This story was originally posted by me in 2014. Unfortunately I've lost access to that accounts email and I can't access any longer. Reposting it here under a new account with some edits to the grammar and sentence structure.
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I wrote down the address and jumped in my jeep. It was late on a December night in Massachusetts. After spending some time in an AOL chat room, I ended up having a lengthy conversation with a guy from a few towns over. He was older at 36 years of age. I, at 21, had been dealing with strong bi-curious feelings for a few years and often found myself cruising chat rooms looking for possible hookups. Finding other guys was rather easy, but I never had the courage to follow through for an actual encounter. However, this guy had some great pics and there was something about older men that was just so hot to me. After getting a little more information and flirting over text he told me to come down to his office. He described a discreet, quiet and warm location where we could have some fun. So I pondered for a moment and then thought to myself, "Why not?"
"Send me your address, I'm on my way," I wrote back.
During the drive my conscience continually weighed out the pros and cons on what I was about to do. I had come close already a few times but always chickened out. But, enough was enough. These feelings had lingered too long and it was time to see what they were all about. After getting off the highway I followed his directions through a little coastal town. Eventually they led me to a quiet main road which was lined with colonial era office buildings. Street lamps lit the still night and I pulled into a back parking lot where I called his phone.
"Hi, are you here?"
"Yep, I just parked," I replied.
"Walk around to the main street."
The brisk winter air chilled the edges of my body as I closed the door. I came around the corner to see a silhouette of a man waving to me.
"Dan!" said the man, with a soft shout.
I walked toward the shadowy figure where we exchanged hellos.
"Welcome, I'm Jack, come on in," he said.
"Hi there, thanks," I replied.
Through a narrow side door I followed Jack up a steep set of stairs. Anxiety began to flood my veins as I took each step.
"This is it," I thought to myself.
The stairs led up the side of the building to the top floor where we entered through a door on the right. I entered the room as Jack closed the door behind us. To the left there was a black leather couch and straight ahead was a desk accompanied by several chairs. Judging from the decor and items throughout the room I guessed that Jack was in sales of some kind. A small wood stove was in the far left corner. It was stoked and burning, but yet I froze with fear. I stood awkwardly in the middle of the room with my chest sunk and my hands anchored in my pockets. Jack took my coat then walked up to me. He was taller, had short dirty blonde hair, blue eyes and a warm strong face that had a pleasant demeanor and told me he had a girlfriend. I raised an eyebrow with curiosity, because it was obvious this wasn't his first time with another guy. As he came in closer I could smell the musk of his cologne. He motioned his hands up and rubbed my shoulders.
"You seem tense, just relax," He said, with a comforting voice.
"Ok," I smirked.
Jack instructed me to turn around and began to massage the shoulders of my skinny frame. His fingers had a firm approach as they tried to loosen up the tension in my body. I closed my eyes and tried to relax. At such a young age I was completely new to these sensations. For the first time ever another man was sensually touching my body. Jack slowly spun me around and moved in closer. His lips lightly kissed the skin on my neck. I reached my arms around, rubbing my hands across his back as the two of us stood and embraced each other. My nerves were lit with uncertainty, but at the same time I trembled with excitement.
