This is a fantasy. All characters are over 18 years of age.
by sheepisheyes » Mon May 06, 2024 1:06 pm
Billy’s cock seemed to have gotten back to normal and the Vaseline was a game changer. Now he could jerk off over and over and not worry about chaffing himself. His mom knowing about is jerking off was humiliating for sure but also a turn on knowing she knew. He still did not realize how much his sisters knew about his compulsive habit but was about to find out.
Nancy started to fathom the extent to which Billy masturbates once he started using Vaseline as a lubricant. He was not very good about wiping is cock off and she found that his underwear was coated with it. Obviously multiple times a day of jacking off. It was to the point where she could literally scrape it off with a knife. She decided the tissues in his room were not enough and handed his younger sister Margret a roll of paper towels and asked her to bring it up to Billy.
Margret headed up the stairs to Billy’s room. She went to open the door and heard the now familiar sloshing sound coming from his room. She thought finally I can see what that sound is coming from, as she burst open his door to give him the paper towel roll. Billy was sitting in his desk chair with his pants off. He had one leg draped over each arm of the chair and had scooted forward. His balls were on full view and his hard cock was glistening with Vaseline while his hand was stroking the shaft. He looked at Margret in shame and embarrassment but couldn’t stop. He felt totally exposed and humiliation washed over him. Margret stood in his doorway stunned. She had never seen a real live penis before let alone a hard one being stroked. She heard her sisters complaining about Billy jerking off all the time, but she really didn’t know what that meant until now.
Billy kept stroking, so she moved closer to watch. This just encouraged Billy and pushed him deeper into his masturbation zone. She admired his big full balls bouncing against the chair as he stroked, the huge penis which seemed to be swelling more and more as he stroked. It was fascinating. “Mom wanted me to give this roll of paper towels to use instead of tissues” she said. Billy just grunted and kept going. She looked at Billy and watched as his mouth make a little “O” shape and his eyes rolled up into his head. He looked ridiculous and she started to laugh at him. “Why are you making that stupid face? Look at you!” she laughed. Billy exploded. Margret had no idea that was coming as his cum shot at least a foot in the air landing on his shirt. Over and over, it spurted out, running down is hand and onto his balls. It was pooling on his chair under his big balls. She stood there shocked staring at the display Billy was putting on. Billy finally looked at her and turned red with shame. She unrolled a bunch of paper towels and walked up and handed them to him, getting ever closer to take in the scene in front of her. She couldn’t help herself and burst out laughing again. “You look ridiculous! You’re covered in goo and you’re naked with your thing in your hand all slimy!”. She turned around and left closing the door as Billy started mopping up the mess.
Later on, Billy came downstairs, and Nancy said “Did you get the paper towels Margret brought up? I want you to use those after playing with yourself not tissues. Your underwear is covered in globs of Vaseline. Make sure you wipe your penis more carefully”. Billy turned red and said, “I got them, and I’ll be more careful”. The shame he felt and the casual way his mom talked about him playing with himself made him horny all over again. Margret must not have said anything he though or she would have mentioned it. Dinner time came and they all sat down at the table. Little Margret said to Billy “Hi Donald!”. Billy looked confused as they all looked at her. Stacy said, “Why did you call him Donald?”. Margret said “Because I caught him in his room making his Trump face” and she made her mouth into an ”O” shape and then started making a jerking motion with her other hand. The table was silent as Billy looked humiliated and everyone looked at Billy. Suddenly Nancy cracked up and then everyone, but Billy started laughing hysterically. Poor Billy felt so embarrassed. “Stop laughing at me” he said, “that’s what makes me play with myself in the first place”. “So, you are admitting it?” Stacy said, “You played with yourself in front of your little sister?”. “Well, she walked in my room without knocking”. “Did you stop, or did you keep playing with yourself?” she asked in a condescending tone. “I kept playing with myself” Billy stammered looking down sheepishly. “Well then we are going to laugh at you. Masturbator Masturbator” she started chanting. Soon all the girls started chanting it. Billy was totally humiliated and went running upstairs. “There the masturbator goes! He’s going to masturbate!” Stacy yelled. Sure, enough Billy closed his bedroom door and started jerking off in total shame.
