Coming of Age

Underwear Night

“Oh, my god!” exclaimed Troy as I stumbled my way into our room. “What the fuck have you been doing?” Embarrassed as hell, I began apologizing profusely, which only caused him to laugh hysterically. “Stud,” he said, “You look fucking hot! I want you to fuck me right now in that suit.” Well, how could I refuse a request like that?

When we stopped panting, I said, “Thank god that Mike and Maria didn’t see me in the lobby.”

“Yeah, but I know who would love to see you in that outfit,” he said. “The Outlaws.” We had exchanged phone numbers with them last night, so Troy called The Flirt and invited the guys to come over for a little show and tell.

The guys whistled and gave me catcalls as I modeled the outfits for them and recounted my experiences with Gabriele. “Everyone in Milan loves Gabriele,” said Dirty Boy. “That is why we all shop there.” When I got to the part about Gabriele pulling down the flap on my leather briefs, The Flirt said, “You mean like this?” and he dove for my cock just as Gabriele had done. Well, that started it, and the six of us ended up in an orgy.

“You should wear that outfit to Dante’s this weekend,” said The Flirt when we lay around in a heap of man flesh.

“Dante’s?” I asked. The guys explained that there were different kinds of gay clubs. The one where we had met them was a dance club that attracted mostly young people. There were also neighborhood bars, where friends got together to socialize, and cruise bars, where men went to pick up other men for a good time. Most bars have “theme nights” such as karaoke, underwear night, naked night, and leather night, but there were also a couple of bars that focused exclusively on the leather and denim fetish, and Dante’s is one of them.

“And the place will be packed this weekend because it’s Pride Week. You will be very popular there,” added Little Cherry, “especially if you wear those chaps.”

I had read about Pride Week on the Internet, but I really didn’t know much about it, so the guys educated me on that point. We also decided to go to Dante’s on Friday night because on Saturday it would be packed and difficult to get in.

“That sounds hot,” I said. “Troy would probably love that, but I’m sure I couldn’t get in since I’m not yet 18.”

When The Flirt learned that I was only a couple of months shy of my 18th birthday, he said, “No problem. We can get you an ID.” He took a picture of me (with clothes on) and said he would have the ID for me by Friday.

“The bars tend to relax their rules on Pride Weekend,” added Little Cherry, “but when you show up in that outfit, nobody’s going to be focusing on your ID anyway.”

We began to discuss which of the clothes I should wear and which Troy should wear, and then it hit me like a Mack truck. In my frenzy, I had rushed out of the store without paying for my merchandise. Once the guys had regained their composure from the uproarious laughter, Dude said, “Do not worry. We will meet you there tomorrow evening to settle up. Gabriele will be delighted to see you again. Besides,” he said, “you have the pants now, but we will help you select some shirts to complete your outfits.”

The next morning, Tuesday, Troy had his Italian lesson as we toured Sforzesco Castle, a 15th century fortress that is one of the largest citadels in Europe. Renovated several times, it now houses many of Milan’s museums and art collections, including Michelangelo’s Rondanini Pietà, and da Vinci’s Codex Trivulzianus manuscript as well as works by Mantegna, Canaletto, Tiepolo, Vincenzo Foppa, Titian and Tintoretto. The castle also contains museums devoted to ancient art, musical instruments, Egyptology, prehistoric archaeology, applied arts, antique furniture and wooden sculpture, as well as the Achille Bertarelli Print Collection. It was impossible to cover everything in one morning, so we committed to come back when we had more time.

After lunch, Troy had his music lessons at the Academy, and I just roamed the neighborhoods around the hotel and worked out in the hotel gym. When Troy got back to the hotel, we made love, of course, and went out for dinner before meeting The Outlaws at Gabriele’s store.

As soon as Gabriele saw me, he rushed over, gave me a great big hug, kissed me, and licked my face teasingly. “I knew you would be back,” he gloated.

Dirty Boy introduced Troy to Gabriele, who nearly melted at the sight of him. With no hesitation or compunctions whatsoever, he lifted up Troy’s shirt and rubbed his hands all over his hairy chest and even stuck one hand down his pants to rub his pubes. “You want to buy some pants, I hope,” he said to Troy.

“Actually,” said The Flirt, “they have enough pants. Now they need shirts to complete their outfits.”

“I know just the thing,” asserted Gabriele, as he grabbed Troy’s hand and pulled him over to where the shirts were.

“Take off your shirt,” he commanded, and when Troy did, Gabriele rubbed his face all over Troy’s furry chest and abs, purring like a pussy…er…a kitten, that is. “No shirt,” said Gabriele. “You must show the world that magnificent chest.” And with that, he pulled a black leather vest off of a rack and put it on Troy. “No button. Leave open.”

All of the gang concurred that the leather vest was a perfect complement to the leather chaps and brief. Gabriele dragged Troy to a mirror, and as Troy fell in love with the sexy look, Gabriele stepped away and came back with a black leather cowboy hat, which completed the outfit perfectly.

“Accessories?” asked Gabriele.

“Like what?” asked Troy, so Gabriele led him to another area where he showed us chain-linked belts, handcuffs (to hang from a belt loop), leather wrist bands, and more. Troy accepted the wristbands and passed on the rest, though he looked very tempted.

