Her First Time Crossdressing – Part 1

Recently a dear friend of mine confided in me about being interested in crossdressing. This might actually be my first time talking about the subject on my blog. However, I have spoken to many crossdressers, sissies, panty boys, ETC. over the years! Anyway, I was so proud of him for being able to tell me something he’s always kept to himself. I do not ever judge. He knows that which is why he trusted me with this subject matter.

He knew that I would have the skills and expertise to help. I’m a kinky phone sex girl after all! So I decided we should just have a slumber party to try on clothes and makeup. Of course he couldn’t resist the offer! I was already thinking of how to dress him. What shoes to wear, stockings, MAKEUP. All I wanted was for my sweet friend to feel comfortable and let his inner girl out!

So I brought out a few things from my closet for him to try on. I taught him how to properly put on my stockings as to not tear them. Then came the actual clothes. A short plaid skirt and a cute black top would look perfect, I told him. So he put them on and then I grabbed some sexy high heels. Oh, and I almost forgot the panties! I brought out a simple but hot black thong. He put it on and told me he liked the way it felt against his body. Afterwards came makeup time!

I knew that once I was finished he would be looking so feminine and sexy.

Lucky for my friend, he’s always looked a bit feminine in the face and body. You’ve probably noticed by now that I have only referred to him as “her” in the title of this story. Well, let me tell you what happened next after I finished making him over!

So next I decided to walk him over to my full-length mirror. Actually, I needed to help him as he’s still learning how to walk in heels. This was his first time trying on ANYTHING feminine too. The whole experience was quite exciting for the both of us. When he saw himself in the mirror he gasped. I could see happy tears in his eyes. Obviously I couldn’t resist giving him a big hug!

That’s when I felt his hard clitty pressing against my body. “Oh no”, he said… He told me that he couldn’t help it. This brand new experience was too much for his clit to handle. I told my crossdressing friend not to worry – that I’m glad he was this excited!

Next, I told him that I would be referring to him as “she” for the rest of the night.

The thought of being sissified turned her on but she also just wanted to feel like a girl. So of course using she & her pronouns was going to help make her more comfortable. This slumber party was only getting started actually. I did mention her clit-stick being hard… What do you think we did next? Well that’s what I’m going to divulge in with part two of this crossdressing story!

You can also buy the audio if you rather not wait until Thursday to hear part 2!

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