tagTranssexuals & CrossdressersMy One True Love Ch. 02

My One True Love Ch. 02


Here's the second part to my romance story. There's sex in it, so for those of you who patiently waited, you've been rewarded.

I posted this in the comments to MOTL Pt. 1 but I'll post it here as well; As I've stated at the beginning of the series the story is supposed to be based on me. Because of this there may be some oddities about my story telling. This is because I've never been in love or been with a transgendered girl, so all of the experiences I'm describing are bits and pieces I've picked up from reading other stories on Literotica and putting my own spin on things. So if things seem disjointed or out of place somehow, it's because I have no experience in either category, so for that I apologize.

And I want to emphasize this next part; I realize my story may not be entirely realistic (like I said, I've never been in love or with a girl/gurl) so please bear with me with some of the harder to believe points. This IS a FANTASY, this is my fantasy, so some things may not be believable or even possible and for that I want people to suspend their disbelief.


Part 2:

Chapter 7

Another week passed and Lindsay and I were going quite strong, I felt. Our team lost another game and there'd been rumor that coach may pull Caleb in favor of me for the next game. It was another Wednesday that Lindsay asked me at our usual spot, after practice, if I wanted to come by her house this weekend. I agreed without question and actually realized that the two of us hadn't really been on a proper date. So I asked her, "Can we make it a date instead? I just realized that I haven't given you a real date yet, and it's well over due. For one I want to experience one and two, most importantly, I think you deserve one."

"Yeah, I'd like that," she smiled.

"Can I pick you up at 6:30 on Saturday?"

"Okay, that sounds great!"

We talked some more and I couldn't wait until the weekend.

Thursday went smoothly and Friday was soon upon us. I didn't end up starting the game, I wasn't surprised because I didn't get any reps with the first team. We ended up tying, which rarely happens, 20 -- 20 so our school record was 3 -- 5 -- 1. Caleb struggled again and I felt like I was going to get my chance to start next week.

Saturday finally arrived and I was dizzy with excitement, it was kinda weird, I felt like a little school girl on her first date ever. So I tried to quell those feelings with some manly video games, I ended up playing shooting games to help that. I'm not a super macho man. I'm perfectly comfortable with being a little metro sexual, I'll wear pink and purple, but I felt I needed to man-it-up a bit.

Anyways, 5:30 came around and I was getting ready for my first ever date with a girl. I put on a nice dress shirt, tie, and sport coat, some nice slacks and a nice pair of shoes. I also had my hair done, so it wasn't all flat. Before I knew it, it was 6:15 ish. I headed out the door and borrowed my parents' car, a 'nice' beige ford Taurus, woo!

I arrived at 6:30 sharp and ringed Lindsay's doorbell. I was let in by her mother and waited in the family room. I chatted with Lindsay's' mother, Cheryl, for a little while. I asked about Lindsay's father because I wanted to meet him and learned that Lindsay's father left them not too long ago and I felt sad that Lindsay was left without a father and Cheryl without a husband. The heavy conversation was quickly changed to a light one and soon enough I saw Lindsay walking down the steps in her house, I know, super cliché but that's how her house was laid out.. I immediately lit up as I saw her. She looked absolutely gorgeous in her dress, a nice blue loose fitting one. It was modestly short, maybe just past her mid-thigh, or ¾ down her thighs. She had her hair down, as opposed to her usual pony tail, and had these elegant looking high heels. They had straps crisscrossing over her dainty feet, leaving them mostly bare showing her pedicured nails. To give you an idea of her beauty, she kinda looked like Kaley Cuoco from the tv show The Big Bang Theory.

I stood up to meet her and gave her a light kiss on the cheek; she was taller than I was in her heels. We talked with Lindsay's mother for a little while before she wished us well and I took Lindsay to the car and helped her in. We were soon off to the restaurant I chose earlier. I didn't know what she liked yet so chose a standard, Italian. We talked lightly on the way there and were seated at the restaurant within half an hour. Being a gentleman, I let her out of the car and helped her into her seat at the table as well.

We talked while we were waited on and I learned even more about her. She had a Norwegian and Polish background. Like me she moved frequently as well. Her favorite color was pink, I wasn't surprised because most of her school things were shades of pink, and she liked video games, which I already knew. And much more, kinda sounds like an infomercial (and wait there's more!). I talked about myself as well. Caucasian background, loved football and cars (formula 1 and Top Gear UK). Enjoyed video games, favorite color black, never had and still don't have many friends, shy, the like.

Even though we knew each other rather well it was rather refreshing to relearn about her and me. It felt like we were starting over, but we weren't, we were getting to know each other even better. I noticed about midway through dinner that her hand was on mine for much of the time and I suddenly blushed. "What's wrong?"

"Oh, I just realized your hand's been on mine for a while."

"Oh, teehee," she giggled. I paused for a moment thinking about what I was about to say.

"Uh Lindsay..."

"Yes Jay?" she looked intrigued.

"I can't believe I'm saying this right now... but..."


"I think I'm in love with you," I blushed. I saw her light up and smile broadly, she didn't say anything for a moment but she blushed too.

"I... uh... think I'm in love with you too."

I was speechless as we sat there holding each others' hands. Our dinner was almost done and here we were confessing our love for each other, on our first date no less! I knew it was weird because I hadn't done anything with her other than some light kissing, and the occasional awkward make out kissing. But I knew I was falling in love with her.

