Life’s Unexpected Pleasures

Maddie excepts Josh’s fantasies even at her worst nightmares

My name is Maddie. I’m 19. I was fortunate enough to get into my dream college. Columbia. I study the history of arts. A subject that’s always been a big interest of mine. I’ve gown up around artists, my parents both studied it so it’s natural I suppose for me to be into it. It’s challenging but I also want to enjoy the experience.

I’ve been here for 6 months and I’ve had an interesting journey so far. I feel like I’ve met the love of my life already. His name is Josh. He is a bit of a geek which I’m super into. He’s a gamer who studies computing here. I met him at an event. We both got drunk and one thing led to another, you already know what I mean. We’re now a happy couple.

Josh is not your obvious typical stud. He is tall (6ft3), skinny and a good looking boy. The best looking out of his friendship group, who I’ll get onto soon. Josh doesn’t really work out as you can imagine. What Josh lacks in muscle he makes up for in a different area. There is a saying about gamer boys and it’s true. His cock is about 7 inches flaccid and grows to 10 inches. The sex is incredible. Now we’re pretty comfortable with each other, Josh likes to talk about experimenting but never says what. It’s frustrating but I let him get on with it.

Now about me. I’m the opposite you could say. I love the gym, I workout a lot. I love to game too. I work hard on my bum, It’s got pretty big you could say. Josh says it’s huge but I think he is just trying to flatter me. I’m 5ft4, I’m slim, I have tanned skin from where I grew up in California. I’ve got blonde hair and freckled skin. My boobs are C cup, I like them too weirdly. I’m proud of my body. I didn’t have many friends growing up, so I worked hard for myself and my family to make them proud.

I’ve made a few friends here but I’m with Josh most of the time. He hangs around with a decent friends group. I’m not the biggest fan of his best friend Brian. He is creepy, he forces himself onto girls and he thinks the world of himself. He always makes weird comments about me and Josh just laughs and plays along. I haven’t really complained to Josh about him as I don’t want to ruin things or cause any trouble.

Brian knew that I go to the gym, so he started going to gym. He would always somehow go at the same time as me and I could literally feel his eyes stuck looking at me. He is around the same height as Josh, he has dorky glasses and a very spotty face. Pale as anything. I have no idea how he isn’t a virgin. He reminds me of an annoying fly who doesn’t go away but Josh loved him like a brother.

Anyway, enough about that dork. To now. Me and Josh were getting it on in his dorm room. It was a rough fucking, just how I like it. He came all over my ass. After we just laid there and got chatting. He finally confessed to his fantasies.
He wanted to use me like a little slut, he wanted to spit roast me with someone else and he wanted to role play. To be honest I was kind of shocked but turned on at the same time. The thought of being used was something I liked the sound of. Role play was a given. Threesome with another boy was not really an interest of mine, but this one was the one he went on about the most.

I couldn’t even imagine two cocks at once. It would have to be someone who I liked too. I don’t know… the thought was all new to me. However I said I was down for anything he wanted, cause that’s what you do for love.

So, this one night there was a party that me and Josh got invited to. It was a friend of his, Dylan who was part of his social group. Lots of drinking and partying was what it was meant to be. But it turned out to be pretty boring. The music was awful, the vibe was just soulless. Me and Josh decided to leave early and go back to his dorm to drink and play games.

We started off playing a drinking game together. It was quite hot. I was starting to feel tipsy already…

*Knock knock knock*

Someone knocked at the door or Josh’s room.

“Hey buddy” it was Brian, he invited himself in. He was a little tipsy too. Since he was also at the party, trying to get with a girl. I can now see he was rejected.

I was pissed off, he chose to come here and ruin my night. He sat himself down on a chair and started to chat so much shit it was insane. Josh was laughing his head off. My buzz was still there and I didn’t want to let it go.

“You guys playing a drinking game?” Brian said

“Yeah you wanna play?” Josh invited him.

I sighed.

“I’ve got a classic drinking game” Brian said. “It was a game called war, whoever loses has to drink” he pulls out a pack of cards.

We started playing and it was kinda fun to be fair. We were all pretty drunk. Brian kept checking me out. I was wearing a tight black dress that came down to just below my ass, I was just trying to ignore him and enjoy myself.

After a while it became a bit repetitive.

“Wanna make this interesting” Brian said. He then whispered something in Josh’s ear.

Josh laughed and agreed. I had no idea what they were talking about.

Josh then whispered what he said in my ear. It was like Chinese whispers.

“This time every time you lose, you have to remove an article of clothing”

I moved myself away quickly.

“No fucking way” I said. There was no way I was doing that with Brian in the room. He’s a total creep.

I argued a little with Josh before giving in. I wanted to be part of the fun and I had a real buzz. Besides, I was going to win anyway. There was no way I was going to strip. They decided that it was them two Vs me. Since I was the only girl.

So we played. You could see Brian became super frustrated that I was winning a lot. The boys were taking off their clothes. I had noticed that Brian had a pretty big cock too through his boxers. Yes, they were down to their boxers and socks.

