Jack’s Painful Lessons free porn video

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Jack’s Painful Lessons

Susan 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 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. 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 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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This story was told to me by my girlfriend Emmy, it happened a few months after our fun summer together when we were teens, and obviously before we started dating 25 years later.This is how she became the best cocksucker around.Emmy was 15 at the time, a sophomore in high school. She's short, 5'2" tall, and chubby, at 170-180 lbs. She had a pear shaped body, with small, A cup tits, and a big, perfectly round ass.Her best features are her nipples, which are as big as my fingernail, and that big,...

2 years ago
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Anatomy Lessons

Anatomy Lessons By billy69boyI was so engrossed in solving my daily crossword puzzle that I hadn't noticed my young neighbor approaching. "Good morning, Mr. Gaines! You're up early today," the sweet voiced girl called out cheerily. I immediately looked up from my newspaper and instinctively closed my legs so as not to embarrass the girl, or myself, for that matter."Hello Kendra, how are you?" I had forgotten that school was done for the summer, and as in years past, Kendra had come over to...

2 years ago
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Allison and the PrimdalesChapter 68 Lessons

Lissa felt a little nervous sitting in Meg's car as the two of them drove to Sandy's apartment. She had never been to Sandy's place before, but that wasn't the reason. It was only natural for a girl to be a little scared knowing that in a few minutes she would be starting on the road to becoming a lesbian. Meg asked her for the fourth time if she was sure this was what she wanted, and Lissa nodded. She had made up her mind. This wasn't just about seducing Alya, though that was a large...

1 year ago
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Driving lessons

Rachel Doyle stirred drowsily in the fragrant bubble bath as the shrill ring of the alarm clock woke her from her slumber. She had fallen asleep for 20 minutes in the warm scented water and reached drowsily for the bath-tub plug to release the soapy suds and quickly shower. The pretty 24 year old brunette was 6 months into her in-turnship with JP Morgan and was anxious to climb the corporate ladder and join the rat race in the world of investment banking. Thus far she was well on her way, with...

Group Sex
1 year ago
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Love Lessons

It was the summer between my freshman year and sophomore year of college. My parents had run off to Europe for 2 months---without me. I was bored and spent a lot of time reading magazines and texting my best friend Veronica from the comfort of a pool chair. One evening after dinner, I was finishing yet another magazine when a frisbee flew over the fence. Through the slats I could see my next door neighbor's face. His name was Lance, and he had been my neighbor for about 5 years. He and his wife...

First Time
4 years ago
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Awesome Ariel in Adam 5 Lesbian Lessons

Awesome Ariel encounters erotic experiments at Professor Peter Poet & Princess Petra Awesome Ariel ends first Friday late, it is Saturday by now, and dawn when she falls asleep.Ariel is in spoons position between Professor Peter Poet and his dear dod Princess Petra.Ariel had nice new erotic experiences last evening and night, as Sex Student of Professor P.Ariel had her 'Intimate Interview', followed by a nice naughty night out, doing 'Dirty Dancing'.Awesome Ariel wakes up, when precious...

4 years ago
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SRU Love Doll Lessons

SRU: The Love Doll's Lessons By Ran Dandel Mike Taggart spent most of his time studying. It's not that he had other things to do, it just that he really didn't have anything else to do. You see, Mike was a member of the Sigma Upsilon Kappa Fraternity. Sigma Upsilon Kappa had the reputation on campus as being the frat where all of the "grinds" lived. Yes, a fraternity of nerds. Mike was no exception. Because he spent all of his time in study, in computer hacking, or surfing the...

2 years ago
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Andreas Dance Lessons

"I don't know honey, isn't that a little...weird for a boy?" said Andy's dad. "No, Sara said there were two guys in her dance class." "Yeah, but still, I don't think he needs anymore feminine tendincies. He's only 10 and look at his hair." His parents were talking about dance classes for him, because he asked. Andy had seen movies with dance parts, and he longed to wear the type of clothes women wore, and this was the only way he could without getting in trouble. "I think it's...

4 years ago
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Samhain Lessons

There was once a shy young woman. She was pretty, but she didn’t know it. She was witty, but she didn’t know it. She was desirable, but she didn’t know it.This young woman was from a noble family. But one so far down the social register they were never invited to the great feasts or balls. This suited our young woman, as that meant she didn’t have to make idle conversation with dull young men while drinking weak wine from golden cups.Her family was an old one and still followed the ways of the...

First Time
3 years ago
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Driving Lessons

Now coming to the day things changed. I was home, my parents left the country for a business trip. I wasnt alone, i had a cook, a housekeeper and a driver. Now i didnt have any friends but i had this online friend who i played games with and he was telling me about how he got into an car accident and wont be able to play for sometime. I felt bad for him but then i had this sudden thought i didnt knew how to drive. It was bugging me alot, i was 18 and didnt knew how to drive, we had all these...

