DISCLAIMER: THESE ARE NOT MY CHARACTERS, THESE CHARACTERS BELONG TO THE CREATORS OF TEEN WOLF!

Stiles was frantically rushing down the hallways. He didn't even notice Scott waving hello to him. He was a boy on a mission. He spotted his target and ran towards. 'Lydia! I need you help!' He said between pants.

'Not even a 'Hello Lydia!'' She said to Stiles while she was looking through her locker.

'Look. I am in desperate need of your help. Please?' She was still uninterested. 'Please Lydia? I need your sexual wisdom.' She heard those words and she was hooked. She quickly turned from her locker and looked straight at Stiles.

So you need that kind of help? Okay. Shoot.'

'As you know, Derek and I have been going out for a three months. We've been having sex just as long. He's actually quite good. Amazing actually. He does this thing with his tongue-'

'Stiles! To the point!'

'He sent me this text in class.' Stiles quickly whipped the phone out of his pocket and showed it to Lydia. The text message read: 9pm, your house. Tonight I'm going to fuck your ass like no tomorrow. See ya then xoxo. 'Normally this would be fine. But I have been bottoming for three months. Three months! Sure not every day, but still. His dick is huge, and having that werewolf strength and speed pound into you can get quite painful. What do I do?'

'Have you tried telling him you want to top?'

'Well it's not that easy. He normally comes into the room and then we are at it straight away. Plus, I don't know if I can fully satisfy him.'

'He's a guy! Guy's are like coke cans. You shake them up a little bit and then they blow. Simple as that.'

'Yeah but if and even get him to bottom, I don't know if a can 'shake him up' myself.'

'Well then use some toys.'

'I don't have any.'

'You can use mine.'

'You have sex toys?'

'Yes. Jackson bought some while we were dating but we only used two. Come by my house after school and I'll give you the rest. You can even keep them.'

'You would do that for me? Wow! Thanks Lydia. Wait! I thought Jackson was great at sex. Why would you need toys?'

'Like a said before: you shake guys up a little bit and then they blow. Women need more than just that. And also, he wouldn't admit it, but he tried it a couple of times.'

'Women enjoy watching guys do that?'

'Not necessarily. He wanted to experience the pleasure of an orgasm while his prostate was being massaged. He set it felt better than usual.'

'It does.' Lydia watch as Stiles smirked and started thinking about the feeling.

'You should probably go.'

'Yeah I should.' Stiles didn't move.

'Now!'

'Right.' Stiles woke from his dreamy state and walked away.

…

Stiles looked at the time on his phone. Derek was going to be there soon. He glanced over at the box of toys Lydia gave him. There were in a Louboutin shoebox. Lydia always had an obsession with her designer clothing. He was getting antsy until he heard Derek walk through the front door. He then opened the door and embraced Stiles in a passionate kiss. Tongues were colliding while hands went in the air. Shoes were kicked off while Derek removed his shirt and started to lift Stiles'. He pulled back. 'Wait! Just wait.'

'Is something wrong.'

'No everything's fine. I just- I wanted to try something different tonight.'

'What do you mean?'

'I-I-I want-'

'Spit it out sweetie.'

'I want to top!' Stiles blurted. 'Please?' He said softly.

'Don't you like bottoming?'

'No, no … I love it! It's just … we've been having sex for three months now, and every time I have bottomed. I just wanted to try topping for once.'

'Wow! We've been having sex for three months? God I've been so selfish. I'm so sorry Stiles. Your ass must really hurt, huh?'

'It's fine. We don't ha-'

'No we are having sex and you are topping! That is that!'

'Really?'

'Of course. I guess the only reason I haven't thought about it is because I've never bottomed before.'

'You never bottomed?'

'No. You're the first guy I've ever been with. And I just assumed the role of top because I was used to it. Sure, I've played with my ass before but I've never actually experienced full penetration.'

'Well I can help with that. I got some sex toys for us to use.' Stiles grabbed the box of toys and opened it.

'Where'd you got those?'

'No where.'

'You got them from Lydia didn't you?'

'How did you know?'

'Louboutin shoebox.'

'Oh right. Well … do you want to?'

'Fuck yeah! Come on, let's get started.' Derek grabbed Stiles into another passionate kiss, making Stiles drop the box on the floor. Stiles started to unzip Derek's jeans and pulled them down. He grabbed the elastic of Derek's boxer briefs and pulled them off too. He then pushed the heavier man onto the bed and removed his own shirt. He hovered over Derek and started to kiss him again. He then moved from his lips and planted kiss from his hairy jaw line to his muscular neck. He sucked profusely on his neck before moving down, now planting kisses past his chest and abdomen. He stopped before the hairy navel and grabbed Derek now hard cock in his hand. A bead of pre-cum seeped from the tip. Stiles licked it up and watched the trail of fluid stick to both the head and his lip. He then opened his mouth wide before lowering his head and swallowing all of Derek's length in one go. He came up and then down again, repeating this for a good fifteen minutes. Derek's dick was now fully erect and coated in a mixture of saliva and pre-cum. Stiles grabbed the lube from his drawer and picked up the first toy from the shoebox. It was a small butt plug with a curly handle. Derek lifted his legs in the air and let Stiles lather his hairy hole with lube. He rubbed lube on the butt plug before asking Derek, 'You ready?'

