Introduction:
Hello readers this is my first story so give me feedback, I’d greatly appreciate it. If people enjoy this story enough I’ll consider doing another. This story doesn’t really relate to anything in my life and the names and such are pretty much random so any likeness to anyone or anything in the text is purely coincidental. So with that all said and done enjoy!
Let me start this story by describing myself , my name is Jimmy I’m 14 and I stand at 5’9 190 lbs. Yeah I’m pretty overweight, but I don’t eat a lot I just don’t get much exercise. So its the summer after 8th grade and I was told that I will be moving to Boston before school starts by my mother. Needless to say I was destroyed by the sudden news. I’d lived in the Lowell for almost 10 years now.
I knew i didn’t have to start packing my things until August, so that meant I had about one months until then. I wanted to spend time with all my friends before I left, but more importantly I wanted to hang out with my best friend Casey. She and I had been friends for about a year now but we were comfortable around each other. I met her through my old friend who I knew since the fourth grade, they were dating back when i first met her. My friend’s name was Hunter and unlike me he had a large amount of girlfriends throughout elementary and middle school. I didn’t think that I was really all that ugly , I guess it was my lack of confidence that kept me from having one for so long. I was pretty social and I had a lot of friends but never got to that level with any of them. I never even got to the level of best friends with anyone until Casey.
As I went through middle school I found a large interest in two things girls, and football. I wasn’t very athletic so I was usually picked somewhere around last for flag football but i still loved playing it. Hunter and i would talk smack back and forth throughout the games , even though he was much better than I was. Pretty much after every game we would go to a grassy spot where Casey and some of her friends would watch us play, and just joke around until we had to go home. Casey and Hunter didn’t really kiss all to much and held hands most of the time they were together. I always found it a bit odd considering they were going out for so long.
Anyway back to my moving and such. I got out my phone and began to text Casey. I told her about me moving and how I wanted to hang out soon. She just sent me a sad face and tole me to go to her house on Saturday. It was a Wednesday when she sent that. I had been to her house about half a dozen times and her grandmother and two sisters seemed to enjoy my company. After I told her that I would see her Saturday, I began to call and text other friends to see when they were free. By the end of the day i had 8 or 9 plans riddled around the next month. The most recent one i had was to go to the movies with my friend Ana and her friend Amanda in 2 hours. I told my mom about all my upcoming plans and she just nodded and told me she’d take me to the movies.
Two hours quickly passed and I was arriving at the movie theaters. I saw both the girls near the front giggling about something. I got out of the car and waved at my mom as she left. Let me describe Ana and her friend. Ana was about 5’5 with auburn hair and big brown eyes, I guessed she had B cup breasts and and toned legs leading to a small but firm looking ass. Amanda was about 5’7 with dirty blond hair and piercing blue eyes her breasts looked a bit larger than Ana’s and her ass was a tad larger. They were both wearing mid thigh jean shorts that showed there long toned legs. Both girls placed soccer and it showed when you looked at there thighs and calves. Ana saw me and immediately darted over to me she yelled my name and jumped onto me latching her arms and legs around me. She was saying something but it was all muffled because her face was mushed into my shirt. My eyes went looked down at the top of her head and then at her friend who looked at us with a puzzled smile on her face. Ana’s body felt so warm pressed up against mine. After a couple seconds of awkward silence her grip on me loosened and I was able to pry her off of me. She was looking up at me with a large smile and i returned it as i spoke. “Well hello to you too.” I said as a warm gust pasted my face allowing me to smell her perfume, it was intoxicating.
Ana looked back at her friend and gestured her over to us. When she began to walk towards us Ana turned and spoke. “This is Amanda, she’s on my soccer team.” She said pointing at her as if I could think she was talking about someone else. Amanda just gave me a small smirk and waved. I waved back and we began to walk in to get our tickets and watch the movie. We had about 15 minutes before the movie started so Amanda went to the bathroom. Ana turned to me as soon as her friend left and started to talk. ” Jimmy im gonna miss you when your gone.” She stated as her hips slowly moved from side to side.
