An Uptight Girls Learns to Relax - Part 5

Click here to read the previous parts of the story.

---

What if you discovered that your girlfriend had bought a butt plug? Would you think she wanted to try anal sex? Would you even consider that she bought it to loosen her up so another man could fuck her ass?

"Ian?"

The familiar voice pulled Ian's attention from the novel in his hand and he turned to see Mark standing at the end of the aisle with a stack of books in his hands.

"Keeping the place in business?" Ian asked as he gestured towards Mark's would-be purchases.

Mark's lips curled into a slight smile, but Ian could see the general disdain he knew that Mark felt for him. If only Mark knew that Ian was fucking his girlfriend that disdain would transform into something far more malignant. The notion put a smile on Ian's face and he tucked his book under his arm and strode towards his friend-but-not-really-his-friend and clapped him on the shoulder.

"How's it going, Mark?"

"Good. Good." He glanced at the book in Ian's hand and saw the cover, which featured a depiction of an alien planet. "I didn't figure you for a science fiction reader."

"I'll bet you didn't figure me for a reader at all, Mark," he replied. "And fair enough. I don't come off as a particularly well-read man, and I suppose I'm not. I tend to lean towards fiction that high-minded folks like yourself won't go anywhere near."

Mark might have wanted to disagree with the notion he was high-minded, but his arms were bursting with books the snobby set (the sorts of people who talked politics (and most other topics) like they understood anything about it) gravitated towards. Ian was being an asshole, of course, but since he'd started fucking Julia he had even less patience for Mark and he knew full well that he wouldn't spend a minute of time with him if they weren't tied together by their participation in a mutual friend group.

"How's Julia?" Ian asked, amping up the assholery.

Mark looked surprised at the inquiry. His eyes lit up, though, and Ian wondered if his efforts to make Julia a more sexual person had bled into her relationship, which would inevitably lead to more orgasms for Mark, or at least a greater variety of orgasms.

"She's really good," he said. Then there was a flash of vulnerability. "Though I...okay, look, you and I aren't exactly good friends. We both know this. But, weirdly enough, I feel like I can ask you this question. Just try not to be an asshole about it."

It was a moment of complete honesty between them and Ian found it refreshing. "I'll try, but no promises."

Mark rolled his eyes, took a deep breath, and said, "I found a butt plug. Or what I learned was a butt plug when I took a picture of it and did the Google Lens thing to look it up." He looked at Ian with a hint of desperation in his eyes. "Oh, wait, sorry, I should say that it's Julia's. Or it has to be Julia's because it's not mine."

Ian tried his best not to smile. He knew the butt plug was Julia's. He'd seen it. He'd put it inside her on a handful of occasions. He'd fucked her ass with it while pounding her pussy from behind. She'd bought the plug at his instruction, after all, so of course he was going to play with it when she came to his apartment to get a heaping helping of the kind of sexual treatment she'd come to crave since Ian first opened her up.

"You still didn't ask a question," Ian said. "So I'm not really sure how I can help."

"Oh, right. I just...what does it mean?" He leaned in and whispered, "Does she want to have anal sex?"

Again Ian contained the smile that desperately wanted to rush across his face. He'd instructed Julia to buy the butt plug because he intended on having anal sex with her and he didn't want it to be painful. What he hadn't said was that he wanted her to open herself up a little more, to think of her asshole as more than just an emitter of waste, to think of it as yet another source of pleasure, if not for her then at least for Ian. So no, she didn't want anal sex. She was going to have it, though, and it wouldn't be long before she'd given up her anal virginity to him.

In the moment, though, Ian grappled with giving Mark something approximating a genuine answer or trying to lead him to a place where he decided it would be a good idea to try and put his cock in Julia's ass. She wouldn't like that, of course, especially from her boyfriend. It seemed cruel, though, even for an asshole like Ian.

"I'd say it's a sign that she's interested in anal play," Ian answered. "I mean, how could it not be? It might be that the toy isn't for her, though? Maybe it's for you. Maybe she wants to introduce ass play to your relationship."

Mark recoiled at the notion, though his posture softened after he'd seemingly let the idea wash over him. "Is that something you'd do?"

"Would I let a girl plug my ass? Yeah, I would. I haven't been with a girl that was into that sort of thing, but yeah, I would. It's just an ass. It's not like putting something in there changes your sexuality, you know? If anything, it might make you a little more open-minded about all things sexual and there's nothing wrong with being more open-minded about sex."

Mark looked away and Ian noticed a slight smile on his not-really-a-friend's lips.

