Uncle Clyde in the First Ward Ch. 01

My Great Uncle Clyde was, well, a great uncle! He was an all the way Chicago guy, whose mother came to the city in 1890 something or another, he wasn't sure. He lived to be 97 years old, and was lucky enough to keep his faculties until the day he died. I loved that man. He was my favorite relative. We shared a loathing for phony bullshit, which made us hard to be around for a lot of our family, who were mostly full of phony bullshit. So on family occasions we'd wind up alone in a corner, happily not talking to anyone. Then we started talking a bit, (mostly because he wanted me to sneak him some bourbon from the bar, which of course I did) And pretty soon we found we actually liked each other, and let me tell you, Uncle Clyde had the best damn stories about his days in Chicago's First Ward. In fact, I will tell you. And I'll going to tell it to you just like he told me.

Being a building supervisor wasn't my first job for Hinky Dink, but it was the first one where I got the fringe benefits. Fringe benefits is everything, let me tell you! I'll take a cut in pay for extra fringe any day of the fuckin' week. You know why? Cuz a check is always one number, and just that number - finite. But Fringe Benefits are nigh infinite, they could be anything. I like that phrase, nigh infinite. This Wop named Nelson who used to do novels and stuff would say that all the time. Yeah, I stole his words a lot. Got me a lot of tail it did.

Anyway, I was 22 years old, wet as Lake Michigan and in charge of this entire building. Three floors, four apartments each, and me in the basement. Hinky Dink McKenna was one of the two Alderman of the First Ward, and he was the guy I hustled for. After a few years of shoveling shit and packing in bums for the vote, he gave me this building to run. He paid me a salary, and I got a percentage of the rents. But it wasn't all a straight deal. The two back rooms on the first floor were call rooms, rooms used by the whores and the guys called Cadets who rounded up the Johns. The telephones were brand new, and off limits except for McKenna's boys, and one of those boys was me. Everybody worked for Alderman Hinky Dink McKenna in those days. He and Bathhouse John Coughlin ran the First Ward, which was the only place in Chicago were Vice was legal...mostly.

Not too many girls used the rooms, because Hinky wanted the building to keep a respectable air about it, so it was only used for overflow during conventions and Holidays. It was my job to keep the girls on the QT, and all the tenants happy. Yeah, I said 'Happy', and I meant that. You see we didn't screw over our tenants, like you see on those movies and shows. God's balls, it pisses me off when they do that. Hinky Dink had good buildings, Good Ones! Running water most of the year around, steam heat, and a guy who took the trash away. And the rent was rock bottom, I mean fuckin' granite on the floor rock bottom. I wasn't making shit as a rent bonus, which at first chapped my hide a bit. But, it was still better than what I was doing, and the second month in, I started to get some of those fringe benefits I was taking about.

We had a, what you kids call today, a diverse bunch in the building. Italians, Irish, Hungarian, Poles and one Scotsman and his sister. I got along with all of them, once they saw I knew what I was doing and respected them. You see, it was mostly Families with single mothers. They don't tell you that in the books, but men were just as shitty to woman back then as they are today, all that Gentleman stuff is Bunk. And the girls weren't allowed to do for themselves like they can today. Buy Hinky Dink helped them out, gave them a place to stay. He was a fucking saint like that. I don't cared how many goddamned votes he stole, he saved lives, buddy.

Anyway, we kept the families on the second floor which added up to two husbands the Scotsman; three men and me, that's it . The rest were women and kids. And I didn't put my hands on them or proposition none of them. I didn't operate like that. And, sad to say, that was a rare trait amongst my comrades in the First Ward. But the thing is, you had to to hard hearted, you know? You had to punch a guy in the throat without thinking about it or that guy's gonna slice your liver, you know? Nah, you don't know, and that's a good thing. It's one thing to be tough, but we had to be cruel. Yeah. Cruel. The kind of things you don't walk away from. I ain't going to talk to about that now.

So, here I am, 22 and a Building supervisor and, to get to the point of this story, I'm horny as hell. But, I'm working all day and a lot of nights, the only people I see are the tenants and the girls who fuck and leave, and I didn't do working girls whom I didn't know personally. You had to careful. Saw a guy with an advanced case of Syphillus once, holy shit! From that point on, I always used rubbers and girls with references only.

Yeah, I slept with prostitutes. We all did. There was no dating, pitching woo or romantic crap. Guys like me didn't have the clock to waste on that. And at the time I had, what's that phrase?...a poor self image. Yeah, I thought I was a piece of shit, and that I should be happy to get any chunk of happiness that I could crap out of this bung hole called life. After all, who would want to be with me? I didn't think the Michigan avenue Gibson Girls would be Arm-in-Arming with old Clyde anytime soon. And you know what? Fuck those uptight Biddies anyway!

Allright, here we go. So one Thursday I'm calling on Mrs. Rosetti, who insists everyone calls her Mama. She has three kids, no husband and her windows are stuck. The kids are off at work and I'm prying up the window and trying to get to the casement inside. Now Mrs. Rosetti had the biggest goddamn tits I had ever seen. I mean they were Mama Mia titties, like they could feed all of Sicily. Now back then, women didn't do cleavage, or let their boobs all hang out like they do today, but some things you just can't hide. Now I'm banging away at the window, and it's just not coming out, and I'm getting frustrated. It had been a rough couple of weeks, and I was starting to let it show.

"Damn this fucking window!" I yelled out, forgetting Mrs. Rosetti was even in the apartment.

"Holy Mother of God, Clyde! Such language!"

