Crossing a Line

Jason checks in but I don't think I've ever been so sure in a sexual scenario before. "Definitely." I assure him with a bite of my lip and with hands on the inside of my thighs he begins to prise them apart. The back of the couch makes it difficult to spread my legs fully, but he does his best to try, and the cool air from the room hitting my glistening center feels truly glorious.

He brings two fingers to my slit and runs them down it a few times making me hiss, playing with the lips but not adding any sort of pressure so he slips inside. "Look at your perfect little pussy. It hasn't been fucked enough." He continues to smear my juices around my sensitive area until he's unearthing my well-kept secret that is barely hiding under its hood, especially because of how horny I am. "Fuck your clit is massive."

"It's my dick."

"In which case..." With a thumb and index finger on either side of my clit he begins to rub as if it is a tiny dick. It's amazing how sweet he's managing to be yet so dirty simultaneously. I'm quickly becoming addicted which should probably panic me, but I'm too lost in the pleasure of him massaging my dick that it is impossible to get stressed. My teeth are pressed firmly into my bottom lip to conceal my moans, but he is quick to be critical about this. "I want to hear you." This isn't a request, it is a demand, and I happily oblige.

Moan after moan tumbles out of my mouth as he plays with my big clit. He skilfully manages to manoeuvrers himself to settle between my legs on his front, without halting his movements, and then his mouth is latching around my tiny dick to give me the best blow job it is possible to give me.

It is not something anyone has attempted with me before and it is almost overwhelming to get accustomed to the new sensations. The noises I'm making are more whines than moans, high-pitched and feeble, but I don't care that they're heard. His mouth... his lips... his tongue... are all making me ascend to heaven -- and that's before he adds his fingers to the mix.

He brings two of his already moist fingers back to my slit and gathers more of my juices with ease. "So wet for me." He grumbles into my pussy, the added vibrations making my toes flex before he pushes the two fingers inside me. They slip in effortlessly thanks to my dripping arousal.

Jason only pumps his digits into me a couple of times before he's curling them to stimulate my G-spot and I continue to moan but now in time with his perfect thrusts. "Fuck... that feels amazing." I somehow get these words out with my mind swimming with all the happy chemicals freed during sexual encounters.

I feel my stomach tense and my pussy pulse around his fingers as I near my release, and I'm grabbing at nothing with my noises getting louder as well as the sound of wetness squelching between my legs. My head gets foggy, and I know I'm about to come crashing down... but then something changes, something on the verge of being painful. I gasp at the addition of the third finger and briefly, it puts my pending orgasm out of reach. "I need to prepare you."

"Are you big?"

"Yes."

"Oh." It comes out as a moan.

"I don't want to tear you apart." He says. "Not tonight, anyway."

My eyes are screwed shut as I get used to the fingers fucking my pussy as his mouth returns to my dick which he continues to suck and lick. It doesn't take long for me to get taken back to the edge, this time with a larger load between my legs. "Shit, Sir, I think I'm going to cum..." Jason doesn't verbally reply to this, but he speeds up the movement of his fingers and tightens his lips over my clit, sending me over the edge with a screaming moan.

My entire body thrashes on the couch as more and more of my juices squirt from my center. I don't think anyone has made me cum so hard before and the convulsions show no sign of stopping, helped along by his continued movements. "Another one." He instructs, not relinquishing his ministrations and I'm about to express that this isn't impossible when my first orgasm rolls right into my second, this one much more sensitive than the first. The noises I'm making... well, I can't believe that it is my mouth that they're coming out of. I'm definitely going to have a sore throat tomorrow, as well as being sore in other places.

Jason gets the hint that I've become overstimulated when I start to scramble away from him, at least I try. He holds me in place with a naughty glint in his eyes, but he has at least removed his mouth and fingers from my throbbing pussy. "Good boy." He praises and presses a sweet kiss to the corner of my mouth. It's oddly nice. "Now it's my turn." But he quickly changes back into the dominating man he has already shown he can be. "Just need to grab a rubber."

He really isn't like this in the workplace. He is very professional and is appropriately nice so colleagues ask for his help, and so he can get what he wants when he needs it. I never could have guessed that behind the smart shirts and the striped ties he is like this. I am hoping that tonight isn't all that can happen because I already long for more, but seeing him remove the rest of his clothes and find a condom from his wallet I know I am going to get so much more.

I didn't see him soft but hard he must be eight inches in length with a delicious girth of around six. I certainly haven't had a dick so big split me open before and this thought has even more of my slick spurting from me in anticipation. He catches me looking and smirks as he tears open the condom's foil packet. He doesn't really need to, but he gives himself a few pumps to get fully hard before he rolls it on having clearly had a lot of practice. In the past, this may have been concerning to me but the events of tonight have already shown me the pros of being with an experienced man. "You're too quiet." He comments, his Midwest accent stronger the more aroused he becomes.

"Just getting my breath back." I reply with probably quite a dazed smile as my chest heaves. "This is- ow!" I yelp because he has just slapped my already red pussy. It is a good pain though. It starts off a sting but a ripple of pleasure travels through my body.

Jason chuckles as he climbs back between my legs. He rubs the tip of his large, hot, and hard dick over my slit between my puffy lips to gather some of the slick, and then his gaze fixes on mine. "You ready sweetheart?" He checks with a pet name that makes me warm inside for a different reason than before.

"Definitely." I echo my earlier consent and it is all he needs to breach my hole with his rock-hard member.

