Caught and Taught Pt. 01

Charlie was a young man of twenty years of age. He was slight of build with shoulder length hair. He had no facial hair to speak of and his body was lithe and sparsely covered in hair. All in all, he went through life not being a threat to others and most others ignored him. If he thought about it, this would probably bother him but he didn't, so he was blissfully unaware.

Charlie lived at home with his father and step-mother and her daughter, Annie who was five years older than Charlie. Annie was not a striking beauty but certainly had a lovely body but Annie fretted about it all the time. She had fads of diets to lose weight and times of attempting keep fit to re-tone her body. Annie was on a mission to find a boyfriend of marriage-quality but the trouble was she was looking in the wrong places and Charlie, in his comparative youthful inexperience knew this but would never tell his step-sister. They were not close, certainly not close enough for him to broach that sort of topic or the topic of his secret.

Charlie's big secret was that he liked to wear female clothing. He liked the thrill of going through clothes drawers. He enjoyed choosing the items of clothing to wear and he loved their feel on his skin. He loved the anticipation of putting them on. Once on, he particularly enjoyed wanking and fantasising about a girlfriend who would be happy with this.

As you may have guessed, Charlie did not socialise much but waited for those rare times when he could dress up at home in Annie's clothing (and sometimes in his step-mother's clothing). Annie on the other hand did socialise a lot but as already noted, she did it at the wrong sort of places.

And so the weeks and months passed.

Over time, Annie started suspecting someone of going through her clothes. She would then leave certain tell-tale items somewhere and they would be altered when she came back. She suspected Charlie and this she confirmed soon afterwards. At first she thought that Charlie was looking for money or some such but this was quickly discounted and she began to suspect the real reason. She was vindictive enough to hatch plans in her head around this and Charlie was naive enough to think that his heavy-handed rifling of her drawers would go unnoticed and unpunished by Annie.

Roll on to the weekend when Charlie's dad and his wife were away, staying with friends and Annie had plans to go out with her friends. Charlie was overjoyed and couldn't wait to have the house to himself. He counted the days down to Friday When it arrived, he waved his father off then watched Annie get in her friend's car and drive off too, saying she would be back some time in the afternoon on Sunday.

"Don't burn the house down, squirt," she told him as she was leaving. He didn't reply.

A couple of hours later, Charlie was in Annie's room, looking through her clothes. He found a new pair of knickers - a black thong and thrilled at it. He picked out a padded bra that he liked as it pulled him together nicely. After that, he found some sheer tights and a summery dress.

In no time, he was wearing the clothes and decided to do the full attempt by putting on some eye makeup - a bit of eyeliner and mascara. He wasn't very good at this but enjoyed the actions nonetheless.

After careful application and finally putting a tad too much on, he stared at himself in the mirror and fantasised about someone making him do this. He was never quite sure if he preferred the fantasy person to be female or male: a man would be worse of course but that thrill was so much greater.

For several hours, Charlie did his own thing around the house dressed up in Annie's clothes. He tried to walk by swinging his hips more, he tried to speak in a higher range and he accentuated his hand movements in some semblance of what he thought women did.

All in all, it was a mediocre thrill since he had done it lots of times already.

Eventually, he ended up in his bedroom, playing on his games console which involved earphones.

Charlie was shooting the baddies, enjoying himself, when he felt he was not alone. Turning, he saw Annie at his door, staring at him.

Charlie went bright red instantly and stammered and pulled the earphones off his head. Bullseye! Caught!

Annie looked at him with disgust on her face. "I was shouting that i had forgotten something and you never replied so i came in. And what do i find? I find you like that. Oh boy, you are in shit now, squirt."

Charlie's world view was rapidly shrinking to a point. Everything else was hazy. He was desperate to find an explanation when he knew there was none.

"I... I.... " he said.

"I bet," Annie replied sarcastically. "You have been doing this for months at least haven't you?" she added.

Charlie could do nothing but nod, meekly.

"Disgusting." Annie said and slammed the door shut.