3 years ago
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Uncle HarryChapter 6 Thursday and More Lessons

The next morning I woke up, as usual, before my two lovers – that sounded strange to me, but really, really nice. After starting the coffee I went back in and woke Sandy up with a few strategically placed kisses and nips. Once she was fully awake we went into the shower and had a shower together which, of course, involved each of us washing some 'special' body parts of the other. After we dried off and went out to the kitchen and sat at the kitchen table. I asked Sandy "How we proceed...

4 years ago
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The Swimming Lessons

It was on 8th standard summer holidays that my parents decided to take me to a one month summer swimming camp. They had separate section for boys and girls taught by two different trainers at different timing. We paid for the classes and I even started going for the evening boys classes for one week. Then it happened. I fell sick, making it unable for me to go for the remaining classes. By the time I became well and got fully recovered, the swimming class was over. Nevertheless my parents...

3 years ago
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Jackies Family Lessons

BEE-1194 JACKIE'S FAMILY LESSONS! by Sandy Bennett CHAPTER ONE I couldn't wait any longer. My bladder was bursting and my father was in the bathroom, halfway through Rigoletto. "Daddy, please get out of the shower so I can use the toilet!" I cried. Both my hands pressed into my crotch to hold back the flood and I trampled about in agony. "Can't you wait another minute?" Dad loved his showers so much that my mother suspected him of having an affair with the nozzle. "I have...

3 years ago
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Spreading Seeds Chapt 5 Private Lessons

Chapter 5 - Private Lessons Authors Note: ( This series was originally title "Goat Testical Soup for the first for chapters. I know, bad title, but What the Hell it was my first published work and it was only a joke anyway. "Spreading Seeds" is better, Let me know if you like the title change) __________________________________________________________________________________ The day after the Great Barney Clusterfuck, as it came to be known, we awoke and the girls all left...

3 years ago
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After school lessons

Bianca Ramwell grinned and nodded. She had always kept an eye out for that Mr.Revin. He was what her and her friends liked to call a hunk. She had no idea why he wanted her to stay after class. Surely a hot teacher like him would have a beautiful wife at home he was just waiting to get back to and fuck. She thought in her head how great it would be to fuck someone like Mr.Revin. Hard and rough...thinking about this made her surprisingly hot. All she could think about was hurrying up after...

2 years ago
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Moms sex lessons

Hi, I am a Divorced woman of age 36, having an 18 year old son. How cute is it, to have incest relationships with teenage son whose sexual ecstasy just starts to blossom. My son is real cute, he is fair and tall. He is slight slim and have a very good features. He is still shy & innocent. That made me bolder in initiating sexual relationships with him. He never used to peep me while I was dressing. He would turn his face down whenever I leaned in front of him with low blouse cuts. I used to...

2 years ago
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I begin my sex slave lessons

I guess you could say I’m a fairly lucky girl, I have a good paying job that I love and I live in a high rise only three blocks from my job in a middle size city. As for me, I’m a five foot six inch tall red head and weigh one hundred and twenty pounds with a thirty four C chest, twenty seven years old and have not been in a relationship for almost a year, ever since I broke up with my ex boyfriend. Every day I walk past a combined massage, nails and bikini wax business that seems...

3 years ago
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Lessons

Like all my stories, this is a work of pure fiction, derived by an active imagination and a lot of wishful thinking. Any resemblances to living persons, including me, are purely coincidental and unintentional. “More lube, baby. Make sure you cover your entire hand.” I squeezed more of the KY over my hand, and then slowly began twisting it into Lida’s pussy. Squeezing my fingers to a point, I carefully pushed them in. I moved in past the first knuckle, and up to the second knuckle, and the tip...

1 year ago
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Military Wife Blow Job Lessons

Introduction: My ex and I began to have some friends among the other jr officers After a while my ex and I started to have some friends among other Jr. officers and their wives. I found that they were in general, prudes, and that the husbands complained all the time about them not doing oral on them and a couple that did not care for any contact with their mouths to a cock My ex and I laughed about it a lot and then one day he came home and said, Hey, the guys wana know if you can teach the...

2 years ago
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Flight Lessons

After my divorce following nearly twenty years of marriage, I settled into a condo in Central New Jersey. The combination of not having a wife and the freedom of condo living gave me newfound opportunity. The time saved by not having to maintain a house combined with the free time afforded me by being single was something I really made use of. It gave me the chance to do things I had always wanted to do but never had the time. Travel and time for my hobbies such as my guitar playing were no...

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