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tall sam
11-27-2010, 02:51 AM
Hi girls.

We all push the limits a bit - and oh what a feeling when it turns out ok and we are buzzing from head to toe!

I am on a business trip and staying in a hotel in Jamaica. Crossdressing/TV and anything odd like that is not really common or accepting here.

Anyway, I brought some clothes with me, including makeup, wig. I have dressed a few times in the evenings in my room but tonight decided to take it one more step. Its 2:30am so decided to go for a walk on the beach.
I took the emergency exit stairs and expected to walk out into a deserted pool and beach area. Out the door was fine, then there was the first couple sitting on the beach loungers. So I headed the other direction just to see one of the local hagglers heading my way, I turned around and walked down the beach and sat down on a lounger.
I think I was pretty well dressed en fem but my height at 6'6 does not help passing. Luckely the area is poorly lit.
So, the local haggler came up and sat down as well, I ignored him then evenetually asked him to leave me along in my best fem voice. I thought this was the end of my problems.
After he left I walked down the beack for a while then on my way back, my "friend" approached again, I just walked past in my best fem stride. He didnt seem to have figured what I really was becouase he left me alone - I am sure he would have bugged and chirped me if he realised anything else!
I then headed back to the hotel but ended up comming across a security person who I think suspected soemthing but luckily let me go. I ended up taking the lift up to my floor.

I guess we all get our thrills in different ways. I get them from going for a walk en-fem, but this little unplanned episode gave me a real buzz.

Enjoy dressing my friends

Sammy! (feeling sexy!)

Rianna Humble
11-27-2010, 05:22 AM
Congratulations on a successful outing. You get boorish people anywhere, but I think you handled that very well. As for the security person, if you want to dress, it's none of his business. All that should concern him is looking after the guests - which includes you!

juligirl1984
11-27-2010, 05:31 AM
thats scary! I once was up in the mountians driving around late at night. then three trucks came up to my truck. I was all dressed up and everything. I just drove away fast and one followed. thank god it was at night because I was not stopping for anything.

MJ
11-27-2010, 06:51 AM
i feel it's all in how you carry yourself. you did well for your first time out. nothing happened you had fun so you better get out again soon while you have your new found confidence it gets better every time sis

Starr
11-27-2010, 09:06 AM
You need to be very careful, Jamaica is not a safe place for those who might be considered to be gay. Some gay advocates have even been murdered there for unknown reasons. Jamica is said to be the most homophobic place on earth, weather you are gay or not being seen as a CD in Jamaica could allow others to take that as you being gay.. Do a search on gay Jamaica and see what all is said about it..

AKAMichelle
11-27-2010, 10:05 AM
Congratulations on taking that step.

tall sam
11-27-2010, 11:36 AM
You need to be very careful, Jamaica is not a safe place for those who might be considered to be gay. Some gay advocates have even been murdered there for unknown reasons. Jamica is said to be the most homophobic place on earth, weather you are gay or not being seen as a CD in Jamaica could allow others to take that as you being gay.. Do a search on gay Jamaica and see what all is said about it..

Thanks for this, and you I was area of it. But when you need to go out, then you have have to go!!
I was hopefully sensible anough. Its a fairly private report - ie I was not out wlking in an open public place.
I dont think the first person who hassled me a bit even realised I was a CD. He was probably a bit stoned as he was trying quite hard to chat me up (or sell me something to smoke!). As for the security guard, Rianna's comment is probably about right, although this could possible still land me in some trouble if he got stroppy.

Thanks for the encouragement and advice
Sammy

danielletorresani
11-29-2010, 12:47 PM
Nothing like the rush of pushing boundaries while dressed up!