A Young Man’s Strange Erotic Journey Around the Globe

America's Finest Ambassador Chapter 52 – A Propensity to Party With the Impoverished

Chapter 52 – A Propensity to Party With the Impoverished

Up until our junior year, students were required to live in the dormitories at Marquette University in Milwaukee, Wisconsin. To promote the safety of all the students living in these buildings, the entryways into the dormitories had been tightly controlled. No one was allowed access without having their individual ID’s inspected and then swiped through a machine by a university official who’d been manning the front desk. Temporary guests of residents who didn’t belong had to leave their identification – as well as that of whoever had been hosting them and subsequently accepting responsibility for all that said guest does – at the front desk to enter. Registering to stay overnight as a visitor in one of these dorms had been a lengthy process that involved paperwork which almost made having guests from other schools not even worth it.

To me, at the time, this all seemed so very excessive. As a freshman and sophomore, I didn’t have an appreciation for this type of security and instead had seen it as no more than an inconvenience that’d made it harder to sneak beer into the building. However, in the summer of 2008 when my friends and I had all moved away from the university-sanctioned living spaces and had gotten our own homes in the surrounding area, it quickly became clear to me why the dorms needed that type of security.

Our house at 931 N. 14th Street had been situated two doors down from some sort of government-funded low income housing project. On any given day, you could post up on the stoop of our century-old crib, look to the north and see some sort of shit going down. I recall one afternoon sitting on the porch with a few of my roommates, casually sipping beers while watching a small group of guys beat the shit out of each other on the corner. What they were fighting about, I don’t know. Did I care to find out or call the police on ‘em? Nah, not really. Did I enjoy the free entertainment? You bet I did. It was a wild-ass lifestyle the people around us were living and I found it to be new, exciting and different from anything else I’d ever experienced.

To get as involved in our community as possible short of doing something gay like volunteering my precious free time that I preferred to spend on nothing other than getting fucked up, I even went so far as to set up a bench and weight set on our lawn for our new neighbors to come and use while drinking their morning beer or going family style on a fat-ass blunt. Although good use was made of this equipment during the time it lasted on our lawn, certain elements of the neighborhood had eventually dismembered our gymnasium for scrap metal, leaving only the padding of the bench and the plastic sand-filled plates on our property.

I’m not sure what they’d had on their minds but at least a couple times when they must’ve thought we weren’t around, we caught vagrants wandering about the vicinity – and sometimes into the interior – of our house. One of the instances I can think of had been on a weekday morning when Tim O’Shaughnessy was watching ESPN while eating a bowl of cereal in our living room. At some point he could hear the front door creak open but none of our roommates had either gone running up the stairs leading to the second floor or came into the living room to greet him as was the norm. He became suspicious and muted the television. From the vestibule, he could hear two voices whispering. “Hello?” he said while setting down his breakfast on the coffee table and standing up from his seat, “Who’s there?” Immediately after his inquisition, Tim could hear shuffling as whoever it was scurried back out the door and down the porch. He ran out after to see who it was. When he got to the porch, he looked out and saw two middle-aged black guys hightailing it down the block, back to the project building.

Naturally, we didn’t like those kinds of uninvited guests coming into our house. That said, there were a certain few neighborhood bums and hood-rats with whom we’d had a good rapport that we’d welcome to our parties with open arms. The most familiar and often-present of these local street people had been a dude named Roy or “Kan Man with a Capital ‘K’” as he’d like to refer to himself as.

Like the guys who’d been sneaking into our house, Roy too was a middle-aged black dude. Unlike those would-be thieves however, the Kan Man – as his name suggests – would make his living not by dishonest means but by going around Marquette’s campus collecting discarded aluminum containers that’d previously held twelve ounces of liquid fun.

During the summer months, when he needn’t wear layer upon layer to cope with the cruel winter conditions while doing what he does, Kan Man would always be wearing a cut-off jean jacket over a black t-shirt atop a faded-ass pair of wide-legged carpenter jeans. Along with a slick set of mutton chops and what would otherwise be considered a pervy pencil mustache had he not worn it so well, Roy would invariably be sporting, during any time of the year, a black do-rag and a pair of sunglasses that concealed a lifeless eye which’d been struck by a piece of shrapnel back during the Vietnam War.

Back when we’d first moved into our house and had met the Kan Man for the first time while he’d been making his rounds, he told us not to bother putting our empties in the garbage but to just throw ‘em out on the front lawn because it made his job easier. Although there’d been rival can men collecting on Marquette’s campus, none of them seemed to have the same work ethic as Roy so rarely if ever would the piles on our lawn be gathered by anyone but the official Kan Man.

