Jason Nice and Easy

There's this guy I work with, Jason. We don't actually work together - I'm in accounting, he's in shipping - but we run into each other fairly often, and for a while now we've been having lunch together a few times a week. We're sort of an unlikely pair, really. Jason is 23, I'm pushing 50, he's straight and I'm gay, he's a big sports fan, and I couldn't care less. Although, I do try to keep up on his favorite teams, just to be able to have a decent conversation with him if the subject comes up. So what's the attraction? Well, I don't know if Jason considers me a mentor, exactly, but he seems to value my opinion, at least on some subjects. We've become close enough that he sometimes comes over to my place on weekends, especially if one of his teams has a game on TV. His wife, Susan, doesn't like sports, at all, and would rather not have him watching games at home. Her loss, my gain.

So Jason was at my place Saturday, watching what he said was a really important game. We had a few beers while the game was on, and when it was over he didn't seem especially anxious to leave. We chatted for a while, nothing worth repeating, then he said, "You're gay, right?"

"Right," I answered. Common knowledge.

"So, you're into anal?"

"Not always," I said. "Depends on who I'm with."

"Well, when you do, which one are you?"

"You mean top or bottom? Again, depends on who I'm with. I'm what they call versatile."

He took a few seconds to process that, then said, "OK, but when you're the bottom, doesn't it hurt?"

"Not if you do it right," I said. "What's with all the questions?"

"Well," Jason said, "I've been trying to get Susan to try anal with me, and she finally agreed. But then she said it really hurt, and now she doesn't want to do it again. Ever. So maybe we didn't do it right."

"It's not really any big mystery," I said. "You just need to take your time, and use plenty of lube."

From the look on Jason's face, I might have been speaking a foreign language. "Lube?"

"Sure," I said, "lubricant. Look Jason, let me 'splain something to you. When a woman starts to get turned on and wants to have sex, her vagina starts getting wet. Maybe you just call it pussy juice, but that's a lubricant. So when you actually get started, you slide in pretty easily, because she is already wet. Lubricated. You with me so far?"

"Yeah," he said, "I guess."

"OK," I said. "Here's where lube comes into play. When you're talking anal, there's no natural lubricant. You have to provide it yourself. Now in the old days, people just used petroleum jelly, and that worked. But then we found out that didn't work too well with condoms, so a few personal lubricants came out. There's one that's pretty popular with straight couples, so you can probably find it in your drugstore."

Jason said, "Yeah, I've seen that. I always wondered what it was for."

"Well," I said, "it's not just for anal. Sometimes a woman doesn't get wet enough, or a couple just likes the sensation. I guess some guys probably use it when they jerk off. It's not really the best for anal though. Gays usually want something more heavy duty. There's a lot of brands out there, but you probably won't see them in the drugstore. I get mine at the adult store."

"OK," Jason said, "you said the thing is to take your time and use plenty of lube. So, how's that going to work?"

And I'm thinking, "Fuck, he wants the whole tutorial. Now what?"

"Well Jason," I said, "let's imagine I'm going to fuck you. I'll walk you through it, step by step, and you can ask any questions you want."

He gave me a suspicious look. "Strictly hypothetical, right?"

"Sure," I said, "absolutely. It's just that it will be easier for me to describe with a real person than with some abstraction. Plus, if I describe it with you, you might be able to imagine how Susan is feeling when you do it with her."

He thought about it for a few seconds, then said, "Yeah, that makes sense. I just don't want you getting the wrong idea."

"No problem," I said. "Ready?"

Jason took a deep breath, then said, "OK, ready."

"OK," I said, "first I'm going to give you a little head, just to get you turned on and in the mood for some excitement. Then I'm going to turn you over and rim your ass for a while."

"Rim my ass? You mean with your tongue?" I just nodded. "Isn't that sort of unsanitary?"

"Not if you keep yourself clean down there," I answered. "I can always get a washcloth if I have to. You've never done that with Susan?"

"No way," he said. "She'd freak out if I tried it."

"Too bad," I said, "she'd probably love it. So would you. Anyway, moving on. I rim your ass for a while, and you start feeling really, really good. You start wondering what it's going to feel like when I actually start fucking you, and you can hardly wait to find out. So, your ass is getting relaxed and loosened up, and when I think you're ready, I drizzle some lube into your butt crack. I spread it around with my fingers, and little by little I work a finger into your ass. OK so far?"

