Special Order Pt. 01

To jump straight to the sex, search for XXX and start after that.

Literal trigger warning. This story has guns. They aren't part of sex, but they're part of the story backdrop.

Yours,

Virginia O.

***

Jason looked out the window of his home office blankly. May was last month where Texas was granted any reprieve from the oppressive heat, and the reprieve was nearly over. Dallas wouldn't see any real end to the summer until sometime after October.

With a wife, kids, and owning his own business in a white collar, one might think that Jason was perfectly happy. People aren't made that way, though. Sometimes they want something different. Something new. Jason's life was picture perfect, but not nearly naughty enough for him. He wanted something very new and extremely naughty. Especially now, cooped up in the house with his family day after endless groundhog day.

He knew what would satisfy his hunger that bordered on need. Her name was Kelsey. Young, blonde, and with enormous tits. They'd been matched through a service. He hadn't touched her yet, but he was anxious to, social distancing be damned.

Virginia's Service connected people with mutual, sometimes taboo interests. Kelsey wanted to be with an older man, and be taken past her limits in bed. She had reluctance fantasies, wanting to be controlled and she had never had that experience outside of fantasy. She had a lot of hesitation about finding someone who would meet her needs without betraying trust.

Through Virginia's Service, Kelsey had posted what she wanted and how she wanted it. Among many others, Jason sent her a message, and Virginia's gave her his email address. A search of his email address quickly provided a lot more information than it seemed anyone would feel comfortable giving a stranger, especially considering the nature of the service, but maybe Jason was more trusting than most. Whatever the reason, it allowed Kelsey to match a face to a fantasy. He was middle aged, white, and attractive. Having a real person to consider went a long way toward personalizing the potential passion, and Kelsey thought a great deal about it before making contact. How they could meet each other in a city under orders to stay home was a logistical issue luckily overcome by her job. It was Friday, and she was able to go back to work.

Jason's days had blended together to an enormous extent, weekend or otherwise, and for 2020, there was nothing all that special about him in that. It was Friday, though, and he was going to see Kelsey in person for the first time. He put on his shoes and picked up his range bag as he opened the front door and started down the steps. The shooting range was across town, and not the one he normally went to. He's always meant to try it out, and now he had more than enough reason to. His fantasy had been given the breath of life.

By the time he got to the range it was almost closing time. He walked in and immediately up to the counter where Kelsey stood. She recognized him instantly, and blushed. "Hi Kelsey."

"Hello." she cleared her throat and darted her eyes.

"Excuse me?"

"Hello...sir."

"Good girl." He watched the blush spread and flush her cheeks. He was grateful he wasn't as fair-skinned as she was, or his attempt to look stoic would probably fail. "Nervous?"

"No."

"Liar. No what?"

"No sir. I'm sorry. No sir."

"You're still lying, but it's better to tell a lie with proper manners. You don't naturally have proper manners, do you Kelsey?"

"Uh...I don't know. I mean, I don't think I'm rude or anything. I don't know." Kelsey heard Jason clear his throat slightly and quickly inserted "sir", as they'd discussed she would on the phone.

"Do you remember our phone calls, Kelsey? Because it sounds like maybe you don't. Communication is pretty important."

"Yes sir. I remember. I'm nervous and I'm sorry for that, sir. I don't have formal mannerisms, but I don't think I'm rude... sir."

"Okay. At least we have something to work on. Do you have a lane available?"

"Yes sir. I reserved one for you...sir. Do you, uh..." Kelsey was a nervous wreck, and it was obvious. Jason got hard just knowing that she was nervous because she was thinking about him fucking her. Touching her. Doing whatever he wanted with her.

"Do I what? Think before you speak, girl."

"Yes sir." She took a deep breath as Jason looked down at her with a slight grin on his face, which she returned. "Do you have your own targets or do you need targets?"

"I brought my own. Show me my lane."

