Tiny Thomas and the New Rules

Author's note: All characters in this work are over 18. This is a continuation of the story Tiny Thomas and the Bad Pool Day.*

Thomas woke up a little disoriented as he realized he was naked on someone's couch, then his memory came back and his heart sank. He was so humiliated and every woman there saw it, his little problem. It was almost unbelievable how it unfolded, his stepmom forcing him to parade his tiny dick around the pool so that all the onlookers could laugh at his diminutive size. He thought about the way they looked and laughed at and teased him. Then something happened he didn't expect, the recollection caused him to get hard.

He immediately got embarrassed again as he realized he was naked and sporting a puny erection in Jess's apartment. A girl he had known in school, who had apparently at one point had a crush on him. He thought about how hard she laughed when she saw how small he was. His heart sank as he realized she would never view him as a real man. He was grateful she let him spend the night on her couch, but now he had no idea what to do. He had no clothes, no money, and nowhere to go. Thomas wondered how far Jess's generosity would go before she kicked him to the curb. His anxiety caused his erection to go away and for him to shrink to a little nub.

To soothe his nerves and clear his head he started pacing the apartment, but to no avail as he felt all to hopeless. A noise came from behind him causing him to jump and turn to its source. It was Jess leaving her room. She had adorable bedhead as her dark brown hair was all in clumps. She wore a baggie t-shirt that came down to just above her knees. She came out yawning and saw Thomas.

"Hi Thomas." She said sleepily. "Hi Thomas's tiny dick." She joked as she passed him. Thomas flushed at the comment and hung his head in shame. He thought about covering his dick but didn't see the point she already knew how small he was and it would be stupid to hold his junk all day.

She started pouring herself coffee and asked if he'd like some joking that it might warm him up as it was apparently very cold in her apartment. Thomas once again was embarrassed by the comment. He replied that he would take some coffee quietly. After she poured the coffee she brought it over to him as he sat on the couch, his little dick bunched up as he sat. Her eyes flicked to it and she smirked a bit.

"So Thomas, what is your plan now?" She asked inquisitively as she sipped her morning joe.

"I honestly don't know." He said in exasperation. "I'm not sure what to do, I know I don't want to go back to Veronica as she'd just try to make my life hell, but I have nowhere else to go."

Her expression was sympathetic as she listened to his answer. "Well you can crash here for a while. Do you have a job?"

"No, Veronica wouldn't let me. Now I guess I have to. Or else how am I going to live?" He hung his head hopelessly.

"It's okay. I'll help you out, but if you're going to stay here I need to lay out some ground rules." She said. He looked at her realizing she had actually offered him a place to stay.

"Sure! Anything! Just please let me stay here!"

She chuckled. "Well, I like the enthusiasm!"

"So, what are the rules?" He asked.

"First, don't take any of my food without asking first."

"Easy! I can do that for sure!"

She smiled. "Next, you need to look for a job every day. I'm not gonna support a freeloader, not even one with a cute ass like yours!" She said with a wink. His little cock twitched at the remark about his derriere.

"I will I promise!" He started feeling like his situation wasn't hopeless as these rules were a breeze.

"Until you have a job you are going to clean this apartment every day, starting today."

"Okay, that's fair."

"Finally, if you want to stay here. You need to be naked. All. The. Time." She said as her face twisted to a devious smile, shocking Thomas with the request.

"I-I-I" He stammered.

"You heard me right. You need to be naked every second you're in this apartment. Oh! And no covering you're adorable dicklette, under any circumstance!" She said her smile never leaving her face. Thomas once again felt trapped, he wanted to say no but he had no leverage and she was being very generous, and besides he didn't have any clothes now anyway.

Trying and failing to find a way out, he finally reluctantly agreed. She squealed in delight. "Oh Thomas! You just made me so happy! Trust me, I know that you can't see it now, but this arrangement is for the best! After awhile you'll see all the benefits!"

He smiled weakly at her, still unsure of the whole thing, but he accepted it none the less. "Good! Now get cleaning! I have to get ready for work!" She said as she went to her room. He wasted no time as he didn't want to disappoint Jess, since she was being so generous. Really the only thing she asked of him was to stay nude all the time while he stayed there. It sounded humiliating and arousing. What arousing!? No, not arousing, just humiliating, right? He wasn't sure anymore. As he picked up somethings off the floor he heard Jess's door open.

