A Friendly Competition Ch. 02

L: hence the wait. who're the two guys?

R: head to this address, and you'll see.

She attached an address nearby, about half an hour from my place. The address seemed familiar, but I couldn't quite place it.

L: sweet. i'm all ready. why all the secrecy?

R: just cause. makes it more mysterious and erotic and shit.

L: leaving now. who's timing?

R: oh yeah. the guys will be videoing. i've already brief them on wha they need to do, and they did a fine job earlier.

L: speaking of. how'd stace do?

S: not great.

L: glad you could join us. good to know i've got a great chance.

I was already out of my apartment, and waiting for an Uber to get me to the location.

S: hey, well, you needed it. call it friendly gamesmanship.

L: you always were a good sport. but don't keep distracting me. i have to get my game face ready.

That consisted only of stretching my jaw preparing for a blowjob. The Uber ride there was uneventful, but I recognized the building when we pulled up. It was the same place where I had gone with Stacy and some other friends to a graduation party. That was the only time I had ever outright had sex with Stacy. But I couldn't remember who actually hosted the party. A shit ton of drugs, sex, and alcohol will do that to you.

I would find out soon enough. I located the specific apartment where I had to be. The building was in a pretty nice part of town, and I remember the apartment being really big, so whoever they were, they were clearly pretty rich. That didn't narrow it down all that much, considering who Stacy and I hung out with.

I made my way up to the apartment, which ended up being the penthouse. I rang the doorbell, and was greeted not two seconds later by a man. I couldn't help but notice I recognized him from around campus and parties, Matt or Mike maybe?

"Hey, I'm Lindsay," I awkwardly began. We both knew why I was here, but I wasn't sure how to start that conversation.

"Mitch. I've seen you a few times before I think." Mitch was shirtless and wearing only short gym shorts. I couldn't help but admire his olive skin tone and muscular physique. The man clearly had a private trainer or personal gym or something.

"Yeah, same."

Another guy popped out from behind.

"Oh my god, Jack Bridges?" I asked in surprise. I should have known it was him. I couldn't believe I hadn't remembered.

"Lindsay, hey, it's been a while! Nice to see you again."

I had hooked up with Jack a few times during freshman and sophomore year (at this point, there were more guys at school I had fucked than the alternative). He was a total prep school kid, whose dad was some venture capitalist. He was a nice, if arrogant guy.

He wasn't quite as fit as Mitch, but was an inch or two taller, and had a more handsome face. It was no surprise he was one of my earliest fucks.

"Please come on in, Lindsay," he said. "I see you've met my roommate Mitch."

Mitch closed the door behind me and moved next to Jack.

"I assume it's the same thing as with Stacy," he continued.

"Haha, yep. Rachel said she had already talked with you guys."

"She certainly did," Mitch responded. "Are you all ready?"

"Uhh, yeah," I answered, taking a deep breath. "Let's do this."

"Sweet. You look fabulous by the way Lindsay," Jack complimented. I couldn't help but blush.

The two guys moved to one of the bedrooms. It was the same one I had the threesome in at the party, and judging by the ruffled sheets and what appeared to be drops of pussy juice, Stacy had just gotten fucked here a little over an hour ago as well.

Jack moved to his ipad, set up on a nightstand. Mitch moved in back of me, and started groping my butt through my jeans.

"Ooh, handsy. I like you," I coyly remarked.

His hands moved to the front of my jeans, and undid the button and zipper. He pushed the tight pants down my thighs until they dropped to my ankles. I stepped out of them as Mitch continued gripping my ass. I felt his dick poking through his shorts against the small of my back.

Jack seemed to have everything set up and turned around to face us. Hey, let's not get started early. The timer is supposed to start when you begin touching our dicks.

I pushed away from Mitch, not wanting to prematurely start. "Wait, I really need to win this challenge. All my hands and holes are available. What gets both of you guys off best?"

"Blowjob," Jack quickly answered. I had already guessed that one.

"Ass," Mitch replied.

Mitch's answer made me hesitate for a brief moment. I didn't do anal all that much. Almost all of my fucking came in one-night stands, and most guys weren't brave enough to ask me for it when they were already getting lucky. Usually I did it with longer-term guys, but considering my insatiable sexual appetite, those were few and far between.

