Awesome Holiday in New York

By Philip Whitney

Published on Apr 27, 2012

Gay

Once again this chapter is dedicated to my three awesome American friends, whom I miss so much.

Chapter Two - Time to Reminisce

Everyone was totally shagged when the rents returned. The younger guys left for their respective rooms and we three spread ourselves in Trev's huge bed. Naturally they both wanted me in the middle and both fell asleep with their hands on my dick.It was may be due to jet lag, but I just could not fall asleep and tossed around in the bed for ages. The boys eventually released my dick and faced away from me. I slipped out of the covers and crawled to the end of the bed. Grabbing a pair of shorts and a T, I quietly exited the bedroom and headed into the kitchen for a drink. Walking over to the picture window in the lounge room, I pinched myself several times as I looked at the lights of New York below me. I could hardly believe I was actually here in New York. Sitting down in one of the very expensive looking arm chairs I started to reminisce about how I ended up here..

I thought it seemed a very long time ago, since I had written that first story for Nifty and Trev had emailed me about it. He asked if the story was factual and thought it was cool. He didn't indicate that he was only just 15 at the time, but he did say that he and his best friend had been messing around with each other since they were ten and had actually 'made it' together in the last spring. I gathered from the 'room mate' that they were rooming together at college or University, little did I know at that time they were at an exclusive private school. As one does I replied to his email telling him it was a fictional story that I had written for a friend and at the time of writing it I was only 17. He replied almost immediately telling me that he thought it was cool that I was close to his age and writing and that his younger brother thought so too. He wrote; " We read the story together and thanks to the story we were able to get off with each other last night."Pictures of faceless nubile brothers fucking each other got me hard immediately, but my dick was sore from our earlier escapades.

The time difference of 12 hours had always made it difficult to chat on msn, but once I had finished school it was easier when I wasn't at work. Trev always liked to chat after he had trained and after he had finished his homework. When we did get to chat he seemed to really be excited. We talked about our sports and since I taught swimming and used to compete, I gave him tips for his swimming comps. We always ended up talking sex and Trev's sexploits with the guys at the private school made my life seem boring. We often chatted till the early hours of the morning for him and on one occasion he hadn't answered for ten minutes and suddenly I got a message from John his roomie and lover. Trev had fallen asleep at the computer and John had put him to bed. He had woken up sufficiently for John to insert his throbbing six inch dick into Trev's warm interior, a night time ritual. That was the start of my friendship with John

Trev had always said that John wasn't the msn sort of guy. He said he spent his computer time playing games. However, John suddenly became besotted by me and started writing emails to me in class. When we did chat we spent a lot of time chatting about his new study partner, Walker. John really found him cute, but was scared to take the initiative. Before chatting to me all they had ever done was rub their knees together. For someone so into sex I found this really amusing. My first advice was to start putting his hand on Walkers thigh and see what happened. It appears that walker had been sitting with a boner every time they studied, but as a complete virgin with any form of sex was unable to take the initiative. Naturally with a bit of prompting from me, within two weeks they were stripping naked, kissing and giving daily BJs. Walker was scared about fucking, but John so wanted him it had to happen sooner or later. The day it happened I got a running commentary from Trev who was in the room for the event. Trev had been chatting to me for ages when John and Walker entered the room and John locked the door. Apparently Walker's roomie had called them faggots and told them to piss off. With the door closed they quickly stripped naked and fell onto John's bed locked in a tight embrace. Trev who was already naked got hard in seconds and couldn't keep his eyes off the action. He shot his load when John's tongue was buried deep inside Walker's hole and Walker was starting to think he was gay. Trev's last words were: "I think they are gonna fuck." before he suddenly went quiet. Some time later his yahoo sprang into life again. He informed me that the whole experience had been awesome and that the sight of John's naked ass thrusting back and forward as he massaged Walker's prostate was too much to resist and he had jumped up behind John and had inserted his five and a half incher into John's welcoming hole and felt he had played a major role in popping Walker's cherry. Again pictures of faceless naked teens shagging in an amazing threesome was too much for me and in spite of my aching dick I shot my tenth load in twenty seven hours.

