Landlady's Rules

Author's note: This story is a work of fiction with fictitious names, characters, places, and events. Any resemblance to actual persons or actual events, is purely coincidental. All characters are 18 years of age or older.

***

Neal's luck went bad six weeks ago after losing his first sales job at a startup. The CEO sent a mass text stating that the funding dried up and they closed shop. The last line of the text read: "Don't come in tomorrow. Your final paycheck will be mailed."

Neal was 23 years old, one year out of college, and suddenly unemployed with no immediate prospects.

Neal lived in New York City. He was fortunate to find a room in an apartment with a woman as the owner, and her spoiled daughter. The landlady's name was Bonnie, and her 18-year-old daughter was Conny.

Neal's parents were divorced and lived in other states. Both were financially strapped.

"Neal, your rent is due tomorrow. Don't be late. Have you found a job yet?" said Bonnie in a direct and short tone.

Neal looked up from his laptop, sipped his morning coffee at the kitchen table, and replied, "Still searching, like every day. It's tough out there now, especially with limited experience in my field."

Neal only had enough money to pay half the rent, and he was nervous.

"You were late last month with the rent...are you paying me tomorrow?" repeated Bonnie.

"I'm doing the best I can. You'll get paid. Don't worry."

Just then, Conny comes out of the bathroom, only wearing a long tee shirt that barely covered her tight round ass. Her huge tits were pressed tightly against the thin fabric. She walked by the kitchen table and as she poured some coffee, shouted at Neal, "You keep dribbling your piss on the toilet! It's gross! And don't forget to put down the fucking lid!"

Neal stole a glance at Conny's ass, and then said, "Finally out of the bathroom! It's my turn now."

Neal ran to the bathroom, before either of them has a chance to say anything else.

Bonnie turned to Conny, gave her a disapproving stare, and said, "Do you like showing off your tits and ass? Put some damn clothes on."

Conny ignored her mother, while she drank her coffee and gazed into her smart phone.

An hour later, Conny left for school, Neal searched for jobs in his room, and Bonnie zoomed with clients in her office.

Bonnie "won" the two story three-bedroom apartment when her husband divorced her seven years ago. Conny and Neal each occupied a room and shared a full bathroom on the first floor. Bonnie had the master suite, master bath and private office on the second floor. The apartment was furnished beautifully: the bathrooms were all white marble; the kitchen had modern high-end appliances; the artwork was tastefully classic throughout the apartment.

Bonnie was 38 years old working remotely as a financial consultant. She was savvy, very petite and attractive. Conny had a few more months to finish high school, and the only thing on her mind was moving out with her girlfriends and having sex.

***

Two weeks later, Bonnie is pissed because Neal only paid half the rent. However, Neal is scheduled for a promising second interview today. He also met a young attractive woman, named Dee. They were going on their second date tonight.

Neal was in the bathroom with the door slightly open. He was only thinking about the interview and his date with Dee, while taking a leak. Conny walked by the bathroom and heard his piss pounding in the toilet water. She was disgusted but peaked inside. She didn't believe her eyes. She saw Neal's tiny cock pissing. She quickly put her cell phone camera on video and recorded him in action. She covered her mouth as she held back her giggles. His dick was just under two inches, and skinny as a pencil.

Neal finished up in the bathroom and Conny quickly and quietly went into her room and stared at the video. So many thoughts raced in her wicked mind.

Neal was of average height for a guy, at five foot nine, with an attractive muscular physique. He was also handsome, with brown curly hair, dark brown eyes, and a square jaw line. But he was very self-conscious about his tiny manhood, and always worried about having sex with a new girlfriend.

Neal left for the interview. Conny was still in her room, as she laughed out loud watching Neal's tiny dick take a leak. Bonnie knocked on her door, and then opened it.

"What are you laughing about? Don't you have class?" asked Bonnie.

Conny looked up with a big smirk, and said, "First period was cancelled today. I'll be leaving soon mom."

"What's so funny?"

Conny could not hold back. She turned her phone toward her mom and said, "Take a look at this!"

Bonnie stared at the video in disbelief, and said, "How on earth did you get that!"

"He had the door open! I swear! I heard his disgusting piss noise and then saw his tiny cock," Conny said laughing.

"Oh my God! That is the tiniest dick I've ever seen!" said Bonnie as she giggled.

They were both rolling on the floor laughing.

