Dear Auntie Helga,
I need your advice on a situation that occurred with me last couple of weeks when I went to visit my aunt with plans of moving in with her. What happened was the airline lost my luggage for an entire week. It was a bigger deal for me than it was for my aunt since she allowed me to wear some of her clothes. Auntie Helga I am not a gay person or a crossdresser so wearing my aunts clothes was more than weird for me.
The first night she played down losing my luggage and gave me a nightgown to sleep in that night. The next morning after breakfast my aunt gave me a pair of her panties a blouse and a skirt to wear. What I learned was her and I were a similar size otherwise I would have lived in a towel all week. With my aunt living so far from the city there was no way for me to buy new clothes while I waited for my lost luggage. On the second day my aunt brought me a dress to wear along with a few more things foreign to me. She handed me a bra to wear with me wondering what was going on. A few words were said when I agreed to wear a bra with the idea of it making the dress look better on me. With panties and bra on she handed me pantyhose once again telling me wearing a dress meant wearing pantyhose. After a few minutes of trial and error I finally was wearing pantyhose. My aunt gave me a slip and the dress which I put on for her.
The rest of the day went great with us spending time together as planned. She assured me wearing her clothes was no big deal for her so all I had to do was not let it bother me. Every day I wore another dress or blouse and skirt including a bra and pantyhose. A few times my aunt talked to me about crossdresser and something new to me, sissymaids. She was trying to let me know what I was wearing wasn't a big deal and many guys do the same.
My time with my aunt was great except for me wearing her clothes even though the clothes I wore to her place were clean. She convinced me to keep them clean for my trip home if my luggage didn't show up. Well the last day I was there after waiting almost 2 weeks my luggage was delivered. When I got back home my aunt talked to me a few times confirming the date I was going to move in with her. Last night which is why I am writing to you today my aunt called to update me on the painting she had finished in my bedroom or soon to be bedroom.
She also shared having picked up a pair of shoes for me and when I asked what kind she told me pumps. I hadn't heard of men's shoes called pumps so I thanked her for the thought. Later looking on the computer I found out pumps are women's high heel shoes. I thought why at first until I remembered our conversation about crossdresser and sissymaids. That got me started reading about both which led me to your site Auntie Helga.
With me understanding more now than last few weeks I think my aunt wants me to wear her clothes when I move in with her next weekend. Can you tell me if this is normal for my aunt to enjoy seeing me wear her clothes? I love my aunt and look forward to living with her but not so sure about wearing her clothes and now pumps. Do you see any issues here Auntie Helga? Is there a long term plan for my aunt and me that I just don't see? If you do reply to emails sent to the address on your site could you reply to me please?
Thank you for your letter Nathan. It is not that unusual for her to want you to dress feminine for her though I feel she would prefer you to have your own clothes rather than wear hers. Perhaps by dressing you she was exploring her own feelings about having a niece instead. I really wouldn't know if there are plans for more but that she bought heels for you would indicate she might wish to experiment a bit further.