Finally Found the Courage

The following is a true story. I am a happily married 35 year old white guy with kids. I just moved to Tennessee from Atlanta where I lived for thirty years. I never thought I would leave Atlanta but opportunity knocked and I had to answer. I am 6' 2" and weigh 228 pounds. I have short brown hair and big brown eyes. I have always been told that I could have practically anything I ever want with my eyes. While I have always been attracted to women, I have always had a strong desire to be with another man. This desire began when I was about 18 years old. I would go into chat rooms and begin talking to guys to see if I could find someone to hook up with. Because of a fear that I was unable to overcome, I would always end up jerking off and then getting off the computer. I was always too scared to actually go through with meeting someone. Then, one day for whatever reason, I decided to meet someone.

He was a guy that I had been talking to for a little over a week and we talked on the computer about my interests and also about my hesitations. I told him how I wanted to try things, but that I was very nervous to go through with my actions. He insisted that he would move as slow as needed to make sure that I was completely comfortable in the surrounding. Early one afternoon he and I talked on the computer for a few minutes and he gave me the address to his house. The ride to his house was about 20 minutes but it seemed to take forever to get there. As I pulled into his driveway I was extremely nervous but kept telling myself that he was going to make sure that I was comfortable with everything. Upon my arrival, he met me at the door in a white robe and invited me in. He looked to be just as advertised; 40ish with salt and pepper hair, hazel eyes and in decent shape. He appeared to be a businessman and his home was very clean. We walked me into the family room and invited me to sit on the couch. As we sat down, he moved the robe open just enough to where the head of his cock could be seen resting against his leg. Before I knew what happened, he grabbed my hand and put it on his thigh and moved his robe open little more. For whatever reason, I got scared and ran away.

I regretted that decision for about fifteen years. I completely stopped going into the chat rooms and simply read stories online and got off watching gay porn on the internet. Anytime I traveled alone or if my wife happened to go out of town, I would go to an adult store to purchase anal toys. I sometimes would purchase clothing as well. I would get home and try on the new clothing and then fuck myself with my new toys. As much as I enjoyed the feeling of having my ass breached by a hard fake cock, I knew that in the back of my mind, that was not what I wanted. I wanted to see what it was like to be with another man. I knew what it was that I wanted as well. I wanted to be with someone older than I was; someone that was going to be dominant with me yet not aggressive. I wanted someone that would not be in a hurry to just fuck my brains out, but was willing to take the time I would need. I also had fantasies of being the girl in a relationship; which is a complete role reversal for me. In everything about my life, I am completely dominant. But in my fantasy, I want to worship a man's cock. I want him to feed it to me like I am his to do with as he wishes.

After spending time surfing the internet one night, I read a story that referenced Craig's List. I was not sure what this was and decided to check it out. I saw postings on there that I only dreamed of. How could this be true, and if it is, no way it could be legal. I checked it out for several weeks. I even responded to a couple of the posts. I quickly found out that many of the guys on there were either fake or down right nasty. Either way, I didn't want anything to do with them. I also figured out that the best way to get someone to look at your ad was to include some sort of image to it.

Finally, one day I decided I was going to put a post on the website. I knew what I was looking for and put it in the ad. I wanted someone that was between 35 – 50 years old. I did not care about size because I clearly was not looking for someone to have a relationship with; I was not leaving my family I just had an itch that I needed to scratch. I wanted someone that could host and was willing to go slow. I included a silhouette of a guy with a cock on the tip of his tongue. I sent in the ad and then confirmed it on my email. It seemed to take forever for the ad to post on their website but once I was able to view it, it seemed that every guy in the city responded to me. Many of them were not what I was looking for and several others vanished after the 1st email. One of them was willing to take time and discuss things with me. He understood that I had never done this before and was a little nervous. After a few emails, I finally worked up the courage to meet him. I decided that I was going to take a long lunch break and go to his place.

His name was Robbie and I was excited, nervous, and scared all at the same time. My stomach was in knots as I drove to his apartment in the city. He gave me directions and told me that he would be waiting at the gate to the parking deck so I could gain access. I arrived and followed him up a few levels and we parked next to each other. We introduced and I followed him through the maze of hallways to his apartment. Robbie's apartment was very neat and clean. He invited me in and offered a drink. "Coke, Sprite, Sweet Tea?" he asked. I accepted the tea yet don't know how the words came out as my mouth was as dry as a desert. I sat down on the couch while he grabbed two glasses of tea from the kitchen. We made small talk as he sat down next to me. Robbie and I had discussed my previous "failed attempt" in previous conversation and so he did not push anything on me. At the same time we did not have a lot of time as I needed to get back to the office. Sports Center was on TV and so we discussed our mutual interest in sports. I was wearing my typical Golf Shirt and Khaki dress pants so the conversation went towards that. He told me that he was an instructor at the local golf course and told me that he would get me a great deal on lessons if I was interested.