"Yeah, I think so. It's not going to hurt?"

"Shouldn't," I say, "I'm going real slow, being as gentle as I can. So, I work a finger into your ass, gently, just a little at a time, and you're liking it. Wanting more. I slide my finger in and out, finger fucking you, and you're starting to get into it. When you are loosened up enough, I might try two fingers at once, maybe even three. Mainly I want to feel you getting loose, relaxed, ready for the main event."

"The main event," Jason said. "You mean your cock."

"Right," I said, "when you're ready for my cock, that's the main event. OK, so let's say you're ready. I get a lot of lube on my cock, and some more on your ass. I start to work my way in, a little at a time. I push in until I feel resistance, then back off. I go again, just a fraction of an inch deeper, and back off again. We go through this routine a few times, maybe five or six, and then your sphincter opens up and I'm inside you. Just an inch or two at first. You might feel some discomfort at this point, OK? I wouldn't call it real pain, but sort of a burning, stinging sensation. That only lasts for a minute or so, then it goes away and you start feeling pretty good. When you're ready for me to go deeper, you'll let me know. You don't have to say anything, your body will do the talking."

"OK, but what if I don't like it after all? What if I want to stop?"

"We stop. No problem. If I kept going after you wanted to stop, that would be rape, right?"

Jason looked kind of shocked. "I didn't stop when Susan said it hurt."

"Well," I said, "that's between you and Susan. But for future reference, if your partner wants you to stop, you stop. No questions asked, no argument. If I was really fucking you and you wanted me to stop, that would be the end of it. Period."

Jason had to think about that for a minute. "OK, got it. But let's say I don't want you to stop. What's next?"

"OK," I said, "you're ready for me to go deeper. So I push in another couple of inches, still not all the way, just letting you feel my cock inside you. I slide in and out a few times, you start getting into it, and then I pull out all the way and get more lube. This time you're lubed up pretty good, and relaxed, so I slide in all the way, till my cock is buried deep inside you. I hold it there for a bit without moving, letting you get used to the feeling. Then I start fucking you, nice and easy, so you feel my cock moving inside you, just a couple of inches each way. And at this point I'm waiting for you to ask for more."

"So you want me to ask for it," Jason said. "What, you want me to beg you to fuck me?"

"I wouldn't say beg, but if it's right, you're going to get verbal. Not begging, but telling me to fuck you deeper, harder, faster, whatever. You might tell me how good it feels, or how big I am (even though I'm not really), what a good lover I am. All I'm saying is, if it's right you're going to really get into it."

"This is all doggy style, right?"

"Not necessarily," I said. "I like to start with you lying flat on your belly. You're more relaxed that way, so it's easier to get started. When you're ready we can switch to doggy. At that point you will be ready for some more intense fucking. I might give you a pretty good pounding, if I think you can take it. Then at some point I'll want to flip you over on your back, and fuck you face to face. I'll put a little bit of lube in your hand so you can jerk off while I'm fucking you. You need to see how great it feels to cum while you're getting fucked. It's so amazing, I can't begin to describe it."

"Cool," Jason said. "You're going to cum too, right?"

"Sure," I said, "you couldn't stop me if you tried."

"Well, will I be able to feel that?"

"Definitely! Sort of a throbbing sensation mostly. You might not be able to actually feel it shooting into you, but then again you might. It's pretty hot, either way."

Jason let out a huge sigh. "So that's it? Anything else I need to know?"

"Nothing I can think of," I said. "Do you think you can remember all that?"

"Yeah, I think so," he said. "Hey, this really helps. Thanks." He looked like he was deep in thought, then he looked me right in the eye and said, "Maybe you should show me."

I looked for any sign he was joking, and didn't see any. "Seriously?"

He took my hand and laid it on his crotch. "Serious enough?"

It felt like he had a flashlight hidden in his pants. Long, thick, stiff as a broom handle. "Jason," I said, "I want you to tell me exactly what you want. I need to hear you actually say it."

He only hesitated for a second or two. "I want you to suck my dick and rim my ass. Then I want you to fuck me, just like you described it."

That was clear enough for me. "Let's go," I said. I headed for the bedroom, with Jason right on my heels.

