The Bet Redux

She had never dreamed that anal could be so great. She wasn't ready to discuss it with her friends, but the thought of him tonguing her ass sent her into a frenzy just thinking about it. One friend, in particular, had always said that maybe she would like anal if she found a man who would do it right. It was difficult to listen to her friend lament the torpor of her sex life. Always the same thing: get in bed, cop a few feels on one another, one climbing on top of the other and some rhythmic moving until unsatisfying orgasms for both. Sad.

She knew what that was like, too, from her first serious relationship. He was the second, and they actually had a pretty good run. It was always tensions with their families, differing opinions about work, and just life that caused them to drift apart and finally end it on good terms before they ended up hating each other. Then a few short affairs with men she knew she would not spend the rest of her life with, none of whom were mean or nasty in any particular way, then The Ex. A year and a half later, feeling much better about herself, she was successfully moving on.

They happened to meet again in a grocery store which she never frequented, but stopped at that day for eggs and diet drinks. He looked good, but then again he always did. Growing up as one of the most popular guys in high school had, surprisingly, not gone to his head. Of course, he was older now, with a sprinkling of grey, but those soft brown eyes, thick lashes, and that one dimple were just the same. They connected again. She had always kept in touch with him, but the last time she saw him was over two years ago, so they decided to grab a bite for lunch the next day to catch up. They ended up falling back into their old routine of frequent chatting, meeting for lunch, and just being friends again.

Then he brought up the bet. The one she forgot. The one she would never forget again. The way he made her feel was incredible; she felt like such a wanton. She wanted more, definitely in the form of another tongue-bath and having her rosebud reamed out. She never thought she would want to be anyone's anal slut, but here she was, getting wet in line at the bank just thinking about it. They were never ones for toys before, but after his introduction of the beads, she remembered a passing comment he'd made about a vibrator. She thought of him filling both of her holes, one with his hard cock and the other with a vibe, and wondered if the cute guy behind her could smell her arousal. When she turned around and saw his mouth slightly open and his heartbeat in his neck, she figured he could and gave him a wink. That was her deciding factor. She was going to the adult bookstore on the way home to find something to fill her needs.

Being in the bookstore turned her on even more. She grabbed a few different flavored lube packs, a movie that looked pretty good, and a blue vibe with little studs on it. Nothing too big; her asshole was tight, and so was her pussy, and she didn't want anything that would actually hurt her. By the time she got home, after checking out the movie in the car (you should have seen the look on the guy's face in the big truck next to her...) at traffic lights, thinking about her new toy, and the flavored lubes, her panties were soaked through. She could smell her own arousal in the car, and couldn't wait to get him over to the house later for some fucking and sucking.

He was supposed to be there for 8:00, but some late-night roadwork on a busy stretch of highway held him up. It gave her time to check out the movie before he got there. She'd never seen double-penetration before, but it certainly looked satisfying. Granted, the girl in the movie had two guys, but there was no way that was happening, so she was going to make do with him and her new vibe. Watching the guys in the movie alternately lick and fuck the girl's two holes touched a primal spot in her, making her hotter and wetter than ever before. It left her wondering if she would even need the flavored stuff instead of him using her own wetness to lube his hardness into her crinkled hole.

He got there about 20 minutes late, and was surprised when she greeted him at the door in a short robe, obviously nothing underneath. He was halfway in the door, already reaching under her robe, probing her with his fingers. When he pulled them away, soaking wet, he knew something was going on. He pulled her over to the chaise, undoing her robe and his own clothes at the same time. Not giving her a choice, he positioned her, doggy-style, with her ass at the end of the chaise. Pants halfway down, he thrust into her soaked pussy, kneading her asscheeks in time to his strokes. Still fucking her, he pulled her into a more upright position so that he could pinch her nipples, making the stand at attention. He pulled out, still pulling her nipples, making her moan with delight.

She was on the verge of her first orgasm, and his withdrawal made her feel empty and deprived. When he moved to the bedroom, she composed herself enough to stand on her own and followed him, sitting on the bed. He saw the box for the movie on the bed, picked it up and read it.

"Oh, someone's being bad tonight. Watching another blonde get both her holes stuffed without me?"

"Well, after what we did last time, and it feeling so good, I thought this might be interesting to watch."

