An Uptight Girl Learns to Relax - Part 4

Click here to read the previous parts of the story.

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Your sex life with your girlfriend has gotten better, but that's only because she's been fucking another man behind your back. He has a hold on her. She can't quit him. She can, however, get jealous when he fucks another girl...

Ian was trying his best to listen to the conversation unfolding around him - it was about the mayoral race, he was fairly certain - but he couldn't bear to commit his full mental resources to it. Politics had never been his thing and the longer the conversation went on the more irritated two his friends - one a liberal and one a conservative - seemed with each other.

It was right as their voices got loud enough to draw the attention of everyone else at the party that Ian attempted to intervene.

"Whoa, whoa, let's take a breath," he said while noting the signs of arousal - not the sexual kind - in both of his friends. One had sweat on her brow and the other boasted an enlarged set of pupils that were not aided by any sort of substance.

"Ian, honestly, what the fuck do you care?" Sarah asked.

He smiled. "I don't and you know that. The question you should be asking, though, is why you care so much about something you have no control over. I'll bet your heart is pounding right now, and not in a good way. I'll bet your hand is a little sore from how tight you've been gripping your drink. I'll bet you feel like you need to get up, step outside, and get some air. It's worth getting worked up like that over important things, but in the grand scheme of things, the election of a new mayor won't have a gigantic impact on your life."

She shot him a look and said, "You're wrong about that, Ian. A conservative agenda will drive this city into the fucking ground. It will be uninhabitable."

Ian knew what Tom - Sarah's partner in argument - would say next. It would be some version of what she'd just said. He'd phrase it differently, of course, and he'd insist that he was making a different point, but he wasn't. They were both so fearful of what the opposite political side would do that they'd collectively lost their minds. Ironically, that fear was the one thing they shared in common and there was probably a way for them to bond over it. Of course, there was no chance of that and Ian suddenly felt like it was entirely pointless to put even an ounce of energy into calming them down, so he got up and walked away as they went back to arguing.

As Ian searched for a new conversation to join he spotted Julia coming his way. She was adjusting her cardigan - of course she was wearing a cardigan - but noted that it wasn't buttoned at all and that her dress was tight around her chest and actually revealed a touch of cleavage, which was a very new thing for her. Ian's loins came alive immediately as he imagined fucking Julia in that dress.

A moment later, Mark appeared. His cheeks were flushed red and he was fidgeting with the top button of his shirt. Ian smiled as he was fairly certain that Julia and Mark had just fucked and that they'd done so at someone else's house. He was stunned. Then, for a moment, he was proud of himself. It was twisted, of course, to feel that way, but he took credit for the fact that Mark had just gotten laid. After all, Julia had only opened up sexually after she'd begun her affair with Ian.

"Mark, Julia," he said while raising his drink in a mock toast, "good to see you both."

Mark nodded, took Julia's hand, and kissed her on the cheek.

"Actually, I need to use the bathroom," she said. "I'll get us drinks afterwards. What would you like?"

"Red wine would be great," he replied.

Julia turned to head for the bathroom and Mark walked past Ian and settled next to Sarah and Tom, which made perfect sense. Mark wasn't especially political, but he was the kind of guy who wanted to seem like he was interested in important things like politics. He'd listen to their conversation, he'd mostly stay quiet, and every once in a while he'd offer his support when someone made what he suspected was a good point. Ian had seen it play out countless times at their gatherings and he knew that it was the sort of thing that made Mark less likable. He'd even seen people roll their eyes when they thought Mark wasn't looking.

Ian watched the party from afar for a short while and then headed for the kitchen. He could have told himself he was doing so to escape, but that wasn't true. He was hoping to talk to Julia when she appeared to get drinks for her and Mark.

To his delight, she smiled at him when she entered the kitchen. He returned her smile and she brushed her hair behind her ear and turned away.

"Was the sex good?" Ian asked.

"What sex?"

He laughed. "Are you telling me that you and Mark didn't sneak away to have sex? That I didn't run into you right after you'd finished?"

She grabbed two plastic cups - it wasn't a high end party - and filled them nearly to the brim with red wine.

"Was it good?" Ian asked.

