Journey to Discovery Pt. 01 - At the Bar

Simon leaned into the bar and tried to keep his eyes focused on the TV above the bar. Shy and 18, he had gone out with his roommates to supposedly celebrate his birthday, but by the third bar they had all scattered. Simon wasn't even sure where they were - but he had promised himself that college was going to be different. College was going to be when he stepped out. He was going to make friends, maybe even a girlfriend!

Simon didn't consider himself a bad looking man. He exercised, he ate well, and he took good care of himself. Where he struggled was his crippling anxiety. Something about meeting new people terrified him. He did alright if someone introduced themselves, but he had a hard time in social settings.

Like at a bar.

He knew he was probably not acting right. He kept glancing around, people watching or people creeping depending on who you asked. Located on a row of bars, the Green Door - where he was - acted as an anchor. A well established bar for a more mature crowd. Normally his roommates would have gone to a few dive bars but his birthday meant "something special", which was how they eventually ended up here. And where he was eventually lost by his friends.

He took a second to look around again, and his attention was immediately caught by an older woman at the end of the bar. Easily in her late 30s or early 40s, she had a dazzling smile. She was dressed casually, but professionally, with her long, dark hair, draped over her shoulder emphasizing her large breasts. Simon couldn't help himself, he was transfixed. She was talking earnestly with another woman, laughing, holding her glass as she talked to her friend. He blushed and started to turn away, but her eyes darted over and she saw him. He swallowed hard and looked away, before looking back with a half hearted smile and wave. She went back to her conversation.

Simon frowned at himself. Even before she looked excuses for why she would say no had started to flow into his brain: "She's older" "She's to hot for you" "You're not her type". Why couldn't he walk up to her? Why couldn't he say something? Frustrated he decided he needed to get away from the press and noise of people, and looked to find the bathroom - to which the sign indicated the stairs down were right behind where that lady was standing. Frazzled, Simon stepped back from the bar, straightened his shirt and bee lined to the door, his eyes focused.

He got past without being to obvious he felt, and started down the steps. A few seconds later he heard heels behind him. As he reached the bottom of the stairs, he felt a hand tap his shoulder. "Excuse me" a woman's voice spoke. He turned and it was her, the lady he had been staring at. She didn't seem particularly upset, more curious, her eyes were watching him carefully.

"Yes?" he stuttered.

She smiled, "I saw you checking me out at the bar." She gestured with her hands to indicate her chest. His eyes went their automatically. "Yes, like that." She laughed. "Do you like them?" He nodded. "It's okay to look I like to know when I'm appreciated." She grinned. "I like looking at you too."

He blushed a bit but smiled. "Do you?"

"Yes! Very much so. You saw upstairs right? Assuming you were looking at all the patrons and not just the ones with breasts, did you notice how most of the men here have let themselves go?" He nodded, though he hadn't noticed. "But you! You are something else!" She reached out and felt his upper arm, he was startled but she smiled and shushed at him. "Nice" she murmured as she squeezed his arms.

A tiny part of his brain was telling him he should be uncomfortable, but a much larger part of his brain - and other body parts was thrilled. He flexed his arm a bit and her smile broadened, though he barely noticed as his eyes kept marveling at her breasts. She grinned, "Want to touch them?" He nodded and reached his hand out, hesitantly touching the side of her left breast. She grabbed his hand and moved it more forcefully and fully into her chest. "There, like that!"

Simon gasped a bit but he was fully engaged at this point. He felt himself stirring as his cock grew rock hard. Finally she pushed his hand back, "Now, I'm sure that got a reaction I'd like to see!" He stammered a bit, and hesitated. He didn't really know what to do here. Especially with someone so forward. She continued, "Look, you've been staring at my chest all night. You just got to feel me up. It's only fair I get something too isn't it?"

"I guess it is," He started, "that makes sense." He nodded, and as if compelled unzipped his pants. He looked around a bit but no one else had come down - it was early in the night and everyone was still filling up.

"Don't worry, I'll stand so no one can see." She said and moved to block the view. Anyone coming down would just see them talking then would go into the bathrooms.

He struggled for a second. This was something he thought he wanted. This is something he was fighting to get. Why was he second guessing it? She wants to see his cock, let her see it! He squelched down the anxiety and dropped his pants and underwear in one fluid motion, allowing his cock to bounce free in full hard on mode. "Ooh!" Was the only thing that came out of her mouth as she took a moment to admire his cock. Then she reached out and grabbed it, wrapping her fingers around his shaft. "Wow, you're thick!" She began sliding her fingers up and down as he stood there transfixed. "Long too. You have a great cock!" She then slid her hand further down and cupped his balls, holding them in the palm of her hand. He ached to just furiously jerk off while she gently squeezed and played with his sack. "Very nice." She said, as if she was out shopping for fruit.

He grinned, "I'm happy you like em."

"I can tell!" She smiled, and used her finger to flick his cock a bit causing it to bounce. "Why don't you jerk it a bit? Give me a show while I hold these." She reached her hand back down to his sack. And he did. He took his cock in his hand and began to jerk off for this woman he didn't even know. He had never felt so confident in himself as he did right now, to the point he really made a show out of it, pulling up and out to give his cock a really good stretch. He even rolled his hips a bit to add to the show, while pulling up his shirt so she could see even more of him. She encouraged him throughout, and never let go of his balls.

After a short while he knew he was going to cum, and she nodded, "Show me how much you can make." That was all he needed to start cumming hard as she gently increased the pressure on his balls. He somehow managed to aim for the wall and floor and his cum landed hard but didn't land on her.

