When I was very young we lived in an old two story house and the up stairs became very cold in the winter time. So cold that we never used it during winter and I remember that I would sleep with mom and dad at night. My parents eventually divorced and I was raised by my mom. I learned at a young age to do as I was told or suffer spankings with a hair brush. Mom suffered from the delusion that I should have been her daughter. Most of the time we played dress up which I was dressed like her daughter. This was on going everyday we played dress up. I remembered getting a little stiffy when I got naked and putting on my panties. Mom would always smile and then go get a hand towel. She would say pull your panties down honey, which I would do. Then she would tell me that we can not have that protruding it will show through your dress as she message my stiffy which felt so good. She would do this until some goo came out and then wipe me off telling me to pull up my panties.
Mom told me that I should never do that by myself because I may do it wrong and permanently hurt it. I should always have her do it so I would not hurt myself. She seemed to enjoy taking care of my stiffy because she would always kiss my forehead once she was done saying what a good “boy” I was. I recall waking up at night with a stiffy and I woke her up pointing it out to her, in turn she would take care of it for me. Then after three nights of this it was the norm that mom would have me stand naked in front of her and massage my stiffy before I would put my nighty on for bed.
By time I went to school mom would dress me as a “boy”. My “girl” dress up time was saved for bed time and weekends. One evening before bed and after my climax, she lay down beside me with her hand on my slowly weakening stiffy. She told me that I will be getting stiffies much more frequent as I got older and should remember to come to her for relief. She also kept telling me they were not a good thing to be getting all the time. She told me that she was going to make my stiffies go away and I would not have to worry about them. I was asked if I would like that and of cores agreed to it. I was given a pile once a day to keep from getting stiffies.
Then one day a friend of moms stopped by and being a close friend she knew I was a sissy boy. I over heard them talking that I should never become erect but some men liked sissies with erections. I also heard her tell mom I would be worth more if I was able to ejaculate with men. I had no idea what they where talking about. When I walked in the room they changed the subject. I asked what they meant about men wanting sissies with erections? They told me that I must try to control my stiffies. I said I can’t they just happen whenever I dress like a girl. Mom asked, you like dressing like a girl don’t you so her friend could witness my acknowledgement. Yes mom it makes me feel so pretty I told them. Mom asked if I wanted to dress up now and I told her I did. Her friend accompanied her to my bedroom and watched as mom told me to take my close off. When I did, her friend commented that I had such a small penis. Mom said that is why I was a girl because I had no man hood. I didn’t mind I just wanted to be pretty for the day.
As I matured I was feminized more and more each year. I became a sissy escort for men by moms orders who also arranged the meetings. I was used for sex and doing things that I thought where not proper for me to be doing. Mom some times watched me as I satisfied men as she gave her approval after telling me what I was to do. I learned how to accept cock in my rear so they could screw me and administer blow jobs. Mom made good money whoring me out to men, I went along with it because she was happy and I knew nothing else. When she passed away I was an adult and continues to be a sissy prostitute. That is how I make my living and eventually had breast implants. I enjoy the life style and if I had it to do over again, the one thing I would have changed. I wished mom would have given me breasts when I was younger.
“SM” Sissy Maker.