It started to become a game with his sisters to try to humiliate Billy to the point of masturbating. It was so easy. Billy would plead with them to stop teasing him until finally he would say “fine” and run to his room. They would all laugh and listen for the telltale sloshing sounds that were soon to follow. The best part was the red-faced shame when he came back down stairs. He couldn’t even look at them. He looked so defeated. It also evoked more laughter. Billy put up with it (not that he had a choice) because he loved the humiliation. That was what made him play with himself. Porn and seeing women’s panties were of course great but nothing matched the humiliation and his foot high cum shots proved it.
His mother thought that encouraging it might cause Billy to find it not so appealing. She thought that it being so taboo, was what made him do it. Now she started to realize that was not it at all. She did sense that the humiliation was a turn on for Billy, so she tried to be nonchalant about it. She would purposefully walk into his room to catch him. She would say “Again Billy?” and go about her business. She tried exposing him by leaving his door open so his sisters could see him. None of this has any effect on slowing him down. She finally started to humiliate him herself out of frustration. Her loser son just like his loser father. “You are never going to have a girlfriend! Look at you, you can’t even talk to girls anymore without running home and playing with yourself” this would just send him up to his room and the sloshing sounds would start.
Nancy had a date and Stacy was babysitting. She decided to invite a girlfriend over. Her friend knew about Billy. Stacy’s friend was named Megan and she was hot. She showed up in a little skirt and a button top showing plenty of cleavage and bra. Billy was not used to seeing this. His sisters were very pretty but this was different. As soon as he saw her he got a boner and almost ran to his room after they were introduced. His sister had to stop him and told him to stay downstairs as she winked at Megan. Megan motioned him to sit down in a chair and started asking him questions. “What grade are you in Billy? Do you play any sports?” Then came the question that made him blush “Do you have a girlfriend?” Stacy had to laugh as Billy just blushed and looked down. “He doesn’t have a girlfriend and never has. And probably never will.” “Why is that Billy?” Stacy asked him. Billy just shrugged his shoulders and kept looking at the floor. “Billy is a compulsive masturbator. He can’t even talk to a girl without getting a boner and finding a place to play with himself. Isn’t that right Billy?” He was so embarrassed and just as predicted he had a boner and couldn’t talk. The girls looked at his crotch and could tell he was hard. Megan said “Oh Billy is that true? Do I make you want to play with yourself?” Surprised by the question he looked up and directly at her cleavage. She was incredibly sexy. She noticed his gaze and pushed her breasts together and said “Do these make you want to play with yourself? How about this?” and she opened her legs exposing her white panties. Billy got so hard he had to adjust himself. “Oh, I guess maybe they do” she laughed. “Have you ever seen real breasts?” Billy couldn’t speak. It was all too much for him and started to stand up so he could run to his bedroom and start stroking.
“Where are you going Billy?” his sister teased “You’re going to play with yourself just from that? Oh, Billy you just have no self-control at all. Stay here!” Billy sat back down and looked between Megan’s still open legs. Megan teased “Do you want to play with yourself Billy? Right now?” Billy shook his head yes and looked at the floor. Megan unbuttoned a couple buttons exposing more of her bra as Stacy grabbed a jar of Vaseline and tossed it to Billy. “Go on then. I want to watch” Megan said. He didn’t need to be asked twice. He was used to the humiliation and embarrassment. There was no point trying to hide who he is.
Down came his pants and underwear as he sat back down. His stiff cock pointed to the ceiling. With his pants around his ankles, he opened his legs exposing his sperm bloated balls. Megan and Stacy’s eyes widened as they took in the view. He was just about to grab his cock when Megan said “Wait! I want to look at that cock for a minute. You really have a huge cock Billy and those balls dangling onto the chair. Very impressive. Ok go ahead.” Billy did as he was told and slid is hand up and down his shaft. His sister had not witnessed his masturbation with a front row seat before either. She had no idea Billy was so well endowed. Megan thought to herself it was such a shame he was so pathetic, even with a huge cock like that she was not attracted to him. He just seemed like a little boy to her in all other ways. She just couldn’t see Billy being a man and throwing her on the bed and ramming his huge cock insider her. He was better off masturbating.
