Tiny Thomas and the New Rules

"I promise, I promise." He said and she seemed to soften at his promises.

"Well, I gotta get to work. I'm gonna shower and go. Get started cleaning!" She said happily. He did as he was told, before long she came out in her work uniform, Thomas didn't look up as he wanted to appear focused on the task at hand hoping he would earn Jess's approval. He was on the floor scrubbing when he felt a soft hand caress his ass, he jolted at the contact and looked at Jess. She had a little smirk on her face, but said nothing. She then shot him a wink and left the apartment. Thomas could feel his dick get hard from the contact. He sighed as he knew he didn't have time for a release.

Luckily it didn't take as long as yesterday to clean as he found a little routine and it was mostly clean already. As soon as he finished he got on Jess's laptop and began applying to jobs. In the end he applied to four jobs, and he felt satisfied. Thomas looked to the clock and saw that he still had an hour before Jess got home. He decided he would have some fun and went to a popular search engine on the internet.

He began searching for some stimulating content when a new idea popped in his head. He started searching for 'man naked before laughing women'. His eyes widened as he found a litany of content like what he was searching for. He clicked on a video that looked like a few women looking at a small guy on a webcam. As he watched he found himself immediately getting hard from how they made fun of the little guy. He wanted to turn off the video, but he was captivated and he subconsciously started rubbing himself. He lost track of time looking at video after video and he saw that Jess would be home soon. He closed the browser and put it away just in the nick of time.

She seemed a little tired and Thomas inquired as to why. She explained how there were these bitchy women at the pool and how annoying they were. He listened carefully as she spoke commiserating with her plight. She then turned her attention to Thomas.

"How about you Thomas, I see the apartment is clean did you apply for 3 jobs like our rule?" She asked raising an eyebrow.

"Yeah! I actually applied for four jobs!" He said proudly.

"Oh Thomas! I am so glad! Hopefully they call you for an interview!" She said excitedly as she grabbed her laptop and headed into her room. Thomas decided he would watch TV while he waited for her to come back out.

Around ten minutes later she came out of her room and seemed a little annoyed. "Thomas did you use my laptop for anything else besides the job hunt?" She said as she tapped her foot. Thomas panicked as she said it, he thought about playing it cool, but the way she spoke made it sound like he'd been caught red-handed.

"Y-yes..." He said hanging his head in shame.

"What did you use it for?" She said like she was coaxing a child into confessing.

"I-I looked at porn..." He admitted.

"What kind of porn?" She said still looking at him with an annoyed expression.

"I-it was porn where girls laugh at small penises..." He confessed. He blushed as he did so.

Jess sighed and closed her eyes. "At least your honest. New rule Thomas, no porn, and no cumming unless I give you permission."

He looked up suddenly with wide-eyes as though to beg her not to take his orgasms from him.

"Don't look at me like that. I didn't want you cumming without me anyway, but I thought I could trust you without telling you. Now I see I have to be stricter, so no porn or cumming!" She said authoritatively. Thomas knew she meant business and so he reluctantly complied. Jess seemed to warm up a bit after he agreed.

They sat and watched tv for a bit before Jess spoke up again. "I'm hungry! Let's order Chinese!" She said, Thomas knew what that meant. He would answer the door and get laughed at again. He looked down shamefully. "Oh, don't get self-conscious now! We both know you like it when girls laugh at your dick!" She said rolling her eyes. He still didn't want to admit it, but he was starting to find that she was right.

She called in the order and about 30 minutes later a knock came. Thomas sighed and stood up to answer the door, as he did so Jess slapped his ass, he turned to her and she had an adorable smirk on her face. He tried not to focus on her smirk as it was stirring things for him. He got to the door and took a deep breath and opened it.

Outside was a little Latina woman, who looked familiar. Then it him it was a girl he went to school with and he panicked. She like the woman the night before recited the order before looking up, and as she did so her eyes bulged for a moment and she seemed dumbfounded. Then he could see in her eyes the glint of recognition he hoped she wouldn't have. Then she looked down and his heart sank, she immediately smirked and looked back at his gaze.

"Well Thomas! I never knew this side of you before!" She said with her smirk never leaving her face. He flushed and he felt himself stirring below as the embarrassment washed over him.

"Hey Elia! How have you been girl? I was hoping you still worked for Wong's."

Elia looked passed Thomas. "Jess is that you?" Jess jumped up from the couch and walked over to greet her friend.

"So, I have to ask girl, before we chat, why is Thomas here, naked?" She said looking him up and down lingering on his short manhood as she tried to fight laughter.

"Hehe! He's my roommate, but he can't pay rent yet so my rule was he had to be naked all the time!" Elia's eyes widened with excitement.

"Oh my god! That is so funny!" She said as she finally laughed.

"Do you want to come in for a bit! We could catch up!" She said as she waved her in.

"Yeah, it's dead tonight so my boss won't care!" She said grinning. Thomas gulped as she walked in.

She set the food on the table and the girls sat down. "Thomas, why don't you get some plates and serve us up!" Jess said with a smile, Thomas too embarrassed to speak complied silently.

"It's been forever Jess!"

"It has girl! I've been dying to see you, I'm glad I remembered you worked for Wong's!" She said grinning.

"I have to say I'm glad you ordered too. Not just cause I wanted to see you again, but also because..." She said as she looked at Thomas's backside. He looked over his shoulder at her and he swore he saw her bite her lip as she looked at his ass, she shook it off quickly. "I wanted to see Thomas too!" She said with a laugh.

"I know I saw him at the pool a couple days ago and I was just as shocked as you!" She said smiling.

"At the pool? Is that how you two got reacquainted?" She said raising her eyebrows.

