Favorite Teacher’s Whaletail

[mastergepetto]

When I was a Senior in high school, we had a half day every Monday for a service project. My service project was at a preschool with a lot of developmentally challenged kids. I loved working with the kids but the best part of the project was one of the female special Ed teachers. Let’s call her Miss Abby, but that is not her real name.

Every week I’d volunteer with the kids, Miss Abby would be there tending to the students. It was a class of about 20 preschoolers and three teachers. Since most kids were around 4, most activities were either on the floor or in small chairs. Every single week Miss Abby would be doing something like reading to the kids in a circle or playing with blocks on the ground and I’d look over and see a massive whaletail. The other teachers frequently wore leggings which hid their underwear better but she always wore jeans that failed to prevent her thong from slipping every time she sat down.

Miss Abby normally didn’t bother to fix it since normally it was just her, two other female teachers, and the preschoolers. However, when I was there, I’d often see her trying to fix her pants or tuck her thong into her jeans. She’d frequently do a little dance every time she stood up to pull her pants back up. It never worked and her thong would always pop right back out within minutes. They were always lace and either blue or pink. One time it was purple with a butterfly on the back. I think she knew how much she was flashing but couldn’t do anything to prevent the show.

Throughout the year I must have seen most of her thongs and rarely saw the same panties twice. However, when I was on Spring break, I couldn’t go anywhere because I played baseball so I spent the week volunteering there during the day before our evening practices. Every day that week, I got unbelievable views of her panties. It was the first time I had managed to see her panties on consecutive days and definitely saw a couple thongs I had seen before.

On Monday—the usual day I volunteered—she wore a navy blue Calvin Klein thong with a white waistband. On Tuesday, when I came into the room, she seemed shocked to see me because I normally didn’t come in on Tuesdays. The other teachers reminded her I was on Spring Break and told her I would be volunteering throughout the week. She seemed oddly embarrassed when she saw me, as she normally greeted me with a hug and a joke. This time, however, she remained on the floor and did an awkward wave.

Then, not two minutes later, I couldn’t believe my eyes when I saw a navy blue thong with a white waistband again; however, this time, the Calvin Klein logo was backwards. She had worn the same thong from yesterday but inside out. I had heard jokes about people doing that but had never actually seen it in real life. Even though it was just a thong, I was extremely turned on knowing she had decided to rewear her underwear from yesterday inside out. I realized this must be why she was embarrassed and wondered how frequently she must do this. The rest of the week she was back to her “normal”pattern of lacy blue and pink thongs.

Normal… Or so I thought. I found out later that week from one of the other teachers that Miss Abby wore the blue and pink lace thongs for me:

“You know she wears those for you, right?” one of the other teachers asked me while Miss Abby was busy lining up the kids for recess.

“Wears what?” I asked, feigning ignorance.

“Those cute cheeky lace panties. She wears them on Monday’s for you. The rest of the week she wears regular granny panties or old thongs so the kids don’t mess up her nice underwear.” She responded.

(The conversation went similar to that but I can’t remember the exact phrasing)

I was surprised and turned on that this teacher in her late 20s would style her underwear choices around when I came and volunteered. I was 18 and she was probably 28 or 29. She was engaged and she knew I had a girlfriend at the time but still wore her favorite panties just for me. I wondered if her fiancé noticed that she wore her nicest thongs every Monday.

I also tried to imagine what granny panties she might wear because I had only known her to wear sexy thongs. I imagined she’d be embarrassed if I saw her cruddy old granny panties.

It didn’t take long to find out, as the next week she wore pink “Fruit of the Loom” granny panties with a scalloped waist band. Definitely not panties you’d want to show off. There was even a slight tear between the waistband and the pink panties on her back right hip. That was the only time I ever saw her not wear a thong.

One week towards the end of the year, one of the kids had an accident while he was in her lap, soaking her pants. These happened frequently and the teachers always had a spare change of clothes. (This is why you’d normally not wear your sexiest thongs to work at a preschool). She went to change into her spare jeans, but they barely fit over her ass. I could tell they were an older pair as the top button was barely hanging on. It was obvious these were her college jeans from the mid 2000s. The waistband of her baby blue lace thong rode up along her entire jeans, even in front. I couldn’t quite tell if she was shaved but I didn’t see any pubic hair underneath the lace.

The other teachers and I teased her about her panties showing and she brushed it off, saying it comes with the job. However, I could tell she was embarrassed by how much she was actually showing. Her blue lace thong even had a small bow on the front. This was the first and only time I actually acknowledged anything about her underwear in front of her and I think she kinda realized how far she’d let things slip. It was definitely not work or socially appropriate.

Still, the next week she greeted me with a hug and a joke and was wearing another cute pink thong.

It was definitely a good year and I still think about her whaletails all the time. One of my favorite fantasies is about the day she had to change her pants. I fantasize that she also had to change out of her piss soaked panties and was forced to go commando underneath her tight jeans. I imagine all the views I would have seen of the top of her crotch. It would be easy to tell whether she shaved or not. Maybe her button and zipper would give way and expose her entire crotch. Unfortunately, that is not how it happened. Perhaps I will write that story in the fictional side of the story board.

[mastergepetto]

This is a very similar image of the whaletails I saw, but she normally wore blue and pink lace thongs, not black.

Unfortunately, this is not her but I did a double take when I saw the image, the resemblance is uncanny. She’d wear the same type of jeans and hoodie, and even had the same blond hair. I had to zoom in on the features of the room to prove to myself this wasn’t her.