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You are here: Home / Adult sex stories / Caught Jerking Off

Caught Jerking Off

FyodorKaramazov99FyodorKaramazov99 May 9, 2020 Leave a Comment

“How did you get that?”

“Boys who beat their meat in front of an open window deserve what they get. I think your parents are going to be very, very upset when they see these pictures. And I think Denise will be furious.”

“Huh? You’re not going to show them to my mum and dad, are you?”

“That’s up to you, Jeff. If you’re a good boy and do what I tell you to do, no one will find out.”

“What do you mean?”

“Well, Jeff. I found it very exciting to see a young man like you playing at being a girl and jerking off. I’d like to watch you do it some more. Right here.”

“I can’t. I have to go home.” He started to leave.

“If you walk out that door before I tell you to, your parents will have these pictures 5 minutes later.”

He stopped.

“Why are you being so mean to me? I never did anything to you.” He was about to cry.

“Don’t waste your tears, young man. Strip naked. Now!”

Jeff gave her baleful look. There was no mercy in her eyes, just a hungry lust. He slowly started to undress.

“Do you need help?”

He shook his head and removed his shirt. He wore no undershirt beneath. Marion admired the smooth hairless chest. He dropped his jeans and stopped.

“What are you waiting for?”

He hesitated for a moment, then slipped his white Jockey shorts off revealing a slender penis that was at rest.

“You look stupid with just your socks on. Take them off, too.”

Jeff did. Marion stepped around him to admire his pale little ass. As she took it in, she knew that this boy had to get fucked. She was going to buy a dildo to wear and she was going to plug him until he screamed.

“Now play with your dick. Get it hard.”

Jeff was miserable. He took his prick and tried to get it aroused, but it wouldn’t move.

“Maybe you need some help. Bend right over.”

She folded him in half when he didn’t move and gave him a stinging slap on the buttocks. She then delivered another dozen. To Jeff’s surprise and chagrin, his cock was stiffening at an alarming rate. As Marion slapped him harder he was afraid he was going to shoot off.

“Start stroking, Jeff, or this little ass of your is going to catch fire.”

Awkwardly, Jeff took his cock in hand and began the obscene act. Hunched forward he began to pick up speed until he shot his load. He automatically caught it in his hand and then was confused since he did not have his handy tissue.

“Taste it, Jeff. It’s your mess. In fact, I want you to eat it. Now!”

Reluctantly, he licked the come from his hand and gamely swallowed it.

“Done like a real lady. Don’t move, yet. I want you to do it again in a minute.”

“I can’t.”

“Oh, you will, Jeff, and you’ll do it again after that. You are going to be a sperm machine by the time I get through with you.”

Marion opened her dress revealing her nude body. Jeff’s eyes gaped open at the sight of the woman’s body naked before him.

“I want my cunt sucked, Jeff. Kneel in front of me and lick it. I’ll teach you what to do.”

Jeff obediently fell to his knees and let Marion guide him. His tongue licked eagerly over her bare cunt, finally lingering on her swollen clit. He let Marion instruct him on taking the clit entirely into his mouth and letting his tongue lick circles around it. He was a quick study and soon had the mature woman groaning through the most powerful orgasm she had ever experienced. She slumped over the boy forcing him onto his back. Her wet cunt pressed like a suction cup over his mouth and Jeff was gagging, but his cock had snapped to attention. He was muling and kicking his legs in fear as his breathing labored. Marion eased up enough to let him take a breath before slumping back and riding his face for a dozen or so strokes. Then she turned to press her big ass right over his nose. Jeff gasped as the large buttocks pressed over his nose. His cock was throbbing. Marion gave the diminutive prick a firm slap and watched it vibrate. She repeated this over and over again lifting herself up slightly from time to time to keep Jeff alive, but dropping quickly to keep him pinned. After 30 slaps the kid shot his load without touching himself. It was a meager puddle and it cooled quickly on his slim stomach.

Marion got up and smiled at the boy who was nearly in tears.

“Let’s go. I want to clean up.” She took his hand and yanked him up. Marion had to pull him along into the bathroom.

“Get into the tub. Now!” She slapped his face hard.

He obeyed with a sob.

“Lie down on your back.” She stepped into the tub and straddled him. “Open wide.”

She started to piss, aiming her stream at this mouth. He tried to move his face, but she dropped to her knees over him and held him in place until she had squeezed the last drop out of her urethra.

Jeff was now crying with great sobs.

“Shut up, Jeff, I want my cunt cleaned up.”

