A Purchased Evening

Lindsay had left the restaurant, her purse feeling ten pounds heavier with all the cash he had given her. For the first encounter, he had paid the two-hour rate, which was $300. Some of that she had to give up to the firm, which was usually a bigger deal because they took 50% of what she would earn. She also fingered the second envelope open, still amazed at the bonus she had apparently "earned," but she separated out the firm's cut and combined the rest into a single envelope, burying it in her purse.

She stopped by the firm, dropping off their share of her money before heading home. It was already late in the day, and she didn't need to take another client now, with the bonus she had gotten.

She arrived home and showered, taking extra care to make sure she was clean-shaven and was clean, everywhere. She got out of the shower and threw on a pair of leggings and a tank top. She was getting ready for bed when her phone dinged. Remembering he said he would text her, she picked up her phone, and found a picture of a girl in a tight white skirt that barely came down past her ass, wearing a crop-top t-shirt and a pair of heels. The text that followed made her heart skip a beat.

"Your outfit for tomorrow night. 8pm. No bra or panties. Bring spare clothes to go home in." An address followed the text.

She immediately went to her closet and found what she needed to match the picture he sent. She laid them out on her desk, and packed a small duffle bag with an extra set of leggings and a sports-bra, as well as a set of tennis shoes that would be more comfortable than the heels she had to wear.

Finished, she decided to call it a night. Tomorrow was going to be a lot of fun, if that picture held any truth to it, and she was gonna need a good night's sleep.

* * * *

Matt moved around the house, ensuring everything was clean and in order throughout the day before Lindsay arrived. The house was modest and small, but then again a single guy living on his own didn't need too much. The spare bedroom had been turned into his "fun-room," as he liked to call it. It's most recent addition was a set of cuffs anchored into the wall at various points, for what would be a small human figure to be cuffed at the hands and ankles with the arms and legs spread. He had requested a petite woman, not someone very tall, and Lindsay certainly fit the bill. He came back to the fun-room one last time and picked up a jeweled butt plug, feeling the cold steel of the plug, smiling as he imagined it going into its home as he tried to warm it with his hand.

The doorbell rang. He picked up a small bottle of lube and headed towards the main room, careful to pull the door shut behind him. Setting the lube down on an endtable by the couch, he held the plug in his hand as he opened the door. Lindsay had done a good job matching herself to the picture he had sent, a low whistle escaping his mouth as he traced the curves of her skirt with his eyes.

"Hi," she said nervously, the small duffel bag hanging from one of her hands as she smiled at him.

"Welcome, Lindsay, to my humble abode," he said charmingly, stepping back to allow her to enter. "You can put your extra stuff there," he said, indicating a table by the door, watching as she picked up an envelope of cash he had left there earlier and slid it inside her duffel. She turned to face him.

"Do I look okay?" She asked, turning around so he can get the full view of the outfit, the muscles on her legs standing out in the heels and skirt. She heard another whistle as she came to a stop.

"Yes, Lindsay, you look wonderful," he said, pausing slightly. "There is one more addition to your outfit I need to make, though. Remember when I said that you would be mine when you are here?"

She swallowed and nodded. "I do remember that."

He pointed to the couch sitting in the middle of the room. "Hike your skirt up and bend over the couch for me, Lindsay," he said, opening his hand to show her the jeweled buttplug he had been holding. Lindsay's eyes fell on it, her breath hitching in her throat. "That's... for me?" she asked quietly, still not moving.

He laughed. "Well, its certainly not for me!" he said with a smile before gesturing again to the couch. "Let's go little lady, I got plans for us tonight,"

That got her attention, and got her moving towards the couch. She walked up behind it and, taking a deep breath, pulled her skirt up over her ass, exposing her tanned, bare ass as she was obediently wearing no underwear. She bent forward over the couch, putting her hands down on the couch cushions to try and steady herself, looking over at him just in time to catch his nod of approval.

"Very nice, Lindsay," he said, picking up the bottle of lube from the end table. "I can always appreciate an obedient slut," he said matter-of-factly, making her blush deeply as she held herself in place.

