Helping my sister lose her virginity [GROUP]

This is hands down my husbands absolute favorite story. The first time I told it to him we were super drunk and fucking like animals and in that state, he likes to hear about my past, so I told him this one, and he actually stopped to listen and then we finished. I could tell he loved it because the next day he was like, can you take me through that whole thing step by step.

Anyways, I was in college still and my sister was a senior in high school at the time – weird fun fact, she currently lives in my old dorm room! She used to come up for weekends every once in a while because she’s kind of anti-social and growing up we were each other’s friends since we’re only a few years apart.

When she came up it was always low key, her and I would have like a glass or wine or two, watch netflix, and just hang out in my room. Now my sister is an insane runner and has like a 10 pack and is all lean muscle, but back then she was a bit chubby and didn’t wear makeup and didn’t really do anything with her hair, it was chopped super short. I basically thought she was a lesbian and too scared to come out, I also just assumed she was asexual.

This was the weekend before Christmas break and we were crashing in my dorm, then on Monday we were driving upstate to my grandmas to meet the rest of the family. I finished my last final of the semester and got to my dorm to find the door open and my sister, Maddie, was talking to our RA who was apparently over the whole RA thing because he had a 12-pack of Pabst sitting on my desk and they were drinking with the door open at dinner time.

Kyle was a really nice guy and totally not a predator so I wasn’t worried. I laughed and did an, “Oh did you meet my younger sister?”

Kyle, always trying to be a gentleman, but honestly just a meat wall of a man – he was around 6’4″ and easily 300lbs. He looked scary, but he was a goofy farm boy from Iowa or Idaho or somewhere like that who had an older brother who gave him too many shitty tattoos when he was like 14 so he looked like biker trash. But, Kyle was awesome and a great friend.

He was telling us how the whole place empties out tonight and it’s pretty much just the RAs left. I explained our plans and he told us how they’d all be drinking in the lounge or his suite later.

Maddie and I decided to shower and go to dinner then we could have some drinks and join them. It was weird drinking with the RAs but even security seemed to be gone from campus at this point. Because my campus is like 100 years old, the shower situation is more like a gym. It’s just a big room with shower heads all around the walls and towel hooks by the door. I don’t know how people in the 20s were so prude but had no issues taking a shower staring at all their friends.

We poured some warm rum and cokes and I was finishing packing when Kyle and two other RAs – Amanda and Gus – showed up saying they were going swimming in the indoor pool in the gym. Apparently Kyle used to be a lifeguard and had a key. They were already in their swimsuits and Amanda, an Irish girl here on a scholarship for swim team was in a red lifeguard trunks that were too big for her and a tank top with clearly no bra underneath.

Maddie didn’t have a swimsuit, so she borrowed a t-shirt of mine and said she’d just wear these old boxers I had in my room that were from an old boyfriend. The only swimsuit I had was a highlighter yellow two piece. We changed while the RAs waited outside and walked with them across the abandoned campus.

The pool was thankfully heated and the giant room it was in was filled with chlorine-smelling steam. The overhead lights were all off and Kyle didn’t want to turn them on, so the only light was the two exit signs and what came in from the giant windows way up by the roof and a single light at the bottom of the deep end of the pool that glowed dull yellow. It was pretty dark.

Gus, a lean asian guy who rarely talked, dropped his shorts and cannonballed into the pool before anyone knew what was happening. Kyle laughed, shrugged and set his beer down, then took his shorts off and swung them around over his head and threw them onto the bleachers before diving in.

“They’re idiots,” Amanda said in her irish accent. She set her towel down and the box of wine she’d been carrying and went down the ladder without getting undressed. Maddie looked at me, like she was asking permission and I smiled and dove into the pool. She climbed down the ladder.

Gus sat on the edge of the pool, very much aware his dick was out and not worrying about it, and looking a bit drunk. We swam lazily around and drank more. After about 20 minutes Maddie and Kyle were wrestling by the steps and giggling.

“Fine,” Maddie yelled in a fake mad way, shoving Kyle back. She took off her tank top and revealed her almost flat chest with her puffy nipples. She had a tree tattooed on her stomach that was kind of sexy in a weird way. She then shuffled around underwater and lifted the baggy shorts above her head and threw them in my face, “Your turn!”

I laughed, and feeling drunk and emboldened by the darkness and water took off my top and set it on the edge of the pool. Then untied one side of my bottoms and pulled them away like I’d done a magic trick. Maddie laughed from the other side of the pool where she’d been talking to Gus. I balled up my bottoms and hurled them at her, “Your turn!”

She had a sudden startled moment then set down her beer and said, “Why the fuck not!” She pulled down the boxers first, then struggled out of the t-shirt, which got stuck on her head for a second, leaving her small boobs with her super tiny nipples exposed to everyone. You could see her fuzzy blonde pubes through the water reflecting in the light. She was about 10 lbs overweight, but she was super cute and it just looked like babyfat kinda.

Gus clapped as she got her shirt off her head. She frowned at him and swung her wet shirt at him, it made a super loud thwack sound and he pretended to be hurt, which made her swoon over him, which he loved. He laid back on the edge of the pool and said, it stings, and grabbed at his side. Maddie climbed out of the pool and bent over him asking if he was ok. He just started laughing and she smacked him and fell back into the pool.

