Tim’s Painful Yet Rewarding Journey

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Oca 17, 2023 // By:analsex // No Comment

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It was a beautiful spring day. Tim had just come home from school and was sitting on the sofa watching his favorite TV show when he heard his stepmother, Diane, entering the front door. She went shopping and had her hands full of bags.Tim was eighteen and was in high school. He was one of the best students in the school, well-behaved, very respectful, and appreciated by teachers. Tim lived only with his stepmother. He also has a stepsister, Emma, three years older than him, who moved out to the university in another city. His real mother had a serious drug and alcohol problem and one day she left her three-year-old son and her husband and moved to another country with a drug dealer. They haven’t heard from her since.After two years, his father married Diane. She, too, had a failed marriage, but had put the past behind her and she and her daughter, Emma, were ready to start over. Things seemed to have settled down, and they finally had a good and happy life. Diane always treated Tim as if he were her own child. She never made a difference between him and Emma and always showed them the same love and care.Tim was happy with his new life. He finally had a loving mother, even though she wasn’t his real mother, and a stepsister with whom he got along great. As for his birth mother, he didn’t even want to know about her. She no longer existed for him, albeit she was probably alive.Unfortunately, life had another surprise in store for them, and shortly after Tim turned nine, his father died in a car accident. Diane never remarried and dedicated her life to her children. So, after his father’s death, the only family Tim had left was his stepmother, Diane, and his stepsister, Emma. Although they were not blood-related, Emma and Diane were the most important persons in his life, and he loved them dearly. They accepted him as if he were their brother respectively, their real son, and those outside their family didn’t even suspect that they weren’t actually blood-related.Growing up without a father wasn’t always easy, but Diane raised them well and never tried to spoil them. She always talked to them and shared both joys and sorrows. Thus, they became very responsible and united from an early age. Tim’s relationship with his stepmother wasn’t a typical mother-son relationship, but rather a strong friendship.Diane was forty, with brown hair, slim but curvy in the right places. She was still very attractive, with a lovely smile and a look that imposed respect. She was a voluble person who always knew when to joke and when to be serious. “Hey, Tim! How was school today?” said Diane, entering the living room. She seemed to be in good spirits.”It was Ok, mom. Nothing special,” responded Tim, still watching TV.”Don’t you have any homework to do?” she asked.”I’ll do it after the game. You know I always do my homework,” replied Tim.”I know, I know…” she said, smiling. After a short pause, without seeming bothered by the fact that Tim didn’t seem too interested in chatting with her, she continued in the same casual tone,” Guess who I ran into today at the mall? “Tim gave her a quizzical look, waiting for the answer, which came after a short pause, “You remember Mrs. Stern, my co-worker from my former job? She has a son, Ben, a year younger than you. He goes to the same school as you. Maybe you know him.”Tim remembered Mrs. Stern and her son and replied, “Yes, I know them both. “Diane continued her story, “Well we went to catch up over a coffee and when I asked about her son, she suddenly became serious and told me a story you won’t believe. Just the other day, she caught Ben spanking himself with a hairbrush and was so furious and shocked she took his hairbrush and blistered his butt he won’t sit comfortably for a while.”The word “spanking” made Tim wince, and he instantly forgot the game he was looking at. He started imagining the entire scene with Ben draped over his mother’s knee for a good spanking, then Ben disappeared from the scene and he took his place. He was over Mrs. Stern’s knee getting the spanking he never had the chance to experience. He felt his penis getting bigger and bigger and changed his position on the sofa to hide it from his stepmother. He was deep in his thoughts when he heard Diane’s kocaeli escort voice sound intrigued, “I think he really was curious about spanking if he started spanking himself. Mrs. Stern was so right to blister his butt! He got what he deserved! ““I guess so,” said Tim, not knowing how to react to the news he heard.“Who wants to be spanked, Tim? And why?”“I don’t know, mum, I don’t know…” said Tim visibly uncomfortable with the discussion. In fact, he knew very well a guy who wanted to be spanked, and that’s why he felt embarrassed and began blushing a bit. He needed to excuse himself and go to his room, so he got up and told Diane, “I’ll be in my room doing my homework.”She found his sudden leave strange, especially as the game was not yet over, but she didn’t say anything.Tim was relieved to be in the safety of his room. He couldn’t have resisted much longer without raising his stepmother’s suspicions. The confidence in his voice was replaced by a strange unease. He was hesitant and didn’t know how to react and his cheeks became redder than they should have. And on top of that, he became highly aroused and could hardly hide the bulge in the front of his trousers. All these signs would have undoubtedly betrayed him if he hadn’t quickly retired to his room.He was fascinated by spanking for as long as he remembered. In schools, spanking was no longer used as a