The Tailor
Introduction:
Interesting trip to the tailor
I was just out of college and doing the kid in his twenties thing by heading to the big city to see what it made of me. I had been in econ major and school and managed to get a staff position with a small stock broking firm. Only problem is, I didn’t have a suit, really any formal work wear. To rectify this, I decided to go the tailor and get myself properly done up (and coincidentally properly done).
An elderly Italian couple owned the nearest place to my apartment. They were somewhat suspicious though in that the only other people I had ever seen working there were very attractive men that all seemed younger than thirty. One of those men happened to be the one that serviced me the day I walked in.
“Good morning sir, is there anything in particular you are looking for today?” greeted a 5’10” blue-eyed blonde who filled out his dress pants and shirt quite nicely.
“Frankly, I need everything. I’ve never owned a suit, now I need a suit, and I have no idea what size I am.” He laughed at that.
“Well I can certainly help you out with that. If you would just follow me, we can do some measurements in the back.” He led me into an octagonal room behind the main one where there were three mirrors side by side, three closets opposite them, a stool against the wall opposite the door, and a small platform in the middle where I guessed I was to stand, which I did after he pointed to it. “ New job?” he asked as he pulled out some measuring tape.
“Yeah, can’t go in wearing the usual rags.”
“Arms up,” he instructed, wrapping the tape around my chest. “Thirty four and a half, you work out.” I blushed slightly at that, but maintained my composure. As he danced around me sliding the tape up and down I started to notice how cute he was. Each time he touched me, my body warmed up, and I was starting to get hard. He kneeled down in front of me taking the tape from my waist to my foot along my left leg and asked looking up into my eyes, “Do you swing to the left, or to the right?”
“Excuse me?” I really had no idea what the question meant.
“Hmm, how to put this…” He still had the tape along my leg. “When you get an erection, which leg does it stay along?” My cock suddenly jumped at the mention and through my pants touched his hand that was near my waist. He smiled, “Oh, so left then.” He continued working and said nothing of the accident.
“Sorry about that. Yeah, I guess it’s to the left usually.”
“No worries. I’m going to need you to take off your pants now.” He sat down on a stool next to be and waited.
“Um, okay.” I took my shoes off and placed them to the side. I then undid my belt and let my jeans slide down before kicking them off. My erection stood out obviously as a thick snake running down my left leg in my tightish boxers. His grin seemed to indicate that he was up to something, so not to be outdone, I decided to make the next move and lifted my t-shirt off my head and threw it to the side too. I didn’t expect the air-conditioned room to be as cool as it was, and my nipples immediately hardened, accentuating my relatively ripped hairless torso. I stood there awaiting his next move.
The tailor got up from his stool and walked towards me, the grin never fading. He kneeled once again in front of me and pulled out the measuring tape once more. Then against all the odds, he wrapped it around my thigh and simply resumed his work. I let an exasperated sigh escape my lips and he chuckled and looked up at me, ”Oh don’t worry, we’re gonna fuck. Just one last measurement first.” With that, he yanked down my boxers in one motion and lined the tape up against my hard dick, measuring it from base to tip. He grabbed the shaft with one hand and said, “Lovely!” before engulfing it whole.
I hadn’t been prepared for such callous action on his part and my knees nearly buckled as I entered his throat. He worked me for a while taking me as far as possible while kneading my butt and squeezing my balls. As I approached my climax I warned him, and he simply stuck a finger into my ass, pushing me over the edge. I exploded in his throat and he took it all like a champion.
Weak from the activity (It had been a while.), I stumbled over to the stool and sat down with by back against the wall, the last of my semen oozing out of my dick. “Thanks, I needed that.”
“Well, we’ve only got twenty minutes until the old man gets back from lunch, so lets make our time worthwhile.” He took off his shoes and socks and then hurriedly began to unbutton his shirt.
I got up and stood next to him on the platform. Grabbing his head with one hand and his waist with the other I pulled him into a passionate kiss. Our tongues darted in and out and we moaned as we ground our hips into one another. I pulled back from the kiss and smiled, “Let me do it,” I suggested, continuing to unbutton his shirt. I finished my task and slowly slid the garment over his shoulders, sliding my calloused hands along his thick well-developed arms. “Beautiful, just beautiful.” I raised my hands back up to his shoulders and slid them down his hairless chest and washboard abs as I lowered myself to my knees. With increased haste I took care of his belt and grabbed both the waistband of his pants and briefs at once pulling them to the floor. What must have been a nine inch long two inch wide monster jumped out at me in the best way.
I grabbed him by his shaft and pumped him a couple of times before looking up at him. “I need this thing inside me.” He smiled ear to ear and ran to one of the closets. His ass was amazingly toned and he must wax or something, because I could see his lovely puckered hole clear as day when he bent over to retrieve something. He stood back up and turned around with a condom and lube. “You do this often?”
“No, but I’ve always wanted to. Lie face up on the platform.” I did as he said and he knelt between my legs slipping the condom on. He then poured a liberal amount of lube on his dick and hands, and began working his fingers inside of me, preparing for what was going to be a jarring experience, regardless of how much dick I had already taken. Once I was adequately prepared (and hard again) he lined himself up and slowly began to fill me.
I was in heaven, already writhing in overwhelming pleasure and pain when he was only two thirds in, but it just kept coming. When he was balls deep I clamped my legs around his back and grabbed my dick. “Ready?” He asked with a smile.
“Do it.” He began to savagely pound my ass, pulling almost all the way out before slamming back in. His grip on my waist as he rode me was tenuous at best because I was sweating like crazy. I clenched my ass as necessary and could tell by his moaning that he was enjoying it. My prostate felt amazing and my hand was a blur on my dick as I jerked myself off to an orgasm (all over my chests) without going soft. By the time my second orgasm was coming along, I could tell that he was close.
I reached up and put my hand behind his neck, pulling him down onto me for a kiss. Our chests pressed together and my dick was squeezed between us. The warmth was amazing. As he leaned back up away from the kiss, I groaned, “Fuck me you fucking fuck.” His pounding became brutal and we came together is an explosion of ecstasy.