“Yeah I’m gonna miss you too.”I said looked at the ground and then back at her. Ana wasn’t really a knockout but she had that girl next door look. Her face seemed to light up after my reply.
“I wanna ask you a question.” She paused then looked at me, I just nodded and she looked down before speaking. “Why haven’t you ever…. you know like asked me out or tried to kiss me or anything. You know I like you so why haven’t you done anything.” She looked back up at me and her eyes a bit watery. I instinctively wrapped my arms around her and held a bit closer to me.
“Well how would I know that someone as cute and great like you would like someone as fat me?’ I asked looking down at her. It was a real surprise to me that she liked me. I had always just assumed that she was just acting friendly towards me i never took it as flirting or anything even close to that. I never really had it in my mind that she or anybody would like me in that sort of way so i never really thought about it. But now I was. ‘Why can’t you see things that are right in your face? You fat fucking idiot.’ I thought to myself as I held the girl tightly to me.
She looked up at me with a sort of confused look. ” You really think I’m that shallow?” She said with a tint of anger in her voice. She pushed her arms between them and created some distance from me and stared at me waiting for me to say something.
I just looked down at her with my mouth open and odd sounds escaped them . I sighed and took a deep breathe, trying to regain my composure. ” No i just never thought you’d be interested in me. I’m just so sorry that I’m so stupid and that I finally see it now when I have limited time with you.” I was looking into her big brown eyes and just couldn’t resist her. I lowered my head and pressed my lips against hers. I felt her body tense up but it soon relaxed and her fingers ran along my neck. Her lips tasted a bit like strawberries and i could feel her tongue lightly brush my lips. Our kiss ended when we heard someone loudly clear their throat behind Ana. We both looked in the direction of the sound and saw Amanda grinning widely at us both. My face was getting hot and red to showcase my embarrassment. She told us that the movie was starting and we both quickly walked to the dark room as the previews rolled on. The movie was about some middle aged woman trying to get custody over her child after she was convicted of some crime, but I wasn’t really paying attention to it. My mind was just replaying the kiss over and over and over again. I didn’t even notice that the movie ended until everyone got up and the screen went black. I got up and stretched then looked at the two girls who were chatting about something.
I called my mom to tell her the movie was over and that she could come pick me up. As I walked out of the room I turned to see Ana talking to Amanda. Before I could even open my mouth she grabbed me and pulled me to a bench and sat me down. “I liked that kiss i really did but……. I’ve been in a long distance relationship before and it just doesn’t work out.” she said as she held my hands in hers. I just looked down with a disappointed look on my face. she cupped my face in her hands and made me lift my head. She leaned in and planted a soft kiss on my lips. I just murmured that it was fine and she got up. I was a bit startled by Amanda’s hand on my thigh. I quickly twisted my neck but she was behind me so i couldn’t see her face.
I felt her warm breath up against my ear and it made my heartbeat quicken. Her hand made small circles on my thigh and was dangerously close to my growing erection. ” She told me about you moving to Boston. My grandparents live there and since you and her aren’t going out I was thinking that maybe next time I went over to visit them , I could call you and we could hang out.” With the last statement she flicked her tongue on my earlobe and gave my cock a quick squeeze. I was speechless and the combination of her breasts pressed onto my back , her warm breath on my ear and her hand placement had my mind in turmoil. I felt her body slowly get up and I saw her ass sway from side to side and then my eyes moved up to her face. She was looking back at me and biting her lip. This made my cock twitch and bounce in my jeans which caused me a bit of pain.