form of discipline, but the majority of his friends were punished by their parents, so spanking was a pretty common subject. Yet his stepmother never spanked or even threatened him or his sister with a spanking. In fact, today was the first time he heard Diane say that word.He often listened to his friends’ stories and often imagine himself being in their shoes. In his imagination, he was spanked by every single friend’s mother or aunt. Well, except by his stepmother. He had never seen Diane as a candidate to give him the spanking he needed.All his friends hated being spanked, but Tim still wanted to trade places with them. He didn’t understand why he wanted to be spanked. Despite the fact that all his friends have told him it hurts horribly and they hate every single part of it, all he could think of was how he could experience a spanking.He thought he could try his luck when having a sleepover at a friend’s house, a friend whose mother uses spanking as punishment, but everyone knew his stepmother, Diane, had never spanked him so that plan wouldn’t have worked. Plus, he was mostly well-behaved and wouldn’t want to upset anyone on purpose in order to get a spanking.He had several girlfriends, and he often thought he could persuade them to put him over their knees for a spanking, but he never had the courage to tell them about his hidden desire.In fact, his fascination with spanking made him feel he was a freak because everyone else seemed to dread being spanked, but he had the best orgasms in his life when masturbating and imagining himself spanked by a strong and dominant woman. Over time, he found out he was more interested in spanking than sex. Well, in spanking and feet because he also had a foot fetish. He often stared at women’s feet, picturing himself licking and sucking on their toes and soles.Apart from these two hidden sides of himself, Tim was an ordinary guy, self-controlled and liked by those around him. He didn’t betray a submissive nature, quite the contrary. However, deep down, he knew he needed a strong, dominant woman, willing to spank him.His fascination with spanking grew over time and became an obsession. Those thoughts began to affect his life, he could no longer focus at school, became short-tempered, and distanced himself from his friends. At that point, realizing he had to find a solution, Tim tried spanking himself. He soon found out that using his hand was inefficient, so he tried with a hairbrush. He spanked himself as hard as he could and he learned that the hairbrush packs quite a sting. He soon realized that having a sore bottom helped him focus and control his spanking obsession. For a while at least. Then he spanked himself again and again.Even at eighteen, about twice a week, when alone in the house, he puts the hairbrush to good use until he ended up with a sore, red bottom. He still wanted kocaeli escort bayan to find someone to spank him but until then, spanking himself was a good enough solution.Tim had a hard time finishing his homework. His mind was full of thoughts and images. Thinking of every line from the earlier conversation, he felt confused and surprised by the ease and cheerfulness with which his stepmother spoke about spanking. He was also surprised by Diane’s opinion of how Mrs. Stern acted when she caught her son spanking himself. He never considered his stepmother an advocate of spanking, and judging by the fact that he had never heard her speak on the subject, he always assumed she would disagree with spanking. However, he was surprised to find that not only she was not against it, but she also would have done the same as Mrs. Stern in that situation.With those thoughts in mind, Tim tried to fall asleep, but he couldn’t. Lying in bed, he began to think again about Ben and the spanking he had received from Mrs. Stern. Then he began again to imagine that he was the one receiving that trashing because he had been caught spanking himself. This made him become very aroused. Then, without him even realizing it, Mrs. Stern vanished from the scene and her place was taken by his stepmother, Diane. He began picturing himself over her knee, receiving a much-deserved spanking. He realized he never imagined his stepmother spanking him.At first, he was concerned about the path his fantasy was taking, because for him spanking also had an erotic side. It was part of his sexuality and it seemed out of place for his stepmother to appear in his deepest fantasy. Then, playing the same scene over and over in his mind, he realized that he wasn’t relating sexually to any of the women spanking him. What really turned him on was the spanking itself, being submissive and losing control. Even if he imagined being spanked by a faceless woman, he was just as aroused. Realizing that, the thought of Diane spanking him didn’t seem so odd anymore.He barely managed to sleep that night and in the following days he became very distracted and his mind was stuck on the same subject that turned his world upside down a few days ago.The thing was, the more he thought about it, the more natural the idea of being over his stepmother’s knee and receiving a spanking seemed. She was after all the most important person in his life and also his best friend. If she didn’t understand his wish, probably no one would. And judging by their recent conversation about spanking, she’d probably even be willing to satisfy his deepest desire. But how could he ask her? How could he explain to her what his needs were without being too embarrassed to even talk? He didn’t have enough courage and with each passing day, he became more and more frustrated because of it.After another three days, his desperation reached its peak, and he decided to take his chances, no matter what might