Page 20 of Loving Jamie
“I only tried it once. I think I was about 18 and I had been watching porn. The next time I was in the shower, I tried sticking one of my fingers up there. It hurt so bad and I never tried doing it again.”
I look at William and see both of his eyebrows raised and his mouth pinched.
Rolling my eyes. “What? Why are you looking at me like that?”
William laughs loudly and I shove his shoulder. “Seriously, why are you laughing at me?”
After a few seconds he says, “Please tell me you used lube and not just hot water?”
I stay silent because thinking back to that moment, he’s right. I only used water.
He wraps an arm around me and pulls me to his side. “Ok, I have homework for you. We are going to write Jamie’s list and then, when you get home tonight, I want you to take some time for yourself and try again, but with a bottle of lube this time.”
The thought of putting myself through the same pain I did all those years ago makes me involuntarily clench, but the idea of William telling me what to do makes my cock twitch in my pants.
“Fine, whatever, I'll try it. But if I hurt myself, I'm blaming you.”
He rolls his eyes and says, “Just try it. You might do it and not enjoy it and that's ok, but I think if you make sure there is no pain you may discover how nice it can be playing with your prostate.”
I shove away from him and pick up the notepad that’s resting on the coffee table. “Ok, I'll try. Now, let's make this list.”
When I get home a few hours later, William’s words are repeating in my head. I have had enough sex over the years to know that people enjoy anal sex.
I make my way to my bedroom and grab a bottle of lube from my bedside drawers. I strip down and get comfortable on the bed with my back leaning against the headboard.
Adding a few pumps of lube to my hand, I start stroking my shaft. I've been hard since having the talk with William, so I know it won't take long for me to blow. I slow down my movements and add more lube to my hand. Massaging my balls, I shut my eyes and allow myself to relax. I slowly move my fingers towards my taint.
The soft pressure feels nice, but whenever I move my fingers towards my hole, my body clenches and I start to sweat. Realistically, I know it's not going to hurt this time, and the lube will allow a smoother entry, but I’m still nervous.
I try a few more times, just lightly stroking along my entrance, using my other hand to stroke my cock until I notice I’ve gone soft.
Fuck. I can't do this.
Porn. Watching some porn might help. I pick up my phone from where I left it on the bed and unlock it. Before I can open the internet browser, I see I have a new message from William.
William
Have fun tonight. Let me know how it goes.
I scoff at his message, but I'm already pressing the call button. He answers within a few seconds, his deep voice blasting through the speaker.
“Hey Justin, finished already?” He asks.
I tut at him and say, “No I haven't finished already.”
I don’t say anything else and the silence lasts a few seconds before he says, “What’s the matter?”
“I feel embarrassed. I can't do it. I tried, but whenever I touch myself, I freeze. What should I do? I really want to do this, even if I hate it.” I tell him.
“Ok, I understand. But if you can't do it, don’t force it. You’ll end up hurting yourself. What are you doing right now?” He asks.
“I’m lying in bed. I was just about to load some porn up on my phone, but then I got your text and decided to call you instead.”
He hums and says, “And why did you decide to call me? I mean, don’t take it the wrong way, you can call me whenever you like, but what was the reason for calling me?”
I think for a few seconds before it hits me. I called him because I need him to help me through this. “I needed you.”
“What do you need from me, Justin?” His voice is deeper than usual and I wonder if this is the voice he uses when he’s telling his subs what to do.