Go for it

You take a deep breath. This is it, if you want the job, this is what is expected of you. You reach up and gently hold Derek's cock. It does look like it's a bit smaller than yours, but not by much and already the tip glistens with pre-cum. Derek places a hand behind your head and gently pulls your head forward. You open your mouth and allow the head of Derek's cock to slip between your lips. You run your tongue along the tip and taste the musky salty flavour of Derek's pre-cum. It's unusual, but not unpleasant. You flick your tongue back and forth, trying to mimic Derek's technique. "That's it" he says encouragingly "see, it's easy. Try and get more in" he says, pushing his hips forward and sliding a couple more inches into your mouth. In the moment, the world drops away; there's just you, Derek, and his cock in your mouth. You begin to relax and give in to the experience, actively sucking Derek's juicy cock, sliding your head up and down his shaft, licking with your tongue. It takes a while for you to find a rhythm, but eventually your technique settles.

Derek thrusts his hips and makes satisfied noises, "Yeah, that's it. You're a natural". His moans become intense and you prepare yourself for his load, but instead he pulls out of your mouth. "Whew" he says "better not get too close or I won't be able to finish the review" he says, taking a condom out of his pocket. "Lie down on the bed." he instructs. You freeze. Sucking a cock is one thing, but getting fucked by a big thick dick was a scary prospect. "It's OK, I know you've not done this before, I'll go slow" he says.

Nervously, you lie down on the bed. "Closer to the edge" Derek tells you, bringing you further down the bed. His cock now has a condom on and he has a small bottle of lube which he applies to himself. "Right, lift your feet up" he tells you. You raise your legs awkwardly, allowing Derek to take your ankles and rest them on his shoulders before spreading lube over your ass. You feel awkward, lying with your ass raised in the air while Derek lubes you up. You feel his finger push inside your ring, causing you to gasp. "Ooooh, nice and tight" says Derek "This lube will numb you a bit, so it shouldn't be too bad, just tell me how you're feeling." says Derek. You nod and try to relax, feeling his finger working in and out of your ring. You feel an uncomfortable stretch as another finger pushes inside. "How's that feel?" Derek asks.

"OK" you manage to say, although it's rather uncomfortable. Not painful, just a strange feeling of pressure.

"Right then, just push down when I go in, it'll help to open you up. Ready?" he asks. You nod and take a deep breath. Derek withdraws his fingers and positions his cock against your hole. You feel something large and hard push past your ring, stretching you. The lube must have helped somewhat, but there is still a mildly painful stinging. You bear down like he suggested and feel your ass open up to take in his cock. He slowly slides in his entire length. "Good job Alan." says Derek as he stands at the foot of the bed, nuts deep inside you.

"It's a bit painful" you say "maybe we should..."

"Just give it a couple of minutes, it'll pass, trust me" says Derek. He begins to slowly rock his hips, thrusting his dick in and out of your hole, all the while the feeling of pressure makes it impossible to relax. "Breathe" says Derek as he continues to slowly pump you. You do as you're told and try to relax some more. Just as you're about tell him to stop, the pressure begins to subside. "That's it, you're loosening up nicely" says Derek, pumping himself into you a little faster. You lie back and relax, starting to feel a subtle but pleasing tingle. "How's it feeling now?" asks Derek.

"It's good." you say, prompting a smile from Derek.

"You ain't seen nothing yet" he says, suddenly increasing his speed and ****, slamming himself into you. There's a spasm of pain as the intensity of the fucking increases, but it is quickly replaced by an increase of the pleasing tingle. You release a moan; "oh fuck!"

"Yeah, that's it, you like that, don't you" says Derek. He grabs your throbbing cock and begins to jack you off in time with his thrusting. The feeling is intense and you can feel yourself quickly coming towards an orgasm.

"Not yet, just hold it a little while longer" says Derek, breathing heavily as he forcefully fucks your virgin ass. "Nearly there".

You try to hold back but the new sensation is too much, before you even realise what's happened, there's a hot wet splash on your chest and stomach as you ejaculate with a load moan. Derek pulls out, removes the condom and jacks himself off, sending his own load over your body to mingle with yours. He stands panting.

"Well, I hope you enjoy that as much as I did" he says, lowering your legs. You lie, exhausted, still reeling in the intensity of your climax. "I'll let the service know that you're ready for active duty. I'd suggest maybe getting some toys for home. Some clients aren't as careful as me, so it'd be helpful to train. Try and learn to hold off for longer too. You can take a shower before you leave. Welcome to the team kid." he says before heading to the bathroom to wash up.