Tyler's Teasing Ch. 03

This is the third instalment of the Tyler's Teasing series. It works as standalone smut, but if you want to know the characters and events leading up to this, I'd recommend reading the previous chapters.

***

Layla pulled Tyler into the room and kicked the door shut, kissing his face hard.

"You really want to?" Tyler asked, and Layla nodded, dropping to her knees.

Tyler thrusted against his jeans as he pushed the button of his pants open, letting them drop to his ankles.

Layla kissed at the bulge in his boxers as she tugged them down, and Tyler pushed her head away, holding her by the hair.

"Say please," he said, the tip of his cock visible, poking out of his underwear, glistening with precum.

"Please, I need it," Layla whined, and Tyler let go, letting Layla free his cock. He had been aching since Layla told him she had prepped earlier, and he had fantasised about it for so long.

"Are you excited to fuck my ass?" she asked, before kissing his tip.

***

Layla had grown more curious about trying anal since watching Sam take it. This curiosity had grown over the months. Tyler had started rubbing her asshole when she rode him, and he'd rimmed her a couple of times. Experimenting with fingering herself had felt taboo, even though she'd done it to Tyler before. This then grew to using a buttplug she'd ordered, and while it had felt strange at first, she'd enjoyed the sensation of being stretched. Though, she still wondered how much better her boyfriend's cock would feel instead.

Earlier that afternoon, while he'd been out, she'd fully prepped herself. She'd taken advice from Sam, and from a blog post she'd found online. He'd been very excited for her, and she'd promised to tell him how it went. He recommended against plugging herself hours in advance, and knew that Tyler would take it slow with her.

After a romantic dinner, she'd hinted at offering something new to Tyler, and when he guessed, she straight up asked him. There were nerves, wondering whether he might not be in the mood for it, but deep down, she knew that he couldn't resist.

***

"Can't you tell?" he said, pushing the head of his cock into her mouth, letting her suck eagerly, bobbing back and forth on the head. His cock throbbed in her mouth, and he started thrusting his hips gently, back and forth.

"I love your mouth," he moaned, and stroked her hair, looking down into her eyes.

He started fucking deeper, and Layla held onto his ass, gagging slightly as his cock hit the back of her throat. She kept sucking back and forth, squeezing his asscheeks, just the way he liked it.

"Oh fuck, stop, now," Tyler said, and Layla pulled her mouth off, giving his tip a kiss. He bent down and kissed her, licking saliva off her chin.

"You're such a good slut," he said, and she laughed, as he pulled her up.

"I did an enema and douched earlier. I even bought a buttplug," Layla teased him, kneeling down and bending over on the bed. She spread her asscheeks, and Tyler bent down to kiss her hole.

"Good girl. You'll still need more prep," he said, impressed, before pushing her further onto the bed, before kneeling and bending to get at her ass.

He admired her beautiful ring, before licking at it eagerly, going round the outside in circles, before lapping at her puckered asshole. Tyler always felt so happy when licking an ass, and loved the pleasure it brought his partners. Layla had felt his tongue there before, but it felt even better, knowing that it was just a prelude to even greater stimulation.

He lapped at her hole, and once it felt relaxed enough, he pushed his tongue into her ass, making Layla moan. He felt the pressure of her ass on his tongue, and felt a bump as Layla started touching herself. Once he'd gone as deep as he could, he pulled out, lapping at her hole a bit more before smacking her ass.

"Spit's never enough, we'll need lube. I know from an old fuckbuddy telling me it would be fine and then making me scream in the least sexy way possible," he said, remembering that painful day.

He walked over to the bedside table and grabbed the lube and a small buttplug from the drawer, seeing how desperate Layla's face looked, and kissing it. She kissed him back fiercely.

"I know it can be a bit scary, but we'll go at your pace. I'll make sure you're really ready with my fingers, and if you want to stop at any point just say," he said, kissing her again as she nodded, before moving back around.

He spread her asscheeks again, before squirting a dollop of lube onto the top of her ass, watching it dribble down to her wet hole. He pushed another dollop onto his finger, and gently rubbed around her asshole for a while, making her moan. He applied pressure to her asshole without penetration for a while, letting her get used to the sensations.

"I'm ready, push it inside," Layla begged.

"The first entry is the bit that can hurt the most, so I'll be slow with it," he said, "and I love teasing you," he whispered.

Layla kicked him in the chest playfully, "You bitch, just push it in," she demanded.