I got out a spare blanket and had Jason help me spread it on the bed. "Don't want any pecker tracks on the bedspread," I explained. "Now get naked. Let's see what we've got to work with."

He was out of his clothes in a flash, and so was I. My eyes went immediately to that flashlight I'd felt. Nice, very nice. Good sized but not huge, probably seven inches or so, pretty thick, sticking out from his body at a slight upward angle. Checking out the rest of his body, I was pleased to see that he was smooth, slender but solid, and his skin had sort of a golden glow, all over. I asked him to turn around so I could check out the whole package. Beautiful! Just about the most perfect little butt I ever saw.

"Lie down," I said, "let's get acquainted."

I laid down beside him and ran a hand over his chest, brushing across his nipples. He didn't say anything, but his body language said he liked that, so I spent a little more time teasing them, pinching them lightly, watching his reaction. No complaints, some sexy moans, and I wondered if he would let me suck them. I didn't want to scare him off, so I decided to let it go and moved on.

I ran my hand over his belly, down to his cock, and gave it a few light strokes, coaxing out a bit of precum. I leaned over him and took him in my mouth, running my tongue over the head of his cock, getting my first taste of him. Delicious! I pushed my lips down onto his shaft and slid up and down a few times.

"Wow, that really feels good," Jason said. I wondered if Susan gave him head very often, or if she was any good at it. Not that it mattered. For the moment, at least, he was all mine.

"You're pretty big," I said. "If you stuck this thing up Susan's ass without any lube, I can see why she doesn't want to try it again."

"Right," Jason said, "but you're going to show me how to do it right."

"Gonna try," I said.

I ran my tongue up and down along the underside of his cock, then down to his balls. I licked and sucked them, and judging by Jason's moans, I guess he loved that too. I took him in my mouth again, but this time I relaxed my throat and took him all the way down, so that my lips were tickled by his pubic hair. He was thick enough that I couldn't keep it there too long. Didn't really matter, Jason acted like that was another first for him. He wanted me to do it again, so I did, a couple of times. I was enjoying myself just as much as he was, but I was afraid he might cum if I kept it up, and we weren't ready for that yet.

"Turn over," I said, "show me your butt."

When he was face down, I ran my hands over his shoulders and back, then down to his ass. Nice, very nice! His butt was close to perfect, at least by my standards. Muscular, shapely, soft, smooth, all the things I like, and not too big. I ran a finger up along the crack, not touching bottom yet, and he let out a sigh of pure pleasure. I did it again, only this time I went deeper, so that my finger brushed across his asshole. His body gave a little jerk, and he opened his legs wider, inviting more contact. I held my thumb against his hole and massaged it gently, helping him to loosen up and get in the mood for more.

When I thought Jason was ready, I leaned in and ran my tongue up his butt crack, from bottom to top, not yet touching that tight little entryway. The next pass, I went a little deeper, so that I just barely touched his hole. He jumped as if he got a small electric shock, and again spread his legs wider. I spread his cheeks apart and ran my tongue all the way from his balls to the small of his back, making sure I hit the hot spot. Again he jerked like he got a shock, and gave out with a soft moan.

"No need for a washcloth," I said, "it's like you just got out of the shower. You OK?"

"Yeah," he answered, "fuck yeah! That feels fantastic."

"Just wait," I said, "it gets even better."

I went back to work, letting Jason get used to feeling a tongue on his asshole. I took it easy at first, running my tongue over and around that tight brown pucker, getting him to relax. Little by little I got bolder, pushing my tongue in a little ways and seeing how he would react. Seemed like he was loving it, so I kept going, pushing my tongue in deeper, swirling it around in circles, gently fucking him with my tongue. I was loving it, and so was Jason, but it was time to move on.

I drizzled some lube into his crack and spread it around with a couple of fingers, then gently worked one well-lubricated finger into his ass. I watched for any sign that he was uncomfortable, or wanted me to stop.

"You OK?" I asked.

"Yeah, I'm good," Jason said. "That feels pretty good. Don't stop."

Just what I wanted to hear. I slid my finger in and out, nice and easy, letting him get used to the sensation. When he was loosen up and well lubricated, I held two fingers together and worked them in gradually. I didn't want to hurt him, but I did want to stretch him and get him ready for my cock. For Jason's part, he wasn't complaining at all. I think he was actually getting a little anxious to try the real thing. Anyway I hoped so, because that's what was happening next.

