A Roadtrip to Remember Ch. 01

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Roadtrip gives lots of time to recall first-time encounters.
5.4k words
4.63
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11

Part 1 of the 2 part series

Updated 06/10/2023
Created 06/10/2021
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Note: My first story, comments/feedback welcome!

Disclaimers: As usual, any and all characters in this story partaking in sexual stuff are 18 or older. Everything about this story is 100% fictional. If you think you know anyone named here, it's purely coincidental.

Having accepted a new job with a consulting firm in a new city, Stephen was reluctant to leave behind ten years of friends and family. He was, however, excited for new possibilities. Steven packed all he could into his late model Honda, sold or gave away the rest, and turned in his apartment keys. After one last goodbye party, which lasted into the wee hours of the morning, Steven was ready to begin anew.

Arising early from crashing on a friend's couch, he quietly snuck out into the early morning light to his fully packed and gassed vehicle. As he watched the Denver skyline go from full scale buildings to what seemed like a toy model in his review mirror, he was on his way. Seattle, a few hours short of a full day's drive from Denver, was exactly the kind of driving challenge Steven love to accept. Most people would split the trip into two parts. But Steven was not most people.

"Google maps, says a few minutes shy of 20 hours. I bet I can easily do it in 17 pushing the limit in the many wide-open stretches if I'm following some other idiot speeding, stopping only for gas, food, and bathroom breaks," he thought to himself.

In the wide-open expanses of Wyoming, moving along at nearly 90 mph, it is easy to let one's mind wander to the past and future, ideas and dreams. Steven fell into the rhythm of the road. He wondered what Seattle would be like. He wondered how he would meet new friends. The only person he "knew" was his new roommate, Andy, whom he had only spoken to through an online connection and was also going to be new to Seattle. He wondered if they'd get along. While he seemed cool enough in their brief conversations, he was experienced enough to realize that you never really know someone until you've spent quality time with them. Steven hoped he wasn't some uptight prick.

As he was driving, Steven reflected on his most recent relationship. Katie was one of the smartest people he had ever met. It's what instantly drew him to her. They had the easiest connection, the kind that makes people fast friends. They had been introduced by a mutual friend at a party. Their playful banter quickly led from meeting for coffee, to phone conversations that bled well into the next day, to dinner dates, and ultimately an intimacy that is reserved for, what Steven believed, only a lucky few get to experience.

On their fourth date, they had gone out to a hole-in-the-wall karaoke bar. They spent the entire evening vacillating between downing shots and making fun of the never-ending line of attention starved middle aged has-beens.

After one painfully bad rendition of Air Supply's "I'm all out of love", Katie piped up, "I'm going to be all out of hearing if we stay much longer. Want to get out of here?"

Without missing a beat Steven shouted back over the newly starting song, "You bet!"

Katie grabbed Steven by the hand and lead him to the front door. Steven loved her assertiveness. She had a delicate way of being a confident leader and yet not completely dominating at the same time. Once outside she immediately was on her phone hailing an Uber. Steven asked, "Where did you want to go next?"

"My place," Katie said with absolute certitude, the kind Steven knew not to argue with. Not that he wanted to argue with her either.

Steven's mind was swimming in anticipation. Up to this point in their relationship, they had only kissed goodnight, but something in the way she said "my place" had, in no uncertain terms, communicated they would be doing more than just kissing by the night's end.

The Uber pulled up and they climbed into the back, Steven first then Katie. He scooted all the way over and she sits right next to him in the middle. As they car pulls away, they put on their seatbelts. Steven glanced over at Katie. He noticed the way a soft curl of her hair has fallen against her cheek. "God she is beautiful," he thought to himself. Noticing his gaze, she glanced over, smiles, and reached for his hand. As he turns to look forward, she leaned over and places a soft kiss on his neck, and then another, and then another.

The sensual string of kisses induced an immediate effect on Steven. He felt a stirring in his pants that millions of years of evolution assured would be automatic. He glanced down to see her short dress had ridden up he legs slightly. He eyed her legs and noticed that above her knees there was just a hint of soft blond hairs that he could make out with every passing streetlight. He hoped that this meant she hasn't subscribed to the notion that women should shave to look exactly like little girls. Steven preferred woman more natural. Not an ape per se, but a woman none the less. Nothing is more repulsive to him than fake tits and a desert where some semblance of a forest should be. He couldn't quite understand the typical modern male's ideal of the female body.