Charlie just stared at the door and gulped. What was he supposed to do now?

Charlie heard the front door slam and he breathed a little easier. That could have been a lot worse he thought to himself. He put the game down and was walking to the kitchen when the front door opened again and a young man stood there, looking at him as Charlie stopped.

"Well, well, well," said the young man. "Looks like Annie wasn't lieing," and he laughed. "You must be Annie's sissy brother then," he stated.

Charlie was caught in the headlights of the moment like the rabbit he felt he was.

The man closed the front door behind him and Charlie took a step backwards, not quite sure what was going on.

"My name is Dan," said the man, introducing himself. I am Annie's boyfriend... well, more of a casual fuck really to be honest." He stared at Charlie in a very predatory manner, looking him up and down.

"Come here, sissy boy" he said. As Charlie declined with a shake, so Dan's demeanour changed and he repeated the order, in a harsher tone.

Charlie gulped and edged closer.

"Annie told me what she thought you were up to months ago. She hatched this plan to catch you at it and like the dumb-fuck you are, you fell for it. You thought no-one would ever know, didn't you?" Charlie stood there, staring.

"Well, didn't you, sissy boy?"

Charlie could only nod slightly

"I bet you fantasise about men don't you. I bet you don't even like men like that, but you still feel the need to think about them." Dan paused, then continued " you are such a dumb fuck" and he laughed at Charlie.

Charlie turned away, horrified.

"Oi, sissy, look..." said Dan. As Charlie turned, he heard a click and realised that Dan had taken his picture. Dan was looking at it on his phone. "Now that picture is going to keep me in blow jobs for months" he laughed again at Charlie's face, drawn with horror at the prospect.

"Tonight though, I want a fuck. Your sister isn't in the mood. She set all this up, as i said. I am pissed. Now you are caught and you are going to submit or else this lovely picture gets uploaded. Then you can kiss your cushy life goodbye. What do you say to that?"

Charlies stared at Dan then said "You're mad. If you think i am doing anything with you/. You are deluded." Charlie stopped short as Dan did stuff on his phone and said "here we go, one more swipe and the pic is live on your sister's feed. You know how many friends and contacts she has, right? Including your step mom i think"

Charlie blurted out "You wouldn't dare" to which Dan laughed. "Dare me, sissy, one more time and find out."

Charlie hesitated, knowing he was caught.

"Come on then" said Dan, indicating the bedroom with his head.. it was Charlie's room.

"Come on then what?" stumbled Charlie. Dan laughed at him. "You know exactly what... we go in there, you lie down, I take my cock out and i use it to fuck you for the first of many times, until you are so broken that i get bored of you and then you beg me not to leave you, because that is the level of your devotion to me. Or something like that anyway."

Charlie hesitated in the room and Dan sighed "look fucker... picture uploaded or fuck. Your choice. Decide now by walking to the bedroom or telling me to leave" Dan stared at Charlie. "Well?"

Charlie died inside and before he could tell Dan to fuck off, he was walking to his bedroom. He walked in and sat on the edge of the bed and waited for Dan, walking a few paces behind him.

"Here we go then, sissy. This is probably what you have been thinking about for months, isn't it? A nice man to teach you the ropes." Dan laughed again.

Dan reached over and pushed Charlie down onto his back, on the bed. Charlie lay there, quietly, not moving, not looking at Dan.

Dan ran his hands up Charlie's legs and gripped them both under the skirt. Charlie turned away as he felt his knickers being pulled down and finally off.

"Now, isn't that a sight? said Dan as he stared at the half erect cock sticking out from between Charlie's legs. "You are enjoying the idea, aren't you." Charlie avoided Dan's look and Dan laughed again.

Dan got himself ready - he stripped quickly and rubbed his cock for a few moments to get it harder. He spat into his palm and then lifted one of Charlie's legs into the air and rubbed at his arse with the spit, pushing it around his hole.

"Here we go sissy. Relax. Don't fight it or it will be painful for you. Not that i care really but hey..." there was that laugh again.

