She Deserves It Ch. 02

"Sit the fuck down pussy," Dan grabbed me by the hair and pushed my face down on the bed next to Riley's. She twisted her head to look at me. Her eyes wide as she watched Dan manhandle me.

Her mouth opened and she wheezed as she came, struggling to scream but without enough air to do so. Her eyes rolled back in her head and her hand shot out, grasping at me. She found my balls, and I grunted as she squeezed hard. I couldn't even double over in pain as Dan pinned me in place.

Her grip loosened and she fell back. Dan released her and me, but we both laid their limply as he continued to fuck her.

"Oh god, I love you Tommy," Riley leaned to kiss me, but Dan grabbed her roughly.

"You're fucking me not him." He pressed his lips against her and the two made out.

"Holy fuck Dan, that was incredible!" Riley giggled. "God that was exactly what I needed!" Dan grunted wordlessly. "God, I love you just fucking using me in front of Tommy. Do you like that?"

He grunted. "Fuck yeah I do. You like my thick cock?"

"I fucking love your cock baby! It's so much bigger than my boyfriends!"

"Ugh I can tell, your pussy is tight as hell. Won't be soon though!"

Riley could sense Dan was getting closer. "Dan baby, I want you to cum in me. Fucking make me yours!"

"Shit really?" Dan was in disbelief, but he picked up his pace. Riley moaned and rubbed his chest and I watched as Dan grunted and then poured cum into my girlfriend. He collapsed on her and they kissed and whispered.

Eventually he fell to the other side of her. "Wow. You two are fucking kinky!"

Riley laughed. "Want to see him eat your cum?" She reached out to stroke his cock.

Dan's eyes widened. "Uhhh." Dan looked unsure, but I saw his cock twitch in Riley's hands.

"HHhmmm, seems like some part of you likes it. Likes how at least for tonight you're my man... How about this. Watch and I'll let you fuck my ass."

"Riley no!" I gasped in disbelief. We had both been exploring anal and she had promised I could have her ass once she was ready.

"What did you say to me?" Riley said her eyes narrowing.

"I mean, uh," I tried to backtrack. "Please, Riley, please..."

"Eat me." Riley looked pissed. I hesitated. "What the fuck are you waiting for? You already swallowed his cum once tonight you fucking faggot." Her words shocked me, and I felt my chest clench. My cock had a different reaction, and I felt a long strand of precum ooze out.

"What?" Dan asked confused.

"Oh yeah, what do you think I did with that mouthful of cum you gave me? He fucking swallowed it right there in the bar in front of everyone like the little bitch that he is!"

I didn't think it was possible to feel any more humiliated, but there it was. I gave up. There was no winning against her, not that I wanted to. I pushed myself up only to be greeted by more laughter.

"See, look how fucking hard he is!" Riley taunted. "A real man would have put me in my place like Dan just did." Riley shook her head and looked at Dan. "Now you can see why I need you. Tommy's good for some stuff, but sometimes I just need a real man."

I settled between her legs. Riley's hand still worked Dan and he was hard as a rock now. I kept my eyes down as Riley spread her legs. Dan had cum a lot and globs of it hung from her pussy. As soon as my tongue touched her, Riley gasped. I heard the sound of kissing. Somehow that felt even worse. She was making out with him and paying intimate attention to him while I pleasured her.

She rubbed my head gently. Usually when I cleaned her, she was aggressive, but this time she stroked me like a favorite pet as I dutifully sucked Dan's cum out and swallowed it. She was starting to moan softly into Dan's mouth. I pulled gently on her labia with my lips and then slid to her clit, my tongue teasing her softly. I traced soft circles, applying gentle pressure that I increased slowly as her hips started to move.

"Ummmph," she grunted, cumming for the second time that night. She broke away from Dan. "Oh Tommy yes baby, make me feel good!" I kept up my work until she gently pushed me away, a happy look on her face. "God that was amazing!"

She looked warmly at me then rolled over and kissed Dan. They made out and I awkwardly sat there on my knees until Riley pulled away.

"Do you want to get my ass ready, or should Tommy?"

She was still going to do it! I couldn't fucking believe it. "Riley..."

She giggled. "Sorry he's being so whiny! He's just pissed because yours will be the first cock in my butt."

"God damn, really?" Dan looked eager.

"Oh yeah. Every time you see me, you'll get to think about that," Riley kissed him. "Think about how you ass fucked your best friend's girl right in front of him. Took my anal virginity. Do you like that?"

"Ugh yeah!" Dan looked down at me. "I kinda think it would be hotter if he has to get you ready. How fucked up would that be?" It was clear he was starting to get into the role.

