Little Richard
by sheepisheyes » Tue Sep 12, 2023 7:44 am
Richard is a shy introvert that has never had a meaningful relationship with anyone other than his hand. He has an obsession about getting caught masturbating. It consumes his life. It all started when puberty first hit around 7th grade. After his first orgasm he was hooked. All he wanted to do was play with himself. It consumed his every waking moment. He came home from school and ran out to the woods where he had a fort his friends built. This was before the days of internet. There was a Penthouse magazine there and Richard took of his pants and underwear and settled in with his magazine.
At the same time three of the neighborhood girls the same age as Richard were walking through woods and came upon the fort. They didn’t know if anyone was inside so the quietly approached it. They peered into the door and saw Richard furiously wanking away. All three of them gasped as Richard suddenly looked up. He could not stop masturbating nor did he want to. Sitting on the ground with his pants off and his legs spread open he continued pumping away as the girls started giggling and stared at him.
“Oh my god look at him” one of the girls said. “Don’t you care that we are looking at you?”. Richard just kept pumping away. It felt too good. The Penthouse meant nothing compared to the 3 girls watching him. “Look at his little penis. It’s so small!”. None of them had actually seen a penis before but Richard’s was small, very small. “We can hardly see it with your hand around it. Stop for a minute so we can see it!” Richard took his hand off his little penis and let them see it. Hard as it can be, pointing straight up in the air all red and swollen from the pounding it is taking. He moved his other hand away so they could see his little balls as well.
They all started laughing. “Well keep going!” He grabbed his little balls and start pumping again. “Look at him! His mouth is hanging open. He looks so ridiculous”. Then Richard shot one of the biggest loads he would ever shoot. The humiliation at being watched was just too much. The cum blasted out of his little penis and splashed right onto his face and then onto his stomach and finally the back of his hand. “Oh my god! It’s all over his face. What a mess”. Richard let go of his penis and dropped both arms to his side. Beat red he looked up at the three girls as the cum dripped off his face. His knees dropped to either side and he sat there for all to see with is little red rocket shrinking down to nothing. The girls all turned and ran.
This was the beginning of Richard’s addiction to being caught masturbating. No porn magazine could compare to the feeling he just had.
Richard would masturbate at home constantly. His sister and mother were well aware of his nasty habit but he never felt comfortable being caught by them. However his older sister’s friends might be a possibility. He heard his sister’s friend Melissa come in the front door. Mom was not home. He decided to leave his door ajar, not enough to be obvious but enough someone might see him. He dropped his pants and went to work. Turned sideways to the door so he could be seen without seeing them. Sure enough Melissa and his sister walked down the hall, he heard them and knew this was it. As they got closer he started stroking faster. He couldn’t see them but he could feel them walking past his door. Just then he heard Melissa laugh out loud.
“Richard! I can’t believe you’re doing that! At least close your door you pervert” his sister said. He turned his head and looked right into Melissa’s eyes, as his sister started to close the door, he spurted another huge load up into the air. She stopped closing the door and both girls just stood there and watched his little penis continue to spurt load after load. He just kept looking at Melissa as a smile came across her face. “You are disgusting” his sister said and closed the door.
Richard was hooked. It was unbelievable the rush he felt at getting caught. Unfortunately though, it was not good for future relationships. Word started to spread about his masturbation habits. He known he was being talked about. The jerk off motions by other girls made it pretty obvious. He hadn’t planned on that but deep down it only fueled his obsession further. He seemed to crave humiliation.
With his growing obsession and reputation, he entered high school. The girls were now young women and many very attractive. Richard was totally intimidated and assumed all of them knew he was a masturbator. His neighbor (who caught him the very first time) had grown into a sexy well endowed woman. They had a pool and she would sun out there with her friends in their bikinis. The pool has a fence and bushes had grown up all along the fence. The perfect place for Richard to peep at the girls and play with himself. It was a hot day and he snuck up to the pool and squeezed between the bushed and pulled down his shorts sat on the ground. The girls were all in bikinis and laying on loungers with their legs open so he could see directly at the little mounds of teen pussy. He was lost in ecstasy as he stroked and paid no attention to anything but the bikinis.
