Coupled With D&S

Real, nonjudgmental advice about dating, sex, love, and life from a thirty-something couple that has seen it all over thirteen years.

Trust us. We live in Brooklyn. (Joking. Kind of.)

Tag: cross-dressing

Cross-Dressing Conundrum

A 42 year-old straight male who cross-dresses, is only interested in women, and only wants an LTR writes, “I’m stuck with a paradox: I have discovered that if I am not perceived as forthright from the start (I don’t always dress up, just like women don’t always dress up), the revelation of what makes me different can be off-putting. On the other hand, if I put who I am out there from the start, no one picks me. OKCupid has in the past provided women who pick me and that has been extremely rewarding. How can I increase my ability to find women who would want, not merely accept what makes me different?”