Three years ago, I used to listen to one of the local community radio stations. This particular night was different from every other night. A deeply masculine and soothing voice spoke “I am a married man secretly searching for an experienced mature gay man for a massage. I am an anal virgin made for your personal pleasure.” I was instantly turned on by his offer. Plus it was free, so why not? He continued “If you are interested in popping my tight cherry, contact the radio station for more details.” I hurriedly contacted the radio station who told me to meet him at the local docks in New York.
That night, I arrived at the docks and looked for him. The radio station told me to look for a man wearing a gay colour coded handkerchief in his right pocket of his jeans. I walked down the docks and looked for the man. I saw him first and watched him from a distance. He had short blonde hair with a fringe, his muscular body was perfectly outlined through his tight white shirt and tattoos covered his arms. Our eyes met for the first time, he smiled through his beard and adjusted his shirt in hopes that I would be the lucky candidate he had asked for.
I walked up to him and we spoke for a long time. I found out that he worked on the docks and frequently traveled out of New York. He had been married for five years but fantasized about his previous sexual encounters with his childhood friends. The sexual experimentation with his friends went no further than peeking at each other’s penises. Ever since then he had countless sexual thoughts of experiencing anal sex with a gay man for the first time. He appeared uncertain about what he was doing, he was so timid and almost powerless.
Since he was a beginner, I did not want to rush him. I decided to invite him over to my house for a drink and personal massage to see if he would like things to progress. I have worked professionally as a part time masseuse for the past couple of years and I had found that it is an extremely pleasant, nonthreatening approach to become more acquainted with somebody. We drove over to my place.
I gave him a cold beer and we chatted for some time until he was relaxed. At that point, I led him downstairs to where the massage table was. I instructed him to undress while I retrieved the oil and towels from another room. When I got back, there he was on the table, absolutely stripped and spread out like a smorgasbord. I took a gander at his ass knowing nobody had ever been in there before. I salivated.
I gave him one of my best and most sensual massages that I possibly could. He began to moan with every stroke. He rolled over onto his back and he placed his hard erection into my hand. I made him spread his legs with my free hand and plunged my mouth onto his cock. I slowly licked, slurped and drooled my way down to his rosebud.
I became harder knowing nobody had ever rimmed him before. I began to do my specialty, he lifted his legs lifted off the table which allowed me to get my tongue into his sweet asshole. He was squirmed and groaned in absolute delight as I twisted and moved his ass checks down into my face, almost like a dog in heat. When he was overwhelmed and could scarcely talk, I slid my tongue right into his rose bud and moved his body back and forth. I stroked his cock until he was about to cum. I quickly placed his cock down my throat and he came in immense spurts down my throat which I was pleased to swallow. As he rested, he groaned with relief.
I was in sweats and my shirt was soaked through. As he got dressed, he told me that nothing he had ever experienced before compared to the massage. He noted down on my calendar the times he was available. As he exited my house, he swore he’d be back.
Early the following week I got a call from him. His wife was going away, he needed to come over and see me once more. He asked “Would it be okay if I spend the night? I’d truly love to.” I of course said yes.
On Thursday, he appeared at my doorstep. He gave me a big embrace and laid a sweet kiss on my cheek. We talked for some time, this time he appeared to be exceptionally eager so I took him down the stairs for another massage. When I got him downstairs it was obvious he wasn’t there for another massage, if his erect cock was any guide.
I ate him out again until he was on the verge of moaning. I peeled my garments off while I went down on him. I placed some SuperSlyde lubricant onto my fingers and inserted them inside. I began to finger him, moving them in and out. He groaned as his ass tightened around my fingers. I slowed down, moved my mouth to his ear and said “Do you want me to top you?” I inhaled into his ear. “Would you like to get fucked by a man?”
“Hell yeah!” he replied. I was hard as stone from listening to him groan and his words simply made me harder. I got the lube and rubbed it on my cock. I moved up on the table and settled between his legs. I pulled at his hips until he was up on his knees with his face still on the table. I gazed down into his totally gaping ass. His hole was a bit red and swollen from the fingering I’d effectively done. It almost sparkled in the low light with the lube I’d placed there. It looked like heaven’s door to me and he moved his hips forward and backward. His gape opened and closed as if it were winking at me. It opened and shut automatically as he knew what was about to happen to him. I grasped my cock at the base and swiveled my hips forward. The tip of my cock touched the wet entrance and simply kissed his gaped ass.
