She Deserves It Ch. 01

Chapter 1

A boyfriend's insecurity with his girlfriend leads to femdom.

Themes: Femdom, chastity, edging, cum eating, forced bi, cuckold, CBT, humiliation, male on male, pegging

*****

"I'm not saying she's cheating or is going to cheat," Dan said, getting frustrated. "I'm just saying she is the type of girl guys are going to throw themselves at in every situation. And not just some random dude on the street, but guys used to getting girls like her."

I frowned as I processed what my friend said. "I don't think she's like that."

Dan shrugged. "Believe what you want. Just know guys with bigger dicks, bigger muscles and bigger wallets are going to be after her, trying to lure her away. You slip up, start taking her for granted and she'll be gone in a heartbeat."

I took a pull on my beer, the doubt eating at me. Riley was something different. I'd dated attractive girls before, but she was just so far out of my league I wasn't even sure we were playing the same sport.

"Hell," Dan continued starting to chuckle. "I've got two out of three and only my deepest respect for our friendship keeps me from taking a pass at her."

***

"What're you thinking about, Tom?"

I snapped back into focus and looked down at Riley as she rested her head on my bare chest. "Are you happy with me?" I asked, feeling insecure as I recalled the earlier talk with my best friend.

I did well for myself, but Dan's words had opened up a chink in my confidence. I had put on a lot of muscle thanks to working out with Dan. I was on the rise at my job and had been promoted to a manager position in the Emerging Technologies division, but there were hundreds of guys like me in the city and girls like Riley didn't grow on trees—motivated, smart, sexy, and horny as an actress in a bad porno, I'd hit the jackpot with her and had no idea how.

"What, that's a silly question babe," Riley giggled. "You need to have more confidence in yourself!"

It was easy for her to say. Before dating her, I had thought the stories about models being discovered on the street was an urban legend, but she had been found on some field school trip when she was a freshman in high school. As if that wasn't enough, she only did it part time to pay for college and had quit as soon as she got an internship at GloboTron.

"I just feel like you're out of my league, like I don't offer enough," I sighed. "Like you're just with me until some guy with bigger muscles, a bigger dick, and a bigger wallet comes along."

Riley smiled sweetly at me. "Aww Tommy," she pulled herself up and kissed me deeply.

"Just, if there is anything I can do better or do for you, please just tell me," I pleaded.

She raised a finger to her lip and tapped it as she thought. "Weeeellll, now that you mention it..." Riley rolled onto her back and started pushing my head down. "Finish me off?"

"Wh-what?" I stammered, the thought of going down on her after sex causing my stomach to flip. "Uh, didn't you cum?"

"Yeah baby, but like really early on. Not my fault you lasted long enough to get me going again, but not long enough for me to finish."

"Uh, sorry."

"It's okay, but I need you now." She moved up and started to straddle me, her blue eyes fixing me in place. I'm 6'1" and 190. She is 5'6" and I would be shocked if she weighed 120. I could have thrown her off, but somehow she ended up settling her pussy down on my mouth. "Oh, fuck yeah," Riley moaned as she made contact with my lips. "Oh yes baby, eat me!"

I loved going down on her—before we had sex, but her current position gave me no choice. I cringed as I opened my mouth and tasted the mixture of our juices. I felt a drip of semen slide into my mouth. The worst part was when I realized that I liked it and was eagerly licking and sucking my own cum out of her pussy. My hands moved to her ass, helping pull her down onto my face.

"Oh, fuck Tommy!" Riley grunted, her pussy mashing down so hard I struggled to breathe. Her legs closed over my ears and the world went mute as she thrashed on my face. "Oh god sorry!"

Riley quickly slid down giggling as I gasped for breath. She kissed me and slid down to cuddle me. My erection bumped her. "Oh, someone's excited!" She reached down to stroke me. "You recovered so fast..."

I grunted and tried to push her over onto her back for another round, but she laughingly fought me off. "No way, you already cleaned me up, I don't want to get messy again!"

"What really?" I looked at her in disbelief. She giggled and blushed, but didn't budge.

"Hey, you asked if there was anything you could do for me, it's not fair to expect something in return."

"I—yeah you're right," I admitted. We cuddled and chatted then she sighed.

"I should go," Riley stood and stretched, her perky breasts bouncing lightly with her motion. "I can't wait to get a real job and not be on coffee and bagel duty for these 7 AM meetings."

