First time
Many years ago, I found an ad on Craigslist about a guy wanting to use a young man for his pleasure. I replied and told the guy what I was into. We agreed to meet at his place. I put on my chastity cage and a cute little teddy, regular clothes over top. I drive over to his apartment building and was so nervous I say in the parking lot for a few minutes before I worked up the courage to go in. I knocked and he said to come on in. I did so and shut the door behind me. He was in another room and said for me to strip at the door. I did so and then he said to go into the living room and wait there. I did in the living room and watched this older chubby guy come out of the bedroom in just a pair of boxers. He took one look at me and ordered me down on my knees. I complied quickly. He sat on the couch legs spread wide and said stand up and turn around. His hands were all over me. He then ordered me to strip naked, said he didn't like sissies. I did and got back down on my knees, legs spread wide so he could inspect my cage. He got up went over to my clothes and fished around until he got the keys to my cage. He came back and switched my lock for one of his. After that was done he say back down on the couch and said to get to it. I reached for his cock, but he slapped my hands and told me no hands. While I fished around for his cock with my mouth, he turned on Jeopardy. I had never seen another man's cock as fat as his was. I remember the salty sweet taste of his precum, as I licked, kisses and sucked. After what must have been a half for her ordered me to get back on my knees. He played with my nipples and balls, while slowly stepping his fat cock. I warned him I was close and he kept on. As my orgasm approached my hand automatically went under my cage and caught my cum as it drained out while he played roughly with my nipples. He was disappointed and told me I had earned a week in the cage for that lack of control. He wanted to see me eat my load of cum. I showed him my hand and slurped it down. He then had me get back to his cock. After a while he said to just open my mouth and be ready, as he began to jerk off. When he finally came I swapped out all like a good sissy. The taste was morning like my watery cum, but was salty and bitter, but oh so good. He grabbed a paddle from his bedroom and gave me three whack for teeth grabbing his cock three times, his fat cock bobbing the whole time. He ordered me out and said come back next Saturday for more training.
I went home that afternoon and finally cut off the plastic pin the lock was attached to and jerked off properly. I was so horny I had two more orgasms that night. I wouldn't go back to him again for another 2 years, but I often jerk off thinking of that experience.
Posted Nov 1, 2023, 3:55 PM UTC