Tiny Thomas and the New Job

*Author's note: Sorry this one took so long. I went through some creative dry spells for a bit, but I've finally finished the next part of the story! The next chapter will probably take even longer as after this one the story will change direction a 'little' bit. Don't worry this isn't the end for Tiny Thomas, just be patient with me and I'll continue to write more for him and my other stories which are all coming along! Without further ado it's time for 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 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 to 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 night previous had escalated their relationship, but 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, 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 a 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 breath slow 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. He 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. He gulped as he realized he was going to be the smallest he's ever been and naked in front 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 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, 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 out 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. "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 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, though 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 records sake." Her devious grin never leaving 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 was ridiculous. He took the ruler and pressed the ruler up against the side of 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." She 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 breath 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. "3.5 inches!" She announced, 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 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?"

"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 explain 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 there were 3 older ladies 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 reached it.

Mary turned to him. "Are you doing alright little guy?"

He felt his anxiety rise and then Jess spoke. He 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 in 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 down time, 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 off towards 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!" She said with a wink as her friends fought a failing battle against their own 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? Made 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 he 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, to say the least.

"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.