By Andrew Diaz©
Some weeks after her first anal experiences, Valentina, my sister, went away with a girlfriend. It was the middle of the summer, and she said she wanted to travel and have some rest from everything that surrounded her. I guess that included me. Valentina traveled with Joanna, a good friend of hers, who was also my friend Matt’s girlfriend.
Valentina and Joanna went to Florida, and during those weeks, she barely communicated with me. Maybe there was something else, another reason why she wanted to be far from me and did not even want to talk to me.
The time passed, and one day I was in the kitchen fixing a sandwich for my breakfast when I heard the door of our house open. I went to the living room, and there was Valentina with her big backpack. She smiled at me and rushed to hug me.
“I missed you,” she said smiling.
“Me too! How was your trip?” I asked out of curiosity.
“Man, that was awesome! We had a great time. I have many things to tell you. But I’m hungry. Is there anything I can eat?”
I quickly made another sandwich for her, and we ate together. She mentioned some things about her trip without giving so many details.
“Dude, I stink. I have to take a shower… Wanna join me?” she asked while she winked at me.
“Sure!”
We went to the bathroom. She took off her top, then her bra, and exposed her nice big boobs. I took off my T-shirt and boxers, the only thing I happened to be wearing, and she removed her pants. We got into the shower, turned on the tap, and while the warm water fell on us, we kissed and touched our bodies. How much I had missed her! I fingered her for a couple of seconds while she stroked my cock, and then she decided to go down on me.
She sucked my cock for a couple of minutes, and after that I penetrated her. It felt so good to be inside my sister again. Our game lasted just for a few minutes because we both came soon. I could tell she missed fucking me too.
Later, we went out for lunch, and as we were eating, she told me more details about her trip. She mentioned places she visited and things she did, and then she confessed something I didn’t even imagine she would do.
“Hey… there’s something you must know… And please don’t get mad like that time.”
“Mmm… What time?”
“That time you found Ron banging me in the shower.”
“Um… Ok… What is it?”
“Don’t ask me why, but I ended up having sex with Joanna.”
“What?” I couldn’t believe what my sister had just said. “You and Joanna? How come?”
“Yeah… Well… Let me try to explain… One night, Joanna and I went to a disco. We drank a lot, and there were hot guys flirting with us. We danced with them, but we didn’t do anything. I guess we were so horny that we got back to our hotel, and we ended up kissing and having sex.”
She went on to give a couple of details about that first night, which in a way made me horny.
“Gosh! So… How did you feel? Did you enjoy it?” I asked.
“Yeah… It was fun and… Sexy. She’s so erotic… Yeah… I enjoyed it.”
Then, she talked about other experiences with her.
“So, this other day, we rented a car and ended up stopping in the middle of nowhere because we were so horny that we needed to fuck right away.”
After her lusty narrations, Valentina stopped and looked at me. That kind of look meant there was something else coming.
“Now… There’s another issue.”
“What’s that?”
“We both revealed some dark secrets to each other. I mean… I guessed that was one of the reasons why we ended up in bed… That night at the club, we started playing dirty questions… A kind of truth or dare, but just with truths. At some point, I ended up revealing you and I have been having sex.”
“What? Are you crazy? Why did you say that?” I asked angrily.
“Hey… I told you… We were drinking and… We were playing this game and having this talk and… Anyway… She’s fine with that. She was surprised, but I told her to keep the secret… And she will. I know she will.”
“I don’t get it! You shouldn’t have opened your big mouth!”
“Hey, chill out. Listen, there’s something else.”
“What? Did you tell her I fucked your ass?”
“Stop! You’re acting like an asshole! Look… She also told me something about her and Matt. They kind of like to have other people with them when they’re having sex, I mean, especially threesomes with other girls. Actually, Joanna proposed that I should have sex with them,” my sister confessed.
“Wow! So now you want to experience more things, and you’re going to fuck Matt too, huh?”
