tagTransgender & CrossdressersLittle Larry Ch. 01

Little Larry Ch. 01


Larry walked tiredly through the gym, his bag slung over his shoulder. He didn't really study the members as he passed. Everyone there had their own reasons for being there. And because it was a high-profile corporate gym, the disparity of people there always intrigued him.

There were elderly men and women still holding onto the last vestiges of physical health. The middle-aged men and women, presumably parents, all trying to hold back the girth that work, good food and alcohol created. The younger crowd all tried to look as good as possible, including the several women he suspected her strippers. Some of them were just too shapely to be natural. And their haughtiness and disdain for men was palpable.

But Larry was not like them. He had read a book once where a smaller man was described as a featherweight. That was him, through and through. It didn't matter how much or how little he ate; since turning eighteen some five years earlier his weight had never varied more than ten pounds from his one-fifteen. On top of that at only five-seven he spent most of his days looking up at people, including many women.

He returned to the beat-up car he drove. It started smoothly enough and he drove the fifteen minutes back to his parents house. On top of being single, on top of being little, he had been forced to return to his parents house to live. At least he got the basement bedroom now, because it had its own shower, and gave him more than enough privacy. But the shame of living at home with mom and dad when he was twenty-three was a bit much. He had landed a full-time job but it paid peanuts, and with the student loans and the cost of rent he had a choice - live at home or starve on his own.

He pulled onto the street and walked into the basement. He heard the commotion upstairs and decided not to go up to see. He knew that his vivacious younger sister Teresa was home for summer from college, and she was everything that he was not. He was quiet and introspective and not physically imposing - all of his mother's traits. Teresa was loud, boisterous, the life of the party, and took after dad's more girthy physical nature. Teresa was not fat although if she did not watch what she ate she would end up that way, but still was rounder and fuller. Even though she was his sister, he was able to look at her and think that she was an attractive woman.

But her boyfriend Austin was a total asshat. Larry had no use for him. When describing Austin to his friends, inevitably he used the phrase douche-bag. Austin was a meat-heat douche-bag, his skin slightly orange from the tanner, his hair cut short, his hat always crooked on his head, his shirts always loose enough to show the bulging pectoral muscles. Austin was not smart on top of everything else. Larry had no earthly idea what Teresa saw in him.

Well, he had one idea but it made his skin crawl to think of it. He had no idea how someone that self-absorbed could actually be good in bed but maybe Teresa liked him that way. He didn't know; he didn't care. He just knew that he wasn't going upstairs to face the two of them and their snickering.

He opened his laptop and began studying. He was taking a class towards a potential MBA and wanted to check to see what was happening in the online class. He read and wrote some replies to the web-board system the university used, and was kind of minding his own business when the door to his bedroom burst open.

"Awww, hell, here I thought I'd bust you jerking off!" Austin proclaimed loudly standing in the door. Teresa, behind him, thought that this was the funniest thing she'd ever heard and snorted several times - each snort making her laugh harder.

"No Austin, I am studying," Larry said tersely.

"On a Friday night? Dude you need to go out. Get laid," Austin said. He casually wrapped his arm around Teresa's waist to pull her in tight against him. "Like I'll be doing later."

"Oh please," Larry said, disgusted. Teresa just chuckled.

"You should go out, Lar," Teresa echoed her boyfriend. "It's not good to be holed up down here in this cave all of the time."

"I have to save money so I can move out, y'know?" he said crossly.

"Living at home with mommy and daddy isn't fun is it?" Austin said mockingly. "Poor little Larry."

"Fuck off, Austin," Larry snapped peevishly.

"Oooh, big talk for a little man!" Austin laughed cruelly knowing Larry couldn't do shit against the bigger young man.

"Just leave me alone please," Larry said more whiny than he had intended.

"C'mon Austin, leave nerd-boy to his studies. I want to go dance!" Teresa said.

"See that little Larry? Going dancing with a hot chick." He winked lewdly. "Then we'll be dancing horizontally after that!" He turned and whisked Teresa away; Larry stared furiously at them as they left.

All hope of continuing to study was dashed; it took a long time before he calmed down enough to even think straight. His phone was silent. He had a few friends and debated calling them, but for what purpose? Then his parents came downstairs to tell him that they were going out for the night, too, leaving him home all alone to watch the house. Great.