He then began massaging my shoulders and chest as I sat back on the couch. The massage felt really good and it helped me relax a lot. He then stood up in front of me and sat on my lap facing me. He continued the massage and ran his fingers through my hair. As he did, I placed my hand on his thigh. He was wearing a pair of athletic shorts and a t-shirt. As I slid my hand up and down his thing, I quickly noticed a tent that was pitched in his shorts. Each trip up his leg I got closer to his cock. Just as I was about to touch his cock for the first time, he slid down off my lap and onto the floor. He pulled me up and looked up into my eyes while removing my belt and unbuckling my pants. He let them drop to the floor and then with his thumbs hooked into the waistline of my boxers removed them as well. My cock sprang free in my mouth and he leaned forward and licked the underside of my purple head. He sat me back down onto the couch and began giving me the best blow job I have ever received. Robbie devoured my cock with his mouth. Each time he went down on me, he cupped my balls in his hand. After a couple minutes, he spread my legs a little further and began probing at my butt hole with his finger. All I could do was hold onto the back of his head. He took my cock into his mouth and had a finger sliding into my ass. Everything was spinning in my head and all I wanted to do was trade places with him.

After a few minutes, he looked up at me and winked. I told him that I wanted to try. He stood up where he was and I slid his shorts to the floor. His cock almost slapped me in the face as it popped free. There it was, directly in front of my face. He started rubbing my shoulders again as I stared in amazement at his rock hard member. I was only inches away from finally tasting what I have always fantasized about. With that, I licked the pre-cum from the slit of his mushroom head. I licked it again and watched the strand stretch from his cock to my tongue. The strand popped and landed on the top of his puffy head. I leaned in and swallowed the head of his cock into my mouth. It was more than I anticipated. I slid it back out with a pop and kissed the tip of his dick. It was amazing and everything I had hoped. It was not too big, but not small. I repeated the same thing several times letting his cock pop out of my mouth. Then I took the plunge. In one shot, I took his entire cock into my hungry mouth. I worked his shaft in and out of my mouth with everything I had. I buried my nose in his pubic hair and inhaled through my nose. I loved the musky smell. I kept trying to remember all of the porn that I had jerked off to in the past. I wanted to do exactly what I had been watching. I wanted to make him happy and show him while inexperienced, I am a eager learner. I licked his cock, I swallowed his balls (and added a little hum, something I enjoy), I played with his ass, and then I buried my face onto his dick. I then moved his hands from my shoulders to the back of my head. I wanted him to feel like he was in control. I let him fuck my face at his own pace and just went along for the ride. After a few minutes, he told me that he could not stand any longer.

He asked me if I was interested in more. I was so eager to please him that I told him that I was interested in anything he wanted. He pulled me up off my knees and ushered me into the back bedroom. I walked in front of him and he held my ass in his hand like he owned it. The room looked like a guest room. It had a full size bed with a dresser and small TV. He told me to lie down on the bed as he walked into the connecting bathroom. He quickly returned with some lube and two condoms in his hand. Robbie walked like a king. His paces were strong, confident, and pronounced. I knew exactly what he wanted and was excited to make this happen. When he walked back into the bedroom, he placed the items he had fetched onto the nightstand. I immediately dropped back onto my knees in front of the bed and he again fed his cock to me as if it was what I was meant to do. I blew him for a few more minutes before he told me to get onto the bed and lay on my stomach. He put a pillow under my stomach and then spread my legs open. I felt his fingers contact my butt and enjoyed how good it felt as they slipped inside me with the lube applied to them. He told me to relax as he continued sliding his finger in and out of my hole. He worked it inside me for a few minutes before inserting another. It felt amazing as he stretched my ass with his fingers. I told him that I wanted to feel him and he insisted that I be prepared.

After what seemed like forever, I felt him climb on the bed behind me. He had already rolled the condom onto his rock hard dick and I felt it lined up with my ass. He told me to relax and then slowly pressed himself into me. It was the most pain I have ever felt in my life and I wanted to jump up and run. I gripped his wrist and he stopped immediately. It felt like I was being stabbed and ripped in two all at the same time. He told me to relax and that if I wanted to stop he would understand. The pain subdued and I relaxed like he said. He rolled me over onto my back and lifted my legs over his shoulders and began to enter me again. This time I stayed as still as I possibly could. It hurt again when he breached me and he slowed when he saw the pain on my face. As I began to adjust he slid further into me. After a couple of minutes, all of the pain was gone and he was sliding in and out of me with no problem. He looked at me with worried eyes and continued to ask if I was ok. I insisted that I was and asked him to continue. Within minutes, he picked up the pace. With the pain gone, I was experiencing the greatest pleasure ever. With my legs perched on top of his shoulders and his throbbing cock stuffing my ass, I was finally enjoying what I always wanted. Robbie was slamming his cock into me with force as his balls bounced off my butt. It was complete heaven. He built up quite a lather about him fucking me into senseless. I kept looking at him as he grunted with each thrust. I was laying on my back begging for him to fuck me harder.

Robbie looked down at me and could tell that I was enjoying myself. All I could say was "Yes Robbie, Fuck me harder", "Oh my God your cock feels so good inside me". Then he seemed to slow down a little bit and told me he was going to blow. I begged for him to shoot it into my mouth. He quickly got up and ripped off his condom and slid his big dick into my mouth. I drooled all over his meat and with his cock pointed directly at my mouth I jerked him off. Within a minute, I was rewarded. He exploded directly down my throat. I did not get to taste much of it as it hit me in the back of the throat and went straight to my stomach. I was more concerned with getting it all down and not choking than savoring the flavor. I licked his cock clean as he deflated and slipped out of my mouth. The smile on his face was priceless as I am sure the one I was wearing was as well. He was spent and satisfied.

More to come.......