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Should I Tell My First Lover That I'm a Virgin?

Dear Betty & Carlin
My Boyfriend Claims He Doesn't Fantasize

Dear Betty,
Masturbation Saved Our Marriage

I Think I'm Afraid to Orgasm

Dear Betty,
How Can I Control Myself & Not Go All the Way?

Dear Betty, (Oh,this is exciting=D)
Why Don't I Enjoy Clitoral Stimulation?

First off, THANK you for living and breathing! This site has helped me realize that I am not alone in wanting to explore and own my sexuality as a woman!
The first and most important question I have is as follows:
I can only cum by stimulating the areas around my clitoris. I've tried stimulating it before, but any kind of pressure feels tender and hurts. Likewise, I find that after I cum (when using a vibrator) I have to quickly remove it or it hurts almost immediately. What is going on?!
Dear L,
Should I Become an Escort?

Dear Betty and Carlin,
I am hoping that you can give me some advice in regards to entering into sex work. I have the opportunity to take up work as an escort in October, but am not sure whether or not to do it. I'm a student that could really use the cash but have never had sex with someone I am not in a relationship with and don't know how I would feel in the moment when it's time to get laid/paid.
Can You Get a UTI Using a Dildo?

Hi Dr Betty!,
Yet another question. Can one contract a UTI by using a dildo for both vaginal and clit stimulation? After doing that (no anal play involved), I got a wicked one that went into my kidney and I'm a little apprehensive about getting off again using that method. (Peeing fire is definitely not fun!)
I know you are not an MD, but thought your priceless experience might be able to shed a little light on things.
M
Dear M,
Need Advice on Lesbian Safe Sex

Hi,
I want to know about the safest sexual practices I can use, besides abstention. I am lesbian, single and want to insure I'm not bringing anything home I don't want. Are gloves and dental dams the only option, besides getting everyone tested? Sucking on a dental dam is about a wonderful as sucking on a balloon and if guys think rubbers suck. They should try to use a dental dam.
Any suggestions?
Thanks,
E
Dear E,