My Best Friend Helps Me with a Toy

My straight best friend Matt had given me a dare. He had dared me not to masturbate all week unless he said to me 'Green Light' and then I could start again. It had been TORTURE. Not least because the last time we spoke, he made me do a forfeit where I twerked for him on Facetime and when I turned round... he'd CUM. He'd cum whilst looking at my ass. I couldn't believe it. It felt forbidden. And that turned me on so fucking much.

The other thing I couldn't get over is Matt had promised me a dare in return. I could dare him to do ANYTHING. I'd had to admit our exploration together recently had been affecting me a lot. I couldn't stop thinking of his hard athletic body. And his beautiful cock. I'd never felt this about any man before. But my straight best friend was making me salivate every time I thought about him. So the idea that I could dare him to do anything I wanted felt so sexy.

I was used to masturbating atleast once a day so this abstinence was making me go crazy. I wanted to touch myself so badly. I'd resulted to just gently rubbing my body all over, just to feel some kind of sensation. I had to admit, Matt's fascination with my ass had intrigued me. I'd never thought about my ass before really. But during this week, I found myself staring at it in the mirror a lot. Matt had said he thought it looked like a girls and I was starting to agree with him. It was rounder and plumper than I'd ever realised. I began to stroke and grope my ass cheeks to try and quash my horniness. But it only made it worse.

That's when I realised there could be a loophole here. Literally a hole I could exploit...

When Matt had said I couldn't masturbate, he would have meant my cock. As a straight man you can't masturbate anywhere other than that.

And with that realisation, I moved my finger down to my hole.

Something inside of me wanted this. No. Craved it.

Besides, if my ass looked as girly as Matt said it did, it's more like I'm fingering a woman than myself. This couldn't be gay.

My ass play started off gently at first, but within minutes I found myself bent over my bed and fucking my hole with abandon. It felt good. Especially after days with no masturbating. I was finally getting some relief. Damn, I could see why gay guys liked this.

Suddenly, I heard a notification from my phone. I picked it up to see a new message from Matt. Damn, I wonder what he was going to say, we hadn't spoken since he'd made me do that forfeit.

MATT: You better not be masturbating 😈

He was so sexy when he was being controlling.

OLLIE: Not at all 👀

MATT: Good. Because if you so much as touch that cock then there will be a new forfeit.

Oh fuck, that kinda made me want to touch it even more.

OLLIE: Don't worry man, I've been good 😇

MATT: Better have been. By the way, I should thank you. Your sexting advice worked a treat.

Matt had recently had a break up and had asked me some advice on how to sext this girl he had been messaging on Tinder.

MATT: She sent me so many pics. It was fucking crazy. Do you wanna see?

OLLIE: Damn, yeah send them over.

Matt sent through photo after photo of this hot as fuck girl he had been messaging. Slowly taking off her clothes for him and revealing more and more. They were so hot.

MATT: DON'T MASTURBATE to these though man. Remember the deal.

He was being a right tease, it felt like he was sending these deliberately to horn me up. And it was working.

Suddenly, a different nude came through.

It was Matt.

It was Matt's naked body and fucking gorgeous dick. The caption read 'Are you craving this dick in your hole right now bby?'.

Oh fuck. He looked SO good and his dick looked amazing. I began to rub my hole again at the sight of it.

MATT: Oh shit man, didn't mean to send that one.

OLLIE: Hah no worries man, I'm getting used to it at this point hahah.

MATT: Are you saying you're bored of it? 😉

How should I respond to this?

OLLIE: Oh yeah, I want nothing else than to keep seeing more of your big cock 😂

I was sarcastically pretty much telling my best friend the actual truth. I did want to see more of his straight cock. I don't know why. I just did. Ever since I'd helped him cum with my fleshlight I had become fascinated by it.

MATT: Don't get too excited by my cock. You're not meant to be cumming remember 😉

OLLIE: Stop being an ass 😂

MATT: You free Saturday anyway?

OLLIE: I'm free Friday if you wanna meet earlier?

MATT: Is that just because you're dying to cum 😂

OLLIE: You can see right through me can't you 😂🙈

Little did he know I was sat here full on fingering my ass right now.

