March 1st, 2024
Views: 4085 
Starring:
Description: Since discovering my sexual orientation and recognizing a specific attraction to older men, I've searched online to explore this interest further. Initially, my focus was on considerably older male figures, particularly those with a friendly and approachable demeanor, one often characterized by beards and chest hair, such as teachers. However, my attention soon expanded to include celebrities and acquaintances of my family: uncles, father figures, and even family themselves. At that time, I was not prepared to share these feelings with others, partly because I was still questioning whether my feelings were appropriate or truly reflective of my desires. I needed a suit for an upcoming function, and for that I needed measurements. I won’t mince words here, I had walked past one particular tailor countless times over the years while hanging out with friends or shopping with family. The tailor was a gorgeous man in his late 40s or possibly early 50s. He was massive and in incredible shape with a classically handsome face. I needed a reason to go in and see him, and now I finally had one. Once I walked in though, the nerves hit me instantly. What if I’m being irresponsible? This man could be married, straight with a whole family, and absolutely no interest in boys my age or of my stature. So I thought, somewhat clear headed, I’ll just get my measurements from this towering hunk, and jerk off vigorously at home. Just don’t be stupid. The junior me that lived in my pants, however, had other thoughts entirely. Even before I walked in, he was inflating and deflating rapidly at every dirty thought about this man’s hands being on me. Thankfully, the tailor, Mr. Steele, immediately disarmed me. He was friendly and charming as he led me to tuxedos in my size. I picked out the one that stood out to me, my mind racing, and tried it on behind a partition he had set up in the studio. I found it odd that in this day and age, a set up like this was acceptable, but I didn’t think beyond that. Especially since the tailor seemed to be watching. Which in turn, made me unconsciously go slow and show off as much as I could. But upon stepping out, I couldn’t read his face. It was stoic, in a professional way, though his demeanor was still warm. But I thought to myself I am so dumb, what’s wrong with me? Let this man do his job and work. Or work me. Whatever he wants… And I was inflating again. My shirt was baggy and loose, as were my pants. Mr. Steele seemed a bit puzzled as he tried to take my measurements. His smell was intoxicating and masculine. I kept looking up at him sheepishly, and then immediately back down any time our gazes met. He told me to take them off and that he would do the measurements without clothing for more accuracy. It didn’t strike me for a second that this was odd in any way. One, I didn’t know any better because I had never been to a tailor, so his request checked out to me. Two, my brain began doing sexual somersaults. I went behind the partition again and he sat in a chair facing me again. I stayed at the end of the partition where he could see me clearly. I was brazen and shameless, but I didn’t care. Or a part of me did, but the part of me that didn’t was a lot stronger. Upon returning to him, he began taking my measurements again. This time, his manly hands made skin-to-skin contact with my body. I quivered on the inside. It might have been in my head, but his hands definitely seemed to linger. Especially when he got to my chest, where he managed to bring the tape around to meet at my left nipple. I felt his finger brush over it at least twice, and he looked me dead in the eye, this time I kept my gaze with him. He kept eye contact as he took my waist measurement, hands still lingering. I was sure of it now. Was this really happening? My cock was getting way too hard as I stood there in my tighty-whities. He was measuring my thigh when I tried to smoothly adjust to hide it, he noticed and immediately looked first at my crotch, and then up at me. He didn’t react beyond that except to immediately take my inseam measurement next. I didn’t know what to expect, I held my breath in excitable anticipation. His hands on my inner thigh, I honestly could have came right there, but then it felt like his hands were making their way off; he got the measurement. Damn. But then, just as he was pulling his hands away, his large index finger stroked the underside of my full sack. It was brief, it was fleeting, but it definitely happened and my cock didn’t just twitch, it practically flung in my briefs. Mr. Steele stood up, still not breaking eye contact with me and informed me we were done and that I could get dressed. I, too, kept my eye contact, and just stood there. What was I doing? He stared back momentarily, and then said again that I could get dressed, but only if I wanted to. Did my ears hear that correctly? What exactly does that mean? Still, I just stood there, and low and behold—this hulking man brought his massive hand back to my waist and began to let it roam up and down my body, even over my crotch. Our eyes were still locked on one another’s. He leaned in to kiss me and let his hands linger at my inflated crotch, groping me. I took the opportunity to bring my own hand to his, an obviously hard, big man cock straining the front of his perfectly fitted gray pants. My body felt electric as this DILF put his tongue in my mouth and allowed mine into his, letting them roll around each other. I couldn’t take it much longer, I knelt in front of him, and he allowed me to unbuckle his belt, undo his pants, and pull out his long, thick, massive meat. I stared at it briefly before taking it in my hands and playing with it. He continued to let me do as I pleased, I could feel it throb in my hand which made my mouth water. And then, almost like an impulse, my head and mouth made my way towards it to have a lick and taste. I wanted to swallow the entire thing whole, but the best I could do was get the first several inches. He didn’t seem to mind at all, his soft moans and grunts told me that. As I continued to try and get as much of him in my mouth as I possibly could, Mr. Steele began to unbutton his shirt. Now almost entirely naked in front of me, save for his briefs at his thighs, and his pants at his ankles. I continued to suck and lick his cock, but soon he wanted to return the favor in some way. He asked me to get on his couch on all fours. He pulled down my briefs, and I must have been lost in some kind of sex-induced haze, because the second his stubble hit my cheeks and his tongue darted for my little puckering hole, I felt it open up and almost wrap around his tongue as it darted in and out of me. It felt amazing; nothing could feel better than this. But I needed more of him inside me. After thoroughly eating me out and slobbering all over my chute, he must have sensed my hunger, because the tip of his gigantic cock pressed against my little opening, popped through, and then slid right in. I was a bit bowled over, there was a lot of pressure and some straining. But the ease in which he managed the fit was incredible. He rested his hand on my lower back and gently pressed, instructing me to arch my back without explicitly saying so. And with that arch, I felt the whole thing make its way into my guts like magic. It was incredible, I felt every inch of him filling up every inch of me and he began to pump. I couldn’t help but let out boyish moans and whimpers with each of his thrusts, which were getting harder and faster. Subconsciously, any time he would pull back for a thrust, I realized I was pushing back to get him all back into me, which only encouraged his pounding. After a while, I think he began to get close so he pulled me off the couch and had me lay on my back on the carpet. He wanted to see my face when he unloaded. He knelt and slid his entire length back into me, I could tell he was deliberately slowing down and speeding up to really build his nut up. His moans and grunts began to get louder and his pumping picked up speed again, it was coming. When he finally let loose, those moans became roars and I could feel his cock pulse inside me with each squirt of his seed. He kissed me as he left the last few drops in my well-fucked ass.
