Date: Mon, 7 Nov 2011 20:44:17 -0800 From: B.E. Kelley <hailcaesar2011@hotmail.com> Subject: Over the River and Through the Woods This story is a work of FICTION. The events described are my own invention. Any similarities to actual events or persons are strictly coincidental. The author retains the copyright, and any other rights, to this original story. You may not publish it or any part of it without my explicit authorization. This story contains depictions of consensual sexual acts between teenage males. It is intended for mature audiences only. If you find this type of material offensive or if you are under the legal age to read said material; please proceed no further. Comments are always welcome at: hailcaesar2011@hotmail.com Over the River and Through the Woods "Goodbye Simon, I love you," said mom, "Be a good boy, okay?" "Bye mom, I love you too and don't worry, I will," I replied. "Come on son, let me show you to your seat," said the conductor. And so began my cross country journey. I was traveling from my home in San Francisco, California, to stay with my grandparents in Greenwich, Connecticut, for the next 6 months. My mother is a world renowned concert pianist, who is going on a European tour with the San Francisco Philharmonic. My father was killed in a plane crash last year. That's why I'm on the train; I've been unable to fly since dad's accident. A couple of months after dad died, I was supposed to fly to Washington D.C., to attend one of my mom's concerts, but I got so nervous that I passed out on the jet way. Mom and I arrived at the train station early. I had to answer a bunch of questions for the station agent before he would agree to let me board. I'm only 13 and Amtrak has some very strict rules for unaccompanied minors. Once I'd answered all of his questions to his satisfaction, he put an ID bracelet on my wrist, then mom and I sat in the lobby to wait for the train. Mom was teary eyed and held on to me tightly. Because of her career, we've said goodbyes like this more than once. Normally I'd be fine at home with dad but he wasn't there to take care of me now and I think that might have been the reason mom held on a little tighter than usual. I followed the conductor onto the train and he led me to my room for the four day trip. With a full day's layover in Chicago and a short layover in Pittsburgh, it would be almost 84 hours before my grandparents picked me up at Penn Station, in New York City. I had what Amtrak calls a "bedroom," all to myself. It's basically a small room with a sofa that folds out into a bed, a tiny bathroom/shower and another bunk that folds down from above. "Do you have everything you need kid?" asked the Conductor. "Yes Sir," I replied, "I've got everything I need, I'll be fine." "Alright then," said the conductor, "My name is Frank and if you need anything please let me know." Frank excused himself so that he could make his preparations for departure. Once I was alone in my room, I started to cry. I love my grandma and grandpa and I'm looking forward to staying with them but I know I'm going to miss my mom. I wanted to be strong, to show mom that she didn't need to worry about me, so I held back the tears when we said goodbye. Now, here, alone, the tears came streaming down. After a few minutes of sobbing, I calmed myself down and blew my nose. By the time the train began to pull out of the station, I was looking out the window excitedly. San Francisco may be weird but it's definitely beautiful. I watched the city scenery pass me by and quickly the grandeur of the skyscrapers and the bay faded into the industrial wasteland of Vallejo. We sped through Vallejo's shipyards and refineries, than slipped into the farmland of the San Joaquin Valley. We arrived in Sacramento at 10:00am and wouldn't be leaving until 1:00pm. Because I was traveling alone, I had to stay at the train station while everyone else was able to explore California's capitol city. Granted you couldn't explore much in the short time we would be here but being able to go for a walk sounded better than sitting around a train station. I amused myself with a few games on my PSP then had lunch at the station's snack bar. When it was time to re-board the train, I checked in with Frank and found my way back to my room. The train pulled out of Sacramento and I played a few more video games then realized I was missing out on the scenery. I put my PSP back in my bag and looked out the window as we entered the Sierra Nevada Mountains. I sat there taking in the natural beauty for so long that I was actually startled when there was a knock on the door and Frank stuck his head in. "It's almost 5 o' clock," said Frank, "The first dinner seating is about to begin, if you're hungry." I had been so focused on the scenery that I hadn't noticed the passage of time. It had been hours since my sandwich in Sacramento and as soon as Frank mentioned food, my tummy started to rumble. "Yeah, that would be great, thanks," I answered. I gave myself a quick look in the mirror before following Frank to the dining car. There isn't a lot of room on a train and in order to make use of all the space available, all the seats in the dining car need to be full at meal times. Since I knew I would be sitting with other people, I wanted to make sure I was presentable. I'm not a vain person but I was pleased with my reflection. I'm 5'1" and weigh a little over 100 pounds. I have short black hair that is combed neatly, in a style typical for boys my age. My eyes are a pale blue and are probably one of my best features. I'm used to people telling me I'm cute but when I'm having a bad day or I'm in a bad mood, my mom says I look more like Damien from The Omen. I didn't get the reference until I saw the movie for myself and, reluctantly, had to agree. But hey, everyone seemed to think that boy was cute so why should I complain? What I was wearing was mostly my mom's fault. For some reason, she thinks it's important to dress nicely when traveling. I was wearing a white undershirt with a blue oxford button down, khaki trousers with a leather belt and penny loafers with a pair of argyle socks. Fortunately I have more casual clothes with me and the rest of the trip will be a bit more comfortable. When we arrived at the dining car, Frank led me to a table and seated me with a family of three. The boy, who looked about my age, put down his menu and smiled at me the moment I sat down. I smiled back, nervously and then his mom made the introductions. "I'm Angela Wallace, this is my husband, Philip and our son Emery," said Mrs. Wallace, "What's your name sweetheart?" "Simon, Simon Cooper," I answered shyly. "Where are you headed, Simon?" asked Mr. Wallace. "I'm on my way to Connecticut to stay with my grandparents for a while," I replied, "they're picking me up in New York." "Oh, we're on our way to New York as well," said