"The problem is that she has two holes and two cocks to fill them, while you have two holes and only one cock, although I'd be happy to accommodate both eventually."

"I bought something I thought you might like..."

When she showed him the flavored lube, one eyebrow went up. When she showed him the vibe, the other followed. She left the thought in the air, waiting to see what he would say. Without warning, he grabbed one ankle, pulled her over to him and turned her on her stomach, and smacked her ass with his open palm. It wasn't that he did it hard; it wasn't intended to actually hurt her, but it shocked her, drawing a gasp.

"Did you like that? Did you like when I smacked your ass? I think you did, and just like I made you beg for my cock in your ass, I'm going to make you beg me to spank you like a bad, bad girl."

She lay down on the bed, waiting for him to climb atop her. He did, marveling at how wet she was. He stroked in and out, bending his head to catch a hardened nipple in his mouth periodically. He alternated fast and slow, always bringing her to the point of orgasm but never letting her get there. After the fucking and one smack she'd had already, she was going crazy waiting to come. He wasn't going to let her off that easy; he wanted her to the point of begging and pleading because that's when he knew she finally let herself go completely to enjoy what he was doing. He got her up on her knees again, legs spread as wide as she could, and he dove into her from the back. He licked her clit, lapped up the juices that coated her swollen pussy, and tongued her rosebud until he felt her breathing heavy. Grabbing the lube, he coated his fingers and dripped some onto her.

She squeaked at the cold liquid, asking him if he was going to fuck her again and was given a choice. He could fuck her with his dick and plunge her ass with the vibe, or the other way around, but while he was asking, he had already started to massage her rear hole with his fingers, preparing for either one. His finger buried in her ass left her speechless. When she felt him start to stroke it in and out, her pussy clenched. Before she could answer, he smacked her ass with his free hand, leaving a pink handprint on its whiteness. She gasped, and he buried another finger in her, stretching her tight hole even more. He added another finger, and she began pleading with him to touch her pussy, to let her come. He started a rhythm, his fingers stroking her hole and his other hand smacking her now pinked cheeks.

When he felt her ready to come, he withdrew completely. She was now in a frenzy, waiting to orgasm, her asscheeks pink and her labia swollen and blood-red. He could see her aching need, and again gave her a choice. She begged him to screw her, on her knees with her ass high in the air. He skewered her with his hardness, driving it in and out of her pulsing wetness. When his thumb touched her rosy hole, still open from his assaulting fingers, she bucked back against him, causing his thumb to sink into her ass.

She came, moaning and whining, begging and pleading, her hot juices running down the inside of her thighs. He watched her still-pink asscheeks quiver, waiting to be spanked again. She shuddered, still begging him to fuck her. He ground into her until she finished and collapsed on the bed.

After she caught her breath, he told her he was not done with her. He reminded her that he was going to make her beg for a spanking. He began licking her juices off of her thighs moving up to suck on her clit, reaching occasionally to pinch her nipples. When she tried to push him away, he sucked that much harder, and sank two fingers into her sopping pussy. She came immediately, and tried to pull him on top of her. He flipped her over, re-inserted his fingers, and told her that he would not pummel her senseless until she asked for that spanking. He fingered her slowly, bending his fingers to touch her g-spot, stroking it until

"Oh, please, please, spank my ass! Smack it and show me how bad I am. Smack it until it's hot and red and then fuck me!"

He began a light tattoo on her ass, left and right, while she wriggled and undulated at him. He continued, rapping her cheeks harder and harder until the only way to keep her somewhat still was to bury his cock in her. He chose her ass, presenting it at her opening and slowly inserting until he got past the stretchy ring of muscle, then filling her with one push. He began a new rhythm, this time with him in her lubed, loosening rear and his fingertips, lightly slapping her cheeks.

When her orgasm began, he went with it. She shrieked, ramming herself back against him. He grabbed her hips and bored into her, waiting to fill her ass with his hot come. He waited until she was at the peak of her peak and he let loose, shooting jet after hot jet into her. They both finished, falling to the bed in an tangle of sweaty limbs and sated appetites.

Afterwards, when she pointed out that they had never even used the vibe to try a double-penetration, he just smiled and thought about that for next time.