The summer before Junior year started was really great. I got a new car and everyday I would hang out with my three best friends. There was my best buddy Matt and his girlfriend Claire. There was Natalie. And then there was me. David.
We would all go to Matt’s house everyday. We liked it there because his mom was tight. She would look the other way if we ever had any alcohol, and she always bought all kinds of food.
Yeah I pretty much lived at Matt’s house. I frequently spent the night and his mom never seemed to care. Sometimes Claire would spend the night too, but she had to sneak in while Matt’s mom was asleep.
One day we were playing cards in Matt’s basement when Matt jokingly said that we should just play strip poker. Claire laughed, but Natalie said, “Okay, we’re better than you anyway.”
Now, Matt knew this was a challenge and he never backed down from a bet. “Alright,” he said. “Two lowest hands, take off a piece of clothing.”
Matt and I lost the first hand. We both took off a sock. Matt and Claire lost the next. Matt took off the other sock. Claire looked down. “Damn,” she said. “I’m not wearing socks.” We all started laughing even though it wasn’t very funny. She took off her shirt instead.
I had never before realized how big Claire’s boobs are. I realized I was looking at my best friend’s girlfriend’s tits. I looked up and noticed that she was looking at me smiling. I turned red and looked away.
The next round, Natalie and I lost. She took off her shirt and I took off my sock. Her boobs were even nicer than Claire’s, and I swear to God, she slyly smiled at me when she took it off.
“You like what you see?” she asked smiled sweetly. I nodded. “Well you won’t see much more, cause were gonna kick your ass,” she replied. Not if I can help it, I thought.
Matt and I both lost the next few hands. We were in our boxers. What the hell was happening? Matt and I walked upstairs to talk for a moment. “Dude, were getting our asses beat,” he said. “We can’t let them win.” I had an awesome idea. “How about you text me your cards and I’ll text you mine, and we’ll just act like were texting someone else,” He liked the idea, so we went back downstairs.
The next hand I was dealt Jack of Diamonds, Jack of Spades, Ten of Spades, King of Spades, and Ace of Spades. I decided to go for the straight, but then I got a text from Matt. Damn, he had the Queen of spades. I kept the jacks and laid the rest down. I texted him mine and ended up with 3 of a kind. We won that round and they lost their pants.
The next round was close, but we won. They reluctantly reached for their bra straps, but Matt stopped them. “Wait, we want to do it,” he said. Matt and I walked over behind the girls and we undid their bras. They put their hands over their nipples immediately and I didn’t even get a glimpse. We sat back down. “Come on,” Matt said. “How can you play cards without any hands?”
“Like this,” Natalie said. She reached one arm over both boobs and held up her hand. “I can play with one hand,” she said. Claire followed suit. Even if I couldn’t see their nipples, I was still hard. My seven inch cock was trying to get out of my boxers. If Matt wasn’t here, I wouldn’t even mind losing, I thought.
The next round was tense. Dammit. My hand sucked. I kept the ace and got four more cards. They sucked. I sighed. I knew that it was game over for me. At least someone else would be losing too. I hoped it wasn’t Matt.
I wasn’t surprised when I lost, but I was still a little disappointed. I looked over and realized that Natalie lost too. My penis got even harder at just the thought of Natalie naked. She sighed and used one hand to remove her panties. She quickly put her hand over her pussy, but I managed to get a glimpse. It was shaved and looked wet.
As I slid my boxers off, I wished we were playing at a table, instead of on the floor. Natalie and Claire both looked at my cock. Natalie seemed amazed. She sat staring for a second and then quickly looked away. She kept taking glances when she thought I wasn’t looking though.
“I guess that’s game over,” Matt said. He seemed happy.
“Oh no,” Claire said. “We keep playing, and the losers have to do dares,” No one had a problem so we kept playing. The girls both lost again. Claire removed her panties and since Matt had won, he dared Natalie to lick Claire’s pussy. She obeyed and me and Matt watched as she stuck her tongue in Claire’s pussy. It was very arousing. And I’m sure everyone could tell how aroused I was.
We started the next hand and I could tell nobody was trying to hide anything anymore. Natalie smiled and pushed her breasts together when I looked over. I suddenly had a crazy scenario in my head, where she loses the next round and has to suck my dick. God, I hoped she lost.
Well, my wish did some true, but I lost too. I saw Claire walk over to Matt and they whispered for a second. Then Claire spoke up. ‘I dare you guys to fuck,” she said. Natalie and I both looked at her open mouthed. Then we turned to each other, both of us blushing.
“Well, it was a dare,” I said.
“Yeah,”She says. “I guess we have to.”
The look on her face told me she wanted to just as bad as I did. We walked over to the couch. She laid down and spread her legs. I looked over and saw Matt and Claire watching us. I walked over and laid on top of Natalie. I kissed her mouth and she kissed me back. I could feel her boobs pushed against my chest. “Ready?” I asked. When she nodded, I pushed the tip of my penis into her pussy. It felt so good. I would not last long, I thought to myself. I pushed in farther and then pulled out. I did it again, and she followed my rhythm with her hips.
