My Roomates and a Kinky Straight man went into business together and opened a Leather Shop. My Roomates put up the money and the Straight guy made the merchandise.
The business caught on and was doing well, but they needed to expand into mailorder. That's where I get involved. They asked me to draw the items for a catalog. So began my summer of drawing ball stretchers, tit clamps, gates of hell etc. etc.. The straight guy took great amusement in describing just how and where each implement was used. He got a kick out my blushes, gasps and occasional shudders. My sex experience at the time was limited to cocksucking and buttfucking. I have to admit sometimes as I'd draw a picture of a hunky stud sporting one of the toys my dick would get hard.
I got to be kind of a fixture around the shop. Regulars got used to seeing me there and sometimes I got a first hand look at how some things worked and fit. I was being paid and educated at the same time.
Now most of the merchandise sold was apparrel, chaps, vests, harnesses and such. All custom made and fitted. Sometimes I'd envy the straight guy, in the back room measuring some hot stud for new gear. My one roommate loved to measure for cock rings. I envied him that job too. I occasionally got comeons form customers, but for the most part was too nervous. I may be drawing such things, but no way was I ready to give some S&M Daddy a crack at me!
Sometimes for some reason or another I'd be left to mind the shop. Maybe a run to the bank, or to pick up more leather. Most people just browse maybe buy some small item. Anything custom had to wait for the Straight man.
One such time, a really gorgeous man walked in. He browsed for a while, kind of nervous and sheepish. That's a sure sign usually that he wants to buy something more kinky, but is embarrassed to say. I just leave them alone, they usually blurt out what they want eventually.
This guy was tall, dark and well built. His tank top and white cutoffs framed his body nicely.
He was handsome, with brown eyes and a black mustache. He had a bubble butt and nicely packed crotch. Kinky Roomate would have been all over him in a flash. I'm too shy.
I was abit surprised too finally find out all he wanted was a cockring. I was even more surprised when I asked him what kind and size. He kind of shyly pointed to the biggest one on display. ' That one I think?' Like I was supposed to know. I sighed, rummaged around under the counter and pulled out a measuring tape. ' You want to be sure with these things, too loose, they fall off in embarrassing places, too tight and thay could hurt something. Take this into the dressing area, get your self hard and measure around the base of your shaft and balls.' I was perhaps a bit brusque, but hey I'm not the most socially adept person in these situations.
He took the tape, went into the alcove and I went back to my drawing.
All of a sudden I heard a load thump, followed by a sliding sound from the alcove. I looked up to see a pair of legs, tangled in shorts, slide out from under the curtain. Alarmed I sprang up, ran to the curtain and pulled it aside. ' Are you all right?' He was lying there, eyes rolled up in his head ina faint. Pale as a ghost. And between his legs was the biggest damn dick I've ever seen outside of a horse. As his hard on receded I could see color come back into his face. I had no idea what had happened or what to do. As his eyes focused he looked up at me and blushed. I reached in a hand to pull him to his feet. As he stood wobble legged, I helped him to a chair. ' I'm sorry, sometimes that happens, when I get a full hardon.' At my uncomprehending look, he sighed. ' Sometimes all the blood leaves my head and goes into my dick!' I thought back on the monster I'd seen. It made sense somehow. ' But why the cockring? It'll keep all of the blood down there, won't it?'
' Yeah, but blood will get to my head shortly, but if I don't keep it in my dick, I'll lose my hardon. I'm gonna lose my sugar daddy, if I can't keep it hard enough to fuck him once in a while. So I need a cockring! I'm really a bottom, but I got keep him happy. The only reason he keeps me is this big old dick of mine!'
For some reason, ludicris as the whole thing seemed, my heart went out to him. I was full of questions, like if he couldn't stay hard, how did he come, but I kept them behind my teeth. Besides I wanted to see that club again. I went and put up the temporarily closed sign, and locked the shop door. He was still sprawled on the chair, flaccid cock hanging out six inches. Soft it was about the size of most hardons I'd seen. I retrieved the tape from the alcove and walked back up to him. ' Try again, take it slow, stay in the chair, and I'll measure it for you.' He smiled then began to stroke his dick. It grew, and swelled and grew. Seemed like it was never going to stop. It was like a Tom of Finland drawing coming to life. He looked up at my slyly, ' It would really help if somebody played with my ass while I jerk!' As I have always been an ass man, it didn't take long for my hand to reach down between his legs under his balls and start rubbing his hole. That monster jerked even higher and wider. I know my eyes got wider! The head was so fat I doubted I could even get it in my mouth. The guy slowed down, his eyes were closed, and face was pale. Making a quick decision I wrapped the measuring tape around his dick and balls and pulled it tight. His dick stayed hard, his colr came back. I couldn't resist. I ran the loose end of the tape up his dick. Eleven and a half inches. Still holding the other end tight I wrapped the loose end around the flange. That thing was six inches around. My God it would be like a fist punching into my gut! Still holding the tape tight I began sliding my hand up and down the colomn. He gasped but didn't ask me to stop. As I stroked him he scrunched on the chair and lifted his legs up a bit. He wet his fingers and started fingerfucking himself. All the while I'm jacking him and keeping pressure on the measuring tape. Not able to take the whole head in my mouth I did lean over and suck as much of it in as I could.It didn't take long, after that, this guy must have been desperate to pop. He shot off all over my face and shirt! Still holding the tape measure tight I marked it with my thumb and finger and let go. I held it up and whistled. ' Buddy, you are gonna have to custom order a leather ring, there is nothing in this shop that's gonna fit that monster!' He groaned. 'That going to be expensive?' ' Not the first one buddy, that one's on me! Noone would ever believe me, but it's one treat I'll never forget!'