Crossdresser Confesses to Girlfriend

I confess that last night I decided to confess to my girlfriend that I am a crossdresser. It went better than I thought and not as well as I had hoped.

Like most crossdressers I have chatted with online, I first started crossdressing when I was little. I didn’t understand why my two older sisters pajamas and underwear were so much softer and interesting than my boring tightie-whities,. How did I know that to be the case? Older sisters! They thought it would be “cute” to dress up their little brother in some of their old clothes; party dresses, sundresses, jumpers, etc. That escalated into nighties, petticoats, slips, and panties when they realized I was enjoying it as much, if not more, than they were. I still remember quite vividly how it felt to be dressed by them on those long weekends when mom and dad were off visiting my aunt and uncle on the coast. Lot of wonderful stories. So, Darlene was born and I continued dressing, with and without them right up through high school. On the night before I went away to college both sisters were home visiting. They wanted to see their baby brother leaving the nest. They took me downstairs and gave me an “extra” suitcase to take with me. Told me not to open it until I got to my new dorm room. It was filled with my favorite dresses, panties, slips, and nighties. I was thrilled but nervous, I had a roommate. Turns out I needn’t have worried and I had a lot of fun in that coed dorm for 4 years.
But a year after graduating I met Cindy. He is amazing ; gorgeous, smart, and so sweet. We have been dating for two years now an I didn’t want to hide it any longer. It wasn’t fair to her and I felt so guilty hiding this secret. Well, I decided that seeing is believing so yesterday I got Darlene ready in her prettiest lingerie; matching black bra and panties, cute little chemise, and one of my favorite A-line dresses. I put on some light make-up, my long, curly, auburn wig and pair of 3” black patent leather heels. I had asked her to come by because there was someone I had wanted her to meet. Extremely curious, and apparently a little nervous, she arrived ten minutes early. Knowing her and knowing she would do exactly that, I was ready 20 minutes early ;-D I answered the door, invited her in and watched as she slowly figured out who I was. We spent the next hour sitting on the couch, with me explaining how I got to be here, who Darlene was, and how she is just me with a different wrapper. She asked some questions but mostly just listened. No screaming or yelling things like, “Weirdo, pervert, or crazy.” She finally said, “I knew you were hiding something. I had started to think you might be seeing someone else. “ Apparently she had found some panties that weren’t hers in the bathroom one morning and wasn’t sure if it was someone else or a souvenir from a past love. “I need some time to think”, she said and I haven’t seen or heard from her in 12 hours. I really love her and I hope she comes to understand that and accepts me for who I am. Wish me well!

Dec 8, 2020

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  • My girlfriend talked me into cross dressing for her, I actually love it. Thrown away all my male clothes, and only wear leotards and tights for her, or cheerleading uniforms! I've been taking female hormones for two years now. I have nice C cup b****** now! My b****** are so soft and bouncy, and she loves them! I love showing them off to family and friends.

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