Jack’s Painful Lessons

Jack’s Painful LessonsJack’s Painful LessonsSusan called me and asked me to stop by her house after work. Susan was a real pain. She was the widow of my dead ex-partner and, as far as I was concerned, a real nut burger, to put it mildly. Jim, my old partner, had been a good friend. I owed him (and his family) I guess.While Susan was ditzy, she was also very beautiful and she had a handsome son, Jack. Jack had been a marriage surprise. Susan thought she was putting on a few pounds when her doctor confirmed her pregnancy. Susan went from being a young trophy wife to becoming a mom, Jim a dad, and I was soon “Uncle” Richard. Lord, help us all!When I arrived that night, it soon became clear that one of my old promises to Jim was the main item on the dinner menu. Jack, a teen just in middle school, already was a very poor student. My late night wine induced pledge to help Jack be successful in school was going to haunt me. I only intended to write a letter to help him get into a good college. This was so far in the future; I thought I was home free. Alas, I was on the hot seat.As I recently announced my early retirement at work and as I had no immediate family, Susan thought I would have loads of time to set Jack on the path to a good education. Bat shit!I told Susan to have Jack start getting off the bus at my house starting in two weeks. I would begin the tutoring sessions from then until time to send him home. As I lived about a half block from Susan, this would be convenient for everyone.The first time that Jack arrived after school, I found that he was bright but lazy. His mind wondered. He failed to focus on anything worthwhile for more than a few minutes. It was a shame really, since he was otherwise a very special little boy. He had this incredible little smile and golden hair. His eyes were bright blue and his skin unblemished. His breath smelled of warm apples. His body was straight and he was tall for his age. He was not muscular but seemed soft and rounded.I had always liked him and now I was spending every afternoon sitting beside him. If I could just get him to focus on his lessons!I discussed this with his mom the following weekend.Susan: What are you saying?Richard: He’s as lazy as a hog!Susan: Oh my Lord. What can we do?Richard: I don’t have a clue. You know him better than I do. Any suggestions?Susan: I know what helped me when I was a girl.Richard: What?Susan: Nooooo… I cannot allow you to spank him.Richard: Oh really. Why not?Susan: He has never been spanked. It would traumatize him.Richard: Who spanked you, Susan?Susan: Daddy.Richard: Did sinop escort that help you?Susan: After daddy spanked me a few times, I became very focused on avoiding the experience whenever I could. All I had to do was to be in my dad’s presence and my bottom would begin to get hot. My little panties would feel so tight. Susan’s voice grew faint and she got this dreamy look in her eyes. After a few moments she seemed to remember I was present. Her voice returned to normal and she told me that all her dad would have to do was to tell her to do her homework (or anything at all) and she would immediately comply. I wondered if Susan would act saner if she were spanked regularly. Regular discipline might the path to getting her mind to deal with the world in a more rational manner. Oh well, first let me fix the son; then who knows about the mom.The following Monday afternoon, I informed Jack of some new “rules”. I would begin to keep track of his inattention and would spank him before sending him home.Jack: But Uncle Richard, mom would never allow you to spank me.Richard: It was her idea, sweetie.Jack: Oh No…Richard: I will not permanently hurt you but I am going to make your tiny bottom sting like crazy every time you do not concentrate on your homework.Jack: I will do much better today. I will be a good student! I do not want to be spanked.Richard: We’ll see.During our study session I could tell that Jack was trying harder than usual, at first, but his lazy traits soon took over again. Every time I noticed him failing to try, I took a small notebook from my shirt pocket and jotted it down. Jack dropped his head each time and muttered something that sounded like: Oh shit. Before sending him home, I ordered Jack to my home office. Jack was visibly shaking as he stood before me. His body quivered and his thin arms had goosebumps. His little face was flushed and his eyes were focused on the carpet. He looked adorable!I sat in the middle of a long leather couch and had him lay across my lap. His head and feet were supported. As I spanked her through his pants, he squirmed. His squirming had a special impact on me. I erected. I ended the spanking a lot earlier than my notebook indicated. I was experiencing too much pain/pleasure.I thought about little Jack until bedtime and awoke with him still on my mind. When he arrived that afternoon, he and I were both subdued. One short spanking was not nearly enough to change his lazy manner so I frequently got out my notebook. Jack said nothing but a slight wince of pain seemed to flash occasionally across his expression. escort sinop We continued until it was time for him to leave. I left for my office telling him to