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Hello Mistress Jane: I'm a 38-year-old male who has been cross-dressing for about ten years. I love the feel of silk and satin and often wear panties, nylons and garters to work. At home I'll add a bra or a chemise.
However, I still have trouble with something. I like to masturbate while I'm wearing my lingerie and some of the fantasies I have are very exciting. I fantasize that I serve a mistress and she makes me buy lingerie while she is with me. She makes me wear lingerie to work so that my secretary notices my lingerie. She makes me suck another slave's cock. This culminates with a mind-blowing orgasm, but then I often feel guilty. I feel guilty that I fantasize about serving a mistress, sucking cock, and even sometimes I feel guilty because I wear lingerie. Help!! Any suggestions on how to feel more comfortable with this? -- "Tanya" Dear Tanya: Just one letter from me is probably not going to assuage a lifetime of guilt, Tanya, but let's at least discuss this.
It sounds as though you've reasoned out and made peace with your lingerie-wearing intellectually but not emotionally. Hence, the guilt. And some of that guilt, I suspect, stems not just from the submissive part of the fantasies but the cock-sucking part, the gay part. Remember, Tanya, that you cannot control your fantasies. They are going to be there no matter what. Fantasies don't mean anything . . you are not gay because you have this fantasy. You are not bad because you have any of the fantasies you have. Even if you wore long-johns under your suit all day, you'd still have intense submissive fantasies. The fantasies you have are gifts to you, my dear. It's your right to enjoy them. Life is too short not to. -- Jane Dear Jane: I have been cross-dressing for over 30 years, but my wife only recently caught me in my wig and makeup, bra, garter belt, and high heels. After much duress we finally agreed I could wear panties when we make love, but I had to throw away my other girlie stuff.
However, after a couple months under this arrangement, I knew I had to go back to dressing up all the way. I did enjoy my shopping spree for new women's attire. Should I tell my wife that I can't give up cross-dressing-and that I don't want to? Or do I take my chances that she won't catch me in the act again? She told me if I couldn't give it up we would have to go to counseling, but I know that I don't want to give it up, even at the risk of our marriage. Thanks. -- Randa P.S. I think you're a wonderful and understanding woman, Jane, not to mention great-looking in pantyhose. I loved yours in the December issue, so silky and luxurious. Can you tell me what brand, color, and style they are? I want to try some, even if I won't look as good in them as you. Dear Randa: You assume that going to counseling spells the end of your marriage. It does not. Choose a counselor who is familiar with cross-dressing and open to varied styles of sexual expression.
Go into therapy, and if you value your marriage, work to save it. That needn't mean giving up your alter ego but it does mean being honest with your partner and yourself. Good luck. And, about the pantyhose... don't be so sure you wouldn't look good in them. I always notice how you cross-dressers seem to have amazing legs. -- Jane
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