The way this dude would show up every time we were drinking – the way a shark would after getting a whiff of blood in the water – made it seem as if he’d been equipped with some sort of party-detecting radar. Well, maybe not party-detecting radar – that sounds too high-tech for a street bum. Maybe it was something more like hobo intuition that, upon sensing the tabs being pulled back on the day’s first round of Busch Lights, his ear would prick up from a mile away, he’d drop whatever he was doing and scamper right over for his aluminum payoff.

Because the Kan Man was always the first one on the scene, he’d often show up way before the party had ended and would just hang out, collecting cans one-by-one as the college kids emptied ‘em. Once we’d become familiar with him and he with us, we’d start offering him beers, cigarettes and the occasional puff of sticky icky. Obviously he liked this and it didn’t take long for these interactions to turn routine. He’d show up to collect the cans, say “hi” to everyone and if we failed to offer him any of the aforementioned intoxicants, he’d often broach the subject by asking if we’d let him get “a hot one.” This was his way of being humble and letting us know that although he wanted a drink for free, he wouldn’t wanna deprive us of our cold, refrigerated beer. Since no one I know in the history of the world sets aside and keeps hot beers on hand just in case a homeless guy comes around and happens to ask for one, we’d never hesitate to throw a few cold ones in The Kan Man’s direction.

Although Roy had hung out at my house every now and then during my time at Marquette, he was most often seen and had become a staple at parties over at my buddy Hoffman’s house. At Hoffman’s, these parties – if they can even be considered parties – consisted of the same group of ten or so guys and two or three girls inflicting extreme punishment on their bodies every time they’d gotten a chance to do so. Whatever you wanna call these gatherings, it was a guarantee that there’d be enough booze at the place to fill a fucking swimming pool and more often than not, the assemblies would carry on well past daybreak. Before moving on, allow me to give an example of what it was like to be at one of these late-night Hoffman sessions.

During a frigid night – or morning I should say, as it was close to five AM – amid a cruel cunt of a Milwaukee winter, a group of the usual suspects, Kan Man not included, had still been chugging away at the immeasurable beer supply, chain smoking cigarettes and blasting music from Hoffman’s new iMac that’d been attached to the house’s speaker system. He’d recently gotten that new laptop because during a separate late-night episode at his house several weekends previous, he tossed a few too many back then pissed on and subsequently broke his old one.

Most of these after-hours get-togethers had taken place in – had it been a normal house occupied by a single family and not an animal one rented out by college bros – what would’ve served as the dining room. In the center of this late-night party spot had been the pool table which was perpetually in use. A few feet away from the billiard, up against the exterior wall and sandwiching a little shelving unit on which Hoffman’s new computer had sat were two reclining chairs. Although there were other places to park your ass in the living room had you felt the need, these were the only seats available in party central – the rest was standing room only.

Somewhere along the way on the road to self-destruction, our freshman buddy Schneider had reached the point of zombified intoxication and had been sitting with his head hanging low as he began to nod off on one of the reclining chairs. A couple guys had been shooting pool while one or two more had stood around smoking cigarettes and ripping bowls. Pretty standard late-night scenario.

As the story goes, Schneider at some point had stood up and turned his back to everyone else which left him in a position that looked to the guys shooting pool like he was about to pick the next song on the computer. Since this type of musical self-service was often carried out by people with requests, no one had thought anything of it.

After the song previous had expired on YouTube and a new one had not yet come on however, Hoffman looked over and realized that Schneider – as he wobbled back and forth in front of the iMac – was not standing there to pick a new song. In actuality, he’d been fumbling around with his zipper and removing his fire hose from the reel to extinguish the laptop which to him must’ve looked like a toilet with the seat up. Figuring he wouldn’t be able to convince his parents to buy him a second new laptop in as many months that’d “mysteriously stopped working,” Hoffman rushed over to save his computer. Just before Schneider’s stream had started to spray, Hoff grabbed him by the shoulders, pulled him backwards and threw him down on the floor. Schneider’s back hit the ground and as he laid there, he started pissing up into the air and all over himself. Before a total mess could be made in the most important room of the house, a dude named Flaherty who’d been shooting pool helped Schneider to his feet and led him outside the back door so he could finish off the evacuation from the porch. As I mentioned, it’d been a frigid-ass night and Schneider had not been dressed for the conditions. This of course would’ve been okay had he been coherent enough to just take a piss and get his ass back inside, but that wasn’t the case.