"Have you already gotten a little more open-minded, Mark?" Ian asked. He knew the answer, of course. Prior to Ian convincing Julia to cheat, her sex life with Mark had been as vanilla as it gets, including almost always having sex in the dark and sticking largely to missionary. Now there was sex all over the apartment, there were multiple positions used, there was facesitting, there was even a bit of Mark tasting another man's cum in his girlfriend's pussy, though he didn't know that. Ian did, though, and it thrilled him every time he thought about it.

"A little, I guess. I don't know. It's all driven by Julia. She's...different. Not in a bad way. But different."

"Well, you could just ignore that you found the butt plug," Ian said. "Or hell, you could get one of your own."

Mark shook his head. "No. I couldn't do that. No."

"You can. Of course you can. You don't have to, but you can. But there is some risk, of course, since you don't know why Julia bought a butt plug." Ian studied Mark for a few seconds and then asked, "If she wanted to have anal sex, would you be up for it?"

His eyebrows shot up. "Weirdly, I hadn't thought about it. I guess I would, though. I mean, it strikes me as kind of gross, if I'm being honest, but I think I'd still be happy to do it for her."

"And what if she wanted you to be on the receiving end? What if the butt plug leads to a strapon leads to her taking you from behind?" Ian asked.

Mark seemed a bit put off. "Never. No way. Why would you even suggest something like that?"

"I'd do it," Ian said. "I mean, I'd try it, at least. Why not? What's the harm?" Ian was fairly certain he wouldn't like it, but he was fairly certain he really would do it.

Mark looked away for a second and Ian could tell he was uncomfortable. He considered pushing it - there was bound to be a sex toy shop somewhere nearby - but he decided to let Mark go.

"Alright, man, I'm going to get back to finding a sci-fi book and I'll let you get back to buying your high-minded literature," Ian said.

Mark chuckled and it seemed clear that they'd actually bonded a little, that despite Ian's dislike for Mark that there was probably a road that would lead to some sort of genuine friendship between them. That wasn't really possible, though, not with Ian fucking Mark's girlfriend on a regular basis.

"See you around, Ian," Mark said.

Ian waved and watched Mark turn and head for the register. He pulled the book out from under his arm and resolved to continue his free reading session - the bookstore didn't exactly frown on it, but they couldn't have been excited that he testing out books before even considering buying - but instead he pulled out his phone and considered sending Julia a text. Should he let her know that her boyfriend had found the butt plug, or should he let her discover that on her own and struggle to come up with an explanation?

Ian decided a warning was in order so he fired off a text and returned to reading.

---

Ian was tucked into a booth in a darkened corner of the bar. In front of him was a tumbler with a single, massive ice cube surrounded by a mixture of dark liquor, brown sugar, and bitters. A twist of lemon rested on the rim of the glass and Ian hadn't yet tossed it onto the table. As it turned out, he liked a bit of visual flair with his drinks.

A woman slid into the other side of the booth and for a moment Ian didn't recognize Julia. Her blonde hair was down and wavy. She'd done her makeup to accentuate her cheekbones and was wearing lipstick and eye shadow. She wore a skimpy black silk camisole and her nipples were quite clearly showing through the thin material. Ian had caught a glimpse of a dark red skirt that left quite a bit of thigh exposed. Julia had worn a slutty outfit at his behest in the past, but this wasn't that. This was sexy. This was the kind of sexiness he wasn't sure that Julia could pull off.

"Damn," he said, bringing a smile to her face. "You look stunning, Julia."

"So do you, for what it's worth."

Ian had on slacks and a button up. He didn't often dress to impress, but he could pull it off when he wanted to.

"Did Mark see you before you left?"

She shook her head. "I think he would have been confused. He's out with a few friends tonight. A bachelor party, but the nerd version. They're playing board games and watching a movie, I think."

Ian smiled. 

"What? No snide crack about my boyfriend?"

He shook his head. "No."

"Is that because of your bookstore run-in with him?"

"Maybe."

Julia smiled and Ian felt her foot against his knee. She slid her hips forward a little and he smiled as the journey continued until her foot rested between his legs. Then, with a bigger smile, she asked, "I hear you'd be willing to let a woman fuck you with a strapon."

Ian returned her smile. "Be honest, how did Mark share that bit of information with you? Was he smug? Did he act like I was a freak?"

She shook her head. "I think, in a weird way, he looks up to you. You're far more worldly when it comes to women than he is and he's a bit envious of that. I think, more than anything, he was mystified by it. He can't quite wrap his head around the idea that a straight man would get fucked in the ass for any reason."

Ian's cock was hard under the table, but a high-heeled footjob will do that to a man.

"Did you mean it?" she asked.

Ian nodded and Julia studied his face from across the table. "Are you getting any ideas?" he asked. It wasn't the conversation he'd pictured them having when he showed up at the bar, but the drink in front of him was his second and he was feeling loose.

