The Hike (Part II)

It did not take Victoria long before she found exactly what she wanted to wear on her hike with Tony. She pulled her hiking boots, which had actually not seen a trail in about a year, from the trunk sitting in her closet. They were cleaner than she anticipated remembering a number of muddy treks she had made the last few times she wore the boots. She tossed them toward the chair at the side of her bed.

In her drawer she pulled out her hiking socks. Not very sexy, she knew, but a girl still needed to be practical! But that was as far as she was willing to go for this first meet with Tony, as far as practical was concerned. The impracticality of denim shorts that revealed too much of her ass cheeks were not going to be practical, but she was for sure going to be wearing them. And the more she thought about it, panties were also practical but quite unwelcomed. Without a second thought, she closed her panty drawer and moved down to the drawer with her tops.

Victoria rifled through the drawer picking out one and holding it up while looking in the mirror. “No!” she said tossing it on the bed and, repeating the motion of pulling out a shirt, holding it to her torso, and then looking in the mirror, Victoria repeated her “no” mantra and tossed shirt after shirt to the bed. Moving to her next drawer, Victoria pulled out a tank-top with thin shoulder straps. It cut quite low on her cleavage and she wore it so infrequently because of how much it exposed her. It was, of course…impractical. Which is why she knew she had to wear it. She debated on wearing a bra. She had one that pushed her tits up high and tight and would certainly show her off in the tank top. But, as she thought of what might happen during the hike and why she was meeting Tony in the first place, Victoria decided that it was too practical, and slid into the shirt sans a bra.

After sliding on her socks and lacing her boots, Victoria touched up her make-up and worked her hair into a ponytail. She knew she looked “outdoorsy” and hoped that there was enough sex appeal to get Tony’s attention. And that’s when Victoria’s knees buckled and her hands started to shake. “What the fuck am I doing?!” she said to her reflection in the mirror. She was once again questioning the entirety of her actions. Her mind was challenging her self-confidence, her age, her lack of dating experience in the last twenty years, and, of course, could she actually have sex with Tony, which she had inferred with her profile picture and Natalie’s not-so-subtle profile suggestions. Victoria felt her mouth dry and beads of sweat formed on her forehead.

In a panic she called Natalie. The phone rang and rang and Natalie failed to pick up. “Why doesn’t she answer?!” said Victoria out loud to herself. “Bitch got me into this mess!” She dialed again. And when there was no response, she dialed yet again. On the third try Natalie finally answered.

“God dammit what?!” said Natalie. “I’m kind of getting some cock right now!” Victoria felt her face flush. She had totally forgotten that Natalie was on a date.

“I’m so sorry! I can call later!”

“No, no,” said Natalie. “Go ahead. Just don’t go away if I start to cum while talking to you. He’s got a magnificent tongue…don’t you baby?” Victoria heard Natalie voice quiet as she pulled the phone from her mouth and talked directly to her date. “Jeezus he’s made me cum twice already and he hasn’t even got his cock out yet.”

“Okay, fine, whatever!” said Victoria completely aware of how short she had become with her friend.

“What is it, love?” said Natalie breathing heavy.

“I can’t do this!” Victoria felt her voice catch as she spoke.

“Of course you can.” Natalie’s voice trailed off and she moaned for a moment before coming back on the line, with her breathing heavier than before. “You not only can do this, you need to do this! We both know it’s been too long and…fuck…” Natalie trailed off and all Victoria could hear was her friend moaning, clearly having an orgasm. Victoria listened and felt her body tingle and arouse. She squeezed her thighs together and listened intently to the phone and the moans escaping her friend’s throat. The orgasm seemed to carry on for longer than Victoria thought necessary. Though Victoria wanted to be upset with her friend, angry even, she knew Natalie was right. And the more she heard through the phone, the more her body ached for the same.

“Oh my god, Vic, I’m so sorry!” said Natalie barely able to speak. “That one was a good one.”

“Clearly,” said Victoria. Her mind racing between fear and outright desire.

“Go on this date,” said Natalie. “You don’t have to hook up but go. Prove to yourself you can at least do that much.”

“You’re right,” Victoria said after a lengthy hesitation. She could hear  Natalie exchanging loaded words with her male counterpart through the phone. Then Natalie started to giggle.

