The Best Night I'll Ever Regret

"What I'm trying to say is," I tried starting again, at this point I'd honestly kind of even forgot what I was trying to say. My search for the words left a long pause in the air. Thankfully, again Logan filled it.

"Molly, I think I get what you're saying." Well that makes one of us at least. "We gotta stop now before we go too far."

"Yes! Thank you!" I exclaimed. Oh, thank goodness, I breathed a sigh of relief. Intellectually, I knew this was the right call, but I couldn't help feeling a pang of disappointment.

"Can I be totally honest with you..." Logan trailed off. The darkness was working against me now, I couldn't make out his expression at all.

"Yeah, of course," what was he about to say?

"To use your words, I think you're insanely hot..." my stomach did a complete back flip and the little itch between my legs? Well, it wasn't little any more.

"I've been stealing looks at you all night, I'm surprised you didn't catch me." So, he had been taking peeks! "Your ass is incredible, and it's been hanging out of your shorts this whole time..." instinctively, I reached to pull down my shorts even though it was dark.

"And then you said we were gonna sleep in the same bed...and now it's my turn to be rambling with no end in sight." We both laughed at that. "It's...I've had a fun night Molly, but...how about we just go to bed and leave it here? I think we both get it."

We both laughed again. "Yes please! We will never mention it again." I added my two cents earning a chuckle from the bed. I absolutely did not want to let it die now though. Could we go back to how he had been checking ME out all night!?

"Air cleared? We can go to bed now?" Logan asked as I started climbing into bed.

"Yes, bed time NOW." I emphasized. Internally, I was wondering how on the planet I was supposed to go to sleep though. There was an absolute forest fire going on between my legs.

Logan slid over to the wall side of the bed to make room for me. I plugged my phone into the charger and sent Dave a goodnight text. He still hadn't messaged back from earlier, definitely annoying.

Logan had made sure to turn away from me, a fact that I was simultaneously disappointed about and glad for as I joined him in my bed. I did my best to quiet my mind, trying to ignore the desperate need between my legs.

As I lay there in bed, with my sister's husband, I did the mental gymnastics required to forgive myself for ogling Logan. Dave hadn't texted me back all night? Nothing happened with Logan! I just got a few good looks, that's all. I drifted off to sleep, rationalizing with myself.

I awoke to the sound of laughter and the closing of a door. 'Haley must be home' I thought to myself. The hallway light turned on, sending slivers of light through the cracks in the door, making things just barely visible in my room.

I snuggled back into bed, ready to go to sleep. Only, I realized I wasn't snuggling back into bed. I was snuggling back into a man's body.

I put two and two together and realized Logan must have rolled over in his sleep. I'm not proud of myself for what happened next, but I was operating as a purely instinctual being. I nestled into his chest with my back and pushed my ass into his groin.

I felt it. I promise I was just going to snuggle and go back to sleep, but I could feel that damn cock up against my ass. I couldn't help it. My physical needs took over and I started grinding my ass back against it.

No thought was governing my actions. Pure sexual need drove me. I needed an orgasm. It had been building in me since the afternoon. In the moment, I didn't care what the consequences would be.

My left arm was tucked underneath me, but I was able to wrestle it up to where I could grab my breasts and nipples. My right hand plunged itself into my shorts. There, it found my pussy already soaked. I pushed myself back into that cock, grinding on it. I enjoyed feeling it grow against me.

I was getting closer to my climax when I felt Logan shift behind me. I'm sure I was the reason he woke up. Until this point, his cock had been a disembodied prop, my breath caught with the realization that I'd need to answer for what I was doing.

To my surprise though, he reached his left arm under me and replaced my hand on my breast with his. I fell into him, pushing myself back harder into his waiting body. All thought left me and I was operating purely on lustful instinct.

I melted with pleasure when his right hand travelled down my stomach into my shorts, following the same path mine had. I whimpered with need when he removed my hand from my desperate clit. I gasped with delight when he started making the same motions I had been.

Ceding control of my pleasure to Logan, I reached behind myself with my hand. I needed to touch him, to feel him as he was feeling me. My hand found its destination without me even really knowing that's what I was looking for.

