Dear Auntie Helga,
My auntie used to tease me about dressing me up like a girl if I continued being bad. That was when I was 8 years old. When I was 16 she was still saying that to me whenever I stepped out of line. It was always her way of making sure I grew up as a good boy and not one like she heard on the news. On my 20th birthday my auntie took me out for dinner and we talked about some of the funny times. I asked her if she remembered teasing and threatening me to wear dresses. She remembered telling me that that still stands if I test her far enough she will. I laughed thinking no way my auntie would get me to wear a dress ever. She advised me to look up petticoating on the computer when we got home so I did and found your email.
The next day my auntie asked me if I looked into petticoating which I said yes I did. She then said you see Cam there are women that dress their boys and men in pretty dresses. Me being a 20 year old laughed telling my auntie no way would that be me. My auntie made a bet with me that she could have me wearing a dress in one week with ladies underwear and shoes. We shook hands with me figuring I already won the bet. The next day when I cam home there was a used dress hanging in my room with a pair of shoes below. I just ignored them while my aunt was smiling at me when she saw me.
My auntie asked me at dinner if I liked my new dress and heels with me laughing again. The following day I found a bra, a pair of panties and pantyhose on my bed that I tossed in the corner. Once again my auntie asked me how I liked her purchases with me shaking my head. By day 4 I was pretty confident there was no way she could win. The morning of day 5 I woke up with a chastity device on my penis that I couldn't remove no matter what I tried. I never told my auntie that I used sleeping pills to help me sleep better. She put that thing on my penis without waking me up. I tried to get it off and tried to find the key for all of days 5 and 6 with no luck at all.
Day 7 was a Saturday with me determined no way was I wearing that dress for my auntie. On the morning of day 8 I went to collect my money from my auntie which she paid me with no troubles. When I asked for the key to the chastity she pointed to my room. I won my bet but she wanted to see me in the dress for the $50.00 she paid me. To be a good sport I went with her to try on what she bought hoping to hear the end of it. That was the first time I ever wore women's clothing before and it was just plain weird. My auntie was quick with her cell phone taking a couple of pictures of me. She talked me into wearing the dress for a few hours just to see if I started to like it. That cost her another $20.00 which she paid me again. We were watching TV with me also surfing with my laptop when my auntie asked if I would go to the petticoating website for her. She sat beside me as we looked at some pictures of sissymaids commenting on the ones she thought looked cute.
My auntie looked at me asking what I thought about being her sissymaid for fun. Right away I wanted nothing to do with it wanting to take off that dress and stupid bra thing. My auntie calmed me down pointing out that it would be a nice thing for me to do for her. Again I wasn't interested in a sissymaid thing but agreed to help her. She thought it was a good idea and wanted me to do it for a while with her. Before I said no again she suggested I write to Auntie Helga to see how many 20 year old men accepted the offer to be a sissymaid.
I thought alright sending an email is no big deal but that was as far as I was going to go. My auntie decided to wait for a reply from Auntie Helga before giving me the key for the chastity. I was hoping to get a reply soon and stop this sissymaid talk stuff. When I went to take off the dress my auntie brought me one of her long nightgowns for me to wear. I started to get annoyed with her but thought if I just wore it she would get off my case. So I went to bed in her nightgown and panties. I forgot to send the email which I am doing tonight otherwise this chastity thing won't be coming off soon.
Auntie Helga will you reply with something that convinces my auntie this is a nutty idea?
Thank you for your letter Cam. Your aunt sounds like a wonderful person. Becoming her sissymaid would be a great thing for you to do for her, to sacrifice yourself to another person is an honor. Many many 20 year olds would love to have this opportunity, I don't feel its nutty at all and suggest you become her sissymaid, now whether you will tell her what I said I suppose is up to you.