We all swam around naked for a while and started to turn pruney. Kyle called it quits and said let’s go! Gus, being an asshole, grabbed everyones clothes and ran like crazy back to the dorm across the empty quad, his dick flapping in the freezing weather.

We grabbed our towels and half ran after him carrying our booze and keeping a lookout. We got to the dorm and were frozen solid, so Kyle led us to the men’s showers and we all washed off, and then Kyle gave Maddie and I some of his giant t-shirts and we continued drinking.

Gus pulled out his phone and showed us this app he had that was a spinning wheel like Wheel of Fortune mixed with spin the bottle, but the wheel spokes were all dares. Kyle and Amanda were sitting together on the bed and us three were on the floor by the wall with towels in our laps covering up we had no undies.

Gus spun the wheel first and it said take any one piece of clothing from any player you want. He took Maddie’s shirt and she sat there looking a bit uncomfortable being totally naked, so I draped my towel over her shoulders. Then it was Maddie’s turn according to the rules Gus probably made up, and she got the same thing, taking Gus’s trunks in return – and he sat there proudly with his dick out.

We went a few rounds and it was taking some clothes off, chugging beers, and flashing people type of stuff. Then Gus got Kiss any player for 90 seconds. So he chose Maddie and having never seen or heard about my sister kissing anyone, I was surprised when they started heavily making out and groping each other right next to me.

Maddie leaned back against me when they finished and I laughed. She said, “What?” I shook my head. Nada. I always thought of her as such a prude and here she was.

Kyle spun and got Perform Oral Sex on the Player to your Left which was Amanda and fitting because they were all over each other. She laid back and put her head on his pillow, and from the floor all we could see was Kyle’s arm and her leg and face. She was biting her lower lip and arching her back. Maddie grabbed my arm and when I looked at her, she was pretty wide eyed. The timer went off on 90 seconds and Kyle sat up, wiping his chin and laughing. Amanda was bright red.

Amanda spun and got Use Vibrator on Player Across From You, that would of been me but we didn’t have a vibrator. The group conferred and were deciding between spin again and hairbrush. It went hairbrush and for the first time in my life I was getting fucked by a cute irish girl holding a hairbrush. She didn’t make eye contact as she slid it in and it didn’t feel horrible.

I rolled and got Masturbate for the Group. So, I leaned back against the wall, not looking at my sister, and put on a show, rubbing my clit softly and keeping my eyes closed. I didn’t look at Maddie when I was done.

Gus rolled and got Get Oral from the Player of Your Choice and he chose the obvious person. I couldn’t take my eyes off of her taking Gus’s girthy dick in her mouth, it was surprising. She had her ass up in the air, pointed right at me, and I could see her face in the mirror on the wall. Gus was smiling wide at me and looked at Kyle who looked a bit shocked it happened so fast.

We went another round of chugging and I kissed Amanda when Kyle drew a make two people kiss spoke. Amanda drew the same one and had Gus and Maddie kiss. Then Maddie drew a spoke for Take any Player in the Closet for 7 Minutes card.

Kyle’s closet was a small room with a sheet stapled at the front to hide his messy pile of clothes. She stood up, took Gus by the hand, fucking winked at me, and led him to the small room. Gus was laughing and he handed me the phone which had the timer on it. I started it.

All I could see through the curtain was bodies moving. The dresser creaked some, and I saw the curtain puff out a bit and heard Maddie moaning softly. I could hear them whispering to each other and Maddie said oh god softly. The three of us were all locked on the curtain. About two minutes in, the rhythmic fucking sounds started and I thought woah, that’s happening. Maddie’s hand grabbed the wall on the edge of the closet and it was all we could see, she had a white knuckle grip on it and he must’ve had her bent over from the angle of it. It got louder and faster and in the silent room we could hear their breathing perfectly. I could hear the sounds of her getting fucked, the wet sliding, all of it and it was shocking. I felt like anxious and a bit turned on too.

I looked over at Kyle and Amanda and she had her hand rested on his hard cock and they both were smiling at the curtain. Maddie’s hand went back into the closet and the wet slapping stopped, and it seemed they changed positions. Feet were poking out from the bottom of the curtain and they were on the ground. There was about two minutes left.

I heard Maddie softly saying, Fuck fuck fuck fuck fuck over and over with each thrust. Then Gus groaned loudly, too loudly and Maddie yelped a bit and started laughing. The curtain opened a minute later as the timer was going off and Gus walked out triumphant, and Maddie followed looking flushed and panting a bit. She slumped down next to me and wiped at the cum between her legs with the towel.

Kyle and Amanda kicked us out immediately after that and were fucking before we could even get out the door. We went back to my room and kept drinking. Gus asked if we wanted to keep playing. Maddie was all for it, I felt a bit cautious. We played a couple rounds, I gave Gus a limp 30 second hand job and we made out. He and Maddie kissed a few times.

Then I called it a night and we went to sleep.

Source: reddit.com/r/gonewildstories/comments/a88zjb/helping_my_sister_lose_her_virginity_group