There's so many types of crossdressers that it's a tricky fetish to discuss as the motivations from one person to another can vary tremendously. Crossdressing is often part-and-parcel of an entire fantasy scenario with several other fetishes, though can also be a stand-alone fetish.
Before I begin this discussion, I want to clarify that I am discussing crossdressing specifically, not those who are transgendered. Transgendered folks may or may not have fetishes, but being transgendered itself is not a fetish.
I also want to clarify that I am speaking primarily about heterosexual men. I have known a few queer drag queens, but don't know enough about their motivations to discuss it knowledgeably.
Here's some "levels" of crossdressing:
- wearing women's underthings during sex
- Often, the foremost motivator in this type of crossdressing is the physical feeling of women's clothing. Silk panties, nylon stockings and a satin garter belt feel significantly different to the wearer than a pair of boxer shorts; the physical feeling of these fabrics is erotic to the wearer.
- wearing women's clothing under normal street clothes
- Unfamiliar clothing during a typical work day causes a heightened awareness of sexuality throughout the day. Here, a big part of the turn-on is doing something naughty and "getting away with it" or alternatively, the rush from the fear of being caught.
- shopping for lingerie
- Part of the fun of buying sexy underwear is the fear that the clerk waiting on you knows it's not really for your girlfriend; the threat of exposure and that a woman will use this knowledge against you put this into the realm of domination and submission.
- adopting a feminine persona
- A sissy is someone who likes to go all-out with the crossdressing, with a complete feminine outfit, often including a wig, makeup and nail polish to complete the look. The fascination with being a woman is understandable when you look at our culture; women are eroticized much more than men are. Becoming a woman means becoming desirable, sought after, sexy.
- going out dressed as a female
- Some find it hot to go out dressed as a female, whether they pass or not. If she does pass, the feeling of being desirable is heightened, whereas if she does not pass, the turn-on comes from feelings of naughtiness, being "caught", and/or humiliation.
- hard-core sissies
- Some devote much time and energy to understanding feminine things and hence become much more knowledgeable than most women about fabrics, clothing design and cosmetics. As an ex truck-driver, I am not the type of female who is very into this sort of thing myself, hence I've learned a lot from hard-core sissies.
While a crossdresser may progress from one level to the next, there is no need to do so. Someone can be comfortable at a particular level and enjoy it without going further. As with any fetish, you enjoy what you enjoy.
When crossdressing has progressed to the sissy-level, there can be a lot of variety in the preferred look:
- the glamorous look
- a long gown and gloves, perhaps even a tiara (think "Ginger" on Gilligan's Island)
- the french maid
- often this look goes along with providing service as well (tea parties seem popular)
- dressing like a whore
- lingerie with black garters, fishnet stockings and fuck-me pumps and a significantly unsubtle application of cosmetics
- "teen" look
- this could be a cheerleader outfit with pompoms
- "little girl" look
- an example would be dressing with laced panties that peek out from under a too-short skirt
Fetishes that often "go with" crossdressing:
- domination & submission
- Forced feminization is when a crossdressers is "forced" to indulge in their fetish by a domme; others like a dominatrix to act as a "big sister" in advising them, giggling with them and shopping with them. Conversely, some find crossdressing to be an expression of submission itself, rather than a direct turn-on; they find it hot because it seems so extreme to them and so counter to their own inclinations.
- humiliation
- Many find crossdressing humiliating for many different reasons: perhaps they feel crossdressing is their dirty little secret and someone knowing makes them feel out-of-control; if they do not make a pretty girl, the crossdressing itself may feel humiliating much as dressing like a clown would be; some find crossdressing as a "punishment" for not being man enough to be deeply humiliating.
- strap-on cocksucking
- Being used as a cocksucker is an activity that can make a sissy feel very "slutty" and "dirty." It can also be hot when combined with small-dick humiliation, that the sissy is being used as cocksucker because his "clit" is too small to satisfy a real woman.
- strap-on anal sex
- Though each fetish can exist singularly, it is common that being a sissy and being used by a domme anally go together. The sissy's "pussy" is fucked to simulate male-female intercourse in a manner that avoids the stress of homophobia.
- forced bisexuality
- This is more often a fantasy than a reality, but there's exceptions. There's a variety of motivations for this which I've discussed previously on this blog.
If you'd like to discuss your crossdressing fantasies with a sympathetic ear, give me a call:
