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.”
Amanda smiled, “It’s okay Charlie. Nothing to be ashamed of. I want you to be completely honest with me. How often do you masturbate?”
“Um, usually a couple times a day. Sometimes more, on the weekends.”
“Do you use pornography? What do you fantasize about when you masturbate?” Amanda asked.
Charlie looked around to make sure there wasn’t anyone to overhear. “I look at naked girls. Sometimes I look at she-males, or…men.”
“Do you think about sucking cock?” came Amanda’s blunt question.
Charlie couldn’t help blushing more, “Yes.”
“But you still like woman, too, don’t you.”
“Yes, very much.”
“Have you ever had sex with another man, Charlie?”
Amanda waited to continue when a waitress arrived, ordering herself a beer. “Well, Charlie. I need someone like you to help with my husband and I. You see he’s much like you, only worse. He’s a total faggot cock-sucker. Women don’t interest him. After we got married the sex was dreadful; he could barely get it up. For years I thought it was me, that perhaps I was doing something wrong. Then I caught him on the computer looking at gay pornography and found out he likes the cock. I need someone to satisfy his filthy urges, as well as my own needs. You’d have to quit your job and move in with us. You’d be responsible for household chores and you’ll have to do whatever I say. I’m not looking for a another worthless husband or a boyfriend or a lover. I want a horny pervert to help manage our sexual needs. Do you understand?”
“I think so.”
“Good. Then why don’t we get out of here and try you out, shall we?”
“Try me out?” Charlie asked.
“Yes. Let’s go to my place. I want to get a look at that cock of yours.”
Charlie readily agreed.
They rode in Amanda’s car to a suburban neighborhood a few miles from the bar. The house was very nice, much larger than where Charlie and his mother lived. Once inside, Charlie noted that the house was decorated very tastefully and everything appeared normal.
Amanda led them into the kitchen, “My husband is in the basement, that’s where I keep him.”
Charlie was a little confused, “Keep him?”
“Yes Charlie, he has a room down there I allow him to have. You see, after I found out he was a worthless cock-sucker we came to a little arrangement. I don’t reveal his lust for dick to the world, or kick him out of the house and divorce his penniless ass, in return he has surrendered control of his life to me. We pretend to be a normal couple, in front of family and for social occasions, but otherwise he is my slave.”
“What do you make him do?” Charlie wondered.
Opening a cupboard, Amanda removed a small plastic bowl. “He keeps the house while I am at work. If I take you on you’ll help him with those chores. I make him pleasure me orally, since his cock is useless to me. Why don’t you take off your clothes, Charlie.”
Looking at the plastic bowl, Charlie asked “R-right now? Right here?”
“Yes.” Amanda replied, turning to look at Charlie expectantly.
Charlie wasn’t sure about this strange situation, but felt curious to learn more. He undressed in the middle of the kitchen floor while Amanda watched him. When he was fully naked, she regarded his flaccid cock with slight amazement.
“My god, Charlie. Your balls are huge.”
Charlie felt very self-conscious under Amanda’s scrutiny as she stepped closer to him, reaching down to cup his scrotum in her palm. His balls were indeed large; bloated and puffy. “You really do masturbate a lot, don’t you?”
Charlie could only nod. His shaft was slowly growing erect as Amanda felt and squeezed his sack. “They get like that when I don’t jerk off.”
Letting go, Amanda moved to a drawer. “Have you masturbated today, Charlie?”
Charlie shook his head, “No, I was at work today.”
Amanda pulled out a rubber glove from the drawer, then a jar of Vaseline, “Get on your hands and knees, Charlie. Right there on the floor.
Charlie blinked, unsure of that glove and Vaseline. ‘Is she going to stick her fingers in my ass?’ he thought, but did as she said anyways, kneeling down onto the kitchen floor.
Amanda kicked a small stool over beside Charlie, sitting down upon it as she snapped the glove over her hand. She placed the plastic bowl under Charlie, beneath his penis, then coated his dick with the Vaseline. Charlie groaned in pleasure, his penis growing fully erect as Amanda applied the slick substance all over the hard shaft.
“Lately my husband is whining that he doesn’t get any dick.” Amanda said as she started squeezing Charlie’s penis and pulling it to point downwards at the floor. “I’ve tried to find another submissive bisexual man to move in with us, so there’s another cock around to help fill his homosexual urges, but it’s not been easy.”
Charlie started breathing heavily. It had been a while since anyone else had touched his penis, and the way Amanda’s slick rubber glove felt on him was amazing.