"I remember those days," I laughed, recalling my own time as an intern. She grabbed her panties and slid them up her legs into place. "Maybe we can meet sometime tomorrow?"

Riley gave me a wicked grin. "I found this storage closet off the red-way. Think you could get away at 1?"

I scrambled for my phone to check my calendar as she laughed at my enthusiasm.

***

"Fuck me," Riley groaned as I pounded her from behind. She was bent over slightly, using a storage shelf to support herself. I had pulled her skirt up over her hips, and her pantyhose and panties were just below her ass. She made soft moans of pleasure as I worked her pussy.

I pulled her hair back so I could kiss her, her lips meeting mine aggressively. "Ugh, fuuuuck," Riley grunted and I felt her pussy clench on my cock as she came. "Damn Tommy, you make me feel so good!" Riley sighed. I had slowed my pace and met her lips as we kissed tenderly.

Suddenly my work phone blazed out, deafening in the small closet. "Shit!" I fumbled for it and saw an urgent message from Jack, my boss's boss. I read it in and moaned. "I have to go. Some idiot messed up something in the underlying calculations for the quarterly report. It's an all-hands situation."

"Awww, poor, poor Tommy," Riley laughed as she stroked my cock with her hands.

"You're not making it any easier on me," I complained, but her hands felt so good.

"Oh, I know," Riley's eyes glinted at me in the dim light. "It's fun though! Besides, I think you like it..." Riley stared at me, challenging me to disagree and I couldn't. My phone beeped again and she danced away and started straightening her clothes. We slipped out and I hoped when I joined the team they would think my flushed face was from running to join them.

***

I sat in my apartment frustrated and horny. The incident that had pulled me away from my work tryst with Riley had turned into a two day emergency that kept me busy seemingly all day and night. That was followed by Riley having to attend a late meeting to take notes for her team during a call with Asia. She was expecting it to go pretty late and was going to head home after. I was beyond horny and grabbed my laptop.

A few clicks and a wealth of porn was available. I clicked on popular and scrolled until something caught my eye. A pretty brunette with blue eyes looking into the camera and stroking a hard cock. I remembered the way Riley's hands had felt on my dick and if I squinted I could almost pretend the girl on the screen was her.

I started the video and pulled my cock out. I matched my strokes to hers, but soon realized I needed some lube like she had.

I moaned once I had settled down naked, my cock slick. The woman on screen worked the stunt-cock slowly, varying her technique to keep the dick hard and aroused. I found myself gasping along with the video, totally sucked in.

"What are you watching?"

I felt like I jumped a mile in the air and reached forward to snap my laptop shut, inadvertently catching my dick with the edge of the screen. "I grunted in pain as I tumbled off the couch.

Riley was standing above me laughing and holding her sides. "Oh no, are you okay?"

"I think my ego took the main beating," I groaned as I pushed myself up.

"I don't know, you seemed to be beating yourself pretty soundly when I came in," Riley looked so pleased with herself that I couldn't help but laugh along with her. What else could you do when caught jerking off?

"What are you doing here?" I asked, hoping to divert attention from what I had been up to.

"I wasn't needed so I thought I would come and help take care of you," Riley reached out and poked my dick, stroking it lightly with one finger. "Seems like you had it all under control though."

"Uh, look I uh-"

"Oh relax, I watch porn too," Riley grinned.

"You do?" I was shocked. Riley had never mentioned anything like that before.

"Oh yeah," Riley settled down next to me on the couch. "What were you watching?"

"Uh, just something I found online," I hesitated. She was looking at me expectantly. "Would you want to watch together?"

"Aw, I thought you would never ask!" Riley shrugged her jacket off and curled up next to me. I opened the laptop and propped it safely on the coffee table. "'Edging towards ruin'" Riley read out loud. "What's this?"

I shrugged. "Just found it on the popular list. I think it's just a long teasing handjob." I restarted the video and leaned back.

Riley giggled and wrapped her hand around me as the actress on screen did. "Hmm, and your choice had nothing to do with the fact that she looks kinda like me?"

"It could," I admitted slyly. "Fuck it's so much better with your hand." My cock was twitching as she worked it. I leaned my head back and just focused on the pleasure.

"Does that feel good baby?"

"Yes! Thank you so much," I gasped out. The wet noises from the laptop picked up in speed and Riley's hand quickly followed suit. I groaned and felt myself getting ready to cum when suddenly her hand was gone. "Fuuuuuuuck!" I groaned and raised my head to look at her. "What the fuck?!" She was laughing and pointed at the screen where the dick on stage was similarly twitching in frustration.

