Ski Weekend Road Trip

Bill loaded his bag into the van. He was going to get his ski on with his college friends, John, George, Helen, Gina, and Nancy. They shared a dorm and knew each other pretty well. John and Helen were a couple, sharing a room at the ski resort, Bill and George were sharing a room, and Gina and Nancy sharing.

They had rented a van to fit all their ski gear, but it was going to be a tight fit with everyone together for the 4-hour ride.

George was driving and John called shotgun. Gina and Helen claimed the middle row, and Bill and Nancy got the third-row bench.

Gina said, "Bill you are going to need to squeeze in there with Nancy. It's going to be tight with all our stuff."

Bill looked in the back seat. "We'll make it work, I suppose." He said it like he was resigned to his fate, but he was secretly thrilled. He'd be sitting next to Nancy. He'd had a crush on her for a while now but was too shy to tell her or make a move on her.

Nancy sidled up to him, looking in the window. "We'll be fine. I don't mind sharing space with you, Bill." She flashed him a smile and his breath caught a little. Her face lit up when she smiled like that. This was going to be a long trip.

John called out, "Let's get moving, we're burning daylight here." It was 5:00 am and the sun was nowhere near burning anything.

Bill crawled back to the third row and settled in. Nancy followed and snuggled in next to him. They squeezed together, the gear pushing against them.

Everyone else took their seats. With the gear loaded, only their heads poked out, effectively hiding them from view.

Gina turned back and asked, "You guys okay back there? We can switch out later if you need to."

Nancy said, "I'm good, how about you Bill?"

He gulped. She was pressed against him, and he barely noticed the tight space. "I'm great."

John got on the road. "We'll stop halfway and stretch. If anyone needs to stop before that, let me know." Everyone acknowledged, and off they went.

****

They'd been on the road for about an hour chatting and everything and nothing. Every movement of the van rocked Bill and Nancy against each other. Bill was in tortured heaven. He loved being this close to Nancy, in semi-seclusion. There were no distractions to their conversation, besides the occasional comment from Gina or Helen.

"Bill, do you mind if I put my legs on yours? I'm feeling squished."

"Sure thing." He reached over and pulled her legs up onto his as she twisted her body. Her legs rested on his, the weight pressing into him.

He had to close his eyes to concentrate. Something as simple as her legs resting on his was driving him wild. He rested his hands on her thigh right above her knee.

"You know, if you wanted to massage my legs, I wouldn't object," she said to him quietly.

He looked at her. She had an impish smile and winked at him.

Her legs were encased in skin-tight black leggings. They clung to her firm thighs, revealing the shape of her muscles.

He started massaging her leg, squeezing, and rubbing it. He had no training, but he was trying to make her feel good.

Her legs felt just like he'd imagined. He'd dreamed of touching her intimately and now she was in his lap. Her legs were solid from running. She ran in the mornings before classes. He'd often see her running across campus as he walked to his early classes.

His hands slid down to her calves. He took one in his hands and applied firm pressure to the muscle, trying to release the tension he felt. She moaned as his fingers pressed into her calf. "That feels great. Keep doing that."

He massaged her calf for a while more, before switching to the other calf.

She was leaning against him, whispering to him as his hands stroked her legs. "That feels so good, Bill. Your hands are like magic. If I'd known you were this good with your hands, I'd have had you put them on my body a long time ago."

He blushed furiously at her entendre. He also wished he'd been touching her before. He was too shy and nervous to tell her that he was interested in her.

"Bill, how much do you charge for your services?" Gina had turned around and watched him massaging Nancy. "If the sounds she's making are any indication, you're pretty good at that."

He jerked his head up. He hadn't noticed that she was watching them. His blushing face gave him away, as she giggled and turned back around.

"Don't worry about her, she's just jealous. I've got the cutest guy at school rubbing me, and she can't have any." She teased him gently, her head resting on his shoulder.

"You think I'm cute?"

She looked at him. "Of course. You are a good-looking guy. I've been waiting for you to make a move. I might have thought you weren't interested, but I see the way you look at me. So, I figured I'd make the first move on you."

"Nancy, I've had a crush on you for a while now. I'm really shy and I've never even been on a date before."

She kissed him on the cheek.

"Keep rubbing my legs please, it feels good to have your hands on them.

"Okay."

He continued to massage her legs. She moaned when he found a sensitive spot, and he applied more pressure to those spots.

