My First Time!....

I had always wanted to get fucked by a man all my life. I can remember as far back as six when I got caught by my mom with a picture of a hairy construction worker cut out in my drawer and got away with the “birds and bees” story instead. I vowed to hide my feelings better after that one.

Fast forward ten more years. I had a bad year in school and miserably failed my night grade year. Shit, my Dad was pissed off! I can remember him standing there yelling at me, telling me that I was the worse kid he had. Then he did something that got me excited. “You are going to live with your sister in San Mateo!”, he yells. My insides jumped. I had heard that the San Fran area was teeming with hot men and I thought that maybe I might get lucky and have my first experience with a guy.

I was at the time very skinny and lankly on a five foot, seven inch frame. A very cute face with dark brown hair and brown eyes, and very unsure of myself. Talk about the lack of experience. I had not started experiencing men in my local hometown mall. My now hairy legs and butt did not fully develop tell I was almost 20, but it showed signs of promise.

I landed at my sister’s apartment with nothing to do. Seems her and her husband needed a place to stay while he was stationed there for the Navy. Like any smart person, my Sis saw an opportunity to manage an apartment complex to get free rent. I was kicking around for about three days when the apartment’s regional manager stops by to visit and makes a suggestion. He need a grounds keeper for my Sis’s apartment and I could earn some cash doing it, so I took the job.

After cleaning most of the grounds that week, and working my body off I finally got some time to myself. Cleaning the grounds got me the chance to learn the layout of the place and see who lived there. While I did not get so see many people, I did get to know the grounds. A lot!  The place was laid out like a big tee formation with most of the apartments on second floors and the parking below. To one side of the tee was a stone courtyard and the other side was a small garden with a hardwood patio, enclosed and gated, and a hot tub. Little did I know that hot tub would become the start of my hottest experiences and a great summer. All I knew was that I had to clean it and manage the PH levels. More work. Pah!

I decided since I had some time and grew some sore muscles after a long week of working that I take a break and climb in and finally enjoy myself.  Settling back to let my aching muscles relax and closed my eyes. It did not even occur to me to open my eyes when I heard an apartment door open and close and flip-flops come down from the second floor level apartments and in to the patio. I thought who ever it was would just lay out on the lawn chairs scattered around the patio, but I was wrong.

“Hello.”, said a deep strong voice.

I opened my eyes to a man six feet tall, about 190 lbs. At that moment I saw a man that had the looks of Tom Sellick, and Robert Redford combined, with an athletic body. Brown hair and deep blue eyes, but I was not looking at his face, I was face level with his crotch, which had a pair of black Speedos on and yellow stripes. From what I could see those Speedos were trying to keep in a big package and not doing well at all.  Those very defined hairy legs to match that very hairy chest and goatee.

“Hey”, was all I could blirt out.  I think he noticed I was staring, but did not say or show much.

“May I join you?” He flashed me a smile. The kind that Tom Sellick uses in Magnum and my heart flipped!

“Sure.” I moved from laying in the deep pocket to a bench so he could take the other bench across from me.

He settled in and proceeded to asked me some small talk. I barely remember what was said. Something about being the apartment managers brother, and that he had heard of me and had been watching me work all week. He told me his name was Steve and that he had lived in the Bay area for almost 10 years. That whole conversation was pretty much a blur. I just could not stop watching his hairy chest and wonderful smile. The conversation pretty much waned fast. It was then he complained he was hot and moved up to sit on top of his bench area. He continued to make small talk and then he did something that almost made my eyes pop out. He rubbed his crotch with his finger! Now for a sixteen year old, virgin gay man that was like seeing the Pope, the President, or a UFO show up at that moment. I know it showed on my face as well starting in my crotch. I got a huge boner! I got out on the edge as well, and thought “What the hell”, and proceeded to copy him.

A huge grin came across his face and he dropped back into the water. I followed him. He reached across the tub with his foot and proceeded to rub my crotch with it. I got even harder.

“What do you like to do?” he asked. The look he gave me was deep and warm. The kind of look to this day makes me melt all over.

“Dun no”, was all I could blurt out.

“Then come over here”, he said.

I pushed across the tub to reach out and touch his dick in those Speedos. I then proceeded to pull out his seven inches and rub my hand across it under the water. I heard him mown with suppressed pleasure. I wanted so much to suck on that dick. To see this hairy bearish man respond to my actions. I wanted to see this gorgeous man cum so bad, I know I was oozing precum under that water. Then to my bad luck we heard a noise and quickly moved apart.

We both agreed that it was not safe to be there. I asked him if we could go up to his apartment and he explained he had roommates and that there would be no privacy. I told him then that I had a master key to the complex and that we could meet in an empty apartment. He agreed. Time was set for 30 min from when we left the patio. I almost ran back to my room in my sister’s apartment to chance into some shorts and dry off. I told my sister that I was going for a walk and would be back in a few and excitedly walked to the empty apartment to wait for Steve to arrive. I paced the apartment, knowing that I would get some sex with a man for the first time in my life. I was both existed and scared at the same time. I heard footsteps down the walk and peeked thru the peep-hole to see him walking up to the door. He was wearing a sweatshirt and jeans and still looked so very good looking and hot!