"Would it be weird if I did have ideas?"

"No. I mean, given all the things I've done to you, I suppose I couldn't blame you for wanting to pay me back."

She rubbed his cock harder and bit her lip. "I like the things you've done to me. I don't want or need revenge, Ian. I gave myself to you so you could do those things. I surrendered happily."

"And now, perhaps because of the things I've showed you, you find yourself wondering if it might be fun to fuck a man? To stroke your cock and slide it into him from behind? To grab his hips and fuck him while he grunts and groans?"

"Something like that, yes."

Ian couldn't take his eyes off of her. Not only did she look sexier than she ever had, but she'd seemingly discovered a level of confidence she hadn't possessed before.

"Are you wet, Julia?"

"Yes."

"And are you wearing your plug?"

"Yes, I am."

Ian slid out of the booth and stood by the table. Julia looked up at him and licked her lips. He gestured to where he'd been sitting and said, "Join me."

Julia got up and slid past him, pressing her ass into his crotch in the process. She paused for a moment to extend the pleasure she offered him and then Julia stepped past him and moved into the booth. Ian joined her and rested his hand on her thigh.

Their lips met a moment later and his fingers traveled up the smooth skin of her thigh. He found her panties quickly and pressed his fingers hard against them. He was greeted with warmth and wetness. An excess of wetness, in fact, signaling that perhaps merely dressing in such a sexy manner and strolling down the busy city streets was enough to dampen her loins.

"What did Mark think of your plug?" Ian asked as his lips trailed over her neck.

"He asked if I wanted to have anal sex."

Ian moaned. "And do you?"

She didn't answer at first. Instead, she moaned as Ian pulled her panties aside and slipped two fingers inside her.

"Do you want my cock up your ass, Julia?" he asked.

Her eyes were closed. Her back was slightly arched in her seat. "Yes."

Ian pulled his hand from her panties and his fingers slipped into her mouth. Julia sucked them clean like she was fellating him and her hand found his bulge through his slacks, stroking it vigorously in the darkest corner of the bar.

Eventually, Ian pulled his fingers from her wet, eager mouth and leaned away from Julia. She looked disappointed at first, but then she reached across the table, grabbed her drink, and took a sip.

"Did Mark ask anything else about the plug?"

She smiled. "He asked if I wanted him to wear it."

"And what did you say?"

"I asked if he'd be willing, after I got over the surprise of him asking, that is."

Ian sipped his drink. "And was he willing?"

She nodded. "Amazingly, he was. I guess wearing a plug is a lot different from getting fucked, at least in Mark's mind."

Ian studied Julia and marveled at how different she looked from the bookish version of herself she usually presented to the world. The most incredible part, though, was that she seemed comfortable in her new skin. Ian wanted to believe it was because she was comfortable with him, because she liked dressing sexy for him, though he wasn't convinced that was the case.

Julia threw back the rest of her drink and set the glass down with more force than was necessary. She swallowed hard, grabbed Ian's cock through his slacks, and said, "I've decided that I want to fuck you, Ian. Maybe not anytime soon, but I want it. I want to wear a cock. I want to bend you over. I want to slide into your ass. I want to pull your hair and spank you as I fuck you, as I call you names, as I make you take my cock until I'm screaming with pleasure."

"Well, look how far you've come."

"How far you've brought me," she corrected him.

"Fair enough. I'll tell you what, you can fuck me right after you fuck your boyfriend."

Ian spotted a fire in her eyes, though he wasn't sure if she was frustrated at his demand or eager to take on the challenge of convincing Mark to bend over and take it up the ass.

"He'll do it for you, Julia," Ian said. "I saw it in his eyes when I talked to him at the bookstore. He might not enjoy it, but he's enamored with you and growing more so with each passing day. If you want to fuck him, Mark will bend over, spread his cheeks, and take it."

She leaned over and kissed his neck. He could smell the alcohol on her breath. "Is that what you'll do, too, Ian? Will you bend over, spread your cheeks, and take it for me? Will you beg for it like a good slut?"

Julia was throwing his words back at him and Ian was surprised at how turned on he was. He'd unleashed a monster of sorts when he'd shown Julia the joys of expanding her sexual boundaries beyond missionary in the dark and now he got to play with that monster.

"We'll see," he said. "I suppose that's up to you. After all, if the person with the cock is compelling enough than they can get just about anyone to bend over and offer their holes."

She kissed him fiercely. "I want you. I want your cock inside me."

"Then let's go."

They rushed out of the bar and got in an Uber. They touched incessantly on the ride and rushed into Ian's building and up to his apartment. He stripped off Julia's camisole and tossed it on the floor. Her panties followed, but the skirt stayed on.

