She Deserves It Ch. 01

"Whew, wow!" She looked up with a bright smile on her face. "Nothing like a nice thick dick, right?" She smiled and lifted herself off and then moved the dildo away. She sat on the stool and spread her legs. "Keep stroking for me, we're almost there."

She reached her hands down pointed at her pussy, which was open and messy looking. "MMMmmm, look what that dick did to my pussy. Do you think yours would make me feel so good?" She glanced down and started giggling. "How do you think I would feel now? All stretched out. I bet you still wouldn't be able to last even after that big dick opened me up for you."

The timer on the screen reached zero and the egg timer buzzed. "Wow, twenty minutes!" She beamed and clapped her hands. "What a good boy! I can't believe you actually did it this time!"

She wrapped her arms around herself like she was giving a hug. "You've done such a good job I think you can get yourself off tonight. Can you do that for me? Can you stroke that dick and show me how big of a load you can make? I know you'd really rather cum on me. Maybe my face? I'm not sure you've earned that despite how good you were today."

"Yeah, like that, cum for me baby, yeah, keep going. Don't hold back anymore!" Miss Claire squirmed and her eyes were wide and eager. A vision of Riley encouraging me instead of this stranger flashed into my head and my balls boiled. Cum shot out across my abs and chest. I felt the shots of hot liquid splash across my body and I groaned, my back arching pleasure. My mind blanked. I felt calm and more relaxed than I had for months, years even.

"MMMmmmm, that's right, good boy..." I drifted off to sleep as the video ended.

"Ssshhh, it's okay," I felt warm hands and a cloth wiping at me. My eyes struggled open and I saw Riley wiping at my naked body. She smiled at me. "Close your eyes baby, let me take care of you."

I grumbled half-awake then slid back to sleep as I felt her start to wash my crotch. I grunted as she pulled a bit on my balls but was too exhausted to stay awake.

***

I heard the beeping of the coffee maker and stretched as the door to the bathroom opened and Riley walked out naked drying her hair with a towel.

"Morning baby!" She said happily. "You're gonna be late if you don't get up."

I groaned and reached for her. She giggled and bent to search the drawer she kept at my place. My hands stroked her legs then moved to her ass. "Come to bed," I begged.

She stood and grinned at me. "You think I'm going to fuck you after last night?" She had a playful smile and I put on a big fake frown as I recalled how she had found me passed out covered in my own cum.

Fuck she looked pretty! I felt my cock twitching and start to stiffen. I reached down as my manhood caught on my underwear as it tried to grow.

"What the fuck!?" I bolted up and threw the covers off. There was a pink cage enclosing my penis. My balls had been pulled through a ring. I tugged on it, but it wouldn't budge. "Riley, what the fuck is this?"

Riley giggled at me as she pulled her panties up. "It's a chastity device. I told you not to jerk off last night."

Memories of my night returned. "Riley, come on, what the hell?"

"You should shower," she continued as if she couldn't hear me. "I tried to clean you up, but you made a real mess of yourself. I'm not going to make myself late just because of you."

She left the room, her panty clad ass causing my cock to stiffen painfully. I looked more closely and saw a small lock on the side of the device. Immediately I started looking for the key. It was laying out where Riley usually left her jewelry, strung on a necklace. She hadn't tried to hide it at all! I picked it up then hesitated.

"Riley, is this the key?" I asked.

"Yes, can you bring it to me?" she asked sweetly as if asking me to bring her a glass of water. I hesitated. I could unlock myself if I wanted to. She couldn't stop me. I looked up and she was standing in the doorway watching me.

"W—why?" I asked.

She shrugged and held her hand out but made no move to approach me. "You know what you want baby, now be a good boy."

I couldn't believe it, but I found myself walking up to her and handing her the key. She kissed me on the lips and slipped the necklace around her neck. "Thank you, baby," Riley giggled then moved to her drawer. "You like pantyhose, right?" I nodded dumbly. I loved when she wore them, but she rarely did. "Well, I think you deserve a little treat..."

I watched as she slid the nylons up her legs. She seemed to glow from my attention, but soon I groaned in pain as the show proved too much for me. She smiled. "Maybe a cold shower would help?"

"Ugh, Riley we need to talk," I said.

"Later, go shower or we're going to be late," she stood, topless with her hand on her hip. Fuck, she was just god damned perfect I didn't know how to respond. She smirked as I turned and headed to the bathroom.

