Worth the Wait

No amount of mental preparation could ever make me ready for anal intrusion regardless of the limited number of times I had done it, and I couldn't help but cry out a little and tense up as Jason wedged just enough of his tip inside my butt. My heels sank deeper into the mattress on either side of Jason's knees, and my hands gripped the comforter above both of his shoulders while Jason sank my body lower onto his cock.

Despite my cries of initial discomfort, I loved the feeling of Jason in my ass. Shifting myself a bit, I got that prick wedged nice and deep inside me until I was all the way down on it and sitting on my friend's balls. Both of us were breathing hard as we slightly realigned our bodies to prepare for an evening of wild sex. Jason put his hands on my hips while I continued to plant my hands and feet on the mattress. Then I took the lead, needing only a little support from Jason as I lifted my body and began to screw my best friend with my ass.

As a low, uncontrollable moan escaped from my mouth, Jason cursed beneath me while I forced myself up and began to slide up and down his cock, taking it deep up my behind. It was Jason's first time giving me anal without Leo in my pussy at the same time, so I hoped I could make it special for him as I slowly ground on the entirety of his shaft. As I rode his cock with my ass, I couldn't help but sink back farther, my hair swinging down into Jason's face while my dear friend supported me from underneath, his hands on my sides, as I shifted up and down him.

As Jason held onto me and I grew more comfortable taking him in my shitter, I was able to bounce on him a little faster, eliciting louder and more pleasured moans from him. My cries were already morphing from adjusting discomfort to delighted enthusiasm, and I began to shift and rotate my hips more adeptly the longer I fucked his cock with my ass. For a while there I all but forgot that Leo was even in the room as he just watched me take another man's dick up my ass.

Jason helped me by lifting me up and down, but we were a team, neither one of us outworking the other as Jason's cock slid in and out against my raw anal walls, a feeling that didn't ever thrill me at first but got hotter as the activity progressed. Jason stirred a little beneath me, but for the most part we just let my body slide up and down his fuck stick while the bed creaked beneath us. Each time my body came down, Jason's balls touched my taint, but only for a second before I went back up, over and over again.

Leo watched on for about five minutes before snapping me out of his trance by joining us in bed. He stood up between my and Jason's legs as we all awaited the real fun. I couldn't help but grin like a moron again and giggle a bit as we all prepared for the main event.

"Do you want to make a Jessie sandwich?" I said sweetly to Leo as he began to kneel down. I lifted both of my legs straight into the air and spread them wide for Leo while Jason held me still and helped balance my ass on his prick. "I make the best sandwiches," I said, far more confident than I had been when I tried the sexy talk earlier. "They're hot and wet and delicious."

My heart was pounding as Leo knelt in front of Jason and me, holding himself up by one arm and guiding his cock into my remaining vacant hole while my ass was stuffed full of Jason. Our first threesome had been so unreal and so long ago that I couldn't believe we were actually doing it again. Beneath me, I swear I could feel Jason get even harder inside me. Clearly I wasn't the only one who was excited beyond belief right now.

The intensity, pressure and pleasure I felt as Leo leaned forward and sank his cock into the opening of my vagina was unreal. I couldn't help but moan loudly while Leo pushed forward, entering into me inch by inch. To feel a cock penetrate me while one was already in the adjacent hole is an incredible feeling, one that every girl should experience at least once. My toes curled in my high heels as I felt as full as I had felt only once before in my life, and I had all the assurance and every reason to go through with such a depraved and decadent act.

Leo pushed forward gently, his cock separated from Jason's by a mere membrane, my tight holes filled to capacity. We were all quietly groaning as each of us was affected by the pressure of my having two cocks inside me. It took a minute, but Leo finally shoved his whole length into my pussy so that both boys were balls deep in my tight, slender body.

All three of us cursed, my cry being the loudest once Leo finally bottomed out in me. I felt Jason's nails sink into my hips as he remained still in my ass for just a moment longer. With Jason beneath me, I looked up into Leo's eyes, both of us beaming as I was double-stuffed. My outstretched legs lay on either of Leo's shoulders, the heels on my shoes pointing toward the ceiling. As my two best friends sandwiched me in that cheap motel on this freezing winter night, I knew what a lucky girl I was. Just like that, my best friends who almost never seemed comfortable around each other were more than happy to make a little incidental male-on-male contact in order to give me all the love they could.

Once we were all settled, I left one arm planted nearby Jason's head but reached up with my right hand to clutch Leo's back, still adjusting to being sandwiched for the first time in more than a year. Leo lay on top of me, leaning over my right shoulder, while Jason positioned his head under my left shoulder. In a strange way, I felt secure being pressed between the boys I trusted the most. Like the first time, the passion and intensity of being double-penetrated and this close to these men simultaneously had my sensations in a tizzy. I kept my legs kicking straight out of this mass of flesh as the pleasure from both cocks inside me ran through me entire body. For the first moment, we all kind of just gyrated on the bed as we adjusted to the intensity of the two men being joined to my body at once. Finally, Jason really got things started when he thrust up into my ass.

