Thomas hung his head as he plodded on along the dirt path toward the large oak tree that stood ominously behind the main house. In his right hand he held a thick strap made of brown leather. In his left hand was a piece of paper, folded carefully in half. As the mid morning sun warmed his face he thought for a moment about what awaited him. He knew that there was no amount of pleading, or argument that would spare him from his sentence. Nor was there an alternative form of punishment. His was a small family settled on the plains of Kansas. Each day was filled from sun up to sunset with the drudgery of survival. That meant hunting, and building for him, Mr. Jackson and his two sons. For the women it was preparing food, washing, and tending the home. There were no privileges that could be taken away, save the satisfactions that came from time with loved ones, a good meal, or work well done. Additionally, the plains were an unforgiving place to live. Winters were harsh, and even when the weather was favorable, attacks from the indigenous population, disease, and even small errors in judgement were a constant threat to their homestead. The Jacksons had no choice but to live as a highly disciplined unit. So it was understood that wrongdoing had only one consequence: swift and harsh corporal punishment.
Thomas and his wife Ellie Mae had been separated from their families three years prior when they were only 16 years old. They were taken in by the Jacksons. The two were deeply grateful, and were careful to do right by the family. Thomas, however, had a tendency to drink, and to sometimes act irresponsibly. That was how he found himself sentenced to the whipping tree.
As he walked he could hear the sound of the women talking amongst themselves. He looked up to see what awaited him. His wife, Mrs. Jackson and her two daughters stood around the large oak tree as Mrs. Jackson taught them how to tie a rope at the top of the trunk that would secure him for his chastisement. The women were in dresses which was a typical formality for scheduled punishments such as this one. Ellie Mae was the only one in her work clothes since it was understood to be her responsibility to deal with her husband the most harshly. It was hard for Thomas to make out what the ladies were saying, but he could see clearly the interest that Ellie Mae was taking in learning to tie the intricate knots that were a specialty in the Jackson family’s set of survival skills. Normally Thomas would be delighted to see this group of attractive young women, all dressed up, and waiting just for him. This situation, however, was much different.
As he approached, the women fell silent. They turned and stared at Thomas as the young man, normally brimming with confidence, stood before them, shoulders slumped, unable to utter a word without being spoken to.
Ellie Mae was the first to speak. Her face was stoic as she spoke firmly.
“Hello husband. Thank you for fetching the strap as I asked you to. Did you also prepare a note of contrition?”
He nodded, and handed the strap to his wife. She took it and held it down by her side. He opened the piece of paper, cleared his throat, and began to read. As he did, a strong wind blew through the homestead.
“Dear Mrs. Jackson, Ellie Mae, Victoria, and Mary Beth,
I am deeply sorry for the way I behaved the other evening.”
Mary Beth interrupted just as her blue dress flew up in the wind. “Louder Thomas, we can’t hear you!”
He spoke up, allowing his voice to cut through the wind as it began to die down.
“I am deeply sorry for the way I behaved the other evening. I was wrong to peek at the girls as they were bathing, and I was also wrong to lie about it to Mrs. Jackson. Furthermore, what I did was a betrayal of my wife’s trust and for that I will now be severely punished by each of the women that I have offended.”
He folded the paper again and placed it in the back pocket of his blue trousers. Mrs. Jackson spoke next. She walked toward him, and folded her arms. She stopped just short of him, allowing her tall petite frame to tower above him. He stared at the dirt.
“Well Thomas, I’m afraid this whippin’ is gonna be worst than the last. Now that the girls are grown we’ve decided to whip you with your britches down. If you can see them naked, then they can see your naked bottom get the thrashin’ it deserves.”
“Yes Mrs. Jackson,” he replied.
“Well, Ellie Mae. Let’s get this over with. He’s all yours,” Mrs Jackson said as she stepped back. Ellie Mae grabbed Thomas by the ear and pulled him along as she led him to the whipping tree.
“Hands up,” she commanded as she released his ear. He put his wrists together and lifted them high above his head where the tie for his hands had been prepared. Ellie Mae quickly tied the rope around his wrists and pulled it tight. She then positioned herself behind him, and reached around him. She unbuckled his belt, and took his pants down to his ankles. Mrs. Jackson, and her daughters immediately stepped back to make sure they would not see any more of his nakedness than his bare backside. Mary Beth couldn’t resist the temptation to take a quick peak before she joined the other two. Luckily, nobody seemed to notice. Ellie Mae began to lecture her husband.
Mrs. Jackson looked suspiciously at her girls who were smiling sheepishly, trying not be noticed by Ellie Mae. Mary Beth leaned over and whispered to her sister.
