Whaletail Stories

3 results
Orientation
Length
Source
Infinite Scroll

A Good View

by mkokp on Apr 22, 2025

You are single, and have some free time. You decide to go out and get some fresh air, maybe do some shopping. You are minding your own business when you spot someone really hot. It's been a while since you had a partner, or even sex at this point, so any sexy sights get you interested. You take some time to admire the person surreptitiously, trying not to ge...

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We're Good Friends

by toughpinkpanties on May 15, 2019
First Time

Kayla and I were incredibly close friends in our senior year in high school. I was so hot for her, and she knew it. She dyed her hair different bright colors every month or so, was about 5'4", 105 lbs with a huge ass and A cups. I towered over her at 6'2", and thin as a rail 160 lbs. We would hang out almost every day after class. She was the type of free sp...

Britney Bought Me a Thong

by twiddershins on Sep 14, 2017
Fetish

Subject: Britney. Hair: Dirty Blond Cup: D, pretty sure Age: 19 Location: Backstage Dressing Rooms Britney and some of her friends were standing around me. "Awww... Little Inch Worm." They weren't calling me that, just reading the front of the thong she had just handed to me in front of all of them. But I was expected to wear it throughout the first pe...