Right after the incident, someone had put a new song on the almost-pissed laptop as Flaherty and Hoffman resumed shooting pool while everybody else continued drinking and smoking, instantly forgetting about Schneider on the back porch. About twenty minutes later, someone finally realized that the dude had never returned from finishing his half-piss and went out to go check on him. Upon opening the back door, they found Schneider standing there shivering. As his teeth chattered, his eyes had been rolled into the back of his head and the piss stains from the first part of the errant evacuation inside the house had frozen on his shirt. His penis was tucked away but his ballsack remained hanging out his fly which he’d apparently taken out by mistake and had forgotten to put away upon completion.

During these late-night congregations at The Hoff’s, it was pretty much a guarantee that somebody would end up getting piss-on-yourself, ballsack-out drunk and the Kan Man was no exception. One time, following about eight hours of partying with Hoff and the rest of the alcoholic crew while listening to anything by “dat bad mafucka Elton John” or a song called “Stomp” by the Brothers Johnson which Roy had requested on repeat, our buddy reached the point of no return. During the wee hours of the morning, good ol’ Kan Man With a Capital “K” had been standing next to the pool table when his eyes rolled back and he suddenly fell face-first onto the billiard. The impact of his body weight caused all four of the legs to break off the table as Roy and the rest of the mess went crashing down onto the black-and-white tiled chessboard-looking floor.

Although the Kan Man was the most well-known and most partied-with bum in the area, there were several others who I’d only gotten fucked up with once or twice that still managed to leave a lasting impression. One of them had been a forty-year-old crack whore named Gina.

The first time I’d ever seen Gina had been when she wandered into our backyard while we’d been grilling and day-drinking about three weeks after we were handed the keys to our house the summer before our junior year. My roommate from freshman and sophomore year, Tommy – even though he’d transferred schools at that point – had been up there getting it in with the rest of us.

To set the scene for you, Tommy had been manning the grill and I was standing nearby next to an inflatable kiddy pool that’d been filled with murky water, blades of grass, several empty beer cans, one golf ball and a raw bratwurst that someone had thrown in there after it’d fallen out of the packaging onto the ground. That someone was me. While Tommy and I had been off to the side grilling, drinking and controlling the music, a few other guys had been tossing around a football and a few girls had been sitting in lawn chairs, sunning.

Even though there’s a big ten-foot-tall chain-link fence with barbed wire atop it in between the backyard area we’d shared with two of the neighboring properties and the parking lot of the housing project on the corner, pretty much everything we did was visible to any and all shady characters who’d been hanging out yonder.

While we’d been doing our thing on this beautiful summer afternoon, the music from the stereo had attracted the attention of this short-haired bony-ass black chick who’d come up out the ‘jects and clung onto the chain link fence while looking in at our drunken fun. A few minutes later, she decided to join the festivities, walked around to the front and over into our backyard. Since Tommy and I had been the ones closest the front of the house, we were the first ones she greeted.

“Hell yeah,” she said, “you white boys know howta party. Uh-huh.”

“Yes we do,” Tommy said while flipping a burger.

“Y’all think I could get one them beers?”

“Yeah sure, help yourself.”

She picked one out the case, cracked it open and slugged half of it down in one sip.

“Ah, that’s that shit,” she said then wiped off the bit of beer that’d been dribbling down her chin. “So whatchyall names?”


“Tim. Yours?”

“I’m Gina.”

After the introductions, Gina took another massive slug of her beer and emptied the can.

“Whoa,” Tommy said, “that was pretty impressive.”

She burped.

“Can I get one more?”

“Yeah sure, take another.”

“Thanks,” she said.

While sipping on her second one, Gina stood there watching the sweaty shirtless bros as they tossed the pigskin around the backyard.

Tommy had always felt the need to ask bizarre questions of people he didn’t know that he considered freakish and our new friend was prime real estate.

“So Gina, what’s your favorite farm animal?”

“My favorite what?” she asked with eyes glued to the football as it flew back and forth across the yard.

“Your favorite farm animal.”

“My favorite farm aminal? Sheeyit. I don’t know nothin’ ‘bout them farm aminals.”

“What?” Tommy and I laughed. “You don’t know ‘bout them farm ‘aminals’?”

“Naw. I don’t fucks wit them farm aminals.”

“Okay. Well, what do you ‘fucks wit?’”

“I love me some football. I tell ya that.”

“Oh yeah?” Tommy asked. “Who’s your favorite football player?”

“Brett Favre,” she responded without hesitation. “I love that Brett Favre.”

“That’s cool. I like Brett Favre too. He’s a good player.”

“That’s fo sho,” she said, “and a fine hunk o’ man too.”

“I agree. I wasn’t paying attention though. I forgot already. How many homeruns did Brett Favre hit last year?”

“Imma say that Brett Favre hit at least…seventeen homeruns last year.”

