold both my arms above my head with one hand and used the other to attack my armpits. It felt like torture but I know part of me enjoyed it. Bill was playful and never pushed me to hard and the feeling of him being able to hold me down and control me definitely stirred something inside.
Bill stopped after a while and I just lay on the floor panting. It was then I realised my cock was hard and throbbing. I was hoping to find a way to get Bill to play with it when he started apologising. I told him it was okay but he seemed embarrassed by what had happened. I tried to keep talking but all the playfulness had gone, it seemed more awkward now. I ended up going home and masturbating cumming and starting again. Over the next few days I couldn't stop thinking about what had happened. I seemed constantly horny, was even dreaming about Bill tickling me and would wake up hard and would cum almost instantly. The idea of being tickled by Bill again scared me but I knew I would try and make it happen. Problem was Bill seemed to be avoiding me. I shouted out a couple of times but he just waved and went straight inside.
I became more and more frustrated and decided I would have to go and talk to him. I had been dreaming of him tickling my feet which he didn't touch. I was nervous and kept putting it off but ended up knowing I had to try. I did everything I could think of to tempt him, shower colonge and shorts with no underwear in case I got really lucky. I went to see him and was invited in. We talked again and he kept saying sorry. I told him I thought it was fun and wasn't worried. He laughed and told me I was like a little kid who liked to play tickle monster. I seized the chance and told him he wasn't a very good tickle monster as he didn't touch my feet. Next thing I knew he was grabbing hold of me and ripping off my shoes.
My shoes came off and he ripped off one of my socks before I knew it. I was being held in some sort of hold and couldn't move my legs. His fingers hit my sole and my response was instant. I was howling with laughter, and when he started tickling my toes I was shrieking. I couldn't believe that only a few minutes before I wanted this. I started begging him to stop but he just laughed and said I asked for it. My only relief came when he started sucking on my toes, it still tickled but it made me almost cum. Then he started dragging his teeth down the back of my toes nd that was the worst of all. I was lying face down, legs held tight with my fists pounding on the floor begging him to stop. That's when he mentioned he had the other foot to do next.
I endured it all again and just got hornier as my desperation increased. When he finally finished on my other foot he flipped me onto my back. I could feel my cock standing up in my shorts. Although it is small I knew it was still making a little tent and he would have to notice. He laughed and told me to spread my legs. I felt his hands slide up the inside of my thighs. They slid inside my shorts and just when I was ready for him to touch my cock he started tickling the very top of my inside thighs. I bolted straight up from my back to sitting facing him, grabbed his arms and tried to pull them away but he was too strong. I never thought anything could tickle so bad yet it was also sending shivers thru my whole groin. I begged him to stop but couldn't stop him, I needed the tickling to stop and I was desperate to cum. I felt I was going to pass out.
Finally he grabbed my cock and gave it a squeeze, I started cumming straight away. I had never felt anything like it and he just kept squeezing and pulling. I couldn't believe how much I came, the inside of my shorts were soaked, his hand and my cock were covered in cum and he kept playing with me. I tried to pull away but he just kept going. My cock was so sensitive and I was bucking as he touched me. Soon my cock was hard again, I was moaning and he kept going until I came again.
I went home spent, legs hardly able to support me, shorts looking like I had pissed myself and warm cum slowly dripping down my thighs. Due to me moving to University not long after and Bill moving interstate not long after we only had a few more sessions and most were similar. I tried to push things further, started dreaming of sucking him, even him fucking me but he said he was straight and it was just a game. The day before I left he let me take his cock out and play with it until he came but that was as far as it went. I moved away and part 2 will pick up a few years down the road.
My story starts around 15 years ago as a young man living in suburban Sydney. I was 18 years old and still a virgin, although I was desperate for that to change I had major confidence issues.
My problem was I was chubby short received no attention from any girls and knew my cock was small. Even if I could get a woman interested I was sure she would burst out laughing once I dropped my pants. So I was stuck reading adult stories and watching porn wishing I could experience something.
Our next door neighbour for the last few years was a big man called Bill. He was well over 6ft tall, barrel chest, a big stomach and massive hairy arms. We always got along well and I used to be in awe, he seemed to be everything I wasn't. Often I'd see ladies go to his house in the evening. One of those times I was letting the dog out at night and heard some noises. I had watched enough porn to know what I was hearing and stood next to the fence pulled my cock out and came almost instantly. After that I tried to catch him again and did succeed a couple of times. I had no thoughts about Bill, it was always his women I thought about and fantasised it was me making them feel like that.