He kicked her legs a little further apart, taking the tube of lube and letting a few drops of it fall down at the top of her ass crack, watching it run down between her cheeks. He put a few more drops on one of his fingers, tracing the line between her ass cheeks that the lube had run down with his finger before finding her anus. He turned his finger around in place, touching her sphincter but not pressing into it yet. Seeing her body shudder, he smiled, pressing forward with his finger. "Best to just try and relax yourself, miss Lindsay, I am lubed but you are also very small and," feeling his finger penetrate her, her anus squeezing his finger tightly as he pushed it inside, letting it slowly sink down to the knuckle, "very tight," he finished, hearing her groan as he invaded her asshole.

Lindsay had only had anal sex once before, and that had been a bad experience. The cock was too big, it hurt a lot and she just generally didn't want to remember it. Still, she had remained interested in it, just never had a lot of chance to explore it. Now, she felt herself get penetrated by a single finger, and the feeling made her entire body shudder as she felt his finger sink deep inside her.

He pulled back, almost letting his finger escape her asshole before sliding it back again. "I've gotta get your asshole warmed up a little bit," he said. "It's not good to just go in raw when it comes to anal sex, especially with a lithe, petite young woman," he said. "Training is key, for something like this," he said, repeating the same back and forth motion with his finger. He set the plug down on the edge of the couch, grabbing her hips with one hand and pulling his finger out altogether. "Want to try two fingers?" He asked, grabbing the lube and spilling a little more onto his index and middle finger, another couple of drops in between her ass cheeks.

She watched as he lubed his fingers up, before nodding obediently. "I am willing to try it," she said as she felt the two fingers press against her asshole, already slightly loosened from having the one inserted. She groaned again as he pressed inside her, his fingers spreading her sphincter as they penetrated her, again sinking all the way inside her, making her body shiver in pleasure as she held onto the couch.

"How are you feeling about this, Lindsay,?" he asked quietly as he began slowly finger fucking her ass.

"It feels... good, sir," she said, not knowing exactly where the "sir" came from, but letting it go. "I've always enjoyed the thought of anal sex, but I've never.... Ahhhhh.... Had a good experience with it."

"Really?" He said, finally withdrawing his fingers, eliciting a whimper of frustration from her. "We will have to change that," he said, finally picking up the plug and dripping some lube onto it, spreading it across the surface of the plug with his already-lubed fingers. "Ready for something a little bigger?"

She nodded, having watched him lube the toy. She braced herself, feeling the tip of the plug being pressed against her asshole. She knew it was flared, smallest at the tip with a fairly wide body at its widest point, with a little pedestal on the end, holding the jewel she saw earlier. It really was quite pretty, she thought, before her thinking was interrupted by the pressure of the plug being pressed into her ass.

Matt pushed the plug forward, watching it slowly begin to disappear into her ass, her sphincter stretching to accommodate the plug. He watched with a satisfied smile, hearing her deep moan as the widest part of the plug slipped into her ass, swallowing everything except the little heart-shaped jewel on the end of it.

He tugged on it once or twice, making sure it was secure. He looked at it and noticed the plug was sideways, so he twisted it so the heart was facing upright, hearing another deep groan come from the blonde bent over his couch before stepping back and grabbing his phone off a nearby table. "Reach back and hold your ass cheeks apart for me, Lindsay," he commanded, smiling as he saw the full shape of the jewel come into view. He took a couple quick pictures before walking back up to her, pulling her back to a standing position. "You can fix your skirt," he said, eyeing his phone.

She quickly pulled her skirt back down, the plug giving her a sensation of fullness that she really enjoyed. "What's on your phone?" she asked quietly.

He turned the phone to show her the picture he had taken, watching her face turn beet-red as she looked at the toy, clearly visible with her hands holding her ass cheeks apart.

Seeing her reaction, he spoke. "It would seem, Lindsay, that we are going to have a lot of fun together." She giggled and nodded as he grabbed her hand.

"Come, let's take a short tour of my house. He led her through the living room towards the hallway that held the back of the house. He opened each door in turn, so she could see the layout. "Bathroom," he said, pointing it out. "I stocked it with various fem-care products, I don't know what all you might need so I kinda guessed but if there is ever something specific you want me to keep on hand, just tell me."

