Finally My First Time Pt. 03

It's been a while since my last chapter. The reason for this is that I met a girl and settled down. I truly thought that I'd found the right woman for me. Then Covid hit. We were trapped together in my house twenty-four hours seven days a week. At first it was great, we were having sex constantly, sometimes even when we were working. More than once she went down on me when I was on a conference call while on webcam, it was so difficult not to show everyone my cum face.

This good time lasted about five weeks, after that boredom set in and the arguments started. The sex stopped very soon after that and within two months she'd moved out. I was home alone, bored and lonely every day.

It was during this time I began to masturbate a lot. I was constantly at it sometimes four or five times a day. I began to reminisce about my time with Nick and the couple in the hotel. My arse hadn't been fucked in so long it had tightened back up. I began to slip myself a finger or two when I masturbated, I was so tight I couldn't even get a third in. So, I decided to buy myself an anal trainer kit and dildos to help ease myself back into being penetrated as I'd thrown my old ones away when I moved in with the ex.

Gradually over the next few weeks my arse became much more accepting and I gradually built up the size of my toys. I finally got to the point where I really wanted the real thing and felt my hole was ready. So, I did what I did the first time, I went onto a gay chatroom. The site was nothing like I remembered, it was full of spam, lots of subs looking to be dominated and any tops were just utter degenerates. It was a complete mine field, any guy you spoke with would have a weird fetish. I'm no prude but these were on a level I wasn't prepared to go to. So, I turned to the apps, there was no luck there either. The problem was nobody wanted to meet or they were also perverted and there's only so many dick picks you can sift through.

I got a call on a Thursday evening from work asking me to call to site the next day to pick up some new equipment. To be honest I was pleased to be getting a break from being in the house. The next day I set off around eleven after I finished some outstanding work from the day before. Work was about an hour away. It was a lovely warm June day, I had the windows down and the music blasting. The roads were quiet, I was enjoying my drive and being out the house finally. I arrived at work in record time.

I didn't stop to talk to anyone in the building, not that there were many to talk to. I put the equipment in the boot of my car. I didn't want to head home straight away and I wasn't expected back at work for the rest of the day. I quickly remembered about a nice picnic spot next to a race track set in the grounds of a large private estate nearby. It had a large grass area and also some woods. I thought about stopping there for a break and to enjoy some sun. I wasn't sure if it was open so I took out my phone and googled the area. The result showed it to be open, most of the other results showed cancelled race events but another link caught my eye. It was a newspaper post from three months earlier. The headline titled, "Local's fury as gay cruising in woodland." I read the article with some intrigue, it mentioned encounters with men doing things from masturbation, to various kinds of sex acts. The date set this around the beginning of lockdown but I thought it was definitely worth a look. So, I started my engine and set off.

I pulled up in an area just outside the estate because I didn't want my car to be seen inside the estate and I didn't want to get trapped inside if they closed their gates early. I was really nervous but at the same time I wasn't expecting anyone to be there. I left my car and walked along the road into the estate. It's a really lovely walk into the estate, the road is flanked by woodland on both sides. It's really quiet except for the singing of the birds and the gentle rustle of the leaves. It's just past lunch and the sun is high in the sky as I make my way to the entrance of the woodland.

I walk about fifty yards inside. The woodland thinned out a little and I had a look around. The place looks deserted. My nerves subside and I relax, I'm enjoying my afternoon stroll in the woods. I get deeper into the wood. I walk past an area with a lot of thick bushes when I hear a noise. It's the sound of wood snapping, I stop and look around. There is nobody around from what I can see, I wait mouth open, taking quiet breaths, listening intently. I stay like this for around a minute when I spot two men emerging from the bushes around seventy or eighty yards away. I can only see the back of them as they are walking away from me back in the direction of the entrance to the woods.

I wait until they are out of sight and head towards the area where they emerged. There's a small well-worn dirt path leading up between the bushes. I follow the path until a small clearing appears in the middle. It's not big at all, probably a two-meter circle. The path cuts through exiting on the other side. I quickly identify the area as being the main meeting point as it's littered with condoms and both male and female underwear. The vegetation is flattened down in places, probably by people either kneeling or laying down.

