He Cheated on my Bestie with Me

Hey guys I need to confess something new here. So about two years after graduating college I was invited to an out of state wedding for one of my old high school friends. I had a decent job, but money was still a little tight when factoring in the plane ticket and hotel. One of my best friends Laura mentioned we could share a room with two beds, but that her boyfriend Tom might be coming.

I really hoped that he would not be coming, because I couldn't stand her boyfriend. I didn't know him very well, but he was one of those finance guys that just seem to think they're better than everyone. He was also about ten years older than us. Laura was a gorgeous petite blonde and was one of my only friends from high school that I could still share clothes with. I also had a petite frame at 105lbs but was slightly taller at 5'4". The one benefit of him going was that he was going to pay for the room.

Cut to the night of the wedding and Laura is a bit of a lightweight and got drunk before the band had even started playing music. She was honestly probably drunk just from the pregame. Her boyfriend was the type of guy that seemed to make friends easily and was vibing with some of my high school guy friends oblivious to his girlfriends increasing somnolent state. One of our other friends was pregnant and agreed to take Laura back to her room since she was also getting tired and couldn't drink. She just said to stop by her room and grab her when we turning in for the night. So the rest of us continue to drink and dance for several more hours.

At more than a few points I wound up dancing and even briefly rubbing up on her boyfriend. I noticed he liked to get his hands on me whenever he had had a chance as we danced. His hands felt large. My dress was long enough that I didn't wear any underwear with it. And I suspect that through Tom's causal groping he was now aware of this.

As the night wore to an end everyone started pairing off and headed up to their rooms. It was a large hotel and the elevators each served specific floors. And wouldn't you know that the the elevator that Tom and I needed didn't have anyone else in it. I had definitely warmed warmed up to Tom at this point I thanked him for paying for the hotel room for Laura and I. He said it was no problem. But then a smile came over his face. He said if I really wanted to thank him I would play truth or dare with him.

I nervously agreed and chose dare. He told me I had to take of my dress and walk to the room in my underwear. At this point I knew he had felt through my dress and therefore knew that I wasn't wearing any underwear. I didn't want him to win so without hesitation I pulled my dress off right as the elevator chimed as it came to a stop and our doors opened. I ran out if there leaving my dress and shoes behind. He walked behind me and picked them up. I yelled at him to hurry as I turned the corner down the hall.

I stood in front of the door trying to cover myself as best as I could with my hands although my 32B breasts were difficult to conceal on my small frame. He just slowly walked up smiling. Then the smile softened and he reached out his hand and stoked the side of my cheek with the back of his large finger. He then told be to get onto my knees. I don't know what had come over me but I meekly complied. He then told me that I knew what to do. And then without thinking I pulled out his cock and started sucking like little whore I had become.

He grabbed the back of my head and made me take all of his large cock. I was gagging loudly but somehow seemed to have forgotten that I was still in the hallway. Our room was at the end of the hallway and about ten feet from our door were floor to ceiling windows. After he fucked my face for several minutes he stood me up and pressed me up against the floor to ceiling window. My tits felt cold pressed against it. He put his cock inside me deeply from behind and started thrusting hard. I noticed that directly across from us through the window was a rooftop bar.

It wasn't super busy, but here probably 30 people scattered about drinking and talking. Soon I realized most their attention was aimed at me. I should have felt ashamed and told him stop or let's go inside the room but their eyes only turned me on more. He seemed to be able to tell that I liked the audience and he told what a good little whore I was. He slapped my ass and the grabbed my hair and pulled back hard. Next I felt his thumb in my ass. I had never done anal before.

I tried a few times with my ex but it always hurt so I stopped. His thumb felt amazing though. I told him to fuck me harder. He did and for a second I was afraid he was going to fuck me straight though the glass. He told me he was going to cum soon, but I told him that he couldn't before he fucked me in the ass.

He let out a greedy laugh. I heard him spit and then I felt his huge cock push deep in my ass. It hurt a lot at first but luckily I was drunk and the pain actually felt amazing. I came so quickly and hard that I nearly collapsed. He then threw racial slurs at me calling me his black cumslut whore.

His strong hands though kept me planted against the glass as he kept thrusting away. Eventually he said he was going to cum again and without taking I got down on my knees in front of him and opened my mouth. I was expecting him to jerk off into my mouth but instead he started facefucking me for about 30 seconds. He rammed it into what felt like my lungs. Then he pulled back and let go a huge load all over my open mouth, face, and tits. I licked him clean. I looked back and could see a few people from the roof top bar clapping. A few others had their cell phones out too.

Tom and I made our way into the room and I grabbed a towel to start cleaning up. Before I could turn on the shower on he grabbed me by the hair and brought me to the bed where he laid down. He then said we're not done yet and he pointed to his cock which was somehow still hard. His hands were behind his head and I made my way between his legs. I sucked his cock for what was probably 30 min before he had me climb on top and ride him. He then had me turn around so I was riding him reverse and he slid it in my ass again.

As I rode him harder he grabbed my hair and asked if I was a bad girl. I told him I was and I deserved to be punished. He slapped my ass red and then had me lay on my back and he fucked my asshole missionary. His hand made its way to my throat and I begged him to choke me. The feeling of being choked hard with his cock throbbing deep in my ass was enough to almost make me pass out from how hard I came.

He slapped me back to reality but then his hand was right back on my throat and I was cumming again. A few minutes of that and then he was straddling my face pounding his cock deep into my throat again. As I gagged he held in there. Until eventually he pulled it back and came again all in my mouth and on my face. Then he shoved it back in my mouth for me to clean him up.

We both showered after that and changed into sleeping clothes while he ventured to Laura's room several floors below to collect her. He returned with my sleeping friend in his arms. We woke up the next morning and everyone claimed to be very hungover and not to remember much from the night before lol. We never talked about it again. Laura and Tom got married 18 months later. I was a bridesmaid and don't know how to feel about it and if I should tell her.