My Summer With Aunt Sarah Chapter 10

The Finale

Tyler’s dull life marched onward. His senior year of high school was uneventful and provided little excitement to look forward to. Tyler’s parents had obviously fallen out of love, and now held their marriage together out of spite. Everyday blurred together as he confined himself to his room, reading, playing video games, and his time with Sarah ever on his mind.

He texted with Sarah quite frequently when they first separated at the start of the school year. But now they only texted once every few weeks at the most, sending pictures of cute outfits or funny memes to each other. They were nowhere near as close as they’d once been. As the year went on Tyler realized his relationship with his beloved aunt was unfortunately slipping away.

As his senior year of high school was coming to an end, Tyler was facing a crossroads in his life. He was already enrolled in an online college for video game design next year, but now he’d have far more free time to spend his life as he pleases. All the plans he was beginning to make for his life were halted shortly after his 18th birthday however; his parents were getting a divorce. They waited until after Tyler turned 18 to avoid a legal battle over custody and child support. 

Tyler’s parents were also going to be selling their home, and moving into separate apartments after Tyler graduated High School. Since neither of his parents had particularly strong parental instincts, they left it up to Tyler if he wanted to move in with either of them, or strike off on his own. He’d initially planned to live with his father since he was footing the bill for Tyler’s college. However one morning when he reached for the pair of panties his aunt had given him it all clicked. This was his chance to return to Sarah!

Both of his parents at separate times floated the idea of Tyler getting his own apartment during college, so he knew that they’d be ok with him not living with either of them. All he needed to do was reach out to Sarah and ask the big question. But how to ask, they had become so distant, it seemed like an impossible request to fully move in with Sarah after so long apart.

Well after fixating on the idea for weeks, he finally bucked up the courage to ask. He spent hours drafting the text asking to move in with her, and after a while longer of nervous anticipation he sent it. He eagerly awaited a response and could hardly focus on anything until at last his phone vibrated with a text from his aunt. It said only a single word, but it made Tyler’s heart skip a beat.

Yes.

His heart was racing, his dreams coming true! After a year of agony he was going to return to Sarah and the magic of her house of feminine dreams. Neither of his parents seemed to mind the idea when he told them he would be living with Sarah, probably he'd finally be off their plate. But his parent’s indifference didn’t matter any more, he was going to a home where he felt love.

After graduation day the time had finally come. He packed his bags, swiftly said his goodbyes and left for the train station. He couldn’t sit still on his journey; he was so excited! After a long taxi ride he finally arrived at Sarah’s beautiful home. Tyler swiftly collected his things and practically ran to the front door. After a ring to the door bell, there she was, his beautiful Aunt Sarah. She flung her arms open and hugged him tighter than ever before. 

At last she kissed him on both cheeks and held him at arms length, saying “welcome home Taylor”.

Sarah then sent Taylor up to her room to see a “little surprise” Sarah had set up for her. When Taylor opened the door to her room, her jaw dropped. The whole room had been redone! The walls were painted light pink, there was a canopy over the bed, a huge lighted vanity with a massive makeup collection, and sparkling string lights creating magical mood lighting. As if the shock of the room wasn’t bad enough when she opened the closet her mind was blown once again. It was almost completely full of clothes, some of Taylor’s favorites from Sarah’s closet but also new things as well! Dresses, jackets, blouses, skirts, swimsuits, nightgowns, robes, so many wonderful goodies! As she filed through the hangers and reached the end there were still more surprises still! Taylor’s prom dress from the prom night she and Sarah shared, but a variety of new costumes as well. Princess dresses, Wonder Woman, Sailor Moon, a lolita dress, a french maid uniform, and at the back an extravagant wedding dress. Every drawer in the room’s dresser was filled too! Bras and panties of every color and style, pantyhose, slips, shapewear, pajamas, and an entire drawer dedicated to various shapes and sizes of breastforms.  In the bathroom there were pink towels and all manner of feminine self care and hygiene products such as a dozen or so different skin care creams and sprays, deodorants, maxi pads and pantyliners of several sizes, and even some always discretes. 

It was an overwhelming spectacle; every possible aspect of replicating femininity was now at Taylor’s full disposal. She knew her life was to be forever changed from here on out. After spending the next hour fully shaving, doing some skin care, and applying makeup, she threw on a nightgown and robe and headed down to Sarah.

“There she is, my beautiful girl!" Sarah said with outstretched arms.

Taylor flung herself into Sarah’s arms and at last the world was right again. She was here, in this magical home, where she could be herself and enjoy all the joys of womanhood. She was with her Aunt who she loved more than anyone in the world, and who so desperately loved Taylor as well. Her summer with Aunt Sarah left Tyler forever changed, and now Taylor looked forward to the rest of her life with her new Mother, Sarah.

The End...

Chapter 9<--------

My Summer With Aunt Sarah Chapter 9

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.

After a brief moment Tyler finally said “Well….thanks for everything", and opened the door to leave. 

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. 

“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!