***

Later that night, Neal arrived back at the apartment. Bonnie was preparing dinner, and asked Neal, "How did the interview go? Did you get the job? When can you pay the remainder of this month's rent?"

"It went well. I should know something soon. I need to get ready for a dinner date. Talk later," said Neal as he went into his room.

"I better have it soon!" yelled Bonnie as his door slammed shut.

Neal took a shower, changed clothes, and was leaving the apartment when Conny smirked at him in the hallway.

"What are you smiling at?" Neal said suspiciously to Conny.

"Oh, nothing much at all," Conny said with a big grin.

Neal looked puzzled and left for his date with Dee.

***

Neal met Dee through a dating app. Dee was 24 years old, had long blond hair, blue eyes, and long sexy legs. She stood five foot seven with a knock-out figure. Dee worked for a high-profile advertising firm as a marketing analyst with excellent pay. Neal hid the fact that he lost his job and was currently unemployed, hoping he would get this new position soon.

The dinner conversation went great, but Neal avoided her questions about his career. He asked if she would like to have a nightcap at his apartment. She agreed but emphasized that she is only staying for a drink...nothing more.

Bonnie and Conny were watching the Bachelorette in the family room, when Neal and Dee arrived.

"Hi, meet Dee. This is Bonnie, my landlord and her daughter Conny," said Neal as they headed to his room.

Bonnie said, "Hey Dee, nice to meet you."

Conny stared at Dee, smiled and said "Hi."

Dee said, "Nice to meet both of you. You have a lovely apartment in such a great location. I work only a few blocks away."

"Nice to hear someone is working," laughed Bonnie.

Neal quickly said, "Have a good night. Enjoy your TV show." Neal took Dee's hand and led her into his room and closed the door.

"What did Bonnie mean by that?" Dee asked curiously.

"Oh, she is always blabbing about something. Would you like rum and coke? I also have some scotch," asked Neal.

They had a couple of drinks and started to kiss. Neal's hand made its way down to her thigh, and then around her firm ass. Dee liked him and was feeling good, but said, "Well, it's time for me to go, it is only our second date."

Neal said, "Are you sure you don't want to stay longer?"

"Not tonight, but we should do this again soon."

"Absolutely. How about tomorrow night?"

Dee looked at him with a sexy smile, and said, "Sure...looking forward to it."

***

Bonnie got bored quickly with the routine and had many affairs while she was married. One day her husband came home early and caught her giving a blow job to the neighbor. The divorce was ugly. He was a very successful investment banker. In court, the judge awarded Bonnie the use of the apartment, alimony and child support until Conny turned 18. Bonny decided then that marriage was not in her future.

Bonnie had no trouble finding companionship. She had long black wavy hair, green eyes, a sexy face and a dark complexion that would make most men hard in an instant. She was only five foot two and weighed 95 pounds. Her attractive body was extremely petite, with all the right curves.

***

The next morning Conny was at the kitchen table staring into her phone when Neal came in for breakfast.

Conny said, "You keep squirting your damn pee on the toilet, and you never put the fucking seat down."

"I'll try to remember to put it down. But you can clean-up your shit too, like those damn used makeup wipes all over the place," Neal said.

"That's bullshit, they go in the trash," replied Conny. She paused and then said, "Besides, can't you aim your tiny dick over the toilet, and quit dribbling your pee."

Neal was frozen in shock and stared at Conny. He had no words.

"Yeah, I saw your little cock. You need to close the bathroom door when you take a piss."

"What the fuck are you talking about?"

"I'm talking about this!" Conny smirked, turned on the video and put the screen in Neal's face.

"Holy shit! You little perverted bitch!"

Bonnie heard the commotion all the way upstairs and came into the room while the video was running.

Neal was red as a tomato. Bonnie and Conny laughed out loud.

Bonnie said, "Get over it. That should be a lesson for you. Keep the bathroom door shut...even if there is not much to see."

"I can't believe this shit! Delete that video!" demanded Neal.

"You're in no position to make any demands. Just get a job and pay the rent, or you will be out on your little ass!" yelled Bonnie.

"You mean his little cock," giggled Conny.

Neal stormed out, went into his room, and slammed the door.

***

Neal was terrible with interviews. He came off arrogant and conceded, and he did not realize it. He was nervously waiting for a reply from the company all day. He sent a thank you note, and the hiring manager said it was between him and one other candidate.

