#20) More Cherry – GRAPHIC CONTENT

I did exactly what I said, I went straight back to my dorm room, stripped off my clothes, and admired my still-slightly-red bottom in the mirror as I masturbated. The spanking and especially the strapping were extremely sexy. That middle-aged Headmaster, someone I’d always thought of as dodgy, now seemed simply mature and so masterful. And his cock felt so sinfully delicious between my butt cheeks, at least for the half-minute until it popped-off. So much cum, all over my bum! I bet the Headmaster hadn’t climaxed since he spanked Charlotte years ago. Charlotte… ummm, I dwelled on her image in my mind as I frigged my erect little clitoris; I wish she were still here at St. Martin’s Academy. I’d LOVE to spank and be spanked by her!
And that’s pretty much how I spent my whole weekend, rubbing out orgasm after orgasm. The Headmaster’s discipline did leave my bottom bruised, which was a turn-on. And I added to it with a lot of self-spanking, dreaming about the Headmaster, his large hand, his stiff cock, Charlotte, her creamy white ass and the cream that comes from our excited pussies… I certainly didn’t get around to studying.
On Monday, I didn’t have to attend that dreadful old Professor William’s class at the end of the day. Instead, I went to the Headmaster’s office and got trained by Miss Evans. Mostly, I did clerical stuff like typing letters and filing papers. Once, I had the file drawer pulled out and the Headmaster needed to pass by behind me. He brushed up against my backside, and I swear, it seemed like he had another erection tenting his trousers!
At dinner that evening in the dorm cafeteria, I could tell that I was the major topic of conversation, especially by that gossip Cherry. Why wasn’t I in class? Was it true I was allowed to do something special for the Headmaster? But no one approached me, so I just sat there like the cat that ate the canary.
So, Tuesday afternoon, just after I arrived smiling and cheery in the Headmaster’s office, Cherry made her appearance. By contrast, she looked mad and scared simultaneously. She had a demerit slip in her hand stating that she’d been talking in class (again), and was, in Professor William’s opinion, in need of further discipline. The Headmaster escorted Cherry into his office. I tried to hang by his closed door, but needn’t have bothered. The Headmaster raised his voice to announce that Cherry was to go stand on the stool and bare her backside while he prepared to give her another spanking.
“What the hell are you doing here?” she whispered furiously as she stood there and folded up her pleated skirt and pulled the green knickers down beneath her curvaceous bum.
“Working!” I smiled. “I don’t need to ask what you’re doing here…” and I patted her bared cheek. I knocked on the Headmaster’s office door. He answered by opening it. “Could I speak to you, please, Sir?”
“I’m very busy, Jean.”
“I know, but it’s important.” He let me in and closed the door. I spoke to him as if he was a peer, a fellow co-ed, not the boss. “I know Cherry. She’s a vile gossip. She’s already been spreading stuff about me, probably about you and me. You need to stop her in her tracks!” The Headmaster looked puzzled, so I connected the dots for him. “Don’t just spank Cherry Smith… Spank her and strap her and cane her deserving plump ass! Send her back to class with the news that any young lady who darkens your door repeatedly for discipline will receive the same strict treatment. Do a good job of punishing this trouble-maker, and you’ll put an end to it. If you don’t nip it in the bud, Cherry will cause more trouble than you can imagine…”
“I think you might be right, Jean. Thank you!”
“I have one more thing to say, a favor to ask…”
I stepped forward into his space. I smiled lasciviously. I reached out and rubbed the turgid protrusion in the Headmaster’s trousers, and asked, “Let me hide behind your desk and watch. I hate Cherry. I want to see her punished hard. I think I can make it worth your while afterward…”
The Headmaster caught my drift. Whipping Cherry’s callipygous bottom would excite us both. I’d be able to “relieve the pressure” when the errant student was dismissed. He put his hand over my hand on his throbbing manhood, and answered, “Hide yourself well and don’t make a sound.”
“Yes, Sir!”
He opened the office door. “Cherry, come in here.”
The dejected girl stepped down off the stool and into his inner sanctum. She looked around for me.
“I dismissed Jean through that door,” he said, nodding his head toward the door at the back of his office. Cherry didn’t know that this was just a closet. He pulled the spanking horse out into the middle of the room. “Over you go, girl,” he ordered.
Cherry assumed the position. From my squatting vantage, I could see a profile of her proffered backside and the Headmaster’s clothed erection. I pulled my knickers out of the way, applied the fingers of my right hand to the familiar duty of playing in my pussy, while the fingers of my left tickled my anus. This was how I usually masturbated. I realized that I was already panting noisily, and tried to quiet my breathing, but my handiwork made this impossible.