MATT: You need it don't you? What would you do to make me say Green Light right now?

OLLIE: Anything man. I need it. Please.

It was true, however nice my ass play was. I'd given anything to touch my cock right now.

MATT: You'll have to wait till Friday then 😈

OLLIE: Don't forget you owe me a dare too.

MATT: You better get thinking about what you want then.

And with that. He stopped messaging.

Friday couldn't come soon enough.

FRIDAY NIGHT

The night I had been waiting for finally arrived. I heard a knock at the door of my apartment. Suddenly I felt quite nervous. I think the teasing throughout the week had got to me. I was getting butterflies at the thought of my athletic sexy best friend turning up. Excited by the possibilities of what could happen.

I opened the door to see him there waiting for me.

"Hey Ollie, long time no see" he laughed.

I let him in and we moved into the living room to sit on my sofa.

"Did you wanna watch a film or..." I asked.

"Have you kept your promise? " He cut in immediately.

"Yes." I replied.

"No masturbating at all? Bet that was hard for you" he teased.

"Hard is definitely the way to put it." I laughed.

Something felt different to the last time we'd sat on this sofa when I'd invited him round for a movie night. Something had changed within us. But why?

I mean, I'd held a fleshlight for him, drank his cum and twerked on camera for him. But we were still best friends right?

But as I looked into his eyes, I didn't see the eyes of a friend. I saw the hungry eyes of a man who wanted something.

"I wanted to ask you something." I said hesitantly.

"Sure..." he replied.

"Did you cum the other night?" I asked.

"When?".

"When I was doing that forfeit for you. Shaking my ass.".

Matt paused.

"No way man." He laughed.

"But... I thought I saw.." I started.

"That would have been pretty gay if I was cumming to you shaking your boy ass."

"I thought you said it looked like a girls?"

"True. It does." he sighed.

"Then it wouldn't be gay if you liked it would it?"

"You've got me there." He laughed. "It is an amazing ass man. Girls would be jealous of that thing."

"Thanks, I never realised." I laughed.

"Really? You never had a girl venture down there before?" Matt asked.

"No never! Have you?" I said in shock. Keeping my ass play this week secret.

"Hell yeah man. Lacey put a finger up there when I was cumming once."

Wow, it was hot to imagine Matt experimenting with his ass too.

"Damn really?"

"Yeah man, it was so intense. With an ass like yours you'd probably love it."

"Well... I may have tried it." I said nervously. I decided to be honest and see where it would lead.

"What, I thought you just said you didn't." Matt asked.

"You just asked if a girl had, I've tried my own finger." I replied.

"Holy shit. Well good for you man. Did you like it?"

"Yeah, I kinda did."

"I bet you did." he replied boldly. "You really are a horny slut aren't you?"

"Maybe I am." I replied.

"With an ass like that I'm not surprised. That thing was made to be fucked." Matt exclaimed.

This was some of the boldest, most direct language he'd used yet. And it was turning me on so much.

"Are you still dying to cum?" he growled.

"Fuck yeah."

"Bet you just can't wait for me to say Green..." Matt started.

Fuck, as soon as he said Green my cock shot up. I was rock hard in seconds waiting for his command for me to cum.

"Not yet bitch." Matt laughed.

"Fuck you man. I'm so horny."

"Well, I think you've earned your dare then. Go on. What do you want me to do?" He asked.

This was the moment. The moment I could make him do whatever I wanted. And I had a plan.

"You know how I helped you with the fleshlight?"

"Hahah. I see where this is going." He replied.

"You really don't." I replied.

I pulled out a box from behind the sofa.

"I want help with a toy too." I replied, my voice shaking with nerves.

"What kind of toy?" He asked confused.

"This." I said and opened the box to reveal a DILDO. A big 8 inch black coloured dildo. I'd bought it online during the week after getting incredibly horny and curious from my ass play.

"Holy shit dude. Are you joking?" Matt replied as he picked up the dildo and examined it.

"I think you're right. My ass needs this." I replied pathetically.

"It definitely looked like it did when you were twerking. You were begging for it man. You looked so GAY." Matt replied.

