It was senior year of high school, we were all off to college in a few months and Max has the house to himself for the weekend. Jessica and I had recently broken up, which was problem because we were in the same circle of friends. The breakup wasn’t good as I cheated on her with Ashely, another one of our friends, so she decided to cheat on me with Drew, our friend we thought was gay but ended up having sex with Jessica. Regardless Max convinced us both to come, saying in a few months we wouldn’t see each other anymore for a while .
The six of us were there, myself, Jessica, Max, Drew, Ashley and Mimi. We played a bunch of drinking games and were all pretty buzzed when max said, anyone interested in a little Truth or Dare? We all agreed, Jessica looked at me and said no matter what the dare is we have to agreed to do it, I not wanted to back down or seem scared said no matter what. The tension in the room was obvious, we started with the BS dares, ring the neighbor’s door and run, eat the year-old candy bar, little stupid things. When Max started it daring Mimi to take off her top, she looked at him rather displeased and took her shirt and bra off, two C cup breast plopped out. It was Mimi’s turn, when Jessica leaned over and whispered in her ear, Ryan, get naked! She went right for the throat, I started to protest saying your just…. when everyone started booing, I stood up and dropped my pants and boxers, turning beat red.
Jessica and Mimi giggled, Drew laughed and said, did that little thing actually please you? To which the other guys laughed, I turned beat red further and sat down with my hands covering my cock. I wouldn’t say I was the biggest but 6 inches is normal sized isn’t it? Beat red everyone knew the next dare was for Jessica, I was ready to make her mad. Jessica, I dare you to eat Ashley’s pussy, hey maybe you’ll still taste my dick? I said laughing, Ashley looked at me with disgust, are you fucking serious! She said, fuck you, Jessica exclaimed. I stared the two of them down, a dare is a dare right? Now start lapping the pussy, it was better than yours anyways I said.
Everyone was bright red, not sure how to react. Max spoke up, a dare is a dare, you gotta do it. Right there we all knew how intense the game was going to get. Ashley stood up first and took off her shorts and panties, she sat down on the couch and spread her legs apart. Jessica, with a sad look on walked over locking her arms underneath Ashely’s thighs. She dove right in, starting with a long lick at the base of her pussy up to her clit, making a circular motion right around the clit. There were audible loud wet kisses coming from her crotch as Jessica buried her tongue into Ashley’s pussy. Ashley was now panting and moaning, her arms up over her head. Jessica’s tongue continued her assault, poking and forcing its way between her sweet lips. Ashley’s moans grew louder as her orgasm built up, her hands now firmly behind Jessica’s head as she assisted Jessica to ride her pussy with her face.
Mimi had begun to touch herself ever so cautiously, biting her lower lip as she watched the show, the guys all covering their crotch except me as my cock grew hard, I had nothing to hide it. Jessica’s face now glistened with Ashley’s juices as the intense oral session grew more furious. Ashely was now moaning and screamed out in a loud pant, Oh my gawd, oh my gawd, oh my gawd I’m gonna fucking cum all over your face face, holy shit! Was the last words she blurted out, her body wilding bucking, Jessica’s face taking an assault, holding onto her legs for dear life. As Ashley collapsed, Jessica finally pulled her face out with a loud gasp catching her breath as she was buried deep between Ashley’s legs.
Everyone was silent, Jessica’s face glistening and looking directly at me with an evil look. My turn, she exclaimed, looking to Max, do your parents have any lube she asked. Max looked confused, I don’t know he said back. Well go fucking look she said, and bring in your condoms, Ryan’s ass is about to get fucked right in front of us, she turned to Drew, Drew I dare you deflower Ryan’s ass for us and cum down Ryan’s throat when your done! She exclaimed in an authoritative voice. I went to go speak but before a word could come out, Jessica said loudly, a dare is a dare, I don’t want to fucking hear it Ryan now legs up on the couch, hope he doesn’t wreck your ass.