As she walked him to his lane, she let him know they were closing in half an hour. As a special customer, his reservation had been extended. She told him she would come back after closing to make sure he had everything he needed, and still stuttering over some words but remembering to say "sir", she left him to his practice. The first 15 minutes he spent shooting worse than he had in 20 years. He replaced the target so she wouldn't see how clearly nervous he was. God she was gorgeous! Porcelain skin and a huge rack, both of which looked wonderful on the body of an 18 year old. Oh, his cock ached for her. His mind focused on the range and reconsidered whether it was the best idea to shoot so distracted. Men will take enormous risks for both girls and guns, though. He hadn't held either in his hands for too long.

Kelsey watched him from the corner of her eye as she performed closing duties. He was good looking, but that wasn't where his appeal was for her. His voice held such command. She wanted to follow it. When they first talked on the phone, she felt sure there was a good match. Meeting him in person she was no less sure, but she was much more nervous. She wanted everyone to leave as quickly as possible so they could be alone together. At the same time, she was terrified. Her experience had been limited and vanilla until this. So far it had only been talk with Jason, but tonight they planned on a lot more. She didn't know what his experience was, not exactly, but he was more than 20 years older than her, so he certainly had enough. She didn't want to disappoint him.

Kelsey's affinity for older men had its beginnings in her puberty. She was an early bloomer,and it came with a lot of attention from older boys. Then, in her late teens, she had a few friends that saw older men. One of them gave her a lot of details about their relationship. More details then she asked for, but not more than she wanted. He'd had money, and lavished her friend with gifts. She called him her sugar daddy, leading Kelsey to Google the meaning of that, spending hours lost trying to decipher what exactly a Sugar Daddy was. She concluded that it was whatever was agreed to. She was tired of having boyfriends that couldn't last more than a few minutes in bed, even if they could get hard again and have sex multiple times a day. She wanted it to last. She wanted their attention to last.

A sugar daddy that would fulfill her fantasies seemed ideal, and that's what she was looking for when she went to Virginia's Services. Jason shared her sexual fantasies, and was willing to discuss giving her an allowance, but he insisted she do homework that he would assign to her. Not having to do homework since she wasn't in school anymore was perhaps her favorite part of being an adult, but she agreed, thinking it would probably be erotic. The homework he assigned her was not at all arousing, though, and she was confused by that.

After the last customer left, Kelsey went to Jason's lane. He had stopped shooting, and was taking down a target he could be proud of. Noticing her, he said "Ready?" to which she nodded before remembering how she was supposed to answer him.

"Yes sir."

"Sit. Wait for me to be ready." Kelsey turned around to go get a stool, but was stopped by Jason's hand around her wrist, his face close to hers as he pushed her against the wall. "I told you to sit."

"I was going to get a stool." Kelsey's throat felt like there was a lump in it and her pulse quickened. He was so much stronger than her and...now they were alone. She lost confidence.

"Did I tell you to get a stool?" Kelsey didn't answer, but her eyes grew wide. "Ok. Kelsey. Breathe. Deep breath." Jason let go of her and backed away so she was no longer pinned to the wall. She laughed nervously and took gulping breaths. "I have my work cut out for me with you, haven't I?" Jason asked.

"I'm sorry. Sir..I...am thinking before I speak, sir. I didn't think I'd be so nervous. You're really big."

"You don't know how big I am yet. It is big, though. You'll like it."

"I don't mean that. I mean you're really tall and you're a lot stronger than me."

"I'm not particularly tall. You're incredibly short."

"Right. Sir. Yes...sir. My heart's racing."

"It's supposed to be. That's part of a point. You need to keep breathing, though. You also need to remember to end your sentences with sir or other agreed upon titles. Did you think I wouldn't take your breath away or make your heart skip a beat? I will. I absolutely will."

"I didn't expect it to feel this intense already sir. I think I'm scared."

"Your adrenaline is pumping. That's not necessarily the same thing as fear. I'm not going to hurt you. Well... not beyond what we've agreed to. Are you wet?"

"I don't know."

"Check. Unbutton your pants and check." Kelsey nervously fumbled with the button on her jeans, which suddenly seemed impossible to unbutton. Eventually she managed to get them open and unzipped. She reached her right hand into her panties and her facial expression turned into one of utter shock.

"Woah."