At this point, I had all of my clothes on, my dress, my bra, panties, socks and shoes on. I need the use the loo. So the game paused for a couple of minutes. When I came back I could see both of the boys had semi’s. I giggled.

We started playing again and then this is where I started to lose.

I lost the first one. Off came my right shoe.

“It’s shoes, not shoe” Brian said and Josh agreed.

I had white trainers on that had now came off.

I lost again, off came my socks. My bare feet were out. Brian couldn’t take his eyes off of my feet the little perv.

I really tried but I couldn’t win. It was like it was rigged against me. (I later found out a couple days into the future that it was).

Then I had to remove my dress. I tried to protest but the games the game. I slowly removed my dress and I was just there in my bra and panties. There I glanced over and my boyfriend and his best friend were both hard. Two big cocks pressing through their briefs.

“Holy fuck” I heard Brian mutter under his breath.

Josh was loving it of course. He was so drunk.

I sat back down awkwardly. We played again. Now I still had two bits of clothing to remove they had one. It was a do or die situation for me.

I lost… Brian laughed in the most evil way possible and cheered. Josh starting to laugh like a child.

As I said a game is a game. I unhooked the bra from the back and it slipped off. I covered my boobs instantly. So my nipples couldn’t be seen. There was four eyes staring at me. It was like Josh hadn’t seen them before.

Then we played again.

“If no one wins this round, then we all have to remove the last article”. Josh said. At this point I was flustered and horny at the same time. I wanted my boyfriends cock.

The cards were shuffled and we played again. Strangely, there was no winner.

So we all stood up. I felt super shy, still covering my nipples. The two boys removed their boxers. The size of Brian’s cock shocked me. It was huge like Josh’s just more thicker. I pulled down my panties, trying to cover up as much as possible. We were all naked.

Josh then came over to me and we started to make out. It was pretty hot. I started to jerk him off, completely forgetting that Brian was in the room. After a few minutes, I glanced over and Brian was jerking himself off to the sight.

It was awkward. Josh then whispered in my ear. “Will you let one of my fantasies come true baby”. I felt disgusted at the fact that it was Brian. I tried to protest against it. He begged me. I gave in, my heart sank.

“Hey buddy come here” Josh said.

Brian walked over. Both of their cocks pointing towards me. Josh grabbed my hand and put it on Brian’s cock. Holy fuck it was big. I was jerking both of them off while they touched me up.

“Her ass is so fucking sexy” Brian said.

They touched me up. I ended up on my knees with both cocks pointing towards me. I closed my eyes and pretended it was someone else. I started to suck Josh off while jerking Brian. I then switched. I had Brian’s cock in my mouth, it tasted funny. I have no gag reflex, he started to fuck my throat. I then tried put both cocks in my mouth, I was giving these boys the time of their lives.

Josh then picked me up and put me on the bed. I was on my back and he put his cock inside of me. While I sucked on Brian’s cock. Brian grabbing my tits. While they bounced up and down. It was rough, but it felt amazing. I felt like I was a proper slut.

It was then time for them to switch. Brian flipped me into doggy position, I started to suck on Josh’s cock. Brian started to tongue my pussy. It was quite good to be fair to him. He then moved to my virgin asshole, I screeched as he buried his face into my cheeks and tongued it. It felt unbelievable. He then got up and placed his cock again my cunt. He then slid in.

It fucking hurt. A muffled scream, from where Josh’s cock was inside my mouth.

“Look at that ass jiggle it’s incredible” they both complimented me. Little did I know I was getting filmed.

He fucked me hard. He was rubbing my asshole at the same time. I came all over my boyfriends best friends cock. How strange?

It was good tho. I then got up and onto Josh’s cock where he started to fuck me. I look back to see Brian using Josh’s lube to lube up his cock. I had no idea what was going on I was too drunk to think straight with a huge cock fucking me.

I then felt Brian’s cock push against my virgin asshole. I screamed and tried to push him off but I couldn’t. It slowly inserted.
He moved the tip in and out. It was so painful, I couldn’t take it. I was moaning and screaming at the same time. Josh didn’t do anything he was enjoying my pussy. This creep was taking my anal virginity. He pushed in and I was getting double penetrated. It was rough. It felt so good and painful at the same time. I could feel my own ass bouncing against these two cocks.

After a couple of minutes they switched, I was in reverse cowgirl. Josh entered my ass, while Brian entered my pussy. He fucked me, put his hand around my necked and looked into my eyes. I tried to look away.

They then got off of me. Stood up over me and started to cum all over my face. I was drenched in cum. It was so hot. I wiped the cum off of my face and sucked it up. Trying to be sexy. They enjoyed it, I just laid there naked.

Without me seeing, Brian picked up his phone that was recording, picked up my panties that were on the floor and left.

This may just be the start of it. It was hot although I still thought Brian was an ugly piece of shit.

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