Locked Up Ch. 04: Party games

I shivered, torn between my love of Gwen, and my fear and discomfort. I had never done anything with a guy before and never really wanted to... but Gwen wanted me to. Finally, flushed, I nodded. Gwen giggled happily and unhooked the gag from the back of my head. I wiggled my jaw, able to close it for the first time in hours. Gwen then uncuffed my hands from the chair, but quickly cuffed them behind me again. She pushed me off the chair onto my knees, and steadied me there, kneeling behind me. All too soon, the dancers were standing before me and the ladies had me surrounded in a circle, all giggling and catcalling. I flushed red, and both guys moved closer, their thick cocks bobbing before me. I shivered, but leaned forward, taking the slightly smaller cock into my mouth. It was thick, and much hotter than a strap on had been. I could taste sweat, and their flesh, and a slick, salty tang that I realized was precum. Both guys had been fondled and played with by every lady there, and I could tell they were close. I started to suck a bit and heard the man moan. I was going to slowly try and swallow him, but Gwen grabbed the back of my head, and pushed, forcing me down the guy's shaft so far and so fast I gagged as it bounced off the back of my throat, and then forced its way down.

Gwen pushed until his cock was balls deep in my convulsing throat, and then pulled me off, and pushed me down the even thicker cock of the smaller dancer. I knew it was coming, and relaxed my throat, so he slid in a bit more easily. Gwen kept her hold on my hair, face fucking me on first one guy's cock, and then the other. Both were close, and my mouth and throat were quickly coated in thick, salty precum.

Before long, I heard the first guy cry out, and Gwen held me tight against him as his cock jerked and spasmed. I tasted a stronger salty slickness as he pumped a huge load across the back of my tongue, and down my throat. I knew how Gwen would feel if I made a mess, so I forced myself to swallow it all, my stomach clenching a bit as it sank in what I was doing, and who was watching. As soon as the first guy was done, the second took his place, fucking my face now, groaning above me. He pulled back as he came, leaving just the head of his cock between my lips, making me taste every drop as he pumped into my mouth. His orgasm seemed to go on forever, and I thought my mouth was going to overflow before he finally stopped. I forced myself to swallow once again, gulping once, twice, three times to get all the thick cream down my throat.

My job done, or so I thought, Gwen let me go, and I collapsed forward, hiding my face in the floor, my bound hands not letting me catch myself. Vaguely, I hear Maria comment on how good a cocksucker I was... but that it had clearly not been enough.

"Aww, those poor boys are still hard. They must not be finished yet. Good thing Davey has another hole huh?" My eyes went wide, and I tried to struggle up, but someone knelt beside me, rubbing my back and putting their hand on my neck.

"Just one more thing, Davey. You've never had a real cock up your boicunt before, and you won't get another chance. You'll do this for me won't you?" Gwen's sweet voice was in my ear once more, and once again, I nodded, unable to deny her anything.

With Gwen still holding me down, someone straddled my back, and spread my cheeks wide. My legs where still trapped by my pants, leaving me in a perfect face-down ass-up position, my cock and balls trapped between my legs. I felt incredibly exposed like this, all the women watching, and two thick cocks about to fuck my still technically virgin boicunt. I knew from some bathroom mirror gymnastics what my hole looked like, slightly open, Maria's training having left it permanently stretched and ready.

Someone drizzled some lube across my crack, and all too soon I felt the warm head of a real cock pressing against my hole. He shoved it home and I could not help but moan, feeling real flesh up my ass for the first time. My cock had never gone down despite the humiliating treatment, and it jerked now, my whole body responding to the anal stimulation.

"Fuck, he feels pretty loose," I heard a male voice complain, and I flushed all over again. Hearing such a well-hung guy complaining about my hole was more embarrassing then anything I could have imagined. What I heard next, however, made me shudder.

"Aww, poor guy. We don't want you to have to finish in a loose hole. I bet it will be nice and tight if you share though." I gritted my teeth, vowing to kill Maria once Gwen and I were married. There was a chorus of giggling from the ladies watching, and then I felt everyone shifting. The cock in my ass shifted down a bit, and I felt someone new straddling my ass. Another warm cockhead pressed against my hole and started to push inside. I moaned, feeling my hole stretching from a different direction. Maria had stretched me, sure, but I had never been double penetrated before, and neither of the guys was small. I whimpered as the pressure increased, and Gwen stroked my back, leaning down to whisper to me.

"You can take it baby, he's almost in. Your boicunt was made to get fucked like this, just relax, it will all be over soon."

Her words soothed me, even as the pressure grew, and I cried out as the second head popped into my hole and started to slide deeper. Neither guy was patient, and the second cock was soon balls deep in my hole as well, stretching me, the two cocks pulling away from each other, forcing me even wider. They started to fuck me, alternating their rhythm, one guy pulling out, another pushing in. Both were somehow hitting my prostate, and my cock was throbbing.

When someone reached between my legs and started to stroke me I lost it. The painful pleasure of the stretch, the humiliation of being watched, the unfamiliar sensation of not one but two warm cocks forcing their way in and out of my hole all combined, and I had the largest orgasm of my life. My balls throbbed and pulsed harder and harder, and I felt like I was going to pop. The ring did its job, and the pressure and pain mounted along with the pleasure, and the sensation just built and built, one blocked orgasm triggering another. My hole clenched around the two fat cocks forcing it open, and I cried out, writhing under them. Despite their recent orgasms, neither guy lasted more than a few moments longer, and as my own endless orgasm ravaged me, first one guy, and then the other cried out and slammed himself balls deep, both pumping their cum deep into my stuffed backdoor.

I think I passed out, or just lost track of time. The next thing I remembered was waking up with my head pillowed in Gwen's lap, feeling someone, presumably Maria, pushing a plug into my sore, freshly fucked ass. I felt the cuffs click free, and I reached between my legs, my balls feeling hot and swollen to the touch, aching fiercely, the ring still in place.

"You did really well my love," I hear Gwen whisper, stroking my hair. "All the ladies agreed you're a perfect match for me, and we shall be married this time tomorrow. As soon as you can walk, we'll head home. I think we deserve a nice long shower, and then bed, don't you?"

I nodded, and eventually was able to stand, the plug shifting in my stretched out asshole, but I left it in, figured it would keep me from leaking on the way home. I blushed imaging all the cum filling my ass, but I pulled up my pants, and waddled to the car, trying to ignore the stares I got from most of the women still in the club on the way out. For once Maria left my cock alone, and I rode home in something like shock, trying to process what all had happened. In the end it did not matter, all that mattered was tomorrow, I was going to be wed. Tomorrow night, I would be free of this ring, and finally free to cum with Gwen for the first time.