Julia closed her eyes and took a deep breath. Ian couldn't help but stare at her breasts, which looked full and soft and perfect in the dress. He wondered if she was wearing a nice bra that pushed them up a little, if she'd purposefully dressed to look good, if she'd dressed to look good because she knew he was going to be at the party.

"It was good for one of us," she replied.

Then half of the wine in her glass disappeared down her throat.

"Did he leave you hanging?" Ian asked.

She nodded.

"And are you feeling quite pent up?"

"Yes," Julia admitted, though her voice was rather soft, like she was embarrassed to say it out loud. The rest of the red wine slid down her throat. She'd finished a full glass in two gulps. She quickly refilled it, though.

Ian studied her for a handful of seconds and asked, "Did you fake an orgasm?"

Her head whipped towards him and for a moment there was genuine surprise in her eyes. "How did you..." she began before trailing off. She gripped her plastic cup of wine but it remained on the counter.

"Just a guess," he said. "An informed guess, I suppose. You see, I'm pretty sure that you've become, well, let's say awakened, sexually speaking. I'm also pretty sure that what was once a decent sex life with Mark has taken a downturn. I'd bet that he used to make you cum, let's say, half the time he fucked you. Now I'd bet that it's a lot closer to never. Maybe ten percent of the time."

"Fuck you," she said, but her heart wasn't in it. She wasn't disappointed with him. She was disappointed with herself, or Mark, or the universe at large.

Julia lifted the wine to her lips and this time she took a measured sip. She closed her eyes and a tremor of emotion worked its way through her before she looked at Ian.

"He's fallen deeper in love with me," she began. "Since I started...since we started...since that first time. He's...I don't know, he's more devoted to me. He sends me loving texts multiple times a day. He gets me flowers. He buys me gifts. He did all of that to a certain degree before, but there's way more of it now. The thing is, it feels fucked up because you're responsible for it."

"How so?"

She sighed loudly and her shoulders sank. Another sip of wine made its way down her throat. She looked at the counter, ran her fingers over the smooth surface, and then looked at Ian once more. He noticed that her chest had turned a gentle shade of pink, like she was turned.

"You've changed me. Sexually speaking. I'm more open and eager. I give him blowjobs. We fuck in different positions. We fuck outside of the bedroom. We fuck with the lights on. I wear lingerie for him. You opened me up sexually and then I opened Mark up sexually." She gulped the wine, took a deep breath, and looked over her shoulder before saying, "Our sex life - and our relationship, if I'm being honest - is better because I'm cheating on him with his asshole friend-but-not-really-a-friend."

Ian wanted nothing more than to pull Julia close, push her to her knees, and slide his cock into her throat. He wanted her beautiful eyes to look up at him as he fucked her mouth, as he told her what a good slut she was, as he pushed his dick deep down her throat and climaxed while she played with her wet pussy. He wouldn't be doing that at a party filled with his friends, of course.

"But your sex life isn't actually good, is it?" Ian asked. "Your sex life with Mark, that is. I think we both know that I make you cum every single time I see you. Multiple times, in fact. I think we both know that I give you orgasms even when I'm not with you."

"You're such an asshole," she said. A moment later, Julia added, "And I really, really need your cock inside me."

Ian couldn't help his excitement, which manifested in a slight bulge in his pants. He shifted his body to hide it - he didn't want someone to walk in and see it - and resisted the urge to pull Julia close, push a hand down the front of her dress, and shove his tongue in her mouth.

"You should stop faking your orgasms," he said. "Mark will never learn of his inferiority if you keep faking your orgasms. He'll never adapt. He can't get better at fucking you, of course, but he could eat your pussy after he underwhelms you with his dick. He could use his fingers. He could let you use a toy while he's fucking you."

She laughed. "Yeah, emasculating my boyfriend is a great way to keep him happy. Keep the suggestions coming, Ian."

"Okay. Here's a suggestion. Ride his dick until he cums. Then immediately sit on his face and ride his mouth until you cum. If he complains about it afterwards, tell him that you deserve to have as good an orgasm as your pussy gave him."

"He's got a point."

Ian and Julia both looked towards the voice and saw Sarah standing at the edge of the kitchen.

"Sorry. I should have knocked or something. I didn't hear much. Just the part about you sometimes faking orgasms with Mark," she explained. "And Ian's right. I've done that. Faked orgasms, I mean. It seems like the nice thing to do when you're in the midst of it, but then it's six months later and the sex still sucks because he thinks he's a god in bed or something."

