How a night of roleplay might send my girlfriend and I to hell! [Mf]

**TL:DR** My girlfriend Chelsea and I rented a Priest and Nun costume and chose to act out a kinky roleplaying fantasy. The two of us defiled each other and acted out every porno fantasy we could think of.

I’ve written many stories about my now wife and I’s adventures before we tied the knot, but this one goes down as one of our most infamous. For starters, my girlfriend Chelsea and I come from religious backgrounds. She was raised by ultra-strict and devout Catholics who attended Mass every Sunday, rain or shine. Because of that, she was very bit the repressed rebellious Catholic schoolgirl stereotype. She went to private school, broke all the rules, got detention, smoked behind the bleachers, basically a hellion daughter. As punishment, she was disciplined by her parents the old-fashioned way. Often having to choose the method of being reprimanded. Meaning; by paddle, spoon, switch or belt. Through her own admission, she had to choose from these quite a lot.

Her parents’ frequent punishments would keep her somewhat in check but had an unintended side effect. While attending college out of state with her new boyfriend, she would soon learn that she loved and thoroughly enjoy spankings when they weren’t from her parents. The more she was exposed to the freedom away from her upbringing, the more she grew to hate authority figures, the Catholic church and everything having to do with anyone telling her what to do. Her entire life was centered around Shame and Guilt for being the sinner that she was. So, it’s not difficult to see how she found power and freedom in twisting shame and guilt in her new-found sexuality by getting off on them. For additional background [[see my other story](https://www.reddit.com/r/gonewildstories/comments/ccb8p2/how_it_almost_ended_withmy_sexually_repressed/)]

Because of all this and more, Chelsea’s entire concept of sex and her sexuality was in short, fucked up. All this frustration, repression and anger manifested in many ways. Usually lashing out at those close to her, but with her boyfriend, it was through sex. She took out her anger by asking to be spanked, through shame based roleplaying sessions and her favorite guilt-ridden pastime; thoroughly being “*violated*” through depraved acts of sodomy. It was her way to get back at her parents, the church and anyone who looked down upon such acts because it felt sinfully good. She had many fetishes she discovered in her adult life, but it was roleplay that related to her inner soul the most.

___

**The Roleplaying Surprise!**

Fast forward to when she’s graduated college, boyfriend broke up with her in a fiery mess, she and I met one fateful evening and now you’re mostly caught up. As timelines go, it’s now 10 months or so into our relationship and things are good for the most part. Sexually speaking, we are now a finely tuned machine where it’s frequent and different enough to keep things interesting. We both are heavily into roleplay and acting out our fantasies. Roleplay is so frequent in our sessions that it’s normal for us to change clothes before we start our evenings bedroom activities just so we can get into character.

So, it came as no surprise to me when I got a coded text from Chelsea saying she has an extra special surprise for me that upcoming roleplay planned weekend. “I’ve got everything for this Sat date night. Including your costume.” She did a poor job of hiding her reserved demeanor through all her excitement. A big part of our relationship together is that we lead two lives. The perfect innocent public persona, while the other is our secret wild and kinky bedroom life. So, her dropping hints left and right that this was going to be an amazing date night was far out of character for her. I couldn’t help it, I got excited through her excitement and she fed off my excitement. By the time Saturday evening came around, the both of us were so horny that neither of us needed foreplay. Just two revved up, crazy sex fiends.

Finally, 4pm arrives and Chelsea pulls up to my house with two garment bags hanging in the back of her seat. She gives me a Cheshire-grin and cackles menacingly as we make the small hike through the side gate and back to my rented pool house home. It’s nestled in a secluded part of the property, complete with overgrown foliage that makes it completely obscured from all the surrounding neighborhood homes. Heavily insulated, almost soundproof while being totally unseen, Chelsea can be as loud as she wants, which is usually pretty loud when orgasming.

We migrate over to the living room where Chelsea can finally show off the contents of the garment bags. She makes me sit on the couch with my eyes closed as she removes the pieces to present them to me in grand fashion. “Ok!” she says excitedly, “Now open!” I do and I’m stunned into shocked silence.

In one hand she is holding a [[Catholic clergy](https://miro.medium.com/max/360/1*7mw8U9qYZSTY8NyhDqHL5Q.jpeg)] robe and in the other, a [[Nun’s outfit](https://i.ebayimg.com/images/g/6-AAAOSw8UtbNO3T/s-l640.jpg)] complete with prayer beads, cross, stockings and shoes. I’m literally speechless as a thousand things are racing through my mind at that exact moment. This has got to be some sort of sin. I know what she wants to do in them, what she wants to roleplay, what she wants to, ehem… “do” in them (in the sacrilegious sense). Chelsea and I share every dark little secret with each other. I figured that it was just fantasy or a fun thought. Looking up at the outfits, I grossly misjudged her desires.

___

**The Priest and the Naughty Nun**

It took a long time, and a couple of whisky tumblers to convince me this was a good idea. But, eventually I caved and we each headed to separate rooms to change. Chelsea was cackling to herself in the bathroom, clearly admiring herself in the outfit. For ease of access sake, both of us agreed to be completely naked under the get-up and the fabric was itchy as hell. Strange things you remember when looking back.