“Shut up! I won’t do that! I mean… I told her we could get all together. You know… Have a foursome.”
“What do you mean?” I asked naively.
“Gosh! That means I want to do this with you. Don’t you think Joanna is hot?”
“Well… She’s fine… I mean… Yes, she looks good.”
“Okay, so what do you think?”
I ended up accepting my sister’s proposal. We would have a foursome with our friends. I had known Matt and Joanna for a couple of years now, and I thought we could do that without feeling uncomfortable.
My sister was in charge of talking to Joanna and letting her know we would have sex with them. Then some days later, I bumped into Matt at a gas station.
“Dude! Joanna told me you and Valentina are in for this little, um, game,” he said enthusiastically.
“Yeah… It’s, uh, cool,” I answered nervously.
“Isn’t it? Man, I have always wanted to be with your sister. She’s just so hot. I mean, I like Joanna a lot, but if only she had such jugs as your sister does… Wow! I just can’t believe it.”
“I know.”
That was Matt. He was straightforward, and he would never keep anything to himself.
“Joanna told me about you two. I just want you to know I’m totally fine with that and your secret is safe.”
“Thanks, man. I really appreciate it.”
I was just speechless. On the one hand, I found it exciting to be part of this foursome, and I even thought it would be so arousing to see my sister being fucked in front of me once again. I mean, some weeks ago, my cousin and I had fucked her, and I knew Ron would not tell anyone about this. I just didn’t want more people to know what was going on between us, so I really hoped Matt and Joanna could keep this secret.
We also talked about creating the right mood for that special night, which would take place the following Saturday, just four days ahead. We said we should buy some wine and maybe plan a game as a warm-up for the big moment. Matt said he would be in charge of planning the game and I could buy the wine and some snacks.
The week passed quickly, and the day finally came. Valentina started to get ready early in the afternoon. She looked hotter than ever. I felt so anxious and excited and wondered how everything would turn out. We had agreed on meeting at Matt’s place at 7 pm, so at about 6:45, we left our house. When we got there, Joanna had already arrived, and Matt was finishing cooking something in the kitchen.
“I made us some salmon. I hope you guys like it,” he said.
Joanna laid the table, I poured some wine, and Matt served the food, salmon, a purée, and some vegetables. Everything tasted so good. We talked a little bit about the summer, the girls’ trip, and some other plans before classes started. Joanna even suggested going on a road trip with some other friends.
We finished dinner and moved to the living room. We grabbed our glasses, and I brought another bottle of wine. There was a sensation of excitement and nervousness in the air. It was Matt who broke the ice. He suggested playing Truth or Dare, and the rest of us accepted his proposal. Matt brought a set of cards, and we all sat in a circle on the carpet.
“Ladies first,” Matt said. “We’ll begin with Joanna.”
“Why me?” Joanna inquired.
“Because you’re on my right. So… Truth or dare?”
“Um… Truth.” “Okay.” Matt grabbed a card and read it. “Have you ever had sex outdoors?”
“Wow… Um… Yeaaah. It was last year. Freddie fucked me next to the university soccer field. There were some bushes near the field, and that’s where we had sex. It was late at night, and nobody was around. It was pretty exciting.”
“Gosh! You fucked Freddie?” asked my sister.
She was surprised because we had never heard about it, plus Freddie, a good friend of ours, was dating Andrea, another friend.
“Yeah, but just that time. We had been drinking after a game, you know, and… Things just happened.”
“Alright. Valentina, you’re next.” Matt announced. “Truth or dare?”
“Dare,” my sister called.
“Well… lick someone’s ear for thirty seconds.”
“But whose?”
“It’s your choice,” said Matt while he set his cell phone’s stopwatch.
Valentina turned her head towards Joanna, held her waist, and slowly directed her mouth towards her right ear. Joanna grabbed my sister’s arm and caressed it while she moaned softly at the same time. I could tell it totally aroused Joanna.
