Little Larry Ch. 02

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Little Larry goes a step further.
5.7k words
4.63
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Part 2 of the 2 part series

Updated 06/08/2023
Created 05/07/2017
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The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Monday's work that his ass finally stopped throbbing. The hell of it was, he thought, was that the ache in his ass seemed to trigger an erection that demanded attention. He did his best to ignore it, which was made easier when he realized that he was running a little late.

The work week was a blur. The new position required more time, effort and thought. Having already joined the workforce he was used to the daily drudgery of waking, showering, leaving, working, working out and returning home. It was only in the evenings, after supper, when his thoughts turned to the previous weekend.

He lost count of the number of times he browsed chastity devices on various websites ranging from Amazon to more fetish-targeted sellers. He had added then removed them from his shopping cart a half-dozen times, each time chickening out. Yet the mere act of browsing through the devices resulted in an erection, and the erections resulted in him pulling it from his shorts and stroking to orgasm.

And each night he went to bed more deeply confused. Was he a sissy? Why was the fetish so powerful for him?

Thursday afternoon he was called into a meeting. The result of it was that he went home immediately, threw together a quick travel bag and then drove four hours for a big meeting the next day. The bosses were already there; his appearance would be as much window-dressing as it was a learning opportunity. Since he got a late start, the lonely sex toy store about half way along the drive had to be bypassed.

But Friday evening, as he was just one of many drivers on the busy interstate, he found himself watching for the exit very carefully. Seeing the bright block all-caps letters advertising the store was his beacon. Almost without conscious thought he turned on his turn signal and smoothly exited the highway.

He'd not been into a sex toy store in a long time. He hesitated for a second, but gathered his breath and locked his car. His was one of about seven in the parking lot. Just prior to walking inside he checked his credit card balances. They were paid in full and he had plenty of credit. Whether that was good or bad he wasn't sure. He opened the door.

Rather than a dungy, dank place reeking of stale cigarette smoke the store was brightly lit and attended by two younger people who greeted him like he was walking into a mall department store. One, a heavily tattooed young woman with long hair dyed electric blue, came up to ask him if he needed any help. He smiled at her and shook his head. "No thanks, I'm just going to look around a little," he said.

There, in the corner, was the mother lode. The back corner was a long wall of fetish devices. Things that he'd only seen in pictures were now there in front of him. He felt his heart race pick up a tick or two; there was a younger couple in the corner in front of him browsing as well. He saw the young lady pick up a device, turn it over in her hands, and show it to her man. "No hard on with this one," she said with a chuckle before returning it to its place. Her man looked at it for a mere second and scoffed, saying something he couldn't quite catch. Whatever he had said tickled his girl's fancy as she chuckled again, this one a little louder.

He moved in and studied the wall of devices. There were ropes and clamps and gags. Toys that filled one's asshole and ropes to do all kinds of bondage. And yes, there were several styles of chastity devices. He picked one up and looked at it. He'd seen the brand and knew that it was one of the better ones, although it's one hundred and twenty dollar price tag seemed excessive. But merely holding it in his hands made him recall how he'd felt when Jasmine forced him into hers.

The realization had been there all along; studying the devices and thinking about them made him realize that had had wanted to get into the device again. He had simply needed the push. So he browsed some more, and picked up some more toys. Finally, almost in a frenzy of shopping lust, his final item that went into his little cart was a black lingerie set. "In for a penny, in for a pound," he whispered under his breath as he added the garment to his assorted items.

To say that he had his gas pedal to the floor the entire way home was only a minor exaggeration. Typically Larry was a sedate driver, content to do the speed limit or a couple of miles over. Not this time; he was pegged out near eighty, constantly monitoring his mobile's app to ensure he wasn't hit with a speeding ticket. He got home around nine and practically sprinted into his apartment.

He laid the toys out before him. First was the set of three anal plugs in small, medium and large sizes. They were black and made of a mostly hard rubber. He turned the smallest over in his hands several times before setting it down. Next, he opened the gag. Why he'd bought the gag he had no idea, except that he thought that being dressed up like a sissy and screaming helplessly into a gag while someone (namely Jasmine) ass-fucked him held a dark allure.

