Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one.
Extended Vacation
Chapter 1
Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a very smart decision two years ago in regards to my cross dressing. I spent almost a year preparing to be Cassie. I bought a new wardrobe, had spa treatments, lazer treatments to remove hair on my legs, underarms, chest and arms..also body waxing for the remainder..and hired a personal trainer to get in the best shape of my life.
This resulted in Cassie becoming a bigger part of my life. I travel a lot on business and I took advantage of those business trips as an opportunity for Cassie to come out and play. I learned so much about her, especially the fact that when I put on a dress I became a cock loving slut. I had sucked so much cock and got laid so many times that if I didn’t keep a diary, I would have no idea how many times I had been Cassie the slut.
I don’t know if it was a coincidence or the fact that I was so happy being Cassie, that my business career was doing better than ever. I made more money the past year than I had the previous five years combined. My company was so happy; they gave me an additional four weeks vacation to the three I already planned on taking. I thought about the options of vacations to the regular places (i.e. Caribbean, Hawaii, etc.). but what I really wanted to do was have a period of time where I could be Cassie 24/7. I wanted to know what it would be like to live my life as a woman for a consistent period of time. So instead of flying somewhere, I decided to stay in California where I lived. I was going to be Cassie the cock loving slut for the entire seven weeks.
My vacation was going to take time and a lot of organizing, so I laid out a detailed plan on how I was going to make this change and what I would need to do prior to starting the plan. It took a couple of months to execute all the details with the last two weeks of work prior to my sabbatical being very hectic as every free moment I was doing something to achieve my detailed plan. Those last two weeks I spent every evening doing the final details; One night I traded in my car for a different model, another night I rented a furnished apartment in Bakersfield (about two hours north of where I lived) and another I spent at the mall buying lots of clothes, make up, supplies and jewelry. Every night I went to the tanning booth tanning my entire body as I lay in the tanning bed wearing only a pair of thong panties. When I finished my last work call on Friday morning, I knew I could now be Cassie for the next seven weeks.
I had been packing for my adventure the past couple of weeks; the results were ten cardboard cartons and four big suitcases full of the necessary belongings I needed for Cassie. I felt like I was totally prepared and could not wait to begin my temporary life as Cassie. My last item on my list was to go to a local barber shop and have my head shaved; this would make it easier for me to wear my wigs all the time.
After my haircut, I came back to my condo and started loading up my new Ford Expedition. I had to fold down the rear seats to fit in all the boxes and bags. Then I returned upstairs and brought out a small duffel bag that had the things I needed for my road trip. I took a hot shower and as usual shaved my body all over even though I had done the same thing yesterday. I came out of the shower and looked in the mirror and couldn’t believe there was not a hair on my face, head or my entire body except for a small triangle directly above my small 4” (when hard) cock.
I emptied the contents of my small duffel on the bathroom counter and my dressing table. I put a light coat of make up on just to make my face look feminine (not overdone), but with a lot of mascara and pink lipstick. I slipped on a pair of white thong panties with a gaffe and a white lacey 34 B bra. I stuffed my small breast forms in the bra and pulled on a short (about three inches above my knees) denim skirt. Next was a white (wife beater) tank top t-shirt and then a long sleeve white blouse and after rolling up the sleeves to my elbow, I tied in a knot at the bottom instead of buttoning the shirt. I slipped on some jewelry including a long necklace with a cross that hung between my cleavage. The last touch was my most comfortable wig, a just above the shoulder black straight number featuring very subtle bangs.
I slipped on a pair of flat gold gladiator sandals and put the duffel on my shoulder. I headed out the door saying goodbye to Tony (my real name) and hello to Cassie. Once I was in my car I drove to the freeway and started my north bound trip. I was amazed of the feeling as I started the trip; it was Friday April 1 st: the first day of my new freedom. I was driving along the freeway singing along with the radio and I realized that this was Cassie’s first road trip. I looked at the clock and made note that it was 2:30 PM, I would record that time in my diary as when the real Cassie was born.
It is amazing how the mind works, after driving for about an hour, I was not thinking of anything other than the words to the song I was singing (Roam by the B 52’s) when I received a honk from a car beside me. I came back to reality and checked out the situation. I was driving through the “Grapevine”, this is the mountainous area that separates Central California from Southern California, with my air conditioning blowing (it was about 80 degrees) and was not paying attention to anything. I was in the middle lane and the car that was honking was actually a pick-up truck in the lane to my left with two young men in the cab. Well, I was shocked as these guys (probably in their 20’s) were trying to get the attention of a 42 year old cd.
I wasn’t sure what to do in response to the guy in the passenger side waving his hands out the open window of the truck. I looked in the rear view mirror and there were no cars behind them or me so as we matched speed I rolled down my window and put a big smile on my face. I turned down my stereo and air conditioner so I could hear him.
“Hey baby, one of your back tires is low on air.” The boy on the passenger side screamed so I could hear.
“Thanks!” I yelled back.
I slowed down from 75 to 55 and pulled in the slow lane. There was an exit approaching, but it appeared that there were no services at the exit. I thought I should probably pull over and take a look so I took the off ramp and noticed the boys in the pickup had slowed as well and followed me down the off ramp. As I approached the stop sign at the end of the off ramp I slowed down and pulled off on the shoulder of the road. The off ramp was very isolated as there were no buildings or businesses in sight. Looking in my rear view mirror I saw the guys in the truck pulling behind me on the shoulder. I decided to put on my emergency brake, but keep the car running.