Well my last memorable excursion with Jim came right before I entered college.
I was continually seeing Jim on a regular basis. One day when I had visited him, he had suggested that we should get away for a weekend up at his cottage. Summer was coming to an end, and Jim hadn't gone to his cottage for almost a month. With my work schedule, and of course with the family, this made it tough. However, after some switching of shifts, I managed to score the upcoming Labor Day weekend off. I would tell my mom that I was going away to a buddy's cottage of mine for the weekend with a group of friends. She bought the story, and let me go.
I arranged to have Jim pick me up from my work. I packed only one bag, which I brought along with myself. We would leave the Thursday night from my work, and would travel up to his cottage. I snoozed on the way up. It was about a two-hour haul to Jim's cottage, but we eventually made it. It was a quaint two bedroom cottage. It overlooked the lake, with a small path that led down to a small beach and the lake. The cottage was surrounded by woods. We unloaded our stuff, and we called it in for a night. I passed out in the guest room, as I was very tired from the day.
The next morning, I awoke to breakfast being made. We sat and ate breakfast. I took a strole down to the lake. Out on the lake, there was a small raft anchored out just a little ways from the beach that could be easily swam to. Jim had a boat as well that was rowboat that was beached. Jim's cottage was on a small lake. There was no activity on the lake. I'd learn that his cottage was one of five cottages on the lake. Most of the cottages were to the southern part of the lake, which were out of view from Jim's cottage. Jim's cottage was to the easternmost point of the lake. There were a few new cottages being built to the north side of the lake. I decided to go for a swim after breakfast. The sun was out, and the temperature was right for a swim. I hopped into my Speedo's and took a swim. Jim would join me a few minutes later. He strolled out in a robe. When he disrobed, he was completely naked. I thought this as being bold of him, especially if anybody was to pass by the cottage on a boat. Jim came out into the water. I questioned why he was being so bold. He'd explain that nobody passes by his cottage at all, and that his portion of the lake was quite secluded. The only traffic came late at night when people were combing the lake for fish.
He swam out to the raft, getting onto it, and diving off of it, naked in all his glory. He would eventually convince me to lose my Speedo's, which I did. We skinny-dipped, boldly during the day time, however it was Jim's confidence which let my inhibitions go. We would eventually go and dry off on the beach, and tan for a bit. We talked about his cottage, and how long he had owned it for. Eventually we'd stroll back up to the cottage for lunch.
After lunch, we had decided to go for a hike. I put on my t-shirt, and some shorts with my hiking shoes. Jim put on his tank-top, and some athletic shorts. He took his camera with him, and we brought a couple bottles of water with us. Jim would lead the way, deep into the wooded area around his cottage. We would hike for quite some time. We passed by some of the cottages to the southern part of the lake. Jim literally took me on a tour of the lake. We actually hiked all the way to the western side of the lake, which looked right across from Jim's cottage. We'd stop to rest in a secluded area. Jim sat on a tree stump while I rested on a log. Jim decided to snap a few pictures of me. I jokingly lifted up my shirt, trying to do sexy pose, which Jim snapped. He then asked if he could see more. I was a little shy at first, asking if somebody would see us and joked about mosquitoes biting my ass. He assured me that nobody hiked through here. Again, I was shy and nerves took the best of me. Jim gave me a look of assurance and asked me to trust him. He walked over to where I sat, cupping my face and looked me in the eyes. His look sold me on trusting him.
I took my shirt off first. Jim snapped some pics of that. I slowly slid of my shorts, and my underwear. Jim started to snap pics. I was his model, and he was my photographer. I layed against the log, in a sexy position for him. Jim snapped away, exclaiming that that was good. I proceeded to touch myself, getting myself hard. Jim snapped away, smiling. I would go the nearest tree, and posed. First I posed with my ass out, and finally posed against the tree, with myself jerking my cock. Jim loved every pose I did and snapped away. I must admit that was immensely turned on by doing this. I stared at Jim lustfully. I think he knew by the way I looked at him. His hand touched my chest, while his other caressed my cock. I closed my eyes. I was in extacy. He pressed his lips against mine, gently kissing me at first, before diving his tongue into my mouth. I deeply kissed him, taking his tank top off. My hand went for his cock. I felt his hard-on against his shorts. My inhibitions were gone. I didn't care if anybody would see us. I wanted him.