"It's not gay though. I don't want an actual cock. It's just a toy. It's like masturbating."

"I don't know man." Matt said sceptically.

"Was it gay for you to use my fleshlight?" I asked.

"No."

"Then this is the same thing isn't it. It's just a toy." I reasoned.

"Hm. sure. So what's the dare?" he asked.

"I've been struggling to find a good angle to use it myself. So I dare you to help me. Use it on me." I demanded.

"This is crazy man."

"Hey, you owe me."

"True. So how do you want to do this?"

I got off the sofa and gestured for him to follow. I couldn't believe this was actually happening. Was I going to do this?

Ofcourse I was. I needed it. All my horniness this week had led to this moment.

I leaned over the sofa and presented my ass in my sweatpants for my best friend.

"Damn Ollie, you nearly took my eye out with that thing." He joked.

"Just you wait." I laughed.

And with that, I slowly peeled my sweatpants down to reveal my naked ass.

"Wow. It's even bigger in person." Matt exclaimed. "It really does look like a woman's ass holy shit."

"Does it look like something your tinder girl could have sent?" I asked.

"Hell yeah man. Even better than that."

Something inside my loved the fact that he appreciated my ass. He was complimenting it. The whole situation was wild.

"Let me just lube it up." I said as I reached into my pocket to find some lube.

My best friend just stood behind me and watched as my finger rubbed lube into my hole. I felt so exposed. So vulnerable. I wondered what was going through his mind.

"I can't believe what I'm seeing." he said, breaking the thick silence in the room.

I begun to force my finger into my hole now. Fingering myself in front of him.

Quickly I built up pace and was pistoning my finger in and out.

I felt like I was putting on a show for him. But was he enjoying it or was it completely freaked out?

"Okay man, I'm ready. Put that thing inside me." I pleaded.

"I don't know if I can do this man. This feels weird."

"After everything I've done for you man? Please just try it?" I asked.

Matt thought for a second. I think he was running through everything I HAD done recently. I'd helped masturbate his dick with a fleshlight for gods sake.

"True. You've been such a good friend." Matt said. "Here you go."

He leant forward and whispered in my ear.

"Your reward." he said.

Damn that was fucking hot feeling his breath in my ear as he said it. And with that, I moved my finger away from my hole. It was quickly replaced by cold plastic.

Matt had picked up the dildo and positioned it at my entrance.

"Are you sure you want this?" he asked.

"Fuck yeah." I replied.

"Damn. Horny little bitch." He joked.

I felt extra pressure as Matt started to push the toy up my virgin hole. It felt so alien. So much bigger and wider than my finger had been. And the fact my straight best friend was doing it made it all the crazier of an experience.

He kept pushing and pushing until it was nearly all the way inside me. As Matt slowly penetrated my ass with the dildo, my own cock began to rise higher and higher. What did this say about me that I was getting so turned on by my ass being filled. Fuck. Was this still straight.

He bottomed out the dildo in my hole as I felt the plastic balls brush my own.

It was one of the strangest sensations I ever felt.

But as he started to pull it back out. It quickly turned from strange to FUCKING amazing.

Matt was right. This was intense.

"How does it feel?" Matt asked curiously.

"Good. Fuck, it feels good man."

"I told you it was intense didn't I?" He teased.

"SO intense." I moaned.

My cock had become rock hard at this point. I wish I could see what was happening, but as I was bent over the sofa in a doggy like position, I had no idea. I wanted to see Matt. How this hunk of a best friend was responding to all this.

"Fuck I'm so horny." I moaned as he fucked me with the toy.

I couldn't help it. I needed to touch my cock.

My hand moved round to grab it and start pulling.

SLAP.

Suddenly Matt's hand slapped mine away from my cock.

"When did I say you could start masturbating?!" He said.

"Fuck, sorry man." I said hastily.

"You realise you broke the dare. I'll need to give you a new forfeit now." He commanded.

"Oh fuck, I'm really sorry. Please not another forfeit." I begged.

"Too late. You know the rules bitch."

With that, Matt yanked the dildo out of my hole. My ass felt so empty without it. Like it needed to be filled again immediately.

"Please Matt."

