[Part 2] The Catholic Schoolgirl shtick was real [MF] [Long-er]

Thanks for the overwhelming support for my first story. I didn’t think I would be writing a part two this soon if it wasn’t for your words of encouragement. **[Part 1 can be found here](https://redd.it/b3c760)** in case you want a full background

…

After our epic first night together, I saw Chelsea blossom into the world of sexuality untethered. Where she had hidden her deepest desires while with her ex, only letting a little bit of her repression at a time. She was now free to unleash the beast with me every chance she got. The security of having my own place plus my constant encouragement that her sexual desires didn’t repulse me like she believed they would. Every confession, no matter how deprived only got encouragement and joy from me. I respected her wishes to never talk about our bedroom acts outside of the designated safe zones. She saw my effort and trust grew in and out of the bedroom. Our public life was normal and healthy for a budding couple, but years of sneaking and hiding her sexual lifestyle from everyone made it difficult to have anything “normal” in the bedroom. Normal healthy sex was literally a foreign concept to her. How others experienced it and described sex to her, simply didn’t compute. Her subconscious Freudian ‘id’ could only translate these acts to something she was familiar with. What was familiar to her? Shame and humiliation. They had both been a cornerstone of her Catholic upbringing so it’s not that hard to understand how twisting their meaning can have adverse effects. In fact, another verb for ‘twisting’ something, is to ‘pervert’ it. Yup, the wires of her mind had been crossed along ago and it was her brain that perverted out a new way to process the concept of sex. This new way of thinking worked for her.

This is just a glimpse into Chelsea’s upbringing and how she saw things through jaded eyes. The act of sucking a cock was fun and desirable in her eyes because her parents would be outraged if they found out. Watching fetish porn videos was a sin yet she revealed in knowing other sinners out there like her. An act of having a shameful orgasm meant she got to make the parents in her mind feel discomfort and guilt. Sexual spankings were merely redirected desire because shame was her comfort. Every act could be perverted if she felt it was somehow wrong in the eyes of her parents, the church, her teachers. But it was anal sex that was the ultimate act of defiance in her eyes. Why? it was shameful to have sex through a technicality because it didn’t break religious law. She could remain a virgin with her b/f while shamefully being defiled by sodomy. Gentle passionate love making didn’t interest her, for it was not shameful enough. A hard ass pounding where she took carnal pleasure in being degraded, called a slut/anal whore, now that was appealing to her. Because, only sinners full of shame did such a sick and humiliating thing. It was taboo, so it must be something good. It was her One-Ring and she was obsessed with it (double pun intended). Any sex act she could think of where others deemed it wrong was at the forefront of her thoughts. For a sexually repressed teenage maturing into young adult woman, it was on her mind a lot.

In Chelsea’s eyes, mommy and daddy would completely disapprove of her actions and that was ideal. If they knew the things she fantasized about or even did, they would feel shame at how she turned out. Humiliated, because they had failing as parents. Guilty, at their daughter’s outcome for steering her so wrong. She felt all these shames growing up, so the parents in her mind would feel that too. She would crave, desire, do these humiliating sex acts because they held her back all these years. By hell or high water, she was going to love doing them. All of them. There was no other way to think about enjoying any of these things unless “Shame and Humiliation” was present. The more depraved the act, the more she desired to try it.

…

It would be a long time before Chelsea and I, together figured out the root of her obsessions. Where all these extreme fetishes and desires stemmed from. She and I have come a long way since the early days. Neither of us regret how any of it turned out even if the reasoning behind why we did could keep a psychologist in business for decades. We grew to love and trust each other fully in the battlefield of her sexual repression. All the above text is not as bad as it seems. This isn’t a sad tale, we promise. Chelsea and I took full advantage of these early good times and learned from of the bad as well. We made our sexual adventures/misadventures our own and we are stronger as a couple because of it. Both of us remember these early days of our relationship fondly and it’s our pleasure to tell our tale. She’s beside me as I type this paragraph and agrees with me when I say, Trust and Communication is essential for what we had and still have.

We wish you many happy endings if these stories get your motors revved, so Enjoy!

