tagTranssexuals & CrossdressersMy One True Love Ch. 01

My One True Love Ch. 01


Apologizes to all, I was a moron and didn't even think when I started this story in the junior year of high school (which would mean the characters are underage). Because of this I had to rewrite most of the story. This work is completely fictional, none of this happened, and everyone is over eighteen years old.

I based the character on me, for all intense of purposes it's me. So what he says and does is how I react in those situations in real life (for the most part). I also tell this story as if I'm narrating it back to the reader, so it's rather casual. This story starts out slow, slower than 'High School Love,' but I promise once the sex gets going, it'll get good and happen often.

I'll be posting this about once a month, sprinkled with some shorter stories in between (hopefully). Hope you all enjoy!

Oh yeah, sorry about all the American football references and Formula 1 references (I try to keep it brief), like I said it's based on me...


Chapter 1

Hi my name is Jay and this is my story on how I met my one true love. It started in high school, my senior year there. I'm an average guy, 5 feet 8 inches, 175 pounds, dark brown hair. I was in the high school jazz band and band, played tuba, and played quarterback for our junior varsity team.

Anyways, I transferred to a new school and didn't know anyone really except for some of the football players and band members. I didn't consider myself a jock or geek, kind of somewhere in between. The first day of school was when I saw her. She was the prettiest girl I had ever seen. I didn't really know anything about her except that she was blonde and had the best smile. I just hoped I had at least one class with her, but I knew with my luck that it wouldn't happen. For starters I was a shy guy, never had a girlfriend, barely talked to girls for that matter, and had pretty low self-esteem. But I was so happy when I saw her walk into my biology class. She was stunning to say the least. As it was still hot out she was wearing the cutest set of khaki short-shorts which showed plenty of her legs and a cute tank top which showed off her perky breasts. At the time I wasn't sure what size her breasts were so I guessed somewhere in between a large A cup and small B cup. She walked in, her smile and laugh filled my eyes and ears as I saw her with her friends. I only hoped/didn't hope that she would sit near me, but I knew I was pressing my luck just to have her in my class.

But then she started walking down the aisle I was in and smiled at me. I blushed and smiled back meekly and reverted my eyes. From the quick glance I guessed she was 5 feet 7 or 8 inches tall, and not much more than 130 pounds. For whatever reason I've always had, and still do, have a problem making eye contact with people. For me it's a sort of phobia I guess, I don't like it when people look at me, and eye contact is a sure fire way of knowing that someone's looking at me. To my horror she sat right next to me.

"Hi," she said.

"H - hi," I stumbled.

"Looks like we're lab partners, I'm Lindsay."

"Oh we are? Okay cool, I'm Jay." I looked up to her and she smiled. I smiled again but still felt embarrassed.

Class went by smoothly and we chatted a little, not much just mostly small talk, which I hate. But it was nice to talk to a girl for a change. We said our goodbyes and left. I didn't see her again in any of my other classes, but I did see her in the hallways a couple times, she waved to me and smiled, and I thought I saw her at lunch but I wasn't sure. That was my first day of my new school, and I felt pretty good, football practice went well too.

Chapter 2

The next day I couldn't wait to see her again. After the first day I felt I got some courage and talked to her some more. We chit chatted again during class. I was surprised that we stayed after class for a little while and talked. I told her I was in the band and on the football team, albeit junior varsity, she seemed impressed though that I was so diversified. I learned a little about her as well, she tried out for the cheer squad and got in to which I congratulated her (She wasn't super preppy or anything though, which was a relief). Before we left I asked her if she could show me around the school since I was new here.

"Sure, I'd be happy to!" she smiled.

"Cool, wanna meet after practice or something?" I asked.

"Sure, I'll see you on the field then," she said.

"Okay cool, see you then!" I couldn't help but smile as we parted ways for our next class (I didn't smile that often).

I saw her again at lunch but didn't decide to sit with her. She was surrounded by all her friends and I didn't want to interrupt or seem too anxious. We met up after our practices; she looked more pretty than usual. She was sweating from practice and had the cutest outfit. I learned that for cheer practice the girls all wore tank tops and shorts, but come game day they wore their uniforms all day, much like the football team. We wore our jerseys (no pads though) in school during game days as well.