Sarah leaned towards the wall and her eyes went wide. She reached up to balance herself and Ian smiled. She was a little tipsy, which was probably why she was more than happy to offer up her thoughts on Mark and Julia's sex life.

"Did you ever...can I ask, did you ever do the other thing he mentioned? The thing about..."

"About sitting on his face after I sit on his cock?" Sarah asked.

Ian realized that both women were tipsy and he could scarcely contain his delight at getting to witness the conversation. It was a million times more interesting than anything having to do with the mayoral race.

"No, but I wish I had. To be honest, if a guy isn't willing to let you sit on his face, I'm not sure he's worth being with. You know?"

Julia leaned against the counter, smiled, and said, "You know what? I think you're right."

Sarah made her way to the counter with all the alcohol, positioned herself in the generous space between Ian and Julia, and silently made a drink. It was heavy on vodka with a few ingredients to take the edge off, though Ian couldn't imagine it would taste good.

"Would you let a girl sit on your face, Ian?" Sarah asked.

"I would," he replied. "I have, in fact, though not after sex."

"Why is that?"

"Because the women I'm with cum when I fuck them," he said.

Sarah looked at Julia. "He's confident, isn't he? Do you think he should be that confident?"

"I wouldn't know," Julia replied.

"Is it terrible if I can't help but want to find out if he's earned that confidence?"

Ian saw that Julia tried her best to hide the jealousy she must have felt. It was on her face, though. It only lasted a moment and Sarah might not have noticed, but Ian did.

"You know I'm still here, right?" he asked.

Sarah turned to him, sipped her awful drink, and smiled. "Ian, let's not pretend that you're some sort of chaste man. Everyone at this party knows that you're something of a man about town. That you fuck. The truth is, you have an excellent reputation, which is why I'm pretty sure that you've earned that confidence you displayed. I guess I'd have to sit on your face before sitting on your cock if I wanted to do both."

She didn't seem drunk - tipsy at best - and the woman standing next to him seemed utterly unhinged compared to her typical self.

"Well, I think I might leave you two alone," Julia said as she grabbed the two glasses of red wine she'd poured and departed the kitchen. She did manage to shoot Ian a look right before she walked out, though. It was too quick for him to fully parse, but he thought he saw both jealousy and a sense of desperation on her face, like she was pleading for him not to fuck Sarah.

"You were right, you know," Sarah said as she inched closer.

"Right about what?"

"The politics stuff. I mean, I disagree that it's not important. In fact, that's a really fucking stupid way to think about it. But, you were right that I was way too worked up about something I have no control over."

She kept moving closer until their arms touched. Then she looked up at him and stared at his lips, which was a near universal signal that she wanted to be kissed.

"Sarah, are you drunk?" he asked.

"No, Ian. I have control of all my faculties. I haven't had sex in two months. I haven't sat on a man's face in years. I know that you're probably the only guy at this party that could fuck me without it being a huge ongoing thing. I'm not going to get pathetic texts begging for another hook up. I'm not going to be berated if I don't get in touch with you. I'm only going to get what I need, which is a face to sit on for a while and a nice big dick to ride until I have a really great orgasm."

It was an intriguing proposition, which was why Ian happily accepted. He left the party first, Sarah departed not long after, and they walked back to his apartment to have exceptionally good sex that included her sitting on his face and his cock. There were two more rounds after that, both ending in thoroughly pleasurable orgasms for them.

Ian invited Sarah to spend the night, but she declined, got dressed, kissed him deeply, expressed her gratitude for his service, and left.

After his refractory period had concluded, Ian was struck by a desire to be a little bit of an asshole, so he grabbed his phone and composed a text to Julia.

"It's a shame I didn't fuck Sarah bareback. If I had, I could invite you over and make you suck her pussy juices off my dick before I pumped my load down your throat while telling you how hard she made me cum."

His relationship - such as it was - with Julia had unleashed a chaotic side of Ian that he hadn't been fully aware of before indulging in his desire for her. He liked how he felt when he tapped into that chaos, though, when he pushed her buttons and her boundaries.

"Fuck you," she replied just a few minutes later.