They arrived at her condo a short 8 minutes later. Katie led him by the hand as they sauntered up to her door. She reached into her purse and pulled out her keys. Steven's heart was already beating a little faster in anticipation of what he imagined would follow. He was looking forward to going in and see what unfolded next.

Katie suddenly turned around and wrapped her arms around his neck. Their bodies started to pull closer together as naturally as two magnets. At first it is just soft on the lips, but soon their kiss evolved from a teenage crush to adult intimacy as they shared the most deep and passionate kiss. Their mouths began to open, and they gently explored each other's mouth with their tongue. Steven loved the gentle probing, the sensation of giving and receiving in the same moment. The excitement seemed to spread to every inch of his body.

This is the first time that Steven has held her this tight for so long. Sure, they'd had their goodbye kisses, but it wasn't a full embrace. Now he was holding her, really holding her. Katie's thin summer dress gave him the opportunity to sense the outlines of her body. Katie was an avid runner, and as such, had a runner's body. She was very fit and lean, but not the kind of lean that makes you want to send a girl to an all-you-can-eat buffet.

Oddly enough, the first thing Steven noticed as he wrapped his arms around her is how firm and muscular her mid riff was. His arm rested just above her hips and he could feel that most womanly defining curves. He could also feel the hem of her underwear just below the surface layer of the dress. He wondered what she looked like in her underwear.

With each passing moment they pulled each other tighter and tighter into each other. Steven started to notice other, more exciting outlines. He could feel the soft swells of her chest pushing into his. She was not a large chested woman, he guessed a B cup, but he loved the feel of her breasts against him. That soft cushion that provides curves and comfort.

But it was the last outline that brought definitive swelling to his member. The more they pressed together the more he could feel her mound grinding into him. His holding her had informed him that all that lay between her naked flesh and him was a thin summer dress and her panties. This was more than his manly senses could process, at which time he allowed nature to take over and let the blood fill his cock. He wasn't hard as a rock, but there was no way that she didn't notice and feel the lifting bulge in his shorts. In fact, Steven felt like once he started to grow, she pushed a little more firmly against him.

After a short while, Katie slowly pulled away from their kiss, while their bodies remained pressed.

"Unless you want to give the neighbors more of a show than we already have, I suggest we continue inside," Katie half spoke, half whispered. Her cheeks were flush and her hair falling a little on the sides of her face. As she turned to unlock the door, Steven glanced down to take in her backside. She had a well sculpted ass that one gets as a result of running regularly and being all of 29 years old.

The door swung open, they went in, kicked off their shoes, and closed the door. She once again led him by the hand up the stairs from the entry way. The hem of her dress performing a mesmerizing swaying dance which was keeping him transfixed on her backside. As she climbed the stairs his eye level was that staring right at her ass. The definition of which, could be made out as the thin material bunched up now and again in her crack as she sashayed up the stairs. With his cock still semi hard, he badly wanted to rub it gently between those beautiful ass cheeks.

As they reached the top of the stairs, Steven found himself in a combined living room and kitchen, common in many modern 3 story condos, with a sleek bar separating the two. The condo was very nice, recently built, with high ceilings and a chic tasteful design.

"You want something to drink?" Katie asked as she moved into the kitchen area.

"Well, what do you have?" Steven replied as he took a seat at the bar.

Opening the fridge Katie leaned over and said, "For beer I have Stella, some crappy IPA, and a pils. I also have some scotch my dad left when he came for a visit."

"What kind of Scotch?"

Katie moved over to the cabinet besides the fridge. She opened the door and took a step back to be able to see what was in there on the top shelf. Katie wasn't short by any means, she told me 5'10, but being 6' 1' myself I'd say she is nearer 5'11' as when we kiss I don't have to lean over much the way I do with other women. My guess is she says she is shorter cause it probably sounds more feminine, but I find her tall athletic figure gorgeous

"Looks like McCallan 15." She squinted a bit to read.

