She Deserves It Ch. 02

"Oh good to know!" She did a test squat then frowned. "I think it might be hard for him to properly see the way my muscles are moving with this dark fabric. What do you think?"

"Uh, I don't know, I think I can see them fine."

She shrugged then slipped her leggings and panties down in one go. She grabbed a black thong and slid it on then picked up a pair of white yoga shorts. They left her entire legs bare and in the inseam was so short that her cheeks peeked out.

"Oh, that's better!" Riley squatted and then looked at me over her shoulder. "What do you think?"

The white material stretched across her ass and became transparent. I could see not only her thong, but even the crack of her ass. "Um, they're kinda see-through when you do that..."

"Perfect!" Riley grinned, pulling them off. "I think it's important that he's able to see everything if he's going to give me his best."

I wanted to protest, but something about the way Riley had asked if I trusted her told me it wasn't a good idea.

The next day was rough. I was a morning lifter, so Riley had gone to the gym right after work alone. I waited anxiously at home. When I heard the key in the door, I tried to pretend like I hadn't been sitting there eagerly waiting and opened my laptop.

"Hey, waiting for me?" she giggled as she came in.

"Oh, no, just hanging out," I said smoothly.

"Looking at women's hair inspo?" Riley pointed at the laptop. I cringed. I had grabbed hers and not mine. "I think it's cute that you were waiting for me." She set her bag down. She had on the white shorts and the white top and was still sweaty from the gym.

"How was it?"

"Oh god he fucking killed me babe. How the hell do you keep up with him?"

I laughed. My reaction to working out with him was similar, even now. "Yeah, he's a bit crazy about it."

"Just a bit?" Riley rubbed her legs. "Can you give me a massage? I am barely going to be able to walk tomorrow! I'll tell you all about my workout."

I gulped, wondering what kind of workout she was talking about.

"Ugh, yes, right there," Riley sighed as I worked in left glute hard, putting my full bodyweight into it. It turns out she had meant a real workout, and she was groaning as I attacked the knots that had formed in her muscles.

I was glad that nothing had happened with Dan, right? I kept telling myself that, repeating it over and over in my head to wash out the nagging disappointment that nothing had happened between him and Riley.

"Fuck, this is better than sex!" Riley gasped. "I always thought girls that said massages were their favorite part of sex were crazy, but apparently I have just never pushed myself in the gym before!"

"So, you'd give up dick for this?" I teased knowing just how into fucking she was.

"Oh, hell no," Riley giggled. "But maybe this plus dick would make my life even better."

"Hmmmm," I rubbed my caged cock against her ass.

"Ugh, not right now Tommy," Riley sighed. "You've showered with Dan, right?"

"Uh, yeah..." I didn't like where this was going.

"How big is his dick?"

"I don't know." Riley twisted and looked at me waiting. "It's big I guess."

She put her head back down. "Eat me babe."

"You don't want to fuck? I thought you wanted dick."

She turned and looked back at me. "Not yours. Eat me."

I found myself groaning as she rolled over and I slid down. Her pussy was soaking wet and she grabbed my head and pulled me to her roughly. She was sweaty and her scent was strong and intoxicating. I had trouble breathing she was so aggressive.

"Ah fuck yes. Right fucking there!" Riley screamed as I licked her. Her eyes were closed, which was different. She almost always watched me. Got off on watching me serve her. "Yes, yes, uuuuuggggggghhhhh!" Her legs wrapped around my neck, pinning me in place and I felt the world going black as she cut off my air.

I sputtered backwards gasping for breath, my chest heaving and unable to even speak properly. "Riley," I gasped hoarsely.

"Mmmmm, sorry Tommy," she said dreamily reaching for me. I wrapped her in my arms and she sighed happily. "Wow, that was incredible! I will have to do that more often!"

"Oh? I can give you a massage whenever you want," I wanted to make her happy so she would let me out to play.

"Oh yeah that too," Riley giggled. "I meant I should think about Dan while you go down on me more often."

"What?" I gasped.

"God, he got me so fucking hot today babe! He was helping me with my squat form, and I felt his cock! And god those muscles..."

"Riley..."

"Don't worry, we didn't do anything yet," Riley said as she drifted to sleep, my mind spinning at the off handed way she told me she was going to fuck my best friend.

***

"Having fun babe?" Riley asked as she pressed against me. "I am!"

"Uh, yeah," I admitted then glanced around. We were away from our friends. "What's going on with Dan?" She had been following him around all night, pulling me with her like a lost puppy dog.