Chapter 8<--------> Chapter 10

My Summer With Aunt Sarah Chapter 8

Prom Night

“Oh my gosh, you did such a good job!” Sarah screamed excitedly at the sight of Taylor’s makeup, and immediately running over to hug her.

“Thanks!” Taylor said while blushing. “It doesn’t look quite as good as when you did it.”

“That’s totally fine, it was your first time! You still did a great job!” Sarah said getting a better look at Taylor’s makeup.

“Yeah…..the eyeliner was really hard” said Taylor.

“Eyeliner is hard for everyone, don’t cut yourself up about it” Sarah said releasing Taylor.

“You certainly ordered a lot of packages” Taylor said, gesturing towards the mountain of boxes that had been delivered earlier in the day.

“I know, isn’t it exciting! Thanks for bringing them in for me!” Sarah said while surveying the boxes.

Taylor was about to tell her funny anecdote with the knock at the door, but Sarah interrupted her, clapping her hands together and saying “OK, let’s begin!”

The next two days were filled with unending feminine bliss. They painted each other’s nails, did facials, had a slumber party, performed fashion shows and photoshoots, tried on costumes and did just about every activity that Sarah could think of that Taylor had yet to do as a girl. Taylor was in heaven, everything Sarah had planned was so much fun; and Sarah always made Taylor feel so uplifted. 

The grand finale of their weekend was to be a mock prom (Since Tyler didn’t get to attend her junior prom as a girl). Sarah had bought Taylor a pink satin prom dress with rhinestones around the bodice. As Sarah put decorations up downstairs, Taylor stared at the dress, lying delicately on her bed. As she lightly brushed her fingers over the soft satin fabric, alll she could do was smile, she had no idea how quickly her life would change, but she had found such joy in what it had become.

She slipped her arms into the thin straps, the fabric sliding coolly against his skin. As she guided the dress up over her shoulders, there was a brief shiver, part nerves, part thrill. Looking in the mirror, she thought to herself that she looked exactly like the kind of girl she would have liked to take to prom. Now she had become that girl. 

When she came down stairs Sarah was waiting for her, wearing the blue prom dress she had worn to her original prom. There were streamers, a red carpet, a punch bowl, everything they might have needed for their at home prom.

“You looking ravishing darling!” Sarah said as Taylor came down the stairs.

“Thanks, I love this dress!” Taylor running her fingers down the sides of her dress.

“I knew you would! I have impeccable taste after all!” Sarah said gesturing to her surroundings.

“It all looks so amazing!” Taylor said awestruck at the obvious work Sarah put into decorating.

“I know right it came out super well, and don’t worry I only spiked the punch bowl a little bit” Sarah said with a coy smile.

They then proceeded to take lots of fun photos, eat some snacks, and dance like crazy to modern pop hits. The night could not be any more fun for Taylor and Sarah, the spiked punch certainly helped their glee as well. Their electric energy came to a standstill however when a slow song came up on Sarah’s playlist. The pair stopped dancing and stared at each other. 

Sarah chuckled and said “Come here”. She grabbed Taylor’s hands and put them on her waist saying “here, like this.”

The two swayed back and fourth, slow dancing together, eyes still locked together like a hypnotic trance. The moment seemed to carry on forever, the air between the two heavy with spellbinding affection. At last Taylor broke her gaze to put her head on Sarah’s chest as they continued to slow dance. Sarah held on just a little bit tighter and kissed Taylor’s head. When at last the song came to an end, their swaying stopped but Tayler didn’t let go of Sarah, in fact she seemed to hold her more tightly. 

At last Taylor looked at Sarah and said “Thank you for everything”

“Of course darling” Sarah replied. “Anything for my little girl”. 

After some more stops at the punch bowl and some more crazed dancing their night finally came to an end. Their night of frivolity had left the pair exhausted. After helping each other up the stairs, Taylor led Sarah to her room when Sarah went to drop herself on the bed she accidentally took Taylor down with her.

“Oops” Sarah said. “Well I guess this just turned into another slumber party”. She then chuckled. 

It was only mere moments later that the two of them had fallen asleep, still wearing their prom gowns and all. They drifted off to sleep in a literal feminine embrace. Their night among the most fun, and affirming either had ever had in their entire lives. 

Chapter 7<--------> Chapter 9

My Summer With Aunt Sarah Chapter 7

A Knock At The Door

After his heart to heart with Sarah, the night before, Tyler, or “Taylor” as she was now known, was feeling feminine euphoria the next day. Like she had earlier in the week, she spent her day doing a little fashion show with all of Sarah’s clothing. Only this time she had her new breast forms that she got to try out. There seemed to be no end to Sarah’s collection of clothing, so many different items and outfits to try. Taylor was so excited for whatever new feminine education Sarah was going to whip up with her, that she just had to spend her time doing girly things in the meantime!

At long last, after a day of anticipation, Sarah returned home. Once again she walked through the door with a box in her arms. She also seemed to be glowing with excitement and anticipation for the time ahead.

“Taylor, your new mother is home!” Sarah excitedly called out not long after coming inside.

