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Coming Out As A Crossdresser In Real Life (5 Years on GD Special)

Posted 12-29-2020 at 07:42 AM by SissySlutSamantha

Today marks my 5 year anniversary here on Getdare, and what a 5 years its been.

Most people who know me on the site know me as an avid crossdresser who likes to dress up whenever I have the chance, I've made so many friends here on GD who have seen me in a whole host of outfits. GD has been a massive source of confidence boosting for me and people such as MaidJay and Ethancole have been so amazing and people Like Victoria85 have been so inspiring to me, so I thank everyone Ive spoken to or done dares with

Ive been dressing up for as long as i remember, I think I was 7 or 8 when I realised I liked to dress as a girl but had been put into dresses by female friends as a younger child.

I have suffered from mental health issues for a few years now and found that crossdressing calms me and helps my brain out.
I originally thought that I was maybe trans and actually came out to an old friend as trans years ago. Ive since realised that I am just a man who likes to dress up as a woman from time to time which is sad really cause i would have loved to have had all the perks of being a woman: soft skin, pretty as heck (yes all of you) and the boobs would have been nice as well XD

I've dressed up in front of people in real life only a couple of times but always under the guise of something else, so no one has ever really been suspicious.

The first time was for halloween when I purposefully lost a bet to a friend with the loser wearing a witches costume for halloween.

The second time was for Fancy Dress party, we thought it would be fun to all throw TV and movie characters into a hat and dress up as what we pulled. As the host of the draw i may have rigged it so I got a female character and even rigged some friends to be dressed up as women to.

But after 18 years of hiding this secret from everyone I knew, I realised it was time I had to finally tell someone.

I have been with my partner for almost 2 years now, I love her dearly and wouldn't change her for the world. We live together and spend as much of our time together as possible. I have worn my Dress from the fancy dress party in front of her on a few occasions for minutes at a time just as jokes. She's never really liked me wearing it and has told me to throw it away on many occasions, I've even put one of her fancy dress costumes on as a joke (from the same party) but she's immediately told me to take it off and stop being "gay".

My mental health has suffered during this pandemic as im sure it has with many of you as well. But not being able to use my comforter of dressing up as my partner was home a lot really made me suffer. Ive had a few sporadic times of dressing up but never as much as I needed.

Yesterday I decided after many sleepless nights that I just had to tell her. I was so scared as I didn't know how or if it would affect our relationship, or if she would even want one at all any more.
We spent the morning cuddling in bed watching Netflix as I sat there running the best way to tell her over and over again in my head. I almost told her on like 10 occasions yesterday but wimped out everytime.

Until I finally bit the bullet and told her I had to tell her something that i had been hiding from her.

I told her it wasn't anything like cheating or being gay to brace her, I paused for what felt like a life time. Then I finally blurted out "IM A CROSSDRESSER"

My heart almost stopped, I couldn't believe I had actually said it. Another lifetime passed before i heard her laugh.

She said "Thank god I thought you were gonna say you were on drugs"

I looked at her and started apologising over and over agin as if id ruined her life. She told me not to apologise, "If thats who You are then I'll do what ever I can to support you" she said. At this point I burst into tears as the weight of 18 years had just been lifted in an instant. I reassured her that I wasn't any different then the man she loves. She told me she loves me as a man but if ive got to do this then she's not gonna argue or tell me not to.

I told her that I had saved loads of reading material about being a crossdresser which she read and then she asked some questions which I tried to answer as truthfully as I could.

Truth be told, now that ive told her im less inclined to dress up in front of her, but I'm going to pitch a ladies night to her where we can break the ice and she can see me in my crossdressing glory.

After such a rubbish year it feels great to end on a high note. And I hope this helps people who are struggling to come to terms with things like crossdressing to realise its really not that bad.

I wish everyone a happy 2021 and look forward to the next 5 years.
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  1. Old Comment
    Im so pleased for you. What a lovely blog post to read. Id love to hear how it goes over the next while. Maybe it'll inspire others to do the same. Well done and I hope you feel proud!
    Posted 12-30-2020 at 12:46 PM by Clueless1 Clueless1 is offline
  2. Old Comment
    SissySlutSamantha's Avatar
    Thank you so much, will definately keep a blog of how things go in the future, hoping for some big changes in the coming months
    Posted 12-30-2020 at 03:02 PM by SissySlutSamantha SissySlutSamantha is offline
 

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