The Very First Time

She lay frozen, almost mesmerized. Lying there naked, Billy's rough callused hands pressed along her body, squeezing too hard, pressing his semi hard cock firmly against her leg breathing heavy as he tongued her ear. That odd look younger men get, like a starved dog finding some frozen meat. Sloppy and wet. This was going to be her first time? She had waited years for this garbage?

"Are you okay with this?"Billy asked coldly, "Do you want me to stop?" releasing his grip on her right breast, the blood rushing back making it red and flush.

"No, it's totally fine. I am just trying to figure out what I am supposed to be doing, do I lie here or what?" Anne replied, barely blinking not bothering to turn to face him.

"I know what you should be doing..." Billy breathing, grabbing her hand roughly, placing it on her cock. Sticky and hairy, she felt a small rush pass through her, she turned her head with a questioning look.

"This is what you should be doing, grip your hand and start moving it up and down....ohhh just like that....fuck girl, slow down or I'll cum on your hand." Billy's face was almost in a painful grin.

He slipped two fingers along her now wet clit, his other hand moving Anne's back down by her side. He pressed his head against her stomach moving it down towards her groin. Listening to see if he could hear his fingers slip in past her hymen with a quick hotness of blood mixing with her excitement. He looked up to see Anne's face a pleasant pain he had seen before, with his last virgin. He enjoyed that little gasp when he broke through, he was sure he was close to finding the best place to hear his fingers enter her.

Anne felt the sharp stab and instant tingling deep inside her cunt. She could see why girls kept going to get to this. So dirty and happy all at the same time. She'd be marked now, one of those girls, easy, cheap date, fuck friend extraordinary now.

Her best friend Marissa lost hers last year to a senior, but not just any senior he was 21 years old having failed on purpose to keep placing high school sports, hoping to get drafted. Sadly, he was too poor of a player, and hadn't come to terms with why it wasn't happening. Greg, 6'5 and about 300 pounds of the kind of muscles you only get from four hour sessions at the gym, thick and uncut he had accidentally put his cock in her ass.

Marissa explained that it was like getting a needle in your mouth for a filling, that sharp blinding pain that takes your breath away then the hot release when it takes effect and starts to feel not too bad. Greg, she often said, had taken her not yelling out as a sign that this was okay. The first five minutes felt like she was paralyzed, trapped tightly against the bed her odd angled head was being held down by her hair by Greg's massive hands. He told her to relax and he would press in slowly. His fat head pressing through to her anal canal, she took long breaths and bore down on his massive head. By now Greg realized he needed lube, and quickly globed on his cock thick Vaseline. The pain subsided once the lube reached deep in her asshole. It felt much better now, she almost came as he bottomed out his cock in her tight ass. Greg sighed, and started pumping slowly at first in and out, leaving her feeling waves of deep pleasure. He pulled all the way out, then quickly plunged in, hot waves started. A deep sensation in her body rippled her back and pulled Greg deep inside her, he gasped unable to hold back anymore the came hard in time, leaving the sheets wet.

They had showered and de-virgin another hole ending in an awkward three some with his 33 year old roommate Fred and his 19 year old brother Gary. She told me she sometimes cried herself to sleep that she let it get so far, and vowed to never have sex again. Only, instead she ended up sleeping with half the towns men, and a third of the towns women.

Billy took her thrusts to mean that it was time, he quickly got in place between her legs and took her breath away when he shoved his cock roughly up her tight cunt.

Anne, froze again, almost too much. Would she ended up like Marissa, the town whore, it was a damn miracle she didn't get pregnant. Billy slowed his pace watching her face with little interest, really being more turned on that it didn't seem like she wanted this, he grinned putting her legs up over her shoulders and tilting her cunt tightly over his cock, he could see his head press up against her belly happy to see she was slim enough to pull this off for him.

Slamming hard against her ass, he pulled out quickly and fumbled to get back in. Anne wiggled up his thighs trying to line his cock up with her ass. Billy pressed his thumb into her cunt and pressed it down into her tight asshole several times until his thumb finally popped in. He pressed firmly against her tight ring angrily pushing his head in, trapping her from trying to escape like she now valiantly was.

In now Billy enjoyed the softness he so enjoyed of this hole, even if he griped the girls hand tighter he couldn't even get a hand job this tight. Pressing her legs up higher, she aided his advancing cock into her ass. The hot waves of pain slowed into tight spasms of orgasm. Billy pressed down on her belly, changing the grip to his favor by the arch of her back. Anne wriggled down as the full length entered her. She purred, and rolled off him feeling the beginnings his balls about to release his cum. She quickly took his cock into her mouth, the smell was overwhelming but the thick gobs of cum squirting down her throat kept more of her interest.

He breathed deeply, and Anne slipped off the bed quickly gathering her thing, headed for the bathroom. Once inside, she latched the door and took a quick hot shower. Barely drying her skin she dressed fast. By now Billy was tapping on the door asking if everything was alright, she replied she forgot she had an important doctors appointment and had to go right away, but to call her after 6 to go for dinner.

As Anne rushed down the street on the bus, she called her cell phone company to change her number, she wouldn't be needing to meet with Billy again. He had served his purpose, taking something that was so pure and making it filthy. She rung Marissa and asked her what her dinner plans were that right and if she planned on going clubbing later and getting laid. Marissa, smiled, finally the little virgin lost her shine, and was down to fuck now, a hunting partner.

That night Anne met a new conquest, a middle aged man just starting his mid life crisis currently separated from his wife, he felt it would be too lonely to go home alone. He told Anne that he found her exquisite and would really like to get a mouthful of her ass if it wasn't too much to ask, pressing his middle finger twisting the fabric against her asshole. She turned to him and.........

To be continued...