How Many Times Could It Happen?

"Just think, tomorrow you'll be able to see what's underneath."

That's what Mandy, my girlfriend, told me after I complimented her on how amazing she looked in her dress. Mandy and I had been dating for over two years, and I have never seen her in anything less than a bikini. There are two reasons for this: one being that she was extremely conservative by nature, and the other being that she was incredibly self conscious about her body. For most of the time we had known eachother, she was fat, and everybody in school would let her know about it. She was also one of the two sweetest people I knew (the other being my mom), and she was the only person not related to me that would ever talk to me. We started dating, and everybody in school would make fun of us and pick on us as we walked the halls holding hands.

That was at the beginning. A few months ago, Mandy started to transform. She lost weight in almost every part of her body. Every part except her ass and tits. She was hands down the hottest girl in our school now. The guys went from picking on her to staring in amazement at her body (the same way they stared at my mom every time she came to pick me up from school). The girls went from picking on her to being jealous of her body.

The reason I was finally able to see her naked tomorrow was because tomorrow was my birthday, and this was going to be my present. It was going to be the greatest day of my life. First, I just had to get through a night that I had been dreading for a week. Mandy works at a fast food restaurant, and there is one customer that eats there every day that she tells me about. He is our age, but doesn't go to our school. He's always really nice to her at work, and a week or so ago, he invited us to a party (she said she always talks about me to him so he knows all about me). Neither of us have ever been to a party, but she thought it would be a fun way to celebrate and it would be something new for us to try together, so I agreed to go.

As soon as we got to the address, I started to get even more nervous. The party was being held in an abandoned house, and I knew we couldn't be there. I knew it was illegal because my dad is a police officer, and he makes sure I know how to stay out of trouble. I expressed my concerns to Mandy, but she promised me that it would be fun, so we went inside.

There was really loud music blasting throughout the house, and I could smell marijuana smoke in the air. As soon as we stepped inside, someone ran up to us and gave Mandy a hug. I noticed a long scar down the side of his face, and realized it must be her friend from work, since she told me about the scar. He didn't even acknowledge me, and in the middle of Mandy trying to introduce us, someone else ran up with a bottle of liquor and placed it up to Mandy's lips. She was shocked, but did her best to swallow down a shot. Her and I have had liquor before, under my father's supervision, but we never drank it straight out of the bottle like that. Mandy made a face and everyone around us laughed at her reaction.

As the night went on, I got more and more uncomfortable as Mandy's friend, who I finally learned was named Brian, fed her more and more alcohol, and with each drink, started making more and more physical contact with her. It started with hugging and shoulder touching, to rubbing her thighs and lower back. Finally he spoke to me and asked if I wanted to play some Xbox, which was what I wished I was doing at home. We got up and walked to another room and Mandy stayed behind. Brian introduced me to a couple of his friends and got the game set up, and then told us to have fun and walked out of the room, which I thought was weird.

I played one game and then thought I should go check on Mandy and make sure she was alright. She had drunk more than she's used to and I wanted to make sure she was handling it ok. When I walked back into the room I left her in, I finally saw her in a thong for the very first time. She was on her knees sucking Brian's cock as he relaxed on the couch. I had never felt so humiliated or angry in my life, but I knew there was nothing I could do to stop what was happening. To save myself any further embarrassment, I turned around and joined the guys, who had already started another game without me. One of them asked how my girl was doing, and the rest of them fought hard to hold back laughter as he asked. I guess everyone knew what was going on in the other room.

For the next 45 minutes or so, I sat in horror while Brian fucked Mandy. Once they started actually fucking, they started getting so loud that I couldn't even pretend not to know what was happening. The rest of the guys laughed and made fun of me for letting my girlfriend get fucked.

When Brian finally came back into the room with the rest of us, his friends all gave him high fives and stuff like that. Brian came up to me and thanked me for bringing Mandy over. I just sat in silence while everyone laughed again.

Brian went back to fucking my girlfriend, and it felt like the night would never end. Then all of a sudden, there was a knock at the door. It was the police.

One of the other guys answered the door while Brian and Mandy continued to go at it. I hid under the couch, scared for my life. As I heard the officer telling the guy that answered the door that it is illegal to hold a party in an abandoned house, my heart started racing even faster. It was my dad. Brian, oblivious to the fact that there was a policeman in the house, or maybe he didn't care, was fucking Mandy harder than he had all night. Hard enough for her to scream and moan, and definitely hard enough for my father to hear. My dad, worried for a young girl's safety, pushed into the house and saw them fucking.