Mrs. Wallace. "We're on vacation but dad doesn't like to fly," said Emery, "how long are you staying with your grandparents?" "About 6 months," I replied. "Wow, how come so long?" asked Emery. "My mom is on her way to Europe, she'll be on tour there for 6 months," I answered. "On tour?" asked Mr. Wallace. "Yeah, she's a pianist and she's playing a bunch of concerts with the philharmonic," I answered. "Cool, is she famous?" asked Emery. "Well, yeah, I mean if you like classical music," I smiled. The waiter arrived and after we ordered our dinner we continued to make small talk. I didn't say much, I'm naturally shy around strangers, and I had a hard time taking my eyes off of Emery. He might be about the most beautiful boy I've ever seen. Over the course of our conversation, I learned that he was 13, like me. He was about my height but weighed a tiny bit more, he had short, but shaggy brown hair and sparkling, intensely blue eyes. I never felt myself attracted to girls, Emery, however, was causing a definite stirring in my underpants. Emery and I both ordered the burger and were quiet when the food came. I think he must have been as hungry as I was because we both wolfed down our dinner in no time. "So why are you dressed like that?" asked Emery as he gobbled up another mouthful of fries. "Em, don't be rude," his mom admonished. "It's ok, I don't always dress like this," I replied, "my mom just has this thing about dressing nicely when you travel, so she made me put this on this morning." Emery was wearing a black Pittsburgh Steelers jersey over his white t shirt, khaki cargo shorts and a pair of black Converse low tops with white ankle socks. He looked really cute. Occasionally his leg would brush against mine and I wished I had changed into shorts before dinner so that I could feel his skin brush against mine. "Have you been to the sightseer car yet?" asked Emery as we finished dinner. "No, I've been in my room since we left Sacramento," I replied. "You wanna go check it out?" he asked. "Sure, that would be cool," I agreed. "Simon, you're more than welcome to join us for meals over the next few days, if you'd like," said Mrs. Wallace. "Thank you Mrs. Wallace, that would be great," I replied. "And Emery, be back before 10:00pm," said Mr. Wallace. "Yes dad," Emery agreed. I followed Emery to the sightseer car, which is basically a traveling observation deck, and we took two seats in the rear. "So what's it like living in San Francisco?" asked Emery. "It's ok I guess, it's just home, you know what I mean?" I replied. "Yeah, I guess so," said Emery, "It's gotta be better then Roseville though." "Roseville?" I asked. "Yeah, it's in the Sacramento suburbs," Emery answered. "That sound nice," I replied. "Nah, nothing ever happens there," said Emery, "so what do you do for fun?" "Just stuff, you know, reading, music, video games, hanging out with my friends," I answered. "Yeah, me too. Do you play any sports?" asked Emery. "Soccer and a little baseball," I replied, "how about you?" "I play football, baseball and I wrestle," said Emery. "My school doesn't have a football team," I stated. "Mine doesn't either, I play in the Pop Warner league," said Emery, "But I am on the school baseball and wrestling teams." "What position do you play?" I asked. "First base and pitcher, how about you?" said Emery. "Shortstop," I replied. "Cool," said Emery. "So how do you like junior high? asked Emery. "It's ok, I like not being in the same class all day," I answered. "Do you like looking at the boy's in the locker room?" Emery asked innocently. "Uh..." I stuttered and blushed. "Don't be embarrassed," said Emery, "I like looking." "You do?" I asked. "Yeah, some of them are really cute," he replied. "Are you gay?" I asked. "I don't know," said Emery, "I know I like looking at the boys though." "Cool," I stated. "So do you?" he asked. "Do I what?" I replied. "Like looking at the boys," said Emery. "Oh, yeah, sometimes, I guess," I admitted. "Cool, you're a cute boy," said Emery, "I'd look at you." After that admission, we sat quietly, looking at the scenery until it started to get dark. "So do you jerk off?" asked Emery. Emery didn't seem at all shy and I had to answer in the affirmative. "Sure," I replied. "Cool, ever done it with anyone?" asked Emery. "No way, have you?" I asked. "Yeah, me and my friend Eric do it all the time," replied Emery, "no big deal." "You have your own room, right?" asked Emery. "Yeah," I answered. "You wanna try it?" he inquired. "What, jerking off with you?" I asked. "Sure, it'll be fun," he replied. I thought about it for a moment. I didn't know if I was gay or not but I knew I liked looking at boys and I knew that Emery was about the cutest boy I had ever seen, even if he was a little brash. Did I want to see his dick? Oh yeah. "Ok, I guess," I answered nervously. I led Emery back to my room and as it turned out, he and his parents were just up the hall from me. When we got inside, I quickly locked the door and made sure the blinds were closed. Then we stood there, face to face. "So what do we do now?" I asked. "Let's take off our clothes," said Emery. "Ok, cool," I agreed. Emery kicked off his shoes and pulled his jersey and t shirt over his head. I stood there staring as he pulled open his belt then unbuttoned and unzipped his shorts which then slide down around his ankles. He boldly stood there in his socks and red Hanes boxerbriefs, his proud 4 inch boner pointing straight ahead. "You're turn," said Emery, snapping me out of my gaze. "Right, sorry," I blushed. I undressed a little more slowly. I unbuttoned me shirt and tossed it aside then pulled my t shirt over my head. I kicked off my loafers then, with a deep breath, I pulled my belt open, unbuttoned and unzipped my fly and let my trousers fall to my ankles. I stood there in my black argyle socks and blue Hanes briefs. Emery was a bit more muscular then me so I felt a little self-conscience as he looked me over. "Cool, I like your underwear," said Emery. "You do?" I asked. "Yeah, I was afraid you would have boxers on," Emery admitted. "What's wrong with boxers?" I asked. "They aren't as sexy," said Emery, "I like how briefs show off a boy's butt and his package. Your stiffy looks pretty good in those." I was proud of my four incher and it made me happy that Emery liked it. "Thanks," I replied as my dick twitched in my undies. "Hmm, you're a little taller than me but I bet I could pin you," said Emery. "What?" I asked, I hadn't been expecting that comment. "Sorry, I was thinking about wrestling. You'd be in my weight class but I think I could take you," he smiled. "I don't know," I replied, "I'm not on a team but I wrestle with my friends and I'm pretty good." "You wanna wrestle?" he asked. "Do you?" I replied. He didn't respond, he just pounced on me. We grappled and rolled around on the floor of the tiny room. I wasn't so much