In these times of restrictions and lockdowns (that hopefully will soon be a thing of the past) I thought it might be a good time to provide a compilation of my writings about my first time attending a CD/TG conference since many of our current members weren’t around back in 2016 when I wrote them. It’s a bit long but I think it flows well as a travelogue and a story of taking the first BIG steps in a journey of exploration.  Hope you like it!

My first conference trip to a CD/TG conference

This will be an ongoing saga of my trip to Florida for the SCC. I am posting some of it now cause I will be busy packing the next few days before leaving Sunday morning! So here we go!

Cyn’s Trip to Florida September 25-Oct 2, 2016

Crossdresser Superstore

Thursday, September 22, 2016

So, the trip I’ve been waiting for all year is only days away. The first opportunity for Cyn to experience multiple days as herself at the Southern Comfort Conference (SCC) in Fort Lauderdale, FL! I’m simultaneously excited and terrified. While I have had several one-day or one-evening outings, and I’ve stayed dressed at home for days in a row, the prospect of going 3-5 days straight and interacting with the world that whole time is daunting. Fortunately, I won’t be alone as Samantha G will be going as well, and we will be able to support each other. I’ve just about decided what I am taking with me though it still needs to be packed. So much still to do and so little time. I have league pool tonight and am also going to the Homecoming football game for Virginia Tech in Blacksburg Saturday (kickoff 1230pm but leaving from Richmond at 5 am to catch the parade at 9am-will return to Richmond by about 9pm.) So before then I need to let my sister hem my gown for the Saturday ball at the SCC conference, make any last minute purchases for the trip, pack up the car for the football game and –oh yea-I suppose I SHOULD try to get at least SOME sleep in there! After returning from the game, I need to unload the car from the football stuff and pack it with the stuff for the SCC tripl then SOMEHOW fall asleep to get up and leave for FL on Sunday morning about 7am. Ten hours later, I should arrive in Orlando where I will be stopping by to visit Disney World for a day-Magic Kingdom part. I’ve never been so that should be fun (but doing it in male mode since I would be too worried about Cyn’s wig flying off on the rides to enjoy it). Will leave for Lauderdale on Tuesday mid-day. I hope to keep this topic updated as the days go by. I’ll be too busy the next few nights to do that so I pre-loaded the discussion of the first few days of the trip here but I’m bringing my laptop so once I get to the conference itself, I will endeavor to update it daily with posts here. Love for you to follow along as Cyn has her “great adventure” and learns more about herself! Please comment/reply as much as you can/want. Til then, it’s TTFN!




EnFemme Style



On the road! Florida Here I come! Watch out!



Safely in Orlando-arrived about 9pm. Disney World on Monday!

More tomorrow!



Monday late night

OK we only had one day so no time for anything but Magic Kingdom (no EPCOT) Thunder Mountain was closed for refurbishment (very disappointing!) it was quite sunny and hot and humid in the morning while we did Pirates of the Caribbean, Jungle Cruise, and then the animatronic bird show and then it was on to Splash Mountain but….after waiting 30 min in line thunder pealed and they shut it down. initially we hoped it was a quick storm that would be over in 30 minutes as often they do in Florida. Alas after another 60-75 minutes of waiting we gave up and minutes later the skies opened up. So much for that ride as it rained for the next 5 hours!! We did see a lot of other stuff including Space Mountain, then watched the Main Street electrical parade and then the fireworks. After leaving the park we met for a VERY nice late dinner and conversation with Captain Sally; we chatted til 330 am or so! Tomorrow we head to SCC at about lunchtime. will update then get there am settled


PS Thanks for all the lovely comments/replies! Till then



Travel day today-was up talking to Captain Sally til abut 330 am then caught up on site til about 630! Woke up at 10 am-packed up and we headed to Lauderdale (BTW it was 83 degrees a 10am with heat index of 101–dew point was 83 also so relative humidity was 100%! Ran into heavy traffic and thunderstorm so we relaxed early evening and Sam went to pack her stuff. Imagine she will have less than the carload of stuff I brought with me(see pics of Cyn’s stuff on my media gallery page)Tomorrow we have Princess Day! (Description below). Not sure what doing Wed evening yet but Cyn will 99% LIKELY) be 24/7 til Sunday am. Will write about Princess Day tomorrow night!

Nature Day 3


\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\”Princess Day (10 AM to 2 PM) for $30 including lunch

First Timers and the Experienced alike enjoy this event! Join the group as we leave the hotel around 10 in-route to spending the morning “Getting Pretty” and meeting new friends. We alternate between getting new nails, beauty tips at Sephora, strolling and shopping, and meeting for a nice lady-like-lunch before heading back to the resort around 2. While the transportation and lunch are included, you will need to budget for nails ($ 35-75) and your shopping budget.\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\”

Also posting a couple Disney Pics on my media gallery on profile page! (but not a lot cause is SLOW internet at hotel;) Did some wishing on a star during the castle fireworks program. Partially that Sam and I have a good time here but most importantly that each and every one of you ladies finds joy and happiness in whatever is the best thing for you in your lives-be that dressing or transitioning or any other path! Love you all!



