I arranged my time away for the trip up into Springer Mountain with my staff and it turns out that Jim was working down that way and was going to meet me at the base of the trail head on Friday afternoon.
On the hour trip out there I was going over the dozens of articles I had read online about fucking a virgin ass, most of which condensed to; use too much of a good lube, warm it up, stretch it out with your fingers and move super slowly and take cues from the take-ee. I found out that Jim had never even stuck a finger up his ass, so he really was a virgin with the exception of the beer bottle which I also found out was going in big end first. Oi.
I've only had sex with one person, my wife, who had a lot more experience than I did while we were apart at colleges across the country from each other. I was trained to wait until marriage to have sex, my family is old school and it was never a question for me, so I did. I've never compared my dick to anyone else's except in porn, but it's hard to tell if the guy is shrimpy and his dick just looks massive and then there are those with 14" schlongs that are so huge they never get rock hard or the guy'd pass out from blood loss. I don't trust my wife, because she loves me and sounds like a used car salesman when she says it's massive, girthy and too long, too long because I apparently blast into and past her cervix in an uncomfortably painful way sometimes. I've measured Pop-eye a few times and looked it up online and he is larger than average at just over 8" long and 7-1/2" round with my foreskin left in place, 7-1/4" with it pulled back. All I know for sure is I've never put anything that big up my ass and was worried about Jim.
When I got to the trail head he was there in his hiking outfit, a plaid button down shirt, drab shorts and mid-calf hiking boots with red sock ends sticking out. He looked like an LL Bean catalogue model. I was in my regular old tan cargo pants and a beaten but trusty wool sweater I've had for 20 years. We chatted about what we had brought for food and beverages because we did not plan together and sorted out the gear which we split between our packs... ready for the forecast of rain for 3 days. The hike is about 6.5 miles and it is uphill for sure, I've hiked it a few times and it will get your heart pounding. We locked up the trucks and headed up the trail.
It was warm and still buggy out, the mosquitos had not taken the hint from Mother Nature to sleep despite it being the first week of December so we slapped on some bug dope my wife makes that does not smell like a chemical factory, but works well and we continued. We stopped a few times to catch our breath and once at the overlook spot that offers an amazing view south-east into the Georgia flat lands and in general talked about work, trucks and kids on our way.
The campsite we were hiking to was first come, first serve and we were apparently the only ones coming because it was moments from dark and no one else was there which meant we got the lean-to! The weather was not in our favor and having a lean-to to setup in was a glorious bonus, we would be on a raised wooden floor and have a roof to keep the tent from the rain and a place to sit in front that was covered by the roof. It would become our kitchen, living room and bedroom for the next few days.
We lit the lamp and Jim put the tent up while I gathered some firewood by headlamp in the woods and lit a fire. We decided to cook Big Bill's Beans and Rice from its dehydrated package, complete with chocolate pudding and orange drink. I told him,
"It's a meal for for a King!"
Then I whistled for a dog to come, patted my leg and said,
Jim laughed and we ate. I spiked the orange drink with shine and we had an enjoyable hour by the fire before the rain rolled in. The wind that came with the rain was blustery and we were getting wet, even under the roof, so we decided to pack it in for the night and headed to the tent.
As soon as we were inside I asked,
"Are you ready for this?"
"Yes. I've been dreaming about and jacking off to the thought of it."
I realized at that moment I've never hear Jim say yes directly. If I ask him a yes/no questions he will say, I reckon, Oh hell no!, Ummhmm, nod or just go into a story about agreeing or disagreeing.
"Come here" he said
and he reached in and pulled my shirt off, rubbed down my chest and pulled me in for a kiss. One thing we are is passionate kissers, I could kiss him for hours but like all kissing eventually someone has to make the next move and it was Jim. He laid me down on my back, stood up and stripped himself, reached down and pulled my pants off and knelt right between my legs and sucked my dick until I was wriggling in ecstasy. I pulled away and rolled him over before I blew and it was time to put all of my academic research to work. I got out the bottle of anal lube I picked up online, lifted his legs up to my shoulders and began by riding my tongue around his hole, I looked up at him and he said,
"I can't believe I'm going to let you put that thing in me."
