The Casanova of Juno Terrace Ch. 04

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Chapter 4 – Dee Dee/Bailey: Two for One Special

Being that Juno Terrace was home to all female tenants, one of the common activities to do during the summer was sunbathing. For years, there were complaints because some of the tenants would sunbathe nude and wouldn’t bother covering up their balconies, assuming all of the tenants were women and forgetting that there were children who could see what was going on.

After enough complaints were levied, a compromise was made. When the apartment complex was initially built, the roof of the complex contained the fitness center where the penthouse suite would normally be. The fitness center contained an indoor and outdoor pool. Adults were only allowed in the fitness center, but there was a separate access elevator for the women to bring their children up to use the pool.

The compromise was that a new pool was constructed on the grounds around the complex that was family friendly, and the pool on the roof was made adults only and was the only place where nudity was allowed at any time for women to sunbathe.


Deidre Dales, who called herself Dee Dee, was one of those women who loved to sunbathe nude and having the complaints levied against. She was a carefree spirit, to a fault. Dee Dee was a single mother all her adult life. As a freshman in college, she got caught up in the party scene, getting too drunk for her own good. Combined with her ADD, she constantly was ending up in a drunken haze in a different frat guy’s bed every morning.

Naturally this led to her getting pregnant, never knowing who the father was of her daughter, Bailey. For years, Dee Dee lived with her mother while raising Bailey, but continued to be a carefree, ditzy slut her adult life. She worked at the nearby truck stop as a waitress, and would earn extra money prostituting herself to the truckers that would come and go. Continuing to not be careful, she was caught by the owner of the truck stop disappearing from her shift. Once he realized what was going on, he blackmailed her and threatened to call the cops if he didn’t get to fuck her as well.

Dee Dee kept this a secret from her mother, only seeing customers at the truck stop. But after years of not worrying about condoms and being careless with her customers cumming in her, Dee Dee got pregnant again, but miscarried a few months later. After this and realizing what was going on, her mother gave her an ultimatum to stop sleeping around. She lied to make an agreement, instead got her tubes tied so she could never get pregnant again and continued to prostitute herself to the truckers, becoming more and more of a Lot Lizard.

After her mother died a few years ago from cancer, Dee Dee and Bailey moved into Juno Terrace Apartments. Dee Dee had done her best trying to keep Bailey from knowing what she did. However, Bailey was just as carefree and rambunctious. While she was already having problems with her school grades, and no desire to go to college, Bailey was expelled from school at 18 when it was discovered she was caught fighting with another student over marijuana Bailey had tried to buy from her.

Uncannily, Bailey had remained a virgin until 18. Unsure what to do with Bailey after she was expelled, Dee Dee sold Bailey’s virginity on some internet forums, Initially, Bailey was furious at her mom for doing that, but begrudgingly went along when Dee Dee told her it was for $5,000 with this rich executive. Meeting at an upscale hotel one night, Bailey went in as an innocent virgin, and by the next morning, the nymphomaniac inside her that she inherited from her mother had been unlocked, and she fucked the executive so many times that she wore him out and got paid $10,000.

For the last two years, Dee Dee and Bailey have become full-time escorts. Dee Dee worked out of the motel adjacent to the truck stop diner. As long as she gave the owner of the diner, who also owned the motel, free service, he gave her a room for free and looked the other way on her business. Because of the lack of truckers working the weekends, Dee Dee spent the weekends at her apartment, taking care of her body. The 39-year-old, greasy blond haired MILF would spend the weekends at the fitness center taking care of her 5’4″ 225 lbs chunky body. All of her regulars preferred her MILF body, especially her large hips and ass. Her overweight body still produced natural 42DD tits, but it was her ass that her clients kept coming back for.

Still being 20 and having been recommended by the executive who took her virginity, Bailey became more of a high-end escort. Bailey was the spitting image of her mother, being 5’1″ 165 lbs, Bailey had a round ass, but her 40DD looked bigger on her smaller body. At the behest of Dee Dee, Bailey had her tubes tied as well. She makes good money fucking all of the rich men in the tri-county area as one of the few escorts that will let her clients fuck her without condoms with a valid STD test.