"Mmmm! I can get used to seeing that ass all day!" She said causing Thomas to turn to her in surprise.

She really likes my butt? He felt his cock twitch to life and it took all his will power not to cover up. Jess noticed the motion of his dick and smirked. She stood there silently staring at his dick she shifted her stance and put her hands on her hips in a domineering sense. Thomas wanted nothing more than to cover up, but he knew he couldn't right after agreeing not to. Unfortunately for him her attention seemed to bring him to full attention. Finally, once his dick sprouted to its full 3 and half inches she returned her gaze to his eyes and narrowed hers.

"New rule. Anytime I want you hard, you get it that way. I like it when it's hard even though its still quite small. And I'll give you credit it's a LOT bigger than when it's soft, which isn't really saying much." Thomas flushed. "Now, get back to cleaning! I'll be home at 3. We'll talk about dinner then."

With that she left, but as she left she looked back at Thomas with an odd look he couldn't identify. It had a sort of warmth to it, but beyond that there was subtle hint of...attraction? No, it couldn't be, she couldn't be attracted to him with his pathetic little worm, could she?

He did his best to clean the apartment all day working up quite a sweat as he did so. He seemed to have lost having got really into it. As when he finished he saw that it was almost 3. His heart sank as he realized he never applied to a job. He hoped Jess wouldn't remember and he could get away with it.

Before long she came home as he was finishing wiping down the kitchen still covered in sweat. He heard the door opened and didn't turn. He was about to stand up all the way when he felt a slap across his ass causing him to jump.

"Hehe! Sorry, it just looked so shiny and smooth from all the sweat! I have to say that yours is surprisingly firm!" She said grinning.

"Um thanks!" He said awkwardly.

"Well come on and turn around I want to see your little dick again!" She said cheerily. He sighed and complied, she giggled at the sight of him again. "It's so funny how hot you are but your dick is sooo small. Well go on make it hard!" She said with a wink. Thomas was at a loss trying to process everything. She thinks I'm hot...but that my dick is small...

"I'm waiting!" She said crossing her arms. He set down his supplies and started stroking, it felt surprisingly good. "That's it little guy get it hard for me." She said with devious lust over her lips. That was all it took and his dick was as hard as a...pebble. "Okay that's good! I don't want you to cum silly! I know that you can spill a little load any time and you did such a good job cleaning! I'd hate for you to mess it up!"

He dropped his dick and it throbbed soliciting some more giggles from Jess. "Sorry! It's just so cute when it moves like that! It's like a little chihuahua trying to jump up but it just can't reach!" Saying the last few words like she was talking to a baby. It made him feel small, but for some reason it made him feel something else. Did he...like it? NO! He hated it he wanted a big dick and he hated being reminded of how small he was. Yet he was still aroused somehow.

"So, did you find a job today?" She asked smiling warmly.

He hesitated but proceeded to speak. "N-no I didn't look. I was too busy cleaning..." He hung his head in shame.

Her expression shifted from amused to serious. "Really Thomas? That was one of my rules." She sighed. "I want to let it slide, but I'm worried about setting a precedent. I'm gonna have to punish you." Her expression once again shifted to a devious smile. Thomas gulped. "Now, since it is your first offense, I'll go easy on you, but don't get used to it! Now get over here and turn around!"

He did as he was told standing in front of her presenting his ass. She stood behind him running her hand slowly down his spine, it tickled causing him to shiver. She gently cupped his ass and whispered in his ear. "You deserve this you naughty, naughty boy." As she did that she bit his ear and his dick jumped from the sensation. Suddenly she removed her hand from his ass and then brought it down hard causing Thomas to jump forward.

"Get back here! I'm not done!" Her expression was still a devious grin, he did as he was told and she smacked him again, this time he was able to brace himself. She brought her hand down 3 more times swiftly. Whack! Whack! Whack! "Did you learn your lesson Thomas?"

"Y-yes!" He squeaked.

"Good! Now I'm gonna get my laptop and your gonna search for jobs. You can't stop until you apply to at least 3!" With that she walked to her room quickly returning with her laptop. Thomas was rubbing his burning bum when she returned, she smirked a bit at the sight. "Here! Get to work tiny!" She said with a wink.