I sped up a little and she was moaning. I started playing with her nipples while I fucked her. Damn, this girl had nice tits. “Yes, Yes,” she was moaning. “Fuck me like I’ve always wanted, Dave,” she moaned. I was pounding her as hard as I could.
I looked over and noticed Matt was fucking Claire on the table. Way to go, Matt! I looked down at Natalie. Her eyes were closed and she was still moaning. I”m gonna cum,” I said “I better pull out.”
“I don’t care,” she said. “Stay inside me!” I shot my load deep into her pussy and she screamed in pleasure. I stood up and helped Natalie up too. She could barely stand. We walked over to the table just as Matt and Claire finished.
“Wanna keep playing cards?” I asked. Everyone seemed eager to play. Especially Claire. She had a mischievous little grin on her face. We sat down, and I noticed Matt didn’t put his boxers back on, even though he hadn’t lost them yet. We gave up on our old texting system, as we really didn’t care anymore. We both lost that round. Claire got first, so she would choose our “punishments.”
“Matt, I dare you to fuck Natalie, and Dave I dare you to fuck me,” she said. We all looked astonished. Matt didn’t seem angry, and neither did Natalie. I had always wanted to fuck Claire anyway.
We climbed onto the table as Matt and Nat walked over to the couch. I was about to stick my dick in Claire’s pussy when she said, “No, I want it in the ass.”
She got down on all fours and stuck her ass towards me. I got on my knees, and pulled her ass cheeks apart. This was it. I was going to Have anal sex with my best friend’s girl friend. I gripped her thighs and pushed my dick into her ass. She seemed tense at first, but after a moment she loosened up. It felt amazing. I had never tried anal sex before, but I loved it. It was so much tighter than a pussy.
As I fucked her ass, the table started rocking. “Oh shit,” I said as the table started to creak. It fell over and Claire and I ended up on the floor, my dick still in her ass. We were so horny at this point, we didn’t even stop. Right before I came, I stuck my dick as far as it would go and squeezed her extra tight. “Oh yes,” she moaned. I shot my load and then pulled out. We both got up
“We better fix that table,” Matt said as he and Nat came up from behind me. Natalie reached her arm around me and squeezed my penis. It got hard again.
“Yeah,” I said. “Your mom would…” I was interrupted as we heard someone coming down the stairs. We all froze.
“Hey are you guys hungry cause…” she stopped when she saw us. Her eyes scanned from the four naked kids to the broken table to the cards lying everywhere. Everybody stood still. Nobody said anything.
“I ordered pizza,” Matt’s mom said, breaking the silence. “You guys can go grab some if you’d like.”
We all walked towards the piles of clothes near the table. Everybody put their clothes on and headed upstairs. I was the last. “David, wait a second,” she said.
I turned towards Matt’s mom. “I never knew you were so large,” she said. She sounded really sexy. My penis got hard again. She noticed and walked towards me. “You can take your clothes back off,” she said. I’ve already seen you naked. I was shocked. Yet I went along. “I think it would only be fair if you got naked too,” I told her. She was really pretty for a mom. She was about 35 but looked way younger. She had brown hair and large boobs.
“Only fair,” she said. She started to undress. I took off all of my clothes and walked over to her. I was desperate to fuck her, yet I knew she would tease me for a while. “Oh my,” she said rubbing her erect nipples. “It must be really cold in here.”
“Well let’s get hot,” I say, reaching up and rubbing her nipples for her. She smiles and gets down on her knees. Taking my cock in her hand she starts to lick it. Then she pushes it to the back of her throat.
“Oh my god,” I say as she pushes my cock down her throat. She works magic as she sucks, but I’m eager for sex. She must feel the same way, because she stands up and leads me to the couch. “I’m on top,” she tells me knocking me onto my back. I do as she says stretching my hands behind my head. She gets in a reverse cowgirl position and starts to move up and down. I follow her rhythm and after a while we flip over and I get on top. I love playing with her boobs while we fuck. I lean down and bite one. She moans and I move to the other nipple.
We keep fucking and right before I cum, I pull out and shoot it all over her face. I hear the “THUD THUD THUD” and look over at the stairs. Natalie, Claire, and Matt are standing there. Oh shit this looks bad. I’m on top of Matt’s mom with cream all over her face.
I have no idea how it happens, but the next thing I know, everyone is taking their clothes off. Then it turned into a giant orgy. Matt and I fucking Natalie(I’m in back), while Matt’s mom and Claire lick each other’s pussies. Then after a while we change it up, and we’re fucking Claire. When were done with that I go back to Natalie and I’m surprised to see Matt fucking his own mom. I finish with Natalie and move to Claire. I’m just horny as hell from watching all of this.
We wrap it up after a few hours and everybody is exhausted. I call my mom to tell her I’m staying at Matt’s tonight. Claire tells her parents shes staying with Natalie, and Natalie says shes staying with Claire. We all crash in Matt’s basement. His mom brings down several blankets. I’m so horny I’m not even sure I’ll be able to fall asleep tonight.
Who knows what tomorrow holds?

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