Extended Vacation Part 2

By cassandrababy

Original link: https://www.lushstories.com/stories/crossdressing/extended-vacation-part-2.aspx

Tags: Crossdressing, Oral, Quickie

Added: 13 Apr 2011 Views: 9921 Avg Score: 4.69

Cassie continues her new life
Chapter Two in my novel of Cassie living 24/7 as a woman...please read Chapter 1 and let me know if you want more.


Chapter 2

After experiencing a great sexual adventure less than two hours after becoming Cassie full time, I was now in a even better mood as I got back on the freeway and headed north. Due to the low air pressure in my tire, I drove around 50 MPH for about ten minutes until I saw a big truck stop and gas station at the next off ramp. As I took the exit, my two new friends waved good bye as their truck passed me. I had driven by this truck stop many times over the years, but have never stopped. I was amazed at the size of it. It had a huge parking lot that featured at least 35 large trucks. I was just ready to pull into a parking spot, when I saw a truck driver walking from the restaurant towards his truck. I slowed down to pull up beside him.

“Hi.” I said after rolling down the passenger window. “I need some air for one of my tires, can you please tell me where I should go? This place is so big.” I used my best feminine voice.

He was a handsome man, about 45-50 and flashed a big smile once he saw me and knew that he could be helpful. He took a couple of steps towards my car and rested a pair of big hands on the open window and looked at me. His eyes started at my face, but before he said a word I watched his eyes discreetly look downward all the way down to my feet and back up to my face.

“You know young lady; you should know how to fill up a tire when it needs air, especially if you are travelling by yourself. But if you need help, I would be glad to help you, may I hop in?” He asked.

I told him “of course” and he directed me towards the gas station section of the truck stop.

“These days they charge you for everything, including air for your tires. However, since you are with a regular I know where we can get some free air; pull over there next to those two big rigs.” He was pointing to a section of the truck stop that specialized in gas and service for the big trucks.

I followed his directions as I explained to him it was my rear driver’s side tire that needed air. During the short drive to the service location I could feel his eyes checking me out over and over from head to toe. I was trying to do the same to him from my peripheral vision to insure I was safe, but more importantly that he was a candidate to have some fun with. From my occasional glances and my side vision, I could tell that he was indeed handsome and a strong candidate. My initial assumption was correct, I was sure he was pushing 50 and handsome. His hair was very thin on top and the little that he had was turning gray from his natural black. A full well groomed gray goatee confirmed the fact that he had transitioned from black to grey and also he took pride in how he looked.

“My name is Cassie, I expect you meet my type a lot at these truck stops.” I said. “You know girls in distress.”

“Hi Cassie, my name is Buddy. Stop right here and I will fill your tire.” He replied ignoring the second half of my comment.

“You don’t have to do that, I can do it myself, I know how!” But before I finished my comment he was already out of the car and headed for the hose to fill up my tire.

I looked in the mirror and decided to put on a little more lipstick, I also pulled my skirt up a little baring some more leg, my skirt was now just about two or three inches below my panties. When Buddy returned to my car, I noticed his immediate attention to my legs, so the adjustment to my skirt had done the trick. “Do you mind driving me back to my rig?” He asked.

“It is the least I can do for my Prince Charming.” I laughed.

My mind was racing on how I should approach this; I was still very horny as my young friends just got me warmed up. I really wanted to get into his pants whether it was a blow job or a nice hard fuck, but unable to come up with a plan. I was hoping he would make the first move, but he might too much of a gentleman. I was thinking I could tell him I was a hooker, because I knew that a lot of hookers hung out at truck stops, but I didn’t think at 4:00 in the afternoon, this would be the time. Before I could complete my thoughts Buddy started a new conversation direction.

“You sure have a lot of stuff in this Expedition; may I ask where you are going?”

“I sure do have lots of stuff, I am moving temporarily to Bakersfield from Los Angeles. I am renting a furnished apartment, but I had to bring a lot of my clothes and personal belongings. Where are you going on your trip? “

He replied in an upbeat tone “Well I am headed to Fresno, I don’t do really long hauls, I usually go between Arizona and Central California. I will get to Fresno around 8 or so tonight and then I will turn around and spend the night near Bakersfield. In the morning, I will head back to Phoenix and arrive around 3 or 4 in the afternoon tomorrow.”

He pointed to his truck and as I pulled the car up to his truck I said “Too bad you won’t be in Bakersfield earlier, my first night in town, I would fix you dinner to say thank you for helping me with my tire.”

