Little Larry Ch. 01

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

"Hmmmm." It was odd to be in it, he thought. He very much wanted to get erect but the plastic denied him that ability. "Well, I'll tell you this," he said gazing down at it before making eye contact with her again, "if you put Peter in this before long he'll do anything that you want."

"Oh?" Once again a single eyebrow arched up. "Why is that?"

"Control," he said simply. "Control over cumming. Do what she wants and maybe you get to cum, that kind of thing."

She nodded and grinned hugely. "You gonna do what I say then?" she teased.

He rolled his eyes. "This is practice, right?"

"Well, you are wearing a chastity device, Larry," she deadpanned.

"Well if this is practice then give me the key," he said holding his hand out.

She kept her hand back. "If I say no?"

"Then we're done."

"Fine." She groused but turned the key over to me. I walked it into the kitchen and hid it before returning. "I hid it."

"Why?"

"So you don't know where it is, but I do, but to add some spice to it, to make it seem more real. You want practice, after all," he added.

"You sure you're not turned on by all this, Larry?"

"Fine, I am, a little. Something new, right?"

She winked. "If you say so!" She picked up the smallest butt plug. "This should go in next."

"Why?"

"Because ultimately I want to practice fucking your ass so I can do the same thing to Peter," she said. "And because the internet says to stretch out your ass before doing it." She handed the plug to him. "Or do you want to find out whether it hurts as much as they say?"

"No thank you, and I'm not sure we're going that far anyway," Larry said cautiously.

"We'll see." In the background the video kept playing.

She handed him some lube and he lubed up, and slipped it inside. "Oh god damn that's...weird."

"Hot?"

"Uh...I don't know." Every movement of his body made him feel the plug in his butt. It wasn't thick and felt like it might slip out at any second. "Kind of...good, actually."

"Yeah?" she asked. "Nice!" She looked down again. "What else do we have here. Oh, wait, I know!" She stood up and swiftly yanked her pants and her panties down, and then stepped out of them. She prised her rolled up panties out of her pants and handed them over to Larry. "Here, you need these."

"I'm not wearing those."

She smiled and while still standing spread her legs a little. "This pussy is hot and wet as fuck, Larry. Now if you wear those panties you may, may, have a chance to bury that thick cock inside of me as a reward. If you don't wear them, then you can forget it. Get the picture?"

He was on the verge of refusal when the aroma of her heated sex wafted into his nostrils. He inhaled deeply and whatever defenses he may have had crumbled swiftly. He grumbled as he put one leg in, then the other, and then slowly slide her pale purple panties up his legs and over his bottom. The cage prevented him from having a massive erection; the desire to rip it from his body and let his cock swing freely was overwhelming.

"Awww, you look so cute!" she said with a giggle. "I need some attention, Larry. You're game, right?" she asked, turning around and wiggling her somewhat ample backside at him. "You gonna lick the cream from my cunt, Larry? Or do I have to make you do it?"

He was down on his knees, pressing his face into the heated flesh of her backside without another word. She bent over and granted him access to the slippery wet slit of flesh between her legs. He dove it, savoring the taste, the texture and best of all the slick heated juices. She was the hottest woman he had ever enjoyed - and the third one ever, so there was that - and he didn't stop his enthusiastic licking until she cried out over and over that she was cumming. She then fell to the floor, panting heavily, curling up into a ball to escape it.

"Stop, god that was good, but stop!" she moaned. He wiped away her thick juices from his face, and grinned.

"That was tasty."

"Yeah? I'm glad. It felt really good, Larry." She sat up a moment later. "Let's switch out that plug, Larry, to the bigger one."

"Okay." He reached behind and pulled the first out, and decided to walk to the bathroom to wash it off. She had the other one lubed up. "Can I put it in for you?" she asked, holding it up so show him the dripping lube on the toy.

He climbed onto the couch and angled his back and butt to thrust it out for her. "Slowly, be careful please," he said softly. She stood behind him and rubbed her hand over his panty-clad bottom as she nudged the tip of the plug against his tight hole. She applied a steady pressure forcing him to relax his muscles. And then it slipped inside, bigger than the last, and creating far more pressure and pleasure at the same time.

He dropped his head down and moaned aloud. "Ooh god that's something else!"

"That was hot as fuck, Lar," she said. She patted his butt. "Sit down on the couch." He turned and sat and she crawled onto the couch on him, kneeling over him. She pulled her shirt off and unhooked her bra, tossing both aside. She held her breasts up to him and he suckled on the offered flesh, slowly at first, then more passionately, using his teeth to nibble especially after she cried out at how good it felt.

"I need to cum again!" she moaned. She turned around and crawled up on his coffee table, on all fours, offering herself to him again. "Lick my pussy, Larry, make me cum again!" she moaned.

He moved forward and again lost himself into the pleasures of oral servitude. He poked and prodded her tunnel with his tongue, sliding it down to tease her clit a little and then in a moment of cock-locked inspiration, slid his tongue up over her asshole. She cried out again, loving it, telling him to go more, faster, harder, deeper, and alternated between ass and pussy until once more Jasmine's body let go, sending waves of muscular contractions throughout her lower body. It was so powerful that her thighs quivered.

