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,
"Here King!"
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