…

Chelsea walked through my front door and greeted my dog Rufus in her customary way. All loves, cuddles and doggy kisses from the both of us. The Judas pooch even preferred her treats from her purse over mine. Bahh! We played with him for a bit, gave him good scritches behind the ears and let him go outside for his nightly rounds around the swamp pool. I could tell she was getting excited for things to come because her hand gestures would become overly animated and calculated. Because we were still outside and in the public view, discretion was in order in how I phrased my wording, “breath babe… It’s almost time”. Her focus solely on the task of watching Rufus sniff the 15th bush and tree to find his spot. She heard every word but didn’t acknowledge them in any way. “Do you need to freshen up first?”, she paused in her attempt to hide her masked excitement and responded by casually shaking her head as if a fly passed by. “Good, take care of the mutt then, while I go inside.” No visual response from her, controlled breaths of self-restraint calmed her growing eagerness. I lowered my tone and spoke in a firm voice that only she could hear, “I expect you to be presentable and in position before I finish up” A louder exhale followed by the faintest of humming came from her throat. She was excited.

I took my time washing up. Put on my tie over the casual button up shirt and straightened it with care. Off went the causal sneakers, on came the fancy-dress ones. I wanted my look to be business presentable. The look of authority had been achieved but the coat was not going on like last time. It only hindered my movement anyway. Chelsea had already put Rufus away in his kennel and her footsteps had long since ceased from the other room. She would be ready and in position for the start of our evening. I gave my reflection another minute or two of prep work, not for myself but to heighten the wait for my girlfriend. Anticipation, the waiting game, the knowing of what was about to happen was all Chelsea would be thinking about at this moment.

I let my shoes click loudly on the floor as I entered my family room. Her anxiety and excitement were pushed to her inner limits. Gone was her need to be in a darkened room to do what we did together. Now, a single soft light from the floor lamp illuminated the room. Chelsea’s bare ass and legs were on full display as her top half was out of sight and bent over the back of my couch. Her pants and panties securely wrapped around her ankles. Shoes remained on like I required. I adjusted my cuffs, gave a non-committal grunt of approval and walked over. I paced with a purpose behind her exposed and vulnerable ass. I revealed in the sight of her gorgeous apple-bottomed posterior before me. “You did as I asked, very good” my was voice neutral, but spoken with authority, “…now why are you in this predicament?” she mumbled something into the couch cushions. “Speak up please” I spoke to the ceiling, enjoying her embarrassed torment. She rose a bit and meekly replied, “because I’m a slut…” heels clicked for another turn and I continued my assessment, “Yes you are, but that’s only part of it, what else?”

Her big ass was perfectly still but not yet clenched in anticipation because this was our roleplay. A few weeks back, she made me watch one of her favorite Schoolgirl spanking videos she bookmarked. I did my due diligence afterward and memorized the lines the Headmaster said, the play-by-play of what took place and melded it with what I knew about Chelsea. The first time we tried acting this out, it got her so excited, she broke character and we stopped everything to talk about why it was so hot and scary to her. But today was a different day. She knew that I was taking her fantasies seriously and with respect towards fulfilling her fantasies. She tried her best to remain in the moment, but occasional squeaks of excitement and the frequent humming were tolerated. I knew not to take my role too seriously, this was all for her after all.

I gave her a few moments to respond but she wasn’t answering, “… what else did you do to deserve this?” I could tell she was thinking hard as this was off script and new dialogue. I helped her along, “…last week you inserted a toy into your… privates,” dawning realization came to her and she played along, she nodded silently in agreement. “… then you were discovered sucking a man’s cock.” Bolder now, she replied, “Yes headmaster”. “…Not just once but, several times” Sheepishly, she exhaled loudly, controlled breaths, a quick hum and then her reply, “Yes Headmaster” I allowed a few moments for her to reel in her excitement. I feigned mock outrage in a tone of disgust “But the most disturbing of all…” letting the moment hang in the air. “You were caught performing acts of ‘sodomy’ with your boyfriend.” The damning word emphasized for her humiliation. She hummed loudly to calm herself down. She was visibly clenching her ass cheeks and appendages to regain control. She answered back in character, “Yes Headmaster”. Staring at the ceiling, knowing my voice reverberated as though I was looking away at her shame, “You were ‘Sodomized’ repeatedly, as if you enjoyed it…” the question had been phrased as a statement. Her humming continued but she replied immediately, “Yes Headmaster,” she continued, much to my surprise “I enjoyed getting my vile and wicked ass sodomized. Please discipline me for my sinful ways.” I acknowledged her bravery. Her admitting this to me openly was still extremely hard for her and I gave her bum a few pats of approval.