Still, I had said all three holes were open, and I meant it. If taking it in the ass was what I needed to do to win, so be it. It just might be a little more painful than normal due to my lack of recent stretching down there.

"You got lube?" I asked. I certainly wasn't taking it dry.

Mitch pulled his shorts down and ran out of the room without even saying a word. Jack stripped of his t-shirt and sweat pants. His cock was already semi-erect in front of me, and inflating to its six inch or so length.

Footsteps echoed through the hallway and Mitch came rushing back in, KY jelly in hand. "Let's do this," he proclaimed.

Jack and Mitch both got on the queen-sized bed, and I pulled down my panties. Mitch's eyebrows raised as he got a good look at my proudly displayed bush.

"Natural redhead," he pointed out.

"Course," I said. "That's the whole reason I keep it." I clambered in between them and got on all fours. Jack was a few inches in front of me on his knees, Mitch behind in the same position.

Jack reached over to the ipad, whose camera was pointed straight at our trio. "Tell me when."

I heard squirting behind as Mitch applied the lube to his hand. I took another deep breath.

"Go."

Immediately I reached out and grabbed Jack's dick. I felt it harden in my hands as I began to jerk the shaft. I began slower, out of habit and instinct, before remembering how much of a rush I was in. My hand began to slide back and forth much faster, lightly squeezing Jack's rod as it did so. He was fully erect in a matter of seconds.

At the same time, two of Mitch's fingers began to probe my ass. He rubbed the lube in around the edge of my hole, before pushing some inside and coating my walls. I heard him stroke more onto his cock. I was getting really wet imagining Mitch taking my ass, especially with the work his fingers were doing. God, I needed to cum so bad.

I craned my head forward, and opened my mouth. Jack shifted his hips, and the head of his cock slipped in. He rested it on the tip of my tongue for a brief second, before I closed my mouth and really went to work.

With one hand gripping the base of his shaft, I bobbed my head up and down his entire length. Compared to how much I had taken from Jerome, Jack was not a challenge, and I devoured his cock with a hunger he had probably never seen.

My tongue ran over the underside of his shaft and tickled his head whenever I moved back. My cheeks were drawn in, providing more pressure on his dick. I removed my hand from the base and shifted it to his balls, which I began to fondle.

Mitch was completely lubed up by now. He had a tight grip on one ass cheek, and was spreading it open. With his other, he rubbed his cock against my hole, rimming me and teasing me. It felt so good. But damnit, I didn't have time for that now. Sadly, the cock in my mouth prevented me from really chastising him.

To my great satisfaction, Mitch began moving his hips forward, and his cock pushed into my ass. His crown slipped in past my tight ring, and I let out a very loud moan, albeit stifled somewhat by Jack's dick.

Mitch took that as a "go" signal. He gripped my hips with both hands, and pushed forward, faster this time. I felt his cock sliding deeper and deeper up my ass, making me squeal the whole time.

My ass was quite tight from a period of disuse, but it was definitely being stretched out again. I could feel the walls of my rectum being expanded with each new inch that I took. It was painful, but I knew from experience the pleasure would come soon, and very powerfully at that.

Mitch's stomach met my round ass, and his pubic hairs tickled my hole. His whole seven inches was inside me. My ass gripped tightly around his cock, trying to adjust.

It would not be given the opportunity. Mitch withdrew his shaft about halfway before plunging it back in. My body rocked forward from the strength of his thrust, and I let out a gasp. Without pausing, he immediately repeated his action met this time by a moan of pleasure. I could feel the nerves in my anus being stimulated now. My pussy was burning.

Mitch began to plow my ass for everything he was worth. He obviously was not trying to tease or hold out as long as he could, and that was exactly what I needed right now to get off. He fucked my tight ass with a ferocity I hadn't felt in a very long time, leaving my whole body on edge, and ready to blow.

Speaking of blowing, I had become so concentrated on Mitch that I had begun to neglect my duties to Jack. Luckily, as aware of the competition as he was, he had taken the initiative.

Jack's hands held each side of my head tightly in place as he started thrusting his hips back and forth. His cock slid in and out of my mouth, hitting the back of my throat whenever he pushed in all the way. I was suppressing my need to gag as much as I could, but saliva still dripped from my now-open mouth onto the sheets below.

