Keith's Caught in a Costume Pt. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Relax your throat Keith, you don't want to choke. Try to swallow it as it hits the end of your mouth," Beth seemed to revert to her nice girl voice for a minute as she gave tips and tricks. She then slapped his ass, "Ooh, you little slut. Wiggle your ass for my boyfriend while you suck his dick. She leaned up and over Keith and began to make out with Jake while Keith continued to suck away and wiggle his pantied bottom.

After a minute or so of making out Jake seemed to focus back in on Keith, now placing one hand on the back of his head to guide his pace, no longer having to force him down. Without realizing it, Keith had given in to his new reality of being a cocksucker much like he had all the others along the way here. He was now sucking a dick on his own with only minimal guidance. Soon, Jake breathed out, "I'm gonna come baby," looking at Beth, "where does the sissy want it?"

Beth looked at Keith, thought for a moment and then laughed. "Stand up next to the bed, Christy." Keith followed her instructions. Beth reached out and grabbed the front of Keith's panties and pulled them forward, away from his body. "Okay, honey, come here on top of his dick. Maybe he can use it as jerk off lube in a minute." Jake laughed at the cruel idea and Keith couldn't believe it. This sweet girl had turned out to be a monster all along, baiting him along and tricking him into this. Jake pumped away at his dick and Beth said, "Here Christy, hold your own panties open for him and beg him for some lube for your sissy stick. Do a good job if you want to jerk! Tell him how manly he is!"

Keith was incredibly horny by this point, and still afraid of the possibility of the video getting out, and so he followed instructions again. "Please Jake, cum all over my little sissy clit with your big manly dick. I want to jerk off and eat your delicious cum. I'm a sissy fag for you and Ms. Beth." Keith nearly sobbed out the words as he held his panties out and the big jock picked up speed. Finally, Jake aimed his dick down into Keith's panties a blew spurt after spurt inside, coating the chastity and creating a pool in the bottom of Keith's panties that his dicklet now rested in.

Jake fell back on the bed with sudden exhaustion and Keith took a stunned step back. He stood there for a moment watching Beth and Jake make out again before Jake whispered something in Beth's ear. She paused, then turned towards him with an evil smile. "Hey sissy Christy, so if you can get Jake hard again he says we should let you out of your cage to jerk while we fuck. Does that sound fair?" Keith began to nod almost immediately, his horniness overcoming any good sense he might normally have had to warm him. "But, you've got to get him hard using only your ass and mouth. He wants a lap dance or a blowjob to get him going." Beth's vicious smile seared into Keith's soul but he just had to get this cage off his dick. He leaned back to her computer and set up some music to play. As the beat began Jake lifted himself upon his elbows and Keith pinched his eyes shut and moved towards the hated pair on the bed.

Keith began the dance by straddling Jake's lap facing him and lowered himself down on Jake's lap. Rolling his body in time with the music he was able to feel a tiny jerk in Jake's cock. He then spun around and began doing his best impression of the strip teases he'd seen online and in movies, sensually rubbing his ass all over Jake's dick. Keith didn't have the experience and Jake had just finished getting a blowjob however, so there wasn't much movement. Keith realized he would have to pick it up. He crawled onto the bed and got on all fours next to Jake and then leaned himself down into his crotch. Trying to make his voice as feminine as possible he said to Jake, "You can spank me while I suck, Daddy." He stumbled over calling Jake 'Daddy' but this was the hottest thing he had ever seen in a porn and so he hoped it would work now. He picked up Jake's flaccid dick and popped it into his mouth, putting as much suction as possible down. As he began to lick up and down the length of the jock's dick he felt a sudden pop on his ass. "Yeah, sissy bitch, suck my dick. This may just have to be a regular after school appointment." Keith grimaced at that possibility but remained focused on his current task, continuing to lick and suck while his ass received a dozen swats and many gropes and squeezes in between.

Finally, Jake's cock seemed to stiffen to Beth's satisfaction. She shoved Keith's head away and tossed the key at him. As she straddled Jake she looked over at Keith and said, "You can jerk but you're not allowed to cum unless me or Daddy," she mocked Keith's earlier choice of words and tone, "give you permission." Keith fumbled for the key and got it into the lock and removed his cage hurriedly. Suddenly, his dick was free again and it immediately sprung to its full 3 inches (well, 2 and three quarter). Jake's cum, which had been covering his cage, had seeped through onto his dick and Beth's promise that he could use it as lube came true as he began to stroke up and down. He watched the hot couple on the bed as they switched through several positions. His eyes tried to follow Beth's body, but got plenty of shots of Jake's as well. Finally, the two slid into doggy style and Beth called Keith out of his fugue. "Christy, get up here and put your head under my pussy. Lick my clit and Jake's dick while you jerk that tiny thing." Keith obeyed and soon was licking away at Beth's clit and the enormous dick pumping in and out of her sopping pussy.

