This is another older story I wrote a while ago but couldn’t post it for… reasons, and I’ll leave it at that. This story takes place over a long period of time. A [Caught] and [Humiliation] story starting from back when my wife and I were in the early days of dating.
***
Back when I was first dating my sexually repressed Catholic girlfriend Chelsea, my place was the ideal meeting spot for our date nights. She often parked her car around the block, sometimes walking up to a half a mile or more just to hide any notion of where she was going or coming from. She even concocted alibi’s and fake reasons for visiting the neighborhood in case anyone asked or recognized her vehicle. The area was well-to-do so the idea of someone potentially knowing her CEO Father or mother wouldn’t be out of the realm of possibilities.
One day, she had parked her car some distance away per usual. She was getting her day bag of unmentionables from her trunk when the local UPS driver spots her. He shouts out, “Hey Chelsea! Long time no see!” She was completely shocked and out of sorts at being spotted by a former High School classmate. They briefly chat, catch up on the missed years and eventually say their farewells. The only thing memorable about the encounter was she met an old school friend and her rehearsed alibi convinced him that nothing was out of the ordinary.
Months go by and it’s the holiday season. Chelsea is over and we are having one of our many spanking roleplay sessions. I distinctly recall it was one where she was bent over my knee while we were on the living room couch near the front window facing the pool. I’m paddling her big ass, completely focused in the moment when I hear something outside the house. It takes me a few moments to realize the noise isn’t just natures rustling but something moving. I freeze mid-swat when I hear the distinct voice shout, “UPS” as the pool gate shuts and faint footsteps are walking away. As I’ve requested that I get my Amazon packages left at my poolhouse doormat, the box placed at my doorstep was a dead giveaway he had walked past the window. There was now no doubt the delivery guy heard the distinct paddling sounds, followed by the moaning sobs of my girl as my place is not sound proof from that close distance.
The evening took a weird turn where we discussed the events and Chelsea was convinced it was the voice of her former schoolmate. Because there was no way the driver knew it was her inside; the discussion was eventually dropped and the evenings activities resumed.
This is where the story ties together as it’s now May or so the following year. Chelsea is again at my place on a Saturday afternoon and we just finished up a marathon sex session. She was in the mood for some take-out from our favorite restaurant so I go leave to pick it up. I was expected back at any moment and my girl decided to surprise me at the door a-la Nymphomaniac (movie) style. AKA completely naked. My dog starts barking signaling her that I was approaching so she quickly takes off the rest of her clothes and throws open the door to greet me. Only it’s not me. It’s the UPS high school friend who freezes in his tracks mid-step and she quickly closes the door with a shrieking scream.
He chuckles to himself and drops off the package to the door and walks back towards the side gate. At that very moment I’m pulling up to my place and parking the car. The UPS truck is there and the guy is exiting my gate. He gives me this strange smirk but I don’t think much of it as I thank him for delivering the package. I head on through with food in tow.
When I open my door, Chelsea is nowhere to be seen and my dog is happily whining and barking up a storm. I follow him to my room where I find my girl hiding under the covers and I could tell she’s panicking and in full hysteric’s mode. I get her to explain what just happened and she tells the whole story from the original meeting at the trunk of her car, to high school to what just happened moments ago at the door. It’s only then we both piece-together the spanking incident and she freaks out even more.
The reason she is freaking out is that the UPS delivery guy is a fellow Catholic boy so this could end up getting back to her family. Through reason and a clear head, I ask her a series of questions to calm her down and get her to think straight. He barely knows her, has zero ties to her or her family and barely communicated in the same circle of friend she once had. Not only will this not get back to Father, but the guy probably didn’t get a good look at her as it all happened pretty quickly.
Months later and it’s yet another holiday season and I see the same UPS Driver who frequents my route. I’ve chatted with him before and we get to making friendly small talk. He asks, “Is Chelsea your girlfriend?”
I pause, trying desperately to come up with a convincing lie before a long enough time passes and I eventually fess up, “yes, she and I are together”. He has this shit eating grin on his face and gives me a fist bump out of the blue. “Glad you **tamed** that one, she was a wild cat in high school” long emphasis on the word tamed. I knew full well the spanking event he was referring too but I shrugged it off like I didn’t know a thing. But hat was the end of that conversation and he continued on his route with nothing more ever said on the subject. He had that Bro-code honor about him so I knew he wasn’t going to kiss and tell anyone and as far as I know, that still holds true today.
After some time and passed and the moment was right, I told Chelsea during a roleplay session and she about died of embarrassment. You bet your ass I took full advantage of that repressed Catholic shame she held onto and reminded her of just how bad of a girl she was. Ohh how I made her tearfully repent through moans of pleasure over and over with that paddle. Punishing her by making sure her ass was reddened with strap marks and hand prints. I spanked her for almost 30 minutes and she loved every one of them knowing one of her caught fantasies had been fulfilled. We followed it up the evening with some unmarried guilt-shame sex and topped it off by reaming her up the butt just the way she likes.
And to drive home that shame and humiliation she got off on so much, mid butt fucking during round two, I froze during an especially hard thrust and announced, “…I think I hear a package being dropped off!”. God was she pissed, she beat my arm repeatedly because of it. Totally worth it. =)
P.S. She didn’t need to know that I removed Saturday deliveries from my Amazon and USPS preferences months earlier. That unknown fear and thrill of possibly being caught again added that much needed spice she secretly enjoyed. I smiled wickedly each time I sprung that line on her when she was being a brat. It never got old for me.
Source: reddit.com/r/gonewildstories/comments/enr2sb/mf_how_my_repressed_catholic_girlfriend_flashed
Great story! Ah, Catholic girls!
OMG love your stories so much!! So spicy ;)