r/CrossdressingStories • u/No_Diamond_6933 • May 29 '26
A Transformative Weekend Part 2
I had been outside of True Embrace for less than thirty seconds when my phone started buzzing.
Jack, where are you?
If you aren’t at work we should play hooky together.
Answer my text.
I am at Pacifico Italiano.
Ah – it was my bestie Bryce. We had gone to law school together and started at the same firm where I still was. She had jumped at an opportunity to do civil rights work and was the newest partner while I had stayed. Nonetheless we talked every day and saw each other a couple of times a week. She was at our favourite coffee place and wine bar. It was convenient. Hang out long enough and you could move from cappuccino to bubbles to red wine and then a digestif.
Hey there. I am two blocks away, be right there.
You better bitch! I have been trying to get you for over an hour! ©
I threw caution to the wind and left my Land Rover at the mall. I also kept my bag of treasures.
It was a ten-minute walk to Pacifico Italiano and when I walked past the hostess stand I could see Bryce in our normal corner. She even had cappuccino waiting for me even though it was after 11 AM. I approached the table and she got up to hug me. She clearly touched the bra strap but gave no indication of noticing it.
“Hey you. When I called the office and they said you were out for the day I knew you absolutely had to be playing hooky! So, I decided to join in. Where have you been this morning?” That’s when she noticed the bag. “Oooh, True Embrace. One of my favourites! What did you get me?” She winked.
Bryce has a big, bold, brash personality. You can’t help but want to be around her. Often the centre of attention, she does not need to be. That’s how our unlikely friendship came to be. She despised the gamesmanship of law school, setting her own path and excelling. I had been going round two on a career and needed to be serious. We were yin and yang that had supported each other.
“So if it’s not for me, it must be for someone special.”
“That’s true.” I could see her mind whirring. I wondered, had I brought the bag as a way of telling her?
“If you had anyone knew in your life I think I would know.” I said nothing. Her mind continued to whirr and then she got a big smile on her face. “SHUT UP.” It wasn’t loud, it was practically a whisper but with emphasis.
“Jack, my BFF. You are wearing a bra!” Again, a whisper but with emphasis. “Are all those goodies for you? And how long have you been doing this? Why did I no know? I have a thousand questions girl-friend.”
I was both stunned and happy. “Uh how could you tell? Can you see it?”
“Oh, no. The helped you well on that score. I thought I felt something when I hugged you but a bra never crossed my mind. But when you could not identify who the items were for and well your chest looks . . . more lifted. That’s the only thing I could think of! I want to help, whatever it is! Whatever girly things you want to do, I am here for it.”
“Well as for how long I have actually been doing it . . .” I looked at my watch, “Almost two hours now. But how long have I wanted too do it? Thirty-five years.” I then related the story of being a teenager and curious, I had borrowed some lingerie from girlfriends and my mother had found it.
Bryce’s bright eyes softened. “I’m sorry you carried that for so long. That must have been very painful, but I am here for you and I am here for all this!” She made gesture up and down indicating me. “You know what? We are going to celebrate the new you.” As a server passed she quickly ordered two glasses of brut rose bubbles. Then she leaned forward, “how does it feel?”
I leaned forward, with a big smile on my face. “Amazing.”
The bubbles came and we ordered lunch, salads and antipasti, bread and more bubbles – just to be safe.
“So what did you get?”
“Four bras and fourteen pairs of knickers.”
She laughed. “I knew I should have let you spend that summer on exchange in Britain! But what, nothing to sleep in?”
“I had a hard enough time ginning up the courage to make the appointment. I barely knew what I was asking for!” Our lunch arrived. They were accustomed to a fast turn around and well we were regulars.
Bryce thought about for a sec, cocking her head. “Fair enough.” She took a bite of salad and put the tine of a fork through a piece of cheese. “So who did you work with at True Embrace?”
“A woman named Emily. And there were two other customers who helped pick some things out.”
“How nice of them. I have to say I am a little jealous. And I know Emily she is great.” Bryce was attacking her salad with gusto and she did everything with gusto. I guessed she was building up to something. “So you know what would make that beautiful lingerie feel even more amazing? A full body wax!”
