Truth Story: Kay Oh (M/F) (Patreon)

So this involves my friend who we shall call Kay.  

Kay is a total tomboy, which nothing wrong with that. She is short, has short dirty blonde hair (shaved at the sides longer on top). She is short, a little chubby but not fat. Early 30s and her entire look screams alt lesbain though she is kinda closeted (whole situation to big to get into) She typically wears layers, like jeans and a few shirts. So, never even got a peak at her undies (though there was one occassion where a line of fabric a different color from her undershirt was visible but still not sure) but I knew she was a brief wearer and from a pack cause it just screams her as a person and also confirmed later through talking. 

Now, Kay and I rarely hungout where it was just the two of us but we talked on an off again. She has a lot going on personally. She is also easy to talk to as it feels like she is down for anything and everything to talk about. She is a partaker in herbal suppliments as am I, so we often end up smoking and messaging versus actually hanging out. 

So, starting out mentioned a time where a mutual had given me a wedgie, big one too ripped my undies, which got a response of "boo wedgies" first of many mentions. She also said being friends with our mutual was worth the worst wedgies, which I agreed. She also told me that she'd rather be given a wedgie than talk to a former co-worker. 

This is where we get a bit more fun. She is totally chaotic, in a good way most of the time, so has no issues going down my random talking. She has a complex relationship with her therapist in that her therapist, a woman, is useless and she knows this but she does kind of like her as a person, sort of. These conflicted feelings lead me to throwing out what to do to mess with said therapist. She starts strong with saying she should give her double wet willie. She does really go all in mentioning multiple times that she would wet willie this woman, which was funny. I finally get her to the idea of giving her therapist a wedgie, which gets a laugh and her saying she hopes she doesn't wear expensive undies as she would give her a lot. 

She also joked our mutual would give me a super wedgie if she discovered I stole her as my best friend. We then move on to talking about her crush. She is technically in a relationship with a dude, but he sucks and she developed feelings for a woman she worked with. This is where I start joking I'll bully her into talking to this woman. As we continue to talk goes back to her therapist where she specifically mentions wanting to tie a rope to her undies and hanging her from a tree by them and on a separate occasion giving her a ripping wedgie, mentioning when the waistband is ripped from the undies.

I also played an old favorite game of mine where I guess the person's underwear color. I got it wrong but she gave me the color of grey but I did guess the correct style and brand, Hanes Briefs. Now, here gets us on the road to the actual wedgie as I tell her I'll bully her if she doesn't tell this woman how she feels. She agrees but doesn't.  

Moment of truth.  

We are hanging out with our mutual friend who goes to take a shower leaving us alone. We've also been smoking and Kay brought a very, very strong pen, so my inhibitions are lowered. Now, Kay is wearing a t-shirt and jeans, her normal attire and I start friend bullying her as we sit on the couch. Noogie, indian burn, nothing crazy. Then pretend to go for the wet willie, she does not like that and I could tell she was awkward in this joking friend phase. She gets up to avoid the wet willie, not that I would have actually given her one. She has her back to me and covering her ears, leaving herself wide open. Things are a little fuzzy here as at the time of this writing it was at least a year and a half ago if not two years.  

I reached under her t-shirt and gripped her undies through her undershirt. Like grabbed the fabric of her undershirt and presumably the waistband of her undies aiming at that stop and yanked up. As I did, I got a better grip getting the undershirt out of the way and just getting my hands on her underwear. The two most shocking things here are one, I didn't get the leg holes out and I gave a good yank and two, the Hanes briefs she was wearing were pink. Anyone who knows her would totally not imagine her wearing pink underwear.  

If I had my phone, I would have tried to snap a pic as I gave a one-handed pull but I did not. While she let it happen, she also felt awkward like her brain fried on how to react. I let go, threatened another wet willie before we both sat down and I gave another small tug. I apologized later over messaging saying her strong pen and I maybe went too far bullying. She said all good and we agreed I'd only use my powers of bullying on her therapist in the future. We still talk, though not messaging each other as much. 

I do wish I could give her more, but I did make a vow to save it for her therapist lol.