-
Island Fantasy
Date: 9/10/2017, Categories: First Time Shemales, Author: SandyCrossdresser
... I'm sitting here as Jackie and not Jack. As Jack I'm confident and calm, even cool at times. But as Jackie my body barely functions. I can't believe what I'm doing and more over, I can't believe how I look while I'm doing it. But as I look into your eyes and see how you look back into mine I know I'm doing the right thing. You've not been this relaxed since we met, its as if your need for a friend was more of a need for a girl friend. The bond of two women opening up to each other, sharing things men just couldn't understand. Now here I am, pretending to be that girl friend. But am I really pretending? I remembered the time when I was just 10 and wore that dress around my house for weeks, dancing and twirling for my siblings. It felt so right back then and it feels even more right now,,, if that's even possible. This time I'm not just a little boy wearing a found dress around the house, I'm a grown person who is just realizing how complicated life has just become. I don't know how I'll cope with being in the US Navy, I don't think I could show up on the boat as Jackie, but wow! would that get me a lot of looks.. <grin> After showering and shaving, which I have to admit was a thrill in itself, feeling how smooth my legs felt after,, I came back to your room and you helped me find everything I would need. The only outfit you had that would fit me was a loose clingy sleeveless dress that came to just above your knees but on me it was just a tad bet tighter and hugged me in all ...
... the right places. The hem came to just higher than the middle of my thigh which made it a mini dress. First thing you did was sit me down in my robe and do my makeup. Nothing too heavy but because my features were a little stronger than your more feminine ones you used a little more color on me. You never even let me look in the mirror until after you were done with my face and when I did look.. I couldn't believe it was actually me I was looking at. You then sat down next to me to do your own makeup and when you were done we looked into each others eyes as we leaned together to kiss,,, pressing our lips together and your glossy brown lipstick mixed with my glossy red. Just enough to give you a little more color and tone down my own. Next you helped me on with a pair of your stockings and when you pulled them up my legs and smoothed them upwards, my penis did the same thing.. moved upwards... <blush> Other than brushing against my now erect penis now and then you ignored it as you continued helping me get dressed. Fastening a garter belt around my waist and connecting the tabs to my stocking tops, then holding the dress as I stepped into it. Lifting the dress slowly over my calves, past my knees, allowing it to spread out as you pull it over my hips then my waist, and holding it open so I could slip my arms into the proper openings. Adjusting the straps over my shoulders and smoothing down the dress the same way I did for you. You didn't have a bra or panties that would fit so ...