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Charley's Shocking Over The Lap Experience

Charley's Total Humiliation By His Mistress
Charley had just given his new hairbrush to his mistress, the sweet Miss Abby. He had been instructed at their last date to get one at Amanda’s Beauty Salon.

Amanda, a friend of Abby’s and quite a spanker herself, had fitted a nice oval shaped mahogany one for Charley’s ass. To fit Charley’s personality as well, it was pink. The mahogany hairbrush was a good fit, as it only took the imprints from two good swats to cover each cheek.

Charley was a bit upset at having to drop his drawers for the fitting, but in between the crisp splats of each stroke, Miss Amanda had explained that that was how naughty boys got the proper sized hairbrush.

Amanda’s ten sharp kisses from four different hairbrushes stung. Laid on top of the two dozen Miss Abby’s practiced hand had given him just a few days before, they set Charley’s ass ablaze.

Charley was happy to escape the chambers of Miss Amanda with such a limited, but still painful, over the lap experience. He couldn’t imagine what twenty-four hot cracks of the hairbrush on his bare ass would feel like. Charley hoped his own sweet Miss Abby was not fixated on that number. He quickly went home with his new hairbrush and soaked his sizzling buns in the tub.

Finally, with the proper hairbrush in a cute pink bag, Charley awaited his next date with his mistress.

When Friday arrived, Charley’s dick was swollen with anticipation. He showered and dressed well, hoping that this time Miss Abby would allow him to fully enjoy her delicious body. He was allowed to eat her pussy last time, but was then sent home with a hard cock and a wet face.

This was after enduring a twenty-four slap, over her knee, hand spanking. The burning sensation in his butt lasted several days and was very humiliating. Not exactly what he expected on his first date with the lovely Miss Abby.

Charley hoped his second date with his mistress would go much better. He arrived with his new pink bag, on time, this time. Being a few minutes late last time was one reason why his pants were lowered and his bare ass was handsomely spanked.

Abby greeted Charley in a super mini skirt, high above her silky black hose and shiny high heels. Her outfit got Charley’s cock so big, he almost hoped she would see it.

Actually she did, and grabbed him by it, as it pushed out his pants. Dragging Charley to her couch, Miss Abby crossed her long legs and pretty much exposed her well-trimmed brown bush.

“Charley, if you ever want to stick this useless cock into me, you must learn some respect. We discussed that last week as you received your first spanking over my lap. Most of my boys get the point after their first spanking; how many do you need?”

“I do respect you mistress. You seem upset.”

“I’m very distressed with you, Charley. You totally embarrassed me with the way you conducted yourself at Amanda’s. When you bring the spanking chair here from the kitchen, I will explain your shortcomings to you.”

Charley knew the chair well. It was the armless one from the kitchen set; wooden and sturdy. It was rock solid, he learned, as he bounced and rolled on it last week.

As his mistress awaited him on the couch, swinging one lovely long leg over her knee, Charley handed her the hairbrush and lowered his pants.

Her lush breasts were free of her bustier and Charley stared at them. Before announcing his spanking for his behavior at Amanda’s, Abby put her full tits into Charley’s face and allowed him to work her up a bit. Once her nipples were hard and her pussy wet, she sent Charley for the chair. Tonight she needed his buns more than his mouth.

As previously instructed, Charley placed the chair in the center of the room, almost tripping over his dragging pants. He stood in position on the right side of the chair as Abby slowly walked over and sat down.

Charley couldn’t take his eyes of his mistress’ long black legs and firm white tits. Was it any wonder why his cock grew so big? Charley only hoped his Sweet Miss Abby would agree and put it to use.

Abby handed him the hairbrush, as she needed both hands to lower his shorts.

Charley, whimpering already, pleaded, “I’m so sorry Mistress, I didn’t know Miss Amanda was your friend. I was barely in the salon and she was yanking at my pants.”

Ignoring his blubbering, Abby slipped her thumbs inside the elastic of Charley shorts and brought them down to his knees. Abby then grabbed the fully erect organ pointing at her face and placed Charley into spanking position.

