Personal Ad Leads To My First BDSM

True story

First off, I would like to say that I have never written any erotic stories before. This story is true, and hopefully it will be the first installment in a multipart series of my adventures as a BDSM submissive.

I am a 50 year old married white male. I am new to bi and new to being submissive. I did have a friend in high school (which was a long time ago) whom I played with a couple of times, but I always attributed that more to alcohol than being gay or bi.

Since then, I have never done anything with a man. Sure, I have thought about it - a lot. I have fantasized about being submissive to a man. I have also fantasized about BDSM as a sub. I have read and responded to many gay personal ads for this, mainly on Craigslist. I have even posted a few ads. I have met a few guys in person to chat with about this, but everyone I met or talked with seemed too hardcore and extreme for me, so I have never acted on my desires.

I had pretty much given up on ever being able to fulfill my gay submissive BDSM fantasies, so I placed an ad just seeking a man who I could meet to get naked with and touch and jack with. I figured this would be a safe way to at least explore my bi side.

As usual with Craigslist, I got a lot of really strange responses. But I did get one response from a guy who sounded like he understood my nervousness about exploring bi. Jack said he was in his late 50s, lived alone and could host during the day (which is the only time I can get away to meet). After a few emails, we decided to meet. Jack gave me his address and phone number. I was relieved that Jack lives about 20 minutes away from my house, so if things were weird I would probably never run into him, especially when I am with my wife. I was also happy that Jack lives in a nice area of town.

I drove to Jack's condo and parked outside. I was thinking to myself "This is crazy, just go home". But my curiosity overcame my fears and I went into the atrium lobby. Jack was waiting on the third floor and called down telling me to come up.

I rode the elevator up, becoming more nervous by the second. As soon as I met Jack, he shook my hand and I was almost instantly at ease. We went into his condo and he led me to his bedroom. We made some small talk, some of which was sexual and some of which was not. Jack put in a gay porn DVD and we sat on the edge of his bed. Jack told me that I did not have to do anything and to just be comfortable.

Jack then took off his clothes and laid back on the bed. I looked at Jack and noticed that his cock was somewhat larger and thicker than mine (I am about 5 ½" long and average thickness). Jack also had a huge mushroom head on his cock.

After a few minutes, I relaxed more and took off my clothes. I laid back on the bed next to Jack. We were just watching the porn. I was becoming excited and rubbed my cock. Then I reached over and fondled Jack's cock. I liked the feel of it, and was surprised at how quickly he started leaking pre-cum. Jack started rubbing my cock while I rubbed his.

Jack told me about a couple of his other male friends. He mentioned that one of them liked to be restrained and liked to be spanked and have clothespins used on him. I didn't say anything because I had not given Jack any indication of my submissive fantasies, but I had butterflies in my stomach thinking that maybe I had found the right man to explore this with.

We continued rubbing each other's cocks for a while. Unfortunately it was getting late and close to the time I had to leave to get home to get my son off his school bus.

I decided to risk having Jack think I was weird and I told Jack that I had fantasized about being restrained and was curious to see what devices he used. Jack leaned down to the foot of the bed and brought up Velcro handcuffs (footcuffs?) attached to a rope which was tied to the bed rail. I was really surprised I had not noticed them before that, but I had been pretty nervous.

Jack asked whether I would like to try them, which I readily agreed to. Jack was very gentle as he placed my two legs in the Velcro restraints and drew them tighter to the bedrails, causing my legs to be spread apart. At this point my hands were still free and I could easily reach down and unfasten my ankles if I desired to do so. Jack asked if I would like to try having my wrists bound, too. I was a little apprehensive, but I agreed. Soon my two wrists were bound and the ropes pulled tight so that my arms were spread. I could not believe that I had allowed a stranger to tie me up and make me completely helpless. I realized that Jack could do anything he wanted to me now and I would not be able to stop him. The thought of being completely at his mercy caused me to immediately get as hard as a rock. I noticed that Jack was also getting very hard now.

Jack asked whether I wanted to try the clothespins. I said "Sure, especially since I can't stop you". Jack assured me that he would not do anything I did not want him to. Jack them placed a clothespin on each of my nipples. I have never had sensitive nipples and never really liked to have them played with, but the pain of the clothespins on my nipples was incredibly exciting – it hurt but I loved it. Jack then placed 3 or 4 clothespins on my scrotum. The pain from that was not as intense, but I enjoyed it almost as much.

Jack began stroking my cock and he could tell I was loving it. It did not take long for me to cum. It was one of the most intense orgasms I have ever had. After I came, Jack removed the clothespins and unfastened the restraints. The pain of having the clothespins removed from my nipples was exquisite. Jack went to the bathroom and brought me a warm wet washcloth to clean up with and a towel to dry with.

I thanked jack and got dressed. I left and was able to get home to get my son off the bus with a few minutes to spare.

I have emailed Jack several times, thanking him for the experience. We have since talked about several things we can explore next time, like using a blindfold and a collar and lead, spanking, using a small dildo on me, etc. I have told Jack about my desires to be submissive and to further explore bondage.

Jack has told me to address him as "Master" or "Sir" from now on. Even though I don't really know Jack that well, I feel a great deal of trust and I am eager to be able to expand my experiences with him. I told Jack ("Sir") that within the limits he and I have discussed, I will be his to use as he sees fit when we play. Jack and I have another session planned for Wednesday, so hopefully I will have a second chapter to this story quite soon.