She Deserves It Ch. 01

Jack was unreadable. When I didn't speak more, he grinned. "Oh, thank god I thought you were going to resign!"

"Uh," I started, but he kept rolling.

"Here," he pulled out an envelope and tossed it across the desk. I tried to stop my hand from shaking as I took it. My eyes widened as I read the numbers.

"Um, wow."

"I take it you like it then?" Jack grinned. "It's well deserved. Every penny."

"I—, wow thank you sir."

Jack smiled and pulled out a bottle of whiskey and two glasses. "A toast a think?" I found myself taking the glass. "There's more, but we can't put it in writing yet. Steve is retiring in three months. I'm going to move up and you're going to take my position."

"What?" My head spun. "What about Walter?" He was the long standing second of the division and had far more experience.

Jack shrugged. "He's not interested. He's good at what he does and comfortable. I think the brass have offered him a promotion half a dozen times and gotten turned down every time."

"Wow..." I was stunned.

"Good timing, right?" Jack asked.

"What do you mean?"

"Well, you and that intern, what's her name, Riley? That's a girl that needs spoiling."

"Yeah..." I laughed along with him, but on the inside nervous energy quivered. "My friend Dan was warning me about girls like her. About how I could never slack off because there was always someone better waiting."

Jack raised his glass to that. "How the hell did you even end up with her? I mean no offense, but she might be out of everyone's league here."

"That's how I feel," I laughed and rubbed a hand through my hair. "Honestly, I just asked her like a normal girl. I was having a rough time of it and felt like I had nothing to lose. So, I just asked her to coffee one day. She seemed almost surprised. Turns out guys are generally too afraid to approach her or have to work themselves up and come off as too aggressive."

"Damn, wish I had thought of that," Jack laughed. "Ah, well."

"Aren't you married?" I realized I probably shouldn't have asked this and cringed, but Jack just chuckled.

"I am and happily! But there is not a relationship in the world that would stop me from tapping that," Jack sighed. "Missed chances and all that."

"Yes, sir," I agreed awkwardly. How was I supposed to respond to my boss talking about my girlfriend like that?

"We're going to hire her, but not in the division. The lawyers want her out of your reporting chain," Jack polished off his drink and started typing on his computer. I took this as a dismissal, thanked him again and left clutching the offer letter.

***

"How did it go?" Riley asked eagerly as soon as I entered my apartment. She was still wearing her coat so she couldn't have been there long.

"Uh, well," I handed her the letter. "It went okay."

Her eyes darted as she read the letter. "Okay? You ass!" She jumped on me, knocking me backwards into the door. "Fuck, I'm so proud of you!" She kissed me hard, her face flushed with excitement.

"Do I get my reward now?" I asked as my cock sprang to attention.

"Later, I want mine first," Riley slid down me and started unbuttoning her coat. She let it drop to the floor.

"Damn, Riley," I gaped at her. Her breasts were framed by a cupless black bra and she had on a garter belt attached to black sheer stockings. I stood there flapping like a fish out of water until she grabbed me by my tie and pulled me towards my bedroom. She started undressing me, staring into my eyes.

I managed to recover my wits. "Uh, this is your reward? Wait, why do you even get a reward?"

She flashed a smile. "You silly boy, I get a reward because without my hard work motivating you, you wouldn't have succeeded." She started working on my pants. "And my reward is two orgasms from this nice needy cock of yours." She smiled as she pulled my dick out and stroked me before backing away.

I quickly bent over to get my shoes and pants off as she settled onto the bed on her hands and knees, her ass pointing back at me. I finally managed to get naked and approached her from behind. He pussy was dripping wet and already open.

"Tommy?" She asked turning to look at me as I rubbed myself against. "Don't be gentle. I need it hard tonight. Fuck me hard."

Finally unleashed I obeyed, grabbing her hips and easing myself into her. A few short thrusts and she was taking me fully. I hunched over her, and wrapped her hair in my hand, yanking her face around so I could see her pleasure.

"Oh, oh yes, fuck me," Riley gasped. Her words turned to moans and when I let go of her hair she fell forward. I followed her and started spanking her ass. "Ugh, yyeeessss! I'm gonna cum!"

She groaned and her back arched. Her face was turned to the side and I watched her eyes scrunch and her lips part in pleasure. The teasing and the sex were too much and I lost it, cumming with her. We fell together onto the bed, still joined together. She leaned back and kissed me giggling.