I pushed Jim against the tree, and took off his shorts. It exposed his massive cock. I didn't care of the sweat that permeated us. Lust had taken over me. I got to my knees, and immediately took his cock in my mouth. I engulfed him and sucked like crazy on his manhood. Jim moaned with every bob, and every lick on his cock. His hands reached for my head, controlling my bobs. I tasted his pre-cum. I knew I was getting him off. He would snap some pics of me sucking on him. How he managed to do this while getting pleased, I do not know, but it certainly took some skill from not shaking the camera. He lifted me up again, and we again kissed. Jim put down the camera, and positioned me facing the tree. He got to his knees, and spread my cheeks. His tongue dove into my ass and he tongued my hole. His saliva slobbered it up. I would get into a more doggy style position, as he got more of my hole. I grabbed the tree, moaning. Jim tickled and tongued my hole to no end. He spat his saliva, getting my hole nice and moist. He slipped a finger into my ass, continuing to tongue me. I started to jerk myself off while he did this as the pleasure was immense. I wanted him to fuck me, and made it clear by telling him that.
Jim lathered his cock up with saliva. My hole was covered with his saliva. I wasn't a fan of barebacking, but with Jim, I did not mind. He shoved his cock against my hole. Slowly it slid in. The sweat and saliva eventually eased his cock in me. I let out a moan. Jim began to fuck, first slow, but working up a pace, gripping my ass. With every shove, I moaned. He moaned along as well. I braced myself against the tree, with one hand on my cock jerking myself off. My moans echoed in the forest. I was in complete pleasure. I was loving every minute of it. I would eventually bring myself to cumming, splatting my cum against the tree, moaning loudly while cumming. Jim eventually worked up a fast pace. He asked if he could cum in me, and I give him a loud "yes". Shortly after I felt his cock begin to spasm. He shoved one last time before his cock erupted in my ass. I felt the warmth of his cum inside me. Jim moaned loudly. He pulled out. I must have had gas as I farted out some cum. It oozed out my us, running down my leg. I used a leaf to wipe it away. We got dressed again, resting a little after our workout. I told Jim I had wished he had caught us fucking on camera. He wished that too, however said that he might be able to fulfill my wish. I was a little puzzled by this. We walked back to his cottage from where we were. It certainly was the enjoyable hike.
When we got back to the cottage, I took a shower to wash away the sweat. I cleaned myself up again. Jim prepared dinner for us. We had BBQ for dinner. It certainly filled me up. I emptied myself out after dinner, and had a quick washoff. I was very self-conscience of myself. I always made sure that I had a clean ass for Jim. My biggest fear was having an accident while having sex, so I always made sure I was clean and ready. After dinner, we shared a drink outside, watching the sun go down. We decided to go inside as it started to get cool. Jim then said he had a surprise for me, as we were walking up. We went to the cottage. Jim ushered me to the guest bedroom, and said to put on something nice for him and that he'd call me when he was ready. I was quite puzzled but went along with it. I went to my travel bag, and rifled through, finding some nice tight white briefs. I went to the guest bedroom, and undressed, dressing in my little outfit, waiting for Jim's words. All the while I wondered what he had planned. After quite some time, he called me out. I walked into the living room. Jim had the fire going in his fireplace. He had put out a fur rug just in front of it, of what material, I was unsure of. There set up was a video camera. His old television set was hooked up to the camera, and it was filming the area he had set up in front of the fireplace. He said that I wanted to see myself in action, so he had set something up to that effect. I was laughed, but was a bit nervous. It would be my first time filming a porno and I was a little scared. Jim was dressed in a robe. I could only imagine what he had underneath. I asked if we were going to actually do this. He replied we didn't have to if I didn't want to. I was turned on by the fact I was going to be on film, let alone right there on the TV. My inhibitions though always seemed to be let go with Jim, and I went for it.