Recently Bailey started advertising 2-for-1 specials canlı bahis with Dee Dee. Getting into the same business, the two had become bisexual, having to perform together in front of clients. One of their favorite things to do is eat the cum out of each other’s pussy. It wasn’t uncommon when one came back from seeing a client that the other would eat the creampie in the other’s cunt. Given that Juno Terrace was the best they could afford; they both swore never to bring clients home.


On this hot Saturday, Dee Dee was one of a few woman sunbathing nude at the roof pool. Bailey had an overnight date with another executive, and as Dee Dee sunbathed, she imagined Bailey nude as well as her client was getting one last fuck before Bailey had to check out of the hotel. Between thinking about Bailey and gazing at the other naked women around her, Dee Dee couldn’t help but feel her pussy getting wet.

Dee Dee sat chatting with the other naked women as their bodies roasted and tanned in the heat. Normally, the women come up in their bathing suits and take them off when they get to the pool in private. Dee Dee lived on the top floor near the stairwell that led to the pool access, so she would forego clothes, wrap herself in an oversized towel, and come up to the pool already in her birthday suit. Normally, this wouldn’t be an issue, except this time when she left her keys in her apartment, and because she constantly forgets to lock her door when she leaves for work, the door to her apartment relocks after closing.

After spending a couple of hours sunbathing and cooling off in the pool, Dee Dee wrapper herself back in her towel, put on her sandals, grabbed her bag and proceeded to return to her apartment. When she got to the door, she searched her bag for her keys, but eventually remembered that she left her keys in her purse and never moved them to her pool bag. Seeing that the hallway was empty, she quickly made her way to the elevator, hoping no one would see her. She got into the elevator alone and made her way to the ground floor where the maintenance office was, hoping someone would be there to let her in.


After finishing his shower, Gio had been catching up on paperwork from while he was gone. Assuming no one was going to come by, he worked nude after the shower when he heard a frantic knock at the door. Not expecting anyone, he was shocked at first before quickly finding a pair of boxers, shorts and a t-shirt and heading to the door. Looking through the peep hole, he found a woman who appeared to be naked underneath a towel.

Opening the door, Gio asked the woman, “Can I help you, ma’am?”

Dee Dee said, “Yes, I’m Dee Dee in 969. I left my keys in my apartment when I went up to suntan and am locked out of my apartment.”

Remembering that room number from all of the complaints over the previous years, Gio knew who he was dealing with, but Dee Dee didn’t know who Gio was. She had heard all the rumors about Gio’s sex life, but didn’t know he was the man she was speaking with.

Gio was immediately agitated at Dee Dee walking the halls in an immodest state, quickly deducing that she went up to the pool naked and must have walked the halls like this when she was locked out. However, he was also incredibly turned on by the naked woman standing in front of him. Gio’s sex drive had been awakened from fucking Peggy and Tanya to the point that he was back in his old mindset of wanting to fuck whatever woman he saw. Realizing the power he had, given this tenant’s misbehavior, Gio decided he could use this to his advantage.

Gio sighed and said, “Yes, I remember you, Ms. Dales, Come on it.” Letting her in, he went to his desk, sat down and said, “Please, sit down.” Dee Dee sat down at the chair across his desk, crossed her legs, and held the towel above her tits.

Gio then looked at Dee Dee and said, “Ma’am, I’m sure…”

Dee Dee interrupted, “Oh, call me, Dee Dee.”

Gio held up his hand, “Ms. Dales, do you understand the problems you’ve caused in the last few years?”

Dee Dee paused and said, “Well, those were honest mistakes, but how would a maintenance man such as yourself know about…”

Gio interrupted, “Because I own the place.” Dee Dee’s eyes got wide as she realized it was Gio he was talking with as he continued. “I’m well aware of the complaints we received about your antics that caused us to set up the additional pool in the first place. Now you’re showing up at my office door naked and locked out of your apartment. Clearly you didn’t follow the rules about being properly dressed.”

Dee Dee looked at Gio scared and quietly responded, “Well… my apartment is right by… the entrance to the pool… and I thought… you know… no one would…”

Gio shook his head, “Being wrapped in a towel without any clothes on underneath is not properly dressed to walk the halls, Ms. Dales. If we get any more complaints about you, it may be grounds for terminating your lease.”

