Gloria Gets to Chicago

It was a nice house. She missed Chicago. Hyde Park had its areas, and Gloria had spent time there with friends and associates. She rang the bell again. The drive from Detroit was not that bad, but it would be good to stretch out and get stretched out after so long.

A young lady opened the door. She must have been 23 or so, definitely not 25. She was light skinned, braided hair, not tall, but really thick in the ass and breasts. Like G cup thick. She wore a green wrap dress, and she held a Newport in her left hand. Gloria could smell the smoke. She did not mind. She could also hear the music in the background. Someone was having fun.

"May I help you?"

"I'm here to see Tony. My name is Gloria."

"Ah. Tony's one freaky fucker. What's he got to do with you?"

"I counsel him some times. Is he in?"

"He's in. That's fine. Come in."

She sat on the sofa. It was a nice room, but as she laid back she realized there were mirrors on the ceiling. Tony...

Tony was a weird one. A new friend, recommended by a number of people, he had asked her a lot of questions, but never really said what he wanted. Gloria was not sure if he was scared, or if he was just cautious. He was rich, had some businesses, some property, and was supposedly trying to hire someone. He always had young girls around him.

"Drink?"

"Water please"

"Bitch I know you aren't really a nun"

"Sorry?"

"Tony said someone was coming to fuck us. If that's you you ain't no nun."

"Where is Tony?"

"I'm here. Gloria."

She rose to greet him as he walked in from the next room. He was tall, fine, dark, muscular, with a steely gaze and calm demeanor. He smiled. "Is Jenny messing with you? How are the Sisters of Mercy these days?"

Gloria's silence wasn't due to a lack of comprehension. It was just...the dude wasn't wearing anything but his cologne. He was sculpted, really lean, and hung. It was hard not to look at his dick. It made Gloria really want to get stretched out. But she had to play the game.

"They are fine. Jenny and I were just getting acquainted."

"Well. Do you eat pussy? Jenny take your shit off."

"I'm going to need a drink here, I can't just have a strange chick eat me. What the fuck?"

"I apologize. Get a drink, but definitely take that wrap off. Gloria, do the same."

"Tony, I'm not sure what you thought but..."

"Tell me you don't wonder what my dick feels like. Tell me you aren't even curious. Didn't you drive all the way from Detroit today?"

"I did."

"Would you like a shower? A massage?"

"I wouldn't mind one actually. I feel sticky."

"Jenny, can you help our friend out?"

Jenny walked her to a bedroom. As Jenny walked ahead, she shrugged the dress off. She wore no underwear. Her body was firm, really curvy, and her ass was to die for. A real onion with over and underbutt. She didn't seem as shy as she had been before, and it was clear she and Tony were a bit of a team. This was not her first time. There were towels and robes on the bed.

"Would you like anything else? The shower is on the left."

"Some company?"

As Gloria removed her scarf, she rubbed her hair, and she removed her cardigan and blouse, rubbing gently at where her bra chafed against her breasts. Her skirt came off, as did her panties.

"I think company can be arranged. God you're thick. Those titties!" Gloria's breasts were big, brown and firm. Her nipples were already hard.

"I think I could say the same. I'd eat your pussy anytime."

They got in the shower, and Jenny pushed Gloria under the water, and rinsed her off before soaping her, lathering her in the hot water with a washcloth, and working out all that road grime from her neck, armpits, pussy, ass, toes, legs, and neck. Gloria started to relax as Jenny worked on her back. As she rinsed the soap off she started massaging Gloria's back. Gloria closed her eyes and sighed. It had been a while since she had felt anything so good. She tried to turn but Jenny pinned her against the wall.

"This is for you, you can do me later."

She felt Jenny's legs spreading hers, and Jenny rinsed her crack and then her pussy, slowly, then firmly, Jenny started to stroke her mound. She moved her hips slowly, and then opened her legs more, leaning more against the wall. Jenny kept working, and then squatted, pushing her mouth into her ass, licking her asshole, kissing and gently probing. Gloria's knees were soft, and when Jenny pulled her and turned her, all her resistance was gone.

She was on fire, tingling, wet, and her clit was hard and jutting out of her hairy bush. Jenny licked first and then sucked her clit, licking in counterclockwise strokes. She pushed a finger into Gloria's pussy. Gloria gasped. Her pussy was soaking wet, she closed her eyes.

Jenny put her entire palm over Gloria's pussy, with the base on the clit and the fingers going over her bush.