Our banter continued for a while more. I wanted to prolong this humiliation for both of our benefit. New dialogue, specific towards her open confessions spilled from her lips. Each moment heightened her lust for what was about to come. She was begging me to spank her now. I prolonged it even more until the time for her to receive her sexual reward/punishment arrived. I positioned myself beside her, hand resting on the small of her back. “You will now receive discipline for the shame you have brought upon yourself, your family and this Headmaster.” The first hard smack with my palm jolted Chelsea into giddy shrieks followed by that familiar hum. Another medium swat followed by another. The rhythm to her spanking was established and she kept her lower half as still as she could, despite the mild pain being inflicted. She had figured out that she could allow herself to moan, grunt, and bring sounds of pleasure to her throat during these sessions. They were meant for her desires after all. This was the foreplay she fantasized so often about, the start of a long erotic filled evening.

Her reddening cheeks emitted a glowing heat to them as my hand spanked her willing ass. Time slowed and at the same time, sped up within the moment. Each smack reverberated off the tile floor and her noises of lust and discomfort melded together. Pleasure and pain were one and Chelsea groaned out the first of her smaller orgasms. The moment her body went ridged, the spankings stopped, and my fingers dove into her dripping pussy. I was her boyfriend now and the roleplaying achieved its purpose. Receiving spankings in a sexual manner was one of many steps in retraining all that sexual repression out for her benefit. Reinforcing that the true shame and humiliation of these acts was in her past, we would turn them around for good.

Fast pumping motions drove my two digits in and out with a purpose. Another orgasm followed shortly after the first and Chelsea’s squirming body was pinned down by my hand and her traitorous anklewear. Each preventing her from moving her body away and legs independently. A familiar groan and ridged body spasm told me her second orgasm of the night was successful. I gently guided my girlfriends’ limp body over the rest of the couch to lie on the cushions. I peered over the back to look down on her smiling face. Her eyes were closed, enjoying that orgasmic ride and sensed I was above her. “I needed that…” she purred. “It was perfect, thank you!” I walked around the couch and kissed her tender lips for a while. Softly, gently.

We talked for a bit, reliving the scene we just played out and discussed what worked and what didn’t. For the most part, I got most of her fantasy just right. I missed her favorite scene with the school girl facing the corner with their pants down to their ankles after they received their paddling. I would have to work that in next time. It was something she had to do often in her past and it was one of the pinnacles of shame to her spankings. Use that bad memory for good, mental box checked for next time.

…

Chelsea’s 3rd bathroom visit was finishing up as I sat in the living room with the TV on to drown out the noise. I heard the shower start and knew it would be a few minutes for a quick rinse. She was accustomed to receiving enemas all throughout her lifetime. She had been giving them to her since she was a kid. That was Mommy’s solution to any aliment her kids faced; the flu, a cold, mild sore throat, a cough that appeared more than twice a day. It could be cured by a lubed nozzle inserted up the butt. Purifying water goes in, the bad stuff came out. ‘Like a confession for the bum’ it was playfully taught. By the time Chelsea was in her early teens, lubed shafts going up her rear, releasing warm liquids inside weren’t that foreign of a concept to her. I still say that it was the seed that got her into enjoying anal sex, but she disagrees. Years later when she would recall how many times, she and her siblings got enemas, I told her something that she never really considered. “You know why your mom was so ready with the enemas right? She did it to herself all the time. Catholics don’t believe in condom’s, right?” I let her mind finish the rest of that thought and her eyes widened in horror at the realization. “Like Mother like Daughter, right?” I got a shriek of dawning realization with a mix of disgust and intrigued surpized of what her parents did. I got a playful beating for that remark. Totally worth it.