“You’ve been sent here two times in two days, young lady. You’re going to receive a sound spanking. But your discipline won’t end there…”
And he began belaboring dear Cherry’s bum. He spanked her very hard, for a very long time. Cherry began crying almost immediately, which was a good thing, because I began climaxing just as rapidly. It was all so fucking delicious! Only when her twin orbs glowed hotly did he stop to step back and survey his achievement.
“Do you think you’ve learned your lesson, Cherry?”
“Yes, Sir! I never been punished so hard!”
“Well, I don’t. We’re just getting started. Boost yourself higher over the horse…”
As Cherry wriggled her jiggling curves over the summit of the horse so that her buttocks were split and displayed obscenely, the Headmaster walked to the desk (where I squatted), opened the bottom drawer, and extracted a thick razor strap. Seeing her fate in his hands, Cherry began to whimper.
“Please, Sir…” she implored.
“I appreciate your good manners, but you can save the ‘please and thank you’s’ until I’ve finished punishing you.” He cracked the leather across the palm of his left hand, stepped into position, and began cracking it across her tush. Cherry yelped with the administration of each hard stroke. The heavy leather made such a loud, lovely sound when it impacted her soft, round rump. I diddled all the more furiously. He set a steady beat with the strap across her bum, like a metronome. Ten minutes later, Cherry sprawled across the horse limply, bathed in sweat, her voice was hoarse from crying out, her backside incandescent. As Cherry became all the more exhausted, the Headmaster seemed to grow all the more invigorated. He, too, was sweating and panting, but he didn’t show any other signs of tiring. And his erection seemed to have a life of its own, throbbing and lurching beneath his now tight-fitting trousers.
He stopped strapping to give them both a breather. “You know, when you first came to me, last Friday, I remember thinking that you had the prettiest pair of buttocks. So round and firm and proud. But I have to say that they are even prettier when bright red and hot to the touch.” He reached out and caressed her flesh. I was suddenly jealous; was he just saying that, or did he really find her phat butt infatuating? Did he like her ass more than mine? The Headmaster interrupted my worries. “If I sent you back to class now, your bottom would cool in the autumn air, and look nearly normal by the time you showed it to your professor. You need a more long-lasting reminder of your time over the horse this afternoon. Something that will proclaim that you got a good lesson…” He strode over to the hat-rack and lifted a curl-handled thin rattan cane off it. He swished it through the air. It made a fearful sound, matched by Cherry’s audible gasp. “You’re going to get six of the best with this,” he announced. “And for this, I think you ought to be nude and bent over in the center of the room.”
Accepting her fate, Cherry dismounted, silently removed her sweat-soaked clothes, and bent her nude form over at the waist. By this time, I was squatting over a puddle of jism, as I’d climaxed too many times to count. And the best was yet to come, six of them! I was mesmerized by what transpired before me. That deliciously dangerous sound of the cane cutting through the air. The incredible THWACK sound as it landed across the poor girl’s well-padded posterior. The way her flesh rippled, contorted as her muscles flexed, then relaxed, as a bright red welt blossomed where the cane had landed.
“Count them,” he demanded.
“One! May I have another?”
It was like a litany, repeated over and over.
THWACK! “Ugh! Two, thank you, may I have another?”
I was near-kneeling in a prayer-like state, instead of fingering a rosary, I diddled my love-button. Cherry’s screams rent the air, along with her careful counting, covering my stifled moans. The Headmaster grunted as he served up every lash, like a tennis champion serving up ace after ace across her big bum.
THWACK! “Six, Sir. Will that be sufficient?”
“Yes, Cherry. You took that very well. You may gather your clothing and get dressed in the hallway. You need not spend any more time on the stool. Go back to class and show Professor William’s and his class your bottom. I hope that’ll be a good lesson for everyone.”
“Yes, Sir, thank you, Sir,” she sniffled.
As soon as she closed the door behind her, I rushed to the Headmaster and he to me. We embraced, kissing passionately. We whispered, knowing that Cherry was still just outside the door, struggling into her clothing.
“That was so fantastic!” I breathed.
“I know,” he enthused under his breath.
“You were so masterful, so sexy!” I continued sotto voce.
“Thank you!” he returned. We heard the heels of Cherry’s shoes make a staccato beat down the hallway.
“I think I came about two thousand times!” I fairly yelled, bending across the horse that was still warm.
