TLDR: Girlfriend / Step-sister (long story, short version our parents got together after we were friends) and I (20F) went to concert, went home with 2 guys, fucked them both, lost my anal virginity.

At the time I was only 20 (36 now). My girlfriend / Step-sister and I met a couple of cute guys at a Kenny Chesney Concert in South Carolina. We were in the stands singing and dancing to all of Carrie Underwood’s songs when they noticed us from about 5 rows down, we were loud and having a great time. We saw them keep looking back at us and my friend said, “I think those guys are gonna come up here.” As soon as Carrie finished her set, her prediction came true. We talked a bit and they asked us where our boyfriends were, to which we replied we didn’t have boyfriends. They asked if we’d like to hang with them during the show, and when we said yes they offered to buy us some beers. Just as I was about to tell them my age, “Oh, I’m onl-“ my girlfriend squeezed my hand and blurted “Only having 1. She’s only having 1, she’s the Designated Driver.” That’s no problem one of them replied, we’ll get you home! By the time Kenny took the stage we were on our 3rd beers, and when it was over we were feeling really good. Not super drunk, but pretty buzzed and up for anything… well, almost anything. Making our way out of the venue we were all holding hands. My girlfriend and I holding each others hands, and the boys holding our hands. We got to their truck and they pulled out some weed and a cooler with more beer in it. The guy she was with said “We’re gonna be sitting here a while before it thins out enough to go anywhere, y’all smoke?” as he packed a pipe. My girlfriend was like, “Oh fuck yeah!” So, sitting on the toolbox and tailgate, we smoked and had another beer. As it usually does in those situations, the conversation between the 4 of us turns sexual. We tell the simplest things from how many boyfriends we’ve had to the wildest things we’ve done. Being only 20 and very inexperienced, my wildest thing was having sex in my uncles hot tub with my then boyfriend at 17. As the stories keep rolling, I’m getting very turned on, my breathing getting heavy, and laughing awkwardly when someone’s story has an element of humor. The guy I’m with can tell. He leans over and whispers in my ear, “I think you’re so hot”, and as he’s pulling away, I kissed him. He kisses me back and I’m very excited. As we’re making out, my girlfriend starts yelling “Woo, yeah, get it!” as if she’s trying to embarrass me. I didn’t care. My guy reaches down between my legs and goes up one of the legs of my cutoff shorts from the bottom up to rub my pussy. They were very short 😉. God damn that feels good and I am WET. I reach over to him and start rubbing his crotch over his jeans. He’s rock solid. I go to unbuckle his belt and he asks if I want to get in the cab of the truck. Of course I said yes. We get in the back seat and this is when I get to see it. I swear to god if it wasn’t 8-9” then I was hallucinating. I give him a blowjob for a few minutes and he tells me he needs to be inside me, I tell him I want the same. I get my shorts off, pull down my tube top and start riding him. Just as I was getting in rhythm, the front doors to the truck open and my girlfriend says, “traffic is moving, we’re going back to their place.” Startled by the lights in the truck coming on, I pull up my top and hop off of him. My girlfriend looks back at us and laughs, “Guess I got some catching up to do. Why’d you stop girl? Get back on that thing and ride cowgirl, RIDE!” The guy she was with, the one driving, pulls his dick out, looks over at her and says, “If you’re looking to catch up, you can get a HEAD start right here.” pointing at his exposed cock. I hop back on my guy facing forward so I can watch her give him head. My girlfriend looks back again and says, “Race you!” She starts sucking his dick, and I mean SUCKING. Loud popping sounds when she gets to the head, gagging sounds as she’s taking him to the back of her throat, slurping her saliva as she gets sloppy, I mean she’s sucking him like his life depends on it. Meanwhile I am bouncing and rolling my hips like I’m riding a bull at the rodeo. Not even three minutes in, my girlfriend pops up, cum in her mouth and says “I win.” Not to be discouraged, I keep riding, getting faster, and he finally cums. The driver reaches down in his door pocket and pulls out a roll of blue paper towels for us to clean up. Laughing and joking with my guy, he chuckles “you ain’t get no cum on my seats did you? You gon’ clean it up if you did.” We all laugh and get our clothes back on, to whatever extent we had undressed. With all the traffic, we still had another hour to get back to their house. I start making out with my guy again. He’s rubbing my breasts, kissing my neck, and massaging my pussy. I still haven’t cum yet, so I’m still revved up. We