I got up, I quit everyone, I said loudly, Jessica immediately jumped to her feet, no fucking way you quit, I had to eat out Ashley, your going to take Drew’s cock up that tight little hole. Over here now! She shouted, I walked over the couch and laid back, Drew stood up, dare accepted. Now Ryan, I am going to start by rimming you, I am going to eat your ass to make it more relaxed. With that Drew was now in the same position Jessica just was, his arms around my legs and his tongue leaned forward lapping up my virgin hole. I flinched at first jolting up a little, then it began to feel good, his warm tongue massaging my hole, maybe this wouldn’t be so bad I thought to myself for a second. Finally opening my eyes to see Jessica, Max, Mimi and Ashley all looking over in amazement, I felt so embarrassed and vulnerable.
This went on for a few minutes before Jessica spoke up, enough of that Drew, Ryan get on all fours and wiggle that ass. I looked at her with a face of sorrow, I said on all four-bitch boy and wiggle that ass for Drew, show him you want his big dick. Big dick I thought, how big is he I thought to myself. Mimi come help me lube him up, I hear the sound of a condom packet tearing open, there was no going back. I got in doggy style position and swayed my ass back and forth. Mimi and Jessica popped open the lube bottle and I looked back.
Drew wasn’t a monster like what you’d see in porn but clearly another inch or two on me and a lot thicker. His flaccid cock swayed as he walked closer, his cock was uncircumcised, his foreskin covering the head, his ball dangled down low like two big wall nuts. My mind went into panic, how bad was this about to hurt, I felt a cool dab of lube hit my asshole as Jessica worked a finger in. Just like when I used to give you a blow job, right baby. She said, followed by slapping my ass hard, Right baby, she exclaimed, I said yes baby.
She slowly worked two fingers in and out, opening me up. Jessica whispered into my ear, I hear each inch his cock goes in slowly takes away your manhood, if he comes up your ass, you’ll probably crave cocky you little bitch! Lucky for you he’s wearing a condom. With that I felt his heavy dick slap my cheeks splattering a little lube on the cheek. He laid his still flaccid cock on my back, Jessica grabbed it giving it a few tugs as it got harder. Time to take some dick he exclaimed as I felt the rubbery head of his dick push up against my asshole. He pushed his way in, the expression of pain on my face as I struggled to face the invasion of my ass.
His head made its way through the entrance, I let out a few yelps of pain my ass tightened up, his hands gripped my hips tighter pulling me in closer to him. My body instinctively tried to push away and salvage my manhood. Just relax and stop trying to resist Drew said gently, yeah Ryan, relax, feel your manhood slip away and take that thick cock of Drews. I took a deep breath and arched my back pushing to match his thrust, my body felt a popping feel as his head pressed its way past my initial resistance point. My body let out a moan and sigh of relief, feeling like I just relieved myself but in reverse. Drew slowly pulled out, his cock must have been all the way in, as I look behind me I see my limp cock dangling as noticed he must have only be about half way in. I hear the cap of the lube pop open and cool lube hit my ass crack sliding down into my now open hold as Drews cock met my hole at the same time as the cap.
He thrusted forward, gripping me tight, my back arching up, as I take a deep breath, exhaling as his cock pushes back to where it was. I let out a yelp again as his cock was exploring new territory, I bucked forward and yelped as each inch slide in, my insides feeling like they are being rearranged. Ow, ow, I pant and grunt, stop, stop. I take a deep breath as Drew pauses, just relax baby, Jessica say, take that dick baby, its so hot watching Drews fat ass stretch your tight ass out, your ass hole trying to hold on for dear life as he pulls out it pulls back with it, oh baby take that dick like a good little bitch. Jessica starts caressing my back as she coaches me, Drew give him a good fucking bottom out on this little bitch.
With that Drew withdraws his cock just before the tip slides out before thrusting it back in to where it was, he repeats this motion several times before I finally feel his big balls slap up against my taint followed by his pelvis slapping me forward. His cock widened right around the middle, my ass held his cock there, adjusting to the side and he paused balls deep. I heard Mimi exclaim how hot this was, I could hear everyone’s voice near by I quickly looked up everyone was fascinated by the sight of Drew stretching my tight ass out. I started to have a momentary feeling of embarrassment and shame, what the hell was I doing, as I started to wonder this Drew gripped tight and worked his dick out and then slammed it all the way back in. I moan loudly, I bucked, my body wanting more of his dick, betraying my heterosexual status.
