Opening Up
Human beings are a collection of sexual hangups. Some of these anxieties are time-honored traditions passed on by our ancestors, and others are unique to each of us. These things, by themselves, are mostly benevolent until we infuse them with fear and make them a focal point of our self esteem. Someone, somewhere, is still in the closet about their desire or avoiding intimacy with a partner because of what they perceive to be a problem area on their body.
I recommend that you find a therapist not because virginity is a problem nor is fear of penetration, but because it sounds like you've been breaking off otherwise happy relationships, which is problematic for you. A therapist can provide incredibly helpful support and a great place to learn about how to talk about difficult issues. Ultimately, however, you are under no obligation to have sex, do anything that makes you feel uncomfortable, or tell a partner that you're a virgin.
If you want to work towards penetration, you can purchase a dilator set from Good Vibrations. They are designed for women who have recently undergone sex reassignment surgery and graduate in size from super tiny to average. With patience and a lot of lube, you can practice penetration on your own. Good luck!
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