tagTranssexuals & CrossdressersWas He Becoming A Cross Dresser Ch. 02

Was He Becoming A Cross Dresser Ch. 02


Chapter 2


I was retired and that's how I ended up cleaning house and running errands for the family, I didn't mind, I didn't have to get up too early to go to work! I still was a part time contract recruiter for the company I had worked for 22 years and was expecting a big bonus for two 2 recruits very shortly and decided I was going to spend half on myself. No one actually knew what I made on the bonuses in my household anyway, I had to have SOME secret money, don't we all?

For the next few days I would spend an hour a day bidding or buying like mad for undergarments that were so SLUTTY and sexy, blouses, skirts and even a few dresses! I was going crazy buying sexy cloths but didn't know what size I was exactly so I had a lot of cloth come in the mail to big or too small till I figured out my size! Most of the cloths that didn't fit went straight to my kid's school yard sales they would have all summer but what a waste. Anyway, my biggest challenge was shoes, heels, pumps all new words to me but I found one seller who had a conversion chart and it even had the conversion for males to women's sizes!

I was so excited to order my first pair of heels, pumps and my soon to be favorite thigh high WHITE Patent Leather boots!! All in all I spent over $500 dollars on my clothing shoes, boots, and lingerie in less than a week. I was on pins and needles waiting everyday for the mailman to come, some day's 2-4 packages and some days nothing! I was like a kid in a candy store with all these packages arriving daily, and every time a package would come in I would run up stairs to the bathroom, open it, try it on alone in the bathroom and cum, cum, cum! It was so erotic to be buying cloth and undergarments for myself but the high, the rush was over the top. I was assembling my outfits, but what about makeup?

My wife had 2 drawers she would throw all her used or unwanted makeup and I hit the JACKPOT! I found eyeliner, lip liner, lipstick, mascara, a few different shades of makeup and even some blush! The first time I put on makeup, it was a mess, and nothing looked good on me especially the base. I was olive skinned and my wife was very pale skinned so I had to find makeup to fit my skin tone!

On one of my grocery shopping days, I would cruise the makeup Isle till it felt safe to grab a bottle, throw it in the basket and quickly run to the food isles pushing my basket and slowly open the makeup as I walked and dab a drop on my hand like I had seen my wife match her skin tone many times. Finally after a few bottles I found one that was almost transparent on my skin, it blended well, "this is it" I said to myself! Then I was in a race with time to get home and have at least an hour to play before the house filled up with activity and people!

I arrived at home, put the groceries away as fast as I could, got the roast in the oven, opened the cans of vegetables put them in a bowl ready to heat later and was up the stairs in a flash, I was ahead of schedule. I first took out a new razor, carefully shaved my face closer than ever, then dried my face off and looked into my eyes in the mirror, "what are you doing", I asked myself? There was no turning back now. The sink counter was covered in used and new makeup and I was ready for my transformation.

I first started with the makeup I had bought, smoothed it on as I had watched my wife do for many years, even borrowing a makeup sponge from her makeup drawer and smoothed it on perfectly. I looked pale but it matched my neck which was what it should do, blend in. Next I got the eyeliner pencil and lined my upper eyelid with VERY BLACK eye liner and even did the bottom inside eye lid. It made my eye water a little but as my wife would do I dabbed it with a tissue and was ready for the next step.

I opened a used eye shadow kit and decided to go with pink and white high lights on the inside corners of each eye as I had seen in many glamour magazines my wife had in the bathroom and even opened one to a page with a close up of a made up eye! It went on so beautifully and once the WHITE high light were added into the corners of both of my eyes I was becoming aroused and my COCK was starting to twitch, I was looking beautiful.

I rushed to my closet where I had hidden all my lingerie and quickly grabbed the matching pink set of undergarments, bra and thong panty and slide into them, they fit perfect. MY COCK was so hard the head was purple and throbbing, but it felt so good in my own panties,my own cloths.

I looked in the mirror and was so excited to see me becoming beautiful, sexy; attractive...was this what I wanted to be? I reached for the lip liner and made the "V" in the center of my top lip my wife would make and curved the pencil around my lips even enhancing my upper lip PERFECTLY.

It was amazed at how just watching my wife do this as we chatted in the morning before she went to work I had LEARNED how to put makeup on! Was I subconsciously studying her all these years for this day? I don't know but I was looking beautiful. Once I had curled my eyelashes with a used lash curler, I quickly reached for the used mascara and started to see a new person; I was squirming in my panties and was starting to breath in a panting like breath.

I was so excited for me, I was feeling so HORNY, SO SEXY so HOT! Once I had applied a few layers of mascara on to my lashes I finished my lip with a BRIGHT RED Lipstick and lastly blush on my cheeks, chin and jaw line. I was ready for the full length mirror....would I look stupid, or would I like what I saw? I slowly walked over to the mirror and actually gasped at myself in amazement. I didn't look too bad...Actually looked like my mom a bit in her hay day, and a combination of my sister who was just as beautiful as my mom was!

I was sexy, beautiful and so fucking turned on! I reached for the throw rug on the floor and slide it to the mirror, and lay on the floor rubbing my cock and my bra as if I had breasts and I rubbed my legs together.... They were not very sexy with all that hair but I was still on fire. I rubbed my cock, reached inside my panties and reached my ass hole with the other hand and started to finger myself, moaning and sighing never taking my eyes of myself! I rolled on that rug with my finger buried in my ass and my other hand rubbing my bra, my chest and even caressing my face once in a while blowing kisses at myself in the mirror.

I had done it; I had gotten all made up and wanted nothing more than to cum as a woman being made love to with my finger now pumping in and out of my ass I was close, very close! I stood, looked in the mirror, turned my booty so I could see my hand in my panties pumping in and out, in and out and started blowing kisses at myself as I moaned "mmmmmm, fuck me , fuck me" and my cock quickly pulsed and pulsed HOT CUM into my new panties without me even touching myself!

I dropped to my knees and squeezed my thighs together to feel the hot burning LAVA flow down my legs and my finger was nearly crushed in my ass with the sensation of cuming with my finger buried in my wet, wet ass hole! I slowly eased my finger out of my now sore hole and I looked at myself one more time before I had to quickly get all the makeup off, the bathroom back in order, get myself back to being the man of the house and getting dinner going as I normally would by this time and lastly, rehide my cloth and makeup. It was a race of time I had to win or be discovered!

CandyCane XOXO

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