NEEDING SOME HELP
from Wendy

Dear Helga,

I would like to ask for your help on a matter that has occurred here.

I am seeing a man who has divulged his desire to be submissive to me and to dress as a girl. I have never had a relationship like this but find myself intrigued and wanting to explore this. He has had these desires for many years but never found someone he could be open to about this.

We have explored together the basics about dressing him in girl clothes and personal hygiene as a girl. He happily takes commands from me.

When he has been naughty he has been punished by me with a strap across his bottom and understands the love involved in his punishment.

As I am new to this, I need to ensure that the progress of this new relationship is going as it should be. I realise that every relationship can be different to the next but I have several questions and would appreciate your input.

I have my submissive dressed in girl clothes, happy to do anything at my beck and call and is wanting to service me. What I would like to understand is if this involves just my submissive pleasuring me orally? We have not had sex as man and woman since the roles have begun. I understand that my submissive should not be allowed to release regularly but I am wanting to know if it is good to leave my submissive so long without releasing. Are we able to have sex as a couple? Also would like to understand if it is okay to pleasure my submissive orally.

I thank you for any help you can give in this matter.

Yours sincerely
Wendy


Thank you for your letter Wendy. Each of us approaches this lifestyle in our way, many have regular jobs and live otherwise normal lives. So far from what you've described his opening up to you and being honest are positive signs for a long term commitment.

Of course your acceptance and willingness to participate and to experiment as well as trying to learn more also, in my opinion also bode well for a positive relationship, one where you are in charge and define the parameters and her role, both limits and direction.

Oral services are to be expected usually, though see my point above about your defining this for yourself, that said, should you chose to have intercourse with her occasionally, sure, this is not about one way or anther, this is about your way, its all up to you. Providing her with oral sex could be a reward for something extraordinary I suppose. As far as her regular release is concerned, every two or three weeks the sissy should be drained, either conventionally with sex or by physical manipulation like a prostate massage, so called 'milking'. You did not mention if she is in a chastity device, but I feel she should be.

You are at the start of something that will be quite amazing.

Helga

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Letter 6