“Vic, I really need to go,” Natalie said with an urgency. “I’m about to get this guy’s cock and as much as I’d love to talk and have you listen, I need to just focus on this.”

“Of course!” said Victoria. “I’ll call you tomorrow.”

“Can’t wait to hear how it goes.” Natalie’s call went silent. Victoria imagined that Natalie was probably bent over with her stomach on the bed and her skirt rolled up her hips and she was already nearing an orgasm with her partner’s cock inside. Victoria lamented how lucky Natalie was at that moment. Luck, however, really had little to do with it. Natalie simply put her needs out and those needs were met. She really was only just following through.

Victoria looked in the mirror. She scanned the middle-aged woman in the mirror, who had been let down by a man she loved. She stared into her own eyes and allowed the fear to subside. Victoria stood straight. She fondled her tits and adjusted them. “I know what I want,” she said to herself in the mirror. “I’m going to go get it!”

A short drive later, Victoria was at the trailhead. She glanced at Tony’s picture and recognized him as the man standing in front of a four-door sedan just a few parking spots away. Victoria started doing breathing exercises that reminded her of the exercises couples learn in birthing class. Her nerves were completely rattled. She felt dizzy and even nauseous. Victoria nearly screamed when she heard a knock on her window. She had not noticed that Tony had approached her car. She let the window slide down.

“You’re Victoria, right?” said Tony flashing a devastating smile. Victoria was drawn to his beautiful, hazel-brown eyes. He was every bit as attractive as his photo implied but he was shorter than Victoria anticipated. Her fears of age were immediately dispatched as Tony appeared to be similarly middle-aged as she.

Victoria finally nodded that she was indeed the woman Tony thought she was. “You have a beautiful face,” said Tony. “It’s too bad you don’t have it on your profile too.” His gentle complement put Victoria at ease and she realized that indeed there was no way for him to know for sure that she was the same Victoria from the profile on the app because she had left out her face on the image.

“Thank you, Tony,” said Victoria fighting a blush. “You’re very kind.”

“And honest.” His smile lit up as he opened the car door. Victoria watched his hazel-brown eyes explore her cleavage and the length of her legs. She was showing a lot of skin for him to look at. “And I must say,” he said, “you’re incredibly sexy!”

“Again, thank you,” Victoria said sliding out of her car. She reached back into the car for her keys and purposefully bent over so Tony could see how short her shorts actually were. She felt naughty. Sexy. Aroused. She heard the slightest groan escape Tony’s throat and she smiled feeling her confidence grow.

Standing and closing the car door, she said, “we better get going. Sunset is not too far off.”

“Agreed!” said Tony and they set off down the trail. The light was already fading but a full moon was already high in the sky. Light for the return walk to the cars would not be an issue. They encountered few people on their walk and they talked about their work pondered why they had never noticed each other on the trail. Afterall, they discovered, they both frequented it, though Victoria tended to run it while Tony simply hiked it. Still there was a connection.

“So this is the spot I wanted to show you,” said Tony pointing to a side trail. Victoria had never noticed it before. “It winds around for a bit with some brush, but then there’s a clearing on the other side that overlooks the city. It’s perfect at sunset. Should we check it out?”

Victoria knew that Tony was a stranger and she knew she was vulnerable in the middle of nowhere with him, alone. On the other hand, if she didn’t take some risks, she would never get the rewards. “Absolutely,” she said. “You lead the way.”

“I’d rather follow you and watch those shorts of yours.” They both laughed.

Feeling her confidence grow, Victoria said, “how about on the way back.” Tony nodded with approval, then turned down the path. She watched Tony’s cargo shorts stretch around his ass as he walked the trail. She watched the flexing of his calves while he hiked ahead of her. He may have been mostly an average looking guy but her clearly had muscular legs and tried to take care of himself. With each step down the path Victoria’s excitement grew. She was convinced that this would be a moment she would brag about to Natalie. She wondered what all they might do to each other in this hidden, quiet spot Tony was sharing with her.

The moon was the primary light by the time she and Tony stepped into a clearing. A few more strides and Tony pointed out the view. Victoria looked out over a valley and the sprawl of city lights. The moon hung above the city as though the residents should be able to reach up and touch it.

“Tony, this is beautiful.”