When she stood it was on weak, trembling legs. "Now for the coup de grace," she said. They took about twenty minutes to get her fully into the strap-on harness, making sure that it was adjusted correctly. Finally, she made him turn around on the couch, took the butt plug out, lubed up the plastic cock and thrust.

The assfucking was unlike anything he had ever experienced. It did not start out pleasantly, more pain and discomfort than pleasure, but after a while, after he got used to it, the penetration became more pleasurable. She was enjoying herself, moaning and groaning but her rhythms were not regular. She had to keep stopping to adjust, to move around, or to move him. Finally, after perhaps fifteen minutes she pulled away.

His very sore ass made him move slowly, but once he turned around to look at her, he saw that she was sweaty and looked tired. "That was more work than I thought," she informed him.

"I know," he said tenderly rubbing his backside. "Ow."

"Hurts?"

"Yeah. You might want to practice a lot more with Peter before ramming him with that thing," he judged.

"Good point." She unhooked herself from it and let it fall to the floor. He was seated on the couch and once more she climbed onto him.

"So you want to fuck me now?" she asked, slowly running her hands through the hair above his ears.

"Yes."

"There's a condition," she said.

"I might have known."

"I want you to fuck me, to fill me up with your cum..."

"Okay."

"Then I want you to eat me out again until I cum, and I want you to eat me out knowing that my cunt is filled up with your semen."

"Oh." Yet the excitement coursed through him. "I will."

"Thought you might," she grinned knowingly again. "Go get that key." He got up and retrieved it, and unlocked himself. He carefully removed his balls from the loop and then she directed him to sit on the couch again.

She positioned herself on top of him, and then reached under him to guide him into her. The sheathing of his cock by her pussy was the hottest, best sensation he'd felt in a long, long time. She quickly began rocking her hips back and forth. "I'm gonna make you cum as fast as I can so that you have to eat all that cum from my pussy!" she moaned into his ear. "Just come quick, Larry, be a good boy and fill my pussy with that hot, sticky, delicious cum. I can't wait for you to lick me clean, Larry, you know you're gonna be a hot cum-eater, eating your cum from my pussy, shoot it in me Larry, give me all your cum!"

Not that he needed the encouragement. Maybe sixty seconds passed before he groaned and jammed his hips upward. "Oh fuck I'm cumming!" he moaned and then his balls let go, shooting several thick, ropy strands of come deep up into her pussy. He panted heavily as his orgasm ripped through him.

Sensing he was done, she scrambled up onto the coffee table on all fours again. "Don't let any drip out, Larry, lick it all up, you cum-eater, c'mon Larry, lick your cum from my cunt!" she moaned.

The hesitation was natural but didn't last long. He dove in, the mixture of his slippery cum and her slick juices creating a new but not unpleasant taste. He sucked, licked and swallowed and it did not take Jasmine long before she enjoyed her final and most powerful orgasm yet, so much so that she ended up collapsing onto the table and rolling off to hit the floor with a solid thump.

The two of them panted heavily, and Larry wiped the mess away from his mouth. It took several minutes before Jasmine finally sat up. "Thank you, Larry," she said with sincerity. "I know that wasn't what you were expecting today."

"I don't know to say thanks, that it was my pleasure, or that it was the hottest sex I've ever had. But maybe all three?" he grinned.

"Yeah? It was hot? You liked it?"

"I liked it," he confirmed.

"Which part?"

"All of it."

"Oh? You're a sissy too?" she asked.

"I don't know about the sissy part but the domination part was awfully fun."

"Hmmmm." Jasmine sat up and began putting things away, and then got dressed quickly. She embraced Larry in a big, warm hug.

"Let me give you a suggestion," she said just prior to departing.

"What?"

It was in a whisper. "Buy a chastity device. Put it on for me. Text me a picture of your cock all locked up." She winked at him. "Maybe then I'll bring Peter by for some real fun. What do you think?"

"I might be able to do that."

"I hope so, Larry," she said and gave him a light kiss on his cheek. She brought her lips close up to his ear. "Because I want to get you so hot and horny that you'll be begging me to allow you to suck Peter's cock. I think you'll both love it!"

And with that, she was gone.

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
12 Comments
DeniseGraceDeniseGraceover 3 years ago
Thanks!

Good story. I LOVE sissy hypno videos

AnonymousAnonymousalmost 6 years ago

kind of dumb dweeb isn't does he not know she is turning him into her sissy and that is her plan all along not peter i don't think her and peter are even going out together he needs some balls and keep the bitch away or next his sister will be there as well

AnonymousAnonymousover 6 years ago

I hope you wright more to this story very soon

FailedscoutFailedscoutalmost 7 years ago
Nice and Fresh

a little simplistic but fresh and new.

Thanks for writing and posting here.

BambiBimbetteBambiBimbettealmost 7 years ago
Good beginning!

The way you built the characters that they were people you would be interested in was a nice beginning. I liked both Larry and Jasmine and loathed Austin. He is a meathead and a douchbag. A couple of typos but nothing really annoying. Looking forward to chapter 2. Thanks for your effort.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Payson's Wedding A gentle young man and his fiance make wedding plans.in Transgender & Crossdressers
My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
More Stories