Welcome to College

The picture taken and added, there was but one thing for Trip to do now, get to business. He undid his jeans and shed them and his boxers in one move. His more-than-decently-sized cock was already at attention and ready. In a moment of mercy he decided not to completely torture the girl by making her look at the rod that was about to enter her tiny ass. Instead he just grabbed a bottle of lube and made sure to get his cock more than ready--her hole looked tinier than any he could remember and it wasn't like he wanted to completely destroy the girl. Once he was sure he was lubed up he dripped a copious amount of the cold liquid onto Becky's exposed asshole and used a finger to start working it around and getting her ready. Once he was satisfied he placed his cockhead at the tight virgin hole of his latest conquest and once more paused, his cock looked like a monster compared to what it was about to enter. That pause wasn't enough to cause him to hesitate, just more something to notice. His mind back on the prize, he grabbed Becky's hips and pushed forward until the head of his cock disappeared and he could see the ring of her ass stretched firmly around his shaft.

Becky wanted to scream as she felt her hole being forced open, so she screamed right into the pillow. She'd heard about anal sex, she'd read about it, she'd even seen some erotic stories on it. The girl always laughed when she read about girls in stories complaining that it felt like a giant log was being shoved up their backside, that it was splitting them in half, thinking of it as poetic license on the part of the writer. Now Becky knew differently, she felt like her ass had been pried open to let a truck through. Her screaming and crying into the pillow lasted a minute as her mind and body adjusted to the new feeling--after all she didn't relax, she didn't know to relax. But considering that he hadn't pushed any further inside, she was finally starting to acclimate a little.

Trip was good at reading women, especially their bodies when they were getting his cock up their ass. It was a little mean to not tell her to relax, to not help her through this but he wouldn't change that for the world--he couldn't believe how tight this eighteen-year-old's ass was around his cock, and he only had the head in. "You can let go of your ass now," he told her as he started to push forward to work on completely filling her.

Her hands quickly surged forward to grab the pillow and squeeze it tight as his cock started to invade further into her most private spot. She wasn't screaming into the pillow anymore but she was breathing hard and fast to try and dull the pain as she felt the large cock slide further and further into her. She hadn't seen it before he started so she wasn't quite sure how much there was to go, though as she felt each push that buried it a bit deeper inside she was starting to think that it would never be all the way in, too much had entered already. She was a bit surprised when she felt something soft brush against her pussy and the movement stopped. Not being accustomed to it, she hadn't realized that it was his balls, that he'd gone as far as he could into her.

Heaven. Her ass felt like absolute heaven to his cock and Trip couldn't help but be surprised as he had her almost all the way filled up. Oh, he knew he could get that last little half-inch into her, but for now he was happy to just savor having his cock so far into the tiny teen's ass. He waited there a good long minute just feeling how her ass gripped and wrapped itself around his cock, twitching on occasion and giving him a gentle squeeze. He knew he had something special here, and there was only one way to make it better. Even though he normally wouldn't, he pulled out of the girl rather quickly, admiring the temporary gape of her ass before it started to close again and went to grab something.

If Becky thought having a large cock completely fill her ass was a new experience, she was in for quite the shock as the cock quickly exited her ass--it was familiar but not at the same time. The most surprising aspect of the whole thing to her was that she now felt a bit empty without having her ass filled, not something she expected after the amount of pain it had caused going in. She dared not look up from her pillow while he was out of her ass, she instead chose to just lay there, enjoying the fact that she was getting this temporary reprieve because she knew it wouldn't last forever. When what seemed like minutes had passed, she started to get a bit worried until she felt something cold and wet, yet hard and plastic touch her pussy lips and push into her. Whatever he was filling her pussy with was long yet slender, a relief for her. Once it was firmly nestled into place she felt him twist it a little and felt the swell throughout her entire body as the vibrator started to work inside her. She had to admit that her pussy had been wanting something and the vibrator felt good, distracting her until that pain started again as his cock re-entered her ass and pressed forward.

Normally Trip didn't take his cock completely out of a girl's ass once he was inside, he knew that the initial penetration was the worst part of the experience, and preferred the girls would accept their fate instead of hating the whole experience. Now that he was back in and could feel the vibrator in her pussy as his cock was in her ass it was perfect--not only was she just a bit tighter with how everything was crammed in such a small space, but if she came first his cock was really going to love it.

Becky was glad that Trip took less time getting all the way back up into her ass this time, it didn't feel as excruciating as the first thrust in had been to her. With him just sitting there holding it inside of her, it wasn't too bad for her, and the vibrator was definitely nothing she could complain about. She was hesitant as she felt the pullout start again but a little more relieved when he started to push in slowly again. He was actually starting to fuck her ass and it wasn't as bad as she thought it would be.

Trip watched as his newest conquest started to relax, by his six thrust inside her ass she was starting to let go of the pillow. By the fifteenth she managed to turn her head to the side and didn't look to be suffering anymore. Even with her relaxed this was still one of the best buttfucks he could recall. The only thing left to do was to ratchet it up and bring it to its rightful conclusion. Once more asserting his hands on her hips, he increased speed and started to hammer Becky's no longer virginal ass.

The rough pounding didn't elicit screams from Becky, but a lot of grunts and some cries of "oww" as he got going faster and faster. This was not something she was unfamiliar with when it came to her pussy, but having it happen in her ass was a whole different story. Her body was conflicted by the fucking she was getting--the pain in her ass primarily centered on her hole, and the pleasure that were running themselves through her pussy. She put her face on his pillow once more and just cringed, taking every inch of thrusting cock in and out of her ass, knowing it couldn't last forever.