"Oh, ah, Sorry Mama Rosetti. This window is really bugging me."

"Yes? The window is it? I think it might be something else as well? Eh?"

Mama Rosetti was 5'5, plump and had a huge smile with laughing eyes. She could be on a jar of Spaghetti sauce, you know? She was about forty, but no grey hair at all and she dressed just like every one else did, shirtwaist, big dress, high boots, you've seen the Ken Burns documentary, you know what I'm talking about.

But she was right, it wasn't the window pissing me off. I hadn't been laid in a few weeks for various reasons, and I was getting anxious as hell. Waxing my Carrot wasn't cutting it, and it's bad for ya anyway. But I couldn't tell Mama Rosetti that, even though she had those Mother Powers that some Moms have, you know, how they can look right into your soul it sometimes? Nobody in the building could get away with lying to Mama Rosetti.

"Yeah, I'm just working a lot I guess. And, uh, Haven't got a chance to get out much. You know?"

"You don't have a steady, Mister Clyde?"

"Mama, nobody has a steady in The First Ward."

"Ahhh...this is a true thing, but sad. A man like you, you should be with someone, for their sake if not yours. So many pigs dressed as men out there, but you...you a good one."

"Well thanks Mama, I sure wish the girls out there agreed with you."

She looked at me very seriously for a few seconds. I thought I had done something wrong. Then she clapped her hands together with a decisive flourish.

"OK, tell you what I'm gonna do. My little Giorgio, he needs some kinda book for this class. I need a little extra money this month. So..." She untucked her shirt waist, unbuttoned it and took it off, revealing a voluminous construction of lingerie, that was not the corset most women wore. She saw my questioning look.

"My chest is so huge, I have to get this made special." Her arms reached around her back as she undid something and the contraption fell off revealing her massive boobs in all their glory. They had to be 44, 48 with a D Cup at least. I had never seen tits so big, and I had never seen tits I hadn't paid for.

"You like them?" She said, and the sweet matronly look had vanished from her face. Her eyes smouldered, and she began to message her breasts, and was able to lift one of her nipples to her mouth with ease, which she sucked on while staring me right in the eyes. She let out her nipple with a pop and then put her arms akimbo and gave me a deal.

"Okay. Rent is 5 dollars. For fifty cents off the rent, I'll let you play with my tits, and give your cock a little tug? Whaddya say?"

"Mama Rossetti . . .I can't give a break on the rent, Hinky would. . . "

Then I realized fifty cents was my percentage on her rent. So, in a sense, I'd come out even if I just didn't take my cut, and...I looked at Mama's huge breasts, and I realized that I was extra turned on by the fact she wasn't a whore. You know? Is that one of those fetish things? Ah, never mind. So, I said yes.

She smiled wide and sat me down in a chair, unbuttoned my pants and took out my cock, which was already hard as a board.

"Oh, Clyde, thatsa nice cock." Mama Rosetti said, stroking my 8' dick. "It's gonna look so good between my tits." She lifted her boobs and dropped them on my cock. They landed with a plop on my thighs. I could feel their hanging weight on my legs, it's a feeling I'll never forget. But my cock wouldn't come through the cleavage. So Mama got up, and went to her kitchen and then came back. She had a bottle of olive oil and she poured it on her tits and rubbed it around. The sheen of oil made her breast look even better, and this time my cock slid right into her cleavage when she dropped her tits on me.

"Oh, thats soo nice." She purred as she began to jack off my cock with her tits. She pressed them close around my dick, and moved her whole body up and down. She was fondling her nipples as she did it, I watched her as gently rolled the nipple between her fingers, without pinching them.

After a while bit she stopped and said, "See if you like this." She then alternated her tits sliding on my cock, like juggling. It was a sight to behold. She knew a bunch of little tricks, some where silly, all of them were sexy, and she smiled and talked happily all the way through it. You know, like it was just a friendly thing you did for someone. It was the first time that sex was, well, fun.

"Allright, now show Mama what you can do, eh? Take a turn and screw my titties all by yourself." She held her tits firm around my cock and sat up a little higher, forcing me to lift my ass to get a good stroke on her tits. But damn, it felt as good as any snatch I'd paid for down on Archer avenue, even better. And Mama was getting a serious look on her face as I thrust my cock between her two mammoth globes. I was getting a good work out, holding myself up like that while fucking her. I saw Mama looking at my straining forearms and thick German thighs, and her nipples seemed to get harder in response. Finally, I could feel myself about to shoot my load. Mama sensed it as well and began to jack me off again as I kept thrusting. I stifled a yell as I came hard and large all over her tits. She kept gently stroking my cock with her warm, glistening boobs as I settled down, spent and relaxed.

"Dang Mama Rosetti, I guess I sure did need that."

"I thought so. So, fifty cents on the rent this month, and we are even?"

"Yeah, yeah, and uh I don't know what you expect from me in the. . . "

"Clyde, say no more. This is just about a trade. You know, like on Maxwell Street with the Jewish merchants. It's just business, I am still Mama Rossetti and you are still Clyde the Super. Can you keep to that?"

"Mama Rosetti, I guarantee I can."

"Good. Now hurry up and fix my window. I have to make dinner for the kids."

She left me in alone and went back to her cooking. Since I was thinking clearly, I got the window fixed in a snap and left, both of us smiling. It was nice having sex with someone who didn't have to be paid. And a nice person to boot. It felt weird to me that it had made a difference, you know? That she actually kinda wanted to do it.

But over the next couple of days, I was going to get a lot more to think about.