An Introduction to Crossdressing Pt 2
Add: 5 August 2015 / 17:00
So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong.
The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and much more.
I had not noticed that Jacky had quit talking a few minutes ago when he saw my mouth hanging open like a fool as I took in everything. As I came to my senses and closed my gaping mouth, I looked over at Jacky and he had the biggest grin I think I’ve ever seen. We both said simultaneously that this was going to be too much fun.
Once we were done giggling like school girls, Jacky introduced me to Heather, the owner of the shop. Heather was about our age and an attractive woman with short dark hair and about 5’10’’ with her black two inch heels. She was rather conservatively dressed for such an establishment wearing a knee-length black skirt and a white blouse buttoned up all the way.
Heather went over the services that they offered and suggested that she accompany us into a dressing room to evaluate what we would need. She asked who wanted to go first and I said I would, then I asked Jacky if he wanted to go together. Jacky quickly agreed that we should go together since we wanted to share everything this weekend.
Heather led us to the dressing room and once inside asked us to strip so that she could figure out what services we might need and what accessories would work best with our bodies. I considered the fact that we had only just met in person about twenty minutes ago, but when I started to undress it didn’t seem to matter. We were both stark naked in about thirty seconds and so very excited.
As she looked us over, Heather noted that we had very similar body types which would make choosing clothing much easier. She also noticed that we were both already hair free, so there wouldn’t be a need for waxing. She took our measurements including shoe size and said she would be back in a few minutes.
As the door closed, I moved up behind Jacky and pressed my throbbing member up against his perfectly shaped ass and wrapped my arms around him while whispering in his ear how badly I wanted him. Jacky reached behind me and grabbed both of my ass cheeks in his hands and whispered back to be patient and enjoy the transformation.
While we were gently rubbing all over each other, Heather announced that she was coming in with our outfits to try on. We untangled just in time and, as I backed away from Jacky, a thin string of pre-cum that had attached itself to his lower back stretched out from my cock until it finally broke off leaving a nice dab and line down his sexy ass.
Heather handed us each a red corset and suggested pushup breast enhancers rather that forms so that our natural breasts would be on display. She also handed us red lace g-strings which we both slipped on immediately to try and tame our hard-ons, to no avail. After we slipped on the corsets, Heather suggested that she tie Jacky’s and he tie mine to shorten the dress-up time since we still had make-up and hair to get done before closing time.
After all the air had left my lungs, we from the tightening process Heather gave us some four inch red pumps to wear. She then has us slip on our matching little black dresses for fit, and fit they did, then she told us to take them back off and put on the plastic ponchos for hair and make-up. As I slipped on the poncho, I started to remove the heels, but both Heather and Jacky suggested I leave them on for the practice in walking.
There was no question that I needed practice walking in heels as I stumbled and tripped my way over the hair stations. Once we were settled in our chairs, Heather introduced us to Kim who would be helping us with our hair.
Kim was almost the complete opposite to Heather’s conservative look wearing a pink tank top and a short denim skirt. She was a very attractive petite red-head and about five feet tall in sneakers and looked to be about thirty years old. Kim said that she could probably style our current hair to look feminine if we wanted to go natural, but we both wanted to go for the long hair look and opted for wigs. I was to be the blond bimbo and Jacky the brunette.
We tried on a few different styles and both settled on fairly straight hair with a length about four inches below the shoulders. I must say that, even without makeup, we were both starting to look rather girly with just the wigs. Kim put the wigs to the side and took us over to the nail lady, Linda.
We sat at Linda’s table and, after a lengthy discussion of the different nail types available, we decided on pre-painted removable nails trimmed to be about a inch longer than our own nails. Linda showed us how to apply the nails on a couple of fingers and then had us each apply our own. I picked a flowery design while Jacky went with a fire engine red and then we graduated from nail school.
The make-up lady was still busy with another customer, so Jacky suggested that we take a walk outside. I wasn’t crazy about the idea, but Jacky said that we need to get some air and I needed some more practice walking. As we headed into the parking lot, it was already getting dark so my anxiety about being seen in our high heels and plastic ponchos started to ease a little.
As I followed Jacky towards the back of the building, I began to take in all that we had done so far and what was still to come. Jacky stopped at a picnic table and turned towards me pulling me in for a light kiss while squeezing my ass through the poncho. I responded with a hungry assault on his lips while raising his poncho and fondling his growing bulge.
After some deep tongue probing, I dropped to my knees pulling his panties aside and sucked him into my mouth as far as I could take it. Jacky tried to stop my onslaught, but I wasn’t stopping until he came, and cum he did. I think he must have saved that load for a month, but I gobbled it all down and then headed back inside leaving him breathing hard.
As I walked back into the shop, I noticed that the make-up table was now empty, so I strutted in that direction. Amanda was the make-up girl's name and she was gorgeous. She was another petite one with long black hair and her make-up was perfect. I felt quite comfortable with her as our make-up artist.
Amanda went to grab our wigs just as Jacky came in with a big smile on his face. When Amanda came back with the wigs, she helped us put them on and then started working on the makeup. First she had to decide what worked best with our complexion, hair and eye colors, then she started showing us how to apply the make-up.
The make-up took the longest time to figure out and we applied and removed several times before we got the hang of it. After the final application, Heather brought over our dresses and had us remove the ponchos and slip into our little black dresses. She then had us walk over to the full-length mirrors to see the finished product.
OK, so we weren’t supermodels, but we were quite passable as women our age and I was amazed.
As we settled up with Heather and hugged all the girls that helped us, I couldn’t wait to get out and show off. Jacky asked me to follow him to a hotel where we were staying and said that he knew of a few places that we could go where there were others like us. I was quite excited!
To be continued . . .