On the Trail

by Habu

9 Mar 2007 6055 readers Score 7.9 (43 votes) PDF Mobi ePub Txt


I had never tried to seduce another guy before, but Dale was just there at the right time and place. We were both runners he because he was on the college football team and running up and down the Pine Mountain trail helped keep him in shape and I because I wasn't that long out of college myself and I was doing the best I could to keep my fine form in shape.

We had passed each other a couple of times going up and down the trail that morning. It was a hot one, and as I was coming down the mountain, I saw that Dale had his sweaty shirt off as well, as his shoes and socks, and he was just standing under the shower by the maintenance hut, letting the water cascade down his beautiful body. He was a square-cut blond, with great pecs going down into washboard abs and a small waist. He had his heavily muscled arms over his head, and all of the muscles of his torso were stretched out to perfection. His calf and thigh muscles showed that he was both a football player and a serious runner. I just stood there and watched him in awe for a few minutes. The shower was sticking his running shorts to his legs and I could see that he had a pretty fine basket confined by his jock. He turned the water off as I was approaching and gave me a shy smile.

'Hi, Jack. It's just too damn hot out here. I couldn't wait to get cooled down.'

'I'm right with you, Dale. There's a picnic table over behind those bushes. Let me shower too, and I'll come over, and we can jaw a bit while we both dry off.'

'Sounds good,' Dale said, and he headed for the picnic table. After making a short instinctive visit to the car for a tube of lubricant, which I plopped in my pocket, I returned and stood under the shower for a couple of minutes. This was crazy, I thought. There would be no way I was going to pull this off. But, just maybe so. I had seen Dale look me over on the trail before, and if he was at all inclined, there just might be some fun to be had here.

When I sauntered around the bushes, I saw that Dale was sitting about two thirds down the bench, his back to the table, and his legs v-ed out at a good angle. He seemed to be wincing.

'What's the matter, Dale?' I asked, as I sat down beside him.

'You don't wanna know,' he said morosely.

'Sure I do. You look like you're in pain.'

'Yes, I guess I am a bit.'

'What's the problem?'

'There are two problems and you probably don't want to hear them.'

'Now you have me interested. Shoot.'

'That's the main problem. I can't shoot. And my girl, Cheryl Ann, and this here tight jock are the main problems.'

'Now, I'm intrigued, spill.'

'I can't,' he answered with a little grin. 'As I said, that's the problem. I have the hots for my girl, Cheryl Ann, and she won't put out. I've got all this stuff built up, and this tight jock is driving me crazy this morning.'

'Well,' I laughed, 'I can't do anything about Cheryl Ann, but you're out here alone this morning and you've finished your run. There's no reason you can't just take your jock off and hang free.'

'Hey, I guess you're right,' Dale said with a chuckle. He stood and turned his back to me, pulled his shorts down, pulled his jock down and off, pulled his shorts back up and sat back down in the same stance he'd been in. I hadn't seen his package, but his bulbous butt cheeks had been mighty interesting. I took a peek and saw that his shorts were tented up real nice now. I could actually make out a huge knob against the wet material.

'There, is that better?' I asked.

'A little, but not much,' Dale said sadly.

We sat there for a few minutes.

'You know that guys have a way to take care of that themselves,' I ventured.

'Yeah, I know, but that doesn't really do it for me. I apparently build up a lot and fast, and it just never seems complete when I do it myself.'

Another short pause.

'And you know that sometimes guys let other guys help them with that when it's really bad. I mean it isn't a queer thing or anything. Just playing around and releasing some tension when their girls won't put out. It's really unhealthy to just let it build, you know. It might hurt performance later.'

'Really? I hadn't heard that.' Dale sounded a little scared.

'Yes, really. I'm a doctor, and I'd do something about this if I were you. You wouldn't want to ruin yourself for later, when you and your girlfriend have finally hooked up.

Dale looked both dubious and scared now. And he was still wincing.

'Go ahead and do yourself, Dale. You obviously need some release right now. No one else is here. I'm a doctor, and I've seen it all. Just pull your pants on down and give yourself some relief while we talk.'

Dale hesitated, but the tension must really have been getting to him, because he lowered his shorts to his thighs and took a very nice, erect cock in his left hand and began to slowly jack off.

I could hardly keep my hands and eyes off him, but, beyond a few glances when he was looking away, I kept off him. I could feel my own cock hardening and giving me some of the same jock problem he'd had.

'You said I should do something about it. What could I do?'

