[MF] Halloween 2017 – I slept with my best friend’s date.

So this is a long story, it happened 4 years ago when I was 20. I used to live with some friends of mine, we shared an apartment during college and my friend was a bit of a ladies man. He was good looking, tall, and although not in the best shape I imagine his chill personality and confidence made a good impression with others. We’ll call him John.

I’m sharing this story because it started on Halloween, so the season brings back memories.

So it’s the last week of October, John sees me gaming on my Xbox as usual and gives me the heads up to go to a Halloween party being hosted by some friends. Said it would be fun to kick it and drink around.

“And meet some ladies?” I asked him with a knowing smirk. He smiled back and shook his head.

Apparently he already met one, described her as a Milf taking her bachelor’s to make better money for her kid. Single Mom I guess, okay. Well, the party would be in a few days so that gave me enough time to get a costume. The party arrives and it’s cramped, the apartment was decent in size but some of the guests had to pile out in the balcony just to move around and have some fresh air. The music was booming, drinks were all around, it was the typical college fiesta you’d imagine. And yes, every drink available had some sort of hard liquor mixed in. Punch, Gatorade, Soda, that kind of stuff.

I make myself comfortable at the couch and John walks by with his arm around his date, a beautiful woman dressed as the princess from the Princess and the Frog movie, I forget her name. He was dressed as Woody from Toy Story, he had the height for it so it fit well. He introduces us, we’ll call her TJ. Honestly, she seems uninterested and not all into the party, like she had some concerns that wouldn’t let her enjoy herself. Well, most of the conversation is between John and I but I felt bad about her staying idle nearby. I was dressed as Ghostface from Scream, kept my mask on to stay in character. At some point during conversation I pulled it off, it was making me sweat and when she and I locked eyes she turned her gaze and motioned for John that they should go get more drinks. They left and I felt a bit emasculated, like wow am I that ugly? Needless to say, I put the mask back on until I sit down for more drinks.

I’m focusing on dismissive details here, but be patient with me. I write stories for a hobby and telling a real one here is making me caught up in emotions, don’t worry the good part is coming soon.

Skip to midnight, most of us were buzzed or high or a mix of both. Someone shouted we play some party games to keep things interesting, the first vote was strip poker but too many gals disagreed and no one was interested in a sausage party. So we tried a classic, spin the bottle. I wasn’t planning to join, I felt a bit like shit and my face was tingling from the amount I drank. Whatever they spiked in that punch was starting to kick in. It was John who pulled me in, had me sat down in a circle with plenty more. I didn’t know what we were playing until someone downed a whole coca-cola glass bottle and placed it in the center. Yea, it was that kind of game.

I’m taking too long, so I’ll skip to what matters. After about 40 or so minutes of playing, it lands on TJ and John. Yeah, you probably thought it would land on her and I didn’t you? No no, he made sure to sit at the opposite of her just to be safe. They went into the closet and had their 5 minutes of fun, once the time ran out he walked away with lipstick smeared on his face and her hair was rather messy. People cheered, and the party went on. But I admit, I did stare at her dazed look as she sat down. She licked her lips and cleared her throat before the game continued. I did get my shot at the closet with a shy girl, she looked to be goth. I won’t lie, we didn’t do much. She was reluctant and said she was playing because her friends pushed her too, so we kissed a few times before time ran out. Needless to say, it was not the best day for me.

It was 3 in the morning, John was our ride home but he was shitfaced. Couldn’t walk straight, couldn’t stop smiling, always had his arm around TJ. She and I looked at each other and agreed that he’s in no state to drive, so she offered to drive us home. In the car ride home, he was a mumbling mess and we had a few scares of him puking in the car, fortunately it didn’t happen. I even took my mask off when it looked bad, she saw me offer it to him and it made her laugh. I showed her where we live and we make small talk on the way. She takes a class with John and they were paired together for a group project, that’s how they met. She helps me lift him up the stairs, we put him to bed and place a trash can next to him just in case. So we sit down at the couch and laugh it off, by this point we’re getting comfortable and we’re vibing about college, projects, and eventually we talk about the party.

She asked if I got lucky with any numbers, I said nope. She followed with “but you did have fun with that one girl, right?” I shook my head and explained what happened. Said I was looking forward to it, but the encounter left me horny and wanting more. Then she sighed and leaned into me, hugging my arm and chuckling to herself. She says John was a messy kisser, he was uncoordinated and possibly drunk so it left her wanting more as well. So I smirked and said “Guess that makes us two people in need of a good fuck.”

She agreed. Then I felt her arm slide toward my thigh. My heart skips a beat and I feel my member start to respond, my thoughts start to scramble and I ask myself if this is real. She squeezed my thigh and I wrap my arm around her by instinct. She looks up to me, we are so close I can smell the hint of cherry from her lipstick. We edge closer and closer until we kiss. Her lips were so warm, and I felt her fingers stroke my crotch.

I’m sorry to say that I can spend all day figuring out the little details and what we did that night, but this isn’t a fantasy, it’s reality. We went at it, I felt out of control. She pushed her dress down and I saw a pair of the sexiest tits I ever saw. We went down on each other, then she pushed her dress up and laid back for me to enter her. It was my first time having raw sex, and I have to say the contrast in our skin color when I entered her really left my head spinning. The moans she made, feeling her hands slide down my arms, the words she spoke. God it was amazing, but the scary part was when I was getting close. She locked her legs and looking into my eyes she said the sexiest thing I ever heard.

“Cum in me daddy, cum inside me and make me yours.”

I had no chance, it felt like she controlled me and my body gave in. For those of you wondering how it feels to finish inside a woman, it’s fucking amazing. We kissed and cuddled each other, and by morning she shot up awake and we realized we slept naked in the couch. She got her dress and woke me up too, said we have to dress up before John sees us. That woke me up fast and I rushed to put on a pair of jeans. She couldn’t find her panties though, she was starting to panic then said she had to rush home to take care of her son. I had forgotten she was a mom, she was beautiful and around our age. We kissed and she whispered thanks for the good time, then left. I fell back on the couch wondering if last night really happened when my hand touched something sticky, it was a reminder of our intimacy the other night. Couldn’t tell if it was hers or mine, just knew that I recoiled and grabbed a washcloth to clean it up haha!

I didn’t get her number. John woke up and felt like shit, so I offered to buy him breakfast. Not going to lie, I did it because I felt like shit for having sex with his date the other night, but he thanked me for being a good friend and appreciated my help. Just one last thing though, as I was cleaning up around the place I found her panties stuffed between the sofa cushions and stuffed them in my pocket in a panic. Then I realized, I left my mask in her car.

John would never guess what I did to him. My friends know I dislike cheating and whenever the subject comes up I would say better to dump your partner partner to cheat on them just out of fun. That night I realized a few things. I realized I was a hypocrite. I realized I had unprotected sex with my friends date.

And I realized it would not be the first time we would have sex in the future.

Source: reddit.com/r/gonewildstories/comments/qe1lo9/mf_halloween_2017_i_slept_with_my_best_friends