“Time’s up,” called Matt. “Your turn, dude. Truth or dare?”
“Truth,” I chose.
“Have you ever measured the size of your penis? If so, what’s its size?”
“Ha-ha… Well… Yeah, I have measured my dick… It’s, uh, seven inches long, I think.”
“Wow… Really? That’s good. I hope I can get to confirm that tonight,” said Joanna in a sexy voice.
“Honey, calm down!
“Ha-ha! Anyway, it’s your turn, hon,” Joanna announced. “Truth or dare?”
“Truth,” Matt chose.
Joanna took the top card on Matt’s deck.
“Have you ever fantasized about being in a porn movie?”
“Yeah! Sometimes I think it could be a good career choice. I mean, being paid to fuck! That’d be awesome!”
We all laughed. Then after a pause, Matt told Joanna it was her turn. Joanna picked dare.
“Lick someone’s intimate parts for thirty seconds,” said Matt.
“Oh gosh! Who should I choose? Um, I guess I won’t taste your cock so much today,” said Joanna while she put her hand into Matt’s shorts and took out his dick, which got totally erect in less than five seconds. Joanna put Matt’s thick cock into her mouth while my sister and I watched curiously.
It seemed it took longer than a minute since Matt was not really taking the time, so I had to tell them to stop.
“Wow! That was hot,” said Valentina.
Matt put his wet dick back into his pants, and almost out of breath told my sister to make her choice.
“Truth!” She exclaimed.
“Have you ever had sex in a pool or the sea?” asked Matt.
“Um… Ha-ha. I have. Actually, Joanna and I did it in the ocean on our trip to Florida,” my sister confessed.
“What? She didn’t tell me that. Oh, gosh!” said Matt totally surprised as he looked at Joanna.
“Yeah… It was this hot afternoon. It might have been around 6 pm, and it was still so hot. We were swimming, but it was so packed that we decided to move away from the crowd. We walked, got to this area that was kind of lonely, and got into the sea again. We started making out and began to have sex there in the water. It was fun!”
“You didn’t tell me about it,” I said.
“I don’t have to tell you everything I do, Andrew,” replied my sister.
“Well, Andrew, it’s your turn,” Matt said.
“Dare!”
“Dude, kiss someone’s cheeks for thirty seconds.”
I moved towards Joanna, who uttered an exclamation of surprise when she saw me grabbing her hands to make her stand up. I walked her toward a wall and made her turn around. She put her hands against the wall, I pulled down her denim shorts and underwear, and put my mouth on her ass.
I started kissing her cheeks, softly, slowly, some kisses here, some kisses there. Then, I spread her cheeks and got to see her asshole, so I targeted her little hole and licked it. She moaned, and I could tell she liked it. Then, I introduced two fingers into her pussy, and Joanna moaned louder, but that’s when Matt said time was over.
“Oh my gosh, Andrew,” said Joanna while she pulled up her shorts and tried to catch her breath.
“Next! Matt, what’s your choice?” Valentina said.
“Well, truth,” he said.
“No way, you picked truth in the previous round,” complained my sister.
“Okay, okay… dare, then,” Matt said.
Joanna picked the top card from the deck and said, “You have to show your butt, and someone in the group must draw an imaginary smiley on it by using their tongue.”
“And who’s gonna lick me? Not Andrew, please,” Matt demanded.
“I will,” said my sister.
“Oh, yeah, baby,” said Matt happily.
Matt stood up and got in front of my sister, who kneeled and pulled his pants down. Matt leaned a little bit, and Valentina started to draw the imaginary smiley on his ass. Matt’s erect cock pointed to the ceiling. Valentina finished, and Joanna and I clapped.
Matt pulled up his pants again while we could see this huge bulge underneath his pants. He sat down and looked at us.
