The Rest Stop Digest - The Jill Jordan story

I woke up some time around 2 pm. I was still drunk with lust from my first taste of a strangers cock. I could still taste his semen in my mouth. I couldn’t wait to go back. I decided I was gonna get ready and go early. I still had a good supply for cocaine and I was gonna start into that soon. I showered , clean my self appropriately and began to pick out my outfit. It took me a few hours to get my self ready. I choose one of my sisters cheerleading outfits. It fit so well my pussy quivered. It was about 5pm when I headed to the rest stop. It was still light out , but it seemed to be somewhat eventful. I park in a spot. Turn the engine off and say in silence for a min. I was feel nervous but I was still eager to find a cock.

I did line of coke and It hit me hard. I was keyed up all over again I decided that I would take a walk. I stroll down over to the truck parking lot. All the 18 wheelers sitting side be side. There had to been about 30 of them facing the facility. I walked over to a picnic area in the middle of the car area and the truck area. Even though it was in sight of everything, it didn’t matter to me. I sat down at a picnic table and I crossed my legs. My plug was pressing my G-spot and I fell a sizable drip. I grabbed for my bag cocaine , opened it and took a large shot that was at the edge of my car key. It hit me fast as I humping the bench of the picnic table . Suddenly , I came out of my trance when I head a large stick crack behind me. As I quickly turn and look behind me , a chubby man was standing a few feet away.

He looked middle aged , of average height , chunky and had a long beard. He was just a little taller than I. He had on a black t- shirt , and blue jeans.. As he walked towards me, my heart was racing in anticipation. The drugs had taken affect and I was completely vulnerable. I had no inhibitions and he this stranger seemed to know it. I stood up as he walk my way. As he got close to me, he put his hand on my shoulder and turned me around so that my ass was facing him. I made sure to stand in the most sexy way I could . Sticking my ass out and arching my back. He stood behind and immediately I felt his hand on the inseam of my legs as I felt his rough hands move upwards under my dress . He reached my hole and realized i was plugged.

“ mmm “ he groaned as he slide his hand underneath me to grab me clitty that was locked up

He asked me how old I was and how long I’ve been living as a sissy.

I told him 18, and explained that I am fairly new to it. He then pulled my hand to his crotch. I could feel a very thick package underneath his jeans.

He ask me if “ This is what I want?”

I immediately answered “ Yes. oh please yes”

That is when he said “Come down to my rig.

He then grabbed my hand ( as if i was a child) , and led my on a short journey passed a few 18 wheelers. Then reached and open the door to a red one close to the end of the roll of trucks.

He climbed in first and lead me to the back where there was bed.

He immediately said “ Get on your knees”

I saw him fumble around with something in a corner . He then removed his shirt and the black on his protruding belly caught the light for outside. I was so turned on. I then grabbed my baggy of coke and took a. Monstrous rip into my nose. As the cocaine rushed down my throat , I gagged.

The man stand “ you partying eh? Thats good. It makes this a Better experience.

He asked me about other people I’ve been with.

I explained that other than a guy I met less than an day ago , I had no experience.

“Ahh Fresh sissy pussy”. He remarked in a delightful tone

“ As long as you do what you told and follow my directions, you will learn alot. Your job is to please me and my cock. You got that?”

“Yes” I eagerly Answered

Then he took a step forward and grabbed the back of my head and pressed hard against is crotch. I felt his cock twitch throw his jeans .

He said “. Take a big whiff in and smell my crotch. From This day on , a mans crotch will be your job site, and your responsibility.

I said “ yes daddy “ as I reached up to unzip his fly . He smack my hand and said you do not have permission just yet to touch my cock

“Kiss my crotch and lick around the outline of my cock. Inhale again and smell my crotch. “ he directed.

Smelling his crotch began to drive me crazy. I needed his cock. He knew it too .

He said “unzip my pants pull them down. But keep my cock covered by my underwear.”

I did exactly what i was told .

He then said to kiss his cock through the underwear. He told me to kiss it a few times.

