I'm 31 and have never been in a relationship. I'm used to being independent and spend much of my time alone. However, I would like to have a relationship one day and ideally I'd like to marry and have a family. My parents have been married for 35 years and I kind of envy what they have in each other. I'm naturally shy and awkward, especially around women and at 5'5" and 130 lbs I'm not really considered attractive or boyfriend material.

I've learned to accept my size (and actually love tall women in heels!) but beyond my size and shyness I also enjoy crossdressing every now and then. I'll dress up and go out for a few drinks and maybe a meal. It's fun and I have no intention of giving it up. Ideally I'd love to find a female who also enjoys my dressing but I understand that's not easy to find. Add to that the fact that I have other kinks and fetishes, some kind of bizarre, and my dating pool gets smaller and smaller.

I want to be upfront and honest about my sexual interests but I don't want to scare everyone away.

When is the best time to bring it up? How do I introduce it? Anyone else have experience with this?

Cross dressing is one of the more common of the fetishes, not everyone is going to be open to it, but it is also not something you tell them on first date either

Crossdressing is one of the few kinks I don't enjoy, although a kilt is amazingly comfortable.

Are you shy because of your fetishes, or are you a fetishist because of your shyness? In my youth I was in the former category, so it isn't the total roadblock to relationships it sometimes seems.

Take baby steps. Talk to the checkout clerk at the grocery about your purchase. Talk to a female co-worker about fabrics and prints, even if you never want to go out, just to get in practice.

Once you can talk to the ladies, then worry about steering the conversation.

I'm just naturally shy, kinks or not.

I don't havr much contact with females due to my job. I'm in security on the overnight shift and my coworkers are mostly former military and police males. Most nights I am posted alone. I work most weekends and holidays so I don't see many females. My female friends pretty much no longer talk to me.

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Originally Posted by kevinkylie

I'm just naturally shy, kinks or not.

I don't havr much contact with females due to my job. I'm in security on the overnight shift and my coworkers are mostly former military and police males. Most nights I am posted alone. I work most weekends and holidays so I don't see many females. My female friends pretty much no longer talk to me.

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The point was that you know something about women's wear, so use it. Is the clerk at the 7-11 female? Is her uniform knit polyester or cotton? Does the color flatter her? How about the (one) cute girl in Wal-Mart?

Talk to any married females, especially. First, they are safe so rejection won't be an issue. Second, they have single friends.

Working nights alone will lessen your opportunities to work on your shyness, it doesn't eliminate them. Only you can do that.

Depending on what your kinks are, joining a fetish site and maybe attending events held by the local kink community might be a good bet. You can be open and honest about what you like from the beginning, and any woman you start a relationship with should already know and accept your kinks.

Fetlife is a social networking site, much like Facebook, and Collarme is a dating site. Both cater to the link community. Just remember, always treat women with some respect, and not like a fetish/sex dispenser, and you're more likely to get good responses.