She Deserves It Ch. 01

"Riley," I started.

"Okay you're right," she breathed heavily. She grabbed the drink in my hand and chugged. "We're leaving."

I followed her out and we called a car. "You kissed him!"

She blushed and grinned. "Uh, yeah. He said he had to take another shot at me. That he would rather go home alone than not have given me his best."

I groaned as my cock tried to get hard but was painfully confined by the cage.

"Are you going to be sick?" Riley asked concerned.

"Ugh, no, it's..." I blushed.

"Oh." A twisted grin spread across her face. "OOOohhhh. I did read it was very painful to get an erection in one of these." She reached out and grabbed me, which only increased the discomfort.

"Oh fuck, please," I begged.

"Awww, what a horny boy!" Riley slurred louder than I wanted.

"Riley!" I pulled her hand away and led her further down the block to an emptier area.

"Babe, there's no reason to be embarrassed about making your girlfriend happy." Riley smiled encouragingly. "I love you!" She pulled me down and kissed me, softly but soon we were making out until a car honked.

Riley laughed as she crawled in and I was treated to a view of her bare ass framing her thong covered pussy. She turned and wagged her hips at me smiling. I crawled in after and she leaned against me, her hand fell into my lap and started playing with my caged cock.

"Oh fuck," I groaned. "Babe..."

The driver chuckled. "Looks like someone's getting lucky tonight."

"Oh yeah, he's a very lucky boy," Riley grinned as the car pulled away.

***

"Fuck," I gasped as the lock clicked open and Riley pulled the cage off. Her hand grasped me and started rubbing life back into my dick. I hardened immediately, the feeling of simply having an erection feeling overwhelming.

"Feel good?" Riley was watching me closely.

"Oh god Riley, that feels incredible!" It really did. Her hands had never felt like this before. Hell, I bet this gave her pussy or mouth a run for pleasure!

"HHHmmm, well don't cum yet, I need mine first!" Riley pushed me over and climbed on top.

I was wrong about her hands being as good as her pussy. She was hot and wet and had no trouble guiding me in, clearly as eager as I was. She took me slowly though, probably to make sure I didn't blow my load prematurely, and truthfully, I was grateful. The slow torturous decent down my manhood was beyond comprehension. It made every other sexual encounter pale in comparison.

"Fuck Riley, you feel incredible!"

"Oh god, so do you baby," Riley groaned. She bottomed out and leaned forward to kiss me. "God I'm so hot!"

"Yeah baby, see? Did you see how Darren went right for you?"

Riley started laughing. "No Tommy, I meant hot like horny! But yeah, I saw how he went for me." Riley put her hands on my chest and started slowly fucking me. I could barely speak, and I put all my will power into not disappointing her by cumming before her.

"Ugh, he got us so worked up babe. Did you see him kissing me? Is that why your cock was trying to get so hard?" I didn't trust myself to respond and she took my grunting and moaning as encouragement to continue. "God I could feel him grinding against me. I think he was bigger than you."

"What?" I gasped, by dick lurching.

"His cock baby. Didn't you say all the guys with bigger cocks were going to try to steal me away?" Riley moaned and her eyes glazed over. She treated me like a dildo and slammed her hips up and down. "Well, he tried baby. He was rubbing that thing all over my ass."

"Ugh, please baby," I begged, wanting her to stop talking about this right now. At least, that's what I told myself, but my cock had never been harder.

"Yeah, you liked it too? Seeing him kiss me?" Riley's head dropped forward to hang over me as she somehow fucked me even harder. "He even made me put his number in his phone! I didn't want to at first, but then I saw you watching him feel me up. Squirming as your cock tried to get hard!"

She'd seen me?! "Riley—"

"FUCK! OH GOD FUCK YES!" Riley's hips sat down hard on my dick and she ground in a circle as she came. Her pussy massaged me as I felt it clench and release repeatedly. She fell forward, breathing hard onto my chest.

I rolled us over to finish fucking her, but she moaned and flopped limply. "Riley?"

She didn't respond and was clearly passed out. I looked down at my hard cock and her wet open pussy. God, I wanted to so badly, but she was clearly done. I gently undressed her, then myself, and cuddled in bed. She sighed as my cock nestled between her cheeks. This night—hell, this whole week!—had been pure torment. I just wanted it to be over. My dick had other ideas.

Fortunately, the alcohol helped me get to sleep despite my unsatisfied sexual need.

***

"Ugh," Riley groaned as I ground against her slightly. "Babe, later please. I am so hungover."

"Oh, sure," I sighed. "Let me get you some stuff to help." I got up, my erection leading the way and found her some water and painkillers.

She joined me in the living room a few hours later, looking much better. I was hanging out in my boxers watching college football. "There's some breakfast in the fridge I can heat up for you."

"Thank god," Riley sighed. She was wearing just a pair of panties as she followed me into the small kitchen. She ate quickly and stretched, her abs forming a V that pointed to where I was desperate to put my cock. She looked at the erection that was poking out of my boxers but didn't comment on it. She looked like hell, and guilt flooded her face. "I, uh, sorry about last night."

I wasn't sure what to say. It had been an incredibly strange night. I had watched her make out with another guy while locked in a cage then been left unsatisfied again. And yet, somehow, I felt happy? Admitting that was... difficult and I didn't think I was ready. She took my silence as me being upset.

"Well, his game reminds me a lot of Darren Willis, if you remember him from a few years back," the talking head on TV said. Riley cringed at the mention of his name.

"I think I fucked up," Riley said. She looked like she was about to cry.

"Riley—" I started.

"I was having so much fun! I just got caught up and I went too far," Riley curled up on the couch, wrapping her arms around her legs. My heart melted when I saw how hard she was being on yourself.