“I wanted to!” my lover replied. He released the raging stead from his pants. It leapt forth like a thoroughbred out of a starting gate.
“Fuck me!” I implored. I parted my buttocks for him.
He aligned his horse-sized cock up my crack, pressed the flesh of my buttocks around it and began rogering. I sighed. I wanted to ask who had the prettier set of cheeks, skanky Cherry or me, but decided to wait until later.
Instead I asked, “Do you like hot-dogging me?”
“Passionately!” he panted. “What? Don’t you?”
“I do! I was just thinking how it could be better… We’ve got to keep your big thing away from my pussy; I can’t afford to get pregnant! But…”
“What?” he grunted.
“I just wonder how delicious penetration could be… Do you?”
“Of course!”
“Do you wanna… maybe put that… up my butt-hole…?”
No sooner were the words out of my mouth than the Headmaster was pressing his cock head against my backdoor.
“Whoa, there, cowboy! Do you happen to have any lubricant?”
The Headmaster spit on my rosebud and into his hand, which he rubbed on his cock head. I took him by that hand and led him across the room to behind his desk. My puddle of jism had cooled to luke warm, but it was still as slick as snot. I fingered some up my tooter while he coated his cock with some more.
“That’s better,” I sighed. “Take it slow; that’s a big peg you’re trying to fit into my small hole. That’s it…! God, that’s fucking sweet! Yes! Push it up there… all the way…”
I diddled my abused clit. I climaxed. Apparently, that made me grip his cock in spasms, because he orgasmed right after me. It felt like he was giving me an enema of cum, he filled my bowels with so much ejaculate.
“That was… amazing!” he finally uttered.
I was silent.
“Are you okay?” he solicited. “I didn’t hurt you, did I?”
“No. The butt sex was amazing, just like you said. I just… I think I feel guilty for enjoying something so dirty so much…” As if adding punctuation to what I said, his shrinking cock popped out of my butt-hole, followed by a raspberry of a loud fart. He’d pumped a lot of air up there and it had to come out. I reached back and clasped a hand across my crack. In actuality, I didn’t feel guilty, I just wanted him to think I did, to get what I wanted. That fart just helped me blush like I was actually feeling blue.
“What… what can I do…?” he asked. I tried to keep from smiling at how easy it was to manipulate a man.
“I think… maybe I need a little of the medicine you gave Cherry. I need… a taste of the cane, to punish my nastiness… I just feel so sinful for enjoying the butt fucking so much…”
“Oh… okay…” he said, sounding bewildered but fine with my reasoning.
I pushed him backward until he sat on the edge of the desk and threw myself across his lap.
“Spank me first, warm me up for the cane,” hunger evident in my voice.
He complied. He spanked me just like I like it, with enough umpf behind each swat for me to know I’m getting spanked, just this side of too painful, each blow intense, but not so intense that I couldn’t take it, even as the swats added up and started to really burn, covering the expanse of my expansive buttocks. I rubbed my pudendum against him, feeling my sap start to flow anew, feeling his cock grow hard against my hip. I leapt up when I didn’t think I could take any more without regretting it.
“Thank you, Sir! Do you think two good stripes will answer my needs?” I said as I bent over deeply. Another fart escaped my well-trafficked anus. “Make it three, Sir, for that rude outburst. Please.”
I was scared. I was excited. I feared what was to come. I desperately wanted my backside to be marked. I felt the dreaded rod tap my tush. My buttocks clenched. I reminded myself to relax. The taps were gone. I heard that sound…
Swish, THWACK!
“Yeow!” I stood bolt upright, clutched my wounded cheeks, rubbed furiously, which only intensified the burn. I danced in place, tears coursing down my face. Then I remembered how stoically Cherry had accepted her caning. Maybe she was worn-out and couldn’t fuss any more. Maybe he gave me a harder stripe than Cherry, I thought. But it motivated me to take my medicine. “Thank you, Sir. One. I’m a lascivious butt fuck whore, I enjoyed being nasty. Please, may I have another?” I expected to feel those aim-taking taps, but instead just heard that atrocious whistle.
Swish, THWACK!
The image of Cherry’s big bum rippling beneath the harsh tutelage of this same cane made me take the lash with more grace. With a clenched jaw (and buttocks to match) I enunciated, “Thank you, Sir. Two. I need this whipping. Please give it to me without mercy…” I stuck my ass out for it and tried not to fart.
Swish, THWACK!
The hardest of the lashes cut across that tender crease where butt meets thigh. I stood up and let it propel me into my lover’s arms. I pressed my naked length against him hard. His hands caressed my stripes. I sobbed uncontrollably, then demanded, “Do you like Cherry’s body more than mine?”
Surprised, the Headmaster recovered to answer, “She’s a girl with a baby-fat butt. You’re a woman, with a woman’s appetites.” He kissed me hard.
