Penny's Story

Author's note: The main character in this story has a LOT of sex with various white women. It's almost comical. Most of the scenes are alluded to or hinted at. The scene with the main characters is obviously written out.

Ladies if you'd like to read more of his adventures with white women, fantasizing you were one of them or fellas if you'd like to live vicariously through his cock, leave comments below. I may write more stories from Ulysses' point of view.

All sexual activities occur with people at least 18 or older. Penny has a very troubled past, but no details of her sexual history/activities before age 18 are given.

Editing thanks go to Todger65.

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Chapter 1

Ulysses stood nude in front of his full-length mirror thinking about what to wear that evening. He was tired and didn't feel like going out, but his half-brother TJ was moving to Tampa Bay, Florida soon and this was his last weekend in town. Much to Ulysses' chagrin they had decided to go to a new strip club that was opening. TJ's father, Tony was in town to help him move, and suggested it. Nicole was going too, since the magazine she occasionally models for, Elite Magazine, was sending several models to attend the big opening. Her sister, Taylor, another model for the magazine, was arriving from Miami to attend the opening as well.

He would rather go to gym as he had missed a few days. As a fitness model, this made him feel quite guilty. Plus, he didn't like strip clubs. He felt they were trashy and dirty, and felt sorry for the girls working there. But he was a good sport and went along anyway.

He smiled softly as Nicole's hand slid around his torso. He watched her hand trail his abs in the mirror, her white skin contrasting with his dark-chocolate tone. The short blonde peaked around him and smiled at his reflection in the mirror. She was TJ's soon-to-be former police partner. The two police officers crashed at Ulysses' apartment the previous night.

"I'm going to grab a shower, want to join me?" Nicole asked. Ulysses smiled and nodded, following her past his bed, glancing over to a still sleeping TJ as they made their way to the shower.

Her ass was amazing. Ulysses often wondered how many squats and lunges she did a day. Out of the few times they've slept together, Ulysses always had trouble with his stamina while with her. The steam from the shower rose to envelop them both. Nicole moaned loud enough to wake TJ. He would no doubt want to join them.

Ulysses was right. TJ knocked on the glass door of the shower a few minutes later, "Can I come in?"

"No," Ulysses told his best friend and half-brother. "Let me finish and I'll come out. 30 seconds." He didn't want to share a shower with both Nicole and TJ, since TJ was much taller and larger than him. Fitting two people in his shower was difficult enough, adding a massively muscular black man like TJ, was near impossible.

Nicole went to her knees like she normally does when receives cum. She gobbled up as much as she could from Ulysses' spurting cock. He smiled at her and made his way out of the shower, stepping aside so TJ could enter, grabbing his towel and heading to his closet. He looked through some shirts, not really wanting to dress up, as the orgasmic moans of Nicole in the showered filled the apartment.

Ulysses decided on a simple t-shirt and cargo shorts. It wasn't anything special, but he didn't care.

Later that day he groaned inwardly when Nicole's sister, Taylor, showed up with not one, but two friends. A Puerto Rican named Claudia, whose sister, Fernanda, was organizing the opening event, and a gorgeous brunette named Angela - all three women had big, muscular, backsides, just like Nicole. They were all models for the magazine, which catered to African-American males between the ages of 18 and 35, and were all wearing short cocktail dresses of varying solid colors. He tried to hide his sigh of annoyance. He knew he wouldn't be getting any sleep tonight.

The four women split up. Two went to each to TJ's arms; the remaining two went to Ulysses'. Nicole and her sister were on the arm of TJ, Ulysses was stuck with the other two. He knew Claudia somewhat but didn't know Angela. He was polite enough, attempting to make chit chat through dinner.

When they arrived at the strip club, Ulysses begrudgingly made his way in with the two women on his arm. It was very crowded, but at the same time, very nice and upscale. The six of them found a table and ordered drinks.

Ulysses sighed again, taking in his surroundings, thinking that it was one night only and that it was no big deal. He took a sip of his drink when he felt a tap on his shoulder. He stood and smiled, instantly recognizing the woman. It was Fernanda. She was a six feet tall Puerto Rican goddess. He knew, through his step-mother, Devin, that Fernanda worked for and with the developers of this shopping center, which contained the strip club. She oversaw its construction for her boss. Claudia stood and greeted her sister as well.

