Gay stories 

The Ascension of Will Ch. 02

August 26, 2013 / by gaystory

Will was once again locked in the cage. He stared blankly at the ceiling, not really thinking about anything. He was pleased that he was at least allowed to have some books to read. Though by now, he’d already read them several times. They had also removed the chastity device only out of necessity…he kept getting sores from where it rubbed against his skin.

Will had been a slave for several months now. Until the last few weeks, he was kept chained inside the house. He was expected to keep the entire house clean and service the Master and Mistress in any way they demanded. When they wanted to punish him, they found a reason. Each punishment seemed to grow more and more sadistic, but somehow Will continued to endure it.

Most days and nights, Will was allowed to roam the house freely. If he had done something wrong that day they would keep him caged at night and only give him dog food to eat.

When they grew tired of corporal punishment, they would humiliate him in other ways.

Will recalled what happened when, the week before, he forgot to do the laundry. As a punishment, they made him put on one of Amy’s dresses with thigh high fishnet pantyhose and tacky high heels. The Mistress forced a large butt plug into him before they drove to the mall.

Once in the mall, they forced him to walk up to a boy about his own age and solicit him for sex. The boy looked as embarrassed as Will did before he walked away in disgust.

The Master and Mistress laughed hysterically as they watched from a short distance away.

Will considered trying to find someone to help him or simply walking away, but he had no where else to go. He hadn’t talked to his parents in months and he was too stubborn to ask for their help now. He also took into account that he was dressed in drag and he was not sure anyone in the mall would have helped him if he had asked.

His idea to persuade Amy to help him had not worked out either. She took advantage of him as much as the Master and Mistress did. However, she seemed to enjoy fucking Will more than her Master and it sometimes earned him small favors.

Will’s thoughts were interrupted when the door to the cage suddenly opened and the Master appeared. Will could tell from his red eyes that he had been drinking.

“I’m having a party tonight,” the Master said. He looked down at Will with contempt.

Since his arrival, Will discovered that the Master was a heavy drinker and often hosted parties. All of their friends seemed to know about Will and were happy to take advantage of him as well. Some of the worst things that had happened to Will were at the parties. He had been used as everything from a piece of furniture to a urinal. Sometimes, they would let Will get drunk with them only so he would be more willing to participate.

Will stood up and followed the Master out of the bedroom. Will began getting ready for the party by making sure everything was clean before the others arrived.

Will soon noted that the Master appeared to be hosting a poker game and all of the arriving guests were men. Amy and Julia were no where to be seen. Will did not recognize some of the men and he worried about what the Master had planned for him.

Even though he had been naked in front of many strangers since becoming a slave, Will was still embarrassed. The other men did not seem to be bothered by his lack of clothing and some were openly leering at him. Will tried to find something to busy himself with in the kitchen.

“Get in here, boy!” The Master called from the dining room.

Will was still standing in the kitchen and he made his way into the dining room as if he was heading for his own execution.

Will counted six men in total. They were sitting around the dining room table with cards in hand. Will paused in the doorway to wait for further instruction.

“Dan won the first hand, so you’re gonna suck his cock until someone else wins.” Will’s Master said through slurred speech.

Will tried to appear emotionless as he made his way across the room to Dan. He had met Dan before and did not care for him. He had fucked Will once and was particularly rough with him.

At one point in his life, Will questioned his sexuality. He felt more physically attracted to women, but he had found himself intrigued by the taboo of gay porn.

However, he still dreaded every act of anal and oral sex before it began. He tried to train himself to not think about what he was about to do or have done to him before, as the anticipation only seemed to make things worse. It was easier if he was mechanical about his tasks.

Will got down on his knees and crawled under the table. Dan had already taken his cock out and Will slipped it into his mouth. Will remembered from fucking him that Dan lacked stamina and he hoped that he could get this over with quickly.

Before the next man won, Dan came in Will’s mouth.