OMG! About to go down, register and then head out on Princess Day! Wish us both Luck!!! Details later today!



So, Princess Day was FABTASTIC! Got a mani-pedi and that will definitely NOT be the last one of those!! What a heavenly experience! and they look absolutely fabulous! That was followed by a delightful lunch! (Yes Denise and Codille and anyone else who was curious -I DID eat something besides peanut butter -I ate filet mignon and fries and it was yummy!).

Join Our Community-cdh

And now the question everyone wants to know-did Samantha survive her first outing? The answer is a resounding YES!! 🙂 She looked great! Pics to follow on my media gallery from the salon of both of us at the salon! WE then walked down the outdoor mall sidewalks to the restaurant-FYI walking longer distances in heels is painful but doing it in 90-degree heat is even worse! But that was NOT all we did today! When we returned to the hotel, we decided to go to the big Sawgrass Mills indoor mall and do some shopping! And yes, we went dressed! We went with some other girls from the conference and had a great time including making some purchases of lotion and scents at……. Victoria’s Secret! Everyone at all the places we went were great! Friendly, smiling, and accepting (at least what we saw). So, Sam went from never having left her apartment to walking around the biggest mall in town in just one day! So proud of her! Be sure to send her PMs or public comments/messages of congratulations to her!

We are also telling folks here about the site so you may see some new folks visiting the site and chatroom! Be sure to welcome them as y’all ALWAYS do with kindness and a friendly smile! Relaxing tonight-seminars start tomorrow! Hopefully, I’ll stop by chat later tonight! Miss all you girls and SO wish you were all here with us!

Love to all of you fabulous ladies!



Herbal_breast_enlargement_naturedaycom (1)

Its 320am on Friday morning and I just got back in my room. I slept a lot earlier Thursday until around noon or so then spent a leisurely afternoon catching up on emails and watching TV and getting ready for the evening activities. Tonight, we went to dinner and a drag diva show at LIPS in downtown Lauderdale. (Again, for those who doubt my ability to eat food other than peanut butter, I had mashed potatoes and a broiled chicken breast that had to be a DD cup at the very least!). I also had a wicked Long Island Iced Tea! The show was quite good with about six performers ranging from Ella Fitzgerald to Tina Turner to Cher to Reba McIntyre to Taylor Swift. We then drove back to the hotel where they had karaoke (which Sam and I WATCHED but did NOT participate in (I will THINK about it if I have enough to drink later this week! 🙂 LOL, met lots of people and are telling them about our site. One of the “couples” we met were a girl form New Jersey and her CD partner from England. Great folks who had gone for a late-night dip in the hotel pool the night before. Long story short, I ended up joining them and another attendee in the pool from 145 am til just a bit ago and was wearing my pink bikini! Had blast and some great conversation. Sam took a pic or two of us and declined to swim herself! I’ll post then once I get them from her!
More to come tomorrow!

Visit Transgender Heaven



(Below is A comment from my good friend who accompanied me on the trip)

NEWS FLASH !!! I Got Cynthia to eat some fish at tonight’s dinner. I’m not sure what kind it was but it was very mild and not fishy tasting at all. Told her to pretend it’s a chicken that can swim really well haa haa.
One more day to go tomorrow with the big gala dinner Sat. night.
Thank you all for the support and well wishes. I’ll have more details on my thoughts later I like to sleep more than Cyn does. She is the postmaster.





Saturday morning and I survived another late night at the pool/hot tub. As Sam mentioned I Actually ATE some FISH for dinner last night. Unfortunately, while HELL may have frozen over, Ft Lauderdale did NOT cool down! Great speaker during dinner-the former boxing manager of world-famous boxer Lennox Lewis-she recently transitioned and told us her story which was both amazing and extremely poignant as well! At lunch they had a world-famous surgeon, Dr. Marci Bowers spoke and was introduced by the mother of Jazz Jennings (the teen transsexual that has the show on TLC on cable TV). That was followed by karaoke which was great to watch-didn’t sing last night but am considering doing so tonight with a couple other girls-depends on the flow of alcohol! 🙂 LOL Then went out to the pool/hot tub at 130am till 330-4am (Sam was the responsible adult and went to bed instead!). Pics in my gallery of Cyn with hair au naturel and my one-piece monokini (the ones from Friday overnight pool adventure in the neon pink bikini I will post when I get from Sam! Time to get ready for lunch! I’ll post later about today’s final day and the ball and karaoke!

