Sweet Caroline's Adventures

I’m a boy who loves to dress up like a girl on occasion. I’m truly beginning to embrace to who I am, and it’s a marvelous feeling. A large part of that feeling comes from having so many of my friends and family that accept me for who I am - something I would always have been terrified wouldn’t happen when I lived back in the South. To those who I have shared my most person secret, and who have accepted me as I am with open arms: thank you for all of your love and support.

At this point, I’m really just getting started in my adventures.

Planning has begun!

It’s been an amazing day so far! After yesterday’s excitement in finally getting a date set for the fashion show and private shopping event at Lane Bryant, I set out to start the planning process.

I spent my evening last night creating a to-do list that covered every little thing I could think of to prepare for the event. From budgets to decorations, I’ve got everything on the list. It’s a lot to think about, but I’m confident in my ability to get this done.

I’ve already spoken to some potential sponsors and the response thus far has been overwhelming. I’ve received a pledge from my favorite breast form supplier to provide a pair of forms for a raffle as well as a pledge from the House of Wigs in Los Altos to provide wigs for the fashion show and a gift certificate for the raffle.

I’m also going to contact a few salons in the Gilroy area to see if they’d be interested in doing makeup for the event. Hopefully I’ll be able to find someone that’s willing.

One of the more interesting developments is that I’ll be doing an interview withhttp://www.tgforum.net about the event. This is exciting because I’ve never really been interviewed for anything. I’m a bit nervous about it because I feel that my writing style is a bit lacking. Regardless, I look forward to talking with Angela, the Editor at TGForum.net in the coming days.

The next big step is to really solidify the budget for catering and decorations and start getting the word out.

I’m so excited!

Today was a very fortunate day

After deciding to leave work early, I received an email notification on my drive home that my recent Lane Bryant order had arrived at my local store. Looking forward to the sweaters I’d ordered, I made my way there before going home.

When I arrived, I noticed the manager talking to a gentleman so I waved and let one of the associates know I was there to pick up my package. While waiting, I rifled thru the racks looking at the new things and the manager pointed out some new arrivals.

That’s when she mentioned that the man she had been talking to was the district manager. This is the person I’d been waiting to approve the private shopping event I’d mentioned before. She then asked if I’d like to meet him and I enthusiastically agreed.

We talked about the event, what the manager and I were considering for the event, and any particulars we’d already considered. After hearing the plan thus far, he agreed that it sounded like a good idea and told us to set a date. 

If I hadn’t made that order; if it hadn’t been delivered today; if I hadn’t left work early; hadn’t checked my email before getting home… a lot of ifs and it just all worked out.

At this point, I’m in full out planning mode. We have a tentative date in mind and we’re working securing catering, makeup artists, wigs, decor, and more. I’ll be sure to post the event details as soon as I have them fully confirmed.

Flattered by Lane Bryant


It’s been an interested past few days.


Friday, I had an appointment to get my eyebrows waxed. I was running really early, so I ended up stopping by the local shopping mall and browsing. While I didn’t find anything at Torrid, I did find some great stuff at Lane Bryant which was having it’s “Buy One, Get One” sale. I ended up with a couple of dresses and a couple of belts. Once I’d wasted enough time, I headed over to the salon.

Upon entering, the owner quickly asked me where I had parked and told me I should move my car around back because of a movie that was going to be shown on the street and I’d be towed otherwise. So I moved.

As I was leaving, I realized that I’d parked right in front of House of Wigs! I had no idea there was a wig shop any where near my office but this was just too good to pass up. So I went on in.

It was a decent size shop, lots of selection, and the owners were super nice. Here I am, full beard and all, and they’re happy to help. Anyway - I ended up buying two new wigs. I went with something different on one of them: I got a short brown and blonde wedge cut wig. It just really framed my face well! 

So fast forward to home.

I’m trying on my purchases and I realize that one of the belts from Lane Bryant is too big! Luckily, there’s a Lane Bryant near my house that I frequent (albeit not in many months) so I just planned on exchanging it the next day.

me!So yesterday morning, I wake up and get all dressed up. Wearing my new short wig, I began running errands and stopped by Lane Bryant to exchange the belt. The store manager recognized me immediately and exclaimed, “I thought you’d forgotten about us!” We spoke a bit and they encouraged me to look around and find another belt that fit. I ended up picking up a couple t-shirts, 2 more belts, and a leopard print cami.

As I was checking out, the manager said “Can I ask you a question? I’ve been thinking about holding a private sales event for others like you. Most of them are just so intimidated by the shopping process. You’ve just got so much confidence and present yourself so well. Would you be interested in helping me organize this event?”

I was almost speechless (a rarity for those that know me). I was so flattered. I gave her my little calling card and let her know that I’d be more than happy to help.

I’m so excited about helping put this together. My mind has been racing about what could be possible. Should I talk to the wig shop about having someone on hand to show off wigs, teach people how to wear and care for them, etc? What about a make-up artist to teach some tricks? I’m be talking to the manager about all the ideas and see what she’s up for and how much she wants to do.