The games continued for hours. Two more men came while Will was sucking them. He had no choice but to swallow their cum. Will could not remember feeling this humiliated before. Thoughts of biting one of the men or running away occurred to him, but the thought of what they would do to him made his blood run cold. He tried to tell himself that giving blow jobs was better than the alternative of being gang raped by all of these men.

The tournament finally ended in the wee hours of the morning. A man that Will had never met before, Harold, won. To his horror, Will found out that he was the prize.

“Go with Harold, boy. He is your Master for the rest of the night,” Master Rob said.

After being allowed to put on a pair of shorts and shoes, Will followed Harold out to his car. Harold did not speak to Will during the drive; instead he turned up the radio.

Once they got to his house, Will nervously followed the man inside. He did not know Harold and he had no idea if he was going to hurt him.

“You can take your shorts off,” Harold said casually.

Will kicked off his shoes and pulled down his shorts.

They were in Harold’s bedroom. His house was very small and he apparently lived alone. Harold appeared to be in his early thirties and he looked like the epitome of the stereotypical homosexual male. He was clean cut with short, perfectly cut black hair. His clothes were too stylish for someone who obviously didn’t earn much money. His form was one of someone who worked out, broad shoulders, muscular arms, and a tapered waist.

“Go down on me again,” Harold said eagerly.

Will automatically dropped to his knees, unbuttoned Harold’s jeans, and slid them down just enough to expose his already hard cock. Will began sucking. His jaw still hurt from the earlier events and he had to force himself to focus on continuing.

“Oh god, stop,” Harold moaned and pushed Will’s head away.

Will tried to prepare himself for what was going to happen next. At least his cock isn’t that big, he thought.

Harold removed his own jeans and shirt. Will watched as he walked to a small nightstand next to the bed and opened a drawer. He took out a condom and a tube of lubricant.

“Come, get on the bed,” Harold said with a slight grin.

Will stood up, walked over to him and slowly climbed on the bed. He could hear Harold opening the condom wrapper and then the lube. Will closed his eyes in an attempt to relax himself. He wished he could have drunk more.

“Your Master tells me you’re a good fuck,” Harold said with a sudden icy inflection in his voice. Will did not respond. A moment slipped by before he felt Harold’s cock pressing against his ass. Will could not stop from wincing as Harold entered him with one stroke.

Harold began fucking Will earnestly.

“You like this don’t you, queer?” Harold asked between thrusts.

Will grunted, but did not answer. He was still in pain from Harold’s rough entrance.

“Say it…say you like it,” the man growled again as he rammed sharply into Will. He reached across Will’s back and grabbed his hair, pulling it until Will could feel some strands of hair pulling away from the base of his scalp.

“Yes, I like it,” Will said into the mattress.

Satisfied, Harold continued quickening his pace.

The pain finally eased and Will began to find a little enjoyment in what was being done to him.

Will felt Harold hardening more and knew he was about to cum.

Harold groaned again as he ejaculated. He ground his cock once more into Will’s ass before pulling out.

Will quickly slid his legs underneath him and sat on his haunches. He had not been able to cum, but he was still very hard. He looked at Harold hoping that he would offer to blow him or even give him permission to masturbate.

Harold pulled off the condom and tossed it in a trash can next to the nightstand. He sneered at Will.

“You are a good fuck,” he said, “but, you can go home now.” Harold picked up Will’s shoes and shorts and threw them to him.

Will’s eyes narrowed. He was at least five miles away from the house and he was not exactly sure how to get back to it.

“Please don’t make me walk,” Will tried to ask humbly as he got dressed.

“Get out,” Harold said and grabbed Will by the elbow. He walked him back through the house to the front door and shoved him outside.

It was May and the weather was warm. Will walked off the porch and looked up at the sky. There were only a dimly lit few stars out and he could see the orange glow of the sun getting ready to rise in the east. He hoped that he could pass as a jogger. If it had been any earlier in the night he was sure that he would have gotten picked up by the police. Especially with the noticeable erection that was trying to escape from his shorts.

Will looked around and did not see any lights on in the nearby houses.

He began walking in the direction that he had come from. He noticed an alley between houses. Will stepped into a shadow and paused. He had been so close to cumming that he doubted it would take much now.

