So where should I start…

My names is Jordan and I am 18 years old and I am currently a senior in high school. I am about 5’8″ and about 145 lbs, although im somewhat skinny I am considered to be cut and very strong for someone my weight. I also play 3 sports, football, wrestling, and track. Life these days have been a shit load better than it has in the past. As I am laying down in my bed with a girl next to me, I stare out of the window watching the sun rising and I wonder, how did we end up on the same bed?

The beginning

It all started during the end of my sophomore year (around May), I went with my two friends Kevin and Eddie who were both juniors at the time, to a party at an old friend’s house. While we were there, I met a girl, her name is Lindsay. She had an above average looking face (at the time it didn’t seem that she took care of her face that well, but still looked good nevertheless), but an amazing body, as she had great hips, huge tits, and probably the fattest ass I have ever seen. Although she is from the same town as me and my friends, she goes to the other high school in the district as our town is pretty big so its split in half. Anyway, at this point, I haven’t even kissed a girl, and my confidence with girls were… to say the least very low as I was (and still am) a very shy kid. Eddie and Kevin already knew Lindsay, as they were in the same SAT night classes held at the middle school. Eddie was “talking” to Lindsay already as he has already gotten a blowjob from her, so since they were “together”, I didn’t even bother hitting that. So that night my drunk ass was pretty much chilling on the coach watching TV and having random convos with Kevin as everyone else were probably sucking each others dicks or fingering their pussies or whatever the fuck they wanted. The funny thing is, although I do not remember how, but me and Lindsay ended up exchanging our numbers.
The next morning, I woke up around lunch time as I fell asleep at around 3 am the night before after I was dropped off at home. I checked my phone and I got a text message from Lindsay, it read “You are so fuckin funny when ur wasted I fuckin love u”. I obviously thought nothing of it but I still smiled as I was reading it. Obviously, at the time I did not have feelings for her (or any girl for that matter), especially because she was talking to Eddie. I wasn’t the attractive type of guy anyways. The town I live in is considered really rich, and I live in a very small house and am considered very poor compared to other kids. At the time I was about 5’6″ 120 lbs, very scrawny, although strong for my weight and athletic compared to others. I was generally a very unhappy kid with only few friends despite playing 3 sports. School ended about 4 weeks later without me and Lindsay ever speaking or seeing each other once.


Summer/Junior year

Summer came along, so did football training. I kept myself busy with football for most of the summer, my friends also played football so I still talked to them. Kevin, Eddie, and I went to a party in the same house as the one before after one of our football training sessions. Then I see Lindsay walk in with two of her friends, Jess and Bailey. There was nothing special about Bailey, as she definietly had breast implants and had an average looking face. Jess had a good looking face and a nice body, but was chubby. Still nothing compared to Lindsay. I ended up drinking a ton, but little did I know Lindsay was sober, as it was her turn to drive her friends. As I was passed out on the couch a few hours later, my friend Lance woke me up and told me we needed to catch a ride, as Kevin was supposed to be our ride but his curfew was midnight so he left early. Lindsay ended up giving us the ride home as we packed into her car. I thanked her and all she replied was “I love you”… to this day I still don’t know why she would tell this to a kid she barely talked to.
Eddie and Lindsay stopped talking at around August, as Eddie said she was an idiot because she did everything with him.. except for sex. Football started around then, so that meant triple sessions, which also meant no jacking off as I would usually come home at around 9 pm all tired as fuck. I did get to see Lindsay a few more times before the summer ended. Still nothing ever happend between us, as I was too shy to even have a real convo with girls. Junior year started, and on October I finally got a car for my 17th birthday. This meant it was my turn to drive, Kevin and Eddie continued to take turns driving, so they didn’t really need me to drive them. So I ended up usually giving Lance rides to parties when he drank as he was only a sophomore and didn’t have his license yet. For a while, I went to different parties which were mostly sophomore kids, but in the back of my mind I still thought of how hot Lindsay was. Then one day, Kevin and Eddie needed me to drive because Kevin got in an accident so his car was in the shop. So we go to another party, and we run into Lindsay and her friends yet again. This time, Jess was driving so this meant Lindsay was the one drinking. I found this funny because last time I wasted and she was sober, and now she was wasted and I was sober. Lindsay ended up giving blowjobs to 3 guys that night and making out with about 7. But then it was the next morning when the problems started.
I can’t lie, I was somewhat upset I didn’t have the balls to make a move on Lindsay. But whatever. She texted me that morning, and she wanted to hang out. I picked her up, and she wanted to go get some food. As we were eating at the diner, she started to really piss me off. She was talking about how amazing bla bla bla’s cock was and how bla bla bla is a great kisser. Now I thought, why the fuck did she tell me this? I was starting to think she was considering me as a guy friend, which I absolutely hate. To me, girls and guys can’t be friends unless they do shit with each other. I went through the whole time listening to her shit, I dropped her off and went home, I then called her and went off on her. She seemed very confused (I just realized then that she wasn’t a very bright girl).