Road Trip


Who said conventions were fun? Sure, it’s a tax write-off but when you boil it all down, it’s just a pain in the behind. Spend all week getting ‘ahead’ at work and ready to go just so you can spend your time off doing something work related. Have I mentioned yet that I was saddled with a college student that works at the library for this trip?

Just so you know, I do enjoy my job. I’m not fond of the conservative aspect of it, but the books… I love the smell of books. Hardcover, soft cover, new and old; they all smell fantastic. I enjoy the peace and quite of the library. I like to flirt with the guys when they come in; I’m subtle, to be sure, but it’s still fun.

So Friday night I found myself on the road, driving to an unfamiliar city in less than favorable conditions with Jack in the passenger seat. We left right after work and there were severe snowstorms to the north… the way we were heading for the convention.

I’d been working with Jack for the past couple months and he still hadn’t opened up to me. Our conversations could only be called such if we were discussing something work related. Anything else and Jack resorted to one syllable replies. And I get to spend the weekend with him… hooray.

I’m not one to give up easily, so for the first part of the trip I attempted to engage Jack in conversation. “How do you like school?”

“Uh,” was his reply. I took it to mean not very well.

I tried another route… “Do you have a girlfriend?”

“Un-uh.” Wow, two syllables on that answer! I think he meant no.

I pushed on asking any questions I could come up with that I thought might get him talking. Within a couple hours it was dark and I’d come to the conclusion that Jack wasn’t going to be drawn out of his shell. I’d used up my store of small talk. I’d also just gotten to the dangerous part of the trip. The snowstorms had passed through a couple hours before and the road crews hadn’t finished getting the roads cleaned up yet.

I was driving about the same speed as my conversation with Jack. So as I meandered down the interstate, Jack sat quietly in the passenger seat. Occasionally some SUV or another would go flying by, making me nervous. I stopped trying to engage Jack and shortly afterwards he fell asleep. Although Jack isn’t much of a conversationalist he’s really cute, especially when he sleeps, as I just learned. His dark hair was messed up from trying to get into a comfortable spot and his black-framed glasses had slid down his nose and were slightly askew. I could hear his slow, rhythmic breaths through his slightly parted lips. And sleep removed those worry lines that were always in existence from stress. All in all, the effect was charming and I spent too much of the trip watching him sleep instead of watching the road.

I continued driving; slippery roads, slow speeds and darkness. The sun had set and we should have been arriving at the hotel by now. Unfortunately, because I’d been driving so slowly from the snow and ice I was still an hour away in good road conditions. As things were progressing we wouldn’t be there for another two or three hours.

His soft breathing (it wasn’t quite snoring, but close) was starting to make me really tired. Now I was fighting to keep my eyes open in addition to keeping the car on the road. I saw a sign for a Rest Area in a mile. There was nothing for it, I was going to have to stop and get some rest before driving any more tonight.

I angled into the Rest Area, slowly weaving between semi-truck after semi-truck. I pulled into a spot near the end of the row and backed in under a light for safety. Sleeping beauty was still out cold. I didn’t want to wake him, so I grabbed my keys and my travel bag and went inside. Actually, I flew inside! The night was so cold that just that short distance had my teeth chattering from shivering so hard.

I did my nightly routine there in the restroom, brushed my hair and teeth and changed into some cotton sleep pants and a white T-shirt. I already felt better; the knots in my back from driving in the crazy weather were already starting to work themselves out.

Bracing myself against the cold I headed back out to my car. The semi-trucks were all running, keeping their occupants warm in the cold weather. Most of the drivers had their cab lights on, talking on their cell phones or reading. As I passed the truck parked closest to me, I looked up into the cab. Oh my goodness! He was being naughty! I got a great view of his cock as he slowly stroked himself up and down. I stopped in my tracks, standing outside his truck looking in despite the cold. He hadn’t noticed me so I watched him for a few more strokes and smiled, heading back to my car.

I don’t know what had a greater effect on my now hard nipples, the extreme cold or seeing the trucker. I quietly got back into the car and tried to see into the truckers cab. I could never pass up a show like that! I couldn’t see much, but enough to go on with. I could see that he was still working himself slowly, taking his time, enjoying it. I looked over to see that Jack was still asleep.

