Anal Virginity

**Names have been changed...

I'll leave it up to my readers to decide whether or not this ever truly happened...ax

Cindy moaned softly as Dane slipped two fingers inside of her. She felt the familiar ripples of orgasm overwhelm her senses, body tightening around his digits, juices dripping onto his hand. She stood there, rigid as his fingers worked their magic, rubbing and caressing her secret places.

She looked down at him sitting in front of her, arm muscles tensed, and saw the predatory gleam in his eyes, he wanted her... NOW... She whimpered at this, remembering the other times he had made her cum until it felt like her head would explode. He seemed to be holding back now, teasing her, his fingers stroking her g-spot as his thumb rubbed her clit.

Suddenly his fingers withdrew, and her pussy clenched, already missing the pleasure he gave her. She whimpered, expecting him to turn her around, drop her shorts and enter her. Instead she felt his finger pressing into her ass, rubbing her juices around the rim to ease his entrance. He slipped inside.

Cindy threw her head back, God how his finger in her ass turned her on. Her clit throbbed with anticipation; she needed him inside her so badly.

For the next half hour she didn't know what was where, two fingers in her pussy, one in her ass, or two in her ass and one in her pussy, the time passed so swiftly, and before she knew it she was hitting her ninth or tenth orgasm, this one making her teeth clench and her legs tremble.

Dane looked up at her, green eyes smiling, "You just came from me finger fucking only your ass, Cindy."

Her head spun, did she? "Wow I knew it was possible but I never knew that I could cum from anal." she said softly.

"Ok baby, now let me fuck you, I'm so hard it hurts." Dane whispered. Cindy looked around, thinking, her grandma was asleep in the house, they were out on the front porch, where anyone could see or hear. She turned off the porch light and took up a position outside the living room window to keep watch, bending over a tool bench. Her pants dropped to her ankles as she presented her tight tan little ass for his pleasure.

He entered her pussy so swiftly she gasped, his thick, hard cock filling her tightness. She moaned in pleasure as he started to move in her, bringing her to orgasm after orgasm.

She began to wonder after a few minutes, he seemed to be holding back from his pleasure, purposely not cumming. Since they were pressed for time before one of the kids woke up or her grandma got up, she urged him on, pushing her hips into his, but he still held back. She felt an extra width inside her as he pushed in two fingers alongside his cock.

She reveled in the even fuller feeling, being stretched to her limit by the thickness of cock and fingers. After a few minutes he withdrew them, and she felt him sliding them into her ass, keeping rhythm with the thrusting of his hips. Feeling so filled and content Cindy's excitement peaked, throwing her into an orgasm like none before.

Suddenly, he withdrew, holding her hips in a vise grip as she looked back at him questioningly, the light from the window lit a strip of his face up, what she could see looked like a mask of control, he was holding back from her. She felt his hands caress her back and buttocks, squeezing her cheeks. His hands parted her and she felt his fingers withdraw from her ass, to be replaced with the head of his cock.

Pressing into her, she felt the head slip inside, the pain making her whimper, but it wasn't as bad as the times he'd tried before, his fingers had been stretching her all night.

She looked back at him, hunched over her, slowly sliding another inch inside her tight passage, it burned, she whined. Dane stroked her back, encouraging her to loosen up her muscles.

He slid in inch by slow inch, her whimpering all the while, the burning pain turning her on yet hurting her. Finally he was fully inside her, she could feel him throbbing, as her tight little ass gripped his cock with everything it had, trying to expel the invader.

She felt the heat of his crotch pressed against her buttocks. Her insides felt sore with him in there. Cindy concentrated on the tightness, and soon figured out how to let go of those muscles, so different from the muscles of her pussy. Dane felt the release and gave a sigh of his own, slowly pulling it out of her virgin ass.

He gently fucked her for a while; she reveled in the new sensation, as he started moving harder and faster. She felt an orgasm building, and whispered loudly, "Fuck I feel so DIRTY now. Make me your dirty little slut!!"

Now he was slamming her ass, balls slapping against her swollen pussy. She dug her fingernails into the bench as she came so hard; her knees went weak with exhaustion. Suddenly his cock seemed to swell even bigger inside her tightest hole as she felt it start to jerk and she came again, knowing he was cumming inside her ass, where no man had ever came before...