When Eliza caught Jason sleeping naked it came as a shock. He had always been the quiet, shy type and seeing him lying sprawled across his mattress, sheets wrapped incongruously around his body seemed out of place. It took a good effort on her part to even get him into swimming trunks and out of the shade when they went to the pool together. Now to see him in such a way, this normally reticent man, openly naked in the guest room excited her more than she would have believed.
His cock, now resting peacefully on his inner thigh, gave her a start at first. In the time she'd known him she'd never thought of him in a sexual manner and now, as she anxiously studied the full of his body, she couldn't help but think of him in any other way. He was large, larger than she would have guessed. Larger even than any man she'd ever seen. Though he wasn't erect, he still looked thick as he rested. It weighed on his body, rising and gently falling with each breath.
She crept closer and cautiously sat on the edge of the bed. Moonlight entered from the window, allowing her to see the shadows as they outlined his body. Jason was always cute though their relationship kept her from acting on any urges she might have. He was more of a little brother to her, her childhood friend from the hometown she had long since left, more likely to dump water balloons on her than date her.
Time does strange things to people and in the years since she'd left, gone away to college and created her own life, Jason had grown into an attractive, well formed man. When she spotted him during her morning jog through the park, she had to look twice. Still not believing it she continued her exercise, only hear him running behind her yelling her name. On her run he kept pace and then followed it with a wind down at a juice bar on Central Park West. They've remained close since. She's introduced him to the best restaurants and he fixed her cable when it went out. She's teaching him how to cook and he brings the occasional take out when she's in the mood. Though their behavior is that of a couple, she did everything she could to not think of him in such a way. He was still a college student, after all, while she was an up and coming photographer.
Friday was their evening together. Most nights it was take out and a movie to wind down for the week and tonight was no different. It was midterms and he'd shown up later looking worse than she'd ever seen. He was unshaven, with bags under his eyes. The clothes he wore were dirty and wrinkled. Ushering him in quickly, they opened up the Chinese takeout he'd provided and settled down to watch tonight's movie. Unsurprisingly, within the first half hour he had fallen asleep, his portion of Lemon Chicken uneaten on the coffee table. Eliza dimmed the lights and, with a gentle prod, helped him stand and led him to the extra room. As she closed the door, she heard him collapse on the bed.
Now this. Kneeling between his spread legs, arms clasped across her chest, she couldn't look away. A mixture of guilt and arousal settled in her belly. Her conscience told her to get up, leave the room and forget what she'd seen but how could she? How could she ignore the fact that the bratty boy turned shy college student had the biggest cock she'd ever seen in her life?
Cautiously she reached with one outstretched index finger to touch him. The very tip of her finger touched the sleeping head of his penis. It felt warm and inviting. Growing bolder, she slowly ran the finger down until it stopped on the little hole on the end of his shaft. Only then did she notice the change. It seemed fuller, heavier, more malevolent somehow. In front of her eyes it grew, like an animal awakened from a long slumber. It didn't rise quickly, as some she'd seen but slowly, as if readying itself. He murmured, still entrenched in some deep dream. With a nervous yip she jumped from the foot of the bed and bolted. Outside in the hall, she listened at the door, cursing herself for being so easily surprised.
She retreated to her bedroom but lay quiet on her bed, unable to remove the image of Jason sleeping naked, his huge cock growing in front of her eyes. She masturbated anxiously and only after two fitful climaxes was she able to rest and drift back to sleep.
When she returned from her jog the next morning, he was already in the shower. Realizing her chance, she held her ear to the door and listened. As she hoped she heard more than the sounds of running water. Doing her best to remain unseen, she inched the door open and peeked inside. She couldn't get a good view from the billows of steam but what she saw was unmistakable. Jason was angled toward the shower running his hand up and down the length of his cock. Eliza watched hungrily. Seen in its full state, she was awed. It had to be nine, ten inches at least. A fat plum of a head sat at the end of his tool and she noticed, with not a little interest, that he preferred to swab the head of his prick at the end of every stroke. Soap coated his member, making the sensations all the more pleasurable for him. When he moaned, she closed the door and took a moment to compose herself.
She must be careful. A wrong move at this stage would cause him to run. Well aware of his past with women she knew what she was up against and had to plan her actions accordingly. Still...that cock....It's going to take all of her willpower to not pounce on it and all of her feminine charm to get him to come around. She brazenly slipped out of her jogging clothes and left them in a trail in the hallway. With her blood still churning from her run, she flopped down on her bed and parted her legs. Images of Jason pumping his cock filled her head and caused her pussy to awaken.
When she went for her shower, Jason was in the living room reading the paper. She crossed in front of him wearing only a towel. She allowed it to drop so he had a good view of most of her ass and though she saw him look he quickly turned away. The shower was still warm with the scent of him and she lazed under the hot water in the same spot where he had moments ago been rubbing his beautiful member.
Showered, shaved and lotioned, she sat next to him on the couch, her hair wrapped in another towel. She stretched her leg onto the coffee table beside him and began indifferently painting her toenails. From the corner of his eyes she saw him shift the paper and watch. Her legs were one of her best assets and she acted unaware that he could see all of the smooth, pink flesh of her thigh as it swelled into her firm asscheek. When she heard him shift she asked, as if it just came to her, "Why don't you date Jason?"
He was flustered, most likely by the sight of her leg and the hint of cleavage she showed as she bent to her toes, and could only skip over words in response.
"Is it because you're shy?"
There was a nervous laugh at that.
"Because we all are. Women, especially." She turned to face him, her towel opening slightly at the meeting of her thighs. Though he forced himself to resist, Eliza could see he desperately wanted to look. She rested her elbow on the couch, their bodies almost touching. "You need to meet a woman though. I know you'd like to."
A smile at this, as if she'd just come upon a secret. She continued, "I mean, when's the last time you've been laid properly?"
The look on his face was priceless. Immediately his expression dropped and he responded with a look of both shock and embarrassment. She pressed on, "A man your age shouldn't go without. It's not right. A nice guy like you shouldn't have to jerk off." She stopped when she saw the affect this had on him. He was biting his lips, his cheeks slowly darkening. "Not saying you do," she quickly added. "I'm sure you probably don't. I'm just saying you shouldn't. There are lots of women out there that would love to help you out. You're a very cute guy." She placed her palm above his knee, hoping it wouldn't cause him to jump.
They both sat there motionless for a few moments considering her action. Finally he rose, awkward on his own two legs. "Thanks 'Liza, I'll take your advice," he said grinning stupidly. "But now I've got to get to class."
She had made the first move and he'd reacted just as he predicted. Being so close, she knew the ins and outs of his dating life, as well as his predilections and all that he liked in a woman and planned to use those to get through to him. A shy boy shouldn't be kept alone with a cock like that. Such a fine example of maleness should always have a woman around to please it, play with it and relieve it. Eliza would do whatever she needed to be that woman.
They didn't get together for another week and she began to worry that she'd scared him off. Friday night came and still no word from Jason. Finally, as she lay in bed late Saturday morning, he called her, rousing her from the last traces of sleep. Hearing his voice, she threw the comforter off the bed to display her naked body to the room. She felt more comfortable talking to him while naked. Even his voice caused her pussy to dampen. As they casually talked about the week her finger snaked down her belly and teased her eager clit. They made plans to share dinner that evening and, as he provided the food last time they got together, she promised to cook for him. When the conversation ended she quickly jumped from her bed and ran across the apartment naked. Jumping into the shower, she began to plot on how she could win his attention. The image of his cock remained in her head and, directing the shower massager between her legs, she brought herself to a powerful orgasm, one that almost caused her to rip the showerhead from the tiles.