Jim set up the camera to record. I gave Jim a look to come over to me. We started to make out. Jim grabbed my ass as his tongue meshed with mine. I peeked out to see what was going on and sure enough the camera was catching everything on the TV. I felt Jim's hard cock poking through his robe. Sure enough he was naked underneath. He began kissing my neck, and then down to my nipples, sucking a bit on them. I was immensely turned on. I began stroking his cock underneath the robe. He was fully erect and hard.. I began to unravel the robe strap, and parted his robe, exposing his rock hard cock. I got to my knees, stroking his manhood, looking at the camera doing this. I asked if he wanted me to suck his cock. He obliged. I licked his hood of his cock, staring at him in the face. Jim closed his eyes while I did this. I started licking alongside his shaft slowly, working my way up to the hood of his cock, sucking on it. Eventually he couldn't take anymore and asked me to suck his cock. I took Jim's cock in my mouth and started to bob. Eventually I worked up a good pace, and I moaned in pleasure, sucking on his cock. I couldn't see much from the TV screen, but I caught a glimpse of myself going down on his cock.
I pulled away from Jim after a quite a bit of sucking. He got to his knees and kissed me again. He pushed me on my back. He went for my shorts. I was hard already, getting turned on by sucking on him. I let him slide my briefs off, exposing my hard cock. He took off his robe, and Jim got on top of me. His cock touched mine, and he started deeply kissing me again. My cock rubbed against his, sending goosebumps on my body. My hands grasped his ass as Jim rubbed against me while kissing me. Eventually I wrapped my legs around him as well. He then asked if I wanted his tongue on my ass. I responded quickly, obliging him too. He turned me around facing the camera. He spread my cheeks wide, spitting on my hole. He quickly dove his tongue into my ass, and started tonguing my ass. His moustache tickled my ass, while his tongue lathered my hole. I was in extacy. I moaned while he did this, trying to make my porn star moans for the camera. I jerked my cock while he did this. I was loving every minute of it.
Jim couldn't take any more of the foreplay, and wanted to fuck me, making it clear, telling me that he was going to fuck me. He grabbed the bottle of lube sitting on top of the table and lathered my ass and his cock with the lube. He positioned his cock on my asshole, and slowly shoved in. His cock easily slipped in. He started slowly to fuck me, but started to work up a torrid pace. Soon he was fucking, hard and fast. I moaned loudly. It was the loudest I had moaned for him. I talked dirty to Jim, encouraging him to fuck me good. He started to moan from this. I turned to the TV, watching us on television going at it. It turned me on immensely. He continued to fuck me hard and fast. I continued talking dirty, telling him to "fuck me daddy". It got him off so good. I grasped the fur below. I couldn't take much more, and I moaned loudly, as I began to cum, bursting on the floor below. It wasn't long before Jim was going to cum. He pulled his cock out, turning me around, and holding my head back. He jerked his cock and moaned loudly. His cum splashed on face. I stuck my tongue out and tasted all of his sweetness. My face was covered with his cum. I wiped off some of the cum, licking my fingers of his sweet cum. We'd clean up and watch the video. Watching myself definitely was a turn-on again, and seeing my facial expressions while he fucked showed complete pleasure.
We'd tape again, but this time it was a solo job for myself. He taped me playing with myself and jerking myself off behind our fuck session. He would give me the tape as a keepsake. We'd spend our last night at the cottage, but we didn't fuck, and just spent a night in bed together, holding and kissing each other. We'd pack up the next day, and head back to the city.
Afterwards, I didn't see Jim as much because I was busy with school. Whenever we got a chance, we'd see each other and enjoy our time with each other. It was like we hadn't seen or fucked each other each time we had our little sessions. However, as time grew, they'd dwindle and dwindle. Jim got busier at work, and myself, busier with school. Jim would eventually tell me one night that he was leaving the city, for work. He'd eventually move out of my building in November. I was devestated. I actually started building some feelings for Jim. He truly was my first boyfriend and broke me in well. I would go on a drought of sex for quite some time. It wouldn't be until the following year that I'd have sex again, and a new encounter with an older male, which I'll share with my next story.