Thomas did his best to apply for jobs, but was distracted by Jess, he couldn't help but feel a tension around her. His dick simply wasn't relaxing for some reason, all in all it took around an hour before he got to 3 applications. Once done he informed her, she smiled and gave him a hug.

"Oh Thomas! I'm proud of you! Your shaping up to be a full-grown adult...well except in one way." She said with a smirk. He smiled at her feeling a little weird about the comment at the end.

"Well, now we've both finished up with our work and you finished your chores so I say it's a good time to relax!" She said excitedly as she ran her hands down to his ass grabbing it firmly as she smiled excitedly. Thomas dick throbbed from the contact and Jess giggled. "Let's sit on the couch and watch some tv!"

With that she released him and sat on the couch patting the space right beside her, he quickly joined her and she nuzzled into his chest, laying into him. Her warmth felt very nice to the naked Thomas. She turned on the TV and some movie came on. It was a movie about some college students at the pool and one of the men lost his trunks causing everyone to laugh at him.

Jess laughed raucously at the movie apparently finding it hilarious, Thomas didn't find it so funny, but for some reason his dick was responding to it. Jess noticed his discomfort and asked him what was wrong.

He hesitated. "It's just I feel bad for him it's just so humiliating..." He trailed off.

She furrowed her brow in concern. "Oh Thomas, I know it is, listen though, you have nothing to be ashamed of. Embarrassed, humiliated...submissive, sure all those things are appropriate, but you'll see those feelings aren't always bad...sometimes they can be quite...arousing." She said with a devious look that made Thomas feel uncomfortable.

"I-I shouldn't be ashamed that I'm...so small." He said uncomfortably.

"NO silly! You have such an adorable little itty-bitty little pee-pee. Oh! It's excited when I say things like that! Hehehe! Embrace it! Enjoy that people find it amusing! You may not be able to pleasure women with it physically but you can bring them happiness by letting them laugh at it! And if you own it and embrace the pleasure their laughter brings you, you'll find its better than anything you've ever experienced!" She said excitedly. Thomas wasn't so sure, but he couldn't deny that it sounded...interesting. He always thought his dick was useless and he should feel shame, but now this beautiful girl was telling him that it didn't have to mean the end for him. He sat there silently while the movie played, thinking.

"Well, I'm gonna order some pizza! You want some?"

Distracted Thomas delayed his response. "Huh? Y-yeah that sounds good." Jess smiled and began dialing her phone. They continued watching the movie while they waited, after the pool scene it was just some generic college b-comedy, both of them seemed sort of bored by it. Then there was a knock at the door and Jess smiled.

"Well Thomas, go get it!" She said smiling wickedly at him and his face betrayed his shock.

"I have to answer the door...like this?" He questioned timidly.

"Actually, new rule, you always have to be the one answering the door!" She said with a twinkle in her eye. Thomas hung his head and her expression shifted to concern, she put her hand under his chin and lifted his head so their eyes met. "Thomas look at me. You have nothing to be ashamed of, your hot, you just have a small cock. It's okay, the delivery girl will get a kick out of it." His heart raced at hearing it was a girl. "Now, you answer the door and you pay her. She'll look at your dick and try to fight a laugh in an attempt to be polite. When you notice her fighting laughter you say 'I have a tiny dick and I'm not ashamed!' Then you stand there proudly with your head held high!" She said with an encouraging smile. He still wasn't sure. "Look, if you don't do it you're gonna force my hand to do something I don't want to...I'll have to kick you out." She said flatly.

Thomas's eyes widened in panic, his heart raced as he tried to find a way out, but could see none and so he accepted her terms. There was another knock at the door and he knew he couldn't keep the new woman waiting. He got up and went to the door. He hesitated, standing before it shaking with dread thinking of what would come after he opened it, one more knock came and he knew he could delay the inevitable no longer. He reached for the door and opened it swiftly holding his head high.

Outside the door was cute little blonde woman, who appeared to be in her 20's. She looked at the receipt reciting the order with a bored tone, apparently not noticing the state of Thomas. Once she finished reciting the order she looked up and her eyes bulged in shock. She looked down and her eyes zoned in on his little package, she smirked apparently trying to fight a laugh. Thomas confirmed their order with a squeaky voice and turned to reach the money. When he turned back he saw that her eyes had been locked on his ass and she was now blushing. She still was obviously fighting a laugh, he quickly handed her the money.