She shoved herself onto her his face and made the kid eat her to another orgasm. Once she had sated herself, she ordered Jeff to have a shower and clean himself up. As she watched him, she planned tomorrow’s shopping trip. She imagined his tiny ass in the air, her new huge dildo driving up his shit spot. It was a fantasy that was soon going to come true.

Chapter 2

“Perhaps I should call you, Jessica, rather than Jeff.”

The boy was not amused as he stood in front of Marion’s full length mirror. He had had two days to try to figure out how to get out of his predicament. His presence in her room indicated his complete failure. He had not attended his sister’s room yesterday.

She had been waiting for him to get in from school this afternoon and had flagged him over to her house. She knew that his parents would not be home for hours. And his sister would not miss him.

She had ordered him up to her room where he stripped in front of her. Rather than immediately abuse him, she had forced him to dress up in some lovely and very sexy lingerie. He had stiffened in the new panties. Marion took him into her bathroom and gave his face a complete makeup job, finishing with a long brown wig. The effects were unbelievable. Jeff stayed rock hard during the entire procedure. Once the wig dropped over his head, he was looking at a stunning young girl in the mirror.

“You look like a little slut, Jessica. One who needs her bare ass whipped raw.”

Jeff turned to look at Marion.

“Did you think that dressing up would change my plans? Jessica, I’m going to take your panties down and use a leather strap to teach you to keep your hands out of other peoples drawers. Then we’ll do something else.”

Jeff was wobbly on the 5″ heels. He tottered out into the bedroom as Marion observed his awkward movements.

“Jessica. Please get the leather strap out of the drawer by the bed and bring it here.”

The boy slowly obeyed and once he had the strap in his hand, he couldn’t resist stroking it. He knew that his naked ass would be the next thing to feel it’s touch.

Marion wore a leather skirt and a leather jerkin of a very shiny black leather. Jeff could smell the leather. Her huge breasts were pushed way up and swelled over the restraining cups. She wore black high heel boots.

“Kneel in front of me, Jessica. Now hand me the strap. Tell what is going to happen now?”

“I don’t know.”

Her hand lashed his face.

“I just told you, you stupid slut. I want to hear you say it.”

Jeff put his hand to his face. A tear formed and started to slide down his cheek.

“I’m.. . I’m going to take my panties down so you can strap me on my bare ass.”

“Exactly. Well? What are you waiting for?”

Jeff stood up and started to lower the panties.

“Leave them at your knees for now. Bend right over. Just like that. Don’t move an inch while I whip you.”

Marion carefully pulled back the strap and let the first stinging slap catch Jeff on the fullest part of his slim cheeks. He jerked and cried out. She followed with two more to punctuate her distaste at the noise he had made.

“Not a sound, you little bitch.”

She then went to work with a will. She moved around and held him from time to time as she measured each blow. Crack!! Crack!! Slap!! The noise filled the room. Jeff was whimpering softly, but to his horror his tiny cock stayed rigid. In fact, he couldn’t believe the fire that was building in his balls. He was afraid he would shoot his load without touching himself. The desire to grip his prick was almost overwhelming. He watched himself-looking like a beautiful young girl-getting her bare ass strapped to an angry red. Marion’s huge breasts heaved in a way that thrilled the young boy. He couldn’t help himself. Finally Marion paused, and though Jeff was relieved, he was disappointed in a way. He had been fascinated by the sight of the young girl getting strapped. He had become a voyeur at his own chastisement.

Then Marion pulled off her leather skirt to reveal a large dildo strapped in place with large leather straps. Jeff stared at the plastic prick and suddenly knew what was next. He was too slow to move, however, with his panties at knee level and the heels making him almost helpless. Marion gripped him and forced him to his knees. She held him as she slid the pre-greased pole against his blazing cheeks, then forced them open. She managed to drive the cock head up his little rosebud about three inches. Jeff was in real agony. Marion stroked into him. She was not adept at this initially, but quickly found the rhythm. Jeff’s asshole started to ease with the huge dildo coring him out. In fact, as he watched in the mirror he was reaching the point of no return. He grabbed his cock and wrenched it a few times, causing him to become spastic as the fluid shot out of his urethra. He almost screamed with a mixture of agony and ecstasy. Marion continued to hammer his ring as he pulsed in a near frenzy.

Jeff finally began sobbing. He realized what he was. A homosexual. A young effeminate suitable for fucking in the ass. For now, it would be Marion’s plastic prick that trained him, but soon the real thing would be replacing it. Jeff realized that he really was a Jessica. With that knowledge suffusing his mind, his sphincters eased and he pushed back to take an extra two inches of the massive latex replica. A final dribble of semen was forced out the end of his throbbing prick.

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