My first encounter with Santiago ("San") altered my mind and body more than I would have expected.
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.
I loved the feeling of his full weight on my back as he squirmed and wiggled in delight and the feeling of fullness I felt from his warm shaft filling and stretching my inner channel. It was then for the first time I understood the joy of giving someone complete pleasure by using only your body. In time I learned to use my internal ass muscles to milk his cock, adding to both our pleasure levels.
His youthful vigor made him get hard again in only a few minutes as I felt my channel expand again to accommodate the growing cock when I would relax completely and let him fuck me with full deep strokes. His first load deep inside me provided a welcome amount of additional lube that added to the longer more pleasurable fuck where I was more relaxed and was also able to wiggle and flex my ass in providing additional pleasure to both of us. The second fuck was always better, longer and I was able to enjoy and experience more of the fantastic sensations. No matter the room temperature, the second fuck never failed to bring both of us to a complete sweat until my ass was again filled with a new load of cum. When he finally recovered and withdrew from my cum leaking ass, he always took the time to suck me off before getting up to clean up before he left.
Our relationship got deeper and more intense as we entered this new phase of sexual intimacy and I thought it would go on forever until I made a greedy mistake that ended it all. In addition to having a fantasy of being anally fucked that I had finally realized I had always wanted to be fucked at the same time as I was being sucked. I thought receiving pleasure from both front and back would be the ultimate erotic experience. My error was in acting on that fantasy.
Before San and other partners, I had an older guy who love to come over just to suck me off on a regular basis. He would show up with a chilled six pack, sit on the floor with his back to the couch and let me face fuck him as long and as often as I wanted as long as he had another beer handy to wash the cum down. He was a master cock-sucked and did things to my cock no one had ever done before and always managed to suck at least two loads out of me with no problem. When I ran out of cum or he ran out of beer, he left until I got horny again to call him to come over and drain me dry.
To realize my fantasy I arranged for my cock sucker, Dave, to come over at the same time as San. I let them both know separately and beforehand that I wanted to do this and both of them had no problem in helping me fulfill my fantasy by pleasuring me at the same time. San arrived first and decided he didn't want to strip naked in front of a stranger so just dropped his pants and briefs and was just starting to fuck me as I leaned over the couch, when Dave arrived. He arrived with his usual chilled six pack, two of which were already gone and when he saw me naked answering the door and San half-naked standing by the couch with his 10+” cock glistening with lube that had just been balls deep in my ass, Dave wasted no time in popping another beer, taking off his pants and boxers and sitting on the floor with his back to the couch. I also wasted no time in getting into position by standing in front of Dave, leaning over him as he took my rigid cock into his mouth and down his throat. As I leaned forward over Dave and rested my hands on the couch behind him, San slowly re-enter my still lubed hole without any problem or discomfort on my part.
As the two of them started a rhythm of me entering Dave's mouth and slowly down his throat, San would slowly enter my ass up to his balls. Dave also licked San's cock as it came out of my asshole as well as rimming me. My fantasy was realized and was more pleasurable than I could have imagined. I was ecstatic. I had never felt so much pleasure at any one time. It took only a few minutes for me to cum immediately down Dave's throat as I felt San's load shoot deeply into my ass and at the same time I felt Dave's load shoot on my leg. No one stopped what they were doing, San continued to fuck me with renewed vigor, Dave continued to suck me until I was hard and we repeated the experience for another half-hour until we all came again.
San and Dave dressed and let themselves out as I lay prone on the couch exhausted thinking I had finally found the complete sex act I had always been looking for. After that one time San's visits started to drop off and when he did come over, he had a hard time getting hard and fucking me, He still sucked me off but the passion was gone. When it was getting obvious he just wasn't “in to it” any more with me I finally sat him down without sex involved to find out what had changed. It was then I learned that after my “three-way” when they left together, Dave had given San a blow-job in the garage of my apartment before they parted. Dave also offered to give San a lift to my place anytime he was coming over and he would wait for him downstairs until he satisfied me and then he would drive him back to his Aunt's place. The only catch was that Dave would give San a blow-job before he came upstairs for my meeting and gave him another when he took him to his Aunt's. San was being drained and enjoying it. I fell to second place and eventually when San moved in with Dave, he stopped coming over all together. They stayed together for a couple of years.
I ran into San a couple of years after that, by then he was thinking of moving out since Dave had become a complete alcoholic and most of the time was passed out. I offered to invite him over again, he feigned interest, took my number but I never heard from him again.