He put it into his mouth and cinched it tight behind his head. It was odd, yet the fact was that his cock was fully erect and throbbing in his pants just from putting the gag into his mouth. He sat there and tried to get used to it. He was about to take it out when he suddenly decided against it.

Instead, gagged, he sat there and opened up the coup de grace, the chastity device. This was made of a very stiff plastic. He read the instructions and then it took him a solid fifteen minutes to get himself into the device. His erection did not want to be stuffed into the cage, and having it in there made him feel so submissive. Before he donned the lingerie, he lubed up the smallest plug and slipped it easily inside. It was tight and a constant reminder that something was plugging his asshole. In the plastic prison, his cock continued to throb.

When he undid the lingerie, he realized his hands were shaking. Sliding his legs into the panties made his cock throb impossibly desperately inside the cage. He was moaning behind the gag, even drooling a little, and that plug in his ass just added more fuel to his sexual fire. By the time the panties were snug around his waist he was in a pure frenzy.

He walked to the mirror and looked at himself. It was utterly ridiculous. Yet it was the sexiest thing he had ever seen. He moaned again as his balls began aching; the worst part was that he'd not even touched himself yet!

In that state of heightened frenzy he found his hand on the phone. He snapped the pictures, of himself in the panties, then lowering the panties to show off his caged cock. Jasmine's number was in there, and he had the text message prepared with the photos attached. But his hand shook and he just could not hit send on it.

The message was simple: How does this look on me?

He stared and stared and stared. Just then, a bird flew into the window with a loud, resounding thump. Larry squawked, startled, and as he did so his thumb pressed down on send. He didn't realized that he'd sent it until his heart finally started calming down from the sudden scary noise. But the soft ding on his phone drew his instant and immediate attention.

Behind the gag his mouth went dry. He realized instantly that he'd sent the message and the photos. Jasmine's replies started coming in fast. The first response was a giant smiley emoticon. Then came the instructions.

Put the key in a glass, fill the glass with water, and put it in the freezer. Send me a text message with a photo of both keys (I know the model you bought comes with two keys Larry) now and in an hour. I want to see the keys frozen. Send me the first picture in five minutes. Or else. :)

The steady streams of "fuck fuck fuck fuck fuck" were rather muffled and incoherent from the gag. But he did as he was told, and dropped both keys into a glass and filled it with water. He snapped the picture of the cup in the freezer and a close-up showing both keys were there.

Her reply came moments later. Good boy. Now by any chance did you get butt plugs?

After confirming that he had, she instructed him that he was to sleep with the plug in his ass. He acknowledged her text and in the interim removed the gag. He gathered up his stuff and put it all away.

One last thing Larry. You will be sleeping in those panties as well. And when I get there tomorrow, the only thing you'll be wearing when you answer your door are those panties. Got it?

He slowly typed out y-e-s before sending. Her next message asked whether he had purchased a dildo. He replied that he had not.

Do you want to make Mistress Jasmine happy?

Seeing her refer to herself that way made him shiver. He was not entirely certain whether it was an icy one of fear or one of searing heat. He replied back quickly. Yes.

Good. You know the sex toy store on Lincoln? Go there. Now. Purchase a dildo. I don't care what it looks like. When you get home, I want you to text me a picture of it and the frozen keys.

He was horrified. His heart hammered in his chest, and his abdomen felt weak and watery. And just as he had been preparing to pull the plug from his ass, his phone chimed again.

Oh, and Larry? Don't you fucking dare remove that butt plug!!

The trip took about thirty minutes in total. Walking into this store took every ounce of his courage. He got it into his mind that everyone in the store would know that his cock was locked, his ass plugged, and that he wore a pair of skimpy sexy panties under his jeans. But no one even looked his way. This clerk was bored and barely looked up from his phone as Larry purchased a medium-sized dildo. The transaction done he drove home, and took the required two pictures and sent them to his newly-named Mistress.

Well done my pet. A moment or two later came the next text. Now this is very simple Larry. I want you to watch the same Cock Worship sissy hypno that we watched that one night in your parents' basement. Except this time I expect you to keep that dildo in your mouth the entire time. Don't remove it once, Larry. You'll make me proud and happy if you follow my instructions!

