She Deserves It Ch. 02

I had no idea what to say. Nothing made sense. Why hadn't she made me clean her, or spit my cum into my mouth?

"Hey, want to go see the new dinosaur exhibit? It's supposed to be pretty cool. Sandy wants to so I thought it would be fun if we went together. She's lonely since she left Scott and really likes hanging out with us." Riley rubbed shampoo into her hair.

"Oh, yeah that would be nice," I said. We showered and then went to get dressed. My underwear drawer was full of boxers, the panties gone. I looked over at her and caught her watching and smiling happily. She blushed again. I wondered what twisted game she was playing with me.

I kept wondering after the museum, a pleasant time with my girlfriend and her best friend. I kept wondering after she begged me to spank her and to fuck her ass. I kept wondering after a trip to go hiking a week later. After a night out with friends and Riley not flirting with Dan and him not messing with me. I wondered for a month as Riley cuddled me and our relationship became normal.

Well, normal for society, but it felt alien to me.

I tried to revel in my freedom. In the loving attention from Riley. I hated it. I wasn't sleeping well and started skipping the gym, burying myself in work to distract myself. I tried talking to Riley, but every time the conversation was deftly derailed and I never found anyway to bring it up.

I knew something had to change though. It was nine on a Friday and I had skipped going out to stay at work but had gotten nothing done. I sat at my desk, staring at my screen and moved my mouse every time it tried to go to sleep. Finally, I got up and went home to an empty apartment. I went to the bedroom and started searching. I found a box in the top of Riley's closet. I opened it and there it was. The cage, sitting on top of a pile of my panties with the key in the lock. There was a note. I picked it up with trembling hands.

Tommy,

I want you to know that I love you no matter what. I love you and will be with you no matter what. Whatever life you want. You have done so much to make me happy and I have enjoyed every moment of it, but I want you to feel fulfilled and happy too, whatever choice you make.

-Love,

Riley

I stared at the note. It was so short so simple. I looked at the contents of the box and just stared and stared. I picked up my phone and texted Riley, I love you.

The chastity device locked into place easily. I placed the keys on her nightstand then found a garbage bag and loaded up my underwear. I picked out one of Riley's favorite pairs for me and slipped them on and then crawled into bed.

I woke in the morning with Riley naked and curled up around me, spooning me from behind. I shifted slightly and she kissed my neck. "Morning."

"Good morning," I said uncertainly, unsure of how she would react. I felt her hand slide down and rub my caged dick through my panties.

"I like your outfit," she grinned at me. "You're sure?"

I nodded.

"I'm gonna be a real bitch to you..." Riley grinned. The key laid on her right breast, glinting in the light.

"I'll do whatever you want." I meant it.

"Oh, I know," Riley smiled and pushed my head towards her pussy. She was soaking wet and I moaned in pleasure as she pushed my face against her.

***

My month of freedom didn't come without repercussions. Riley told me upfront I wasn't going to be unlocked for a month and after three weeks we were both showing the frustration. I went down on her every day, but I could tell she needed cock and I wanted to give it to her.

"I could fuck you," I said as I used a dildo on her. "I promise I won't cum."

"Damn it, Tommy!" She complained pushing me away. "I was so fucking close!" She looked frustrated. She had been getting short with me. "Look when I've got my eyes closed and am thinking about Dan fucking me keep your mouth shut, okay?"

I was taken aback. "I—I'm sorry." She leaned back.

"Let's just go to bed." She rolled over and pulled the blanket around her. She looked miserable and I could tell my punishment was rough on her too.

"Why don't you fuck him for real?" I asked softly.

"No."

I didn't understand her reluctance. She had basically promised she would fuck him again. "Why not?"

She turned and looked at me. "You have to prove you want it."

"Of course I want it..." I was blushing.

"No. I mean prove it. Don't just say it. Words are fucking cheap." Riley turned away from me. It was clear the conversation was over, and I had no idea what she meant.

***

Sweat poured off my body. Dan grunted above me as he helped lift the bar off my chest back onto the rack. "Damn, close on the fourth, but still a PB right?"

"Yeah," I gasped out, letting my arms flop down. He laughed and started unracking the weights.

"Sign of a good workout when you can't even get your arms up."

