RP:]] St Luke's Reform School For Young Gentlemen

I hiss out a breath as Brian smooths out the latex on my dick I open my eyes as I feel his hand fall away from my dick and move down to my thigh where he gives me a gentle squeeze with slightly quivering hands.

"Now, I'm just gonna prepare you, OK? I don't want to hurt you," I don't say anything about how the first time hurts because I don't even know if I am his first time.

That, and I don't really want to insult him. I mean, doing the first thing with sex at the age of forty. We've supposed to have done it all in sex, hell even 69'd in a bar backroom if you can.

I smile at Brian simply before squirting some of the clear lube on my fingers, and quite a lot too if I must say so myself. I start with just the one finger, teasing his hole with the tip, watching his face for any fear so I know if I need to stop.

I push my finger into him, loosing him up and almost moaning inwardly at the possible heat and tightness I am about to feel from him.

"This OK for you?"

I smile at the smile on his face, glad that he is happy about this and not all wincing and gripping the bedsheets yet. But i guess this is only one finger.

"OK," I say to him as I find my other finger and push that into his hole as well.

I bite my lip in concentration as I scissor my fingers inside of him, watching his face as it turns into a slightly pained expression.

"You OK, Brian?"

"It's likely to be," I say to him as I continue to stretch him out.

I scissor my fingers as much as I can without tearing the muscles in my palm, just so I can stop the pain as much as I can. I pull my fingers from him slowly as I pop the cap of the lube with my other hand before dripping it onto my wrapped dick.

I shudder a little from the sensation as I coat my dick in a very thick layer of the clear liquid. I shot a look up at Brian as I pull my fingers all the way out.

"Good to go?"

"You're not 16 again baby," I say with a smile before leaning down and leering my lips over his, "you're much better looking than you were when you were sixteen."

I grin as I kiss his lips, trying to distract him from the sudden pain he is going to feel. I push the head of my dick to his entrance, pushing myself in slowly and I can feel Brian wanting to bite down on my lip as I do this.

"You've gotta relax baby," I tell him as our lips are mere centimetres apart.

"Don't be sorry, it's OK," I tell him reassuringly with a smile still on my face, kissing him randomly around his face to distract him from the pain as I fill him to the halt.

I stay in place for a little while, letting him get used to my size and the feeling. I just want his face as he adjusts to me, letting my hands full down to his thighs where I hold onto him and caress him in another method of calming.

"Just tell me when you're ready," I whisper to him.

I bite my lip a little from the sight of Brian looking so pained but I do what he says none the less. I pull out of him gently, just as slowly as I went in.

I push back into him a little faster this time though, just to built up a rhythm.

He's so tight, it's almost painfully pleasurable how tight his muscles are holding my dick in place. It's enough to make me explode because I can't go any faster than this. But the strain and teasing will do me, and him good in the long run.

"Brian?" I ask him as I pull out of him again, just leaving the head of my cock in his tight heat, "do you want to stop?"

I don't want to stop this, not at all and with anymore else I would just carry on and forget about the pained expression on their face by closing mt eyes. But I can't do that with Brian, I care about him too much. Plus the fact I can't keep my eyes off of him.

"Because if you're not feelin' it we can do something else, whatever you want," I tell him with a smile, my breath a little out of sync with the amazing feeling he is giving me.

"OK, OK, I'll make this amazing, I promise," I whisper to him as I kiss his lips again and push into him again.

I groan against his lips at the tightness gripping me, not able to keep in any noises anymore.

I do feel bad that it feels so good for me, and he's just left in limbo right now, wondering whether he's going to get the pleasure that I know he deserves. I don't want to be the one that couldn't get him off, but I'm sure I can last out. That's one of the great things about being a more experienced lover, you know how to hold yourself.

I smile to myself as Brian's left panting and wriggling under me. I grin at Brian as he grips his fingernails into my shoulders and obviously tries to calm himself down a little.

"Did I mention that when you get older it's gets better to bottom?" I smirk as I pull out of him slowly and push in a little faster.

I watch him as he closes his eyes and his mouth fulls open as I hit his prostate dead on again.

"Oooh really?" I ask him breathlessly as I push into him again as far as I can go.

I watch as his back aches and he moans, not sure what to do with himself as I keep my dick pressed against his spot, pushing into it in a pattern of small fast jabs.

"Because something is telling me different," I grin as I look down to see his once limp cock is now standing to a-straining-ttention once again.

"But I'm not sure what, it could be," I once again jab at the stop inside him at a speed that would be seen as heart attack worthy of someone my age, "the moaning and you whispering..."

I lean down to his ear as I continue to jab into him, rocking my hips at the same unknown speed, "Ooooh Coby, harder, harder...uhhhh..." my whispering vibrates into his ear.

"Mmmm, yes please Angel," I tell him with a grin on my face.

Angel, man I haven't called anyone else that since... since Brian actually. No one else has had the pleasure, or the love for me to be called such a personal nickname by me.

"Ooow," I am snapped out of my thoughts as I feel Brian pull on my hair, "bitch."

I laugh it off before glaring down at him and doing what I was doing before, but this time I grab onto his ass cheeks and grip my fingernails into the baby soft skin there.