My dad saw Mandy being bent over the couch and fucked, and he froze in astonishment, seeing his son's conservative girlfriend being fucked by this hoodrat. Brian stopped fucking Mandy and walked up to my dad.

"What, you never seen a white bitch take black dick before?"

Before he could respond, Brian punched my dad in the face, knocking him to the ground. He then took my dad's gun and aimed it his friend who answered the door.

"How stupid are you letting a cop in here?" and then fired at his own friend, hitting him in the thigh.

The rest of the night was a blur for me. I ran out of the house with the rest of the guys and Mandy, leaving only my dad and Brian's injured friend.

The next day, my mom and I visited my dad in the hospital. He was finally coming to, having been knocked out for 24 hours after the one punch he took. We could only talk for a few minutes before more police officers came in and asked us to leave the room.

It was a confusing few days after that. The guy that Brian shot had told the police a story about how after coming to break up the party, my dad tried to have sex with the girl that was there, and he tried to stop them, which is when my dad pulled out the gun and shot him. There was no evidence of this, and all my dad had to do was tell the truth, about what really happened. But he loved me too much, and he didn't want the world, or me, to know that my girlfriend was fucking some loser. My dad made a plea deal, and took two years of prison just to protect my feelings.

My dad explained to me and my mother that he did nothing wrong. But because of the current racial tension around America, he knew he would lose in court, so he decided to take the deal. My mother believed him, I of course knew he did nothing wrong, since I was there. But my neighbors did not believe him. My mother spent the better part of the next two years defending her husband, and Mandy left me and dropped out of school.

Fast forward to the day before my dad gets out of jail, and my mom and I couldn't be happier. Not only because of the fact that the man we had visited in prison every day since he was put away was getting out tomorrow, but because it was my one year anniversary with my new girlfriend. I was still a virgin, but I was promised she would take my virginity after we got back home from our little anniversary celebration. Since it was also the day before her husband got home, we decided to party all three of us. My mom, my girlfriend and I went out to a club for some drinks.

The night was going fine. My girlfriend had left to the bathroom when I saw her phone go off. I saw the name Brian pop up as the sender, and I got paranoid, even though I knew it wasn't the same Brian. I still casually read the text, and it said "fuck u u slut, ill go wherevr i want." I read more of the conversation and it seemed that my girlfriend had told Brian about her plans for the evening, and asked him to stay away. I thought the whole thing was odd but I tried to forget about it.

A little later, I got a huge shock as I was standing at the bar with my girlfriend, and Mandy walked up to us.

"Hey baby" she said to me. Then she looked at my girlfriend and said "Who is this, your sister?"

My girlfriend got upset and said she was my girlfriend, to which Mandy said "Well he didn't mention a girlfriend when we were fucking the other night."

I had no idea what Mandy was talking about, but my girlfriend didn't give me a chance to explain. She stormed out of the club and I followed her.

As we argued outside, to my shock, Brian emerged through the doors. The one who got my dad thrown in jail.

"Hey Brieanne, what are you doing here?" he asked my girlfriend with a smile.

I was just standing there dumbfounded when Brieanne said "You should meet Brian. He's the guy I've been fucking for the last three months. Now that I found out about you cheating, you should find out about me. Brian, please take me home."

Brian declined, explaining that he had better plans for the night then fucking the same old slut he's been fucking for months. He hailed a cab, threw Brieanne a few bucks, and sent her on her way. He then put his arm around my shoulder and said "Let me take you to Mandy. You and her have some catching up to do."

He brought me to Mandy and walked off.

"What was that about?" I asked.

Mandy explained that Brian wanted me to get Brieanne to leave, and she apologized about me finding out that she had been fucking Brian. I asked her why she doesn't mind him fucking other girls, and she told me Brian wasn't her boyfriend, but her pimp. I was shocked once again. We talked for a few minutes when I felt a tap on my shoulder. It was my mom asking where Brieanne went. I told her she felt sick and left but she wanted us to stay. Then, Brian walked up and handed us all a drink. My mom seemed impressed at how quickly he got service, and Brian said he gets served really quick since all the bartenders love him. My mom said "You probably just flash that smile of yours and they give you whatever you want." Brian laughed and agreed.

My mom seemed excited to see Mandy after not seeing her for so long. She kept talking about my father to Mandy and to Brian. It was nice to see her in such a good mood, knowing her husband would be home soon. Brian of course, pretended not to know who she was talking about.

Eventually, my mom asked Brian about the scar on his face. He told her he didn't want to talk about it, and Mandy put her hand on his shoulder, as if to comfort him. She dropped the subject, and the night went on, until last call finally came.