He checked his bank accounts. They were full but not full enough. He needed another five or maybe ten grand in there before he could afford to move out. That would take another six to nine months. Fuck!

He was debating whether to take his cock out and jerk off when he heard the house doorbell ring. He went to answer it, and when the door opened he saw with some surprise that it was Teresa's good friend Jasmine standing there.

"Hi Jas. Teresa's not here," Larry said immediately.

Jasmine looked a little downcast. "Damn. She's with...him?" Her tone indicated as much disgust with Austin as Larry had.

"Yeah." A bitter chuff. "Unfortunately."

"Shit. No wonder she's not answering her phone. Too much to hope for that she would be around. And I need someone to talk to!" she said.

"Sorry I can't help unless you want to talk to me," Larry offered.

Jasmine looked up, her expression still showing dismay. "I don't know it's kind of a girl thing," she explained.

"I'm not good at that either. I guess I'm not good at any fucking thing," Larry spat bitterly.

"Whoa whoa there!" Jasmine exclaimed.

"Ah, I'm sorry, I'm just...bitter tonight."

"Bitter, party of one, eh?"

"Something like that. Plus Austin really pissed me off earlier and and...and I guess I'm just in a funk."

"Poor little Larry."

"That's all anyone has said to me tonight!" he snarled through gritted teeth. "I can't help it I'm a goddamn feathermerchant!"

"Easy, Lar, I'm sorry, I was just teasing a little, I didn't mean to set you off!"

"Yeah." He wasn't so easily mollified at the moment.

"Listen, if it'll make you feel better, I'll talk to you. Is that what you want?" she asked.

He looked mutely at her for ten, maybe fifteen seconds. Then opened the door wider. "Sure, why not. My parents have a beer, you want one?"

Jasmine came into the house. "Sure, but I don't want to talk up here. Don't you...aren't you living in like an apartment here in the house?"

"It's in the basement but yeah, I have it."

"Down there, then," she said. After they got some beers, she followed him down the steps into his little apartment. It was little more than a bed and a desk with a chair and his bathroom, but that's all that was necessary at the moment.

"So, what's up?" he asked after uncapping their beers.

"You really want to hear this?" Jasmine offered him one last out.

"You're being coy, whetting my appetite."

She sniffed. "Fine. You know the guy I'm dating?"

"What's it, uh, Peter, right?"

"Yeah, him," Jasmine nodded. "So he dropped a bomb on me the other night."

"Dumping you?" Larry asked in astonishment.

"No, something else."

He frowned a little. "What, then?"

"He wants to be my sissy."

"He wants to be your...sissy? Sister you mean? Wait, what?"

Jasmine shook her head slowly. "No." She chuffed hard. "He wants me to make him wear my panties and stuff."

"Holy shit," Larry thought aloud.

"I know, right? Here's the thing." Jasmine took a pull on her drink. "Every time I think about it my skin crawls...but I get so wet and turned on. I can't figure it out!"

"Why the skin crawling?"

Her shrug was quick. "Doesn't he just want to fuck me?" she asked plaintively. "Why all...that other stuff?"

Larry studied Jasmine for a moment. Maybe she wasn't the hottest girl he knew, with kind of a plain-jane face and average body, but she was still kind of attractive to his eyes. "I uh well." He shook his head. "Maybe that's just what turns him on."

"Look at me, Larry," she said, and cupped her boobs under her hands and lifted them. "Boobs, Larry. Boobs. Men go crazy over D cup boobs. Not Peter. Peter goes crazy for me making him wear panties and stick my dildo up his ass."

"I'm not sure how I'm supposed to answer that."

"What insights does your male mind tell you?" Jasmine pressed.

"Either he's submissive or bi-sexual but wants to be forced into it I guess."

She tilted her head a little to one side. "Okay that's interesting. How do you know about that kind of thing?"

"You can learn about anything you want on the internet," Larry shot back quickly. "Besides if you deep enough on those porno tube sites you can find just about any kink you can dream up, and some you can't!"

Jasmine issued her own short, bitter sound. "Yeah, so I've discovered. Do you know that there are a huge number of these videos, they call them 'sissy hypno' videos. I think they're Peter's favorites."

"Sissy hypno? I'm not familiar with those."

"No?" she asked, and then nodded her head towards the computer. "Want to see some?"

"I uh...well...if you want."

