Unexpectedly fucking [m]y [f]riend at a Halloween party

Apologies ahead of time for a ton of background and a complete inability to write dialogue!

In college I had a friend named Caroline. Caroline was a very intelligent, loquacious and outgoing girl. She could always bring me out of a lowly mood and was always a welcome addition when a group got together to go out drinking at the bars. On top of her great personality, Caroline had an amazing body. She had green eyes, jet-black hair and skin that was extremely smooth and pale in a very appealing way. She also had smaller breasts that I can only imagine were maybe B cups (not that that’s a bad thing) but her ass was amazingly sizeable and round and she liked to joke that it was her one redeeming feature. I highly disagreed with that. She had several features that made her extremely physically appealing. Nonetheless, for some reason it really turned me on that she knew she had a nice butt and was proud of it. She always wore skirts, dresses and tights that accentuated and showcased her lower half. One time she came to a study session for a test in a class we shared wearing those tight Nike Pro shorts. I maintain to this day that her wearing those shorts is the reason I got a D on that test (insert joke about her getting the D).

I met Caroline early in my sophomore year. We had the same business ethics class together during our first semester, but didn’t actually talk to each other for the first couple of months. I definitely noticed her though. I’m not going to pretend and act like she struck my eye all semester and I constantly thought about her, but I for sure saw her and acknowledged to myself that she was attractive. It’s always nice to have eye candy in any class. Anyways, I first talked to her at a mid-term study group that was set up between several students in the class. It was held in an empty lecture hall and everyone just casually sat towards the front of the room. I ended up sitting close to Caroline and introduced myself after a while. We started discussing where we were with the study material and how comfortable we were leading up to the test. I suppose some of the things we said could be described as flirting, but it wasn’t really crazy and when we exchanged numbers, there wasn’t anything implied. We began texting each other in class and joking about our professor and other students. I’m sure this sounds like the initial stages of a budding romance but it really never ended up like that.

Throughout our entire undergrad, we remained strictly friends. We never discussed any attraction and neither of us made any moves. We were just really good friends and spent a lot of time together. I would hang out in her dorm room and she would visit me at the house I rented with a few friends. I would meet up with her at bars and she’d come pregame with us. That’s a lot of words to essentially just say that we were two people who had a lot of fun together but never moved past that. Of course, people implied and joked that we were hooking up. I would deny it when it came up, but I honestly didn’t mind. Nothing wrong with people thinking you’re having sex with a hot girl. I’m also not going to act like I didn’t think about fucking Caroline. I don’t want to paint her as a ‘bro’ and just some girl that’s fun to play video games with, but not dateable. She was very much a woman I liked looking at and I never took her presence for granted. I never put the moves on her, but I definitely saw for what she was: a knockout. Most (if not all) straight men think about having sex with their female friends. It’s just a fact. Ladies, if you have any male friends, they have thought about fucking you. It doesn’t matter how attractive you are, they have thought about it; probably have even masturbated to it.

Fast forward a couple years and we finally graduate. Caroline and I actually end up finding jobs in the same city. However, with most new jobs, we soon found that we had a lot less time to just hang out and shoot the shit. We still did, but we probably saw each other four times in as many months after we left school. However, we still texted all the time and exchanged Snapchats and I never felt like we ‘lost touch’. The good news is by the time Halloween rolled around, both our schedules calmed down and we had more time for socialization. Caroline invited me to a Halloween party in her building and I started to get excited about going. I planned to go as a Lifeguard simply because I had actually worked as one in high school and I still had my trunks and rescue tube (the big red floatation device). Once I told Caroline what I planned to go as she got super excited and asked me if I’d be okay with teaming up and having similar costumes. She wanted to do a sort of “Baywatch” type of thing. I remember hoping we didn’t look like a couple of dorks, but I told her it was fine with me. Halloween night rolls around and after I pull in to the parking garage to Caroline’s building I called her to let her know I was there. She sounded a couple of beers in and told me she was already at the party but told me to leave my stuff in her apartment down the hall. The door was unlocked. I walked in to her apartment and set my stuff down on her couch and as I walked back out I notice she had a bunch of pictures on her fridge so I stopped to admire them for a minute. There were a couple of us from parties and tailgates during our not-too-distant college years. I was kind of flattered to have made the fridge. As I turned around the door opened and Caroline walked in looking for me. A smile appeared on her face that instantly took her from a 9 to a 13.