Will was not allowed to masturbate without permission but, at the moment, there was no way anyone would know if he did. He put his hand into his shorts and began stroking his cock. Just before he came, Will took his cock out so he wouldn’t get cum on his shorts. He cold feel every muscle in his body tensing as his cum spilled onto the ground in the alley.

After he finished, Will put his cock back in his shorts and began walking again. Since he was driven away in the dark, he hoped he could navigate his way back home.

As he walked, Will thought more about his current situation. Sometime ago, he managed to convince himself that he had no other options left. In some ways, he had even come to the conclusion that he deserved to live as a slave. The Master had told him he was worthless and stupid so often he was starting to believe it.

It took Will almost an hour of walking and jogging to reach the house again. Each step made his sore ass hurt even worse.

When he reached the house, Will found the front door unlocked and he let himself in. The house was quiet. He looked at the clock in the living room and saw that it was after 8am.

Will stopped in the kitchen and fixed himself something to eat before going to the bathroom. He tried to be quiet as he used the toilet and showered. Before going in his cage to sleep, Will looked in the bathroom mirror. His reflection unnerved him.

He saw a too thin boy with dark circles under his eyes. He looked like a junkie. Or worse, a whore. His once fairly healthy long hair had become as listless as he felt. He had lost some of his muscle tone in his arms and legs due to lack of exercise and food. Will saw what he was becoming…a soulless orifice.

Will turned away from the mirror in disgust and went to his cage. He laid down on the floor. He hoped he would fall asleep soon.


Almost two months had passed since the night of the poker game. Somehow, things in the house managed to deteriorate even further. Amy and Will continued to have their secret daytime play sessions. The Master began to notice that Amy wanted to spend more and more time with Will and she was becoming less submissive.

Julia was also spending less time in the house and this did not help soothe the tension. The Master was drinking more and taking out the majority of his frustrations on Will.

“I’ve got someone I want you to meet, boy.”

Will looked up from his book to see his Master standing with another larger man in the bathroom outside of his cage. He noticed that his Master was holding a camcorder.

“He paid to fuck you on tape,” Will’s Master said. It was obvious to Will that he was intoxicated.

Will glanced at the man again. The way he was staring at Will was making him uncomfortable.

Will raised himself to his feet. Just as he was about to plead for mercy, the strange man lunged at Will and forced him back down to the floor.

As the man laid on top of Will, he unfastened his jeans with one hand and pulled his cock out. Will was already nude, so there was nothing he could do to protect himself. The man attacking him was much stronger than he was and he too easily held Will in place while he positioned his cock at the entrance of Will’s ass.

“No, don’t…” Will cried out as he tried harder to get away. He realized that the man intended to fuck him with no lube and, from the brief glance he got, Will saw that his cock was thicker than any he had taken before.

The man snorted with rage and grabbed Will by the hips and jerked him towards him. Will could feel the man’s firm cock rubbing against the back of his thighs as he struggled. He squirmed more. Suddenly, Will’s Master came into view. He put the camera down on the floor and took out a pair of handcuffs. He grabbed Will’s wrist placed one cuff on it and attached the other to the cage’s chain link. Will’s arm was now awkwardly positioned above his head giving him little balance to resist.

Will knew he should try to relax, but he also knew that what was about to happen was going to be excruciatingly painful no matter how relaxed he was. He looked at his Master with contempt. He had picked up the camera again and was watching the events through the screen.

The man placed one hand on the Will’s right hip and dug his fingers in. He used his other hand to guide himself to Will’s ass.

Will braced himself and he felt the man entering him slowly. Apparently, the lack of lubricant was making it difficult for the man even with the force he was using. The man continued pressing himself inside and Will felt a white hot jolt of pain course through him. He could not keep from screaming as he felt his insides being torn. The man’s cock suddenly went in all the way aided by blood from the tear.

The man began thrusting into Will. The pain continued to be as intense as it was in the beginning. Will hoped that it would soon ease like it usually did.