Each time that I did it twitched. It felt so good as I pressed my lips against his sweaty tidy whites.

Then he gave a nod and said

“ pull it out”

I then pull his underwear down and out came his thick gorgeous cock. It wasn’t extremely long but it wasn’t small by any means . Probably between 6 and 7 inches. But very thick . And a very pronounced mushroom head. I was in complete awe with the moment. I was on my-knees with this amazing cock twitching in-front of me. Periodically hitting me on the nose as he twitched it.

He said “Smell the head of my cock then kiss it in appreciation for it.” As he laid his on my face . His big hairy balls pressed firmly on my chin .

His cock a smell to it . I guess you could say a bit “ rank”. Probably didn’t shower that day, at the very least.

He slide is cock down my face and left his beautiful mushroom head on my lips. I began kissing his cock. He had a good amounts of precum all over his head..I instinctively licked it all up. The taste of his precum sent me into deeper trance of lust. The thought of me licking a strange mans spunk, as I worship his gorgeous cock was so dirty as a thought. I was shaking in excited as I kiss his cock slowly and softly.

“ Ah good girl!” He affirmed

“ now slowly slide your tongue down’h shaft to my balls. “. He directed

I followed orders. And slide down to his balls

“Kiss them softly” he said

Kissing them as if I absolutely loved them .

“Now lick them”. Lick them slowly and then lightly suck one in your mouth.

At this point I was in Ground zero of man funk. But it only turned me on.

I continued to focus on the balls, until he stopped me and took a seat on his bed . He was leaning back on his elbows. His use his finger as he beckoned me towards his. I got my self over to him. On my knees , almost eye level with his thick cock and sweaty balls. He then leaned back and spread his legs. He grab the back of my head and pulled my lips right to his asshole.

Oh!! He moan as I began to lick his asshole. And at this point I couldn’t believe i was licking a mans asshole. Truth be told , I love it. I lick and kiss his asshole and slide my tongue in.

He said “ yeah eat my ass “

His cock was now rock hard and standing at full attention. With the taste of his ass on my mouth. He then stood back up and placed his cock on the tip of my lips. I began swirling my tongue all around his manly mushrooms tip helmet. The ridges of his cock head were so pronounced. His beautiful cock was almost throbbing. I began to give intense suction as began bobbling my head up and down. I was producing a-lot of saliva and was getting really low on his cock. The man began to moan more erratically. He definitely approved of my job . I gagged a few times as moved at a quicker pace. Finally he grabb my head shoved his cock all the wAy down . His black pubes where mashed in my face. And my forehead Was pressed against his beer belly. I began to gag and puke up saliva. It was too much for me.

I think he was about close to cumming cus he changed things up . He then released my head. As I came up gasping for air .

He said “ Get on the bed . On all fours and ass up”

I knew what was coming and I was extremely excited. I reach over to my purse and grab the bag of coke. I took another big hit and I was ready.

The man slap my ass with serious force . It startled me. Then Felt him pull on my plug. The pressure got more intense the further he pulled. He in no way was gentle about it. I took a deep breath as my plug popped out. He took the plug and reached up and put in my mouth.

“ Keep that in there til we are done” He ordered

Then I was started when I felt him begin to lick my pussy. I had never experienced someones soft tongue against an area so private to me. It seem to get better the longer he did-it. Feeling his tongue swirl round and around. It was a novice feeling to me. But it was so amazing. His tounge darted all around my pussy. Then I felt him suck my hole into his mouth. But he countered the feeling, as I felt his tongue press hard inside me. I was in absolute ecstasy. He pulled off my pussy.

“ Wow, I love licking teenagers assholes. So tight”

I look behind to saw him standing there, aiming his cock at my boy twat. I was overcome with excitement and anticipation. I was about to be fucked by this complete stranger. I was letting this man stick his penis inside me body.