Neal felt the pressure from Bonnie and was humiliated with Conny's video. His goal was to get the job and move out as soon as possible. He looked forward to his third date with Dee tonight, hoping it would go smoothly.

Neal spent the entire day in his room, applying for other positions and waiting for that call.

***

It was 7 pm, and Neal and Dee arrived at the restaurant at the same time. They hugged and were seated at the table right away.

Dee was dressed in a black short skirt, a red silk blouse and black high heels. Her legs were bare, and she looked sexy. Neal thought the conversation was going well until she kept asking about his job and what he did for a living. Dee was still unaware of Neal's predicament. Every time she asked about his job, he changed the subject. She began to think that Neal was hiding something.

Dee broke up with her boyfriend two months ago after dating him for almost a year. She caught him lying regarding just about everything.

Neal suggested that they go to her place for a drink, but Dee said that she shared a room with her girlfriend and there was no privacy. She explained that she was looking to move into her own place but was helping her long-time friend by staying there and paying half the rent. It benefited Dee as well, as she was able to save a lot of money over the past two years.

***

Neal and Dee arrived at apartment around 9 pm.

Bonnie and Conny were on the couch streaming social media.

"Hi again," said Dee to Bonnie and Conny.

Just as Bonnie and Conny greeted Dee, Neal's phone rang. It was the hiring manager. He excused himself and went into his room to take the call.

Bonnie, Conny and Dee did not seem to mind. They were all getting along very well and chatted about a variety of topics.

Neal's bad luck streak continued. The hiring manager said they selected the other candidate, and he just accepted the offer. He apologized for the late call but wanted to let Neal know without further delay.

Neal was shell-shocked. He sat on his bed and stared at the ceiling for several minutes. He finally came out of his room with a blank expression.

Dee looked at his face and asked, "What's wrong? Did something happen?"

Bonnie knew right away, and said, "You didn't get the job."

Neal stared at the floor and said, "They offered it to someone else."

Dee looked puzzled, and asked, "You were looking for another job?"

Conny jumped-in, and said, "He lost his job weeks ago. Didn't he tell you?"

Dee's face turned angry red, and shouted, "You have no job, and you didn't tell me after three dates!"

"I'm sorry Dee, let's go in my room and talk," replied Neal with a whimper.

Dee thought to herself she was not going through another relationship with someone she could not trust. She crossed her arms and stared at him in disbelief.

Bonnie said, "Neal, I need the rest of the rent now, or you need to move-out."

Neal's world was crashing down, and he had no control.

"You haven't even paid your rent?" cried Dee.

"He is a loser, and to top it off, his tiny dick would only tickle you," Conny said to Dee as she smirked and giggled.

"You fucking little bitch. I've had enough of you!" shouted Neal.

Bonnie yelled, "That is it. You need to pay me right now or pack up and leave."

After a few moments, Neal looked at Bonnie and Conny, and said, "I'm sorry. This is the worst night ever. Please give me more time. I'll come up with the money."

Dee was pissed. She looked at Neal and said, "We are done." She then looked at Bonnie, and said, "This apartment is perfect for me. How much? I can pay you right now."

Bonnie said, "It's $1,200 a month plus a $500 security deposit."

"Done deal. I'll send the funds right now. Give me your preferred payment method, and I'll send the prorated rent for the remainder of the month."

Neal was in shock, and shouted, "Are you fucking kidding me!"

Within a minute, Dee sent the funds to Bonnie. All three women were smiling, while Neal was close to tears.

Neal looked at Bonnie in desperation, and said, "I paid you half of the rent. Please let me stay and get together a plan."

Bonnie snapped back, "You paid half the rent, and it's more than halfway through the month now."

Neal looked defeated and desperate. He begged Bonnie to stay longer. Neal said he would do anything for more time.

Conny put her lips to her mom's ear and whispered.

Bonnie smirked, and then stood right in front of Neal. She was seven inches shorter than Neal, but she glared up into his sad eyes, and said, "You can sleep on the couch until the end of this month, but you will need to obey all my rules. No exceptions."

"What rules?" Neal asked in a wimpy tone.

"Rule number one: don't argue with any rule. Rule number two: you must wait to use the bathroom until Conny and Dee are completely done. Rule number three: you must do all the chores, including cooking and cleaning every day you are here. Rule number four: you must always be naked; this is your punishment for being rude and deceitful. In addition, any of us can add a rule at any time."

Conny and Dee were smirking like schoolgirls.

After a pause, Bonnie said, "If you agree to the rules, then strip. If not, get your things and leave."

