Though he was twenty six years old Charlie still lived with his divorced mother; in her basement in fact, because he couldn't afford a place of his own. Charlie wanted to move out and get an apartment or perhaps rent a townhouse, but with his meager salary his prospects were not good. He worked at a magazine & collectables store where they sold things like comic books and baseball cards. His pay was barely a couple dollars above minimum wage.
In the back of the store was a small area where pornography was sold; just dirty magazines and a few triple-x videos. Charlie was addicted to this pornography and usually purchased a small stack of glossy stroke books each payday to bring home and masturbate to. His addiction started with girly magazines featuring young naked women, but his curiosities led him to more kinky fair when he found the common stuff no longer fully satisfied him. Charlie began buying magazines with she-males and transvestites, and hardcore stuff featuring two males and a girl in a bisexual theme. He imagined what it would be like to suck a cock when he jerked off, or to have another man fuck him in the ass. Always his fantasies involved a woman watching him perform these dirty acts, encouraging or forcing him to do it. Charlie even tried tasting his own sperm after he would cum, which turned him on so much he would have to jerk off again while looking at pictures of men sucking other men's cocks. His favorite pictures usually featured a sexy woman looking on or joining in.
While reading one of his bisexual themed magazines, Charlie came across an add in in the personals section which the publications often had in the back. It read:
'Live-in bisexual man wanted for regular milkings and degradation by dominant female. You will be expected to suck cock and more. Must be completely submissive. Room and board provided.'
Charlie got an instant erection by the simple words. It was as though the woman who wrote the ad was straight out of his masturbatory fantasies. He grew even more excited when he saw that the woman lived in the same city. Dreams of moving out of his mother's basement and living out secret dirty fantasies filled Charlie's mind. He simply had to call the number provided.
As the phone started ringing, Charlie was suddenly very nervous. What was he doing? Could the ad even be real? Could he go through with it even if the ad was real? He started shaking in anticipation when the line on the other end answered with a female voice, "Hello?"
"Uh, hi. Um, my name is Charlie."
"Can I help you Charlie?"
"Y-yes, um, I am calling about a personals ad?"
There was a brief pause, then the woman asked "I see. Tell me something Charlie. Are you a naughty cock-sucking slut?"
Charlie was stunned by the bluntness of the question. "W-what?"
"I asked you a question, Charlie. I expect an answer. Are you a filthy cock-sucking slut?"
"I-I'm not sure. I never have but I've always..."
The woman interrupted, "I'm not looking for someone on the fence, Charlie. I can deal with inexperience, but you don't sound very certain of yourself."
Worried she was going to hang up, Charlie blurted "No wait! I mean, yes, I'm a filthy cock-sucking slut. At least...I want to be."
"All right, Charlie. Why don't we meet. Are you free tomorrow night?"
Charlie quickly agreed to meet this mysterious woman from his fantasies at a bar the following night. He was to wear a white tee-shirt, a red ball cap, and she would approach him. After hanging up Charlie was incredibly excited and aroused. He jerked off three times before going to sleep, thinking that he was about to actually live out all his naughty fantasies.
The following day at work was difficult for Charlie. He had a boner most of the day and couldn't stop thinking about dirty things and what was to happen that night. When he finally got off work he rode his bike to the bar and put on a red cap. The place was fairly busy with the happy hour crowd, but Charlie was able to secure a small table and ordered a beer. He didn't get more than two swallows into it when he felt a hand on his shoulder, and a woman's voice asked "Charlie?"
Turning his head, Charlie saw a woman who appeared to be in her early forties with shoulder-length dark hair and blue eyes. She was dressed modestly in a white button blouse and a grey skirt that went past the knee, though Charlie could tell she was shapely and fit. He found her to be very attractive.
"Yes, I'm Charlie."
She sat down at the table and said, "Hello Charlie. My name is Amanda. I believe we spoke on the phone last night?"
Charlie nodded, "Yes, um, hi. It's nice to meet you."
"You're cute." Amanda commented. "I saw you walk in. I was glad to see that you're not overweight. A little shy though, aren't you. Do you have a girlfriend, Charlie?"
Charlie shook his head, "Um, no. Not since high school."
Amanda nodded as though she already knew. "Well, Charlie, why don't you tell me about yourself."
"Um, okay. I'm, uh, twenty six. I work at a magazine store as a cashier. It's a pretty good job, but it doesn't pay a lot. I live over on London avenue with my, um, with my mom." Charlie couldn't help blushing a little.
"That's all very nice, Charlie." Amanda said in a cool tone. "But not really what I'm interested in. Do you masturbate a lot?"
With his cheeks coloring even more, Charlie nodded. "Y-yes."