 “Now what for you, la mia piccola faccia da sborra?” Gabriele asked me, squeezing my face like a baby’s. The guys practically fell on the floor laughing. “What did he call me?” I asked. “He called you ‘my little cum face,’” said Troy. “Fuck,” I said to Troy, “You’ve been working much too hard at your Italian lessons. You’re gonna have to teach me all those dirty words you’ve been learning.” 

Gabriele led me over to a table stacked with all kinds of shirts. He pulled many off the table, tossing them in the air like the day’s discards. Finally, he pulled out one, yanked off my shirt, and helped me on with a sheer black sleeveless muscle shirt. “Perfect with leather pants or white pants,” he said, referring to the items I had bought (or run out of the store with) the day before. And everyone agreed that he was right. It was the perfect shirt to go with either pair of pants…or with the chaps, for that matter. I also accepted a bicep band to accentuate my muscles. When Gabriele selected a black band with blue piping, I asked him if a colored arm band had the same significance as a colored handkerchief, and he just said, “Maybe…if you are lucky…but you, handsome man, will not need luck.”

“Boots,” said Gabriele. So, Troy and I each got a pair of ankle-high black lace-up leather boots.

“Anybody want to go over to Costolo di Adamo (Adam’s Rib) tomorrow night?” asked Dirty Boy after we paid for our new clothes. “Wednesday is underwear night there.”

Dude explained that on “underwear night” the bartenders all served drinks in their sexy underwear, and customers who stripped down to their undies could get drinks at a discount. It sounded interesting, so we all agreed to meet there the next night.

When we got to the bar, which everyone just called “Adamo” for short, we all stripped down to our underwear and put the rest of our clothes in bags that we marked with our names. Those bags, along with our shopping bags from Gabriele’s shop were tucked safely behind the bar. All of the bartenders and most of the customers also wore nothing but underwear, most of which were sexy, but not overly daring, which pretty much describes what The Outlaws were wearing. Apparently, there are regulations as to how revealing the underwear could be, but some of the men cavalierly flaunted the regs.

For example, some guys wore jock straps or undies with open bottoms, which were against the regulations. Some wore regular undies, but they were pulled down low to expose their pubes and butt cracks. Some wore sheer undies that left nothing to the imagination. And some wore undies with flaps, like my new leather ones, but with one of the snaps undone. Troy was wearing a red thong, and I wore a pair of my Trophy Boy briefs, the kind for guys with extra-big cocks. As expected, we drew lots of stares and quite a few gropes.

“Groping is allowed,” said The Flirt. “If you don’t want it, just politely say, ‘no grazie,’ and they will usually respect your wishes.”

Troy got as many guys who wanted to rub his hairy chest as grope his package. Some guys just wanted to feel our muscles. But, of course, most of the guys who approached me wanted to feel my cock. Some even pulled out my waist band to get a good look at the merchandise.

Around 10:00 p.m. the lights in the back of the bar dimmed, and many of the guys drifted in that direction. “What’s going on?” I asked. “Come,” said Dirty Boy. “I’ll show you.”

Back in the darkened area, guys were groping each other openly, by which I mean that they pulled down one another’s undies and, in some cases, removed them altogether. Some guys were getting blow jobs, and some were even getting fucked. Naturally, everyone wanted to get a good look at my Texas-size schlong, even in the dim light, so it wasn’t long before I was surrounded by guys tugging at my briefs and groping my cock and balls. They lined up to take turns sucking it, and they even placed bets to see who could swallow the most of it. And when they weren’t sucking my dick, they were kissing me, licking my neck, or nibbling on my tits.

“You have the right to stop it if you want,” said Dirty Boy, “It’s your body.”

“My body is enjoying it just fine, thank you,” I said.

After a dozen or more guys had sampled my meat and gotten it stiff as a bone, one backed me up against a wall and gave me a kind of lap dance before he spread his ass cheeks and covered my cock with his eager hole. I didn’t have to fuck him; he did all of the work. After about 10 minutes or so, he pulled away and made room for another guy to ride my throbbing dick. This parade went on for nearly an hour. Normally I would have shot my wad before that, but having the guys pull off every 10 minutes or so was like edging.

When I finally did come, two guys descended on my cock to suck up whatever drops of cum they could retrieve, and another went for the cum oozing out of my last victim’s ass. When they began to swap the cum among themselves, I pointed to my mouth, so they rose up and fed what was left of it to me.

All the while, I was so preoccupied that I never even thought about where Troy was or what he was doing. As it turned out, he was getting his ass worshipped by a parade of cazzos (cocks) and getting blow jobs at the same time. “There’s nothing better than fucking somebody’s face while another guy is fucking your ass,” he told me later.

By midnight, Troy and I were both completely spent, and Troy had to go to class in the morning.

“Tomorrow night is naked night at La Casetta,”said Dude. I knew immediately that La Casetta meant The Little House because it is almost identical to the Spanish La Casita, which is what Carlos calls our guest house/bunkhouse.

“Sounds wonderful,” said Troy, “but I don’t know if I’ll be able to walk tomorrow.”

All the guys laughed, patted him on the back, and told us to rest up for our big trip to Dante’s on Friday night.