The Lesbian Diaries

Category: S through Z > Vampire Diaries
Dragon prints: 13607
Disclaimer: I do not own The Vampire Diaries or Legacies. I do not make any money from the writing of this story.

Dear Diary

Today will be different. I'll smile, and mean it. I'll say I'm fine, and mean it. Maybe I'll even say I'm okay.

I'll be good. I'll be normal. I'll be straight.

I won't lust over the other members of my cheer squad, who don't deserve to be leered at by a lesbian who can't control herself.

And most of all, I will not have inappropriate thoughts about my best friends, who I love dearly, and would never want to make feel uncomfortable.

I won't checkout Caroline's ass. I won't stare at Bonnie's tits. I won't think about stupid Vicky, and the things we could be doing if she hadn't moved away.

I won't have to give up something I love, or worse the friends that I love, because I'm a gay mess who can't control herself.


Hopeless Lesbian



Elena Gilbert never used to have a problem with changing in front of other girls, as she always prided herself on being athletic and thus did it all the time. Hell, she and her best friends had recently become cheerleaders, meaning that it really, really shouldn't be a big deal, but it was, and it was all Vicki Donovan's fault. She had shown Elena just how much fun girls could have together with their clothes off, and ever since then she just couldn't stop thinking about it. Which had been bad enough when she had Vicki around, who Elena could go straight to after cheerleading practice to work through her inappropriate feelings for her teammates, but the Donovan family had just moved away, leaving Elena without a boyfriend, and worse without a girlfriend.

Just thinking that made her feel so bad. Oh God, she was the type of girl who would cheat on a guy with his sister, or just because she was too much of a coward to admit to him, or even herself at first, that it was the sister that she truly wanted. So as frustrating as it was Elena was kind of relieved they had left, meaning Matt never had to find out how thoroughly she had screwed him over, without ever actually screwing him. But now she was constantly horny, and being surrounded by the perfection of the female form which was her fellow cheerleaders, particularly her best friends Bonnie Bennett and Caroline Forbes. God, Elena had become such a desperate little lesbian slut she could barely look at her friends without thinking inappropriate thoughts about them, and in moments like this, when they were changing in front of her, it was impossible.

So she kept her eyes straight ahead of her while she slowly changed into her cheerleading uniform for another long practice in which she would be surrounded by girls getting hot and sweaty with each other, counting the minutes and seconds before she could go home and masturbate herself furiously to those inappropriate thoughts rattling around her head. But she couldn't help but write some of them down in her diary, increasingly making it rather XXX-rated reading material. Which sometimes helped with the masturbation, but mostly it just left her feeling even more embarrassed, as it was proof she had betrayed their friendship by thinking about her friends that way. But she just couldn't help it, she had to do something otherwise she was going to go crazy.

"Okay everyone, get out there and start with stretches, I'll join you in a minute." Caroline announced, the squad already obeying their Captain as the blonde turned to one of her best friends and stopped her in her tracks, "Elena, can I have a word."

"S, sure." Elena stammered, trying and probably failing to hide her fear.

Oh God, this was it! Caroline had finally noticed Elena's longing stairs, either at her or the other girls, and was about to confront her. Or maybe she just smelt the desperate dyke slut on her? Or worst of all, she had somehow seen Elena's filthy diary entries on her and her teammates, and was about to not only kick her off the team but yell at her for being so disgusting, and threatened to kill her if she ever came near her or Bonnie again! And yet, Caroline didn't seem upset. No, she looked like her normal wonderful self, with even a hint of concern towards Elena. Which Elena really, really didn't feel she deserved for her thoughts, but she couldn't deny she was relieved when Caroline came up to her and smiled encouragingly at her.

"Seriously, are you okay?" Caroline asked, before immediately pushing, "And don't give me that I'm fine bull-shit, you're clearly not."

"But I am." Elena lied weakly.

"Is this about Matt?" Caroline guessed, "Because I'll miss him too. And Vicki. I mean, I know it's different, because you guys were dating, but I didn't think you guys were that serious, were you?"

Elena literally froze with horror, then she realised that Caroline wasn't implying that she was dating Vicky, and then relaxed and simply brushed it off, "You wouldn't understand."

"Try me!" Caroline insisted, pushing even further when Elena tried to leave, "Seriously, talk to me. We're not leaving here until you tell me what's going on with you, and do you really want to leave the rest of the squad stretching all day? Think about it, do you?"

There was a brief pause, then Elena lowered her head and softly said, "I can't!"

"Why not?" Caroline pushed.

"You'll hate me." Elena whined.

"Hey! Elena, look at me. Look at me!" Caroline demanded, stepping into her friend's personal space and pulling her chin up to look at her directly in the eye, "I could never hate you. I love you. I always will. I think you're amazing. I-"

Hearing such soft encouragement was the straw that broke the camel’s back, Elena did the one thing that she had sworn to herself she would never do, lose control around one of her beautiful friends. Oh God, she had to lean forward and press her lips against Caroline's. Instantly she recognised her mistake, but she was frozen with such horror that she just couldn't pull away, meaning the kiss seemed to last for hours. In reality it was only a few seconds, and it could be almost mistaken for an awkward sign of friendship, or at least Elena hoped that would be the case as she found herself staring wide-eyed at a very confused looking Caroline Forbes. Then to her surprise Caroline actually grinned.

"Took you long enough!" Caroline chuckled.

Then Caroline Forbes, easily one of the most beautiful girls in the entire school, if not the entire town and maybe even the entire world, actually kissed Elena! And this wasn't a simple gentle peck, but full on lips caressing lips, Elena's body thankfully working a lot sooner than her brain so she didn't embarrass herself again. Which was an extremely good thing, as she was pretty much unable to think for the next few long seconds, which again felt more like hours. Sadly she did embarrass herself a little at the end by chasing Caroline's lips as her friend pulled away, which caused the blonde to let out the most adorable giggle before pressing her lips against Elena's ear and whispering something which almost made the poor young lesbian literally cream her panties.

