Tiny Thomas and the New Job

By Psndeviant.

Read Tiny Thomas and the Party Here.
Read Tiny Thomas and the Bad Pool Day Here.


Tiny Thomas and the New Job…

Thomas shivered nervously as he sat next to his…well, he didn’t know exactly who she was to him. Her name was Jess, and he had lived with her for nearly a week now and he had some interesting interactions with her in that time. The night before chief among them. They still hadn’t talked about the party that Thomas attended naked as… well as he was at present. They were driving to a familiar destination for both of them. It was a pool where Thomas had been before. It was an immensely embarrassing experience, but it did reunite him with Jess, a girl Thomas was falling for.

It seemed the previous night had escalated their relationship. However, despite the erotic nature of it, there were still other women there, and so Thomas was unsure. His uncertainty distracted him, but also the anxiety of returning to the pool where he had been so thoroughly humiliated. Not only was he returning, but he was returning naked. This was apparently the job that Jess had landed for him. She didn’t reveal what it was till the morning after the party, and she also revealed he would interview naked as he had been for the last week.

He shivered as he considered being naked in front of a group of people like he had been a week before. He tried to take deep breaths to calm himself, but it wasn’t working. Jess seemed to notice. “You doing okay there, little guy?” she asked.

He smiled at her with fake confidence. “Yeah, I’m doing okay,” he said with a squeaky voice. Jess seemed to smirk at his nervousness.

“You’ll do fine, little guy. Just remember you have nothing to be ashamed of,” she said with a warm, reassuring smile.

He returned a weak smile, still unsure of the whole thing. They parked soon after and exited the car. Being naked outside gave Thomas a great deal of anxiety. He had to breathe slowly and even to prevent an outright panic attack. Jess grabbed his hand and looked into his eyes and gave a sympathetic smile. He looked at her and remembered he did this for her, he would do anything for her. Thomas lifted his chin and put on a brave face, and the two of them started walking towards the pool. With each step, he felt his nerves grow and his boyhood shrink.

Thomas didn’t dare look down at the state his already diminutive stub was in. They made it all the way to the fence without running into anyone, and he glanced down at himself. His ‘little guy’ couldn’t have been more than a half inch. Thomas gulped as he realized he was going to be the smallest he’d ever been and naked in front of a person who was presumably his new boss. He wanted to stop Jess and call the whole thing off then.

Seeming to sense this, Jess turned to him, squeezed his hand, and looked into his eyes. “What do we say?”

“I-I-I have a tiny penis, and I’m not ashamed?” he questioned, not even sure if that was true right now.

She smiled at him, still sympathetic, and turned to bring him in through the employee entrance. It soothed his nerves a bit that he didn’t have to go in front of the entire pool. They made their way to a small office, and Jess turned to Thomas one more time.

“Okay, Thomas, this is the manager’s office. Her name is Mary, and she’s really nice. I explained everything about you already, so she shouldn’t be too surprised.”

Jess gave his hand one more squeeze and shot him one more smile before departing, leaving him naked and alone. As soon as she left, Thomas almost turned and ran, but stopped himself when he considered how much Jess would be disappointed. He found his bravery and moved his shaking hand up to the door and knocked. He held his breath as he waited for his latest humiliation to begin.

A minute later, the door opened, and a middle-aged woman, just shorter than Thomas, answered the door. She had dirty blonde hair, some mild crow’s feet, and piercing green eyes. Her lips were thin, curling to a small smile as she looked Thomas up and down, her gaze pausing on his tiny dicklette. Her lips seemed to press together then as she apparently suppressed a laugh. She returned her gaze up to Thomas’s and spoke.

“You must be Thomas. Come on in, and let’s get this interview started.”

She smiled and turned to return to her desk. Thomas stared as she turned. She wore the same uniform Jess had worn: a green shirt with khaki shorts with a brown belt. Mary’s ass seemed to stretch the khaki shorts she wore to their limit with her wide ass, and her breasts similarly stretched her shirt. He found her curvy body quite enticing, but his nerves overpowered his libido at the moment.

He followed her inside nervously. He went to take a seat, but Mary stopped him. “Actually, please stand. I don’t want my chairs getting dirty,” she said with a smirk, and her gaze went down to Thomas’s shrunken self.

Something told Thomas she wasn’t making him stand to keep her chair clean.

“So, let’s get started,” she said, looking through some papers. “I take it you’ve never had a job before, have you?”

“N-no, my…stepmother wouldn’t let me work, but I don’t live with her anymore…” he admitted.

Just thinking about Veronica sent chills down his spine, and his boyhood somehow shrunk even more. The additional shrinkage didn’t go unnoticed as Mary’s eyes darted down, and she smirked. It looked to Thomas like she was stifling a laugh.

“I’m familiar with the events. Jess had filled me in. Well, not much point in going over your job history then. Did she happen to tell you what this job will entail?”

Thomas shook his head nervously.

“Well, I’ll start with the why before the what. Since the last time you were at the pool, we’ve had a lot of questions from our regulars.”

Thomas gulped, feeling sweat beading on his brow, recalling the humiliating event.

Mary said, “They’ve been asking things like ‘Who was that naked guy? Will he be back? It was the best day ever watching his big butt bounce.’ And finally, stuff like, ‘I’ve never laughed so hard. His…’” she paused, apparently choosing her words. “‘…shortcomings were quite the sight; will he be back?’”