My mind begins to race just thinking about the things that happen here, my heartbeat quickens and my cock begins to harden. I stand there for a few minutes, I think about masturbating and how dirty and exciting it would be. I walk back to the entrance of the path and check the area. The place looks deserted, so I head back and continue further down the path to see where it leads to. The path weaves and meanders around the bushes before coming to a dead end probably around forty meters from the clearing.

I head back to the clearing and after a brief look around, I dropped my trousers to my ankles. The warm summer breeze felt amazing on my balls and my semi erect cock. I take a hold of my cock and begin to stroke it. Within seconds I'm hard, I close my eyes and begin to imagine a cock being in my hands, mouth and even fucking me. The smells and the sounds sweep over me and I quickly lose sense of my surroundings. With my free hand I reach around and begin rubbing my hole, the sensation is amazing coupled with the slight warm breeze. I attempt to widen my stance to allow better access but stumble instead. I crash back to reality just long enough to prevent a fall and to catch a glimpse of a man standing in the pathway.

I panic, grab my trousers, pull them up and take off in the opposite direction. I quickly realise my mistake that it's the path towards the dead end. I reach the end and freeze. I look back down the path, heart in my mouth. Who was he? Is he going to report me? What's he here for?

I didn't have to wait long, soon a quite tall and very thing man rounded a bush. Wearing shorts and a hooped t-shirt, he walks towards me. He looks to be around his forties, short hair slightly spiked up and very long legs and arms. He isn't a bad looking guy to be honest, he's kind of nerdy looking which is accentuated by the glasses on his face.

He closes the gap on me very quickly. Soon we're less than a meter apart. He towers over my 5'10" frame probably standing at 6'5 or so. We both stand and look at each other in silence for what seems like an eternity. My heart's in my mouth, my throat feels like I was being choked and my stomach feels like it want to empty its contents onto the floor.

"Wha...What are you here for?" He says eventually sounding very nervous. I freeze I no longer knew the answer to that question.

"I don't know," I reply.

"I saw you masturbating, why did you run?" He asks.

"I don't know," I reply again.

"Is this your first time here?" He asks. I fail to answer. "Don't worry its pretty quiet around here there's very little chance we will get caught nobody comes this far up to be honest and if they do, they'll just watch or leave us alone," he continued.

"Ok," I reply, I suddenly realise my conversation skills are very much lacking at this point.

"Why don't you take your cock out?" He asks.

I nod at him. My hands are already grasping my trousers to hold them up, as I hadn't managed to close them back up and my balls are being squashed by the band on my underwear. I let go of my trousers and let them drop to the floor and quickly slipped my underwear down. He leans in and kisses me while his hand makes its way down to my soft cock. His hands are huge and my cock feels so small in them. I waste no time in reaching up and pulling down his shorts. With my head tilted backwards accepting his kiss my hands feel around for his cock. It was soft but still felt pretty big in my hands.

I begin to gently stroke his cock which begins to grow and harden in my grasp. I quickly become aware I'm now fully hard too. I break the kiss between us and look down at our cocks. His hands make my seven-inch cock look tiny, meanwhile his cock sticks straight out towards me, probably around eight inches, possibly more and reasonably thick. I remove his hand from my cock and squat down in front of him. I aim his cock at my mouth and lean in to take it into my mouth. Excitement bursts from within my body, I'd missed this way too much as I begin to lick and suck his cock with huge enthusiasm. I feel his giant hand wrap itself around the back of my head as I bob and suck his cock.

"Oh fuck! Yeah!" Comes out of his mouth, "Just like that," he continues. I look up at him, his eyes are closed and his head is slightly tilted back. I begin to play with his balls and he moans even more. I'm really enjoying myself and the moans just encourage me to keep going. I put his cock right to the back of my throat and start to force his cock against it, I choke a little but persist. A few seconds and with some gagging, with a pop his cock slides down my throat all the way to the base. I try to stick my tongue out to lick his balls but this causes me to gag more. I withdraw to catch my breath before going in for a second go.