interested in winning the match as I was in touching Emery all over his smooth, athletic body. I wasn't concentrating and it didn't take long for Emery to pin me down. "Told you I could take you," smiled Emery. "Yeah, yeah," I grumbled, "I feel your stiffy poking me." "I know, I feel yours rubbing against mine," he smiled, "do you like it?" "Yeah, it feels really good," I admitted. We lie there for a moment, our hard little dicks stretching the thin cotton fabric of our underpants and twitching with each sensual touch. "I'm gonna kiss you now," said Emery. "Oh, okay," I agreed. He leaned forward and pressed his lips against mine then held them there for a moment. When he pulled back, he looked down and smiled at me, I couldn't help but smile back. "How was that?" asked Emery. "It was ok," I admitted. "Ok, I'm gonna kiss you again, only this time open your mouth a little and do what I do," said Emery. I parted my lips ever so slightly and this time I felt Emery's tongue dart into my mouth. I lay there for a moment feeling his lips against mine and feeling his tongue explore my mouth then I remembered what he'd said. I pushed my tongue into his mouth and our soft pink muscles began to rub against each other, sending an electric shock through my body that I felt even in my dick. We kissed like that for a few minutes, it was wet and sloppy but I would have to say it was the best thing I'd ever felt up to that point in my life. "Spread your legs a little bit," said Emery. I did as he asked and felt him slip between my legs, making it easier for our boners to rub against each other. "Mmm that feels good," Emery moaned. "Mmm, yeah, it does," I agreed. "Me and Eric do this sometimes," said Emery, "Put your hands on my butt." I again followed his instructions and rested my hands on his firm, athletic little butt and gave it a squeeze. Emery smiled at me then began to move his hips up and down. We still had our underwear on but the friction that caused as they rubbed against each other felt amazing. "Do you like it?" asked Emery. "Yeah, don't stop," I replied. Emery began to hump against me harder and faster, I started to rub up and down his back but always returning to squeeze his cute little ass. After a while Emery started to get tried and I rolled on top of him and continued the humping. His hands felt great on my ass as he kneaded my firm buns like dough. "I think I'm gonna cum," I moaned, as Emery rolled back on top. Emery kept thrusting his hips then pressed his lips against mine. The feeling of his mouth on mine sent that familiar new shock through my dick and I fired shot after shot of cum into my underpants. Emery must have felt the same feeling I did and he collapsed against me as his dick drenched his underwear. We lie there panting for breath before I spoke up. "Wow, that was like, the coolest thing ever!" I exclaimed. "I'm glad you liked it," Emery smiled, "That was way more intense than it's ever been with Eric." We lie there, smiling and grinning like idiots for a moment then Emery looked at the clock and that snapped him back to earth. "Crap it's almost 10:00," he exclaimed, "I've gotta head to my room." We stood up and I helped Emery gather up his clothes. We stopped for a moment and giggled as we looked at each other's crotches, both soaking wet. "I've got an idea," Emery giggled, "Gimme your underwear." "Ok," I agreed as I slipped my briefs off and tossed them to him. "Put these on," said Emery, as he threw his boxerbriefs at me. "There, now we're cum brothers," Emery laughed as we stood there in each other's wet underpants. "How do I look?" asked Emery, once he finished dressing. "Perfect," I smiled. "Do you want to hang out and you know, maybe do some other stuff tomorrow?" asked Emery. "Um, hell yeah!" I exclaimed. "You're cute," Emery smiled. "See you in the morning," said Emery as he kissed me good night. I savored the kiss for as long as I could. "Night Emery." I stood there in Emery's wet boxerbriefs and couldn't help but marvel at the day I'd had. Up until today I'd only jacked off thinking of some of the boys from school, now I'm standing here wearing the cum soaked underpants of a boy who I just got off with while we made out. Amazing. I slept better than I had slept in months that night, gee I wonder why? I woke up the next morning, somewhere between Salt Lake City and Denver, when I heard someone banging on my door. "Who is it?" I groaned. "It's me, Emery, wake up," he answered. I reluctantly climbed out of bed and padded the couple of feet to the door, which I opened for a smiling Emery. "You're still wearing my underwear," he smiled, while I blushed. "Uh, yeah, I kinda fell asleep right after you left," I replied. "That's ok, I slept in yours too," he winked. "What time is it?" I yawned. "Almost 8:00am, we're about to go eat breakfast and my mom told me to come and see if you wanted to join us," said Emery. "Oh, yeah, I'm definitely hungry," I answered. "Cool, why don't you put that away, get cleaned up and meet me at my room?" asked Emery as he reached over and patted my morning erection. "Ok, give me ten minutes," I yawned again. Emery took off down the hall and I headed for the tiny bathroom/shower. It was probably the least satisfying shower I've ever had but at least it got me clean. Remembering what Emery had said about how dorky I was dressed the night before, I wanted to make sure I looked more casual today. I slipped on a fresh pair of briefs then put on my khaki shorts and a brown leather belt. I put on a white undershirt then selected a charcoal grey polo to go over it before I sat down to put on my socks and black Converse low tops. I smiled at my sneakers, I remembered Emery wearing an identical pair the night before. I walked the short distance to Emery's room and arrived just as his family was leaving for breakfast. "Good morning Simon," said Mr. Wallace, "I'm glad you could join us again." "Thanks Mr. Wallace, it will be nice to eat with you guys rather then have to sit with different people at every meal," I replied. We headed for the dining car and I looked Emery over carefully. He was just as cute as the night before and when I looked at him I had this terrible feeling that I'd wake up and discover that this had all been a dream. He was dressed pretty much the same as he had been yesterday only instead of his Steelers jersey, this morning he was wearing a pink polo shirt. I don't know a lot of boys our age that wear pink and I don't know if it was his skin tone or his eye color or what, but it looked great on him. We were seated quickly, when we arrived at the dining car, and my pancakes seemed to arrive almost as quickly as I ordered them. I learned a lot more about the Wallace's while we shared our morning meal. Mr. Wallace was a deputy sheriff with the Sacramento County Sherriff's Department while Mrs. Wallace taught English at Emery's