"Yeah his bitch stepmother was punishing him. You should've seen how embarrassed he was, it was so funny...well at first...she kinda went too far." She said with a more serious tone.

"Wait! What did she do?"

"Well, I won't tell you all of it, but she made him come to the pool naked and she spanked him." She said with a little smirk.

"Haha! Wow, that sounds hilarious! I would die if I were him especially with...so little to show." She said as she giggled.

"He even got hard! Let's just say it's not that impressive!"

"I'm not surprised, but I am curious. How small does it stay?"

"Thomas you know the rule, get it hard!" Jess demanded giddily. Thomas stared at her in shock as he was bringing plates to the table. He looked at her for sympathy, but her face said it all. Reluctantly he set down his plates and touched his dick. Elia immediately started giggling uncontrollably, her laughter seemed to make his dick grow even faster than usual. In less than 10 seconds he was fully hard.

"Wow you weren't kidding that thing isn't impressive at all!" Elia said laughing to the point of tears.

"Thomas what do you say..." Jess said almost like she was a mother talking to a child.

"I-I have a small penis and I'm not ashamed." He squeaked.

Elia laughter slowed a bit and she spoke. "Well that's good! I'm glad you're not ashamed! Small dicks are dicks too, they just, you know, don't satisfy women. Still it is kinda cute!" She said as she stayed transfixed on his little dicklette. Thomas wanted to fight it, but he couldn't help but be turned on by the whole situation, especially Elia's attention. He looked to Jess and saw her looking at him sweetly, he didn't really understand why she looked at him that way, it was almost affectionate.

"Well c'mon Thomas sit and eat dinner with us!" Jess invited. He sat down and they chatted catching up. Elia kept giggling every now and again at the absurdity of the situation, but even so Thomas started to get comfortable with how casual it all was. He didn't know he could feel that way while being naked with clothed women. His dick even got soft as the conversation continued. Before long Elia got a call from her boss and she had to get going.

"Sorry guys! I gotta get back to work! Feel free to buy more Chinese any time or just invite me over! It was great to catch up and see how you guys are doing!" With that she stood up and hugged Jess. She turned to Thomas and looked at him like she wanted a hug too, he looked to Jess and she nodded her head confirming it was okay.

He stood up and she looked at his now soft dicklette and smirked, he felt himself growing almost instantly. They hugged and she pressed her body against his running one of her hands down to grab his ass and she squeezed. The contact caused his semi to go full hard. She giggled at the pressure against her belly.

She pulled away and said bye seductively looking at his little dick one last time and she laughed. Thomas turned and picked up the plates as she left, he caught her staring at his butt again, this time she definitely bit her lip.

As soon as she left Jess broke out laughing. "You know it's funny because, like me, she had a...little crush on you back then. It seems like she still thinks your body is pretty hot and she clearly liked laughing at your little dick!" She said smiling cutely.

He blushed a little as he realized that another woman who formerly liked him saw him naked and hard, and she laughed at his little hard-on. "Well, little guy, finish up the dishes and then I think we should get you to bed!" He did as he was told while Jess just stared at his butt while he washed dishes. He caught glimpses of her as he did so, whenever he looked she smirked. He knew his dick was not going to calm down while she looked at him like that.

Before long he was done and said as much. Jess just said good as she sported a blushing smile, and she went to bed. He watched as she left, her hips swaying dreamily the whole way. Thomas laid on the couch and he tried to sleep, but found that he was too aroused. He wanted to get off so bad, but he knew that she would know and be disappointed he broke her rule. He did eventually fall asleep, but it took a while.

He woke up the next day to Jess jostling him. She told him she was leaving for work and for him to get to work with a smile. He complied and went about his day. He spent all day cleaning and applying for jobs. Jess came home and they went through the same routine, her teasing him about his size, tonight though she asked him to cook and he gladly complied. She watched dreamily as he did, and he admitted her attention was nice. They ate dinner at the table and she seemed quite happy, which in turn made Thomas happy.

The next day was much the same as the previous one, with a similar routine. Jess came home and announce happily that the next day was her last day of work before the weekend, and she was excited. And so, the next went much the same yet again. When Jess came home though she was smiling giddily.

"Thomas guess what?" She asked.

"What?" He asked incredulously.

"We're having company come by tonight. My old friend group from high school!" She said grinning from ear to ear. His expression betrayed his fear.

"Listen, I know it's embarrassing that they'll be here and see all of you." She said sympathetically as she looked him up and down again smirking at his little dick. "Only Elia knows our arrangement and I asked her not to say anything."

"Wait so they're coming here and they don't know that I'm gonna be...naked." He said his voice hushed for the last word.

"Hehehe! Yep! It's gonna be a...little surpise. They're gonna die laughing!" She said laughing.

Thomas's felt his nerves rise at the prospect, of course something else rose at the thought as well.

"Looks like your little guy likes the idea!" She said still grinning, her face red, probably from laughter. "Well we have work to do so let's get started!"

With that they started arranging things for a party. It took all evening and they just barely finished as the girls were set to arrive.

"Alright now, you go in my room and wait for me to say 'okay girls, I have a little surprise for you'. When you hear that come out and the real fun begins!" She said shooting him a wink as she giggled.

With that knock came at the door and she told Thomas to get in her room. He did grateful for the last bit of privacy he was sure to have that night. He heard Jess open the door and greet the girls, the feminine voices joking and laughing made his nerves reach a peak, as did his erection.

Before long, he heard her say the magic phrase. "Okay girls, I have a little surprise for you!"

Thomas took a deep breath and reached for the doorknob, shaking from the nerves and...excitement? He wasn't sure. He felt the cool knob in his hand closed his eyes and opened the door holding his breath in anticipation. He knew this was gonna be a long night.