Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one.
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, body waxing 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.
A little concerned about being on this deserted exit ramp, I exited my car and strolled towards the back of my SUV. I could immediately see that my driver’s side rear tire was low in air pressure and needed some attention. Questions ran through my mind of if I could drive with the low air pressure or should I call AAA; what should I do? My thoughts and questions were rushing through my mind and I had to deal with the two guys stepping out of their truck. I relaxed as my thoughts went back to my planning over the past few weeks; I am not Tony, I am Cassie, so just act that way a woman would act in this situation. Then as I looked again, I knew the tire was not that bad and I could definitely drive for a while without danger.
“Thanks for flagging me down.” I said to the driver, who approached me first.
“No problem, do you want us to change your tire for you?” He asked.
“That is so nice of you to offer, but we both know that I am fine to drive on this tire for at least 30 miles.” I said as I looked him straight in the eye. “So were you just having fun trying to see if you could get me to pull over or something?”
By this time his companion had walked up beside him and we were about a foot apart. I was standing behind my Explorer in a very sexy pose. I took the moment in silence to check out my new acquaintances; they both appeared to be around 25 (maybe younger) and almost dressed exactly alike. They were wearing t-shirts, shorts, athletic shoes and white socks. The only difference was the color and brands of their clothing. The driver was probably about two inches shorter than the other guy, but both were over six feet tall. They both wore their hair a little long, not to their shoulders but certainly to the bottom of their neck. One featured blond straight hair and the other black curls. Yes, they looked like great fucks! I am very good at judging people’s character and I knew these two were good guys and wouldn’t hurt me.
“We were just trying to be nice, didn’t want you to get a blow out or something.” This was said by the passenger, who by the way had the curly black hair.
“That’s too bad, I thought you wanted to try and pick me up!” Before the words were finished, I stepped forward wedging between them and placed a hand on each of their crotches. “If you play your cards right, I might suck your cocks.”.
I must have shocked them, because they became stone silent. “Get back in your truck and follow me if you want a quickie.” I said.
Of course the followed me, but I think I stunned them long enough that I was already closing my door and releasing the emergency break and driving away when they finally got back to their truck and follow me. I was laughing at myself and was curious what they were thinking. I turned right at the end of the off ramp and sped up to about 50 miles per hour. I drove for almost a minute when they caught up and I pulled over to the side of the road. I looked around and there was nothing in sight for more than a mile. I opened my door and waited for them to stop behind me.
I approached the passenger side door and when it opened the black hair young man stepped out. I walked up to him and stretched on my tippy toes and kissed him on the lips and immediately slipped my tongue between his lips and danced my tongue all around his mouth. At the same time, I slipped my hands under the waistband of his loose fitting shorts and found his cock which was becoming hard. I broke off the kiss and guided him to sit down sideways in the passenger seat as I felt a set of hands grab my hips from behind. I turned around and saw the driver who was a little shorter and I didn’t have to stretch as much to give him a very wet kiss as well.
I unbuttoned his shorts and pulled them down as well as his navy blue boxer shorts. I pulled a condom out of my pocket and quickly opened the wrapper while stroking his hard cock. I slipped the condom on him as soon as he was hard and I whispered in his ear “It’s my time of the month baby, but I want your cock inside me. Fuck my ass baby.”
This is when having a small cock is handy; I could conceal my balls and cock by shifting my gaffe around. Unless he tried to rub me (which after saying I was on the rag was not likely to happen) he would not see or feel my manhood. While I was making this shift I noticed the black hair passenger had pulled down his shorts and I had a nice hard six inch cock practically staring at me. I slipped my lips around his hard cock and felt his friend trying to find my ass hole to shove his seven inch pole inside.
It took a minute or so, but we made the unusual setting work just fine. My mouth was all the way down on one guy’s cock while the other one was starting to get a rhythm of shoving his dick inside me. Before long I was swallowing every inch of a cock in my mouth and ass at the same time. The guy behind me grabbed my hips and lifted me a couple of inches up in the air and my ass slid down the entire length of his big cock. I felt impaled on his large dick as he shoved hard to get leverage and to bury his sword in my tight asshole.
I took my mouth of his friend’s cock and started to lick the underside of his balls and stroke his cock. “God damn, you are so fucking deep inside me. Fuck my fucking ass honey.”
My language must have turned him on as he started to moan. “Oh baby, here I cum, I am going to cum so hard.”
“Me too!” His friend said.
“Pull your cock out, I want both of you to cum in my mouth.” I said.
I felt him pull out and I immediately went to my knees. The pavement was hot and I could feel the heat of it on my knees and I could also feel the heat of their cocks in my hands as the passenger stepped down out of the truck and I grabbed each of them. I went work on both of their cocks with my tongue and could taste the start of a powerful jet of cum juice that was forth coming. When I knew it was only seconds to go I opened as wide as I could and guided both of their cocks in my mouth. I don’t know who it was but one started cumming immediately.
One of the guys tried to shove the back of my head so I could swallow them both, but my mouth was not wide enough to take more than just the head of each cock. The other cock started to spew as well and I felt more cum in my mouth than ever before. I took their cocks out and they were both jetting cum and I directed it all over my face.
When they were done and I had swallowed as much cum as possible I told them to wait as I returned to my SUV. I pulled out some wipes and grabbed my camera. We took some pictures of my face and I took pictures of their cocks. I told them I was making a scrap book of all the cocks I was going to suck and fuck the next seven weeks and they laughed. I cleaned up my face with the wipes and also wiped their cocks and balls to make them clean. We said our goodbyes and I was on the road again. What a delightful way to start a road trip.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/extended-vacation.aspx">Extended Vacation</a>