“If I choose you Charlie, you must understand that I am in charge. I will use you any way I see fit, sexually or otherwise. I don’t think much of men who like the cock, so I will degrade you. I’ll make you do perverted homosexual things with my husband for my viewing pleasure. Do you understand?
Charlie was delirious from the attention Amanda was paying to his penis. She was stroking her hand from the base of his shaft down to the head of his cock, as though she were milking a cow. “Y-yes, I understand.”
Then Charlie felt Amanda’s hand leave his cock, which was leaking pre-cum and twitching with desire. “Stay there.” she said, and moved over to the basement stairs in the hallway nearby. When she returned she was leading a middle-aged man by a leash and collar. He was naked and slightly chubby, with a massive erect penis. Charlie couldn’t believe the size of it.
“Douglas, I want you to meet Charlie. Like you, he craves the cock. Charlie, this is my worthless faggot of a husband. Would you like to suck his cock?”
Charlie swallowed as he stared at Douglas’ erect shaft. His fantasy was about to come true, he was actually going to have another man in his mouth. And what a cock! It must have been ten inches in length. He didn’t know how to answer, unsure if he could go through with all that Amanda was proposing. Douglas didn’t say anything, passive in the presence of his wife, but he was staring at Charlie’s kneeling body with something akin to lust.
Amanda didn’t wait for Charlie’s answer, bringing Douglas to stand in front of Charlie’s face. “Go ahead, Charlie.” she said, reclaiming her stool.
Charlie’s heart was racing. This was the moment of truth. He felt Amanda’s rubber-clad hand go back to milking him just as Douglas took his cock and pointed it towards Charlie’s mouth.
He did it. Charlie opened his lips and let Douglas slide that big cock between them, filling his mouth. Closing his eyes, Charlie started sucking on it, licking and tasting the head of the cock with his tongue. Douglas groaned with pleasure.
“Are you a cock-sucker, Charlie?” Amanda asked as she jerked him off with her milking strokes. “Are you a perverted homo who needs a mouth full of cock?”
Charlie was in heaven, nodding his head. He had a cock in his mouth and a sexy older woman was giving him a kinky hand job. He could feel his cum filling his balls. Douglas started to grunt obscenely and grabbed Charlie’s head, fucking his cock into Charlie’s face with urgency.
“Look at you two dirty faggots.” Amanda said, increasing the pace of her milking strokes on Charlie’s throbbing penis. “You are filthy men with naughty desires.”
Despite her degrading comments, Amanda’s free hand was down her skirt; masturbating herself at the sight of the two men. “I bet you two want to fuck each other in the ass, don’t you? I can’t believe how worthless you both are to me, all you do is crave the cock, forcing me to masturbate.”
The degrading talk turned Charlie on even more. He was moaning and grunting, swallowing and choking on Douglas’ huge cock. His hips were bucking in time with Amanda’s masturbating hand. He knew he wasn’t going to last much longer.
Douglas was first to orgasm as he held Charlie’s head in place, his cock down Charlie’s throat. There was so much cum that it filled Charlie’s mouth, forcing him to swallow quickly. Even then some squirted out between his lips and decorated his face and chin. Charlie loved it, loved the taste of the cum and the feel of the massive twitching cock in his mouth.
“That’s it, Charlie! Swallow all of that filthy cum down.” Amanda coaxed with her words. Her hand was coaxing as well, pulling and stroking swiftly on Charlie’s cock. “Look at your big disgusting balls, so full of the man-milk.”
Amanda abandoned masturbating herself and used her free hand to squeeze Charlie’s bloated balls. He grunted like an animal and his cum began shooting out. Amanda aimed it into the plastic bowl, the milky fluid landing in splattering ropes. Charlie’s orgasm was immense, emitting a copious amount of sperm that almost filled the dish.
Taking the dish, Amanda handed it to her husband. “Here is the cum you have been whining about, ‘dear’.”
Charlie watched as Douglas took the bowl and started licking up all the hot cum, slobbering and tonguing it all into his mouth to swallow. It was so naughty and beautiful.
“I think you’re going to work out just fine, Charlie. Tomorrow you are going to quit your job and tell your mother that you are moving out. Tonight you’ll stay here. Watching you two filthy boys has made me horny, and I want to try that cock out for myself. My husband can’t get it up for anything but a man, but maybe you’re not totally worthless. Can you get it up for me, Charlie?”
Charlie looked at Amanda’s sexy body as she sat on the floor, her legs spread within her skirt.
He nodded eagerly. Yes, Charlie’s fantasies had come true.