~ If you play, you play for keeps ~

Disclaimer: I do not own TVD only the twisted plot. Wouldn't mind having Damon to play with for a couple of hours or days though.

Sorry for the delay, this chapter was really complex to write! Hope i got it right. Thank you readers for keeping me inspired!


We belong to the light, we belong to the thunder
We belong to the sound of the words we've both fallen under
Whatever we deny or embrace for worse or better
We belong, we belong together

We belong -Pat Benatar

Normally Damon wouldn't think twice about indulging a lover's request for having anal sex. Hell, he had compelled and ravaged his fair share of beautiful behinds over the years. What made this particular request uncomfortable is that the lover in question was his sweet, ok, not so sweet anymore, Elena and Damon's instinct was to always protect her. Indulging in anal sex and corrupting her body and innocent soul went against it. Then again…he knew how to make it pleasurable and she had asked for it. Damon sighed… he didn't even want to think about the fact that the first time he had indulged in that particular pleasure it had been with Elena's doppelganger…Damon held the bridge of his nose wondering when had he become this whipped pathetic vampire.

Elena's soft hands on his cheeks brought him back to earth. She was looking at him with very concerned eyes.

"Damon" – she whispered softly –" If you keep running around your head like that you are going to do permanent damage… What's the matter?" – Elena pouted –"You don't want me that way?"

Damon snorted.

"Yeah Elena, my hot girlfriend that I love desperately just asked me to have anal sex with her, every man's basic fantasy, and the reason I am hesitating is because "I don't want you that way"" – Damon bit back.

"So what is holding you back?"- she asked caressing his cheek – "I really want you to do it." - she murmured seductively looking at him with heavy eyelashes.

"What's holding me back is that I love you and I don't want to damage you body" – he ran his finger along her jaw and tipped her chin to look at her eyes –"or your soul."

It was Elena's turn to snort.

"You really should have thought of that before you indulged in anal sex in front of me! Now the damage is done." – she said sarcastically but then kissed his lips softly –"And I knew what I was getting into when I gave into you. My body and soul are totally fine with it too." – She winked at him seductively.

"So… every man's basic fantasy uh?" – Elena said with a smirk looking over her shoulder at him as she walked out of the shower, purposely swaying her hips to bring attention to her behind. When she felt Damon's eye practically burn a whole through her, she let her hand trace the soft curve of her left cheek and smacked it hard letting out a moan and leaving an angry hand mark visible as she leisurely left the bathroom.

After that Damon didn't need any more convincing, he was practically felling deranged with lust as he turned the shower off and ran after Elena, his wet body slamming hers onto his bed. He was kissing her all over and quickly buried his cock inside her wet core.

"Common baby, let's make some noise." – Damon chuckled darkly.

Elena moaned at the pleasure of being handled so roughly and suddenly. But deep down she was loosing patience with Damon's unwillingness to give into her wishes.

"You really don't want to do this…."– she groaned and pouted as he filled her to the hilt.- "Ahhh Damon"- she squirmed.

"Trust me Elena, we are doing this"- he growled seductively into her neck and gave her another body splitting thrust – "I am just getting you warmed up."- he purred.

"It feels soooo good Damon..." - she panted as he established a delicious salvage rhythm with his hips, sliding in and out of her sensitive core. - "but..."

"But what Elena?"- he asked as he licked circles around her nipple.

"Oh god"- Elena arched her back into his mouth-" i-i-is not-not where I wanted you."- she mewled lustfully.

Damon moved down her body and scrapped his fangs on the underside of Elena's breast. Desire to consume her making his hips pick up speed.

"Tell me where you don't want me." – he whispered as he pumped roughly in and out of her.

"I – I don't want you in –in- my - pussy. Ahhh…" – Elena screamed as Damon plunged his erection with blinding force into her hitting all the right spots.

"I looove when you talk dirty." – he said nipping at her lower lip –"So tell me Elena, where do you want me?" – he asked pumping relentlessly but varying the angles to give her new sensations.

"In– in- the back." – Elena mumbled shyly. Damon drove his fangs in lightly around her right nipple and Elena bucked from the pleasure.