She sat there silently, looking at Thomas. Her words, though humiliating, stirred something in him. His shrunken dick was returning to its normal, yet diminutive, size. “I’ve never been asked so often about a visitor to this pool. It seems the women who witnessed had a lot of fun, and the women who have heard are also very titillated. Given all that, I felt that we could use you, which brings me to your position. You would be serving the women drinks here at the pool… in the nude.”

Thomas knew it was coming, but hearing the words made his heart race. It was bad enough he was forced to be nude in front of so many, but now he was being asked to lay himself bare voluntarily. He had done so a few times now but for much smaller audiences. He thought about all the jeers and laughs he had experienced so recently, and the memory sent chills across his form. Even with the chills, there was something beneath it all, something he was still afraid to admit…arousal. He knew that Jess wouldn’t let him say no, and now, despite his fear, he wondered if he really wanted to say no.

It seemed Mary sensed the mixed emotions of Thomas and continued. “You would be paid fairly well for your service. After all, the duties certainly exceed the normal call of duty for employees here. So, before we proceed, I need to ask if you are still interested in this job?”

Her formal words seemed incongruous to the actual situation. Thomas was standing there nude with his tiny dick exposed to his prospective boss, and yet she was asking him if he wanted a job, a naked job. They waited in silence while Thomas nervously mulled it over until he decided, a decision he knew he was going to make all along. However, he didn’t want to admit it.

“I want the job..,” he said quietly as he dipped his chin, lowering his gaze.

He caught Mary’s reaction out of the corner of his eye, a devious smile spread across her lips. “Good! Well, I’ve heard enough. You’ve got the job!”

Thomas looked up in surprise, shocked that was all it took for him. He was now very nervous as he realized what he just agreed to.

“I’d say today is as good a day to start work as any!” she announced.

Thomas’s eyes bulged in shock as he thought today was only going to entail the interview. He gulped as he tried to prepare himself for the onslaught of eyes he was surely about to face.

“Before we get started, Thomas, there is one more thing I need to do…I need to measure you…for record’s sake.”

Her devious grin never left her face. Thomas had never been measured before. He had himself just to check and was disappointed in the results. Another person measuring him, though, was unthinkable. She stood up and walked to Thomas with a ruler. With each step, he felt his manhood retreat. He looked down, and it was as small as he’d ever seen it. She handed him the ruler, and he knew what to do. He wished his appendage hadn’t withdrawn. He was always tiny, but now it was ridiculous. He took the ruler and pressed the ruler up against the side of his shrunken package. He didn’t dare look down, but he saw Mary had no such qualms.

“A half inch!” she said as she turned around and wrote the number down. Thomas’s heart sank as he realized his size was a matter of record, a record kept by his new boss. “Good, now I need the measurements complete, so if you don’t mind…”

Thomas looked at her, confused. Seeing his confusion, she sighed.

“I need your full measurement,” Mary said as she gestured to his dicklette with her hand.

Thomas blushed as he realized she wanted to know the size of his little dick hard. The thought of being hard in front of this new woman seemed to breathe life into his little guy.

She noticed. “Do you like that? The idea of showing me your itty-bitty hard-on?” she said in a tone like she was talking to a child.

Her words and tone had the desired effect as his dick filled to its full but pathetic size. Thomas felt even more embarrassed by the fact that he not only grew hard while standing nude in front of his new boss but also that her teasing him was what precipitated the growth.

“Well, go on, I’m waiting…” she said as she raised her chin, asserting her authority over him as she walked closer until there was barely a foot between them.

He once again pressed the ruler against himself. “Three point five inches!” she said, and Thomas’s heart sank. He thought it was at least a little bigger than that, but alas, the ruler didn’t lie.

Mary turned and wrote down the measurement, returning to look at Thomas, clearly fighting a laugh at his expense.

“I-I’m sorry,” he said, hanging his head.

“Sorry? What on Earth are you sorry for?” she said incredulously.

“F-For being so…small…”

Mary sighed. “Jess told me you were over this. You had a phrase or something you repeat,” she said.

“I-I have a tiny penis, and I’m not ashamed?” Thomas said.

“Is that a question?” she said, raising her eyebrows.

Thomas realized what she wanted, his confidence, something he didn’t know he could provide.

“Listen, Thomas, Jess talked to me. She wants what’s best for you. She believes, and I happen to agree, that the best way to deal with your past and your insecurities is to face and take ownership of them. That’s why she wants you to have a job here. I don’t have an issue, and I didn’t lie when I said so many women were asking if you were coming back. Now repeat that phrase, with all the conviction that statement deserves, and be a fucking man.”

Thomas had never been spoken to that way. Somehow, her forcefulness emboldened him like a challenge. In truth, he had never felt stronger, and so he said once more, “I have a tiny penis, and I’m not ashamed!”

He had never felt taller as he stood up and now stood just above his new boss’s height. Her expression shifted to a satisfied smile. “Good, I must say you look way better confident. For a second, I forgot how little your dick was!” she joked.