She grinned, releasing his balls she reached into her purse to find some napkins to hand him. "Clean that up. Then meet me upstairs after you take a second to compose yourself."

Simon nodded, out of breath as she turned and walked off. He had never been so excited in his life. As she left he took a few minutes to get his breathing under control and get dressed again. He then went back up to the bar though the mysterious woman wasn't there. She was over by the door. She gestured for him to come over. "Let's go!"

Simon followed her out the door. They headed towards the parking lot where she went towards a fairly nice Mercedes. She gestured towards the car, "Get in." He climbed into the passenger side and she got in and put the key in the ignition but didn't start the car. "Take off your pants." He immediately started to get hard again, but did as she asked, quickly unbuttoning and unzipping his pants and pushing them down till his cock was exposed again. She shook her head. "All the way off. Throw them in the back seat."

"Oh sorry" He said and quickly did as she asked, getting his shoes, socks, and pants off and throwing them into the back seat. His cock was super hard. He spread his legs slightly so that she would have complete access to his balls as well.

She nodded, "Very good." She reached out and grabbed his cock. "No cumming in the car. So keep your hands off." With that she gave his cock a quick slap to make it bounce and started the car. "If you can make it back to my place while keeping it nice and hard, you'll get a nice reward."

They drove for a little while, her hand gently stroking his cock the entire way. He focused very hard on not cumming, desperate for his reward. It was hard and he struggled not to rock his hips. His cock was throbbing. They left the city for one of the nicer suburbs, his need to cum growing into an almost overwhelming urge. They finally pulled into a nice secluded driveway of a fairly large brick faced house. She pulled up and into the driveway.

She turned to face him, now using both hands to squeeze his cock. "Take off your shirt." She ordered him, and he did so without hesitating. Now fully naked, moved her hands to glide up and down his body. "Very nice. Let's go inside."

He hesitated a second, and she laughed. "No one can see you. Get out of the car. I'd prefer it if you don't wear clothing while at my house." He nodded dumbly and got out, stretching a bit as he felt the cold pavement beneath his bare feet. She came around the car, and took him by the cock and led him to the house. He followed along his feet slapping against the pavement in time with her heels, and he never felt so horny in his life.

They got inside and he looked around a bit at her house. It was nice, brightly painted, clean and sharp. It was warm and he relaxed a little bit. She tugged gently, "I'll give you the tour after your surprise!" She purred leading him through the house. It was strange for him, being fully naked, in a strangers house, led by his cock like it was a leash, but he just couldn't help himself. He followed along like a puppy. Up the stairs until they reached her bedroom. She finally let go of his cock and grabbed his face to give him a kiss. "Lay down on the bed."

He did so, on his back so his cock stood straight up. She grinned, and ducked into the master bath, closing the door. He stared around the room, taking a moment to take it in. It was nice, though he was immediately struck by the pictures. Every picture seemed to be of a naked man, or a close up of a cock. He wanted to look more closely, but he had been told to lay down so that's what he did.

A few moments later the door opened and she stood in the frame staring at him, wearing a tight satin top that draped over her gorgeous body. He stared at her large breasts which completely filled the material, and she sauntered over, causing the material to dance around her body. "Like your surprise?"

He nodded, "You're amazing!"

She grinned and climbed up on the bed, straddling his legs she grabbed his cock again, "I can tell you're into this. Maybe we should think about making this a long term thing." He nodded even more vigorously. "I'll tell you what," She said as she leaned over to grab a condom from the bedside table, her heavy breasts rubbing over his body making him gasp in delight, "Let's see how you do tonight. If you're going to be my boy toy, you have to be a good toy."

She undid the condom and rolled it over his throbbing cock. He knew he wasn't going to do super well, because he felt the cum ready to explode just from her hands. But she leaned forward, and then guided herself onto his cock. He had never been in a woman before, and didn't know what to expect, but the tight sensation and warmth were almost overwhelming and he involuntarily began grinding his hips against her. "Oh someone is eager!" she gasped out as she pressed her hands down into his chest and began to ride him, savoring his young thick cock inside of her. She knew she was going to fuck him the second she caught him staring at her, and now she was. Her sex drive was in high gear. She wasn't wasting time on pointless dating when all she wanted was young virile cock. She fucked him till he began to cum, sadly only after a few minutes.

He gasped out, "Oh I'm sorry."

She shrugged, "If earlier was any judge you'll be back!" She laid down next to him and ran her hands up and down his body while making out a bit. He went to go touch her, rubbing his hands over her hips and breasts though slightly frustrated at her clothed status. "Easy there, you might get to see more but you have to be a good boy toy." She leaned in to kiss him again to take the sting out and that was enough, something about the erotic combination of objectification, her warm hands all over him, and the feel of satin against his skin caused his cock to begin to grow. He took her hand and placed it on his growing cock. "Oh!" She exclaimed sitting up to get a better view.

She admired his cock for a few minutes while stroking it to get him ready to properly pleasure her, then again mounted him and began to ride him. He lasted much longer this time, eager to please and be the best boy toy he could be. She enjoyed the ride, using him and squeezing his cock inside of her. She gasped as he began to cum again, feeling his pulsating cock was enough to finally push her over and she began to cum as well. Warm and satisfied she crawled off of him "Go get clean" She smiled, her voice husky and out of breath. She gestured towards the bathroom. "But leave the door open so I can watch."

He did so, climbing unsteadily to his feet he washed himself off with the door wide open before she had him come back to bed. He collapsed and fell asleep as she admired his body, her hands gently cupping his balls.