Ian pushed her to her knees and gathered her long hair in one hand. Julia lunged for his crotch but he pulled on her hair and kept her back. He unzipped his pants, freed his cock, and stroked himself slowly as she watched with genuine lust in her eyes.

"Is this what you want, slut?" he asked.

"Yes, please."

Ian inched his cock closer and her lips parted. "Can you feel it, Julia? That tingling between your legs? That overpowering desire for a cock that makes you feel so much better than your boyfriend's dick does?"

She nodded. "Please, let me suck it."

Ian thought of Mark watching or listening to his girlfriend offer herself. It put a smile on his face and a charge of electric pleasure went off between his legs. He slid his cock into her mouth and kept going until her nose was buried in his pubic hair. Julia could deepthroat and she could do it well. She'd learned quickly, too, a surefire sign of her desire to please him.

With a firm grip on her hair, Ian fucked Julia's mouth slowly and deeply. He gave her the opportunity to breathe every so often, but his rhythm was steady as her mouth and throat pleasured his cock and left him soaked in the thick saliva that came from deep in her oral cavity.

Finally, Ian pulled back and released her hair. He helped Julia to her feet and she smiled at him. He couldn't resist kissing her. She stroked him vigorously as their tongues danced.

"Please, Ian, fuck me," she said.

"In my bedroom. On your hands and knees in my bed."

Julia hurried to the bedroom and Ian followed. He undressed as he enjoyed the view of her ass with her skirt flipped up around her waist. He stroked himself and said, "Fuck yourself with the plug."

Julia reached back, grasped the plug, and slowly moved it in and out of her ass. She moaned and he saw her wince a few times, but it seemed that her training with the toy had prepared her for what was about to happen.

"I'm going to fuck your ass now," he said. "I'm going to cum in your ass, too. When I give you permission, you may rub your clit and have an orgasm. Then you're going to put the plug back in and go home to your boyfriend with my load in your rectum."

Ian took the plug from her and set it on his nightstand. He crawled into bed behind her, spit on his cock, spit on her asshole, and then pushed himself inside her. She gripped the bed sheets and groaned as he filled her slowly.

Ian pulled out and smiled at the sight of her ass gripping his cock. He knew it was wrong to take pleasure in having anal sex with Mark's girlfriend, but he fucking loved it. He loved that Julia was willing to give it up for him, that she was eager, even, to give him what he craved, what Mark would never have.

"When you get home, I want you to clean the plug, empty your ass, and then give your boyfriend a blowjob. While you do, though, I want you to rub the plug around his asshole. I want you to lube it before you do so. I want you to slide it into him eventually. I want you to anally penetrate that little bitch and make him cum while you're doing it. Take his load in your mouth, swallow it, and then kiss him deeply while you work the plug in and out of him. Prime him for the ass fucking you're going to give him, Julia."

She arched her back and moaned. "Can I masturbate?" she asked.

"Not yet."

Ian fucked her harder. Her ass was spectacularly tight and the view of his cock filling her was more than enough to bring him to the brink of a climax. "Play with your clit. Cum while I blow my load in your ass."

Julia dropped her head and reached back to rub her clit. Ian fucked her face down, ass up and spanked her ass while doing so.

"Fuck, I'm cumming!" he cried out before burying his dick in her ass and unloading. The notion that he was cumming where no man had cum before made the orgasm so much hotter. He pictured his seed spilling into her rectum, shot after shot flooding her anal canal while she filled his bedroom with wild, wondrous screams of pleasure.

Ian pulled out and slipped the plug back inside her. He collapsed onto his back and Julia straightened her body in his bed and crawled towards him until her head rested on his heaving chest.

"Do you want me to clean it?" she asked while grasping his cock at the base.

"No."

"I...I think I would, you know."

He smiled. The bookish, shy, buttoned up girl was now offering to give an ass to mouth blowjob. It turns out that good dick was all she'd needed to find her true self, sexually speaking, at least.

"That's not necessary," he said. "Though maybe next time I'll pull out and make you suck it clean before I cum in your ass."

She situated her pussy against his thigh and moaned softly while rubbing her clit against him, leaving a trail of wetness on his skin.

"Do you want to cum again, my little slut?" he asked.

"I do."

Ian slipped three fingers into her mouth and she rubbed herself vigorously against his thigh while sucking like she had his cock in her mouth. She came in less than a minute and he couldn't wipe the smile off his face.

"It's time to head home," he said. "I expect a text confirming that you did exactly as I instructed. Before the night is over, you'll have penetrated your boyfriend's asshole for the first time. I won't be the last, though."

Julia sat up and smiled at him. "I'm going to penetrate your asshole, too. Don't you forget about that. I will fuck you, Ian, and I will fuck you hard."

Surprisingly, Ian was looking forward to it.