My girlfriend is going to college about an hour away, and I keep my crossdressing items at her apartment (she knows). We talk every now and then about crossdressing, and the general place we're at right now, is that "it's all new to her" and "a few years from now, it won't phase her in the slightest".
She let's me buy things and ship them to her apartment, which is awesome because I'm currently living with my parents while I finish college. I ordered a nice set of tall heels, and when they showed up, I opened the package and checked them out but didn't put them on (im still self conscious dressin around her). Well a couple hhours go by and she says "how did the heels fit?" I replied "dunno yet, haven't tried them on" she says "well why not?" I reached down where I had set the shoes and slipped them on "they actually fit nicely!" "good!" she said.
Well bedtime rolls around after a few beers and I ask "do you mind if I sleep in a pair of my underwear? (Victorias secret Hipsters)" she goes "I don't care?" so I slip in them and fall asleep beside her.
She's never seen me in a bra, even though I had a bra at her apartment. Well the morning rolls around, and I wake up before her. I slip my bra on, and cover my chest with the blankets until she wakes up. We lay there talking for awhile until I say "babe, please don't be mad at me, but I put my bra on lastnight to sleep in." she says "why would I be mad?"
We continue lying there as she talked on the phone with her mom, as she rubbed my shoulder, every now and then grazing over the bra strap. As she talked on the phone, I let the blanket slip farther and farther down until my bra was completely exposed! It was such an amazing feeling being dressed in a bra and panties in front of my girlfriend for the first time and her being okay with it!!!
We spent all morning laying in bed cuddling while I was still in my bra. We eventually got up to get food, but before I took it off, I asked if she could adjust my strap, and she did
That night, I slipped into another pair of VS underwear and crawled into bed. I grabbed the bra and put it on and she asked "can I ask a question without you getting upset? Because it's just a question" I said "sure babe" she asks "is this something you're going to do every night?"
I said "well I don't have to. I mean, I would like to, but I guess it depends on the mood im in? But the answer is no, this won't be every night. Why? What would you say if my answer was Yes, I want to do this every night?"
She said "I'd be okay with it, I just want to know what to expect"
I'm trying to expose her to my crossdressing so that she can get more comfortable around it. So far she seems to be okay with me in a bra and underwear and shoes. I've showed her a pic of me completely transformed, and she basically said she's fine with everything but a wig, makeup, and breastforms. I don't like dressing without those 3 things, because dressing without them, I feel like a creepy guy in women's clothes :/ with them I feel like a sexy woman.
What should I expose her to next? Is there another way I should be doing this? Thanks for reading this far and for any helpful tips!
I am actually attracted to "her" forms and all which scares me a little, but it's true. I am not sure that is true for everyone. It would be difficult to find the whole thing a turn off and I'm glad that I don't have that issue. Communication is key. Let her be in control. If she says, "not tonight", then you need to be supportive of that. In all fairness she is with you because she was attracted to you as a man. To then ask her to be okay with you dressed as a female can be quite a mind screw. Patience and honesty are key.