She nodded, each step making her pussy throb now as the feeling of fullness intensified as she walked through the house in the heels she had worn.

"My bedroom," he said, opening the door on what was clearly a bachelor's living room. At least it was clean, she thought to himself, eyeing the four poster bed in the middle of the room. He closed the door and led her onward, a full blush creeping into her cheeks as the plug made her pussy throb again.

He opened another door but held an arm out to make sure she didn't enter. She peered inside and saw a set of stairs leading down. "Basement access, washer dryer, furnace room, nothing that exciting," he said with a shrug, closing the door again and leading her onward to another door, this one with a sign posted outside. "Enter at your own risk." She eyed the sign carefully before looking back at him. "And this one?" she said carefully.

"I call this my 'fun-room,'" he said with a smile, opening the door to what was ostensibly a bedroom, although there was no actual bed. In one corner, a sawhorse stood, cuffs hanging down un-used from the side of it. One wall was lined with a shelf full of toys, with a second shelf of whips and floggers underneath it. In another corner was an array of smaller toys, each with four cuffs, clearly meant to bind a person in different positions. She swallowed as he stepped inside, indicating the room.

"We will spend a lot of time here, most likely. There are a few things in here we will get to tonight, but for now," he said, grabbing her hand and leading her back out to the hallway. "Back to the living room," he said, leading her back out to where the "tour" had started.

He sat down on the couch she had just been penetrated on, beckoning her forward with his hand, indicating she should stand in front of him.

"How are you feeling, Lindsay?" he asked, curiously, looking up at her.

She considered, her weight shifting a little side to side as she was growing to enjoy the feeling of the plug inside her. "I've never had a toy like this before," she said quietly. "I already feel like I'm on fire," she said with a shy laugh.

He laughed, "well, I'm glad you are enjoying it, but now it's time we get down to business. He pointed to the floor in between his legs. "Down," he said commandingly.

She obeyed, glad to be off her heels even though it meant getting onto her knees. She watched him carefully as he unbuttoned his pants and pulled them down and off, along with his boxers. His cock wasn't hard yet, laying softly against his balls. He pulled his shirt off, but her gaze was locked onto his dick, watching it twitch a little as she stared at it. "I think you know what to do," he said quietly.

She moved forward, her hands sliding up her thighs to his groin, grasping his flaccid cock in one hand, gently squeezing it as she lowered her face to it, letting her tongue slip out, swirling it around the head of his cock, feeling it throb in response as she let go of it, sucking it deeply into her mouth. She could feel it starting to fill with blood but she sucked deeply and enthusiastically, his soft cock sliding easily between her lips as he rested his head back, one hand slipping into her hair gently as she got him hard, one of her free hands coming up to start playing gently with his balls.

She could feel his cock growing quickly in her mouth, his hand in her hair kept her from sliding all the way off of it as it pressed against the back of her mouth, encouraging her to keep sucking.

He felt himself growing almost fully hard in her mouth, her kneeling position only allowing her to take so much of his cock before she had to back off of it. He let her continue for a few more minutes, listening to the slurp and gurgle of her sucking him off before he wrapped his fingers tight in her hair, letting her push herself down on his cock before seizing control of her head, holding her in place with her mouth wrapped around the front half of his cock. She immediately tensed, but continued her ministrations on his cock as he held her in place.

With a deep groan he finally pulled her head off his cock, pushing her backwards against the floor as he stood, his hand still wrapped tightly in her hair. He looked down at her, head twisted slightly sideways but still keeping her eyes on his cock. He smiled.

"You have excellent skills with my cock," he said, coming to stand directly in front of her now, his cock pointed at her face, her hair held tightly in his hand. "But do you remember what I said at the restaurant?"

She looked at his face now, trying to recall their conversation over dinner. "You said you wanted me," she said vaguely.

"Yes.... and no," he responded with a dark smile. "I said I was going to try to put my dick through you. The first part of that begins now," he said, pulling her head forward onto his cock, his fleshy tip pushing apart her lips, feeling her jaw open for him.