Will closed his eyes, he tried to place himself outside of the present, but the pain engulfed his entire mind. To Will, it felt like the man was using his entire arm to fuck him instead of his cock. Desperate for relief, Will tried to push his rectal muscles outward, but he could scarcely tell if he was doing anything.

Will barely heard the man grunt as he came. The man abruptly pulled out of Will and went back into the bathroom. Will slumped against the tension of his suspended arm. Even though the man was no longer inside him, Will was still in pain. He was afraid to see how much he was bleeding.

He was lost in thought when his Master released his arm. It had gone slightly numb and Will let it fall to his side.

“Go clean yourself up,” the Master said before he left Will alone.

Will dazedly remained on the floor for almost an hour. He decided that the next chance he got he would call his parents. Since his arrival he had been living in a constant state of fear, but now he was beginning to fear for his life. He was going to wind up with some kind of STD or worse, someone was going to go too far and kill him outright.

Will gingerly got up and saw that there was a small pool of blood from where he was sitting. He walked into the empty bathroom and climbed in the shower. Will turned on the water to as hot as he could stand and stood underneath the showerhead drenching himself. He used soap to clean himself from head to toe.

After Will was done showering, he went to the mirror to comb his hair. He noticed that his eyes were red and puffy as if he’d been crying, but he didn’t remember crying. I’m losing my fucking mind…he thought as he shook his head.

He retreated back to the relative safety of his cage. Will did not want to take the chance of seeing his Master or the man. He picked up a book and tried to lose himself in the story.

The next week passed by slowly. The man had injured Will and the Master reluctantly agreed to send him to the doctor.

Will slowly got out of Julia’s car. He walked into the waiting room of the free clinic and checked in.

He tried to look through an old magazine, but he was too nervous. He was embarrassed about telling the doctor he was having gay sex, let alone injured during it. He was relieved that they had at least taken the collar off before he left the house. It was the first time it had been removed.

“William?” A matronly nurse called from the doorway.

Will got up and followed her down a hallway into an exam room. She asked Will a barrage of questions. He managed to answer each one. She did not even pause when he told her he was having anal intercourse. Will tried to reassure himself that she had probably heard much worse things.

“The doctor will be right in. Change into this gown,” she said as she left Will alone in the room.

Will took off his clothes and put the gown on. He sat back on the table and tried to calm himself.

He almost jumped off the exam table when someone knocked on the door. Before Will could answer, the doctor walked in.

“Hi, William,” the doctor said.

Will drug his eyes up to look at her. She was a slightly overweight woman in her forties with long black braided hair. She smiled at him warmly.

“Hi,” he answered.

She glanced down at his chart and asked, “Are you having some bleeding?’

“Yes,” Will did not look up at her this time.

“Well, I need to take a look,” she said kindly.

The doctor instructed Will on how to position himself and began her exam. While she prodded, she instructed him on the proper use of lubricants and condoms. The doctor was nice enough, but it was obvious that she was in a hurry. She did not bother to question Will about what had happened. He was too humiliated by the experience to consider telling her anyhow.

“You’ll heal, but you need to refrain from sex for at least a week. I also want you to stop at the lab for some tests,” she said as she left the room.

Will scrambled to put his clothes back on. He left the room and was directed by signs to the lab. They drew a blood sample. While he was walking out the door, Will stopped to note the time, 10:45am.

Will went outside to wait for Julia. She wasn’t supposed to pick him up until 11:30. It was October and the Florida weather was mild. Will decided to take a short walk. He walked until he spotted a pay phone.

It was a Monday morning and he doubted either of them would be home. He thought he remembered his mother’s work number. Will stared at the phone, debating what to do. He slowly, thoughtfully, picked up the phone and dialed.

“Hello, this is Beth,” a voice answered.

“Hi, Mom. It’s Will.” He blurted out.

“Will? Where have you been? I’ve been worried.”

“Sorry, Mom….I’ve been staying with some friends. I guess time just got away from me. Sorry,” Will stared down at his feet. He knew he was not going to be able to tell her the truth.

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