Everything changed one day when I helped him assemble a pool table he had bought. He had a big room out the back he had converted into a bar. The table was up and I was reaching across the couch when I felt a hand grab my side. I jumped so high I must have nearly hit the roof. I turned to see Bill laughing at me. I was laughing too but said stop that. He asked me why and if someone was ticklish. I tried to deny it but he just held his fingers up and started wiggling them. I burst out laughing and tried to run out of the room but he caught me before I got to the door. He lifted me off my feet, threw me on the couch and started tickling me all over. I was in hysterics and couldn't do anything about it, he was way too strong. He was able to hold both my arms above my head with one hand and used the other to attack my armpits. It felt like torture but I know part of me enjoyed it. Bill was playful and never pushed me to hard and the feeling of him being able to hold me down and control me definitely stirred something inside.
Bill stopped after a while and I just lay on the floor panting. It was then I realised my cock was hard and throbbing. I was hoping to find a way to get Bill to play with it when he started apologising. I told him it was okay but he seemed embarrassed by what had happened. I tried to keep talking but all the playfulness had gone, it seemed more awkward now. I ended up going home and masturbating cumming and starting again. Over the next few days I couldn't stop thinking about what had happened. I seemed constantly horny, was even dreaming about Bill tickling me and would wake up hard and would cum almost instantly. The idea of being tickled by Bill again scared me but I knew I would try and make it happen. Problem was Bill seemed to be avoiding me. I shouted out a couple of times but he just waved and went straight inside.
I became more and more frustrated and decided I would have to go and talk to him. I had been dreaming of him tickling my feet which he didn't touch. I was nervous and kept putting it off but ended up knowing I had to try. I did everything I could think of to tempt him, shower colonge and shorts with no underwear in case I got really lucky. I went to see him and was invited in. We talked again and he kept saying sorry. I told him I thought it was fun and wasn't worried. He laughed and told me I was like a little kid who liked to play tickle monster. I seized the chance and told him he wasn't a very good tickle monster as he didn't touch my feet. Next thing I knew he was grabbing hold of me and ripping off my shoes.
My shoes came off and he ripped off one of my socks before I knew it. I was being held in some sort of hold and couldn't move my legs. His fingers hit my sole and my response was instant. I was howling with laughter, and when he started tickling my toes I was shrieking. I couldn't believe that only a few minutes before I wanted this. I started begging him to stop but he just laughed and said I asked for it. My only relief came when he started sucking on my toes, it still tickled but it made me almost cum. Then he started dragging his teeth down the back of my toes nd that was the worst of all. I was lying face down, legs held tight with my fists pounding on the floor begging him to stop. That's when he mentioned he had the other foot to do next.
I endured it all again and just got hornier as my desperation increased. When he finally finished on my other foot he flipped me onto my back. I could feel my cock standing up in my shorts. Although it is small I knew it was still making a little tent and he would have to notice. He laughed and told me to spread my legs. I felt his hands slide up the inside of my thighs. They slid inside my shorts and just when I was ready for him to touch my cock he started tickling the very top of my inside thighs. I bolted straight up from my back to sitting facing him, grabbed his arms and tried to pull them away but he was too strong. I never thought anything could tickle so bad yet it was also sending shivers thru my whole groin. I begged him to stop but couldn't stop him, I needed the tickling to stop and I was desperate to cum. I felt I was going to pass out.
Finally he grabbed my cock and gave it a squeeze, I started cumming straight away. I had never felt anything like it and he just kept squeezing and pulling. I couldn't believe how much I came, the inside of my shorts were soaked, his hand and my cock were covered in cum and he kept playing with me. I tried to pull away but he just kept going. My cock was so sensitive and I was bucking as he touched me. Soon my cock was hard again, I was moaning and he kept going until I came again.
I went home spent, legs hardly able to support me, shorts looking like I had pissed myself and warm cum slowly dripping down my thighs. Due to me moving to University not long after and Bill moving interstate not long after we only had a few more sessions and most were similar. I tried to push things further, started dreaming of sucking him, even him fucking me but he said he was straight and it was just a game. The day before I left he let me take his cock out and play with it until he came but that was as far as it went. I moved away and part 2 will pick up a few years down the road.
