Lolita Tea Party (RP with TerraZero22) (Patreon)

I didn't know what was going on or what we'd be doing but all I had been told was that I had been invited to a party, and my friend would be coming to help me prepare for the coming event. I had nothing else to do, so I figured I would give it a try.

You had been told to arrive at your friend's house at 11 am. You walked up the stairs to the front porch and knocked on the door.

I didn't know what was happening, only that my friend was a fan of odd fashions. I had no problem with that. Everyone was different. Knocking on the door, I stopped and waited for him to answer. "Hey, it's Ryan, you in there?" I called out.

But it was not Jack who opened the door but a girl dressed up to look like a doll.

I could only blink for a moment, looking around before turning back to the girl. "Oh sorry... I was looking for Jack. Is he in?"

The words that came out of the girl's mouth shocked you. "Wow Ryan I can't believe you don't recognize ur best friend." she giggled.

I blinked again, looking him up and down before shaking my head. "No way... Jack? You look... so feminine so... girly." I couldn't believe it. I really couldn't believe it.

I giggled. "So what do you think?"

"Well I knew you were into some odd fashions, but... you look pretty good, I must admit," I said to Jack, looking him up and down. "So... is this what you're wearing to the party?"

"Yes, it is" I answered. "Come inside"

Well, it was strange, but who was I to judge. I walked in, following Jack and closing the door behind me. "So what's happening then? What is this party we're going to?"

I gestured to myself. "It's a Lolita Tea Party," 

"Okay... and what's a Lolita tea party?" I ask, seeming to get nothing else from Jack at this point.

"Lolita is what I'm wearing." I went to sit down smoothing my skirts down and keeping my legs together as I did so.

"Okay... is everyone wearing Lolita? Come on Jack, you're not giving me a lot to work with here." I tell him before sitting across from my friend.

"Yes. Lolita is a fashion style originating in Japan. It's inspired by victorian and Rocco styles. There are a couple of sub styles like sweet which consists of pastel colors and has an emphasis on cute or kawaii. Then there is gothic which is much darker."

Well, that was interesting, I'll admit. "So is everyone going to be dressed as you are?" I asked, before realizing something. "Am I?"

"You don't have to. Do you want to?"

I blinked for a moment, looking towards Jack and what he was wearing. I was nervous, and... well I guess... it did look good. "You'll help me, right? You'll do my makeup as I've... never worn makeup before."

I smiled "Of course." I then took your hand and lead you upstairs and into a room that you had never seen before. "This is Jackie's room. It's what I call myself when I'm dressed" I explained.

I was quite amazed. This was a side of Jack I had never seen before. "So... Jackie then. How long have you been dressing this way?"

"for about a year. I made a bet with Molly and lost as part of the bet I had to dress up as a Lolita. So I did. I liked it so much that I asked her to do it again." I explained.

"Oh, that's fair," I responded with a small smile, looking around at everything. "So Jackie, where do we go from here?"

"First step we need to get you dressed," I said. I took you to a large walk-in closet. It was filled with all sorts of girly clothes and not just lolita.

It looked as if Jackie had more interest than just Lolita clothing, and honestly, I didn't mind. It was all beautiful. "Are these all yours?"

"yeah," I admitted with a blush. "After dressing in lolita it kind of spiraled from there. one day Mom came home early and caught us. We had a long chat and now Jackie comes to visit at least once a week. Now I go out with Molly and her friends as Jackie."

I smile, and I had to admit, Jackie was very cute. I don't know what it was, but it was nice seeing Jack like this. "Well, I'll leave myself in your capable hands. I'll let you dress me up."

"I am so excited." I squealed as I began to get you ready.

I smile and let it happen, trusting in Jackie's skills to transform me into someone suitable for the coming tea party.

An outfit now in my head I began by telling you to strip.

I got up, turning around so I could remove my jeans and t-shirt. My socks went next and soon I was in nothing but my underwear.

"Do you want to wear panties as well.?"

I thought about it for a moment, and as weird as it might have sounded, I agreed. "Sure, sounds good."

I handed you a pair of frilly black panties. "Good, here you go."

It didn't take long, but soon my boxers were replaced with panties. And what a difference. They were far more comfortable than anything I had worn before.

I then handed you a pair of tights with crosses on them.

Sitting down to put them on, I rolled the tights up my legs before smiling, feeling them brush against my legs. "I'm starting to see why you like some of the clothing, Jackie."

I giggled. "Next up is a petticoat. This will give the dress some volume."

I stood back up, looking at the net-like skirt before smiling and nodding my head. I had to admit, I was getting really excited.

I helped you put it on by stepping into it.

It traveled up my legs and settled around my waist. It reminded me of a tutu that ballet dancers wore, though not as stiff and not as wide.

I then gave you a frilly white blouse. Helping you to put it on.

I smile, and couldn't help but blush as I feel you close to me. It was strange, I had never felt like this before, yet I really liked it. As the blouse was done up, I smiled and looked at Jackie. "I'm really glad you suggested this."

"I'm glad you said yes. I've wanted you to meet Jackie for a while. But I was scared you would freak out." I admitted.

I can't help but smile at the comment, before shaking my head. "It was strange seeing you in your complete outfit, but as long as you're happy then that's all that matters."

"Well now you'll be wearing a strange outfit," I said handed you a black jsk. Which again had a motif of crosses to match your tights.

