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View Full Version : North Carolina was kind to me, or how crossdressing saved my life.



Elizabeth Ann
09-13-2008, 08:57 PM
Well, it might have saved my life by keeping me awake.

I dismasted my sailboat, and found a used mast in Florida. Insurance not being overly generous, I decided to economize by going to get it myself. And that is how I found myself in khaki shorts and a woman's top (and panties of course), driving up I-95 with a 52 foot mast on a 29 foot trailer. After about 1,500 miles and a lot of work building a cradle, lifting, climbing, tying, etc., I was exhausted, stopping every hour and a half or so, to recuperate.

The woman's top was fun. It was pretty simple t-shirt like material, but it had a lace hem, low neckline, and that cute elastic gathering right between where my breasts should have been. I'm not sure any men noticed at my frequent stops, but several women had flashes of recognition and made eye contact and slight smiles.

Coming into North Carolina, I saw a billboard for a sexy lingerie place called Adam and Eve, and pulled in. I have always wanted to try a corset, and found a very pretty under bust style in a red satin with a small floral pattern. It was marked down from $60 to $30, and they said sure, I could try it on. Now I know there are corset aficionados on this site that will tell you that a $60 corset is overpriced by $60, but I was delighted with a shrinking waist and the development of that little shelf over the hips that you see in photos of women in corsets. I loved the look in the mirror and I bought it.

An hour or two later, I see billboards for a wig place. My only wig is a nondescript thing I got on the Internet, so I pull in. It is a mom and pop wig shop with several women customers. I am warmly received, had discussions about several types of wigs, am put in a chair and fitted with several different wigs. About the only curiosity they show about me is why I am pulling that big light pole behind my SUV. I leave with a beautiful blond mid length wig with that style where it curls in about three inches below your chin.

Now I am beginning to get excited and not so drowsy. Next stop about an hour further, is at a sort of downscale outlet place (J&R something), where I wander over to the cosmetics. Now I am mostly an indoor girl and know almost nothing about makeup. I am looking at the way too large array of stuff when I see a sales woman in her 60's watching me with interest but no discernible disgust. So I pick up several shades of concealer and walk over to ask her which one is right for me. Turns out, she used to help a friend who was a CD and she takes me under her wing, showing me what I should get and what the right shades would be for me. I ask if I can pay for a training session, but she says I don't need that, just put this on this way and this on that way, and you can do it.

Now I am so charged up with my new corset, wig and makeup, that I stop at the next rest area, which has a family, unisex bathroom to get dressed up. This is a bit of a dilemma. My wife is in the "I'll tolerate it but not deal with it" camp, and is completely opposed to any shaving of chest or legs. Moreover, I have only been out a few limited times, and most of my clothes, including those I brought with me, are more sexy than practical. I finally settle on my favorite dress: a simple black knit dress with little gold flecks and a high neck line (to hide the hair). It is probably knee length on most women, but on my 6'2" frame, it is about 6 inches above the knee. I combine it with opaque black tights and sandals with 3" heels.

After shaving and working on the new makeup, I think I look pretty good in my blond wig, black dress and tights, and black 3" heels, but know that there is no possibility of passing. For one thing, I am now a 6'5" woman. But that is okay. As long as I don't be beat up or arrested, I don't mind.

I exit the restroom about dusk, and immediately one male motorist says something to me. I am spooked enough by this that I confess that I rudely ignored him. The rest area did get to enjoy the sight of a tall sexy woman checking the lines and tiedowns on a large trailer.

After an hour or so of enjoying the drive, I pull in to a fast food place for some dinner. I couldn't go through the drive through if I wanted to, so I park the rig on the edge of the lot and stride right in. To my amazement, the other customer barely seem to notice. I know that I would stare at anyone walking into a hamburger joint in a little black dress, hose and heels.

About 10:30, I pull into a Walmart to get a couple of things. By this time, I am pretty comfortable and don't mind the stares at the well dressed CD. Presently, a very attractive black woman comes up to me and tells me I have great legs. She said she had been stalking me for 5 minutes and thought I looked great. She asked if she could take a couple of cell phone photos, to which I said sure. We have a nice chat and she introduces me to her 20's black daughter and white daughter-in-law. When I told her she didn't look old enough for those two, she said she was about as old as me at 46. Now I am really feeling good, since I am 58 and I told her so.

