Sissies love truckers!

Story Info
A weekend of sissy fun gets started early w/ lucky trucker!
1.6k words
4.71
5.5k
13
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was almost quitting time on a Friday afternoon. I was so excited to get on with the weekend of fun. The rest of the guys on the construction site were planning to hang around and drink a few beers after work and I knew they were going to chastise me for not hanging staying around. I had worn a sexy pair of white lacy panties under my blue jeans and I was leaking precum, I was so horny to show off my feminine body. Possibly some lonely truckers or straight guys not getting what they need. Just generally see what kind of girly trouble I could get myself into for the weekend.

I parked my tractor pulling my t shirt down to make sure my panties were not peeking out when I hopped down to the ground. Of course all my coworkers were egging me on to stay and have a few beers, as it became evident to them that I was not going to stay, I was walking to my car when one of my coworkers jokingly yelled out "don't be such a sissy!" ...if they only knew!

I started off down the road, I was headed to a motel a few towns away to get fully dolled up but thought I would have a little fun on the way. I pulled off the road a few blocks away and stripped off my jeans and put on a bra and a white spaghetti strapped tank top. I love riding down the interstate with my sexy white lace panties exposed, putting on a show for the truckers as I passed by.

I was born naturally hairless and have always been told that I had "great legs if I had been a woman". So when I shave my legs the are spectacular, tanned and rise into a great ass with a waist just made for wearing panties.

As I got onto the freeway I was passing truckers, getting a few honks here and there. A few truckers would increase speed as I passed so as the enjoy the show a little longer. As I approached a white truck with green stripes pulling an empty flat bed trailer, I could tell the driver was adjusting his mirror and was looking back at me as I approached. I could tell he knew I was coming, there must have been some CB radio chatter about my little exhibition and knowing that, made me even hotter. I drove up next his cab and intentionally rode there next to him for a while so he could get a good look. As I started pulling away the truck sped up too. I sped up a little more and he matched my speed again. I did not want to risk getting pulled over by the police while dressed in lingerie so I slowed to duck in behind the truck as he passed he lowered his hand with a thumbs up of approval and waved his arm as if to direct me to follow him. I knew there was a rest stop a few exits up. Normally I don't play with Men until after I am fully dressed with make up, hair and slutty clothes. But I was very excited at the prospect of what this truck driver had in mind. I wasn't 30 seconds or so that I saw his blinker turn on and then we passed the sign "Rest Area Next Exit". Oh my! what was about to happen. I wondered if I should even pull in or just keep going. But, like something inside had already made the decision, I was following this truck into rest area.

As his truck slowed, my mind raced with thoughts of what this man wants to do. Would he want to fuck me? just let me suck his dick? Hell, I still had no clue what he looked like accept that hairy arm out the window and I really like hairy men!

I was digging in the bag next to me in the passenger seat desperately trying to find my daisy duke cut off short shorts so I wouldn't have to walk all the way to his truck in just my panties. Finally, after digging and causing a storm of nylons, garters and panties I found them. Just then the truck had turned into a truck stall and I turned in the next stall on his passenger side. I do not think he had even stopped yet and he had reached over and flung the passenger door open as an invite to hop on in.

I stepped out of my car, I could feel a warm breeze over my lacy lingerie clad body as I stepped into those daisy duke shorts. As I pulled them up and could feel them snug up against my little smooth hairless boi pussy, I had never felt more feminine than I did in that moment. I didn't know exactly what was gonna happen as I stepped forward. But, as I climbed up into the passenger seat and saw that square jawed country boy looking at me, I knew I was gonna submit and satisfy this man.

He said hello, smiled and motioned for me to climb between the seats and back into the sleeper portion of his rig. As I did, i felt his big hand cup my little ass cheek. One of his thick fingers slipped under the denim fabric of my shorts and I could feel it touching my lacy panties. In that moment, feeling the rustling fringe from daisy dukes and this masculine hand manipulating its way under my lacy thong with a mission to get to my little pink hole, a shudder went through my entire body, goose bumps shot up all over my smooth feminine skin and my back arched as I pushed back into his hands. I knew my body was all his now!

His hands pushed and moved me all the way back onto the mattress as he followed behind. I glanced back to see that his pants were undone and could see his stiff fat cock escaping his jeans. About that time I felt his hand between my shoulder blades pushing my upper body down to the mattress while his other arm was under my waist making sure my ass stayed in the air. He unbuttoned my shorts and wrangled down, pulled my panties to the side and buried his face between my ass cheeks. His tongue darted in and out of my sweet hole. As he worked to get my shorts all the way off I turned and sat facing him so he could slide my sexy little shorts down my legs. He commented how smooth and sexy my legs were and he never knew that even a sissy boy could have legs like that.

As I sat facing him all I could look at was that monster cock, he had taken his jeans off and his hairy body with that impressive cock sticking up was irresistible. I lunged and planted my mouth around his cock, it was big but it fit just right. Like my mouth was molded to be around a cock or something. I was on all fours with my mouth around his cock and he was reaching across my back and fondling my hole. Then I felt the lube hit my hole and his finger darted in and out and I knew it was time for me to turn around and give him what he needs. I turned around. He again pushed my upper body and head to the mattress and held me just where he wanted me. I felt him pull my panties aside and adjust them just how he wanted. Then his cock slapped against me I could feel drops of his pre cum splash around as it did. I could feel the head of his big dick pressing against my hole. I relaxed, let myself be all his and his cock slid slowly into me. Two times he pushed about half way in. Then that third time he kept pushing and I finally his hairy masculine body touch mine. He was all the way inside of me. His hair tickled and excited my smooth skin as it pressed against me. With each thrust I would feel that tickle again and again. He would occasionally have to re adjust my panties out of the way, so I reached back with one hand and held them out of the way as he put both above my hips, pulling me towards him as he thrust deep inside of me. The pace of his thrusts was quickening. I could feel his massive shaft getting even stiffer. Then he slammed into me, pulled me hard back against him and could feel his cum exploding inside of me. Three huge spurts and he started slowly sliding back and fourth enjoying that wet mess he had made in my boi pussy. As he pulled out I could feel his cum soaking the thin crotch of my panties as they returned to between my ass cheeks.

The satisfied truck driver sat back, his softening cock glistening, he asked I lived around the area and said he passes thru this part of the country every couple months or so and would love to do it again, so I gave him my phone number as I adjusted my panties and pulled back on my daisy duke shorts. I climbed from the truck and as I walked back to my car I could feel that breeze finding it's way to that wet spot of panties and a little drip of cum working its way down my inner thigh.

Wow! What a start to my girly weekend and I have not even made it to the hotel yet.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
TeriLeighTeriLeigh13 days ago

You go girl!! Any truckers in Ewing NJ? Great story girlfriend.

EricaDoesNowEricaDoesNow13 days ago

Truck stops ARE fun!

Share this Story

Similar Stories

A Night at the Adult Book Store A trans woman goes to an ABS and things escalate from there.in Transgender & Crossdressers
Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
My First Solo Sissy Night... A guy explores the sissy kink on his own for the first time.in Transgender & Crossdressers
Becoming Fuck Meat: A Sissy Tale Sissy Kristy goes back to Sir's motel room.in Transgender & Crossdressers
A College Whore Pt. 03 Sean (Now named Candy) is blackmailed into modeling!in Transgender & Crossdressers
More Stories