"How was practice?" I asked.

"It was good, but tiring."

"Looks like it," I said, "so was mine."

"I'm looking forward to the game this Friday."

"Yeah me too, although I may not be on the field all that much since I'm only the backup."

"So, that doesn't matter, the fact that you're even on the team means something. There's what, 3,000 or more students here and you're good enough to be on the team, that means a lot." She cheered me up; I guess that's her job as a cheerleader.

"Yeah I guess so," I said with a smile.

We talked some more, actually for quite a while because the next thing I knew it, it was almost 7 at night. We both realized how late we'd hung out and decided to call it a night. We said our goodbyes and left for the next day.

Chapter 3

The next couple of days were uneventful. I had class, talked to Lindsay and went to practice. Friday, game day, arrived and I was a bit nervous. I knew I wasn't starting for the game, but I had heard the starter, Caleb was often injured (our O-line (Offensive line) wasn't all that great).

So there I was in biology class. As usual I came early, in my jersey, and waiting for my lab partner. I was so happy when I saw Lindsay walk through the doorway. I didn't think she could have been any cuter than she already was but she proved me wrong. My hormones were ragging as I saw her. I knew that her skirt would be short, but it was ridiculously short. I was dumbfounded as to why the school allowed their shortness, but I wasn't complaining. From where I was sitting, Lindsay's skirt just barely covered her cute little butt. Even if she walked the material was dangerously close to exposing her panties. Our school colors were blue and white and I wondered what color Lindsay's panties were, blue or white? As she walked towards our table I tried to rid my mind of those thoughts, I didn't want to be a creep. But I couldn't help myself as I gazed upon her long smooth legs, her socks went well up her leg but still showed more than enough, and she certainly had the body to show it off!

Class finally started and quickly ended. We said our goodbyes again and she wished me luck at the game. "Thanks," I said, "see you there!"

"Yeah!" she smiled. I thought I caught a wink at the very tail end but wasn't sure.

The rest of the day went by and finally school was let out, I went straight to the boys' locker and got ready for the game. Even though it didn't start until 7 pm, coach had us suit up and get some light drills in before the game.

An hour before the game we were on the field warming back up and stretching. I saw Lindsay getting ready with her cheer squad. I wasn't able to say 'hi' or anything but I was glad to see her again. Half an hour before the game, coach had us all in the locker room for a pep-talk.

Finally it was game time. We selected to receive the opening kickoff and we were underway. As the backup I stayed on the sidelines with the coach, I listened in on the play calling to get an idea what he was trying to do. I followed the game very closely, as I loved the game, and by halftime we were down 28 -- 3.

Coach was a calm mannered man and gave us the new 'game plan,' what little game plan there was, for the second half. Hopes seemed to be quite low as we were getting killed in the first game of the season. Halftime was over and we jogged out to the field ready for the second half. We kicked off and the other team scored another field goal to go up 31 -- 3. On our next drive, the third play in Caleb went down with an injury. I saw this and put on my helmet. Having overheard and paid a lot of attention to the game plan I ran out onto the field and took over the offense. They announced my name over the loud speaker and got no applause or cheer, I wasn't really expecting any, my parents weren't there and no one really knew me.

I jogged out onto the field and huddled up with my teammates. I gave the play and we were set at the line. I saw the defense and changed with an audible. With the snap of the ball I dropped back and went through my progressions quickly before finding my man down the left sideline. I lofted the ball to him and dropped it right in his hands and he ran the rest of the way untouched for a score, we were down 31 -- 10.

Our defense held them to another field goal, 34 -- 10. On the next drive we went 83 yards in 14 plays with another touchdown pass by me to my tight end, Justin Thompson, 34 -- 17. The crowd seemed to be getting riled up as our team was starting to fight back. On the opposing team's next position our defense picked off the quarterback and ran it back for another score, 34 -- 24.

Both of our teams stalled the next few drives. It was now the fourth quarter, with 4 minutes to go. We were now down 37 -- 24, after they scored another field goal. We were able to stage a 7 play 67 yard drive that ended in another touchdown, our running back, Thomas Smith ran it in at the goal line to put the score 37 -- 31.