"What? A little louder Elena, I can't hear youuu." – Damon said as he gave her another body splitting pump that made Elena throw her head back in pleasure and scream.

"I want you to fuck me in my virgin ass Damon!" – she hissed once she found her voice.

Damon stopped moving shocked into stillness.

Elena looked at him angry and frustrated – "What now?

"You never done it before?" – he asked slightly taken aback his eyebrows arching in disbelief.

"No, of course not!" – Elena snapped at him slapping his arm hard –"What kind of girl you think I am? AND BTW, that was my first foursome and my first time with a girl too you idiot!" – she frowned trying to get up and leave the bed.

"Oh, no you don't." – Damon pinned her down –"I am sorry Elena, don't pout." – he said trailing her lower lip with a finger – "I am just happily surprised to be your first in something." – he smiled at her genuinely.

Elena rolled her eyes – "Men and their egos!" – but giggled bringing Damon down to kiss him.

Oh this was too good to be true Damon thought. He was definitely making sure to ruin her for any other men. She may not give him her love, but her body was going to long for his as his heart longed for hers.

"Your wish is my command" – Damon kissed her mouth softly.

Elena mock rolled her eyes to hide her sudden nervousness – "It's about time, I was starting to feel like a bad influence." – she giggled.

"And we wouldn't want that would we?" – Damon said teasingly as unburied himself from her and flipped Elena on her knees.

"Elena, lay your head on the mattress."

"Katherine didn't have to..." – Elena pouted looking back at him.

"Katherine hasn't had a virgin ass in many many moons my dear." – he sighed –"Trust me, I am just trying to make this good for you."

Damon moved around the room at vampire speed as Elena leaned her upper body over her tights

"Okay…" – Elena said as her nether regions were exposed and she pressed her face on the soft sheets. When she looked up she saw that Damon had placed several big mirrors around the bed and she could see herself reflected from various angles.

"Damon! This is a bit too kinky even for you."- Elena tried to sound outraged when in reality the idea of seeing themselves doing it was almost making on the spot.

"Trust me Elena, anal sex is strongly connected with taboo and visuals. Seeing is almost as exciting as doing it." –Damon leaned closer and whispered against her cheek – "Almost…"

His hot breath and words sent a shiver down her spine. Elena looked to see the two of them reflected a million times around her and got wetter just from seeing their naked bodies so close together.

Damon kneeled down on the floor by the end of the bed and snaked his lips from her pussy to her crack, making Elena squirm with pleasure.

"Don't close your eyes Elena, watch us." – he checked to see if she was paying attention –"This is called rimming."

Damon circled her back hole with his tongue eliciting moans from Elena that only made him harder. To add to the sensation he followed the trail to her wet core playing with her clit as he pushed three fingers into her core. As he started to pound his fingers into her, the pad of his hand kept hitting her back entrance and Elena was making the most beautiful sounds. After a couple of minutes of pleasing her this way and looking into her eyes as she saw what he was doing to her Damon reached for a tube of lube and spread the cool gel over Elena. When she saw Damon applying the gel, Elena stopped breathing. Damon expertly smacked her backside, the shock making her breath again and the vibrations doing wonderful things to her core and stimulated behind.

"Relax sweetie. You are going to enjoy this." – Damon started exerting some pressure on top of and around her hole, threatening to dive one finger tip into it whilst still moving his other hand in and out of her to keep her distracted. Damon was desperately trying to control the urge to screw her immediately as her moans filled the room. Elena was seeing stars at this point. The visuals alone were so delicious and the anticipation was killing her. If the pressure felt this good, being filled by Damon's cock was going to be off the charts she reasoned.

Damon massaged her crack, slipping his cock up and down between her butt cheeks. Elena was melting in his hands, drunk with pleasure as he returned his fingers to her core. She was making guttural moans of pleasure when she felt Damon's finger plunge into her ass.

"Fuuuuck me"- she screamed as she felt the pain, and her whole body stiffened.

Damon feeling her vice like grip on his finger, leaned over her body and whispered soothingly into her ear.