“I think I’m gonna enjoy this more than I should!” she said trying not to giggle as Ellie Mae warned Thomas of the trashing that was only moments away.
“Be quiet you!” Victoria snapped under her breath. “If Mama hears you and finds out we’re both gonna get whippins!”
Just then the first crack of the strap sounded. Thomas bucked forward and let out a loud cry. The force of the stroke caught both of the girl’s attention. They each covered their mouths and looked at each other.
Ellie Mae brought the leather across her husbands bottom again, eliciting the same reaction. Then again, and again repeatedly until Thomas’ bottom was covered in red marks, and his howling was the only sound that could be heard. Ellie Mae whipped him in silent anger, methodically bringing down each stroke with all her might. After only a few minutes her husband’s otherwise pale backside was a deep shade of red, and the strap marks had all blended into each other such that they could no longer be seen. The whipping continued for several minutes interrupted only by short breaks for Ellie Mae to catch her breath.
Once the last stroke was given Ellie Mae turned to face Mrs. Jackson as she wiped the sweat from her brow. “Well?” she asked, handing her the strap.
“Ohhh, I think you gave him enough of a whipping for the both of us Ellie Mae. He’s not gonna be able to ride a horse for a few days as it is, and that doesn’t make him of good use to us now does it? Let’s let the girls have their turns and then we will get back to work in the house.”
Ellie Mae stepped toward Victoria, and handed her the strap. Unable to remove the sheepish grin from her face the young lady took it in her hand. She looked down for a second, feeling its weight in her hands. She looked back up at Ellie Mae.
“How many should I give him?” she asked.
“Give him 10, but make them hard. We have a lot of work to do today so we should get it over with quickly.”
Victoria positioned herself to the left of her prisoner, just a few feet behind him.
“Thomas, stick your butt out for me. I’m not used to using the strap.”
Victoria had been on the receiving end of the strap herself before. She knew that as much as it hurt when it whipped across her bottom, it was nothing compared to how it felt when it went across her thighs, or wrapped around her hip.
“Yes ma’am,” he replied as he put his hips back and stuck his bottom out.
Victoria drew the strap back and laid a hard slap across his right side. Thomas hissed, and pedaled his legs.
“Harder Victoria,” said Ellie Mae. “My boy has a real weakness for beautiful women like you and your sister. We’re not gonna put a stop to his behavior by going easy on him.”
She nodded, and drew the strap back further this time. She whipped him with all her might. Thomas jerked and began jumping up and down.
“That’s better,” said Ellie Mae. “Nine more just like that.”
Victoria did as she was instructed and laid nine licks, just as hard, across his bottom. She took her time, letting him react just a little before interrupting his howling, and jumping with the next installment. By the time she was ready to lay down the last stroke, Thomas had broken his position and was no longer bending forward as instructed. She turned toward Ellie Mae.
“Should I give him an extra one for breaking his position?”
“Noooooo, please!” he pleaded.
Ellie Mae nodded in approval.
“Back in position boy. Stick your butt out!” Victoria commanded.
He obeyed and soon after the hardest of all the strokes striped across the lower half of his butt followed by another, equally forceful, across the tops of his thighs. Thomas jumped into the air, and let out a loud cry as Victoria handed the strap back to Ellie Mae.
“I sure hope you’re learning your lesson boy,” Victoria scolded him as she returned to her original position next to her sister.
“Your turn Mary Beth. 10 good licks just like your sister did,” Ellie Mae instructed as she handed the strap off to her.
Mary Beth wasted no time. She positioned herself where her sister had been, drew back the strap and began the last of his whippings. He held his position for the first four or five strokes, but could not resist the temptation to stand, and jump with each stroke after. Mary Beth whipped in quicker succession, giving him little time to recover or reposition himself. The final stroke landed across the tops of his thighs. The boy howled beneath the gust of wind that picked up just as the strap struck him.
Mary Beth handed the leather back to Ellie Mae who approached her husband to check in on his condition. She took a handkerchief from her back pocket and wiped the tears from eyes as she whispered to him.
“I’m sorry we had to do that sweetheart. You know the rules. If you disrespect the Jacksons you get no leniency cause without them we’d be out on or own. Thomas nodded in agreement and muttered softly, “Yes Ellie Mae. I’m sorry.”
“Good boy,” she said. She squatted down and pulled up his britches. She buckled his belt and then turned toward the girls.
“You two are free to go. And Mrs. Jackson, thank you for coming to bear witness. I trust you’ll report to your husband that we dealt with him severely?”
“Of course Ellie Mae,” Mrs. Jackson replied. “Thank you for being thorough. Now girls, I want you to go to the house and back to your chores. We lost some time so make sure you work extra hard to get them done by supper.”