"Come, to my place after school and we'll... talk, about this." Caroline promised, before then turning around and leaving almost like nothing out of the ordinary happened.


Honestly Elena should have just changed back into her ordinary clothes and headed to Caroline's, maybe after dealing with her hormones in the toilets by fucking herself to climax. At the very least she should have taken a cold shower, but no, she headed straight out to the field where she proceeded to embarrass herself for an extremely long hour. It would have been bad enough with the memory of that kiss, and Caroline whispering in her ear like that, but her so-called friend made the whole thing impossible by giving her smiles throughout which could have been mistaken as encouraging. Elena knew better, although by the end Caroline had to do was look at her and Elena would mess up, almost seriously hurting another girl one time.

Which led to Caroline to suggesting when they were done, "You better let me give you a ride. From what I've seen you're in no fit state of mind to drive."

Sadly Elena couldn't disagree, so she found herself getting a ride to Caroline's house, something which had happened hundreds of times now, and was normally no big deal, but this was different. Of course, Elena didn't know exactly how different, and she was afraid to ask. Did Caroline just want to make out some more? Or did she want to have sex? Was she ready to have sex with one of her best friends? Sure, she did it with Vicky, but they never had the kind of close relationship she and Caroline had. What if this ruined their friendship? Which was something Elena really, really didn't want, but she couldn't turn back now, not after wanting this so badly. So after a long car ride filled with mostly silence, and a little awkward small talk, Elena found herself walking into Caroline's bedroom... and finding Bonnie there waiting for them.

"Oh, hi Bonnie..." Elena said awkwardly, then after her friend return the gesture she gently tried to get rid of her, "Erm, no offence Bon, but I really, really need to talk to Caroline alone. It's nothing bad, I swear, we just... I just..."

"Want to be alone with my girlfriend?" Bonnie smirked.

"Your-" Elena began, but she was unable to say anything else as she was just too shocked.

"Surprise!" Caroline beamed, the sound of her locking her bedroom door deafening in the mostly silent room before she explained, "We've been trying to find the right time to tell you."

"I wanted just to tell you, but Caroline was convinced you were having such problems keeping your gay under control that you'd make a move on one of us sooner or than later." Bonnie explained.

"And I was right, BTW." Caroline pointed out proudly.

There was a brief pause, then Elena finally managed to speak, "And... and you wanted that?"

"Hell yeah!" Caroline grinned.

"Vicky told us all about your arrangement before she left." Bonnie explained, "Vicky wanted us too... look after you. Have the same arrangement with you that she did. Obviously there would be three of us, which makes things more complicated, but Caroline and I  have talked about it and we really, really want to give it a try."

"Although to be clear, we're not asking you to be our girlfriend." Caroline added helpfully, "Just friends with benefits. So whenever you feel the need, you can call us. Ideally together, but we can pair off, as long as Bonnie and I are honest with each other when it happens. That way no one feels cheated on."

There was a brief pause, and then seeing that her friend was unsure Bonnie quickly added, "Of course, we don't expect an answer right away. Right Caroline?"

"Right." Caroline said, clearly disappointed by the idea, but as confidently as she could she added, "Take as much time as you need."

There was another pause, this one longer, then Elena stammered, "Seriously, you guys better not be pranking me right now, because if you are that so messed up."

"We're not." Bonnie reassured.

Yet another pause, this one brief, and then Elena asked, "So, I... I can kiss you?"

Bonnie smiled, "As long as were not in public. We're not ready to be out yet."

Elena nodded in acknowledgement, then turned to her other friend, "And I can kiss you?"

Moving closer Caroline reassured, "Oh, please do."

Bonnie was thrilled when Elena put that to the test, closing the distance between herself and Caroline, pulling the blonde into her arms and kissing her. Of course Caroline kissed back immediately, Bonnie's two best friends melting together in what was easily one of the most erotic things the young black girl had ever seen, which was really saying something considering just how kinky things between herself and her girlfriend had become. Thinking of Caroline as that label never failed to put a smile on Bonnie's face, and this time was no different, even though her girlfriend was currently kissing someone else. Which should have definitely made her jealous, but it didn't. Maybe it was because it was Elena, or just because it was so hot, but Bonnie just loved watching these two girls make out.

It then somehow became even better as her two friends broke the kiss with each other, and turned their full attention to her. They then smiled, joined her in sitting on the edge of Caroline's bed, and then took it in turns to kiss her. Elena first, making this their first kiss ever, something which was just as good as Bonnie had dreamed it would be, and she had been dreaming about it a lot. Although even then it couldn't compare to the joy of kissing Caroline, something Bonnie would always love above all other kisses. Then for who knows how long that pattern was repeated, until ultimately Caroline became impatient and started pulling off her own clothes, and thus earning a stern look from Bonnie.

"What?" Caroline protested, "She just said she was cool with it, right Elena?"

Before Elena had a chance to reply Bonnie told her, "I just want to make sure you know that any time you want to stop, just say the word. We don't have to do anything you wouldn't want too. And we can just make out. If, if that's what you want."

"I know." Elena smiled softly and hopefully reassuringly, "You guys are my friends, and I know you wouldn't do anything to hurt me. But to be clear, I never want you to stop. Not ever. I trust you. I want this. So please, do whatever you want to me."

Almost overwhelmed with lust Bonnie grinned and pointed out, "You should be careful about making promises you can't keep."

"Who says I can't keep them?" Elena flirted.

The two friends exchanged a smile, and then Caroline butted in, "Does that promise apply to me?"

"Uh-huh." Elena grinned.

"Good." Caroline grinned back, "Then how about letting me go down on you?"

Elena blushed, "Well-"

"Please!" Caroline whined, "It's like so unfair Vicky got to taste you first. I mean, I'm a way better pussy licker than her. Just ask Bonnie."