Dan positioned his cock at Charlie and rubbed. Charlie certainly felt it and squirmed. Dan repositioned himself and pressed his cock against Charlie once more. He pressed it harder and Charlie could feel his sphincter moving. He tried to push Dan away by concentrating on his sphincter. Dan noticed and pulled the leg he had hold of, further back.

Dan was on Charlie now, pressing his cock remorselessly against Charlie. In and out. Grazing the sphincter then back out. Pushing in again. Then out again. Little thrusts of his cock against Charlie.

He pulled away, to spit again on his palm and he rubbed the saliva against Charlie, this time a finger disappeared inside Charlie. "There we go" said Dan as he finger fucked Charlie hard for several seconds. "This is what is going to happen to you, isn't it, sissy?" Charlie lay there in shock at the feeling the finger inside him had generated - it was a violation but it was triggering all the fantasies he had ever had about a moment like this. And actually, the feeling of the finger wasn't too bad.

Dan locked his gaze onto Charlie and got his cock ready again, pressing it ever forwards.

"This is it sissy. Tell me to fuck you now. Come on sissy, now is the time. You can feel it, can't you. It is slipping inside you. Nod then sissy. Nod to say yes."

As Dan repeated his little thrusts in and out to graze past the sphincter, Charlie nodded slightly and Dan laughed and growled at the same time. With his weight on Charlie and his cock wet with saliva, he pushed and Charlie's sphincter yielded: his cock slid 3 inches inside. Charlie rolled his eyes at the invasion and gurgled something as he felt the rest of the cock slide inside him until he felt Dan's balls slap on to his bottom. He was well and truly penetrated. Charlie moved slightly on the bed and raised his free leg up slightly.

"That's it sissy. Get ready because here we go." said Dan and he began to thrust in and out, making squleching noises from the saliva and slapping noises as he rammed into Charlie.

"This is lovely isn't it, sissy? Tell me you like being fucked"

Charlie lay there, saying nothing, accepting the cock and its fucking. He was taking in the weight of Dan over him. He was getting used to the cock inside him. The speed of the thrusts was a shock but the strange thing was... he was responded with little thrusts back, in time to Dan with both legs in the air and his feet bobbing around - he was watching them around Dan, as Dan worked hard. There was a certain level of disassociation for sure in Charlie but over and above everything, he was enjoying being fucked as a sissy.

"Why, the little sissy is enjoying it, aren't you?" hissed Dan into Charlie's ear.

Charlie opened his mouth then, moaning aloud finally and nodded quickly, "yes. Fuck me more" he panted, staring at Dan. Charlie even put an arm around Dan and held him and Dan moved back and forth.

Dan growled and rammed inside him, fucking him harshly then. Faster and faster, as deep as he could. "Ready, bitch?" he growled as he felt his orgasm approaching

"God yes," screeched Charlie then, who was pinned to the bed and bouncing around with the thrusts. "Do it" he panted then felt the first jet of cum shoot from Dan's cock. "Oh my God" Charlie shouted. "Yes, fucking hell. Do it. Do it. Fill me up. Please" His eyes rolled as Dan's orgasm filled him up.

The after thrusts by Dan were awesome - so much lubrication in him that Dan's cock flew back and forth, squeezing cum out of him with every pull.

Eventually Dan collapsed onto Charlie and Charlie found himself wrapped around him: his arms across his back and his legs around his thighs, pulling Dan back to him.

"Holy fuck." breathed Charlie. "That was awesome. Thank you so much." he added shyly.

Dan looked at him hard for a moment then laughed aloud. He pinned Charlie's shoulders down and fucked him a few more times. "There you go sissy. I think you earned that."

"Mmmmmm, yes. I can't believe you did it to me. I can't believe how much it affected me... i feel so wired. So..... I don't know what," said Charlie, laughing a little.

"How about horny, eh?

Charlie thought about it and his eyes lit up with the realisation. "Yes, i feel horny."