I couldn't help but smile at the comment, before nodding my head. I unzipped the back of the dress before putting it on over my head, feeling it drop down and settle on the petticoats. "Could you zip me up?"

You turned around exposing your back to me. I happily zipped you up. "So how do you feel?" I asked you. 

I had a smile on my face, and I nodded my head. "I feel really good. A little nervous I'll admit but... I have to say I'm loving the clothing. I love... well I'm loving the fact you're dressing me up."

"I'm glad." It was now time for your hair and makeup. "Ok time for makeup," I told you. We made our way over to the vanity. I taught you how to smooth your skirts to sit down. "You're a natural." I praised as I began to get to work.

I don't know why, but the praise given made it so much better. I looked at myself in the mirror. I was a guy in a dress, but I had faith in Jackie's skills that I'd become a beautiful Lolita in due course.

I started with foundation as a base. I then began to contour your face hiding masculine features like your jawline and highlighting feminine ones. I then gave you some blush on your cheeks. Turning my attention to your eyes I used a combination of eyeliner and eyeshadow to make your eyes bigger. Almost doll-like in appearance. I then finished up with lipstick to finish the look-off.

I couldn't believe it. Watching as Jackie transformed me from male to female, I was thinking that this wouldn't work, and yet here it was. I was a beautiful Lolita. My heart was pounding, and I struggled to contain my excitement. "You're amazing Jackie, you truly are."

"We're not done yet," I said my voice taking on a sing-song voice. I then got a wig for you.

I could only giggle at the comment before looking towards Jackie. "I've been thinking, we can't really call me Ryan this afternoon, can we? Or looking like I do. I was thinking that... well what about Faith as a name?"

I put the wig on your head. "Yes very true. I think Faith is a wonderful name."

Then it was settled. When I was wearing a dress, I would be known as Faith. I smile and look at Jackie, before taking his hand in my own. "Thank you," I said before looking back to the mirror.

"You are very welcome, faith," I said squeezing your hand back. I then quickly grabbed a headband bow and put it on top of your head. "All done" I pronounced.

The result was a very pretty and very beautiful Lolita who was about to go to her first tea party. I was excited. I smiled warmly before standing up, turning around, and wrapping my arms around Jackie in a hug. "You're the best," I tell him with a smile.

That made me blush. I returned the hug. I looked at the time it was now 1 pm. "Oh yeah. The guests should be arriving." I said to you.

It was time to face the guests. I could only smile and nod my head. "Let's get started. I told Jackie before walking with her from the bedroom and down towards the dining room.

Once we got done we marveled at how cute the setup was. The table had a white tablecloth on it and each seat at the table had a small plate as well as a teacup. In the center, there were multiple cupcake towers and the table was decorated with pretty flowers as well.

It was hard not to be impressed with what I saw, and I could only smile as I looked over everything. "How often do you host these parties?"

"This is only the 2nd time I've hosted. There are 6 of us that host we take it in turns." I explained.

I could only smile in response before looking to Jackie. "Well I look forward to meeting them all... and... well if you'll allow me, to spend more time with you."

I blushed at that last part "Of course Faith." It was a sweet moment but unfortunately it was broken by a doorbell. "Oh, guests have arrived," I said in a very feminine voice. I walked over to let them inside.

I gave a small smile, even with the doorbell going off. Looking to the door, I take a moment to compose myself before seeing the guests enter. Everyone was dressed as Jackie and I, though there were various colours and styles included.

Indeed I introduced you to all the girls. Everyone was super polite and kind. We then sat down for tea.

I took a seat next to Jackie and with a pink haired Lolita in a white dress that reached her ankles named Rose. They probably knew I was a guy, but thankfully no one commented. I was treated like I belonged and loved that feeling. And most importantly , I loved being beside Jackie.

We sipped tea and ate delicious finger food. It was delightful as was the company. However Faith was by far the person I was paying the most attention too.

I had never felt so comfortable in my life. It was amazing and I loved every minute of it. Smiling and finishing, my cup of tea, I set it down before picking up a cake. The best thing about it though had to be Jackie.

Eventually the party came to an end. We bid the guests farewell giving each of them girly hugs. Now we were alone.

It had been such an amazing experience, and I couldn't believe that I had been accepted by the others. I couldn't help but wonder if some of them were like Jackie and I, boys in dresses, but I didn't care. I smiled at the thought of it, and then looked to Jackie. "Thank you again for this... I... I have really enjoyed looking like this, spending time with you."

"I'm so glad you feel that way." I said. I then got really serious. "Faith I have something to confess to you." I took a deep breath before continuing. "I really like you. Like more than a friend I always have. Would you like to go on a date with me?" I asked you.

My heart was beating quite quickly at that point. I couldn't believe what I was hearing. I smiled, especially because I felt the same way. "I would love to go out on a date with you." I said before leaning in, kissing Jackie on the lips and wrapping my arms around her.

I was so relieved you felt the same way. I smiled against your kiss. Returning both the hug and kiss. I was so happy not only had you accepted my secret but also you had accepted a date as well.

I could only smile, stepping back when the kiss was broken. I looked to Jackie, taking hold of your hands. "You've brought out the best of me Jackie. Is there anyway I can repay you?"

I thought for a moment. "I can think of a few ways" I said in a very flirtatious tone.

I blush a deep crimson beneath the makeup before smiling and nervously nodding my head. "Well then... lead the way."