Her First Time Crossdressing – Part 2

So before I get into this crossdressing story, check out part one if you haven’t already! Really, me and my dear friend were having so much fun. But as I was saying in part one, I felt and saw her hard clitty. It was something that I wasn’t exactly planning on to happen. She was looking in the mirror and just couldn’t help how she felt. I don’t blame her at all… In fact, I began to encourage her to let her feelings flow. No matter how naughty they may have been.

She was standing there for a moment longer. Admiring her figure while in my clothes. I asked how she felt and she told me she felt beautiful. Then I slowly came up behind her. My hands reaching for her hips in that short skirt she was wearing. I started to realize that I also liked the way she looked. I am attracted to girls after all. Although she was only crossdressing I still thought of her as a sexy girl.

With one hand on her hip, my other hand reached underneath the skirt.

She quietly gasped and asked me what I was doing. Well, I couldn’t help but giggle and whisper in her ear “you’re too sexy to not touch.” Of course her clit was harder than ever in this moment. I didn’t think she could get any harder! She didn’t stop me and clearly she didn’t want me to stop teasing her clit. So I reached underneath the front of her thong and started to rub her clit-stick.

Then the cutest soft moans came from her pretty lips. I wrapped my hand around the shaft and began slowly stroking. Up and down. Squeezing tighter while she squirmed around a little. The whole time she could see herself in the mirror as I touched her. Oh yes, she was definitely loving this treatment!

Next I had her lay back on my bed.

At first she seemed slightly nervous but I assured her everything would be okay. I smiled and told her she was going to love what I do next. So as she was lying on her back with her legs spread I went into my closet. I found something that I knew she was going to love! It was my trusty vibrator. She was blushing. Knowing that I was about to use my toy on her clitty.

Her legs spread open a little bit more as I sat in between them on the bed. She was looking so hot while biting on her bottom lip. Watching closely as I turned on the vibrator. I then lifted up her skirt then pulling down her thong just enough so she was exposed. That’s when I asked if she was ready. She looked up at me and shyly said “yes I am, Ruby…”

So I began to slowly tease the tip of her clit. Instantly the vibrations made her twitch. Her body tingly all over while I slowly worked the vibrator around the head. I could tell that she was in bliss. Sometimes I would have to turn off the toy so she wouldn’t squirt quickly! After having to do that a few times I knew she wouldn’t last much longer. I told her to get ready to squirt for me. She tilted her head back and started cumming while the vibe kept going!

She really sounded so feminine as she came too. I was so proud of her for feeling this comfortable with me. She did great while crossdressing for the first time. I know it won’t be the last time either.

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