Sissy Advice – Ask Mistress!

Dear Mistress,
i would be honored if You were to reply to this message with either suggestions or even feedback concerning my situation.

i am a 59 yr old straight male, but am obsessed with the thought of being sissified, and put on display for public humiliation.

One of my obsessions, strangely enough, is having my own hair set in curlers. In my younger years, i would call a salon and make an appointment for a wash and set, using the pretense that it made my male hairstyle lie better on my head. my hair was not all that long, but still when the stylist was done, i was able to go home and style it in a short flip style since it had so much body and took to the curls very strongly. This went on for over 20 years, 8-10 times per year, and what a great feeling that was every time.

There has been many private crossdressing episodes also in those 20+ years, but for now, i’ll just stick to the hair obsession. i bought my own rollers and tried doing it myself, but could never get it right like they did in the salons. i bought my own curling iron, and was able to style my hair much better, but the feeling of being in curlers just wasn’t there, nor the feeling of public humiliation. i have had several girlfriends and was even married for 8 years, but was never able to broach the subject with any of them, except for halloween, when “somehow” the subject of what to go as came up, & i would suggest going as each other, but instead of wearing a wig as she would suggest, my argument was that we wanted it to look real, so we should try putting it in curlers.

All girls were receptive to that, and most set it themselves, although twice, they took me to a salon, where i got the works, including make-up and nails. Then finally, in my late 40?s or maybe 50, there was a lady who took an interest in me, and i in her, but i wanted to be totally up front with her before we got too far into the relationship. i carefully broached the subject, making sure she promised this would stay between us, and not get out to my family or friends, she agreed. i fumbled through my confession, and surprisingly, she said that was “cool”, and i should be able to dress the way i wanted to.

But not only that, she also told me that she had had beauty school training, and would be happy to do my hair for me. Needless to say, i was wearing dresses, sleeping in nightgowns, and wearing curlers around the house quite often. She had 2 daughters, 19, & 23, whom she invited over while i was in curlers, and dressed in some manner, adding to my embarressment, but still a thrilling feeling.

On my birthday, she surprised me with a visit to the beauty salon. She had set up the appointment, telling them that she wanted my hair done in an ultra feminine style, and that i had no say in the matter. The salon agreed, and that’s just what they did, feminine cut, shampoo and set. Although she would set my hair 3-4 times a week, still about once every three months or so, she would make an appointment at the salon for a female style, and i again never had a say in the matter. i was in seventh heaven!!!

This went on for about 2 years or so, and in the last 4 appointments, she always had some type of barrett or hair ornament that she had them put in my hair before we left. the last couple, she made me carry a purse to the salon. i over heard her laughing with the beautician, that pretty soon, she would have me here in a dress for my appointments.

Then it happened! we had a big argument, and she left me. i was lost. i tried styling it myself with my curling iron, and dressing on my own some, but it was just not the same. A year or so later, i was introduced to a good buddy ‘s  sister who moved back into the area. We got together, and started living together, and have been together for the last 5 years, but no way can i broach the subject of my obsessions with her, as again, she is my good buddy’s sister, and i just can’t afford to be found out by my group of friends.

So here i am in my own agony, unable to explore my obsessions. The only thing i can do is to go to a site called hairmixer.com, where i can at least integrate my face with various female hairstyles, then save the pics in a private file.

In closing, my questions is, “am i insane”, and what am i to do? i can’t get this feeling out of my mind.

Thank You so much if You have taken the time to read this long (and probably boring to You, i’m sure You’ve heard it all) email. i look forward to any suggestions or comments You might have for me concerning this obsession. Again, Am i insane?

Best Regards, don

Dear Darling Don,

Wish I could see you all decked out!

Now for the insane part:  do you believe you are insane, probably not. Perhaps you are just embarrassed not to have told your current SO the truth about yourself. Perhaps you are correct to keep things to yourself.   Are you saying that your current SO has no suspicion that you like a little feminizing from time to time?

As forward as you appear to be, I would guess that she knows something.  What do you think?

Let me know what you are thinking about doing.

PS   I like curlers, too.

Sissy Susan should be butt plugged every day for 3 hours. The plug should be held in place with a double pair of girdle control panties. When removed Sissy Susan should make sure her butt plug is cleaned with her sissy mouth and ready for the next days use. Any complaints from the sissy should be dealt with by making her stand in a corner with a used didlo in her slutty mouth

Oh wow!

Is this an assignment?  Maybe it is something the writer has done.  Gee.  I am glad I’ m me,  and I do try to stay out of the kind of trouble that would get me disciplined that way.