school. Emery also had an older brother, Avery, who was in college at Northwestern and would be meeting them in Chicago so they could spend the day together. After breakfast, Emery and I grabbed our PSP's and headed back to the sightseer car. You might think that at 13 we would be so horny that we'd go straight to my room once we got away from his parents, and in fact, we probably were that horny, but I think we were also sharing that morning after shyness. It turns out that we both liked the game Ace Combat, Joint Assault, so we spent a couple of hours trying to best each other's scores on various missions. We got tired of playing games, somewhere outside of Denver, and Emery moved from his seat across from me and took the seat next to me. Emery kept bumping his knee against mine and giving me his sly smile. I love that smile. He's so cute and bold; he seems to say whatever he's thinking without any concern about what might happen. Normally I'd be annoyed by such brash behavior but for some reason I find it charming in Emery. "So can I tell you something?" asked Emery. "Sure," I replied. "You know yesterday, when you asked me if I was gay and I said I wasn't sure?" said Emery. "Yeah, I vaguely remember that," I chuckled. "Well, I wasn't exactly 100% honest," Emery admitted. "What do you mean?" I inquired. "I'm gay, I just wasn't sure I should tell you," said Emery. "Why?" I asked, "You didn't have any problem saying any of that other, personal stuff." "I know, but I thought if you knew I was gay you would feel different about messing around with me," he admitted. "I don't think it would have mattered," I confessed, "I'm really not sure if I'm gay yet but I know that I've never been all that attracted to a girl, I know I like checking out other boys, and I know I liked everything we did last night." "So you're not mad then?" asked Emery. "Course not," I smiled. "Ok, good," said Emery with a sigh of relief, "so do you want to go back to your room and..." "I thought you'd never ask," I interrupted with a smile. We headed back to my room, talking and giggling like a couple of cheerleaders and I realized that I wasn't just attracted to Emery, I really enjoyed his company. His irreverence was contagious and I enjoyed being silly with him. I think I'm predisposed to being uptight, my mother is always reminding me that I'm 13 not 40, and being with Emery seemed to really loosen me up. When we got into my room, Emery pulled me close for a big hug and a quick peck on the lips. "That was nice," I smiled. "I wanted to do that all morning," said Emery, "I'm glad you're not mad at me." "Stop worrying about it, it didn't matter at all," I stated. "Right, time for sex," Emery giggled as he took off his shirt. We stripped down to our socks and underwear again. This time Emery was wearing white Hanes briefs with his ankle socks and I had on a pair of grey Hanes briefs with mine. We hugged each other tightly, so that our boners could rub against each other, than started to kiss. We began with a couple of quick pecks to the cheek and lips then we began the tongue wrestling. We made out slowly at first but the more turned on we got, the faster our tongues darted in and out of each other's mouths. We ground our packages together and rubbed each other's tight, cotton covered butts, than Emery pulled away. "Let's get in your bed," said Emery. We folded the sofa back into a bed, I lay on my back and Emery jumped on top. We immediately began to kiss again and Emery started to hump me vigorously. We were both enjoying the tingling in our little boners but before either of us could cum, Emery stopped humping and lay down on my chest. "What did you stop for?" I asked. "There's something else me and Eric do sometimes," said Emery, "I wanna try it on you." "What is it?" I asked. "Do you know what a blow job is?" he asked. "Yeah, I've heard about that," I stated, "You and Eric do that?" "Sometimes," answered Emery. "What's it feel like?" I inquired. "It's kinda hard to explain," said Emery, "That's why I want to show you." "Ok," I answered a little nervously, "go ahead." Emery slipped down between my legs and started to rub my boner through my underwear. His touch felt good, it was the first time anyone else had ever touched my dick. As he fondled my package I began to relax and enjoy the sensation, then Emery hooked his fingers into the waistband of my briefs. "Lift your butt up a little, so I can take your undies off," Emery instructed. I did as he asked and in one swift motion he pulled my briefs off and tossed them aside allowing my four inch stiffy to slap against my tummy. I was a little nervous, after all no one had ever examined my dick so closely before. Emery seemed to be studying my penis; he looked at it from different angles then started to stroke it a little. "I like you're dick," smiled Emery, "it's cute." "How can a dick be cute?" I chuckled. "I don't know, it just is," said Emery. I was about to say something else when Emery placed his tongue at the base of my dick and licked up the shaft and up to the head, like he was licking a popsicle. I lay there and shuddered from the exquisite feeling I experienced. Emery grinned at me then licked me again. He licked all over my dick, rubbing it with his tongue, tickling the tiny cum hole and then he put his mouth around it and started to bob up and down. I never knew anything could feel so unimaginably good. Emery's mouth was hot and wet; it seemed to envelop my dick with its warmth, as he swallowed me to the hilt. I reached down and grabbed handfuls of Emery's soft brown hair and began to buck my hips, trying to get further into his mouth. I don't know how long I lasted but it couldn't have been long, the feeling was so intense and before I knew it I was shooting my watery load into Emery's mouth. I lie back on the bed panting for breath as Emery curled up next to me and waited for me to relax. "So what did you think?" asked Emery. "WOW," was the only word I could think of to express the feeling. "Yeah, that's how it felt when Eric did it to me the first time," Emery smiled. "Do you want me to do it to you now?" I asked. "You don't have to, if you want to rest," said Emery, "I can just keep jacking myself off." I hadn't noticed before but as I looked down I saw that Emery had his hand in his briefs and was slowly stroking his boner. "But I really want to try," I stated eagerly. "Ok then," said Emery, as he rolled over on his back, placed his hands behind his head and spread his legs. "Take me, I'm yours," he giggled. I didn't waste any time. I slipped down between his legs and grabbed the waistband of his briefs, then tugged them down around his hips. "You know, yours is cute too," I stated, as I examined Emery's little pole with its spongy pink head. "How can a dick be cute," Emery laughed while doing his best impression of me. "Yeah, yeah, I know. Still, it is