"It's true." Bonnie smiled fondly at her girlfriend.

"Please Elena, I love pussy soooooooo much, mmmmmm, and I swear, I'll eat yours so good. Make you cum nice and hard while my girlfriend watches. Make you beg me for more. Mmmmmm, make you think about my mouth all the time. Oh yes, please Elena, mmmmmm, give me your pretty little cunt!" Caroline pleaded, admittedly getting carried away.

When Caroline finally stopped talking Elena blushed a little, and then admitted, "I was going to say, well, I guess that would be okay."

"Oh..." Caroline mumbled, before grinning, "Great."

The last part of that little exchange made Bonnie chuckle that her girlfriend's inpatients had kept her from what she wanted longer, but the humour was quickly forgotten when Caroline pressed her lips firmly against Elena's again for another passionate kiss, this time involving her pulling Elena's shirt up and off of her. Obviously the kiss needed to be broken to achieve this, but it was a extremely positive sign that Elena had helped the process every step of the way, and then welcomed another kiss after it. During this one Caroline pushed Elena down, and removed the other girl's bra with practised ease. Then after about another minute of kissing Caroline started kissing her way downwards.

Again Bonnie was amused by Caroline's inpatients, but this was their first time with Elena, and surely they should be savouring this? Bonnie almost said as much, but then she supposed this could be seen as Caroline simply racing through the foreplay and leaving that to Bonnie. If that was the intention Bonnie shouldn't just be sitting back and watching, but she just couldn't help herself. She had just wanted to see this for so long, she didn't even scold Caroline when she barely spent any time on Elena's tits before undoing the pants of their friend and pulling them down as she kissed her way down the other girl's flat stomach to where she really wanted to be.

Caroline just couldn't help herself. She had been fantasising about eating Elena's pussy since before she and Bonnie got together, and ever since Elena had kissed her Caroline could practically taste it. Besides, Elena seemed pretty confident that this was what she wanted, but they were still in danger of her freaking out at any moment, which would blow their chances with their precious Elena, which Caroline just couldn't let happen. Not when she was confident as soon as her best friend felt her tongue on her twat any thoughts of stopping this would seem absurd, and she'd quickly become addicted to Caroline's tongue. After all, Bonnie did, and Caroline was confident in her abilities that she could do the same with Elena.

So Caroline raced to get to the finish line, although ironically when she was there she couldn't help watch for a few long seconds, and admire just how pretty her prize was. And just how delicious, Caroline actually licking her lips before she closed her eyes, leaned forward, stuck out her tongue and slid it over the tasty treat in front of her. Which was somehow even better than her fantasies about this, Caroline letting out a gentle cry as the taste of Elena's pussy hit her taste-buds, which in turn was followed up by a long moan as she slid her tongue upwards. Both of which were drowned out by the loud cry and moan that Elena let out, although Caroline was barely aware of that, as she was too lost in this heavenly flavour.

For the most part that continue to be the case for the next few minutes, Caroline lulled into a completely content state that she wasn't aware of what she was doing, or even the sounds her friend was making. Luckily she had spent so much time in between Bonnie's legs, and to a lesser extent Vicky's legs, to be able to switch to autopilot, and that's exactly what happened here. Oh yes, of it's own accord her tongue continued sliding from the bottom of Elena's pussy right up to the top, allowing that heavenly pussy cream to slide right down her throat and into her belly were it belonged. She even managed to mostly avoid Elena's clit, only occasionally teasing it as a hint of the pleasure to come.

Of course, even in that state Caroline was listening out for a protest from her best friend, because while it was literally a nightmare right now if Elena really wanted her to stop she would. Luckily that wasn't the case, and Elena just kept gasping, whimpering and moaning in pure pleasure. At least until she was silenced by Bonnie's lips, Caroline grinning against Elena's pussy as she looked up to see her best friend kissing her other best friend turned girlfriend, which again was literally a dream come true for her. Ironically it pushed her out of her daze so she could focus on the beautiful show that the other girls were putting on for her, much like Bonnie had been left to watch as she had her way with their precious Elena.

Bonnie had thoroughly enjoyed just watching the show, but inevitably she craved to join in on the fun. So she crawled up the bed until she was hovering over her best friend's face, who had her eyes closed, clearly lost in the pleasure she was feeling. After a few long seconds Elena seemed to sense someone was above her, and she opened her eyes to give Bonnie a smile, before leaning in to the inevitable kiss between them. It might have not been the first, not by a long shot, but it was still pretty new, and this time Caroline was licking Elena's pussy, causing the other brunette to moan, gasp and whimper into Bonnie's mouth, making the kiss that much more delightful.

It was the kind of kiss Bonnie never wanted to end, but after Caroline had raced through the foreplay it seemed only right that she pick up the slack, even if it was late. Besides, breaking the kiss and beginning to concentrate on Elena's neck meant that she could more clearly hear her best friend's sounds of pleasure as her best friend turned girlfriend worshipped her cunt. Oh yes, these wonderful sounds had Bonnie grinning against Elena's neck as she kissed, licked and sucked the soft flesh beneath her. She even bit down gently, hoping to mark another girl as hers. Not that she wanted to have another girlfriend, or worse, replace Caroline, but in that moment Bonnie felt possessive of Elena. Which she knew was wrong, but she just couldn't help it. Not after Caroline had so wonderfully encouraged those thoughts.

Thoughts she hope to make a reality real soon, but if she was going to do that she was going to have to do more to please Elena first. Luckily Bonnie was just getting started, the next part of her plan, involved her kissing her way down to those previously neglected breasts. She then kissed her way up one and swirled her tongue around her friend's nipple and then taking it into her mouth to gently suck on it, causing Elena to cry out joyfully and press Bonnie's head firmly against her boob. This in turn caused Bonnie to grin around that nipple, and then after a few minutes of giving it some attention. She kissed her way down that breast and up the other to repeat the process with the other nipple.

