Everyone has a first time; this is the story of mine. It is a true story presented as closely as I remember it. Yes, there may be some who think this is too wordy and I understand that. But this is how I write.
It was 1986 and I was 28 years old, stood about 5 foot 10 and weighed about 160 pounds. An encounter with a man had simply never happened, but I also had a very rich fantasy life and sometimes imagined a man was playing with my cock when I jacked off. The thing that made a real change was a 3 week journey through Germany the summer of 1985. I visited the Sex Shops in several cities and spent time in the video booths where I found gay porn. Jacked off a few times in there and my interest for an experience with a man was growing.
There was a local newspaper that had an extensive “Personals” section. I’d read the gay ones with interest, but none really sounded right. Then I read one that said “Gay male, 55, seeks younger male for conversation. Phone 905-555-XXXX for more information.” So I called and talked with Jerry who sounded like a nice guy. He explained he liked to entertain younger men who were interested in new ideas. He wouldn’t explain more on the phone but I got the idea. The whole time we talked I was nervous and Jerry noticed this. He said nothing would happen that I didn’t want to happen and we could stop the conversation at any time. I agreed to come to his apartment that afternoon.
The drive was short from Oakville to Hamilton and I arrived at his building on King Street. He buzzed me in and I rode the elevator to the 12th floor. I knocked with my stomach in knots, but I knocked. Jerry answered and asked me in, his door opened into the living room. He directed me to a big easy chair in the corner, the blinds were drawn and the room was dimly lit. He was welcoming and I started to feel comfortable as he sat on the couch across from me. We talked about my circumstances, no experience and nervous, but he made me feel calm. He was about 6 foot tall and about 225 pounds, grey hair and beard.
As we talked he went and got a short stool and set it in front of me. He sat down and continued talking saying he wanted to give me an experience I would enjoy and never forget. His hands glided up the sides of my legs over my jeans and then his hands moved to the inside of my legs he pushed them apart and started to caress the inside of my upper thighs. My cock is about 7 inches long and 5 inches wide and it was getting hard in my pants but he wouldn’t touch it. His hands pushed up under my sweater and he started to play with my nipples. My nervousness was gone replaced by my hormones, this felt really good. He pushed my sweater up over my head and rubbed my chest and belly. He leaned forward and took each of my nipples in his mouth and sucked and licked them. Then he stroked my face and ears, smiling the whole time, and asked if everything was ok so far. I answered yes and he asked me to stand and take my pants off. As I did so he left the room for a minute.
When he came back he had a blanket and a face cloth. He laid the blanket on the floor and directed me to lie face down on the blanket. I didn’t know how I was going to do this as my cock was standing straight out but he asked me to try. I lay down as best I could and then knelt down behind me, parted my ass cheeks and washed me with a warm face cloth. The sensation was unreal as I’d never been touched back there before and he was going up and down over my hole. I involuntarily groaned when he put down the cloth, parted my ass cheeks and started to lick me up and down back there. I’m sure my eyes opened real wide at the sensation of this man’s tongue in my crack, then stopping over my hole and swirling around it. While he worked his tongue into me I was completely lost in the sensation and didn’t notice Jerry pulling me up onto my knees. His tongue was focused on my hole now, digging in, swirling around and driving me crazy.
I felt a hand around my cock as he slowly, really slowly, jacked me. He would stop and twist the head of my cock and then stroke it again. I looked down and my cock was dripping pre-cum onto the blanket making a small puddle. I was so close to cumming but he knew when to stop, when to ease off or change what he was doing. He was toying with me and I felt helpless to stop him. Also, I didn’t want to stop him, I had never experienced this kind of sexual sensation before.
I don’t know how long this went on before he asked me to lie on my back. He started licking my nipples again while pushing my legs apart with his knees. His mouth went down my belly to the inside of my thighs to my balls where he took one then the other into his mouth and warmed them, then ran his tongue all over my sac. Eventually he moved to my cock and was licking it from the base to the head and back down again. Without any warning he took me into his mouth, taking me a little deeper with each downward stroke. His mouth felt like a velvet glove with just the right amount of pressure, not enough to make me cum but more than enough to make by balls ache. I grabbed the blanket and held on for this wild ride, I was not in control of my cock and that was new for me. He continued to suck on me like I’d never know, his mouth was a dream, varying speed from fast to painfully slow.
I could feel his hands under me, stroking my ass cheeks as my legs were spread wide around his body. Jerry was running a finger up and down between my cheeks and started to rub my hole a little. He stopped sucking me and reached to the side for a bottle I hadn’t noticed before, it was lube. He poured a generous amount into his right hand and looked me directly in the eye. Jerry said I was going to enjoy this next part but it might feel a little uncomfortable to start with. His hand went between my legs and I felt the cold gel being rubbed up and down my ass crack. His concentration soon was on my hole and he rubbed around it without going inside. Then she started to probe my hole with his finger and slipped one inside me and slowly worked it in and out. He smiled and continued to work his finger into me asking how this felt; all I could do was moan and whimper.
Jerry asked if I wanted to cum? I groaned yes and he put his mouth on my cock again, all the way into his throat. His finger continued to push in and out of my ass, stroking my prostate sending electricity through my cock. My cock head had electricity running through it as he swirled his tongue around it and nibbled on the underside. I lay my head back and tried to endure this as much as possible but it was not my choice, this man was going to make me cum. And then I did, squirting cum into his mouth which never lost its grip on my cock, it was the first time I had come into a mouth and it felt amazing. I think I sent eight or nine streams into his mouth at least. As I was finishing I could feel his finger slide slowly out of me and I relaxed onto the floor again. He kept my cock in his mouth for a few more minutes and I was surprised at how sensitive it still was. Eventually he let me go and stood up.
Don’t know if I slept but I was definitely in a daze for a few minutes. Jerry sat on a chair and admired his handiwork; he asked if I felt ok. I told him I felt fantastic. Eventually I dressed and left with a big smile and an empty cock.