Okay, so let me start out by saying that I'm a terrible story teller so please keep that in mind. Also I'm not using real names because I dont want my mom to get exposed. Because of this I will also not be posting her picture. So with that out of the way, let's get to the story.

At the time I was 14. I was friends with this guy, Jack. He was a grade below me. I was a freshman and he was in 8th grade.
Jack is a guy that got all the good genes. He was about 6 ft tall and had semi long brown hair. He was in good shape and was able to get almost any girl he wanted.
We were friends, but he kinda bullied me as well. He was taller and stronger than me and anytime we hung out with other people he would embarrass me or make fun of me. I was only 5'3" at the time and pretty chubby. There were a few reasons that I stayed friends with him. One was that he was a natural leader and I was a follower. He just had that Alpha personality. Another was I got to go to cool parties because of him. He dated and hung out with people years older than him. I guess I thought I could get laid if I hung out with him. (Never happened)
I remember we were hanging out with a few other people. Having some beer and smoking weed. He was harassing me as usual and this time, as he did many times, he was talking about my mom and how he was going to fuck her.
My mom was about 5'4" and 135 lbs. She had big tits and a big ass. I never really was attracted to her sexually, but I understood why some guys did. She had bleach blonde hair and brown eyes.
So Jack was laughing and saying how he was going to fuck her with his huge cock. (He was very big. Probably 9-10") It pissed me off and so I told him to shut up and pushed him. His friends grabbed me and held me against the wall.
He told me that was a good way to get my ass beat if I ever did that again. Then he had and idea. I got shoved to my knees and held there.
Jack slapped me then to my surprise said I was going to suck his dick. (I dont think he was gay, but I think he enjoyed the power.)
He walked up to me. And pulled out his cock. It was soft. But still bigger than mine. I'm not gay but I couldn't keep my eyes off of it. It was huge and very impressive.
He pressed it against my face and said if I sont start sucking he and his friends were going to kick my ass. So I did what i thought i had to do and started sucking. It grew in my mouth and eventually started hitting my throat causing me to gag. That just made him shove it in further. Before I knew it I was deepthoating his dick and licking it. About halfway through I realized I wasnt being held down and I was doing this on my own. But I figured I should keep going so I didnt get my ass kicked. Finally I heard him say he was cumming. He pulled out and came all over my face.
His friends  started taking pictures of me on my knees with cum on my face.
Jack said he was going to send everyone in school this picture. I begged him not to. I said I'd do anything.
It almost seemed like he planned this. Because almost immediately he said "You're gonna let me fuck your mom."
"I know I can, but the only issue is she wont do it when you're around. So you're gonna invite me over and then go to sleep early so it's just me and her. Then I'm gonna fuck her. And shes gonna beg for it."
I couldn't stand the thought of him having sex with my mom, but I definitely could have him send the pics of me with cum on my face to everyone. So I agreed.
That night he came over to my house to stay the night. My mom was always happy for me to have friends over. She really wanted to be the "cool mom".
We were there watching tv. I was sitting on the recliner. And Jack was sitting next to my mom. She was wearing a white tank top with no bra and pink booty shorts. Just things she wore to be comfortable. Jack sent me a text saying to go to bed in 10 minutes. My heart dropped. I felt like this couldn't happen. There was no way my mom would fuck him. Even though I've seen him get college girls to fuck him. My mom was 32. There was no way.
I decided to trust my mom. I said I wasnt feeling that good and that I was going to lay down. I went to my room and just listened at the door. I couldn't hear a lot because my room was at the end of the hall, but I could tell they were talking. I tried to look through the crack between the door and the frame. I could kinda see from there. The living room was dark, but because of the tv light I could see a little bit. I was shocked to see my friend have his hand on my moms thigh. He just had it laying there for about 20 minutes. Then he started rubbing her thigh slowly. Then he stopped.
They continued talking. It seemed like forever, but was probably about an hour. Then I heard what sounded like my friend saying "it's fine. Hes definitely asleep by now." At that point he started rubbing her thigh again. He was rubbing closer and closer to her pussy. Then my mom did something to make my heart skip a beat. She opened her legs and let my friend rub her pussy over her pants. I could hear some soft moaning from her.
My friend then grabbed her hand and put in on his crotch. And she started rubbing his dick over his shorts. This went on for another 10 minutes or so. Then my friend stood up and pulled his shorts down exposing his hard cock. I heard my mom gasped and say "Holy shit that's fucking huge!" To which Jack replied with a laugh. She started to sucj his cock.
I couldn't believe it. There Jack was getting his cock sucked by my 32 year old mom in my living room. I didnt know what to think.
Then they decided to move to her room. Which was right next to mine. Within a minute of going in there I started to hear her moan. Softly at first but as time passed it got louder. I couldn't help but get hard hearing it. I could hear the slapping sound of him fucking her and her loud moans. She no longer cared if I was able to hear.
She was yelling things like "fuck me harder sir." And "this is the biggest cock I've ever had."
I was jacking off at this point. And within minutes I was cumming as hard as I ever had.
My friend was still fucking her hard. I guess he decided to take pictures because I heard my mom say "no please no pictures" and he said they would be just for him and my mom agreed. The strong orgasm I had made me tired.  I passed out to the sound of them fucking and woke up at 7 am. I walked out of my room and saw Jack's shorts still in my living room floor and he was still in my moms room. I decided to take a peak. I slowly opened her door and saw him laying there on his back asleep with my mom curled up to him. I decided to go lay back down in my room. About an hour later they woke up. And I heard them leave the house. I got up at this point. Made some cereal and waited. My mom came back 30 minutes later. She said hi to me and said she dropped Jack off at home. She seemed normal which surprised me for someone that just got fucked by a 13 year old. She asked me how I slept and I said good. And we continued on as normal. To this day she doesn't know that I know. They've fucked multiple times since and now he lives a few states away.