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Hitchhiking America (EtherealElvenEmpressxDrake93)

Elena let him take the dry dom get fingers as she went back to finish the last of her Coke. He was at least being honest saying how many he picked up. Listening as he even decided to tell her his size the only reason she chuckled was because she saw the waitress reacted to listening in. “The only other question is how many you think we need. Most men say like 5 boxes but I have feeling you are a realist. Sodo you think you can use a whole box? And…” she leaned in to whisper. “I think the waitress is listening maybe we should head out before you cause a scene…”
 
Tyler smiles then after looking at the waitress smiles even more. "Oh I think we both have already. She's clearly trying not to draw attention but she looks wet... Maybe she wants to try hitchhiking herself.." Tyler knew she was out of ear shot when he said this. He finished his own drink off leaving ice cubes in the glass. "Well in the box I'm getting are 40 condoms. I might grab two just to be safe but it really depends on how far I'll be driving you." Tyler wasn't really framing it like a question more like giving her the choice. In most cases Tyler would buy two boxes of it ment crossing state lines and only one box if he was staying in new York state.


Tyler smiled as they stood up ready to go even as he was still waiting on her name...
 
“ I hope you don’t plan on coming back here ever again I’m sure she’s going to tell her coworkers about you not sure I could be good could be bad I usually don’t draw attention to myself with the staff.” once they finish she grabbed her bag which wasn’t much and was on her merry way. They stop by the convenience store and she let Tyler pick up when he needed but he paid for their food and drinks of course. “ sounds like someone’s eager and it sounds like he pick up waitresses and all sorts on the way it’s probably best way to get protection I’m not sure how many waitresses you’ve slept with.” Seeing what he bought she figured he must get around quite a bit. It was always better safe than sorry So having a big pack meant no accidents along the way to wherever they were going.

Elena didn’t forget that she didn’t say her name but do you like being mysterious for a little bit so she decided not to say anything until they got near the truck and he figure out where she was sitting.
 
Tyler nodded his head looking after the other girl. He wasn't intending on coming back here anytime soon. But he was thinking he might find her hitchhiking one day. The shop was small and to his surprise had the exact box his was looking for. The cashier asked if he was planning on a weekend of fun with the sexy blonde he'd walked over with. Tyler chuckled and winked. Not saying anything either way. As Tyler left the store bag in hand. "Well that depends. Are you a waitress?" Admittedly Tyler had slept with two waitresses before. One right after a nasty breakup and the other well a brunette he was driving to a new city wanted to try a threesome. So if she was he was going to sleep with a third and only two if she wasn't.

Tyler's truck was pretty big. A red dodge 3500 that looked like it'd be just as at home on the freeway as it would be covered in mud. Tyler unlocked the doors before looking back at Elena. "You feel good about sitting up front? Make it easier for you to give directions."
 
Elena didn’t pay much attention to the clerk as Tyler bought what he needed and she listen to his story about waitresses and his last break up and she nodded. “ what better way to celebrate a break up then fucking someone new.” She chuckled a bit when she said.” Sorry to burst your bubble I’m not a waitress if I wear I’d probably be working somewhere like there. If I were to be waitress I’d probably pick hooters.” That will be a perfect place for someone like her considering her large breasts.

Elena looked at the door and looked at his truck giving it a nod of approval and she might hop in the front seat because yes I would help with directions but she was just literally trying to get to the nearest city. “I can I have a ride in the front seat the city isn’t that far I think right?” She was hitchhiking just to see the country and she didn’t feel like paying for a plane that’s expensive so she figured hitchhiking around the country would be easier not only that but cheaper. “ Maybe you want me in front so you can just look at me maybe even touch. You ready to hit the road?” She asked curiously she still had not given him her name but maybe what she got and she might.
 
Tyler nodded his head at her response to his question about if she was a waitress. As they got into the truck he added "I mean I could definitely see you working at a hooters... Probably make good tips too. " He didn't say he was ready to get on the road instead he used pulling out onto the road as his answer. Tyler put the bag with the condoms in the back seat. He pulled out two 500 ml(millilitres) bottles of pop and two, one litre bottles of water "figured some drinks would go nicely with this drive. Now let's get out of NYC and into the highway."
 
