Don't Date the Bitch in Apartment 23 Ch. 04

Disclaimer: I do not own Don't Trust the Bitch in Apartment 23. I do not make any money from the writing of this story.

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June was really starting to worry. Even by her girlfriend's standards, Chloe had been acting weird, and whenever June thought that she had seen the craziest thing ever Chloe had a tendency to introduce her to a whole new level of crazy. The same could be said for the twisted and kinky things in their sex life.

So in other words, this was either going to be really good, or really bad. Or maybe a mix of both, but June was definitely hoping for something good. Although honestly, at this point she just wanted to get it over with. Rip it off, like a Band-Aid. Or just for Chloe to really talk to her again. And really talk, not just dismiss her with a few words. So when they settled down to dinner she push the issue.

"Seriously, what's wrong Chloe?" June pushed, "And I know you, remember? I know when you're lying."

There was a long pause, and then without looking up Chloe admitted, "It's our anniversary."

June frowned, "No it isn't."

"Yes it is." Chloe repeated, before clarifying with a sigh, "It's the anniversary of you moving in right away because you're such a big lesbo and... and... that means it's-"

"The anniversary of the day we met." June's eyes went wide and doe-like, "Awww, Chloe-"

"You see this, this is why I didn't want to mention it." Chloe huffed.

"No, it's really sweet." June beamed.

"I don't do sweet." Chloe growled.

"Oh we both know that's not true." June scolded, before grinning, "I remember too, by the way, I just didn't think you'd want to make a big deal of it given we didn't do much last time."

"Didn't do much?" Chloe raised an eyebrow, "Is that what we're calling a day of my face buried in your vagina?"

Which of course caused June to blush becomingly, "Yes, well... I mean no. I mean... you know what I mean."

"Yeah, but it's so fun to watch you squirm." Chloe grinned, before becoming serious again, "I know that's not when we got together, but... it was the beginning of us, you know?"

"I know." June softly agreed, and then after a pause added, "We were such different people then."

"I'm still not sure how I feel about that." Chloe grumbled.

"I know." June smiled softly, treading very carefully as she told her girlfriend, "But I love this, ever so slightly, relaxed version of you."

"Same." Chloe smiled softly, before grinning wickedly, "Plus I loved pulling that stick out of your ass, and replacing it with my flag."

"Yes, well..." June blushed, admitting after a brief pause, "So did I. But then, I enjoy everything we do together."

"That's pretty obvious." Chloe pointed out quickly, before admitting as she reached over to take June's hand, "Me too. Which is also pretty obvious. But it's not just the sex. It's everything. Everything is better with you. And I hate that. I promised myself I would never be that girl, but here I am, that girl. That girl who defines happiness as being with someone. And remembers sappy shit, like anniversaries. Birthdays. Names. God, we even remember the things each other likes, and worse, tries it. I would barf if I wasn't so happy. And, and I always want to have you in my life. But being friends, or whatever we were at the start isn't enough. I need you to be mine. All mine. And I need guys to stop hitting on you. Or at least a little less. So... I just need you to say yes, okay?"

June frowned, "To what?"

"You can't tell?" Chloe gave a little laugh, before sighing, getting up and walking round the table and then she got down on one knee in front of her now wide-eyed girlfriend. There was then a long pause and then Chloe groaned, "Please don't make me say the words."

After gulping softly June gave a little smile, "I think you kind of have too."

"Oh come on June, you know what I'm saying." Chloe whined.

"Yeah, but if we're doing this, you're going to do it right." June smiled, "If it helps I'll totally say yes."

"Fine." Chloe grumbled, "June... will you marry me?"

Initially June was too busy grinning madly to respond. Then a look of betrayal crossed Chloe's face and June quickly snapped into action, pulling her hand free of her girlfriend's, cupping her face and then softly kissing her. June had imagined this moment a thousand times, and had technically already experienced it once, but that had been the wrong person.

It felt right at the time, but now June regret saying yes to him. She couldn't imagine ever regretting this though, as there was no doubt in her mind that this was truly the right person for her, and Chloe had proven it by being more loving and romantic than most people would ever give her credit for. Which was why although the kiss was soft and gentle it was easily the one of the most passionate kisses of her life and as June put everything she had into it.

"Just to clarify, that's a yes." June beamed once the kiss was over.