"Ugh." I sat up and grabbed my notebook, and recording my accomplishment then helping finish the weights.

"Well good shit dude. Legs tomorrow?"

"Please no."

"Cya at 5:30?"

"Okay."

Dan grinned then started to head towards his office. It was early and there were only a few others working out.

"Wait, Dan, can we talk?" I was nervous. It had taken me ten minutes outside the gym just to psyche myself up and go inside.

Dan shrugged. "Yeah, but I gotta hit the shower man. I've got a date."

"What, at like 8 AM on a workday?" I was confused.

Dan grinned. "Easy time to tell your husband you're going for a workout session."

I rolled my eyes and followed Dan to the lockers it was empty. He didn't hesitate to strip naked and head to the roomy shower cubes. Our gym was expensive, but it had its perks. He left the curtain open between the dressing area and the shower.

"So uh, I wanted to talk about Riley..."

"Look if you're worried about us Riley shut that down. I won't lie that I tried, but she was pretty fucking clear."

"No, uh," I hesitated and blushed.

"Oh, you want me to fuck her again?" Dan grinned now.

"I, uh, yeah."

"Did she put you up to this?"

"Uh, not exactly. She said that I 'needed to prove it' with actions not words. So uh, here I am I guess."

He looked at me then grabbed his phone. "Hold on, gonna cancel my date."

"What why? Riley is probably on her way to work."

"Yeah, but I don't care about this chick. Honestly only picked her up to get my rocks off. I'd rather save it for your girl." Dan punched away on his phone then grinned at me. "I thought you would understand the whole deny then satisfy thing."

"Uh, yeah. It does make it better."

Dan tossed his phone on his clothes, but it bounced and slid to the floor behind me. I bent down to pick it up. "Is that a fucking thong?"

I jumped up my face bright red. I had on compression shorts over it, but it was a thong. I was holding his phone as he stepped towards me. He reached out and grabbed my shirt and lifted. At some point one of the waistbands of the thong had slid out and over my hip.

"Dan..."

"Does she like that?" Dan seemed amused. I nodded and he dropped my shirt and took his phone back. "So, actions, not words eh?" Dan stepped back in the shower. "I hear a whole lot of mouth flapping. I think Riley prefers you to put your mouth to other uses."

My eyes widened. He was hard. I suddenly realized how fucking weird it was to follow your naked friend into one of the shower cubicles and beg him to satisfy your girlfriend. "Dan..."

He shrugged. "I'm not going to make you, but you know I'm right."

"You're hard," I whispered.

"Yeah," Dan seemed entirely unconcerned. "Turns out I like putting bitches in their place no matter their sex."

I would like to say this was the point in time that I grew a pair and stormed out. That sucking cock was where I drew the line. Instead, I found myself stepping forward. All I could think about was how pissed Riley had been last night. How badly she needed cock, and Dan's looked to be exactly the one for her.

"Strip."

I hesitated, then obeyed, pulling my shirt and shorts off. I started to drag the thong down with my compression shorts, but Dan was having none of it.

"Leave panties. They suit you."

I kept my eyes down. There was no way I could look at him. When I was eye level with his manhood, I recalled the view from the night he fucked Riley. How good the two of them had looked together. How his cock felt in my hand. He groaned when I touched it.

Riley had had me suck dildos while she masturbated sometimes. She had one that was close in size to Dan's, but the similarities ended there. The silicone dildo felt dull and lifeless, and despite its expensive price tag it did not replicate the strange combination of firmness and softness against my lips and tongue.

The wet noises of my mouth sliding on his cock were thankfully masked by the sound of his shower in the background. I struggled to handle him and wondered how Riley, a girl so much smaller than me, had pleased him so completely. Whatever inadequacy I might have felt, Dan wasn't so concerned.

"Ah fuck dude, you're actually good at this," he grunted. The worst part about his complement is I felt proud, like if I was going to be a cocksucker I might as well be good at it. I glanced up at him and froze. He had his phone out and was filming me. I tried to pull away, but he grabbed by head. "Just finish bro."

I struggled but had no hope against him. I had put my arms on his thighs to try and push myself off him, but my elbows bent as he forced himself deeper in me. He didn't stop until his full length was buried down my throat. I struggled for air and then realized he had pulled his hand off the back of my head. I eased him out, but it was all too much for him and he started filling my mouth with cum.