I stopped and replied,
"Well I've let you put your thing in me several times and it was awesome."
"I know, I know, I'm just scared its gonna hurt."
I eased his fear, I think,
"I'll take my time, I'll be gentle and you'll be fine."
"All right." he said
and plopped his head back on the pillow and I started in again. I hear him ask if I'd taken Viagra and I pulled off his dick and said,
"Because Pop-eye's strong to the finish and I want to be sure there's gonna be a finish."
I told him that,
"You're probably so tight I'll last ten seconds if I'm lucky."
and went right back to rimming the shit out of him. After it felt like he was going to come, I stopped and dripped some lube on his ass and rolled my pointer finger around in it. I played around his hole with my finger and slowly slipped in one knuckle, then two and decided that was a good depth for now and twisted it around, I could feel just the edge of his prostate and decided ½ inch further would do the trick and I did. Once I could feel his walnut sized g-spot I traced the outline of it and softly rolled around over and over in small circles. He was moaning wildly and jerking around slightly. I could feel his tight ass loosen just slightly after a few minutes and I decided on two fingers, so I started to suck his dick while I lubed up my middle finger also, overlapped the tips of my fingers and pushed them in while twisting slightly and I was able to slide them both in about half way and Jim jerked slightly and his ass tensed. I stopped moving my fingers and went to licking his ass just above my fingers, his ass had a little nub at 12 o'clock and it loves to be licked. Once his ass let go of my fingers I just twisted them without going deeper for a few moments and pushed past my second knuckle and flattened them side by side. I could tell Jim was deep breathing and asked,
"You OK up there?"
"Yes." he answered on an exhale.
Now I had 2 fingers in far enough to tap dance on his prostate if I wanted, so I did. He had been running a finger up and down the bottom of his dick for a while so I took his hand and looked at him as I put his finger in my mouth and sucked it and laid his hand on his stomach and took his dick and sucked it while I was tripping the light fantastic around his g-spot. He said,
"I'm gonna cum, let me finish"
So I pulled off and let him work himself, he was grinding his ass against my fingers and arching his back and rolling his hips a jaw dropping load blew all over his chest. I cannot control myself when I see that, so I moved to his side and lapped it all up making sure to give his nipples a long slow lick. He was holding his breath and as he let it out just said,
"Jesus" and smiled.
I had taken the opportunity of him grinding his ass to stick my fingers in up to the hilt, he didn't even seem to notice and I was now just twisting them slowly 45 degrees from side to side. He was pretty loosened up and his hole stayed slightly open after I pulled my fingers out and I asked him if he was ready.
"Yes, I want it in me, do it."
I don't think hotter words have ever been spoken to me and I was just as ready.
I slipped my folded up sweater under the small of his back, lubed up his crack, slathered my dick, pulled back the foreskin and slathered my head. I slowly circled his ass with my foreskin forward which felt incredible, then I slowly pulled back to reveal my head and pressed it against his now fully puckered hole.
I was kneeling and his ankles were on my shoulders, I pushed my dick down to his now puckered hole and gave it a slight push that had no effect, so I pushed a little harder and in it went just past the head and I stopped and looked up at Jim. He was wincing but then he looked up at me and said,
"No, it's just weird feeling."
I didn't have the heart to tell him he had 1" of 8 potential inches in there.
So, I did, I pushed another 2" in until my head was past the tight part and I stopped and looked at him again. He looked like his eyes were about to explode out of his head, he was not breathing, just mouthing words I could not make out. So I stayed perfectly still and so did he. After about 30 seconds he said,
"No, it's just massive and I need a minute."
