I awake, alone in bed. Last night was another long night of watching Ryan plow you deep and hard, while I masturbated in a chair next to the bed. You’d let me sleep in bed with you and Ryan afterwards, after I’d cleaned your messy pussy with my mouth. It was a comfort to be held in your arms, after all that, and I’d slept well.
I heard the shower shut off, and Ryan stepped in to the room, a towel around his waist. At this point, there wasn’t much privacy among us; I’d been fluffing Ryan at your direction for some time, and you two were bringing me in to watch and help out for some time. I sat up in bed and looked over at Ryan as his towel slid away. His body was amazing – I’d come to appreciate why you enjoy it so much as time had gone on. He was in amazing shape: hard, angular, chiseled. It didn’t hurt that he kept his cock and balls shaved bare, It also didn’t hurt that he was so large, stiff and straight. You’d made sure I knew about that, and in the past months you’d guided my hands and mouth over it so often, I felt like I knew him as well as you did. Ryan caught me staring at his cock in the mirror.
“You like what you see?” he said playfully, turning toward me. He was half hard, but I was showing off a serious boner, I’d realized. He sat down on the bed next to me and caressed my penis. “I guess you do, buddy. Look, I know it’s been a little rough with Josie pushing you around and all that, but honestly, I’ve really come to like you. It’s super cool that you agreed to let her fuck around, and to be sure, you really are a wonder with your mouth. Have you thought about trying to seduce Jo, tho? I mean, she still loves you, you know?”
I look at Ryan earnestly. “I know. It’s just that, you know, it seems like I can’t please her. Not like you do, at least. I mean, I love watching you two and the…” I trail off, a bit embarrassed. “The, um…”
“The wanking, it’s cool to admit it, man. I like to jack off, too, sometimes,” he says, squeezing my erection gently. It feels fantastic to have a hand other than my own on my dick. “Yes,” I say. “I’ve been enjoying the wanking. But like, when she does let me fuck her, it seems like she’s bored with a smaller dick. And I always cum so fast.”
“Well you know, she really likes anal. it’s tighter, so you might seem bigger to her. And if you wear a condom, I’m sure you’d last longer?” he offers helpfully.
“Anal?” I say dubiously. “I mean, we’ve never tried that. Do you think she’d go for it?”
“Never tried it? It’s great! The thing is, tho, you have to start slow. And for me, at least, I’ve had something up there myself before. If you know what I mean.”
“Really?” I aks, surprised.
“Well, yes. I mean, it’s only fair, right? You can’t ask a partner to do something that you’ve never had done to you, I think. You know, I’m heading back home for the weekend. That might be a good time to pop that question on her.”
“Wow, I mean, I just don’t know. I don’t even know where to start….” I trail off. Ryan wraps an arm around my shoulder. “Look, man, I can help you, OK? Would you like to try? I mean, I can show you how it’s done, and then you’ll be ready to take her. Plus, you’ll be able to say it’s nothing you haven’t tried yourself.” I notice that his cock is standing at full attention now, rock hard as he talks to me. And I have to admit, it’s gotten me a little aroused as well.
“I can tell you like the idea, too,” he says, stroking my now hard dick. “You must really love Josie.” he says, gently pushing me back on to the bed. He comes up behind me, resting his cock on my hole, my ass up. “Well, what do you say?” he says.
“Yes,” I whisper, horny but nervous. “Yes what?” he asks, laughing slightly. “Yes, I’ll try this with you. For Josie.” I feel just the head of Ryan’s cock penetrate me, and although I’ve had him in my mouth a number of times, I get a sense of just how large he is. I don’t think I’ve ever felt this vulnerable before. Ryan slides slowly into me, all the way, and I can feel his hefty balls press against me. I don’t think I’d ever felt so full before. “How is it?” Ryan whispered in my ear, his chest pressing against my back as he slowly pumps in and out of my tight hole. “Um, it’s a lot to take?” I say, reluctantly. “Yes, that’s what Josie said the first time, too. But how does it feel?” I don’t say anything, not wanting to betray myself to Ryan. I feel his hand reach around and grip my balls. “You’re really got quite the stiffy going on there, Jack. I think you must really like this,” he says, giving my penis a few rubs. I moan as he does. “Aye, you do like it. It’ alright, tho – be a man and take it. It takes a certain amount of confidence to admit that you like something, tho.” Ryan presses deep inside of my, splitting my hole wide open. My head is down on the pillow of the bed; the bed he sat on as I sucked his cock to get him ready to fuck my wife, the bed he fucked Josie in last night, the bed I cleaned his cum out of her pussy in. The bed I woke up in and watched Ryan come and talk me into letting him fuck my hole. I could feel his cock sliding in and out of me faster, each thrust pressing on my own dick in a way I’d never felt before. Ryan was right: it did feel good. So good, in fact, I could feel myself coming to a climax. As he drove his massive rod deep inside of me, I let loose with a large orgasm. Bigger than any I’d produced with my own hand last night. I could feel my hot jizz shooting all over the bed, and across my own belly and chest. I closed my eyes, enjoying the pleasure of this man’s hard cock inside of me, but also trying to wish away the humiliation of having cum on the cock that my wife worships nightly. “I knew you’d love this!” Ryan says excitedly, He shifts me into a new position, so I am sitting on his cock, riding him face to face. My flaccid penis is bouncing up and down as he bucks his hips against my ass. He lays back, and I realize I’m riding him as Josie often does during their morning quickies. I can feel the heat on my face as it burns red with shame. I look out the window, hoping that this will be over soon.
Ryan cums, hard, and he holds my hips as he drains his balls deep inside of my hole. I slide off of him, and slink to the shower. As the hot water runs over me, Ryan’s spunk running down my thighs, I hear him dressing in the other room. He pops his head in. “Hey man, thanks for that. I’m sure you’ll be able to give that back to Jo, too. She loves it, just like that.”