"Ugh, so good, I really needed that!" Riley kissed me and rubbed my cheek. "You have no idea how hot teasing you gets me."

"HHmmm," I said happily. I felt my cock softening and when it popped out Riley flipped over on her back and looked down.

"You came? I thought I asked for two orgasms for my reward," Riley pouted.

"Sorry, you had me too worked up! If you wanted me to last longer you should try being uglier and worse in bed," I said with a grin.

"Flattery will only get you so far and it won't get you out of this," Riley leaned back and pointed at her pussy. "Eat me."

I leaned on my elbow and looked at her pussy, which was dripping my cum in a steady stream. Her teasing had worked me up and I had left a big load in her. I gulped. "Uh, you're just teasing right?"

"Eat. Me."

I didn't move and Riley's eyes narrowed as we stared each other down.

My cock is what did me in. The look on Riley face was one of absolute certainty that I would obey and that she deserved it. A slight smirk appeared on her lips when my cock twitched and I knew I was done.

"Ah yeesss," Riley's fingers played with my hair as my lips and tongue went to work on her messy pussy. "Yeah baby, clean me up. Make me cum." I cringed at the reminder I was eating my own cum out of her, but the soft moans from her and the way she rocked her hips made me realize just how into this she was.

She pushed my head down and I found my mouth positioned right at her entrance as cum flowed out of her. When she was satisfied I had cleaned her, she moved her hips to bring her clit beneath my tongue. Riley didn't need the direct stimulation for long, and within a few minutes she was pushing my head away and giving me a warm smile.

"That wasn't so bad was it? At least some part of you liked it..." Riley let a finger trail over my throbbing erection causing it to jerk and leak precum. She pulled me in for a kiss and then giggled. "You taste like cum."

"Yeah right, thanks a lot," I replied sarcastically, upset that my cock gave me away by twitching in her hand at her teasing.

"Aww, poor boy," Riley pulled me onto the bed and pushed me onto my back. "A raise, a hot girlfriend, and crazy sex not enough for you?"

"Riley..."

"How about this?" Riley dropped her head and engulfed my erection.

"Oh!" I gasped. Her eyes sparkled as she looked up at me. Her lips and tongue ran around the head and then she slowly took more and more of me in, massaging the sensitive underside with her skillful tongue. "Oh Riley."

Riley took her time, her mouth stretched around me cock and I struggled to prolong it. She popped it free and used her hand while she spoke. "It's okay baby, you can cum in my mouth. You were a really good boy today, so I think you deserve it."

I have no fucking clue why, but her sweet words, her pretty warm face, and her skillful hand combined to overwhelm any form of self-control I had left. I groaned and she quickly took me in her mouth, cupping and massaging my balls as she drained my cock. I felt like I came forever. The sensation of time returned only when I squirmed as my dick became too sensitive to handle her tongue.

I collapsed backwards as she pulled herself off and slid up the bed next to me. "Fuck, I love you Riley," I said as she snuggled and moved in for a kiss.

I should have seen it coming, but I was relaxed and oblivious until her tongue forced its way into my mouth followed by the load of cum I had just left there. I was shocked and swallowed reflexively only to have my mouth filled again. I tried to pull away, but she had me by my hair, tugging painfully when she felt me move. I lay there stunned as Riley curled up happily next to me.

What the fuck was going on? Why couldn't I stop her from using me like that! The worst part was that as I thought about it my cock started to get hard again and Riley giggled and ran her fingers across it as she drifted off to sleep.

***

"Riley, can we talk about last night?" I asked softly. We were at a small table in an atrium at work that was relatively private, but there were a few people hanging around on nearby benches.

"That was great, wasn't it?" Riley was beaming. "God, that was the best sex of my life!"

I was a bit shocked by her enthusiasm. We had both cum hard. Really hard. But I felt uneasy about it, unsure of where it was headed. "Uh yeah..."

Riley frowned, sensing my unease. "You didn't like it? I knew I should have gone with the red lingerie!"

"Uh, no, the lingerie was perfect," I leaned forward and lowered my voice even more. "It's the... uh, why do you keep feeding me my cum?"

Riley looked confused. "I like it. Because you like it. You get hard again every single time."

"That doesn't mean I like it!"