I showered and shaved, trying not to look at the pink cage locked around my manhood. Despite my best attempt, when I left the bathroom Riley was gone. I quickly grabbed my phone.

Me: Riley, where's the key? I need to take this off before work.

Riley: We'll talk later. Jack wants a meeting with us at 9. You'd better hurry.

I cursed and scrambled to get dressed, grabbing some granola and a travel mug. The cage felt awkward and I was worried someone would see it somehow. I was pouring my coffee when I noticed my small apartment tool kit sitting in its place above the cabinets. There was a cutting tool in there that I knew would have no problem with the plastic material.

I paused, considering it closely, but the thought of Riley being disappointed in me somehow seemed more important. I cursed at my weakness as I grabbed me things and ran out of my apartment.

***

"Wow thank you so much!" Riley grinned standing and leaning across the desk to shake Jack's hand. I beamed at her and could not help checking out her legs and ass as she reached forward to shake Jack's hands. She had just been offered a position in the compliance division. Jack and HR had wanted to speak with us both to talk about how our relationship would be handled.

I saw Jack's eyes twitch down to Riley's cleavage. "Oh, what's this necklace?"

Riley glanced down as Jack reached out and held the key that was dangling from her neck. His hand was inches from breasts, and I felt my face burning. Riley looked up at him and smiled before turning to grin at me. I felt my face burning, but fortunately Jack's attention was firmly on the view down my girlfriend's top.

"Oh, it's a key to something very special to me that I have locked away. I decided to start wearing it just to remind myself how important it is to me," Riley was looking into my eyes as she said this and turned back to Jack. She made no move to pull away from him.

"Huh," Jack let the key drop. I was thankful he was distracted by Riley, because I was squirming as my dick struggled to find the space to form an erection, a confusing reaction that had me completely off-balance. "Well, I hope you consider the offer Riley. You've been one of the best interns I've ever worked with. Tom here was great, but he certainly doesn't add to the office ambiance like you do."

Riley beamed and smiled at him. I felt myself tense up. He was flirting with her! "Aw, thanks Mr. Falton. I try to bring joy to all parts of my life."

"You've certainly brought it to all parts of me," Jack said smoothly. His words about how no relationship would stand in his way flashed through my mind. I had thought he spoke about his marriage, but did he mean mine too? Why did that fear make my dick strain against its cage? "Please call me Jack now though. I only do the whole Mister thing with interns and in bed."

Riley laughed. "Okay then Jack. I'll look things over and talk with Tom. I expect I will make a decision really soon?"

"Glad to hear it. After you accept, I should take you out to lunch sometime to celebrate," Jack stood and shook her hand.

"That would be nice!"

I moved to stand but Jack gestured for me to stay. "Hold on Tom, I have some other things to talk with you about."

"Oh, sure," I said. Riley kissed my cheek and then turned to walk away. Jack stared openly at her hips and ass, and I wasn't sure how to react.

"Damn, you're a lucky guy," Jack said shaking his head after the door closed.

"Uh yeah," I said, wondering what he would say if he knew she had locked me into a chastity device!

"Alright well, I wanted to talk to you about Jerry. I get the impression he's been struggling lately, but you've been working more closely with him and since in a few months you'll be sitting here, I thought we could work through this together..."

***

"Show me," Riley told me as she sat across from me in the corner of the cafe.

"What, here?" I hissed, my eyes darting around. It was Friday after work, and we had met in a small cafe for some dinner. We had a small corner table in the back. I knew what she wanted to see, the cage she had put me in.

"Why not?" Riley looked around.

"Riley..." I hesitated. "Why are you doing this to me?"

I saw a brief crack in Riley's smile. "You like it, don't you?"

"I—I just don't understand. I never asked for this!"

"That's not the same as not liking it," Riley answered. She took the key off her neck and set it on the table between us. "Answer me please."

"I don't know..." I looked at her and suddenly it felt like a dam inside me broke. "I just don't want to lose you."

"I know baby, I don't want to lose you either," Riley giggled. "I'm having way too much fun!"

"Yeah, but like," I sighed. "This thing isn't helping me feel like I am pleasing you. Look, you could have anyone here. I just feel so helpless around you!"