He knocked and I opened the door. Walking in he proceeded to grab me and while closing the door kiss me so passionately that to this day I remember how that felt. He proceeded to slowly take my shirt all the while still kissing me sucking around my neck, mouth and ears. I reached under his shirt to rub my hands thru his very thick chest hair. God it felt so good! I had a hot man right next to me and could do anything I wanted. I fumbled down his shirt to unbutton and unzip his jeans to grab his very big hard on of seven inches.

He pushed me back a bit and told me to get down there and suck on that cock. I eagerly accepted. I got on my knees and grabbed that tool. All my time cruzing the bathrooms in my hometown mall helped me take that seven inches with no difficulty.  I wrapped my lips around that head and proceeded to take all of it down my throat. He let out a load mown. I took that full dick and proceeded to let him fuck my face with it. It was exhilarating feeling that cock-head hitting the back of my throat. He started to pant heavily as I looked up thru his pole to his now fully exposed hairy chest. Those Pecs and nips showing thru the mounds of chest hair. Somehow I did not notice him removing his sweatshirt, and what a sight!  Guys, if you ever done that you know what I mean. It is something I never get tired of seeing.

He stopped me. “Man, stop or you going to make me cum,” was all he said. I stood as he proceeded to remove his shoes and jeans to stand totally naked in front of me. I paused for a sec to admire his fantastic body. I was very hard by now. He saw my distress and smiled. “Want me to suck that for you?” he asked.

“Please?” I pleaded. “Suck my cock.”

He got down his knees to take my hot dick in his mouth. His moves were of a man experienced and knowing what he likes. Grabbing that dick in his hand he proceeded to slowly pump on it with his hand, slowly admiring every angle and movements it made. He then did something at the time that I did not even think was possible at that time. He started to lick the head and shaft, slowly still, taking his time and making me shiver and convulse in ecstasy. He then wrapped his lips around the head and proceeded to take it all down into the back of his throat. That moment sent a shockwave thru me and I gasped with pleasure. Combining that deep throat action with a vigorous pumping movement sent me to climax fast and I came in minutes. Swallowing every drop he held on to my shaft in his mouth for a min or more, teasing me with his tongue. I just could not stop shuddering and convulsing with the shockwaves running thru me.  It was the best blowjob I had ever had at that time and one of the best in my life.

I thought we were done, but Steve had other plans.  “Get down on your hands and knees. I am going to fuck that tight ass and you are going to like it.” He said. He sounded so forceful, so masculine in that one statement that eagerly complied, but wondered if it how it would feel and if it would hurt. This was my first time and it both frightened me and made me want his hard dick even more.

He started by lubing up my asshole and stuck a finger in to try and loosen me up. God the pain!  I thought the whole world had been shoved up in there. He noticed my discomfort and said, “You think that hurts, just wait a min.” I then heard him chuckle and fear really did get the best of me right then. I thought about calling it off and ways to say I did not want to. Reveling in my thoughts, I did not pay attention to his movements tell it was to late. Next thing I felt was his big head on my asshole. That brought me back to the now really fast! The push was both the most painful experience I ever felt and the best at the same time. I felt him slowly penetrate that tight ass and mown again with pleasure of it all. He did not stop tell he was totally in me and our asses were touching. He paused for me to get my breath and proceeded to start fucking my as fast as a male rabbit would, or a man that it would be his last. God if felt so HOT! The pleasure moving through my body rocked my mind as well and my dick responded by getting rock hard all over again.

“Yah, what a tight ass”, was all he panted along with “Fuck ya!” He fucked my ass what seemed for hours, but probably more like several minutes tell he stopped, pulled out and ordered me on my back. I eagerly complied. To be separated from that dick in my ass was like not having your best desert for a long time. I wanted more!

I got on my back and he slid back into me so fast I did not even know he was all the way in. The look of him fucking my ass and seeing that hairy chest rippling and his ass moving in tandem to this day wants me to recreate that moment, so I pick that position over most others. He started to fuck my ass harder and faster yelling out a range of statements from “fuck”, to “Oh yes!” I felt his hard dick get even harder and bigger and then he pushed one final thrust in me and came with an explosion in my ass I felt the cum in my stomach, pulsing thru my very well cooked asshole. God, that was so hot.

He paused and still in side of me grabbed my very hard dick again. Using the cream he proceeded to jack me with his dick inside me. That feeling of his hot, still hard dick in me and his masterful hands did not take me long to cum again. I exploded on my stomach and chest for the second time as much as my first and managed to even hit my chin. He then pulled out of me and collapsed on me, kissing my neck and mouth. He pulled away enough to flash me that impish grin to this day I will never forget. I felt so satisfied at that moment. My ass felt like it exploded, but I did not care. I had the hottest man and experience I had ever had in my life up to that moment. My first ass fuck and I enjoyed.

We separated from each other and cleaned up. He left the apartment and went back to his. I proceeded to erase any evidence were there and go back to my room in my sister’s apartment. I spent many moments with Steve that summer getting fucked and seeing stars from it, but I did not care. I had my experience and came to love it even more over the years. When I did finally leave to go home after that summer, I got to see him one more time during the Christmas holidays when my parents came to my sisters for Christmas. I never did see him again after that and sometimes wonder what ever happened to the man that popped my cherry.

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