"Let's dry up. I'll give you a massage."

She turned and walked out of the shower. Gloria wanted to die. What a tease!!

Jenny had a variety of oils, and after drying Gloria she lay her face down on the bed, and started rubbing her neck, shoulders, and back. Gloria felt sleepy, and tried to stay awake. She failed. She woke to Jenny rubbing her butt. Firm, deep strokes, which led to her pussy being as wet as it ever had been. Besides some tickling strokes to her inner thighs, Jenny played it straight, worked her sore hamstrings, her tense calves, pushing deep and making her scream. She then got to the ankles and her feet, where she worked the muscles and tendons, and brought Gloria to a new place.

"Turn."

Gloria turned over. She was stark naked, on a strange bed, being rubbed down with lavender oil by this young, thick, sexy woman. She was wet, her nipples were hard, her clit was hard, and she wanted a lot more than a massage.

Jenny was naked, and with a flat stomach, huge breasts and small nipples, she was cute. She was waxed, and had a neat pussy, and a thick, muscular ass. She was very strong, and easily separated Gloria's muscles with her fingers. Clearly she'd never had kids or anything, and she was young. Her breasts despite their size were still firm. She gave the massage as if she did this every day. As she exerted herself she breathed a bit firmly, and her breasts jiggled gently as she worked.

As Jenny moved up from the feet, she worked the front of Gloria's thighs, and then gently stroked Gloria's pussy, teasing again. She got on the bed, and then slowed down, making long strokes from Gloria's knees to her waist, working out the tension of that long drive.

She leaned down, and started tracing the same path on Gloria with her tongue. Gloria was going mad with anticipation. Was she gonna get some head? Jenny passed her pussy, and massaged her abdomen in circular strokes, moving up to straddle her and work her boobs. She ignored the nipples at first, and worked her chest in a circular motion, before finally licking her nipples, sucking on them, and quickly working the milk out, and getting a good flow going. She sucked first one then the other, gently, and then harder, getting strong suction and a good flow of milk.

"Fuck you should have just said you had milk."

"How was I supposed to do that?"

Jenny sucked her into a trance, and by the time she reached back to finger Gloria it was more than Gloria could bear. Her orgasm was deeply felt but mild, and she shuddered as Jenny kept sucking her breasts and squeezing them.

She faded into a fog, reached out to hold Jenny to her. Jenny was warm and thick, and was a great hug.

"I wish I could have you work on my pussy too.."

Jenny pushed her fingers into Gloria. Slowly stroking in a beckoning motion, deeper and deeper. As Gloria got wetter, she arched her back, and rolled her hips. Jenny pushed deeper, and then licked and sucked her clit. It was delicious. She pushed her face further in, getting juices to run all over her face. Gloria sighed. This was not what she expected, but it was what she needed.

As she recovered she looked up to see Jenny on her knees with her face plunged into her pussy. She smiled. Suddenly Jenny paused. As she opened her eyes she saw Tony behind Jenny, stroking her pussy. Jenny moaned. Tony kept stroking Jenny as Jenny adjusted. Then Jenny stiffened. Tony was inside her. He slowly pushed his hard cock into Jenny's pussy, and stroked her. Circular movements, really slowly, but really deep. Jenny was distracted now, and not as gentle with Gloria's clit. Gloria got used to it. Jenny's fingers were deep inside, and she was sucking on a particular note that Gloria needed.

She lost a sense of how long this was going on, but suddenly Jenny tensed, and Gloria could feel Tony speeding up behind her, giving her more direct thrusts. Jenny got up on her hands, and she could see Tony's hands gripping those massive breasts. He squeezed Jenny's nipples, pinching, twisting, and Jenny screamed. His thrusts were deeper and harder and faster, and then Jenny froze.

"Fuck Tony. Fuck. Fuck you Tony. Ohmigodnomgoaogoaoaaaaaaa!"

Tony didn't stop stroking, seizing her shoulders to keep fucking her through her two orgasms. Jenny collapsed whimpering, with her hand over her pussy.

"Tony back up I'm done. Fuck. I need ice."

Gloria heard Tony pull out of Jenny. He knelt at her feet.

"I didn't get to come. Not fair."

"Maybe I can help you, I need a dick."

