Like most guys, I had entertained a gay fantasy or two in my 50 years of life but since I had been moderately happily married and had raised three kids. Unfortunately my wife was an alcoholic and we seperated.

The longer I went without sex, the horier I got. I watched normal porn and jerked off alot but still craved the touch of another person(re-enter my gay fantacies). At first I was content to just imagine what a guy would feel like. I soon transitioned to gay por, then gay chatrooms and cber sex.

After almost ywo years I felt that the time was right to take it to the next level. I had chatted with alot of guys that volunteered( some a little to forcefully) to be my first. I finally settled on a guy named Steve.

He was not pushy at all. He said he was a bottom that liked to cross-dress for special occasions. We had been talking and role playing for over a month when I decided that this was it. I made arrangements to meet him for dinner that Friday night( just in case it turned out to be a long weekend) and we met at the appointed time and place.

I already knew I was drawn to him mentally and emotionally, but I knew the face to face meeting would make or break the deal. We decided to meet in a coffee shop near his house. I arrived first and when I did'nt see him, I seated myself and waited. To say I was nervous would have been a gross understatement. I had ordered a beer and had just finished thinking(for the umpteenth time that I must be crazy. I started to leave a dozen times but something inside me said to stay.

I had just finished my drink when someone touched my shoulder, "Excuse me, are you Ben?', the voice asked. I turned and was not prepared for what I saw. Standing there was a very tall and strikeing(hot) ...women? "Steve...?", I managed to say. Breathing a sigh of relief she sat accross from me. I just stared and(after scooping my jaw off the floor) managed to stammer outa barely audible, " Hi".

This may be a good time to describe her. She was tal and slender. She had shoulder lenghth blonde hair that I'd swear was real if she had'nt told my different during one of our all night sessions. She had on a long black trenchcoat( which seemed odd since it was not cold that day) and red four inch,'fuck-me pumps. Sitting accross from me, she asked for a glass of red wine and just sat and smiled at me. " I have that effect on some people", she chuckled.

Well to make a long story short( I know, too late), we talked for hours like we'd known each other for years. Finally, she put her hand over mine and said two words, "Stage two?, she asked. This was it. This was the next step. "Why not?", I said throwing caution to the wind.

We agreed to go back to her place for a few more drinks. She only lived a few miles away, so within twenty minutes I found myself sitting on her couch and enjoying her company. She asked if I had ever seen any gay porn and I told her that I had seen some here and there. She asked if I'd like to watch some now and I agreed..

She must have had it set up because all she did was grab the control and hit play. She had to move close to me to reach the control. When the movie started I thought it was a strait porn, but it soon became clear that it featured a very well built older guy abd a very passable cross dresser. We had made small talk at first but stopped when the real action started. As the movie progressed, I could feel my cock start to grow. When I looked back at her she was stareing into my eyes. "I want you ", she whispered.

At first she leaned in as if to kiss me, but smiled and stood up and threww off her trenchcoat. Now I knew why he wore it. He was wearing a red coresett, red panties and fishnet stockings. Mesmerized I reached for him. Sitting back down he put his finger to his lips and whispered, "shhhh, let me do the work." I had learned during our long talks that he considered himself a total bottom and that his pleasure came from pleasing his partner.. "Ben", he began," If it ever gets too uncomfortable just say the word and I'll stop,ok? I was able to nod in agrrement which he thought was cute.

He pulled me to my feet and quickly pulled my shirt up and off. I had already kicked off my shoes so he slowly onbuttoned my levi's and slid them to the floor. I had worn a light blue pair od bikini underware , which he also peeled down. By this time my cock was as hard as a battleship and stuck strait out. He pushed me onto the couch again and I was soon sitting there , totally naked and aroused. Dropping to his knees between my legs he reached up and ran a finger down the shaft. I thought I was going to shoot right there and ask him to slow down. Smileing up at me he told me that first timers like me always came real quick. "So", he said, " pulling my cock towards his moth(complete with candy apple red lip gloss,"lets get this over with so the fun can really start, and yes I do want you to cum in my moth. The taste and feel of a guys first orgasm drives me nuts."