"OOhhh, fuck that is hot!" Rile gasped. She crawled on top of him and started kissing him. "I'll just keep this warm while he gets to work." She grabbed his cock and lowered herself onto it. From my vantage I had a clear view of just how thick he was. My girlfriend's pussy was stuffed to its limit and her lips gripped his manhood tightly.

"Start with your tongue," Riley moaned between kisses. I had a perfect view of her ass hole in this position. I normally loved eating her ass, but Dan's cock was way too close for comfort. There was no way I wasn't going to bump into it. "If you don't get going you can leave and close the door behind you. Five, four—" I had no time to think, only to lean forward and get to work. "Ah yes," Riley sighed as my tongue found her ass.

The sound of her and Dan making out filled the room as I licked then tongued her backdoor. I was painfully aware of Dan's cock just inches from my mouth, as he kept himself hard using gentle thrusts. Riley started to relax as I got her wet and when she was easily taking my tongue I sat back, ashamed of my own dripping erection.

I wet my finger and then started to work it into her butt. I could feel Dan's cock sliding inside of her, her ass tighter than normal thanks to his thick cock filling her pussy. I could hear the wet smack of their lips as they kissed.

Riley's ass was soon taking my finger easily, and I knew it was time for a second. I eyed Dan's cock and figured three would probably be necessary. I got up to grab the lube and Dan and Riley just kept kissing, making out like teenagers that were alone.

The second finger was harder to add. Her ass clenched tightly around my fingers, resisting until I suddenly felt her relax. She groaned as I eased them in to the second knuckle before starting to slowly fuck her rear passage in rhythm with my friend's dick.

I used my fingers on her ass until I was able to drive the full length in and out easily, then lined up a third. She was warmed up now, because this time she took it easily, groaning in pleasure. "Oh god yes, I'm ready!" Riley gasped after just a few minutes. I eased my fingers out and watched how her tight virgin ass gaped slightly. Riley rolled off onto her side and popped her leg up. Dan slid in behind her, wrapping his hands around her and fondling a breast. She turned her mouth to kiss him.

Her pussy was wet and open, and I watched as Dan ground against her. His cock slipped into her pussy and Riley giggled. "Wrong hole!"

Dan chuckled. "A little help bro?"

Riley gasped and looked down at me with wide eyes. "Oh god yes Tommy. Put him in my ass!" I shook my head, trembling. "Baby, if you don't help him out, I will never let you in my butt."

"Riley, but—"

"No buts!" Riley laughed. "Well, no butt for you."

Dan chuckled. "Come on man, no big deal. We're all friends here." It was easy for him to say since he wasn't the one helping his girlfriend lose her anal virginity to a friend. I reached out and slid my hand towards Dan until my fingers made contact. His cock was hot and hard and twitched as my fingers brushed it. Riley watched me intently. "Bro don't play with it, just guide it in."

Riley's face was flushed and I knew she was enjoying every moment of my humiliation. I wrapped my fingers around his cock and pulled him out of my girlfriend's pussy. He felt huge in my hand and my face burned with shame. He pulled his hips back and I moved the tip back to Riley's ass. I glanced up and Riley was watching me as Dan kissed her neck and ear.

He pushed forward and I had to grip him tightly as Riley's ass resisted the intrusion. He pushed forward keeping the pressure up and I watched as Riley's tight backdoor parted to accept my friend's cock. He went slow and it wasn't until my hand bumped her butt that I realized I was still holding his cock and didn't need to be. I jerked away and glanced up to see Riley watching me still.

"Fuck you feel huge," Riley moaned. "Please go slow."

"I know what I'm doing," Dan grunted. He was going slow. Taking very small slow strokes that progressively opened her up. Riley's body quivered and I couldn't believe she could fit his huge cock in her.

"Ah yeah baby, hold it there," Riley begged when Dan had lodged himself fully in her. She leaned back and started kissing him as she got used his dick. Dan's patience wasn't infinite, and he soon started slow thrusting motions. "Oh fuck yeah..."

Riley let her head fall to the bed, breaking the kiss but making it so we could watch me. She just stared at me as she took it up her ass, making small soft mewling noises with every thrust. "Oh, Dan baby, you might make me cum."

Dan just grunted. "What a fucking great ass, you really fucked up letting me in here Tommy."

"Oh, shit," Riley groaned. "Oh, keep fucking talking to him. Call him Tommy."

My face burned but my cock leaked precum. I wanted desperately to stand up and bury myself in my girlfriend's vacant pussy, but knew she would get upset for ruining her time with Dan.

