It started at home where I was not getting much sex from my wife so I decided to start looking for something on the side. I signed up for AOL, this was several years ago when they had easy to access chat rooms, to see what I could find.
I would go from room to room looking for someone interesting to chat with about sex. I went from men looking for men ( I was really in need of sex so I even thought of trying to find a sexy guy for some fun ) to women looking for men to married and looking to just about any room where I thought I could find someone.
My first experience was with a married woman who was also looking for that missing piece of sex in her life. We had lunch and discovered that we were not meant to move any further with each other.
I was getting discouraged more and more each day until one day in a male chat room one of the guys suggested that I head to a local adult book store. I took his advice and while I did not find what I was really looking for I did find some video booths with glory holes. I had read about them and even saw a few in action while watching a porn movie but never did I ever expect to find myself in a situation that one was available for my use.
I put in a few quarters and started to watch the video when I heard something coming from the glory hole. I looked down and saw a finger wiggling in the hole, not sure what to do I took a sneak peak and saw a guy with his pants down around his ankles. I was amazed when he bent over and brought his open mouth to the hole. I panicked and left the booth.
I wondered around the store looking at the various adult magazines and videos. Then I realized, this is what I needed a blow job. With my courage built up I went back to the video area and looked for a booth that had someone in the booth along side. This time I was crazy aggressive, I mean, I stepped out of my comfort zone. I decided to unzip my pants, pull out my cock and gently play with it. I put in a few quarters to start the video but did not even watch what was playing, I stood back and looked at the glory holes on each side of the booth.
Finally it appeared, a cock, I was shocked because I was expecting a finger calling my cock. What to do??? I was desperate so I slowly and gently started to touch that cock. It is probably not the right thing to do but shortly after I started playing with that cock a finger calling me appeared in the other hole. I instantly dropped that cock and stuck my cock through the hole. Within a second I felt the warmth of the strangers mouth sucking my cock. It did not take long for me to be rock hard followed by shooting a load into his mouth. When I felt him come off my cock I pulled it back and while I was putting myself back together I heard a “thank you” from the hole.
On the way home my head was spinning, I started to play with a strangers cock then had a blow job from another stranger. But still I did not find what I was looking for – female sex.
About two months later it happened – I set up a meeting with Carol, a married woman who was also looking. She invited me to her home which was about 50 miles away. We talked for almost 2 hours and it was time for me to head home. On my way out it happened, we hugged and started to talk about another meeting when she kissed me. It was kind of a surprise but it was the reason I came to her house. After some heavy kissing I gently tugged on her sweater and that was all she needed. She stepped back, pulled it off, followed by her bra. Her tits were well shaped and waiting for my touch. I played and kissed them for about 15 minutes then told her I really needed to go but if she was willing I would visit her again, she agreed.
About a month later I made the trip to her house but this time she had company, Kathy. She was a single girl about ten years younger than me. All three of us chatted then I left.
As time passed Kathy and I traded more and more emails, then we met for lunch. After lunch we went to the ocean where we sat on the rocks, watched the waves and talked for over 2 hours. While we were there she sat in front of me and I was gently playing with her hair as we talked.
The next few months we had lunch a few more times but never did it go beyond that until one day we started talking about bondage. It was then she told me she was a dominate mistress, that totally intrigued me as I wanted to learn more.
Well we are now where I wanted to bring you. I was at her apartment just chatting when we started talking about what she does and with whom. She told me she had a few subs that come by and just follow her direction. The details of what happened just had my head spinning and bringing up things I thought of but never thought I would say to anyone.
I told her what I had thought then she surprised me when she asked me if I wanted to try. With a little hesitation I agreed, we set the limits and began.
She told me to totally strip; this would put her in a superior position.
At this point she made me walk across the room so she could look me over. When I came back to her side of the room she stood up with something in her hand, it was a blind fold. She got behind me and put on blind fold, then took my hand and led me into the next room. When we arrived she told me to stand still and it seamed like ten minutes when she took my wrists and placed them in cuffs then I felt them being pulled up to the ceiling.
She told me to stand still that she would be back; the anticipation was growing with each passing second. Finally I heard her coming, it sounded like she had on her full mistress outfit including the boots and heals.
Without warning she grabbed my balls with ice cubes in her hands. To say it was shocking would be an understatement. After my balls were totally frozen she used her warm hand and held them for a few seconds but at the same time the ice then arrived on my left nipple. More ice was placed on my right nipple then all over my chest.
Now I was standing there with nothing happening until I felt her hands on my hips, she was behind me. Now she was rubbing my back with her tits, I could feel her nipple on one side and the pierced nipple on the other side on my back. Now came the next shock, she slid her hands up to my nipples and one at a time she place on a clamp, tight enough to give some pain but not enough to hurt, if that makes sense.
With the clamps still in place she lowered my hands and told me to get on my hands and knees. I felt her attaching something to the back of the blind fold strap but I did not know what was happening. I then felt a heavy string or rope on my ass – with a jerking motion she dropped a weight pulling my head back with this rope in the crack of my ass. She started to swing the weight so it was going in and out of my ass as it also hit my cock and balls.
This continued for what appeared for fifteen minutes, I can’t be sure as my head was spinning. Next I felt her pushing something into my ass – not sure what it was but I am guessing an average size dildo. She was working that in and out, slow then fast, deep then shallow before she finally pulled it out.
Then I felt something else pushing on my ass – she was putting is a butt plug. When it was totally in she then started to pull my hands back up so they were again above my head attached to the ceiling. She began to rub her body against me again but this time she was also stroking my cock. Before long I started to breathe hard as I was beginning to cum – she said I could not cum but she was rubbing me harder and faster. Again telling me I could not cum as she continued to rub me. When she sensed I was going to cum she slapped my cock then squeezed it hard, needless to say I did not cum.
A few minutes passed and she started to stroke me again but this time she said I could cum. I was shooting my load to where I did not know until I finished cumming. I was told to open my mouth and I was expecting an ice cube but instead I got a handful of my cum. She said do not swallow or spit – just hold it in my mouth. It was hard not to swallow or spit but she finally told me to open my mouth because she wanted to make sure it was still full of cum.
When I opened my mouth she said very good as she could see it was full of cum. Keep it open she said – then without warning I felt her tongue inside my mouth. This turned into a passionate French kiss with cum moving back and forth and finally swallowed.
This unbelievable time ended with taking off my blind fold to see a camera running. She filmed the whole encounter, but it was not over. I was ordered to jerk off for her. As I did she took off her mistress clothes and put on her regular clothes and transformed back to Kathy.
Now that she was Kathy she said she wanted to help me so she untied my hands and asked if she could do something for me. I told her she had done more than I ever could imagine but she said that was the mistress and not Kathy. Kathy wanted to do something – I said she could do what ever she wanted. She got on her knees and gave me a wonderful blow job. With a mouth full of cum she asked if she could kiss me and I agreed.
This was the only time we ever played like this even though we met many more times before I moved to the Mid-West for a few years. We are both back in the same area and still talk and meet with nothing ever happening again.