The Moment of Truth...

Jared found himself on his knees looking up in those hopeful light brown eyes. The soft features of the face were pretty, the breasts small, but round. His gaze crept lower to the mostly flat stomach and the soft, shapely thighs. And then they rested to the dick just mere inches from his lips. It was the moment of truth. How did he find himself in this position?

Jared stopped in Ruby Tuesday's to grab a bite to eat. Not being from this city, he stopped at the first non-hamburger place he saw. The conference had two days left, and after the weekend, he would be back in his own city, his own bed. Well, it would be empty now that he and Pamela broke up. Strangely he felt nothing towards her. He was the one who called off the relationship, but he felt he should have felt some sort of pain. Well the past was the past.

Jared was quickly seated and looked through a menu while waiting for his waitress. It was late and the establishment was fairly empty, so he didn't have to wait long. His waitress was a beautiful dark-skinned female who was tall, almost as tall as he was. She had soft features and a gorgeous smile. Her hair hung to her shoulders and she wore it down and behind one ear. Her smile was infectious and he found himself smiling.

"Why are you smiling so?" she asked him playfully.

"I can't help it. Your smile makes me." Jared replied honestly.

The server's smile seemed to widen, Pepper was what her tag read. He ordered a rib platter and a beer and she disappeared. After a few moments, Pepper returned with a bowl of chips and dip for appetizers.

"I didn't order those." Jared informed her with a confused look.

"I ordered them for you. You seemed hungry and your food won't be ready for about seven to ten minutes." Pepper responded. Her smile seemed hopeful.

"Well thank you. I don't want to ruin my appetite by eating them all, so why don't you join me?" Jared asked.

"Sorry. I can't. I'm on duty." Pepper replied, and she eased to the back, looking back at him occasionally.

Jared watched her go. She was fine. She had decent hips and a round ass, with a smallish waist. Her legs were long, as she was so tall, and her ass was kind of high, but still luscious. He let his mind wander into thoughts of having her for dessert. He picked at the chips and sipped at the glass of water. Minutes went by and Pepper returned with his food and his beer. She put them down gently and asked him if there was anything else. He responded that there wasn't and she disappeared. With a sigh, Jared dug into his meal.

Minutes went by, and he was halfway through his meal when the attractive waitress returned.

"How's everything?" she asked.

"The meal's great. Are you sure you can't sit for a few. I'm here in town by myself and I have no one to talk to." Jared told her.

Pepper looked around, and then sat down. "I guess I have a minute or two." Jared and Pepper were soon talking like they knew each other for years.

"I have to get back to work. But maybe we can talk when I get off?" Pepper asked hopefully.

"I'm counting on it." Jared replied smoothly. He finished his meal and gave his number along with the tab and tip. He then got up and left, returning to his hotel room.

After showering and relaxing, his phone rung. Pepper's pleasant voice was on the line and they soon were chatting like they grew up together. He told her of his job and how it brought him here for a conference, and she told him of the more interesting places in the city. Since it was late and she was tired, they agreed to meet the next day for a movie. Jared had to masturbate to get himself to sleep, for thoughts of her big, sexy ass wouldn't leave his mind.

The next day the conference was a fog. Jared daydreamed about his date for most of the day. The minutes felt like hours as he looked at products that held naught his attention and half heard words from speakers he didn't know. Finally the day's festivities ended and Jared went back to his room to shower and prep. After several hours and a beer or two, his cell phone rung and Pepper announced that she was ready. He scribbled down the instructions and hopped in his rental, and soon he was at Pepper's apartment door. Seven stern knocks announced him.

Pepper answered looking stunning. She donned a white button-down shirt and a flowing blue skirt that reached just below mid-thigh, which seemed short on her impossibly long, fit legs. A touch of makeup here, some red lipstick, and she made Jared drool. She smiled at his reaction, and only then did he notice that his jaw hung lower than it normally did. He closed his mouth and greeted her. She kissed him lightly on the cheek and led him out of her apartment. After locking up, they entered the rental and were on their way to the movies.