"Well, that's pretty decent. You dad has good taste. I'll take a glass of that if you don't mind."

As Katie approached the cabinet, she had to get up on her tiptoes to reach the bottle just on the edge of the topmost cabinet shelf. Steven couldn't help but notice how this pose made her look even more attractive. Her lean lithe body draped by a such a figure-defining dress assaulted his visual senses. Being on her tiptoes caused her already perfect ass to jut out even further and only increase his desire to mount up behind her.

She laughed breathlessly as her continued grasping for the bottle remained unsuccessful as it was just out of her reach. She looked over and caught Steven checking her out.

"How about you come grab this for me rather than just sitting there staring at my ass," Katie said playfully.

"Sorry," Steven said feeling a bit sheepish.

Steven moved around the bar counter to come grab the bottle. To his surprise she didn't move out of way and continued to try and grab it. He hesitated, for not sure how to handle the situation.

"Are you going to try and help me or not?" she asked coyly.

Steven came up close to her from behind, but not close enough yet to touch her body. He reached an arm up and out, but the futility of getting the bottle from this distance was readily apparent. He knew he'd have to be right up against her to actually reach it.

As Steven inched forward, he formed a perfect match to the contour of her curves. He reached up again towards her hands still fumbling with the edge of the top shelf. From their thighs to their arms, to their hands and fingertips, their bodies were in complete contact. He felt the soft and warm skin of her arms and the light wisps of hair thereupon. He could smell the subtle hint of lavender of her hair. He could feel the warmth of her body radiating through to his skin.

He slowly put his head slight to the right side of hers.

"Almost have it," he said quietly in her ear. He could feel her breathing as part of him, as if their lungs collectively were supplying oxygen to a single organism.

With Katie on her tiptoes, her ass completely aligned with the positioning of his groin; a ball and socket designed for each other. She somehow managed to push up a little further into him, her shapely behind was entirely in his crotch. He loved the feeling of her ass in that position. It such a natural position to him.

Whatever intervening time his dick had to return to a flaccid state between their passionate kiss out front and that moment was now but a memory. He could feel that familiar tingling and warmth of his arousal. He resolved to just let it happen without embarrassment. In this position as his cock stiffened through his shorts it raised up right between her legs and into the cleave of her firm behind. There is no way she doesn't feel his bulge now. Katie moved up and down on her tiptoes a little. Steven just completely forgot himself in the moment. He loved being this close to her.

"You able to get it," she said slightly short of breath, suddenly bringing him back from some faraway place. He noticed only one of her hands was still on the shelf. Her other hand was placed firmly in front of her on the counter, centered on her body. From his angle he couldn't tell if she is using it to steady herself, or if it was positioned, at her groin level, advantageous to stimulate herself as she had been raising and lowering herself on her tiptoes.

Steven was able to just grasp the bottle as his mind worked very hard to shift focus from her body to the bottle. As he pulled the bottle down and moved away from her body, he longed to still be one with her, to still have her nestled into him.

Katie grabbed two glasses in the next cupboard over. She turned around to face Steven. "How do you take it?" she says with a demure smile on her face.

"Holy fuck," he said to himself, "she more intoxicating than the alcohol."

"Neat, of course." Steven replied.

"Good, me too. Pour us two glasses while I go to the bathroom. Be right back."

As Katie retreated from the room, Steven is glad for the moment to take it all in and savor the experience. The touches, the looks, the kissing, the warmth of her body, her smell, her deliberate sexual teasing. On top of it all, he can't believe she also like Scotch. "How fucking lucky am I?" he mused to himself.

Steven handed her a glass upon her return with smile and a "thanks" from her. They both took a slow sip. They stood facing each other in the kitchen about 4 feet apart, he was staring at her, Katie was looking down at her glass. She looked up and smiled. Her auburn hair falling to one side. They continued to take small sips, all the while looking at each other without talking, but always playfully smiling. Her countenance was as smokey as the Scotch. He couldn't help feeling anything but luck and joy.

"Why don't we go sit down?" she said after a little while.