Neal turned red and had no words. He just stared at the floor in defeat. All three woman were looking at him and waiting for his decision.

Without saying a word, Neal sat on the couch and took off his shoes and socks. He stood up and unbuttoned his shirt, revealing his broad hairy chest. He unbuckled his belt, unsnapped his pants, and pulled them down. Neal faced Bonnie, Conny and Dee in his briefs. He closed his eyes and pulled down his shorts.

Dee could not believe the size of his tiny pecker. They all covered their mouths and laughed. Neal threw his shorts on the floor. His masculine physique and his tiny two-inch cock were an odd pairing.

"I told you he could only tickle you with that little thing," Conny said laughing in Dee's ear.

Neal looked to the floor and covered his cock with his hands.

Bonnie said, "Never cover your little dick." She paused and said, "Go get your bedding and put it on the couch. You can clear out your clothes and bathroom items, and stuff them into the storage closet. Dump whatever else does not fit."

Bonnie looked at Dee, and said, "You can move-in any time dear. The bed and furniture in the room are mine. You just need to bring your own bedding. Welcome to our home."

Conny gazed into Dee's eyes and kissed her on the cheek, and said, "I'm so glad you are my roomie."

Neal got angry and yelled, "This is so fucking unfair!"

Bonnie got mad and yelled, "Neal, if you speak to us like that again, you are out of here! Understand!"

Neal paused, looked to the floor and said, "Yes, I'm sorry."

"I don't want sorry! I want compliance!" Bonnie paused and then said, "As a matter of discipline, you can kiss our asses."

Conny looked excited while Dee just stood there trying to take it all in.

Neal looked dumbfounded, and asked, "What...are you serious?"

Bonnie took off her robe. She was only wearing a lace bra and thong panties. The tops of her firm tits were pushed up from her skimpy bra. Her ass was petite, perfectly smooth and unblemished. She turned around, bent over, and said, "Kiss my ass right now."

Neal got on his knees, and kissed Bonnie's bare rear-end. The feeling of her flesh against his lips got him excited.

Conny said, "My turn."

Conny was five foot four inches, had long dark brown hair, blue eyes, a small round face and lush pink lips. Her tits were large, firm and gorgeous. She was petite like her mom, weighing only 105 pounds. Her tone legs were slender. Her perfect thighs led up to her perfect tight ass. Conny was wearing lose gym shorts and a thin tee shirt. She stuck her ass in Neal's face and slid her shorts down to her ankles. She was not wearing panties. Her nice round ass was in his face.

Conny said, "Kiss it good!"

Dee was getting turned-on seeing Conny's ass. She never had a desire for another woman, until now.

Neal's cock started to get a little stiff, after his lips pressed against Conny's bare ass.

"Looks like the tiny thing is getting hard," laughed Bonnie.

Neal was still on his knees when Dee stood in front of him, and said, "Time for you to lick my asshole."

Bonnie and Conny looked amazed after hearing the surprising bold demand from Dee.

Dee lifted her skirt and pulled down her panties. Her pretty blonde pussy was a few inches from Neal's face. Her snatch was perfectly groomed with a narrow strip of blonde fur.

"This is what you will never have," said Dee with a vengeful voice. She then turned around, bent slightly, and spread her ass cheeks, and repeated, "Time for you to lick my asshole."

Conny got moist between her thighs after seeing Dee's pretty pussy. She never desired a woman, until now.

Neal was staring at her pink asshole two inches from his mouth. His four-inch boner was at a full erection. He could not believe he had to lick her asshole. Neal stuck his tongue on her starfish and licked it.

Dee pressed her ass onto his tongue, as he licked her a few more times.

Bonnie and Conny laughed while thoroughly enjoying the scene.

Dee stood up, put her panties and skirt back in place, and stared at Neal's little hard-on.

Bonnie said, "Time to relieve yourself, little fellow."

"Go on. Beat-off," laughed Conny.

Dee bent down and spit on his cock.

"Jerk-off, like a bad boy," shouted Dee.

Neal was hard as a rock and had to comply. He stroked his boner as they commanded. They each took turns spitting on his cock, as he jerked-off. He could see Conny's tits through her thin tee shirt. Her nipples were hard and pointy. They bounced freely as she laughed. Neal got more excited and stroked faster and harder. He exploded with an intense orgasm and came all over his hand and stomach, while his cum dripped on the floor.