Teenage Encounters

By James Woodard

Published on Jan 9, 2012

Gay

The following series is a continuing series of fantasies which i have been experiencing for a few years about some of my classmates from my school life. Names have been changed. Hope you enjoy and i would appreciate your feedback. Thanks. Please don't reprint it, in part or in whole, without permission.

This is the second part of the series and there is ongoing continuity so some parts may not make sense unless you have read earlier parts which can be found elsewhere in this archive. Thanks for reading and i appreciate any feedback from readers at my email address.

I watched as Brad knelt down on the floor and brought a box out from under his bed. It was padlocked shut. He went to his drawer, opened one of the boxes of condoms and produced a cleverly hidden key, which he used to unlock the padlock, opening the box to reveal his supply of what could only be lube. There were six massive tubs. He certainly wasn't going to run out any time soon. He produced the tub which had been opened and removed the lid. The tub was about three quarters full. I wondered how long he had had the tub as it looked like it would last at least a year.

`I'll cover my cock. You better lube your arse.' He advised, getting some lube from the tub onto his hand.

But that's not going to happen.' I said, putting it plainly. It's not fair if you get to cum twice and I don't. Here's how it's gonna go down. You can lube my cock and I'll lube your arse.' He smiled, accepting and getting excited at the prospect. He began slowly covering my cock with the lubricant and I could feel with each touch it was getting more and more slippery and my pleasure was increasing by the second. I breathed heavier as his hands flew magically over my cock, rubbing it in. I pulled him off me and pushed him onto all fours like a dog.

I moved in and slowly began to lick his hairless hole. It definitely tasted different. It wasn't the worst thing in the world but it certainly wasn't the best either. But because of the person who I was licking in this delicate place I didn't care and carried on to his delightful moans. I placed one of my fingers into his hole and gently wiggled it around, inserting another when he started to loosen a bit until he was able to house three fingers opening him up bit by bit. I slowly gazed as his cock deflated in size and then resumed its rise.

I slowly withdrew my fingers one by one feeling his hole instantly contract slightly attempting to return to its original size. Not that I was about to let that happen. I lifted his legs onto my shoulders like I had seen in porn movies and commanded him to Hold your butt cheeks apart.' I said, lusting for his tight boy arse. I need you right now.' I said, my brain yearning to take his arse cherry. I slowly lined my cock up against his tight hole, before gently pushing the tip of my knob into the extremely tight entrance. He gasped painfully as he kept holding his cheeks as the pleasure hit me like an explosion. I moaned in delight and noticing his gasp I slowly removed my cock a tiny bit before reinserting it a little further. We repeated this until I had just over half of my knob inside him. He soon adjusted to my cock size and that is when the real fun was to begin.

I told him to let go and felt the flesh near the entrance snap back into place and tighten around my cock. The pleasure was so immense due to the tightness of his virgin arse which delighted me beyond anything else. I began to increase my speed as I thrusted harder and faster into him, his screams of pain, which later turned into screams of pleasure, turning me on, with every whimper. At one point he screamed so loud I worried that anyone within a mile radius would be able to hear and was thankful he lived in a mansion and we were alone in the house. I kept pushing on, my climax now not just what I wanted but what I needed...

As I finally felt my orgasm approaching, I slowed down a little, which gave me a lot more pleasure when I finally felt my balls tighten and my cock jerked inside him as it unloaded. I felt like I was going to collapse from the pleasure and was unsure how I remained standing. After the last squirt left my cock, I slouched forward, my cock sliding out of Brad as I slid over his toned body and my lips found their way to his.

I lay still and after a minute, I felt Brad moving out from underneath me. I was still face down on the bed with my eyes closed when I felt a finger intruding around my arse. I guessed his game and allowed him to rub me and loosen me up. By the time he got the third finger in, I was crouched on the bed, ready to be taken doggy style, my arse was stinging and I was trying my best not to yell out in pain. When he put the fourth finger in me, however, it was all I could take and I winced quietly and he got the message, working at me again with three before I heard him soaking his cock in lube and rolling his foreskin back and forth with audible effect. When I felt his alien massive monster cock enter me for the first time, my arse felt like it would be ripped apart at any moment. His breathing spurred me on so I slowly moved my arse back and forth over his cock, despite the amount of pain I was experiencing.

