Prep

“Fuck yes…” Kimmy mutters as her semi hard cock breaches my mouth. She places her hands gently on my head and joins me in the rhythm as I slowly bob up and down on her dick.

I could feel it growing in my mouth with every thrust. Can feel it expanding against my lips. Being able to take less and less in because it kept growing longer. Kimmy’s hands on my hair get tighter as she slowly takes over the rhythm of the blow job. Her movements become slightly harder, slightly faster. The bulbous head of her cock now firmer as it barges straight into the back of my mouth. Trying and failing to get past, before its rebounded causing me to cough or splutter around her dick.

Her cock now fully hard stretches my lips quite considerably around its girthy middle. I can barely take about half its length. Kimmy’s movements have gone from slightly harder to mercilessly hard as she seems to just use my face as a toy. My hair, her grips, as she shoves me up and down her length. My whole face is soaked with spittle as I drool around her. I can taste something as well in the sea of spittle that’s become my mouth. Something slightly salty. When I realise its pre cum I’m shocked by the fact that that doesn’t really seem to bother me.

While the only sounds coming from me are the slurping, coughing and gasping for occasional breath. Kimmy has turned into some kind of potty mouthed, sex craved sailor, who’s just found port after months at sea.

“Fuck yea! **** on the dick!”

“Mmm, you like that don’t you.”

“I can’t believe we waited this long to do this! All those fucking jocks getting off with their bitches in free periods and I could have been doing same… Mmm.”

“Christ you have such a sexy mouth Keiran.”

“Can you feel how hard I am baby!”

“Ooo, yea cough around my dick like that again!”

“Yea slut! Worship my cock!”

“Remember Kimmy has the biggest dick! Your all mine tonight sweetie!”

“Grab my balls and massage them”

My hands have naturally gravitated to her perk bum to steady myself while she was fucking my mouth. But, with one quick order I bring one hand away and start massaging her large set of balls.

Kimmy had always been a little domineering. It was always her that would push the group to do something daring. She could also be the most upfront of the group; quick to point out mistakes or call someone an idiot, especially Kieran, in a friendly but mocking way. She was also the headstrong one. If Kimmy didn’t want to do something, she would drag her feet to the point of obstinance. If she wanted to something though, the group just usually went along with it. It was easier than trying to argue against her.

The current Kimmy was taking domineering to the next level. Barking orders and dirty name calling. Part of me kept urging myself to just take her cock out of my mouth, stand up, put my clothes on and leave. But that part was in the minority. I found myself trying to take her deeper with every name call, trying to lick around her shaft with every violent thrust. I was completely enthralled by her words and actions.

Suddenly with a particularly violent tug I’m taken right off her. I gasp to take in **** breaths that I wasn’t aware my body was craving. Hands now on my knees as I take breathes in. I look up to see Kimmy standing there, her rigid dick standing impossibly horizontal in defiance to its own absurd weight.

She reaches down and grabs me by the shoulder to pull me up. I allow myself to be led back to the bed where she pushes me forwards and I land on my stomach on the soft sheets. She gets up behind me and shimmies me forwards until my whole body lies length ways across the bed.

“Fuck I can’t wait to get inside this tight hole!” Two hands slap down on my cheeks causing me to gasp. She then starts massaging them both deeply.

“Jesus, Kimmy… don’t be so rough.”

“Oo be quiet, you love it” she laughs.

She was right, I did. I feel her move and then she’s on top of me, thighs either side my legs, pinning them. Her wet cock lands right between my butt cheeks as she saw’s gently up and down in a lustful passion. Turning around looking at, I can’t help but gaze at how gorgeous she looks. So sexy and confident.

She puts her hands on either side of my back and starts to hot dog my ass more aggressively. Her cock is soaking wet from my earlier work, and I can feel the spittle drip into my ass. I find myself really wanting her to push in, really wanting her to aim just a little lower. The idea terrifies and excites me.

Watching all those girls do anal in porn, watching how their tiny holes stretched around those giant dicks. I’d always imagined myself being the guy in that scenario. Pushing in. Never in a million years would I believe it would be me getting fucked. Fucked by a cock that would make ninety percent of those male stars gasp.

Kimmy gets off my body and then gets on to the floor behind on her knees. She pulls my cheeks back and instantly plants her face between them. I gasp “fuck!” as her tongue pushes into me. “Holy fuck Kimmy!” I blurt out as she starts mercilessly tonging my hole. Her hands pinch and knead my bum on either side as she seems determined to push her face in as far as possible.

After a few minutes she withdraws her face and I look back to her panting. Face covered in a sheen of shiny saliva. “You have such a nice ass…” She raises a hand up with a finger extended and slowly starts rubbing it around my hole. I start panting, squirming under her touch. “Don’t worry. I know I’m big, I’ve spent ages researching how to prep someone.”

Due to her early tongued **** everything is soaked, and my opening is slightly loose. So, when the first digit enters there’s only a slight amount of pain. She pushes in and out slowly, with every thrust going a little deeper until the first then the second knuckle sink effortlessly inside. My moans and squirms intensify as I feel the second finger added.

“Fuck fuck fuck…” she’s now sawing both fingers in and out quickly. “Slow down Kimmy.”

She slows down her rhythm a little. “Jeez, such a baby” She giggles. Her hand shifts position and as she pushes into me this time and I feel her contact something and a jolt passes through my body.

“Eu…” I moan as she contacts it again.

