Santiago by Larry Malone

I don’t know how long I stood at my opened apartment door with my mouth hanging open when I first saw Santiago, but it was longer than polite would allow. “San” was there in response to a general ad of mine I was running in a local sex magazine offering to host any one interested in a mature uncut cock for oral sex. Whatever I was expecting, it certainly wasn’t the strikingly gorgeous young Hispanic standing there. He was a little over six foot tall, (and as I later found out 18 years old), with iridescent brown skin, a trim body, longish, shiny, straight, jet-black hair – classic Mayan Indian features – high cheek bones and full chiseled lips. My cock started to get hard immediately.

I really didn’t believe his initial response letter to my ad stating that he was a “younger guy looking for an older man, slightly out of shape, with graying hair…” but since it described me perfectly, I took a chance and invited him over. I found out in our later conversations that San had a sexual relationship in his hometown, Mexico City, with his much older Uncle with a similar deion starting when he was younger. When his father found out several months earlier, he was sent to the U.S. to live with an Aunt to get him away from the Uncle.

San was shy, didn’t talk much,and was very embarrassed by his thick accent and broken English, but we talked enough to know that we were interested in each other. He said he didn’t have a lot of time that first afternoon, but he made it very clear that he wanted to “please me” by sucking me off before he left. Since I thought I was dreaming and would soon wake up, I wasted no time in closing the door and right there letting him unzip me, kneel in front of me, and fish out my 7-1/2”, uncut cock, which was already hard and oozing pre-cum. It was obvious that he was experienced and knew what he was doing. He was not only an excellent cock sucker, but he actually made love to my cock. He kissed the tip and licked the clear liquid from the head and then used the tip of his tongue to search my cock slit for more. Slowly he sucked my fully rigid cock into his hot wet mouth and at the same time created a sensuous vacuum that enveloped the full length of my cock.

I never remembered anyone taking so much pleasure in sucking my cock, and giving me such pleasure at the same time, as he appeared to be. Within a few short minutes, to my surprise, I was filling his mouth to overflowing with a large load that he eagerly swallowed. Before he left he made sure we set up another meeting for the next week, and as the door closed behind him, I stood there stunned, happy, and satisfied with my semi-hard cock hanging out of my pants with a last drop of cum on the tip.

I could think of nothing else all week as I waited for his next visit, which San promised would be longer. When the day came, I was hornier than I had been in years and was hard before he was actually in the room. We spent a little more time talking, but neither one of us wanted to waste a lot of time, and as he requested, I stripped naked and lay on the bed and, by his choice, he stayed dressed.

With more time to spend on our mutual pleasure, San spent more time kissing and licking my cock, blowing warm air all over the tip, lapping up the pre-cum as fast as the clear drops formed on the swollen red tip of my cock. He slowly sucked in my full length through those magnificently formed lips, licking the shaft as my cock slipped past them. When he had all of me in his mouth, he used the soft inside of his cheeks to rub my cock head, which was a new sensation for me that drove me wild and that I came to love.

As he sucked my cock with full deep strokes, one of his hands palmed my exposed cock-shaft when ever it was not in his mouth as the other hand eased under my body to gently tease my large balls and ass pucker. No matter how often I wanted our sex sessions to last forever, I never could last very long, and no matter how hard I tried, I couldn’t hold back my full load from exploding and filling San’s warm mouth after only a few minutes. Fortunately the two of us were never satisfied with just one load.

After I shot my first load, San would keep my half-hard cock in his mouth, gently sucking and licking it and playing with my ass-hole, until I was hard again. Then he would really throw his energy into sucking out my second load. Sometimes he would push my legs over my head and lick and tongue my asshole, which also was a first for me, and which would guarantee a second load in a very short period of time.

After the first few visits, he relaxed a little more with me each time and eventually even got undressed when he was with me. The first time I saw him nude, I gasped. He had at least 8-1/2” of thick prime meat hanging between his legs and that was when he was still soft. He was embarrassed he was so big and that was why he never wanted to undress. He grew up with people making fun of him because of the size of his cock.