"You made me put this dildo inside you man. It's humiliating. The least you can do is follow the rules and do a forfeit."

"Urgh. Fine. What is it?"

Suddenly I heard movement behind me. The noise of rustling clothes filled the air.

"The forfeit is..." Matt started.

Suddenly I felt the dildo back at my ass hole.

"You have to take this." Matt grunted.

Matt's hands grabbed both of my ass cheeks as he forced the dildo back inside me.

Fuck it felt so big. So thick. It was hitting spots it hadn't hit before.

Wait...

If both Matt's hands were on my arse... how was he holding the dildo?

I turned round to see Matt's naked body was fully collapsed into me. His head tilted down with eyes closed in concentration.

It wasn't the dildo inside me. It was A COCK.

MATT'S COCK.

Oh shiiiit.

Suddenly Matt opened his eyes and gazed down at me. His expression filled with authority.

"Take this fucking cock man." he demanded. "You've been teasing me so fucking much."

His muscular arms held my cheeks as he yanked his massive weapon in and out of my tight virgin hole.

"Do you like it?" He asked.

"Oh Matt." I moaned.

"I asked you a question bitch, do you like it?"

He brought his head alongside mine, grabbed my hair and pulled my head up as he whispered in my ear.

"Do you like my COCK in your ASS?" he repeated.

"FUCK YEAH." I screamed.

"I knew it. This ass was made to take cock."

He continued his absolute assault on my insides. Thrusting in with a strength and force I'd never felt before. This is what it felt like to be dominated. To be taken by a real man. To be his TOY.

"I thought you weren't gay." I asked as he fucked me.

"It's hardly gay if a little slut like you is begging for it this much. I mean you wanked my dick with a fleshlight for gods sake." he replied.

"I was just helping you."

"Were you just helping when you teased me all night with your sexting?"

"Yes." I moaned.

"What about when you used my voice to make you cum when we were gaming?"

"I was just horny." I replied.

"No. You wanted this. You craved it ever since I showed you that nude in this living room. I could see it in your eyes. You wanted me."

He carried on attacking my hole with a passion as he let his words sink in.

"Tell me I'm right, you wanted to be my little slut." he demanded.

"Ughn fuck. It's true."

"What did you want?" He asked as he carried on holding me. Pulling his massive cock in and out of me.

"I wanted your big FUCKING cock inside me."

"Too. Fucking. Right." Matt replied.

He suddenly withdrew from my ass and flipped me round. He let me hang on the arm of the sofa, my legs pulled up to his shoulders. From this angle I could finally see him. His sculpted naked body infront of me. His beautiful pecks and gorgeous body hair. In that moment I was the most attracted to any person in my entire life.

I could also see his thick meat for first time as he pushed it back into my hole.

In that moment it felt right. Like my ass had been built for his cock.

"And do you wanna know the truth?" Matt asked. "I wanted you too."

I couldn't believe what I'd heard.

I didn't have long to think about it though as Matt's face came crashing down to mine.

He kissed me.

Time stood still in that moment as I locked lips with my straight best friend.

And I kissed him back.

I kissed him back with a passion. And we didn't stop. For twenty minutes. We made out as he destroyed my tight little anus.

"I've got one thing left to say Ollie." he said sexily.

"What?"

"GREEN LIGHT." He commanded as he grabbed my cock for the first time.

He jerked me off in my hand and I finally exploded after a week of teasing. Cum SHOT everywhere. It was the biggest load I'd ever had.

"FUCK MATT" I screamed.

"FUCK I'M CUMMING TOO." he yelled.

"YES. CUM FOR ME MATT. Paint my hole with your seed. Make it YOURS." I couldn't believe what I was saying but I meant it.

"Gonna breed that slutty little hole bitch."

I looked up at his eyes as he scrunched them up in absolute focus.

He needed to cum.

He just needed a push.

"Green light." I whispered.

It was the magic words. With a massive GRUNT. Matt came in my ass for the first time. My straight ass had worked a massive load of semen out of my straight best friend. I couldn't believe it.

"Fuck. I don't need your fleshlight anymore man. You're my fleshlight now." Matt exclaimed as he collapsed on top of me.

The End.