Riley smiled warmly at me. "Baby, I know it's not manly to swallow cum or whatever, but you don't have to be that way with me. I think it's hot as hell that you trust me so completely." She reached under the table and pushed my hand under her skirt all the way to her crotch. "I've been watching those videos you like. Doing research."

"Whoa, you're really wet," I gasped in surprise as my fingers found her panties. The feel of her arousal drove questions about what videos she thought I liked away.

"Yeah, even talking about it turns me on," Riley giggled and pushed my hand away. "Look, I know it's not something you've done before, but it makes me happy and I know you want it. And I know you want me to make you do it."

I wasn't sure how to respond to this at all. She watched me and I felt myself blush. Suddenly her hand grabbed my crotch and I groaned as roughly jerked my cock. She sipped her drink and smiled as she jerked me hard and fast then suddenly stopped. I gripped the table, my head spinning.

"Do you want to cum?" Riley asked as she packed up the rest of her lunch. I nodded weakly. "Then admit it." She stood and walked away, leaving me wondering what was next.

***

I threw my coat on the back of my couch and reread Riley's text for the twentieth time.

Riley: No jerking off. ;p

"Fuck that," I grumbled. My mind drifted to the video and how Riley had apparently been doing research. Whatever she had found had put twisted ideas in her head, and I wanted to find out what she thought I liked. I pulled my laptop out and quickly found it in my history. The channel was called 'Miss Claire' and when I clicked on her name, I found a few dozen videos.

I clicked on her most popular one and her body filled the screen. She had implants that were a few sizes too big for my taste, but otherwise had a pretty good body. She was wearing a pretty normal looking outfit. Tight jeans and a top that showed a lot of cleavage.

"Hey there dirty boys," her voice said teasingly. "Hope you've been practicing because I'm not going to make it easy for you today!" She pulled out an egg timer. "You're really going to need some good lube handy, so get naked, grab your cock and let's see if you can make it."

The screen faded to black with white text instructions to pause and get ready. I figured I would play along. I unplugged my laptop and headed to my bedroom where I got naked and laid down in bed to resume the video.

Miss Claire pulled out the timer and turned it to twenty minutes, a countdown appeared on screen. "Okay you know the rules by now. No stopping. No cumming. Do what I say."

She smiled sweetly for the camera. "Is your cock nice and hard for me? I want you to get your hand dripping wet with lube and wrap those fingers around your needy little dick."

Her eyes hardened as she spoke. "What's that, you want me to do it? Well, you should have thought about that before you came. I told you not to cum, but you just can't stop yourself, can you?

"But I don't think it's my hand you want, right?" She brought a finger to her lips and ran her lips and tongue along it before taking it in her mouth and sucking it gently. "Yeah, I know what you really want. But do you really think you deserve this?" She made a show of sucking her finger, closing her eyes and working her head like she was servicing a dick.

Her eyes flared open and she froze. "Keep. Fucking. Stroking. I did NOT tell you to stop." I realized I was holding my dick without sliding my hand and quickly started masturbating again, groaning as I played with myself. She was good at this!

"Good boy. Now, I want you to close your eyes and think about that girl in your life and if you really deserve her."

"Oh," I gasped as I imagined Riley. My dick throbbed.

"Yeah, keep playing with yourself. You can't stop, can you? What do you think she would say if she saw you right now? Not every girl is so understanding like me. Do you really think she wants you sitting there naked, alone, playing with yourself instead of pounding her?" She giggled. "I guess if you could pound her properly, we wouldn't be working on your little control problem, would we?"

"HHHmmm, now I know this is going to be hard," she giggled. "But go ahead and start stroking yourself faster. Like you're fucking her just like she needs. That should be her pussy wrapped around your cock. It isn't, but it's okay to pretend, right?"

"Yeah, just like that! Keep stroking! Yeah, now go as fast as you can! Five...Four...Three...Two...One... STOP!"

I gasped and released my dick, a steady stream of precum was oozing from me and my eyes flew open to see Miss Claire's smiling face. "I hope you didn't cum there..." I groaned.

"If you did, you know my rules. Playtime is over and you'll have to try again next time to get your reward. Oh, and don't forget. Good boys always clean up after themselves." She mimed a scooping and swallowing motion, her fingers licking her fingers clean.