"You know the rules, Charley. Hold onto the chair legs or the count begins anew. You may cry all you want, as no one is in the building at night."

Abby had specially chosen this loft as her apartment, as the warehouse below emptied at 5:00 P.M.

Feeling Charley’s member stiffen a bit, Abby placed it between her thighs, pointing down. Slipping Charley’s shirt up a bit, her target was right where she wanted it. Charley’s butt still bore the different colors of his two recent spankings. The brightness was starting to fade from Abby’s smartly delivered hand spanking, but the fresh marks from Amanda’s fitting were still clear.

As always, Amanda had selected the perfect hairbrush for Charley’s sorry ass. Abby would not only thank her, but explain that her insolent date had been properly punished for the way he had spoken to her. Naturally, Amanda would be advised, her hairbrush played a prominent role.

“Now listen up, Charley. I will only say this once. My dear friend Amanda was very upset at the way you disrespected her. She was trying to help you and you argued with her. I have already apologized for your boorish behavior and hope she accepts it. If not, you will have to go there and do it in person. I’m sure you’ll have to bring your hairbrush.”

Gliding her hand over the still bruised cheeks lying across her lap, Abby contemplated where to begin tonight’s spanking. Charley, although as dumb as her hairbrush, did have an excellently curved bottom. Abby slowly caressed every inch of it.

Abby called for the new hairbrush and Charley obediently handed it up. Abby agreed with Amanda’s assessment that it would only take two crisp strokes to cover each of Charley’s ass cheeks.

“Count them out, Boy. Loud and clear!”

Charley’s Sweet Abby delivered the first loud crack on Charley’s right butt. A nice red outline appeared.

“Yowee, That was ‘One!’”

“One what, Charley?”

“One, Miss Abby.”

“Very good. Charley, but we have to do that one again. Hope you don’t mind. Keep singing them out. You wouldn’t want me to lose the count, would you?”

The second hot crack blasted Charley’s left cheek. “That was ‘One,’ again, Miss Abby.”


“Don’t talk back, and this one doesn’t count either!” Charley heard before his groan.

The loud cracks continued, as did the count, with the Miss Abby attached. Right and left, up and down. As Amanda had predicted, it only took two oval imprints to cover each of side of Charley’s ass. After four kisses from the new pink hairbrush, Charley’s entire bottom was marked. From now on, Abby knew, the rest were gravy.

And Charley knew it too. Never a new spot to be hit. His Sweet Abby kept hitting one tender spot after another.

Charley’s tortured bottom rolled and twisted. No matter what he did, Abby was right on point. The pain was so intense, Charley never thought about his cock and what was pressing against it. He pleaded and screamed, bucked and danced. But his sweet Abby kept going.


“I will be so good, Sweet Abby, please stop my spanking,” he squeezed out between a bunch of “Owee’s” and “Ouch’s.” “It hurts so much, Miss Abby. I am so sorry.” Charley’s legs kicked as far as his pants would allow.

Charley stopped counting at about fifteen, but Abby didn’t mind. His yelping and yowling did continue though. The show caused pussy juice to run down her legs.

Charley’s last few efforts at counting were unintelligible anyway. He did lift his hand once or twice, but a loud “Hands” and Charley grabbed for the chair legs again. Charley never heard the last few spanks as his brain knew only pain.

Abby smiled down at the bouncing red cheeks dancing on her lap. “The boy is starting to learn,” she thought. "Maybe now he will listen."

Finally, the loud thunder burst ended, but Charley didn’t realize it. The stinging pain would continue for days.

Abby loved the dance Charley put on for her, shaking left and right, up and down. Charley’s ass never stopped moving, nor did he stop singing.

Eventually he realized the loud smacks of the hairbrush had stopped falling. Abby allowed him to lie there until he could breath regularly again. Still, with the fires raging in his butt, Charley looked around and asked his mistress if he could get up.

“Sure, Charley, but why don’t you lie there awhile and rest. Then you may thank me for your lesson.” Abby just loved watching the shimmering spectacle wriggling over her knees.

