My name is Jill, and I have a boyfriend called Simon who I have been with for 3 years. I am writing to you in the hope that you may be able to help me to make Simon into a little girl.
Let me explain please. Last year Simon and I attended a party dressed as school girls. I admit that I conned Simon a bit by telling him that someone else had got the boys school uniform and I had to accept the girls school uniform. To be honest it was the best thing that I could have done to stimulate our relationship. Simon looked lovely in his short pleated skirt, which just hid his navy blue knickers. All of my friends thought that he looked a sexy dish, especially when his knickers were exposed as we danced. The party was really enjoyable and everyone agreed that it was a great success. Admittedly we had had a bit to drink and I was feeling very randy and excited that myself and Simon were dressed as school girls. It was so sexually stimulating to be fondling each other, up our skirts and through our knickers, whilst kissing passionately. The night was truly wonderful, ending in the best sex we have ever had.
Sadly I have been unable to engage Simon in any repeat of our wonderful school girl antics. I haven't been able to get him to agree how much he enjoyed our sex on the night of the party. I am sure that he loved being dressed in girls clothes, the giveaway being how rock hard his penis was when I was fondling him through his knickers. He dismisses the conversation every time I mention us being dressed as school girls together.
I have a passion to dress Simon as a little girl. A passion to have him wear sensual satin underwear trimmed with luscious lace, and a short dress which almost exposes his frilly knickers. Selfishly I also want him to wear a baby doll nightie so that we can be girls together. My feelings are very strong and I want to get him to admit how much he likes being a little girl and wants to be one. It's a mad thought perhaps, but I just can't help it.
The question is where do I start? Can you help please?
Thank you for your letter Jill. Your wishes are not at all mad, they sound reasonable to me. It may be that the memory is embarrassing to him. This may well take some time, but many girlfriends use knickers to start.
As for introducing him to his new knickers. You could tell him that you have had this fantasy since you were younger of making love with your boyfriend while he is wearing a pair of knickers, it won't make him gay or anything and of course it will remain a secret, etc. Buy a pair or two of full brief style nylon knickers, large enough that he can get an erection in them, and once you talk him into them, make it memorable, fondle him through the knickers, talk to him, tell him how turned on your are by this, even masturbate him to completion into the knickers, have that second pair ready since he couldn't control himself the first time.
Maybe this will give you some ideas, but do so with love, a little force, and tease, most men will agree to anything when you have your hand on their penis, even if doing so through knickers, use that.