Bowing to the inevitable, he replied back that he would. He sat down heavily in front of his computer, called up the file, and then clicked play as he wrapped his lips around the latex toy. It felt like it took forever, but the longer the video played the more that Larry's need to suck an actual cock grew. The dildo was no longer just a sex toy; it was so easy to imagine that it was a thick, hard cock and that he was pleasuring that thick hard cock with his mouth.

Sleep did not come easily that night. Not with his ass stuffed and his balls aching with a deep pain he feared would never leave. Yet sleep finally came, and when he woke the next morning and gained consciousness, he realized that sleep had not taken the edge off of his acute need.

He was eating breakfast when his phone dinged. He retrieved it and saw that it was Jasmine - or rather - Mistress Jasmine. Hi Lacy. My sissy Priscilla and I will be arriving around noon. Take care Lacy!

"Lacy?" he said aloud. She had named him? The return of the hammering heart and leaden ball in his stomach and dry mouth was instant. As was the sudden but stunted growth of his prick still caged in plastic. He moaned and sort of twisted as he braced his hand against the fridge. The wait, he knew, would be the purest form of hell.

When the triple rap finally came on the door, Larry practically ran to the door. He had a spyhole, and peered out and gave an instant thought of thanks seeing that it was indeed Jasmine. If once-Peter-now-Priscilla was there, Larry didn't see him. But he opened the door anyway, and greeted Jasmine wearing the black panties, now the medium-sized plug snug in his ass, and of course the locked up cage.

"Lacy!" Jasmine said in a happy, indulgent tone.

"Mistress Jasmine, please, do come in," Larry said with a degree of formality he did not feel. But the greeting was proper. She smiled as she swept inside, and then following her was Priscilla.

The two sissies looked at each other. But the moment passed quickly; to Lacy's eyes, Priscilla looked miserable. But there was no time for that; Lacy closed and locked the apartment door and then went inside.

Jasmine had taken the very full glass of ice out of the freezer and set it on the counter next to a second practically identical one. She looked over at Lacy. "Pris's has been melting for maybe ten minutes. It won't make much of a difference anyway," she said and smiled.

"No, it won't Mistress," Lacy said.

Jasmine's head tilted as a big smile erupted on her face. "I like the sound of that!" She then turned towards Pris and swatted the bigger sissy's upper arm. "How come you don't call me that?" she demanded.

Pris's mouth open and shut rapidly a few times without sounding words. Finally in a great rushing whisper she spoke. "Sorry Mistress I won't let it happen again Mistress I'm sorry please please!"

She tilted her head again. "Whining already Pris?" She made a tsk-tsk noise while shaking her head. "Not a good start." She then turned towards Lacy. "And how are you dear?"

There were perhaps thirty words that ran through his mind in a fast jumble. Terrified-horny-worried-excited. But what tumbled out was "Curious."

"Curious." Jasmine smiled thinly. "About?"

Larry/Lacy shrugged. "All of it. I'm realizing that this is more enticing, more exciting, more erotic than I could have imagined, but it's...really...different," he said more slowly, picking words carefully.

"Fetishes are different, that's why they're called that," she said. She patted Lacy's arm lightly. "Come, offer me your arm please," she said, and Lacy extended an elbow. She hooked her hand into it and allowed Lacy to lead her and Pris to the couch.

Jasmine made both sissies sit flanking her center position. She then spread her legs and hooked them over both sissy's legs. Although she was rather lewdly positioned, the tight yoga pants she wore did not exactly show anything other than the spread legs. Except, Larry/Lacy noted, the very obvious wet spot at the deepest part of her crotch.

"So, Lacy," Jasmine said once she was settled, emphasizing Larry's new feminine name, "please do tell me all about the story of your purchase of your new chastity device, and the plugs, and the sexy lingerie that you are now wearing!"

Lacy felt her face color up instantly, and took several breaths to calm her unsteady nerves. Slowly and haltingly she related the tale, but once she got to the point of returning home and trying on the various products she'd obtained, she spoke with confidence. She related the trip to the sex toy store, how upon walking in all she felt was that everyone there would know her secrets but pretty much realized that no one cared, not even the clerk.

"How did it feel to have a thick latex cock in your mouth while watching that sissy hypno video?" Jasmine prompted.

"Sexy...but ultimately not all that rewarding," Lacy replied.

"And why is that?" Jasmine wanted to know.