At first we got together once a week and later twice a week. Each time he got a little more comfortable with me and I made sure I complimented him on his cock and its size until he accepted the fact that it was something to be proud of, not hidden. Eventually he would even let me stroke, kiss, and lick that wonderful piece of manhood. I even got a few inches into my mouth, and once or twice I managed to suck a load or two out of him.

As our relationship progressed, San started to spend more and more time on my asshole in between taking my loads, not only licking it but actually tongue fucking me into shear joy and ecstasy. He also started to drop hints and wondering out loud in English and Spanish how it would feel to put his cock into my tight hole and fuck me. He even asked me if I had ever thought of what it would feel like to be fucked by something more than a finger or a tongue. In reality I had spent a lot of time when growing up thinking about having a cock in my ass and getting fucked but never did anything about it. Technically, I was an ass virgin. I had dildos, fingers, and tongues in my ass but never a real cock and certainly never anything as large as his huge, magnificent, wide, formidable cock. I also never had the opportunity to try a real cock and I never met anyone I trusted enough and cared enough about to give my cherry to until San had suggested it. After awhile and a lot of thought I decided I would try it at our next meeting but I would surprise him by not telling him in case I backed out at the last minute.

On the day chosen, I not only took my regular preparatory shower before San came over but I also took a deep cleansing enema and after, packed in a lot of lubrication high up my rectum. When San arrived, I opened the door naked, and told him what we were going to do. He parted those luscious lips in a broad grin, asked no questions and wasted no time in getting out of his clothes, his cock was rock hard and sticking out a good 10+” as it bounced up and down as he followed me into the bedroom.

I placed a generous amount of lube along the full length of his rampant cock and shivered in anticipation of what I was about to try and marveled at the sheer size and heft of the warm flesh I held in my hand. Just in case, I added more lube to my asshole. I leaned over the bed, spread my legs, and grabbed both of my ass-cheeks with my hands and spread them wide, my glistening pucker twitching in anticipation. San stood behind me, got between my legs and gently placed the broad tip of his cock head at my entrance. He teased it with little circles, found the center target and gently pushed.

As my sphincter tried to adjust to the pressure and width of his cock-head, I felt enough pain to tense shut. San was sensitive, tender, and patient, but all his attempts to enter failed, as my ass fought to keep its virgin cherry status against the new monster invasion. San was willing to give up rather than cause me any pain or discomfort and lose the warm relationship we had developed up to then. But I was determined to keep trying, since I had made up my mind to have my ass fucked for the first time, nothing was going to stop me.

I had read somewhere that if you sat on a cock, your ass opened wider and it would be easier to control the rate of entry. I decided to try it. I had San lay on his back on the bed, his rigid lubed cock sticking straight up. I straddled his hips, and as he held his cock steady with one hand, I positioned my ass directly over the tip. I slowly lowered myself until I felt the warm slippery column tip touch my pucker target, but this time I controlled the rate of entry and knew I could stop at any point. By millimeters I lowered myself onto his cock, stopping when I had to adjust to the stretching or the discomfort, raising up when it got too bad, but eventually I took it all. I sat on that beautiful love instrument as I savored for the first time the pleasurable emitting warmth it generated and the feeling of shear fullness of it in places nothing had ever been before.

When I was comfortable with the new sensations and there was no more pain or discomfort, I eased myself slowly up and down on that pillar of mounting pleasure until I felt fully relaxed and I could rise and lower myself in full deep stokes with only new intense feelings of pleasure flooding me. When I passed that milestone, I eased off San’s cock, laid face down on the bed and had San lay on me and re-enter me causing no pain at all, and had him fuck me with full deep strokes deep in my ass. My virgin tightness and his pent up desire made him cum in minutes, but neither one of us wanted the feelings to end, so we stayed connected with his semi-hard cock deep inside me bathe in his cum until I felt him slowly get hard again and he fucked me for a second load.