`Oh, fuck, that's good.' He confirmed as he thrust into me as I leaned back on him, making his cock go deeper inside me. I moaned quietly as the pleasure turned into pain and then when we had both got into a rhythm, he reached down below me and started masturbating me with his right hand, while his other was on my back, supporting himself as he continued to thrust deep. His wanking was almost in time to his thrusting but I guessed the amount of pleasure he was in was preventing him from focusing on moving his hand any faster. I moaned louder as he continued to rub my foreskin over the extra sensitive head of my cock. I was in heaven, and I could feel my cock getting a little sticky from the lube still on his hand and also from the precum that was leaking steadily from the tip.

`Hmm. Take it like a bitch, baby.' He murmured as he was getting close to his climax, which I could sense from his frenzied need to suddenly thrust faster and deeper into me, his cock noticeably swelling up within my tight hole.

Feeling this within me led to the familiar feeling of a massive build-up of my own liquid and pretty soon his muscular hands had me squirting all over his bedcovers. I yelled in complete ecstasy as this happened and my arse started contracting which I'm pretty sure sent him into a whirlwind of pleasure and kick started the resulting explosion from his missile. He slowed down slightly and kept thrusting as jet after jet of Brad's man-juice launched an invasion on my no-longer-virgin hole.

I collapsed onto the bed, landing on some of my cum and feeling it sticky and wet on my chest. He turned me over and bent over licking my cum off the bedcovers and then from my chest, as I stroked whichever part of his body I could reach. After that he laid down beside me and took me in his arms. I did hold back, but I was extremely close to tears.

I had only ever imagined something like this event happening. And even my wildest dreams had never been this amazing. I could never have hoped in my entire life so far that my virginity would be lost to the man who I loved and would give my all, partly because he didn't seem gay in the slightest and I expected him to be into girls but, it was just what I had dreamed of for so many years. And because of that he would always hold a special place in my heart. Brad had changed dramatically in my mind. He was no longer the boy I had fancied for what seemed like millennia. He was now the man who had proudly taken my cherry and though I was now satisfied with what had come to fruition, what was to come would be even more of a shock. Because things with Brad were about to get even wilder...

Afterwards, as I lay cradled in his bulging biceps and resting on his pecs, we just lay there for what seemed like hours and talked. And even though it seemed like hours, it was no boring task. Because I was learning about the man I loved. We had many questions for one another. But it all started off with a simple, honest declaration.

`I dunno about you but that is one of the best things I have ever experienced in my entire life. It was the best, even though I haven't had any other experience in this matter beforehand.' I said, still at his side, unaware that I was about to start the conversation that would be the most important of my life so far.

`So what are you saying? That you are a virgin?' Brad asked, me sounding a slightly shocked.

Are you really that shocked?' I said, chuckling. Yeah I was, and I couldn't imagine losing my virginity to anybody but you in the entire world. To tell you the truth, I've had crush on you for ages. I've also wanked over you quite a bit, actually. You're my number one image in my wank bank, so it is quite nice to think that you are also now my first time.' I said, my hand stroking the big mass of muscle he normally hid under his sleeve.

You've wanked over me before?' He replied, again, sounding shocked. I wish I could say the same, babe, but I don't normally wank that much. And when I do it is over porn or just a cock, not an actual person. `And I wasn't a virgin before, although in the gay sense of the word, I guess I was. Never had an all-male experience before, just one time with a woman, when I was unsure of my sexuality, but, it was awkward and I knew as I was fucking her that I was definitely gay. And, tonight... well that just proved that theory 100%. I mean, your arse was just so tight, I wanna make permanent reservations in there. I mean, now that I know the difference between pussy and arse, there's no changing this mind.' He chuckled, and I smiled. Every sound he made was so sexy.

`Same here, dude, except for the fact that I haven't even done it with a woman before. You got one up on me there. I don't know how but I've always known since I was about 5 that I was gay. That's probably when I noticed my first attraction to men.'