cute," I replied. "Tastes even better," Emery joked. That was all the encouragement I needed. I stuck out my tongue, tentatively, and licked Emery the way he had licked me, from the base up to the head. I expected it to taste musty and sour, kind of like that old jock strap smell you find in locker rooms, but it wasn't like that at all. Emery tasted clean and fresh with a hint of saltiness, it was good and I wanted more. I happily lapped at his penis, licking it up and down, painting the shaft and tickling the cum hole. When I had satisfied my appetite for my new favorite flavor, I engulfed his dick in my mouth and wrapped my lips around it. "There you go," said Emery, "now just start sucking on it." I started to suck on the throbbing boner but Emery stopped me almost as soon as I began. "Careful, don't use your teeth," Emery instructed. I tightened my lips and started sucking again, this time earning Emery's praise. "Yeah, that's it Simon," Emery moaned, "that feels so good." I started to bob up and down on the cute stiffy and was rewarded by more soft, guttural moaning from Emery. I copied the motions he had used on me and before long, he began to buck his hips and grab my hair, just like I'd done to him. "Mmm, I'm gonna cum," moaned Emery. I felt Emery's load shoot into my mouth. The taste was surprisingly good, salty and a little sweet. When he was finished I scooted up next to him as he pulled up his briefs. "So what did you think?" asked Emery. "You were right, you're delicious," I smiled. "Are you tired?" He asked. "Yeah, I kind of am," I admitted. "Come here," said Emery as he scooted over and opened his arms. I lay next to him and he spooned in behind me then wrapped his arms around me. It felt good to be in his arms, almost safe and reassuring. "Is this ok," asked Emery as he nestled close behind me. "Yeah, I really like it," I confessed. "Good," said Emery, "Eric is always in a hurry to do something else after we cum, he never likes to snuggle." "Well, he doesn't know what he's missing," I yawned, I'd never felt more relaxed or comfortable. "Thanks," said Emery as he kissed me on the cheek. I drifted off to sleep after that, enjoying the sensation of Emery's warm breath on the back of my neck. When I woke up, Emery was absentmindedly playing with my nipple. I rolled over and found him propped up on his elbow, just looking at me with his goofy, sweet smile. "Sleep good?" he asked. "Yeah, real good," I admitted, "how long was I out? "Only a couple hours," said Emery, "It's still earlier then I like to get up on vacation." "It's after noon lazy," I giggled. "What can I say, I need my beauty sleep," said Emery. "You must get it, I think you're pretty beautiful," I blushed. "Awww, thanks Si," said Emery, "But why are you blushing?" "I'm just not used to saying whatever I'm thinking the way you do," I admitted. "Yeah, I've sensed that, like we're talking and I get the impression you want to say something but don't," said Emery. "I've always been like that," I replied. "It's ok to let loose Si," said Emery, tenderly, "you don't always have to act so grown up." "Yeah I do," I sniffled. "But why?" asked Emery as he gently brushed his fingers across my cheek. "It's just me and my mom now," I stated. "What about your dad?" asked Emery. "My dad was a corporate pilot, he flew business jets for CEO's and stuff," I began, "Last year he was killed in an accident while landing in Tokyo." "Oh Simon, I'm so sorry," said Emery as he hugged me tightly and I sobbed. I cried in Emery's arms for a long time, he was so gentle and tender, so caring and concerned that I just let it all out and sobbed on his shoulder. He didn't ask me any questions, didn't try to get me to stop, he just ran his hand gently up and down my back, it almost felt therapeutic. "So you've been holding all of that in for a year?" asked Simon, when I'd regained my composure. "I cried for him when it happened but I guess I wasn't done grieving," I admitted, "I've been trying to be strong for my mom." "I get that," said Emery, "but I'm sure she wouldn't want you to hold in all your feelings." "When my dad used to leave on business trips, he'd always tell me that I was the man of the house, while he was gone," I sniffled. "You are the man of the house now Si, but that doesn't mean you can't cry for your dad," said Emery. "I guess I know that in my mind," I admitted, "but you're heart and your brain don't always communicate so well." Emery was a very comforting presence. It felt good to get a few things off my chest and I was grateful to my new friend for his caring and compassion. We lie there a little longer, just looking at each other, when I felt the urge to ask him a few things. "Is Eric your boyfriend?" I asked. "Nah, we're just buddies," said Emery. "Even with all the stuff you've done together?" I replied. "Yeah, every time we screw around he's always quick to remind me that he's straight and just likes to get off," said Emery, "and he doesn't like to kiss or snuggle, he says that's gay." "And that doesn't bother you?" I asked, "Doesn't make you feel like he's using you?" "Sometimes it does," Emery admitted, "But then I'm kind of using him too." "How do you figure?" I inquired. "Well, sure, he likes getting his dick sucked, but I like sucking it. See what I mean?" said Emery "Kind of, it's like you use him back?" I asked. "I wouldn't call it using exactly, I mean we're both having fun, what's the harm?" said Emery. "Yeah, that makes sense," I agreed. "I still think he must not be to smart if he doesn't like to kiss and snuggle with you," I smiled. "Thanks," Emery giggled, "I'm glad you like it." "You know what I think?" I asked, moving to another subject. "Huh?" said Emery. "You must look really hot in your little wrestling uniform," I stated as I grabbed his tight butt. "Those things are so tight," laughed Emery. "Do you wear anything under it?" I asked. "Just my underwear or my jock strap," said Emery, "There's no way anything else would fit." "Hmmm, you in a jock strap, that's another pleasant image," I giggled. "If I knew I'd meet a boy that liked my butt so much, I'd have packed one in my bag," laughed Emery. "I can't help it," I said as I continued to rest my hands on his perky rump. "Whose complaining?" Emery retorted. "When you wrestle, how do you not get a boner?" I asked next. "It's hard sometimes," Emery admitted, "I've wrestled some really hot guys but I'd rather not get my ass kicked so I think that keeps Little Em soft." "Doesn't feel so soft right now," I giggled as I moved my hand to Emery's groin and rubbed his boner. "You do have that effect on me," Emery smiled. "Likewise," I replied in reference to my own hardon. "Wanna suck each other again?" Emery grinned slyly. "Uh huh," I nodded. "Cool, let's try it like this," said Emery as he moved into a 69 position with me. He wasted no time by just licking