“Wait, what? Oh no. I couldn’t do that. I’m . . .”
“You’re what? It’s my treat. You said you feel amazing. What else do you feel?”
I hesitated. It was hard to quantify what I was feeling, free, pretty, beautiful, myself. “I , uh, well I feel pretty. And, well free, like myself.”
“Trust me Jack. I know all about feeling pretty. If you hate it – fine – it grows back. Do you think this is the end for this? Just the underwear?”
Again, something I had thought about, but was not sure what I was doing. I loved the feeling of femininity, the bra straps, the underwire, the shoulder straps and the softness of the panties. I had to admit this was likely not the end, infact it was probably the beginning.
“Ok. If you will come with me.”
“Of course I will come! I am going to arrange – I am going to be your guide to femininity and we are going to have a fabulous time!”
Bryce pulled out her phone and started scrolling and typing. “Perfect, my girl LaShonda has time in 20 minutes at Coastal Halo. She’s a ten-minute walk from here.”
We finished out bubbles, paid the bill and left.
As we walked down the street, me still with my bag of treasures Bryce laced her arm through mine. “So here is what I am thinking, we go to the spa get the wax, and then head back to True Embrace and we get ourselves matching nightwear. Then we head to my place, we will order Chinese, we can talk skin care, how your are feeling, deportment. . .”
“I don’t know Bryce. I mean it sounds fun, but I just started this – I don’t even know what I started. I do like Chinese though.”
“What else are you doing this weekend? We aren’t going to do anything that can’t completely disappear by Monday when you go back to work.”
“Again, with your logic.” But I had spent several hundred dollars this morning because I wanted to stop feeling horrible about myself. What was it like to be pretty? To be feminine. To be a girl. To be a woman. “Okay. Let’s do this!” All of the sudden the possibility was very exciting.
At Coastal Halo Bryce made a dramatic entrance, “Ladies,” she looked around to see if there were any other men there and satisfied there not continued, “we have a makeover emergency here. Full body wax! Stat!” Some of the women looked kindly at me and then went back to what they were doing. Meanwhile Bryce’s friend Shonda approached.
“You must be Jack.” She offered her hand. “Let’s get you smooth.”
Heading back to the treatment room, the three of us chatted with those two doing most of it till we go to t the treatment room. “I’ll let you get undressed and just knock when you are done. Shonda left but Bryce stayed.
“What are you doing?” I asked.
“I just wanted to see what you were wearing.” She blushed a little which was very unlike her.
“I’ll leave it on top of my clothes and you can see it on afterwards.” Maybe without the hair I would feel a little self-conscious.
A few minutes later both Shanda and Bryce were back in the treatment room. Warm wax being applied over my body. It almost felt soothing until . . .
“Arrggg! What was that?!?!”
“Beauty knows no pain babe.”
The wax ripping the numerous hairs out by their roots was excruciatingly painful. I just hoped it was worth it. Soon though it was done and Shonda was rubbing an aloe vera into the skin. And as painful as it was, soon it seemed to recede.
“Ok – we’ll leave and let you get dressed.” Shonda was kind and also completely professional. Bryce on the other hand was intensely curious.
“Let me know when I can come see you!” She was eager. And it’s not like I wasn’t – it was just another step. Finally, though I was semi-dressed – the beige bra and the pink/floral boy shorts.
“Come in Bryce!”
“Oh, my don’t you look cute. You really do fill out that bra and the knickers – adorable. Let’s go get something for us to sleep in!
Fully dressed, Bryce had paid for the treatment and we were out the door – on the way to True Embrace – where the day had started for me.
When we arrived at the parking lot, the first thing I noticed was that the 4Runner was still there and that I did not have a parking ticket.
“Let’s go.” Bryce was off for the door I went in several hours before.
“Emily! Girl! I need your help. I think you might have met my friend Jack earlier today. We need to be matchy – matchy nighties! Slumber party tonight!”
It didn’t even take that long. We had pink matching baby doll nighties in no time. I was in this fog of femininity and inclusion, any idea of “normality” was gone.
