Going gay at 40

I saw him at the other side of the bar. Our eyes locked and I searched my memories where we had met before, as he must have too at the same time. At 40 I had never been with a man and the that thought wasn't going through my head at the moment. All I wanted to do was to figure out where we had met before...and then it hit me. He was a lawyer representing management, and I had represented labor in a contract dispute six months earlier...and he was good.

My expression must have changed as soon as I thought of it, and he smiled, picked up his glass and strolled around the bar to where I sat.
"I wondered if you remembered me," he said with a grin. "Let me buy you a drink for all the bad stuff I put you through."

I guessed his age at 60, but he carried it well. Today, he was in a black turtle neck, sport coat and jeans. Earlier, I had only seen him in a suit.
"Jim," he said extending his hand. "And I like your style."

Jim suggested we move to a booth and we did where we begin to swap stories of labor dispute conquests...nothing riveting. Then he mentioned one of the shop stewards I had represented.
"Great guy...great kisser and one helluva fuck," he said with a smile.

I was completely thrown off guard. Here was this GQ lawyer telling me that he had sex with one of the burly men I had worked with.
"Of course you don't want details, do you?" Jim said with a grin, already knowing by my facial expression I did.

He reached over and touched my hands and said, "Some things are best to be discovered on your own."

I must have blushed a thousand shades of red, because he laughed and pulled my hands toward him and suggested we get out of this bar. I was excited, nervous, and then realized, I was getting an erection. I wanted to dive across the table and kiss him, which was an urge I had never felt before. My heart raced and I blurted out "you lead the way."

Outside in the cool air I realized he was slightly taller than me and maybe 20 to 30 pounds heavier, but it wasn't fat. He was very fit.

"Come on...I know a great place around the corner," he said, placing a hand on my middle back and steering me in his direction.

We walked a half block and turned the corner to what was his law office. Turning me again, this time his hand was on my ass and I suddenly realized that I liked it there.

Jim unlocked the door and we entered inside. I stepped to the middle of the empty reception area. Lit only by the light filtering in from outside street lights and the glow of a few standby buttons on computers and printers, felt Jim's hands on my shoulders.
Turning me toward him, he pulled me close and our lips connected. Not a hard kiss, but a moist kiss with just the tip of his tongue darting and dancing with mine.

"I'm not gay," I finally managed to whisper, as if someone else in the dark room might hear.
"You don't know what you are," he whispered back as his hand slide down my back and around to cup my now full erection through my pants."

I knew he was right. I wanted more. I pulled him to me and kissed him deep and passionately. My hands inside his jacket and tugging at his turtleneck. I loosened it from the front and slide my hand up his chest....it was a nice feel of hair.
"Come on," as he took me by the hand and led me down a dark hallway. We turned and went into a room in the back of the office. Still dark, Jim turned on a small light that illuminated the room is a soft warm glow.

"Let's see what wants to get out," he said with a smile as he tugged at my belt and pants button. My pants dropped to the floor and I quickly kicked off my shoes and shook off the pants. Next he pulled my underwear to the floor and as I removed them, I pulled both my socks off as well. Now I was standing naked with only an oxford shirt on...

I started to unbutton it and as I took my eyes off Jim to concentrate on my buttons, I felt him slide up behind me and kiss me on the neck. His right hand reached around me and began to stroke my now very hard cock as his left hand pulled my shirt off me. I was now totally naked.

Pulling me backwards I realized he was guiding me to sit on a very large leather couch, and he was now also totally naked. His cock was huge, and bulging. His balls and area around his cock was shaved...and I couldn't take my eyes off it.
"Go ahead," he whispered. "Touch it."

I reached over and started to stroke him, at the same time he stroked me. It was soft, but at the same time very firm. His cock was at least 8 inches and much thicker than mine. It was the first cock I have ever touched other than my own, and it felt wonderful.
On the leather couch, he kissed me again without letting go of my cock. Then he slowly lowered himself down my chest kissing it as he went. I arched my hips to meet his mouth as he began to slowly circle the tip of my cock with his tongue.

Our positions made it such that I couldn't reach his cock now without straining, and I started to lean toward him when he raised up and slide me under him. We were now in perfect position for 69 and I felt his cock brush my face.

I chased it with my tongue and begin to took the head of his cock into my mouth. It felt so good. Not once did I stop and wonder what I was doing. Everything felt so natural. His hips pushed his cock into my mouth and I begin to suck it...first hard, then soft, then just licks. then hard again.

Meanwhile I felt his mouth on my cock and I tried to do what he was doing for me. Suddenly he sped up and I couldn't hold back as I spewed a shot of hot cum into his mouth.

On his cock, I begin to taste precum as his hips began to rapidly bounce up and down, as he literally fucked my face. His cum hit the back of my throat and I instantly gagged, but quickly regained my position. He came more and more...and it was hot, saltly and thick. I swallowed and it seemed so natural.

We both lay there for what seemed liked minutes catching our breath. Jim turned and we were now laying on the big couch side-by-side with my head on his shoulder. It felt so right. He kissed me on the cheek and said it was a good beginning.
We lay there and I reached over to play with his now limp cock. Jim moaned a bit as I begin to stroke it again and it begin to become hard.

"I'd really like to fuck you," he whispered into my ear as he nibbled on my earlobe. "Would that be okay with you? I promise you'll like it."
I nodded approval not really knowing what I was about to experience.

As I lay there, he sat up and positioned himself over me. I could see that his semi-hard cock was a full erection now. Mine was still limp, but the excitement built in me.

With a gentle hand under each thigh he spread my legs apart and slid a pillow under my lower back to arch my ass toward the air. Jim reached over to a table with a drawer and pulled out a small bottle of lubricate. He squirted some in his hand and begin to rub it around my anus. Now and then he would dart a finger into my ass.
He knew I was tense now, and said "relax...you'll like this."

Slowly he worked his hands and fingers around my ass....first one finger in, then two...then using both fingers, he began to finger fuck my ass.
I moaned as the initial pain subsided and the feeling of pleasure increased. Now Jim worked some lube onto his cock and placed the German-helmet head of his erect cock against my anus.

"Push back, like you are taking a poo." Jim instructed me as he raised my legs into the air to better position my ass.
I did and his cock slipped right into my hole. At first an intense pain shot through my ass and I let out a scream. "It hurts!"
"Easy," him said, as he stroked my hair and shoulder. He stopped pushing and allowed my ass to adjust to his cock.

Then Jim begin to slowly pull back, and then thrust again. The pain was gone and now with every thrust I felt my own cock come alive.

"See, I knew you would like this," Jim said with a smile as he continued to fuck me. His rhythm keeping pace with his moans. I began to thrust my hips up to meet his eager cock and we both developed a rhythm of moans and thrusts.
Suddenly without much warning my cock erupted with cum. Flying into my face, on my chest and into my hair.

Jim didn't even notice because he at the same time was erupting with his own climax deep into my ass. He let out the biggest moan of the night and I immediately felt my ass fill with his hot cum. And when I thought he was finished, he chugged more cum into my waiting ass.
Jim collapse on top of me and kissed me deeply. His cock, now going limp, slid out of my ass and I lowered my legs.

We lay there lightly kissing each other until I realized that tomorrow was a work day and I had to leave. We kissed and then dressed.

The next day, I entered the conference room to deal with another labor-management dispute and across the table smiled a familiar face alone in the oak-paneled room.
"We meet again," Jim said with a smile.