“Okay, final round,” Matt announced. “Only dares from now on. Honey, this is what you have to do,” said Matt to Joanna while he picked a card. “Do a strip tease dance with some background music.”
“Oh gosh! No!” said Joanna complaining.
“Yes, you have to do it,” said Matt. “I have a perfect song on my cell phone.”
He searched through his cell phone music library and played a song. The melody of “Girl, you’ll be a woman soon” got into our ears.
Joanna sighed and stood up. She started to move sexily, executing some rhythmic steps while she slowly touched her legs, her waist, her belly, and her small breasts. She put her hands back on her waist, moved them toward the center, and unbuttoned her shorts. Then she unzipped them and let her shorts fall down. Her red underwear was revealed as well as her well-formed ass.
She continued dancing slowly and pulled her shirt up, little by little, until she took it off. She wore a sexy red bra, which protected her nice little boobs. She kept on moving and advanced to where I was sitting. She moved closer and closer until her pelvis was in front of my face. I could smell the sweet aroma that came from her pussy. I put out my tongue and licked the line that was sticking out of her panties. She stepped back, put her hand behind her back, and unfasten her bra, letting it fall too. Her nice perky small tits were revealed. I felt like eating them right away, but I had to be patient.
Finally, she moved close to Valentina. Valentina caressed her waist and her sides while Joanna pulled down her panties very slowly until she finally took them off. She sat down, and we all clapped. She looked very sexy.
“Alright! Valentina, here’s your dare,” said Matt. “You have to play with someone’s genitals for thirty seconds. So, who‘s it going to be?”
“Do you guys wanna see how I play with Andrew?” she asked, looking at Joanna and Matt.
“Yeah, that’ll be hot,” said Matt.
Valentina crawled very slowly toward my spot. Matt stared at her intently. I could see how much he wanted to fuck her. Valentina unbuttoned my shorts and took them off. Then, she did the same with the boxers I was wearing. She told me to stand up. She grabbed my cock and stroked it. She licked the tip of my dick and then started to suck my cock unhurriedly, introducing my shaft into her mouth little by little without using her hands. I moaned and caressed her hair.
It felt like she had had my cock inside her mouth for just five seconds when Matt said, “Time’s over.”
Valentina went back to her place, and I could see Joanna looking at my erect penis as I decided not to put on my pants. Matt said it was my turn, grabbed a card, and announced my dare.
“Give a boob massage to one of the girls in the group for thirty seconds.”
I stood up, went out of the circle, and stopped behind my sister.
“Alright! This is gonna be hot,” Matt exclaimed in delight at the scene.
I approached Valentina. I pulled her top upwards, and as she didn’t happen to be wearing a bra, her big tits were immediately exposed. I could see Matt didn’t take his eyes off her big boobs. I grabbed them and started to move them gradually, first up and down, then to the sides, and then I massaged them and moved them gently in circles, taking care of her nipples too. In the meantime, I pressed my free dick against her back.
“Time!” Matt said, ruining this fun moment.
“The last one, and this is for you, hon,” announced Joanna while she took a card. “Do a sixty-nine with someone in the group for thirty seconds,” she commanded.
Immediately, Matt stood up, took off his t-shirt, shoes, shorts, and boxers, and pointed at my sister.
“Come here, Val,” he told Valentina.
My sister obeyed his orders. Matt put his hands behind my sister’s ass and rushed to take off all her clothes. Then, he lay on the floor. My sister aligned her pussy with his mouth and crouched until Matt’s tongue made contact with her hole. Then, she expanded her body, and her mouth aimed for Matt’s erect dick until it was inside my sister’s mouth. I looked at Matt’s tongue and how it started to have a taste of my sister’s delicious pussy.
Joanna came close to me, knelt down, and pushed my chest, so I ended up lying on the sofa. Joanna went down on me straight away. I took off my shirt and placed my hands on her naked skin while she sucked my dick.
Next to us, Valentina uttered some sounds of pleasure while Matt worked on her precious pussy.