I headed out of my bedroom and lined up the arsenal of tools and toys on the table while getting myself into character. Chelsea was doing the same in the bathroom while freshening up and trying to be her outfits alter-ego. This was our ritual, our routine, procedural method acting for heightening our roleplaying sessions. This was mostly for her benefit, but I would be lying if I didn’t say that I greatly enjoyed acting out these fantasies of hers too.

Chelsea appeared out of my bedroom in the full Nun outfit complete with headdress and hard soul shoes. She was walking in a regal and saintly fashion, hands clasped together in prayer and downcast eyes that kept her face serene and void of expression. I was seated at the far end of my dining room table, back rigid with a face of unemotional stone. I gestured with my whole arm, complete with full hand for her to stand before me a few feet away.

“Sister Chelsea, I must say, I’m most disturbed by what I heard from Headmistress Kathryn.” Keeping my voice firm with authority and a hint of accusatory blame. She nodded with her head; eyes still downcast.

“You were caught repeatedly performing *indecent behavior*.” I paused for dramatic effect. “For that, what do you have to say for yourself.” The both of us roleplayed the Dominant/Submissive roles enough that dialogue was mostly the same every session. So long as my tone made her feel guilty or shameful, and my accusations vague enough that her mind got to fill in the blanks, she was in high heaven so to speak.

“I’m sorry Father, I am a promiscuous woman and I need to be punished.” Her subservient tone acting the part. Hands fidgeting and occasional hums of anticipation escaped her throat.

I proceeded to drone out an imaginary list of infractions she supposedly done. Each more serious or extreme than the previous and all for the intent of heightening her lust for the moment. Chelsea has always gotten off on the shame & guilt aspect of sex. The more I called her roleplayed alter-ego a whore, a slut, seductress and temptress while condoning her for being a sodomy lover, the more she loved it. We went back and forth in our roleplay interchange, negotiating her punishment while in character until it finally concluded.

“…and for that disobedience, you must give me a Hail Mary for every swat with the switch I give you.” Her innocent response wanting more out of the roleplay. “I shall Father, but I fear the switch is not enough.” My stern reply followed, “Very well, 20 from the paddle, a dozen more from the switch. But we haven’t addressed your repeated transgressions with the young parish boy. You allowed him to sodomize you and were caught in the act moaning like a common whore!”

“Yes Father, my urges with the young parish boy have been many. Perhaps another Priestly cleansing with his staff will cast out my wickedness?”

Like I said, we roleplay to get into the mood. Cheesy dialogue works for us.

___

**The Nun gets her Priestly Spanking**

Chelsea is bent over at the waist, arms resting on the back of the couch with her Nun outfit hiked up to her upper back and headdress still on. She’s otherwise naked except for the shoes and black stockings. Her big ass is completely exposed and showing a nice reddish hue as she takes her punishment stoically. She’s cooing in both pain and pleasure with each swat of the paddle. She’s experienced enough to take these in stride and I’m only giving each smack a moderate amount of force behind them. Not enough to cause real pain, but it was close to 15 minutes of this and it was adding up.

My mind is almost completely in roleplay mode but deep down I know how wrong this scene is. I’m wearing a full Priests outfit, paddling my girlfriend’s bare ass who’s dressed as a nun. This is beyond wrong, yet I can’t stop thinking how hot this is. The paddling continues to 20 and I swap tools and start again with the switch. The stinging sensation after a paddling is one of her personal favorites so she’s moaning in between gasps and coos. Each crack with the thin rod brings new reddened marks across her large cheeks and upper thighs. I can hear her mood heightening, breathing ragged with anticipation. I speed up my switching and quickly follow up with guiding her over to my couch’s footrest. It’s the perfect height for over-the-knee-spanking and I help her down across my lap. I give her medium to hard swats, alternating between each cheek for 5 smacks each. Then, sooth and caress it. I repeat the process, speeding up the rest times so that she’s feeling the swats sooner and less recovery.

Within a few minutes, Chelsea is moaning and wailing continuously from both pain and pleasure. She is remaining in character despite the spanking being almost over. “More Father, cleanse me of my wicked ways!” Typically, we stop at this point so we don’t leave lasting marks (and so she can sit down without wincing). But she clearly wants more so I continue with renewed vigor. Within moments, she is crying but not from physical pain. Tears are clearly forming in her eyes, but this is an emotional journey rather than a physical one. I’m giving her hard swats now and she is arching her back up while trying not to squirm.

Suddenly, she gets up off my lap, tears streaming down her face and quickly goes to the table to grab the thick leather strap. It hurts and only used on occasions when she wants to feel it. It makes an extremely loud crack when connecting and its fair to say it’s bark is worse than it’s bite. She heads back over to the arm of the couch, kicks off her shoes and leans completely over it. With her ass now the highest part of her body, she hands me the tool, unable to look me in the eye as I wordlessly accept it. I know she needs this to finish her emotional trip, so I remain in character. Her hands are burying her face in real shame and she arches her butt as high as she can go while in that position.