She then went back and forth between those nipples for what seemed like an eternity, Bonnie impressed with the length of time Caroline was able to tease Elena with her tongue. Of course inevitably Caroline couldn't resist increasing her attention, which was made very clear from the way that Elena's sounds of pleasure and the way she was writhing on the bed increased. But that was alright, because by that point, Bonnie was more than ready to increase her own technique, initially meaning that she increase the force of her licking and sucking, even adding gentle biting to the equation, just like she had done with Elena's neck. Then after a few long minutes of that she kissed her way upwards and pressed her lips to hers again, this time Elena initially resisting before giving into it.

Elena didn't mind kissing Bonnie again. On the contrary, her best friend was an amazing kisser, and she kind of wanted to make out with her forever. Just like she wanted Caroline to eat her pussy forever. Which was why she was holding back on the urge to beg for more, just as Caroline had promised she would, because she had wanted longer to enjoy this heavenly moment. But inevitably it all became too much, and she opened her mouth to make the aforementioned promise. However, as if sensing what she was about to do Bonnie suddenly crawled up her body and kissed her, and try as she might Elena just couldn't resist those forceful lips. Especially when Bonnie's hands went straight to her tits, giving them just as much attention as her mouth, if not more.

It was a sweet torment the likes of which Elena had never experienced before. Sure, Vicky could be a frustrating tease, but that was momentarily compared to this, and the connection wasn't quite as intense as the one she had with Bonnie and Caroline. Then there was the obvious fact there were two of them! Two people worshipping her body at the same time! Two girls! Oh God, Elena was having a threesome with her two closest female friends. It was an all girl threesome, and she was at the centre of it. God, she had never felt so worshipped and loved, and yet so naughty and slutty. And again, it was something she very much wanted to never end, but that the same time she desperately needed more.

Suddenly Bonnie broke the kiss and whispered into Elena's ear, "Vicky said you were a bottom. Is that true?"

"I..." Elena stammered and blushed, before answering truthfully, "I don't know."

Bonnie pulled back slightly, looked at her thoughtfully, and then said, "I think you are."

"I-" Elena began, before being cut off.

"Or at least, I hope you are." Bonnie admitted with a wicked grin, "I definitely identify as a top, and Caroline totally identifies as a bottom, so we're perfect for each other. Mmmmmm yeahhhhhh, there's nothing my girl loves more than eating pussy like the hot little bottom she is. And she is good, isn't she? Yeahhhhhhhhh, I bet she's making your little pussy feel so good right now. Huh? Are you close to cumming, Elena? Huh? Are you close to cumming in my girlfriend's hot little mouth, ohhhhhhhh, and all over that pretty face of hers? Huh? Are you? Oh yeahhhhhhhh, does our best friend want to cum for us? Well, does she? Answer me you bitch!"

"YES!" Elena cried, "Yes, yes, YES! Yes to all of it. Just please, make me cum!"

"Be more specific." Bonnie pushed with a wicked grin, "Mmmmmm yeahhhhhhhh Elena, answer my questions, all of them, and ask Caroline nice enough, and maybe, just maybe, we'll make you cum."

Without hesitation Elena replied, "Please, please make me cum! I want you to make me cum so bad. Soooooooo bad, oooooooooh Goooooooooddddddddd, Caroline, you're going to make me cum! Mmmmmm yessssss, you're going to make me cum in your hot little mouth, and all over your pretty little face. That's what I want! I want to cum for you Caroline! Cum for you and Bonnie! Oh Bonnie, ohhhhhhhh fuck, your girlfriend is so good. Sooooooo goooooooooddddddddd at eating my pussy! I love it so much, mmmmmmm, it feel so good. Oh my God, I'm so close, soooooooooo close, mmmmmm! I'm so close to cumming in your girlfriend's hot little mouth, oh fuck, and all over that pretty face of hers. Oh Bonnie. Please, please let me. Please, let me cum for you and Caroline!"

"I suppose that will do." Bonnie said almost thoughtfully, before turning her attention to her girlfriend, "Do it Caroline! Make Elena cum in your hot little mouth, and all over your pretty face. Oh yes, fuck her Care! Fuck her good."

Unsurprisingly Caroline was quick to increase the pleasure, making it harder and harder for Elena to speak, and yet the little tease just wouldn't let her go over the edge. That mostly involved concentrating on Elena's clit, taking it into her mouth and switching between licking and sucking with increasing force, until finally the brunette was on the edge of climax, only for the blonde to slow her role just enough so she could keep her there. Which was both wonderful and agonising at the same time. Wonderfully agonising? Yes, that seemed accurate. Especially when Bonnie quit her encouragement and went back to Elena's tits, which was enough to leave poor Elena incoherent, but not enough to give her what she wanted.

Then in one swift movement, which was so well timed it had to be something they previously agreed on, Bonnie bit down on one of Elena's nipples while Caroline slid her tongue down to her friend's entrance and shoved it as deep inside of her as it would go. Which of course was more than enough to push Elena over the edge of a monster climax, stronger than even the many, many orgasms Vicky had gleefully given her. And like Vicky, that first orgasm was only the start. Oh yes, Elena barely had a chance to get over that first earth-shattering orgasm before she found herself being pushed over the edge again, and again, and again, until she could no longer think coherently. Although one kind of echoed in her mind throughout, that being she hoped that this would be a regular thing.

Caroline definitely wanted that, which was extra encouragement, as if she needed it, to make Elena cum as much as possible. Which she found to her delight was just as easy as it was with Bonnie, and as it had been with Vicky, proving Caroline Forbes was an excellent pussy pleaser. The thought made her submissive heart flutter, but she couldn't get distracted by such wonderful things. Especially when there was another distraction she couldn't help but get lost in, especially at first, that being the taste of Elena's cum. Oh yes, she had been dreaming about being able to taste Elena's cum pretty much since she hit puberty, and it was just as good as she had imagined it would be. Hell, it was almost as good as Bonnie's, which was really saying something.