"Oh, I know, and I like it," Riley said cheerily, but then she turned serious. "Is this the whole 'bigger wallet, bigger dick, bigger muscles' thing you were talking about? You don't have to worry about any of that. You're hot as hell and make more than enough money just by yourself to give me the lifestyle I want."

There was one thing noticeably absent from her list. "What about... you know?"

"Oh," Riley started laughing. "Sorry, your dick is perfect for me! It really is. It's the biggest I've ever had. Honestly never thought dick size was mattered for me until you."

Her talking about her past lovers had an unexpected effect on me. I squirmed and she smiled knowingly at me.

"Look you're the best I've ever had, in and out of bed. Although a girl does get curious sometimes..." She leaned in with a twinkle in her eye. Her hand slid up my thigh and I groaned as she wrapped it around my restricted dick. "You're still wearing it."

"Y—yeah," I gasped.

"Good boy," she leaned back. "I'm just teasing you. Trying to make you desperate to please me."

"Well, it's working," I admitted.

"I know baby, I know. But you really don't have to worry about other guys. I think you way overblow how interested they are in me."

I stared at her in disbelief. "You know you're hot right? Like eleven out of ten, face and body?"

Riley blushed. "I'm not like that..."

"You got scouted on a field trip to be a model!"

"That was just a random happy accident!"

"Guys flirt with you constantly. Every time you enter a room everyone is watching you! I see it every day. Hell, the guy over your left shoulder has been sneaking glances at your legs all evening."

Riley glanced at him. "Oh, he's kinda cute..."

"Riley..."

"Sorry! Look I think you're just imagining things."

"Really? Okay what about Jack today. He was hitting on you right in front of me!"

"No he wasn't?"

"Riiight, you just add to the 'office ambiance' through your desk decorations and it's totally normal to grab a girl's necklace and look down her blouse?"

"Um," Riley seemed less sure now.

"Never mind the whole 'mister in bed thing' and the fact that he asked you out on a date!"

"It's just a work lunch!"

"Yeah, but he didn't invite me, did he?"

Riley's face flushed. "He was just being friendly. That's just how guys are!"

"To you. Because they want to fuck you."

Riley giggled and shook her head. "No that's just what you see because you want to fuck me so you assume everyone else must."

I stared at her in disbelief wondering how she couldn't see herself like everyone else did. "All right, let me prove it to you."

"Yeah, how are you going to do that? Just walk up and ask some guys?"

"No, let's go to a bar and then dancing."

"Oh yay!" Riley brightened up at that. She loved going dancing and usually had to bribe me to go. "Yes! I need to go home and change though."

Riley rushed through dinner and I was soon watching as she slipped on a short black dress over her thong. The dress was backless, and she left the bra off.

"There's a new place over on Jackson I want to go to. It's just a bar, but they bring in DJs at eleven and it's supposed to be pretty fun!"

"Sure, sounds perfect. Um, would you take this off?" I pointed at my crotch.

Riley frowned. "No, now quit annoying me." Her cold refusal set me back on my heels and for the next few hours I did my best to keep her happy and carefree. The drinks helped, and we were soon both feeling no pain.

"Can you order me a drink?" she asked as she returned from the bathroom.

"How about you do it?" I needed her to go up there alone for the next part of my plan. She needed to understand just how desired she was. "Go up there and just hang out, see if a guy offers to buy you a drink."

Riley rolled her eyes. "Guys offer to buy any girl a drink. Doesn't mean I'm special. They just want to get laid."

She had a fair point, but I wasn't going to let her win. "True, but you don't have to say yes. Just count how many you get and see how many other girls get."

Riley shrugged and I watched as she walked up to the bar. I really did have to pee and wandered away to find the bathroom. It was one of those crappy single person bathrooms that inevitably had a big line.

When I got back, she was standing there laughing and sipping a cocktail. I almost approached, but something stopped me. Riley was giggling and smiling at a guy. He was about my height, but fit and black. He probably had twenty or so pounds on me and it looked to be all muscles. He looked vaguely familiar, but I couldn't place him.

Riley seemed to be enjoying the conversation, and after a particularly funny joke when she leaned forward to playfully push on him, he slid his arm around her waist. I decided this had gone far enough to prove my point and moved to join them.

"Oh, hey Tommy!" Riley beamed at me. The guy made no move to pull his arm off her, but Riley stepped forward to kiss me. "This is Darren, he went to your school!"

