Hi, last week I had the chance to experience one of the best whaletail and wedgie moment ever, all at a work party. Our boss was celebrating his birthday, so on Friday afternoon we went on a little outing, then out to dinner, and finally to a bar.
Of course, our office manager, 45-year-old Jane, was with us too. She’s a very tall blonde with a curvy figure, and she’s extremely cheerful and friendly. She always wears low-rise jeans or pants, but I’ve never seen her in a thong. Sometimes the edge of her underwear peeks out, but it’s always panties. You can often tell by the VPL. So I figured a long time ago that there’d be no whaletail with her.
However, everything changed on Friday. It was around 10 p.m. at the bar, and we were all pretty drunk by then. We were standing at a bar table with some other colleagues and Jane when, all of a sudden, her beer coaster fell to the floor. She immediately bent down to pick it up, causing her white T-shirt and black sweater to ride up slightly, and from her blue high-waisted jeans with a black belt, a full butt crack peeked out, revealing a totally tiny and wedgied black G-string. It lasted only a second, but I stood there in shock. A tiny little black G-string thong digging into her butt-crack. Above the butt crack was a small black triangle from which strings ran around her hips. From that moment on, I knew I had to stay close to Jane throughout the evening and night so I could see that whaletail again.
After about half an hour, a great opportunity arose. We moved over to a table with some empty bar stools along with the group we’d been talking to. I sat down next to Jane, and as soon as she sat down on the bar stool (which had no backrest), her thong peeked out again. Low-rise hipster panties, a butt crack, and a tiny G-string completely wedgied in her ass. After a while, some colleagues who were nearby called me over for something. I got up and went to them, hoping no one would sit in “my” spot next to Jane. Unfortunately, an older female colleague sat down there.
I stayed with the new group of colleagues, and as we made our way around, we ended up right behind the table where Jane was sitting. I had a good view of her whale tail; two female colleagues were standing there with me, and we were chatting. It’s important to note that we were all pretty drunk at the party by then, so the atmosphere was relaxed. Suddenly, the first colleague, about 30 years old, said with a laugh, “Hey, look, is Jane wearing a thong?” The second colleague, around 40 years old, replied with a laugh, “Yeah, woow, her thong is peeking out.” I’ll admit I was afraid of embarrassing myself, so I didn’t say anything and just laughed.
The first coworker said, “I hate this. Why can’t women tuck their underwear in so it doesn’t show? Whenever I see a girl like that, I just want to give her a wedgie.” Suddenly, the best moment happened. The second coworker suddenly walked up to Jane laughing, grabbed her thong, yelped “Weeedgie” in her ear, and yanked on the thong.
I was in shock, my heart racing with excitement. My colleague pulled on her thong, pulling it up to the middle of her back. Jane screamed, “Nooo!”
She started to turn away, but my colleague was quick and pulled the thong even higher, all the way up to her shoulder blades! Jane screamed again, louder this time, “Nooo, that hurts.” She jumped up from the chair; you could see and hear from her movements and voice that it clearly really hurt. Which makes sense—that thin, tight string must have cut into her extremely deeply.
My two coworkers and I started laughing hysterically, as did the people at the table. Poor Jane was red with embarrassment, and she was pulling the exposed G-string off her back with her hand. Then she started laughing too, saying, “Sorry about the whale tail, but now I have to go to the bathroom.”
She went to the bathroom, and the first colleague said, “Well, at first I was glad she got that wedgie, but now I feel bad for her. You really pulled her thongs very high. It must be deep wedgie for her.” The second colleague replied, “Yeah, I didn’t even expect it to go that easily.”
After that, the colleagues started talking about something else with the others. But I was still reeling from the experience.
Jane then came back from the bathroom, and unfortunately, there was no more whale tail. She had obviously carefully tucked her thong under her pants. Not long after that, Jane and a few other people left the party (not because of the wedgie, but because they were obviously going home to their kids). It was one of the best thong experiences I’ve ever had in my life. The work environment, my female colleagues, and an older woman whom I would never have expected to be wearing a skimpy G-string. It was amazing!