So Caroline felt like she almost had no choice but to pull her tongue out of Elena's pussy almost the same second she pushed it in, and then wrap her mouth slowly around her friend's entrance so she could swallow every drop of that precious liquid. Luckily all that time going down on Bonnie meant that Caroline was well prepared for this, and she was very proud to report that she got every drop, even if it was difficult, as she was overwhelmed with both the taste and the fact that she was finally able to swallow her other best friend's girl cum. Sadly she wasn't so lucky with the following orgasms. In fact she was increasingly unlucky, although at least that meant that Elena's cum was covering her face and marking her as what she was, a pussy addicted slut.

After that first climax was over, Caroline shoved her tongue back into Elena's cunt and tongue fucked her best friend to another orgasm. She then repeated the process for a few wonderful minutes, before replacing her tongue with her fingers, pushing first just one, then two fingers into her friend's pussy while her mouth returned to her clit. Which she didn't want to do, as it meant missing out on some wonderful juices, and it was kind of a top thing to do, but Caroline would literally do anything if it meant doing this again. So she pulled out every trick she knew to please Elena, and was rewarded for it with not only yummy liquid but the other girl quivering for her, and of course letting out the most wonderful sounds of ecstasy.

While sometimes it felt like Caroline was born to please women, and could do it forever, she was actually kind of glad when Elena reached down and pulled her upwards into a passionate kiss. Mostly because she selfishly wanted some attention herself, but also because as much as she adored Elena, she just wasn't in love with her like she was with Bonnie, and Caroline really, really wanted to do something to please her girlfriend. Also, she really enjoyed it when another girl tasted herself on her lips and tongue, and Elena didn't hesitate for a second. Hell, she even licked some of the cum and pussy cream off of Caroline's face, causing both girls to giggle, pretty much making this moment perfect.

Then Elena rolled them over, only for Bonnie to stop her, "Wait!"

"What? Want me to go down on you first?" Elena offered with a happy grin.

"Actually we had something else in mind..." Bonnie said.

"Like?" Elena raised an eyebrow, genuinely intrigued.

"Well, Vicky told us that you played with toys, so how would you feel about trying a strap-on?" Bonnie asked, before checking, "You do know what a strap-on is, don't you?"

"Yeah..." Elena quickly confirmed, then after thinking about it for a few long seconds she smirked, "What, you want me to fuck you and Caroline with a strap-on?"

This earned Elena an unimpressed look from Bonnie, which in turn caused Elena to laugh, and Caroline to butt in before things got out of hand, "Actually, I was hoping both of you could fuck me with strap-ons. I've never been double team before, not like that, and I really want it to be you guys who do it, because you mean so much to me. And I think it would be so hot. Don't you think it would be hot, Elena? To fuck me in both my holes?"

Elena frowned at this, as Caroline looked like she said more than she meant too, leading her to ask, "Which holes? Your pussy and mouth... or..."

"Or. Definitely or."  Bonnie admitted truthfully, deciding that was the best course of action.

"Really?"  Elena raised an eyebrow as she stared at Caroline, who blushed furiously.

"Caroline?" Bonnie gently pushed.

"I love it, okay?" Caroline forced herself to admit to Elena, still blushing even as she began to get carried away again, "I love it in the butt. I never thought I'd be one of those girls, an up the butt girl, but I am. Oh God Elena, it makes me cum so hard! And Bonnie is so amazing at it! Mmmmmm, I don't even think it can get any better, but I want to try. I want to try taking a cock in my ass and my pussy at the same time. I want to know what that feels like. I, I want both of you inside me, at the same time. Oh my God Elena, I want it so bad! Please give it to me. Fuck me like I've never been fucked before, and make me cum like I've never cum before. Please?"

There was a brief pause and then Elena gulped, "Yeah, we can do that."

"YES!" Caroline exclaimed, peppering kisses all over Elena's face, "Thank you, thank you, thank you!"

"You won't have to do anything." Bonnie promised, "All you have to do was lie back, and we'll do all the work."

"Yeah, I figured." Elena admitted softly, before asking out of curiosity, "Wait, so are you going to be the filling in the sandwich next?"

It was a very positive sign that Elena could joke about this already, so instead of being insulted Bonnie smirked, "Oh, I can cum just from fucking a hot bottom, isn't that right baby?"

"Yeah you can." Caroline grinned dreamily, ading after kissing her girlfriend, "You're a total stud."

"Damn right, now get us some toys." Bonnie ordered, smacking Caroline's ass and causing her to yelp and giggle with delight.

Elena actually smiled a little as she watched her go, then she got nervous again when she saw the toys she retrieved. They were a lot bigger than she was expecting, especially considering where one of them was going. Of course, after the ecstasy that Caroline had made her feel it felt wrong to deny her friend what she wanted, especially when all Elena had to do was lay there and let the other two girls do all the work. And to be fair, she really, really enjoyed the first part, in which Caroline helped attach the device, while Bonnie attached one of her own, and then Caroline took Elena's newly acquired cock into her hand and stroked it as if it was real. Although what was even better was when she took it into her mouth.

Her best friend since childhood wrapped her pretty lips around a cock strapped around her waist and started bobbing her head up and down on it! God, Elena had never imagined anything like this before, but she had to admit it was incredibly hot. Also the other end of the harness was pressed against her clit with every little movement, quickly explaining why Bonnie could cum from fucking Caroline. And why it was likely Elena would do the same. Cum while Caroline was on top of her, riding her cock, and fuck, this was so hot! So hot Elena felt that she could cum again just from watching her best friend Caroline suck her cock, while her other best friend began rubbing some sort of lubricant into her strap-on.

