Outing Archives - The Crossdresser Report

First Crossdressing Outing Before Diva Las Vegas – Sami’s Week

Sami — Thu, 04 Aug 2022 07:00:45 +0000

Well, it’s Friday the 8th of July. I’ve already registered for Diva Las Vegas, happening in October. I haven’t really crossdressed for a couple of years, and definitely not out in the open. How am I going to start getting…

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Why Be Afraid of a Sandwich? Sami’s Week

Sami — Sun, 08 Apr 2018 15:00:00 +0000

As a crossdresser, I have overcome several of my fears. My biggest struggle is direct contact with strangers. I have no problem walking among people while dressed, driving, etc. What I do fear is one-on-one interaction. Overcoming crossdressing fear is…

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Susan Miller’s Neighbor

Sami — Wed, 14 Mar 2018 22:49:31 +0000

Long before I started writing this blog, I followed a number of others. One of those is by Susan Miller. Over the years, some of her stories have amazed and inspired me. In my opinion, one of the best stories…

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Overcoming Fear & Churchill: Sami’s Week

Sami — Fri, 09 Mar 2018 20:04:45 +0000

I didn’t know until Tuesday night that Winston Churchill, the leader of the United Kingdom during World War II, and I, a somewhat timid crossdresser, have something in common. That something is overcoming fear. My wife and I decided to…

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Limited Crossdressing OpportunitiesSami’s Week

Sami — Tue, 09 Jan 2018 03:11:28 +0000

For all of us crossdressers, we have our share of ups and downs on our crossdressing journey. The past few months were an up for me, but I’ve had a setback. I now have more limited crossdressing opportunities. Adjusting to…

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Sami’s Week appeared first on The Crossdresser Report.

Crossdresser Shopping Trip with a New FriendSami’s Week

Sami — Tue, 19 Dec 2017 22:42:28 +0000

I got to do something last week that I never thought I could do in this rural part of America! No, it wasn’t tipping over a cow, nor was it waiting to pass a slow-moving tractor. No, my friends, it…

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Sami’s Week appeared first on The Crossdresser Report.

Sami’s Week:Dealing with Fear as a Crossdresser

Sami — Fri, 08 Dec 2017 18:48:42 +0000

One of the main reasons why I wanted to start this blog is because I want to grow as a crossdresser. The opportunity to check out restaurants gives me a place to have as a destination in mind for crossdressing…

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Dealing with Fear as a Crossdresser appeared first on The Crossdresser Report.