I lost this week's challenge so as punishment I have to post for 5 days on a subject of Her choosing. She decided the post name and topic then I must be a good boy and do as I'm told.
This story is one of my first positive experiences being a sub, it was back when I was in University and I decided that I wanted to explore more about myself sexually, this was also one of my sexual experiences with a man.
I forget where I met them but we had been chatting to each other for a while, started off as mundane things to what we were both looking for. I was honest and stated that I was looking to explore and try different things. It started off online, with him giving me different tasks or challenges to take me out of my confort zone and to try and find new things I liked and things I didn't like.
One of the first things I discovered that I enjoyed was edging, and pretty quickly it was decided that if I wanted to cum, I ALWAYS had to ask for permission. Sometimes he would let me, sometimes I wasn't allowed to but each night I would have to masturbate (for how long it would vary day to day). It continued like this for some time before we eventually decided to meet. We met at a bar so there we could both be sure we wanted to continue and if not, there were no hard feelings.
We went back to the hotel that he had booked for the night, were I was ordered to strip naked and he walked around looking at me and made several comments about my body, after he finished that he asked me to help him out of his clothes before getting on my knees and proceeding to give him a blowjob, I wasn't allowed to touch myself and I wasn't allowed to cum unless I asked for permission. We didn't rush anything and took our time, he came a couple of times, but I had yet to cum despite asking for permission, he eventually put me on my back and started to prepare my ass so that he could fuck me. Whilst he was doing that he told me to take myself to the edge, but not to cum. Once I was on the edge, he slowly eased into my ass and let me adjust to him, once I had gotten adjusted, he started to move slowly, at this point I was so desperate to cum that I begged him and he let me. That was the hardest I had cum, legs shaking but thorougly relaxed. The night didn't end there ;)