Tony moved up the bed. He was hard, veiny, and clean. Like he waxed or shaved. His cock was very sensitive, and at that size she felt every inch. She raised her feet to the ceiling, and he entered her slowly. She felt the stretch. God he was huge. She was wet, and gripped him with her pussy, rippling down his length. She squeezed him, and he fucked her back, reaching between her legs to squeeze her milk-sodden nipples. She had started leaking, and it got to a point where every stroke brought more milk to her boobs. He sprayed milk all over the bed, and his face, and her body. He pushed her legs down and drank her. Squeezing. He was strong, and it hurt, but the pain made her pussy wetter and turned her on more. He fucked her harder and harder, until she felt the pounding was going to break her. But she needed it. She felt high, like she had taken something strong. Her vision was blurry, and the top of her head hurt. But he fucked her. And sucked her. And held her to him. She wrapped her legs around his waist.

This one she felt. An eruption in her pussy, as she grunted, and squirted. She she felt her fluids burst out, and she felt light headed. Then he came, blasting his seed into her for what must have been a couple of seconds but felt like hours.

"Tony!! Oh my God! Tony!"

"Shhhhhhhh".

She sat on the bedside, looking at him as he lay there, with his tool hanging over his thigh to the side.

"What brings you to Chicago? I need that milk. I haven't had that in a while."

"Work."

"What kind of work? I know you aren't a nun."

"I'll do whatever is needed. What do you do?"

"Property. I own buildings, and I rent them for money."

"I need money though. I have a kid to feed, and I need something to show my PO. I don't think she will be happy I'm out of Detroit."

"Figures for the milk. What can you do besides fuck?"

"I'm smart, I work hard, and I'm versatile."

"Men do more for you when they want it than when they get it. Don't be too versatile."

"I don't fuck for results though. I fuck to fuck."

"How's that gone for you? You need to fuck fewer people, but hang the prospect over those you don't fuck. We don't all know what good pussy is like, and we don't all appreciate it."

She laughed. "Are you gonna be my pimp now?"

"Nah, but I've lost enough agents who need a hard dick to validate them. Doesn't work. Tell you what. I'll do a flat fee, $3,000 a month, for errands. Pick up, drop off, messages. Part time. I'll call when I need you. Would that work? "

It wasn't a lot of money, but it was something, and Tony seemed to be sincere. Her pussy was still throbbing, but it was rare that a man actually thought about her wellbeing.

"I'll take it. But first I gotta get that magic dick in my mouth. Jenny can't have it all."

"Maybe later. I gotta get dressed and run some errands. Jenny works for me, and has come a long way. As you can tell she doesn't mind sharing, and she follows orders. That's important to me. "

Gloria wasn't a stupid woman, or lazy. She just couldn't resist a direct come on, and she was always confident she would work a solution out of any situation. It led to lots of excitement, and lots of dead ends. All Tony was getting at was that she didn't need to take on all comers, just the ones that met her predetermined means. She got dressed.

He liked her. She was strong, hot, and bold. She just hadn't learned subtlety in some aspects of her life. He wanted to work with her, not just because her tits were filled with nectar, or because her pussy gripped like an asshole, but because he liked her. And anyone who ran a hustle dressed as a nun had to be special. Time would tell. She walked out in that gear, and he touched himself. Maybe he had been rash to run her off.

"Jenny, what did you think about Gloria?"

"She was really stiff, really tight."

"Did you like her?"

"I'd do her again. You came and fucked it up. I was about to teach her about pussy eating."

"Hahaha. That buzzard would have eaten you alive. She's a hungry one."

"I could see that, but she was hungry in a way I could handle."

"So you wouldn't mind working with her?"

"Or on her..."

"Don't get hooked on grown pussy. She'll turn you out. Watch her and learn something. We'll see."

Gloria thought of the envelope Tony had given her. He called it an advance. Well if she already had the money, what was the point coming back? Maybe it was a test. Tony was a talker, she could see, and he lived for some future somewhere. Gloria didn't think that deeply. Men liked women who let them control things, and rich men thought money solved every problem. The key was to fuck rich men. Then she reflected. That wasn't so simple. Some rich men were cheap. She remembered Mike, who promised her a car, and left her with a lunchtime belly full of cum for weeks before she figured out he just cleaned cars and didn't own any of them. She remembered Saul, with his little dick and quick fists. She had to lay him out cold to stop that nonsense. She needed order in her life. Some predictable cash flow, and some predictable dick. She made her way to Chatham to see Debbie. Debbie always had something to say.