I felt the warm of his body against mine as he started to run the tip of his thick cock up and down the crack of my ass. His cock felt extremely warm. I was so much better than i ever imagined. After a few swipes I felt him right at the edge of my boytwat. Then he pushed in and I felt the most wonderful feel I have ever experienced. My dildos were no compassion to this man cock. It was as if it was meant to be in there. He kept pushing in and I felt clitty drip with a steady flow. I had a tiny orgasm and it felt like ecstasy. I let out a moan that was genuine and real. When he finally bottomed out I was in a different world. He stayed there for a short time. I felt his large chubby belly on my back. If felt amazing to have this man behind me. I moaned again and just as he pulled back again. Just when it felt like he was gonna pull out , he push in again. And bottomed out.

This time he let out a grunt, as he remarked
“ So fucking tight. I don’t know how long I can last”

“ Oh My God, Daddy fuck me”. I encouraged in a mumble due to my butt plug in my mouth.

He started to saw in and out of me. Each thrust cause me clitty to leak . Is hands where on my hips as he began to speed up the pace. In and out going the full length each time . He began to slam me and grind hard with every thrust. I began to feel a strange pressure building and building. He was ramming me and grunting. His cock seemed to get harder as he continued. The pressure in my hole was beginning to be a little uncomfortable. And my hole was spasming on its own. Suddenly, I realized what that pressure was as I felt the familiar feeling of an orgasm. I was losing control as he thump me with blow. My hole was tightening up on its own. The wave of paradise hit me.
I screamed “Ohhhhh!! Im cumming ! Ohhhh my gosh” as I accidentally dropped my plug out my mouth.

It the most intense orgasm I ever felt. He never relented as he single handedly push me into heaven. I lost touch with reality for what seemed like days . When i finally gain my reality he was still pushing hard. Between his grunts and his heavy breathing, he began talking dirty.

“ Yeah, take that cock you little bitch.” You love cock in your ass faggot, don’t ya? You gonna take me load soon bitch . You gonna take me sperm inside your ass. You hear me?

He began to pump a tad hard and I felt him stiffen up. Just as he did , he hit my spot. Once again I was cummimg . This orgasm hit fast and hard. Just I began my peak he began to grunt like a beast and push hard into me. He was barring all his weight on me and I couldn’t support it, I went from being on all fours to flattening out with my immense chubby lover on top of me . He was squeezing me tightly as he climaxed . And I finally came back from another intense orgasm. He did too . He was still on top of me just laying there breathing heavy. He kiss my neck as he regained his composure. He finally began to get up , as i felt beautiful cock leave me body .

“Don’t get up just yet” he ordered. You need to be plugged with my semen”

He placed my plug back in , and it was a slight disappointment , for that I already missed his cock.

I Sat up and began to gather myself. I was quiet , because I was honestly lost for words. It was everything and more than A ever expected. I was in shock of how amazing it was.

The man spoke. He ask me my name.

“Jill“ I said

He nodded and said “ Im shawn “

His sweat had covered my entire body . I was extremely hot in the truck. I needed some air and began to make my way out . He opened the door and let me out as he followed.

As we both hit the ground from the truck , he pushed to my knees. And he his cock was in front of my face.

He said “ You have one more responsibility. i need to piss after sex. And your mouth is my toilet. Now open up”

I was still completely high and I actually wanted to drink it. So I put his semi hard cock in my mouth and began to piss. I immediately began swallowing. It was bitter and salty. I just keep swallowing it. It was so dirty drinking this anonymous sloppy chubby hairy mans urine. It was l disgusted with my self for drinking this mans urine. But I that fact only turned me on more. After what seemed like a while, he was done. He then shook the remaining drips in my face and whipped me with his cock a few times.

“You are a good fuck “ he complimented.

He said “ I am here tomorrow night too. Come by and I could line up a few surprises.

I nodded and began my shameful walk to my car.

I keep on thinking how much I loved having Shawns sperm swimming inside me. And having a stomach full of piss just added to the excitement. I felt so feminine and so used. It was exactly what I needed. I knew that I was truly a woman after that moment.

To be continued…