The joke knocked him down a peg, but he was still more confident than when he arrived. It also helped to know that Jess orchestrated this job in an effort to better Thomas and make him more of a man. Mary ushered him to follow as she exited the door, and with his chin held high and little dick on display, he followed her. They got closer to the pool with Mary explaining some mundane things about working at the pool that apply to every employee until they reached the area where the patrons would be.

She stopped and faced Thomas. “Ready, Thomas?”

He hesitated, unable to form words with his mouth. He somehow managed to nod his head yes. She opened the gate leading to the pool and Thomas reluctantly followed, all his former confidence instantly washed away as he exposed himself in public once again.


Luckily, as the pool was just opening there were very few there. Unfortunately, it wasn’t empty, as three older ladies were lounging in some chairs. They instantly noticed Thomas and began giggling and whispering to each other as they stole glances at Thomas, not so subtly. He saw one of them pinch their fingers together while talking to each other, and they all laughed. Thomas gulped as he started regretting agreeing to this whole thing.

“Thomas?” Mary said.

“Huh?” he said, breaking his eyes off the laughing ladies.

“I said, ‘Follow me to the soda bar,’” she said as she smirked and rolled her eyes.

He blushed and followed, doing his best to ignore the stares from the amused women. He saw Jess behind the soda bar, and he flashed back to the previous week. He started breathing heavily as he walked, almost collapsing, needing to catch himself on the bar as he reached it.

Mary turned to him. “Are you doing alright, little guy?”

He felt his anxiety rise, and then Jess spoke. She turned to him. “Thomas, what do we say?” she asked with a beautiful, reassuring face.

Looking at her, he felt warmth spread across him. He gazed into her eyes and remembered why he did this. He stiffened his upper lip and stood up tall.

“I have a tiny penis, and I’m not ashamed!” he said proudly, then immediately regretted saying it so loud as he heard the women behind him start laughing out loud.

He blushed crimson as he realized they heard him. Jess gave him an affectionate smile.

“Good boy,” she said softly.

Mary smirked and shook her head. “Now that we’ve moved past that. Let’s talk about the actual job you’ll be performing. So, you are to walk around to the various patrons who come through here and ask them if they’d like anything from the bar. You’ll take their orders and give them to Jess. She’ll prepare them, and you’ll return to the patrons with whatever they asked for. If there’s downtime, they may ask you to perform for them in some way or another. If it’s not too audacious, I expect you to do as they ask. If they offer you tips, feel free to collect them!”

Tips sounded nice, and collecting orders wasn’t so bad, but “performing” that vague term sent chills down Thomas’s spine. “That’s about it for now. Obviously, we have some closing duties and opening duties as well. We can go over those when the time comes, but it looks like we have a few customers already.”

Thomas gulped as he realized the laughing older women were about to get a closer look at him.

“Well, get to it, little guy,” Mary said with a wink and a smirk before walking away.

Thomas stood there dumbfounded for a moment.

“Thomas?” Jess said, getting his attention. “It’ll be alright, okay? I’ll be right here if you need a friendly face today,” she said once again, smiling at him affectionately.

He smiled weakly at her, mustered all the fake confidence he could muster, and started toward his first customers of the day. As soon as it was clear that he was approaching the ladies they fell silent and watched him walking towards them. Each wore a devious smile, eyeing down every inch of the tiny Thomas. It felt like it took forever, but Thomas eventually reached them.

“Hello, ladies,” he squeaked nervously. “I’m here to take your order. Is there anything I can get for you from the soda bar?”

The ladies looked at each other with their lips pressed together, clearly suppressing some laughs at Thomas’s expense. The first lady had salt and pepper hair and a purple one-piece bathing suit; her figure was slim, and while her hair and skin betrayed her age, she was still quite becoming. Her attractiveness only exacerbated Thomas’s embarrassment.

“Sure, I’ll have a lemonade!” she said with a small smirk, her eyes darting down every few seconds to the tiny dicklette a few feet from her.

He turned to the next lady, who was already giggling softly. She was a heavy woman with brown hair with grey roots. Thomas didn’t find her especially attractive except for her massive tits. On her body was a black one-piece with a swimming skirt. She pressed her tits together and leaned forward with a mischievous smile.

“Well, I guess I could have a…little something,” she said, and the first lady turned to her and pushed a little bit after a guffaw she failed to stifle.

She gave her order, and Thomas took note, turning to the last woman. She was the most beautiful of the three, with silver hair and a look of mature elegance. On her body was a blue floral one-piece suit. Her body was slim and seemed youthful, considering the marks of advanced age on her face and of her hair. She had blue sparkling eyes and a humorous smirk.

“I’ll have a water with lemon, please!” she said as her eyes darted between

Thomas’s and his shrunken package. Thomas blushed and nodded. He turned to leave and felt a hand on his ass softly caressing. He jerked away from the touch and looked back.

The brunette wore a devious smirk. “Sorry, I like your butt!” the brunette said with a wink as her friends fought a failing battle against their laughter.

Thomas blushed and walked back to the soda bar and Jess. She smiled knowingly at him the whole way.

“Looks like you’re a natural!” she said happily. “It looks like you’re enjoying yourself too!” she said as she referenced Thomas’s now rigid little guy.

Thomas flushed a little deeper. “I-I can’t help it!” he admitted.