"Yeah, got that, thanks..." Chloe mumbled.

This response cause June to frown. Chloe still seemed nervous for some reason, which was weird. And worrying. Actually more worrying than anything else, but before June could really think it through Chloe was kissing her again, and this time there was nothing gentle about it. It was hard, and rough, and June almost felt like she was fighting for her life instead of kissing back.

Which she did, a lot. Her clothes weren't as lucky and they got ripped along on the way to their bedroom, which would never not be hot, even if it was very costly. It was also very encouraging, because it felt normal. Just Chloe ravaging her again. But no, Chloe had one more surprise for her, which revealed shortly after dumping a completely naked June on their bed and then crawl on top of her.

"I got you a ring, BTW, but I returned it and got another one." Chloe explained after a sigh once she was in position, "Then I returned that and got another one, and again, and again, and again, because nothing seemed, I don't know, good enough for you. We can pick one out if you really want, but it's nothing but an expensive accessory, and I have thousands of those. And I've given you thousands of those. Which is why tonight I wanted to give you something else. Something I haven't given anyone. Something I wouldn't give to anyone else. So... I guess you could say I'm giving you a ring, just not a diamond one."

When Chloe didn't immediately elaborate June gently pushed her, "Meaning?"

"Meaning... I want you to take my anal cherry." Chloe revealed.

"Oh." June blushed.

"What? Don't believe I'm still a back door virgin?" Chloe frowned.

"No! It's not that. It's just that..." June initially stammered, searching for the right words, "You've been very clear that I'm the bottom, and you're the top, in this relationship."

"Yeah, and that's still technically true given this is my idea and all." Chloe quickly pointed out, before sighing, "And I kind of miss men. And I'm certainly not willing to share. And I didn't think you would be up for giving me a freebie."

"Is that's something you want?" June asked softly.

"God no. Which is why I'm suggesting this." Chloe admitted, before quickly adding, "But more importantly I want to prove this is real to me."

June smiled, "I know that?"

"Do you?" Chloe frowned, quickly adding, "Because I had a talk with Luther, and he was only too happy to tell me all about you're chat with James about me and your doubts about us."

Looking horrified June quickly protested, "Chloe, I'm so sorry-"

"It's fine." Chloe grumbled.

"It isn't." June protested.

"This isn't my first time asking someone to marry me. And it sure as hell won't be my first time getting married." Chloe pointed out, "I've done it tons of times. I've pretended to be in love. I've even pretended to be pregnant. I've done it a lot for a cheap thrill, or to screw someone over, or for money, but not you. Never you. At least, not again. I'll add it to my vows too. And I'll do whatever it takes to prove this is real. But I thought we were past this. I thought you knew you could ask me anything, and I would tell you the truth."

"I do. I just had a moment of stupid doubt. I'm so sorry Chloe." June apologised, then after a long pause asked, "That's not why you wanted to marry me, is it?"

"No, I want to marry you because I love you." Chloe said, "I just feel I need to prove that love."

"You don't, and I'm sorry I made you feel that way." June said softly, biting her lip briefly before adding, "But if you seriously want to try this, we can try."

"I do." Chloe smiled softly.

"Then how about we warm up first?" June smiled.

"My thoughts exactly." Chloe beamed.

For a moment they just stared at each other, then they simultaneously leaned in for another soft kiss. June would have been more than happy with like an hour of that before they moved on, followed by another hour of foreplay, but unsurprisingly Chloe had other plans.

Plans which made June increasingly nervous, but also turned on, as Chloe retrieved her harness, strapped it to June and then started sucking it like it was real, making June gasp softly. She'd given many blow jobs in her life, mostly to Chloe at this point, but she'd never seen it from this angle and despite herself she found it hot, and weirdly relaxing, June smiling nervously and then placing a hand upon the top of Chloe's head to show she approved of this.

Chloe looked up at June and grinned around the cock, which of course caused her new fiancé to blush again, to her credit June maintained eye contact, making Chloe fall just a little bit more in love with her. Which was now a regular occurrence for her, which was why Chloe had done the unthinkable, actually propose to someone for real.

Just as she had said, it wasn't a scheme to get money or just a cheap thrill, Chloe genuinely wanted to be with this person for the rest of her life. And not just anyone, but another girl! Which seemed like a practical joke on her given her previous dislike of women and fondness for men, but maybe this just proved you couldn't help who you fell in love with. Because Chloe would have never picked June, but now she couldn't imagine her life without her.