"Ugh, you hear that Tommy? Your girl likes my cock in her ass. You'd better get used to seeing this because I plan on fucking it often." Dan grunted. "Fucking hell dude, you're such a bitch. If I had known, I would have fucked her months ago!"

"Ugh, yes oh fuck yes," Riley groaned. Her eyes were wide with lust. "Come here baby!" I got up on the bed and she pushed my head down so I had a close up view of Dan's cock working her over. Her pussy was soaking wet and her juices were leaking out and down her leg.

"ACH!" I screamed as I felt her fingers grab onto my balls and squeeze them hard. She slapped my cock and I curled up.

"Cup his ball baby, make sure he puts a big load in me," Riley hissed. She had a wild look in her eyes, and I felt her start to twist my balls sending waves of pain and nausea up my abdomen.

I desperately reached for Dan and slid my hand gently underneath him and felt his heavy balls in my hand.

"Oh fuck baby, oh fuck!" Riley came hard. "Oh god I love you Tommy! Oh fuck!" From my viewpoint I saw her pussy clench trying to milk a nonexistent cock. Her ass spasmed and I watched as Dan had to force himself deeper to avoid being pushed out. It must have felt amazing because I suddenly felt his balls start to move and then he was grunting out an orgasm. I could see an inch of exposed shaft swelling with each jet of semen he shot into my girlfriend's ass.

The two collapsed together exhausted, Dan still firmly embedded in her ass. They were quiet and probably headed to sleep. I stood, my cock hard and my balls aching from weeks of arousal and the torture Riley had inflicted on them. I pulled a sheet over them then decided to head to the couch.

The chastity device was sitting on the end table. I hesitated. I knew she would want me to wear it, so I grabbed it on the way out, gently shutting the door behind me. In the kitchen I looked at my hard cock and dreaded what I was going to have to do to get it on.

I got some ice water ready and groaned as I dipped myself into the chilly bath. It was awful and uncomfortable, but my dick didn't flag.

"Tommy?" Riley's voice startled me, and I dropped the bowl spilling water and ice cubes all over the kitchen floor. She was standing there naked, looking sleepy. "What are you doing?"

"Um, I thought you would want me to put this on," I gestured to the cage on the counter. "I, uh, the ice isn't working..."

Riley looked so happy. I thought I saw tears in her eyes as she approached and wrapped me in a hug. "Oh Tommy, you're fucking amazing. I love you so, so much." She reached down and gently stroked my shaft. "I hope you had as much fun as I did! That was incredible!"

"Oh god Riley, oh god please, I need to cum so bad!" I was practically crying it felt so good.

"I know baby, ssshhhhh, I know you need it. You did so good tonight. Just let me help you," I hugged her tightly. "You just got too excited seeing me and Dan. Just let it all out."

The orgasm crashed down on me hard. My knees started to buckle and I found myself using Riley to avoid falling. She ripped her hand away as the first jet of semen shot out. "Aaahhhh," I groaned in frustration as my balls emptied itself all over the floor. I looked at her with need.

"Awww, poor baby," Riley smiled at me. "Did you really think I was going to make it good for you after you told me no?" She reached down and slapped my sensitive cock then picked up some ice cubes. She rubbed them on me. I tried to pull away. It felt like cold fire and I shriveled instantly. She had the cage in place before I could think.

"Oh god Riley," I moaned. I wanted more. She kissed me on the lips.

"You made a mess. Clean it up then join us in bed." She walked off, her naked ass taunting me as I bent to start cleaning.

***

I woke and stared at the ceiling. From the light coming in I knew it had to be after eight, but I didn't feel like moving. Riley and Dan had fucked twice in the night, once in her ass and once in her pussy. Each time Riley had shaken me awake roughly to watch, but otherwise the two had ignored me.

I rolled over and found her looking at me. She kissed me and moved her lips to my ear. "I want to be alone with him this morning. Can you make us some breakfast?" I was done resisting. I nodded and started to slide out. "Hey I love you. I love you so fucking much."

Despite everything I loved her too and to hear that she still loved me made me feel unbelievable. "I love you too Riley. I—" I felt like crying.

She reached out and grabbed my hand, squeezing hard. "Ssshhhh, just think about how sexy I am. You're feeling the drop. Just a few more hours and then this will be over."

"Yeah," I said, not feeling any better.

"Here," she pulled the key off her neck and handed it to me. "Go play with yourself while you listen to us. Don't cum though."

I left the room gripping the key. I started some coffee and bacon. As soon as I heard a soft moan I moved over to a stool and unlocked myself. Despite everything I was hard quickly.