I was holding onto Jack's thighs for support as the two guys took complete control of my body. I was in the middle of a true spitroast, with both my mouth and ass being mercilessy fucked. Beyond repeated "glug" sounds as Jack fucked my mouth, the only other noises were my loud moans and the sound of flesh slapping together.

Despite how intense and hot it was for me, I really needed the guys to cum. I didn't know how fast Stacy had done it, so I was really operating in the dark.

My tongue extended and began to lick along Jack's shaft as it slid forward and back in my mouth. I had been blowing him before Mitch entered me, so Jack was naturally closer to his orgasm. Pre-cum was already leaking heavily from his tip, giving me just a taste of what was to cum.

Jack's cock started heavily throbbing, and I knew he was right there. Wanting to push him over the edge for good, I shifted my hands to his butt and pushed him all the way into my mouth. I took all of his cock as deep as I could, leaving my nose squished against his torso.

My tongue flicked out and licked the base of his shaft and his balls while my throat reverberated against the tip of his cock. Jack's cock pulsed and he cried out.

I was preparing to take his load down my throat, but at the last possible second, Jack

pushed me away. I took a deep inhale as his cock finally left my mouth, and looked up to see Jack's cock a few inches in front of my face.

Two quick strokes of his hand later, and he erupted. A thick rope of cum flew right out and hit me square on, dangling from above my right eyebrow across my nose to my left cheek. Another spurt rocketed out and sealed my left eye shut as it trailed from my forehead down to my jawline on the left side of my face. A third big strand landed on my right cheek and ended at my chin.

Jack moved his cock up a little, and deposited the remaining smaller spurts of cum onto my forehead, before dribbling off another drop or two onto the bridge of my nose. Much of my face was now covered in thick pearly ropes of his warm cum, and I was left feeling so much wetter than before.

Jack flopped down on the bed, and grabbed his ipad to get a better camera angle. I just had Mitch left, and it didn't seem like he would be much longer. For that matter, nor would I.

He was really fucking me with everything he had, rocking my whole body back and forth. His balls slapped against my swollen pussy lips. I thrust my hips back against him with each stroke, letting him bury his cock even deeper in my tight ass. My whole pussy felt alive as the ridges of his cock stimulated every inch of my ass.

I reached one hand back between my legs and found my labia. I was quite literally dripping wet, and my fingers were now sticky. I trailed them back up to my clit, partially matting my red bush in the process. My nub was engorged and hard as a rock. I pressed down hard against it and started circling it, trying to maintain the same pace as Mitch's frenetic thrusting.

My loud moans finally reached their crescendo. My pussy pulsed, and my ass clenched around Mitch's cock. I felt waves of pleasure radiating from my cunt right down to my very core, making every hair on my body stand on end, and I exploded in an intense orgasm. It was one of the best I could remember in a long time. I collapsed my upper body down onto the sheets as my heart rate slowly returned back to normal.

More juices trickled out of my pussy onto my hand, and my ass gripped onto the shaft inside tighter. Mitch pumped in and out a few more times, before letting out a loud grunt.

He gave one last thrust, burying his cock as deep inside of me as he could. His dick throbbed, and then I felt his load spewing out, coating my rectum in thick, warm, jizz. I l gave a contented sigh, and Mitch's cock began to deflate.

He pulled out of me, and I felt some of the cum trickling out as well. It dripped down to my pussy and mingled with my own juices. Quite a lot of Mitch's load remained inside me though. That would take a while to fully get out.

Jack broke the silence. "Well, that was great. I'm pretty sure you were faster than Stacy too."

My head perked up. "Really?"

"I don't know exactly. I'm sending your video over to Rachel. I guess you'll have to wait and see."

I clambered off the bed, and stood up. A mixture of cum and pussy juice began to slowly trickle down my inner thighs as I did so, giving me goosebumps. I was going to go to the bathroom to clean up, remembering that my face was wearing a sticky load as well.

But an idea popped into my head, and I turned to face Mitch and Jack, both still lying down on the bed.

"You know..." I began. "You boys were so good to me, and I gave you a great treat too. I think we can mutually work together a little more before the night is over."

Mitch's eyebrows raised. They both knew what I was talking about.

"What exactly do you have in mind?"

I got back on the queen bed and began to crawl towards them on my hands and knees. I could see both of them getting hard again at the sight of my pretty face covered in a layer of jizz.