"Look we were drunk, and I was basically setting you up. I—I love you."

"I don't see how. I made out with him and then threw it in your face!" Riley sighed. "And the worst part is I liked it. I liked doing that to you! I don't want to be that person."

I wasn't sure how to respond to that, but it was clear I had to. I knew what she meant though, about liking something but maybe wanting to not like it? "I, uh, feel like that too. The sex last night was honestly the best I have ever had, and it wasn't even close." Riley looked up surprised. I could feel my face burning. "It's hard to admit that I liked it though. Even harder that I want it again..."

"Aw, Tommy," Riley reached for me and we wrapped ourselves around one another. "I love you. I didn't mean to go so far, I just wanted to dance with him a bit so I could tease you."

I answered her with a kiss, and we made out few a few minutes just to feel connected again. When we broke apart and she looked at me happily.

"So, you liked it last night?" She asked with uncertainty. "Even the uh..."

"The teasing about Darren?" She nodded. "Yeah, I think I did. Fucked up right?"

"No more fucked up than me liking it," She said, then started giggling. "So how did my pussy feel after being locked away?"

"Oh god, unbelievable! Like the first time all over again."

"I bet your orgasm was incredible! Thanks for cleaning me up by the way, I hate waking up sticky."

"Uh, I didn't finish."

"What?" Her eyes widened and a huge smile spread across her face. She jumped in my lap, her bare breasts pressing against me. "You still haven't cum?"

"No? You passed out after you came. It would have felt wrong..."

"Oh no Tommy, you're such a god boy!" She stood and pulled at me. "Come on!"

In the bedroom she pushed me onto the bed and pulled my shorts off. "How do you want it?"

"I get to choose?"

"Oh yeah, good boys get rewards," Riley pushed her panties down. "Want me to ride you? Doggy? Sixty-nine?" She looked most eager at the suggestion of the sixty-nine.

I decided to go for broke. "Anal?"

She laughed and shook her head. "You're not that good of a boy."

"I considered my options.

"Or you can let me choose!" Riley grinned and had a sparkle in her eye that terrified me. And apparently aroused me because my cock started hardening and was soon at full mast. "Oh, looks like someone knows what he wants..."

She reached out and took hold of my dick with her fingers. "Oh, fuck yes," I moaned.

"How mean can I be?" Riley asked.

"Oh god, as mean as you want," I begged, shocked at the words coming out of my mouth. "I'll do whatever you want!"

I was drunk last night, which always dulls the senses. It turns out as good as her pussy felt, her mouth when sober and the denial of the week was even better. "Oh Riley, oh my god!"

She grinned as she ran her tongue along my shaft, tracing the veins and running small circles at sensitive spots she found by watching me squirm. She moved to the tip and circled it with her tongue. I raised my hips, but she backed away and playfully slapped my cock.

"Down boy!"

I groaned as she resumed her slow, soft worship. She kept her gaze on me the whole time, her pretty big blue eyes sparkled with how much fun she was having. I have no idea how long I lasted. It could have been three minutes or thirty, but in the end, she put her lips and tongue on the sensitive underside and massaged the same spot until I groaned and begged her. She kept at it, adding a hand at the base of my shaft and stroking until I couldn't delay any longer.

"Oh yes! Fuck I'm gonna cum!" My balls tightened and I felt her lips move to the head of my cock. Suddenly her hand was gone, and I groaned as my cock pulsed helplessly. At the last moment she ran a finger along the underside, and it sent me over the edge. My cock pulsed as jets of cum shot out into her mouth. Her eyes widened as she struggled to catch it all. She only had the tip in her mouth, so plenty missed and flowed down her chin.

"Why?" I sighed in frustration as she sat back, her mouth closed and thick globs of cum on her chin. The crest of the orgasm was minimized by the bare physical contact she had maintained. Riley opened her mouth to show me all of my cum. "Fuck that's a lot!" I laughed at how full her mouth was.

She gave me a thumbs up then crawled over top of me. I realized what she wanted and tried to plead. "Ri—"

Her pussy enveloped me and she pressed her lips against mine to feed me yet another load of cum. I could either swallow or choke and found myself going along with her. Even after it was all gone, she kept kissing me, grinding against me.

"Eat me," she said when she finally pulled away, pushing me down the bed.

***

Afterwards we lay in bed. I had gotten hard again eating her, but she had made it clear I had gotten my reward. We cuddled and talked about anything except sex and last night. Eventually though we had to come back to it.

"I, uh, I like being mean to you," Riley admitted. "That makes me an awful girlfriend, doesn't it?"

"Maybe not for me," I admitted.

"What? Why?"

"I—" I looked at her. "I am going to kick myself for admitting this, but I like when you're mean to me too."

"Oh."

"You've always seemed too good for me. Like you should have some movie star life with a boyfriend that's better than me."

"Ha, the whole 'bigger' thing?" Riley laughed and stroked my chest. "You're plenty big in all departments for me."

"I'm glad you think so, but it's still hard for me to know that, to believe it." I paused. "I have no idea if that made sense or not."

"I think I get it. Kind of like how I couldn't believe every guy really wants me."

"Yeah, like that!" I sighed. "Anyways, uh..." I trailed off. I knew what I wanted to say, but I felt like I couldn't ask for it. I looked away from her and my eyes settled on the chastity device sitting on the nightstand. I didn't realize I'd been staring at it until she reached for it.

Riley knelt between my legs and started slipping the ring around my balls and dick.

"Uh, Riley? What are you doing?"

She looked up at me and smiled warmly. It was the kind of smile someone gives when they see you for you. "What we both want." She slid the cage on and clicked it into place then removed the key. "I love you Tommy."

"I love you too," I pulled her in and kissed her.