Everyone probably remembers their first time. For me, my first time brings back something I've tried to chase for a long time and have never come close.

I was browsing an online site for younger men to meet older men, given that's what I was into. I was twenty-one years old at the time and had plenty of straight sex, but realized that I had a side of me that wanted to explore gay sex, and with an older man – preferably a much older man, given that's what I found myself having an attraction to.

I had a reply from an older man who I will call Bill. He was in his late seventies and from the correspondence, he seemed like a very kind older gentleman. He sent me a profile pic of himself and I was immediately attracted to him. He had a portly stature, but he was clean shaven, had a pair of glasses on, and was so handsome that I knew I had to meet this guy. We agreed to meet a few days later and I couldn't wait to meet this guy, and I was also nervous at the same time. I was very naive to gay sex and didn't know what I wanted, or even if this guy wanted to go there.

He invited me over for what he said would be “afternoon tea.” I went to his home and right from the beginning, I was attracted to the guy. He was slightly shorter than I was, wearing a forest green colored cardigan with a white oxford shirt, black slacks, and a pair of black penny loafers. I had on a pair of blue jeans, t-shirt, hoodie, and a pair of skateboarding shoes.

We sat in his living room and talked. He was very kind to me and asked me questions such as to where I was in my life and I explained that I hadn't been to college given I had a comfortable job and made a decent living. We talked about various other subjects and then he said, “Well my young friend, what makes you attracted to older men?” I told him that I didn't know, it was an attraction that I had with no explanation. We agreed to go to lunch to a local restaurant and continue our conversation, and I found him to be very intellectually stimulating. On the way home, he put his hand on my leg as he drove and I sat in the passenger seat, and then took my hand and said,

“Well my dear, what do you think?”

I told him, “I think I really like you.”

He smiled and said, “Good, I've enjoyed getting to know you.”

As we drove on, he let me know he was once married, but that his wife had passed away about ten years before. He told me he explored gay sex before getting married, was happily married for a lot of years, and then picked up exploring gay sex as an older man.

“I have a confession,” I told him. “I have not been with another man sexually.”

He asked me “Why not?” and I explained I was too scared to try or explore that. When we returned to his house, we discussed it further and he asked me more questions such as, “Do you know if you're a top or a bottom?” and these were terms I was sort of familiar with and told him I wanted to try both, but he informed me, “Well, I'm a top.”

It was around 6:00 at night and I had spent about 6 hours talking with him and I sort of figured that nothing was going to happen and he'd be pushing me out the door soon. He was on the couch next to me and he put his hand on my back and said, “I don't want to frighten you, but I really like you. You're a very nice young man.”

I smiled and said, “You're a very nice older man.” He gently took me in his arms and hugged me while sitting next to me.

He pulled away with his arm around me and said, “How would you like to go upstairs to my bedroom? You don't have to, but I would like to be your first and I promise that there's no pressure and we'll take it at our own pace.”

I agreed.

When we made our way to the stairs, he took my hand and escorted me up.

As we undressed, he asked me, “Do older men's bodies turn you off?”

I said, “Absolutely not.”

When we were both naked, he took down the bed and invited me in between the sheets with him. I remember how gently he embraced me and planted a kiss on my mouth, and I gently kissed him back and we began to kiss with our tongues and he felt me all over the place as I felt him. We did that in a very gentle fashion for what seemed like awhile. When I took a moment to lay on my back, he put his hand on my chest and kissed me on the cheek as his hand moved down to my erect cock, which he took gently into his hand. He pushed the covers back and slowly made his way down to my cock as his hands ran down my chest, and the minute I felt my cock inside of his mouth, I was in absolute pleasure and couldn't believe how nice it felt, almost to where I almost came and and told him,

“I'm going to cum! I'm going to cum!” and he pulled away and said,

“Ok! It's ok! If you want that to happen, you do it and let it go.” I wasn't sure if that's what I wanted at that moment, but I remember we embraced for a few moments.

I looked down at his cock, and his was quite large.

“Very good. That was incredible. You did well.”

He took me back in his mouth and slowly pleasured me with his mouth as I moaned and enjoyed every minute of it. His other hand pleasured my balls, and one of his fingers tickled my taint area and I noticed him pressing gently against my hole. He took a break for a moment and opened a drawer pulling out a bottle of lube, putting some on his fingers, and telling me,

“Just relax for a moment.” He gently teased my hole and then entered the tip of his finger inside of me, which I didn't know how to respond to, but didn't want him to stop. A few minutes later, his whole finger was inside of me and I was breathing heavily and he put his other hand on my chest telling me,

“Easy... Easy... Just relax.” He began to massage my prostate, telling me what he was doing and why my prostate was important. He gently pressed and released inside of me, while he held my hand with his other hand and my gentle moaning as a sign I was enjoying it.

“I want to be inside of you,” he told me. “Will you let me?” I didn't know what to say and I felt a wave of fear. “I promise that I will be gentle and if it's too much, you tell me, ok?”

I nervously told him, “Ok.” He took his finger out of me and went into his drawer taking out a fresh box of condoms that he hadn't even opened yet. When I saw him tear the wrapper and saw “MAGNUM” written on it, I became a little bit more nervous knowing what kind of condoms those were. When I saw him unroll the condom on his hard cock, I was a little bit more afraid. He took the bottle of lube and put a lot of lube on his fingers, inserting them into my ass and getting me nice and slick a couple of times. He wiped off his hand and got between my legs.

When he gently pulled me to the edge of his bed and stood in between my legs, he told me,

“You're going to feel a little pressure,” and he began to insert the head of his cock inside of me, which didn't feel painful, but I still felt nervous. He gently manipulated my hole with his cock for what felt like a few minutes before I felt him start to really insert himself into me, which didn't feel too painful at all and felt amazing. He raised my legs higher and over his shoulders, got himself at an angle, and slowly began to thrust in and out of me, which at first felt a little painful, but started to feel amazing.

“You like that?” he asked me in a kind voice as he thrust in and out of me.

“Yes!” I said in-between my moaning. He took his time at first, but he picked up the pace of thrusting, and I began to feel both some pain and a whole lot of pleasure as he thrust in and out of me and my moaning became louder. He began to moan a bit, and even when he was fucking me fast and a little harder as time passed, he felt gentle but firm and made sure that he wasn't hurting me and I was enjoying it.

As he grunted to me, “Ohhhhh, I'm going to cum!” I reached out and put both of my hands over his, and he took his hands off my thighs and held them as he began to grunt a little more and thrust in and out of me a little harder until he let out a growl and I immediately started to feel a warmth inside of me through the condom of his hot cum.

After he pulled the condom off and laid down next to me, he took me in his arms and embraced me, laying kisses on the top of my head as he had my face in his chest and holding me.

“That was beautiful,” he told me. “Thank you so much for letting me be your first,” I hugged him tight and began to cry against his chest.

“Oh, my! Are you alright?” He asked me for concern, and I told him, “Yes, I'm just happy... Thank you,” I told him. He held me for what was probably an hour. We pulled the covers over us and I fell asleep in his arms, feeling content and very relaxed with him, and awoke to his kisses the next morning.

We saw each other for a period of time, until he unfortunately passed away soon after. There has never been anyone else like him in my life since, and I will never forget his gentleness, his gentlemanly demeanor, our intense love-making, and how he taught me the joys of gay sex.