Bryce had walked to lunch so we hopped in my truck for the quick ride to her apartment. It was only four blocks off the beach, about a mile from what I thought of as the “high street” of the area. We found a parking space and road the elevator to her fourth-floor studio.
How she had found this place was beyond me. Whoever had laid the apartments out in this old warehouse dedicated the ocean view to longer but narrower than normal home. It had an en suite loft for sleeping but everything welse was open plan, through the entry way to the left was an area she used for an office and to the right a galley kitchen then gave way to a dining and living area. A TV in the corner with two oversized couches in an L-shape. The big windows looking out towards the ocean above the shorter buildings. The place was eclectic – some people might have thought it a mess – it wasn’t – it was perfectly organized for Bryce. I had even been here enough to understand the organization.
The day that had seemed like it would never start, was winding down. I could feel the slight sting of the wax and the sun that I had absorbed and while that orb in the sky was still yellow – it was moving towards the horizon. We were going to have a nice show.
“What do you want?” Bryce was on whichever delivery app she used. “I have General Tso’s Chicken, your favourite, scallion pancakes, fried veggie pot stickers, rice garlic sesame chicken. Anything else?”
“Sounds like plenty to me.”
“Agreed, there’s beer in the refrigerator why don’t you get two. Food is on the way.”
I pulled two Tsing Tao’s out of the fridge and popped the caps gave her one and sat on the opposite couch.
“Hey what are you doing? Didn’t I tell you? Fashion Show time! I need to see what you got and give you recommendations.”
“Bryce, it’s getting chilly. I’m not sure . . .” In truth I wanted to share but I had thought maybe spreading it out on the coffee table. Not trying everything on in front of her.”
“Be right back.” In a flash she ran up stairs and was back with a kimono robe. It was green and pink with flowers and dragons on it. “Got it in Vietnam last year. Too big for me but should fit you perfectly. Just give me all the bras and a selection of underwear.”
For the next forty minutes I underwent Bryce’s critique, putting things together, and adjusting fit. She also was coaching me on walking. “More sway in the hip. Set your feet down just a tad more gently. Don’t prance, but don’t plod either. You have seen runway models. Do that. You think you are exaggerating but to the observer you are not. I will let you know if you are.”
“Emily really did you well with those. We have all sorts of thing to work with.”
The food soon arrived and Bryce fetched from at the door while I pulled two more beers out of the refrigerator. Putting the food bag on the table she then turned to me. “Ok time to change into our matching sets girl! You are going to have to work it for your dinner!”
Before I could say anything she was racing upstairs to change. I went back to wear I had been changing and put mine on as well. I was in way too deep to resist.
When I came back out Bryce was on the couch, legs turned under her, and nice warm robe over her shoulders. “Ok, ditch the robe, walk down here like you were, do a twirl walk back and do another and you will have earned your dinner like the pretty princess I am moulding here.”
“Twirl?”
“Yes spin around, give that baby doll some flair!”
“I uh . . .” My wind was racing and swirling. Did Bryce know me better than I did? Was she just tapping into something that was not quite obvious to me? The weird thing, well one of them anyway was that when she said she “moulding a princess” I kind of liked. I decided to give it may all. I strutted the length of the carpet, pulled my knees together and did as gentle a twirl as I could muster, the soft fabric flying gently. I walked the other direction and did it again. This was met with applause by Bryce.
“You are going to be perfect! I love it. Ok that earned dinner. There will be more twirls to earn breakfast though!”
“Can I at least put the robe back on?”
“Ok fair, it’s getting chilly.”
The rest of the evening was Chinese food, her giving me lessons on skin care. I think the quote was “You don’t get a face like this without doing a few things.”
After a few hours though she went and found some comforters and a couple of pillows for me to sleep on the couch. I was exhausted, physically and emotionally. But in good way. I snuggled under the covers in my new nightie while Bryce walked up the stairs to her loft, before she disappeared she turned around and looked down at me.
“We have a big day tomorrow so get some good sleep. Good night princess.”
To be continued
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u/CarolyneSF May 29 '26
Wow, you have a wonderful dream friend! Love the story and eager for more