"That wet, huh?" Jason moved forward again, pinning Kelsey's left wrist above her head, pressing his body against hers, and her body against the wall. "Do you want more of that? Do you want me to turn you on?"

"Yes sir."

"Then learn to follow directions. Be a good little daddy's girl." He kissed her earlobe, and whispered in her ear. "You belong to me now. Sit." Jason moved back slightly and Kelsey slid down the wall, sitting on the floor. "Take your hand out of your pants and tell me about your homework"

"Oh. My. God." Kelsey said as she looked down at her dripping hand. She looked back up at Jason and smiled, big and not half so bashful as she'd been since he came in.

"You like that?"

"Yes Daddy."

"Good. Behave and talk about your homework."

"I didn't like it." Kelsey blurted. "Sir."

"You don't have to like it. You just have to do it. Why didn't you like it?"

"Can we skip to...the sexual part? Please?"

"No."

Kelsey sighed. "Fine...sir. It seemed invasive."

"You want me to be invasive. That's not why you didn't like it. Why didn't you like it?"

"It feels inappropriate."

"Wrong again. You want to feel inappropriate. Why didn't you like it?"

"It's boring. Sir."

"Almost. Why really?"

"It's embarrassing. Sir."

XXX

"There you go. Honesty works with me. I like honesty. It turns me on. Here. Taste it." Unbuttoning his jeans, Jason surprised Kelsey. He pulled his cock out, precum glistening off the end. She gasped at both the size of him and the strength of her own desire pulling her toward him "Stick out your tongue and taste how turned on I am." He bent down and rubbed the precum onto her tongue, then put himself back in his pants. "Good girl."

"Give it back!" Kelsey's tension had reached a breaking point. She heard how ridiculous she sounded as she screamed it, but couldn't stop herself. Jason grabbed her around the chin, pulling her to a kneeling position, and slapped her across the cheek, though not very hard at all. She heard him laugh as he did it, and then he slapped her across the other cheek.

"Give it back? It doesn't belong to you, does it?" Kelsey's hair was in her face and she looked down, embarrassed. Jason pulled her chin back up to face him. "Does my cock belong to you?"

"No Daddy." His left hand wrapped in her thick golden hair as his right hand pulled her shirt down, exposing her bra.

"Be specific, Kelsey." He pulled her up to a standing position, and her hands naturally went to his chest. He pushed aside the hand in the way of his access to her bra, which he pinned behind her ass. He pulled down her bra, and leaned back to take a long look at her. Her shirt and bra made an impromptu shelf for her bosom to rest on, and he made a mental note to give Virginia's Services 5 stars as he took in the sight of her. She was quite a find, and he was sure she didn't know it, making her all the more fun. "Specific." He pinched a nipple as she winced and panted. He pulled her to the tip of her toes and kissed her neck. "Speak."

"Your cock doesn't belong to me Daddy! Your cock doesn't belong to me sir." Her chest heaved. Jason decided to let her catch her breath a bit. Letting go of her hair, he pulled her wrists up and put her hands on her head. She intertwined her fingers, and he patted her hands there to indicate she should keep them on her head. As he sucked on each nipple in its turn, he smiled inwardly at the panting and perfectly lovely girl he would possess.

"Keep your hands there baby girl. I need to see how wet you are."

"Very Daddy. Very wet. I need you inside of me please."

He pulled her pants down and she stepped out of them. Putting a hand in between her thighs, he nudged her so she spread for him. She was wet, and slippery. She had shaved as he told her to. Brought to his knees by the pull of her scent, he spread her labia with his thumbs and licked at her juices as she moaned. "I like to hear you beg for it. You have no idea how good you're going to feel belonging to me. You're a good girl, aren't you? Are you a daddy's girl?"

"Yes. I'm a good girl. I'm a daddy's girl. Please fuck. Oh god please."

Jason walked the few feet needed to grab a stool, and brought it back, setting it in front of Kelsey a couple of feet from the wall. "Come around here. Bend over this while facing the wall for your daddy. That's my girl."

Kelsey's feet didn't touch the floor, and her hands didn't either. she held onto two of the stools legs, anxious and anticipating Jason's entrance. Instead of entering her he asked her a question. "Did you bring your homework to turn in?"