'Well, guys come to me all the time for this sort of relief. There's something we can do called prostate massage. It's all medical, of course, not a gay thing. It's just that some guys have to be what we call 'milked' manually regularly because they can't get enough sexual release otherwise. It isn't a sign that you like guys; it just means that you are extra virile. It's usually young guys like you who have this problem.'

'It's all medical? Is there much pain in the procedure?'

'Sure it's medical, and, on the contrary, there's the same or more pleasure you'd get from penetration sex. It's just a medical procedure to alleviate a normal medical problem. The pleasure is just a bonus. And you'd lose that tension and pain you've got for a couple of days at least,' I said, making it up as I went along and hoping this sounded reasonable. And before he could raise more doubts about this, I steamed on. 'You've heard about the prostate, haven't you?'

'Yes, guys get testicle cancer from that, don't they?'

'Well, yes, they can, and that can be an added risk for someone like you who doesn't take care of the problem at this stage. The prostate is a gland behind the testicles. It's where all that sperm is being manufactured that you can't get rid of fast enough. Surely you've had a prostate exam during a medical checkup before.'

'Oh, yeah, that's where the doctor put his finger up my ass.'

'Did it hurt?'

'Naw. It felt a little tight and strange down there, but it didn't hurt.

'Well, in that exam, the doctor was just checking to see if your prostate was enlarging, which would be sign of trouble. In prostate massage, the doctor massages the prostate from inside your anal canal for several minutes, which milks the built-up sperm out of you more effectively than jerking off does and also gives you more pleasure than jerking off can. I hope you can follow what I'm saying; I'm trying to use words that you would understand rather than the fancy medical terms for all this. In extreme cases like yours, the doctor milks the penis at the same time.'

'It sounds . . . interesting, Doc. And you say I can get this done by going to a doctor?'

'Yes, certainly.'

'And could you recommend such a doctor for me?'

'I can do better than that, Dale. It doesn't require sterile surroundings. I can save you the money and give you immediate relief by showing you how it's done right here and now.'

'Right here and now?'

'Absolutely, you're already in a good initial position, and I just happen to have a tube of lubricant with me, which is all we need. Just strip those shorts off. I'll need you fully erect, so I'll have to do some preliminary work on you, and, with your serious condition, I'd better take charge of the penis for a while.' Dale pulled his shorts off and put both beefy arms back on the table.

'There, that's right; arch your back for me.' I put my left leg over the bench so that I was facing his side. I tentatively wrapped my left hand loosely around his cock, which made him twitch. 'Okay?' I asked. 'Any problems?'

'No,' he answered, although not really sure. I continued quickly, not wanting to give him too much time to think about this.

'Okay now, I'll do some preliminary rubbing of your pecs and nipples until I feel your penis fully engorge, and then we can begin. 'Okay with that?'

A muffled affirmative; my right hand went up to his chest and I lightly ran it around his pecs and nipples, slowly increasing the pressure and taking a few nips and squeezes of his nipples. I could tell he was stifling some grunts.

'Our goal is to release the tension here, Dale, not compound it. Just let those grunts and moans out. There's no reason not to enjoy this medical procedure.'

'But it's so . . . weird. I mean it doesn't seem right.'

'Would it seem right to have sex with Cheryl Ann, if she'd let you, Dale? Of course it would. Why would it be wrong to take care of a medical condition and still have sexual pleasure out of it? Everything's just fine, Dale. Ah, there, your penis seems to be ready. I'm going to be manipulating your penis now with one hand and doing some checking and preparing for the prostate massage with the other one now. We'll move slowly, and I'll tell you what is happening as we go along. I was slowly pumping his cock now, and he was beginning to pant and moan.

'There, yes, that's good. Just go with the flow of your feelings, Dale. We're alone out here, and this is just a medical procedure. Be natural.'

I took his balls in my right hand and weighed and teased them, rolling them around gently. Dale flinched.

'This is the testicular part of the procedure. I have to examine your testicles to make sure everything is okay there. And it does seem to be. And you were right; you seem to have a lot of semen backed up in here. We'll see what we can do about getting all of that cleared out. I'm now going on down toward your anus, Dale. Don't be alarmed, I won't enter the short way I have to go for this procedure without having you well lubricated. So, there will be only pleasure, no pain.'

Dale tensed up a bit as I put the heel of my hand under his balls and ran my finger to the rim of his ass. I would have liked to have gotten my mouth on that asshole too, but I couldn't think of any medical excuse to do that. So, I just left my finger there on his hole, applying a little pressure, while I took the fingers of my left hand up to the glans on his cock.

'Any problem with the glans, Dale?'

'The glans? What's a glans?'

