Three years ago, at age 53, and after several years of thinking about it, I decided that I really wanted to have sex with a guy. I'm fairly well known in town, so I knew I needed to try a different location for my experimentation. I was heading to Chicago on business in a month, so I went into the AOL directory and looked for a guy in Chicago who might have an interest in an older, bearish kind of guy.
As luck would have it, I found a guy who claimed that he really liked men who were older and bigger than he was, so I emailed him. I was pleasantly surprised when he responded that night. We exchanged a couple of emails and I explained my interest and situation. He asked if he could call me so we could talk more clearly about it, so I got his number and called him the next day from work.
He sounded great, and he said he didn't see any reason for waiting a month for me to come to Chicago, since he was a flight attendant and could route himself through Austin pretty easily. Before I knew it, we made plans for him to fly in that week and for me to go to his hotel before work. It was easy to make an excuse to leave early, since I worked long hours anyway.
After I hung up, I was immediately nervous and unsure if I knew what I was doing. I didn't know anything about this guy! But I knew I really wanted to get my first taste of cock, so I decided to go for it.
That morning I found myself knocking on the door of his hotel, feeling huge butterflies in my stomach. He answered the door wearing a t-shirt and shorts, and I was pleasantly surprised that he was a good-looking guy, about 5' 9", with short hair and a goatee like mine. He immediately told me that he was also pleasantly surprised with me, so things loosened up pretty quickly.
We talked for a little while, and then he asked me, "So, should we get naked?"
I laughed at that, but stood up and started getting undressed. He took off his shirt, but left his shorts on.
"What are you interested in doing," he asked? "I'm up for about anything."
I knew what I wanted. "I really want to suck a cock, but let's work up to it, OK?"
As an answer he took my hand and lay down on the bed. I lay down next to him, and we kissed. That seemed pretty wierd at first, since we both had beards, but I got interested in it and we had our tongues pretty much entwined right away. He was rubbing my ass, and I really wanted to feel his cock, so I stuck my hands down into his boxers, and felt another guys cock for the first time. It was really long, although not as thick as mine, but I loved the way it felt. I then pulled his boxers off and really got my first good look.
I couldn't stand it any longer, and leaned down to slide my lips along the shaft. I sucked his balls into my mouth, and was amazed at how natural it all felt. I then moved up and took his cock into my mouth, marvelling at how hard and soft it was at the same time. Not being so thick, I was able to handle it without any problems, and slid it pretty far into my throat. All the practice with vibrators paid off!
I was in a real state of bliss, sucking on his delicious cock, and I went at it with all I had for ten minutes or more, then I surprised him. "I really want you to fuck my ass."
"Are you sure? This is your first time isn't it?" Good question, really.
"Yep, I'm sure. I know I can handle it, and I've thought about it for a long time."
He then had me turn on my stomach, put on a condom, and applied some lube to my waiting hole. When he slid into me, I knew I would be doing this again. It was wonderful. He started sliding in and out and I never felt a second of pain (probably because he wasn't that thick). I told him to do it hard, and he started pumping me faster and harder. I couldn't believe I had waited this long to do this! After a few minutes of very sexy pounding of my ass, he stopped, and said it needed to be my turn.
"Turn over," he said. Which I did.
He then dove down and gulped my balls into his mouth and sucked them hard. I loved it, and grew harder. Then, suddenly, he slid his tongue up my cock and took my all the way to the hilt down his throat. I'd had lots of blow jobs, but he really knew his stuff. The only bad thing was that the feeling was so intense that I could feel myself cumming after only a couple of minutes. I told him to stop, and he said, "Just warn me."
I just barely was able to tell him I was cumming, but he took me out of his wet mouth and I shot all over my stomach. He smiled at me and I spasmed over and over, "Wow, that was fun."
He then slid up and we snuggled for a bit. He said, "I'm gay, and you're not, so we need to practice safe sex...no swallowing, condoms for fucking...OK?"
"Absolutely," I said. "I really appreciate you beng smart about it, but I need to make you cum. How do you want it?"
"How about just jerking me off? I realy like that if we can kiss at the same time."
So, that's what we did. I really enjoyed masturbating someone else's cock for a change, and got a kick out of watching him shoot all over both of us. It was great!
We did actually meet when I went up to Chicago, and it was fun, but by then I had realized that he and I were both really bottoms, and he was looking for someone to top him really hard...as was I. And as I still am. I only had one other experience, giving a guy a blow job in his office on a Saturday. That made it very clear to me that what I really enjoy is servicing the other guy, but so far I haven't had much luck finding a bi or straight guy who will let me suck his cock once in a while...but I'll keep looking.