A Speeding College Boy Pt. 06

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Sheila finishes Derrick's lesson.
1.2k words
4.41
7.3k
8

Part 6 of the 6 part series

Updated 06/09/2023
Created 09/21/2019
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MsCarol
MsCarol
337 Followers

"Alright little Derrick, here it comes, forty strokes on your sorry ass!" chided Sheila. "The last ten will be even more 'special' for you," she intoned, breaking into loud laughter.

CRACK, CRACK, CRACK, SMACK!! The sound of the studded strop biting into his already sore ass echoed throughout the room as Sheila laid on every stroke with all her strength. Derrick, although well gagged, continued to scream in agony. His aunt commented on how well Sheila must be doing considering all the muffled sounds emanating from her nephew.

After thirty blistering strokes, Sheila abruptly stopped. "Well boy were you counting?" she inquired. The only response was some more grunting noise from behind his gag, causing Alicia to start laughing and to comment, "Guess that is a no my dear! Maybe you need to add some extra strokes or start all over!!"

"Oh heavens, dear, I am not sure he could take more! But I will give him some strokes of my riding crop just because I will enjoy it and I think you will as well," Sheila coolly stated. The grin on Alicia's face confirmed her thought!

"Since his ass is so red already and seems to have quite a few deep bruises, I will give him the next ten on the back of his thighs! They certainly need some color," chuckled Sheila. And so pronouncing delivered ten full force strokes across the back of Derrick's thighs, beginning just above the knees and finishing with the last two right where the thighs join his cheeks. Those last couple of strokes really earned some wonderful muffled screams from Derrick as the pain burned deep into his body.

"Oh Sheila, those marks on his thighs look so painful! I am so impressed with how well you can use that nasty strop!" intoned Alicia.

"Thank you dear, but I must admit I really enjoyed dishing those out, my panties are soaked!" replied Sheila. "Now boy I am going to give you the last ten strokes, vertically, right between your ass cheeks!"

"Wow, I bet these will really hurt," his aunt replied while smiling. "I bet he is hoping you don't hit his cock and balls that are so exposed!"

"Well I will try not to hit those, but you know..." chuckled Sheila.

Derrick once again started to lose control of his emotions, fearing that his cock and balls would be struck. As he laid there he also heard his two tormentors, as he was thinking of them, discussing how painful it would be if his private parts did take a stroke or two. His fear was increased as the two ladies both admitted how much they were enjoying Derrick's punishment, adding to his belief that these ladies had some type of history together. But before he could dwell too much on that thought he felt his aunt pulling his ass cheeks apart!

"Here it comes you naughty little boy," exclaimed Sheila, just before the first searing stroke of the studded strop bit deeply between his spread cheeks, with the end of the strop biting right on his asshole!

"What a perfect stroke!" extolled Sheila. "Listen to his muffled scream!"

Encouraged by her very good friend, Sheila let loose with eight more strokes, hitting his asshole nearly every time. "Only one more stroke to endure, little Derrick!" she chided.

Motioning Alicia to move to the side and release his cheeks, Sheila let loose with the final stroke of the strop, aiming lower on the poor boy, and hit pay dirt. The tip of the strop curled below his cheeks and struck him on his well exposed balls! The shock of the pain caused Derrick to scream even more loudly through the gag, much to the delight of the two ladies.

As he continued to shriek through the gag from the immense pain in his ass and balls, Sheila and Alicia embraced in what could only be described as a lust filled deep tongue swapping kiss. As they broke apart after several minutes, they realized that Derrick had finally settled down some and was now only whimpering from the pain they were sure must still be coursing through his body.

"Now for the extra strokes you earned, Derrick, for not counting!" laughed Sheila. Thinking this was hugely unfair as he was gagged and was never told that he had to count, Derrick heard her continue. "Of course I know you think this is very unfair, but I really don't care what you think! If you hadn't earned those demerits so fast, your lovely aunt would not have had to ask me back so soon. So you really have nobody to blame but yourself! So I am going to give you ten smacks with my riding crop...right on your cock, which I see is still somewhat erect!"

As Derrick worried about this new twist, he heard his aunt laughing heartily, surely not a good sign. But then he was surprised as he felt the gag being removed from his mouth and hearing his aunt tell Sheila, "I want to hear his painful sobs as he gets his cock beaten. Since I am naked already I want to masturbate while you punish his cock! I am so horny I need a good orgasm!

"Of course my dear," was Sheila's reply. "I will prolong the ten strokes so you can get off on his pain. Seeing you orgasm at his expense will be a wonderful way to finish this session with him!"

Standing near his feet so she could see his cock which was flat against the end piece of the bench, Alicia started rubbing her clit. Sheila smiled at her, then raised the riding crop and brought it down right on the head of Derrick's cock. They were rewarded with a high pitched scream from his mouth as the pain burned into him. Before allowing him to recover, Sheila delivered the second stroke to the very same spot! Again, another high pitched scream came from Derrick's mouth and Sheila smiled as she noticed Alicia's fingers rubbing faster on her clit.

Realizing she would not have to prolong the cock beating very much for Sheila to reach orgasm, she delivered five quick hits to his battered cock, resulting in even louder screams of agony (and pleasure for Alicia). As Sheila saw Alicia getting closer to her orgasm she felt her own panties getting even wetter. As Alicia started into the throes of her orgasm, Sheila delivered the final three strokes of the crop to poor Derrick's cock. The screams of terror that those strokes brought forth from his mouth only heightened the intensity of Alicia's orgasm.

Gazing at Alicia as she shuddered though the last spasms of her orgasm, Sheila licked her lips as she saw her hand covered with her juices. Finally sated, Alicia and Sheila stood by Derrick's head. Taking her hand, Sheila licked the cum juices from Alicia's fingers, savoring the taste of her pleasure.

"Now if you hadn't been such a disobedient boy, you might have been allowed the pleasure of tasting Alicia's cream! Maybe next time," chided Sheila. "Now you can just stay bound right here while your loving aunt and I have a glass of wine in the living room and think about what you just endured. It would do you well to remember what happens when you foolishly earn those five demerits. I guarantee you next time I have to discipline you I will not be so easy on you! "

Laughing at Derrick's continued sobbing, Sheila took Alicia's hand and they walked out of the room.

MsCarol
MsCarol
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AlonThorAlonThor3 months ago

Fantastic. Hope you add more chapters. Read all of the chapters in this story with a collar on, clover clamps on my nipples connected to the collar plus clothes pegs on my nipples as well and let us not forget a big red butt plug up my ass. No orgasm though as I am in a chastity cage.

maamsboytoymaamsboytoy4 months ago

An excellent story and just what that miscreant deserved! Cheers MsCarol! Well done.

And for all those narrow-minded individuals out there, why om earth are you reading something that you know you will dislike? The story is clearly tagged! Such masochists!

AnonymousAnonymous10 months ago

Suspect MsCarol is really Mr Sad Bastard who wanks himself off to fantasies of being beaten to a pulp by an abusive woman.

AnonymousAnonymousover 1 year ago
Gratuitous shit.

Ridiculous story probably only liked by sadistic morons or feeble submissives.

AnonymousAnonymousover 2 years ago

And the "beat" goes on? I guess not! Ms Carol got tired out?

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