I sputtered and choked as I swallowed, cum dripping down my chin. I sat back panting. Dan had a content expression on his face. "Damn have you done this before?" He lowered his phone. I shook my head. "Well shit, I'm impressed!"

I sat there on my knees as he tossed his phone back on the pile of his belongings and went back to showering. I reached for my clothes and started dressing, my wet skin sticking to the fabric.

"Hey dude, want to go to the driving range this weekend?" Dan asked as if nothing had happened. "I got this coupon for some free buckets."

"Uh, yeah sure," I said not knowing what else to say. I slipped out of the cubicle and drew a deep breath when I found the locker area still empty. I moved to a sink and started wiping Dan's cum off my face and neck.

I grabbed my things and slipped out. I usually showered at work, safe from prying eyes in the private bathrooms they furnished for bike commuters. When I got to my office Riley was standing outside waiting. She flung her arms around me, kissing me hard.

"Awww," she said pulling away. "I can't taste him!"

"Riley!" I hissed unlocking my door and dragging her inside. "I brushed my teeth..."

"Oh Tommy," Riley grinned. "How was it?"

"Uh, he was rough."

"Yeah, isn't it great!" Riley said. "I can't believe you fit the whole thing!"

"Ssssshhhh!" I glanced at the air vent.

"Don't worry he left for a meeting a few minutes ago."

"Oh." I looked at her and her flushed face. "Did, uh, you and he...?"

"No," Riley grinned and winked.

"What, do you want me to..." I did NOT want to suck Jack's cock too.

Riley laughed. "I think he would fire you if you tried. He's not like Dan."

"What? Like Dan?" I was confused. I had known Dan for years.

"Yeah." Riley grinned. "Did you know back in college he fucked Stan's girlfriend?"

"You know Stan?" I asked shocked. He was a friend from college. Not a close one, but we swam in the same circles.

"No, but Dan showed me a video. It was fucking wild!" Riley smiled at me. "Let's just say turns out Dan is really turned on by being dominant."

"I could tell." I rubbed my jaw.

"Oh no, you sore? Don't worry, you'll get used to it! Trust me on that." Riley looked so eager I didn't want to argue with her. "Anyways, thanks so much! I invited over Dan after work. I know you have that dinner meeting, but you can join after?"

I found I was looking forward to it.

*****

I looked at the two pussies spread in front of me, both oozing cum. Riley and Sandy were giggling.

"This isn't fair. It could be anyone!" I complained.

"Well life isn't fair!" Riley laughed. "How about a hint. Someone you know. You've tasted their cum before."

"Uuhhh," I looked. The game was simple. They each had messy, just fucked pussy and I had to guess whose cum it was. At this point all I knew was it wasn't mine. I gulped, thinking about the stakes. Riley had me wearing our largest butt plug most of the day, but the dildo sitting on the nightstand looked bigger. I much preferred to get it right and enjoy a night of freedom with the two of them.

"How about I give you one question." Riley suggested. "Yes or no, only."

I thought hard. Riley had been with Sean, Dan and Jack. I had no idea how to phrase a question that would help me narrow it down. Suddenly a thought occurred to me. "Can I taste you?"

Sandy started laughing and Riley looked impressed.

"Ohh interesting strategy! Yeah, go ahead."

I leaned forward and started tasting her. I don't know what I was expecting but all I could taste was cum and pussy. I sat back, frowning. "Well, that didn't help at all."

"Maybe not, but it was hot as fuck," Sandy had a flushed look on her face looking at me. "Do mine now."

"Uh," I hesitated, but Sandy bumped Riley out of the way and pressed her pussy to my lips. Cum and pussy again but it was definitely different.

"Alright so two different guys. At least that's something." I looked at them both then grabbed my phone. A quick search and I found out Sean was on the other coast. I had to take a guess. "Alight. Sean is a thousand miles away, so he's out. That leaves Dan and Jack. I don't think Sandy knows Jack. So I will say Jack in Riley and Dan in Sandy." I sat back and grinned.

"Wow that was quiet some logic!" Riley said. "I'm so fucking proud of you!" I beamed at her happily.