"This is fun!" Riley's face was flushed and I tried to pull her towards me and kiss her. "Nope! Hands to yourself you naughty boy!" She slapped at me until I gave up. "Hhhmmm, how does this feel?" she asked as she wrapped her fingers around me again.

"Oh god you're torturing me!" I gasped. "Please!"

"Aww, I can stop..." Riley started to withdraw her hand.

"No please!" I begged.

"Wow, I bet I could get you to do anything I wanted right now," Riley said happily.

I was in no position to disagree. Riley's hand was starting to move quicker and I heard groans of pleasure from the laptop and knew I was finally going to get to cum. I looked at Riley's beautiful face, her sparkling eyes. A grin formed on her face and she turned to look at me, her hand a blur on my cock.

"Ah, oh fuck, I'm gonna-" Riley's hand disappeared again and my hips thrust up involuntarily seeking stimulation. Muscle spasms ran through me and I reached for dick, desperate to finish myself off.

"No!" Riley grabbed my hand and pinned it. Cum shot out of my cock, coating my chest and abs. My dick twitched helplessly.

"Fuck Riley, what the hell?" I groaned. "Why did you do that?"

"It was in the video," she said as she stood, pulling her pants and panties off. She pushed me back on the couch and settled onto my dick. I realized I was still rock hard.

"Fuck, I haven't cum in a week, you didn't have to be a bitch!"

As soon as I said it, I regretted my words and braced for her anger, but Riley just started moaning. "Yeah! I was a real bitch, but you liked it, didn't you?" She was riding me hard and her pussy was hot and wet. "Fuck yes, oh fuck yes!" She leaned forward and kissed me hard, practically biting my lips as came, mashing her hips down hard on my cock. I felt a gush of liquid on my thighs and realized she had squirted!

"God damn Riley!"

She started shyly giggling. "I guess I needed that."

"You needed it? I recall a certain someone getting theirs on Tuesday and leaving me hanging..."

"True, but I deserve it don't I?" Riley looked sweetly at me and kissed me gently. My mind flashed to Dan's warning. "Isn't that what you said you wanted? To make me happy?"

"Yeah of course you deserve it. You deserve whatever you want," I assured her quickly, stroking her back.

"Good boy," Riley muttered softly. I felt my cock twitch at her praise. I don't know why she said that, but made me feel strange and good. "Have you had dinner? I'm starving."

"Not yet, maybe we could order something? We would have time..." I moved her on my lap some to bring attention to my needy cock.

"I was kinda thinking that taco place down the street? We can get tequila!" Riley pushed herself up. "I'll take care of this later," Riley twisted away leaving me hard in the air and playfully poked my erection. "I'm starting to think keeping you horny is good for me." She was smiling at me as if it was a joke, but something in her eyes made me wonder.

***

Tom watched as his girlfriend set out nail polishes for her Sunday night ritual of painting her nails.

"Do you want me to do that?" I asked, desperate for contact with my girlfriend. Riley had been true to her word and kept me horny all weekend. It honestly hadn't taken much teasing on her part.

Riley gave me a surprised look. "What's up with you? You usually hate when I do this."

It was true I had found it annoying. She spent a long time on it every single week. "Just trying to be a better boyfriend."

Riley laughed and tapped at her lip. "And it has nothing to do with the fact that I've been teasing you all weekend? I wish I had learned this trick earlier..."

I shifted uncomfortably, not sure how to respond. She leaned back and put her feet out. "What color?" I asked when I realized she wanted me to do it.

She grabbed her kit and I heard the clink of the bottles. "Pink I think! Here's the topcoat too." Riley settled back and put on a streaming TV show.

I took her foot gingerly and started by cleaning off the old polish. I tried to be gentle, holding her foot and carefully applying the polish to each nail as she watched TV.

As I finished up, I looked up to see Riley watching me with a smile.

"What?"

"You're really good at that," Riley complimented.

I felt myself blush. "Um, thanks? I've watched you do it a bunch."

"I guess you were paying more attention to me than I thought." Riley looked thoughtful.

"It's hard not to pay attention to you when you're around. Doesn't matter what you're doing."

Riley smiled and shuffled forward on the couch. My eyes darted down to her normal Sunday evening bottoms, a pair of panties. There was a distinct damp spot on the crotch. "That felt so good, I need you babe."