I felt an erection pressing against me, even though I thought I’d drained his balls with intercourse up my tight tush. “Then fuck me,” I offered nakedly. “Again, not up my ass this time. You wore my poor pooper out for a while. But hot dog my butt. I need you…!”
He did, roughly manhandling my sensitive ass flesh around his cock as he rogered me hard. He came in strong jets of spunk that splattered across my back and dribbled across my bum.
We cuddled as if we were in a satin-sheet-covered bed instead of leaning against his desk. “Did you like fucking me up the butt?” I coyly inquired.
“I hope we’ll do it again, regularly. Did you like caning me?”
“Honestly, yes, very much!”
“We’ll have to do that again regularly, too. I need it.” He smiled. I took his spent cock in my hand. “And I want to practice sucking you off. Will you teach me?”
“Oh, yes,” he stated with sincerity.
“Right now, I think I need to go back to my dorm and take a nap.”
“Sleep tight, beautiful,” he smiled. I kissed him.
But I didn’t take a nap. I took a shower, wrapped my damp nudity in a thick terry-cloth robe, and went down the hall to knock on Cherry’s door.
“Just a minute,” I heard her say. She answered the door still pulling on her robe. She seemed sweaty, as well as slightly out of breath.
“Can I come in?” She closed the door behind me when I was inside. I smelled the distinctive scent of aroused vagina. “Word along the corridor is that you were sent to the Headmaster’s office for gossiping about me in William’s class.” Cherry just stood impassively before me. “They’re also saying that you got a memorable thrashing…”
“What if I did, what’s it to you?” she countered.
I turned around and let my swirling robe hem flash Cherry with a glimpse of my welted bottom. It was fast enough so that she could see vivid red stripes, but brief enough so that I don’t think she could count them. “He called me into his office right after you, saying that he wanted to put an end to our bickering. He spanked and strapped and caned me, too!”
Cherry melt, hugged me like I was suddenly her long-lost sister. “Wasn’t it terrible?”
“It hurt like hell,” I said honestly and hugged her closer. “…At the same time, it made me feel kinda funny inside, kinda sexy…”
“I know!” she returned conspiratorially. I tried to rub some cold cream into the welts and ended up masturbating.
“Me, too!” I confided. We giggled, still hugging. She looked up at me. I had the suspicion that Cherry was a lezzie, so returned her unquestioning gaze, the type of look that only bad stage actors and gays falling in lust give each other. “Would you like me to… continue rubbing cold cream into your bum?”
“That’d be… nice…” she said, shrugging off the robe and lying face down on her bed. I didn’t take off my robe, wanting to keep the severity of my welts secret, but straddled her waist facing backwards, and made sure that Cherry could tell that my naked vagina was rubbing against her spine, and that it was wet. I painted each of her stripes with cold cream, then rubbed it into her large, well-toned cheeks. Cherry moaned. I leaned down and kissed those cheeks softly but repeatedly. She moaned louder. I kissed her into the crevice, frenching her rosebud. I trailed my tongue down the length of her crack, across the pink perineum, and lapped at her labia.
“I’ve never been with a woman… though I fantasize about it constantly… teach me how to lick you…”
“Just do what you think would feel good,” she answered. I did. Apparently, it was correct because Cherry climaxed. I spun around and laid my length against hers. She kissed my glazed mouth, then leaned up to kiss her way down my length, spending a lot of time sucking my nipples, then tonguing my innie navel, and finally really getting into my pussy. Cherry knew what she was doing; I came hard. I pulled my knees up so that my ass was lifted off the mattress. I reached down and tickled my rosebud.
“You don’t mind if I touch myself back here while you do that?” I asked.
“You’re anal-erotic?”
So, Cherry concentrated on my anus with her talented mouth. I wondered if she could taste the Headmaster’s cum, or my jism that we used as lube there. I tried not to think about what else she might taste, just focus on the sublime sensations.
“You’re licking my bum-hole and I’m about to cum from it!” I exclaimed. “God, that feels good!”
“We are naughty, aren’t we?” Cherry asked rhetorically before diving back into my anus. “We ought to be spanked for it…”
“If you’ll spank me, I’ll spank you,” I suggested. “Not like that mean Headmaster does it, but lovingly…”
Cherry smiled conspiratorially, then tongued me energetically.
Now knowing how I was going to spend the evening, I came again in a series of really good orgasms. At least I didn’t fart.
Charlotte had graduated. I wish I’d known her. But I now had a new Charlotte in Cherry, someone I planned to play spanking games with, someone for soft, cuddly sex. I had the Headmaster just where I wanted him, someone who would punish me hard and fuck me harder. St. Martin’s Academy suddenly seemed a whole lot more fun!