"Thanks! This is going to be so fun!" I stood up and waited for her to unlock me. Instead, she reached for the dildo and harness. "Uh, Riley?"

"Good logic, but wrong! I mean I guess half right. Dan did fuck Sandy."

"He was good!" Sandy grinned.

"You were so close, but you knew the rules." Riley was putting her legs through the straps of the harness.

"But who? Sean? How?"

Riley giggled and shook her head.

"It was Darren!" Sandy burst out, unable to control herself.

Riley stared daggers at her. "Maybe I should fuck you in the ass!" Sandy laughed and shook her head.

"Darren?" Who the fuck was Darren? I wracked my brain.

"Darren Willis," Riley offered grinning. She picked up the dildo and started to struggle to fit it into the holder. "Fuck, should have put this in first!" She started removing the straps.

"Oh!" The receiver from college that we had met in a bar. The guy that had convinced Riley she was as hot and desirable as I said she was. "I thought you said I had tasted him?"

"You have! Last Tuesday? When I had that 'late workout class?'" Riley threw up some air quotes. "Well, I guess he did give me a workout!"

I remembered that night. I had fallen asleep on the couch watching the game and been woken up as Riley settled her dripping pussy onto my face. I had assumed it was Dan's as they had been fucking multiple times a week lately.

"You cheated!" I complained. Riley had the strapon on in place now. It looked intimidating as hell. Also fucking hot. Like really hot. I gulped realizing how into this look I was.

"It's a bit late to be complaining about me cheating when I've been fucking other guys for months now. No one likes a sore loser Tommy. Well, I guess I will still like you even though you are about to be a loser with a sore ass." Riley smeared lube all over her thick fake cock. "You got it half right, so I'll let you choose the position."

I gulped. "Uh, my back? I, um, I want to watch your face."

Riley advanced on me. "Aww, that's the sweetest thing you've said all week!" She pushed me back onto the bed. I felt her fingers pulling on the plug. It resisted, moving slowly, then shot out. Riley wasted no time, and I felt the head of the dildo press against my ass. I tried to relax.

"Oh god, please go slow," I begged.

The look on Riley's face told me she was going to be anything but gentle. She didn't jam it all in at once, but it wasn't slow either. I felt stretched to the limit and there was a burning sensation that quickly subsided.

"How does it feel?" Sandy asked curiously. I had forgotten she was here and turned to see her openly masturbating as she watched.

"Ugh, it's fucking big," I grunted. I had watched Riley cum from anal and had no idea how. I had to admit the butt plugs felt good once I had gotten used to them, but this felt different. Not unpleasant, but certainly not good.

"Ugh, take it bitch," Riley grunted. She grabbed my hips and started fucking me harder. I gasped and tried to focus on staying relaxed. The change was so slow and subtle I didn't notice. "Yeah, moan for me bitch."

When had I started moaning? I realized it felt good. "Oh, fuck Riley. Oh god fuck me!" By this point I knew I was submissive. I had done some fucked up things for Riley's entertainment and enjoyed them. But nothing Riley had done to me made me feel as vulnerable, as in her control, as hers, as her fucking my ass. I mewled with every thrust like a bitch in heat, like Riley when Dan came over and fucked her ass.

Riley's face was one of focus and sweat poured off her lithe body. Her muscles twitched and flexed as she put her all into dominating my ass.

"Oh god Riley. Fuck me! Please let me cum. Oh god can I cum?!" I could feel it rising and wasn't sure I could stop it.

"Cum for me Tommy, fucking cum you dirty bitch!" Riley reached forward and grabbed my neck. Her hand was too small to really choke me, but the message was clear, and it drove me over the edge.

No matter how dominant Riley was, she was way smaller than me. My thrashing nearly threw her off the bed and it was all she could do to keep the dildo lodged in my ass. Cum poured out of my restricted cock, pooling on my abdomen.

"Holy fuck," Sandy said from the side. Riley and I were both trying to catch out breath, but I could see in her eyes just how turned on she was.

Riley eased herself out of my ass and then quickly took the harness off and then laid back on the bed. "I need you Tommy. Fuck I need you bad." I could hear Sandy moaning as she came. I groaned and rolled over, crawling between my girlfriend's legs to give her the release she deserved.