“Alright, I’m going to slide in. Push out, as if you’re taking a dump.” I said.
He kindly pushed out and when I saw his little gape open, I quickly began to squeeze the tip in knowing this would be his very first gay anal experience. At first I felt the resistance, but it began to give way which gave me a chance to slide it further into him. His little gap was only able to tolerate the head of my prick. When I popped it further inside, he snorted like he’d been punched. I halted totally still for a minute and he began to move his hips once more. He backed into me and pushed a couple of inches of me into his cherry butt. He whimpered a bit under his breath. His back was completely covered in sweat, the inches that he inserted had inspired him to push even deeper back onto my cock.
I was completely inside of him, my balls were tight against his ring and my pubes scratched up against his butt cheeks. He groaned and gasped for a moment or two. I kept still and absorbed the mind boggling warmth and tight hold of his virginity. I ran my hands up his sides and down his spine which calmed and unwound him to get him prepared for more. I was going to ride his virgin ass hard, however I needed him to be completely invested so that he could always remember the hot and steamy moments of his first time.
I stayed still until he began to move under me. Then I slid myself out by only an inch and inserted it once more deeply inside. I rested as his hot ass grasped onto my hard cock. After every two breaths, I would move out and then back in. He groaned even louder and snorted each time I thrusted into his virgin cheeks. Each time I would go as deep as possible, with a throaty snort I rammed my cock right up into his pelvis. He began to move his butt once again into me and countered my strokes. His back broke out in shivers.
I was delicate with him but I used incredible power. I needed him to realize that it was a man in his rear end, that his virginity had been taken and there was no retreating. He angled his bum up into my groin with a full stroke and made a higher pitched groan. He did it again and made a little snort when it bottom. He was somewhat freer now, his virgin gape took me in more easily and it was beginning to feel great. The floods of joy were beginning for him and I knew the time had come to turn up the power a bit.
I lifted him up a little on the following stroke. This time I massaged my cock over his prostate. He made a startled sound. He moved once again into me and I pushed somewhat harder back in. His head swung to the side, his eyes were shut however his mouth was open and a little dribble spilled out the side of his lips which wet the sheets. I went into him quicker and harder this time. His body quivered under the blow, yet he continued to groan.
I thrusted in hard, his head lifted off the table somewhat and he groaned louder. I reached around his waist and held onto his prick which was rock hard. It spilled out with pre-cum. I massaged his pre-cum everywhere on his cock head and stroked it with a tight grasp. He intensely shivered as he yanked his head back hard when I pummeled into him.
After a few more hard strokes, I hauled my cock out of him. He grunted as I dragged him off the table and I pushed him down over it. I kicked his lower legs apart and slid into his rosebud with one hard stroke. I continued to stretch around and jerk his throbbing prick. I used his own pre-cum as lube. I fucked his butt for the following 20 minutes, blending short hard thrusts and long moderate strokes. He adored every moment.
At long last, his groans got louder and higher pitched. He thrusted back into me harder on every stroke. His head was going here and there on every stroke. I fucked harder into him, his prick swelled significantly harder and it knew it wouldn’t be much longer. I wasn’t too far away myself, I could feel my nuts tighten and the humming sensation that lets you know it will be a huge load.
All of a sudden he was there. I extended my body over him, I beat my hips into him and jacked him hard. With a profound snort, his prick spasmed in my grasp. He raised his head back. He spurted and spurted all of his seed over my massage table. His rosebud held me inside as firmly as it had when we’d initially begun. He discharged cum out everywhere on the table, his entire body writhed like a snake and his ass spasmed on my cock.
I beat two more strokes into the tight grip his ass had on me. I held myself hard and deep inside. I hammered out a hot and substantial load into his virgin ass. I shivered and gasped. It felt sweat and smooth. My cock pulsated in him as his ass drained out the last drops of my cum. I held him tight in my arms, one hand placed on his chest and the other cupped his balls. I lay forward over his back and simply inhaled into his neck for a minute. I rubbed my facial hair against his delicate skin for a minute.
He turned his head and looked at me. He wore a grin of a sexually fulfilled man – a bit timid, however extremely fulfilled.
That was the story of how a man of the docks lost his cherry for the very first time.
Anna has been writing original erotic works for quite some time and specializes in Asian fantasies. When you have a few minutes and want to relax by reading some FREE original hard core adult stories you are welcome at the adultsmart blog.