Anal Adventures of Alex Ch. 02

Over the period of a couple weeks, Alex got a little bored with fingering his ass while he jerked off... although it still felt good, it was often lacking that feeling of a painfully pleasurable stretch. If he left his ass alone for a couple of days then it would tighten up again, but in lieu of having anyone else's ass to plunder he enjoyed being able to play with his own. Especially because it felt so good. His ass was quite accepting now, almost immediately, of two fingers, and it left something to be desired...

Alex was quite sure that he was ready for bigger and better things, which is how he found himself wandering around a porn store. It made him a little nervous, especially because there was a very attractive girl his age re-stocking in the dildo section... in fact, she was the only other person in the store. He didn't want her to think he was gay, because he desperately wanted to hit on her... but at the same time, if he hit on her could he buy a dildo from her?

She was smiling at him from the corner of his eye.

Duh, she works here, he thought, forcing himself to concentrate on looking at the wall of various rubber and silicon implements, and not down her cleavage as she leaned forward. Part of him wanted to scoot back to another part of the store... not just because he felt slightly uncomfortable looking at the dildos with her just a few feet away, but because the few glimpses that he'd gotten of her ass were pretty arousing.

Instead he shoved his hands in his pockets and tried to concentrate on choosing a dildo and getting out of there. The thing was, there were so MANY. And they all promised different things... he was feeling a little intimidated by the vibrators and so had decided to stay away from them for now, but all the anal toys and dildos came in so many varied shapes and sizes.

He was just deciding that he wanted something more naturally shaped, some kind of dildo that actually looked like a cock, when the girl stepped closer.

"Can I help you?" she asked.

"Ah..." Alex's mind came to a screeching halt as he looked down into her brown eyes, trying to think of a response. ANY response.

She smiled, "You've just been looking at the wall for awhile, I thought maybe you were having trouble deciding... if you have any questions just let me know. My name's Jen."

Alex found a response, "Thank you."

Jen smiled again and walked towards the front of the store. Alex watched her go... those jeans weren't even very tight but they hugged her curves delectably, keeping that cute little bubble butt quite snug in its denim casing.

Shaking himself, he turned back to the wall. He couldn't hit on the porn store girl... he was about to buy a dildo from her. Something about that just seemed incredibly awkward. Besides, she was only talking to him because she worked there, not because she was hitting on him, he reminded himself.

Looking over the wall that he'd been staring at for about twenty minutes, Alex finally grabbed a box for a decent sized, flesh colored dildo. It was definitely much bigger than his fingers, but not one of those shocking, frightening looking ones. Walking to the front of the store he could feel his heart pounding a little... for some reason he really didn't want Jen judging him. Probably just because she was pretty.

As he approached the counter she looked up and smiled, "All ready then?"

"Yeah," he managed to say, putting the box down.

Still smiling, her smile got a little bigger as she looked down at what he was purchasing, and she picked up the box and started to open it. Alex was startled, but didn't know what to say or do so he just stood there as she pulled the dildo out of the box, it flopped slightly to the side on its own weight.

"This is one of the good ones," she told him, holding it out, and he belatedly realized she expected him to take it. It was soft but firm in his and, surprisingly so... for some reason he'd expected it to be very hard, less pliable, "Do you have lube?"

"What?" he asked, blinking, his hand still wrapped around the fake cock.

"Lube," Jen repeated, "You'll want it with one of these, they can be... sticky isn't quite the right word, but I can't think of a better one. Anyway, you want something to make it a smoother insertion." She smiled at him, somewhat mischievously as he blushed and he got the distinct feeling that she was very much enjoying setting him on edge.

"Oh." God he sounded like an idiot. She must think he was completely monosyllabic.

He was trying to think of something to say when she reached back out and took the cock from him... it was a little strange to see her hand on the realistic looking dildo, and his mind immediately brought up the image of what it might look like to have her hand on HIS cock. Which of course meant that he was standing there staring blankly as she scanned the box and popped it in the bag.

"Is this for you, or a gift?" she asked, running his card through.

Finally he was surprised out of being a total dunce, "Isn't that a little personal?"

Jen laughed, "I suppose so, but I was really just wondering if you wanted a gift receipt."

Alex blushed hot red again, "Oh. Um. It's for me."

Her eyes got just a bit wider and he wasn't sure if he wished he'd lied or not... she didn't seem to be judging him... but it wasn't something that most guys would probably admit to. Too late now.

There was a certain quirk of amusement to the corner of her mouth as she wished him a "nice evening".

"I'll let you know," he quipped, raising his eyebrow suggestively, finally getting a little of his own back as she looked startled and surprised, then burst out laughing as he walked out the door. He'd made her laugh... maybe he'd go back sometime and get her number.

Getting home, Alex hurried to his room and closed the door, he lived alone but somehow it just seemed right to have the door closed for activities like this. His lube was already ready on the computer desk...

Stripping down he kicked off his pants as he opened the box, trying to figure out the best way to do this... Somehow the dildo seemed even bigger now that it was at home and about to go into his ass. His own cock twitched in anticipation. Setting it on the computer desk, it pointed up at the ceiling as it bobbled slightly.

Coating his fingers in the lube, he sat in his computer chair, scooting to the edge of it and spreading his legs, resting them on the computer desk so that he was completely open. His fingers slid in easily and with very little resistance... it felt good having them sliding and out of him, a slick plundering and his other hand found his cock as it stiffened with arousal. Enjoying the feeling of masturbating while his fingers pushed in and out of his ass, Alex closed his eyes and pictured the girl from the toy store and the way her hand had looked on the fleshy dildo.

Without opening his eyes, he pulled his fingers from his ass and reached out to grab a hold of the waiting dildo. Picturing the pretty girl in his mind, he pretended it was her hand holding the fake cock as it pressed against his asshole...

Oh dear god.

His ass stretched open, much further than it would have to for his fingers... it felt painfully tight, and his neck fell back and strained a little as he began to push the fake cock in. The pliable nature of it made it a little hard to open his tight ass, but it also meant that his hole could spasm and grip it.

Panting, he jerked on his own cock, feeling his body relax a little as he started working the tip of the dildo in and out of his ass, feeing his hole opening and closing again... painful in a way that just hurt so damn good. With every push, he got a little bit more in, squirming in the chair a little as his ass was stretched open. Keeping his head leaning back against the chair, he tried to spread his legs a little wider, making it slightly easier to accommodate the invading toy.

Arching his back, Alex rubbed his cock harder as he pushed a little bit more of the toy into his ass, gasping at the full feeling... he could tell he had a lot more of the toy to work into his tight hole, but his pleasure was already mounting. Pulling the toy out a little, he began fucking himself with it, keeping his other hand going on his dick, just working what he could in and out, pulling back every time the pain started overcoming the pleasure.

As his full ass tightened on the toy, it pushed through thanks to the lube and he groaned loudly with the pleasure of feeling it force its way through his grasping ring. Shoving the fake cock deep, the deepest he'd managed to get it yet, his hand squeezed hard as his own cock began to spasm and spurt against his palm. Writhing a little in the chair, he could feel his ass tightening and loosening around the toy, and his body bucked a little with the new pleasures.

As his orgasm subsided, he felt his ass working to eject the intruder, and he pulled the fake dick from his spasming ass with a slight 'pop'. Putting it back onto his computer desk, he reached down to rub his poor abused asshole, his eyes widening a little in wonder as he felt it gaping just a bit.

"Fuck..." he groaned, closing his eyes again as he leaned back, "That was good."