Morgan’s Misadventures – My first boyfriend by DerekTanner

My first boyfriend, sean

November 3, 2008

“psssst! don’t stare people will see” Mary-Lou swatted at my shoulder whispering quietly. I looked over and saw her wearing a devilish grin on her face. I responded with a stern look and snapped my attention back to what I was staring at. She knew, he probably knew, maybe they all knew, who knows. The only thing I knew is I was looking at the back of Sean’s head, a guy I recently took interest in.

Sean and I had known each other since middle school, like most of our high school, we lived in a small-er town so it was a moderately sized school that most of the kids around here go to. Anyway, so Sean, right? He’s not the tallest most muscly guy but I always feel at ease talking to him, he can make me laugh whenever he wants and his brown eyes look so shiny behind his messy hair. He’s in my grade and he’s in one of my classes, math. I was never really good at math so I’m in the lower-tier class in the school along with him, he’s in mostly these classes though, he’s had kind of a rough upbringing and doesn’t do super well in school. I twirled a strand of hair with my fingers as I watched him fill out his quiz, my gaze shifting to his arm every time it flexed up. Is he thinking about me? Can he see me right now on some reflective surface in the room? Did he actually figure out this dumb extra credit question? The class ended with us passing our quizzes up and a dull ringing from the bell. Sean got up and quickly gathered his things, I knew he had to get to practice so he would be in a rush, I stared at his butt the whole time until he was out of the room. I remembered Mary-Lou was still sitting next to me and I looked over, she had been looking me the whole time and just offered “you done? Or ya ready to head home” I shook my head a little to get out of my daze and with a “yeah” we were off.

When I got home I said a quick hi to my parents and brother in the front room before basically sprinting upstairs to cool off in my room. I slammed the door behind me and fell face first onto my bed. I couldn’t stop thinking about Sean on the whole bus ride home, or even the whole day, or all last weekend. A couple weeks ago I figured out from one of my friends Allison that Sean told his friend Mike that he liked me, OMG. I never really thought about him like that before but knowing he liked me and wanted me really made me feel a certain way about him. I stewed over these feelings for a week or so until I couldn’t take it. I told Allison to tell Mike that Sean can go for it, hoping he would get the message. He hit me up on snap last Friday and I added him right away, we talked that whole night. In typical Morgan fashion, I started to feel rather horny with these thoughts, and since I was finally free from school for the day and in the safety of my bedroom I decided to take care of it. I stood up and dropped my backpack on the floor, turned around an kicked off my shoes. I laid down on my bed on my back this time and stuck my hand down my pants to give myself a little tease before I stripped. It was at this moment I felt my phone buzz. I reached over for it and brought it up to my face only to feel my heart drop into my stomach. I had a new notification “Sean is typing…”

Sean and I hadn’t spoken since last Friday, I sent him some messages here and there but didn’t really hear back until like, right now. I was staring at my phone waiting for the message to deliver when I get a text from my dad telling me that he and my brother are going camping this weekend, whatever. I swiped that text away and finally had a new message to read from Sean. “Hey, whats up?” I have never been more disappointed in my life. Mainly because I couldn’t figure out what to say back. After a few minutes of staring at the phone fumbling I asked him about our math homework and that turned into talking about school and talking about people at school. I was so entranced in this mundane conversation that I was surprised to see a text from my dad asking if I was coming downstairs for dinner, I thought it was a little early but upon seeing the time stamp I was floored, I had been talking to Sean for 4 hours and it was time for dinner! I texted Sean that I had to go deal with family, then probably pass out soon after. After that, finally, I get this from him. “Are you free this weekend? The weather is really nice, I was thinking we could go on a hike? Just the little trail down the street from us.” I couldn’t believe it, he finally did it, he asked me out! AAAAAAAA. I told him sure that sounds awesome. I couldn’t keep myself from smiling and blushing as I walked downstairs to the dining room to eat.

