Charity Walters was just 22 years old when she accepted the fact that she was obsessed with giving oral sex to men. It was her ultimate kink. As much as she enjoyed sex and receiving oral herself, for whatever reason, she found herself to get the most pleasure out of sucking men off.
It started back in high school with her ex boyfriend, Derek. He talked her into it their senior year after several months of trying, and she found out that she enjoyed it. After graduation, they were at a friend's house for a party, snuck off to a room so she could give him head, and two other guys walked in. They stood there, watching the show and encouraging her as Derek enjoyed himself. Before long, she found that she was giving these other two guys head as well. One of them went so far as to facefuck her with his 8 inch cock, and Charity was loving it. Turns out Derek was enjoying the show as well, but not for the reason why Charity thought.
A few months after that, Charity went through a breakup after Derek was caught giving head to another guy in his car in the parking lot of the local gym. Although she was absolutely hurt over the act, she opened the door to let Derek explain. It had turned out that Derek was struggling with his sexuality for a while, but after only a few days after their breakup, Derek came out to Charity as being gay. Still slightly angry about the situation, but being the type of woman she was, she forgave Derek for how things ended.
This ultimately resulted in Derek and Charity becoming best friends instead of a couple, and Charity was absolutely okay with that. Now, she found that she had someone that she could confide in to discuss her oral fetish. She was able to sit there and talk about it with Derek, and they would find themselves amused when they would see a guy out in public and they would both try to size him up through his pants. One day, Derek invited Charity over to his place, where he showed her his new 10 inch realistic looking dildo, along with a matching one for her. He said it was so they could practice their skills together and coach each other along the way. They met together at least once a week for blowjob practice on the dildos.
Whereas Derek was skilled, he was still amazed at Charity's abilities. After some practice, she found out that she could deepthroat the entire 10 inches of the dildo with no problem. She ended up having Derek order a 12 inch dildo, and she worked her way up to that as well. Before too long, she could take the entire 12 inches without gagging.
After a while though, Charity grew tired of the practice sessions. She longed for the real thing. She started to meet up with guys through work. Word traveled fast at her job about how much she enjoyed giving blowjobs behind the store building. She found herself giving head to five of her male coworkers on a weekly basis. When she was caught by her boss, she thought for sure that she was going to get fired. Instead, when he called her into his office, he asked for her service. She gave him one of the best blowjobs she'd given up to that point, and to secure the deal, instead of having him unload on her face and breasts, she swallowed cum for the first time. Not only did she get to keep her job, but she discovered that she enjoyed the act of swallowing along with giving head.
Over the next few years, Charity made it a point to suck cock at least ten times a week. Usually it was the same guys, but after a while, she turned to hookup apps. Luckily for her, these all turned out to be decent guys with no bad intentions, but she still felt uneasy about it. The silver lining was that she got to have the guys show up at her place, where she kept a 9mm pistol within reach should anything go wrong. She was fortunate enough to not have to use it.
The blowjobs with random men came to an abrupt stop though. The owner of the apartment she was renting sold the building and the new owner opted to make it a apartment building for people 50+ in age only. The majority of the residents there got to keep their living space, but for Charity and a few others, they had to vacate within a month. She looked everywhere she could, but with just a week left to move, she got a phone call from her dad, Jim. He offered her a room at his place. She accepted and moved in with her dad.
Initially, Charity was more than happy to be living with her dad again. She found herself pleasing her coworkers and boss more often now that her hookups were limited due to her living situation, but her dad insisted that she didn't pay rent. He just wanted some help with groceries or an occasional bill or two. It was a perfect opportunity for Charity to save back some money for her future.
That was, until the day that it was announced that the store she worked at was being closed. The national chain of the store announced that they would be downsizing over the next several months, shutting down some of their stores in less populated areas with less customers. Charity's store was one of the first to be shut down. She was going to have to live off the money she saved back until she found a new job. Her first thought was to call Derek and see if he had any leads.
*****
"Hey Char-Bear! How the hell are you?" Derek answered the call like he always did. It never failed to bring a smile to Charity's face when he did that. The man truly was a great friend, and in spite of the history with their breakup, Charity was happier with him as a friend than she was with him as a boyfriend.
"Hey Derek! I need your help with something."
"Anything for you doll. Hit me with it."
"Well...do you know of any job leads in the area? The store is closing soon. I need to find something."
"Aww shit. I'm sorry Charity. I wish I could help, honestly. But, I'm looking for something too." Derek said. He paused for a moment, and Charity started to reply.
"Well, okay. I'll keep looking. Thanks anyw---" she said before getting cut off by Derek.
"Wait one second. I've got an idea, but I want you to be completely and totally open about it and don't chew my ass out for suggesting it. Okay?"
"Okay...Derek, what are you thinking?" Charity asked, unsure of what her best friend was thinking about. This was unlike Derek. Ever since he came out to her, he's never been one to be shy about things, whether it was talking about sex or giving an honest opinion about something. For whatever reason, he was slightly hesitant about spilling the beans for thus idea of his.
"I'm really not sure how to even say this delicately, so I'm just going to ask." he said. He took a pause before continuing. "And I mean it.. don't chew me out..."
"Just say it. I promise to be open or whatever. Not mad." Charity reassured her friend. "Now, ask away."
"How...how would you like to suck dick for money?"
Charity was shocked for once when it came to something Derek said. She never expected to be asked that question by anyone, but especially not Derek. She stayed quiet for a moment before Derek came back on.
"Charity...you promised not to be mad at me. I'm being sincere with you right now. It's only a question and I'm not trying to push you into anything you don't want to do."
"Are you trying to pimp me out?" Charity asked. Derek couldn't help himself and laughed at her question.
"No, not at all. No prostitution! Well...mostly none."
"Okay, then explain this to me!" Charity replied.
"Have you ever heard of a gloryhole?" Derek asked point blank. "It's where there's a hole in a wall and guy will stick his ---"
