Andrew's Day of Shame

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Status: Finished  |  Genre: Adult Romance  |  House: Booksiesilk Classic Group

As an adolescent, Andrew has no real success with girls. Because he helped her in an awkward situation, Cathy is interested to become his friend. They go for walks together and in the end, Cathy invites Andrew to visit her at her home when nobody else is there...

Andrew’s Day of Shame


Something bothered Andrew for months at a stretch. He was ashamed that he had hidden something important from everybody. It had to do with a humiliating experience he had with a girl from his neighborhood…


Ever since Andrew was thirteen, he had sinful thoughts when it came to girls. He was much too shy back then to speak about his horniness to those beautiful creatures. He also presumed that girls never or never were assailed by the bad thoughts he was having. They were too virtuous, too chaste, too angelic for that… And also, he was well aware that even if he approached them, he would have no success whatsoever and they would laugh at him. At that time, Andrew still was too short and too fat for his age…

Still, there was one girl who didn't laugh at Him. Cathy Thompson lived in his neighborhood, on Millbrook Street at Reapertingue. Her father ran a bicycle shop there that wasn’t really thriving. Yet, he seemed to have a good income, mainly from the repairs he did on bicycles and mopeds.

Cathy was one year older than Andrew. It was at the Reapertingue municipal primary school that he met her. Because he was short and fat, the girls didn't take any notice of him. Cathy was actually not popular either, neither with the boys nor with the girls. Andrew thought it was because she had red hair and a lot of freckles in summer. Someone who also knew her claimed it was because she contradicted and even challenged the dreaded neurasthenic Miss Quinten in class. That teacher would then take out her frustrations and her anger on all the pupils. Miss Quinten would fly around the classroom like a raging fury, roaring, and raving. She banged the wooden meter around and pulled the girls' hair… Needless to say, Cathy more than shared in the blows, but that didn't seem to bother her. But many of her classmates blamed her for causing Miss Quinten's outbursts of anger.


One day after school, two assholes had taken Cathy's book bag. She wanted it back, but the boys laughed at her and threw her bag from one to the other. When Andrew saw that, he intervened. All he had to do was give one of those big guys a single well-aimed punch in the stomach to end their game and make them both run off.


Cathy Thompson really appreciated that. For the rest of their time at primary school in Reapertingue, she sought Andrew’s company, both on the playground and after school. He protected her from pupils who came to harass her. As compensation, he got candy or chewing gum from Cathy almost every day.


After their primary education, Andrew and Cathy lost touch. His parents sent him to Saint-Joseph’s College in Hazelstead. Cathy went to the Royal Athenaeum in Saint-Troyan. She had an aunt who taught there.

However, Andrew’s study career at Saint-Joseph’s College was rather short. He couldn’t get decent results there because the level went above his hat. Therefore, much to his mother's regret, his father sent him to the Hazelstead Secondary Trade School.


During the summer holidays, between college and trade school, Andrew reconnected with Cathy. That happened by chance. He went to buy two new inner tires for his bicycle from her father. Cathy was in the bike shop too, and she seemed happy to see Andrew again.


It was their summer vacation. They started doing things together, Cathy and Andrew. In the beginning, they went for a walk together. Together, they explored the woods on Cobbold Hill but most often, they walked in the direction of Jommertingue. Then they followed, as best they could, the course of the Mask Brook. That narrow stream passed very near to where they both lived. They stopped under the bridge on Cross Street, not far from Mask Brook castle. Hiding in the shadows of the bridge, Cathy taught Andrew how to give hot French kisses to a girl.


One day, she said a spider had fallen behind her dress, and it itched. Andrew had to unzip her dress and unhook her bra. He didn't know if there was a spider involved, but that day, Cathy showed him her tits, and a few days later, he was allowed to play with them. He would have loved to see her pussy, or to feel it with his fingers, but Cathy didn't want that under any circumstances. So, Andrew just did what his girlfriend allowed him to do and muddled on with her. After all, there was no other girl at that time who had any interest in him...


One year later, when Cathy was sixteen, she told Andrew that she already had some experience with sex. Boys had fucked her a couple of times in Saint-Troyan. Andrew wasn't quite there yet. Even at fifteen, he didn't jerk off his cock like most of his comrades at trade school did. However, he was no longer very religious by then and he was not afraid of going to hell. It's ridiculous that he believed that, but his mother had told him when he was twelve that some boys had grown weak backs or had gone blind from masturbating. Every now and then, Andrew felt like jerking off, but he didn't risk it after what his mother had said.

One day during their second summer holidays together, Cathy was home alone. Her parents had planned to cycle that afternoon with her and her younger sister Tina to the Beechrich County Park and take a walk in the woods. Nothing came of it for Cathy. She called Andrew and said that she had fallen off her bicycle. She had injured her ankle and sprained her foot. She could barely walk, and if Andrew wanted to, he could visit her at her home when her parents and sister were away. She didn't have to ask him twice.


Once at her house, they started teasing each other. They kissed and fondled each other too. Andrew wanted, as always, to play with Cathy's tits, but she didn't allow him to at first. She did feel between his legs for the first time. Andrew wasn't sure what Cathy’s intentions were. Suddenly she said:


I am so horny… If you feel like it, you can fuck me.”


Andrew wanted to, but how that would go, he didn't know that first time. Cathy took him by the hand and led him to her younger sister Tina's room. They lay down on her bed. Cathy pulled her orange-colored skirt up, got rid of her panties, and opened her legs. She had a very nice pussy, Andrew thought, with rather small labia and already a lot of dark pubic hair. It was not the first time he saw a girl’s pussy. He had already played "little doctor" with other girls from Reapertingue, usually in the bushes on Cobbold Hill. That had happened much earlier when he was eight or nine, and none of those girls had even one hair on her pussy. So, Andrew could compare a bit, but just seeing Cathy's hairy pussy made his dick stand straight up. She was wearing a top. She pulled that down a bit, so he could still play with her tits.