I groaned as Jason's cock stretched out my tight asshole, which allowed even less give now that the adjacent hole was stuffed as well. My back was pressed close against Jason's chest and stomach as his hands slid up my sides until his thumb and index finger squeezed the outer sides of my boobs while he slowly pumped in and out of me. Meanwhile, Leo began to move as well, pulling back and then slowly sinking his cock back into my pussy. With both boys now moving in and out of me, I was in my glory.

Being only the second run at double penetration for all three of us, I'd be lying if I said it didn't take a minute for us to remember what exactly we were doing. However, it wasn't very long at all before the boys had a steady rhythm going like the first time when they teamed up on me. Before long, I could feel Leo's cock sink into my pussy right on cue whenever Jason pulled back in my ass and vice versa. With more range of motion, Leo was able to simply push back and forth into me, while Jason, with the weight of two bodies on top of him, had to hold firmly to my sides and breasts as he pushed his whole body up and down in an effort to fuck my ass most effectively. Ever the problem-solver, Jason was expertly sticking my rear end with no issues.

After a couple minutes, we had it together. Sandwiched between the two men, my head close between theirs, legs spread and outstretched, I closed my eyes and cried out with joy as my two boyfriends started to fuck me harder and faster. Jason and Leo paced themselves perfectly, their cocks moving like pistons in and out of my body as I panted and moaned. Sweat leaked out all over my flesh as the boys grunted with me. Time seemed to slow down as my two lovers joined their bodies with mine in the most intimate sex sandwich I could have ever imagined.

"Fuck, Jessie!" Leo practically shouted as he pleasured my pussy with his rigid manhood. "You're so damn hot!" I opened my mouth and laughed, unable to respond any other way as I was captivated in this glorious moment. I could feel beads of sweat rolling down all over my body, and I realized I wasn't sure if the perspiration was mine or one of the boy's. It didn't matter. I felt warm and safe - and aroused as hell. My pleasure sensors were going out of control.

"Oh yeah, Jessie," Jason panted. "Oh, Jessie, oh fuck yeah, Jessie." I loved hearing them say my name. It sounded like a mixture of praise and love, and it made me feel even hotter. "You're so fucking hot, Jessie," he continued.

I wanted to call out their names as well, but all I could do was close my eyes, open my mouth and either moan with pleasure or laugh with joy. My two best friends double-fucked me hard and fast, sliding in and out of my ass and pussy steadily and firmly for several minutes. I felt sharp and alive as I let the realization sink in that, after more than a year of frustration, my friends were simultaneously sawing in and out of me again. I wished dearly that we had been doing this dirty act of love and lust all along but was glad that at least we were finally doing it now. It was certainly worth the wait.

My legs and feet bounced in the air as our collective mass of flesh bounced on the mattress in this motel room, which was filled with the sounds our heavy breathing. Eventually, I realized the audio was more than just the breathing and that we were actually getting pretty loud. I was the main culprit, moaning and shouting, using my fair share of profanity but making out few other intelligible words as I was delirious with excitement while these two sexy men sawed in and out of me. Even the fan that Leo had turned on couldn't have been enough to cover up everything. There was a good chance someone could hear us, but in that moment I didn't give a care, and I doubt the boys did either. We just carried out our passionate, hot, dirty group sex shamelessly in that motel no matter who could hear our moaning and yelling emanating from the room or that ungodly squeaky mattress.

My knuckles on the hand that gripped the comforter were ghost white beside Jason's head while my other hand was fixed firmly into Leo's back. Eventually, I could hear even the squelching of of my ass and pussy along as they pummeled them expertly. For how awkward these guys usually were around each other, they sure made a good team when it came to fucking a girl together! Adding to the sounds were the rattling of my jewelry and, of course, the smacking of the boys' damp, sweaty flesh on my own.

After several more minutes of blissful group sex, Leo slowed to a quick stop and pulled out. My legs collapsed as Leo withdrew, at which point Jason ceased from banging my ass after four more hard pumps into it. Then Leo got off the bed and directed me to turn over. I was pretty wrecked in the best possible way at this point, gasping for air and drenched with sweat, but I was still up for more fun and had no problem with doing what I was told. All I needed was a couple seconds to catch my breath a bit!

I dropped to my hands and knees and straddled Jason, my hair falling wildly and messily into my face as I looked down, my flesh gleaming from sweat that dripped from it. Jason put one hand on my back and the other on his cock, setting it up directly underneath my pussy.

"Are you excited to fuck my pussy, Jason?" I whispered sweetly to him. All he managed in response was a smile and a nod. I smiled back and sank down on top of him, taking his whole shaft into my pussy. Then Jason briefly squeezed my boobs once he was fully inside me before putting his hands on my hips and beginning to lift me up and down his sexy cock.

Leo asked Jason to fuck my ass, but I couldn't help but look over my shoulder at Leo and say, "I want you in my ass!" For now, Leo stayed back as I rode up and down Jason's cock, faster and faster. My hair and boobs jiggled as I took him inside my incredibly wet and tight cunt over and over again. We moaned in unison as we fucked for a few minutes. As hot and absolutely wicked it was to be sandwiched by these two men, it was a very overwhelming experience to, at long last, have sex with Jason one-on-one for the first time after so many years of faithful friendship.