me; instead he swallowed me in one gulp and began to bob on my knob. Emery still had his briefs on and I was kissing and licking at his package when he reached down and pulled his dick out. His dick slipped easily into my mouth and I was rewarded with that same fresh, salty taste as before. Emery bucked his hips in time with the bobbing of his head and we were both moaning around the other's dick. I grabbed Emery's undies and pulled them down as far as I could so I could feel up his smooth ass. I was so drawn to Emery's ass that it felt like iron and my hands like magnets, I couldn't feel it enough. From this angle, with Emery's dick in my mouth, I had a great view of his tighty little pucker and it seemed to draw me in. I reached up and tickled the tiny hole and Emery seemed to like that so I pushed my finger against it. When Emery gave out a little moan I was further encouraged and pushed my digit into his opening. "Wow, keep doing that," said Emery, before taking my dick back into his mouth. I continued to move my finger in and out of his tight rectum. Sometimes I would push it in as far as I could and that would really make him twitch. I didn't notice it because I was so into fingering Emery, but I was moaning almost as much as he was. When he shot his cum into my mouth it sent me over the edge and I exploded in his. "That was so hot," Emery exclaimed, "Eric keeps asking if he can fuck me but I never let him." "I'm sorry, I should have asked first," I apologized. "No, it was cool, I really liked it," said Emery, "What made you do it?" "I don't know, I was sucking on you and looking at your butt and it just seemed like the thing to do," I stated. "It felt awesome," Emery smiled. "How come you won't let Eric fuck you?" I asked as we started to get dressed. "Cause," said Emery as he pulled his shirt on, "I'm saving that for someone special, you know?" "Yeah, I understand and I think that's cool," I replied. We were both hungry after our morning romp, so we headed off to find some food. We had a half hour stop somewhere in Kansas, and after getting permission from Emery's parents, we got off the train so we could grab sandwiches from the Subway inside the terminal. We made it back to the train well before it departed then ate our lunch and spent the rest of the day in the sightseer car, playing games and just talking. That night at dinner, Emery's parents talked about what they would be doing in Chicago the next day during our layover. Emery's brother, Avery, was going to meet them at the station and take them on a tour of the city. They were going to have lunch, take in some of the sights and be back in time for the next leg of our trip. Emery begged his parents to bring me with them but before they could answer, I had to explain that I wasn't allowed to leave the train station. Emery tried to talk me into it anyway but I knew I couldn't, Amtrak's rules were pretty strict and I didn't want to have to call my grandpa and tell him I'd missed my train. Not to mention, I didn't want to miss out on spending more time with Emery. Emery sulked during the rest of our meal but his mood perked up once we headed back to my room after dinner. His parents had agreed to let him spend the night in my room when we left Chicago tomorrow and that seemed to cheer him up. We were naked almost as soon as I locked the door. I was leaning against the wall and Emery was on his knees giving me another expert blow job. I didn't think anything could ever feel better but then he began to finger my ass the way I had done his and WHOA. It felt so good; it made the blow job even better. After I came, I had Emery sit down so I could return the favor. When we were both sexually satisfied, Emery returned to his room. He told me he would be by to pick me up for breakfast again and I promised I'd meet his brother and see him off before he left to explore Chicago. At least I was awake when Emery pounded on my door at 7:00am the next morning. When he came in he gave me a peck on the cheek, which I thought was really sweet, then he smacked me on the ass and told me to hurry up. I took another unsatisfying shower, in my too small to be real bathroom, then put on a pair of khaki shorts, a white undershirt and a grey t-shirt with the philharmonic's logo on the front. I grabbed my flip-flops then went to join Emery and his parents. Sure I looked like a bum but why get dressed up to hang out at a train station all day? At breakfast, I learned that Emery had a slight case of hero-worship when it came to his brother, Avery. Avery had been a star baseball player in high school and had won a full scholarship to Northwestern, where he pitched for the Wildcats. He was, apparently, also really smart, he was studying biochemistry and if he didn't make it to the major leagues he planned to go to medical school. Being an only child, I was a little jealous of how excited Emery was to see his brother, but all I had to do was look at him with his happy smile while he bounced around in his seat and I just smiled. When we pulled into Chicago, just after 8:30am, I followed Emery and his parents to the front of the station, where they would meet his brother. I was taking in the sights of the crowded station when Emery raced off. I turned my head just in time to see him practically tackle Avery right there in the lobby. When the brothers broke their embrace, Avery hugged his mom and dad then Emery introduced him to me. "Avery this is my friend Simon I met him on the train the other day he's from San Francisco and his mom's a famous pianist and he's on his way to Connecticut to stay with his grandparents for a while they're going to meet him in New York," said Emery without pause for breath or punctuation. "Anything you left out?" Avery teased his brother. "It's nice to meet you Simon," said Avery as he extended his hand, "I'm glad this guy had you to hang out with on the train or he would have probably driven mom and dad nuts." "Nice to meet you too, and I don't mind hanging out with Emery, it's been a lot of fun," I responded, which caused Emery to blush a little. "Yeah, he's not so bad as far as little brothers go," said Avery as he patted Emery on the back. "Anyway, I better go check in with the station manager before they issue an amber alert or something," I stated, "I'll see you guys later." "Are you sure you'll be alright here, Simon?" asked Mrs. Wallace. "Yes ma'am, I'll be ok," I answered, "I've got my PSP and a book to read, and it looks like they have a pretty good food court." "Alright then, we'll see you at dinner," said Mrs. Wallace. "Bye Si, I'll see you later and tell you all about Chicago," said Emery. I left the Wallace's and checked in with the station manager then grabbed a seat in the terminal coffee shop and ordered some hot chocolate. I took my book out of my bag and started to read it but I kept thinking how much Emery looked