Becky's ass was having the effect on Trip that he desired, though it was happening just way too soon for his liking. He frowned knowing he'd have to cut this shorter than usual but thought he could at least make this go out with some fireworks. He slowed down his thrusts, once more going deeper instead of faster and finally he held. Letting go of her hips, he grabbed the girl's shoulders with both hands and pulled, getting that last half inch of his cock up her ass. He delighted in the squeal as he held her there with his right hand and moved his left hand underneath her body to her soaked pussy, knowing just the right way to finish Becky off.

Pleasurable moans escaped Becky's lips, intermingled with the gasps and howls from the cock managing to find its way just a bit deeper inside. The feeling was unlike anything she had ever experienced, she actually felt as if she were conquered, owned by this beast of a cock that had been ripping through her backdoor. As the moans increased she couldn't believe what was about to happen. The moans changed into whimpers not unlike the mewling of a cat as her body shuddered and she was brought to orgasm by combination of the pain, the vibrator, and Trip's fingers that could do no wrong.

The moment finally arrived as Trip felt the tiny girl's ass squeeze around him while her pussy experienced pleasure. The pulses of her body as she was taken by her orgasm was too much for his cock as he started to fill her bowels with his hot cum. He let out a grunt of his own, something nearly animalistic as he claimed his newest prize.

Becky was surprised by the almost thumping feeling of the cock in her ass and the warmth that increased with every beat against her conquered rectum. The new experiences helped to prolong her orgasm, making her face flush at first then turn red with embarrassment as she realized that she was getting off with a cock buried in her ass. Her mind started thinking about what kind of slut that must make her, and her body responded to that thought too, prolonging it still.

When Trip was spent he was surprised by how long she had gone on--either he found a girl who just had really long orgasms or she truly enjoyed his cock in her ass. Either way, he didn't care, he knew she was special and he started to formulate what he would do next. Even though he was done, he kept his cock in that tight butt of hers, it just felt like it was the natural place for it, like his cock had found its long lost home.

At long last Becky started coming down to Earth, her orgasm subsided, and she felt Trip finally withdraw. She knew he was done, she could feel his cum in her ass, but she just remained laying on the bed, still trying to catch her breath from an orgasm unlike any she'd had before.

Trip just watched the soon-to-be college freshman laying on the edge of his bed as he cleaned his cock off and started to get dressed again. He couldn't believe he was thinking it, but maybe here was a girl who might be worthy someday of actually getting her pussy fucked by him, especially if every time she got assfucked she was like that. He finally reached down and removed the vibrator from her pussy before he grinned and started speaking to her.

"All right Becky, so here's the deal. See the camera up there?" He pointed to a corner that had a camera with the red light on it. "I'm sure you don't want to become infamous on campus. Show up the first Friday night you arrive in the fall at six. We'll go out, get food, do something like a movie or a party or something, but we'll always end up here with you on the bed like this. We'll do this every Friday, maybe you'll eventually get lucky and I'll take a turn in that cunt of yours."

Becky watched him as he spoke and noticed something a little different about the guy, that this time he wasn't as confident as he'd been with every other spoken word. When she felt like she might have some energy back in her arms she finally pulled herself up off the bed. She looked around for her clothes but didn't see them.

"They'll all be neatly in a pile on the pool table downstairs," Trip told her, no longer looking at her. He was still a bit uneasy, this was the first time he had made definite plans to see one of his victims again.

As Becky started walking rather gingerly toward the door, Trip held out her cellphone which she grabbed. Reaching the door, Trip said one last thing, "Oh Becky, welcome to college."

Not knowing what to say she just stared at him for a moment and opened the door and left. It felt strange to be walking through the frat house completely naked, but no one was out in the hallway. She finally found the stairs with the help of the signs pointing to emergency exits and headed down them. There wasn't anyone in the common room either--she realized she didn't even know what time it was. When she got to the pool table she was a bit stunned to see her clothes, nicely folded in a pile just like Trip said. She was even more stunned when she saw ten other sets of what were obviously girls' clothing also in neat piles on the table.

Becky dressed in what she started to figure was the early morning sunlight in the common room, starting with her bra and shirt. She hoped to find something that she could wipe herself off with. Again she was surprised when this request turned out to be rather reasonable as she saw several towels piled on one of the chairs nearby. She wiped up the juices around her pussy and the lube from around her ass and felt odd standing there so brazenly in a public area, feeling the cum traveling through her ass with every subtle movement. She'd take care of that later.

She checked the time on her phone and saw it was 7:30am, about the time she'd be waking up back in the Sorority. She was pretty sure she remembered her way back as she put the phone in her purse and finished dressing. Looking up to the board, sure enough she saw what she figured was her own ass clad in purple panties already posted to it. She shook her head and walked out of the frat house.

As she started to make her way back to the Sorority, she tried to think about what led her there in the first place and she couldn't remember much. Reaching the Sorority house door, she paused before opening it. Her ass was going to hurt for days she knew, and she'd have to go through it again in the fall. On the plus side though, the cute-yet-not-very-popular girl in her own school could have something to tell when she got back home: Since she'd be seeing Trip every week regularly, she could honestly tell them that she was the first girl in the class to have a college boyfriend. She smiled at that idea, wondered for a moment if it was worth the price before she said quietly to no one as she opened the door and went inside, "Welcome to college indeed."

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