A December Night

This is the story of my first time with another man. Enjoy.

*****

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 for 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 lead 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 me. 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 closed the door and walked up to me. He was taller, had short dirty blonde hair, blue eyes and a warm strong face that had a pleasant demeanor. He told me he had a girlfriend but I could tell this wasn't his first time with another guy for his body language moved with too much confidence. As he came closer I could smell the musk of his cologne. His hands rose up and rubbed my shoulders.

"You seem tense and nervous, just relax," He said, with a comforting voice.

"Ok," I smirked.

Jack instructed me to turn around and he 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 swooped 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 even more as our wet lips kissed in unison. My senses were awakening all over and 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. At which point he 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.

"Holy shit!" I gasped, with my head back. Heavy breaths expelled from lungs and my hands gripped the leather. His finger was rocking my prostate wild and I moaned in zealous heat as his mouth worked my cock with his strong stroking style.

"Ohh fuck! Ohh fuck!" I howled, feeling my body twitch as I was pinned within the clutches of an emerging orgasm. Jack lifted off my cock and rose up to my face. Again, he pressed his lips against mine and we kissed passionately for a few moments. I grabbed his cock and stroked it as we stared at each other. My orgasm had subsided but Jack had edged me to the point of no return and I knew exactly what I wanted next.

"I want you to fuck me," I demanded. "Fuck me with this big cock."

"I'm happy you said that," he replied with a smile.

Jack walked over to his desk and pulled open a drawer where he retrieved a condom and a bottle of lube. As he made his way back over I glared at his thick eight inches. It swung rigidly from side to side, angled upward revealing its engorged features. Feeling like I was about to be punished, I thought to myself, "Is this going to hurt?"

He rolled the condom on and applied an ample amount of lube to all areas. I sat back with my head towards the end of the couch. Resting on a couch pillow I propped my left leg up on the backrest while Jack pushed my right leg wide and got into position. His dumbbell of a cock was seconds away from my longtime fantasy coming true and I could feel my heart rate start to rise.

"Here it comes" Jack said with a steel look as he took aim. I quickly felt the pressure of his cock against me. His hot purple head moved in and I yelped in pain from the initial stretch. "Ow! ow! ow! Slow slow!" I shouted. Jack pulled back a little and then plunged back in. He was slow but firm and wasn't backing off.

"Owwww!!," I screamed as his cock broke into me.

"Take it out! Take it out!" I demanded, but he didn't. He came in close and held me down as I tried to wiggle free from his penis.

"Relax, breathe," He whispered, in a comforting voice. The pain was intense, and I grit my teeth as the fibers of my rectum stretched to new lengths. Jack slowly pulsed back and forth with his cock about halfway. I stared up at him in discomfort, biting my lips to get through the sting. Eventually I felt a hot flushing feeling as the blood in my body rushed to the area. I continued to breathe and tried to relax my hole. The less I fought the less it hurt and finally my little hole started to adapt to Jack's size. He slowly pulsed in and out with half strokes, and I continued to let out little whimpers as remnants of pain still shot through.

"Mm ahh fuck," I would cry.

He pulled out to give my hole a break and I collected myself for a minute. I massaged my little gape which was hot and tender to the touch.

"My god you're so big," I remarked. I had used dildos before but it didn't compare to this.

"You're doing great; you have such a hot ass," He replied with encouragement.

More lube was applied and his cock was back in. This time was much easier and it was really starting to feel good. Jack started working it in deeper and I stroked myself as he rocked into me with his powerful hips. His well-built mid 30 year old body looked so hot. Sweat beaded on his chest and stomach, and I became even more turned on watching the pleasure he was getting from fucking me. He was my dominant top and I was his bottom boy. Soon my ass was fully warmed up and he was fucking me with nearly the full length of his cock. A few times he went too deep and I had to have him back off, but once he figured out a good depth he really started to go hard. I held on the best I could as my legs dangled wide while Jack punished my little hole. I was helpless to his big cock, which forced pathetic little cries out of me with every inserting pulse.

"Uh...Uh...Uh..," I moaned in repetitious fashion, "Uh...Uh...Uh...Oh god."

Before long the heat was back to full tilt and I could feel my juices starting to really move. Heavy sweat poured from both of us as Jack fucked my young body. The leather became slick and the air humid. Restrained under the manhood of this creature I felt completely free. My lingering homosexual thoughts, emotions and insecurities escaped their traps as I lost myself under the hunger of Jack's frame. His masculine groans rumbled through as he too released his own closeted frustrations. The wet slurp of his veteran cock pummeling my virgin flesh crackled wildly and we both soughed in pleasure. As he got closer to climax he would slow up, pull his cock out, watch my hole pucker, and then punch his cock back in with a violent thrust. I dripped in lust as pre cum started oozing from the tip of my budding cock.

I grabbed my ass and spread myself wide. I wanted him deeper, further, completely in me. At this point we were both so hot we could only mumble inaudible moans to each other. I was close, my chest was tight and my breath became shorter by the stroke. Suddenly, my flood gates opened and I moaned in a craze as I began to experience the most ground shaking orgasm of my life. My body bucked as strings of cum ejected wildly from the tip of my cock. Waves of incredible sensations soared through every part of me. I thumbed massive amounts of cum onto my stomach in complete pleasure and after watching me blow Jack wasn't far behind.

"Give me that cum baby!" I growled, with an eager and lustful tone.

He fucked my ass faster and I cheered, telling him I wanted to his cum. His escalating moans were getting much louder and I watched his face contort with agonizing pleasure. His orgasm came to the surface and he pulled out, ripped off the rubber and hustled up to my face where he blew a heavy load.

"Uh yea! yes! fuck!" He bellowed in a long heavy liberating moan. Sticky hot globs of Jack's seed shot forcefully from his cock as I waited with my mouth wide open. His salty juice felt like such a reward splashing across my mouth and face in chaotic fashion. The tension in Jack's body released with more heavy moans as I suckled the last drops. I was in heaven and my intense orgasmic feelings were still flowing. My legs shook uncontrollably while my whole body fell into a complete feeling of ecstasy.

Exhausted, Jack collapsed onto me. We kissed hard, our tongues exchanging his cum as we relaxed in the midst of our mess. We gazed at each other, exchanging mutual looks of approval and satisfaction.

"That was incredible," I said.

"So hot, that was just what I needed," He replied.

Jack pulled a blanket from the top of the couch, nestled next to me, and we fell asleep.