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.
After a few moments we both started pulling at shirt bottoms and waistbands. Piece by piece each one of us lost an article of clothing. Before I knew it I was kicking off my underwear and I stood before him completely naked. I let my hands roam as Jack tried to warm me up with kisses on my neck and ears. The rough surface of his masculine build was new territory. I felt the strength in his muscles as my fingers grasped his backside. He pressed against my stomach and I noticed he was rail hard. I looked down and my eyes became wide. Veins rippled across the surface of his sizable shaft as I stood in awe. So robust and erect I took it into my hand. As I gently stroked the foreskin across his tip, Jack had found my flaccid package. Even with my excitement I was still racked with fear, and I couldn't muster any type of erection. My face went red with embarrassment and I tried to apologize.
"I'm sorry, I'm very nervous," I muttered.
Jack put his hands up to my face and quietly hushed into my ear, "Shhh just enjoy."
He was not deterred by my shyness and with his strong arms reached down and grabbed my cheeks lifting me into the air. With my legs wrapped around him a weightless feeling swept through me. He walked us over to the couch and lowered me down. I felt the presence of his hard cock graze the line of my bottom which sent a tickle up my spine. I was getting warmer and the fear began to shake loose. Then he came nose to nose and pressed a warm kiss on my mouth. Initially I resisted and tried to pull away, but then decided to engage. Our mouths opened up to each other and our tongues met. I eased up more and mt senses were awakening all over. The whole experience was making me incredibly hot. Here I was, naked with another man, embraced and kissing. It was trance-like.
My cowering manhood had now risen and I was rock hard. Jack dry rubbed his shaft up against mine and the sensation of cock against cock was electric. His hips pulsed into me, spreading my legs wide. I felt the air of the room hit my hole and all of sudden my whole body was buzzing. Jack pulled off my lips and moved lower. His mouth traveled my bare body, kissing my nipples and stomach, eventually landing on my hard six. His seductive blues gazed up at mine while he performed strong salivating strokes. I stared back; jaw dropped in amazement echoing subtle moans. He was swift and smooth and his saliva glimmered on my shaft in the low light. His strong hands pushed up my hips as he nudged beneath where he moaned with heavy breath right over my hole.
"Oh my god," I uttered, in a sultry tone as Jack slotted his tongue into my back door. The feeling overwhelmed me and my trance-like state elevated to a new level. I rubbed my cock as his tongue lapped and prodded. Feminine twists began to expel from my body and I arched my back as my fingers grazed my stomach in delicate motion. My legs were wide and I stretched my toes, succumbing to the curious sensations I had wanted to feel for so long. I felt completely raw and exposed but loved every second.
"Yesss, I like this little ass," groaned Jack, as if he were enjoying a delicious meal.
He forced his tongue in further and I squirmed in pleasure. While I moaned he added to the list of my new sexual experiences and inserted his middle finger into my virgin hole.
"Oh god," I hushed in delight, while his small extremity ventured inwards.
With his finger in my hole he moved his mouth back to my cock and started to simultaneously suck and frig me with incredible intensity.