Dee bahis siteleri Dee was panicking. She had nowhere to go. Even with her escort money, this was the only place she could afford. Looking at Gio, she said, “Mr. Polo… You can’t… This is the only place I can afford… My daughter and I have nowhere else to go…”

Gio looked at Dee Dee, understanding the power he was in at this moment, and his cock started to harden. He decided that this was an opportunity worth pushing further. “Well, you should have thought of that before you broke the rules.”

Dee Dee knew the pickle she was in, as well as the rumors about Gio, and decided to play the only card she had. “Please, Mr. Polo, I’ll do anything.”

Gio crossed his arms. “Anything?”

Dee Dee then stood up, opened the towel, letting it drop to the floor, and standing nude in front of Gio, said, “Anything.”

Gio’s cock jumped. He kept himself subdued and said, “You realize what you’re doing, Ms. Dales. You are propositioning the owner of this apartment complex for sex in exchange that I let you off the hook for breaking the rules. I could have your lease terminated for this.”

Dee Dee couldn’t help but feel herself getting wet, she was getting excited trying to use her body to get out of trouble. “Well, if you’re threatening to terminate my lease, I might as well appeal to your manly desires, Mr. Polo.”

Gio was internally very excited at the prospects before him. There was a small voice in his head saying what he was about to do was wrong and not what his mother would want. However, with Peggy tearing down the barrier in his mind regarding the women here at the apartment complex, the head on his penis was doing all the thinking.

Letting his eyes wander and inspect Dee Dee, Gio said to her, “Is your daughter here?” Dee Dee shook her head no. “Ok, you are going to put your towel back on while I get dressed. I’m going to take you back to your apartment and I will fuck you there. Once I leave your apartment, we’ll pretend this didn’t happen.”

Dee Dee silently nodded as she bent over and picked up her towel and wrapped it around her. On the one hand, she was scared and ashamed that another man was about to use her, but her pussy was soaking wet, in some ways hoping the man in the rumors she had heard was about to use her. Part of being such a nymphomaniac was she liked it when men used her. She was a submissive and loved the feeling of being used by men to satisfy their needs. However, she was so engulfed in the current situation that she forgot that Bailey would be returning soon.


Gio got the rest of his work clothes on and silently led Dee Dee back to her apartment. As they walked back, Gio couldn’t help but ponder what was about to take place. All throughout college, he had plenty of women ready to bend over for him and let him fuck them, leading him to be very picky.

He had a couple of college girls that were his regulars, fuck buddies that knew he fucked other college girls like they fucked other college guys, but were willing to help each other keep their sexual appetites satisfied, and Gio could trust them to keep their ongoing affair private. Gio always said that those friendships would end when he left college, to ensure they didn’t become anything other than fuck buddies.

Then, there were the secret weekend orgies off campus at the vacation homes the rich, preppy guys had access to, that were drug and booze filled nights of endless fucking. Having the largest cock of any of the guys, he always had plenty of pussy for the whole weekend and many of the rumors of his sexual feats was born from these orgies.

Most of the other college girls Gio fucked were girls he met, either in class, at parties, clubs or bars, and had one night stands with him. These were the ones that he had to be careful about. Usually if they mentioned the rumors about him, he stopped socializing with them at the party. He did his best to weed out the girls that just wanted to fuck his massive cock, or try to get at his money, and only took the girls home that genuinely showed an interest in being with him. Usually the ones that lost out were the ones spreading the rumors about him.

The girls that would go back with him to his dorm after picking them up at the club were the girls that he relished the most, the ones that willingly surrendered to his wishes for the night, that after a night of Gio paying for their drinks, and access to the clubs, repaid him by going to their dorm and surrendering their bodies to him, staying up into the wee hours of the morning as Gio fucked them until he was satisfied, loving every minute of the passion they were receiving from him.

As Gio and Dee Dee arrived at her apartment, Gio realized it had been a while since a woman truly surrendered to him, and as Gio unlock the door to Dee Dee’s apartment, he knew that was about to change.


Opening the door, Gio walked into Dee Dee’s apartment as she followed bahis şirketleri behind him. Without saying a word once the door was closed, Dee Dee immediately removed her towel again. She took Gio by the hand and led him to her bedroom. She wondered for a brief second if Bailey was home, but she found no evidence of the sort.

