Young nervous thin dark red/white skunk [Eric] walks into a tailor shop, tailor tells him to go into the back room, strip, and sit in the chair - the tailor will be back to do measurements shortly.

Eric goes to the back, strips down to skivies. Tailor comes back and says, "Well, try these on while I get the tape", hands Eric a small pair of boxer briefs that looks a bit big in the pouch for the skunk. While the tailor stands there, Eric shyly strips then puts it on - yeah, it's loose in the front. Then the tailor takes a few measurements, lists them off, poking and proding the young skunk as he starts to flush. Tailor finishes then notices "The underwear was the wrong size, why didn't you say anything", Eric was about to say it was obviously too big when he feels the fabric tighten. Confused, he looks down to see his junk overfilling the jock, then comments "It felt fine a moment ago..."

Tailor harumphs, then says "I'll need to get another one. Sit down and enjoy some of the complimentary liquor", then leaves again. Eric sits down and inexpertedly pours himself a small drink of whisky, knocking it down. The burn goes down his throat and he coughs a little as the warmth spreads through him, his form bulking up as he begins to age a few years, growing a bit taller, his chest barreling out a bit, but noticeably, the hint of muscles developing on his otherwise naked form. 

Eric squirms a little as the fabric tightens again, then lets out a soft sigh of relief as the tailor returns with a medium sized pair of boxerbriefs, "Put this on." Eric does so, standing less embaressed and more confident as the tailor begins to measure him again, this time listing out larger numbers than before. Once again, Eric starts to feel a cramped pinching feeling, looking down to see his bulge very much visible through the straining fabric. The tailor sighs and says "Again, why dind't you tell me if it didn't fit right, I'll be back with another. Help yourself to the complimentary liquor," before leaving. 

This time, Eric took the jock off and let his baseball-sized balls dangle as he confidently poured himself more whiskey, knocking it back and chrring pleasently at the smooth warmth flowing down his throat and into his gullet, the warmth spreading through his body as he gained a few additional years again, his form filling out to maturity, his face losing the last vestiges of youth, pockets of fur on his chest, arms, and crotch growing a bit bushier. He lets out a soft sigh of contentment, his voice deepening as it escapes his muzzle.

The tailor walks back in, raising an eyebrow for a moment to see Eric and his grapefruit-size balls standing confidently, then handed the skunk another pair of boxer briefs, large around the waist and with additional space on the crotch. Without a worry, Eric slid them on, the extra fabric in the front not needed. The skunk stood confidently as the tailor once again measured him, only just now noticing how handsome the tailor was, before a sudden pinching down below happened again, both the skunk and tailor looking down to see Eric's hefty cauntelope-sized balls swelling, then tearing the boxer briefs. The tailor lets out a small gasp, and stammers "Er, I'll... get another pair, I'll be right back, um, there's... some booze there..." before fleeing, but Eric noticed a growing blush on the tailor's face.

Pouring himself a double shot and downing it with ease, Eric sat back in the chair and gave room for his soccerball sized nuts to be comfortable, enjoying the gathering warmth in his middle, a few more years settling on him as he became a confident middle age, his belly becoming pudgy, then bloating up and outward to become quite expansive.

Eric was slow to get up as the tailor, blushing furiously, meekly entered the room and pointedly not looking at Eric's watermelon balls, handed over another pair of briefs, then stuttered as he called out another set of measurements, squeaking as Eric 'accidentally' brushed the tailors hands with his beachball sized nuts, fitting snugly and comfortably in the skunk's underwear.

"Er, allright sir, um... I've got your measurements now... Is.. there anything else I can do for you?" the skunk blushed and stammered. Eric grinned, "Oh, there's something you can do for me, kid."