“Yes mother,” the girls replied in unison. They turned and began walking toward the house. Ellie Mae turned toward Mrs. Jackson. “Well, shall we leave my husband to think on his actions?”
“Yes, I think this time we should keep him there for a few hours. We can come in and check on him later. I’ll have the girls bring him some water.”
“I trust what you think is best,” Ellie Mae replied as the two women walked toward the house.
Thomas stayed bound at the whipping tree for a little over an hour before he heard Mary Beth, and Victoria giggling in the distance. As he heard their voices getting closer, he breathed a sigh of relief. Within a couple of minutes the girls reached the tree.
“We brought you some water Thomas,” Mary Beth said as she put the bucket down. Victoria had brought a blanket that she placed on the ground near the water. She dipped a tin cup into the bucket and put it up to his lips. As he drank Mary Beth untied his wrists. He took the cup in his hand and sat down against the tree. The girls joined him in the small patch of grass that surrounded it.
“Sorry we spanked you so hard,” Victoria said. “We didn’t want mama or Ellie Mae to get suspicious.”
“It’s quite alright ladies. How did your mama get to thinking there was something going on in the first place?”
“She saw you come out of the wash room a couple times with your britches sticking out like a tent!” Mary Beth said, giggling along with her sister. “So we told her that you were spying on us!”
“Ahhhh I see,” said Thomas. “Well I guess you would have gotten a woopin’ yourselves if she knew the truth.”
“Exactly,” Victoria said. “And you would’ve gotten whipped just the same, and Ellie Mae would hate us forever!”
“No, I reckon that last part ain’t so. Ellie Mae and I care for each other very much, but our arrangement exists more out of necessity than anything else. She has her needs. I have mine.”
“Well you two sure put on a good show for my Mama, and Daddy,” Victoria observed.
“Gotta do whatcha gotta do little lady,” Thomas replied.
“Well, actually right now…you gotta do what we say. Cause if you don’t we can report back to my Mama and Ellie Mae that you were being ornery.” Victoria teased as she placed her hand on his leg, and inched it upward.
“Ladies…all they have to do is look out the window and see us.”
“Nope,” Victoria replied. “They went for a long walk. They said they have a lot to talk about. I think Mama and Daddy had a big fight or something.”
Victoria reached up to his belt, and began to unbuckle it slowly.
“I’m gonna go cut a switch so we can whip your bottom some more,” Mary Beth said as she stood up and ran off to the next tree.
Victoria continued to unfasten his belt, then his trousers. She pulled them down, exposing his manhood which had swelled nearly to stiffness. She touched the tip of it and noticed that it was wet. She circled her index finger at the tip and smiled in delight.
“You have such a pretty dick Thomas. I’m a sucker for a well-endowed circumcised man. I love how big it gets when I play with it!”
Thomas began to breathe heavily.
“Are you a bad boy Thomas?” she asked him as she giggled. He nodded with a smile. She responded with a sharp flick of her index finger the tip of his dick.
“Owwww!” he cried as he reached to grab her hand. Victoria slapped it away.
“No, no…you’re in punishment right now boy. You’re lucky we took you down off the tree. Don’t make us put you back now.”
She flicked him again and giggled as Mary Beth returned swishing the branch she picked in the air.
“Ok, we should do this now while we still have time,” Victoria said looking up at Mary Beth.
“Agreed,” her sister replied. “You go first, and I’ll do the switching.”
Victoria stood up, and laid out her quilt blanket onto the grass. She lay down on her back and hiked up her dress. Thomas, seeing her bare legs, realized that she was naked underneath. He knew exactly what to do.
He crawled over to Victoria grinning from ear to ear. There was no time to remove his trousers from his ankles or to remove Victoria’s dress. He lifted it and inserted himself inside her. She wrapped her legs around his torso as he began to thrust into her. Mary Beth stood behind and began to whip him softly with the switch. Victoria began nodding, and moaning as she felt his cock pulsing and pushing inside of her. Watching him receive a whipping at the same time only seemed to heighten her enjoyment.
Mary Beth smiled in delight as she whipped Thomas’ tender behind. She began to time the strokes with his thrusts letting him feel the sting of the switch just as he pushed himself into Victoria’s pussy. She felt her own pussy becoming wet as she brought the switch down on her victim’s behind, which was still red from the strappings he received earlier. She knelt on the blanket just behind Thomas and lifted her dress, revealing her silky smooth legs and and a well-trimmed bush between them. She began to touch herself gently as she continued to swing the switch.