Well, I'm glad that you are. I mean, even though, you have only wanked before, you acted as if you were really experienced and had done it about a hundred times.' He shook his head frantically, and I wondered what was going through his mind. Sorry,' he said, noticing I was staring at him, confused. `I just can't get it out of my head that you have wanked over me before. I don't see why, but it turns me on so much, I could just screw you again right now and I could probably last all night long.'

I smiled. Whilst that would be nice,' I confirmed, I have to be home quite soon as my parents will kill me if I'm not back by 1 o'clock.' I paused a second, before asking him the one important question, of which I was dying to discover the answer. `So, it doesn't matter if it doesn't, but does this mean we are kinda together now? I mean, in a relationship? You know, secretly?'

Yeah, I suppose we are.' He said, standing up and reaching out his hand to me. Come on, I'll give you a lift home.' I took his hand and he helped me up, where we began searching the room for our clothes before we got dressed and then he led me downstairs to his garage.

Brad had two great cars. I don't know much about cars but these ones looked amazing. He had a 2011 Bentley and a brand new Mini Cooper. He walked over to the Bentley and I followed. He opened the back door and played the chauffeur, holding it open, `Sir.' He said, nodding to me, and I got in without saying a word, acting the gentleman. I sat in the middle seat, as he got into the driver's seat, making sure he had me in view in his mirror.

`So how long have you had your licence?' I asked, not knowing that Brad could drive.

He smirked at me in the mirror. `I haven't. More exciting that way. After all, where's the adventure in getting a licence and driving legally.' This made me think and I realised that for me, being with him was all the adventure I needed. He tilted the mirror so he could see me more clearly and he turned on the ignition and set off. During the journey I kept glimpsing his eyes on me, and I couldn't tear my eyes from him, finding it unbelievable that less than an hour ago I had been involved in sexual acts with that very man.

After a while, I slowly took off my shirt and started massaging my nipples, knowing full well that he would be enjoying the show I was performing just for him, glad that he had tinted back windows. I unclipped my seatbelt, not caring about safety. I watched as he made glances back towards me in the back and whenever I saw his eyes on me, I moaned quietly, pretending I didn't know he was watching. I rubbed my pecs and pinched my nipples to give some variety in my motions and in my moans, then I had had enough of touching myself and I reached forward and began stroking his neck around his headrest, feeling his larynx moving up and down under my touch as he swallowed. I massaged his shoulders as best as I could and he smiled at me in the mirror.

`How am I meant to concentrate on driving when you are driving me mad and giving me a massive hard on?' he asked, directing the question right at me, but not in a non-the-spot way. I just chuckled and slowly took off my jeans, revealing to him the very obvious bulge in my boxers.

You weren't concentrating anyway, unless by driving, you mean, my body.' I smirked. And anyway, just looking at you gives me a boner, so as your boss, I order you to get in the back of this car and service me. Right now. My head needs some mouth action.' I commanded. His face revealed that he obviously liked being ordered around and he pulled into the next layby and turned off the ignition, getting into the back of the car with me, after removing his shirt. He strapped on my seatbelt, took off his belt and tied it tightly around my hands which he positioned above my head. `Ooh, blow job in bondage. What a way to finish the night.' I remarked, getting more turned on by being tied up. I tried to push my cock a little higher in the air so it was just that one bit closer to him. He pulled my boxers down completely and placed them on top of his head, covering his mop of hair. This sight was even more of a turn on.

After that, he bent down and took my knob into his deliciously warm, wet mouth and I was in another world. I closed my eyes and pictured all the acts of sexual activity me and Brad had committed that night which made me even more glad that we now had a real relationship. Kind of.

I lost myself in the moment and just blurted out my innermost thoughts and desires as he got busy on my cock. `You know, I wish I had a body like yours. Massive guns that a soldier would envy, huge pecs and the best six pack I've ever seen. Plus a monster cock. I mean, it's so big, I was scared to have it inside me.' I divulged, staring at the filled out jeans, smiling to think that he was also hard. In a tricky move I manoeuvred my hands over my head and down to his head, forcing it down further down on my meat. He began to choke a bit and I moaned in delight, his choking noises sounded so hot. I let go and he resumed normal sucking as my hands found their way down to his arse, clenching it as best as I could with the belt around my wrists.

