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The following story is a fictional account of a boy's experiences in cross-dressing. It depicts sexual encounters with other boys and men. IF you do not enjoy reading this type of material, TAKE A HIKE... DELETE THIS FILE NOW!
IF by some chance you are under the age of consent, (whatever that may be in whatever part of this God's green earth you may calling from) then you should go to alt.barney.insults, and play there.
For those of you ABOVE the age of consent, I hope you enjoy the story. Feedback is always appreciated.
Last chance to quit... OKAY, let's get on with the story. The writer takes no responsibility for accidents that may occur (such as cum on your monitor, blisters on your dick, etc.) for reading this work.
Billy's "Problem"!
Billy had been dreading gym class all day. He had figured out a way to start the class, but was worried about changing after class. Billy was 13 years old, the age where boys become self-conscious of their bodies, but his problem was a little more complicated than that. Fortunately or unfortunately, gym was the last class of the day, so he had all day to worry about his problem and think of a solution.
Throughout gym class, Billy's mind was somewhere else. Several times during their basketball game, the ball went sailing right past him. Coach had asked him if something was wrong, but Billy just shook his head. Finally, the class was over and Billy had an idea to solve his problem.
While the other boys hurried to get dressed and leave school for the week, Billy took his time. He undressed slowly and self- consciously and took a long shower. When he was sure that he was the last one in the locker room, he finally turned off the hot, steamy water and headed out. He walked towards his locker, with a inward sigh of relief.
He unlocked his lock and bent over the bench to dry his feet. Billy had finally relaxed, confident that his little secret was safe. He didn't even hear the Coach walking by towards the shower. It was hard to say who was more surprised, Billy or the Coach. Billy looked up at the Coach, who was nude, wearing only a towel draped over his shoulder. Billy couldn't take his eyes off his body, muscular and covered with hair. Billy's eyes looked down and took in the sight of his cock, large, even semi-erect as it was.
The Coach spoke first, "Billy, I thought all the boys were gone. Are you sure everything is OK, you were acting awfully strange today?" As he spoke, Coach noticed the red marks on Billy's ass. One cheek was slightly bruised, the other bore the outline of a handprint. Coach looked up and noticed a bright pink pair of lace panties laying in the floor of Billy's locker. "Why don't you tell me what happened to you, Billy?", the coach said, sitting down next to the boy.
With emotion cracking in his voice, Billy began his story. Billy lived with his mother, his father had left the family years ago. Last night, his mother had gone out for a while. Billy was bored, being left alone, and had pulled out a lingerie catalog that he had gotten a hold of. While his radio was blasting away, he opened the catalog and was swept away. As he marveled at the beautiful lace and leather outfits, he wondered what lingerie his mother had. So he had looked around his mother's bedroom, taking out several items. As he had felt the smooth silk against his cheek, he found himself trying on the apparel. He put on a black lace bra and some panties.
The lingerie had more of an effect on him than he expected. Billy was surprised to feel the rock-hard erection that developed as he stared at himself in the mirror. He played around, dancing in front of the mirror, pulling the panties down to reveal a cheek of his ass or the head of his cock. He was so engrossed in his secret pleasure that he didn't hear his mother arrive. She walked into her bedroom to find Billy dressed in her lingerie, fondling his erect cock.
She was furious. She called Billy every name in the book, "freak", "queer", "faggot", "fairy" and a few others. She announced to Billy that he would be punished for his behavior. While he was told to stand in her room, she took off her fancy dress, leaving on her bra and panties. Placing Billy over her stocking clad thighs, she gave him a severe spanking. Not satisfied with that, she also told him he would be required to wear her panties to school the next day. Billy was mortified, he ran into his room crying. Yet at the same time, he couldn't help feeling his hard cock and remembering how it got harder and harder while his mother spanked him. Billy finally fell asleep, after masturbating under his sheets.
All day, Billy had dreaded gym class, trying to figure out how to avoid displaying the bright pink panties his mother had put out for him. She had even watched him get dressed to make sure he wore them. Billy had managed to pull them down quickly when he undressed, throwing his pants into the locker. But he was fearful that some one would see him when he got dressed. As he told the whole story to the Coach, the Coach put his arm around him, their two naked bodies side by side.
Coach said, "Well, Billy, the first thing we need to do is put some salve on those cheeks of yours. Your mom really gave you a beating last night. I have some lotion that will help heal things up quickly. Come with me, into my office." Billy nodded approval and followed Coach into his office. Again, Billy marveled at his powerfully build body. His ass cheeks just twitched a little as he walked, his strong leg muscles rippling up and down. As they entered his office, Coach pointed to a small couch against the wall. "Sit down, there", he said. "Let me get the ointment for you." Billy sat down, nervous about the situation and his nudity. In contrast, Coach seemed 100% natural and relaxed, without a stitch of clothing. He pulled down a bottle of ointment and sat down next to Billy. "Now, Billy, why don't you lean over my legs, I'll spread some of this over that ass of yours."