The shower stopped and the door opened a few minutes later. Chelsea’s towel wrapped body appeared beside the couch. She gave me a playful flashing and a giggle to complete the mood. Being naked was part of that comfort-of-shame but becoming less so as she was more relaxed around me. The TV turned off and the tone in the room changed in a moment. Hungry eyes met mine and she was ready to continue the evening where we left off. “Blow job or another spanking?” She thought about it long and hard before answering. “Spanking later?” she questioned hopefully. I smiled, “Again? Glutton for punishment I see. Ok, only if you’re good with the blowjob though”

She grabbed the other cushion and placed it at below my seated position. Most of my clothes were removed by this point and I was just in my boxers and undershirt now. She stooped to the floor and got comfortable on her knees. Her hands gripped my legs and she slid her entire body forward into my crotch, all the while looking me straight in the eyes. I loved her enthusiasm in performing this act for my pleasure. She enjoyed watching me build up my own anticipation for what was to come. I lifted my waist up and her fingers pulled at the shorts and deposited them to the floor. Priding herself in not using hands, she licked my shaft like a floppy Popsicle allowing it to rise on its own. When enough of the thick shaft was standing on its own, she engulfed its length into her moist mouth. “That’s right, suck it you slut.” A smile through sealed lips told me she loved the shaming. Hot saliva coated my cock and a warm tongue danced its way around its partner. Nearly choking until she was out of breath, the gasp for air she spewed was music to my ears.

She hungrily devoured my shaft with slow and deliberate motions. Torturing me into doing the very thing she wanted me to do. I complied by grabbing the sides of her head and controlling her bobbing actions. “You like me making you suck, huh?” Up and down I forced her mouth to take my entire length to the back of her throat. Her nose buried in my pubic hair one moment then pulled back enough so that her lips were straining to keep my tip inside without falling free. My groans became louder and Chelsea’s sucking became more deliberate and noisier. Her moans matched mine as my orgasm grew. Grabbing the towel still around her waist, she pulled it up near her mouth to catch the awaiting load about to appear.

Hot cum exploded from my cock and her throat caught most of it as her mouth began collecting its contents. Waiting until every drop was accounted for, she brought the towel up underneath and pulled off so that her lips remained sealed. Opening wide to see my own cum dribble out of her mouth and down her chin. A waterfall of sperm. “Good little slut” I breathed, “…you loved that didn’t you?” She nodded with wide eyes and a toothy cum covered grin.

…

The ass punishment continued with Chelsea now bent over my knee. Smack after smack tanned her big ass and she cooed in pleasurable pain. We discovered that the corner of the foot rest had the best results for bend over the knee spanking. The position was ideal for her to receive the discipline she desired and to fulfill those humiliation fantasies she longed for. She loved these light to medium swats I was giving her over a long period of time. “You’re enjoying this aren’t you?” Cooing, she hissed, “yes.. I’m loving it” Her pussy dripping by the time her rear was completely pink and glowing with heat. “You are depraved, a sinner.” She purred, “I am…hmmmm” In fake disgust, I humiliated her mind even more by timing my swats with each pause “You cum … from … being… fucked… in… the… Ass!”. The last three smacks being the hardest of these warm up sets, “I doooo, uuuhh, I do love it up the butt”

She groaned in the pleasure, but mostly the humiliation from my words. I stopped to apply another healthy coating of baby oil to keep it nice and glistening. I parted her cheeks, making sure to lube up her anus once more because she was going to get it fucked there eventually. She had been craving it all week in her coded texts. The bottle of oil was snapped shut and the flagellation began anew. Covered in a liberal coating of oil, tiny splashes hit my chest, her back and upper thighs. Fresh moans of lust escaped her throat, “ohh, please.. fuck me!” I ignored her pleas and increased the intensity of the hand spanks. She had broken our rule in our spanking session. I sternly replied, “We agreed, 10 full minutes of discipline, it’s been less than 9 minutes.” she whimpered knowing another 2 minutes would be added to the next part of her punishment. The sounds of stinging slaps across her butt and moans of lustful pain filled the remaining minutes left. The timer to her phone went off on cue and her defeated vocalizations pleaded with me. “please…”

I knew her enough by now that her whining was partially an act. She did and didn’t want me to stop. This was our little game and the next part was how she wanted it to end. “Up. You know the drill.” She slowly crawled up and off me to stretch. She rubbed her butt dramatically as she gave me an exaggerated frown. The brat in her surfacing every now and then. “Ehh!” I scolded her for the look, and she changed it to a saddened whimper. “Do you want another 5 minutes added on?” A resounding No parted her lip. By her tone, she meant it. “Ok then, now turn around…” waiting for her to comply, “bend over and grab the back of your legs” She obeyed without question and that told me that she wanted what was coming next. Over the knee spanking was fun, a 10 on her fantasy ‘want’ scale, but this position for the end of the play was her 11.