Join Our Community-cdh

Wish ALL of you were here!



Saturday was the final day and it didn’t disappoint! The ladies were all resplendent in their gowns-well Sam G and the others anyway-I don’t know if I would consider myself so but I didn’t look horrible anyway! 🙂 Dinner and dancing (no karaoke tonight though-maybe next year! 🙂 ) . Lots of drinks including a shot of Jack Daniels for most of us. We didn’t want the night to end so we went out to the pool for another late-night hangout and chat! Then sadly around 3-4 am we had to let the horses change back to mice and the coach to a pumpkin! And Sunday morning we packed our things up and headed for home! The events are now fond memories but WHAT memories they ARE! 🙂 Words can’t do the experience justice and we made many new friends that we hope to see next year. And we hope YOU will choose to join us as well! I’ll be writing an article to summarize the whole week but will say in conclusion here that this was one of the most fun and memorable experiences of my life to date and one I Will never forget! Thanks to all who read and commented/replied and if you have any questions feel free to ask me (or Sam G as well)



Some final thoughts on the trip to SCC in Florida


I’ve been back from the trip now for several weeks and yet it seems like it was just over yesterday. It was back in January that Samantha G and I bucked up each other’s courage and signed up for this year’s Southern Comfort Conference (SCC- a TG/CD conference) in Ft. Lauderdale. We each had trepidation as this would be the first extended time spent as Cyn and Samantha for each of us. For Sam, it was her first time EVER outside her apartment and to top it off the conference was in her hometown! For me, even though I had been out as Cyn a few times for a day or evening and interacted a little bit with others, this would be an entire week spent in close quarters with both other TG/CD folks as well as hotel staff and guests and even folks out in the other parts of Lauderdale as we went to some ‘off campus’ events.

Nature Day 3

We got a chance to meet first in ‘guy mode’ in Orlando for a day at Disney World and were also fortunate enough to be able to have dinner with Cap’n Sally afterwards. Both Disney World and the dinner were fabulous experiences. I had never been to Disney but plan to return when I have more time in the future and Cap’n Sally rocked her pirate boots!

Next it was time to drive down to Lauderdale on Tuesday. We stopped to eat lunch at McDonalds and as I finished using the facilities, I reached into my pocket for my debit card and realized with a fair amount of panic that I did not have my car keys! Fearing the worst, that I had locked them in the car and would have to find a locksmith, or Dodge dealer, 700 miles away from home to unlock my car loaded with Cyn’s things, I walked back to the car. To my tremendous relief, I discovered that thankfully my car will not allow the doors to be locked with the key fob still inside the car. Anyway, we ate and then continued our drive through a typical South Florida afternoon thunderstorm.

Arriving at the hotel, I checked in, though Sam’s reservations weren’t ‘until Thursday evening. The hotel is a resort type setup with a main building and then apartment style buildings for the rooms. It was a fair little walk from the room to the main building in a sauna-like atmosphere, one we would ‘enjoy’ often in full femme mode that week, sweating through our wigs and makeup! We parted ways that evening as Sam needed to finish her packing at her apartment.

Visit Transgender Heaven

Wednesday morning was Princess Day, which I described in detail in my forum post above and we thoroughly enjoyed our visit to the nail salon, an experience I plan to repeat ASAP! After lunch with the girls, we (Sam and me and three other girls we made friends with) returned to the hotel and then went to the largest mall in the city and walked nearly the entire mall, including a stop in Victoria’s Secret where we took advantage of a great sale on lotions and scents!

The rest of the week was fabulous as I described in detail in the forum posts above.

I want to thank Samantha for being there as support for me. She will tell you she didn’t do anything but that is not true! Her encouragement and willingness to try things she had never done before were an inspiration to me, as were the many speakers and other attendees. We made several new friends, some of whom have joined our site, and are looking forward to next year’s conference.

For those who wonder if it is worth the time, money, and travel, I can say yes, it is! Especially for those of you who live in ‘less enlightened’ and less tolerant places than others who are more fortunate. We had attendees from all over the US as well as the UK and even India!

So, whether you are at the very beginning of your CD/TG experience or a seasoned vet, whether CD or TS, shy or outgoing, you can have a fabtastic time. I guarantee if you make the effort, you will have the time of your life. Below is a poem I wrote, as is my nature, with some of my thoughts. I hope you enjoyed reading about our trip and that we will see you in 2017 at next year’s conference if not before then.


Thanks to all of you ladies for the wonderful love and support that you have all provided me. No matter what my path, I know I do not walk it alone!




Emerging from the Chrysalis

The long-anticipated day had finally arrived;
Would fear cause me to cringe and hide or would Cyn find she thrived?
I’d longed to let the world see her but always had held back-
Afraid that she’d be ridiculed, or worse, might be attacked.