“Thought you might like it,” he said. Victoria felt his body behind her. He was careful in his approach. She sensed he wasn’t wanting to be too presumptuous but clearly he was hopeful. Victoria pressed back against him when she felt him pause to give him a clear sign he was safe. She felt his hard cock pressing through his shorts and teasing at her thigh gap. Her nerves caused her to tremble feeling a hard cock touching her for the first time in years. She reached around and pulled his hips closer. Tony bent forward and kissed Victoria’s neck, sending chills through her body and ignited her pussy. His hands slid under her tank top and caressed her stomach.  Victoria moaned and pressed her ass harder against Tony’s hard cock. She moved her hips, coaxing his cock to get harder. The more she did so, the more he moaned and the harder his kisses were on her neck. Victoria too could no longer fight her own moans and let them escape freely.

Tony’s hands unsnapped Victoria’s shorts. Though they were tight against her his hand slid down the front and his fingers quickly found her swollen clit and wet pussy. “Oh my god, yes,” Victoria moaned spreading her thighs apart so Tony’s fingers had complete access. His fingers slid inside and his palm pressed against her clit. Victoria wrapped her hands around the back of Tony’s neck and she leaned into his chest. Her hips pushed forward and she bent her knees. Sensing how badly she needed this, Tony’s hand pressed hard on her clit and he shook her pussy with his fingers buried deep inside. The ferocity of the shaking made Victoria’s whole body melt. The only thing she felt was her pussy and the climax building inside of her. She squeezed her hands on Tony’s neck harder as the climax built inside. Victoria moaned the closer it got. Her stomach tightened at the first trigger of her orgasm. Her eyes clenched tight and her mouth gaped open. Her head bent forward.

“Cum for me,” said Tony in her ear.

VIctoria moaned loudly as her body erupted. Tony’s hand never slowed and her body shook with each wave of her orgasm. She lost her breathe and was moaning without any sound. Her hands squeezed so tight on Tony’s neck that he had to twist his head to remind her to loosen her grip a little.

“That’s a good girl,” he said as her climax slowly subsided. Aftershocks caused her to tremble even as he slowed his hand against her pussy.

            Barely able to speak, Victoria managed to whisper, “My god I needed that.”

            “I’m glad I could help.”

            “Me too,” said Victoria turning into Tony. He reluctantly took his hand out of Victoria’s shorts. She pressed her body against his and kissed his neck. Her fingers fumbled with his shorts before she finally gave up on the button and unzipped them instead. Tony’s cock sprang from the zipper and her spindly fingers wrapped around his shaft and started to gently tug on its length. Tony moaned his approval and Victoria smiled feeling confidence she hadn’t felt in a very long time. She had remembered the taste of cock but it too had been so long. She had no intention of waiting any longer.

            She glanced into Tony’s hazel-brown eyes and smiled at him. She watched him while she maneuvered to her knees. Her mouth watered with anticipation. Her lips slowly wrapped around the tip of his cock and squeezed eliciting a moan from Tony. Her fingers snagged his balls and pulled them from his shorts. She wanted all of it.

            Victoria held Tony’s balls in one hand, gently squeezing them, while she stroked his cock with the other. Her mouth focused on the tip of his cock and would periodically slide down the length of it before releasing it again. She tasted the salty precum and all she wanted to do was to make him cum.

            She bobbed her head faster and squeezed his balls and cock tighter. She felt Tony’s hand hold her ponytail and, with his other hand, gently press her head up and down. His thrusts increased with her pace. His cock shaft actually seemed to expand further inside her mouth. He started moaning. Victoria felt her pussy quiver hearing him groan. Finally, she heard him warn her, “I’m cumming.” Victoria figured that Tony was anticipating her pulling her mouth away, but she didn’t. She let him cum in her mouth while she stroked him until his groaning and flexing cock became silent and still.

            Tony helped Victoria to her feet and just as he was about to say something, they both heard rustling of tall grass from the trail and voices. “Someone’s coming!” said Tony. He and Victoria quickly manipulated their clothes back into their rightful places and nervously headed towards the path, like two teenagers about to get busted. A group of young adults met them on the path. Victoria was certain some of them were smirking, as though they knew what the two “older” people had been up to. Victoria didn’t care. She had accomplished something she never thought possible.