Suddenly he was grabbed by the ear and yanked to his feet. It was their mother! “What in the hell are you doing! Oh my God your pants are down and you are masturbating!” All the girls jumped to their feet as the mother dragged Richard to the pool area. He had to shuffle with his shorts around his ankles and his little penis pointing straight out. They all started laughing and pointing at his little penis as the mother announced “Look who I caught peeping at you girls? Look at him with is pants down and his hard …” She looked down at his small penis and smiled then said “little penis”. The all started laughing including the mother. Richard has bright red and totally embarrassed but his little penis was still pointing to attention and everybody was noticing.
The mother dragged him over to a chair and pulled him across her lap. His little penis and balls suddenly clamped between her legs as all the girls gathered around. “You want to peep at these girls and play with your little willy, well they are going watch you get you little bottom spanked” mother said. With that she rained down on his bottom with smack after smack. She was wearing her own bikini and her bare legs were with slick with baby oil. Each spank hurt like hell but also cause his little penis to slid up and down between her legs. The combination of pain and pleasure along with the absolute humiliation was brining poor Richard to orgasm. He could feel himself losing control and suddenly his little penis started to squirt.
The mother instantly felt his warm sperm sliding down her leg. “What did you just do! Did you ejaculate?” and she rolled him off her lap and he landed on his red bottom. His penis was still spurting cum and all the girls gasped as it landed on poor Richard. The girls start laughing at him. Richard stood up and started rubbing is bottom. They could all see the dark red hand prints. The mother said “Now you get out of here and I don’t ever want to see you back here again”. Richard gingerly pulled up his shorts as they all silently watched him run home.
The thrill of the humiliation at being watched by all these girls as they laugh and ridicule him was too much. There was no porn magazine in the world that could turn him on like that. The more that everyone knew he was a masturbator the more he didn’t care and even wanted them to know. It also dawned on him that they were making fun of his little penis. He knew the men in the porn magazines had large ones but he was realizing that he was well below average. Interestingly this turned him too.
Richard continues to masturbate so people could see him. He stood in the window of his house playing with himself as people walked by. Once he got his driver lisence, we would park in front of the women’s gym and play with himself in his car as they left the gym. Often he would hear snickers and laughs as they walked by. He did not go out on dates, no woman would even talk to him. Any women he approached even at the grocery store would look at him with a smirk on their face and shake their head at him. He would bow his head sheepishly and not look them in the eye. It got to a point where women openly harassed him for being such a pervert.
None of this mattered to Richard. He was totally addicted to being watched while he masturbated. He craved the ridicule and the humiliation. Women seem to sense this as well, the more pathetic he acted the more pathetic they treated him. He went to a park and saw a group of women there that knew who he was. He purposely sat close to them just to hear them. Sure enough “There’s that creepy guy who masturbates all the time!”. They started whispering and giggling. This was music to his ears. Even though he was embarrassed we was also quite hard. One of the women said “Hey wanker, masturbate in front of any girls lately?”. Richard just looked down. “Why don’t you do it right now in front us?”. The other girls looked at each other and laughed. He stood up pulled down his pants and sat back down and started playing with himself. “Oh my God” “I can’t believe he is actually doing it!” “What a loser!”. They just sat there watching him. “Look at his little dick. It’s so small!” “That’s why they call him Little Richard!”. He hadn’t heard that nickname before. It was all too much. He came in his hand as they laughed and teased him. “Get lost loser we’ve had our fun. Now go away” He pulled up his pants and ran to his car.
This was an interesting development for Richard. He was really starting to get a reputation and women seemed to like to see if they could humiliate him in public. He took advantage of the situation but quickly found out he had to be more careful. One time at a bar parking lot the boyfriends of the girls saw him masturbating in front of the girlfriends and beat him up pretty good. He was so pathetic he just crawled into a ball has they punched and kicked him. The girls laughed and encouraged their boyfriends to keep hurting him. He realized he did not want any guys around when he played with himself so he would find places where just women were hanging out.