Fernanda introduced her associate, a very wide and muscular black man named, Fat Rob, and the four of them chatted for a few moments. Fernanda had to go backstage to check on things with Fat Rob, but told Ulysses to please stop by and see her next time he was in Miami. He agreed and told the family friend goodbye.

TJ's father, Tony, came by the table a few minutes later to join them. He was with an older white woman. Ulysses didn't catch her name, but within a few moments she dragged TJ off for a private dance. Tony, watching his son head to the private area, asked which one of the ladies was his son's partner. Nicole smiled and raised her hand. Taylor added that she was her sister. Tony slipped to the empty chair left by TJ and put his arm around the two blondes. Ulysses watched them giggle and flirt with the older black man.

After a few minutes of flirting and whispering, Tony nodded to the door, "We can get back in," Ulysses heard him say. Taylor told Angela and Claudia they'll be right back. The two blondes nodded to Tony and followed him as he stood, leading them out of the club. Ulysses watched Tony place his hands on each one of the woman's asses as they left.

It was just Ulysses and the remaining two women at the table. They were sitting, idly chatting with each other, with Ulysses in the middle. He was bored out of his mind. Their hands caressing his thighs under the table didn't even excite him much. He just wanted to go home.

Then she took the stage. She was tall, maybe Ulysses' height, around 5'10." She had short, pageboy style, blonde hair that curved her face, a beautiful hourglass figure, fairly large breasts, and even through all the makeup, Ulysses could tell she was young. She was younger than all the other women he'd seen there. He couldn't take his eyes off her. There was something about her, something that made him feel sadness but attraction at the same time. He wondered how old she was as she worked the pole like a pro. He wondered if her parents knew she was there. He wondered if she even had parents. He watched her move and gyrate, slowly removing her sequined bikini, revealing those lovely breasts. He was mesmerized and he wanted to talk to her, to find out more about her.

"Want me to buy you a private dance from her?" Claudia whispered into his right ear. "My sister may be able to see that I get a discount."

"Huh?" Ulysses was shaken from his trance as he turned to face her.

Claudia glanced down at his crotch, "Looks like you like her. It feels like you like her," Claudia grinned, her hands squeezing and rubbing an erection that had grown down the length of his thigh, the cockhead nearly extending from the bottom of his cargo shorts.

"I, uh, sure," he replied, watching the girl exit the stage to change outfits and make her way to the large room like the rest of the strippers did.

At this point, Ulysses noted that Nicole and Taylor had returned from wherever they went with TJ's father. They both had tale-tale smiles on their face. The kind of smile Nicole had last night and today when she exited the shower with TJ. Claudia had gotten up to go find the dancer. Angela took over cock squeezing and rubbing duties. Ulysses smiled politely at her and looked around the room. He saw TJ talking to his dad and the woman that dragged him off. They finished their conversation and headed back toward the table.

Ulysses was annoyed and was hoping Claudia would return soon as he was looking for an excuse to leave the table. Angela had pulled his cock out from under his cargo shorts and began jacking it under the table as she went on and on about much she loves black cock. She said she's glad she's not staying with her Aunt Emily in town, complaining about her seven children in her crowded home.

"You have an aunt named Emily?" Ulysses said, starting to see some resemblance.

"I do. Do you know her?" Angela asked.

Ulysses thought back to about to a year prior when he sprayed semen all over Emily's pregnant belly, and then a few months following that event, grabbing her pregnant belly tightly in his arms as he pounded her relentlessly, hoping to induce labor.

"I just used to be a yoga instructor, and there was an Emily in one class. Probably wasn't her though," He said, turning his gaze away from Angela and gulping.

Finally, after about 15 minutes, Claudia returned. She wasn't alone, the stripper was with her. Angela put Ulysses' cock back where it belonged, pulling his cargo shorts down to conceal it. "Here she is," Claudia presented the stripper to Ulysses.

"Hi," he awkwardly said to her.

"Ready for a private dance? Follow me," She said, smiling energetically, holding out her hand. Even her voice sounded young. Ulysses stood, grabbing her hand, following her to the rooms to the side. He turned around back to his table, to see TJ talking with Nicole and Taylor, and Tony leaving the strip club with Angela and Claudia just like he did with the other two women earlier in the night.