He pushed forward, feeling his cock slide over her tongue and hitting the back of her mouth, letting her feel the shaft throb in her mouth as it occupied the whole of her mouth. He could feel air being drawn over the tip of his cock as she breathed through her nose.

"I am going to use your mouth now, slut," he said matter-of-factly, "and don't bite," he said, pushing into her throat a little, enough to feel her body tense before withdrawing, leaving just her lips wrapped the crown of his cock before plunging back in, careful not to choke her completely, but feeling the tip of his cock enter her throat again, holding her head in place now as he buried as much of his cock as he could in her mouth, feeling her tongue running over his shaft as he held her place.

He slowly began face-fucking her, his cock withdrawing and then driving back into her mouth, careful to let her breathe on occasion but forcing her to spend as much time as possible with his cock buried at the back of her mouth or pushing into her throat, feeling her gag several times, her throat closing on his cock as she did.

After a few minutes, he looked down and finally noticed the line of drool that had escaped her mouth, dampening her neck and the top she wore. He smirked, slipping his cock deep into her mouth, pressing gently on the opening to her throat, before speaking.

"Look at me," he said, waiting for her eyes to move up to meet his. His cock throbbed at the sight of her eyes, framed by the cock jammed deep in her mouth. "I've been told by previous partners that I cum a lot," he said slowly, feeling her tongue slipping along his shaft as he held her mouth full. "All I know, myself, is I want to cum on that pretty little face of yours. And in that tight little pussy. And in that even tighter asshole of yours." He sighed, enjoying the feeling of her mouth around his shaft, but finally withdrawing, letting her breathe normally as her mouth was suddenly free of his cock.

He walked over to the end table and set a collar down on the couch, sitting next to it. He looked back at Lindsay, "There is one other rule to the 'fun-room' I didn't tell you before," he said gesturing to the collar. Now Lindsay could it was black leather, with a gold-threaded inlay that proclaimed, quite largely, "SLUT".

"This collar is the only article of clothing you are allowed to wear in the fun-room. And you have to earn it if you want it." He let the sentence hang in the air.

"Earn it?" she asked quietly, kneeling before him, her eyes on the collar as she waited for an answer.

"First, strip," he said, motioning to the dress and top she wore. "You can leave the heels on though," he said with a touch of fondness. "I like what they do to your legs," he explained needlessly.

She stared at him for a minute, but feeling the throb of her pussy radiating throughout her lower body, the damned buttplug making her feel so full, she stood and stripped. It wasn't necessarily meant to be sexy, but he whistled appreciately as she took her top off, revealing her large B cup breasts, standing firmly at attention before wiggling the skirt down her legs, stepping out of it. She picked up the clothes and set them with her other belongings before returning to face him.

"Good," he said slowly, enjoying her walk across the room, his cock throbbing in anticipation of what is to come. "Now, come wrap your mouth around my cock again, as deeply as you can. While you are doing that you need to hold your hair away from your neck so I can fasten the collar around your neck," he said with a smile.

Her eyes fastened again to his cock, and she immediately sunk to her knees, crawling forward towards him and putting her arms in her lap. She closed her hand around his shaft, feeling the moisture from her mouth still dripping off his cock as she stroked him. She smiled at him one more time before enveloping his cock in her mouth, reaching back to hold her hair up like she was trying to put it in a ponytail as her cock moved back into her mouth, the tip of it brushing against her throat again, as she held her hair in place.

Once his cock was deeply embedded in her mouth, he reached down and picked up the collar, taking his time but leaning forward slightly, his cock expanding a little bit in her mouth as more blood was pushed into it, feeling him slip the collar around her throat, buckling it in place. It wasn't tight, just comfortable around her neck, but her cheeks burned a little, the image of herself in that collar playing in her eyes as she felt it lock in place.

He leaned back, admiring the sight of her with her hair held back, collar in place and near-gagging on his cock before giving her a quick thrust of the hips that made her gag and sent her backwards off his cock. She went back onto her hands, giving him a cross look but he barely paid any attention, standing up and coming to stand in front of her, his hand running through her hair gently as she looked up at him.