Photo published with permission from Asa Jones @ spanking-emporium.co.uk

3 responses to “#20) More Cherry – GRAPHIC CONTENT”

  1. These characters are a great example of ones who continued to speak to me after “The Display Stool” was submitted as a contest entry. So I wrote this continuation, which was published first about a year ago on Mr. Jones’ site. I like this story A LOT; I’m deeply in lust with Cherry (and many of the women pictured on Mr. Jones’ blog)! I hope this tale has the same effect on you; enjoy!


  2. I loved this line:

    “I rubbed my pudendum against him, feeling my sap start to flow anew…”

    My first GF to let me spank her did exactly that in our first spanking fun. Spanking turned her on! And I got to watch her excitement build and build. That’s when I realized – “Oh God; I’m in love with a slut!!!” (Insert big grin here.)

    Never forgot how turned on she got and loved watching her do that during our future spanking fun. Sometimes I’d have her straddle and grind herself into a bolster while I slapped her bottom in encouragement. So much fun to watch women orgasm!

    Thanks for the memory.


    • Thank YOU for taking the time & effort to comment! I, too (obviously), find spanking to be the epitome of sexiness. I’ve encountered Tops who didn’t, didn’t let me “rub-off” during their spankings. Needless to say, things with them didn’t last long. It ought to be FUN, it ought to get both partners off!


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