“I know! Every time a girl touches your butt, it turns you on. Who knows, maybe I’ll spank you on your first break…would you like that, little guy? If I spanked you every day at work? Was that a part of your job? Hehehe, it looks like your little guy really likes that!”

Thomas gulped as he felt his dicklette pulsing towards Jess uncontrollably. He started some slow, deep breathing as he recalled the last time Thomas was at the pool, where he had some embarrassing…spillage. The last thing he wanted to do on his first day was explode all over the pool deck. Jess was making it hard not to.

“J-Jess, can you ease up a bit? It’s embarrassing enough to be naked here again. I don’t want to…lose control…again…”

“Okay, little guy, I’ll ease up. Here I’ll make a deal if you don’t cum all day, I’ll do something nice for you when we get home!” she said with a wink, which once again made

Thomas’s ‘lil guy’ pulse towards her once again. Somehow, the vagueness of her promise was even more alluring than if she just said it to begin with. Jess turned and prepared the drinks for the ladies. Thomas couldn’t help but check her khaki-covered butt out as she turned. This, of course, did little to relieve Thomas of the mounting pressure in his ‘lil guy’. She turned back and caught Thomas staring. Thomas looked down shamefully as she smirked. She came up to the counter and looked at Thomas’s tiny erection.

“See something you like, tiny?” she teased as she winked at him.

“Yes,” he admitted as he blushed.

Jess giggled flirtatiously as they shared some charged eye contact. They lingered there for a bit, just looking at each other, Thomas naked and Jess clothed.

“Well, go on then!” Jess finally spoke up. “Give them their drinks,” she said as she rolled her eyes.

Thomas smiled sheepishly and walked back over to the ladies with their drinks. They were all chatting and sneaking peeks at Thomas as he turned. As he approached, they stopped speaking once again and stared Thomas down as he came closer. Their eyes darted between Thomas’s face and his shortcomings.

He handed them each a drink, silently giving them shy smiles as he still felt self-conscious about his nudity. Each of them now openly staring at his diminutive package, clearly holding back laughter. As he handed the last drink, the elegant silver-haired woman clad in the blue floral one-piece spoke up.

“I just have to say I admire just how brave you are doing this! I would have never guessed a man…well boy…with such a small…you know, would be willing to show it so publicly! I mean, it’s the smallest I’ve ever seen!” Her friends were snickering now. “I mean, it did get bigger after you spoke with the girl behind the bar. Do you like her, by the way? Still, you’re clearly not a grower, either. I just have to ask, how do you find the courage to show such a pathetic little thing off?”

Her friends were desperately trying to suppress their laughter now as their snickers snuck through tightly shut mouths.

“I-I,” Thomas started nervously, trying to find words.

The truth was he was humiliated beyond belief by his nudity and the fact he never wore clothes anymore, but he felt he had no choice. He thought of Jess then, and how much she seemed to enjoy his enforced nudity, he remembered why he really did this then, Jess, the girl of his dreams, the girl who laughed shamelessly at his short dick. This girl still seemed beyond all odds to find him attractive, even with his tiny little nub of a penis. Thomas, remembering her, realized the only thing he could actually say to such a line of questioning.

“I have a tiny penis, and I’m not ashamed!” he said as he puffed his chest out and stood tall.

The women could no longer hold back as they laughed once again openly at Thomas. It was more embarrassing to have women laugh in his face, but he still stood tall as the color rose in his cheeks. For her part, though, the beautiful woman who asked the questions only seemed to smile at the little guy.

“I admire your confidence…little guy.”

Thomas nodded, blushing furiously, and he turned to leave, feeling a pinch on his ass as he did. He jumped and looked back to see it was the beautiful silver-haired woman. She smiled deviously

“At least you have a nice butt!” she said happily.

The brunette with grey roots spoke up then. “I know, right!?” the brunette said as they all looked at each other and laughed unreservedly as Thomas hastily dismissed himself.

He walked over to the soda bar once again, seeing Jess giggling to herself from the whole interaction.

“Hehehe, sorry, little guy, that was just too funny!”

Thomas, still blushing, laughed nervously along with her.

“Don’t worry,” Jess said. “You’re already a smash hit! You’ll probably make lots of tips,” she said with her cute little smile, looking at him adoringly.

They lingered, looking at each other for a bit when it seemed something drew Jess’s gaze as she smirked humorously past him. Just as Thomas turned to see what it was, he felt a sharp slap against his ass, causing him to jump. He turned and saw a mischievous Elia standing in a yellow one-piece that contrasted against her tan skin. He black hair in a bun, her ample tits showing some generous cleavage. Thomas had to admit she looked pretty good.

“Hehehe, I’m glad you told me about this, Jess! I couldn’t miss out on seeing his fine ass again!” she said as she looked Thomas up and down again, her eyes lingering on his ‘lil guy,’ giggling the whole time.

“H-hi Elia!” Thomas squeaked nervously.

He felt renewed discomfort as he was nude before her once again. It was the third time she had seen him naked, and he still wasn’t used to it.

“You know you look way better in the sun. Really get to see that whole…body,” she said as she bit her lip, looking him up and down.

He gulped as he felt her eyes rake over him. If he wasn’t blushing before, he sure as hell was now.