I grabbed his cock through his underwear, it was so fucking big. "Fuck," we both said in unison, for different reasons. I just tried to grip his cock and hold on has he gradually increased the pace of his fingers on my clit. My orgasm was getting closer and closer to blowing over the top.

"Yes...keep doing that...it feels so good!" I implored him to continue. Wave after wave crashed through me. I felt myself clenching with anticipation of what was to be a massive climax.

"Are you sure...what if I stopped?" Logan removed his hand from my breast and the pressure of his fingers from my clit.

"Ohmygod, please don't I need to cum so bad," I begged him to continue. I squirmed in his arms, trying to get him to continue doing what he had been just moments before. I had literally never, been so on edge before. I felt like I was so close.

"What do I get out of it?" He teased into my ear. I tried to grab his hands and return them, but he resisted me. Placing them both firmly against my toned stomach.

"Anything, literally anything, just fucking make me cum!" I begged him. I meant it too. I was so on edge and in need that I didn't have any boundaries.

"I'm going to make you cum Molly. And then I'm going to fuck you, and make you cum again. But only if you ask me to." Logan whispered it all in my ear so matter of factly. It was the hottest thing I'd ever fucking heard.

"Please make me cum?" I breathed back.

"No. Ask me to do what I just told you I would." The wait was agonizing.

I'd teased myself before, and Dave had as well. I loved the buildup and then the eventual release of orgasm was incredible. This was a new high though, I'd never been on edge like this and I literally couldn't control my shaking and squirming body.

"Logan. Please fucking make me cum. I need to cum so fucking bad. Logan, I need it. I need you inside me." The stream of consciousness escaped my lips, probably a little louder than necessary, but I was more concerned about other matters at the moment.

Logan decided that was satisfactory and resumed his attention to my clit and nipple. It couldn't have been 10 seconds before I was noiselessly screaming in ecstasy. I think an actual bomb had gone off in between my legs and wave after wave of pleasure was emanating through my body.

"Fuck, fuck, fuck, fuck, fuck, fuck," was all I was capable of articulating as the longest orgasm of my life continued to rock my body.

I held onto Logan's forearm with one hand now, riding his fingers for all they were worth. I clutched his other to my breast and smashed my face into the pillow to keep from waking the entire neighborhood.

He slowed down, and my breathing slowly came back down to earth with him. When I had collected the shattered bits of my mind, I turned over to face him. I put my forehead to his and with both hands I reached down to feel his cock.

"I need this. You need this. I'm begging you to take this fucking thing and blow my mind." I implored him. I felt his breath against my face and in slow motion we started leaning into each other's lips. Just before they met, I removed one hand and put it to his lips.

"Logan, just please don't kiss me..." I whispered. I don't know why I felt like it was okay for everything else, but kissing just felt like some line we couldn't cross.

My resolve wasn't strong. If he had fought me on it, I would've caved immediately. Thankfully, he just nodded into me before he began to pull my t shirt off.

Fuck, I was so turned on. The gorgeous man in my bed, the massive cock I had my hands on, how wrong everything about this was, the genuine chemistry we always seemed to have, everything combined to make me more turned on than I'd ever been.

As soon he had my shirt off, I grabbed his face. I knew I'd just said no kissing, but I needed this boy more than I'd ever needed anything. He grabbed mine and our foreheads were touching again.

"No, please don't," he breathed at me. His vulnerability in that moment was so fucking hot, it only made me want to kiss him more.

I knew exactly what he was saying, because I was feeling the same thing. Somehow, we both knew if it just stayed sex we could survive it, but as soon as we kissed it would be more than that.

I grabbed fistfuls of his hair as if my life depended on it. My entire body was on fire, from the remnants of my orgasm and from the passion I felt in that moment. Our noses touched and for the briefest of moments I felt our lips brush together.

With a superhuman effort I didn't know I was capable of, I managed to tear myself away and plant the kiss I needed onto his chest. He had my arms in his hands, but lost his grip on them as I moved my way down the bed.

His cock was pulling me towards it as if with its own gravitational pull. I completed my journey down his musclebound chest and stomach to find my prize awaiting.

His penis was still, somehow, trapped in those boxer briefs. I couldn't totally see it in the dark, but I imagined a cartoonishly large pipe in his pants to fit what my hands felt. A large wet spot at the head betrayed that Logan needed this as badly as me.