It took a while, but Charley, without pressing on Abby’s left thigh, lifted himself up and presented himself before his mistress.

Abby made Charley stand there and began her post spanking ritual. Pants still on the floor and hands to his sides, Abby held his limp useless member and looked him in the eye.

“What did we learn today from your new hairbrush, Charley? How have we benefited from today’s spanking?”

“Mistress, I am so sorry I disrespected you and Miss Amanda. Can you ever forgive me? You gave me a very hard spanking, but I know I needed it. Thank you for taking the time with me.” By this time his cock started to stiffen as Abby questioned him.

Abby kept him standing there in his shame. His sniveling would add to his lesson and help him remember what was expected of him. At least, that was the plan. As Charley regained his composure, he tried to step back and reach for his pants.

“Not yet, Boy. We are far from over.”

Still holding his growing penis, Abby used her free hand to slap Charley’s hand reaching for his pants. Abby squeezed the now tumescent member and looked up at him.

Charley was looking down. All he saw were tits and shiny black legs and a very large cock in her hand. With each new question, Abby gave him a gentle squeeze.

“Charley, I am very confused. You’re not a stupid man. Your attitude should have been adjusted after your first bare assed spanking and my allowing you to eat my pussy. You do want to fuck me, and enjoy my body, don’t you? There must be another reason you continue to defy me. What is it? Why are my spankings ineffective? Should I double the strokes, Charley? Do you enjoy having your bare buns spanked over my lap? Should we go down stairs and spank you on the sidewalk? I don’t know what to do for you, Charley.”

“Well, Miss Abby,” he squeezed out between sobs, “I’m sorry I disappointed you and made you take time away from your other duties to spank me. I hope someday soon you will allow me to make love to you. You are so pretty, I think of you every day. Thank you for caring about my training and our relationship. I will try to do better, but I just wasn’t feeling all that well this week. Maybe I have come down with something.”

“Charley, I am very concerned that you may have a physical problem. Maybe we should look into this.”

Taking a very comforting tone with him, Abby finally dropped his very swollen and pulsing cock and asked him to step into the restroom.

“You will find a thermometer there and some Vaseline. Bring them to me.”

Afraid to defy her so shortly after this most recent spanking, Charley, although very confused, did as he was told.

Dragging his pants and feeling his ass burn with each step, Charley came back with both.

“Here Mistress, what are they for?”

“Just get back into position. I’ll check you out.”

“What are you going to do, Miss Abby?”

“There you go again, and right after your spanking. Your problem must be something physical, I know I blasted all the disrespect out of your butt. Just get down here before I forget my concern and get the hairbrush!”

Charley assumed the position and heard Abby fidgeting with something. Next Charley felt his butt cheeks being separated with Abby’s fingers and something being slipped into his asshole.

Whatever it was, Abby pushed it in and twisted it. Then out a bit, and again in and around. It was as if she were looking for the right place.

“Charley, I am taking your temperature. That will be a good indication if you have a physical problem. I am trying to set it right for an accurate read. We don’t want to do it again and again, do we?”

“No, Mistress, once is enough.”

After several minutes of ass fucking him, Abby announced there was a reading of 99 degrees. “Just what I thought Charley, I found the problem. When did you last move your bowels?”

My bowels, Miss Abby?”

Knowing by now not to question her, Charley said it was probably a few days ago.

“Just as I thought. Come with me into the restroom and we will deal with this issue.”

Abby put the thermometer into the sink and the Vaseline on the vanity. Then she looked in the cabinet below.

She came up and handed Charley a shiny black nozzle, about eight inches long with a bulbous head at one end and a round handle at the other.

In her other hand was a large pink rubber enema bag with a long hose running down from the bottom and a hook on top.

If Charley was wide eyed and aghast the first time a spanking was announced, it was nothing to the look on his face now.

“What are you doing, Miss Abby? I don’t want or need an enema.”

“Charley, I thought we have long passed your wants and desires. I know what is best for you. Have all your spankings been in vain? Now you just hold this nozzle while I get your tonic ready.”