The stretch of him pushing inside makes my eyes bulge out of my head. Even with all that preparation and two orgasms, it is like he's ripping me apart. "You're so tight." He groans as another two inches slip inside. "With how you're squeezing me... shit... I ain't gonna last long baby."

I can feel so much, and it is difficult to know what to focus on. The burn, the heat, the wetness, it is close to being overwhelming, but in a good way. "Keep going." I plead, already feeling like the head of his cock could burst through my stomach but still he is shifting his way forward with two strong hands keeping my thighs firmly apart. "Fuck." I curse and he does finally stop, with every available inch fully inserted inside me, and his balls resting against my ass. "A-are you?"

"Yes." He simply says but there is a slight croak in his voice. I use a small source of energy to lift my neck up off the arm of the couch to catch a glimpse of him filling me to my hilt. It is almost unbelievable that he's managed to fit, but he has. "You've had time to adjust. Now time for fun." The words send a shiver right through me.

I let him set the pace -- which he does. His first couple of thrusts are shallow and the sneaking of the arms around my back is a kind of affectionate act, but quickly I realize that is not what he intended. He holds me close to anchor himself, to get more leverage, as he snaps his hips forward at a brutal rate like he is trying to bruise my insides. It is initially a little painful, but the burn quickly feels good, and it is something that I've definitely been missing. "Yes, yes, yes..." I chant as moans in time with his strokes, my arms loosely hanging at my sides as he holds me to his chest. The hairs scratch a bit at my skin, stimulating my nipples and inflaming my surgery scars.

"Oh Mikey..." He groans next to my ear. "Where have you been hiding? Huh?"

Jason then lowers me back onto the couch just so he can kiss me forcefully, mapping out the inside of my mouth in his mind. His teeth nip my bottom lip, he sucks at my tongue, and he makes me feel like the hottest man alive. He makes me feel actually attractive. I feel him blindly grab my wrists and pin them above my head with one hand, his other being used to lever himself off the couch so he doesn't crush me. "Jason..." I moan against his lips and he pulls back with a faux glower on his face.

"That's not my name." He tells me, making his grip on my wrists stronger but not painfully so just in a way that stokes the fire within me.

My back arches off the couch as a whine escapes the back of my throat. "Sir." I correct, giving him exactly what he wants, and he mischievously smiles.

"There's my good boy." Jason praises and I desperately roll my hips, hoping to encourage him to fuck me so hard that I can't walk for the next week. I don't just want it, I need it. Now. He meets my request with a deep thrust that starts with him almost pulling out entirely and finishing with him probing so deep that I cry out with desire. "You feel so good, Mikey."

I clamp around him with need after hearing these magic words, and suddenly I can't stop the dirty mutterings from leaving my mouth. "Fuck Sir, don't stop. Please, don't stop."

Jason pleasurably grunts and continues his hard thrusts which perfectly meet my own, needy, downward movements. "You already so close again my slut?" He questions with humor in his voice mixed with his pants. "Don't worry, I'm not going to stop baby boy."

My entire body is trembling, the vibrations are getting stronger the nearer I get to completion. It is crazy how quickly I'm near the edge once more and it shows just how much I needed this. I needed someone to wreck me tonight. "Please Sir, can I cum? I need to cum."

"Not yet." Jason firmly states in reply and I'm about to protest, but I'm stopped by him releasing his hold on my wrists and pushing up my legs so that my feet are on either side of my head. This creates a new angle that makes his hard dick perfectly massage the special spot inside me. "I'm going to cum first and then maybe I will let you cum for the third time tonight you slut."

Every word in my vocabulary disappears from my head apart from 'please' and 'Sir' because Jason is ruthlessly pounding into me, not even giving me a chance to breathe. I bang the back of my head on the arm of the couch on every thrust, but I am so far gone that I don't care if I get concussed if he lets me have my release. If this is what he does on our first night together, it excites mr to wonder what might happen on the second or even months down the line. He's surprised me but definitely in a good way.

His hairy chest pushes against the backs of my legs which somehow heightens my pleasure as our lips connect in a sloppy, open-mouthed kiss. It is impossible to reciprocate because of my breathlessness so he goes back to tongueing and sucking my neck instead. "You're incredible, Mikey." He murmurs near my skin, and I gasp because his fingers find my engorged and very sensitive clit again. He resumes rubbing my tiny dick, still pummelling into me so his balls slap against my virgin asshole that he has hinted will be breached next time.

"Please, Sir. I need to cum."

"I've got you." Jason tells me before producing a powerful rock of his hips, and then another, and then he's spilling inside me with a grunt. "Fuck." He moans and I feel the additional warmth even with the layer of rubber as he shoots every drop of his hot, creamy load. "Cum for me, Mikey."

"F-fuck." I shudder and then I'm practically exploding all over him, shivering underneath his body with my wetness making a mess of the couch below. "Yes, Sir. Feels so fucking good." Jason coaxes me through my orgasm with shallow thrusts of his softening cock and delicate fingers touching my dick. He mutters praises under his breath that I can only just hear over my loud pants and groans.

"Good boy." He mumbles and then he's pulling out.

And just like that, Jason switches back to a caring gentleman as he helps me to sit up against one of the cushions before he picks up my forgotten glass of water from the coffee table and helps me take a few sips. "There, you've got this." He unnecessarily continues to praise me, and it turns me gooey inside. "Beautiful boy." He compliments and wipes away a dribble of water that tried to escape my mouth. "Did you want to stay the night, baby?" I don't take much persuading.

I have a feeling that this is going to be the beginning of something beautifully messy.

-----------------------------------------

Author's note: Thank you for reading my first story! I might make this into a series... What do you think?