Whale Tail Stories

I recently began working at a law firm and my managing attorney is super hot, super small, and she’s young (no older than 40). I would always look at her butt trying to see if she wears a thong. And FINALLY, during a deposition while she bent over to show our client something, out popped a nice black lace v string. I tried not to stare with opposing counsel looking at me and she might have felt it coming out bc she came back and pulled her shirt down so fast. But I’ll definitely be on the lookout more now that I know she wears thongs 😋


Well-known member
Just a quick story; but a couple days ago we went to another kids birthday party party at an arcade. My wife was wearing some low rise True Religion jeans that are really low and they lace up in the front, there’s no zipper or buttons. So as she was walking around and bending throughout the day they would loosen up a little and her bright blue Puma thong would show. A couple of the other guys there were catching on and staring when it popped out.

Caught a pic before we left



Active member
This is an older story, over seven years ago, but one that will be forever etched in my mind.

For those of you who haven’t seen my only started thread here, of my older sister, let’s just say that I’ve been attracted to her since I first remember seeing her thong slip back when she was just a teenie.

Back in her prime attractiveness days, she was a fit, athletic brunette with a sexy ass and plump boobs for her size. This was over a decade ago, and right in the middle of the whaletail fad. But this story isn’t about her thong slips, but about another erotic moment that I had the courage to pull off.

Fast forward a couple years after I graduated high school, during the summer, when I was on break and living back at home until traveling back to college.

My sister, two years older than me, also was living at home with the parents. We had a pretty big, two story house, although with a couple other siblings, and lots of storage, there wasn’t enough bedrooms for everyone to have their own. And since I was just back for the summer, I, along with my sis, were the ones left without a bedroom.

In our upstairs, she had moved her bed and dresser and a bunch of her other stuff, sort of like a bedroom but in a big living room type area. Also in the living room was a pull out couch bed, which I slept on all summer, probably just 20 or so feet away from her bed.

Right off the bat, this sleeping situation drove me absolute crazy. She would watch movies on her tablet, talk on the phone, and just straight up be noisy late into the night while I was trying to get good sleep for my summer job. More often than not I would be up way later than I hoped and wouldn’t get very good sleep thanks to her, and there’s nothing I hate more than being bugged while trying to sleep.

I dealt with it though, not knowing at the time how lucky I was to be in this situation.

Another thing I forgot to mention about our upstairs area, is that there is no air conditioning and it gets unpleasantly hot in the summer time.

About a month or so after putting up with her and not getting great sleep, I was out late partying at my friends down the road. She also was out at the bars downtown, and she had a bit of a reputation as being a party girl who sometimes drank a little more than she could handle.

This particular night, I had a bit to drink and was feeling great, and around 1-2 in the morning started walking back home. But, both our front and back doors were locked and I was without a key. Not wanting to wake the whole house up, I called my sis and was relieved when she answered.

“Good, she’s home,” I thought while waiting, thinking she must have been dropped off at home not too long ago by the douche bag group of boys she hangs out with.

I waited by our door, and although it was dark inside the house, my eyes widened when she opened the door for me. She wore just a grey towel wrapped around her 23-year old body.

I said something along the lines of “thanks for hurrying” or some smart ass reply and she just mumbled back to me.

She immediately took off back upstairs, and I quietly followed and caught a glimpse under her towel at the bottom of her ass cheeks, as she reached the top stair and went to her bed. Seeing that got me rock hard, and also got me thinking about what she had on underneath the towel.

But ... I didn’t think much of it, went and got something to eat in the kitchen, and made my way up to bed about 20 minutes later.

I was still slightly drunk, it was really late, and I had to be up for work in the morning, so I needed to get a good nights sleep. She had a movie playing on her tablet, but I just rolled over and tried to fall asleep ... but couldn’t. The stupid sound was just way too loud for me to fall asleep.

I quietly blurted our her name ... nothing. I said it again slightly louder ... again nothing.

So I rolled my ass out of bed, stood up, and walked over so I could turn her stupid movie off and get to sleep. I turned her tablet off, but while doing so, realized that she was completely passed out.

I felt a tingle in my stomach, as I realized the golden opportunity that awaited me.

She slept on her side, her entire body covered by a thick, goose down blanket, with just her head peeking out of the blanket.

Feeling slightly confident and wondering again what kind of panties, if any, she might be wearing, I knew what I had to do.

Ever so gently with the tips of my fingers, I pulled the thick blanket off her warm body, inch by inch.

Peeling the blanket off her took ages, mostly because of my caution and thinking about what would happen had she woken up. But she didn’t.

What was just her cute face poking out of the blanket, now was her bare shoulders as I realized she wasn’t wearing a bra or any type of shirt. My cock got hard and I got excited, wanting to continue to see the rest of her body.

I kept slightly pulling at the blanket, seeing her bare arms curled up and covering her boobs, her chest, and finally pulling the blanket far enough down to reveal the bottom half of her body.

It was a mild disappointment to me, realizing then that she had just a regular, bikini type panty on, and no thong. However, the white panties with pictures of mini coke bottles everywhere, was super tight and wedged deeply into her ass.

Her entire body was now visible and the blanked pulled aside, as I stood and gazed at her. She looked so hot, lying on her side with her entire ass visible, and parts of her boobs also exposed, although her arms slightly covered them.

I pulled out my old smartphone, which didn’t take the best pictures, turned on the lights, and went to work.

I captured about half a dozen pics of her full body, her ass, and her boobs, and immediately went downstairs and jerked off in the bathroom.

I finally had nude pics of her! I had seen some of her before from her phone, but having these pictures was just more special.

Before I went to sleep, I logged Into the old whaletail site and posted the pics to a threat called “sleeping ass in panties.”

Not only do I have nudes of her, now all the people on this site will see her sexy, naked body!

But that night wasn’t the only chance I had to creep on her sleeping!

A week or two later, past midnight, I was at home, having to work the next day, but waiting up for my sister to return home from the bars.

Hours later it seemed, I finally heard the door open, and somebody stumble around before heading up the stairs and into bed. I was sleeping downstairs at the time to remain cool, and waited about 20 minutes before creeping quietly up the stairs.

Same situation as before, she had her whole body covered by a blanket except her pretty face.

I did the same as I did before, gently peeing the covers off her body, only this time to reveal a sexy, Victoria’s Secret leopard print bikini panty, which was too small and wedged deeply into her ass.

Leopard print is a huge turn on for me, so my cock got instantly rock hard after seeing her ass eating them up.

Another thing, was that she had fresh bruises up and down her legs. Could those have been from that same night? Could the group of guys she hangs out with had their way with her before dropping her off at home? Was she ra ped? Did she get gangbanged? I can’t believe that she would have been able to consent because she was completely out by the time I stripped her.

This time I had a better camera and got a dozen pictures to study each and every inch of her exposed body.

The leopard panties wedged in her ass, the fresh bruises on her legs, and her tits slightly exposed made for a great batch of pictures.

They too, were instantly posted on the old whaletail site.

The pictures were posted there and deleted from my phone and the camera. I thought the pics would be safe, but they were lost forever when the old site went down.

Let me know what to guys think of this story! Hopefully it wasn’t too long.


New member
Few months ago I had to help move in a friend to a new apartment. She’s 20 and has an athletic build. She was wearing a sweater low cut with jeans that were just way too lose. The entire time her VS thong strap was sticking out. She kept trying to hide it by pulling up her pants but right after her red laced thong kept sticking out. Towards the end of the day I couldn’t help myself and I gave her a wedgie.Also managed to steal a thong or two.