Riley smiled. "Nothing? It's just fun hanging out with him! We've gotten so much closer the past few weeks!" I shifted uncomfortably and Riley leaned against me. "You don't mind me hanging out with him right? You trust me."

"Uh, sure...," I muttered. I knew she was up to something and the pain from my restricted manhood trying to swell told me just how okay I was with it even if I didn't want to admit.

"Great! Come on, try to relax baby," Riley giggled. "I know it's hard for you to just let it all hang out sometimes."

"Fuck, Riley..." I moaned. I had been locked up for three weeks, blowing past the previous one-week marks Riley had kept me in chastity. She had been dropping hints all week though. I had taken her shopping and given her massages after every workout with Dan. I knew she was aching for cock, so I liked my chances tonight.

"Everything okay?" Sandy asked joining us. She was grinning widely and didn't bother to hide her interest in my condition.

"Yeah, was just chatting with Tommy, trying to get him to let it all hang out," Riley laughed, and Sandy wrapped her in a hug laughing.

"God Riley, you're such a bitch!"

"Hey, that's not nice! At least I don't leave him all scratched up!"

I shifted awkwardly, not sure how to respond as the two girls took such glee in my discomfort.

I felt a heavy arm on my shoulder. "Dude, you need to come hear this," Dan spoke loudly. He was standing next to me but staring hard at Riley. I didn't blame him. She was wearing a short bouncy dress that kept flashing the bottom of pantyhose covered ass whenever she moved.

Earlier Riley had bent to whisper into Sandy's ear while she sat at a table. Her dress and pulled up exposing her ass and it was obvious she had on no panties. I had caught Dan looking, but he didn't seem phased. He winked at me as if we were sharing a look at some random girl and not my girlfriend!

"Remember that time when we snuck into the stadium at night?" Dan continued, unaware of where my mind was drifting. "Well John has an even crazier story." I let him lead me over and soon was being forced to listen as John recounted how in college, he and his mates got drunk and snuck into their college football stadium only to pass out lost in some tunnels. Despite myself, I was drawn into the story. They had woken late the next day and wandered out to discover they were on the sidelines while the teams warmed up.

"Bullshit dude," I said. "They have security everywhere!"

"Yeah, they do, but it turns out we had slipped in behind them." He pulled out his phone and fumbled with it. It took him a few minutes. "Here look!"

He had an album of photos and videos and sure enough there he was with his friends. They all looked like shit, with dark circles under their eyes in the bright sun, but they were smiling. They even had some pictures with a few of the players.

We all laughed about this and I told them about running into Darren Willis months back, careful not to mention how he had made out with my girlfriend or how they had exchanged numbers. The drinks and conversation flowed from there. I didn't even realize I had lost track of Riley until she pressed herself against me.

"Ah, there you are babe!" I said as she slid into my lap and rested her head on mine. "Want a drink?" She smiled and nodded then moved in for a kiss, her hand stroking the back of my head gently.

I should have seen it coming. Her smiles were normally wide, not hooded, and her lips usually parted, not pressed tight together. I didn't though. It came as a complete surprise when her tongue forced its way into my mouth, and she jerked my head back. Cum poured into my mouth and I struggled to swallow the surprise load.

"God you two make me sick!" Scott laughed. If only he knew...

"I think it's sweet," Sandy said, looking pissed at her oblivious husband with a flushed face. "Tom treats her right." Scott looked at Sandy and shrugged then turned back to John.

"Love you," Riley said, kissing my cheek. "Maybe just a seltzer for me? I don't want to get too drunk tonight. Need to keep it together for later!" She slid out of my lap. I found myself standing and walking past a satisfied looking Dan who just slapped me on the back.

When I got back Riley wasn't even there. Sandy was sitting off to the side and beckoned me over. "She's dancing with Dan." She took the drink I'd gotten for Riley and sipped it while looking at me thoughtfully.

"Everything okay?" I asked, she looked unhappy.

"I'm going to divorce Scott," she said. My eyes widened and I looked around for him. "Relax he went to play darts with his buddies."

"Fuck, that's rough to hear. I'm so sorry."

Sandy smiled softly. "It's kinda your fault, you know. You showed me how much a guy can care. How I shouldn't settle."

"Oh," I wasn't sure about how to feel.

"That's why Riley wanted me to sleep with you," she sighed. "She thinks Scott is an ass and I can do way better."

"You can," I agreed. Honestly if I wasn't with Riley, I would be on her in a heartbeat. She was easily one of the most attractive girls I had ever known, she just had the misfortune of being friends with Riley.