"Hhhmm, I'm so proud of you right now! Five whole minutes!" Miss Claire giggled. "I bet you'd really like to see my boobs, wouldn't you? Okay, but you still can't cum and you're only going to make it more difficult for yourself..."

She stood and started to pull her shirt off then stopped. "Oh sorry, I almost forgot! Get that hand back on your cock and keep it hard for me. I'm sorry I have to be such a bitch about it, but you need to trust that I have your very best interests at heart."

I started playing with myself again, sighing in pleasure as Miss Claire slowly slid her shirt up. She caught her breasts with the hem then they bounced free and she giggled. I groaned as her large breasts popped into view and she started rubbing them.

"MMMmm, stroke your cock while you look at my tits? I bet you wish you could play with them. Slide your hard dick in between them until you came all over my face..." She pulled her tits up to her mouth and started licking and her nipple while staring into the camera.

"Too bad!" She released them and leaned forward, her breasts filling the camera, only cleavage and lips visible. "I don't think you've proven you deserve to touch these."

She leaned back and was holding a dildo. It was a huge and realistic looking caramel cock and she smirked as she held it up. "Oh, don't worry, I'll still like to torture yours even if this fills me up so much nicer!"

She stuck the dildo to the table and produced a bottle of lube. She wrapped her fingers around it and started to stroke it, spreading the lube until the dildo was shiny. Her fingers could barely fit around it. I found myself following her actions, copying her pace and how she was playing with the dick. All thoughts of researching Riley's inspiration and why I had started watching this video were long gone.

She was silent as she worked it, staring into the camera as she moved from gentle teasing to using both hands to stroke it wildly. I groaned and grunted as I imitated her. She started laughing as her tits bounced around from her vigorous motion. "Wow ten minutes!" She wasn't letting up and I was struggling not to cum.

"Whew, I could use a break!" She leaned back and I released my cock, groaning. "No, I think you can keep going. It's not much of a workout with yours..." She held up her fingers as if she was measuring a small dick. "Keep stroking for me. Prove that you want it."

"Fuck," I hissed as I wrapped my hand around my dick. She hadn't said how fast, so I was gentle and slow as I watched her stand. She grinned as she unbuttoned her pants, gyrating slowly to imaginary music as she pulled them off her hips.

She had on red panties that matched her lipstick. And she twirled to show off how they clung to her ass, riding between her cheeks. "Look how fucking hard that dick is for me!" Her face was flushed, and I groaned as I realized she was turned on, just like Riley got when she teased me.

"Yeah, keep playing with it. You want me so fucking bad, don't you?" She moved over the dildo and started rubbing it along her panties. "What could I make you do to get your dick where my friend is here?" She reached down and stroked the dildo then held it in place as she circled her hips on it. "I bet you would do anything, right?"

"Well, all I'm asking of you today is about..." she glanced over to the side. "Seven more minutes. That's not so hard right? I mean any loser can last seven minutes."

"But that's just with your hand," she let her fingers slide down her stomach to her panties where they moved in lazy circles on her clit. "Do you think you could last that long in me?"

She moved her panties to the side, and her labia spread around the head of the dildo. "Fuck that thick cock feels good. Sorry it's not you, but why should I settle? You have to prove you're good enough first."

"Ah, yeeessss," Miss Claire lowered herself down. "Fuck yes, watch me. Oh yes watch me on this thick dick." Her pussy spread obscenely around the thick toy and she had to slowly work herself up and down to get it in her. When she rose up, I could see some of her arousal left on the shaft. The view was entrancing I watched wide eyed as she pleasured herself.

"Wait, did you stop stroking?" Miss Claire's eyes shot open and she started giggling. Despite the fact that I was alone, I blushed when I realized that I had again stopped stroking. "Awww, poor baby, you have to keep playing with yourself! I know watching me on this big dick is making it so much harder for you not to cum, but I need you to keep playing with yourself. Yeah, like that, just stroke it like I was actually fucking you."

I matched her slow pace, but soon she started picking it up, eventually leaning forward with her hands on the stool in front of her as she fucked herself mercilessly. "Oh! Fuck yes. Oh, fuck yes! Just hold on for me. Please just hold off. I'm. Almost. YES!"

Her hair fell in front of her face as her hips slammed down and twitched on the dildo. Her moans were soft and almost shy, which was surprising given how sexually aggressive she had seemed earlier. I felt a stream of precum running down my fingers, but still managed to hold off.