'I'm ready.'

Derek felt Stiles place the plug at his rim. He breathed out as Stiles slowly pushed it in. It was small so there was little pain. Stiles pushed it in further till it was at the hilt of the handle. He wriggled it around before pulling it out and in again. Derek liked the feeling. Derek looked a little disappointed when Stiles pulled it out and put it away after ten minutes. Stiles picked up another item. This time it was a clear rubber dildo with a pink tinge. Derek wanted more and eagerly nodded to the question before Stiles even asked the question. Stiles pushed the tip into Derek and watched as his ass contracted around the dildo multiple times. He pushed it in deeper and watched as his lover thrust his abdomen into the air. He quickened his pace this time when pulling in and out, but it was a lot harder to control than the butt plug. This one was a little more painful but it was nothing the werewolf couldn't handle. Stiles pulled it out and grabbed the final toy. This time it was a vibrator. He looked at Derek again. He was unsure. He knew he wanted more but he didn't know if he was ready. 'Fuck it. Let's do it.' Stiles slowly pushed the off vibrator into him. He waited until it was fully in and then grabbed the controller. He slowly scrolled it and watched as Derek started to feel the vibrations. He stopped at half way and put the controller down. Stiles started sucking on Derek's dick. It was so pleasurable that Derek protracted his claws and dug into the back of his thighs. He started to bleed a little bit and unintentionally grabbed Stiles' head. Stiles could feel the claws and pulled away. He stopped the vibrator. 'We should probably tie those up. I'll get the rope that you used on me. Stiles quickly ran to his closet and grabbed the red rope of the floor. Derek got on his knees and turned around as Stiles tied his hands behind his back. 'Are you okay with this?'

'It's fine. I don't want to hurt you and I shouldn't if I'm lying on them.' Derek laid back down as Stiles put the vibrator back to halfway and started sucking again. Ten minutes had passed and Stiles decided to swap places with Derek. Stiles removed his pants and underwear and put his head against the headboard. Stiles pointed both hands to his dick. 'Suck.' Derek was eager. He quickly started licking Stiles' dick up and down before swallowing it all. Derek's lips felt perfect. He still had his hands tied behind his back and vibrator in but was doing an excellent job. Stiles decided to up the vibrator to full and felt the vibrations of Derek's moan on his dick. Both boys were in heaven. Another fifteen minutes had passed and now both boys wanted Stiles to use his own cock. Stiles untied Derek, stopped the vibrator and pull it and out of him. Stiles went to grab a condom but Derek stopped him and said 'I want to feel the real you inside of me.' Derek got on his hands and knees and faced the headboard. Stiles got behind him and put the head against Derek hairy, wet hole. He pressed his cock all the way in and Derek let out a moan as his hands gave way and fell to his elbows. Stiles grabbed Derek's hips and started to thrust into him. With each thrust, Derek let out a moan or a shallow pant. He dug his nails into Stiles' bed and sheets and just let Stiles plough his ass. Stiles was great at sex, much better than Derek was when he first had sex. Derek bowed his head and rested it on his arms. Derek was getting it good from Stiles. He was much better than Derek expected. Stiles then rested his head on Derek's tattoo but didn't lose rhythm. Derek loved the feel of Stiles' cock inside of him and Stiles loved the sensation and how tight Derek's hole was. Stiles pulled around and wanted to try a different position. He got up and then laid back down on the headboard, slightly higher this time with his and shoulders against the headboard. Derek stood up on the bed. He positioned himself so he just had to sit down on Stiles' dick. He put his hands on the top of the headboard lowering his ass closer to Stiles and grabbed his cock in the other hand so that they would meet. He felt the tip of Stiles go in him. He lowered himself further until the cock was completely in. Stiles put his hands on Derek's ass. Derek started gyrating his hips and grinding into Stiles. Both men started to moan loudly. They looked at each other with great desire. Stiles could feel the pre-cum drip from Derek's dick and land on his abdomen. Both boys watched the sweat beads on each other's foreheads. Stiles the pushed Derek on his back and pressed their bodies together. Stiles put his face against Derek's chest and moved one hand to the bed and the other to his hair. He grabbed both sheets and hair as he thrust deeper into Derek. Derek moved his hands from Stiles' shoulder and caressed the teen's body as he lowered them near his ass, feeling the little dark brown hairs on it. 'Don't stop Stiles! Don't stop!' Derek said between moans and pants. Derek was getting closer. He knew it was going to stop soon but this felt too good. He wanted this to last forever. Derek could feel his cock begging for release. 'I'm gonna cum.' Stiles lifted his body off Derek and continued to hammering into him. 'I'm gonna cum! I'm gonna-' Derek erupted like Lydia said. Creamy cum travelled through the air and landing all over Derek's face, even hitting his stubble. Muscles were contracting and Derek was wheezing and moaning. Stiles was close too so he pulled out of Derek laid back down against the headboard. Derek followed and put his face in between Stiles' legs. Stiles pumped his dick and felt the beginning of the orgasm.

'Oh fuck!' Stiles said as his thick cum spurted out, sticking do Derek's beard, cheeks, lips and eyebrows. Stiles pulled him up and kissed Derek. Derek pulled away.

'You have to top more often.' Both boys smiled and continued kissing as Stiles rolled Derek over and covered each other under the sheets.