“You know Thomas, I couldn’t stop thinking about last night at the party…you performed so well for me…or should I say on me.” She winked at him and bit her finger, pressing her tits together.

“Elia, stop!” Jess admonished half-heartedly. “Look at how excited you’re making him!”

Thomas looked down, and sure enough, his dicklette was so hard it was pulsing right at Elia.

“He’ll…spill all over the pool deck if you keep teasing him like that!” Jess said.

“Don’t threaten me with a good time!” Elia said as she laughed. Jess couldn’t help but giggle, too. “But okay, I’ll stop teasing the little guy! I mean, I get why he doesn’t want to humiliate himself,” Elia said as she rolled her eyes.

“Yeah, I mean cumming on the pool deck again would be so humiliating for him.”

“Again?” Elia asked incredulously.

“Oh yeah. When Thomas was here last time, he came all over himself!”

Elia’s jaw dropped as she looked at the now-blushing Thomas.

“Really?” Elia asked, and Thomas hung his head shamefully.

“Don’t rub it in. It was SUPER embarrassing for poor Thomas,” Jess said.

Thomas looked at Jess with a pleading look, hoping she would stop bringing it up. She sported a sly smile.

“Don’t worry, Thomas, I’ll stop. I just thought she’d get a kick out of it!” Jess reassured him.

Elia laughed. “Well, I certainly did! And don’t worry, little guy, I don’t want to embarrass you like that. Although watching you cum does sound…exciting,” she said with a wink.

Thomas felt himself pulse, and Elia bit her lip as she looked at it.

“Well, Thomas, Elia here is a customer. You should get to work and offer her a drink!” Jess said encouragingly.

Thomas looked at her, though he thought it a little silly to ask since Jess was right there and could take the order herself.

“Can I get you something to drink, Elia?” he asked sheepishly.

“Such a gentleman! I’ll have a lemonade! Thanks!” she said as she turned to walk to a chair by the pool.

Thomas couldn’t help but check out her big butt bouncing underneath the swimsuit as she walked.

“Well, Thomas, what was her order?” Jess chided, knocking Thomas out of the trance he was in, staring at Elia.

“Uh, a lemonade?”

Jess rolled her eyes. “You know, for such a little guy, you sure have a big libido!” she teased, getting the drink ready.

Thomas smiled at her sheepishly as she handed him the drink, shaking her head while smiling. Thomas turned and walked to Elia. He saw out of the corner of his eye that the older women were all stealing glances, whispering, and giggling amongst each other. Elia, for her part, was watching Thomas approach with her mischievous smile, her eyes hidden behind sunglasses.

As he got close, her grin grew. He handed her the drink, and she said, “Such a gentleman, and so well dressed!” she teased as she lowered her sunglasses, shooting a wink. Thomas could only laugh nervously in response. “Now go back to Jess and show me your best side!”

He did as he was told and started to head back to Jess. As he did, Elia slapped his ass.

He looked over his shoulder and said, “You know you don’t have to smack my ass every time you see it.”

She laughed. “That’s where you’re the wrong, cutie!” she said with yet another mischievous grin.

He continued back to the soda bar blushing slightly as he felt Elia’s eye’s on his bare ass, still stinging from her recent slap. Just as he was about to speak to Jess, who had her back turned working, he heard a shout from the entrance.

“Oh my god! Baby dick is back!”

He turned slowly, dreading the source of the shout. He saw then three familiar college-age girls: A black girl with a big ass wearing a skimpy yellow thong bikini; a slim, gorgeous brunette wearing a green bikini; and another brunette with ample tits spilling out of a black bikini top and matching bottoms. Thomas watched with dread as the three girls sporting lascivious grins approached him. He retreated until his back was against the soda bar.

“I can’t believe you came back!” the slim brunette said. “I thought you’d never be in public again after last week! But here you are and still naked!” she said with a laugh.

“I know, right?” the black girl added. “You’re pretty brave to come back here and flash that little dick again?”

“Dick? You mean dicklette!” the slim one interjected, and they all laughed.

“Hey, little guy, remember what happened the last time you saw these?” the ample-titted one said as she bent forward, winking, showing off her generous cleavage.

Thomas gulped. How could he forget the only tits he’d ever seen in person and the…accident that resulted after he saw them.

“Look! The little guy likes it!” the slim one shouted as she pointed at Thomas’s now pronounced but tiny erection.

He felt his blush reaching a maximum as he felt nearly as humiliated as he was a week before. He kept trying to get back into the soda bar, but the counter held him in place. He felt a hand brush his elbow. He peered over his shoulder and saw Jess smiling reassuringly. Thomas knew what he needed to do. He stood up with fake confidence and a mighty blush, stuck his chest out, and said those magic words.

“I have a tiny penis, and I’m not ashamed!”

His veneer of confidence was betrayed as he squeaked out the last few words. The college girls all fell silent and exchanged humorous smirks.

The black girl looked back at him, still smirking. “Well, I’ll give you an ‘A’ for confidence! I mean, you showed up here, stood naked, and acted proud of your…little guy. Listen, in all seriousness, I am really glad you’re back. It was so entertaining last time! I’m sorry we teased you so hard last time.” With the last phrase, she winked and grinned.