"I want a picture of your pussy. Right now. Go to the bathroom, spread your lips, and take a picture for me. I want to see that you're wet, Julia."

"Mark is sleeping right next to me."

"I don't give a damn about your boyfriend. That much should be clear by now. I know you got wet at the thought of sucking Sarah's cunt juices off of my cock. I know that it triggered your slutty side, that the thought of it made you want to masturbate and I want to see the evidence."

Ian didn't actually know if any of that was true, but he was fairly certain. He didn't have to wait long to find out. Julia took the picture. She was wet. Her pussy lips glistened with desire.

"I want you to go back to bed. I want you to put your hand in your panties and masturbate. I want you to think about me as you do. Think about sucking my dick after I've fucked Sarah. Think about swallowing my cock. Think about me cumming down your throat. Think about me fucking you. Think about me pounding your tight cunt while you scream my name. You will masturbate for at least half an hour and you will not cum. You will not cum until tomorrow morning when you show up at my place."

"Okay," was all she texted back.

Ian expected to be called an asshole or told to fuck off, but it thrilled him that she'd simply surrendered. "Oh, and I want you dressed in as close to a slutty outfit as you own. Day slutty, I suppose. No night club stuff. A short skirt. A cropped t-shirt or sweater. That sort of thing."

"You're such an asshole, Ian," she replied.

He smiled. He'd grown to find the response rather charming. He was an asshole, but he also happened to be an asshole that she'd developed an obvious sexual affection for.

"I'll see you tomorrow, Julia."

She offered no response, but Ian knew she'd do as he told her. She liked doing as he told her. She liked the risk. She liked how naughty it felt. She liked being his slut.

Julia showed up in a pleated mini skirt that barely reached mid thigh. She'd paired it with an exceptionally tight cardigan that also revealed a little of her stomach. She was carrying a bigger bag than usual and he could see an article of clothing poking out of it. She'd likely changed into the outfit she was wearing somewhere along the way. He smiled at her ingenuity.

"Unbutton the cardigan," he said.

"What? No. Please, let me in."

He shook his head. "Unbutton the cardigan right now or you can turn around and go back to your boyfriend."

Julia looked up and down the hallway and then hastily unbuttoned her cardigan. She had on a push-up bra that made her breasts look spectacular. Ian imagined them painted with his cum and made a mental note to ensure he remembered to finish on her tits for at least one of the orgasms he'd be having that morning.

"Good girl," he said. "Come here."

Julia stepped into his arms. They kissed as the door shut slowly. He lifted the back of her skirt and grabbed her ass with both hands. He ran his finger over the thin fabric of her thong and rubbed her asshole, eliciting a surprised moan into his mouth.

"Did you do as I told you last night?" he asked. "Did you masturbate without cumming?"

Julia nodded. "It was really fucking hard, you asshole. My panties were soaked by the time I was done. Like so wet I had to change them."

His fingers found their way into her panties and slipped between her pussy lips. He grabbed a handful of her hair, pulled back to expose her neck, and leaned down to kiss her.

"Fuck," she said softly.

"What do you want, Julia?"

"You, Ian. I want you. I'm...I'm such a fucking slut and the world's worst girlfriend, but I want you."

"Tell me more, Julia. Tell me exactly what you desire."

He was fingering her vigorously by that point and her eyelids fluttered as she moaned.

"Ian...I want you to do whatever you please with me. I want you to use me. I want you to fuck me like Mark can't fuck me. I want you to show me just how fucking worthless my boyfriend is in bed. I want...I want you to fuck my throat and my cunt and I want you to fill me with your cum."

He pulled his fingers from her pussy and slipped them in her mouth. Julia sucked dutifully and he kissed her neck while fondling her tits with his free hand. She was his to do with as he pleased. She was a toy for him to enjoy, though Ian found great pleasure in the notion that using her would also bring her great satisfaction.

Ian took her hand and walked Julia to his living room. He removed her panties and instructed her to undress him. She did so slowly, showering his skin in kisses and caresses, though he forbade her from touching his cock, which he could see was all she really wanted.

Ian then sat on his touch as Julia stood in front of him in her miniskirt, bra, and unbuttoned cardigan. She looked fantastically sexy and she seemed to feel that way, too, as there was not even a hint of self-consciousness.