“Ha, there it is. Aha” She pushes down in again with both fingers and I squirm. “Wow your super receptive, I read that some people were more than others, but you seem to be super sensitive.” Unable to keep the glee from her voice.

“Wha-t! What are you doing?”

“Ha, relax. I’ve just found your prostate.” Her fingers are now rubbing up and down on this sensitive spot. “It’s like a boy’s version of a clit. Apparently, there’s even some men out there who can cum just from having it played with. Not even touching their dicks.”

I pant heavily as her two fingers once again graze the same spot. “Erg…” My body spasms around her touch and my toes curl inwards as the feeling before sweeps through me with even more ****. My eyes close as I gasp.

“Seriously, you really are a slut aren’t you Kieran?” Kimmy laughs and I can feel her fingers going in and out of me with more purpose, she starts curling her fingers inside, as if to do a ‘come hither’ motion as she exits. Again, this elects another stronger moan from me. “Ha, sensitive little slut indeed.”

“Fuck you… Kimmy” I moan out, a part of me in defiance to her name calling, but I know inside it’s a hollow insult. I don’t want her to stop, I want more.

Kimmy as If reading my mind laughs again. “No Kieran” I feel her lower her body over my back, her ridged nipples contacting my skin. Her fingers continue their magic as she kisses the top of my back just bellow my neck. “No Kieran, I’m afraid that’s not on the table for you.” She continues down my back planting kisses. “You lost Kieran…” kiss. “There’s no fucking for you…” Kiss “Also…” Kiss. “I don’t think you want that…” Kiss. “I think you want this…” She slips her third finger in.

“Fuck” I moan as I feel myself stretch further. There’s pain, a full throbbing pain as her third finger barrels inside, joining the other two that had so forcibly made themselves at home. My toes curl even further in she pushes in with all three. “Fuck fuck fuck Kimmy it hurt’s!” I close my eyes hard as I cry out

She leaves her fingers in there, pushed into their max. I feel her plant a kiss on each of my cheeks, softly, tenderly. We both lay there, me eyes close, ass throbbing. Her, repeatedly kissing both my cheeks in succession as she leaves her fingers still inside of me.

I feel her shift her weight as she sits up, fingers still inside. I turn around and look at her, thighs still trapping my legs, her face split in a confident grin, still shiny with a sheen of spittle. “Ooo yea you really want me to take them out.”

As I go to answer I feel her move them again inside of me, grazing that same sensitive spot. “Yessss……Oo fuck” I finish, my sentence cut off.

“Ill ask you again Kieran, do you want me to take them out” Her fingers now lay motionless inside again.

As I begin to answer she flex’s her finger once again. “Fuck! No!” I shout as I writhe around the on the bed. All I can hear as her cute little laugh as she once again starts playing me like a fiddle.

Her free hand goes to my hard cock which I realise I had been rubbing against the fabric of the hotel’s duvet in rhythm with her own time. She jerks my dick along with her own motion as well.

We continue this way for a while, her laughing and me writhing under her. I can feel myself getting close, feel myself reaching that point. That build. Almost there, I can feel myself cresting that sweet, beautiful wave that was about to shot out of my dick, and then…

At once I feel her pull her fingers out from inside of, her other hand comes away from my dick. I feel her start to stand up. “I think that will do…” I hear her say.

I whip around angry and confused. I was so close, “What the fuck Kimmy I was just about to cum.”

Kimmy now stands off the bed and laughs as she walks over to a pile of her own discarded items, her long cock ridged and bouncing with every step. “Ha, don’t worry Ill make sure you cum tonight” She turns around and winks.

“But I was just about to cum then!” I retort back still peeved, but eyes betray me as they keep moving down her body switching between her perfect tits and throbbing member.

My ogling doesn’t escape her attention as she reaches down and picks up her clutch bag. She rises and opens it pulling out a purple bottle of some kind. “Oo did you forget that tonight isn’t about you Kieran…” She flips the cap and pours a generous amount of what must be lube into her hands. She reaches down and starts massaging the clear liquid all over the ridged mass protruding from her tiny body. Her other hand joins the other as it spreads the liquid up and down. “You lost Kieran, tonight’s about me” She smiles even more sweetly as her eyes remain locked on mine. “Don’t worry through, you’re definitely going to cum… but that will be on our terms” she finishes before looking down at her cock and pointing towards me.

I gulp audibly in response. Then a tiny part of me raises a thought that rocks my entire brain. ‘why does she have lube in her bag…’

Almost as if reading my mind Kimmy looks down at the bottle and laughs. “A girl's always gotta be prepared.”

My mind bites back the questions it was about to raise. ‘Does she always carry lube?’ ‘Did she plan this from the start?’ ‘How long has she been planning this?’ These questions disperse almost as quickly as they rise as I stare at the shiny obelisk she’s pointing towards me.

I was still terrified, but I was also excited. Who knew that the past thirty minutes or so of her prepping me could awake such a feeling. I was nervous, nervous of it being anywhere near me, but I also couldn’t wait, couldn’t wait… to have it inside of me.

Kimmy walks over confidently. She reaches the bed and goes to grab my legs and slow rotates my body so that Im now on my back with her looming over. Her beautiful face, her stunning tits and lastly huge prick.

She moves forward and pushes the head towards my slightly gaping hole. I feel the head make contact as it moves past my vision of sight. Kimmy looks up at me, our eyes meet, and I see my friend. “Ready?” she asks. It’s a simple word but the connotations behind it were anything but simple, there was no going back after this, ‘Was I ready?’ I take a breathe, look into her eyes and nod firmly.

She pushes in…