As they move into the living room side of the bar, Katie dimed the lighting, walked over to the window, and closed the blinds. Steven looked at the L shaped couch and decided to sit at one end with an arm rest. As Katie moved towards him, she set her glass down on the coffee table. As she drew close, instead of sitting down, she stopped short and stands tall right in front of him. She reached her hand out to take his glass and set it down next to hers.

Katie slowly bent over at the waist, placed her arm on the back of the couch, and kissed him softly on the forehead as her hair fell all around him. He loved the feeling of her soft moist lips on his forehead. Her dress gapped open at the top a little now that she is bent over. From his vantage point of sitting on the couch, he could look straight down her dress as gravity worked to his advantage. While she isn't fully exposed, he can't yet see her nipples, it is clear now that she had no bra on, as he could see through her cleavage down to her toned stomach. Her soft breasts hung down like two mounded temples to feminine beauty. His eyes feasted upon them.

Her kisses move down his cheek until their mouths meet. Unlike their slow intertwining at the front door, this kiss is immediately deep and passionate like familiar lovers. With her free hand she caressed his arm, rubbing slowly up and down. As they kiss longer her hand moved down to find his. She grasps his hand and slowly lifts it. Steven knew where she was going, and his heart raced fast in giddy excitement.

She placed his hand on her breast and let go. The firmness of her breast was exhilarating for Steven. He cups it gently and brings his other hand to match the current activity. With both breasts in his hands, Katie gasped in their kissing. He gently messaged them and marvels in their perfect size, neither filling nor overflowing his hands.

With his hands occupied with the roundness of her breasts, his thumbs ventured out for their own exploration. As he makes a gentle sweep inward, he soon passes over her very erect nipples. He loves the contrasting feeling of soft flesh of her breast with the hard posture of her nipples. With each sweep of his thumbs over the protruding center of her tits, Katie let out a soft moan of pleasure.

Feeling her breasts has made his stomach flutter full of butterflies. That wasn't the only location of flutter in his body. His loins began their ascent again as well. Steven loves this kind of building sexual teasing and anticipation. He was happy to have his cock responding again after a brief retreat.

Katie broke their kiss and stood back up. Her deep blue eyes staring deep into his. Without breaking her gaze, she folded her arm in the way that only women learn to do, to pull off first one strap of her dress, then another. She held the dress up momentarily with the straps off her shoulders in her crossed arms before relinquishing her light grip as the fabric floated noiselessly to the ground.

Steven drank in the entire scene. She stood before him with her arms still across her chest wearing nothing but the softest of looking blue floral panties. Her soft skin seemed to glow. He can see her firm stomach and follows it down to the line of her underwear. He noticed the curves of her sides the widen out upon her hips in such a feminine way.

Slowly, Katie lowered her arms to reveal the most amazing breasts. They seemed to hold their shape perfectly. Her creamy skin accentuated her breasts and made them stand out from the otherwise tan hard body. At the center was a dark pink areola that was slightly puffy. Her well defined nipple extended proudly beyond the surface of her breast, beckoning him to bring his mouth to it.

More blood filled his manhood and his tented shorts are began to strain against the fabric.

She moved her body between his legs causing him to spread them. She placed one knee between his legs on the couch and her hands on his shoulders as she moved in for another deep kiss. This time he didn't need any direction to reach for her breasts. He couldn't believe how much more amazing they were to the touch of his hands now that the fabric barrier had been removed. He gently rubbed her nipples again, but with the removal of the last barrier between them, she now let out a very audible gasp.

Katie pulled back slightly from the kiss and reached for the bottom of Steven's shirt. She quickly pulled it up over his head. Steven was fit, but not crazy muscular. She ran her hands over his chest and stomach. This only further stirred his need to be free of his shorts. As if she could read his mind, she placed a hand right on his bulge and pressed. He pressed back into her lifting slightly off the couch. As her hand continued to wander, she reached the buttons on his shorts and undid it. She unzipped his shorts, grabbed both sides, and started to lower them as Steven raised his hips and his shorts slid away.

As the last of the material passed over his cock it sprang up and out and slapped his belly. Katies let out a giggle. Steven was just pleased his dick has room to extend and was anything but embarrassed. He loved the feeling of his hot hard dick out free. He loved more that she wanted to do something with it. She slid the shorts off his legs and then got down on her knees.

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