Ex needs to find someone tolerant of cross-dressing

By: Miss Lonelyhearts Posted: 2:00 AM CST Tuesday, Mar. 8, 2016

Dear Miss Lonelyhearts: I had a perfect new boyfriend for a month —he was gorgeous, we shared the same interests and we had great chemistry in bed. I thought that would be a cause for celebration, but it wasn't. My feet were cold the other night, so my boyfriend told me to get some socks out of his drawer. He had a funny look on his face. I went to his sock-and-underwear drawer, and what did I see but pairs of fancy women's underwear in red, purple and black lace, folded up beside regular men's underwear.

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Hey there, time traveller!
This article was published 08/03/2016 (3866 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I had a perfect new boyfriend for a month —he was gorgeous, we shared the same interests and we had great chemistry in bed. I thought that would be a cause for celebration, but it wasn’t. My feet were cold the other night, so my boyfriend told me to get some socks out of his drawer. He had a funny look on his face. I went to his sock-and-underwear drawer, and what did I see but pairs of fancy women’s underwear in red, purple and black lace, folded up beside regular men’s underwear.

I walked up the hall carrying the panties and asked them whose they were. He said, “Mine. You need to know I cross-dress.” I asked him how far he goes with it, and he said, “Just underwear, so far, but it will probably go further.” He said he couldn’t tell me before because he hoped I wouldn’t reject him and would accept him. He said he used to have a long-term girlfriend who was fine with it.

It was a very sad parting. I cried outside in the car, but I’m just not into it. I don’t want to feel like the second woman in the bed. I will miss him. He keeps phoning and leaves messages in his deep voice. What should I do?

— Shocked and Devastated, Downtown

Dear Shocked and Devastated: Unfortunately, it’s not just about being open-minded and tolerant. As the “straight” woman in this situation, it also affects the role you play in the sexual relationship. If that role is abhorrent to you, then there will be shaming ahead for this cross-dressing man, and it’s a good thing for both of you if you move along now.

Hopefully, the man you’re leaving behind will find someone who is OK with his situation, possibly be bisexual or lesbian, and the roles aspect can become blurred with little or no adjustment as things change. He hinted he had further to go in this journey. Sadly, since you had a good connection in the beginning, you won’t be able to go along that road with him. You need to look for a guy who has the qualities you liked about him, but not the sexual complications. And, he needs to find a woman who is good with him in his evolving situation.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6

Miss Lonelyhearts
Advice Columnist

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