(AUTHORS NOTE: Many of the characters that appear in this story were first introduced in "14 Inch James - Undercover Cop.")
*****
Tim woke up with morning wood, as he usually did. He could be excused for thinking that he was on top of the world. He had just turned eighteen a few weeks back, and the trust fund left to him by his grandfather had kicked in. He was now a wealthy lad, with the promise of even more wealth one his parents passed away, as he and his sister Mandy were the sole heirs.
But back to that morning wood...Tim was a very sexually active young man. He loved women, he loved fucking, he loved it all, but he was not without his quirks. When he was about twelve years old he had accidentally seen his mother in her underwear. He just happened to walk by her bedroom while she was getting dressed, and the door just happened to be open. He was mesmerized at the sight of his scantily clad mother. That it was his mother was of less importance then the fact that he had seen a woman in her underwear. The image of those white panties and white bra stayed with Tim all through puberty, but what was even more arousing was the embarrassment his mother seemed to feel at having been caught by her son in that condition. She tried at first to act nonchalant, but she quickly went over and closed the door. Tim interpreted that to mean that he had seen something he wasn't supposed to see. It was right around then that he got his first erection.
From that moment on, a woman wearing nothing but her bra and panties became his greatest turn-on. Once he began masturbating, that was the image he clung to. Not just a woman in her underwear, but one who was embarrassed at being seen in that state.
But back to the woodie...Tim looked over at his girlfriend, Lynn, who lay next to him. She was his high school sweetheart. They had been having sex for about six months. Lynn never wore a bra; she had no need. Her breasts, while not large, were exceptionally firm, as befitting an eighteen-year-old girl in perfect shape. Lynn always slept in white cotton panties. Tim slept nude. He loved Lynn's choice of underwear. There was a little pad right over the vagina area, and the remainder of the material was thin enough so he could make out the presence of pubic hair. She didn't have much; just a small patch over the top, but what she did have was dark gold in color, matching the hair on her head. Lynn was a fox. She looked so beautiful and peaceful when she slept, Tim would sometimes wake up in the middle of the night and gently lower the blanket so he could look at her white cotton panties. He had mastered the art of masturbating quietly, so as not to awaken her. Once Lynn did wake up, unbeknownst to Tim, and she watched with fascination as he jerked off. The next day she had asked him if he would masturbate in front of her so she could watch, and Tim happily complied. Complied? Hell, he was ecstatic. It was a perfect marriage of fantasy and reality. Pretty soon it became a lovemaking ritual. Their sex sessions would begin with a jerk off. From Lynn's point of view, getting that first orgasm out of the way meant that her lover boy wouldn't cum too quickly the second time around. He would stay hard for a long while inside of her. And even after his second orgasm he would come back for more, eventually ejaculating three or even four times before petering out. Tim was a stud.
Oh yes, the woodie...Tim remembered one summer night about three years back he and his family were vacationing at a beach house. One evening Tim, Mandy and a friend of hers named Lisa were all sitting around in the backyard shooting the breeze. Lisa was Tim's first crush, although she never knew it. How could he tell her? She was two years older than he was and would probably laugh at him had she known. Plus, she was Mandy's friend, and he imagined that the humiliation of his rejection would be unbearable.
Lisa was wearing gym shorts that warm summer evening and was sitting in a chair with her legs drawn up. To Tim's delight, a little tiny corner of her underpants was sticking out from under her shorts. Tim felt like he had just died and gone to heaven. He sat and talked with the two girls for as long as he could, sneaking furtive glances at Lisa without making it too obvious. But eventually he knew that he had to go inside and take care of business. He went into his bedroom, laid down on his bed, and masturbated, thinking of Lisa the entire time. The next morning at breakfast his sister was looking weird at him. Tim couldn't figure out why. Later that day he ran into Lisa, and she too looked at him weirdly. That's when it hit him, and he suddenly realized that he had left the bedroom light on when doing the deed. His bedroom was on the ground floor, overlooking the backyard, and the window was right by the bed. In a panic he realized that the two girls must have seen everything. Tim was mortified, he wanted to die, but as the day progressed, and the more he thought about it, it got more and more arousing. Knowing that Lisa had seen him masturbate became a turn-on. Lisa might not be his girlfriend, he'd never have sex with her, but what he did have wasn't bad. In a way, it was the best of both worlds. Tim could fantasize that Lisa was in the room watching him, but what really made it work, what excited him the most, was that he knew she had seen him, but she didn't know that. Tim could still act perfectly normal around her as if nothing had happened. To be sure, it was a bit of a buzz-kill that his sister had seen him too, but if you want to make an omelet you have to break a few eggs.