"Did it make you jealous that I fucked Sarah?"

She nodded. "I know I don't get to be jealous. You're not my boyfriend. I understand that. I do. Still...I felt it. I...I don't know why, but I felt it. Like, a lot. I thought about sneaking out of the apartment last night. About coming over here. About begging you to fuck me so that you'd fall asleep thinking about me instead of her."

"I still fell asleep thinking about you," he said, putting a bright smile on her face. "I was thinking about today. It makes me an asshole, Julia, but I liked making you jealous. I liked the idea that you were at home with your boyfriend and wishing that you were the one I was fucking instead of Sarah."

Julia stepped towards him but Ian held up his hand. He then wrapped his fingers around his cock and began to masturbate as she watched.

"Did you and Mark fuck again after the party?"

"We did. I was horny."

"And did you sit on his face after he disappointed you?"

She shook her head. "I couldn't do it. I faked my orgasm again."

Ian smiled. "You need to stop doing that, Julia, but it's not really my concern. In fact, it's probably better for me if your boyfriend continues to be a disappointment. That way you'll continue to want my cock, to want to give yourself to me, to want to cheat on that pathetic unknowing cuck."

A twinge of guilt crossed her face. Ian held out a hand and Julia approached and took it. He pulled her into his lap. He guided his cock into her pussy. The guilt disappeared.

"Ride it like a good slut," he said. "Ride it. Cum on it. Make me cum inside you. Then you can climb off it and suck your cunt juices and my seed off of my shaft. You can throat it. You can show me what a good girl you want to be for me. Then you can stay on your knees and keep on sucking until I'm hard again."

Julia did everything he ordered. She rode him with wild abandon. She came twice while doing so. She made him cum inside her. She climbed off his dick and sucked it clean. She kept on sucking until he was hard again. She did so while occasionally pushing her fingers into her pussy, scooping out some of his cum, and shoving it into her mouth.

Once he was ready to go, Ian had Julia get on her knees on his couch. He moved behind her and rubbed his dick over her pussy lips. He pushed the head inside her and quickly pulled out. He rubbed the head over her ass cheeks and pushed between them. He rubbed it over her asshole and her hips moved forward immediately.

Julia didn't say anything, though. Ian slid his cock into her pussy once more and noted the residue of cum and cunt juice over her asshole. He reached down and rubbed his thumb over it. He had his other hand on her waist so Julia had nowhere to go.

Then he pushed his thumb inside her. She moaned as he filled her asshole while fucking her pussy.

"That's a good girl," he said.

Ian thought of having anal sex with her, of splitting open her asshole with his cock. He thought of fucking Mark's girlfriend in the ass and it turned him on immensely. He liked that he'd get to have a hole that Mark didn't get to have. He liked that Julia would let him have her asshole, that she wouldn't necessarily want to but that she wouldn't fight it, either, that she'd give it to him because she wanted to make him happy.

Ian resolved to take her asshole at some point. He'd work his way up to it, though, as he wanted it to be a decent experience for her.

He kept his thumb moving in and out of her ass while fucking her pussy. He told her to rub her clit. He came inside her with his thumb in her ass. He came inside her while she came.

When he was finished, Ian pulled out and Julia spun around and sucked his dick clean without being told.

"You need to buy a butt plug," he said as she throated him. "You need to start wearing it regularly."

She looked up at him. He saw the fear in her eyes.

"Yes, I'm going to have anal sex with you," he said. "It won't be anywhere near as painful as you're fearing, though. We'll take our time. We'll work our way up to it. Then, when I take your ass, you'll give me an orgasm unlike any other and it will feel good to have done so. I think we both know it will feel good to give me a hole that Mark isn't allowed to have."

She moaned, confirming his suspicions.

"We're getting breakfast after this," he said. "You're wearing your slutty outfit. Then I'll bring you back here and fuck you a few more times. Then I'll send you back to your boyfriend so you can ride his cock and ride his face. I know you've done it before. I know you can do it again. He needs to understand that he doesn't always satisfy you, Julia. He needs to be put in his place."

She moaned loudly at that and Ian resolved to push her harder to put Mark in his place in the future. He sensed that it would work to his advantage in some way. He wasn't quite sure how, but it was good to keep an open mind.