"Ah well," Sandy sighed and smiled. "So how did his cum taste?"

I froze. "What're you talking about?"

"Dan's." Sandy giggled and leaned forward. "Riley wasn't very subtle about it."

"I..." I withered under her gaze. "I always like kissing Riley..." I whispered.

"HHmmm, good boy," Sandy sipped her drink and looked out at the crowd. "Don't tell Scott anything. I checked the joint account for the first time last week and the asshole has been moving money out somewhere. Lawyer says I need to play oblivious for now. Can you believe it? He doesn't even make more than me!"

Sandy seemed to be working herself up and I felt I needed to distract her. I knew Riley would want me to keep her friend happy. "Hey, want to dance?"

Sandy stopped and turned, a blush spreading across her face. "Really?"

"Do you think Riley would be okay with it?" I turned to look and saw Dan and Riley dancing, their bodies pressed together. It looked like at any moment they would kiss.

Sandy pulled me up and led me over to them, whispering in Riley's ear. She just smiled and Sandy pulled me to her. I wasn't great at dancing, but not awful either. Sandy and I danced and had fun, grinding against each other. I smiled as she started laughing and looking happy.

Another song came on and we were both breathing hard. She fell against me and just rested her head on my chest, peering up at me. "You're wearing the cage. I feel it."

"Uh, yeah," I blushed. "Riley makes me wear it all the time."

"HHhhmmm, you're making me wet," Sandy giggled then sighed. "I need to go get Scott drunker so he passes out and I can fuck myself tonight. I have a dildo named Tommy now!" I started laughing at that. Sandy smiled at my mirth then her face hardened. "You're one to laugh, not like you're getting laid tonight either."

"Hhhmmm, I like my chances. I can tell she wants dick, and uh," I hesitated. "She's always really horny after, you know..."

"Being with another guy?" Sandy smirked. "She does want cock, but doesn't mean it has to be yours..."

I froze and realized Sandy was right. I started searching the dance floor, Sandy trailing behind me, but Riley was gone. "Sandy, do you know where Riley went?" I knew she did. Her grin told me everything.

"Dan and she left about twenty minutes ago."

"Fuck!" I flew out of the bar, pushing my way past people until I was outside. I pulled out my phone to call a car then realized I had no clue where she went. She could have gone to Dan's place or ours or even a hotel. I called her but it went straight to voicemail.

I thought about going back inside, but if anyone else had seen her leave they would wonder why I was still around. The thought of Sandy's smirking face would be too much to bear. I called a car to our apartment and resigned myself to a lonely night of fitful sleep.

I slid my key into the door and was surprised when it was unlocked. "Yes, fuck me!" I heard Riley moan. They were here!

I opened the door then followed the noise to our bed. Riley was on her hands and knees, Dan behind her. She looked tiny in front of his huge muscular frame.

"You made it babe!" Riley said grinning as Dan's thrusts slowed.

"Sorry we didn't wait dude, but Riley said you would be cool with it since we have all night," he stroked her ass and shook his head. "Get naked and let's show this slut how it's done."

Riley giggled. "I'm not a slut!"

"Is this your boyfriend's cock in you?" Dan slapped her ass and Riley moaned.

"Yeah, but you're wearing a condom," Riley looked up at me then reached back to fumble between her and Dan. "A true slut always goes bareback."

"Ah fuuuuck that's good pussy!" Dan groaned as he resumed fucking her. Riley held up the limp condom then tossed it at me. She wanted him bare so I could eat the cum out of her, I suspected. "Fuck dude, can't believe you're sharing her! I mean I guess you gotta do what you gotta do to get that girl boy girl action, but I don't think I could do this if she was mine."

So that's the lie Riley told him. I felt oddly grateful for the cover story.

"Ugh, fuck," Riley grunted as Dan fucked her.

"Dude, come on, she's hot for it!" I stood frozen. There was no way I was getting naked.

"Yeah baby, take your clothes off," Riley said. She was staring at me. I shook my head and her eyes tightened.

"Hey dude, it's no big deal I've got a bigger cock, but you've got the bigger wallet," Dan laughed. "We all have to work with what God gave us!"

I started unbuttoning my shirt, slowly, my face a mask of terror. "Riley..." I said plaintively.

"Come on Tommy, get naked." Riley said.

She wasn't moaning or reacting at all to Dan anymore. All of her attention was on me. I fumbled at my belt then dropped my pants, stepping out of them. My hands went to my boxers and paused, fingers trembling as they held my waistband. "Those too." I took a deep breath and then pushed them down. "Good boy Tommy." Riley said smiling.