I was relieved to be done with Brian, but then my mom did something I didn't expect. She invited them both to our house to keep celebrating. She also thought Mandy and I could use some more time to catch up.

At my house, we continued to drink and talk. Brian left the room to use the bathroom, and Mandy moved over to my mom. She said "You have to ask about his scar again. Make him tell you the truth. It's really important for you to hear. Brian is my best friend in the whole world, and I was there to see him get that scar. I've wanted to tell you what I saw, but I love you and your family so much that I couldn't. You need to ask him again though."

I started panicking. It seemed like Mandy was up to something again but I didn't know what. Mandy stood up as Brian returned to the room and asked me to show her my bedroom. She missed it and wanted to be reminded of what it was like. As we walked past my mom, she whispered in my mom's ear "Believe what he tells you, no matter how terrible it sounds. I'm sorry."

When we got up to my room, I asked Mandy what was going on. She told me that Brian went to the club to embarrass me about fucking my current girlfriend. But when he saw my mom, he knew he had to fuck her. I told her it would never happen, but she said it would after the story Brian was about to tell her. He was going to tell her how my dad gave Brian his scar by pistol whipping him that night two years ago. How Mandy tried to tell him to stop but he just shoved her away and hurt her. How Brian was just trying to protect his girlfriend from getting raped by my father when my father decided to injure him. How that boy who got shot was trying to help Brian, and paid the price by getting shot in the thigh. I told Mandy my mom would never believe that story. I told her that in about eight hours, my mom and I were going to pick my dad up from jail and be a family again. That's when I heard the footsteps coming up the stairs. Two sets of footsteps. Then I heard a bang as someone got thrown into a wall. Brian was hurting my mom! But then I heard her say "Hold on baby. Not out here. In the bedroom. Fuck me on that bastard's bed." Then I heard her bedroom door slam shut.

I looked at Mandy and she laughed. "Told you." Is all she said. They weren't even trying to be quiet. I could hear almost everything from my room. Bed squeaking, headboard knocking, my mom screaming and moaning. Then Mandy starting getting text messages. She showed me pictures of my mom deepthroating Brian. Videos of Brian throatfucking her. Videos of my mom's ass bouncing up and down on his cock.

I started to get hard and Mandy laughed again. She told me she knows I'm still a virgin, but that she was willing to jack me off for $100. I didn't say anything but she grabbed my cock and pumped it three times before I came. She wiped my cum onto my sheets and then grabbed my wallet. She found $200 in there and put it all in her purse. She told me she owed me another handjob so she would do it again next time I got hard.

By the time I fell asleep, I had been listening to Brian fuck my mom endlessly for hours, and I was $700 in debt to Mandy. I promised I'd pay her as soon as I could.

I only slept for about an hour before my alarm went off. It was time to pick up my dad from prison. I knocked on my mom's door and she opened it, looking like a complete whore who had fucked all night and gotten no sleep. She told me she wasn't going to go with me to pick my dad up. She was going to stay here with Brian, and she told me not to bring that piece of shit man home with me. She gave me some money to get him a hotel room.

When I got to my dad, he had tears in his eyes. I asked him what was wrong and he showed me his phone. My mom was sending him pictures and videos of Brian fucking all of her holes and cumming all over her, all in my father's bed.

My parents got a divorce, and everybody knew it was because of Brian. After the divorce was finalized, Brian revealed to my mom that he made everything up. He told my mom how he lied to her just to fuck her, and how my dad was really just being the great man he had always been. This might have been enough to save my parent's marriage, but my dad had committed suicide out of the shame the whole situation brought to him.

There were a lot of people at my father's funeral. His police buddies mostly. Brian was also there, staring from a distance at my mother. My mom told me she was scared and couldn't take it so she was going to go sit in her car for a while. 15 minutes later I got a text from my mom. "Come to the car" is all it said. So I did, and I was horrified when I got there and saw my mother in the backseat, her dress pulled up and Brian fucking her from behind. He looked at me through the window and smiled, waving my mom's phone at me. I knew he was attacking her, there's no way my mom would willingly do this. Either way, the sight was too hot for me to look away, so I watched as Brian filled her with his cum.

I then saw Brian make a phone call, and my phone rang, so I picked it up. He put the phone down and he was basically letting me listen in on what was going on without my mom knowing. "Thank you so much Brian. I'm glad I could convince you to give me your dick again. I've been going crazy without you." They then kissed passionately, and I ran away so my mom wouldn't see me.

From then on, Brian would come around to fuck my mom every once in a while. My mom ended up marrying a man she worked with, but that didn't stop her from fucking Brian.