November 7, 2008

“This week has been too fucking long” I proclaimed, sitting down at my normal lunch table with my friends. I was met with a chorus of “I feel that,” “tell me about it,” and “for real.” Mary-Lou didn’t say anything though, just a soft chuckle. She was the only one I confided my plans with Sean to so she was the only other one at school who knew, at least I hoped. I had been talking with Sean all week about our weekend plans, then immediately relaying to Mary-Lou so she could coach me through talking to him. She is a super solid best friend for doing that all week, staying up with me, though she always seems sad when I mention Sean and how excited I am. I think she’s scared to lose her friend to some guy. As shitty as it may sound, I’m more focused on my feelings at the moment, I can’t help it! Maybe it’s those hormones people talk about. I looked up and caught Sean looking at me from across the cafeteria, he smiled, I smiled back and watched him go on with his friends. Looking back down at my food, I decided to just eat quietly and make my way to my next class. I’m worried I’ll gush about Sean if I hang out in the cafe too long. “Had to escape, they’re trying to figure me out” I sent a quick text to Sean on my way out. “hahaha, yeah trying to figure out why you’re weird lol.” Our texts had been getting more and more flirty, I wanted to send him a special one before we hung out outside school.

Later that night I was on my bed trying to recover from the HUGE meal I ate. I knew it was a mistake but dad took me and my brother to our favorite pit beef restaurant for dinner and we pigged out hard. I sent Sean a “whats up?” while getting ready for bed. “Hey you” he replied, “I thought you don’t talk to me after dinner, I’m more of a before dinner friend.” It was true, I usually check out after dinner and just get some rest, but that’s because I have to wake up early to feed the pets. This night though, I still had work to do. We set a time and place to meet tomorrow, exchanged our normal pleasantries, and then it was time. I took my sweater and undershirt off exposing my breasts, and I put on my best yoga pants. I got my phone ready and splayed out on the bed. I attempted the sexiest pose I could think of that showed off my boobs and stomach and sent it to him with the caption “Getting ready for tomorrow!” Almost instantly I got a “:O” and “Those are amazing!” back from him, I was happy with that, I love being a little tease for him. I slid off my yoga pants and tried to fall asleep, it was difficult but finally I got past the excitement and let myself rest.

November 8, 2008

The next morning I woke up and did my normal routine. I woke up before the house and fed the pets, then I made myself some cereal and ate before going to the bathroom to get ready for the day. I turned on the shower and brushed my teeth, then made sure to grab a new razor out of my dads drawer before stepping into the shower. I gave myself a good washing then shaved my whole legs and crotch. I pictured him while running my hands over my body, letting myself get lost in the thought of him, but before it took too long I rinsed off and got out of the shower. I looked in the mirror and checked myself out one last time before I donned a towel, grabbed my wake up clothes and went to my room. Sean was already texting me by the time I got back to my phone. I confirmed I was awake and on my way before putting on my hiking clothes and taking off before anyone woke up.

I walked down the street to our meeting place, the intersection between the street we live on and the local hiking trail. I saw him there waiting for me before he noticed me walking toward him. He was wearing these kinda dorky athletic pants and an old tank top, god his arms looked nice, did he start working out? He had a blue baseball cap on which was pushing down on his thick, moderately curly brown hair. I couldn’t wait to spend today with him. He looked over once I was in earshot, his face lit up a little and he said “Hey!” “hey there” I replied, probably smiling way too much. “you all ready morgs?” he asked to which I replied “hell yeah lets do it.” We awkwardly set off toward our destination, a small scenic overlook of a neighboring town. The walk up was about an hour we talked a bunch and even held hands for a good amount of it, coming up on the view when we finally got there was breathtaking.

“Holy shit thats cool” he said. “I know isn’t it incredible!” I cheered back “I love coming up here to decompress” “me too” he said back. He looked over at me right in my eyes, I noticed and looked over back at him. He stepped closer to me, almost touching, god he smelled so good. Still staring into my eyes he says “ya know Morgan, I’ve always had kind of a crush on you.” I couldn’t believe it, I mean I could, I had a pretty good feeling he felt that way, but I was still shook. “yeah?” I said, smiling and trying to hold back my excitement “well for what its worth, I like you too” I barely got those words out, I was actually sitting there congratulating myself on getting through the moment, not realizing it wasn’t over. He put his hands on my arms, holding me. “can.. can I kiss you?” he asked. I almost screamed “OF COURSE” and I embraced him. I moved in closer for the smooch and when our lips met I almost fell over, it was awesome. I felt the warm, soft, wet texture of his lips on mine and reveled in it. We pulled apart from each other and I say “well what now?” “How about we walk back down” he suggested, and I followed. On the way back down to our street I remembered, HOLY SHIT, my dad and brother are out camping all weekend! I had completely forgotten, I asked Sean if he would like to hang out at my place when we got back and he said of course. We made our way back to my house, which was just a few houses down from his, but on our street that meant a little over a mile extra. We were both too excited to care though. We held hands the whole walk down.