Everything clicked into place and my eyes widened. "Oh shit, you're the receiver!"

"Yeah, guilty," he laughed.

"You played in the NFL!"

"That was a few years ago," Darren laughed. "Turns out I didn't much enjoy feeling like I was hit by a bus every weekend. In college I was the big guy, but everyone's huge in the pros. When did you graduate?"

"Uh, 2012, I was there for your breakout season my senior year."

"Whew, now that was a fun year. If only the pros had been like that maybe I would still play."

"What do you do now?"

He shrugged. "Rich parents pay me to train their kids. Definitely not what I expected to be doing, but the pay is good and the connections are amazing."

"Yeah, didn't you say some of them pay to fly you with them on trips?" Riley chimed in.

"That's just the one family. They're convinced their son is going to be the next Jerry Rice and who am I to argue if they want him training during their trip to the Caribbean."

"Wow, damn," I couldn't believe I was talking to him. "Sounds like a sweet gig."

"It's okay," Darren laughed. "Honestly best part are the housewives."

Riley's eyes widened. "Oh Darren, you don't? Do you?"

"I pride myself on my customer service approach." He grinned slyly and stared into Riley's eyes.

"But they're married!"

"And willing," Darren grinned. "Besides, most of the husbands know."

Riley turned bright red. "Wow, okay!" She glanced at me as I shifted uncomfortably. The talk of him banging married women and Riley's reaction were causing some minor swelling that was a bit uncomfortable.

"How's the drink?" Darren asked.

"Really tasty, thanks for the suggestion!"

He looked over her shoulder and smiled. "Well, I'd love to stay and talk, but the game doesn't play itself." Riley glanced at where he was looking, a blonde woman in tight jeans with her ass sticking out as she leaned over the bar.

"Darren!" Riley giggled.

"What? She's not the prize you are but if I only chased girls like you, I'd go home alone way too often." Darren slid past Riley, their fronts brushing.

Riley looked surprised but pleased. She moved closer to me. "He was nice."

"And clearly interested in you."

"Stop it, he's interested in every girl here."

"He tried you first."

Riley didn't have a reply to that. "Well, uh, five guys asked to buy me a drink." She blushed. "It's a crowded bar, I couldn't tell how many offers other girls were getting."

"Why'd you let him?"

"It just kinda happened..." Riley blushed and seemed unsure of herself, especially in comparison to how she'd been treating me lately. "We were chatting and the next thing I knew he was handing me the cocktail."

"And putting his hand on your waist," I reached down and tugged at the cage seeking relief, but it was futile.

"He was just trying to hear me!" Riley protested without conviction.

I decided to let it go. She might not be willing to admit it, but I think the encounter with Darren had given her a glimpse of how the world viewed her. We drank and talked with some others as we waited for the dancing to start. The vibe of the bar started changing and within an hour there was dancing and the crowd level increased. Riley and I split up to use the bathroom before we danced.

I was done first and headed to the bar to get us some drinks. I saw her come out of the bathroom and start walking towards where we had agreed to meet. Suddenly, Darren appeared out of the crowd near her. The two talked and I saw her searching for me, but I wasn't there so she shrugged and followed Darren. I was immediately concerned but had just ordered drinks had to wait for them.

As soon as I had them, I set off in the direction they were headed, pushing my way through the crowd. They were right on the edge of the dancing mass, dancing together but separated by a half a foot or so. Their focus was entirely on one another. Nothing inappropriate, so why did I have an uneasy feeling in my gut?

The crowd pressed tighter, and I watched as she backed up and he pulled her body to meet his. She laughed and I saw him bend down to whisper into his ear. I didn't realize I had been drinking until I hit the bottom and cringed as I realized I had downed a drink in just a few minutes.

It seemed to happen in slow motion. Riley tilted her head back to look at him and her lips parted as his face drew closer and then they were kissing. His hand slid up and cupped her breast through her top as they made out. Time lost meaning for me as I watched my girlfriend kiss another man with a surprising amount of enthusiasm.

The songs blended into another one and they broke apart, her face flushed. He said something and she laughed and shook her head as he kept talking, but eventually seemed to give in as he handed her his phone and she typed away on it.

And just like that, it was over. He vanished back into the crowd and Riley turned and started to search for me. I went to her quickly, whatever paralysis that had held me frozen, gone.