“Alex!” she exclaimed “I’m so glad you’re here! The party’s already super busy but really fun.”
I barely heard her say any of this. I was too busy taking her in. Her costume was a red one-piece bathing suit with “BAEWATCH” printed on it in block letters. She also had on a cheap party store whistle and white Chuck Taylor shoes. She looked fucking amazing. Usually when people think “Baywatch” or lifeguard, they think of tanned people with blonde hair. But Caroline’s smooth and milky skin look so god damn sexy clad in a bright red swimsuit. It was a contrast that instantly turned me on. I regained my composure quick enough to not be awkward and greeted Caroline with a huge hug, noting how great she smelled. She wore a Chanel perfume and to this day any time I smell it I feel a familiar twinge and think of her. We decided to take a few shots in her kitchen before moving to the party down the hall. After the first two drinks, I started to get hot and took my jacket off. This left me to only be wearing my red swim trunks and a cheap pair of flip flops. I’m not a cocky person and I’m not saying I’m an Adonis but I would say I’m attractive and I’ve spent time in the gym. I have a moderately chiseled chest and boast a 4-pack as well as pretty good arm definition. The feature I’m proud of the most however is the “V-cut” of my lower abs. Almost every girl I’ve been with has complimented me on it and I can’t thank my genetics enough. After I removed my jacket, Caroline gave me a sexy smirk.
She jokingly said, “Damn Alex, you didn’t tell me you were packing.”
“You’ve seen me without a shirt on before try to control yourself, woman.”
I told her this with a huge smile on my face. I was being reminded of just how fucking hot Caroline was and it felt great to be admired by her as we both stood here scantily clad in her kitchen. We ended up taking one more shot of vodka and started heading down the hall to the party. As Caroline led me down the hallway, I took the chance to admire her ass in her swimsuit and I was not disappointed. Seeing her walking in front of me with her ass jiggling and bouncing with each step was something I locked in my mind and it is an image I will return to until I’m 100. I’m pretty sure I may have even mouthed the word “Fuck” and looked to the heavens hahaha. Anyways, we make it to the party and it was absolutely crazy. Everyone was hammered on alcohol and the music was blaring. Caroline introduced me to her neighbor whose name I can’t remember to save my life. Let’s just call her Jenna.

Jenna takes my hand and says “So when should I pretend to drown so you can give me mouth-to-mouth?”

I’ve honestly never had someone be that forward after 5 seconds of meeting them but it was flattering as hell and a top-notch pick up line.

I laughed and told her “They actually don’t teach that anymore so I’ll have to just straddle you and give you chest compressions.”

In my peripheral I saw Caroline smile but roll her eyes and she started to walk away. After a few more seconds of flirting with Jenna I found Caroline in the living room where some people were drunkenly dancing.

“Why’d you wander off?” I asked.

“I feel like I haven’t seen you in months and I’m just tired of Jenna flirting with everything that moves”, she said over the music.

“I get that. I’m sorry I didn’t mean to annoy you I was just a little thrown by her.”

“Don’t apologize. She’s just a bit of a slut and it gets on my nerves. Plus, I’m tipsy and just wanted to be with you tonight.”

She glanced at the dozen or so people on the “dance floor”.

“Would you want to dance?”

“Sure!” I told her.

I was good and tipsy up until this point and I wasn’t going to pass up a chance to dance with Caroline while she was wearing her skimpy lifeguard suit. I still remember that the song playing was “How Deep is Your Love” by Calvin Harris. Now I’m a terrible dancer, but that was okay in this situation because apparently Caroline knew what the fuck she was doing. I had danced with her at other venues before just having fun but she was on a whole other level this night. She danced her ass off (not literally, thankfully) and I could do nothing but stand there moving to the music watching as she moved in front of me turning on everyone in a 25-ft. radius. The next song to come on was a little slower and Caroline proceeded to change the tempo of her dancing to match it. Another thing changed too. She was now dancing on me, and pretty seductively too. She was rubbing herself all over me with her back to me and grinding in to me. At one point she looked at me and gave me that sly smile after she saw the look on my face. That’s when I started to catch on to what she was doing. This wasn’t the first time I’ve been seduced on the dance floor (check my post history). She wasn’t just dancing as a friend this time. She had me and she knew it. I couldn’t keep my eyes off of her body. She grinded her ass in to me and I held on to her hips to hold her closer. My dick was growing larger by the second. If this continued for long, everyone would have been able to see my raging erection. Caroline half turned, put her hand on the back of my neck and breathlessly whispered, “I’ve missed you so much, Alex.” I can still hear the words in my mind in her sexy ass voice. Where the hell was this coming from? Caroline was coming at me with all she had and she was irresistible. This all continued until the song ended. As the next track started, Caroline took my hand and led me towards the door. I knew where we were going.

“Sorry I just feel like we could have more fun at my place,” she said as we entered the hallway.

Once we were in the door to her apartment, it was over. She immediately turned around and pinned me to the door. She planted her beautiful red lips on me and we melted into each other. I wished we had kissed years ago. This felt so good and I couldn’t keep my hands off of her. I grabbed Caroline’s ass for the first time and squeezed, pulling her closer to me. I’d wanted to do that for a very long time. Caroline suddenly broke the kiss and then put her hand on my bare chest to push me back into the door.