As we walked into the house I looked around just to make sure I didn’t see anyone home, I knew they were gone but I was paranoid as usual. I turned back around toward Sean as he was closing the door. “So?” I said “What do you think of casa Morgan?” I looked at him with a little smile. “it’s really nice and cozy in here… y’all got a bathroom? I really need to pee” he asked. “Come on I’ll show you, it’s right across the hall from my room,” I took his hand and led him up the stairs, I showed him the door to the bathroom and opened the door to my room. “Meet me in here when you’re done!” I said, he nodded and smiled before turning in to the bathroom. I dashed over to my dresser as fast as I could and pulled out my sexy bra, I had one, and my most revealing pair of panties. I changed into those from my hiking clothes faster than a guy could pee. I then sat on my bed and waited for Sean to come in.

I heard the toilet flush and the sink turn on, then soon after it turned off and I heard the bathroom door open. I heard a timid knock on my door and said “come in!” He opened the door and walked in, I swear I saw his jaw actually drop, he looked at me up and down and said “whoa, Morgan! Did you wear that under your hiking getup?” “hahaha” I chuckled “no, now close the door” I said, and he obliged by gently shutting the door, then moved his eyes back to my body, then back up to my eyes. I walked up close to him and embraced him, taking in his incredible scent. It was weird most boys smell bad all sweaty but he smelled just a little musky, a little damp, and a whole lot of I don’t even know what, hot guy smell? That stuff. With his arms around me he started squeezing my back and roaming around with his hands, I pulled away slightly, looked in his eyes then dove in for a kiss. I pushed my lips on his hard, moving one hand to the back of his head and with the most courage I’ve had so far stuck my tongue in his mouth. It was definitely awkward at first but we got used to each other’s rhythm and feel and lost ourselves in the moment. When I finally puled away again I noticed his hands had not moved. “are you gonna grab my butt or not?” I beckoned, leading on with a little smile. He gave a big grin and reached down with his arm, cupping my butt and giving it a tight squeeze, then a little spank. I was so excited I could already feel myself getting wet. My heart was pounding. I was about to burst, I was ready for it all. I pulled away from his arms, then came back close and lowered myself to my knees in front of him. With his mouth slightly open he quietly says to me “whatcha doin down there morgs?” “Isn’t it obvious?” I said, and started grabbing his shorts “take these off” I commanded. He lowered his shorts to the floor leaving just his tight fit boxers with a bulge in them. I looked up at him as I moved my hand toward his waist, I cupped the bulge and felt the warmth from it, that turned me on so much. I played with and prodded at the bulge till it got a little harder, then motioned for Sean to take his underwear off. Finally it was revealed. As he slid his boxers down emerged the cock of my favorite guy in the world, and I wanted to treat it that way. It was honestly a really nice looking cock, well sized for our age but not big enough that I was worried it would hurt. I stared at it for a few seconds before looking up at him “nice cock” I said with a fiendish grin “thanks” he said back blushing. “can I touch it?” I looked up and asked, with the sexiest look I could come up with. He laughed “sure but stop looking at me like that” we both laughed and I reached out. I felt his cock in my hand for the first time and started to stroke it back and forth slowly. The skin was so soft and smooth, loosely holding onto the more sturdy core. I pulled it along with my hand as I stroked him up and down increasing my grip slightly. I moved a little closer to him, making sure my head was right at dick level and then the smell of his arousal hit me. From hugging him I got a little bit of this scent but it was intense straight from the source, it was intoxicating. I felt myself getting more and more excited as I stroked him. I could tell he was getting more excited too, with his member turning hard in my hand.