“Yeah, I know we took it pretty far, but making you cum just by showing my tits was awesome! I never felt so good about my looks! Who knows, maybe I’ll let you see them again? You know if I do, you better give me a…repeat performance.”

Thomas felt his pulse quicken as he recalled the lovely tits being bare before him. He also found himself excited by the prospect of cumming in front of… NO, the last thing he wanted was to repeat that embarrassment, right?

“So why are you here, though? Like I don’t see your stepmother around. Did you just have an itch to show off how teenie tiny you are?” the slim one asked.

Jess spoke up then. “He actually works here now. This is his uniform!” she said with a hint of lusty mischief in her voice.

The three college girls’ faces lit up with excitement.

“You mean he’s gonna be here all day…naked?” the black one asked.

“Yep!” Jess answered happily.

“This is gonna be sooo much fun!” the big-titted one said, sporting a particularly devious grin.

“We are gonna come by so much more often!” the slim one added.

“What is his job, though?” the black one asked.

“He gets drinks for all the people here at the pool!” Jess said excitedly. “He’ll take your order and bring it over to you once I’ve finished preparing the drinks.”

“That is awesome! So, he has to get up close and personal with everyone here?” the slim one said, her enthusiasm shining through.

“Getting close seems like a requirement, or else how could we see it?” the black girl asked jokingly, and all of them, including Jess, laughed.

“Why don’t you ladies have a seat? Thomas will stop by in a bit for your order!” Jess invited the group.

“Sounds good!” the slim one said. “Don’t keep us waiting too long, little guy!” she said as she referred to Thomas, winking.

Thomas watched them walk to their chosen spot, ogling their butts much the same as he did to Elia.

“Thomas, you know if you keep staring, it will only make it more likely you have another…accident,” Jess teased.

“I-I can’t help it. They’re just…hot,” Thomas said as he looked down, blushing.

Jess shook her head with a little smile. “Just don’t get carried away, tiny dick.”

Thomas collected himself and started toward the college girls to get their order. They all smiled at him as he approached. Thomas was trying not to get aroused by them as he walked. He failed, but they didn’t fail to notice.

“Hey, little guy, excited to talk to us again?” the black one asked, looking with a sly grin.

Thomas chuckled nervously, his little guy pointing straight at her. “I, um, am here to take your order, ladies.”

“Do you guys have cocktail weenies?” the slim one said with a humorous smirk.

He heard the others snicker softly at her comment.

“N-no, just drinks like, um, soda,” Thomas replied nervously, trying not to think about the comment too much.

He felt his little guy get a little stiffer from the embarrassment, nonetheless. He took each of their orders in turn, all while they would steal glances at his little guy, suppressing giggles with smirks and smiles.

He turned to leave to tell Jess their order, and as he did, he heard a comment in a low voice. “At least he has a cute butt!”

The girls chuckled at her comment. He returned to Jess and gave her the order. She prepared the drink, and she handed it to him. As she did so, she shot him a wink. Thomas smiled sheepishly, still not used to her flirting. He carried the drinks back to the girls handing them the ones they ordered. They each smiled at him, still stealing glances at his little stiffy. Just as he turned, the black girl spanked his bare ass, and they all laughed. All Thomas could do was blush at how much he enjoyed it.


The day carried on as more women showed up. Their reactions would vary from shock to mild amusement to outright hysterics. He would every so often hear comments on his size, usually followed by laughs. He would also hear about how much they enjoy his butt. He really liked those comments.

By the afternoon, the pool was mostly full of ladies. Many continuously looked at Thomas and his nudity, despite everything he was getting used to the exposure. As embarrassing as it was, he was also starting to find it genuinely thrilling. He couldn’t help it or deny it.

The college girls walked up to the bar while Thomas chatted with Jess in between orders, having served everyone at least once. He turned to them, getting hard almost instantly upon their arrival. They gave an obligatory laugh at his lack of self-control.

“Hey! We wanted to ask you something tiny,” the brunette started. “Do you have other duties for your job?” she asked with a hint of mischief.

Jess answered Thomas. “Yes, he’s supposed to ‘perform’ for the patrons when they ask while he’s not taking your drink orders. Tips are required, of course.”

Each of them smiled deviously as they looked at one another. The black one spoke up then. “That’s perfect!”

They turned and whispered to themselves, periodically stealing glances at Thomas while giggling softly. Thomas could do nothing but stand there, nervous and exposed.

The slim girl came forward first. “Can you lean with front against the bar?” she requested. Thomas nodded and turned around, confused by the request. She came up behind him and whispered. “I just wanted to feel these buns.” Then she grabbed his cheeks, nearly causing him to jump. “Mmmm, spankable,” she said breathily. “You really do have a nice ass. I could look at it all day.” Thomas gulped as the action was rapidly turning him on. He was worried that the magnitude of the arousal he felt would be too much for him. She withdrew then. “C’mon girls, you have to feel it.”

The black girl came up next and gave it a light pat, followed by a squeeze. She then bit his earlobe and whispered. “You’re an ass, man. I know for a fact, but we’re all ass girls too!”

She moved aside, and now the big-titted brunette came up behind him and pressed her tits into his back, her hard nipples digging into his flesh. He gulped as he was desperately trying to calm himself. She ran her hands down his back slowly, digging her nails in lightly, tickling him the whole time.