Chelsea’s large ass was glossy with oil, splattered with pink hand prints. She was humming steadily to herself again, and this was a good sign that her anticipation was ebbing. I comforted her rear by stroking it gently, savoring her humiliation at this position. I slid a finger down her ass crack, she reacted by cooing. I slid the same finger into her cleaned out rear once again for the 3rd time that session and finger fucked her for a few moments. Another oily finger joined in on the fun and Chelsea panted in heat. I pulled them out and quickly followed that action with a hard crack across her left cheek. She yelped in shock but only moved a bit while in place.

“2 Minutes added to the 3 we agreed too.” Another hard crack and another softer yelp. I was giving her the real spanking she desired and fantasied about often. This position; hands on the back of her calves and getting a real hard ass spanking is what she often talked about. The seconds counting down on her timer was her only friend. My hand was numb with pain, but I continued the assault for both our benefit. Her humming mixed with pained gasps as she endured this torture. She could take it and had done so on previous nights, but that didn’t mean it wasn’t hurting her. 3 Minutes down turned to 2 and then 1. The Medium to hard slaps left her pink ass and rising red. 30 seconds to go, now 15 seconds remaining. The final swats where longer apart but the hardest of the night. Each swat made her sway in place from the force and pain. “Owwww!! please!! OUUWWW!!” The last caused her to shriek in pain with the pleasure being clouded in red. The timer sounded off and she collapsed on the couch with her head buried in her arms. The tears were real. Equal parts pain and shame, but mostly it was the emotional journey that were causing them.

I comforted her for a long while as she sobbed herself into gentle coos and sniffles. I soothed her bum with gentle caressing strokes. I kissed her back and sat by her side for a long while. She winced now and then but her body was relaxed and accommodating to my touch.

…

Giving her enough time to rest from her ordeal, I made us some food in the kitchen, and she ate while still laying on the couch ass up. Naked with a fading oily red rear, she was mostly back to herself now. We joked a bit, caught up on the activities of the week (well, since last Wed anyways) and discussed plans for next week. I mentioned how I was getting tired and if she was good for me to take her home. An honest to goodness face of sadness greeted me and she looked disheartened. It was hours before she needed to be back at home. My smirk betrayed my rouse and Chelsea threw a pillow at me. “Ok then, ready for more?” She nodded with smirk. “We will try something new then”. With those words, she was back to being giddy with anticipation.

I had her stand up, position her big ass over my lap and rest her knees up onto the couch. My seated body was in between each of her legs. I then told her to bend her upper body completely over to place her hands on the floor. She hesitantly complied through all of this, not knowing where this was going. Her position was awkward for her, but not entirely uncomfortable. Like a body of sorts. I got a solid view of her under pussy and tenderized bubbled butt. A perfect position for the next part of her anal humiliation experience. I ordered her to stick her ass back towards me. I applied more baby oil to her entire ass and lubed up her anus once more for good measure. I probed her rear once again that evening just to keep it nice and loosened. She cooed with pleasure.