Abby then turned to the sink; poured some shampoo and something else from another jar into the enema bag and added warm water until it filled. Hanging the full enema bag on the top of the shower door by its hook, she turned back to Charley.

“Almost ready. Let me just get it lubricated.”

“Please, Miss Abby,” Charley begged her. “I really don’t need an enema. Can’t I just get dressed and leave?”

Becoming stern again, Abby remarked, “Charley, your choice is lubricant or none, that’s all. Haven’t I taught you anything? This should clear up all your problems, don’t you realize that?”

Abby picked up the jar of Vaseline and took the nozzle back. Making a show of fully lubricating the working end of the very long nozzle, Charley watched in utter amazement, as his whole body started trembling. “Don’t you have a smaller nozzle, Miss Abby? This one is way too big.”

Ignoring Charley’s complaint, Abby hooked the nozzle to the end of the pink hose. She left the flow clip in place and ordered Charley to bend over the commode.

All it took was one mention of the hairbrush for him to comply.

“Spread your legs a bit, Charley. It will make this a lot easier.”

Abby used the thumb and forefinger of her left hand and opened his anus, slowly pressing in with the long black nozzle. Charley tightened up and tried to deny her entrance.

“OK, Charley, let’s try it your way. Let go of the commode, stay bent over and spread your cheeks yourself. Show me some pink! Remember, the hairbrush is right here. Maybe you need a few more hot kisses,” but instead ran four fingernails sharply across both red cheeks resulting in a ferocious yowl from down below.

Charley gave off a pitiful, “Yowweee, that really hurt. Oh, Oh, I am so sore, Miss Abby,” and danced a few steps, before grabbing his butt cheeks and spreading them.

Now having two hands to work with, Abby pressed the nozzle assertively against Charley’s puckered butt hole. She twisted it and slowly applied pressure.

“Don’t fight it, Charley, this will make you feel better and might even prevent another unnecessary spanking.”

As he held both of his battered butt cheeks, he felt for the first time how swollen and tender his ass was. Not touching your bottom after a spanking was another big rule Miss Abby had. Charley gave both his burning buns a brief squeeze before performing the ordered separation.

After a few seconds of pressure, his butt hole opened involuntarily and admitted the humiliating intrusion. The well-lubed nozzle slowly entered Charley’s asshole and began disappearing. Abby twisted it and worked it in. She went in and out, working all the curves, always turning and rotating the invading nozzle for a smooth and full insertion.

She told him he could replace his hands on the commode for support. Abby worked the nozzle in very slowly. She went in three inches, then out two, in four and out three, each time searching for the right angle. She reminded her charge of his good decision to go with the lube.

Being a very thorough enema technician as well, Abby took about three minutes to properly insert the nasty end of the enema tube. Abby wanted it deep inside her recalcitrant subject where it would do the most good. Charley probably needed a good cleaning anyway; young men just did not attend to these things.

“Ahhhhh,” was heard from his other end. “Oh, oh, no,” was blurted out with each forced invasion. “Please stop, it is so big.” He couldn’t bring himself to say her name but only kick a leg out forcefully to no avail.

By then, most of the eight inches was gone. Abby gave it a final twist and a slight out and in again motion, before being satisfied with the position of the nozzle. Charley wasn’t so sure, as the offensive foray into his butt hole nearly split him in two. He leaned forward on his toes and emitted a long “Owwweee”, but the long pink hose and nozzle remained in place.

Charley could only imagine how he looked with the long water hose hanging out of his ass. Abby was able to get full insertion. She used the special-wheel like handle affixed to the end of the nozzle thru which the hose went.

Abby simply held the wheel as she twisted and pushed, getting the entire length of the long shiny nozzle deeply set far up his ass. Now that the nozzle was ready, Abby went to the flow clip and released it.

“Here it comes, Charley. Nice and warm and full of soap and something soothing. You’ll feel much better in a few minutes.”

As the warm soapy mixture filled his bowels, Charley started shaking his butt. He tried to expel the huge slippery nozzle but it wasn’t moving. The mixture flowed in regardless of what he did.