Like many had before me, I had let the world define
Who I “should” be- despite the feelings deep within my mind.
I knew that there was more to me than what I showed the world,
But did I dare reveal the thoughts that in my soul had swirled?

For decades now the answer was a firm and fearful “No”
Until a friend broke through the walls I’d built and let me know
That I need not be fearful to let others know the truth
And let them see the girl I’d buried ever since my youth.

And so I let the curtain part the slightest little bit.
I ventured from the bedroom where before I’d always sit.
And though the progress I was making seemed so very slow,
Once I relaxed, the fears decreased and Cyn began to show.

Like peeling back an onion, as each layer I’d unwind
I liked the person who’d been hidden deep within my mind.
She seemed to represent the person I was meant to be
And slowly I allowed the world this special girl to see.

The Florida trip to SCC had long ago been planned,
And finally the time to go was suddenly at hand.
The nervousness returned as I began the long, long drive-
But at the same time, never had I felt quite so alive.

I’ve posted lots of details of that most amazing week.
At this stage in my journey, that has been the highest peak.
And though I’m back at home, I know I’ll never be the same
For Cyn has tasted freedom and her passion set aflame.

She may decide that getting out as Cyn more is enough;
Or is transitioning a need? Decisions can be tough.
But no matter which path she takes, Cyn’s not going away-
The time to hide is over-and THIS girl is here to stay!


I encourage each of you to go to one of the conferences and let yourself explore your feelings and be true to your inner soul. I think you will find it incredibly liberating, and possibly even life changing. (And of course, amazingly fun too!)



More Articles by skippy1965 Cynthia

View all articles by skippy1965 Cynthia
The following two tabs change content below.

skippy1965 Cynthia

The Original Cyn, or OC for short. Cynthia is from Richmond Virginia, she crossdresses every day (lucky gal!) and has a knack for tracking down niggling technical issues so we can fix them. She is also on a journey of self-examination to figure out where her feminine journey will lead her, and is always willing to talk with others about their feelings and questions or her own. Update January 2023- the above was written by Vanessa on my behalf back when I joined in 2015. So much has happened on my journey since then. From a shy CD who had hardly been outside as herself to being pretty much full time Cyn 24/7 now. I told work about me and started HRT last year. Everyone knows about me in my life now too. I've socially transitioned for the most part but not sure if I will do anything regarding legal name or any surgeries at all. It's taken mea long time to accept myself for who I am but the site has helped me reach that level of self-awareness. I say dating below but that's just the best status I can say. I have a friend who is very special to me that I HOPE will be more a life companion as time goes forward.

Latest posts by skippy1965 Cynthia (see all)

5 2 votes
Article Rating
Inline Feedbacks
View all comments
Active Member
3 years ago

Wow! TY Cyn! You have nailed several of the emotions, excitement, and fears I am feeling right now. This will be my first time as Pru, in another state/world. I cant wait. And I see that happening to me. Plenty of time too get ready, but the day of departure. I will probably be scrambling like crazy! I know with You and Sam, I am safe. And I cant wait to meet you!! Hugs Pru

Roberta Broussard
Noble Member
3 years ago

I must have missed something, whats in 48 days ?

Kate Carter
Kate Carter
3 years ago

Thanks for the memories Cyn! I can still credit that trip as my first time out in what seems like a lifetime ago. Still can’t believe I flew all the way across the country to Florida by myself and knowing exactly zero people and just walked on out and was myself. Miss you all!

Kate Carter
Kate Carter
3 years ago

Yes, apparently I had deleted my previous one in some dark moment. I’ll try to take it easy on this one.

Roberta Broussard
Noble Member
3 years ago

Thanks for offering your story. It leaves me wondering if that is something that I might like to do. Love the fearless attitude..

Samantha G.....
Active Member
3 years ago

Thanks for posting the memories again Cyn. It seems like it just happened the other week but also feels a lifetime ago.

Mika Malone
Active Member
3 years ago

I loved reading about this. I have not even bought my first skirt or heels yet and a conference like this would be the kind of setting that I would enjoy being full femme for a first time in public. I do plan to be en femme at the next cosplay or Pride Fest whenever all this COVID stuff diminishes and we can gather in large dense groups again. Hopefully, I can get some makeup skills by then. It’s also great to read about Samantha experiencing her first time out of her apartment en femme. Thanks for such a detailed… Read more »

Barbra Heaps
Active Member
4 months ago

Cynthia, I just finished reading SCC 2016 a- Reprise! You girls are so brave I do not know if I could overcome my fears to go out in public. Cynthia, may I say you are such a wonderful role model CDH is lucky to have you as a member. I just love reading your poetry it always makes me feel warm inside and brings me Hope! May I PM you some time?


Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?