follow. When he arrived, Jack found me standing by my large chair. I made him climb on it and lean forward over the back while on his knees.Richard: The first spanking wasn’t nearly hard enough.Jack: Oh, but it did hurt. My bottom ached all night.Richard: I do NOT believe you!Jack dropped his head.I moved his hands behind his back, crossed them, and held them both with one of my hands. His waist was so slender that I just jerked his pants downward to his knees. I then laid into his tiny brief covered ass with a strong, firm spanking. His little ass was dancing in a matter of seconds. What a sweet sexy dance!The next afternoon was a repeat. And the next… and the next.At the end of the week, I slipped his briefs down for the first time. Jack made no sound, nor any attempt to stop me. He had learned to accept my corrections. This time, I got a chance to watch his sexy little butt cheeks turn slowly from white to pink to red. When I released him, he stayed in the position for several minutes, panting and treating me to a wonderful sight without the bother of paying attention to my strokes. When I peeked under him, I noticed his tiny little balls were as pink as his bottom. He was stiff as well. I realized that he was just as turned on getting a spanking as I was from spanking him. Now that was an eye-opener. This event changed things between us.The next study session seemed different… Jack was still being inattentive but I got the impression that he was doing it deliberately. Could it be true? I actually wanted him to be a good student so what would I do now? Before the two of us went to the office for the spanking, I asked Jack to stay and talk.Richard: Jack, I believe you are cheating!Jack: I’M NOT! I’m still stupid!Richard: I believe you are deliberately being inattentive so I will spank you. Is that true?Jack: I’m sorry (as he dropped his pretty head).Richard: I will make a deal with you. If you concentrate on doing your homework and do a really good job, I will continue to spank you.Jack: Ok… (Shyly and faintly).Richard: In fact, the better you study, the longer and stronger will be the spanking.Jack looked up at me and grinned like a Cheshire Cat.I picked him up and carried him into my office. I completely undressed him and had him stretch out across my lap again on the couch. I spanked and he wiggled. He wiggled and I spanked. After I stopped, I let him continue to lay across me. I rubbed sinop escort bayan my cock mound against his belly until I was sure he had felt it. I gently caressed his bottom until I had the over-whelming urge to check out any stiffness he had. I used my hands to guide his legs open. He was stiff. I gently touched his cock and balls with one of my finger tips and his body twanged like a bow string being plucked. I asked him to stand. After he arose, I handed Jack his clothes and left the room, telling him that her mom would be waiting.We took another step forward after that experience.His grades rose to A’s and B’s… which was surprising since we were spending far less time in the study room and more and more time in the office… spanking him and exploring our new relationship.His little peter grew to love my fingers. Even his tight bottom hole learned to bloom open like a flower greeting the morning sun when I blew across it. Jack’s love hole was too small for my cock but we soon discovered that his mouth was just the perfect size. He nibbled, he licked; he gently bit and sc****d his tiny teeth across it. I was in heaven! I explored both his love hole with my fingers, thumbs, and tongue.In a few months, Susan called and asked me to stop by one weekend. After I arrived, she kept thanking me. Her son was at the top of his class now. His teachers were so impressed and kept asking Susan how had she had accomplished this.Susan: I cannot tell them the truth!Richard: Why not?Susan: k**s his age are not supposed to be spanked.Richard: Maybe I am doing more than spanking him.Susan: What are you saying?Richard: When your dad spanked you, did he go further?Susan: (Face turning red) Absolutely not!Richard: Did you want him to?Susan: Maybe… (Quietly and softly).Richard: I think you and your son are very much alike. Would you like me to demonstrate on you the exact way I motivate your sweet little boy? Would you like to be a little girl for me? Susan: Yes, you can be my daddy (Said with lowered eyes and the beginning of a sweet pant.)It took only another few months until I was father, husband, and lover to both members of my new family.I especially liked it when the three of us would spend an entire weekend in bed… the same bed, of course. It always began with me spanking them. Susan helped me train Jack to spread hi love hole for my cock. Susan did this with a set of increasingly large strap-on dildos. Both adults tongued Jack’s pretty love hole until he relaxed it and then it was my turn for insertion. We opened and filled Jack’s sexy ass over and over.I think Susan had a special yen for being double-fucked. Jack in his mom’s pussy and me fucking Susan’s bottom. Usually Susan yelled the word “daddy” numerous times during the weekend. Then Jack started calling me “daddy” too. What a wonderful family!

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