And with that he wrapped his hand around my shaft and brought his mouth down and engulfed my swollen and throbbing head. He was right, I would'nt last long like this. I could feel his tongue flick over the purple head. Already I could feel the cum building in my nuts, and just like that he had my cock all the way down his throat and back up again. I was only seconds away from what I knew would be the biggest and greatest orgasm in my life. His head plunged down agai and he kept it there for just a moment. My cock swelled and we both knew what was cumming. He pulled his head back up until just the head was in his mouth and stroked my cocked with his hand, using his own saliva as lubricant. I screamed out some unintelligble sound as the first shot flew from me. It was followed by not two, not three, not even four or five but sixshots of superheated, molten cum that erupted from me and went right down his throat. I had'nt noticed but he was moaning pretty loudly around my cick as he swallowed and swalloowed and kept swallowing til it was spent. I was covered in sweat and just flopped my head back breathing heavily. He just sat there smileing. "Round one", he said

After I caught my breath and he had used the bathroom, he led me into his bedroom and guided me to his bed. I watched as he removed his panties to reveal a 7-8" cut cock that was still hard. He had a devilish grin as he walked toward me.

Sitting on the bed he reached for my hand and placed it on his cock. I had never touched another guys cock so I just tried to do to him what I knew I liked. I ran my fingertips up and down the uderside of his cock. The vein was huge and pulsed ever time I touched it. I finally wrapped my hand around it and started to stroke him. He closed his eyes and moaned softly. Reaching into his nightstand he pulled out some warming lube and dripped some over my hand. Immediately my hand was glideing up and down his shaft. We stayed like that for what seemed like a long time. This guy had great staying power. Then he dribbled some onto my re-hardening cock and began his own strokeing motion. Ten minutes, we were both hard as granite and moaning loudly. Removeing his hand he bent over and kised my lightly on the lips. I had'nteven thought about this aspect but I still returned the kiss.

Finally raiseing his head up, he said only one word, "Ready?" I was'nt sure what he meant but at this point I was too turnrd on to care. He slowly brought one leg over my torso and straddled me. He just sat there for a moment before he started to undulate his hips. I could feel my hard cock rubbing againt his balls and crack. Any other time and I probably would have exploded instantly, but he knew what he was doing when he sucked me off earlier. Then, almost in slow motion, he rose slightly, grabbed my cock and placed the head against his tight hole. He was already lubed from our stroking and his sweat. I felt the head pop in. He stopped for a second and I thought he flinched. "You ok?", I asked. "Oh yeah, baby. Your just bigger than I'm used to".

Bit by bit he eased himself down until I was buried inside him to the hilt. He stopped for just a moment and then began to undulate his hips again. God, this was tight and hot. He raised himself up until just the head wad in and slid back down. "Oh yeah, that fits just right, baby he moaned. He began t slow up and down motion, getting just a bit faster every stroke or two. I took one of my hands off his hips amd started to stroke him agian. This brought out a louder moan and his pace quickiened. I found that as my stroking sped up so did his gyrations. Ten minutes later we were both going at warp speed. Finally, I reached my own peak. He felt my cock swell again. His eyes popped open an he looked down at my. "Are you...?" he managed to rasp. All I could do is grunt in the affirmitive."Tell mee... he start ed to say but just then my balls boiled over and my cock start to explode again deep inside hime. This set him off and his cock swelled and twitched. I had never seen a guy cum before. His head turnrd a deep purle just before he screamed something to god and rope after rope of white hot seman shot from his cock. It was like my cum was shooting up his ass and out of his cock. Three shots hit the backboard, two mre landed on the pillow next to my head and four gushed onto my chest and stomach.

Trembling he collapsed on top of me and just laid there breathing heavy. My first trip into the world of gay sex was a successfull - I liked it.

This is my first attempt at erotic writing. I would greatly appreciated and comments on how I could make it better or if I should try it again. Let me know. Thanks for reading!