Before he could reply I leaned over and put my right hand on his thigh and gave him a kiss on his left cheek. It was not a peck, I deliberately let my lips stay on his cheek and I could feel the roughness of his day long stubble on my lips. When I removed my lips from his cheek, I let my hand linger a moment on his thigh and then I straightened up and I could feel my skirt rise another inch up my thigh. My aroused sex drive was getting really heated and I wanted to reach over and stick my hand down his pants and feel his manhood in my hands.

“I would like that sometime, but we truckers have really odd schedules. Early morning and late nights, especially when you are like me doing short trips back and forth.” He said.

I saw a way that I could get his attention turned to sex so I told him “I guess that’s why they have hookers at these types of rest stops, you guys are always alone so much that you must want some company. I have thought about doing that sometime to earn money, but I prefer hosting in my hotel room or apartment.”

“Are you saying that you are a hooker?” He asked.

“Not really, but I have done it for money a few times. I really love sex, like if you would have come over for dinner, I would have wanted nothing more that you to fuck my brains out. You are so handsome, and I love sex, but I am not a normal girl in that way and other ways too.” I said.

“Well then, why don’t I just come over to your apartment tonight for the sex around 11 or 12, instead of dinner?” He laughed, but I knew he was serious.

“Baby, I would love that, but we won’t be able to have sex tonight, I am having my monthly visitor, but I would sure love to suck that cock of yours tonight.” I said.

We chatted a few more minutes and I gave Buddy a piece of paper with my cell phone number and address. He agreed he would call me around 10PM to confirm he was coming by and to give me an update of when he would arrive. When he stepped out of my car, I got out myself and met him by the side of his truck. I put my arms around his shoulders and realized for the first time he was well over six feet tall and strong. I kissed him on the lips and when he slightly opened his mouth I stuck my tongue inside his mouth and slid it under his tongue. He wrapped his strong arms around me and pulled me closer to him as his hands slid down to my ass and grabbed my cheeks in his strong hands. I ground myself into him sliding my belly sideways against his crotch and felt an immediate hardening of his cock through his blue jeans. I broke off the kiss and stepped up on my tippy toes whispered into his ear.

“Let’s do this now; forget tonight. I want you so bad, let’s go in your truck.”

I didn’t have to convince him as he opened up his door and stepped inside. He reached down and lifted me up into his cab. He slid a curtain aside behind the seats and there was a full bed. I guided him down and he sat on the edge of the bed. I leaned over and kissed him again and our tongues explored each other’s mouths. He held me tight with his arms around me and I wrapped mine around his waist.

We broke off the kiss and I knelt down on my knees in front of him. “Wow Cassie, you are so hot, I can’t believe how lucky I am to have met you.”

Before he could finish saying this I was already unbuckling his belt and starting on the buttons of his Levi’s button fly jeans. I could tell that he was very hard before I undid the first button as his cock was straining to come out of his underwear and jeans. I slipped his jeans down so they were around his ankles and I started to pull down the waist band of his briefs. A fully aroused cock popped out and smiled at me, it was not overly big about six inches, but beautiful.

I stroked it a few times and looked into Buddy’s eyes and I could see he was in heaven. I wanted to suck it so badly that I stopped stroking and slipped my lips around it and my whole body tingled with pleasure. I slid my mouth slowly down the entire length of his shaft and adjusted my angle so his cock slid down the entrance of my throat. I held my position so that my mouth was fully stuffed with his cock and my lips were around the base of his dick. After three or four seconds I started to rise up and as I slid my lips up his beautiful cock; I used my hand to stroke his manhood.

At this moment I realized this was not going to last long so I decided to let him shoot his wad. I went down on his shaft again this time very fast and then did the same action about ten times in fifteen seconds. I made loud slurping sounds each time I went down on his cock and after the second or third plunge I felt the familiar presence of two hands on the back of my head shoving my mouth down on his cock.

“Fuck Sandy, I am going to cum, and I am going to cum hard.” Buddy roared.

He was right he came very hard. It took a full effort to swallow his big load of cum without losing it out the through my lips. However, I kept in every last precious drop and savored the taste as I swallowed his love juice down my throat. I kept my lips around his cock and stroked the base to get every last drop of sweet cum out of his dick. When I finished I slowly removed my lips and looked at Buddy with a face that was glowing from ear to ear.

“God I love your cock, Buddy. What a sweet load of cum!” I said.

“Thank you Cassie, that was an unbelievable blow job, I came so hard, I feel great!” He replied.

Our goodbyes were short and he said he would call me sometime to set up a date. I stepped out of his truck and back into my car and in no time I was off to my new apartment.