Tyler laughed and pushed his index finger in ever so slightly. Layla moaned gently, and Tyler pushed around her ring, moving in circles and diagonals, stretching her hole. It amazed him that an asshole could stretch to take a cock as girthy as his, and that it could go so deep inside.

He continued playing with her hole for a while longer, before pushing his finger in deeper, moving it slowly back and forth.

"That feels good. Weird but definitely good," Layla said, getting used to the feeling.

Tyler stroked her back, proud at how well she was taking it.

"I'm going to hold my finger still and I want you to rock back and forth on it," Tyler asked, and Layla eagerly complied, pushing her ass back and forth. She had such a nice ass, and Tyler loved watching it move when he fucked her from behind. She continued pushing back and forth until she got to a good pace.

"You ready for a second finger?" he asked, and she nodded again. "Of course you are, buttslut," he teased, and Layla started touching her clit.

"Good girl," he said, and pushed a second finger inside. He stretched her ring with two fingers, and then squeezed some more lube onto them, before he thrusted into her ass. This time, he tried to simulate how fast he'd be fucking with his cock, going slow at first, before speeding up the intensity.

"I can't wait to feel your cock inside me," Layla begged, desperate.

"I can't wait to fuck you," Tyler said. He wondered whether he could go in now, but as much as his cock wanted to, he knew her first time should be as gradual as possible.

He eventually pulled the two fingers out, and watched her asshole close quickly, before he kissed and licked it.

"Why did you stop?" Layla asked.

"I'm going to plug you now. I want you to be properly stretched so you can take me," he said gently.

Tyler looked at the small plug. He'd taken much bigger, but you never needed a huge one to get ready for sex. He lubed it up, and asked Layla to spread her asscheeks. When he saw a slight gape, he pushed the tip of the plug in, watching her asshole stretch to accommodate the plug. Her asshole greedily accepted the toy, and once he reached the base he twisted it a little, before smacking her ass.

"Good girl," he said, flipping her over and kissing her.

"I love you so much," Layla said, pulling him close to her.

Layla looked at him and shuffled her ass. He squeezed her tits and sucked them.

"Can I eat your ass?" Layla asked, and Tyler smiled.

"Thought you'd never ask," he rushed, and turned over, as Layla got on top of him, kissing down his back.

"You can't wait to fuck my ass, can you? Maybe I'll fuck yours soon," she teased him, running her finger over his hole.

Tyler spread his ass, and Layla bent down, kissing his hole. She licked gently, trying to mimic what Tyler had done earlier. Tyler moaned, loving the feeling of Layla's hot tongue pleasuring his ass, and he bucked his hips back and forth, stimulating his cock.

"You're suck a slutty girl eating my ass," Tyler teased, pushing his ass back onto her tongue. Layla licked even more eagerly, and Tyler grinded harder.

"I think that's all the ass licking you deserve," Layla insisted, slapping his ass one last time.

"I think yours deserves more than just licking," Tyler said, flipping over and kissing her.

"What position's best?" Layla asked.

"It depends. From behind it feels deeper, but we could start in missionary to get you used to it," he suggested. Layla nodded and lifted her legs in the air. Tyler grabbed a pillow and pushed it under her ass.

"And I can fuck your pussy a bit first," he added, lining up his cock with his girlfriend's pussy. She moved her legs down a little, before pushing a finger into her pussy to make sure she was wet enough. She nodded, and Tyler pushed inside.

"Oh fuck, I feel so full," moaned Layla at her first double penetration.

Tyler fucked her slowly, not wanting to be too rough, especially as he could feel the plug pushing at the membrane between her pussy and ass.

"Good girl," Tyler said, stroking her hair as she started rubbing her clit.

Tyler bent down and kissed Layla, speeding up a little, before gently pulling out.

He was going to lube his cock, but it was so wet from her juices.

Layla raised her legs up more, exposing the plug to Tyler. He pulled at her plug, pushing and gently tugging, and Layla moaned a little as she felt herself being stretched.

Gently, he tugged harder, and slowly watched Layla's asshole stretch wide to push out the buttplug.

Eventually, it popped out, and Layla breathed heavily. Tyler watched her gape close shut, and smiled.

"I feel so empty, please fuck me," she desperately moaned, pulling Tyler towards her.

Tyler didn't need asking twice. He pushed his cock into her asshole, and felt himself push through her tight ring. The feeling was incredible, it felt so tight and like his cock was being squeezed with pleasure.

He bent down and kissed her, slowly pushing it in deeper.

"Does it hurt?" he asked, with concern for Layla.

"It feels weird but doesn't hurt," Layla said, and Tyler kissed her hard.