"Umm..yeah. Could we...?" before she finished her sentence, Jason's hand came down on her ass. "Sorry Daddy! Yes. I brought my homework. It's in my pants." Jason picked her pants up off the floor and pulled out a folded piece of paper. He put the piece of paper in his own pants, replacing it with $200.

"Next time, I want it to be as presentable as you are. Understood?" His hand came down on her ass again, and again, and again. She'd taken ten swats before he gave her the opportunity to speak. "Understood?"

"Yes Daddy! I'm sorry Daddy. Yes! I'll...I'll bring presentable homework to you." He gave her a minute for the stinging in her backside to go down. It was a minute he took to review her homework. With his right hand he rubbed her ass cheeks, holding the paper in his left to read. When her breathing changed from labored and loud to slow and deep, he knew she was ready. He put the paper back in his pocket, then pulled his pants down. He took off his shirt and spread Kelsey's thighs with his hands, adjusting her forward so her pussy entrance was easiest to access, but her center of gravity was thrown off and her legs came up off the stool.

As his cock entered her, her body was jolted. She moaned, and her back arched. She put her hands up on the wall and a long "Yeeeees." escaped her lips in between his first and second thrust. In the second thrust she realized he hadn't entered her fully the first time, and she was shocked by how deep he was. It elicited involuntary guttural noises from her, and she felt her pussy clench around him. The heat he had brought to her crotch spread out through the rest of her body. She felt dizzy and overjoyed. He pumped faster and harder. He grabbed her by the hair, pulling her head back and her body entirely off the stool. He wrapped an arm around her to keep her on his cock while he repositioned. Sitting on the stool he pulled her legs together toward her tits, folding her in half. "Oh my God. Thank you Daddy. Oh my God oh my God oh my God." she was tiny and using her body to jerk off with was nearly effortless for him. He continued holding her by the back of her thighs with her back against his chest. He could hear the breath knock out of her lungs as he pumped into her, and placing his head next to hers, he looked down to see her tits bounce with his thrusts. She was a sex toy like nothing else he'd ever experienced. He moved her up and down on his shaft again and again until she came, and then he kept going until she begged him to stop. "Oh. I can't. Please stop. It's too much."

"You can take it for your daddy, can't you?"

"Oh! I want to Daddy. It's so hard. Oh God you're huge. It's so hard."

"Okay. You've been a good girl. Suck my cock until I cum." He let her off of him and back in control of her own movements. She latched onto his cock gratefully, quickly bringing him to orgasm, which he did in her mouth as he held her at the back of her head. "Make sure you swallow all of it, you beautiful little slut." She gagged for quite a while as he came. It was a huge load, but she managed to take it, and he held her head in place to ensure she got it all.

When he finished, they both dressed. Kelsey looked shy again, and he could tell her reaction had surprised her. It was unlike any experience that she had ever had, too, but very much like experiences she had fantasized about. She was so embarrassed by it that she was happy when he brought up the subject of her homework.

"Good job on your personal spending report. For next week's homework assignment, I want a detailed break down of your expenses that aren't fixed. Up to five categories, including other, and up to three subcategories. For example, categories could be food or shopping. A subcategory of food could be fast food and for shopping it might be gifts."

"Why do you want to assign me all this money related homework? it's not very sexy, you know... sir."

"Financial literacy is very sexy you know...baby girl. My financial literacy is why you just swallowed my dick an hour after meeting me." Kelsey turned beet red with embarrassment. "I want to give you money because it turns me on to provide for you. I want you to learn about money because it turns me on to know you can provide for yourself. I want to train you sexually because it turns me on to have you desperate for my cock. I want money, power, and sex. Don't you?"

"Doesn't everyone?"

"Exactly. Now come kiss me goodbye." Kelsey's eyes lit up and she hurried to him asking if she'd done well. "You're a very good girl. Be good until next time."

"When is next time? Soon? How about tomorrow?"

Jason choked on his laughter. "You are 18. That's adorable. No. Not tomorrow. Next week. I'll email you."

She hoped he'd email the details of her assignment, and wondered what he'd want next time.