He got the message and lowered his jeans for me, obediently. Then I managed to get his boxers down, which in the position he was in was no easy task and with that I did my best to move the foreskin back with my hands bound. He moaned so I took it that he was still enjoying my actions even if the movements did feel awkward to me. It wasn't long before I felt his cock enlarge, swelling due to the amount of cum flowing into it and I pointed his cock at my face and felt as three massive squirts of his steaming hot cum landed on my nose and some near my eye which I had closed to be on the safe side, having heard that cum stings in the eye.

He paused momentarily to look at me. `Work of art, babe.' He said, sinking down on my meat again after I licked some that I could reach with my tongue. While he was sucking me, I saw his hand move up towards my face and surprisingly, he scooped some onto his finger and lowered it to his mouth, delicately sampling it.

`Oh, you swallowing your cum is such a turn on.' I whispered, as I let my torrent of semen loose to his eager mouth. He gulped in his efforts to swallow it all and he managed to get most of it although some did dribble out a little bit but he licked it up after swallowing the rest.

Suddenly we noticed another car indicating to turn into the layby and suddenly the look on Billy's face turned to panic. He tossed my boxers from his head and they landed on the floor. `Quick, get out.' He said, pulling up his boxers and jeans and opening the door on the far side, which would not be seen by the vehicle approaching slowly towards us.

`Why?' I asked, wondering what the big fuss was about.

They'll check the license.' He replied, seeing that it was as he had feared: a police patrol car. It's not registered to me. It's my butler's. He did it as a favour so I had something to drive. They'll know I am not a 45 year old man, don't you think?'

`But I'm naked!' I said, nervously, horrified by the prospect of being caught like this.

`Well, get out and I'll grab your clothes. Quick before they see us, unless you'd prefer to be spending the night in a prison cell and having your parents informed.' I knew what the most appealing option was and rushed out of the car as quickly as possible, my hands still bound by Brad's belt. He locked the car and we rushed into an opening which led us to a field, where we crouched down as two police officers got out of their patrol vehicle and turned on their torches. As soon as we were crouching, Billy pulled on his shirt and relaxed for a moment before removing his belt from my hands, freeing me, although we weren't free yet. I pulled on my jeans and shirt as quietly as possible, with difficulty as I still had a hard on due to my recent orgasm, making my jeans bulge out, making it blatantly obvious I had an erection. My cock was rubbing against the jean fabric and I began to wish Brad hadn't flung my boxers from his head, as they were still in his car. I put on my shirt and I felt Brad reach for my hand, which I gladly gave him, as we waited patiently for the police to leave, after they had looked into the windows to see the vehicle was empty. It wasn't clear if they had checked who the vehicle was registered to but they didn't put a ticket onto the car so we breathed a sigh of relief.

We watched them go, but just to be on the safe side, in case they returned, me and Brad stayed in the field for quite a while afterwards.

When he pulled up outside my house, it was 12:56a.m. I knew my parents would be asleep and unlikely to be looking out of the window so I leaned into the front of the car, gave Brad a big, long lasting kiss, and told him he could keep my boxers as a memento of the evening. His reply was to invite me round to dinner that evening, and I smiled, realising I was besotted with him, and then I left, looking back once I was at the front door.

I opened the door and locked it as quietly as I could, had a drink of cold water and then headed upstairs to bed in silence, still savouring the taste of Brad's cum in my mouth and throat. As soon as my bedroom door was closed, i stripped out of my shirt and jeans and collapsed on my bed. Then I wanked myself whilst imagining Brad's toned body and extremely his massive cock and replayed all the action from that night in my head. After I climaxed on my chest, I didn't bother to clean it off, letting it dry there, falling into an easy sleep. I dreamt about my future and with Brad in it, it seemed a whole lot nicer than it had previously.

TO BE CONTINUED...

Next: Chapter 3


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