"They're different that's for sure," she said as they exchanged places. Jasmine drove his computer to a couple of well-known sites. "Hey, you don't have any porn favorites," she commented.

"Incognito mode."

"Smart. I do the same. Peter doesn't. How the hell do you think I found this shit out?" She clicked and typed and then sat back. "Okay, I think that this one is his favorite. It's called 'cock worship'" she reported. She clicked play.

A moment later the sultry tones of a soft-spoken woman came from the speakers. It suggested that the listener should relax as words flashed up on screen. Jasmine made it full-screen, and then they sat back and watched silently. After about two minutes of this, the tone changed to begin discussing how the woman was going to guide the man to suck cock. Pictures appeared on the screen, alternating between beautiful women dressed as Dommes and pictures of large, thick cocks.

"Jesus, it's enough to make me want to suck a cock," Jasmine said quietly after another couple of minutes of watching.

"I don't think you're the intended audience," Larry said softly. He was staring just as openly at the screen as Jasmine. He was also worried. Very worried. Because he felt his cock stirring in his pants, and wasn't entirely certain that it was because he was watching a very exotic porn video with a woman. What if he was being affected by the video?

"You say he watches this often?" Larry asked after another long silence.

"He says no but his browser history tells a different story. I can't imagine it, him sitting there stroking his cock listening and watching this. I mean, really? I'm not good enough for him?" she added acidly.

"Maybe it's just his...fetish."

"It is hot though," Jasmine whispered a moment or two later. "Maybe I'm understanding why he wants me to do this to him."

"Hot how?"

She didn't turn her head to look at him; neither did, actually as both were riveted to the screen. She turned the volume up a touch. "No one's home, right?" He confirmed that to be true.

"I mean, doesn't the idea of lesbians turn guys on?"


"So why not the reverse? Couldn't it turn a girl on to think about two hot guys doing each other?" she suggested.

"Makes sense," he agreed.

"Damn, now that's hot." Rather than just stills, now mixed into the set were some videos of women graphically sucking on hot, hard penises. "It's making me a little wet. Are you turned on a little, Larry?" she asked softly.

"A little."

"You gonna run out and suck a cock now?" He snorted his reply, making her chuckle lightly.

"I wonder what Peter thinks about when watching this," Jasmine said.

"Sucking cock, presumably," Larry said. "Pardon the blinding flash of the obvious."

"I know, right." Jasmine still couldn't take her eyes off of the video. It was getting towards the end and now the tone changed again. When he cums, you're going to cum the woman said. The imagery of orgasmic eruptions spraying onto women's faces or onto open tongues became more regular.

Towards the very end there was a countdown, and the woman suggested that the listener should be swallowing cum now, whether the cock spewing cum down his throat or his own cum, and started calling the listening all kinds of names, little faggot, that kind of thing. Larry was not fully erect but damn if he wasn't on a hair trigger to get there. Jasmine shifted in her seat several times.

When the video finally ended, Jasmine turned to look at Larry. Her eyes shone. "Fuck that was hot. Maybe I will make him suck a cock so I can watch!" she said. "I think I need to go, Larry. Thanks for the talk." She stood and without another word ran off.

Larry sighed in relief. He waited until he heard the sound of her car pulling away, and only then did he take his cock out. It sprang to its fullest and then he stroked slowly, watching the video again. It didn't take long before his own seed erupted from his organ and covered his abdomen.

He cleaned up and turned the computer off. He went to crawl into bed but sleep did not come. Not for a long time.

Three weeks later, Larry found himself walking through the nearly-bare apartment. Things at work had changed; the Monday after that night with Jasmine he had been brought into HR and they told him that he was being promoted and he got a raise. That night he ran the budgets and determined that he could probably afford to get his own apartment. It took a while to find one that was a good mix between proximity to work and cost and once he got it, he signed the lease.

His parents bought him a few things to get started. He took Friday off of work and moved in, and then spent most of Saturday unboxing things. He laid down in his bedroom, on the floor, just to "rest" early Saturday afternoon and ended up napping for two hours. Energized and refreshed from his nap he made short work of the rest of the putting away process and by eight that night he was walking around, enjoying the freedom of having his very own place all to himself.

Austin and Teresa had stopped by. Austin was not quite as shitty as he had been a couple of weeks ago; mom and dad reported that Teresa and Austin had been fighting a bit, which may have resulted in Austin's more subdued personality. After they left, Larry made his first supper at the apartment and then afterwards realized that he was bored.