Now that we had broken my ass in, Drew said, time to really break this virgin ass in, he withdrew his fat cock, a loud spluff sound exposed the gapping hole he creating before bucking it back in. Now gripping my hips tight me matching his thrust as our bodies made loud slaps with each thrust, all 7 to 8 inches driving deep into my bowels like a piston. After about five or six minutes he slowed and told me to get up. He sat back on the couch and told me to straddle him, I went to go sit on his cock and he told me to face away and sit on his cock.
I sat backward into his lap positioning my feet into a squat position as I looked forward, I now saw all my friends mesmerized by our spectacle. I was now hungry for his dick and that was all I cared about. I hovered over his cock, I reach down finally fully feeling the girth of his thick cock, my hand unable to close around it. I positioned it against my now gapped hole and slowly let every inch slide inside me. I repositioned my hands behind me and started to gyrate my hips circling his cock deep in my ass. I readjusted and got used to his girth before lifting myself up and then slammed back down, repeating until I developed a rhythm with Drew.
The group starting to all play with themselves as I rode my friends thick cock. Mimi exclaimed oh my god his little limp cock is dripping, I briefly looked down seeing precum dribble out of my cock. Ashley commented, wow his little cock is still limp just flopping around bouncing on Drews big cock, I wanna ride that one she giggled. Jessica looked at her, oh god you have no idea how good his cock will feel after fucking Ryan’s little dicklet, they both laughed. I didn’t care, I wanted him to fuck me good, I was now moaning and words were slipping out of my mouth unintentionally. That’s it Drew, fuck my tight little ass, fuck me good, I want you to cum up this virgin ass, fuck me harder.
Drew was now grunting, his hands controlling my hips, before pushing me up. Take the condom off and fill is ass up, I want him to get creampied and eat it up, that’s part of the dare Jessica said. Drew lifted me up and I heard a bit of a snap as the condom popped off. Once it was off I sank down into his lap, his cock impaling me feeling his hips up against my ass before pushing me back up. He used me like a fuck doll, pumping his cock deep inside me, trying to push my ass into my body as our bodies made loud slapping noises. I just hung on for the ride my cock failing around as I look down.
Jessica came over and grabbed my cock, I want you to blow your load baby cock for me, she jerked my cock as I slide up and down on Drews meat pole. Oh gawd, oh gawd, my dick leaking precum at a steady pace now. Jessica talking dirty to me, begging me to blow my load all over her tits as she now straddled me while jerking me off, with Drews cock up my ass I couldn’t get hard, my limp cock being jerked hard. Oh my gawd I’m about to cum, I exclaimed shooting rope after rope of thick cum, more than ever all over Jessica.
Drew sank his hands deep into my hips pulling me down and picking me up, that’s it bitch drain my balls he exclaimed, I picked up speed. I felt a warm liquid shoot deep up my ass as Drew let out a loud grunt, my sweaty body collapsing on top of him. His cock continuing to pump me full of his seed, I just gyrated on top of him trying to squeeze out all his cum. From straight anal virgin to cock whore in mere minutes. Jessica instructed me to clean up my mess and clean Drews cock. I got off, as I lifted myself up I could feel his cum start to pour out of my ass, Jessica told me to push his cum out, I did, a squishy fart sound came out ass all his cum feel out onto his lap. I quickly got up and cleaned up my mess, a mix of lube, anal juice and thick white cum was pooled onto his stomach and crotch, I lapped up all the mix of juices and started to clean his glistening cock. The taste, salty and acidic, a bitter and salty taste in my mouth as I slurped up the thick mixture.
Jessica laughed from an anal virgin to a cock whore so fast Ryan suck that dick good. I took his cock in my mouth cleaning it up, I could only take about half his cock before gaging. Well, we now know that Ryan is bisexual, Drew laughed and a bottom at that. We continued the game, everyone a bit spent from that exchange the game became more tamed. After the game Ashely and Jessica kept telling me how hot that was, we ended up having a threesome, I blew the biggest load of my life in Jessica’s ass while Ashley sucked my balls, it was an amazing experience.