Chapter 2

Ulysses couldn't take his eyes off the stripper's gorgeous blue ones. The music started and she started swaying back and forth for him. She turned around, rubbing her thong-covered butt against Ulysses' crotch, causing him to groan.

The dancer moaned, feeling Ulysses' erect cock against her butt through his shorts. She turned around and straddled him, "What's your name?" she asked.

"Ulysses. What's yours?"

"Penny," she answered, grinding back and forth on his lap. "Feels like you got a nice dick."

Ulysses nodded awkwardly,"Is that your real name? Or a fake one you use when dancing?"

"It's my real name," She said, arching her back, unclasping her bikini top, pulling it down, exposing her large breasts. Ulysses looked on in wonder. She was so young looking in the face, but her body was not young looking at all.

"How old are you?" Ulysses asked. Penny moved to her knees in front of him, rubbing her breasts all around his lap.

"I turned 18 yesterday," She replied, looking at him seductively, rolling her shoulders, her tits dragging across Ulysses' hidden erection. His eyes shot open, he couldn't believe she was 18.

"Really? How long have you been doing this?"

Penny rose to his lap again, moaning, running her hands all over his chest, dipping them under his shirt, and running them over his toned stomach. "Almost three years," she replied, dry humping him, moaning in his ear.

"What?!? Are you serious?" He asked, jerking his head back, breaking her of her concentration.

"Yeah, I ran away and came here. Now then, where was it?" She ran her hands up over her breasts as she grinded against Ulysses.

"Wait, you don't have a place to go? Where do you live?"

"Baby, I wouldn't worry about that if I were you. Since you're curious, I live with one of the older strippers and sometimes stay with Fat Rob," Penny explained then continued her lap dance.

"Have you been to high school?"

Penny was getting frustrated. "Stop talking! No, no school. I ran away from home, I lived in Miami. I'm here now, doing this. Alright? Can we continue this now? The song is almost over."

Ulysses shut up, seeing he annoyed the dancer who was simply trying to do her job. He was visibly concerned for the girl, watching her gorgeous ass grind against him. He sighed when the song was over, watched her dress, and followed her back out. She thanked and went on her way.

"Wait!" He called out to her. Penny turned around, still slightly annoyed at him. Ulysses was pulling out a card from his wallet. It had his cell phone number and his work phone number the modeling agency assigned him, along with an email address.

"Here, Take this. If you ever need a place to crash or just want to go get some food, give me a call," he told her.

Penny nodded, taking the card, smiling softly, and went to the backstage area. Ulysses headed back to his table. A few moments later, Claudia and Angela returned with Tony, goofy looks plastering their faces.

The rest of the evening was incredibly boring for him. Penny hadn't taken the stage again. For the next couple ours, he watched TJ's dad chat with Fat Rob, Angela, Claudia, Nicole, Taylor, each woman taking turns following Fat Rob into his office most likely to have sex.

When the last of the four women went back to Fat Rob's, Penny danced again, finally. Ulysses watched her with sadness and sympathy. He felt her pitiful life could've been better. She had no high school education, no college, no real job, and wasn't homeless, though didn't have her own place.

"Everyone ready to go? I'm sore!" Nicole joked, back from Fat Rob's office, straightening her hair. They all nodded and stood to leave.

"Hey give me a minute, I'll catch up," Ulysses said, following Penny as she left the stage. He was able to watch her going into, what he presumed to be, Fat Rob's office. Ulysses carefully snuck down the dim hallway, seeing Penny in the distance dash into the office. Someone walked by Ulysses causing him to pretend he was either working there or waiting for someone. After the moment passed he continued down the hallway.

He heard her. He heard her moaning. "Uh, Uh, Ahh, yess!"

When Ulysses peeped into the door's window, he saw Penny bouncing up and down on the fattest cock he had ever seen. Her head was thrown back, Fat Rob was clutching her waist, and his black cock was covered in creamy, white, pussy juices.

Ulysses shook his head, leaving to go catch up with his friends.

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Nicole and her sister, Taylor, were riding TJ and Ulysses respectively while Claudia and Angela waited their turns. The two men lay side-by-side in bed and the two sisters held hands, bouncing up and down, climaxing together.