Slowly the enema bag emptied and his bowels expanded. If Charley thought he was embarrassed when being spanked, or having his butt examined and penis demeaned, it was nothing to what he felt now.

Soon he heard the gurgling sounds from within his body. He assumed it was the soap doing its job.

Occasionally air from his insides escaped and he was embarrassed by the sounds. How could he ever face his mistress again? When he thought of Miss Abby inserting that long invading instrument up his ass, he wanted to disappear from the face of the earth. He could only imagine how juvenile he looked from the rear.

Miss Abby, with her micro-mini skirt, long black legs and heels, looked anything but juvenile. Those thoughts got his cock jumping again. Then Charley started laughing. Something sticking out front and rear!

“Charley,” using a conciliatory tone again, “even though the bag has emptied, I want you to wait as long as you can before voiding. Give the soap time to dissolve everything.”

Abby even pushed the nozzle in a bit deeper to act as a plug. She heard a grunt from below. Having both hands free now, Abby roamed at will over Charley’s red cheeks and felt the beginnings of the blisters he would have to sit on later. She gave each sizzling bun a good squeeze.

Charley would feel the flames of this spanking for some time and remember it much longer.

Charley responded sharply to Abby’s ministrations. He started a dance indicative of the heat and severe discomfort being re-awakened in his severely spanked and burning bottom. The pink hose, flowing from his red ass cheeks, hung below, greatly adding to his shame.

After what seemed like forever, Abby announced she was going to remove the nozzle. Just as with the induction, Abby removed the nozzle very slowly.

Every time Charley thought it was almost out, Abby slipped it back in and twisted it. Each wet thrust straightened out his cock.

When the entire eight inches had been extricated, Abby placed the nozzle in the shower, washed her hands and reminded Charley to wait as long as he could.

The empty pink enema bag still hung from the shower door as a constant reminder of what was churning in his bowels.

Abby exited the bathroom leaving the door open. In a matter of seconds she saw Charley seat himself on the commode and heard a gushing of escaping water and injected air. It took about three full mini explosions to clean him out. The totally humiliating experience finally being over, Charley could still not get up and face his mistress. He sat there until she called for him.

“Charley, is everything OK? Maybe we should do a clean flush now?”

With that, Charley jumped up and indicated all was fine.

Abby was on the couch when he came out. With her sexy black legs uncrossed, her bush looked Charley right in the face. He had rearranged his clothing but his face was redder than his bottom had ever been.

“Charley, I am glad you told me about this blockage problem. But for it, the training called for another thirty hot ones with the hairbrush next week. Now maybe we can do something else! Don’t you feel better already?”

“Yes, Miss Abby. Thank you again for not sending me home and only spanking me. I do love being with you, even though I am a bit tender when I go home,” he said with a coy smile. “I guess I did need that enema, I was sort of full!”

Abby noticed the protuberance in the front of his pants as he smiled. Giving it a quick squeeze, she told him, “I can see you are feeling better already, Charley. We should do a nice flush like this every few weeks; I’ll mark my calendar.”

Now go back to the bathroom and clean everything up before you go. You can call me in a few days and I’ll tell you if you have to go see Amanda to apologize in person. I think after I tell her you were stuffed up, she’ll excuse your behavior.”

Charley, now horrified that his enema, along with his hairbrush spanking, was to be shared with Amanda, groaned. Never having had an enema before, much less one administered by a scantily clad woman, Charley was unsure of how he felt. Having it discussed with Amanda only added to his embarrassment. At least in the bathroom he could rub his stinging buns.

Abby locked the door after he left, returned to the spanking chair and spread her legs. With her head back, eyes closed, and panties off, her fingers probed for her throbbing little button. Soon she was singing a sweet song of pleasure as she gushed into her warm right hand. When Charley did it, it was nice; this was better!

Rickey Smarts

© 2014

What’s next for Charley? Has he measured up to Abby’s expectations, or will it just be more hairbrush songs to sing.

Will Charley ever bed the lovely Miss Abby? Tune in next time and see.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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