happen. He decided to let his stepmother catch him spanking himself, and hopefully, she would take over from there.All day, Tim was in a strange mood, but at least he was at peace with his decision. No matter how humiliating, or what the result of his play would be, he had to try. Eventually, his stepmom would understand, and their relationship was too strong to be damaged by a weird incident like that. After school, he went straight home, making sure he arrived before Diane did. He felt both excited and scared by the prospect of the spanking he may receive later that day, but he was more and more determined to go through with his plan. When he got home, he immediately went upstairs to his room and changed out of his school clothes. He put on a T-shirt and stopped putting on pants, leaving only his underwear on. He got his hairbrush ready and waited, extremely nervous, looking out the window to see his stepmother coming home.She was going to be home any moment, but the wait seemed like an eternity. He finally saw her coming, and when she pulled into the driveway in front of the house, he went to the bed, pulled his underwear down to his knees, and began spanking himself with the wooden hairbrush as hard as he could. He had done this before countless times, but that time was izmit escort different. He was so nervous he couldn’t even feel the pain of the spanks. After a short while, which again seemed like an eternity, he heard his stepmother entering his room and exclaiming in an indignant tone, “Good gracious, Tim, what’s going on here? What are you doing?”He jumped in horror and while quickly pulling a sheet over his half-naked body he said, “Sorry mom, I thought you weren’t at home!”“Never mind that, Tim. The important thing is not that I caught you, but what you were doing while thinking I’m not at home. Are you spanking yourself?”After the initial shock, the adrenaline was flowing through his body, his mouth was dry and he couldn’t articulate a word, and his cheeks were burning, probably extremely red with embarrassment. His mind was racing and his heart seemed to leap out of his chest. He wanted to scream, to apologize, to say something, anything, but the words stopped in his throat.Diane continued in a stern tone, “Does spanking yourself have anything to do with the story I told you about Mrs. Stern and her son Ben?”Tim couldn’t speak, but he nodded his head, visibly embarrassed. He had expected it to be a rather humiliating moment, but he didn’t think he wouldn’t even be able to say a word to plead his case.Luckily his stepmother didn’t need any further arguments to give the verdict Tim had been waiting for and dreaming about for years and said in the same stern tone, “Then maybe you hoped your action would have the same results as Ben’s, and I’m not going to disappoint you. I’m going to put you over my knee and give you the spanking you seem to want.” She bent over the bed and picked up the hairbrush, saying, “You won’t be needing this anymore. If you are curious about spanking, I’m more than willing to introduce you to the real deal and this hairbrush will help me.”Diane threw the sheet aside, while Tim managed in a desperate gesture to get his underwear on, grabbed him by his arm, and led him to his desk where she turned a chair into the room, sat down, leaving him standing in front of her. She measured him with her eyes then added in a strict voice, “I don’t understand why you put your underwear back on but I like the idea of taking them down for you. Spankings should always be administered on the bare bottom.” She put her fingers inside the waistband of his knickers and yanked them down, then said in a strict tone, “Step out of them, please!”He did as he was told and was standing naked below his waist looking at his stepmother, amazed to see her so strict and in control. He realized he has a full erection, which made him even more embarrassed. Diane noticed it too and was quite shocked, but managed to hide her surprise by miming a restrained smile and adding, “Looks like someone is really looking forward to this spanking.”“Let’s not wait any longer!” she said, pulling him across her lap and adjusting his position until his bottom was in the right place. She felt his erection pressing her tight and found it disturbing. She told herself that she should definitely ask Tim about this. Being a part of her stepson’s sexual fantasies wasn’t something she felt comfortable with. She managed to put that thought aside and began to focus on what was about to happen. So far it’s all happened very quickly, and she hasn’t had time to think too much.She started rubbing his bottom and looked at the back of his head, thinking how he hadn’t struggled when being led to the chair, nor when pulled across her lap. He seemed to accept the inevitable and clearly wanted to experience being spanked. She didn’t want to hurt him, but she still doesn’t want to deny him the full experience. And a real spanking hurts like hell, and that’s exactly what she promised him. A real spanking. He would squirm, gasp and cry eventually, and his bottom will be crimson red and sitting would not be an option for a few days, but at least he would know what it’s like being spanked and she hoped that she would be able to satisfy his curiosity and he would never want to repeat the experience.Tim was swallowing hard at the realization his spanking was just moments away. He still couldn’t quite believe that after all these years of dreaming about being spanked, he was finally over someone’s lap waiting for the first spank to land on his bare, unprotected butt. And that someone was nobody else than his stepmother, the person he loved and trusted the most.

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