“Wait here.” She said before she turned and started walking towards her bedroom.
She paused in the living room to hit the power button on her wireless speaker. I didn’t give it much thought as I was too busy watching every move her ass made. I wanted to fuck the shit out of her. She was no longer one of my best friends in that moment. I needed to be in her pussy. After she entered her bedroom and closed the door behind her, I sat down on the couch and tried to sort through the situation in my head. I was pretty sure my best friend and I were about to fuck each other’s brains out.

A few moments pass and I almost have a heart attack as the wireless speakers came to life. She had started playing “The Hills” by the Weeknd. Anyone who’s heard the beginning of that song will know what I mean. After a few seconds, the bedroom door opens. Caroline walks out completely naked. I see her pink nipples standing at attention, her smooth stomach with freckles by her hips, her trimmed pubic hair. Best of all, I can just make out her soft, pink pussy. I stand up and start walking towards her. I swear to god I’ll never forget this as long as I live because it’s the coolest thing I’ve ever done. Just as the beat drops on the song, I pick her up and slam her against the wall, kissing her deeply and thrusting my tongue into her mouth. She wraps her legs around my waist and meets my tongue with her own. This was honestly one of the most passionate kisses I’ve had in my entire life. My hands are all over her. She digs into my back with her nails and grinds her pussy on to my waist, leaving a wet spot on my trunks right over my dick. We stay like this a couple of minutes and then I wrap my arms around her and carry her into the bedroom.

When we reached the bed, I turned Caroline around so her ass was towards me and pushed her onto the bed. Then I took her hips and pulled them towards me so her face was on the bed and her ass was raised in the air. She arched her back in so that I had the most amazing view of her ass and pussy. I kneeled down at the foot of her bed and buried my face in her pussy. She tasted absolutely amazing. As I thrust my tongue into her she moaned loudly against the bed and grabbed the blankets. I spent the next few minutes alternating between sucking on her clitoris, licking her up and down, and entering her with my tongue. The whole time she was moaning my name and begging me to keep going. After about 5 minutes she pushes herself up with her elbows and gets off the bed. She kneels down in front of me and quickly pulls down my shorts. I am absolutely rock hard at this point and as soon as she has my shorts down my dick springs up in to her face and she smiles up at me.

“I’ve always wondered what your dick looks like. You have a beautiful cock.”

Fuck.

Caroline takes my dick in her hands and the wraps her lips around me. She begins sucking hard and working her way down my length to coat my whole dick in her saliva. After a few moments she looks up at me with her huge green eyes and maintains eye contact as she deep throats me. I never thought at the start of this night that I would be looking down at my friend shoving my cock down her throat. After 4-5 minutes of one of the best blowjobs I’ve ever had, Caroline stands up and pulls me in to a kiss.

“I want you in my pussy. I didn’t know how much I needed to get fucked by you until now.”

Her wish was my command. I laid Caroline down on her back and spread her legs open. After I climbed on to the bed and positioned myself above her, she took my dick in her hand and guided me into her pussy as she looked me in the eyes. As I entered her dripping wet pussy she opened her mouth and moaned, emitting a noise that is a contender for top 10 sexiest. Once I was all the way inside of her, she moved her hands to my waist and laid there getting used to the size. After a while, I began slowly thrusting into her and she grinded her hips into me, matching my thrusts. We slowly picked up speed until we were furiously fucking. I’m sure we looked like pornstars as I railed into her pussy and she screamed my name over and over again. After a while, I pulled out of her and she immediately flipped over and assumed the same position she had when I was eating her pussy. I did my best to memorize the sight of her asshole and pussy as I entered her for the second time. Only a few seconds passed before we were fucking just as fast as we had before. At some point, Caroline’s moans got louder and faster and I could tell she was on the verge of climaxing.

“Fuck, I’m coming Alex! Don’t stop fucking me.”

“Come on my dick Caroline. I want to feel your pussy throbbing on my cock.”

After only a few more thrusts I felt her reach her orgasm.

“FUCK!” she screamed as she climaxed.

Feeling her pussy throbbing and massaging my dick as she climaxed pushed me over the edge and I exploded inside of her. I shot rope after rope of cum into her pussy and coated every inch of her. After what seemed like forever, we fell onto her bed and just looked at each other as we panted and caught our breath. She smiled at me and the moved over to straddle me. She laid her chest on me and we just lay like that until we fell asleep.

When we woke up in the morning, we were both still naked and talked about how we couldn’t believe that had happened. We weren’t embarrassed and I told her I didn’t regret it if she didn’t. She said she loved it. Our talking soon devolved into kissing and from there, we had sex again. The morning sex was much more “romantic” for lack of a better term. We went slower this time and just stayed in missionary for a long time. She had two orgasms that I remember and when I pushed myself over the edge I released into her for the second time. We laid with me inside of her for a while and then took a shower together and had breakfast. After that, I left. We’ve hooked up several times since then (no relationship, sorry) but the first time remains very special to me.

Thanks for reading!

Source: reddit.com/r/gonewildstories/comments/7mbca5/unexpectedly_fucking_my_friend_at_a_halloween