My eyes went from his eyes back down to his cock. It appeared to be standing at attention. I looked at it straight on, from the side, I really wanted to check it out. Once I had my fill of looking I moved my face closer to it. Slowly I moved my lips toward the head and gave it a soft kiss. I looked up at him to see a big smile then looked back down . I extended my tongue and licked under the head of his cock, moving my lips closer until it started to part them, I let some of it in my mouth and moved my tongue around the head sensually. With my right hand I reached around him and grabbed his round butt, squeezing it and rubbing it. Then I moved my left hand just under his balls to fondle them as I explored his dick. I started to allow more of his cock in my mouth, moving down his shaft then back up slowly. Each time make more and more of a suction with my mouth. “Oh my god thats amazing” I heard him say, I was proud of myself, and his appreciation turned me on even more. I started bobbing my head up and down his shaft faster, making sure to keep the suction the whole time. I started to taste a lot of precum and his natural taste, it enveloped me until I couldn’t control myself. I worked on his cock over and over and over until I felt it twitch. “ooooohhhh shit, aaagggghh” I heard from Sean as I slowed down, four big ropes of cum shot into my mouth, filling it up and nearly making me gag, I swallowed with his cock still in my mouth then slowly removed it, gave it another kiss, then looked up at my man. He was looking down at me, with a big goofy smile and just says “Morgan that was awesome!” “haha I’m glad!” I said back. I stood up and he pulled me in for a kiss, his cock still semi hard pushing against my tummy. “you know this isn’t fair” he said. “whatcha mean?” I asked. “I’m more naked than you are” he cood, eyeing me up. “alright, lets fix that” I said. I removed my bra and said “Tada!” as my boobs fell out of it, he was clearly impressed because he couldn’t stop looking, until I took my panties off and revealed all of me. I stood there in front of him and said “well, now it’s not fair for me, lose that shirt.” He took off his shirt and I took it all in, all of him, at once. He was so sexy and in that moment I just wanted to be all over him. Before I could think of something to say he asks “can I touch your boobs?” with an eager look. I said “of course, you can touch me anywhere you want” “ANYWHERE I want??” he shot back “yep” I said with a little pop from my lips.

He stepped closer and cupped my breasts with his hands, both of them at the same time. He was excited clearly, as he fondled and squeezed. He brought his mouth to one of my nipples and gave it a sharp suck. I let out a moan and he looked up at me. “You wanna lay down on the bed?” I asked, to which he nodded. We both laid on the bed and turned toward each other, still touching and running our hands along one another, just exploring and feeling each other. I noticed his cock getting hard again and reached for it, giving it a few strokes up and down, it felt as hard as it was in my mouth, and still all wet with a mix of our fluids. “its ready to go again if you are” he breathed, “oh I’m ready” I replied, “get over here.” I shifted onto my back and he shifted onto me, seeing his face hover over mine and his body cover me completely was an arousing perspective to say the least, I pulled him in for a close kiss before pushing him up and looking into his eyes. “go really slow the first time you put it in, it feels really good” I murmured. One last time he asked “you ready?” “mhmm” I shot back, biting my lip. He tried to guide himself into me with little luck, so I tucked my hand down there to help him get the right spot. As soon as his hit my entrance I let out a sharp gasp “thats it, right there” I signed out. He began pushing in slowly like I asked. I gazed up at him and we stared at eachother. He pushed farther and farther in, I let out a little moan and he dropped his head down to kiss me, we made out while his cock slid farther into me until I could feel his balls drape over my ass. He pulled away from the kiss when he started to pull it away. Slowly he took it almost all the way out, then slowly back in. I watched his cock disappear into me until he hugged me close and I nibbled on his ear as we rocked back and forth like that. Feeling his cock stretch out my pussy was insane, slowly but surely it became more comfortable to accept him and all discomfort turned to pleasure. “you can go faster” I whispered into his ear. He came up and kissed me as he sped up his thrusts. He pumped in and out of me, grunting faster and faster. My arousal was through the roof, I was so wrapped up in the moment a car could crash into the house and not even phase me. From my hips I could feel an ache that turned into shaking, waves of pleasure shot through my whole body as I had my first orgasm with Sean. My whole body tightened and shivered. He must have noticed because he let out a grunt as he started to thrust into me even quicker. Until I felt a few little jolts from his cock inside me, and the feeling of a warm pool of liquid build up inside me. He gave me one more kiss as he slowly pulled himself out of me. He shifted off of me and laid on the bed, we faced each other and got close. We made out a little more before deciding to take a nap together in my room, this was about to be a fun weekend.

Leave a Comment