"Ok our turn," Claudia said, spanking Taylor, Ulysses' cock slurping out of her when she moved off him. Claudia began moaning and riding him to her own climax. The four women did this most of the night, all four taking turns riding the two black men to orgasm. Ulysses was right; he would hardly sleep at all. Thoughts of Penny ran through his head. He couldn't believe she had been doing this occupation, and who knows what else, for so long. She was just a kid.

Chapter 3

A few months later, it was mid-May, and Devin, Ulysses' former stepmother was having dinner at his apartment. Ulysses hugged her from behind, smelling her thick blonde hair, kissing her shoulders while she cleaned some of the dishes. They were both naked and had been for most of the day.

"Mmmm, Michelle doesn't know what she's missing," Devin moaned, referring to a coworker Ulysses occasionally alluded he had feelings for, leaning her head back on his shoulder.

"Desert time," She said playfully, going to her knees. Ulysses loved this woman. Devin and her sisters had been servicing him since he was a teenager. He often thought, now that she was divorced from his dad that he could be with her, thinking maybe she could be the woman that makes him forget all about his coworker, Michelle. Ulysses had all but forgotten about meeting that poor girl at the strip club.

They made love for most of the evening, his bed slamming against the wall, Devin urging him on to finish. He took a break around midnight, standing on his apartment balcony, nude, checking his cell phone when it rang. He didn't recognize the number. He wondered in the back of his mind if it might just be that young girl he saw earlier in the year.

It was. Penny was crying, asking him if he remembered her, to which Ulysses assured her he never forgot. She asked if she could come by for a few days. She said she was running away from Fat Rob, explaining that he's getting too demanding, too aggressive, and too rough with the girls.

Ulysses couldn't say no. He quickly informed Devin of the situation, hearing her remark about how he was too nice. Ulysses moaned, watching her perfectly toned 40 year old body, slide out of bed and put on a bathrobe.

"I'll be naked again soon," Devin promised, heading to the kitchen to warm up leftovers for the visitor.

Penny arrived in about an hour. Someone had given her a ride. She looked haggard, tired, and hungry. Ulysses smiled warmly to her, welcoming her in, introducing her to his stepmother, showing her around. She inhaled the leftover food from dinner, devouring every last morsel, smiling awkwardly when she finished.

"It's fine, I have plenty more," Ulysses chuckled. He showed her to her bedroom, letting her know she could stay as long as she needed. Devin shot him a questioning look as she headed back to his bedroom.

He grabbed her some towels and made sure she had enough blankets if she needed them. "Thanks," Penny said, looking to the floor.

"It's not a problem, I told you, I'm here to help."

"I really appreciate it. I'll only be here for a few days," Penny said.

"However long you need. I'm going to head to bed, don't hesitate to wake me if you need anything." Ulysses nodded and left the guest room.

Right as he got to his door, he paused, thinking he forgot to show her where the laundry room was. He figured she could find it, but wanted to be sure. As he went back to the guest room, he peeped through the door, before opening it all the way. Penny was lying on her side, facing the door, still in her clothes, her eyes shut. Ulysses smiled, entered the room and turned off the light.

Ulysses headed back to his bedroom to find Devin out on the balcony, nude, watching the city lights in the distance. Ulysses stripped down and joined her. Holding her breasts from behind, kissing her neck, she asked him if Penny was ok.

"I think she's asleep," he replied.

"Please be careful. You don't know if people are after her or not," Devin warned.

"I think it'll be fine," Ulysses assured her, bending slightly at the knees, guiding his cock into her from behind.

Chapter 4

After Devin and Ulysses showered together the next morning, she prepared breakfast for him and Penny. Penny, again, devoured it hungrily. Devin flashed Ulysses a concerned look, said goodbye to them both, and headed to work.

"Ok, I have some work to do today at the gym. I teach yoga every once and awhile and I'm a personal trainer. So I'll be gone for several hours. Please just relax and make yourself at home," He told Penny as he tied his tennis shoes.

"I will. Thanks so much for everything," she said softly.

Ulysses patted her knee and stood, smiling down at her, "Please call me if you need anything ok?"

Penny nodded, curling up on the couch, having showered after breakfast.

Ulysses left, wondering if she might be gone by the time he returned later in the day. He wondered if she might steal something, thinking that he didn't have any cash hidden around or weapons, admonishing himself for not completely trusting the girl. He called TJ, who was in Tampa Bay now, briefing him of the situation. He also warned Ulysses to be careful.