"Women who love themselves are threatening; but men who love real women, more so."
From Prude To Lewd
The word "Prude" is generally considered a pejorative term to suggest fear and contempt of human sexuality or excessive, unusual modesty, stemming from such a negative view of sexuality.
This is my experience and what I learned from it.
Backstory
My partner and I have been together for nearly four years. When we first started dating, we were both in our early 20s and she was still a virgin. She was from a very traditional background, no sex before you are married and missionary position once you are.
Coming from a different background, I'm originally from Europe and moved to the US when I was 17. In my family, we got the talk when we were young-- informed about safe sex and sent on our merry ways.
Now, that doesn't mean I was out at clubs all weekend with hundreds of girls. In fact, I am an incredibly shy guy. I've had a few girlfriends but that's it.
Our Trials and Tribulations
We first met over summer after graduating from college and instantly connected. She is an incredibly bright woman and we share many of the same interests. One thing we both differed on were our feelings toward sexuality.
Our love of travel was the first thing that really brought us together. We had been together for about 3 months before I said to her, "Lets go to Europe." We could stay with family to make it cheap. She jumped at the idea of spending a few months traveling Europe. It's every girls dream right? So we flew in to Paris where we have a family apartment for anyone to use, right in the heart of the city.
Setting the Mood
Choosing the right time was the first and most important lesson I learned, though I didn't even think anything was going to happen when we decided to go abroad. But the time was right and the mood was set. Imagine that you are a young woman with her boyfriend in Paris. This is a once in a lifetime opportunity isn't it? Needless to say on the second night of our arrival in Paris, she told me she was ready for that big step.
We went slow and it was painful for her but we both assumed things would get easier there on out. So we tried again a few days later and again and...we had to stop. We always started with heavy foreplay but she was always far too dry to engage in sex and complained of a burning sensation. A little disclaimer, this went on for a while. After weeks, months, and finally a year or two of this problem, I was checking WebMD, forums, instructional videos, buying lubes etc. WebMD had me thinking she could have had some disease or bodily dysfunction. I'll tell you right now all of those theories were bunk. Of all things, it was the instructional videos that helped the most and this was after 2 years of this problem.
State of Mind
We had really gotten into a lot of oral play because of the difficulties we were having with penetration. I was looking up how to hit the G-spot through simultaneously fingering her during oral sex. She wandered over and watched a video which I found on a porn website. It was tasteful but had a lot of nudity. At first she thought it was gross and a turnoff, but sat there with me nonetheless. When it came time for me to try, I had made this great big discovery of my own. She was wet. This is where her fears and reservations about sex went out the window and she realized it was all state of mind. If only I had known that 2 years before! All of a sudden, not only am I hitting her G-Spot, she is having multiple orgasms and we are getting more and more into penetration.
Being Comfortable with Herself
One Valentine's Day I bought her an adult toy set. It included a bullet vibe, a rabbit, a traditional vibe, some lube, toy cleaner and some exercise balls. She was a bit overwhelmed but I had this feeling that the final frontier was getting her comfortable with her own body. Her upbringing had taught her that pleasuring oneself was a mortal sin. At first we started using them together in order to get her used to them; when we used them together, she really enjoyed them.
Patience Young Grasshopper
The biggest lesson of all was time. Put yourself in her shoes for a moment. She has been made to feel ashamed of her sexual feelings all her life. I just gave her the tools to make it easier and let her be. After slowly opening her up to her sexual desires, she began initiating sex. We were on different schedules sometimes for work, so sometimes she would be at home alone with (in her mind) no way to pleasure herself. Luckily those toys came in handy! I came home one evening to see a grin on her from ear to ear. At first she told me she was a little ashamed to tell me, but when she did I simply said: "That's great!" She was so happy to see that I approved of it that she became comfortable doing it in front of me. Slow and steady wins the race.
We Eat With Our Eyes
For a long time we didn't revisit those instructional videos, but we found that when she was feeling comfortable, we revisited them. We started watching the female friendly videos and at first we joked about them and how bad the acting was. Eventually though, I mentioned how she had to imagine herself in their place. She started to see it from a different point of view and started to enjoy it and soon we no longer needed any lubricants; she was ready to go, even wanting to go. And with all the additional inspiration, we could try new things as well!
In Conclusion
With her comfort level growing more and more every day, sex is becoming more and more enjoyable for her. Her inhibitions are melting away and we can enjoy more intimate moments with each other. If there is anything I've learned from this, it's not to give up if you really care about this person. Help them without being pushy and have open conversations. Every few months try something new, starting slowly, a massage, oral, a toy, porn etc., until she is completely comfortable. Remember for her it's about learning to love herself before she can really enjoy her partner intimately.