"Oh my God, you're amazing," he says.

I hold this for a few more seconds before withdrawing again to catch my breath. This time when I go to put his soaking wet cock back in my mouth, he stops me. He stands me up, takes hold of my cock in one hand and moves around to the side of me. I feel his hand on my arse as he stokes my cock with the other. His fingers enter my arse crack and I feel them moving deeper probing for my hole. One of his fingers rubs over it, I feel a shiver come over me. I quickly questioned if I wanted to go further right there in the woods. He leans his head behind me and I hear him spit which is almost instantly felt very near my hole. His fingers quickly move the spit and begin to rub it into my hole. He lets go of my cock and uses that hand to bend me over. I feel his arm over the top of my lower back as he uses his hand to spread my arse. His fingers leave my hole and a second later I hear him spit again before quickly returning to rub it into my hole again.

This time after a quick rub I feel the tip of his finger begin to apply pressure to my hole. The tip enters first for a few seconds before withdrawing, he spits again and his finger probes again, this time for longer with some gentle movement in and out. He begins to edge it deeper into my arse, I feel the knuckle enter me. His finger alone felt like a cock it was so large. He continued to finger my arse and the longer time went on the more my hole begins to accept his finger. He withdraws the finger and spits again, this time I feel way more pressure as he introduces a second finger to my hole. This time he doesn't even take it slow as both fingers enter my arse as far as he could get them. The sensation from this is one of pleasure and some pain as my hole is force to quickly stretch to accommodate the extra digit.

At this point I feel quite stretched as he begins to finger fuck my arse with his two fingers. I try my best not to clench and I try to relax. I focus my efforts on breathing and relaxing and this helps reduce the uncomfortable feeling of my hole being stretched out by his two large fingers. He removes the fingers from my hole and he moves his body behind me. I look back over my shoulder as best I can and I watch as he kneels down behind me. He reaches up and places both hands on my arse, thumbs inwards very close to my hole. He spreads my cheeks apart as he leans forward and begins to gently lick my arse. It feels great as I feel his tongue licks and probes my hole. He spits on it again and resumes licking. I'm surprised at how far I feel his tongue is able to get up into my arse as he practically buries his face in my arse crack. At this point I can feel all the saliva make my hole feel very wet. At this point I'm feeling practically euphoric at the thought of what might happen next.

He stops after a little while. He motions for me to get down on my knees, I step out of my trousers and do as instructed. I look back at him, his cock pointing directly at my arse. He reaches into his pocked and pulls out a condom. He proceeds to open it and I watch as he slides it over his cock. At this point I'm so excited condoms are the last thing on my mind and I'm a little disappointed he wouldn't be shooting his load in me.

Soon its on, he grabs my hips and I adjust position closer to his body. My ankles and knees together and my arse up with his legs either side of mine. I reach back, take a hold of his cock and place it against my hole. He takes hold of my hips and begins to apply pressure to my hole and his cock begins to enter me. I release his cock and get down onto all fours as he edges his cock deeper and deeper into my hole, stretching it more and more with each gentle thrust. Any little amount of pain is quickly gone as my hole relaxes around his cock.

My arse touches his pubic area I love the feeling that his cock is deep inside me. I feel his grip on my hips tighten as he begins to push my body away from him as he gently begins to withdraw his cock and before it exits my hole, he pulls me back towards him as he thrusts it back in slowly. It feels great and I realise what I've been missing. He repeats the motion several more times, I let out a small moan as his cock finds my prostate. For now, he keeps the pace going relatively slowly his technique is to withdraw almost fully then thrust back in balls deep inside me. I drop my head and look down at my hard cock bouncing and twitching with each thrust, pre-cum already starting to leak out as part of a thin silky thread dangling from my cock.

I'm so excited I'm overcome with the need for it harder. I take a little of the initiative from him and start rocking back onto his cock to meet each one of his long thrusts trying to up the pace each time. He takes the hint and each thrust becomes progressively harder and harder. I moan as a slight pain meets intense pleasure radiating from the nerve endings in my hole.

"You like that?" He grunts.

"Yes!" I reply.

