First Time with an Older Man
This is a true story about my first time every being with a man.
I was around 24 when I finally got up the nerve to see another man. I really had no idea what I was in for. This was back in 1993 and there was no internet and the information at hand was not like it is today.
I found an ad in the local newspaper offering a "Massage by Older Man". It was time to go for it, so I called the number and Gerry answered the call. We made arrangements to meet near his house and then he led me back to his townhouse complex. My mind was racing and my cock was trying to split my jeans. Gerry was an older guy in his mid 50's with grey hair and beard.
Once inside we went up to his bedroom and I stripped down to my underwear. Gerry began to give me a massage and rub down. After about 15 minutes he slowly slipped his hand under me and began to caress my cock and balls. Asking if he could remove my underwear, I happily agreed. He then moved his mouth down to my cock and pulled it back under me towards my feet (I was laying on my stomach). Gerry was now giving me my first ever M2M blow job and I was in heaven. I still remember to this day what he did next and I still fantasize about it, Gerry slowly moved up my back kissing me all over and moved to my ear where he asked me "Do you want me to Fuck your ass" The moment I had been waiting for for years was finally upon me. I moaned yes please...
Gerry then gently started lubing up my ass and put on a condom. Now I had played with putting lots of things up my ass but nothing the size of a cock, he was average size about 6-6.5". Gerry was really gentle and patient with taking my cherry and made me really enjoy the whole experience. I don't know how long he fucked me for as things became a blur of pleasure and excitement and I really didn't care about time. I remember the feeling of having him cum while fucking my ass and realized at that point that I love be able to be the source of someone else getting their rocks off.
I saw Gerry about a dozen times or so over the next year at varying locations, his office, in the woods near the US border with Canada among them. I think it was the 3rd time we got together where I got up the nerve to give my first blow job, I knew as soon as he put his cock in my mouth I was meant to be doing this. The pleasure of sucking on another man's cock is intoxicating knowing just how good it can feel. I was a quick learner and received praise for my technique and then a reward of a load of cum in my mouth. I was not too thrilled with the taste the first time but like most things it takes time to learn to enjoy the taste.
I lost track of Gerry over the years but when I need to have a great jerk off session I just think back to "Do you want me to fuck your ass" and blow a load.
I was around 24 when I finally got up the nerve to see another man. I really had no idea what I was in for. This was back in 1993 and there was no internet and the information at hand was not like it is today.
I found an ad in the local newspaper offering a "Massage by Older Man". It was time to go for it, so I called the number and Gerry answered the call. We made arrangements to meet near his house and then he led me back to his townhouse complex. My mind was racing and my cock was trying to split my jeans. Gerry was an older guy in his mid 50's with grey hair and beard.
Once inside we went up to his bedroom and I stripped down to my underwear. Gerry began to give me a massage and rub down. After about 15 minutes he slowly slipped his hand under me and began to caress my cock and balls. Asking if he could remove my underwear, I happily agreed. He then moved his mouth down to my cock and pulled it back under me towards my feet (I was laying on my stomach). Gerry was now giving me my first ever M2M blow job and I was in heaven. I still remember to this day what he did next and I still fantasize about it, Gerry slowly moved up my back kissing me all over and moved to my ear where he asked me "Do you want me to Fuck your ass" The moment I had been waiting for for years was finally upon me. I moaned yes please...
Gerry then gently started lubing up my ass and put on a condom. Now I had played with putting lots of things up my ass but nothing the size of a cock, he was average size about 6-6.5". Gerry was really gentle and patient with taking my cherry and made me really enjoy the whole experience. I don't know how long he fucked me for as things became a blur of pleasure and excitement and I really didn't care about time. I remember the feeling of having him cum while fucking my ass and realized at that point that I love be able to be the source of someone else getting their rocks off.
I saw Gerry about a dozen times or so over the next year at varying locations, his office, in the woods near the US border with Canada among them. I think it was the 3rd time we got together where I got up the nerve to give my first blow job, I knew as soon as he put his cock in my mouth I was meant to be doing this. The pleasure of sucking on another man's cock is intoxicating knowing just how good it can feel. I was a quick learner and received praise for my technique and then a reward of a load of cum in my mouth. I was not too thrilled with the taste the first time but like most things it takes time to learn to enjoy the taste.
I lost track of Gerry over the years but when I need to have a great jerk off session I just think back to "Do you want me to fuck your ass" and blow a load.
10 years ago