"Dude what the fuck," Dan gasped as he looked over at me. I felt like dying. Being exposed to Sandy was one thing. She was Riley's best friend and ultimately got off on it, but Dan was different. He started laughing and stopped moving in Riley. She was turned on, though, and started thrusting back on him.

"Ugh, keep fucking me," Riley complained.

"What the hell is that?" Dan said. He moved in and out of her, but without much attention to what he was doing.

"Chastity device," Riley explained. "I keep him locked up."

"Jesus what the fuck," Dan shook his head. Then chuckled. "Oh shit, that's the key you've been wearing for the past, what three months? Four?" Riley groaned in pleasure. "Fucking hell dude, she's made you her bitch!"

"Ugh, yeah," Riley gasped and came. She was looking at me with need, but it was Dan's cock that made her cum. She fell forward and his cock popped out, hard and slick with her juices. He was massive. Way bigger than me or Sean.

"You get off on this," Dan said in realization, looking down at Riley. She nodded. "Well, no fucking way am I doing anything like that. I'm not a pussy."

"Oh, I know you're not. You're a real man," Riley giggled. "That's why you're here taking care of me." She tried to pull him down, but Dan didn't budge.

He looked at me strangely. "You okay with this dude? I can take the key from her no problem."

"I—" I looked at Rile. She grinned confidently. We both knew I could take it away from her if I wanted to. "I'm okay."

"Okay..." He looked uncertain. "I, uh, I might peace."

Riley sat up on the bed. "Dan, do you want to fuck me?" Dan looked at her. "I see how you look at me. Did you like that blowjob earlier? Fuck me right tonight and you can have me whenever you want."

"Look, I'm not into this whole..." Dan struggled for words and gestured.

"Femdom," Riley suggested.

"Yeah this femdom shit," Dan said.

"Good, that's not why you're here." Riley looked over at me then smiled softly. "Look, my sex life, my LIFE, with Tommy is amazing. I'm not doing anything he doesn't want to do. That I don't want to do. I'm not asking you to do anything you don't want to do."

Dan looked unconvinced. I could see Riley frowning and looking sad. All I wanted was for her to be happy and I realized Dan cared too much about me to give her what she wanted.

"I, uh," I had to clear my throat and take a deep breath I was trembling so hard. "I had a dream about you and her. Um, she's making it come true."

"Fuck," Dan looked at Riley.

"Here let me show you," Riley got off the bed and moved over to me. She unlocked the cage, and massaged me. My cock sprang to attention and she let go.

"Oh please," I begged. Three weeks without being out and her hand felt like silk.

Riley laughed. "HHHmmm, I love you." She kissed me but didn't touch my dick anymore.

"Damn," Dan said. "You're really into this."

I blushed and looked away.

"Come on Dan," Riley tugged at him. "Fuck me. Make me cum again. Make him watch. You can't tell me that doesn't turn you on! Fucking me right in front of him. Would you really rather have a threesome than getting me all to yourself?"

Dan smirked. "Hell no, just don't do any of that weird shit to me."

"What if I tried? What would you do to me if went into my drawer and got out a cage for you wear?" Riley taunted.

"Fucking bitch," Dan grabbed her and threw her on the bed. Riley struggled to sit up, but Dan grabbed her legs, throwing her body over. He slapped her ass hard and Riley screamed so loudly I wondered if the neighbors would call the cops. I stepped forward as Dan seemed to be out of control.

"Ugh yes!" Riley moaned and I froze. I realized this was exactly what she wanted. Dan kept spanking her, not as hard as the first time, but still far harder than I would ever do. Riley's ass turned pink then red and she started trying to twist away from the blows. "Just fuck me!" she finally begged.

Dan was on her in a flash, throwing her body around and mounting her. He wasn't gentle with his entry, and as soon as the head was in, he slammed his body down so hard the bed moved. "You fucking bitch! You need someone that can put you in your place!"

Riley spat in his face. I was stunned, but Dan reacted immediately. He grabbed her by the throat with his left hand and fucked her even harder. Riley gasped for air and I could hear her struggling. I moved forward and put a hand on Dan's shoulder, but he pushed me away.

"Fucking take it bitch. You think you're fucking better than me? I'm going to fuck you so hard you can't walk!" Dan leaned back and with his free hand slapped her tit. Tears sprang to Riley's eyes and I had enough.

"Dan!" I stepped forward.