A couple of minutes later, Matt and Valentina stood up. He gently pushed Valentina down on the sofa, placed one of his knees there, and penetrated her.
My sister moaned loudly while my friend began to thrust inside her hole. I told Joanna to get on top of me. She did that, grabbed my dick, and put it into her cute pussy. It felt good. I touched her beautiful tits and moved my head to have a taste of them. I introduced her firm nipples into my mouth, and she moaned.
Next to me, Matt was busy fucking my sister. He moved fast, so fast that Valentina’s jugs moved back and forth so quickly as if they were going to explode. Joanna also started to move faster and faster, kind of jumping on top of me. She really knew how to move.
Valentina turned her head and looked at me. I looked back and smiled. She stared at me, blew me a kiss, and then concentrated on Matt again.
Some seconds later, Joanna moved away and told me to lie on the floor. I grabbed her ass, made her body turn and lifted her waist, until she was lying on all fours, and I kneeled to fuck her from behind. She screamed loudly as my dick penetrated her hole.
Matt stopped and told my sister to get on the floor too. They came close to us and imitated our position. Matt went behind Valentina and started to fuck her doggy style. She screamed too while her large breasts moved back and forth.
We kept on fucking for a while like that. At some point, Matt stopped, stood up, and moved closer to Joanna, grabbed her head and made her swallow his dick. I kept on fucking her pussy while Valentina got behind me, put her right hand down my ass, and touched my balls. That felt amazing. Then, she moved her hand toward my ass, rubbed my anus, and slowly pushed one of her fingers into my ass. I screamed with pleasure.
Matt pulled his dick out of Joanna’s mouth and went back to take care of Valentina. He placed his body behind her and continued fucking her in this doggy style position. In my case, I grabbed Johanna and made her lie sideways as I placed my body behind her and penetrated her pussy.
I moved faster and faster, and Joanna began to moan and scream louder. I was on the verge of coming when she screamed loudly again, and her thighs contracted rapidly. She screamed one more time and let her head fall on the carpet. I thrust very, very slowly but deeper. Her thighs shook, and she groaned. I took my cock out of her pussy, made her lie down, and caressed her. I lay down next to her, and she grabbed my dick and stroked it.
Next to me, Valentina moaned, and Matt started to make louder noises until he could not take it anymore and exploded inside my sister’s pussy. Valentina stayed on all fours for some seconds and then lay down between him and me. She was facing Matt, so I moved behind her and penetrated her. Matt used his fingers and began working on my sister’s clit. Joanna hugged me from behind and touched my balls.
Valentina screamed louder and louder, and when I couldn’t hold it anymore, she came. I thrust a little bit more and came, too. My sister’s pussy was now an ocean of cum. I turned around and kissed Joanna while Matt made out with my sister.
We rested for some minutes while we kept kissing and caressing our bodies. Then, we had a second round of wild sex. It was just amazing how erotic this whole experience was.
When we were done, we decided to go to bed because we were very tired. Matt secretly said something to Joanna, and as she nodded, he looked at Valentina and proposed spending the night in the bedroom with him while I could spend the night with Joanna on the couch. I looked at my sister, and she nodded.
I went to the couch with Joanna, made out for a while, and fell asleep. The next morning, I woke up with some wild screams coming from Matt’s bedroom. It was Valentina. I guess Matt was banging her. Instead of driving me mad, those sounds aroused me, and I started touching Joanna, who was still asleep.
Little by little, she began waking up, and we ended up having sex again. An hour later, Valentina and Matt joined us in the kitchen. We had breakfast together, and later we said goodbye. An amazing adventure had come to an end, but I guessed this was just the beginning of a new kind of friendship and wilder ventures.
This story is part of a compilation of 25 erotica stories that are included in the book Sex Stories by Andrew Diaz. If you want to buy the book, you can purchase it in our store: https://payhip.com/b/h1RPb