Thankfully my boner subsided before my mom arrived. The next two days went by uneventfully except for a trip to the mall with Hunter on Friday. It was Saturday morning and my mom brought me to Casey’s house. I knocked on the door and was greeted by Ashley. Ashley was Casey’s friend and they had been friends for 9 years. Ashley was a grade below us but she was born the same year as me, unlike Casey who was born a year before me but in the same grade as me. I said hi to Ashley and she told me that the only people in the house was her and Casey. I closed the door behind me and followed her into the living room. Casey was sprawled out on the floor watching t.v. Ashley plopped down onto the couch and resumed watching t.v with Casey. Casey is 5’6 with light brown hair, hazel eyes, tan skin and B cups , her ass wasn’t much to look at though. Ashley on the other hand has a firm little bubble butt her hair and eyes were darker than Casey’s but her skin was fairer and her boobs were a bit smaller. Casey was wearing a black tank top and long pajama pants. Ashley was showing more skin in her white tank top and tight black shorts that ended about half an inch under her ass.
I thought that Ashley didn’t really like me, not saying that she disliked me but she seemed neutral towards me. I sat down next to her and all three of us watched the television for a while before Ashley got a call from her boyfriend and left up to Casey’s bedroom to talk to him. Soon after Casey went to take a shower. I saw some keys next to me and I thought they were Ashley’s, so I went up to give them to her. When i opened the door i saw her weeping into a pillow. “Oh sorry Ashley I just wanted to give you your keys.” I placed the keys on the dresser and sat down next to her. “Wanna tell me what happened?” I asked her. She sniffled twice and began to tell me about how her boyfriend cheated on her. I pulled her close to me and she asked me why men are such assholes. “I don’t know maybe we just can’t help in when girls like you make us crazy all day long. We just don’t know how to handle ourselves when you walk around looking the way you do.” I replied with a smile trying to cheer her up. When I saw her smile I knew I succeeded. My eyes widened when she rose her head to make her lips meet mine. Her body was nudging me and she gently pushed me onto my back.
She straddled my stomach and put her hands on my shoulders to ease her head down to meet mine. I felt her tongue jab my lips and i opened them to let her probe my mouth with it. Our tongues danced for a while and I almost didn’t notice her grinding her groin into my stomach. Our lips parted and she stared down at me for a little bit still grinding into me. Her breasts felt so soft on my upper torso and they bounced a bit when she rose up higher. I looked at her crotch and was able to make out a wet spot on the black shorts. She leaned back and by her facial expression I’m sure she felt my erection on her ass. She grinned and slid down my body until her head was leveled with my dick and her hand went down to my zipper. She unzipped my fly and grabbed my hard cock and got it out of the prison that was my boxers. She looked at my cock as it bounced and stood proudly. I got goosebumps when she blew cold on the swollen head. I looked down at her , she gave me a slight grin then engulfed my head with her warm mouth. I almost came at that very moment but I somehow held it in for a while longer. The slurping sounds she made just heightened the pleasure. A couple of minutes passed and a i felt the pressure in my balls rise. “Im gonna cum soon.” I muttered and she sped up her bobbing. I felt my balls tightened and my sperm begin to erupt from my head.I lifted my hips up into her mouth. Her mouth stayed latched onto my head for a bit longer. When she finally released it i heard a loud audible pop.
I saw her swish my cum in her mouth for a bit and swallow it. She gave me a large smirk. i tucked my soft meat back into my boxers and sat up looking at her. ” I thought it would taste a really bitter but it wasn’t that bad.” I locked my lips with hers again and let my left hand roam to her breast and then put my right hand drift down to her pussy and rub it in small circles. She was moaning into my mouth i could feel her nipple getting harder against my palm. I slid my left hand down her stomach and let my fingers lie on top of her waistband. My fingers coiled around It and slowly pulled her shorts down. She backed up and took the shorts completely off, throwing them to the floor and her cotton panties followed shortly after. I was now staring at the first pussy I’d ever seen in real life. Her glistening lips and her clitoris that peeked out of its hood were staring back at me. I quickly grabbed her around her waist, bringing her pussy to my lips. Now that it was so close i was able to see the short black hairs she had above her mound. i could smell her anticipation and it drove me insane. I stuck my tongue and gave her clitoris a quick flick with it. I knew that it was very sensitive from all the porn I watched. I used my fingers to spread her lips and kissed the pink flesh. I ran my tongue up her slit and poked it into her a couple of times. I took my index finger and popped it into her tight awaiting hole. I directed my attention to her clitoris and flicked it up and down as she began to thrash in my arms. I guessed she was having an orgasm began her body was tensing up so i put my mouth over her hole. I thought that if she tasted my cum I might as well taste hers. I lapped up her thick juices as she flooded my mouth with them. She began to relax but i was still slowly licking up and down her slit.