"Fuck me. You're a good little whore!" He says forcefully.

"I want you to fuck me!" I reply. "I don't want you to stop until you cum!"

"I intend too!" He replies.

He adjusts his grip on my hips once more, his arms now dictating how fast my body moves to meet his long thrusts. The power and tempo of each thrust continues to increase, pain and pleasure in just the right measure cause a wave of endorphins to flood my body. I feel the tell tail signs of a building orgasm inside my cock which is amplified tenfold each time his cock hits my prostate.

Again, I look down between my legs. My hard cock flapping all over, pre-cum going all over. Long threads of it forming and snapping and quickly being replaced over and over. He stops suddenly then withdraws his cock from my arse.

"Why did you stop? Did you cum?" I asked, devastated as I'm so close.

"No, no!" He replied as he stood up. "I'm just changing position."

He shuffled forward and stood over me a little. He places his hand on my shoulder and puts his weight on top of me. I see his legs squat down a little and he guides his cock back to my hole with a fresh coating of spit.

The new angle was perfect, he is a little higher than my hole meaning his cock angles slightly downwards which is perfect for hitting my prostate every time. He brings his other hand up to the side of my neck his fingers wrapping around the front of it applying a slight pressure to my throat. I feel the saliva residue as it rubs off onto my neck. He builds his rhythm up slowly at first adjusting and finding the right position. He begins to pull back on my neck and shoulders as he starts to thrust harder and faster. I love the sensation and with each thrust I teeter on the brink of orgasm and the small pressure on my neck causes a small euphoric feeling in my head.

He grunts and begins to pound my hole as hard and as fast as he can.

"Fuck! I'm about to cum!" He exclaims.

"Me too! Don't stop keep going!" I exclaim while gasping for breath.

Knowing he's about to cum sends me over the edge. With hard thrust after hard thrust I grab two handfuls of the forest floor, push my arse out allowing his cock as much opportunity to get as deep as possible into me. Seconds later I let out a very loud moan and gasp as my cock releases an amazingly intense orgasm. My whole-body spasms uncontrollably. I watch as cum squirts out of my cock, my arms give way but the hand round my neck keeps me up, choking me a little more which only serves to heighten the pleasure more. I can barely stand the pleasure taking over my body. I become aware my hole has contracted tightly around his cock. He lets out a loud moan and forces his cock deep into my hole. I feel his cock pulsing away inside my hole, I love this feeling but he quickly withdraws his cock. I look back over his shoulder and watch him remove the condom quickly. As soon as its off he begins to masturbate furiously for a few seconds. Then without warning he grabs my hip with his free hand pulls me closer and slams his cock straight into my arse. I yelp in pain briefly as he buries his cock deep in my arse. I feel his cock spasm and twitch inside me quickly followed by a warm sensation deep inside me.

"Oh my God!" He exclaimed as he puts both hands on my mid torso and uses it to support some of his weight.

"Now that was a good fuck! We'll have to do that again," he continued.

"Definitely!" I reply.

He slowly withdraws his cock and stands up his cock quickly going soft. He reaches down to pick up his trousers as I stand up and dust off my legs. I feel his warm cum begin to run out of my arse. My shirt slides down from up around my shoulders I feel it cling to my body in the areas where his cum had dripped down onto my lower back.

"Do you come here often?" He asked.

"This was actually my first time," I reply.

"Ah so that's why you ran! Well just as well I caught up to you, isn't it?" He says with a chuckle

"Yeah, very much so. I really needed that," I reply.

"Well, I'm here two or three times a week. You strike out a lot as there's not always someone here and at the moment its very quiet with what's going on. Its usually quite a mature crowd that come here and a lot are staying away." He said.

"Well, I'll definitely be back so I hope we cross paths again," I reply.

I use my underwear to clean his cum off my arse, inside of my thighs and lower back and slide my trousers back on. By now were both dressed and begin to walk. We head out of the thick bushes back towards the entrance making small talk along the way. Once back in the carpark we say our goodbyes and I head to my car.

I sit there for a few minutes by body sticky with cum, arse a little sore and stretched but overall feeling satisfied with plans already to return soon.