So Andrew did, but not for very long. He was bursting with the desire to really fuck a girl in her pussy for the first time in his life. Cathy was also ready to be screwed because she was soaking wet between her legs. She moaned, spreading her thighs even wider and pulling Andrew over her. He wanted to stick his stiff cock into Cathy's dripping pussy. That didn't happen. Even before his cock had touched her labia, Andrew jerked his sperm away. It was quite a lot… Some of it ended up on Cathy's stomach and thigh, some in her pubic hair, and some on her sister's bedspread...


Cathy sat up straight again on the bed. Andrew could see from her face that she was deeply disappointed. Not only that, but she also had to wash off the goo that he had sprayed on her pubic hair, her stomach, and her thigh. Then, she also had to clean the bedspread and try to get rid of all traces of their failed fuck.

Cathy liked Andrew at that time. Not only that. Of all the guys she'd let herself be fucked by, he had the prettiest dick, she claimed. She didn't blame him for his premature ejaculation. However, she didn't want him to have a second chance to fuck her. Unfortunately, when Andrew prematurely shot his semen into her pubic hair, on her thighs, on her stomach, he had signed his death warrant, so to speak. With Cathy Thompson, he had lost his chance once and for all... Two or three times, he asked her if he couldn't try to get into her pussy and squirt his cum inside. She didn't want to hear any more about that. Needless to say, Cathy was very disappointed because Andrew couldn't do with her what a normal boy can do with a girl.


Andrew simply couldn’t describe his shame about what happened between him and Cathy. So far, he had only talked about his misfortune with one person, his dear sister Florence.


With Cathy, things didn't last long after the failed fuck. A few weeks after Andrew’s shameful misfire, she broke up with him. She was honest with him, however. There was someone else, a boy from Rempart Street who studied to be a teacher in Meusemalines, who occasionally fucked her behind Andrew’s back. That guy didn't have Andrew’s premature ejaculation problem, and he had stamina, keeping fucking for a very long time, Cathy claimed, and once out of two, he managed to make her cum.


After Cathy, Andrew was down. He was utterly ashamed of his failure to stick his dick into her snatch as Cathy lay with her legs open before him, ready and eager to be fucked. Since then, he no longer dared to approach other girls. Again and again, Andrew relived that disastrous moment and saw his milky white semen spray from the top of his cock on Cathy's belly and into her pubic hair.


With that whole situation, Andrew felt less and less well. He did realize that he couldn't stay silent and let his shame strangle him. He had to look for help, but where, how, from whom? He took the plunge and spoke to his sister Florence about his problem, without mentioning Cathy Thompson. Flo didn't ask him any further explanation. She probably knew which girl it was all about because Andrew had never made it a secret that he regularly went for a walk with Cathy.

Without asking his advice, Florence passed everything on to Dr. Waymaker, their family doctor. He told Flo that he couldn't help Andrew because he had no experience in this area. He referred her to a urologist in Daiste. Together with her, without informing their parents, Andrew went to see that doctor. That specialist, Dr. Lewtan, examined the adolescent thoroughly. The blood test showed that Andrew had a slightly higher testosterone level than a normal boy his age. According to the urologist, that couldn’t be the cause of Andrew’s problem. Dr. Lewtan also carefully examined Andrew’s penis and testes. The conclusion was that he didn't have an erection problem, so that couldn't have anything to do with his premature ejaculation. What Dr. Lewtan noticed was that Andrew’s glans had a bulge at the top and so, in erectile condition, was also larger and thicker than average, and apparently also more sensitive, perhaps hypersensitive to stimulation. According to the urologist, the premature ejaculation may have been due to this, but Dr. Lewtan was not sure. If Andrew wanted, he could have a prescription for a libido-inhibiting drug, maybe that would help. Andrew didn't want that, because the doctor warned him: those kinds of medicines caused drowsiness, loss of concentration, and had more negative side effects. So, the urologist couldn't really help Andrew. He suggested that Andrew should consult a sexologist. Maybe that specialist could find a solution to the problem of ejaculating too early.


Andrew was too embarrassed to talk about it all with his parents at home. His inability to fuck Cathy Thompson as it should be done had caused him trauma. The only person to whom he told what Dr. Lewtan had advised him was his ever-helpful sister Flo. She laughed and said she would play the part of a sexologist for him if he wanted to. So, Andrew accepted Flo’s offer, and it helped. By talking to her and taking her advice, Andrew gradually overcame his “Cathy-complex”. He regained enough confidence to approach other girls, and even make them “indecent proposals”. Most of the time, they weren't interested in what Andrew was proposing to them, but sometimes they were…


© Robur Quercus, 2022


Submitted: August 01, 2022

© Copyright 2023 Robur Quercus. All rights reserved.

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Add Your Comments:



A very conversational piece, Robur. Poor Andrew. Such a dilemma. I hate it for him. Girls definitely like stamina, though.

Fri, August 5th, 2022 8:56pm


DampKitten, nice comment. Indeed, one should show some pity for all those unhappy men who have Andrew's problem, or only last for a couple of minutes (or even less) before coming...

Sun, August 7th, 2022 2:59am


When some boys first get to actually have sex with a girl, the experience is so exciting that they cannot control the physical act of coming because they haven't learned how.

Wed, August 10th, 2022 4:12pm


You're right. The experience is extremely exciting and the orgasm uncontrollable.

Wed, August 10th, 2022 9:22am

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