Bitter Goodbyes
As the weeks passed by, Taylor delved deeper and deeper into her feminine persona. She wore makeup and a wig every day, she started using a more feminine voice, and did her best to emulate the behavioral cues of a teenage girl. Sarah even encouraged Taylor to wear panty liners every few weeks to emulate the true feminine experience of a flowering teenage girl, which Taylor gladly did.
But as time went on, the unspoken truth became louder and louder. Eventually the summer was going to end, and Taylor was going to have to return to his parent’s home. They were far more conservative than fun loving Aunt Sarah, and there was no way they’d ever allow Taylor’s new lifestyle to continue. Which meant every ounce of time Taylor and Sarah had remaining together was precious. At last Sarah asked the dreaded question that was on both their minds.
“So, what are you going to do when you go back home?” Sarah asked grimly.
“I don’t really know. Probably not this”. Taylor said, gesturing to herself.
“Are you going to tell them about any of this? About how you feel about yourself?” Sarah asked with a sullen curiosity.
“No, they’d never accept me like this, they barely have time for me as it is, when they’re not busy fighting with each other. I think they’d blow a gasket if I showed up like this. It would just be easier to dress as a boy again”. Taylor said with an exhausted breath.
“Oh baby, I’m sorry. I know life isn’t easy living with them; hell it’s the whole reason they sent you here for the summer. But they’ve been trying to work on their relationship while you were away, maybe things will be better!” Sarah said with an obviously fake enthusiasm.
Sarah’s words of encouragement did nothing to soothe Taylor’s worries. But unfortunately there was nothing the two of them could do. They spent their last few weeks together doing as much as they could to make the most of Taylor’s crossdressing. Photoshoots and fashion shows, slumber parties, mini spa days, all helped to keep their minds off the dreaded deadline which was approaching.
The week before Taylor was scheduled to return home, Sarah brought a box down from her room, and set it on the table in front of Taylor.
“What’s this?” Taylor asked excitedly.
Sarah let out a sigh and said “Well….I know you were planning on going back to dressing as a guy when you returned to your parents…. So I figured it was time to replace the clothes you ruined all that time ago.”
When Taylor opened the box there was a week's worth of boys clothes, replacing the set Tyler had ruined several months ago. Taylor let out a sigh as it finally sank in that she’d be returning to her old life soon. She’d live in a home hot with conflict, and in a body she was no longer comfortable in. At last a tear fell down her face, and as she went to dry it, she was suddenly enveloped in Sarah’s warm embrace. In that embrace she felt safe, and loved; and all at once the tears started flowing.
The trip to the train station was bitter. Tyler came downstairs dressed as a boy, all packed up and ready for the return journey home. Their car ride to the train station was quiet, the air filled with a somber tone. When they pulled up to the drop off curb, both said nothing.
As he got out, Sarah suddenly got out and rushed around the car to give him the tightest hug! Tears streamed from both as their goodbye was finally here.After a brief moment Tyler finally said “Well….thanks for everything", and opened the door to leave.
“You’ll always have a home with me” Sarah whispered into Tyler’s ear as they hugged. “Taylor will always have a home with me”.
At last Sarah kissed him goodbye and returned to her car, waving one last time and pulling away. The emptiness Tyler now felt was palpable. He knew his life would never be the same.
While on the train ride back Tyler went into his backpack to pull out a book and found a pink envelope. He opened it and found three things inside, a letter, one of Taylor’s favorite pairs of pink panties, and a photo of Taylor and Sarah from their prom night.
The letter said:
My dearest Taylor,
I can not express how much fun I’ve had spending these past few months with your new feminine self. I will always cherish the times we spent together, as the best moments of my life. I’ve always wanted a daughter, and you gave me the ability to finally play mother for a little while, as you learned all there was to know about womanhood. You blossomed into a beautiful young woman while you were here, and it truly broke my heart to see you have to return to the melancholy of boyhood. If you want to return to womanhood, my home will always be a safe space for you. Enjoy your senior year of high school, I’ll have you in my thoughts.
Love you always, Sarah
*****
While it was true his parents had seemed to improve their relationship a little, his life at home was a far cry from the luxury comfort of Aunt Sarah’s. They still would on occasion sling an insult or angered glance. The air was tense, and Tyler was walking on eggshells. If all that wasn’t bad enough he longed for his time in a more feminine role.
He wore the panties Sarah gave him often, but it wasn’t much to recapture the magic of his summer with Sarah. On occasion when he was home alone he’d sneak into his mother’s room and try on her clothes. She had nowhere near the huge assortment of clothing that Sarah had, but it helped to fill his feminine itch. But given the intense fear of being discovered by his parents, Tyler kept these moments brief.
His life was dull, school provided little excitement, and when he returned home, he had to confine himself in his room to avoid the tension between his parents. He longed for his fun loving feminine days at Sarah’s. Finally Tyler committed to himself that if ever he had the opportunity to escape these doldrums he would!