We both heard the water in the bathroom shut off and she hurried to get her clothes back on. When Casey entered the room she told me to get out because she had to change and I left going to the bathroom. I didn’t want to wash Ashley’s juices off of me but I knew explaining the smell would be a hard thing to do. So I stood at the sink and splashed water all over my face and dried off. When I came out of the bathroom I noticed that both girls were back downstairs in the living room. I joined them and left about an hour later. On the way home all I could think about was Ashley’s blowjob and how her pussy tasted.
The rest of my time in Lowell went by way to fast and soon I was organizing things into my new room in Boston. When school came along I signed up for football. My piggish body allowed me to be a lineman. But I slimmed down and was moved to tight end and linebacker my sophomore year. Throughout my freshman year Amanda came by about 6 times and we would give each other oral sex because she didn’t want to have vaginal sex yet. My sophomore year i was 2nd string on varsity and that made getting girls a lot easier. In the beginning of my junior year my mother told me we were going to move back to Lowell, in July. I never really asked why. In my junior year I started and already had some school scouting me.
My school was in the playoffs and we had made it all the way to semi-finals, Our opponents were actually the high school i was going to attend next year. In the fourth quarter it was 8 to 8 and they had the ball. The quarterback for the team was Hunter and he was having a very good day, he had no turnovers a touchdown and about 350 yards passing. We were playing in zone and i crept up to the line as if I was going to blitz. Hunter fell for it and call a curl by is tight end. The only problem was that when he ran the route it was in my zone. I guess he hadn’t seen me or thought i couldn’t react fast enough. The ball left his hand and was going towards his tight end but I leaped up and snatched it out the way. I made a dash for the endzone but only got to their forty-five before their running back tripped me up. My coach called a 4 receiver set so I was off the field there only 30 seconds left in the game and our quarterback heaved a bomb up to our shortest receiver. The safety extended and intercepted it pretty easily. But unlike me he had tremendous speed and was able to weave his way into a touchdown. I felt my heart drop as I looked at the time and saw we only had 19 seconds left. After the kick-off coach put me in the slot and made me run a go route. So I streaked down the field in pretty much a straight line. I saw the ball up in the air and I knew I just had to go up and snatch it. The safety that had the pick six was looming over me so I had to turn to go up and catch it. I was able to bring it down but I was downed at the ten yard line. I looked up and saw the time dwindle down to zero. one side of the stadium erupted in cheers and screaming the other grew silent. The game was over and they had beaten us by one touchdown and and two point conversion. All the players and coaches went to the 50 yard line to shake hands and such. I was at the end and Hunter was at the end of his. After shaking hands they began to talk.
‘Hey Hunter, next year if I i catch your pass in a game it won’t be an interception.” I said with a grin. I didn’t know if he would get what i was trying to tell him. The huge grin on his face told me he did. They talked about the game for a bit and then the subject moved to girlfriends. “So how is Casey?” Hunter just sighed and shook his head.
“I broke up with her man. She was kind of a prude. We only did it like three times. I could do it three times a day with three different girls if I wanted to.’He said kind of cockily and with a chuckle at the end. Hunter was douche at times but he was trustworthy when it came to anything besides girls. he’s the kind of guy that would fuck your girlfriend with you two feet away but wouldn’t even steal a quarter from you or lie about fucking your girlfriend.
“Oh really I didn’t know you two broke up I kind of lost touch with her after my first year here.’ I said before hearing my coach yell at me to get my ass to the bus. “See ya next year man” I said to hunter before waving and jogging to the bus we would take back home. It turned out that they lost in the finals to Everett.