like Avery. Avery was basically a taller, more muscular Emery, in a purple baseball cap. He was really cute and I couldn't help but think that Emery was going to be hot when he grew up. That's when a shocking realization hit me, our journey was almost at an end, tomorrow evening I would say goodbye to Emery, at Penn Station and I didn't know if I would ever see him again. As I sat there and thought about what it would be like to say goodbye to Emery, I almost started to cry. We only met a couple of days ago but so much has happened since then. Not only did he, uh, punch my v-card, he'd become a true friend. I told Emery things that I'd never told my best friend, Brice. Emery had been so interested in the things I had to say, so caring and compassionate when I talked about my dad, how could I lose a friend like that? I wanted to know Emery for the rest of my life, I wanted to see what he would look like when he was Avery's age and I wanted to know what he'd do with all that excited energy when he grew up. I never got beyond the first few pages of my book; my mind spent the rest of the day just wondering. I moped around the train terminal for most of the afternoon but put on a happy face when the Wallace's returned, just in time to re-board the train. Emery was excited to tell me all about his day but his mother wanted to get settled in. She reminded Emery that we'd be having dinner in half an hour, once we got underway, and that he was spending the night with me tonight so we could catch up then. At dinner, Emery talked a mile a minute. "...so then we went all the way up to the top of the Sears Tower and after that we went to the natural history museum, which was really cool and then..." "Emery Honey, why don't you take a breath before you talk Simon's ear off," said Mrs. Wallace. "You'll have to excuse Em," said Mr. Wallace, "he just missed his brother." "Geez dad," Emery whined, slightly embarrassed. "What's the big deal?" I asked Emery, "I wish I had a brother to be close to. I think it's cool." "Oh they weren't always so close," said Mrs. Wallace. "Yeah, they used to fight like cats and dogs," added Mr. Wallace. "Avery used to think Emery was a little brat, until he grew up a little and started playing sports," said Mrs. Wallace, "once they had something in common, they got along much better." "Ok, let's go Simon, before my mom brings out the baby pictures," said Emery sarcastically. "You have his baby pictures with you?" I exclaimed. "Only the naked ones," laughed Mrs. Wallace, further embarrassing her son. "AHHH, we're outta here," screamed Emery, as he grabbed my hand and yanked me along with him. Emery grabbed his bag from his room and followed me down to mine. When we got into my room, I turned to speak to him but before I could get a word out he kissed me passionately. There was nothing tentative about this kiss, he virtually attacked my mouth. I heard a zipper and felt down to Emery's butt, I discovered that he already had his pants down and I decided to stop him there. I broke our kiss and gently, but firmly, pushed him back from me. I sat in my seat and looked at him, and felt a little bad for the disappointed expression on his face as he sat across from me in his purple Northwestern t-shirt, which clearly had been a gift from Avery, his black boxerbriefs and his jeans around his ankles. "Are you mad at me?" asked Emery. "No, of course not," I replied. "Did I do something wrong?" he followed. "No you didn't do anything wrong," I responded, "I've just been thinking." "About what?" asked Emery. "Well, this time tomorrow I'll be with my grandparents and you'll be on your way to your hotel in New York, what if I never see you again," I explained. "Yeah, I've been thinking about that too," Emery admitted. "You have?" I asked. "Yeah, it was in the back of my mind all day," said Emery, "I was having fun with Avery but, well, I kept missing you." "I missed you too and it's going to suck when we can't hang out," I started, "I know it's only been a couple of days but I feel really close to you." "That's how I feel too," said Emery, "I event mentioned it to my mom." "You did?" I exclaimed. "Yeah, my mom's really cool and she had some good things to say," he explained. "Like what?" "Well my mom and dad really like you, they said you seem like a good influence," said Emery. "That was nice of them," I stated. "Yeah, anyway, my mom said that good friends are hard to come by and that she'll help out so we can stay friends. She reminded me that you only live an hour away from us and that you can come visit us sometimes or I can come visit you. Plus there's always email and Skype and stuff," said Emery. "That's true, I guess it's not exactly the 1800's, just promise you'll email and call me all the time?" I asked. "I promise, but you have to promise too," said Emery. "I will, I just hope you don't get sick of me," I smiled. "Not possible," Emery smiled back. "I was thinking we could try something that would be a first for both of us, an experience we'll always remember," said Emery. "What did you have in mind?" I asked curiously. "We could fuck each other," said Emery. "I thought you were saving that for someone special?" I replied. "I think you're special Simon," blushed Emery, "When I look back at this 20 years from now, I want to remember you." "That's really sweet Em, but are you sure?" I asked. "Yeah," Emery giggled, "not only are you sweet but you're hot too." "Ok then, let's do it," I smiled. We quickly stripped down to our underwear. Emery had a head start so he finished a split second before me. We were both wearing black underwear and thought that was kind of sexy. We started out by kissing and rubbing our boners together, then moved into a 69 position so that we could suck each other's dicks. Once we'd satisfied our hunger for boy cock, Emery bent over the bed, exposing his cute butt, so I could fuck him. "Are you sure about this?" I asked again. "Yeah, go for it," said Emery. "But what if it hurts you?" I inquired. "I like you're dick Si," giggled Emery, "but it's not that big." "Well, it's bigger then my finger," I reminded him. "Yeah, I guess you're right, just be careful then," said Emery. I took Emery by the hips then began to rub the head of my cock against his butt. This was a totally new experience for both of us and it wasn't as easy as we had assumed it would be. I pushed against Emery's hole but instead of going in, it slipped out of place. After a few moments frustration, I took my dick in my hand, placed the head at his hole, then held on to it as I pushed in. I was rewarded for the effort with the head of my dick slipping into Emery. The problem is, once I was in, I didn't realize I needed to hold my position and let Emery grow accustomed to the intrusion, and I slipped into him until my pubes were brushing against his buns. Emery winced and let out a little