Mary Beth increased the pace of her switching, Thomas responded by thrusting faster into her sister. When the switching became harder, Thomas similarly thrusted more aggressively. It was a well practiced routine that the girls had perfected to push each of them to orgasm and to simultaneously keep Thomas from shooting his load too early. Mary Beth was especially skilled at whipping Thomas just hard enough to keep him from coming, but not so severely that he lost his erection.
Victoria’s moans had been getting louder. So much so that she placed her hands over her mouth to muffle the sound. Mary Beth knew exactly what to do next. She began to scold Thomas as she whipped him, punctuating her words with hard whips across his bottom.
“Thomas you are a bad…
Bad…
Boy!” She yelled whipping him forcefully with each word.
Thomas was now moaning from the sting every bit as intensely as Victoria was from pleasure. Mary Beth hadn’t heard Thomas wimper in that way before, and the sound of it overwhelmed her with arousal. She began to finger herself more aggressively while the whips on the boy’s bottom became gentler. She couldn’t help but join in chorus of moaning. She closed her eyes, tilted her head back and made what were now feeble attempts to swing the whip. Now Thomas was thrusting aggressively on his own. Victoria removed her hands from her mouth and began to scream.
“Ohhhh Yesssss!!!!!” She cried out into the still air.
Mary Beth looked back at the house, afraid that someone might hear them. She couldn’t see anyone.
Again Victoria screamed as Thomas thrusted into her with all his strength. Mary Beth ceased with the switch and devoted herself entirely to masturbating while she watched her sister climax. Victoria let out the loudest scream yet as she cried out, “ohhhh Tommy!!”
Thomas stopped moving and watched carefully. He breathed heavily as he felt the lips of her pussy convulse around his cock. He pulled out and laid on the ground next to Victoria as she trembled and squirmed. He looked up at Mary Beth who was still masturbating on her knees.
Their eyes met and she lit up with a smile. “My turn!” She exclaimed as she crawled toward Thomas. She lifted her dress once again and climbed on top of him. The skirt of her dress draped over his body allowing only his face to be seen. She began thrusting on top of him, resting her hands on the blanket. Thomas picked her dress up and watched her as she moved shamelessly on his manhood. Within only a few minutes Mary Beth was making the same noises her sister had only moments before.
Victoria roller over and kissed Thomas passionately. He let go of Mary Beth’s dress and placed his hands at the back of Victoria’s head.
Mary Beth started to thrust more quickly. “Ohhhh Thomas!” She cried. Victoria whispered in his ear as she grabbed onto his hand and guided it beneath her sister’s dress. Mary Beth pulled her dress all the way up until everyone could see her tiny bush being penetrated by Thomas’s cock. Thomas placed his thumb on her clit and began to gently massage in circles. Mary Beth kicked her head back and began to squeal uncontrollably.
“There you go boy. Now you’re getting it!” Victoria said as she watched him pleasure her sister. She kissed his cheek. “I knew those spankings we gave you taught you something after all.”
Thomas didn’t respond. He was too busy working on Mary Beth’s pussy, which he could now feel dripping onto his balls. Mary Beth let out one last fit of screams as she collapsed onto his chest letting her dress drape over his body and her long brown hair over his face. As she lay there Thomas and Victoria stroked her back.
“Mary Beth! I think you just had your first orgasm, didn’t you?” Victoria said sounding pleasantly surprised.
“First one with a man!” She said as she exhaled heavily. Thomas lay still, catching his breath.
“Well good for you. We gotta get this boy put back together.”
Mary Beth pulled herself off of Thomas only to discover that the inside of her dress was dripping with his cum.
“Thomas!! How could you do such a thing!!!” she yelled.
“I’m sorry. It was either the inside of your dress or well…you know…”
“You ruined my dress you dumb boy!”
“I think Mr. Thomas has another spanking in his future once he heals up from the one he got today,” Victoria said with a devilish grin.
“I should say so,” Mary Beth replied.
“I’ll be looking forward to it ladies.” You two better tie me back up though before we all get into a world of trouble.”
“Actually, Mama said we could bring you back to the house. But we should hurry and get that dress off of Mary Beth.”
The three of them hopped to their feet and Thomas put his pants back on. As he buckled his belt they began the long walk along the dirt path back to the main house.
“You know girls, I don’t think that whipping tree is gonna do any of us any good as long as you two devils keep up your mischief.”
“You don’t worry about that Thomas,” Victoria replied. We saved you and Your wife when we took you in. So if Mama wants to whip you, and we want to fuck you, then that’s just the way it’s gotta be.”
Thomas smiled and turned his head. “Yes Ma’am!” He replied.
The girls giggled and responded in unison.
“Good boy.”
A Tender Moon 