My left hand wandered his stomach and chest, while my right hand caressed the biggest cock I had ever seen through the thin material. I desperately fixated on his member with my mouth over his underwear.

I'm not sure where I heard or found out about this, but it was my go-to move. It drove Dave absolutely wild and my other boyfriends before him the same. Logan, albeit different in more impressive ways, was no different than them here.

As I was doing this, I felt Logan's large left hand envelope mine on his chest. His fingers played with the engagement ring that adorned my finger. Mine found the wedding band that rested on his.

I don't know why we did this, but it felt like some tacit acknowledgement of the sin we were committing together. Partly, because I wasn't ready to examine the guilt of all this yet, and partly because it was a job for two hands. I took my hand away and sat back on my knees.

I gripped the waistband of Logan's last piece of clothing and pulled it down. My eyes had started to grow accustomed to the dimly light room.

Looking up at Logan, I could make out that he was biting his lip, the same visage of desperation and need painting his face that I'm sure covered mine. I pulled my gaze from him to take in his cock in all its glory.

"Fucking shit," I said aloud. Seeing Logan's massive cock standing fully erect in front of me was awfully intimidating.

I grabbed the base with my right hand. My middle finger and thumb couldn't quite touch. I placed my left hand on top of my right. My diamond sparkling faintly in the dark room. I slowly began to stroke his cock up and down with both hands. There was still room for at least one more!

A satisfied groan from Logan brought my attention away from thinking about his cock's size, to thinking about his pleasure. He had brought me to an earth-shattering orgasm, I wanted to return the favor.

I bent down until I was at eye level with his dick. 'Shit, it just keeps getting bigger!' I thought to myself. I kept my ass high up in the air, a stance I knew drove men wild. Once again, Logan was no different.

"Fuck, that's so hot seeing your ass in the air like that," I grinned to myself as I licked my way up Logan's impossibly long shaft. Giggling when I reached the top and heard him groan, "Oh shit, that feels so good."

Keeping my grip on his cock I got back up on my knees and brought my lips to his ears. "Say my name," I whispered to him.

My heart was about to burst out of my chest. I wanted to hear him use my name when telling me how good it felt. I didn't know why. I just knew I needed to hear it.

We made eye contact in the dark room, as I once again brought myself to level with his enormous penis. I took the head into my mouth and swirled my tongue around it.

I was no stranger to a blowjob. All four of the men who had received one from me gave glowing remarks. I would even brag about my skills to girlfriends when we talked about sex. I'd never tested myself on a cock this size however.

"Molly..." I heard Logan moan from above me. Hearing my name gave me a primal pride and I moaned into his cock to show my appreciation. I tried working my lips further down, but was having a difficult time getting much past the head.

I wasn't very far down when I started to gag. I pulled off Logan's cock gasping for air, spit hanging from my mouth down to his cock. A deep breath and I dove right back in. A "Fuck Molly, yes," came from above, encouraging me to keep going.

Despite my best efforts I could barely make it down to my top hand. I was no deepthroat queen. I'd never taken all of Dave's cock, but I could get way closer to the base of it than on this monster. I pulled back, gagging and spluttering again.

"I'm sorry, that's about all my mouth can take if I'm being honest," I admitted to Logan while wiping the spit from my cheeks. I wasn't lying either. My jaw was already tired from having to open that wide.

"That's okay, I've got a different idea," Logan grinned at me. "Molly," he added in a soft whisper.

Fuck, I melted after he said that. We could figure out what everything meant and what to do about it tomorrow. But tonight, I needed this man to have me in every way he could imagine.

The whole time I'd kept both hands jerking his cock. He removed my hands from him and firmly turned me until I was on my back, my head on pillows. He reached down and pulled my shorts off, finally leaving us both totally naked.

Feeling how wet my pussy still was with his hand, I watched him use some of my natural lubricant to stroke parts of his cock I'd been unable to reach.

Knowing what was coming, I took a deep breath. "Logan, seriously be gentle. Your dick is so big...I've never had anything close..." I admitted to him nervously.

He smiled down at me understandingly. "Don't worry." He sat back on his knees and I watched as he took hold of his beast and rubbed the head against my clit. Electric jolts of pleasure shot through me.