He gradually pushed in and out, going a little deeper with each stroke. Layla moaned, especially when his cock was putting pressure on her ring.

"I love your ass," Tyler groaned, as he finally bottomed out and lay on top of her,

"I'm so proud of you for taking it all," he laughed.

"Beginner's luck," Layla replied, thrusting her ass back onto his cock.

"You're fucking insatiable," he said, and started fucking her ass harder, his strokes getting faster.

He watched his lover moan and writhe, her whole body moving with each thrust into her ass, and her movements intensified as Tyler squeezed her nipples. He got more and more turned on fucking her, and eventually felt his cock slip out. He collapsed onto Layla, kissing her all over.

"It feels...so good," Layla moaned, desperate to be filled again.

"I'll relube," Tyler whispered, and Layla flipped over.

"I want it from behind," she said, pushing her ass up a little.

Tyler applied some lube to his greasy cock, and stroked Layla's back, before squeezing her asscheeks. He felt so lucky to be able to fuck such a hot ass.

He pushed through her ring again, and though it was now a bit looser, it still felt heavenly to enter. Layla moaned again, and Tyler resumed his earlier pace, confident that Layla could take it.

He pushed in and out of her hole. Just like when he fucked her pussy from behind, he loved watching his cock fuck her, and he could now see her asshole stretching to take him, which turned him on even more.

Eventually, he pushed down on her back, wanting to hold her. They collapsed onto the bed, his cock still buried deep in her ass. He wrapped his arms around her tits, and kissed her neck repeatedly, thrusting more gently.

"Fuck, I'm pretty close now, this is even tighter," he moaned.

Layla was whimpering, and lifted her ass up, pushing a hand down to her pussy.

"Seems like I'm not the only one," Tyler whispered, "You need my cock in your ass, don't you?" he asked, teasing her, as he pumped in deeper.

"Yes, I need it so bad," Layla whimpered, thrusting her ass back to meet his hips. He pulled her hair gently, and she started moaning.

"Fuck, I'm cumming, I'm cumming," Layla said, and her body writhed as she orgasmed. Tyler held his cock still inside her as she came, and she drooped onto the bed.

"That was so hot, I love you, baby," Tyler moaned, fucking Layla's ass harder, feeling himself at the edge. He kissed Layla's back and pushed his cock deep, pounding against her ass, feeling it push against his hips as his cock was gripped by her asshole. He held off as long as he could, but the pleasure was too much, and he felt himself throb before spurting ropes of cum into her ass. He moaned deeply as he came, and collapsed on top of her.

They giggled and kissed for a minute, before Tyler pulled out of her ass and rolled over. He saw cum dripping out, and Layla got up to wipe herself clean. She stood up and held some tissues, before Tyler knelt behind her.

"Let me," he said, before spreading her ass and licking at her hole, loving the taste of his salty cum as her asshole winked at him. He licked at the cum that had dripped down her legs, and within a couple of minutes she was clean. Layla kissed him happily, and flopped into bed.

He washed his cock, and as he looked in the mirror he felt so lucky to be with Layla. He returned to bed, and held her tight.

"Was that how you imagined it?" he asked, not needing to ask whether she'd enjoyed it.

"I think it was better, even. I thought it would be really painful, but you were gentle, and once I got over it feeling new it just felt great," she said, kissing him.

"I love you, baby," Tyler whispered.

"I bet you took it really well," Layla said, squeezing his ass.

"My first time wasn't the best. It hurt a bit and then we stopped and just jerked each other off," he said, shrugging, "I guess that's why I wanted it to be slow and good for you."

"Aw, Tyler, it really was. I love you," Layla said, kissing him passionately, before stopping.

"I'd really like to see you take it, though," she whispered, "you must miss the feeling, right?"

"Not too much. You finger me sometimes, I've got my dildo. I don't crave it too often. I usually topped," Tyler replied. He had been exclusively a top with his ex-boyfriend Dario, but had bottomed on hookups if he felt like it.

"Still though, if you ever want to take a dick, make sure I'm there to see it," Layla teased, before kissing him for one last time that night, and rolling over to sleep.

Tyler stared up at the ceiling, before turning off the light. He thought about that time with Sam, and how hot he'd found having Layla watch. Maybe he would like to get fucked again. He started imagining the things they could do, and his cock stirred, but he was worn out from fucking. He could always talk about it with Layla tomorrow.

***

Thanks for reading, it's been a while! If you're curious about a Ch. 04, let me know in the comments, I have some ideas but would love to hear your thoughts.