Just when Caroline looked like she was going to push the dildo into her throat she suddenly pulled up and away from it in favour of straddling Elena's waist. Than with practised ease she lined the entrance of her pussy over the head of the strap-on and then pushed herself downwards, crying out and then letting out a long moan as the cock slowly started to enter her. As Elena's cock slowly started to enter Caroline's cunt! Oh fuck, Elena had a cock right now, slowly stuffing Caroline's pussy up until one of her best friends was sitting on top of her lap with her strap-on fully embedded inside her. Then she started riding her, and for the life of her Elena couldn't remember why she had been so hesitant to try this.

She was then reminded when her other best friend kneeled down behind the best friend riding her. Bonnie then smirked, wiggled her fingers, and pushed them downwards. From the expression on Caroline's face Elena knew exactly where those fingers went. Or one of them, at least. Not that she really knew how many fingers it took to lubricate a butt hole. Oh God, Bonnie was lubricating Caroline's butt hole! Getting it ready to fuck. Oh shit, Bonnie was going to butt fuck Caroline! DP her, with Elena's help. Which should have disgusted Elena, and it did, but it was also kind of hot, especially when Caroline cried out joyfully as she was anally defiled. And the blonde's reactions got even more favourable after that.

"Oh Bonnie, that's it. That feels so good. Mmmmmm yeahhhhhhh, I love it when you fuck my ass!" Caroline confessed with a moan, grinning wickedly at Elena as she added, "Now give me more. Ooooooooh fuckkkkkkk, that's good. Mmmmmmm, that's soooooo gooooooddddddddd. But you know I wasn't talking about another finger. No, I need your cock. Please Bonnie, stick your cock up my ass and butt fuck me! Butt fuck me right in front of Elena, mmmmmm, while she's got a cock in my cunt. Please give it to me, ohhhhhhhh shit, I really want to find out what it's like to be a little DP slut. Your DP slut! Yours and Elena's, oooooooohhhhhhhh, so please, please fuck me in both my holes like the little DP slut I wanna be!"

"Anything for you, baby." Bonnie smirked, before finally giving Caroline what she wanted.

Bonnie would have loved to hear Caroline begging forever, especially when she was begging for a cock up the ass, but given this was a first for them, and more importantly a first for Elena, she once again started sooner rather than later. So, before she really wanted too, and maybe sooner than was advisable, Bonnie pulled her fingers out of Caroline's back door and replace them with her strap-on. Luckily ever since she took Caroline's ass cherry they'd been pretty much having non-stop anal sex, mostly because her girlfriend couldn't get enough of it, so hopefully they could get through the worst quickly and onto the part they loved the most. Although even during the initial penetration, which Bonnie couldn't imagine was pleasurable, her little anal slut cried out joyfully.

That cry was definitely a mix of pain and pleasure, but the fact that Caroline could feel any pleasure from getting her most private hole stretched wide enough to take the head of a cock baffled Bonnie. Of course, it was also an extreme turn on, as was the fact that Caroline continued making sounds of pleasure throughout the ass stuffing. Which she had done other times they'd had butt sex, but Bonnie was now hyper aware of it because of Elena. Thankfully her best friend seemed to be as turned on by it as she was, which was a really promising sign, as Bonnie was hoping to use how much Caroline loved it up the ass to convince Elena to give Bonnie her anal cherry. Then Bonnie would have taken the anal virginities of both her best friends, hopefully making them her butt sluts in the process. Oh God, that would be so hot.

It was hard to not get distracted by what had quickly become Bonnie's ultimate fantasy, but as that fantasy relied on her being able to give Caroline as much pleasure as possible she was able to focus on the task at hand. Which basically involved moving forwards slowly, pausing now and then so her girlfriend could get used to having a cock up her butt. Or as used to it as possible, considering it was extremely unnatural. And yet, Caroline continued to show signs of loving it, right up until the precious moment that Bonnie's thighs came to rest against her ass cheeks, announcing every inch of that strap-on dildo was now deeply embedded within the blonde's back passage. While her front passage was also taking a cock, no less.

Bonnie gave Caroline a few minutes to adjust, then she softly asked her, "How does that feel, Care?"

"Amazing!" Caroline moaned without hesitation, "Better than I ever dreamed! Oh my God Bonnie, I love having you in Elena inside of me at the same time. It feels so good, mmmmmm, but I need more. Please Bonnie, I need you to fuck me. Fuck my ass, fuck my cunt, oooooooohhhhhhhhh fuckkkkkkkkkkkkk yeahhhhhhhhhhhhh, ohhhhhhhhhhh Gooooooooooddddddddddddd!"

Maybe Bonnie should have given Caroline a few more minutes, or at least a few more seconds, to adjust to having two cocks inside her at the same time. Especially considering she was begging for more, which was a very, very positive sign. But hearing that, hearing Caroline begging to be ass fucked, just caused Bonnie to lose it, as she just couldn't resist fucking that wonderful little ass any longer. So she didn't. Instead she slowly pulled back her hips, pulling about half of the dildo out of Caroline's butt, and then pushed the entire thing back in. She then repeated the process, albeit with shorter thrusts, and thus officially started to sodomise her girlfriend, much to that girlfriend's clear delight. Sadly she wasn't begging any more, but the moans, groans, whimpers and cries more than made up for that.

Caroline actually wanted to continue begging, but she just wasn't capable of it in that moment, because she was just too overwhelmed by the pleasure she was feeling. Sure, the initial anal penetration and ass stuffing always hurt a little bit, but relentlessly getting sodomised by her girlfriend had definitely loosened her up back there so it didn't hurt as much, and also the sheer mental pleasure of getting fucked up the butt was more than enough to make Caroline moaned during that process. However this time had been different. This time there had been a cock in her cunt, and it had been attached to her best friend Elena, who's eyes she had been staring into the entire time. And she was as sure as she could be that Elena was enjoying it, suggesting that they would do this again, which was exactly what Caroline wanted.