"Ugh fuck you feel so good," I heard Riley moan loudly. She was making no effort to hide her pleasure. "No like this. I want to make love to you." It felt like a punch to my gut, but I had to stop playing with myself to avoid cumming.

"No silly, I love Tommy." Riley giggled. "Don't worry we can still fuck. HHHmmmm, yeah just like that." Their voices dropped, replaced by the sound of kissing and Riley's wet pussy being screwed by my best friend.

"Yeah baby, yeah don't hold back, fill my pussy for me," Riley started begging. I heard Dan grunting and knew he was cumming in her yet again. I heard some soft chatter and laughter.

"Yeah, I really do love him," Riley giggled. "He's the best boyfriend ever."

Dan must have rolled over because now I could hear him. "I had no idea he was like this."

"I don't think he did either until we started down this path. He loves it though."

"So, we can still fuck? He won't mind?"

"He doesn't really get a choice, that's the whole point. Sexually, I'm in control."

"Damn." Dan started laughing. "Really glad I didn't end up in your clutches."

"Aww, I can be sweet!" The two laughed and then kissed. "Look I need you to understand something. I am never ever going to leave Tommy or do anything to hurt him."

"Uh, pretty sure I saw you practically rip his balls off last night."

"Oh, yeah I mean a little pain can be fun, right? But that's all in good fun. I'll know when I've found his limits."

"Yeah, and then?"

"Well then I'll sit right at them," Riley sounded delighted with herself.

"Fuck you're actually a bitch," Dan teased.

"Hey, you should be nice if you want to fuck me again."

"You want me to be nice to you? I thought you wanted me to treat you like the slut you are."

"Um, yeah let's go with that one. Actually, uh, this here, this loving stuff. This is Tommy's. I'm only doing this once and never again. You can stick your cock in me, fuck me, spank me, whatever you want, but this is the only time we will ever make love."

Dan was silent. When he spoke, he sounded hurt but trying to hide it. "Okay I can be your sex toy."

"Oh hush. You had to know I was Tommy's. He's your friend! I'm your friend."

There was a deep sigh. "I know. You're just so goddamn beautiful. It's hard not to hope."

"Aww, thanks! Means a lot coming from a man-slut like you."

I heard soft kissing sounds and realized they were screwing again. Dan's voice was deep and loud through the door. "Fuck Riley, I'm not the cheating slut." Riley moaned. "You like cheating on him, don't you? I bet you didn't even tell him ahead of time I was coming over. That whole threesome thing was just a lie to get me here, right?"

"Yes!"

"Fuck and he just stood there and watched like a little bitch."

"Oh fuck yeah, keep going baby. You fucking showed him what a real man is like!"

"Yeah, and he'd better get used to it. Not like he would stop me. Did you see the way he was playing with my cock? I bet he wants to suck it!"

"Oh god yes! Oh fuck!" Riley came and I heard Dan grunting. It was a relatively muted orgasm They both sounded worn out.

"You really like when I'm mean to him, don't you?"

"Oh yeah," Riley giggled. "Feel free to treat him like a bitch, but uh, just remember I need you guys to be friends still."

"Yeah, I go it," Dan groaned. "Fuck I'm hungry."

"Tommy's making us breakfast," Riley said I heard feet. The door flew open and she grinned at me. "Although he may have gotten a bit distracted."

I was sitting there, cock in hand blushing. "I, uh, there's coffee and bacon."

"Good enough for me!" Dan slapped me on the back, his cock dragging across my leg and leaving a trail of his cum as he slid past.

Riley watched me. "Tommy, come clean me up and I'll let you fuck my ass."

I was up in a flash and quickly followed her back into the bedroom. I attacked her pussy with more enthusiasm than I ever had. As soon as she felt clean she pushed me away and rolled over. She grabbed her phone and set a timer.

"Three minutes is all you get. Better be quick!" The clock was already running.

I quickly lined up and started to ease myself in slowly, but Riley pushed back taking me easily. "Babe, you'd better not hold back if you want to finish. Don't worry about me. Dan's cock is a lot bigger than yours and he stretched me out real good!"

I knew he was bigger, but he wasn't that much bigger and her ass still felt tight. The words had the desired effect though and really got me going. "Oh fuck you feel so good babe. Oh my god thank you so much!" I was fucking her hard trying to cum.

"Aww, you're welcome. I love you and you were so good last night. I'm glad to hear my ass still feels good after Dan's big dick!"

"So good, oh fuck so good!"

"Hhhhmmm, do you like the way his cum is lubing me up for you? You'd better because that's the only time you're ever getting in my butt!" The timer went off and Riley squeezed hard, popping me out as I drew back.