As they watched, it did make them both horny. Billy could smell that arousal smell but still didn’t know what it was. Their eyes bored into Billy as he looked back in a haze. Soon his Trump face started causing Stacy to smile remembering what Margret said. He was lost in the moment not caring who was watching or how much of a fool he looked like. He just didn’t care. Megan took out her phone and started videoing him. It was so humiliating, and he knew it could destroy him but that just made him keep going and wanting more. His eyes rolled back as ropes of cum went flying out of his cock, Megan captured every second. He cupped is balls and spread his legs pumping them to release all the pent-up cum. The girls applauded. After the bliss faded Billy was so ashamed. Covered in Vaseline and cum sitting there with his pants around his ankles being laughed at.
Billy’s compulsive masturbation continued until his mother finally felt she needed to intervene. She talked to a psychologist and made a home appointment with Dr. Brenda Wynter. Brenda came to the house and Nancy and Billy sat in the living room with her. She asked Billy if he thought he could refrain from masturbating and Billy answered honestly and said that he did not think he could cutback or stop. “In that case I think the only thing to do is to put you in chastity.” She told them. “What does that mean?” Billy asked. “We will put your penis in a small cage that will prevent you from playing with it. You will still be able to go to the bathroom but only your mother will have the key to open the cage and free your penis” she told him. Billy was not happy. “I think it is worth trying. You should be allowed to masturbate every 2 or 3 days to start and maybe once a week after that. Are you willing to give this a try Billy? We all know you have no social life let alone girlfriends because of your masturbation habit. It is truly turning you into a pathetic loser”. Billy cringed but said “Ok I guess”. “Great. Let’s measure your penis to see what size cage you will need. Pull down your pants please?”. Billy obliged and his penis sprang forth. It was not completely hard yet. “Oh, my you are a large one. Please masturbate some to make it as big as it can get” she said as she took out a cloth tape measure.
This was humiliating but Billy got his cock very hard. Brenda measured his length and his girth. “Very impressive for such a young man”. Billy was on the edge now standing between them so she could measure him. “Can I finish please?” he asked. Brenda looked at his mother and said “I don’t mind. It will be his last time for while soon. Nancy?” His mother nodded her head and said, “Oh Billy go ahead” and got his Vaseline and a dish towel. Brenda was quite interested to watch him. The humiliation moved his orgasm along quickly. Brenda watched as his hips jerked and he spooged into the dish towel over and over. Brenda told Nancy she will order his cage and stop by for a fitting once it arrives.
A couple days later Dr Wynter came over. All the siblings were home and poor Billy had to be fitted with his cage in front of all his sisters. The all watched in wonder. None of them every having seen a chastity cage. It was so humiliating for Billy that when he pulled his pants down his cock was rock hard. Everyone gathered around as Dr Wynter tried to stuff is stiff cock into the cage. It just would not work. “Well Billy it looks like you are going to have to masturbate in front of us, so I can quickly get the cage on before you get hard again.” She told him. So once again Billy was playing with himself in front of Brenda and his mother but this time his 3 sisters were watching as well. The lube came out and the towel and everyone watched Billy degrade himself. He didn’t last long. Brenda quickly grabbed his cum dripping semi deflated cock and stuffed it into the chastity cage and locked it, handing the key the Nancy. His sisters all asked if they could have the key to Billy’s horror. Fortunately, his mother said she would watch after it.
After 2 days Billy was so horny. His cock ached when it got hard, and it felt like he had a bowling ball in his pants. He wanted to play with himself so badly. He lusted over everything. His sisters made him horny, his mother made him horny, he just wanted to masturbate. On the third day he had enough, he followed his mom around the house begging to be let free. “Please mommy I need to play with myself. I’ll do anything I just need to empty myself into a towel. Please!”. Nancy realized it had been 3 days and the Doctor said he should be given relief. “Ok dear but you need to do it in front of me so I can quickly put the cage back on before you get too hard”. She spoke. “Thank you mommy. Anything I’ll do anything.”
