James: Gay Sugar Daddy Part One

James: Gay Sugar Daddy

Part One

I had just moved to the big city and found myself poor, working odd jobs, and lacking a sex life. After my trip to Europe and finishing school, I had hit a 6 month dry spell. Being a cute 24 year old 5'7 bear cub with dirty blonde hair and an athletic build, I had never before had trouble getting laid, but I was getting older. I thought my wild days were behind me, but then I met James.

I found a night job as a bartender at a local gay bar. I made decent tips, always had fun, but the place was pretty much a dive with very little business. It was 15 minutes before closing and I was working the bar alone. I took a shot and started to think about which dildo I would use that night. After another swig I decided to unwind a little. I opened the cash register and lifted the cash box, pulling out a very special DVD. The DVD was a gay porn movie I would watch regularly during the last hour of working at the empty bar. I skipped ahead to my favorite scene where two big bears fucked a young emo cub.

I watched and sipped whiskey as the cub got on his knees to accommodate both cocks slapping his face. I turned up the sound as I felt my cock grow. I was just considering taking my cock out when I heard a deep voice say, “Excuse me.”

I jolted around and saw that a lone man had very quietly made his way to the bar and sat down. He was tall, burly, bald, bearded, but very clean cut, wearing what looked to be a very expensive suit. I awkwardly stood there saying nothing and trying to casually turn off the TV. The man smiled, “Can I have a scotch please?”

I turned around to turn off the TV when the man said, “No no, leave that on please.”

With my cock still hard, I felt the man watch me as I made him his drink. I walked over to the man and placed his drink in front of him, meeting is intense gaze. “On the house sir,” I said, hoping he would tell anyone about the porn. I stood in silence as he sipped and sounds of heavy grunts blared from the TV.

The man quickly finished his drink and motioned me for another. I started to fill up his glass when he began to talk slowly. “I'm James. Looks like you were pretty lonely here tonight. I know you are closing up, but I was hoping for a little special hospitality. Maybe something like that movie you were watching. What do you say? I'll leave you a tip as big as my cock.”

I felt my cock get diamond hard. I lifted my head and really looked at James. He was a older, bigger man, an endearing beer belly, greying beard, and very masculine man. Had I seen him in the bar when it was busy, he wouldn't have caught my eye, but in this setting he looked like the sexiest man alive. Saying nothing, I gave James his drink and walked over to lock the door and shut the blinds. James smiled.

I took a swig of whiskey with James and lead him into the back office. I sat James down in my boss's office chair. I got on my knees and crawled underneath the desk. I leaned up and meet James with a deep passionate tongue massaging kiss. I unbuttoned James' shirt as I bite his lower lip. James pushed my hands down to un-do his belt and groaned, tending to his shirt. Jittery with anticipation, I quickly unbuckled his belt and unzipped him. He lifted his legs so I could slide off his pants. I pulled down his pants down past his knees as he unbuttoned his shirt and let it hang open. I looked up and saw James had a massive 8 inch cut cock, semi erect resting on his leg. I gasped at his picture perfect cock.

I gave James a happy smile, “I like what you have here.” I took off my shirt and started rubbing his legs and inch my mouth closer to his cock, teases him. I kissed his gut and moved my hands up to cup his balls. At this James cock flew up and hit me in the face. “Oh, you want me to suck this cock.”

James closed his eyes and grunted, “fuck yes.”

I started licking the shaft up and down, feeling the rod getting harder and harder. James relaxed his entire body and told me to go to work. Not wasting any time, I wrapped my mouth around his thick meaty cock. Getting only a quarter of the way down, I licked pre-cum off his soft bulb and slurped up sweat and spit. I worked my head around and around rotating his dick with my mouth. James rubbed his hand on my head. “You done this before haven't you?” he asked as I nodded my head while joying working on his hard cock. “Well, then I know you can go deeper.”

James pushed my head further down on his big rod until I started to gag. James pulled out his cock a little, let me catch my breathe, and then pushed me back down even further and longer. James took control and repeated this 3 times until my lips reached the very base of his raging unit. I closed my eyes and just enjoyed the intense pleasure of the moment. James started to work his cock faster and faster, fucking my throat as deep as he could. I heard James start to moan.

The next thing I knew my mouth was full of warm, salty, milky cum. I swallowed a bit and kept sucking and sucking. James grabbed his cock out and started to stroke out huge ropes of cum all over my face. After his last push of cum, I took his cock and started to suck him passionately. “Mmm, fuck, get every last drip on that cum” he instructed. I looked him in the eye as I cleaned cum up his balls with my tongue. I pulled my hair and brought me up to him, giving my a deep kiss and swapping his own cum. He pulled back and caressed my cum plastered face. He put some cum on his finger for me to lick off.

“Good boy” he said with a grin. I didn't know it then, but this was the start of a great sexual adventure.