Trust fund twink pt.2

I knew that the best way to do this would be to take control. Some people say that a new bottom trying anal for the first time should be on top so that they can control the pace. Well if that works for some people then fine, but I think more people give up too easily that way. I say they are better of giving up control to a top who knows how to treat someone on their first time.

What the first-time bottom needs to know is that they are going to experience some new sensations and that the most important thing is to relax. They may be confusing sensations, and there may be a little pain, but if they just relax through it, the pleasure will overtake the pain and will become incredible.

These things I explain to my trust fund twink, as I absently run my hand up and down his body. My words are true, but they only work if they are conveyed with confidence. Confidence that engenders trust. Trust that allows relaxation when the strange new sensations occur. I have a gift for creating that trust it seems. My cock is longer and much thicker than average and experienced bottoms have struggled to take it. The first timers that I prepare with my words while they lie there, wide eyed, in my strong arms, they always take it all – and they enjoy it! And so it was with my blond haired boy, as he lay on his back, legs resting on my shoulders.

I looked into his blue eyes as I teased his hole with my hard cock. Gradually I applied a little pressure and the head pushed inside ever so slightly.

“Just relax, remember I can stop if you need me to. I’ll start gently.” I felt his hole loosen and I pushed the head of my cock a little further in, as I rocked my pelvis slowly back and forth.

I took his own stiff dick in my hand and caressed the tip with his slick precum. The distraction of that relaxed him further and suddenly I was in.

His eyes widened as he sharply drew breath. I paused just for a moment, before repeating my encouragement to relax and resuming my gentle back and forth movements, deeper now. His face flickered between surprise, and uncertainty for a few moments, as I continued to probe deeper into his warm passage. I withdrew a little and picked up the pace. Faster thrusts, pushing upwards towards his prostate. The surprise was back, this time accompanied by a growing childish grin that told me all I needed to know.

Before long he was taking my full length in deep thrusts that made him groan with pleasure. I relished the animalistic abandon that I could now allow myself as I ploughed him deeper and harder. All the time he took it with that big stupid grin on his face, broken only by the O his mouth formed when his moaning was too much to be done through a grin!

I rolled him onto his side, allowing myself a little more penetration. As I thrusted in this new position, my cock roughly pushing past his prostate again and again, he found himself surprised once more. Gasping and writhing, ribbons of cum shot out from his dick, without the help of his hand. Damn it was hot! I pulled slowly out and soon I was shooting my load across his body.

“Do you want a towel?” I asked.

“Can we not clean up yet?”

Fine with me. He lay there in my arms, covered in my cum. An expression of blissful satisfaction on his face. He closed his eyes, half sleeping, and I nearly dozed off myself.

We talked a while before he took a shower. That was at the end of the last university term. He went home for the summer. The new term has just started. I wonder if he will be booking me again.... I wouldn’t mind....