Billy stood in the living room and Nancy sat on the couch holding the key. Billy was so excited, but his cock ached in the cage. His pants were down, and she had a towel and Vaseline ready for him. She slowly unlocked the cage and his huge cock flip up violently. It was so engorged, and his balls were full. Nancy looked at it and licked her lips. It was spectacular. His cock looked so ready to burst. She also realized after 3 days of not cumming there was going to be a lot more cum than usual. Billy went to grab it and Nancy pushed his hands away. “Please mommy I have to” he pleaded. His cock was eye level as she sat there. She knew this was wrong, but she wanted it in her mouth and needed to swallow all that cum. “Billy, I am going to take your penis in my mouth and suck on it. I am afraid there is going to be too much semen to catch so I will just swallow it.” She said looking up into his eyes. “Wwwhat?” Billy knew what a blowjob was but his mother giving him one? His balls literally started filling with more cum at the thought. Nancy cupped his balls in both hands and felt how heavy they were. There must be so much cum in them. She lowered her mouth over the head of his cock and ran her tongue around it. The soft warm of her mouth and watching his mother sucking him made him explode. 3 days’ worth of cum. Nancy was disappointed it happened so quick. She barely had time to enjoy sucking him when she felt his balls start to drain. Her mouth filled instantly as she swallowed. A little dripped out the sides but she managed to swallow in time for the next load. She was gulping away and could not believe how much cum there was. She could feel the sperm swimming in her stomach. Once he was milked of all his cum, she needed her wits about her before he got hard again and quickly snapped the cage back on. His cock filled the cage quickly, but it prevented him from getting hard again. Nancy savored the taste of cum in her mouth as she told Billy to lay down in his room and recover. She quickly ran to her bedroom and masturbated, gushing pussy juice everywhere.
This time Billy had to wait 5 days. After the last time he was unlocked Nancy thought it would be better if his sister Lynne unlocked him this time. She handed Lynne the key and instructed her that she needed to supervise him so that once he was done she could quickly lock him back up before he became too hard again. Lynne was a little intrepid but decided to help. Billy had been a total pain the whole week. Always begging his mom to unlock him and let him play with himself. She kept telling him it has to be 5 days. Billy was literally humping her leg and begging. It was so pathetic.
When Lynne showed up to his bedroom holding the key, Billy was almost drooling he was so happy. “Billy are you ready to be unlocked?” Lynne asked. “Oh yes please.” Billy begged. Lynne giggled at how pathetic he was acting “Alright but I have to supervise so I can lock you back up as soon as you squirt” she told him. “Anything you want I don’t care just let me play with myself. I need to so bad. Please” he kept begging. “Relax Billy, go get whatever you need to play with yourself and then I’ll unlock you”. Billy was beside himself with glee. He grabbed his Vaseline pulled off his shorts and underwear and sat in his desk chair. One leg over each arm of the chair and was lewdly on display for his sister. His giant swollen balls we are laying against his ass and resting on the chair. Lynne just shook her head at how ridiculous he looked. “God Billy you are so pathetic” so told him. Billy didn’t care at all. All he wanted was to play with himself. “Please unlock me”.
Lynne pulled up a chair, so she was sitting directly in front of him. She leaned over and unlocked his cage. His cock sprang to attention immediately. Billy went to grab it and Lynne stopped him. “Wait. I want to look at you”. Billy was humiliated all splayed out with no modesty what so ever but he didn’t care. Lynne took in his size. He really was huge. His cock was fat and angry looking. His balls were giant. She was mesmerized. “Alright Billy go ahead”. He scooped out a big glob and grabbed his shaft with one and his balls with the other. Lynne realized he was a professional masturbator. “Oh, Billy look at you. You are so pathetic don’t you have any respect for yourself?”. “I don’t care as long as I can play with myself that’s all I want. I don’t care who watches or what anyone thinks”. He kept pounding away. Poor thing Lynne thought. “Do you want to look at my titties?” “YES! Please!” Billy shouted. Lynne lifted her shirt over her head revealing her large bra clad breasts. They were very firm. She reached behind her back and undid her bra strap. Billy just stared and stroked as her heavy breasts sprang free of the bra pointed our proudly on her 16 year old frame.