Our defense held and with 1:37 left we got the ball back, starting at our 17 yard line. Within 42 seconds we were at our opponent's 33 yard line with one time out remaining. As I had been doing all game, I led our team to the line and audibled again. A quick slant to my wide-out and we were down at the 17 yard line. Since we had been running it well, the next two plays were draws that got us to the 3 yard line. We used our final time out on 3rd and goal at the 3.

In shotgun formation I hiked the ball scanned the field quickly and then hightailed it to the end zone untouched, a designed QB draw. That put us up 38 -- 37 with 3 seconds left. The other team had one timeout remaining. After the kickoff and fair catch the opposing team tried a Hail Mary pass but failed before the clock struck 0:00, we won! Our team ran out to the field in joy as we won. The school had had a history of losing so this was a great start to the year. After the celebration my teammates and I went back to our locker room and coach thanked us for a well fought game, he gave the game ball to me. Later, I found out that was the largest deficit the school ever came back and won, so that was pretty cool.

After the game I met up with Lindsay who congratulated me on a great game.

"Thanks," I smiled.

"I didn't realize how good you were, that was amazing!"

"Thanks," I smiled again. I wasn't entirely sure what to do next so I asked her if she wanted to get some ice cream.

"Sure, I'd love that! Just let me go get my things."

"Okay," I waited for her and I took us to a nearby ice cream shop. I paid for her and we talked about nothing really, we mainly got to know each other more. I took her home, in my parents' car, that night and wished her a good weekend.

Chapter 4

I relaxed on the weekend, playing some video games and working out and practicing tuba. It went by pretty quick and the next school week was already starting up.

I waited patiently for Lindsay in Biology and was greeted by her wonderful smile. We talked about each others' weekend; I learned that she enjoyed video games as well, although not to the extent to which I played.

"I thought I saw you during lunch last week," she said.

"You did? I thought I saw you too, but I wasn't too sure."

"Yeah, I have lunch B," she said.

"Wow, me too! I didn't know that."

"Wanna eat lunch with me and my friends?" she offered.

"Okay, I've been mostly eating lunch alone or with a few random people. I haven't really found my 'group'," I said.

"Yeah I hear yea, it's tough being the new kid, well I'll see you at lunch then."

"Okay, see you then," I said.

Lunch came and went and I finally sat down with her and her friends, they were all girls, I was terrified! But they seemed to talk with me or each other with no problem, I felt more nervous there than I had at the last game. I managed to survive and the rest of the day went well. The rest of the week was rather uneventful, I talked to Lindsay almost every chance I got, without seeming to be too attached or creepy I had hoped.

At the end of the week, we had another game, an away game, and we lost 20 -- 17. I didn't play but it was still fun. I didn't get a chance to talk to Lindsay on the way back, I couldn't find her but I wasn't too bummed out.

For the next four weeks we had a pretty strong friendship. I had no idea how she felt about me beyond a good friend and never tried anything past talking. To be honest I'm a terrible reader of other people's body language or speech, I take things usually at face value and still do, so it was always difficult for me to gauge how she, or anyone, felt about me. I'd never been in love so had no idea what it was or how to read it. Getting back on track... we'd have some ice cream like the first game on occasion but that was about it outside of school and football games.

Chapter 5

It was now the second week of November, our football team was 3 -- 3 (our school system started later than normal for games), I played in two games, one of them very sparingly. I had another come-from-behind victory and lost the other, we got killed in that one 52 -- 13. Coach had me go in so Caleb wouldn't get injured for a meaningless game.

By now, my friendship with Lindsay was pretty strong. I helped her through some tough times; she had trouble in some classes and some social issues as well. That's when things got a bit weird...

It was when I was helping her out in one of her classes, physics. We were in the library sitting quietly; I had her go through some problems using some of the formulas she needed for class when our hands accidentally touched. Or so I thought. I instinctively pulled away, or at least for me it was instinctively since I've had never touched a girl. To this point Lindsay didn't know that I'd never had a girlfriend or rarely talked to girls, so I guess that's why she was surprised by my reaction.

"What's wrong?" she asked.

"Hm, nothing, it's just..."

"Just..." she repeated.

"Just that... well... uh... um..." I started to stumble and blush here, it was pretty embarrassing.