Tim was beside himself with anticipation for the remainder of the day. He had a baseball game that evening, and he raced home on his bicycle after the game ended, not joining his teammates for an ice cream as he usually did. Sure enough, when he got home he could hear the girls in the backyard. But he didn't go out and hang with them. Turning his bedroom light on to get their attention, he removed his dirty baseball uniform and stood naked in front of the mirror, admiring himself, but that was just the warm-up act. He left his room and went to take a shower. Returning to his bedroom, he turned the light on and lay down naked on his bed. Now that he knew that he had an audience, the thrill was overwhelming. Tim planned to draw it out and delay his orgasm for as long as possible. He wanted to savor the moment.
Tim didn't touch it at first; he just let his penis gradually harden on its own. The window was positioned right between his chest and his lower legs; the girls would have a perfect view of his cock. His arousal only got stronger, and very soon his penis was begging to be touched, so he began to fondle it gently, careful not to rub it too strenuously. Pausing, he listed for voices, and he could hear muffled giggles and excited girl talk. They must have crept closer to the window for a better look. Suddenly overcome by desire, Tim resumed his penis play, but by now he had gotten so excited he could no longer restrain himself. Stroking his cock harder than he meant to, he jerked it up and down as furiously as he could until reaching orgasm. And even then he kept jerking, until all the liquid love juice had been drained from his cock, and he reveled in the afterglow of the ejaculatory release even as the spent sperm began to dry and harden on his arms and chest.
To this day that remained the most satisfying orgasm he had ever experienced, and the memory of that summer evening still reverberated inside him. Ever since, his number one fantasy was to have a woman watch him masturbate. How lucky he was to have a girlfriend like Lynn who enabled the fantasy. He looked over at Lynn, who was rousing from her slumber. He took her hand and placed it over his erect cock. For an eighteen-year-old boy, his penis was average sized. It was six inches. Not bad, but not great. He still held out hope that, as he got older, it would continue to grow. After all, Lynn's taught, firm breasts would ripen and enlarge in a few years, as she filled out, so why not his penis? Lynn smiled as she touched Tim's firm cock with her hand. Six inches was good enough for her, especially when the owner of that organ was a wealthy, trust fund baby.
"You're a real horn-dog," she said, admiring her work. Tim's penis reacted to her touch the same way a man dying of thirst reacts to water. "Do you want to jiggle it for me," she asked? Tim said that he was limiting himself to one orgasm this morning, for they had a big night planned.
"That's even better," she replied. Lynn then closed in and licked his shaft with her tongue from top to bottom. She loved hearing Tim groan with passion. It made her feel useful. But this morning would be a little different, she decided, so rather than bring him to quick orgasm, she climbed up and stuck her panty-covered vagina in Tim's face. He responded to the challenge, and the cotton panty material did not prevent her from feeling Tim's tongue on cunt lips. She pushed back one side of the material, and Tim's tongue went in deep. Shivering with delight, she marveled at his technique. Tim was a good, thoughtful lover, experienced beyond his years.
Lynn reached back with her hand to feel Tim's cock and determined that he was as hard as he was ever going to be, so she slid down, smiled lustfully at him, and put all six inches inside of her. With her panties still pushed to the side, she slid down on the erect organ and began to lift and gyrate, massaging his cock with her cunt muscles. Tim's highway, they both called it, for her vagina had become so familiar with Tim's penis that it had developed and molded into a perfect fit for his love machine.
Their moans got louder and more frantic. She knew when he was going to cum. Before he could even cry out she had slid off of off him and thrust his thing into her mouth, where Tim's semen rapidly flooded her throat. She removed it and rubbed his little cock-head all around her face, smearing it with his secretions. She kept jiggling it too, for Tim usually had a supply in reserve. Just when you thought he had finished cumming he would get a second wind, and more seed would spill out.
With great tenderness and affection they soaped each other's body in the shower. They stood in silence, letting the hot water wash over them. Life was indeed good for the young lovers
"Tonight's the night," he said to her, as they dried off. "It's the unveiling of the video."
"I still can't believe you did homo stuff," Lynn exclaimed. She had a hard time wrapping her brain around that.
"Just some sucking...I had to. It's the Donkey way. They're trailblazing a new type of porn. It's gay and straight at the same time."