“10 final swats, for you to be cleansed of this filth!” I start hard. Not giving her a moment to think about what she asked for. The crack is deafening, and she yelps in the folds of her arms. I follow through again slightly harder and she wails in response. Chelsea is sobbing now but arching her butt up for another swat after she momentarily recovers. Crack! Crack! Crack! She’s screaming into the couch cushion but not wanting to stop. I give her three more over the course of a few minutes and her gasps are wet and throaty. Each time she arches her butt seemly higher than before to signal that she’s ok. Her pussy is wet, her cheeks are red with long marks and my mind has fully betrayed me. I’m rock hard at this point and it’s mostly because of how wrong this all is.

The final crack hits the hardest and she collapses into heap, unable to go on any further. I embrace her, kiss her tears and hold her tight. She’s in both emotional pain and physical pain and I’m there to help comfort her.

___

**The Nun gets the Wickedness Sodomized out of her**

After a long recovery, talked about what made or didn’t make that scene for her, she told me everything was perfect and better than she was expecting. I gave her some more whiskey, put some soothing cream over her tender cheeks and followed that up with more whiskey. More toasted than drunk, she’s snuggling up to me making sure she buries her face and headdress into me.

Our normal routine was to roleplay at the start of the evening and call it quits, but Chelsea wanted to continue. I quickly put on the robes again and we bantered back and forth where we left off. You can use your imagination on what we said but the talk was mostly double meaning playful talk, “Ohh Father, I need my mouth cleansed by your holy rod!” Que Priest whipping out his Holy Paenus and she wolfs it down. “Sister, I see a leak coming from between your legs, we need to plug that leak!” Que porno music and standing doggy fuck.

We did this for both of our enjoyment and made groan-worthy sexual puns all evening until our brains couldn’t think of anymore. We fucked in those outfits while standing, cowgirl, bent over the couch, against the wall. Pretty much anything we could think of. Damn straight I made sure she took communion while kneeling on her blowjob cushion. But the highlight of our sexual exploration of that evening was the sodomy chastisement.

It’s no secret that Chelsea loves it up the butt and it’s also no secret that I love giving it to her up the butt. Chelsea is on her second wind at this point and completely ready to pounce me. My mind is well past the “you should feel guilty for this” phase and settled on, “ahh fuck it, going to hell and might as well enjoy the ride!” phase.

Still in what remains of our character, we banter, “We need to cleanse the wickedness out of you through a ritual sodomy cleansing. Are you prepared Sister?” She coos, not hiding her excitement, “Yes Father, please! My wickedness must be cleansed!”

Chelsea is bent over my bed, outfit now completely hiked up to her arms. Her bare ass is well lubed from using my fingers to prepare her. She still has on the headdress and her hands are grasping the bedsheets above her head in a gyrating rhythm of uncontrollable lust. I take my hardened cock and rest it gently at her rear entrance. She groans with anticipation. I refuse to enter her until she begs. She tries to remain in character but can’t quite finish a complete sentence due to how horny she is. I tease and torment her some more until she finally screams out in frustration. She reaches back, pulls apart her cheeks and groans out in shame. “fuck my ass.. please!”. Roleplay has been dropped; we are in b/f mode which means all out fun!

With almost no resistance, I plunge the tip of my cock into her ass. Her fingers pulling apart her cheeks hard enough her knuckles were turning white. I ease in further and she is cooing in pleasure. The tightness and heat engulf my shaft and I’m soon all the way to my hilt. It’s rare my girlfriend is ready for anal right off the bat, usually there is a long and slow process for her to get used to my size. Not this night, she took me into her with each and I felt she was ready within moments. I started to butt fuck her at a medium pace. Long and deep strides, going fully in and out seeing how open she was. Nothing but moans of pure bliss escaped her throat.

Chelsea gasped and sucked in air with each thrust, seemingly unable to match my rhythm because of the pleasure she was in. I couldn’t have been in her more than a few minutes before I felt my urge coming on hard and strong. I grunted out that I was coming close and kicked it up to high gear. She let go of her cheeks, grabbed onto the bed and held on for dear life. I pounded away into her ass and she held her breath like she’d been taught.

I climaxed hard! Fluids rushing deep into her rectal cavity while she neared her climax herself. Finally, she released her breath and exhaled out a continuous orgasmic scream. I shook involuntarily from the level of orgasm I’d just achieved and flopped down on top of the bed beside my nun girlfriend. “Hooly shit!” was all I could say as Chelsea muttered something incoherently in approval.

___

The aftermath of that night was that we agreed we would not wear those religious outfits again. First off, we would never be able to top it. Secondly, we both realized that what we did was beyond wrong and sacrilegious. Even now, we look back at this moment and at the fun, but it’s not something we could ever do again. We were both angry at the Church at the time and this was our way of getting back at them.

Source: reddit.com/r/gonewildstories/comments/d0grcb/how_a_night_of_roleplay_might_send_my_girlfriend