Captain's Woes Ch. 02

That night, Dan found it hard to think of anything but Casey. He tried concentrating on his history homework, but the Executive branch of the government didn't seem to capture his interest quite like the taste of her pussy or the feel of that perfect ass in his hands. Lying in his bed, he could feel an erection growing, and proceeded to take his semi-hard cock into his hand. With his other hand behind his head, he closed his eyes and started to remember the events of that afternoon.

So caught up with his fantasy, he forgot to close his door all the way. At the time he didn't care, because no one was home when he got back from practice. His parents had gone away for a long weekend. He had forgotten, however, that Ashleigh, his sister's roommate from college, was going to be staying with them for the week. Dan's sister, Hanah was a year older then he was, and had gone to Cancun for spring break, but Ashleigh couldn't afford to go to Mexico. She was on scholarship, and as a freshman, didn't even realize that the dorms would not be open during spring break. She feared that for the first time in her nineteen years she would be alone, because her parents could not pay for a plane ticket back home, but Hanah had offered Ashleigh the opportunity to stay at the Grover's house for the week. She gladly accepted. Given a key, Ashleigh let herself into the house, not expecting it to be empty.

"Hello?" She asked. "Mr. and Mrs. Grover?" No answer came from within the big house. Dan, being all the way upstairs, didn't hear Ashleigh's quiet voice.

Putting her bags down, she began exploring the house. Hanah had told her the basic layout of the house, but it was still kind of confusing, especially since it was so dark. Cautiously searching for Hanah's room, she finally noticed a light streaming from a room with a door slightly ajar. A little nervous since no one had answered, she slowly moved towards the room and peeked in. What she saw surprised her.

Dan was naked on his bed, his eight inch monster sticking straight up, as his hand pumped it furiously. She could hear him softly moaning "Yeah, baby. Fuck yeah. . ."

Ashleigh was entranced. Coming from a small town, she hadn't had much sexual experience until she got to college. Even then, she had only had sex twice, and neither guy had had a penis like this. She realized that this must be Hanah's little brother, but she didn't realize there was nothing little about him. Not only was the penis so big, but he was drop dead gorgeous. Without even realizing it, she pushed the door open wider, and found her hand sliding down into her pants. She found that her panties were already wet, and as she slipped a finger inside herself was amazed at the reaction Dan masturbating was having on her.

Fingering herself, though, wasn't doing enough to satisfy her. She knew it was crazy, but she had to have that cock in her pussy. Quietly peeling off her clothes, she burst into the room. Dan jumped up from the bed, screaming.

"Who the fuck are you!" he demanded.

"I'm Ashleigh. . .um, your sister's roomate. . ."

"What are you doing in my room. . ." he was about to ask when he realized that Ashleigh was sans clothes. Not only was she naked, but she had a great body. Curly brown hair was held back with a tie, and topped off a cute face. She was full-figured, with a slight tummy. She was much different from Casey, especially her tits, which were at least a C-cup. His demeanor changed swiftly. "Were you watching me jerk off?" Ashleigh blushed and nodded. "Did you like what you saw?" he asked, grinning. He moved toward her, holding his dick in his hand. She blushed harder and nodded again. "What do you want to do with it?" he asked. She didn't say anything. "Do you want to suck it?"

"Yes," she said quietly.

"What's stopping you?"

Ashleigh dropped to her knees and began licking the big cock. She had never sucked a dick before, but she had watched as Hanah had gone down on her boyfriend Rick. She remembered her roommate telling her that it's just like sucking on a pop-cicle. Taking that in mind, she took the penis into her mouth, her tongue swirling and licking. Dan's groans of pleasure egged her on, and she decided to try to take the whole thing into her mouth. She had read about deep throating, and knew that guys really liked it. She wasn't sure if she could take the whole thing in, and on the first try, she gagged a little. Ashleigh realized she needed to relax, and slowly she could feel the meat sliding down her throat.

"Holy shit!" Dan moaned, looking down into Ashleigh's green eyes. Having never met a girl who could take his whole cock in her mouth, and coupled with the self-ministrations he had given himself, it did not take him long to come in the complete strangers mouth. Even though it was her first time sucking dick, she took his come like an old pro, not losing a single drop.

"That was amazing," he gasped. Ashleigh smiled, and Dan helped her to her feet. A calm seemed to come over her, and she casually pushed Dan onto the bed.

"You better get hard, Danny-boy," she giggled, straddling his body. He pulled her too him, and the began to kiss savagely. He grabbed her tits and squeezed hard, pinching her nipples between his thumb and forefinger. Ashleigh grabbed his head and pressed it against her chest, and he started kissing and sucking her breasts. Going on in this way, it didn't take long for Ashleigh to notice something.

"That was quick." She lifted up into a sort of squat, and reached back to grab Dan's cock. "Stick this monster into me. Fuck my pussy, Dan." Dan needed no urging, and with her hand guiding his penis towards her vagina, he was soon deep inside her hot tightness.

He grabbed her ass and watched as she sat upright, filling herself with this stud's dick. She started to slowly ride it, never realizing she could feel so full. She loved the way his calloused hands gripped her ass and tits, and she knew she was going to lose control real soon. She picked up the pace, and moaning loudly, gripped the headboard behind Dan's head. Getting the idea, Dan took a firm hold of her waist and began thrusting upwards, matching her frantic humping.

"Oh fuck, your cock is so big. Oh god, you're making me come! You're making me come!" Hearing this, Dan began unloading his come inside a pussy for the second time today as Ashleigh wildly jumped up and down on his cock. The last drop barely out of him, he lifted her off his penis with his strong arms. She gasped as she suddenly felt the emptiness.

"What the. . ."

"Turn around. I want to eat that pussy." Not understanding him, Dan deftly flipped Ashleigh around and positioned her into a sixty-nine. He spread apart her ass cheeks and dove into her dripping pussy. She gasped again, because no one had ever eaten her out. Seeing his semi-hard penis in front of her, she took it into her hand and started to jerk it off. Feeling that it was wet, she curiously put it back into her mouth. She had never tasted her own juices, and the mixture of them combined with sweat and come tasted awesome. It was hard to concentrate with all the attention her pussy was getting from Dan's tongue, but it doesn't take much for a guy to feel good when his penis is in a girls mouth. Not too soon after they began orally fucking each other, both of them arrived at an orgasm.

Sweating and panting, Ashleigh crawled her way up Dan's long body. They kissed, enjoying the flavor of each other.

"What did you say your name was again?" asked Dan.

"Ashleigh," she giggled. She got up to gather her clothes. Looking back over her shoulder, she casually added. "And I'm going to be here all week."

Dan couldn't believe it. There was something in his life now competing with tennis for pre-eminence.