Then a couple of female employees approach, one of which had helped me find something earlier. They were very friendly and wanted to know if I was an entertainer. I assumed that was because I looked so good rather than so silly. One wanted to know why I was wearing hose on such a warm night. I didn't want to say it was to hide my hairy legs, so I just said I like pantyhose. One asked if I was married, and I cracked her up by responding, "is this a proposal?" The checkout clerk called me Dear.

Another hour of driving and I was getting close to the northern state line. By now I love this state, so I pulled into a hotel with a big parking lot, walked into the lobby completely en femme, and in my normal male voice asked for a room. Inside, off came the dress, loosened the corset, and loved the view in the mirror. I sat down on the bed for a minute, and a couple of hours later woke up enough to take off the heels and brush my teeth, but I slept the rest of the night in my black hose, black bra, and red corset.

The next morning, I left North Carolina with considerable regret.

Sorry for the long post. If there are any other CD sailors here from the Annapolis area who would like to race sailboats, let me know. We'll show them what a crew of pantywaists can do (what is a pantywaist anyway?)

Elizabeth

trannie T
09-13-2008, 09:15 PM
If you did so much in just North Carolina I can not imagine what would happen on a coast to coast road trip.

Tracii G
09-13-2008, 11:59 PM
I'd like to party with you salior

Michelia
09-14-2008, 02:04 AM
As a long time sailor (and a while back) I really enjoyed reading your post.

Thanks for the laugh.

I could see how the two activities could mix well together. Makes me fell like I missed out on something not having crossdressed during those years! I must admit to being a wee bit jealous.

Michelia

Sally24
09-14-2008, 08:13 AM
Sounds like a great trip!!

Raychel
09-14-2008, 08:47 AM
I have traveled that road many times, by myself, with my father, with my grandfather, and with my wife and kids. I have to say that never once has it been as enjoyable as you made it sound.

I will tell you that my wife is in love with (J&R something), we have to stop everytime we go by. My only wish is that they had more in the way of lingerie and dresses that Raychel would like.

Maybe I will print your post and show it to my wife, hopefully our next trip will be more fun. :heehee:

Jocelyn Renee
09-14-2008, 05:27 PM
Thank you for sharing such an awesome story. It made my day!

Maibh
09-14-2008, 06:00 PM
pant·y·waist (pnt-wst)
n.
1. A child's undergarment consisting of a shirt and pants buttoned together at the waist.
2. Slang A boy or man who is considered weak or effeminate.

Sounds like you had a great time traveling with your long pole, congratulations.

Kate Lynn
09-14-2008, 07:20 PM
If you did so much in just North Carolina I can not imagine what would happen on a coast to coast road trip.
she'd probably have to stop at every outlet mall,and finish her trip in about 2 years.

:drink:

Amy Lynn3
09-14-2008, 07:44 PM
Elizabeth, glad you enjoyed your time in North Carolina. We love out state and I find it most friendly to Tg's. Next time you are down this way give me a shout out. Loved the story.

docrobbysherry
09-14-2008, 08:10 PM
I need to move to NC! Of course, coming from Calif. with two+ moving vans filled with ladies things, I'm probably better off sailing there!

So, should I go thru the Canal, or around Tierra del Fuego?:unsure:

Elizabeth Ann
09-15-2008, 01:47 PM
As a long time sailor (and a while back) I really enjoyed reading your post.

Thanks for the laugh.

I could see how the two activities could mix well together. Makes me fell like I missed out on something not having crossdressed during those years! I must admit to being a wee bit jealous.

Michelia

Yes, you are right. Many times I have gone singlehanded sailing, and once away from the land, stripped down to my panties. It is wonderful to sail along in as wide open a space as you can get, feeling the sun on my skin, and not worrying about another person or care intruding on my privacy.

I've never tried dressing up while sailing, but now that I think about it, it would be fun. Shoot, now this is going to make the next month or so until the boat is back together even more difficult to endure.

Liz