jennyscott
09-06-2013, 02:12 PM
The day finally came. I told my wife I am and have been a cross dresser from an early age. A little background information before I go further. After reading numerous posts here this summer I resolved to tell my wife. How? When? As usual, there was no shortage of advice. This is a long post. My attention span usually prohibits such offenses. This post may later be supplemented with humorous “Micro-posts” or mini conversations of the weekend as I remember them.
I began by writing a letter. It was actually completed more than a month ago. During the time when I was trying to find the “right” moment I found some sound advice stating that I should do it in person. I thought that was great advice due to the potential for questions and tangents that we as a couple should be able to address on the spot.
When? That sort of resolved it self. I travel for work. As a result, my dear wife is stuck with the household realities without escape. We needed to get away! Beginning mid-July I planned out a three night Labor Day get-a-way to a popular Delaware beach in celebration of our 20th Anniversary :). It was as stress-free as possible. Empty wine (or rum) glasses and decisions concerning dinner were the toughest situations we encountered :). The timing was set.
As an aside – my wife has known and has been fine with limited underdressing for the last 10+ years. All of my work socks are knee-highs and fem t-shirts. I have avoided men’s underwear for longer than that. I only have one pair of “standard” Levis and sleep exclusively in nightgowns. So in a sense, she was aware of some dressing. As this weekend approached I told her I wanted to leave all my male clothes home. Having done this once before (trip to HI) she was a bit leery but gave in. Maybe it was my persistence. Maybe it was because I packed the suitcase. Her apprehension was due to not knowing of my wardrobe. Mind you it was not hidden but stuffed in the limited drawers I had. To compromise a bit I brought one t-shirt from “his” collection, one pair of shorts, and a bathing suit (that I never wore).
So there we were, Friday afternoon, on the beach, enjoying some wine (for her) and rum and cokes for my self. Sipping and talking, I am enjoying the sun, bikini bottoms covered by woman’s swim shorts and a tank top. Hey, I’m trying to “improve” my tan lines after all. After we both had time to relax and after “critical beer” (a service term I coined for the moment my golf game went to crap – usually after one too many “sips”) I broached the topic of cross-dressing. I simply told her that it began long before we married, dated, or met. It began before puberty. I mentioned that I had (hand-) written a letter and had it with me if she wanted to read it. She was quite surprised that I was carrying it around. She deferred at the time but asked to read it the following day on the beach. After reading the four pages she gave me a hug and kiss. Some of you know how you didn’t feel just right as you grew up. Only later did you figure it out. Well that was the case with me.
As you may expect, she had some questions and was very empathetic. She did say she enjoyed me in male mode (with hair). I may add that I was pretty well shaven for the trip. The numerous posts on this site had warned me of not jumping into the pink fog after sharing this part of myself. Knowledge and higher levels of acceptance can be quite exclusive. I told her I would like to dress more as it was just part of me. Of course this all has to be tempered with our home environment. She is still not ready to explain my clothing choices to anyone (hence the distant beach trip). With that understood she has approved of my sun tanning on the back yard patio. Perhaps she knows I can’t sit still and will be working in the garden or yard instead, in more appropriate shirts and shorts.
During the rest of the long weekend I dressed in casual feminine clothes and the usual bra, panties, and shoes/sandals. We spend a full day in Cape May waling from shop to shop. Of course I had to carry her “Whale Tale” beach bag the entire time too :).
Since then, nothing much has changed, almost. Recently, when I went out to cut the grass in a fem tank and shorts she said nothing. In the past she usually would asked me to change the shirt.
We still have topics to explore – makeup, wigs, etc. But if experience has taught me nothing else it has taught me to take things slow. Part of this may need to stay in the DADT arena for a bit longer but one day I hope to go shopping with her as a girlfriend.
I began by writing a letter. It was actually completed more than a month ago. During the time when I was trying to find the “right” moment I found some sound advice stating that I should do it in person. I thought that was great advice due to the potential for questions and tangents that we as a couple should be able to address on the spot.
When? That sort of resolved it self. I travel for work. As a result, my dear wife is stuck with the household realities without escape. We needed to get away! Beginning mid-July I planned out a three night Labor Day get-a-way to a popular Delaware beach in celebration of our 20th Anniversary :). It was as stress-free as possible. Empty wine (or rum) glasses and decisions concerning dinner were the toughest situations we encountered :). The timing was set.
As an aside – my wife has known and has been fine with limited underdressing for the last 10+ years. All of my work socks are knee-highs and fem t-shirts. I have avoided men’s underwear for longer than that. I only have one pair of “standard” Levis and sleep exclusively in nightgowns. So in a sense, she was aware of some dressing. As this weekend approached I told her I wanted to leave all my male clothes home. Having done this once before (trip to HI) she was a bit leery but gave in. Maybe it was my persistence. Maybe it was because I packed the suitcase. Her apprehension was due to not knowing of my wardrobe. Mind you it was not hidden but stuffed in the limited drawers I had. To compromise a bit I brought one t-shirt from “his” collection, one pair of shorts, and a bathing suit (that I never wore).
So there we were, Friday afternoon, on the beach, enjoying some wine (for her) and rum and cokes for my self. Sipping and talking, I am enjoying the sun, bikini bottoms covered by woman’s swim shorts and a tank top. Hey, I’m trying to “improve” my tan lines after all. After we both had time to relax and after “critical beer” (a service term I coined for the moment my golf game went to crap – usually after one too many “sips”) I broached the topic of cross-dressing. I simply told her that it began long before we married, dated, or met. It began before puberty. I mentioned that I had (hand-) written a letter and had it with me if she wanted to read it. She was quite surprised that I was carrying it around. She deferred at the time but asked to read it the following day on the beach. After reading the four pages she gave me a hug and kiss. Some of you know how you didn’t feel just right as you grew up. Only later did you figure it out. Well that was the case with me.
As you may expect, she had some questions and was very empathetic. She did say she enjoyed me in male mode (with hair). I may add that I was pretty well shaven for the trip. The numerous posts on this site had warned me of not jumping into the pink fog after sharing this part of myself. Knowledge and higher levels of acceptance can be quite exclusive. I told her I would like to dress more as it was just part of me. Of course this all has to be tempered with our home environment. She is still not ready to explain my clothing choices to anyone (hence the distant beach trip). With that understood she has approved of my sun tanning on the back yard patio. Perhaps she knows I can’t sit still and will be working in the garden or yard instead, in more appropriate shirts and shorts.
During the rest of the long weekend I dressed in casual feminine clothes and the usual bra, panties, and shoes/sandals. We spend a full day in Cape May waling from shop to shop. Of course I had to carry her “Whale Tale” beach bag the entire time too :).
Since then, nothing much has changed, almost. Recently, when I went out to cut the grass in a fem tank and shorts she said nothing. In the past she usually would asked me to change the shirt.
We still have topics to explore – makeup, wigs, etc. But if experience has taught me nothing else it has taught me to take things slow. Part of this may need to stay in the DADT arena for a bit longer but one day I hope to go shopping with her as a girlfriend.