The rest of the school year dragged on and Amanda’s grandparents passed away so she never came back. I got a couple of random handjobs and blowjobs as year progressed but I was still a technically a virgin. I called Amanda and told her I would be moving back soon and she told me that I should call Ana because she was always asking about me whenever she knew that Amanda was going to Boston. So I did as she said and called Ana .Her voice was just as sweet and soft as I remember it. I told her i was coming back home and she shrieked in excitement she pretty much begged me to go on a date with her. Although there was really no need to as I would’ve said yes anyway. We set up a time and a place and we said goodbye to each other.
Soon it was time to pack and move again. We left early so we got to our new home around eight AM. I had my licenses and my mom let me use her car often so i went to a diner a little ways away to get something to eat while my mom set her room up. When I got to the diner i ordered some eggs and bacon. i heard some girls giggling and laughing. i turned my head and saw that there were three girls , around my age maybe a year younger. I smiled widely when i saw that one of them was Ashley. My food hadn’t arrived yet so I got up and made my way over to them. They went silent when I got close. “Hey Ashley. Remember me, Jim….Casey’s old friend.” Ashley just stared at me and looked me over a couple times. I waved my hands and snapped my fingers. As an attempt to get her out of the trance she seemed to be in. She blinked rapidly a few times and stuttered a bit. I heard a woman call me and when i turned i saw that it was the waitress telling me my food was ready. “Well I’ll see you around Ashley.” i said walking back to my table.
The food wasn’t all to great but it didn’t make me want to throw up either. I paid and tipped the waitress before I left. I headed back home and found my mom snoring on her mattress. I put all my things into my room and laid on my bed for a nap. I woke up at about twelve forty-five , I groaned getting out of bed and saw that my mom was still sleeping. I decided to call Casey and see whats she’s up to. When i called she seemed upset but cheered up when I told her I could come over to hang out. I got my keys and got into my car. I’m not sure why and how I remembered the way to her house but I just did. I knocked on her door, when it opened i saw her and i immediately saw what time had down to her and her body. Unlike Ashley who’s body stayed pretty much the same and just looked a bit older, Casey’s body matured and nicely might I add. her breasts had grown to C’s and her body now resembled an hour glass pretty well. I didn’t notice that she was staring at me because my eyes were fixated on her body. When I did finally notice it I saw she had the same look that Ashley did. “Ashley told me you had grown to be fucking hot but I didn’t know how right she was.”
I just chuckled at her statement and walked inside. When I did three sets of eyes were staring at me. Ashley, Casey’s grandmother and Casey’s sister were all staring at me. I felt a bit uncomfortable but shook the feeling as I want to sit next to Ashley. Casey came and sat next to me but didn’t say anything. I didn’t really know what to do so I just hummed a bit. After a few minutes everyone went back to whatever they were doing before. I turned to Casey who was still looking at me then back at Ashley who was also staring at me. “Okay can I just know why you guys keep looking at me?” I said turning my head from side to side.
“Well you just look so different now. Your actually cute now. It just seems weird” Ashley blurted. I looked over at Casey to see if she felt the same way. By the look plastered on her face I could tell she did. I just laughed and shook my head.
“Really? Wow thats dumb. And Casey haven’t you looked in the mirror? Your not hard to look at. Ashley you’ve always been told your hot so no need to remind you of that.” I said smirking at both girls. We talked for about two hours just catching up and talking about our senior year and Ashley’s junior year. Somehow we got to dates and i said i had one for tomorrow with Ana. Both of there smiles subsided at the mention of me having a date. I don’t understand why.
I left shortly after that and saw that my mom was awake but still in bed. I looked at the clock it was already five o’clock. I took a shower and then watched television until I fell asleep. I woke up with morning wood and remedied it by jerking off in the shower. It was eight and my date was in three hours. Those three hours passed sluggishly. I got into the car and drove to her house. I didn’t know she was home alone. we were watching a move but halfway through it we were just making out rather than actually watching the movie. She told me to follow her ,I did and soon i was in her bedroom. She jumped onto the bed and laid down. Now i was able to really see her and how much she changed. I was glad to see that her legs were still long and looked even more toned than when they were younger. I also noticed that i wasn’t the only one that had gotten taller. She didn’t grow to be 6’4 like me but she looked about 5’9 maybe 5’10. She was sporting some D’s on her chest but the look of innocence is still all over her face. Needless to say I found her even sexier now that i did back in the movie theaters 3 years ago.