While Caroline had been hoping for that last part all the rest she had been expecting, and it really was better than she'd ever dreamed. However there was something she hadn't anticipated, namely that Bonnie's thrusts backward would pull her pussy upwards on Elena's cock, and then when Bonnie pushed forwards into her ass she would also be pushing Caroline downwards onto Elena's dick. So essentially Bonnie was using Elena to fuck Caroline's pussy and ass at the same time, which was mind-bogglingly amazing. Caroline couldn't even try to put it into words, at least not initially. Hell, she was so blown away she could barely think, especially when it got even better as her girlfriend skilfully encouraged the blonde slutty little butt to relax and remember it was made for fucking.

Soon after whatever initial discomfort became a distant memory Caroline felt compelled to kiss Elena as she just needed something to distract her, and in her hazy mind this somehow seemed like an answer. Of course it was a bad idea, because after a brief bit of hesitation which was probably down to shock more than anything Elena kissed her back passionately, giving Caroline another thing to make this overwhelming. So overwhelming that in record time Caroline felt the urge to cum. Hell, it almost felt like she could explode just from this gentle treatment. Sadly that wasn't the case. No, she needed something to push her over the edge, and she knew just what she had to do to get it. Although she put it off for as long as she could, just so she could savour this amazing moment.

Inevitably though Caroline broke the kiss with Elena and began begging, "Harder! Fuck me harder and make me cum! Oh please Bonnie, mmmmmm, fuck my ass harder! Pound it hard and deep and make me cum! Please? Oh please, slam fuck my slutty little butt hole, and show Elena what a little ass whore I am! Ohhhhhhh yeahhhhhhhhh, I'm your little ass whore! Mmmmmmm, we both know that, but now, let's show Elena! Yesssssssss, oooooooooh mmmmmmm, let's show her I'm your little ass whore, I'm your little butt slut, ohhhhhhhhh mmmmmm yesssssssss, I'm your anal loving dyke bitch! I'm yours Bonnie, ohhhhhhhh, all yours, and now Elena knows it. But hammer it, and me, home by destroying my whore ass! Oooooooooohhhhhhhhhhhh yeeeeeeeeessssssssss, AH FUCK! Oh my God, yes Elena, fuck me! Fuck me hard and make me your DP slut! Yessssssssss ohhhhhhhhhh, fuck me Elena, fuck me Bonnie, just fucking fuck me, aaaaaaaaaaahhhhhhhhhhhhh Goooooooooooodddddddddddd!"

Normally Bonnie teased her a bit more before giving her what she wanted, and while it was hard to complain Caroline kind of wished her girlfriend had left her hanging for a bit longer. Then again, hopefully this was the first of many times Caroline was DP'ed by her best friends who had now become so much more to her. Maybe other girls too. After all, she was young, and wanted to have fun. Although it was impossible to imagine it would be as amazing as being fucked in both her holes simultaneously by Bonnie Bennett and Elena Gilbert. Bonnie didn't even have to do that much to make her cum for the first time, but then to her surprise and delight Elena joinned the fun, which made Caroline cum so hard and frequently she completely lost the ability to think coherently.

Elena was amazed by the fact that she came too. At least, she was amazed it happen so quickly. Throughout the entire time that she was double teaming one of her best friends with her other best friend the other end of the dildo was bashing against her clit, which felt predictably amazing, but she wasn't expecting it to make her cum quite so quickly. Although honestly that had a lot to do with the mental stimulation of being a part of giving Caroline Forbes her first ever DP. Something which Elena was really proud of herself for. And oh, seeing Caroline writhing on top of her, of being able to kiss her, of being able to hear her whimpers, gasps and moans, and then later her screams and squeals, of pure pleasure? God, Elena couldn't even put into words how much she loved it.

Maybe the best part was that every time she thought it couldn't get any better, it did. First with the kissing, which she did throughout the rest of the double teaming, even if she had to settle for kissing Caroline's neck, then there was the way Caroline begged for more, especially when she begged to cum, which just drove Elena wild. Most of all though, there was Bonnie building up her pace until she was hammering Caroline's ass with what had to be every ounce of her strength, and the sound of flesh smacking off flesh were almost as loud as Caroline's screams of pleasure. Which was of course when one of her best friends started to cum for her and her other best friend, which almost instantly triggered an orgasm of Elena's own.

Hopefully it was the same case for Bonnie, although it was kind of hard to tell, as she was completely in the zone. Either way Elena suddenly felt a desperate need to do more, so she started thrusting upwards into Caroline's cunt. It was slow and awkward at first, but when this seemed to make Caroline cry out even more loudly, and perhaps even cum harder, Elena was inspired to establish a more steady rhythm. Her thrusts were nowhere near as powerful as Bonnie's, but they were still enough to make a difference, both for Caroline and Elena herself, in both ways which were expected, and in ways which weren't. Because it also made them both cum harder and more frequently, and there was something else.

She found herself thinking back to Bonnie's question about her being a top or bottom, and while Elena hadn't given it much thought she was definitely experiencing the benefits of being a top now. And she'd like to experience more. Oh yes, she wanted to know what it would be like to be in Bonnie's place, and be the one controlling the whole thing. Be the one fucking another girl in the ass. To be able to butt fuck Caroline, while Bonnie was stuffing her girlfriend's pussy. Although, she also kind of wanted to know what it would be like to be Caroline. To take two cocks like that. One in her pussy, and the other up her butt. Or maybe, just one in her butt. It was so confusing, but Elena imagined herself in both roles, and everything she imagined, she liked, making her hope her friends would allow them to do this again, so she could try so much more.

Bonnie was trying to figure out what was going on inside of Elena's head right now. She had assumed Elena was a bottom, but maybe she had been wrong. After all, she fucked Caroline with the kind of skill which had taken Bonnie months to learn. Which would be disappointing, but she could live with it, especially if it meant giving Caroline such ecstasy. Giving them all such ecstasy, honestly. Oh yes, Bonnie came wonderfully hard, and she could tell Elena did too, from the toys hammering their clits, and the sheer joy of fucking their friend like this. But Caroline came harder and more frequently than the two of them combined, which made Bonnie's heart flutter with joy.