Of course that was more than enough sappy words. Chloe was never fond of them, and while she had no doubt June loved them under these circumstances they just seemed like empty promises, words Chloe had said countless times before without meaning them. Which was why she revelled in the chance to prove herself with this twisted act.

Hell, just the build up to it was pretty twisted, given that after several minutes of bobbing her head up and down Chloe grinned again and pushed her head all the way down until her lips reached the base, meaning the full length of the dildo was buried down her throat. And best of all, June kept eye contact with her the whole time, which just made Chloe grin more.

She had always loved sucking cock, and it was so thrilling to get back to something she loved. Sure, it wasn't the warm, yummy treat of the past, and no matter how much Chloe deep throated it she would never receive a hot load from it, but this sex toy had an advantage which no other sex toy or real cock ever had, it was around the waist of June Colburn.

Which automatically made it the most important blow job of Chloe's life, and she gave her all to it like never before. Which not only involved deep throating, it involved holding that position while she choked and gagged on the dick before moving to bob her head again, this time her lips meeting the base with every downward stroke.

It was an extreme she used to give on the daily, but as she was out of practice Chloe ended up choking and gagging more than a high-schooler on prom night who was too chicken to go all the way. Which obviously made June look concerned, and it even looked like she tried to ask Chloe if she was okay, but Chloe just tuned her out and sucked even more enthusiastically.

Of course as much as Chloe loved sucking cock she was eager to get fucked with a cock for the first time in almost 6 months. She was also kind of curious about the anal, but mostly Chloe just wanted to get it over with so she could prove just how much she loved June, and so she could turn the tables back to what they should be.

So eventually Chloe pulled her mouth off the dildo and asked her lover, "So, ready to fuck me?"

"Ye, yes." June stammered unconvincingly, before forcing herself to sound serious as she added, "Yes."

Chloe grinned at the adorableness of her girlfriend, and then told her, "Well, you'd better prepare me then."

"How?" June asked softly.

"Same way that I just prepared you." Chloe said simply, before grinning again as she got on all fours on the bed, "Or more accurately, the way I normally prepare you."

"Oh." June blushed.

"Awww, come on June, don't be shy." Chloe grinned wickedly and wiggled her ass, "We both know you have plenty of experience eating my ass, except now instead of being my ass kissing bitch you're getting me ready to be your bitch. Mmmmm yeahhhhh, you're getting me ready for a butt fucking with your pretty little tongue. Oh yeah, pucker up and kiss my ass June! Kiss it and then fuck it! Oh fuck yeah!"

June wasn't shy, at least not in this case. She was just admiring the view. And enjoying Chloe's words. But the other girl was right, this was something she had experience in, which made her brave enough to get in position behind Chloe and give her what she wanted. Even if it was only a simple peck to her left butt cheek.

The important thing was it was a promise of more, and it was a promise that June soon delivered on, moving her lips back and forth between each of these cheeks and worshipping them just like she had been trained too. Well, mostly. Because this time was obviously different, and it was hard for June not to think about it.

It was incredibly nerve wrecking and out of her comfort zone, but then that was true for a lot of the things she had done with Chloe, and all of them had worked out. Well, almost all of them. There were a few wacky adventures along the way which weren't entirely legal, but if all goes well they would remain just a wacky story she could tell her kids about someday.

Maybe even their kids. But that was getting way ahead of herself, as was thinking about taking Chloe's anal virginity, so as hard as it was June did her best to concentrate on kissing her girlfriend's ass, while of course Chloe was only too happy to continue giving her encouragement.

"Oh yes June, that's it! Kiss my ass!" Chloe giggled with delight, "Ooooooh, that feels so good. You kiss ass so good June. Like you were born for it. Mmmmm yeahhhhh, you were born to be my little ass kissing bitch, ohhhhhh, but tonight June, I want you to make me your bitch. That means you will have to resist the urge to spend all night worshipping my butt, and fuck it, mmmmm, which means you got to spread apart the cheeks of mine and bury your cute little tongue into my fucking ass hole! Come on June, fuck my ass with your tongue, mmmmm, and then use a cock. Your cock! Oh yeah, kiss my fucking ass hole, oh fuck! Oh June!"