“They aren’t wrong. Your ass is so nice. Probably the best I’ve seen on a man. That was another reason we were excited you were here again…and naked.”

Her hands grabbed it then as she dug her nails in nearly causing Thomas to jump. She withdrew her hand and spanked him once. The girls stopped then. Thomas turned to them, and they all sported mischievous, blushing smiles. He swallowed hard as they continued to look him up and down, finally finding the strength to speak.

“Will that be all ladies?” squeaking as he said ‘ladies.’

They all giggled.

“Nope, not even close!” the black one said. “Now get in the pool and do a handstand!” she commanded.

Thomas looked to Jess for support as he really didn’t want to do that. All she did was shrug with her mischievous smile. He surmised that the humiliating act sounded entertaining to her as well. Thomas hung his head as he realized he had no allies. He walked to the pool’s edge, trying not to notice all the eyes that kept stealing glances at him. He lowered himself in the pool and the ladies at the pools started to whisper about him, wondering what on Earth he was doing.

The college girls and Jess just stood by the side, smirking and giggling at his imminent embarrassment. Just as he was about to submerge, the large-breasted brunette yelled, “Hey, everyone! Tiny here wants to give us all a show!”

Now, all eyes were on him. He sighed and knew he just had to get it over with. He plunged his head underwater and kicked his legs overhead, blowing water out his nose to ensure the water didn’t clog his sinuses. Even submerged, he could hear the faint rumble that was the cacophony of cackling above. He held the handstand as long as he could until his air ran out, and he needed to breathe.

He brought his head above water for a gasp, and all the ladies laughed raucously, but they also, to Thomas’s surprise, cheered him on. As silly as it must have looked to see his little dick inverted while his legs stood above his head, they all found it thoroughly entertaining and wanted to encourage him to do silly things like that in the future. He felt a small smile break on his face as the worst outcome of his world coming to an end was far away.

He made his way to the pool’s edge, feeling better than he had felt in a long time. Even better than before the humiliating instance a week earlier. He smiled to himself as he emerged from the pool. He looked at Jess, still smiling. She returned a sweet smile to him, and their eyes lingered on each other for a moment. A slap on Thomas’s ass ended the moment. The familiar sting told him its source immediately.

“Just can’t get enough, huh, Elia?”

She giggled furiously. “Nope! My handprint is gonna get permanently etched in your ass by the time I’m through with you!” she said playfully.

Thomas couldn’t help but laugh. His revery was cut short, though, as a terrible intrusion on his good time came from the gate. A shrill, awful, and familiar voice shrieked, “Thomas! Just what on Earth do you think you’re doing?”


Thomas’s eyes went wide in terror, and his tiny dick retreated to the smallest size it had ever been as he looked, and his worst fears were confirmed. Veronica, his bitch stepmother, stood by the gate with a look of pure fury as she strode angrily toward Thomas.

“Are you seriously flashing your pathetic, shriveled, insignificant, and…and pathetic penis here again!? Did you not learn your lesson? And where have you been? Are some naked homeless loser now?” she shrieked and howled her words.

All eyes were on them now as all other conversations stopped. Veronica continued her furious steps until she was just apart from him. Her glare was daggers piercing his heart. He felt like crying, but somehow, he managed to remain composed, though his terror was plastered obviously across his face.

“I am taking you home at once! When I’m through with you, you won’t ever want to flash your diminutive dicklette again! Then, when you’re at your lowest and wish to hide away, I’ll bring you back and make you feel just as small as you deserve!”

Thomas now was visibly shaking from the fear he felt. He tried backing away from her, but something stopped him from behind. He looked over his shoulder and found Jess standing there. She gave him a small reassuring smile and a hand on his shoulder. Seeing her there was exactly what he needed.

He found his voice then as shaky as it was. “I-I’m not going anywhere with you, Veronica,” he said barely above a whisper.

Her eyes flared furiously at that. “Are you talking back to me!” she yelled.

He started flashing back to all the terrible things she used to subject him to. How relentless her emotional manipulations were so that even as an adult, he still felt like a child before her, how she controlled every aspect of his life before she left him naked and alone outside the pool a week earlier. Then though, he remembered the week, as embarrassing as it was, how it was the best week of his life. The fact that he was shown he didn’t have to be ashamed of who Thomas was or what he had. Jess squeezed his shoulder then, and he found his resolve.

He stood up and squeaked out, “I have a tiny penis, and I’m not ashamed.”

His voice was shaky and quiet.

“What did you just say?” Veronica asked contemptuously.

Feeling a bit more confident, he stood taller, now above the shorter Veronica. “I have a tiny penis, and I’m not ashamed!” he said, almost shouting, now feeling all the repressed anger he had towards her.

His shout was the perfect defiance and the first time he raised his voice at her. She was momentarily taken aback by this, as indicated by her stunned expression. The women around the pool reacted to his motto with a round of applause and cheers. They admired his confidence and wanted to support him. After all, they found his new role at the pool immensely entertaining. Bolstered by the support, he felt he wouldn’t have to back down.

“I ought to smack your ass for talking back to me, boy!” Veronica shouted.

“Don’t you dare lay a hand on my boyfriend!” Jess shouted back as she stepped between Thomas and his tormentor.

