A Bad Bet

That was the bet; one night and no one could accuse me of being a pansy ever again. Also 20 bucks. It might seem pathetic to you, but that 20 bucks will feed me for a week. How bad could it be, anyway?

Harvey sat alone in the bedroom with the lights turned off, listening to the laughter of his friends just outside, apparently still bargaining with her. The idea had been discussed innocently enough at first- theoretical strippers are still mostly harmless- but when it was suddenly upgraded to hooker, plans started getting dicey and now he was cut out of the loop altogether.

The woman they found was an average looking woman with short, blonde hair. She wore a tight, red tank top over a short, denim skirt and walked with a pronounced sway in her hips. Before he was pushed through the bedroom door, she had looked him over once and smiled, showing a gleaming set of white teeth, though one in the back appeared to be missing. Lord knows what they were saying now.

Quietly, he stood and tiptoed to the door. He pressed his ear flat against the wood, but recoiled in shock when the handle began to turn. Luckily, it was only one leap backwards to the end of the bed.

"Paid in advance, such nice boys." She closed the door behind her and put away what looked suspiciously like a wad of bills in a small, black purse, which she then deposited near the door. "Harvey?" Her voice was a pleasant alto.

"Y-yes ma'am?"

"Oh heavens, darlin'. Just call me Ruby. Now, your friends have arranged a little somethin' for you. They say that you're as ripe as a new cherry and I don't rightly know if you're up for this, but I haven't turned down a sum of money quite like this before, so I haveta ask," Ruby stepped closer, her breasts just about eye level, "Are you willin'?"

Little Harvey responded instantly, but Big Harvey took a moment longer. Technically, he could back out and probably no one would blame him too much, but he wasn't about to let them see him chicken out. "Yes."

"All right, then." Ruby took his hands and pulled him up. With surprising sweetness, she touched his face before softly kissing him. Harvey forgot to react, so she pulled back and laughed saying, "I won't bite... yet." The next time, he kissed back.

"Wait," he said when they broke apart, "Why are you... I mean, don't you just..."

Once more, she laughed prettily, brushing a lock of golden hair from her eyes. "It's your first time, sweetheart; you'll remember this for the rest of your life. Besides, dirty tramps need love, too." Her sentiment was sincere, but she immediately undermined her words by pulling off her tanktop to reveal an expanse of smooth, pendulous breasts. "Go on and touch them," she said, noting his transfixed gaze.

Though his hands shook, Harvey did reach out and caress both tits, feeling their weight fill his hands and rubbing her nipples with his thumbs. Impulsively, he leaned down and took one in his mouth, rolling the little bud with his tongue, making her breathe heavily. "You will be fun to teach," she stepped away and turned toward the door.Click. "Let's not let the others bother us."

Ruby then bent over and reached into her purse, taking out a length of something that Harvey completely ignored in favor of ogling her beautiful ass and wondering if his hand would be smacked away from reaching under her skirt. She straightened and approached him, pushing him back onto the bed and directing him to slide back until his hindquarters hit the headboard. "This isn't something I do very often, at least not for my regulars. Your friends wanted you to have the works, so you'll have the whole package. You'll like it." She straddled him in a full kneel, her boobs bouncing around his face and prompting another attack with his tongue, and took his wrist. Swiftly, she bound it to one post on the headboard and then, before he could recover his senses, bound the other.

"Hold on a minute..."

"Shhh." Ruby settled back on his knees, trailing a finger down his chest. "Let me do all the work..." She pulled out a pair of scissors he hadn't seen before and, ignoring his protests, cut his black, t-shirt to ribbons. He received two kisses to the chest to assuage his annoyance, then promptly found himself without pants. Ruby grabbed his ankles and pulled him flat, then bound his ankles to the remaining bedposts. Harvey tested his bonds, pulling gently at first, then full on yanking until he gave himself minor rope burns. This nylon twine was industrial grade, apparently.

"That's a good boy." She stood on the bed and he noticed for the first time that she was wearing glittery red stilettos the color of rubies. Also, she was wearing a thong and watching its string rub roughly between her lips was quite distracting. She paced back and forth over him for a moment as if she had just caught a wild tiger, then sat on his thighs facing him. Her scissors made another appearance pulling double duty by dispatching his briefs and making him fear losing his manly bits via cold metal. On the bright side, his erection was now unrestrained by jeans.

Ruby touched his throbbing dick, teasing him with her fleeting fingers. He swallowed a whine, willing himself not to beg for something more. "Mmm, still not saying a word, are we?" she asked, punctuating her question with a sudden grasp of his shaft. "In this relationship, we ask for what we want. If not, then we are punished." From her back pocket, she produced the scariest, black-leather riding crop Harvey had ever seen. He had no idea how he hadn't noticed the thing before, but now that he was staring down its stick, he wasn't sure he really wanted to see it at all. "Do you understand?"

"Y-yes ma'am."

Smack! His left nipple was suddenly made of lightning. "What did I ask you to call me?"

"R-ruby..."

"That's right." Her fingertips massaged away the hurt. "Now, I think there was something you wanted from me? Something involving... this?" Ruby's lips hovered close to his tip, her hot breath making him close his eyes with anticipation.

Harvey nodded, then quickly said "Yes!" when he felt leather press into his thigh. He could feel her heavy breasts settle on each of his hipbones.

"Tell me what you want."

"C-could... you suck me?" He was instantly rewarded with delicious heat wrapping around his cock. Her tongue stroked the backside of his shaft and swirled around his tip. While her lips caressed him, she held her breasts around him and let her warm skin hold him. She stopped altogether much too soon, sitting up and briefly touching herself before standing and letting her thong slide down her long, curvy legs and kicking it off her ankles.

With delicacy, she straddled his hips again and took him in her hands. "I'm going to fuck you," she said bluntly. "Do you want me to?"

"Y... yes."

"Ask nicely."

He gasped as her lips rubbed against his head. "P-please."

She complied, letting him slide inside her so slowly it made his toes curl. When he felt her clench around him, his head fell back and he thrust upwards to feel as much of her as possible. Ruby moaned softly, rising and falling again. He was better prepared for the sensation this time, but when his eyes closed, he still saw stars. Once again, she stopped far too soon, an actual whine escaping him before he could clench his teeth.

"Now, I'll tell you what I want." She untied both his hands, allowing him to sit up. "I'm going to let you fuck me again and this time I want you to fuck me as hard as you can for as long as you can. Understand?" She didn't hesitate for a moment, but promptly turned around so her back was to him and slammed her weight down.

His mind felt like it was made of fire. Instinctively, his hands grabbed her ass and helped to guide her erratic strokes. Soon, he bent his knees and lifted his back to thrust more deeply. Harvey didn't last much longer past that point- his breath was ripped away by the urgency of his release- but his knees held him for several more seconds before he collapsed.

He was dully aware of Ruby's weight lifting away and off the bed. Eventually, his breath became calm and he was able to open his eyes to see her at the door, fully dressed. "It's been fun, sweetheart, but I've got places to go and money to earn tonight." She winked and blew him a lipstick-y kiss before opening the door and making to leave.

"Wait!" said Harvey desperately, "Aren't you going to untie my feet?"

"Hm... nope! Goodbye!"Slam.

Maybe he wasn't going to live this down after all.