Did me crossdressing at a young age make me a cuckold later in life

Discussion in 'Real Life Experiences' started by latino1974, Nov 1, 2019.

  1. latino1974

    latino1974 New Member

    As far as 5 years old I was drawn to womens clothes and throughout my childhood and into my early 20's I regularly dressed up as a girl. My features were always somewhat feminine and during my teen years I was usually noticed by men that knew about crossdressers, they could tell. My earlier sexual experiences were with boys my age and I always adopted the feminine role and as I got older, even though I liked women I dressed up as a girl and later in my late teens I had sex with a few men while looking feminine.

    Later in life I got married and my wife supported my dressing up so during my first years of marriage I shaved my legs, plucked my eyebrows and had my hair styled in a feminine fashion but still able to look boyish around friends and family that didnt know.

    Eventually this caused resentment in my wife and 8 yrs into our marriage she slept with someone while visiting family mainly because she wanted to be with a "real" man as she put it. It was painful but 5 years later I started getting into cuckold porn and eventually convinced my wife to date for money as a sugarbaby and enjoy herself with other men. She dated older men with $$ that gave her gifts for her time and took her to fancy restaurants, expensive hotels etc.. this was very erotic to me but I am curious how it all connects. Im not sure what everyones thoughts are as to how my years of dressing up and trying to look feminine concluded in me having my wife date other men, even tho the 1st affair was so painful to me...how did it switch and why? thoughts welcome.
    tiruh811 likes this.
  2. Allintogether

    Allintogether New Member

    I think wearing women’s clothing definitely sent messages to my wife, it allowed her to redefine the boundaries of our relationship and gave her room to put her desires in place. She loves a dominant man and actively seeks them out, and I fully understand the attraction for her.
    tiruh811 likes this.
  3. Worth It

    Worth It Well-Known Member

    You're a bisexual Lesbian.
    tiruh811 likes this.

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