A few minutes later Jake yelled out, "Open up Christy." As Keith paused and opened his mouth, Jake pulled out of Beth and shoved his dick in Keith's mouth. "Now, don't spill a drop of Daddy's cum, and don't swallow until you show me," Jake instructed Keith. Keith nodded, looking up dazedly into Jake's eyes with his dick resting between Keith's pink glossy lips. Jake pumped into Keith's mouth twice and then his body tensed and he sent his cum jetting onto Keith's tongue. The size of the load and the saltiness were a shock to Keith, only having seen his own, much smaller, load before. He held the cum in his mouth though as Jake finished, and then, pulling out, tapped his dick against Keith's lips to remove the last globs of cum and deposit them into his mouth. Keith laid there, mouth posed open, for Jake to see the load he had just placed inside the made up nerd's mouth. Jake laughed and said, "Good girl, very obedient. Now swallow." Keith quickly gulped the load down, perversely proud of the compliment he had received.

During this, Beth had moved her hand to take over jerking for Keith, slowly down dramatically. "Now Keith," she said, "If you want to cum, you need to sit up." Keith did so. "Now, slide over here and put your hand back on your dick. If you want to cum you have to beg Jake for permission then cum on his dick and then lick him clean." Where Keith might have balked thirty minutes earlier he now didn't hesitate. He began stroking his tiny dick as fast as he could, looking up at Jake and saying, "Daddy, please let me cum. Daddy, please."

Jake responded, "Who is it that needs to cum, little girl? What's your name? And who's your daddy?"

Keith moaned, "Little Christy needs to come. She's your little girl Daddy. She's been very, very, very good. Please let little Christ come with her little clitty dick? Please Daddy, I'll make it feel so good when I lick it off you." Keith had lost himself in the pleasure and shame spiral he was in.

Jake had a shark-like smile on his face, "Cum for me then Christy, cum then lick me clean."

Keith's orgasm ripped through him as he pumped little spurts on Jake's massive tool. As soon as he finished he was back on all fours, angling to get his tongue all over Jake's dick, trying to clean up his entire mess. As he finished he heard applause from the computer, turning his head he saw that there were video chat windows open to several of the cheerleaders, apparently all of whom had seen him just suck Jake's cock. The reality of all that had happened in the room crashed down on him. While he was processing this he felt something tug at his dick and when he looked down he saw it was re-caged and Beth had reset the lock.

Moments later he was standing with his clothes in his hand being maneuvered out the door of Beth's room by Jake. Beth was chatting at the computer with the cheer girls and simply looked over her shoulder and said, "Clean the bloomers and bring them and your workout gear tomorrow Christy. Tell your parents you're going to the game and plan to ride the Spirit Bus with us. Bye now you pathetic little worm!" With that said, she turned back to the computer.

Jake finished walking Christy to the bedroom door and leaned in to whisper in his ear, while massaging his ass, "You give good head. Next time, I'm taking your other hole for a spin. Now, give Daddy a wiggle." With that Keith stopped walking and gave Keith a firm pat on the ass. Stepping out into the hallway, fully humiliated, Keith couldn't stop from putting an extra wiggle in his hips and blushed when he heard a quiet, "Good girl," from behind him.

Jake closed the door then and Keith was left out in the hallway, still in the pink panties, in absolute shock. He was jolted alert by a door opening downstairs and the voice of Beth's mom saying, "Honey, is Jake here now? I'm going to start making dinner." Keith quickly threw on his clothes and made a beeline for the door, yelling out a quick, "than you" to Angela as he went. It wasn't until he was halfway home and stopped at a light that he thought to look in the mirror and realized two things: 1) the pink bra absolutely showed through his t-shirt and 2) he had cum on his cheek. His head hit the steering wheel as he wondered how this might get any worse.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
13 Comments
scurscuralmost 2 years ago

Good writing. You touched a lot of bases with this one. You hit a lot of bases.

AnonymousAnonymousover 2 years ago

This was great. Hope he cheers at the game on Friday.

AnonymousAnonymousalmost 4 years ago

Really hope you come back and continue this, this is one of the best series on this site

AnonymousAnonymousalmost 4 years ago
Sissy

Omg that’s so sexy I’d love to be used like that 🥰 love from Laciebree

AnonymousAnonymousalmost 4 years ago
A lot of plot holes

First. The blackmail makes no sense. Teach caught him doing something embarrassing so she commits several felonies? Sorry teach you are on the losing end of this one.

Second let's say the blackmail is good and works. What kid can spend $600 and parent not notice? What teen has that kind of money to spend?

Third. Teach lessons a teen girl know about what is happening. The usefulness of the blackmail is slipping away fast.

Fourth. The whole cheer squad knows about the blackmail. You got a week till the whole school knows.

Fifth. Captain of the football team knows about the blackmail. Forget it the whole school knows by Monday morning.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
More Stories