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.
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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 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.
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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.
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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.