Slowly, he pressed the head of his cock to me. It felt like he was driving the breath out of me and filling the empty space with his dick.

He eased himself in, thick pleasing inch by thick pleasing inch. He leaned forward, the muscles in his chest and arms flexing appealingly as he held himself above me.

I gripped his large arms and did my best to breathe. It felt so good, but at the same time the feeling was brutally intense. I'd never felt so stretched down there and looking down, I realized I'd barely taken half of him.

"How are you doing?" Logan looked down at me with concern. I simply nodded. I wasn't sure I was capable of words. Slowly, I grew accustomed to the intensity and I was able to focus on just how good each mini thrust felt.

Logan began to pick up speed. Not pushing particularly hard or deep, but faster than the slow crawl he had been at. I pulled him into me, clawing at his back and moaning with pleasure into his ear.

"Ohmygod Logan. It feels so good! It's never felt like this before," I cooed into his ear. He continued to pick up some speed. Properly thrusting into me now. We were both grunting and moaning in conjunction with each thrust.

I felt another orgasm start to build up from the depths of my groin. Cumming multiple times was a rare occurrence for me, but this was a rare specimen of dick so why would I be surprised? Logan and I were really getting into a good rhythm now.

I met him with each thrust, grinding my clit into him and loving the feeling of being completely full. Then he would pull back and I would shudder with pleasure as his thickness slid out of my pussy.

I had no idea how long we had been fucking, we were both completely lost in the pleasure the other's body was giving us. My orgasm was no longer a light at the end of a long tunnel, now it was a train hurtling ever closer.

"Fuck Logan, I'm getting close again," I grunted into Logan's ear. His pace picked up more and he was giving me a good sound fucking. Each thrust was almost driving the wind out of me.

The feelings of ecstasy he was giving me and the spots he kept hitting were things I didn't even know were humanly possible. I felt like I'd had good sex before, but it had never been like this.

Logan buried his face into my neck and I gripped the hair on the back of his head for dear life. My other hand slid along his muscular back with each plunge of his hips. My orgasm was about to burst through and I was desperately grinding into him in hopes of meeting it even faster.

And then all of a sudden, my body exploded with pleasure. I was spasming and shaking beneath him. Wave after wave of pure electricity crashed through me. I couldn't tell how long it lasted, but it felt like it might never end.

My hips shook and bucked uncontrollably. Each new thrust would send another shockwave through my body, causing my toes to curl. I gripped into Logan, wanting nothing more than to stay in this cycle for the rest of my days.

I slowly regained a sense of the world around me. Logan had pushed himself back off me, but was still deliberately sliding in and out of my pussy. He smiled down at me as he realized I was fully aware of my surroundings again.

I blushed and covered my face, unable to contain a ridiculous smile. "You really know how to use that thing." I complimented him through my fingers.

"So, I've been told," he confidently responded, causing me to roll my eyes. I softly punched his chest playfully.

"Well, it's my turn to impress you then," I made eye contact with him as I seductively bit my lip.

"You act as if you haven't already." He winked down at me. Fuck, that was hot.

I pushed him off of me, his cock sliding out with a satisfying 'pop'. Damn, I didn't know that actually happened in real life. I suddenly felt completely empty, missing his giant puzzle piece. I rolled over so that I was on my hands and knees and presented my large ass to him.

Looking back over my shoulder, I told him, "Fuck me like this. See how long your big cock can handle my big ass." I gave him my sexiest and most suggestive stare, waiting for him re-enter me.

I felt the huge head of his cock begin to spread my tight folds again and immediately dropped my head into the pillows. I allowed him to set the pace at first, he took his time filling me back up, allowing me to readjust to his girth and length in this new position.

It didn't take me near as long to gain my bearings this time round and pretty soon I was throwing my ass back on his cock, feeling it bounce against him with an audible 'clap'.

Logan kept saying, "Fuck Molly...fuck Molly," I happily forgave his repetitive word choice because each time he said my name led to an internal roar of pride.

It wasn't much longer before I heard him say, "Molly, you're getting me close." I moaned at that, and increased my pace. My tits were wildly flopping around beneath me and I was pretty much impaling myself on Logan as fast as I could.