"Come on you can tell me," she soothed me.

"Well, it's embarrassing, especially as a senior in high school," I started. I looked to her and waited for her to say something, but when she didn't I continued, "I uh... I've never touched a girl... on purpose." I finally said.

"You haven't?" She had a look of shock, "How? I mean, you're a pretty cute guy, I really can't believe that you've never had a girlfriend, or even touched a girl... on purpose."

"Yeah, that's the truth; to be honest I've always been shy around girls. I don't know why, they just really intimidate me, especially if they're pretty," I tried to downplay that last part so she wouldn't pick up on what I was trying to say but from the way she smiled at me she knew.

"Don't be embarrassed. I've only had three boyfriends in the past."

"That's three more than me -- "

"- Yeah but, I... like you," she finally said it. I looked at her, in her beautiful blue eyes. She blushed and smiled shyly.

"You mean like like?" I asked in a way an elementary school child might ask.

She only smiled again and nodded. I smiled too and she put her hand back on mine. This time I didn't pull away. It felt nice, her dainty little hand, so smooth and soft. I imagined it was as soft as a baby's bottom.

I must've been in a daze or something because I kept hearing Lindsay repeating my name, "Jay, Jay... Jay... Jay --"


"Are you okay?" she asked with a giggle.

"Oh, uh yeah, sorry. It's just I was thinking about how soft your hand is."

"Oh," she smiled, "thanks."

I didn't even think when I blurted out, "Is the rest of your body this soft and smooth?"

Lindsay turned bright red and didn't say anything. Having heard what I just said I blushed as well, "sorry..."

"It's okay," she said, "to be honest; I think it's kinda cute you've never had a girlfriend before."

"So does that mean we're boyfriend and girlfriend?"

Lindsay blushed again and smiled, "If you want to."

"I do, how about you?"

"I do too," she smiled again. She placed both of her hands on mine and held it there for a few seconds before the warning bell rang.

"I guess we'd better get going," I said.

"Yeah, I guess so too, thanks for the help."


"Yeah, with physics silly," she giggled.

"Oh yeah, forgot about that, yeah no problem. Well wanna meet after practice?"

"Sure, same place and time."

"Okay, see you then."

"Okay, bye Jay," she smiled again and I did too. As I left her I couldn't wait until the day was over.

It felt like an eternity had passed before I finally met up with Lindsay again. I met Lindsay at our usual spot. We talked and giggled to one another like a junior high couple. For much of the time we held hands, which I really liked. It was really cool, I felt like I had butterflies in my stomach the entire time, not really believing that this was really happening. We said our goodbyes and we went our separate ways.

We lost our next football game 48 -- 13, I didn't play again. Our team was kinda depressed since we were 3 -- 4 and in danger of not going to state if we lost another couple games. Lindsay and I hung out together in the days leading up to the game and on that weekend we finally hung out together. It was our first major outing outside of school, (football) games, and after practice. We spent the afternoon on Saturday and Sunday shopping, watching a movie, and at an amusement park. I felt like I was really getting to know her and like her, and really starting to like her.

Chapter 6

Despite labeling ourselves as boyfriend and girlfriend a week ago we still hadn't kissed. But that quickly changed after practice on Wednesday. Lindsay and I were at our usual place after practice and I was talking about my day when she kissed me all of a sudden. To be honest I wasn't sure what she was doing until she pulled away a few seconds later.


"Sorry," she said shyly while turning away.

"No it's okay, it's just I wasn't expecting that."

"I was thinking, since we've been together for a week now, it's about time we kissed," she said with a blush. By now I had noticed that Lindsay blushes a lot, I'm not sure why, but I actually thought it was cute the way she did it.

"I was waiting for the right time, but you jumped the gun on me," I chuckled.

"Teehee," she giggled, "well I couldn't wait!" We paused for just a second before we locked our lips again. Seeing as I had never kissed a girl I had absolutely no idea what I was doing. I felt Lindsay try and open my mouth with hers but I wouldn't allow it at first. She pulled away, "why won't you open your mouth?"

"I didn't know I was supposed to..." I defended, "I've never kissed a girl before."

"Sorry, I forgot. I still can't believe that you've never had a girlfriend before. Try and follow my lead, okay?"

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