Hello y'all! It's been a bit but I'm back from my New York trip and I followed the advice I was given
I was indeed able to make some pantsings happen, a couple of times on the trip!
A little reminder, I, the girl I'm dating (Allie), and her friend (Jessica), were all staying in the same bedroom in an Airbnb in New York. We had the place to ourselves which was nice, and we're all super comfortable around each other. Allie is tall, really pretty, skinny but with a fatter ass. Jess is shorter and petit, but definitely still cute.
Like I said, we have a really comfortable relationship around each other since we've all been friends for quite some time. I'm not sure how to get pantsing going, but on the first night, we are joking about pranks, truth or dare, usual stuff. Allie is wearing these super old, kinda ratty workout pants, really really low cut almost sagging a bit, and jess and I have a couple times joked about them falling down, so I figure this may be my chance, and Jessica and I had made a joke about pantsing earlier, so when Allie left to use the bathroom, I suggested we should pants her when I get back. There was some back and forth about who should do it, but Allie got back and jess and I both waited for our opportunity. It was a little later when Allie was getting something out of the closet, and brushing her teeth, I saw my opportunity! I got Jessica's attention as a crept behind Allie, and pantsed her! The workout pants were so loose it took barely any effort and much to my surprise, Allie wasn't wearing anything underneath! Bare ass out she yelped, and bent to pull her pants back up while jess and I laughed our asses off. After she got her pants back on she tried to get me (she did succeed just a little haha) but jess got her again when she wasn't paying attention. This time jess only got them off a little so just the top of Allie's ass crack was out. Allie then chased Jess (asscrack still out lol) and tried to get her. I took the opportunity to get Allie again, exposing her ass again and at this point we are all dying laughing. Allie finally did manage to get jess (I think jess was just being fair haha) jess was wearing some pajama bottoms and black bikini panties underneath (boring!) I let Allie get me too just for fairness sake, but pantsing became a reoccurring theme for anytime we were unwinding at the apartment! I got Allie again the next night, and she was wearing a black and white striped thong under her gym shorts, Jess and Allie got me (which was kind of fun because I have a little bit of a thing for humiliation, and I didn't mind two hot girls seeing my ass haha), and Allie got jess that night too. Jess was already wearing just black bikini briefs, and while she was picking out an outfit for tomorrow, Allie grabbed the very bottoms of the panties and gave a fast tug so that the top of Jessica's asscrack was out, Jess quickly corrected but still it was a good site! Maybe I'll try some pantsings now that we are back home too