Trying New Things

I cried out around Leo's cock as I felt Jason's cock press against my ass and slowly work its way in. I never was much for anal sex unless my pussy was being stimulated too, so it was plenty uncomfortable to feel Jason push into my shitter while my vagina remained vacant, but I'd never actually told him my feelings about straight anal at that time, and I knew he was just trying to prepare me for the fun that was coming up next. Leo obviously didn't know better either, because he encouraged Jason to penetrate my ass while he continued to fuck my face. Once Jason's balls were on my taint, Leo pulled out, allowing me to gasp and catch my breath.

At that moment, I didn't want to discourage the boys or hurry them to fill up my pussy too, so I not only endured the discomfort, which was fading the longer Jason was in there anyway, but actually tricked them to believe I liked it. "Fuck that ass! I know what you want," I said to Jason as I still tried to catch my breath. Jason proceeded to do just as I urged him, sliding his cock back and forth in my ass slowly at first, which, thankfully, helped me adjust to the anal intrusion. I desperately wanted Jason to lie down and pull me on top of him so Leo could pleasure my pussy at the same time, but, instead, Leo put his cock right back in my mouth and ordered me to suck it. As badly as I wanted that prick somewhere else, I was happy to grant him his wish.

Jason pounded my ass for a few minutes, helping Leo double-team me at both ends again. Jason and I were both panting in no time, and I felt beads of sweat form on my forehead. Leo just had to stand there while Jason slid me up and down his cock, returning Leo's favor from earlier. Honestly, though, the longer Jason railed my ass, the more I liked it. I was almost considering encouraging him to cum in there until Leo snapped me back to my senses.

"Let's DP her," he said.

"Mmm, a delicious Jessie sandwich," Jason mumbled, a phrase he almost always uses when preparing to double-penetrate me. He and my other friend pulled out of me, and I couldn't help but gasp and cry out as I was suddenly empty. Not for long, however.

I kind of forgot I was still in high heels, so when I stood up, I almost toppled right over. I grinned nervously as I caught my balance. Jason took me by the hand and led me to the couch, where Leo had hurried over to and was already sitting on as a bunch of different thoughts swirled through my brain. Some of those thoughts were things like whether or not I would enjoy double penetration as much as I did the first two times or what if my family or coworkers ever found out that I was having a threesome with two men?

Jason turned me around when we reached the couch, obviously offering Leo my ass for this round. I knew just how much Jason liked being on top in this position, so it came as no surprise. I also knew how he preferred my pussy, while Leo was always trying to get in my ass, so it was a pretty ideal setup. I, well, I just wanted to get those dicks in me and feel the hot passion of being sandwiched between two warm, sexy male bodies.

Leo and Jason worked together to lower me down onto Leo. After all those awkward years, I loved how they were now getting along! Next, I pushed my feet down to the floor, the heels of my shoes digging into the carpet as Jason let go of me and Leo began to penetrate my asshole with his prick. My heart began to pound hard, and the boys could hear my heavy breathing. My butt had already been broken in, so it wasn't nerves this time that had my emotions in overdrive. It was pure excitement as I anticipated the double penetration, easily the hottest sexual act imaginable, in my opinion.

I held onto each of Leo's legs while Leo's dick was now firmly wedged deep in my ass. Once we were comfortable, Jason lifted up my left leg, stepped over the right one which was still planted on the floor and leaned toward me, his manhood in hand. My left ankle rested on Jason's right shoulder, while my man neared me until his cock poked my vagina, just above my stuffed butthole. I groaned and giggled a little as Jason pushed into my womanhood inch by inch, my eyes magnetized to those two cocks, which had both of my holes completely stuffed a minute later.

My moans were uncontrollable now that I was at last the meat in this main course, so loud that I could barely hear the panting of the men who surrounded me or the creaking of the couch beneath us. My right leg was pinned helplessly between Leo's and Jason's legs while my other leg was stretched out over Jason as he ground up against me, adjusting with Leo as both boys prepared to make love to my body simultaneously. Both of them holding tightly to me as they remained balls-deep inside me, Jason finally got the threesome going in earnest by pulling back in my pussy and sliding back in.

I'm not sure why, but I laughed once the boys got going. The feeling of two cocks' beginning to go in and out of you to commence double penetration is really indescribable and just something every woman should experience at least once. So amused was I to be the center of this group endeavor that I couldn't help but express that amusement. I continued to laugh so much that it became embarrassing, all the while clutching Jason's waist and forcing him as deep into my pussy as possible while Leo was now matching Jason's thrusts and plundering my ass.

Soon, the laughing turned to moaning as I writhed between the two men. Jason was now lying on top of me, my boobs smashed against his chest as I was firmly backed into Leo beneath me. I threw one arm around Jason, sinking my nails into his shoulder blade, and wrapped the fingers on my other hand around Leo's wrist while he held onto my waist. The poor guy beneath me seemed to have some initial trouble getting going with all that weight on top of him, but it wasn't long at all before he was beginning to ever so slightly push back into the couch cushion, drawing precious inches of his cock out of my shitter, and then sliding back inside me, officially joining Jason in poking my holes.

With each passing moment, Leo caught up closer with Jason's pace until they were both fucking me in unison, in effect taking turns planting deep inside me. I closed my eyes and opened my mouth, lips curled up in a smile as the three of us were pressed as closely together as possible, a boy's head on each of my shoulders as they worshipped their goddess. From that point on, I was lost in the bliss of the double penetration, those two cocks sawing in and out of me, filling my holes while they were just barely separated. Throughout this sexy treatment I alternated between laughs of glee and moans of pleasure. My hands held firmly to both guys as my legs kicked out as far as they could within the confines of those two human bodies.

Being just the third time we did double penetration, it was by far the longest the boys had lasted. The delay allowed me to have at least two orgasms as the boys ripped back and forth in my holes, confidently and determinedly. Each orgasm caused me to first hold my breath and then cry out in bliss. My body would tense and then spasm between the two boys, who didn't slow down as they firmly fucked my love holes. I was starting to think they would never stop making love to me that afternoon!

The next thing shocked me and pulled me back to reality: as the boys relentlessly plowed my holes, Jason unexpectedly shot his load inside my pussy! I sensed how, at first, he tried to hold it off, since I had never let him cum inside me before, but once he had lost that battle, I felt how he relaxed, lying on top of me and just enjoying the fact that he was filling his friend with his baby batter. My reaction was to wrap my arm around his head and press my cheek against his as he emptied out a huge cumshot into my vagina until the cum began to leak out, undoubtedly dripping down to Leo's balls. None of it was part of the plan, but once I got past the initial shock, it made me cum for the third time. Also, I knew what I wanted next.

Practically out of breath, I ordered Leo to cum in my ass while Jason and I were still climaxing together. Leo dutifully fucked my butt even faster, now that he wasn't battling with Jason's thrusts, since Jason had ceased from thrusting into me and simply lay on top of me as he finished inside me. It wasn't long before Leo moaned and came in my ass. Not only was it the first time two men had ejaculated in both of my holes in one session, but it was also the first time anyone came in my ass. It was a unique feeling, and I knew I wanted it to happen again.

I don't quite remember doing this, but the boys said I laughed "demonically" and went limp between them as the final loads of semen escaped Leo's cock. I was so entranced by the experience that I guess perhaps I had been possessed by some sort of sex demon! Seriously, though, the next thing I do remember is shuddering from the thrill of what had just happened and then feeling a chill as our three sweaty bodies heaved in such close proximity to each other, the boys going soft inside me as we just recovered from our hottest session yet.

Our weekend didn't end there, but the story does for now. Please share your comments!