Lucas was my best friend, we were both the same age (24 years old) and we had the habit of making bets over Mortal Kombat.
At the start, it was stupid things like eating gross food, but things escalated. The last two times I made him put his hand on the toilet and worst of all shave one eyebrow.
Lucas was out for revenge. I think he spent the whole week planning the next challenge. When Saturday came and I went to his house my jaw dropped when I saw the bet he had planned.
— Look at this beauty – He said holding a buttplug.
— What are you doing with this shit?
— This will be our bet today, the loser will have to buttplug his ass.
— If you want to sit on a buttplug, you can do it! There is no need to make it a bet – I said laughing – I'm down for it, but I don't wanna see you trying to go back on the bet like last week.
Usually, we waited a little before making the bets, but this time we went straight to the games.
— Bo3 – I told him and he agreed.
I can barely remember the matches, he beat me in a second. I couldn't believe it since I was always the better player, I am pretty sure he spent the week practicing for the match.
My heart started to race once the matches were over, I couldn't go back on my word, Lucas did every single challenge even though he was almost always the loser.
I didn't have any time to think, right after the match he was already pressuring me.
— Don't worry it is only three inches – He said with a stupid grin on his face.
— Can I do it alone in the bathroom?
— How will I know if you did it?
— My word isn't enough?
— It isn't a challenge if no one sees it, I am still with this stupid ass eyebrow on my face. Your challenge isn't even that bad, I am the only one who will see it.
I grabbed the buttplug already shaking, got rid of my pants and underwear, and lay on Lucas bed.
I tried it for maybe a minute, but I was having trouble getting the toy in so I told him almost crying.
— I don't think this will work out, I can't do it.
— No, no you won't get away with it. You lost, you have to pay the bet.
— Sorry man, I can't do it. Just chose another challenge.
— Just wait one second.
He went to the bathroom and came back with a bottle.
— What is this? I asked afraid.
— Just some lube to help you out.
I didn't know if was happy or terrified of him saying that. He grabbed the buttplug from my hand and started to lube it.
— Open your cheeks – He said – I never thought I would hear these words from another dude and comply, but here was I doing it.
He tried to push it inside of me, but my reaction was to flinch.
— No, no! I can't!
He left the toy on the bed and grabbed the lube again. He squirted a lot on his hand and I felt the cold when he started putting it around my asshole. I don't know why but this made me relax a little bit until I flinched again when I felt the pressure on my hole.
— What are you doing? – I asked in shock
— It is just a finger.
— This wasn't the bet.
— You gotta relax dude, I'm just helping you here.
I was about to make another complaint, but I felt his middle finger finally getting inside and the only words that came out of my mouth were:
— Fuck! fuck, fuck, fuck…
— You gotta relax dude – He said again
I could feel him pushing his finger away and in again, each time he was getting deeper and deeper. When his middle finger got completely inside of my ass he pushed it all out filled his finger with lube and put it back in one more time.
— Relax, relax, relax – He kept saying with a calm voice.
— See it? It is in – My only answer was a deep moan of pain.
— You are ready now! – He said while removing the finger out of my ass.
He lubed the buttplug again and started slowly introducing it inside of my ass. I was surprised with how easily it got in and even more surprised when he announced it.
— See! It is all the way in! Can I grab a photo – He said laughing.
— Fuck off! – I told him – Is it over now? Can I take it off?
— Wait a minute – He said.
He moved towards me again, I thought he was about to take it off, but he pushed it halfway out and in again.
— Fuck! – I moved my arm trying to push him away.
He grabbed my arm and told me one more time
— You gotta relax dude!
— The bet is over – I told him
— Let's just play a little bit – He said with a smile while pushing my arm to the side and grabbing the toy again.
He pushed the toy in and out a few times and there was nothing I could do besides moaning.
— You like it? – He asked me.
— No, I don't – I answered him, but the moan that came out with it was one of pleasure and I went completely red.
— How does it few to be a little bitch?
— Fuck off – I said pushing him, taking control again, removing the buttplug and throwing it away.
— This is it! The bet is off.
— You gotta stop pretending you didn't like it – He said with that stupid grin.
— Shut up!
— Dude you are hard as fuck!
I didn't even realize until now but I was keeping a huge boner. I was struggling to admit it, but there was something incredibly hot about this whole situation.
— This will stay between us – Lucas said while moving to the side of the bed, laying by my side, grabbing my boner, and starting to jerk me off.
You should jerk yourself – He said to me and I complied.
I was just enjoying myself and I finally felt his finger finding his way into my asshole. This time I was able to close my mind and enjoy what was happening the pleasure of jerking myself off while Lucas played with my prostate was unbelievable. Between my moans of pleasure, I was able to ask him.
— Grab the buttplug again
He left the bed and grabbed the toy on the floor.
I was eager for the feeling of having my ass full again. Lucas looked at the toy, looked at me again, grabbed his boner under his sweatpants, and said.
— I think I have something better for you right here.
He took off his shirt, his pants and lubed his dick. Felt like the whole process took hours, I couldn't believe myself, but I was eager to have him inside me.
— Open your legs! – He said in a commanding voice.
I could feel his dick working around my hole until he finally started to slowly push in and out.
— I can't believe I am balls deep inside of you – He said biting his lips
I couldn't believe it either, but it felt right I played with his abs while asking him to fuck me. He started slow and I felt like I was in paradise. He was right, this was much better than the butt plug.
I was jerking myself and finally felt the urge.
— I'm coming.
— Yeah? Let me see it – Lucas said while fucking me.
I was trying my best to hold it, but the cum exploded all over my stomach and Lucas started to play with my cum while still fucking me.
I felt I wouldn't be able to take it anymore after the orgasm, he kept fucking me faster and faster until he suddenly stopped.
— Turn over! I want to fuck you doggy style.
I turned over and he didn't waste any time, he grabbed me by my hips and started fucking me again harder than ever. I was about to ask him to go slower, but his dick started pulsing and I felt his warm cum. His pace started to slow until he finally pulled his dick away.
— We gotta do this more times – He said laughing.