One thing I’ve always been curious about throughout my days of femme delight is whether crossdressing has the tendency to lead into homosexual relations, be it with a man or another crossdresser. Keep in mind, I neither care about putting a label on ourselves nor am I trying to prove true the ancient myth that crossdressers are gay.
It just so happens that, from personal experience, the crossdresser evolves into conforming more and more into, not only dressing the woman´s part, but acting out the part as well. It may be take form as going out in public in full dress or just meeting up with other CDs to have a meal.
Yet, since crossdressing is primarily a medium for sexual stimulation, this would also undergo an evolution over time to keep the stimulation at its peak. Much like the way, for example, a married couple might experiment with sex toys to keep their sex life new and interesting. Side note: this does work for crossdressers as well.
So, over time, the usual slipping on pantyhose, silky lingerie and maybe some heels and makeup would lose its appeal to repetitiveness and, ultimately, boredom. You could have a different silky outfit for every day of the year but wanking the poor little cock so many times, pretty much in the same fashion each time, might get you thinking, “Well, why don’t I wank someone else’s instead?” to make things a little more interesting.