"Well..." Lacy said and her voice dropped to a heated whisper, "it wasn't...the...uh...real thing."

"Oh!" Jasmine said sounding pleased. "So you want to suck on a real cock and make it spurt its goo all over your face and down your throat, do you?" she asked smoothly.

Lacy blushed furiously once again. "I...I don't...I don't know..." she hedged. "I've never...done...that."

Jasmine smiled softly, and winked surreptitiously to Lacy. She silently mouthed "thank you" towards her, before shifting her attention to Peter/Pris.

"Now Priscilla, did you listen to a word that Lacy said? She has been so eager and helpful while you've only stalled and complained!" she said. Lacy marveled at how the Mistress's tone went from warm and supportive to cold and distant in so few words.

"I'm sorry Mistress," Priscilla said in tones suggesting abject misery. "I didn't...I don't..." she stammered.

"Stand up Pris. Now!" Jasmine barked. Slowly Pris stood and followed Jasmine's directions. Pris now stood directly in front of Jasmine.

"Remove that shirt," Jasmine said. Priscilla/Peter was wearing a light tee-shirt, and stripped it off revealing his thin nearly hairless body.

"Now the shorts," Jasmine said next in a stern tone. Lacy watched as Pris's eyes nearly filled with tears, her eyes darting between Jasmine and Lacy. But slowly her fingers complied, and the button fly of the shorts was undone, and the zipper lowered, and then the shorts fell away from her body. Lacy dared not inhale sharply though in reality she wanted to do exactly that.

Peter-now-Priscilla wore a pair of pale yellow panties. They were small and wonderfully feminine. The pastel colors looked terrific on her thin body and clearly showed the outline of the chastity device protecting the sissy's clitty. Pris's face was a bright red, and Lacy knew all too well how fast Pris' heart must be racing and the combination exhilaration/humiliation she felt standing so exposed in front of the Mistress and the other sissy.

"Turn around Prissy," Jasmine said in a taunting tone. "Show Mistress that little ass you have all plugged up!"

Lacy saw the way Pris shot a quick, miserable glance her way before turning, and then again following the sharp command of Mistress Jasmine, bent over at her waist with her hands on her ass spreading her cheeks fully.

"Look at that asshole behind the thong," Jasmine said wonderingly, leaning against Lacy. "Looks hot as fuck, doesn't it Lace?"

"Yes, Mistress," Lacy replied quietly.

"Stand back up Pris," Jasmine demanded and then has Pris face them both again. She then made Pris kneel in front of her, down between her legs. "Actually," she amended, smiling broadly seeing her once-boyfriend now kneeling at her feet, "why don't you bend down and lick my feet for me."

Pris hesitated but scooted backwards, and then bent down to comply. Once after Jasmine felt Pris's warm tongue sliding along the tops of her feet did she relax. "Don't stop sissy," she warned Pris, "or you'll suffer for it!"

"Yes, Mistress," Pris muttered in a tight, strangled tone.

Jasmine nodded her head towards Lacy. Once Lacy put her head close, she whispered her plan into Lacy's ear. It was a good thing for Lacy that she was constricted in the chastity device! She nodded assent to the plan, as much an accomplice to Jasmine's ministrations as a subject.

"Stop, Pris," Jasmine said, tapping her foot. "Stand." She waited until her sissy complied, then stood up herself. "Lacy, you stand," she added. Lacy stood and then Jasmine had the two sissies move the coffee table out of the way. She then stripped out of her yoga pants, revealing her bare body.

She knelt on the couch, spreading her legs wide, and between the two globes of her asscheeks her little rosebud winked at the two sissies. "Now, you two - silently now - do rock paper scissors. Whoever wins licks my asshole first. Whoever loses stands there silently until I say switch. I will then tell you two sissies which of you is the better asslicker!" she giggled. She closed her eyes and breathed slowly in anticipation. "Ready? Rock, paper, scissors, shoot!"

I did rock; Pris chose paper. Pris did not smile, but rather turned, and basically put her face into Jasmine's thick ass. Jasmine moaned a little here and there, and wiggled some. She encouraged Pris - not knowing it was her: "Come on, sissy, get in there deeper! Lick faster, mmmm, that feels good. You little asslicking slut!" she added.

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