I opened up my wife's sister a bit over a decade ago. She was such a prude that she wouldn't even let her own husband touch her, and she only had sex a handful of times with her husband, just to have two kids, and that was it.
I "opened her up" in this way: At a cabin with the entire family (12 of us), it was raining, so everyone was playing board games. I hate board games, so I offered massages to anyone who wanted one. Shoulders, back, upper chest, whatever. When it came to my wife's sister, I jokingly asked if she wanted a massage, expecting her to say no. Well, she said yes, so I guess I was committed.
I massage her back (up her shirt), her shoulders (slid her tank top straps down), and moved to her upper chest (I could easily see inside her over-sized bra). She let me go really far down her chest, like I was within an inch of her areola on her A cup breasts. My wife shot me a look, and I just shrugged my shoulders.
Well, after that night, I gave her similar massages regularly for a few years. We also spent more time together (we are/were both pro musicians, and we found reasons to spend time together). She was suddenly way less careful around me when wearing a skirt, she would lean on me when we would sit next to each other, she would walk around in a towel around me after a shower, she would go braless at home and comment on how her long nipples poked out too much, she wore extremely thin/cheap sports bras around me, and one time we were out in the cold and she snuggled with me more than anyone else ever had.
Then one day it all stopped. I am not sure if I stopped or she stopped or what happened, but we haven't massaged or even sat next to each other ever since and it's been a good 8-10 years now. My wife loved seeing me that cozy with her sister, so even my wife wonders what happened. My wife thinks that her sister was started to fall really into me, and that spooked her sister a bit, perhaps. I will never know!
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