Although she did become a little lost in kissing Chloe's ass at least part of it was June teasing her girlfriend before finally giving her what she wanted. Or more accurately the first part of it, which was June spreading Chloe's cheeks and kissing her directly on the butt hole. Then she started sliding her tongue all over it, eventually even trying to push that tongue inside Chloe's ass, just like her twisted roommate had taught her to do.

Just like she loved to do. Oh yes, June loved to give Chloe a long, drawn-out rim job, which was just what June did. Even if it wasn't so much a sign of her love and submission to Chloe as it was about preparing her usually dominant girlfriend to be butt fucked, as much as she was still trying to wrap her head around that.

Then when Chloe was beginning to whine again June brushed her fingertips against the other girl's pussy lips, momentarily keeping her quiet. Then when she started complaining again June reluctantly replaced her tongue with a finger, slowly pushing it into Chloe's surprisingly virgin butt, both girls letting out a cry in the process.

Chloe's mostly of pleasure, although June was very worried that she didn't immediately go back to commentary. June almost stopped because of it, but no, if Chloe truly wanted that she would ask. In fact she would complain if June stopped. So she finished burying the finger inside Chloe's ass, and then after a brief pause started pumping it in and out. She then cautiously added a second finger, which clearly impressed her demanding girlfriend.

"Ooooooh yeahhhhh, that's more like it June. Mmmmm, we're really getting the party started now baby." Chloe grinned with delight, "Ohhhhh, your fingers feel so weird in my butt. And you know how much I like weird."

"Yeah I do." June grinned, "But if you really want to get the party started, why don't you beg for it like the bitch you are?"

"Oh really, you want me to beg like the bitch I am?" Chloe teased, "Well, we both know exactly what kind of bitch I really am, mmmmm, spoiler alert, it's a psycho bitch! But tonight, mmmmm, I wanna be your bitch, so how's this? Pretty please fuck my ass June, mmmmm, pretty please with sugar on top."

"Tempting..." June teased, before adding in a singsong voice, "But we both know you can do better than that..."

"Ooooooh, way to go June. Showing some backbone. I like it." Chloe grinned, before putting more effort into it, "Mmmmm, fuck my ass baby, fuck me with your big cock! I want you to shove every single inch of that giant dildo through my tight little virgin butt hole and sodomise me until I can't sit down without thinking about you. Mmmmm, like we both know you can't stop thinking about me whenever you sit down, mmmmm, or walk, or do anything, because you're a giant lez who wants to do anything to please me. That's why you're doing this, so stop beating around the bush, ha, and just do it already. Tear open that little forbidden hole and enter through the back door. Come on, pound that butt June! After all the ass poundings I've given you, here's finally your chance for revenge. Ohhhhh yeahhhhh, anally pleasure me, like I anally pleasure you. Just do it! Pop my anal cherry! Please June? Do it because you love me."

"Okay, okay." June murmured, having heard more than enough, "But spread your cheeks first. Yes, show me just how bad you want it with more than your words, and give me the perfect view of your pretty little back hole as I take it."

"Oh hell yeah, take it June! Take it!" Chloe gleefully agreed as she did as she was told.

Chloe grinned with delight, genuinely impressed by those words. Almost enough to admit that. Almost. Instead she just did as she was told, pressing her face to the bed sheets and slowly reaching back to pull apart her butt cheeks. There was a very long pause as June just stared at her butt hole, making Chloe second-guess her decision to push June into this.

Hell, she'd been second-guessing it this entire time, and ever since she came up with it, as June was such a natural bottom this just seemed beyond her. However Chloe just couldn't think of a better way to prove she was serious about wanting to marry this girl, so here they were.

Just as Chloe was about to tell June she didn't have to she felt that cock against her most private hole, causing the brunette to grin and open her mouth to offer up the blonde some more encouragement. But all that came out of her mouth was a cry of pain as June slowly pushed forwards, causing her ass hole to stretch.

Impressively she barely paused, and didn't waste time by asking Chloe if she was sure about this, and just got on with it, Chloe gritting her teeth as the one she loved slowly took her anal virginity. Which pretty much sucked as much as losing her regular virginity, except this cock was bigger and there was no chance of June ramming in all the way and then blowing her load in seconds.