Lynne watched his hand become a blur and his eyes start to lose focus as her breasts were exposed. Suddenly she saw the Trump face and knew it was soon. She couldn’t help but laugh out load as Billy looked like a pathetic fool. He was squeezing his full balls when a huge rope of cum shot out and splashed on Lynne’s tits. She jerks back as she felt the hot jism hit and drip down her breasts. She had forgot to have a towel handy and also that Billy had 5 days of cum in his balls. Splat!, the next shot hit her on the chin and chest. Billy looked and saw a white string of cum hanging from his sister’s chin. This triggered another load. At this point Lynne just gave in to the cum splashing on her face and chest. The hot liquid was a kind of a turn on really. All in all, Billy must have ejaculated 8 times on Lynne’s chest. Lynne scooped a little off her chin and tasted the hot salty goo remembering the last blowjob she gave.
Billy was spent and just sat there lewdly splayed out with cum dripping from his cock and hand. He couldn’t move as Lynne saw his slightly deflating cock and quickly put his cage back on and snapped it shut. With his mouth still hanging open Billy just watched as his greasy cock was locked up. He sighed as Lynne got a towel and dried off her chest. She put her bra and shirt back on and left his room leaving the door open for anyone to see the pathetic spectacle.
Nancy asked Lynne how it went, and she said messy. She asked if he is locked back up and she said yes he was. Billy was losing his mind. He was so horny all the time and could do nothing about it. He started following everyone around the house begging them to unlock him. He told his mother he couldn’t take it anymore and this wasn’t working. She said he needed to be patient. His mother went out of town and gave his key to Stacy for safe guarding. Billy followed her around like a puppy dog begging to be released. Finally she couldn’t take it anymore. Alright come to my room with your jerkoff gear and maybe I will release you. Billy trotted off for his lube and towels. Stacy was sitting on her bed with a short skirt and an evil look on her face. “Come here you whiney baby. I’m sick of all your crying. If you had any control at all you wouldn’t be in this predicament. What boy masturbates 8 times a day!” Billy didn’t care and begged her to unlock him. Stacy turned sideways on the bed and said, “Kiss my ass first”. Billy would do anything. He crawled onto the bed and kissed her panties under her skirt. Stacy snickered “Pull my panties off and kiss it again”. It was humiliating but Billy loved the opportunity. His cock strained against his cage as his lips pressed against her soft ass.
Stacy pulled her skirt all the way up and pulled her ass cheeks apart “Now kiss my asshole”. Billy dove in smelling her earthy smell as he planted a wet kiss right on her hole. “Lick my hole” she ordered. Billy stuck out his tongue and began licking her rosebud. It tasted like shit he guessed although he never tasted shit. It really wasn’t bad. “Stick your tongue as far up my ass as you can”. Billy slid his tongue in her hole in and out like he would stroke his cock. She got on her hands and knees and rocked forward so Billy could reach deep into her ass.” Put 2 of your fingers in my pussy and keep tonguing my asshole” she told him. Billy had never touched a pussy before as he slid his fingers into her soft wet warm pussy. “Slide them in and out. Do the same with your tongue. If you want to cum then you need to make me cum”. Billy had no idea what to do but followed her directions. Soon she was gushing on his fingers and moaning. She pushed Billy’s face away. He smelled like her ass. His cock was straining so hard against his cage it ached. “Please let me play with myself?” he asked.
“Maybe later” she teased. “No No No” he cried and started humping the bed. “I have to cum please!” he said. “Stop it! Stop humping my bed and get out of here, and don’t wash your face either!” Stacy said. Poor Billy smelling like shit and pussy walked out dejected almost crying. How could she do this to him. She was being so cruel.