Tommy looked over at me.

“Whattaya think Timmy? Does that sound right to you?”

“Yeah, I think that’s pretty accurate,” I nodded to Tommy and looked over at Gina. “You really know your football.”

She too nodded and then took a step up to the kiddy pool.

“Hey,” she said while lifting the soggy bratwurst from the dirty water, “what’s this doin’ in there?”

“That bratwurst wanted to go for a swim,” I said. “It told me so.”

What?” she replied, squeezing and wiggling the piece of meat around in her fist. “Bratwurst don’t go swimming!”

“That one does.”

Gina proceeded to lift the sausage up to her face and started jiggling it around in front of her mouth while seductively glaring at me and Tommy.

What are you doing!?” my roommate asked.

“Yeah?” she teased, not quite putting the raw piece of meat into her mouth. “D’you like it when I do that?”

“Hey,” I jumped in before Tommy had a chance to reply, “show me what you’d do right now if Brett Favre was here.”

“Aw, if that Brett Favre was here, I be goin’ like this,” she began fellating the brat in front of us. “Mmm, mmm,” she hummed as she slid it in and out along her chapped, bloody-ass lips. “That’s what I be doin’ if Brett Favre was here right now.”

Although that was definitely the most sexually disgusting thing I’d seen a Milwaukee street person do throughout my college career, it hadn’t been the weirdest I’d heard. That honor belongs to a short but built fifty-year-old ex-gangbanger named Cosmo. One night – the last night ever in my house on 14th Street, actually – a few peeps and I had been gettin’ drunk and smokin’ weed on the porch when Cosmo wandered up there and asked if he could get a beer. In return, we informed him that our beer was his.

“So Cosmo,” I said as confidently as I normally would when wasted out of my mind, “what’s your story? Where you from? You married? Got any kids?”

“I ain’t married but I got kids. Ten kids actually. They all back in Chicago though.”

“You’re from Chicago?”


“Me too. Why you livin’ up here now?”

“I live up here now ‘cause I can’t go back.”

“What’s that mean?”

“It means that some people want me dead and if I go back, they’ll fuckin’ kill me.”

“Who’s after you?”

“Lotsa people.”

“Why are they after you?”

“They after me ‘cause I used to bang when I was a youngsta and I did some shit I ain’t proud of. And after that, once you in it, you in it fa life. Ya can’t just say one day to the rival gangs, ‘Aight yall, know what? I quit. You can put ya guns down now and stop tryna kill me because I don’t wanna play no mo.’ It just don’t work like that. The same people that wanted me dead twenty-five years ago would still kill me now if they had the chance. I don’t wanna die and could no longer constantly live in fear of dyin’. So I came up here to start fresh some years back.”

“Damn dude. That shit’s fucked up. Where ya livin’ now?”

“Shit, I don’t know,” he looked around from where he was standing at the edge of the porch. “See them bushes over there?” he pointed to the shrubs in front of the apartment building on the property just south of ours.


“That’s my fuckin’ home tonight.”

“What? Really?”

“Yeah, really. And you know what I say to a rodent or a raccoon if it try to come up in there when I’m sleepin?”

“Nah, whatchu say?”

“I say, ‘Yo bitch, get the fuck up outta here!’ And I punch that motherfucker in the face. ‘This is where I’m sleepin’ tonight!’”

As we sat there for hours upon hours getting fucked up together, I’d learn a lot about Cosmo – the most interesting trait being the way he’d test whether or not a woman he was about to sleep with had been carrying any sexually transmitted diseases.

The exchange went a little something like this:

“All you gotta do to check if a bitch pussy clean is go like this,” he said then stuck his pinky in his ear and twisted it around. “Ya git some earwax on ya finga like this right here,” he showed us the glob removed during his unnecessary demonstration, “then before slidin’ yaself up in there, stick that pinky in the pussy. If she git to squirmin’ ‘round like she gettin’ mo’ aroused than you think she should, lookin’ all like this,” he said through his impression of a smiley-ass female orgasm face, “you go ‘n’ git yaself the fuck up outta there.”

“Really? Why’s that?”

“You get outta there ‘cause the pinky test don’t lie. The earwax have a chemical reaction with the disease that cause the woman too much pleasure. It means ya gotchyaself a pig in the blanket – a dirty bitch who got some shit goin’ on down there that you don’t wanna be a part of, nahmean?”

It had been interactions like these with crazy, poor-ass street folks that made my college experience a great one. And now since my propensity to party with the impoverished has been explained a bit and you might now understand where I’m coming from, you won’t find the information presented in the next chapter all that surprising.

Bum party action in Mil-Town…