It was now 2am and I suddenly felt hungry. Quietly stealing into the kitchen I opened the fridge looking for a snack. Salami and cheese seemed to be on offer, so I procured an ample serving and returned to my chair near the window. My thoughts drifted back to Trev and his lab partner, Lauren. When we first communicated he had told me he had only been fucking for a few months, but in that time he had fucked all of his male cousins and his two bros, Mark and Peter. Peter at 13 was the youngest and had been nicknamed 'pencil dick' because his dick was the longest at 7 inches, but really thin. Everybody liked to get fucked by Peter, because it didn't hurt and he could probe your bum hole where no other dick could go. It always amazed me that 13 year olds would even contemplate fucking and this was confirmed at a later stage when Mark informed me that at an all boys private boarding school like Linwood everybody messed around, but only a few actually fucked. So back to Trev and Lauren. Moving from an all boys school to his co-ed school Trev was hoping for a female conquest, just to see how it was. Lauren gave him the first opportunity and after several weeks working with her he eventually asked her to go to the movies. The closest he got was to hold her hand. "I behaved like a perfect gentleman." he informed me. After a couple more dates he eventually kissed her and he said he was sure Lauren had felt his hard dick pressing into her. Things started to happen when they kissed in the movie theater and Lauren squeezed his dick through his jeans. That was it, from then on Trev got hard every time he spoke to her even working together in class. Lauren seemed to tease him heaps by brushing the back of her hand against his bulging jeans and giggling. She even unzipped him at the movies and squeezed his dick through his Bonds. He was still reluctant to go any further until I suggested that he go commando on all his dates. This worked a treat and with his tongue down her throat and his hand in her pants, she jacked him off. Trev had never ever used condoms on his fuck buddies, but when I told him he couldn't risk getting Lauren pregnant he went and purchased a box full. Finding somewhere to do it was a problem, but John decided to spend the night with Walker and Lauren and Trev were alone in his room. They undressed each other and lay on the bed kissing. Trev heart was pounding as he fondled Lauren's young, firm nubile breasts. Trev's dick was bursting its skin as Lauren unwrapped the condom and gently rolled it down his shaft. He tried to be gentle, but finding resistance he had to push harder, causing Lauren to gasp, but as she relaxed they quickly got into a slow rhythm. In experience caused him to cum quickly and he knew he had not satisfied Lauren. Removing the condom Trev was surprised at the small amount of blood, he had expected more. Even though Lauren was inexperienced she immediately went down on Trev, licking all the cum off his softening member. This had the effect of filling Trev's dick with his hot blood and since Lauren was unsatisfied she immediately rolled on another condom. The second time was awesome. Starting off slow they speeded up as Lauren spread her legs more and gyrated her hips in time to Trev's thrusts. After a good 10 minutes they managed to cum together and Trev had to cover her mouth with his to stop her screaming out. This time they lay together with Trev's dick softening inside her, content at just being naked together.

After a while Trev's dick slipped out and once again Lauren licked it clean, but as it swelled once again inside her mouth she sucked him for the first time. However, her inexperience showed and Trev felt her mouth wasn't as good as John's or his bros. With his dick once again fully hard he wanted to feel what it was like inside Lauren with out a condom and he slipped into her easily. They lay like that for a while, but once he involuntarily started to move inside her, caution took over and a third condom was produced. This time they were able to roll around on the bed, trying different positions and eventually came for the third time with Lauren on her hands and knees and Trev fondling her breasts. Unfortunately it was soon time for Lauren to sneak out of his room and return to her dorm. Trev immediately came on line and reported every detail to me.

At 3am I didn't think anyone would be around so I stripped my T and shorts off and stood at the window slowly and gently stroking my rock hard 7 incher, looking down at the lights of New York. Suddenly my heart skipped a beat as arms wrapped around my body and a naked Trev pressed his dick against my bum. "I have been longing for this moment, since I first saw your pics." he whispered in my ear. I don't seem to be able to get you on your own. Grasping my hand he lead me over to a shag pile rug and lay me down. "Do you realize that you have yet to fuck me?" As he slowly lowered his perfect bum down onto my dick, he whispered once again: " I have waited since forever for that curve to massage my prostate. This is going to be awesome." His smile was to die for.

Even though it has yet to reach a conclusion, this may be the final part as I wait in Australia for some communication from my American friends. I just want to hear that you are all well and why you have stopped contacting. I miss you heaps and i feel you all still love me.

Philip

Next: Chapter 3


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