They settled on a comedy, which wasn't that funny, and after about 45 minutes, they left and went to a park instead. Their conversation was great, ranging on a bunch of topics, and Pepper became more and more inviting with each passing moment. Their talk turned to more erotic subjects and Pepper surprised Jared with a left field question.

"Are you bi-sexual? Or rather, have you ever had urges?" Jared looked at her with shock, but quickly overcame it. As he responded, she stopped him. "I like you, but I don't want you to tell me what you think I want to hear. Think about it and tell me the truth."

Jared silently looked at her, and then he searched within himself. In college he briefly wanted to experiment with this one guy he met, but quickly suppressed the urge as foolish youth. He never thought of it again.

"Well I briefly wanted to try out a guy in college, but it was just this one guy. His name was Damien. He was kind of feminine looking and built small, but very cute. I had urges around him, but it was fleeting. Why do you ask?" Jared asked after confessing. He had never told anyone about Damien, ever. She was the first and last person who'd hear that story.

"Well because I'm interested in bisexuality in men. That's all. I'm glad you answered me truthfully." And with that statement, Pepper leaned in and kissed Jared deeply. The kiss lasted a long moment, with arms sliding around necks and waists.

"You want to go get something to eat?" Jared asked in the ensuing silence that followed the exchange.

"Would you rather get something to eat at my place?" Pepper offered instead.

With a nod Jared agreed, and they headed back to his car. On the drive over, Pepper told Jared stories of how she used to work at a traveling carnival. She was the assistant of a magician. It was fun work, but the hours were long and the pay was horrible. So she came back to the city at the beginning of the year. Pepper was full of surprises, Jared thought.

They arrived and Jared followed the long-legged beauty in. Her apartment was nice, if scarcely decorated. He took a seat on the sofa while she headed into the kitchen.

"Can you come here for a moment Jared?" Pepper called.

He slid off the sofa and eased into the kitchen. Pepper was tip-toeing to look at the goods she had on the shelf, and Jared couldn't help but to admire her goods. She turned and caught him looking at her. With a playful smile, she started rattling off things she had that she could cook. In mid-sentence Jared stepped to Pepper, took her in his arms and initiated a deep, passionate kiss. Her experienced tongue danced with his and her hands moved to his butt. His hands slipped around her waist and he pulled her tightly. Jared felt himself being pulled towards the living room and he went with the flow.

They reached the sofa, and Pepper fell backwards, pulling Jared with her. The kissing got more in depth and his hands began to roam. When they reached Pepper's legs, she stopped him.

"Wait, Jared! Before we go any further, there's something I gotta tell you. I want you right now, really bad, but you have to know this." Pepper announced a hint of nervousness in her voice.

"What is it? Are you married? Is your husband coming back soon?" Jared asked calmly.

"No, it's nothing like that. It's something more personal." She whispered, almost in embarrassment. Jared could not begin to guess what it was, but if it didn't involved someone else then he didn't care. She could have an extra nipple and he wouldn't care. Hell, she could have had a dick and he wouldn't care. He just wanted Pepper. More than he ever wanted any other woman.

"Promise me that you will calmly handle what I have to tell you. If you can't promise me that, than you should leave now." There was sternness in her voice that told Jared she wasn't playing.

"I promise. Now tell me this secret of yours. I'm intrigued, and most likely I won't care. I like you a lot and I want you badly." Jared confessed.

"Well I don't know how to say this, so I'll show you." Pepper told him, and with that, she pulled up her skirt and pulled aside her panties.

Jared, kneeling in front of the beautiful young lady was in shock. He was inches away from a light brown dick. It was semi hard, and aiming at him. His mind was racing to grasp what he was seeing. He never knew. He was with her all day and he hadn't the slightest clue! He looked up into the beautiful light brown eyes, eyes that were hopeful. The moment of truth came at that instant. Jared did nothing.

