SERG – Chapter 4: The Fitting | Dallas Steele and Serg Shepard

I’ve walked past Mr. Steele’s shop more times than I count over the past year. And while the suits and tuxedos are certainly beautiful, the most striking thing is ( and always has been) Mr. Steele himself.

His well-defined muscles are apparent even from afar. His well-fitting tight pants and snug dress shirts look as if they were designed specifically for him. Then again, he is a tailor, but nonetheless, he always looks magnificent. The two of us have met each other’s gaze plenty of times, and every time my eyes catch his, my knees get immediately weak, my cock begins swelling up, and I can feel my hole start to expand as if to make room for what I am sure is healthy slab of meat hiding behind those snug pants, if the visibly heavy bulge of his was anything to base it off of.

As luck would have it, I have an event coming up for which I will definitely need a tailored suit, so I finally had a reason to stroll into his shop and get a fitting. Even luckier, he seems to have no apprentice or help, so Mr. Steele would be the one bringing his measuring tape to run across and up and down my body.

As I browsed around and looked at all the particular cuts and colors, I kept taking as many chances as I could to steal glances of the handsome man, and noticed that he was stealing plenty of his own. I finally found a couple of options that I liked and it was time to get fitted. My body was buzzing at the mere thought of this tall, older hunk touching me even slightly.

Momentarily, a slightly intrusive thought hit me: why was I assuming I was about to score? I mean, he is obviously checking me out, though more covertly than I was. I had become quite good at seducing, or at the very least, managing to score with some of the sexiest older men around. But I probably shouldn’t just assume I’ll get lucky. But alas, when it came time for this specific older hunk to take my measurements, my body felt electrified.

He took me to the back where there was a little dressing room. Everything began pretty typically. As he took measurements of my upper body, his fingers lingered much longer than was probably necessary. The more his touch seemed to linger, the more our eye contact increased in both length of time and intensity. I was clearly on the money with my thoughts, he wanted me just as much as I wanted him.

As he moved to my lower body, I began to leak. The way he measured my inseam didn’t help, what with him fully letting his fingers run into my balls and all over the front of my crotch; He was clearly able to both see and feel my erection. He decided to get bold himself, saying he’d get a “better measurement” if I removed the pants. I wasn’t going to argue, and I dropped them as fast as I possibly could.

My erection was now more apparent than ever, and the wet spot on the front of my briefs was enlarging. He actually came in to take another measurement of my inseam, and again let his hands both linger and even wander all over. He managed to keep a somewhat straight face and facade as if this was all routine, but once finished that facade faded a bit. He told me I could get dressed and quietly added I didn’t have to if I didn’t want to.

Of course, I didn’t want to, and while I didn’t want to get ahead of myself again, it was time for another measurement. This time though, I needed Mr. Steele to measure the depth of my throat and hole with his pole. Which, at this point, was clearly standing at full mast just like mine. We kissed intensely, and he rubbed the sticky moisture my leaky cock was producing as our tongues invaded one another’s mouths.

I took very little time to drop to my knees and pull down his pants, looking up at him as I took his massive length and girth into my mouth. Making sure not to break eye contact, I could tell he loved the idea of watching a little guy like me try to swallow all that meat. He unbuttoned his shirt as I sucked and licked every inch of him. His body was a work of art, perfectly muscular and defined.

Soon though, he needed my hole. He took me to the couch and had me get on all fours, diving in tongue-first, slobbering all over as he darted his tongue in and out expertly. After lubing me up with his spit, he managed to slide into my tight hole with relative ease. As large as he was, the size couldn’t beat the hunger, and my hole was essentially swallowing his cock.

He pounded me doggy style for a bit, but I could tell it was too much for him. He turned me over onto my back, he wanted to see my face while he pounded me, and I definitely wanted to watch him slide in and out of me too. His chest flexed with every thrust as he made love to me. He began to howl a bit as he was getting close, and I could feel his cock pulse inside me as he shot rope after rope of cum deep into my guts. This was too much for me, too, and I shot my own load all over my belly. He leaned into kiss me, a kiss that felt like both a thank you and a you’re welcome.