“If I ever settle on a town with one I’ll get a job but for now I’m good.” She hopped in the car and buckled up and took the drink he offered her and gave him a smile.”The names Elena by the way I didn’t feel like giving it to you in the restaurant because people tend to listen and call my name and I was gonna avoid that from strangers.” Gave him a little background so he can understand why she was a bit secretive in public especially with how she looked
 
Tyler couldn't help a smile forming on his lips as Elena explained herself about why she didn't want to say her name in The restaurants outdoor seating, He understood her reasoning. Tyler took it slow getting out of his parking spot and turned the other direction from where he was before hand. This drive seemed a bit better with fewer taxis and no one was idling. He turned on and sped up enough to push them back into there seats. "Soo now that we're on our way to the highway do you mind me asking what's got you going on this journey? Sight seeing maybe? Or are you just wanting to wander?" Tyler asked this just as they got behind a transport truck trying to merge out of the lain directing drivers onto the highway. Just a few minutes and they'd be out.
 
Has Tyler got the truck and gear Elena would look around. She was a buckled and had a drink. His truck was comfortable and he hadn’t tried anything creepy at least not yet. At least he didn’t think she was too strange for doing what she did in the restaurant by not giving her name out it was just easier that way for her. A small safety measure that went a long way.

When he asked her about why she’s taking the journey she gave him a shrug before she took a sip of her drink. “Why not? It’s vacation that I want to see the country. I mean I can get a part-time job but this seems like my phone.” Pushing some of that beautiful blonde hair behind her ear as she continued to speak. “This Has been a pretty decent option. I’m seeing the country and traveling and saving money in the process if not making someone occasion. Everyone says hitchhiking is fun. To be honest I’ve had some people pay me I never turn down money.” She wasn’t asking him to pay her she’s just explaining her motive and being as young as she was cool as a good motive she didn’t say when she was still in college and enjoying herself this is just a fun road trip.
 
Tyler wasn't into the creepy side of picking up hitchhiker's, he didn't like touching women well they were sitting in his car. He would rather have fun and let things progress. He didn't say anything about this. He just sat and listen to the beautiful blonde talk about why she was on this journey.

Seeing Elena adjust her hair he smiled as she finished speaking. He knew she wasn't necessary saying everything something about her tone made him assume as much but he had no right to ask. He was on the road primarily to deliver stuff from place to place. Much like Amazon. Tyler smiled again before saying "you must be well worth it if people give you money. I could definitely see doing so for the right reasons." As Tyler said this the transport was out of the lain and going on his merry way. well Tyler sped on the turn on for the highway was only a minute away. "There's a nice spot probably about an hour ahead that'll give us plenty of cover and it's approximately half way... "
 
“A Lady never turns down the offer when someone puts it out there but also a lady never asks.” Elena clarified since she wasn’t a prostitute in anyway she was just as you would call it an opportunist. When the opportunity presents itself I got her extra funds for the road and she knew her youth wouldn’t last forever so she might as well use it. Figuring if she’s got it stared at all the time she might as well enjoy the attention.

Elena chuckled as she heard him mention there’s a spot about an hour in. “ Call me presumptuous but I figured you must’ve done this quite a few times if you know the spot. I don’t judge I’m just curious as to saying curiosity killed the cat but satisfaction brought it back he only said you’ve done this a few times but I have a feeling you’ve done in far more. No shame I get it sounds like you’ve been lucky.” Sipping her drink solely as she looked out at the signs on the highway.
 
Tyler looked over at her his eye brow raised. And a smile still on his lips. " I've done most of the highways around NY state. Even some of the adjoining states as well and Canada." Tyler kept his focus on the road keeping pace with the vehicle around them the truck was high enough up that Elena could still see the farm fields and forests they passed. "I can pull over up ahead if you want to take any pictures. " Tyler says this before adding "I've been lucky to travel as much as I have. And I'll say I have been lucky in the people I picked up. You included in that luck... And if you want me to touch you just ask... Or borrow my hand." Tyler had experience with one girl about 19 who insisted on him fingering her tell they reached a hidden spot where they could have fun.
 
Elena listened as she looked out at the country scenery passing by. It was a change to being on a college campus and was a bit refreshing. “So a gentleman and pervert. I don’t mind. When’s the last time you got laid.” She finally asked though he did mention taking photos if she wanted. “You aren’t on a strict time schedule are ya?” Since he was a delivery truck she figured he had a timetable. “So how old are you? Can I ask? You wanna guess how old I am?” She figured a game could be fun!
 
Tyler had no issue with her calling him a pervert and he smiled as she called him a gentleman. With her questions Tyler thought them over before she finally suggested making a game out of it. "okay we can definitely make it a game. I'll let you guess my age as well. As for when I last got laid, almost a month now.'" Tyler felt bad for himself over how long it'd been but then he'd been mostly in areas where hitchhiking isn't normal. "As for my schedule I am typically on a pretty tight time limit but luckily my next pick up isn't tell tomorrow... " Tyler drove for a few minutes in silence before adding. "Hmm I'm going to say 20... "
 
A man could be both and if he picked her out he’s probably a pervert but he was a gentleman for not trying to grab her. “ considering your job and you travel I’m going to guess probably around 30 or so years old maybe if I take if you’re used to being on the road and if you held out for a month that sucks that means you are probably older.” She said giving her ideas I’m guessing his age. When he spoke about his work it helped her kind of guess. “ The question is now that I have your guess and you have mine how do we tell each other if we’re right or wrong?” Elena asked as she cooked an eyebrow when he gets that she was 20. For now she didn’t say anything but she brought her finger to her lips and tapped it as she thought about a way to try and make this game more fun. “What if we said hot or cold or warm to see if you’re close you first since Ladies make the rules?” She teased with a little smirk.
 