"Shhh, you have to relax Elena, you need to get past the initial pain." – he started to lave and bite her ear gently – "Relax baby."

As Elena concentrated on the sensations around her ear she started to relax and the pain was slowly replaced by a dull ache and the pleasure that had been obfuscated so far became so much more present that she pushed her hips against the offending digit.

"Ahhh Damon…mooore." – she purred.

With a satisfied grin, Damon started to slowly move his finger around her anal canal, gently stretching it. As she felt her get looser, Damon started pumping both entrances at once with his fingers, making Elena orgasm noisily. She trashed and moaned and screamed his name as he pushed her to the edge.

As she started coming down from her peak, Damon started pumping her again. Dam! She was so wet and responsive that it was almost painful for him to wait to take her. But he knew she would be worth the wait.

Damon inserted a second finger into her ass and Elena took it on stride and pushed against the pain to find the pleasure, and when he inserted a third finger, she moaned so loudly that Damon was finding impossible to keep the gentle pumping rhythm.

"More… Ahhh…Damon, more." – she pleaded.

Damon could prepare her longer, but he knew she was ready for the real thing. So he removed his fingers from her, wiped them quickly with the wet wipes he had left by the bed and brought her back against his chest. Elena's breath hitched in delicious anticipation.

He bit his wrist and brought it in front of her. Elena looked at him questioning.

"It's just for insurance, that way I cannot do too much damage when I fuck you senseless and then bite you." – Damon breathed .

With fluttering eyelashes Elena grabbed his wrist with both hands and sucked and licked hard letting her teeth scrape the skin, eliciting a moan from Damon as the sensations went straight to his cock. As she sucked he poured lube on his erection and massage its length.

"You make me sooo horny" – she purred leaning her head against his shoulder when the wound healed, her hair cascading around her, making her the prettiest picture of debauchery Damon had ever seen.

"And you drive me crazy woman." - He kissed her softly bringing her to the edge of the bed where he helped he kneel on the floor. As he pushed her down gently on her stomach onto the bed, his hand grabbed a fistful of her hair and the other positioned his very hard erection at her rear entrance.

"Ready love?" – he whispered in her ear

Elena answered by pushing her bum into his groin.

"Elena, if you feel any discomfort you need to tell me ok?"

Elena looked back at him and rolled her eyes – "Will you fuck me already?" – she said with a goading deliciously wicked smile.

Damon couldn't hold back anymore and with a trademark smirk and his eyes fixed on hers he pushed his erection as gentle as he could into Elena's receptive ass.

"Fuck, you are so tight" – he moaned at the sensation.

As she felt Damon's cock impale her, Elena gasped and let out a silent scream but she could not peel her eyes away from the vision of his cock half buried into her asshole. The pain was scorching but the pleasure left her delirious. Damon stilled her body as he slowly dove in, letting her it adjust to his size.

"You really are driving me insane woman..." – he bent to growl in her ear –"Just relax into it Elena, let your body get used to it."

Damon started kissing the length of her neck and Elena started to relax around his erection. The pain receding in favor of the overwhelming physical and emotional pleasure she was feeling from having him do this to her. It felt so good to belong to him and only him in this way.

As Damon moved his hand to her clit and started massaging it Elena started to move her hips, feeling more and more at ease with the cock inside of her. Damon moved with her and soon they were moving rhythmically, Elena panting with lust and pleasure, the discomfort not enough to impede the blinding pleasure. She reached down to her pussy and inserted her fingers to alleviate the need building there alongside Damon's hand as he pleasured her clit. The long wait and Elena's submission and tightness had Damon's mumbling Elena's name in between his pleasure filled growls. Their rhythm increased in tempo, making her come undone and mumble nonsensical words. They both reaching the peak of the biggest orgasmic spiral of their life when he sank his fangs on her neck and both practically cart wheeled into pleasurable oblivion.

Fuck me…" – Elena finally breathed out after many minutes and Damon chuckled into her neck.

"Any day, any time, Elena." – Damon replied huskily as he slipped out of her and brought her into his embrace.


Sooo? Was it good for you?*evil chuckle* Please review! it helps enormously! xoxo