whimper. "I'm sorry Em; I didn't mean to do it like that, are you ok?" I asked, concerned. Emery's eyes were shut tight and he buried his face in the pillow. I think he was crying a little and didn't want me to see. "Em, are you ok," I asked again. "Yeah, I'm alright," Emery sniffled. "Does it hurt; do you want me to take it out?" I asked. "It hurt at first, I wasn't expecting it to go all the way in, in one shot," said Emery, "But I'm getting used to the feeling now." "How does it feel?" asked Emery. I'd been so concerned that I'd hurt Emery that I failed to notice how great this felt at first. Once he'd asked, I could no longer ignore the amazing feeling my dick was experiencing. "It feels really good," I grunted, "it's so tight and warm." I gave Emery a moment to get used to the sensation and once he gave me the green light, I started to hump my dick into his hole. My motions were amateurish and jerky but I didn't care, the feeling on my dick was fantastic. Emery would grunt and moan, which would cause me to stop but he continued to assure me that he was ok. I was only able to fuck him for a few minutes before I felt my cum bubbling up inside of me. By the time I splattered Emery's insides with my juices, he was beginning to let out little moans of pleasure. With my energy spent, I collapsed against his back. Once my dick softened and fell out of his ass, Emery rolled over so that I could see his face. "That was starting to feel really good towards the end," said Emery, "way better than your finger." "I'm so sorry that I hurt you when I stuck it in," I apologized, "I didn't mean too." "It's ok," said Emery, "I know you weren't trying to hurt me." "Are you ready to do it to me?" I asked. "Give me a minute to catch my breath," said Emery, "being on the bottom took more out of me then I thought it would." When he was ready, I nervously got on my back and held my legs up. Since we had already tried doggy style, Emery wanted to see what a different position would feel like. "Just be careful, ok?" I asked as I felt the head of Emery's cock pressing into me. "Don't worry," he smiled, "Just try and relax." Right, I thought to myself, just lie back and think of England. That's something my mom always tells me, whether at the dentist, getting a shot at the doctor or getting scared at a horror movie, "If you're nervous, just lie back and think of England." I know it sounds stupid but it actually works. I relaxed and was surprised when I felt Emery's head pop into me while I was picturing Buckingham Palace. "Mmmm," I groaned. "Okay so far?" Emery asked. "Yeah, it's not bad," I replied. Emery pushed in slowly, my eyes watered a bit but I was experiencing a dull pain, not the sharp pinch I'd inflicted on Emery. By the time I felt his pubic hair brushing against my bottom, he was leaning in close enough to kiss. We had to stretch our necks a little but we were able to connect our lips and brush our tongues against each other. "Can I fuck you now? Emery grinned. "Yeah, just go slow," I giggled. That was all the encouragement Emery needed as he started to rock his hips gently back and forth. "Wow, you were right," grunted Emery, "this does feel good." "Mmm hmm," I moaned. It hurt a little at first but the more Emery worked his dick inside of me, the better it started to feel and like Emery, I was moaning when I felt hot liquid spraying my bowels as he came. "Well, we're not virgin's anymore," said Emery, as we snuggled. "Nope, I guess not," I responded, "How do you feel?" "Pretty good," Emery smiled, "I'm glad we did it." "Me to," I answered, "you only lose your virginity once and I'm glad I lost it to someone so cute and sweet." "Awwww, Si," Emery gushed. "Oh shut up," I giggled. "Wanna do it again?" said Emery. "Does this answer your question?" I replied as I rolled on top of him. We were so horny that we fucked each other a couple of more times before we fell fast asleep. We were still in a deep sleep when Emery's mom knocked on the door at 8:00 the next morning. "Boy's it's time for breakfast," said Mrs. Wallace, "Hurry up now." "We'll meet you down there mom," Emery groaned. We got dressed then headed for the dining car for breakfast. When we finished, we went to the sightseer car and when no one was looking, we held hands. We were both somewhat subdued, neither of us was looking forward to saying goodbye this afternoon. We waited on the train during our hour long layover in Pittsburgh and then we began the final leg of our trip. "You want to go back to your room for one last time?" asked Emery. "Yeah, I'd like that," I smiled. We got into my room and shed our clothes. "Smile," laughed Emery, as he snapped a picture of me in my undies, with his cell phone. "If that ends up on Facebook, I'll kill you," I laughed as I grabbed my phone and took my own picture of a similarly clad Emery. "Nah, that's just for me," said Emery, "I need something to jerk off too while we're apart." "We've always got Skype," I reminded him. "That's true, we can have some awesome cybersex," laughed Emery. We decided to trade blow jobs, one last time, and were swallowing each other's cum as we pulled into Penn Station. We had to dress quickly as we knew my grandparents would be waiting and Emery's parents would be eager to get off the train. "Gimme one more kiss," I said, "We're not going to be able to do that when we say goodbye." Emery just nodded his head then pressed his lips against mine. I savored our last kiss and held on tightly. When we pulled apart we both smiled and headed for the door. We met up with Emery's parents and got off the train, then went to the baggage claim where we found grandma and grandpa waiting. "Hey, there's my kid," said Grandpa as he hugged me. "How was your trip sweetheart?" asked Grandma. "It was pretty uneventful," I answered, as I winked at Emery, "These are my friends, Mr. and Mrs. Wallace, and Emery" The adults traded introductions and my grandparents thanked the Wallace's for looking out for me on the trip across country. "It was no problem," said Mr. Wallace, "He's a good kid and he kept our Emery entertained." "Well, I guess we should get going," said Grandpa, "we don't want to get stuck in that rush hour traffic." I shook hands with Mr. and Mrs. Wallace; they thanked me for my company on the trip and told me I was welcome to visit their family anytime. Then I had to say goodbye to Emery. "Goodbye Emery, I had a lot of fun hanging out with you," I stated. "Yeah, I had fun too. Good luck in Connecticut," said Emery, "Bye." I turned and started to walk away but stopped short when Emery called after me. "Simon!" Emery shouted. "Yeah," I replied as I turned. Emery wrapped me in a powerful bear hug and held on tight. "Goodbye," said Emery with a smile. "Goodbye," I answered. "My, he's certainly an affectionate boy," said Grandma as we walked to the car. "You have no idea," I thought to myself.