"I thought you knew." Pepper started to explain. "I thought you had figured it out and that's why you were flirting with..." Before she could finish her statement, Jared closed his eyes and placed his mouth on Pepper's cock.

It was surprisingly smooth. Jared had always thought that dicks were bumpy for some reason, but it was smooth. He held it in his mouth for a few minutes, getting used to the feeling, but mostly the thought of sucking a dick. Slowly he moved his head. He heard a soft sigh come from Pepper and he opened his eyes. She smiled down at him passionately. As he got more comfortable with having Pepper's dick in his mouth, she started giving him instructions on how to suck it properly. It wasn't long before Jared was sucking it like a natural. He grabbed Pepper's hands and tugged at her to stand up, and then he ran his hands along her legs until he reached her ass. He then began to rub it deeply.

Jared felt Pepper's body start to quiver slightly. This excited him greatly and he slurped on her dick furiously. Although he knew she was a he, his mind still recognized him as a she. She grasped his head and told him she was about to cum. Jared pushed Pepper's dick as far as he could into his mouth before he started to gag. As he backed off of her dick, she spurted in his mouth.

"Cum was salty" he thought. He swallowed some of it, and then let the rest dripped down his chin. He liked watching women do that, so maybe Pepper liked watching him do it? He looked up into those eyes that captivated him and they shone with excitement.

Pepper pulled her semi hard cock out of Jared's mouth and shoved him on the floor. She eagerly removed his pants and thrust his hard member into her mouth. With expert skill, Pepper worked his dick over, licking and sucking with firm lips and warm mouth. Jared stared into her eyes, eyes that stared right back with intensity. He felt the head of his penis slide to the back of her throat, and he had to cry out. This was definitely the best blowjob he ever had!

Pepper slurped and sucked loudly, never taking her eyes off of him. Soon Jared's body became rigid and Pepper tightened the suction on his quaking cock. He felt the build up but didn't even try to restrain it, for he was already on the verge of shouting. His load released, wave after wave of cum entering Pepper's mouth, which she gobbled down greedily. She sucked on his dick until it was dry and then held it in her mouth to assure that he was empty.

Pepper then hopped up and went into another room, returning shortly with a little tube of KY Jelly. Jared watched her as she kneeled next to him.

"I don't think I'm quite ready for that yet Pepper." Jared nervously informed her.

"No silly. This is for me. You got to put that thing in my ass before you go back to your city." She told him excitedly. She hovered over him, her dick hanging above his face and she took his dick in her mouth again. Her sucking felt good, and naturally he reached up and grabbed her cock with his lips. Soon Pepper had him with a full erection and she changed positions and got on her knees, leaning on the sofa.

"Put the KY on sweetie. Make me feel good." Pepper instructed, her voice dripping with lust.

Jared put some of the cool jelly on his member, and then he licked her asshole to lube it. He had never performed anal sex, so he figured that the small hole would be incredibly tight. As he pushed his head against it, the hole parted with ease. Soon he was in and thrusting his full dick inside her ass. It was almost a perfect fit, just being a little tight. The harder Jared thrust, the more excited Pepper seemed to get. She was fully calling out to him, bucking her hips and slamming her ass into his thighs. He looked at her and noticed that she was jerking her own dick while he fucked her. At that sight he couldn't hold it any longer, and he shot another load into Pepper, who shot her own load. Many minutes passed as he kneeled behind her, grasping what had just happened. Sensing his thoughts, she held still and basked in him being inside her. It had been a long time for her.

Slowly Jared pulled his flaccid dick from Pepper's ass and sat there on the floor. She crawled up next to him and laid her head on his shoulder.

"Thank you for being understanding and for the great fuck." Pepper said absently.

"Maybe next time I'll let you fuck me." Jared replied.

Pepper tilted her head up at him. "Next time? Aren't you going home tomorrow?" she asked.

"Yeah, but they've been trying to get me to transfer here and run this region. I think I shall take them up on their offer. I now have a reason to come here." Jared said with a smile. And with that, he scooped Pepper up in his arms and kissed her.