When I got in between them, I dropped down to my stomach and reached a hand out to both dicks. I started stroking, and Mitch and Jack came to life in my hands.

"Well, I've never actually taken a dick in both of my holes at once. Now seems like the perfect opportunity for my first dp." It was actually a little surprising considering how many guys I had fucked, but I was more of a one-night-stand kind of girl in my sluttiness than Stacy's balls-to-the-wall fuckfest/gangbang approach.

Without saying anything else, I turned towards Jack and wrapped my plump red lips around his cock. He was half-hard, but when my tongue flicked over his tip and my lips ran back and forth over his shaft, he immediately grew again to his entire length.

When I was content that Jack was fully erect, I removed my mouth with a slight pop, and returned to stroking him. I turned my attention towards Mitch, who was mostly hard himself. My lips sealed around his slightly thicker dick, and my tongue coaxed him to fully mast. I could taste remnants of jizz and my own ass on his cock, and that just made me wetter.

With both men primed and ready, I got back up on my knees. Jack had set his ipad back on the nightstand, presumably filming me once again.

"Since Mitch has already stretched out my tight butt, he gets my pretty little cunt first," I said, knowing exactly how to turn the men on. "Sorry Jack. You'll have to settle for sloppy seconds."

"Lindsay, I don't think any man fucking you in the ass would complain about anything."

I giggled and gave him a wink. Mitch stayed where he was, lying on the bed, as Jack got up and moved to get the lube. Given the slight break, I realized for the first time that I had never actually taken off my top. I unzipped my sweater and unbuttoned my blouse, fully baring my big round tits to Mitch.

"Shit, those are beautiful. You're really a naturally gifted woman."

I faked slight bashfulness. "Oh thank you."

Jack was back, and I scooted forward so I was straddling Mitch's torso. His cock was right below my aching pussy. One orgasm wouldn't be enough for me tonight.

I heard Jack lubing up his shaft. With my anus thoroughly expanded and slick with sperm, he wouldn't need it, but I didn't stop him.

I reached between my legs and found Mitch's cock. I gave it a few quick strokes, looking down into his eyes as I did so. I loved seeing the pleasure on a man's face from what I was doing to him. I bit my lower lip, and pushed my hips down.

The pink helmet of Mitch's rod split my pussy lips and slipped into my wet opening. A moan immediately emanated from me, and I tilted my head slightly back. My hand moved away from Mitch's shaft, but he took the initiative. With his hands on my thighs, he pulled me down further onto his cock.

Most of it was already inside my delectable pussy, and Mitch thrust his hips up into me. I gave a squeal when his whole length became buried inside me, and Mitch took that as his cue to totally fuck me.

He began pistoning his cock into me, wasting no time at all. Three quarters of his shaft was sliding in and out of my slick channel with each new thrust, making a squishing noise and expanding my pussy, which had previously been untouched that day. My clit was being forcefully rubbed against his torso on each downstroke, and my tits jiggled in front of Mitch's face. I bent down further so they were directly in front of him, which also meant my clit was grinding more directly on Mitch. It took no prompting for his mouth to latch onto one of my small nipples and begin sucking away. I was moaning heavily, with just the stimulation in my pussy bringing me close to a climax.

Jack had been on his knees just behind me, watching the action unfold.

"Come on, big boy. Don't just watch. I've got another hole just for you."

I shook my big butt back towards Jack, once again thanking God or Jesus or whoever for gifting me with such a voluptuous figure. Mitch slowed down his drilling to a more conservative effort, taking the time to slowly push inside me. It was almost as good, feeling each ridge and bump in his cock against the walls of my pussy, slowly rubbing against my g-spot.

It also steadied my body down, giving Jack the opportunity he needed. Prying my ass cheeks apart with one hand, he positioned his cock against my ass and pushed in. His head slipped past the tight ring of my sphincter, and I was now being officially double-penetrated.

I was brought right to the edge of an orgasm right there. I had a cock buried in my cunt, and another one inching its way in my ass. My nipples were hard as a rock in Mitch's mouth, and my clit and twat were aching like nothing I had ever felt before.

It only took one full thrust for me to actually climax. Jack pumped his cock all the way into my ass, and both of my holes were completely filled. My head was tilted back, my eyes were closed, and I screamed out a string of expletives as my whole body shook and spasmed.