Sadly all this pleasure couldn't be never-ending, and ultimately Caroline collapsed with exhaustion. Honestly, Bonnie was kind of relieved, because she was running on fumes herself, and pretty much instantly pulled her strap-on out of Caroline's butt, and then collapsed besides Elena, who also stopped the second it was clear that Caroline couldn't go any more. Hell, her girl seemed to actually be unconscious, which was another first for them. Bonnie was a little concerned about it, but from Caroline's gentle breathing she guessed she would be okay. She'd just have to miss out on the end of their routine. Of course, just as Bonnie was contemplating whether she could talk Elena into it, or whether she should do it herself, Caroline came too, and then practically wept with joy.

"Oh my God, that was amazing!" Caroline exclaimed, "Please can we do that again?"

"That's up to Elena." Bonnie pointed out.

"Oh." Caroline blushed a little, refocused on the girl beneath her, and then begged, "Please Elena, can we do that again? Mmmmmmm, I'll do anything if you fuck me like that again!"

"Right now?" Elena teased.

"No." Caroline whined, "You know what I mean."

"I do." Elena admitted, leaving her best friend hanging for a few long seconds, before grinning, "And yeah, we can totally do that again."

"Yesssssssss!" Caroline beamed happily.

"But you have to eat my pussy again. And do whatever else I want." Elena bargained.

"Deal." Caroline agreed without hesitation.

"We can negotiate later. For now... Caroline, won't you be a good girl and clean those cocks for us?" Bonnie offered in a tone which made it clear it was a command, not a suggestion.

"Really?" Caroline beamed, and then when Bonnie nodded she happily added, "Okay."

With that Caroline slowly and a little reluctantly lifted herself up and off of Elena's cock, crying out several times in the process. They almost sounded fake, or at least exaggerated, although Bonnie wasn't surprised that Caroline was feeling sensitive after the double pounding she had just taken, and she knew for a fact that her girl kind of enjoyed being overly sensitive after sex. Sometimes it would even allow Bonnie to push another climax or two out of her, but not tonight. No, they were already pushing their luck, hence why they had agreed not to do this originally. Ultimately she couldn't resist, but at least Caroline didn't show off her butt hole, which was probably gaping after the battering it had taken. Possibly her pussy too.

Instead Caroline just crawled down Elena's body and then with a flirtatious smile took their friend's cock into her mouth and moaning happily as she tasted her own cum and pussy cream. After savouring that flavour for a few long seconds Caroline began bobbing her head up and down the dick, thoroughly cleaning it as she always did, which was not something Bonnie could normally tear her eyes away from, but this was different. Now she had to worry about Elena's reaction to this latest twisted act. Thankfully another gamble had paid off, as the other brunette seemed enthralled by watching their dear childhood friend cleaning the cock which had just been deep inside her.

Elena had sucked Vicky's vibrator after it had been inside her, and better yet inside Vicky, so this wasn't actually a big deal for her. Honestly she didn't even notice that Bonnie was studying her face to see if she was all right with this as she was just too lost in staring at Caroline, completely overwhelmed by her lust. Also in amazement that after a while Caroline was able to deep throat the dick. God, why wasn't she more popular with the boys? Oh right, Caroline was gay. Or was she bi? And what about Bonnie? Elena should really ask, and she would, but it didn't matter. All that mattered was her friends were like her. They liked girls, and were willing to do wicked and wonderful things with her.

In fact, more wicked then she could have imagined, because right after Caroline was finished with Elena's dildo she moved right onto Bonnie's, and fuck! Just... fuck! Okay, Bonnie had said something about 'cleaning those cocks', but initially Elena had just thought she was going to remove them and then wash them under a tap or something like that, so when Caroline actually started sucking Elena's cock clean of her own cum and cunt cream she kind of forgot what was said. Besides, Bonnie's dick had been up Caroline's butt, so of course she wouldn't suck that, right? Wrong! Oh God, like something out of a porno Caroline wrapped her pretty mouth around her girlfriend's strap-on and started sucking it. Just as enthusiastically as she had with the other dildo. And she even moaned! Moaned at tasting her own ass.

Which should have disgusted Elena, but instead she found it an incredible turn on. Caroline Forbes, one of the most popular girls at school and a dear childhood friend, was sucking a dildo which had just been deeply embedded within her butt! A dildo which was strapped around the waist of Elena's other best friend Bonnie Bennett, who was watching Elena nervously, clearly worried what Elena's reaction would be. Finally realising this Elena gave her friend a wicked smile, Bonnie happily returning it, and the two of them even sharing a chuckle, before they returned their gaze to Caroline, who again, was somehow pushing that giant dildo into her throat. Sure, she was choking and gagging on it a little bit, but nowhere near as much as she should be, and she certainly shouldn't be still moaning with pleasure.

Elena wondered whether that was because of tasting her own ass, deep throating Bonnie's dick, or doing both those things in front of her friends. Whatever the case Caroline Forbes was proving without a shadow of a doubt that she was a lesbian slut, and Elena loved her for it. Or more accurately, loved her even more. Which was a feeling which was only increased when Caroline crawled upwards and kissed Bonnie right on the lips in front of her, her two friends sharing the taste of Caroline's ass, pussy and cum. Admittedly, it made Elena kind of jealous, but mostly it was hot. Besides as soon as the kiss was broken she moved in to kiss each of her friends in turn, who happily welcomed her lips with their own.

"So..." Elena asked after a little more making out, "What do you want to do now?"

Bonnie bit her lip nervously, while Caroline beamed, "Well..."

Oh yes, this was definitely going in Elena's diary.

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