Once inside the bedroom, Dee Dee looked up at Gio, him towering over her being a foot shorter than Gio, and went into escort mode said, “I am yours for the taking. What do you request of me?”

Gio looked down at Dee Dee and said, “Prepare my cock to fuck you.”

Getting on her knees, Dee Dee said “It will be my pleasure, sir.” As Dee Dee unbuckled Gio’s belt and pulled his pants and boxers down, his cock sprung out, already hard. She gasped at how big it was. Putting both hands around it, she moved his foreskin back and forth, marveling at his fuck stick. Indeed, she had heard the rumors that he was big, but she never thought it could realistically be this big. “Oh my gawd! You’re huge!”

Gio let out a low moan as he felt Dee Dee’s hands on him. “No backing out now.”

Dee Dee just sat there moving both of her hands, dragging his foreskin back and forth. She kept trying to figure out how this was going to get in her pussy, or her mouth for that matter. She started licking the soft head, trying to do whatever she could to try to pleasure this cock.

Gio was loving how the power trip he was on. He loved it when he fucked a new girl for the first time, especially the start when the girl is introduced to his cock for the first time, and seeing their scared faces, wondering how it was going to fit in their pussy. His ego was being stroked even more knowing that an experienced woman was just as scared as the inexperienced girls his age.

Dee Dee was scared for sure, but she was even more terrified when she heard a gasp behind her. She turned her head to see Bailey with a towel around her body and her hair wet, showing that she had been in the bath. Bailey had come home while Dee Dee was down in the maintenance office with Gio and was relaxing in the bathtub, hearing them come in and wondering what was going on.

Bailey thought that Dee Dee had brought a client home, “Mom, what are you doing? You said we should never bring clients home?!”

Gio looked at both women and said, “Clients? What are you talking about? We? Are you both prostitutes?”

Dee Dee was terrified, knowing what Bailey had just revealed to Gio and just sat there at Gio getting angry again. But Bailey was scared, too, hearing Gio express that he didn’t know he was getting a blowjob from a prostitute.

Dee Dee turned around to Bailey and said in a very scared tone, “Honey… this is… Mr. Polo… who owns the building… and you just told him… what we do…”

Bailey also became terrified. Being that she never went to college, she never met Gio, but heard all of the stories about him. As Dee Dee turned to face her, Bailey’s eyes got wide as she saw just how big his cock was. “But… why… is… he… and… why… are… you…”

Gio’s ego was getting bigger, because now the stakes were even higher for Dee Dee and now Bailey. He had both of them confessing to illegal activity, albeit not within his property, and even more incentive to let them off easy. Even with fucking four times in the last two days, Gio still had plenty of fucking to catch up on from last week, and now he had two pussies, a mother/daughter duo to boot, who were going to satisfy his needs.

Gio walked over to Bailey, towering over her as well, and said, “Your mother, who has been a problem here, was caught breaking the rules again. She was persuading me not to kick the two of you out.” He then took Bailey’s towel around her body, and pulled it off of her, revealing her naked body to him. “You’ve just revealed to me that you both have been performing illegal activity, and now you’re going to persuade me to not call the police.”

Bailey was initially mad at Gio for pulling her towel off, but like her mother, she was both terrified at the situation, and horny from it. She was staring at Gio’s cock, and feeling her pussy getting wet as well.

Gio’s ego was making him more impatient and more aggressive. He pushed Bailey to her knees and pushed his cock into her mouth, only getting about half his cock in. Bailey choked and gagged at the sudden invasion in her mouth, but slowly let Gio start to face-fuck her. There was a part of Bailey that was still mad at the situation, but she was just as much a submissive slut as her mother, and couldn’t help but moan as Gio was manhandling her, forcing her to suck his cock.

Dee Dee crawled behind Gio, reached underneath, and started playing with his balls, causing Gio to moan louder. For Dee Dee, it was terrifying to her that the owner of her apartment complex was threatening not only to kick her and her daughter out, but that he could have them both arrested. Bailey was a combination of terrified at Gio and resentful to her mother for putting her in this situation, first selling her virginity without her knowledge, leading her into a life of prostitution, and now having to sexually please a man to not get thrown in prison.

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