“Now, don’t pull away.” I slid two fingers in deep, wiggled the digits imperceptibly and slowly pulled all the way out. Being as vocal as she was, her mood was always easy to read. I slid into her ass slow and steady and repeated the previous motions. Each rotation took a full agonizing 10 seconds. Probing smoothly, I continued my verbal debasement, “You actually like this don’t you?” She groaned in approval, “You love me penetrating this big ass of yours. What would your father think?” a long groan followed by humming. “Your preacher seeing you like this…” Humming grew louder. “You did an enema on yourself so you could enjoy this even more…” There was no resistance but mild pressure at my probing actions.
“Look at this loose hole, this has been used so much, how is my cock going to feel anything?” On this pull out, I moved to three fingers on the next penetration. A steady moan from her as she rested her upper body weight on her forearms now. Three fingers now completely inside her hot colon, “Even this is still loose. You love getting this ass fucked don’t you.” She groaned, “uuugh! Fucck meeee!!” I gave her a few moments to get used to this new expansion. “More?” she was no longer responding to my questions. Completely lost in the moment. Her ass moving back and forth on its own now. “Do you want more?” “uuUUUGHH!! YESSSS! GAWWWD”. Four thick fingers bunched up and penetrated her slut ass. I applied enough pressure so that she was stretched full, but not in pain. She bucked out a huge scream. Her limbs went rigid with orgasmic bliss. This was a large one by her standards but not the big one of the night. That was about to come in a few moments.

I gave her little time to recover. I gently but unceremoniously rolled her off me and on to the tiled floor. “Up. Get to the bedroom for your reward.” She looked back at me through dazed and glazed expression as her orgasmic high began to fade. Chelsea’s tangled mop of curly strawberry blonde hair swayed, and she shook herself to get awake. I could tell she was exhausted, but this was a little act she did when she had a fantasy fulfilled.

The cock sucking cushion was below her knees and dreamily she sucked me off until I was hard. She was in her fantasy world now knowing what was about to happen. This took place in parallel to the humming when she was happy and content with her shame and humiliation companions. I helped her up and guided her dreamy body to face the bed. She flopped face first automatically spread her legs out wide to reach optimum height. Her ass was hanging over the edge ready to be used and abused. Another helping of baby oil on both her rear entrance and my cock, I slid in with minimal resistance. “This is what you want!” My voice loud and commanding. Chelsea’s mind was deep in her fantasies now, but my words still got through to her when she was like this. Slowly I butt fucked her while pulling both her hips into me. Chelsea was coming out of her dream state and enjoying the moment. Soft moans replaced her coos of pleasure, sounds of lust came out in short breaths. Shame, lust and desire came back to the surface. “Yes” she barked out, “take me! … fuck me!”. My thrusts were long and deep. Pushing to the base and sliding back out to the tip. Her ass cheeks received more hard swats. Her please begging me to go harder and faster. Her oily rear shook as it slammed back into my cock.

Minutes of sliding my dick in and out of her now loosen asshole, her hips pushing back as I trusted forward. Chelsea was deep in her mind until her back arched up on its own. My thrusting intensified and I slammed into her ass with more force. The bedframe itself began to ebb forward from our energy but neither of us realized. Groaning mixed with screams of passion filled her throat. “Cum…. Aaarrrrhh!! Cum in my ass! UUGH!” Pumping with all all intensity I could muster, my orgasm shot through my body, Chelsea’s rigid form locked, a defeated scream of lust escaped her mouth while her flailing appendage’s gripped the sheets in place. She was holding her breath as her body shook involuntarily. Her gasps that followed were loud and dramatic, riding her orgasmic wave for as long as she could. Writhing limbs slowly followed, then turned to subtle motions of caressing the bedsheets.

“That…” large pauses as she took in gulps of air, “was amazing.” Feeling the need to keep things lighthearted, “I know I am…” letting the comment hang. She snickered a playful look of “yeah right!” knowing how good of a night we both just had.

We cuddled for a bit under thick covers and talked about what we did. Living out her fantasies were something she couldn’t get enough of knowing they were coming true. The next time would be some of the same, some things new and a bit more of the fantasy side.

…

Over the next few months, her need to be verbally humiliated in the heat of moment would lose much of its appeal. Relationships grow and mature and this was one area that needed too as well. We would still do many acts that she felt chastised with in her youth, but now they were for fun and pleasure. Role playing became more of a frequent occurrence as new ways to add to her growing fantasies formed from our experiences. I too began to enjoy her fetishes and she enjoyed the slowly growing list of fetishes that I discovered with her. I was bringing her out of her shell while she was bringing me into hers.
Thanks for Reading. Hope you enjoyed it as much as we lived through it.

Source: reddit.com/r/gonewildstories/comments/b4n4ty/part_2_the_catholic_schoolgirl_shtick_was_real_mf