I felt a surge to my cock and quickly stood, fumbling at my belt, only to be gently pushed back down. "No, eat me babe. I don't want to mess up the polish."

"Really?" I asked in disbelief.

She pouted. "You want to make me happy right?" I nodded. "Then eat me Tommy. Be a good boy and get down on your knees."

I was in a daze as I knelt between her legs. Her scent was overwhelming and when I pulled her panties to the side, I gasped at how wet she was.

"Just don't stare at it," Riley tugged on the back of my head and lowering my mouth to her. I tried to go slow, teasing her, but she twisted her fingers in my hair and pulled hard until I settled over clit. "Oh, fuck yes, good fucking boy."

Her words filled me with the same odd warmth and sense of accomplishment. I looked up and she was fumbling with the remote. The show paused and was soon replaced by the pounding music of the dance music she liked to listen to. "Oh yeah, right there, Tommy." She held my head in place and started rocking her hips. I looked up and her eyes were focused behind me on the TV. Her lips parted and she gasped as juices flooded my mouth.

I struggled to breathe as she pulled me tight against her and started choking as she squirted into my mouth. Her grip ease and I managed to pull away. "Damn Riley!"

"Sorry," Riley giggled without sounding the least bit apologetic. She was watching the TV in her post orgasm high and I turned to see what she was looking at. It was just some DJ on stage with flashing lights.

"Who's that?"

"Oh DJ Light," Riley blushed.

"Got a crush?" I reached forward and tickled her sides.

"Stop!" Riley laughed as she squirmed. "It's not like you don't have celebrity crushes."

"It's fine," I laughed. "Still, making your boyfriend eat you out while you watch him? You going to return the favor?"

"No way," Riley smiled and shook her head. "Maybe something else you would like though." She fumbled with the remote and I gasped as the same blue-eyed woman from the handjob video Friday popped onto her TV. "I think we'll both really like this one. I've done some research."

The look on her face made me nervous, but there was no way I was going to turn down anything with how worked up I was. "Uh, should I grab your coconut oil?"

Riley grinned and pointed out the jar sitting on the end table. She had clearly planned this. "Get naked."

I was out of my clothes in a flash and seated next to her on the couch. Her hand brought me to an angry looking erection at the first touch. "Oh, fuck Riley."

"You'd better not cum early," Riley warned. It was her normal, girlish voice, but there was a steel in it that made me fearful to disobey. I groaned as she worked me to the edge, backing off before I was tipped over. After the third time I was desperate and would have done anything for release. My eyes were closed as I felt my orgasm building.

"Oh Riley, I'm going-"

Her hand jerked away and I moaned in frustration. I opened my eyes and looked at her. "Are we going to fuck now?"

Riley played like she was considering it then shook her head. "Nope, we're going to have a little talk." She reached out and started teasing my cock again. "You need to ask for a raise."

'Wh-what?" I gasped. I could barely focus.

"This week you are going to ask for a raise. You need to learn to stand up for yourself at work," Riley explained, her hand working me over.

"Do we have to talk about this now?" I begged.

"Yeah, because this way I know you'll do it," Riley looked pleased with herself.

I groaned and reached down and grabbed her wrist. "Riley..."

"I know you'll do it because if you do, I'll fuck you again and let you cum."

"Fuck," I felt my balls tighten. Riley somehow sensed it was coming because her fingers flew open and released me. She stood and admired her toes.

"Wow, so cute, thanks!" Riley walked to the kitchen and started washing the oil off her hands.

I sat there naked, confused, and with a throbbing erection. When she walked over, she hugged and kissed me. "Come on and get dressed. I'm doing this for you. For us."

I headed towards the door, but Riley stopped me. "Tommy, if you jerk off, I'll know." She was smiling, but somehow it didn't quite reach her eyes.

***

"Tom, come in and sit down," Jack said, pointing to the chair in front of his desk. He had always been friendly to me, but I felt a lump in my throat. I had requested a meeting with my boss yesterday and was surprised to get one on Tuesday with Jack. I technically didn't report directly to him, but functionally it often seemed like it. "Thanks for stepping in last week, that was a real shit show."

"Yeah of course, glad we could get it together."

"So, what did you want to talk about?" Jack leaned forward.

"Um, well," I cleared my throat and thought about the pep talk Riley had given me that morning at my desk. "I wanted to talk about my compensation. I've been taking on increased responsibilities over the past few years and I don't think my pay has kept up."