By now every girl in town within 10 years of Richard’s age had heard rumors about him and most of their mothers too. Even though he was well known, he was still painfully shy and in a constant state of shame and humilitiation. Women no longer bothered to talk to him, they might taunt him or laugh at him but never have a civil conversation. He was the definition of a beta loser. Occasionally he felt sorry for himself but mostly whenever he though about how pathetic his life is, he would get turned on and have to masturbate. Even his sister teased him about his chronic masturbation.
One afternoon his sister brought a friend over. The friend asked his sister about Richard and all the rumors. She said “Oh its all true. That’s all he does is masturbate. His room is full of tissues and lotion. He doesn’t even try to hide it anymore. Its disguisting”. “Wow” the friend said “Do you saying thing to him?”. Just then in walks Richard. His sister decides now is as good a time as any “Your room is full of tissues can’t you stop masturbating for 5 minutes?”. He turned bright red and hung his head. He was not expecting this, especially in front of her friend. “You are such a wussy. Everyone knows it. You’re a loser wimp.” She began berating him calling him names. “Well what do you have to say for yourself?”. He was red from embarrassment and excitement at being humiliated in front of her hot friend. “You’re right I am a wussy” he whimpered. “What?” “I am a wussy”. They started giggling. His sister shook her head and noticed that he was hard in his shorts. “Oh my God is this exciting you? Look at you, you like being humiliated you’re hard”. Richard just looked down. “You want to go to your room and play with yourself right now don’t you?” Still looking down he slowly shook his head yes. “Well go play with yourself and make sure you shut your door this time”.
The friend was watching all this with amusement. “Wait” she said. The sister looked at her friend puzzled. “Richard would you like to play with yourself in front of us?” “Eew” his sister said. “Its alright he’s done it in front of a lot of people from what I hear, plus we’ll get to see why they call him little Richard” she laughed. “I guess” his sister said. “Well Richard do you want to play with yourself in front of us?” His little penis was straining in his shorts, his face was bright red, still looking down he shook his head yes. “I can’t hear you? What did you say?” Poor Richard looked up into her eyes and quietly said “Yes please”. Both girls started laughing. “Well then run up to your room and get some tissues and lotion. We don’t have all day” his sister said as they laughed more.
Richard returned with a box of tissues and lotion. The girls sat on the couch. They both looked very pretty in skirts and little tops. Richard went to the chair across from them and took of his shorts. His little penis shot up in the air. The friend cracked up as she saw his little penis so hard. “That’s pretty small” she said and the both got the giggles. Richard squirted some lotion in his hand. His sister said “What do you say to us?” He look at them about to grap his penis and said “May I please play with myself”. “Yes you may” they said. He placed is legs over each arm of the chair and scooted with bottom forward so they could have a full view. Then we started stroking with his right hand and squeezing his little balls with his left. “Oh my goodness!” the friend said “I guess he has done this before. That’s the most pathetic sight I have ever seen!” Even his sister who has caught him in the past was amazed at the intensity of his masturbation.
He was so far gone with lust. Staring at his sister and her friend while they shook their heads and laughed at him and told him he was never going to have a girl in his life. He knew this and accepted it. Just being allowed to humiliate himself like this was enough for him to give in to all the rejection and teasing. He craved it. Pumping away in full view was getting him right to the edge. “Uh oh it looks like somebody might squirt. Boy that’s not very long, I guess along with a small penis you are a premature ejaculator!”. That was too much He came once again right onto his face, his stomach and down his hand onto his balls. “Wow! That’s a lot of cum for such tiny balls. Good for you! At least you can do that. Too bad its all for nothing”. They both clapped, then got up and left. He was all alone naked and covered in lotion and cum.
Laying there feeling completely pathetic he heard voices outside. It was his mother and the neighbor. They were opening the door and would see him. He did not have enough time to even unhook is legs from the chair arms. Instead he grabbed his little penis and started stroking again. What else could he do but be the chronic masturbator he is.