This is an older story that I never posted because… reasons. I’ve been in a writer’s slump lately so I figured fuck it, posting it as is. The time-line is a year or soon into our relationship in case you are following my previous posts.
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Quick background and how it ties into this story. Before I met my wife Chelsea, she was the textbook stereotype of the rebellious teenage Catholic school girl. Daddy issues, smoked behind the bleachers in HS and was constantly in trouble with her school and parents. In college, she got herself a steady boyfriend and partook in famous religious loophole of taking it up the butt and giving blowjobs for years to avoid the “true sin” of having sex out of wedlock. Because it was taboo and against the rules, she taught her body that kinky acts were not only pleasurable, but if the sex didn’t involve toys, anal and/or a spanking… she wasn’t interested. Now add the spice of Catholic “shame and guilt” to pervert her eagerness to do these forbidden acts… and this was how I got my gift-wrapped sex machine girlfriend delivered to me.
We start dating and immediately underwent the process of living two distinct lives. The first being our perfect, pristine religious life with button up shirts and never missing a Sunday Mass. But it was our second life that was where we could truly be ourselves. Filled with wild and kinky sex, role playing and usually lots of spanking, anal and or butt play. When we were not together, Chelsea was reading lots of smut novels and occasionally watched porn so she was always in the mood in the early years of our dating life. Our routine consisted of her unloading all her endless fantasies to me throughout the week and when we meet up, we acted out a few that interested the both of us. Roleplay has and still is the consistent factor in most of our sessions together.
After one particular medieval fantasy erotica book, Chelsea had amassed a pillory/stock fetish. For weeks on end she would fantasize about being secured down into one and used in every way imaginable. It was a hot fantasy but I had no stocks, zeri carpentry skills and no “In” with a Renn faire employee. I had to come up with a plan B as she wouldn’t stop talking about it. It’s for this reason that I prepared my MacGyver stocks to eventually make her my own personal medieval slave.
***
Saturday finally arrives and it’s a warm July day when Chelsea arrives on cue. We have an early supper, chat about our week and make our way to the couch with a passionate lover’s kiss. Foreplay consists of a lengthy make-out session, a brief but sexy strip tease (3 items on as it was summer) followed by a detailed conversation of what we plan to do to each other. All the while, she’s oblivious to the window and its modifications directly behind her.
I begin laying out my plan on how to recreate the Stocks scene from her book and she’s completely enthralled at the idea. That is, until I show her the window sill and my intentions to use this as our own pillory. She freezes up with a look of sheer panic on her face. Let me explain, her biggest fear in life is someone she knows finding out about her bedroom life. Even worse if someone finds out about her kinks and sexual preferences. At the same time, one of her biggest fantasies is to have a stranger catching her in the act (preferably a kinky one).
The terror that she is feeling sends her into temporary panic that I eventually calm her down from. Now thinking clearer, she gets up to inspect the pool foam that’s been cut out and secured to the bottom of the up-lifting window. The bottom frame has thick pool towels duct taped in place to make for a cushy guillotine clamp-like device. I order her to peer out the window like the naked Marie Antionette that she was and to see a pair of handcuffs securely fastened from the middle chain-link. I calmly show her the leg spreader bar, the collection of toys/paddles and butt plugs all while her eyes are widening with anticipation. Because the window faces the pool which is completely enclosed by overgrown vegetation and zero visibility beyond it, there is zero risk of anyone spotting her from this precarious position.
It takes surprisingly little coaxing for Chelsea to agree to being pinned by the make-shift window stocks. But on the condition that no hand-cuffs are to be used in case she needs to quickly hide. (spoiler alert, she totally uses them later on). The first few minutes of her pinned in place are an exhilarating mixture of fear and thrill for her as I continue to secure the spreader bar in place and finish preparations. Our roleplaying begins and I take over the role of a medieval Judicator where I proceed to make sultry accusations. I pronounce her as a slut, a Jezebel, and a sodomite. I start with some light (albeit quiet) spanking to get her into the mood, but I found there was no need.
Chelsea was completely wet already and moaning as quietly as she could for me to fuck her. With her bare ass completely at my mercy, I flogged her, fingered her dripping cunt and inserted toys at will. Her first orgasm exploded out of her so hard she had to cover her mouth from the involuntary scream she was letting out. I refused to let up, I fucked her with the toy until her legs were wood-peckering uncontrollably. Practically falling out of the window at the peak of her orgasm, she hit the throw rug hard and shook for a few minutes into giddy fits of laughter. I felt proud for making her cum that hard.