So I leaned down and gave him a long kiss and left the kiss planning to caress his neck, chest, pits and arms without moving my hips. Once I made it to his pits he was grinding his ass against my dick pushing more of it in and scooted down lower to be able to get more of it. When I was done with dressing him with my tongue I leaned back up and he had taken all he could, my foreskin was bunched up at the base of my dick stretched tight inside so I pulled out slightly and slid back in a few times and Jim gave the go ahead nod so I slid out a little further until just my head was in and pushed back in to where I was before. He seemed to like that, so I did it a few more times, each time sliding in just a little further. I was happy with the depth and on one out stroke his ass clenched down hard and my dick popped out, so I put it back to his hole and pushed it back in. He grabbed the sleeping bag in his clenched fists and said,
"Roll over, I'm gonna ride that thing."
So, I pulled out and rolled to my back, he sat on my stomach, knees at my side, took my dick in his hand and squatted down on the head, then squatted harder and took the rest of the shaft as far as he had been before and began riding up and down and back and forth super slow. He even ran his arms up in the air feeling them entwined with eachother, then ran his hands down behind his head, down to his chest and back down to my chest. Up until this point I was 100% concerned about him, but now he was driving and I was just realizing what it felt like for me. Ass is nothing like pussy and if someone says , "Ah! It's just a hole they're all the same" they've never had one of them.
His ass was uniformly tight wrapped around my cock but there were 2 tights; all the way in tight and fucking aircraft cable tight for the first 3 inches. I could also feel his muscles contracting turning already tight into bone crushing tight and I could tell he was squeezing them on his own accord. I knew already that I loved my head bumping into aircraft cable tight on the way out and slamming back in. He reached down and pushed my arms above my head and held them there with both of his arms, his meaty chest above my face, as he rode in circles and back and forth and up and down. He was fucking hot to watch and he was clearly in an erotic, sensual and other world of new sensations. I could have blown my load looking at how much he was enjoying this, he made it so erotic.
I told him I was going to cum and he said,
"Oh, no. You're going to have to wait." So he stopped completely and just sat there looking down at me.
I said, "Wait for what?"
"Me to come."
Rolling my eyes wide, "Ohhhh.... You want any help with that?
So I reached down and took his dick, my hand still lubed up from the fingering session and started to crank it. He slowly began to move again and I started to match his speed on my dick with the speed of my hand on his. I knew he was close when he took over so I reached up with my hands and pinched his nipples.
What happened next was something I've never seen before, it looked like he was in a try-out for a part in The Exorcist. He twisted, bucked and contorted into the most amazing shapes while he screamed at the top of his lungs,
"Holy fuck, holy fuck, holy fuck!"
Then in a low grumble tone right in my ear,
"Fuck me, slam that dick in me as hard as you can"
So I did, I pounded my cock as hard as I could as he came down, I slammed up, arching my back making sure he got all I had. He held my neck and choked me just a little with his weight which was fucking hot.
I could really feel all of his strength and weight now, he was tossing me around under him like a rag doll and I was doing all I could to help him out.
Finally, after what must have been a full few minutes of this I was going to come so I reached up and twisted his nipples and he came so hard it blew over my head in about 10 squirts. I've had mutual orgasms, but this one was like we were in the same fucking body. Each time he slammed his ass down and my oncoming hips bottomed out he blew a load that was exactly timed with my own ball pumping orgasm. When we were done pumping all the nut we had he collapsed on me and we laid there speechless, it was hot having his heavy hard body just lay there limp. I don't know what brain chemicals are involved in an orgasm, but we were overdosing on them. It was 30 minutes before we moved and he rolled off of me and another ten before I spoke.
"So, how was it?"
"I feel so empty."
Concerned I asked what's wrong?
He said, "When your dick slid out... I felt empty"
"Oh, I had that last month when I let this guy fuck me for the first time. I cured it by having him put it back in there occasionally." He laughed, I spooned him, blinked and it was morning.