Now it was the moment of truth, he had to say exactly what Jess had told him to say. He took a deep breath and said with all the strength he could muster. "I have a tiny dick and I'm not ashamed!" He held his head high and fought back tears trying to appear strong. With that she let out a big laugh.

"Clearly!" She said laughing as she turned to go to her car. "Well tiny dick! Feel free to order pizza anytime! I enjoyed the 'little' show!" With that she left shaking her head as she laughed. Thomas was dumbfounded by the experience and despite the embarrassment he didn't die right there. For the first time he felt maybe having a little dick wasn't so bad after all. He closed the door and set the pizza on the counter. He looked over to Jess and saw she was positively beaming.

"Thomas I am SO PROUD OF YOU!" She said as she jumped up and ran over to him. She pulled him in for a big hug, pulled her self away looked in his eyes giddily and leaned in and kissed him. It was a passionate kiss, something Thomas was completely unprepared for. He got over his shock and began kissing her back wrapping his arms around her. They finally finished after a minute and looked to each other, Jess's face now flushed, almost as much as Thomas.

"Sorry, I'm just so happy!" She said.

"I-I guess I'm happy too, Jess!" He said.

She giggled and said. "Let's eat some pizza...hottie!" She said with a wink. If it were possible he would've flushed even deeper. With that they went to the couch and enjoyed their pizza. Thomas was still shocked with how the night was turning out, he had never kissed a girl before and now he was sitting naked next to one who had just given him the most amazing kiss he could imagine.

Before long they finished eating and the movie ended. It was getting late and Jess said it was time for bed. She looked at Thomas's crotch and saw it was hard. "Thomas have you been hard this whole time?" She asked looking at him concerned.

He was embarrassed to admit it, but he definitely had been especially after the pizza girl. "Y-yeah..."

"Oh Thomas," She said shaking her head. "That is entirely too long! Not the size hehe, the amount of time. You can't go to bed like that...here let me help..." She said as she approached him with a lusty grin. Thomas's heart started racing as she approached. Sat on the couch next to him and ran her fingers up his thigh. He watched as her fingers approach and he his dick started...hopping. She giggled at the motion and then she did it, she grabbed Thomas's tiny dick. He gasped as a wave of pleasure washed over him. He looked in her eyes and her grin was still plastered across it. She began pumping furiously and within 30 seconds he felt his balls tighten. He panicked as he didn't want to cum so soon, but it was too late. He held it in with all his might, but to no avail and he spilled his seed all over himself.

Jess laughed as he coated himself in his spunk. "Wow little guy, that was fast! You know I have to admit that's a lot of cum for a dick that size. Hehe, now clean yourself up and get to bed. You have things to do in the morning." With that she skipped happily to her room and shut the door.

Thomas sat there in euphoria after the experience still not comprehending everything, he snapped out of it as another drip of cum fell off the end of his dicklette onto his balls. With that he stood up and cleaned the mess. He was exhausted after everything and welcomed sleep happily. He passed out in less than a minute and slept deeply.

The next day he woke up to Jess getting coffee, she wore sweat pants and a baggie shirt, her hair disheveled. He looked to her and stood up, she turned around at the motion. "Hey little dick!" She said happily. Thomas flushed at the comment, but didn't cover up as per her rules.

"Would you like some warm coffee, you look a little cold this morning." She said with a smirk.

"Some coffee would be nice." He stated ignoring her other comment.

"Thomas about last night, that won't happen often. I mean I'm not a slut and I don't want you to get the wrong idea, I was just a little...well let's just say that I got my fill for a while." She said. Thomas was a little disappointed to hear that, but he accepted it none the less.

"So just like yesterday you have to clean the apartment and apply for jobs. This time don't skip on the job applications, I'll leave you my laptop so you can apply online since you know, you still don't have any clothes..." She said smirking as she looked at his little nubbin.

"I will I promise. I don't want to disappoint you Jess!" He said as he reached for her hand and held it gently. Her eyes twinkled a little bit before shaking it off.

"Words are one thing, but I need a man of action, so make sure you follow through with it or else I will be disappointed." She said sternly.