finally get back to their house. We get inside and my girlfriend flops down on the couch, patting the seat next to her for me to come sit. My guy brings the weed and beers in, turns the TV on, and asks what we want to watch. “TV? Unless it’s porn, I don’t wanna watch shit other than you finally giving my friend here and Orgasm. Her last 2 boyfriends (of which I’d only had 3 by this time) couldn’t even make her cum. So… what’s it gonna be?” His reply, “How bout both?” He pulls a DVD out of a video game box and puts it in the console, fast forwards to the sex scenes, walks back over to me, and flops it back out in my face. God damn it’s beautiful now that we’re not in the dark truck and I can actually see it. I take him in my mouth, I can taste the tang of my juices still on him, god this is hot. About this time, the other guy walks in and laughs, “Oh it’s that kinda party?!” My girlfriend says “Fuck yes it is, now get over here and fuck ME” as she slithers out of her shorts and peels off her tank top, no bra, no panties, and flops back down on the couch. I’ve never been in a situation like this before, but the weed and alcohol have severely lowered my inhibitions. So here we are on the same couch, her getting laid and me sucking dick. My girlfriend scolds the guy I’m with, “What the fuck, you gonna fuck her or what?” I look up at him with a, yes please look in my eyes. He sheds his jeans and then his top. Holy shit what a chest. It was beautiful. Muscular pecs and just the right amount of hair like I like it. Taking me by the hands he pulls me to my feet, undresses me, and picks me up by my ass, wrapping my legs around his waist. Reaching down under my ass, he grabs his dick and probes around my pussy until he slides into me again. He lets me slide down as far as I can onto him, he’s so much deeper inside me like this. I’m so full. He spins around to lay me onto the couch, “No, stay like this I tell him.” The depth and angle at which he’s inside me, coupled with the rubbing of my clit on his pubic bone is definitely gonna make me cum. I’m rolling my hips to feel him completely filling me up as he lifts me up and down. I haven’t cum from sex in 2 years, and I can feel everything start to tighten. Finally, I’m cumming, Jesus Christ am I cumming. My legs extend, stiffening from the intensity, my head slings back, my back arched, he almost drops me, but he continues pounding me until I can finally regain my composure. He lifts me off his cock and plants my feet on the floor. His cock is drenched in cream as he reaches down and starts stroking it. When the ringing in my ears finally subsides, I hear my girlfriend pleading for her guy to go harder. He’s really pounding away at her, bearing down with all his weight on top of her. She reaches out her hand toward me, and I take her hand. “Not your hand, I want to feel your pussy!” she’s says. She reaches up and slips a finger inside me, still getting fucked herself. “Shit girl, sooo creamy, and you’re still clinching! He really got you huh? Good boy. Good boy” Standing behind me, he bends me over, me and my girlfriend now face to face. Just as we’re about to kiss, she cums. He slides back in my pussy and I’ll be lucky if I can wipe after peeing later on, he’s so big and he’s pounding me so hard. Her guy gets up off of her and goes to get some towels. Tired of bending over, I stand up and he slides back out of me. “Which one of you has a king size bed” my girlfriend asks. Well, they both did. We all make our way to my guys bedroom, me and my girlfriend holding hands down the hallway. She spins me around and pushes me down on the bed. “Let’s really get wild, like disappointments to our parent wild. You want to feel him?” pointing to her guy. “You want to feel them both?!” I wasn’t ready for that, “Him, yeah, sure, both I’m not ready for” I explained. “Fine, watch and learn” she says. I scoot up to the corner at the head of the bed as she jump up and splashes down on the bed face up, like you see people falling into pools on commercials. Rolling onto her side, she invites both guys onto the bed, one in the front, one in the back. My guys cock still covered in cream, she takes him up her ass first. I’ve never had anal sex at this point, but how easy she took him inside her, and knowing how big he is, it didn’t look too bad. I’m finally getting a good look at the cock of the guy she was with. Not bad. Easily 7”-maybe another 8”? As she’s getting used to my guy inside her, I suck the other guy, I can taste her on his shaft. She finally summands her guy to come over and get back inside her. I’ve heard of this before but never seen it. I haven’t even watched porn at this time. They’re all really getting into it. She tells my guy to choke her from the back. And her guy to slap her in the face. I’ve never seen this side of her. She spits in her guys face and tells him to slap her harder. I’m