I could tell that my sense of adventure was going to get me in trouble. I was getting really excited watching the trucker. And the thought of getting myself off without waking Jack was quite the turn-on as well. There’s nothing quite like the danger of getting caught.

I started watching the trucker again… cheering him on in my mind. That’s right, sugar, stroke that nice cock of yours. I took off my coat and felt my hardened nipples through my thin, white T-shirt. Mmmm-hmm, I know that feels good! He must have felt me watching him, because he looked up and immediately saw me. I smiled at him as I continued playing with my nipples.

I wasn’t the only exhibitionist in town; he smiled back at me exaggerating his movements for my benefit. I felt my nipples harden even more. I checked to make sure Jack was still sleeping. He was still out like a light, so I slowly lifted my T-shirt up over my head to show the trucker my gorgeous breasts as I played with them. He smiled and nodded as I teased my nipples with my left hand and slid my right hand between my legs.

I was already so hot; I quickly slid my hand under my panties. It felt so good to be touched that I barely suppressed a groan as I slowly slid a finger inside myself. My trucker friend was certainly enjoying the show, he nodded to me again, a look of ecstasy on his face as he licked his lips. I know what he was thinking; I put my finger in my mouth and tasted myself. I saw him mouth to me, “Yes.”

Exchanging my finger for my left nipple, I saw him nod again. He liked watching me lick my own nipples. I felt my pussy flooding with wetness as I teased with my fingers. I alternated between pushing my fingers up inside and lightly stroking my clit as I watched the trucker stroke his cock. I sat up a little further, hoping a bit of a different angle would allow me to see his cock. I wasn’t able to see any better, but he seemed to know what I wanted and lifted up off his seat to show me his beautiful piece. He looked so hard and he was stroking himself so softly, it seemed as if he was on the verge of cumming. The very thought got me so excited.

I felt another rush of heat and wetness between my legs and couldn’t help moaning loudly. Suddenly I remembered that Jack was right next to me, I quickly looked over, he was still asleep. Although something of what was happening in the car seemed to be coming through in his dreams; his hand was on his cock and his cock was so hard it was straining against the fabric of his pants. As I was looking at him he moaned very softly and shifted his hand on his cock. From the look of things, Jack seemed almost as well equipped as the trucker.

I looked back at the trucker who was watching me. He knew what I was up to and found it amusing. I tried to be quieter so I wouldn’t wake up Jack.

Silently I mouthed to the trucker, “Show me.” He was more than happy to and I was rewarded with the sight of him stroking himself. I was so excited, my fingers were totally slick with my wetness. I was so close, but my panties were getting in the way of my orgasm. I lifted up off my seat so the trucker could see and pulled my pants and panties down; taking my time so he could watch me playing with myself the way I had watched him. He nodded to me again, smiling.

I was so close. Just on the edge of cumming, I was making little whimpering noises as I worked myself closer and closer. Well, I thought they were little noises! I saw some movement out of the corner of my eye – Jack was awake! And quietly watching me pleasure myself while he touched his hard-on through his pants. When he finally noticed me looking at him (he had been watching me finger myself) he froze and blushed so deeply that I could easily tell in the dim interior.

I wracked my brain trying like heck to come up with some explanation… and quickly realized that there was no explaining this away. Besides, wasn’t he just touching himself while watching me?

I just smiled at him and shrugged my shoulders. He turned his head away, afraid I’d be upset with him. Mmm, I just love shy men. “What’s wrong, Jack?” I asked slowly, “Don’t you want to watch anymore?”

“I… uh… well…” he stammered.

“It’s alright,” I told him, taking my hand from my breast and touching his shoulder, “I want you to watch me.” I slowly slid my hand down his arm until it was on his hand. I gently took his hand and placed it on my breast. He caressed my boobs, using his other hand without my prompting.

“Your titties feel so good,” he said, “they’re perfect.”

It was my turn to be amazed. I’d never heard Jack speak so much at one time… ever. He leaned towards me and kissed my neck softly, sending chills up my spine. “Mmmm,” I moaned, pushing against his hands and mouth.

“I’ve wanted you since I first saw you,” he whispered against my neck, “I’ve always been afraid to talk to you or you’d know.”

