My First Bottom Experience

I never thought of being with a man until I was 45. It was the internet that sparked my curiosity. I first discovered shemales on the internet and was very aroused by men sucking shemale cock. I realized that cock was really hot and I wondered if it might be fun to suck one.

That lead to a nervous craigslist encounter with a very nice guy who lead me patiently to suck my first gay cock. From there, I would be a "mostly str8" guy but once or twice a year, I would find a guy and suck his cock (and get sucked myself). I never thought about getting fucked. No guy ever suggested it and I never wanted to top. I never felt like a top. I knew I was a somewhat feminine cock sucker though and I had experimented with penetrating myself with dildos which was exhilarating.

My first bottom experience would be a complete surprise. I met a much older man who was 70 years old but in surprisingly good shape. He had a very nice rural cabin where we met. I was nervous as usually but he was very patient and kind. I took time to get to know him. As we talked, I came to learn that this man was a real intellectual and accomplished retired history professor which several books to his credit.

We become more relaxed with each other and at one point, while we were both still fully clothed, I hugged him from behind while he was showing me one of his books. He invited me to go to the living room and asked me the get undressed and lay on the couch. I laid on the couch while he stood about five feet away and undressed.

He was wearing sexy jockey shorts and his package filled them nicely. I had already seen a picture of his cock on SD but when he pulled off his shorts, my heart nearly stopped. I screamed out loud "Oh My God!! Your cock is amazing." It really was so my sexier than the picture. He was at least 7 inches, circumcised and thick. I asked him to come closer. His cock was inches from my face and I asked him if I could suck him (I always ask even though the men I meet are gay and we are there for sex. Don't know why I ask) He smiled and said "Yes." I was in heaven as a let my tongue lick his sexy shaft and mushroom head. He already had precum which I licked away. I was taking a few inches at a time and he was moaning while still standing. He then told me to get on my knees on the floor and he sat on the couch in front of me with his legs spread wide and cock fully erect.

He was so comfortable and I wanted to taste all of him. I kissed his mouth and then worked my way down his chest, stomach and then began deep throating his cock. I have no gag reflex so this is a pleasure and he laid back further, moaned and pushed the back of my head down on his cock to keep me from pulling away. I was so excited. He said he didn't want to cum yet so he told me to go to the bedroom and lay on the bed.

I went to the room and waited for him. He took a minute or two and I was just relaxing face down. He came in and laid on top of me and kissed my neck. I felt all of his body weight on me and I couldn't move. His hard cock was sliding between my ass cheeks and I moaned reflexively. He asked "Can I fuck you?"

I never felt more comfortable for this ever before so I turned my head and said "Yes but I have to tell you something."

I explained that this was my first time bottoming and I needed him to go slow and help me. He was so kind and loving. He put on a condom and lube and moved me to the edge of the bed. Slowly, I felt him push his cock against my hole. There was no hesitation on my part. I relaxed and he went in without the slightest discomfort or pain. He began thrusting and I found myself begging him to push deeper inside me. It was the most beautiful experience. I reached desperately behind and tried to pull him inside me as far as he could go.

He said that he didn't believe this was my first time but it really was. It just happened that I really felt connected to this man and wanted to have him completely inside of me. Unfortunately, he couldn't cum with a condom on and neither of us were willing to bareback so he had me lay on my back and jerked off in front of me. He shot cum all of my face . Then he took my cock and sucked me off.

At the completion, I felt scared because I had just had amazing sex with a man and didn't know how to deal with that. I thanked him politely and left. I didn't see him again but I wrote him by email about six months later and told him he was an amazing lover and thanked him for the best first time bottom experience ever.

I haven't had another bottom experience since because I think it has to be with someone you really like to feel comfortable enough to relax and take it deep.