He worked his hands slowly up her thighs, squeezing and stroking the firm flesh. After a while, she spread her legs a bit. He took it as a sign and moved higher. Higher and higher his hands went, massaging her inner thighs.

As he was rubbing, the van went over a large pothole, and John tried to swerve to avoid it. His hand slipped and pressed against the junction of her legs. He pushed against her pussy through her pants. He jerked his hand away, afraid that she'd yell at him to stop.

She opened her eyes to look at him. "Why'd you stop?"

"I'm sorry. I didn't mean to touch you like that. We hit a bump and I slipped."

"If I asked you to, would you do it again?"

He was surprised. Instead of being mad and him, she wanted him to continue. "I'd love to."

She smiled and closed her eyes again, and leaned on his shoulder again. Her legs still parted, he reached his hand up to her vagina and rubbed at it.

Up in the front, John looked back at Bill and Nancy in the rearview mirror. "Hey man, look at that, he finally made a move on Nancy. About time."

George craned his head around to look. "Lucky dog," he said, with a big grin.

Gina and Helen saw the guys looking and looked for themselves. They had a better view than the guys did, but they still didn't see much.

"Nancy, you doing okay back there?" Gina asked.

She opened her eyes to look at her friend. "Oh yeah, Bill has magic fingers. He's working some knots out in my legs."

"Ooh, can I be next?" She asked, laughing.

"Not on your life, bitch!" She laughed at her friend.

They turned back around, leaving Bill and Nancy to themselves.

"Bill, will you keep doing that? It feels really good."

"As you wish." He smiled and gave her a quick peck on her lips. It was just a moment, but it was amazing. Her lips were warm and soft. He felt lightheaded. This was his first kiss.

She smiled at him and pulled his head to hers. She kissed him. She held him to her, gently kissing him. He was along for the ride as she took charge. Her tongue explored his lips pressing past them.

They stayed like that for a while, neither was really sure how long, and neither cared. He would happily continue as long as she was willing to let him.

After a while, she broke the kiss. "Mmmm, that was nice. We can do more of that later." He had a goofy look on his face.

"That was awesome!" She laughed at his enthusiasm and pecked him on the cheek.

"Could you work on my legs some more? It really does feel good to have you rubbing them."

He went to work on them, kneading and rubbing her thighs. His hands roamed up and down, easing up to where her legs met. Her legs drifted apart, and he stole glances at the juncture, imagining what lay underneath. He knew, obviously what was there. It's pretty hard not to know how a woman was built. Health class and the internet ensured that. But this was Nancy. The woman he'd never thought he'd have the courage to approach and tell her how much he liked her.

Suddenly remembering what she said before their friends interrupted, he made a decision. He slid his hand up to her pussy and cupped it through her leggings.

"Hmmm, yeah Bill. Rub my peach."

He rubbed her, not quite sure if he was doing it right, but she wasn't complaining. To the contrary, she was softly moaning, just loud enough for him to hear. "Keep doing that, you are doing great."

He kept at it. She was squirming now, her legs spread wide as he 'rubbed her peach'.

"Bill, I'm almost there. Don't stop, go faster!" He sped up, rubbing her through her pants. She shuddered and jerked against his hand, and he felt moisture. She pulled his hand away, and kissed him again, gently.

"Thank you, that was great." She looked around the van to see if anyone else was looking at them. Everyone else was ignoring them. "I've never done anything like that before."

Just then, John called out, "Okay guys, we are at the halfway point. We'll get out and stretch and get something to eat."

She hugged him and straightened up. "Are you hungry? I'm famished." She winked.

"Yeah, I could eat."

****

They walked into the rest stop. It was set up like a mall with a central court surrounded by tourist shops and a couple of to-go restaurants.

It was barely 7:30 in the morning, and the only other people around were truckers getting coffees.

"Could you get me a sausage egg bagel? I need to use the lady's room."

"Sure, I'll meet you at the table. Anything to drink?"

"Flat black."

Bill ordered their food and joined the rest of the crew at a table. Helen and Nancy were the only ones absent, presumably in the restroom together.

They walked out and Nancy made a beeline to the seat next to him. "Hmm, coffee." She took a sip and made a face. "Ughh, rest stop coffee."

"Mine tastes fine."

"You have like four sugars and a load of cream in there." The torn packets and creamer tubs were strewn around his cup. "Day-old burnt coffee would taste good with all that crap in it." She laughed, teasing him.

"I'm a simple man, with simple tastes."

"Nancy, don't listen to this heathen. He has awful taste. I don't know how he can drink that swill, even filled with all that sugar," Gina said.