I just giggled. What’s wrong with me knowing? He put his mouth on my breast and suddenly there was nothing to laugh about. The way he used his teeth, lips and tongue on my nipple had me moaning again. His hand slid down my stomach, my hip, down to my knee and back up to my thigh. I took his hand and pressed it against my wetness, moving his fingers on me, inside me, showing him how I liked it. He was good with his hands and soon I was moaning and wiggling on his hand, loving the feel of his fingers inside me.

He took his hand away and I couldn’t help but make a sad, pleading noise. I put my hand in his lap and felt his cock through his pants. Quickly going after the button and zipper, I wrestled him out of his pants and boxers in record time. I looked up to see him tasting me on his fingers. His mmmmm turned into a yeahhh as I lightly ran my fingers down the length of his cock.

It was beautiful: long, straight and moderately thick. Like most college students he kept his pubic hair trimmed short and completely shaved his balls. His cock was so hard that it stood straight up in the air, I found it irresistible. I leaned across the seat and pressed my lips against the head of his cock. He moaned deliciously and his cock twitched against my lips as I slowly opened my mouth and slid my lips down the length of him. The feel of his soft skin and the hardness of his cock as I pushed him down deeply into my throat was incredible.

I leaned towards Jack to get a better angle, lifting my bare ass up in the air. I felt his hand slide down my back and I arched my against his hand like a cat, moaning on his cock.

“You’re a very naughty librarian,” he said, lightly slapping my ass.

“Mmmm-hmm,” I moaned on him, absorbed in what I was doing.

His fingers were inside me again and I moaned and wiggled, loving the feeling. Suddenly it occurred to me what he had said about me being a naughty librarian. Does he know about me? I thought, Or was that just the obvious thing to say? He pushed his fingers deeper inside and I stopped worrying about it, losing myself in the sensation of his fingers inside me and his cock throbbing in my mouth.

I took my mouth off his cock just for a second, “Cum for me, Jack, I want to taste you.”

I went back down on him again, working him faster with my mouth. He moaned in response and pushed his fingers a little deeper inside me. I couldn’t help moaning on his cock as my wetness ran down my thighs in a flood. I used my hand to squeeze his balls as I sucked him fast, hard and deep. His moans grew louder and louder. I took him all the way in my throat, pressing my lips to the base of his cock and moaned. He groaned so loud, he almost sounded in pain.

He tangled his other hand in my hair and kept my face pressed down in his lap as he lifted his hips, driving his cock deeper in my throat. I squeezed his balls even harder and felt him start cumming… his cock throbbing in my throat and the taste of his cum filling my mouth. Oh… yes.! He stopped pushing my head down and I gently sucked him up and down, drinking up all of his cum, toying with his still rock hard cock.

“Mmmm,” I moaned, licking up and down the shaft like he was a Popsicle… an especially delicious Popsicle.

He caught his breath and looked at me, “Now you,” and he pushed me back and flipped me over, lifting my hips up in the air and putting his mouth on me.

His tongue flicked my clit as he pushed his fingers back inside me again making me cry out. He used his tongue to gently tease, making me push against him for more pressure while his fingers stroked deep inside me. He wasn’t going to be waiting long; I was right on the edge of cumming.

I looked outside, remembering the trucker. He was still working himself. “Show me,” I mouthed to him, smiling and playing with my breasts as Jack ate me. He just nodded and lifted up off the seat so I could watch him. Stroking his cock faster and faster, I watched him as he came, squirting his load onto his belly.

It was too much to hold off any longer… I was wiggling against Jack’s mouth and fingers, panting with the painful bliss of being right on the brink of an orgasm. He moaned against me and there was no chance of holding back any longer. I cried out, shaking and twitching as he softly licked and kissed my pussy, working me a little slower with his fingers. I could feel myself cumming and Jack made yummy noises as he tasted even more of me.

I finally pulled away, collapsing into my seat with a sigh. That was fantastic. Jack leaned over to me, kissing me softly as I slowly licked my juices off his lips and chin. “Thank you,” we both said at the same time, smiling.

I looked over to the trucker, we gave each other a ‘thumbs up’ and a smile. Jack and I got dressed and settled in to take a nap before getting started driving again. This was already the best convention I’d ever been to and I hadn’t even arrived yet!

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