Billy was a little nervous, but did as he was told. The ointment was cool against his skin, still bright red. It proved to be a delicious sensation, the cool ointment, followed by the warmth of Coach's hands. Coach put a generous amount into his palms, repeating the application a few times. As his hands moved over Billy's small cheeks, his fingers strayed from time to time to explore the tight crack between his cheeks. After a few minutes, Coach spoke up. "I know this probably sounds funny, right now. But I remember getting spanked by my mother when I was a boy. It would hurt like the dickens while she spanked me, but my cock never got so hard. Sometimes, I think I would misbehave on purpose, I couldn't decide whether the pain was worse than the pleasure of feeling my cock get so hard." As Coach spoke, he could feel Billy's cock growing stiff against his thigh. "And don't worry about all that dress-up stuff", he said. "All of us like to pretend once in a while, right?", he said calmly. As he finished speaking, he lifted Billy up and stood him up in front of him. Coach looked down at the slim body, with just the beginnings of muscle development. He looked too, at the stiff cock before him. "All right, Billy. I hope that ointment helps out. I hope our little talk made you feel better, too." He reached down and swatted Billy lightly on the ass, "Why don't you get dressed and I'll give you a ride home. I'll tell your mom you were helping me out and that's why you're late getting home".
Billy was glad he found someone he could share his secret with. As the Coach drove him home, he thanked him for listening to him. The coach promised to keep it a secret, between them. As they pulled up in Billy's driveway, Billy's Mom stuck her head out the door. "Everything OK?", she asked. "Oh, yes", the Coach answered. "Billy was just helping me put away some equipment at the gym. He's a good boy", the Coach said. "I've been looking for someone to be the equipment manager for some of the teams, maybe Billy would be interested." Billy's mother said, "I think that's a great idea, what do you think, Billy?" Without waiting for an answer, Billy's mom continued. "Thank you for bringing him home." As she waved good-bye, Billy's mom was pleased. She had been a little worried about Billy going through adolescence without a man in the house. She was glad the Coach was taking an interest in Billy. She was so pleased, she forgot all about Billy's punishment. She also didn't even notice the lump that was still in his pants.
Billy had trouble getting to sleep that night. It seemed the hard-on he had gotten in the Coach's office never quit. He kept thinking about the feelings he had laying over Coach's knee, while the Coach applied the ointment to his ass. Billy remembered the Coach's finger, exploring the sensitive region between his cheeks. Billy couldn't forget how he felt when he first saw the Coach's naked body, muscular and covered with hair. He wanted to bury his face in his chest and never let go.
Billy's mother was doing some thinking before falling asleep that night, as
well. She always worried that because of her divorce, Billy would not be raised up properly. Sometimes she didn't know how to discipline him or talk to him about things. She was glad that the school teacher was taking an interest in Billy, it would be good for him to have a man to look up to.
She also worried about the punishment she had given Billy. She wondered if
anyone had seen Billy wearing his pink panties. After the Coach had dropped Billy off, she had remembered, with some embarrassment, about the punishment. She instructed Billy to undress in front of her. She wanted to make sure he was still wearing the panties. Billy protested, but she insisted. As he pulled down his pants and removed the panties, both of them were embarrassed. Billy was embarrassed to undress in front of his mother and his mom was embarrassed to discover a healthy erection on her son. She took the panties from him and mumbled something about, "I hope we don't have to do this again" to her son. Billy nodded and turned away to change his clothes.
Billy finally fell asleep, absent-mindedly stroking his hard cock. He had a strange dream that night that he was a slave on a Roman slave ship. The slaves were all strong and muscular, most were naked or dressed only in loincloths. Even then, most of the loincloths were ripped and torn, revealing the firm asses and the outlines of their cocks and balls. Billy was struggling to keep up with the other slaves, rowing the boat. He could
see other slaves being punished in the corner, being whipped. Suddenly he was pulled up from his seat and pushed into the corner to be punished. As his hands and feet were bound, placing him spread©eagle, the disciplinarian
walked up to him. He was surprised to see that it was the Coach. As the Coach prepared to punish him, he winked at Billy. Was the Coach a friend or someone to fear?
Billy woke up at this point in his dream. As he sat up, he felt the sticky
wetness of his discharge. He got out of bed to find something to clean up with. He reached into the laundry basket and grabbed the first thing he found. Even in the dark, he recognized the pink panties he had worn that day. Sleepily, he cleaned up the sheets, and without even thinking of it, put the cum-soaked panties under his pillow and went to sleep.