Thomas looked at Jess and whispered incredulously, “Boyfriend?”

His thoughts went wild as he realized she just called him her boyfriend. A smile cracked across his face, and his little friend halted and even reversed its retreat. In truth he never felt larger than he did in that moment as his little nub grew to its fully erect three and a half inches. He felt another hand on him, then this time on his ass. He didn’t need to look to know who it was.

“Yeah, back off, you bitch!” Elia said, squeezing his cheek.

Thomas now wanted to tear up for another reason entirely. He had never felt so supported in his life.

“I knew you’d be a problem after your father died, and I was forced to take care of you! Thomas, if you think I’ll let you defy me after all the sacrifices I made!” Veronica bemoaned.

Thomas’s fury peaked then. “Sacrifices! You stole my inheritance and basically held me hostage! You wouldn’t let me see my friends or date, or hold a job, or move out! I was a prisoner! In truth, leaving me here gave me the opportunity I needed to escape! Now I have a place to live with my…” He hesitated for a second only to have Jess look back at him with a smile that seemed to say, ‘Don’t you dare stop now.’ “MY GIRLFRIEND JESS!” he shouted the last bit loudly and confidently, absolutely elated by its implications.

“You little bastard!” Veronica returned as she swung her arm to slap Thomas across the face, only to have her hand stopped by Jess’s reflexes.

“You lay a hand on him, and you’ll have to deal with me!” Jess said with contempt.

“And me!” Elia said, stepping in between Veronica and Thomas.

“And us!” the old ladies from earlier said, standing from their pool chairs and crossing their arms.

“Don’t forget us!” the college girls said, walking behind Veronica.

Veronica looked around at all the other ladies who, one by one, stood up, indicating they wouldn’t let a hair be harmed on Tiny Thomas’s head. Thomas took a step forward, more confident than he had ever been in his life, positioning himself just in front of Veronica, his little dick still proudly erect. Such was his excitement at the situation.

“You have no power over me anymore, Veronica!” he declared.

The crowd cheered.

Veronica was so angry she was shaking. Now, Thomas regretted removing the barriers between them as she was winding up a strike against him. Just as she was about to throw a closed fist at his face, the college girls spoke up.

“Hey, Thomas!” they said in unison. “What do you think of these!” they shouted as they all dropped their tops at once.

Three sets of tits spilled out before him. The black girls were round and slightly droopy with brown areolas, the petite girls were perky and small with tiny pink areolas, and the ample-breasted brunettes were voluminous with massive, rigid pink nipples. His eyes bulged, and his balls tightened. He knew what was coming…him. He let out a tremendous moan as he shot his load explosively at his bitch stepmother, coating her suit in his spunk. She looked down in furious disgust at the mess all over her.

She looked up at Thomas in unrestrained fury. “You…little…SHIT!” she screamed as she prepared to hit him once more. Just as she drew her arm back with a closed fist, someone grabbed it.

“That’s quite enough!” Mary shouted, holding Veronica’s arm tightly. “I’ll not have anyone harass my newest employee!”

“Harass! Look what you’re ‘newest employee’ did to me! I demand retribution!” Veronica demanded.

“Retribution, you say? I’d say that he’s the one deserving of retribution, and he just succeeded at it!” Mary said smugly.

Veronica shook with anger. “Are you SERIOUS?”

“Serious as a heart attack. Now, it’s pool policy that anyone harassing an employee be subject to a ban at the discretion of the manager. And my discretion is you are banned…for life! Now get the hell out of my pool!” Mary shouted as she pulled Veronica by the arm and subsequently shoved her toward the gate.

Defeated, Veronica went to leave, turning back before she left. “If you think you’ll ever get a dime of your father’s inheritance, you’re delusional!” she shouted.

Thomas, more confident than ever, knowing she had nothing to ever hold over him again, stepped forward. “Actually, bitch!” Oh my god, I actually called her a bitch! “You’ll be hearing from my lawyer!” he shouted, now sporting a smug smile.

Veronica was stunned, silent, unable to respond, only able to grumble as she stormed out of the pool.

The entire pool let out a raucous cheer and started chanting, “Thomas! Thomas! THOMAS!”

“Not bad for a little guy?” Jess said as she came around his front, kissing him on the cheek.

“Not bad for anyone!” Elia chimed in. Thomas had no response other than to smile at the two of them.


The rest of the day was far, far calmer as the energy seemed to have been exhausted by the intrusion of Thomas’s stepmother. As the day drew to a close and after the duties for employees to close were completed, the still-naked Thomas and the clothed Jess walked back to her car. Elia was waiting outside for them as well. The girls had Thomas put his arms over their shoulders as they walked together. Each one held a cheek in their hands. Thomas had never been happier in his life.

“Hey, guys?” Elia spoke up.

“Yeah?” they said in unison.

“Do…do you think we could do what we did last night again?” she said with a dirty smile.

“Which part?” Jess asked with a raised eyebrow.

“The part with Thomas’s tongue…and another repeat of that…little contest. You know? Where every minute he lasts, we take off our clothes…” she said mischievously.

“I think that sounds like a great idea!” Thomas said happily.

Both girls looked down then.

Jess spoke. “Getting excited there, little guy?” she said with a smug smile.

“Yeah, a little,” he said with a wink.


The End.


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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