Tyler smiled she wasn't to far off given he was 18 when he first started and was now 28. He could see the smirk then said " okay but we each get 3 guesses... And if you can't get it in time... The other person... Hmm when can choose then haha " Tyler didn't had played this game back in highschool a few times. As he passed under a bridge he added "you're warm young lady."
 
“Two can Play this game you are also very warm. Three gases that are you 32?” She gets out because she wasn’t sure and he said she was warm so she went out and she waited to see if she was getting colder or hotter but she said he was very warm but she was extremely warm but she didn’t know if you would guess it or not she hoped she would guess his first. “ what happens if the other person loses that’s the question of the hour but if I win I’m not sure what I want this is a tough game…”
 
"colder..." Tyler says this joking sticking his tongue out. He can see the look on her face as he says the words as she tries to figure out his age.
"I think if you lose then I don't know. Maybe go full topless tell we reach the half way... And if I lose you get to choose what I have to do." Tyler was genuinely biding time trying to figure out her age, he knew he was close. "Hmm I think your 26"
 
Elena pouted when he said she got colder she thought she was getting hotter but she bit her bottom lip and looked very pensive. “ can you tell me should I go up or down is that cheating?” She asked since he told her she was cold she wasn’t sure if she had to go higher or lower for him. When he said 26 it was her turn to stick out her tongue and pout as she crossed her arms under her very large bust. “Now you’re freezing. so we both have two guesses down and we’re both cold this is a tough game but you said I am cold maybe you’re 26 I’m gonna say the same number you did. I’m probably wrong though.” She said as he probably would be focusing more on how her breast looked as her arms stayed folded right underneath them
 
Tyler smiled then added. "Hmm for a hint I think I should get your touch you boobs." He figured if Elena didn't want to she could offer her own hint price. He looked at her and after thinking for a moment of thinking her response over his guess. "I'll say 25 for you and." Tyler moved his free hand over, feeling her boob threw her shirt lights tugging on the nipple just under the material. "You're going high" he felt her a little more before putting his hand back down.
 
“ if you get that hint what do I get in return?” It was Elena’s turn to be cheeky as she asked.” you are really cold with me and I think your hint should have you taking off your pants improving that you are really the size you said you are and you have to drive without your pants on I think that’s fair.” She said that she let him pull at the very thin fabric of her top. Her large breasts with soft and like a very plush pillow and as he teased her nipple he could see it get hard through the very thin fabric. “ I have a feeling you’re gonna lose this game…. you better be prepared to accept defeat because you are so fucking cold.” She tossed her blonde hair back as she chuckled thinking that he wouldn’t even get her age he went higher.
 
At this point they were stopped behind a blue ford who was seemingly waiting to turn. "I'll except that. Though if I'm not exaggerating my size you have to give me a kiss... And a kiss on the tip." He added the second kiss teasing her a bit. He then In a soft voice adds. "I think this is my final guess.. I'm going to say 20." He didn't know her age or have a clue but he was hoping he was right.
 
“ at this rate I think you’re losing so honestly you’re gonna have to do something for me you can’t guess my age do I have all my guess left? The silly grin on her face told him that he was wrong. Her arms folded underneath her big bust she stuck her tongue out at him.”Nope! You are pretty warm you’re actually steaming but that’s not my age. I’m not good at guessing but you I’m not sure I’m gonna leave it at 27 for you am I right or am I wrong?”
 
"you've got 2 guesses left. I used up my last one." Her sticking out her tongue at him egged him on to do the same just in time for her to offer up her guess. "Very hot, scolding hot... You're wrong but close. Want another hint?" They were getting still a little way out. Just close enough for her to be able to see if his dick was really 7 inches long.
 
“Like how hot?” He said scolding hot but she still had a guess and he was out of guesses. “I’ll let you grope my breasts for a hint. I have a feeling you may like that but technically you lost so you should be driving without pants. I’m a kinda passenger so I’ll only expect to get a peak of of what you’re hiding. Gotta heck your size to see if you are worthy of a joyride.” Now she was flirting and being playful.
 
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