Real Craigslist Encounters: Uncovering the Unexpected World of Online Connections and BDSM

The 5% of the time a Craigslist Post is Real


How many of us have either answered a Craigslist Post or had the nerve to post an ad looking for some sex. To be honest I cannot tell you how many I have answered only to find out it is a dead end or someone trying to get me to sign up on some adult web site in order to chat. Taking it a step further you trade a few emails and you find out that the person is nothing like they said in their post.


I did finally find someone who had very similar thoughts and desires so we decided to meet. He was a year younger than me, divorced and living alone about 4 miles from my home.

The first two visits went just as we discussed. It began with some idle chat while drinking a soft drink. The conversation then moved to the subject at hand – sex! He took me into his bedroom and asked what kind of porn I wanted on the TV. The first time I said straight porn, it ended up being two couples engaged in some very straight sex. Both females had good bodies with average tits and great butts and the guys again were average in size.

As I stood there watching Paul came up behind me, gave me a hug and began to rub my back. Slowly he moved down and gently rubbed my butt then reached and found my semi-hard cock. He then came up under my shirt and began to play with my nipples – which felt very good. As he was kissing the back of my neck he slid a hand down and into my pants where he held my cock. Ever so slowly he unbuckled my belt, and then the button on my pants then slid them down in one smooth motion including my boxers. Placing his hands on my hips he turned me around and took my cock into his mouth. Slowly he sucked it in and out as he held my butt for several minutes.

He finished undressing me and motioned for me to get on the bed. As I laid there he got undressed climbed on the bed and began kissing me all over from my toes unto my nipples and everything in between.

As I am enjoying every second of this attention I do continue to take peaks at the porn that is playing in the room. In one smooth motion he is on top of me in the 69 position. His cock is inches from my mouth so I reach up and place it into my mouth and begin sucking.

After doing this almost to the cumming point he gets off and lies along side of me and while he is sucking my nipples he is rubbing my cock until I shoot a load on stomach. I reached down and begin to rub his cock when he told me that because of some meds he is on he hardly ever cums so not to worry about getting him off.

The next time I went to visit him we had a very similar sex event but this time he had a box of toys open on a chair in the room. The box had cuffs, a medium to large butt plug, a cockshaped dildo that was scary big and an average size cock shaped dildo which I would find out later was a vibrator.

After I came we were lying on the bed and he asked me if I ever thought of trying new things. Instantly I thought of the box I saw with the “inviting contents”. I did tell him that I have thought of various things but never had a chance to try them. He then said to come with him, so we went out into his living room where he had a male bondage video playing.

I just stood there, naked watching what was happening. Without me even noticing he left and came back with a couple of diet cokes. “Returning “to the room I took the drink but never taking my eyes off the TV. I can’t tell you how long we stood there watching but all I can say is that it was very exciting and I felt my cock getting stiff.

Paul gently began to rub my back then butt then put his are around my waist and pulled me close to him. With my eyes still fixated on the TV he asked me what I thought. I said I have thought of it but never had the nerve to mention it to anyone, plus I could not go home with any marks.

He said if you trust me I can take you to a place you have never been. With a cautious hesitation I agreed. As we returned to the bedroom he assured me he would not leave any marks and that I would enjoy every second. He also said if I wanted to stop just to say “its over” and he would stop.

He told me to lie on my back on the bed so I did with my heart pounding in anticipation of the unknown but potentially exciting.

First he took my arms put them over my head and cuffed each hand to the headboard so they were spread out. Next came the surprise – he blindfolded me and said it is more intense if I cannot see anything. His hands were all over my body in all directions, sometimes gently and sometimes a little rough – then nothing for which appeared to be hours.

I then felt his hands on my leg just above my knee which was followed with something I could not figure out at first – it was a Velcro wrap around my leg. WOA – I felt my leg being pulled, he was strapping it to the what I think was also the head board of the bed.

When this was done my hands were stretched out and tied back and my legs were pulled up exposing my butt totally to the room.

I then felt something warm on butt hole – as I lay there I figured it out – he was breathing his warm breath there. Then I almost totally lost it – I felt his tongue begin to rim me. This was something I never expected or experienced – to tell you it was unbelievable is an understatement. If you have never had this done to you it is something you need to experience - awesome. I did not want him to stop.

When he did stop he asked me if I was OK and did I trust him to keep going. I was basically speechless so I gave a small nod of approval. I then felt him moving about the bed and he ended up with a leg on each side of my head and put his cock in my mouth. He held my head and fucked my mouth hard and I did not know how long he would do this since he told me he cannot cum. He pulled out and took a deep breathe. I felt him coming back to my head area and he put one of those “balls” in my mouth a strapped it around my head. I could breathe but it held my mouth open.

I could not even imagine what if anything would be next until I felt him get between my legs. I felt something cool on my but then his fingers entering me. He did this for a while and gradually increased to two then three fingers which were getting me ready for that vibrator. I felt something hard entering me, it was slightly uncomfortable but I held on hoping it would get better. It was still a little painful when he turned on the vibrator, that took away all the pain and replaced it with an unbelievable feeling of ecstasy.

If felt like I was going to explode but worked at holding back. He stopped moving it and asked if I was ready for the next step. Since every step got more exciting I nodded in approval. He took out the vibrator and told me this might hurt at first but to relax and hold on if I could, I nodded yes.

He then inserted that butt plug. I thought I was going to rip wide open but I held on until it was totally in. Once it got past the large part my but closed around it and held it in tight. He started tapping it, moving it around and it was driving me crazy. Then I felt his warm mouth on my cock, he sucked me until I was about to explode then he jerked me off so I would shoot all over my stomach. The intensity of that organism was second to none I had ever experienced.

Once I caught my breathe he unstrapped the ball from my mouth and took it out. I then felt his fingers on my stomach, little did I know he was wiping up my cum. He placed his cum filled fingers in my mouth and softly said to suck them dry – I did - WOW !!

At this point I was totally spent; he released me and laid on the bed along side of me. He invited me to take a shower with him. I just stood there and he washed me like I was a baby.

To say the least this was a great experience and sometimes the Craigslist meeting can work out.

Paul and I still get together on a semi-regular basis but nothing will come close to that night. Depending on how we feel we go from vanilla play to the bondage play.