But his apartment was well-wired and connected so he was on the internet. His doors were locked and the lights were off as he laid on his bed, his laptop next to him, gently stroking his erection to another reply of Cock Worship. It had become something of an obsession; he wasn't sure whether to curse or thank Jasmine for exposing him to it.

After an orgasm he fell to sleep, and woke the next day to start his usual routine. He was at the gym Sunday morning and enjoyed it, and felt slightly stronger which for him was a very positive outcome. Back at his apartment by noon, he was facing a long day with nothing to do.

His phone chimed with an incoming text. It was from an unfamiliar number. But when he opened it, he grinned. "Larry its Jasmine. Can we talk again?"

He texted back a positive reply and was putting her number in his phone when she called. "Hey," she said.

"Hey," he replied.

"So Teresa tells me that you got an apartment?"


"That's cool. So you have privacy now?" she asked.

"Um...yes..." he replied somewhat more slowly.

"Good, because you know our conversation from a couple of weeks ago?"

"I remember."

"Can we talk again? It's...about the same things."

He suppressed the urge to sigh. "Um, sure. When?"

"Now?" she asked hopefully.

"Uh, okay, I guess. Sure, I'm not doing anything."

"Cool." She asked for directions which he gave, and then he ran around his place making sure that it was tidy. He just finished when he heard the knock and opened the door. Jasmine was there carrying a small backpack.

"Come on in," he said with a formal wave of his arm.

"Hey, nice place!" she said, sweeping past him and moving into the living room. "I like it. Teresa said you got a raise so that's how you're affording it?"

"Yeah, pretty cool, right? I'm excited."

"Yeah, that's sweet." She turned to face him. "I have a problem, Larry," she said.


"Here's my problem. I was so fucking turned on by what we watched that I now can't wait to do it to Peter, but I want it to be a surprise." She suddenly pulled her lower lip into her mouth and gnawed on it. "And I don't want to fuck it up."

"What's your point?"

She whispered it: "I want to practice first."

Comprehension dawned slowly but once it did he felt his face coloring up a little. "And you want to practice with me."

She nodded slowly. "Please? It'll just be between us, please, Larry, please?"

"What do you want to do?"

"Well, I have some things here..." she said and unzipped her pack and dumped the contents out onto the coffee table. He spotted a couple of dildos, two anal plugs, some kind of harness thing, a small pale-pink thing that looked something like a penis with a ring behind it, and some other assorted black leather toys.

"Jesus, what'd you do, clear out the sex toy shop?"

"Yeah, well, I had some room on my credit card," she said sitting down next to him. She picked up a lilac-colored dildo, long and pliant. "I've been using this one," she reported with an arched eyebrow.

"And I needed to know that?" Larry rejoined.

"Thought it might perk up your willy," she chuckled.

"The willy is perked up already, I assure you of that." Truthfully he was pretty erect just from the suddenness of it.

"Let's get into the mood." She nodded towards his television. "You have any way to get the internet on that?"

"Yeah, I bought a Chromecast, hold on," he said. He retrieved his laptop and opened the browser (incognito mode) and then went to the porn site and brought up the same video they'd watched last time. He cast it to the television and turned the volume up a little bit - not so blaring the neighbors would hear it though.

"Sweet," she said with a nod. "Cool that gets me in the mood!"

"Okay. So now what?"

"Well, take off your pants Larry, work with me here a little, okay?"

"Okay." He did as she wanted, and when he did his stiff erection poked out in front of him. She studied it.

"About six inches?" she asked after looking at it and then making eye contact. He nodded to confirm. "Nice. Bigger than Peter. He'd be jealous. Thicker, too, from the looks of it. Not so small after all, are you Larry?" she teased.

"Never thought of it that way," he said but was secretly very pleased.

"Okay, so let's start with this," she said grabbing the pale pink thing. "It's a chastity device."

"Why that?"

"Well we wouldn't want you cumming by accident now, would we?" she suggested lightly.

"Oh. Well...okay," he said dubiously. And getting himself into it proved to be a tremendous challenge. He finally had to pop one ball through the hoop, and then carefully push the second one through. He had to wait a bit for his erection to subside and then she was able to put the cage on his cock and lock it. "There."

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bypantywriter© 12 comments/ 46526 views/ 47 favorites

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