“Jimmy are you a virgin?” she asked me. I just nodded my head up and down to gesture yes. She smiled and grabbed me pulling me onto the bed with her. “Well then we can learn together” She said as she began to take her shirt off. After that came her pants and then her bra. Her nipples were quarter sized and I reached out to pinch one and suck the other into my mouth. She was moaning and reaching to find my cock. By now it was as hard as steel and aching to get out of his pants. She finally unzipped it and looked down at it. I heard a small gasp escape her mouth.”Jimmy your huge.” I didn’t really think eight and half inches was huge but i guess she did. She was slowly pumping my dick and my hand found its way into her panties. I stuck a finger in her and marveled in how tightly she was gripping my finger Although I didn’t feel her hymen. I thought about ow tight she would be on my dick considering she had had my finger held strongly.
She back away to take her panties off and I used the time to strip off my clothes. I laid there slowly stroking my dick as some precum leaked from the bulbous head. she moved her head down to my crotch and enveloped my head in her warm mouth. I groaned as her tongue swirled around the head. Her head bobbed up and down as i felt my head nudge the back of her throat a few times. she was trying to deep throat me but her gag reflex was making it difficult. I gently put my hands on the back of her head and pushed down onto my cock. I felt my head slide down into her throat, it was a magnificent sensation. She pulled herself off to get some air. she straddled my waist and held my dick in her hand aiming it up at her wet slit. My penis twitched in anticipation of getting inside her warm tight snatch.She slowly lowered herself onto my rod. A moan left my lips when my head popped into her outstretched hole. Her pussy was hot,wet, and oh so tight. It felt like a very snug oven but her natural secretions were cooling it down at the same time. I saw her face scrunch up and her eyes shut tightly as she tried to take more of me. She was halfway through when she took a deep breath. She looked into my eyes and dropped quickly onto my lap. Our naked pelvises slapped together , my pubic hair was short but it was poking into her bald pussy now. She groaned and moved her hips around after a while. She hadn’t accommodated to my size yet but she was still grinding her clit into me. My hands reached around and grasped both her butt cheeks and i tried to get more of myself inside of her if it were even possible. After a couple of seconds she rose up about an inch and came down softly. She repeating this motion until she was almost lifting off of my dick and slamming down my entire shaft with a loud audible slap.
I felt her body stiffen and tighten then she began to jerk a bit and her pussy was convulsing on my dick. looking up at her face I could only describe it as pure bliss. She was slowly rocking back and forth for a while then looked down at me with lust in her eyes. I raised my arms so they were curled over here shoulders and pulled her down so her back was on the bed. My penis was still nuzzled inside of her. She had her hands on her breasts rubbing and pinching her nipples. I started to pump her with long slow strokes and used my thumb to rub her clitoris at a slow pace. I gradually built more speed in my thrusting and my thumb work. Soon I was thrusting into her hard and her whole body would jump with every thrust. When this happened her boobs would bounce. She bit down on her lower lip as her second orgasm flowed through her. The feeling of her pussy contracting on my dick sent me over the edge, I felt the sperm in my balls rise up through my shaft and I hurriedly pulled out of her and gave my dick three hard strokes before four ropes of cum spurt out of my head. They land on her right tit, her arm and then two landed on her stomach. I laid down next to her and apologized for not telling her he was going to come. She seemed fine with it and enjoy having him cum all over her. our breathing was rapid but it eventually slowed down and I put my arm over her should , placing it on one of her boobs while spooning her. I dozed off a few minutes later.Part 2 could come out soon if I see that people actually enjoyed this.

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