I don't think Jason ever broke eye contact with me the whole time I rode his stiff prick. My body bounced up and down him, over and over, causing the mattress to creak loudly beneath us again. We didn't share any words but just grinned. I giggled a few times amid moans as that thick, hard cock drove deep inside me again and again, getting me lost in the emotions of fucking my best friend.

"Are you ready for that cock in your ass?" Leo said just as my sex with Jason got really intense. His words snapped me back to the reality of our situation, and, as much as I enjoyed intimately fucking Jason, I got hot with the idea of another round of double penetration. I was sure Jason wouldn't mind; after all, sandwiching me had been his idea in the first place.

Leo hopped back into the bed, and Jason's hands slid up to my shoulders. Leo put both hands on my hips and sank right into my ass, somewhat abruptly. I cried out in a mix of pain and pleasure from the sudden pressure in my ass as I felt that cock sliding beside Jason's in my pussy. The sensations seemed to cause Jason to thrust up into me just a little more so that his balls were touching my taint again. Meanwhile, Leo, staying vertical, kneeling behind us, fully sheathed in my ass so that I was stuffed in both my holes again.

The boys got right to it, fucking my holes in unison almost immediately. I propped myself up between the two of them, moaning as I took the double penetration. The air was so hot now that we were all panting and sweating in that tiny little motel. Leo and Jason slid in and out of my ass and pussy relentlessly, establishing the same rhythm as before.

Overwhelmed, I collapsed on top of Jason and slid my hands onto his shoulders, sinking my nails in while I got pounded hard at my back end. My yelling and moaning got out of control at this point. If anyone was nearby, there was no way they didn't hear us. My damp boobs and stomach were pressed against Jason's body, my sweat-soaked hair matted against my neck and pressed against the side of my face. Most of the time I kept my eyes closed as the feelings were that intense, but each time I opened them I would see Jason staring at me with a look of delirious pleasure and satisfaction on his face. I would flash him a smile that was half endearing, half wicked and then close my eyes again and cry out some more.

Those cocks plunged in and out of my holes for quite some time, and I never grew tired of it. I didn't know when the next time would be that we could do this debauchery, so I savored it as it lasted. I loved the way Jason's hands felt on my shoulders and boobs as he pumped in and out of my twat, and Leo's strong grip on my body as he pounded my sorry ass. It was all just too real that at last I treated the boys to my screaming orgasm, the likes of which I had not had since our first threesome and never before that time. Unaffected by my climax, the boys just continued to hammer me straight through my cumming until Jason announced he was about to join me in orgasm bliss. Pinned between the two men still and trapping Jason beneath me, Leo and I had to act fast in order to let Jason do what we all knew he was going to do.

Leo quickly pulled out of my ass, and I hopped off Jason, sad that I didn't have any cocks in me anymore but satisfied nonetheless following my toe-curling climax. As Jason jumped off the bed and stroked his cock, I knelt down in front of him, desperately pushing my messy hair out of my face and closing my eyes and mouth just in time for Jason to finish our threesome exactly how he wanted. I couldn't help but let a grin creep across my face, not knowing exactly when I would be treated to Jason's cumshot.

"Oh Jessie!" he moaned as he worked himself up to the edge. "I'm gonna cum all over that beautiful face!" Then he moaned even louder, and I flinched as jets of semen finally sprayed my cheeks, chin, nose and forehead. By the time he was done, cum was streaming down all over my face and down to my neck. He had certainly saved up quite a load for me! I hoped Leo had too.

Following his orgasm, Jason sat down in a chair across the room and watched shamelessly as Leo put me on my back on the bed, spread my legs and stood over me as he fucked my pussy. I'd never had sex while someone just watched before and certainly never with a face-full of cum. It made my heart feel a funny excited feeling, and I think I grinned like an idiot the whole time. As my one best friend fucked me in front of my other best friend, I clutched my boobs, kicked my high-heel-clad legs straight up into the air and let Leo hold onto my waist and give full vent to his lust. It was even hotter that I had Jason's cum was on my face: one friend railed me while another friend's cum dried on me - what a lucky girl I was! At last, Leo pulled out and came all over my stomach and tits, unleashing a load not quite as impressive as Jason's but still really sexy as I tilted my head up and watch our threesome come to end.

Leo collapsed next to me on the bed, and, for the next several minutes, we all caught our breath and cooled down. Then we took our time cleaning up. The boys got dressed while I took a shower in the motel. I couldn't put that coat back on until I had sufficiently cleansed my face and body from all that sweat and semen!

Once I got dressed, wearing the clothes I'd had on before because they were all I brought, I really started to wonder if anyone had heard us, but the boys couldn't have cared less. What really mattered was that we had finally pulled off a second incredibly hot experience that none of us would ever forget. We agreed that, going forward, we would do whatever we could to make these threesomes occur as often as possible, at least as long as our lives allowed it. I couldn't help but think of how much fun the three of us could have had if only Jason had told me of his fantasy back in college! Even so, as I realized that blissful night in the cheap motel, the wait made it all the more enjoyable.