"I just need a caffeine boost."

They ate their breakfast and talked about the resort. Bill thought about his time in the van with Nancy. He hoped that she'd want to continue when they got back on the road.

****

Back in the van, everyone settled in. This time Nancy sat directly on Bill's lap and leaned back against his chest.

They sat, relaxed and comfortable for a while. It wasn't long before his cock began to swell. The motion of the van and the beautiful woman in his lap conspired to get him hard.

"Hmm, Bill, something's poking me. Any idea what it might be?" She asked, teasingly.

"Sorry, I can't help it."

"It's nothing to be embarrassed about, I'm happy that I can excite you."

"You excite me just by existing," he said. "I like you, Nancy. I wish I could have told you before, but I didn't know how. I was afraid you'd tell me to fuck off."

She turned and kissed him. "I've known. I was waiting for you to ask me out, but since you didn't, I figured that I'd take the lead."

"You knew?"

"Bill, we always know," she said gently. "Why do you think I hang out with you? After I figured out that you weren't going to make the first move, I set this up."

"Wow. I feel so stupid."

"No, Bill. Don't feel that way, please." She kissed him again, this time on the lips.

She felt his cock pressing into her. "I want to do something for you. You made me cum earlier. I want to return the favor."

She slid off his lap onto the floor between his legs.

"What are you doing?" He asked "What if they see us? He was looking at the backs of the heads of Gina and Helen. There was no indication that they knew anything, but he worried still.

"Don't worry, it's cool. They won't know. Here, put my jacket over your lap, they won't see even if they turn around."

"Oh, okay. Good idea." He draped it over his lap, covering her. He wished he could watch her, but this felt like a good idea.

Her hand rubbed along the front of his pants, his hard cock pressing back. He closed his eyes and leaned back. If Nancy wanted to do this, he'd let her.

She unzipped his pants and pulled it out. Bill had never had anyone suck him off before and didn't know what to expect. So, the warmth of Nancy's mouth on him was a surprise. He gasped at the feeling.

"You okay back there?" Helen turned to look.

"Oh yeah, no problem."

"Hehehe, I'll bet." She turned back and giggled. She clearly saw that Nancy wasn't on his lap.

He turned his attention back to the sensations of Nancy's mouth on his stiff cock. Her head bobbed under the jacket, as it went up and down with her motion.

He lifted it to see her. Her eyes met his and he smiled. He thought he could see a smile in her eyes looking back at him. She pulled his hands to her head.

For several minutes, she worked on him, alternating between sucking him deep into her mouth and licking all over. He stared intently at her. The feeling of her split his attention. One part of his mind tried to catalog everything he was feeling. Like how her mouth and tongue were moving around and applying suction and pressure. The other part was telling him to stop being a dork and enjoy how it felt, and it felt great.

Soon, he felt himself getting close and started to panic. Where would he cum. Would she swallow it? Did girls do that? What if she didn't? He looked around for something she could spit into, just in case.

She pulled her mouth off, seemingly sensing his thoughts. She whispered to him, "Don't worry, Bill. Just let it happen. I'll take care of the rest."

He nodded and she took him back in her mouth. Before he knew it, he was cumming, spurting into her mouth. Pulse after pulse of cum shot out into Nancy's mouth. She swallowed all of it as he came from his first blow job.

A groan escaped his lips, louder than he intended. Both Gina and Helen giggled in front of them, and even George looked back with a grin. Oblivious to how the rest of them were reacting, he was lost in the feeling of Nancy finishing him off.

"Come here, I want to hold you," he said. She tucked his shrinking cock back into his pants. He pulled the jacket off her and held her in his arms. "Thank you. That was amazing."

"It was my pleasure. Was that your first time?"

"Yeah."

"Ooh, I've never been anyone's first blow job."

"First anything. I was a virgin. Still kind of am..."

"Oh, Bill. We are going to have a lot of fun this weekend. We might even get some skiing in."

He leaned in to kiss her, but she pulled away. "What's wrong?" he asked, confused by the mixed signal.

"I have cum breath."

"Oh that, don't worry, I don't mind the taste."

She leaned back. "Hold on, you just said you were a virgin?"

"I have a hand, and I have a lot of experience with it."

She thought for a second. "Okay then." She leaned in and kissed him hard. He did indeed taste himself on her lips and breath.

They settled in, wrapped in each other's arms for the rest of the ride to the mountain and their weekend of exploration, and maybe some skiing.