definitely not doing that. Honestly, I’m losing the mood, but then I see her cum again, this one obviously more intense. At one point I thought it might’ve been a fucking seizure!! She couldn’t even speak plain English, just mumbling as she was cumming what sounded like “Don’t kill me. O fuck they’re gonna kill me” but I knew they weren’t. They both pull out of her and she gasps like she’s been underwater for 5 minutes. She looks back at me, “Intense huh?” she’s asks with a giggle. Yeah, to say the least. My guy comes back up to me, stroking his cock. “Wanna taste her ass?” I decline. He asks if I’m ready to get fucked again, but knowing he’s just been in her ass, I deflect and motion for the other guy. “I think I’ll have some of what she had.” I scoot back down the bed and invite him inside me, but to my pleasant surprise, after he slings my legs open, he dives in face first. This is only the second time anyone has gone down on me, and that is mostly due to my insecurity at the time. “You don’t have to do that” I tell him. He asks if I don’t like it, and I explained that he didn’t have to do that since I’d been having sex with his friend, who came inside me earlier by the way, and so if it didn’t smell good or whatever (which, subconsciously was what I was actually worried about) he could stop. He assured me it was fine. Oh, it was fine alright. Knowing what I know now with the experiences I’ve had, even though that was only the second time, it was the best I’ve ever had even to this day. I’ve tried to get other partners to do the things he did, they can’t recreate it. He licked me inside and out, worked my clit, fingered me, teased my asshole with his fingers, it was just a pleasure overload, and when I came I could feel the cream oozing out of me. He rolled me over to prone and cracked me open like a coconut. He slid inside my soaked pussy like a hot knife through butter. My girlfriend licked her fingers, slipped them inside herself to gather some wetness, spread my ass, and put a finger in me. I moaned in pleasure. It was tight, and mildly painful, but once I relaxed, it was nice. Her guy now massaging my insides, and her finger in my ass, my guy from earlier stands on the bed and puts his dick in my girlfriend’s mouth. He orders her, “Taste your ass. Taste your fucking ass. Take it all the way. I want to feel the back of your throat while you clean my cock. As I lay there getting stretched from behind, seeing his cock plunge into her wide open mouth, hearing the gags, watching her throat bulge as tears ran her mascara, her l continuing to probe in my ass with every thrust of him in her mouth, taking in the smells of our passion, I was overcome by the sensory overload. I was gonna cum again. Here it comes. My asshole clinching around her finger like a finger trap, my pussy gripping his cock as the head barely slipped out with every stroke and pressed up against my G-Spot when he shoved it back in me. I was cumming, his weight bearing down on me, holding my arms behind my back, I was helpless and vulnerable, and when the final wave came it felt like a convulsion. I literally blacked out, woke up with him continuing to bury his cock inside me balls deep, and was still orgasming. I begged him to cum. “Cum, please, please, please cum. Wherever you want, where do you want to come?” He didnt answer, only asked me back, “Yeah? Yeah? You ready for me to cum? You want my cum don’t you? You said anywhere I want. I’M TAKING THAT ASS! I’M GONNA CUM IN THAT ASSHOLE. You ready?” I could only reply with a bratty little “Uh-huh”. He continued to pound away until finally he was ready to explode. He removed my girlfriend’s finger, spread my ass, spit in it, pulled out of my pussy and violated my virgin ass. This was not my girlfriend’s little finger. I swear I could feel the tearing as he plowed into me. As I screamed he was relentless, “Oh gawwwwwd, YES YES YES, it’s so GOOOD” my moans heightening the experience for us all. The guy getting sucked off by my girlfriend exploded in her mouth, his cum dribbling from her bottom lip, and almost simultaneously I was getting my ass filled with cum as well. With every eruption inside me I could feel him swelling, stretching my walls further as he sunk himself so deep I thought he might rip me apart. Finally he made his last thrust and let out a manly groan. He withdrew from inside me and I instantly felt the cum spilling out of my ass, running down and over my pussy. Myself and the guy I was originally with retreated to the shower in his room as my girlfriend and her guy did the same in the other bathroom. We stayed the night, woke up, and they took us back to our car the next morning. My fucking ass hurt for the next 5 damn days, BUTT IN THE END, it was totally worth it and I’m glad I got that experience early so that it could “Open me up” to being receptive to more experiences as I got older.