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."