“Hey Mom! Another package?! Taylor asked with curious excitement. 

“Well of course, I promised that I’d teach you more about being a girl, didn’t I? Well there was a few extra goodies I needed”. Sarah said proudly.

“Oh..... that’s exciting” Taylor said with a newly piqued interest.

Sarah chuckled and said, “Yup, but let’s get dinner out of the way, and then our education session will begin!”

Taylor could barely contain herself during dinner, the anticipation was killing her. What could be next in her “feminine education”. Whatever it was, ultimately she was just excited to spend time with Sarah. Although the whole mother/daughter roleplay was still very new, and a little weird, Taylor could not deny how much she enjoyed spending time with Sarah. Certainly, she enjoyed spending time with Sarah far more than her own parents, so maybe the roleplay made sense.

When dinner was over Sarah took Taylor by the hand and once again made the trek up the stairs and into Sarah’s bedroom. She sat Taylor down on the bed and made room for the box of new goodies on her vanity. She opened the top of the box, composed herself and turned to Taylor.

“Ok, you dress like a girl, time to look like one. Every woman wears makeup just about every day; and it’s time for you to learn too.” Sarah said poignantly as she took each piece of makeup out of the box.

“Ohhhh…….” Taylor responded, feeling a little overwhelmed at the prospect of having to do her own makeup.

“Don’t worry we’re gonna keep things simple, a little bit of makeup goes a long way” Sarah said reassuringly. “That being said, this is what will finish the look!” She then said as she pulled a wig out of the box.

“Wow, no way!” Taylor said in disbelief.

“Yes way! You ready to look totally different?” Sarah asked, putting her hands on Taylor’s shoulders.

Taylor nodded, and they were off on their makeup journey. Sarah explained and applied the basics of foundation and concealer, the annoyances of eyeliners, putting on mascaras, touching up eyebrows, a bit of blush, and finally some lipstick to top things off. When all was said and done, Taylor was shocked; she looked totally different. And then came the wig, it was dirty blonde and sat just below the shoulders. After it was on, she looked unrecognizable.

“Well, what do you think?” Sarah asked

“I….I look so different, I look like a real girl” Taylor said in shock.

“You look like you” Sarah said, giving Taylor a kiss on the cheek. “And doing makeup really wasn't that hard was it?” She followed up with.

“No not really” Taylor said, shaking her head and looking up at Sarah.

“Good, do you want to try it yourself tomorrow” Sarah asked.

“Uhm, sure I can try!” said Taylor, still enthralled by her reflection in the mirror

“That’s my girl! I bought all this makeup just for you, so you can keep it in your room.” Sarah said motioning towards Taylor’s room.

“Thanks Mom!” Taylor said as she packaged things up.

Taylor packaged up all her new makeup, and relocated it to her room. The pair then relocated downstairs for their nightly ritual of watching TV together. Taylor was feeling feminine euphoria, she truly felt like a new girl. During one of the commercials, Sarah struck up a new conversation.

"So.... still liking being a girl?" Sarah asked.

"OMG Yes! Look at me!" Taylor said excitedly while gesturing to herself.

"Well you think you can handle doing your own makeup tomorrow morning?" Sarah asked inquisitively.

"If it means looking like this again, I can certainly try" Taylor said excitedly.

"That's my girl!" Sarah  proudly proclaimed. 

As the night came to an end, they said their goodnights and headed upstairs to their rooms. As Taylor cleaned the makeup off of her face, she could not help but stare at her reflection and marvel at the new woman she had become. She was starting to love her new life

The next morning the first thing Taylor did after waking up was skip over to her makeup vanity. Although for Taylor, putting on makeup wasn't quite as easy as Sarah made it seem the night before. But after an hour or so of trial and error, Taylor was feeling satisfied. She then slipped her wig on and paraded around the house, feeling fulfilled. After awhile she found her way to Sarah’s room to pick her outfit for the day. What better outfit than a pink sundress; it certainly went with her new full feminine appearance. 

Later in the day while reading a book on the couch there was a loud knock on the door. Taylor’s eyes shot over to the door in a sudden panic. Who could be there, what do they want, what will they think of the boy dressed as a girl who opens the door? All sorts of thoughts were rushing through Taylor’s mind. She was feeling nervous, none of what was happening to Taylor was normal, but until now she was safe in the bubble of Sarah’s home. 

She needed to determine who was at the door; so she ran upstairs to get a view of what car may have been out front. To her surprise there was no car out front. But then who was knocking on the door? Taylor ran downstairs and slunk her way to the front door. When she took a look out of the peephole there was no one there. Taylor was getting frustrated, did she imagine the sound which made her so nervous?

Finally she opened the door and it all became clear. There were several Amazon packages all lying by the front door; it must have been a delivery driver who knocked. Feeling relieved Taylor started bringing the packages in. Sarah must’ve had quite the shopping spree the night before. Whatever further feminine education Sarah had planned for Taylor, it must’ve been quite elaborate.

Chapter 6<--------> Chapter 8