Releasing her from the spreader bar, I carefully brought her over to the couch where it took her 20 minutes or so to fully calm down. It was every bit the fantasy fuck session she hoped it would be and thanked me profusely for making it amazing. We cuddled for a while and gives me a quick pipe-cleaning blowjob so we could prepare for round two.
Some time passes and she quickly rinses off in the shower and appears before me naked and ready for another go at the “Windory” (our new pet name for the window pillory). Now feeling bolder and showing considerably less fear, she readily gets into position but now puts on the handcuffs (stinging hot from the summer sun). The spreader bar securely in place along with the couch’s footrest supporting her on her knees. I spend a few minutes of lubricating her ass with one, then two and eventually three fingers sliding in and out of her frequently used rear. We resume were we left off only with I breaking out the paddle and start in at medium swats while she tried her damnedest to remain silent.
I toy her pussy some more in between spanking sessions then go back to paddling with different instruments. I insert the “preparation” butt plug and flog her back some more and toy with her loosening ass. Still in character, I seized the opportunity and wasn’t gentle with applying as much lube in and around her ass as possible. I heard her give a halfhearted protest while still in character. I got the go-ahead signal out-of-character and positioned myself behind her helpless pinned body. The butt plug is removed with a satisfying moan of protest and my cock slides in with minimal effort. I enthusiastically fuck my girlfriend’s ass like it was the first time and Chelsea is on cloud 9. Her arms pull on the handcuffs and she is squirming with every body part as the restraints on her wrists and ankles clink in protest. I hear her growing groans and sounds of extasy get louder as she nears her ebb.
“UUUUhhhhh fffuuck my asss!!!” comes shouting out from her and panic sets in as I realize just how loud that was. Chelsea peaks and orgasms hard as I shoot my load into her ass and ride the wave that soon follows. She can’t help herself as flamboyant gasps for air escape her mouth.
Within moments, Chelsea has come to her senses and panic starts to set in that the neighbors just heard and might be coming over at any moment. I’m taking my time, slowly walking around her exposed and defiled rear. She is struggling in place but has managed to lift the window with her back and sit up with her arms still restrained from the outside.
I give her a shit eating grin as I let her panic take over for a bit while not saying anything. She realizes I’m not freaking out with her and she comprehends that I know something she doesn’t. “Pleeeease, untie me! They (neighbors) might be here any second…”. I just shake my head. “But I thought you wanted to get caught?”. She knows me too well and sees through my ruse. “…They aren’t at home, are they?”
I just shake my head while continuing to smile. “Saw them leave for Vacation on Friday and landlord is visiting his son 3 states away”.
She smirks and visibly relaxes. “Well then…” she pauses to let reality set in, “Up for a round 3?”
Source: reddit.com/r/gonewildstories/comments/endejd/mf_my_repressed_catholic_girlfriend_and_i
That was awesome
My reliable test reader asked me if we ever used the “Windory” again and the answer is Yes. Several times over the course of that month before I disassembled it due to the amass of bugs that snuck in because the window couldn’t be sealed. It was more fun than a practical addition to our sex life. The pinning process was awkward and left her legs and back sore after a few minutes so the foot rest was basically required for her to use it. Also, I couldn’t be too rough with her as even with the cushioning towels and foam padding, it was hard on her upper body with all the thrusting motions.
The truly memorable moment came when Chelsea became daring enough to try the pillory pinning process from the outside facing in. The ground was lower here so she got to mostly stand while her upper half got to be bent over from the upper half. She first tried it earlier in the afternoon while mostly clothed to see if it would work. But challenged herself to do it again while completely naked before the nights end. It was twilight before got the nerve and strolled outside like she had done this a hundred times even though she was scared shitless. She allowed me to pin her in place and we got to have an awesome round of standing Bondage sex. It was by definition a quickie, not worth writing a whole new story from it but it was freaking amazing none the less. It wasn’t the first time we had sex outside but it was the best to date at that point.
I made sure to reward her for her bravery and encouraged her to do the outside stuff again if she was comfortable with it.
Wow. Lucky man
Subscribed to you a while ago and your stories never fail to entertain. Keep em coming, this was hot!
I love your stories. (As someone who also has married a formerly repressed Catholic girl.)