'The head, the knob, on your penis. It seems a little distended. But that might be because of how long you've gone without fixing this problem.'

Dale answered with a moaning, 'No, I don't think I've had a problem there.'

'Well, I'll have to put some lubricant on it to examine it well. Here this will feel cool.' I rubbed a small glob of lubricant on his dick head and swirled it down and around the rim.' Dale flinched and moaned. I squeezed the spongy bulb and watched his slit open up. I moved my index finger there and pushed it open farther.

'Oh, oh,' Dale moaned, and he brought a hand down to mine.

'No, hands up Dale, this has to stay medical. There, I guess all is in order with you there; just lubricating up for the massage now.' I lubricated the fingers of my right hand well and took an added glop to start lathering up around his asshole. My left hand went back to stroking his cock, but I didn't do this too vigorously, because I didn't really want him to release yet.'

I did a lot of work on his entry, making it large enough for what I was planning. I made a few forays farther in, just to let him know I was continuing the procedure. When he had relaxed and his hole opening had loosened up, I slid my middle finger in to the sphincter. He gave a little lurch and yelp when the sphincter picked up the finger and sucked it into place at his prostate.

'There, can you feel that?' I asked.

'Yes,' he moaned through pants.

'It will take time to build the sensation up, but this should give you release.' I started a gentle massaging of the prostate, and Dale slowly started to writhe and moan and grind his pelvis.

'Here, this isn't the best position now, because you are naturally going to be moving around in response to the procedure. Here. Get up and move around to the end of the table here. Perch up on the end. There, that's right. Now lay back on the table and wrap your arms around the other end to give you support. There, that's right. This is now more like the table in the examination room. Now, we don't have stirrups. So, can you get your left foot on the edge of the bench there and keep a wide stance with that leg. Good. And now, your right leg, I guess will have to go over my left shoulder so that I have you open enough down there to proceed with the massage. There, that's good. Now I'm entering again.' I gently slid my index finger in to the prostate again and restarted the massage. Dale went back to panting and moaning and gyrating his pelvis slightly. His pants came louder and more quickly together, and my left finger on his glans felt some precum dribbling out.'

'There, is that feeling better, Dale? The milk is beginning to show.'

'Aw, shit yes, Man. That feels great waves and waves of great.'

'Here, I can increase that and quicken the flow. I'll use my thumb rather than my finger. Just stick with me here, Dale, I've got a large thumb.' I quickly slipped my shorts and jock off with my right hand and lathered up my cock with lubricant. I put my dick head up against his now-open asshole and slowly pushed in.'

'Oh, God, that's big,' Dale yelped. I had gotten it in to the prostate, and was manipulating my cock head against his prostate. 'Oh, but it feels so good,' Dale continued.

'Yes, big thumb. Just the right thing to get you off when you need it.'

'Oh, oh, oh, Gawd Damn!' And Dale was spurting several weeks of backup into the air and back down on his chest. He arched his torso up and then thumped it back down on the table. The last time he thumped it down, I slid my cock past the prostate and right on in.'

'What the fuck?' Dale screamed, and thrashed about on the table. He grabbed for me with his arms, but I got his legs in both of mine and lifted them up and out, bringing his butt up to a more open position. I pulled out nearly to the end and then stroked all the way back in to the root.

'Still workin the prostate here, Dale. Want me to stop.'

'YES!' I gyrated my hips in a rotating motion while fully encased. 'Oh, Gawd. No, no.'

'No what, Dale?' I asked, pumping and pumping and pumping.

'No, don't stop. Don't stop,' Dale whimpered. And he began to move his hips in syncopation with my thrusts, and dug his fingers into my chest hair and nipples. We came he for the second time within a few short minutes at nearly the same time. I released his legs, which just flopped down beyond the table, and I ran my hands up his abs to his pecs and collapsed on him. We looked each other in the eye and both leaned into a long, lingering kiss. I started to withdraw from him, but he moved his hands to my butt cheeks and kept me in place.

When our lips parted, he looked into my eyes with a satisfied smile and said,

'You aren't really a doctor, are you?'

'Yes, of course I am,' I answered. 'I wouldn't lie to you. I have a doctorate in geology, which means I'm eminently qualified to get your rocks off. I'm not a medical doctor, but I can do a prostate massage for free, and a medical doctor will charge you $100, and it won't be half the fun I can give you. You'll need another good milking in a couple of days, if Cheryl Ann keeps holding out.'

Another kiss, after which he responded. 'Good. I'll stick with the doctor I've got.. and who's Cheryl Ann?'

'That's my boy.'

by Habu

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