I got up over Jason, put my cock between his cheeks, and slid it up and down a few times. I wanted to get it lubed up, but mainly I wanted Jason to feel it and get turned on to the idea of having it inside his ass. I was already hard as a rock, so that wasn't going to be a problem. I got more lube and gave myself a generous coat, then began to work my way into his ass. I pushed in a little ways, backed off, pushed in a fraction of an inch further, backed off again. Just like I had told him. After a few tries his sphincter opened up, and I was inside him, just an inch or so.

I held completely still, letting him adjust to the feeling. "Take a couple of deep breaths and try to relax," I told him. "Let me know when you're ready for more."

Jason did just that. A couple of deep breaths, a short pause, then he pushed back toward me, inviting me to go deeper. I let my cock slide in another inch or two, pulled back and then in again, and I knew he was starting to get into it. I pulled all the way out and got more lube, then entered him again. This time I slid in easily and didn't stop until I was all the way in, up to my balls. I held still again, waiting for a reaction.

"Wow, that feels like you're in really deep," Jason said. "It feels amazing. I never imagined it would be like this."

"That's as deep as I can go," I told him. "It feels great to me too. You're really tight. I'm going to start fucking you a little bit now, nice and easy. Let me know if I'm hurting you at all. You should enjoy this at least as much as I do."

I began moving inside him, just a couple of inches each way, staying pretty deep the whole time. Feeling him get looser, I went to longer strokes, almost all the way out and then all the way in again. That was feeling smooth and easy, so I got Jason up on his hands and knees for some doggy style. I pulled out, got more lube, and started fucking him a little harder and faster. His ass was well loosened up by then, and there was plenty of lube, so the feeling was fantastic for both of us.

"Wow," Jason said, "I feel like you're really fucking me now. I'm loving it! Unbelievable!"

I pulled out and turned him over on his back. I was happy to see that his cock was still hard as a rock. He didn't lose his erection while he was getting fucked. I couldn't resist leaning in and sucking him a little, just for fun. Then I put his legs up over my shoulders, slipped my cock into his ass, and started in again. The look on his face was priceless, and impossible to describe. Does peacefully ecstatic make any sense?

In any case, I knew we were on the home stretch, so I wanted to assure a Happy Ending for both of us. I took Jason's hand and squeezed some lube in his palm. He knew what that meant, so he spread the lube onto his cock and started jerking off. He tried to go slow and make it last, but before long he was going full blast, building up to a mind-blowing climax. I was getting pretty close myself, but I tried to keep it under control, to be sure Jason got there first.

Jason's breathing got shorter, and his stomach muscles started working overtime, so I knew he was almost there. I looked down and saw a little bit of cum ooze out of the tip of his cock, then he started to cum for real. A thick white glob came shooting out of his cock and landed high on his chest, then another shot reached his neck. If he wanted to, he could probably have cum in his own mouth. There were several more spurts, probably six or more powerful ones, then four or five less powerful, leaving his belly and chest covered with cum.

Then it was my turn. I felt my balls filling with cum, felt it working its way up the shaft of my cock, felt it begin to shoot into Jason's tight little ass. I pushed my cock in as far as it would go and held it there, hoping Jason would be able to feel my cock throbbing, feel my cum shooting into his ass. When I was finished, I pulled out completely, rubbed the head of my cock around between his buns, then pushed in again and fucked him just a little more.

Time for some cuddling. I turned Jason on his side, with his back to me, and got behind him spoon fashion. We didn't talk at all for a while, I just stroked him, touching him lightly all over, helping him come down.

"How you doing, Jason? You OK?"

"Better than OK. I feel great. That was incredible, better than I ever could have imagined. I don't know if Susan will be willing to try again, but if she is, at least now I know better what to do. Even if she doesn't give me another chance, I'm glad this happened. I don't think I"m gay, but I'd let you do me again if you wanted to."

"Well Jason, that's nice to hear. I don't think you're gay either, but I'm glad you're keeping an open mind."

Then it was time for Jason to head home. We had a nice hug, he thanked me again for everything, and hit the road. I couldn't help wondering where this might lead. Time will tell, I guess.