Bre and Sam were a couple of friends out shopping. They had known each other since late middle school but their friendship had truly blossomed midway through college when both of them had gone through messy breakups. Bre's had been dramatic, with her going back to her boyfriend multiple times and Sam offering condolences after each, successively worse, break. Sam should have seen his coming long before it actually happened, but sometimes that is difficult in a long distance relationship. For both of them, when the end finally came, powerful heartbreak ensued. They talked to each other about it online for a long time without either one of them truly getting over their grief. A trip was planned for Sam to visit Bre and for them to go on their first shopping trip together.
They had talked about what they were going to get for a long time beforehand. Bre thought it would be a little bit of fun to get Sam to wear a pair of panties. For his part, it wasn't Sam's first pair of panties, though it was his first since his early teens. He had discovered that it wasn't much fun to do much anything socially unacceptable alone. Bre, as it turned out, was just the catalyst he needed to move his mild interest in wearing women's clothing along. For him, wearing women's clothing wasn't something he felt comfortable with; it was more for the thrill of breaking society's rules, which also got him off. With the introduction of Bre however, the simple act of wearing the clothes became much more fun. Now Sam was to the point where he enjoyed wearing dresses and skirts so he could twirl in them and have them flair out.
On that trip, Sam found himself buying a pink pair of bikinis with little flowers on them and wearing them around New York City the next day. That night they watched movies together and Bre fell asleep in Sam's arms. The next night, while tickling Bre, Sam nearly kissed his friend. Only the moment's hesitation he had before kissing her kept him from doing it. As she slept in his arms that night he couldn't help but think that it would have likely been a mistake.
That weekend was as close as either had ever come to trying to start a relationship. Though Sam occasionally had thoughts about Bre as a potential girlfriend, he had never acted on the occasional slight feelings that he had for her, and he was content with the way things were, most of the time.
Over the next few years Sam and Bre had not only graduated college but had gone on to other things, graduate school for Sam who had just recently graduated, and teaching at an elementary school for Bre. They had also moved on to additional pairs of panties, several pairs of tights, a few leotards, including one that was also a dress, a petticoat, a pair of pettipants, and a square dance dress. Sam had thoroughly enjoyed the square dance dress, as it fit him well and flared out dramatically when he spun. Over that time, Bre had also had several other short lived relationships, one in particular with a man who wore skirts in public. He, on the other hand, had remained single over the years. Their conversations had ranged far beyond the simplicity of wearing women's clothing. One recurrent idea had been started when Bre had said she liked Sam so much she wanted to adopt him. He had responded that she would have to change his age for that to happen and knowing her it would also include a sex change.
On this shopping trip Sam has grown open enough with Bre to do anything from letting her into a department store dressing room to see the dress he was wearing to wearing anything they did buy around her apartment. She frequently encouraged him to be more adventurous, hoping to get him to go outside one day.
They had found themselves at this garage sale largely because of a wrong turn that Sam had taken while trying to get to a mall based on Bre's directions. Sam had wanted to just turn around and keep looking for the mall, but Bre, being more adventurous, had enticed him to stay by telling him that the wife could be his size. They followed the signs to the Dewhurst house, parked, and began to look through the clothes that were out. As it turned out, Susan was a lot shorter than Sam and had few clothes that were all that interesting for his and Bre's purposes. Bre was much closer to Susan's size however, and decided to spend a few minutes looking for something to balance out her fairly conservative yet tastefully trendy wardrobe.
It was Sam who found the medallion. At first of course he didn't realize what it was. Thinking it was a bad piece of costume jewelry, he had actually picked it up thinking that Bre may like it; she did have a love of jewelry that he thought wasn't even worth picking up off the street much less buying. He recognized what it was right after picking it up though. He knew all about the medallion from stories he had read online. When he figured it out he got so excited that he knew he couldn't go up to Susan to buy it, just in case she didn't know what it was but recognized his excitement and decided to haggle. He needed Bre to buy it without knowing what it was. He took the explanation paper out of the box and gave the box to Bre with the money needed when she was ready to leave.
As they drove away, heading toward the mall they had originally set out to find, Sam told Bre what she had just purchased for him.