"I... you... the way you make my life feel full... you always make me happy Lindsay, seeing you during school and after practice really makes my day. I can never wait to see you again, your smile is so infectious and glowing... I... I love you Lindsay." I noticed Lindsay blushing again as I explained myself. She smiled, "Jay, you make me the happiest girl in the world. You're so caring and helpful. You've always been there for me and you listen to me, unlike my past boyfriends. And most of all, you respect me for who I am; I, too, am in love with you."

Our conversation became lighter as our dessert came but I brought up our love one more time, "You know Lindsay, I wanted to also mention that even though I said I love you, I don't want that to put pressure on to you for anything physical. I know it's a little odd to say, considering we haven't been physical, but I just wanted to say again that there is absolutely no pressure to do anything you don't want to do."

Lindsay paused for a moment to digest what I said, "Thank you Jay. I'm glad that you said that, I know I may be a little high and tight sometimes but in my past experiences, going too fast leads to problems."

"I may be a guy, but I'm not like most horn dogs my age. I wasn't telling you the whole truth when I said I don't have many friends. You see, most of my friends are older people, guys in their 40s and 50s. It's kinda funny, I should probably be friends with their sons and daughters but older people tend to be more mature. I guess that's also why I've never really had a girlfriend; most of them tend to be really immature."

"Jay, I'm speechless... I've never known any guy who was so respectful."

"Thanks, well it came from my martial arts, I started when I was only 6 and have been doing it since. I took all that honor, modesty, and truthfulness to heart."

"Jay, thank you. I'm so glad I met you! I love you!"

"I love you too Lindsay, now let's eat dessert!"

We finished dessert and I took her home. We kissed for a little while before I let her go. I was the happiest guy, I couldn't believe I had just told someone that I loved them and someone said the same to me! I slept very soundly that night.

Chapter 8

For a first date, that was pretty weird, confessing my love for someone, but I guess we had known each other for a few months anyway. So that's where Lindsay and I were. I didn't start in the next game, but Caleb was struggling again which led to coach sending me in and I helped lead another comeback, 23 -- 21. We stood at 4 -- 5 -- 1 with still a faint hope of reaching state.

Two more weeks passed along with two more games and numerous dates with Lindsay. I started both games and won them both. We stood at 6 -- 5 -- 1 and we managed to make it to state for the first time in 16 years. Coach named me the starter as winter break was already on us. Our district still played football during winter break and in the first week of break we were able to win another one to go to the next round. But the following week we couldn't get everything together and lost, eliminating us from state competitions.

My relationship with Lindsay was as strong as ever, if not stronger during the past few weeks. Physically we moved up to a bit of groping, which I did enjoy. Feeling her smooth soft tender breasts (just through her bra, hadn't got to touch skin yet) was amazing! I had no idea they were so wonderful. I'm actually a butt man and am not as interested in boobs as I am with a girl's butt. That's not to say I don't like boobs, I do, but girl's butts are just way better. And Lindsay's butt was the most perfect one in the world. Her hips flared out perfectly from her waist and formed the most beautiful little heart shape you could imagine. Having seen Lindsay without her shirt now, I guessed her dimensions were somewhere around 32 (small B) -- 28 -- 34. Earlier when I blurted out if her whole body was smooth like her hands, I found out that she most certainly was.

As I promised her, I never went further than she wanted physically. She was actually the one to let me touch her breasts when she grabbed my hands and placed them on herself. Other than that though, we still hadn't done anything more. I was patient and knew that all this waiting would be well worth it.

There was a school dance in November that I took Lindsay to. It was much like our dates, nothing really happened even though I did enjoy myself. We kissed and danced together and I took her home afterward.

It was nearing Christmas time when I was at Lindsay's. Her mother was out working so we had the entire house to ourselves, like we had much of winter break. I came over and the two of us ate lunch together in her house and watched a movie. We were cuddled up on the sofa, her legs in my lap, when she kissed me in the middle of the movie. I was a little surprised because we usually finished what we were watching before we did anything. But here we were in the middle and she kissed me.

We soon started making out and she pulled her shirt over herself to reveal her bra. I marveled at her perfect breasts and started to kiss my way down to her milky mounds. I cupped them both and joyfully played with them as she moaned above me. It was pretty hot and I felt the insides of my pants stir. As I was playing with her boobies I pulled away when Lindsay took my shirt off and kissed me again. We made out some more before her hands wandered down my body to my jeans. I felt her fumbling with my zipper and start to pull it down. I pulled away and stopped her, I know crazy!

"Are you sure?" I asked. She smiled and nodded. "Before you do anything more," I said, "I want to know that I'll be able to return the favor." She looked at me pleadingly, "but I really want to!"

"I know you do, but I always hate it how I hear about the girl always giving head but the guy never does anything in return. To me it always felt selfish."

"When did you hear that?" She asked.

"You know at school. Girls are usually the ones giving and never receiving, and I've always hated that. Even though we said to go slow, why am I the only one to get physical gratification?"

"But I really want to make you happy."

"You do make me happy, but I'll only allow it if you let me do the same to you too. Because I want to make you happy too."

"But I am..." she pouted cutely.

"You know that feeling you want to do to me?" I began, "I want to do the same to you, so why can't I when you can? It's some stupid double standard in our society, that it's okay for a guy to get physical gratification before the girl. I think we should both experience it." I saw that Lindsay was tearing up now, "What's wrong baby? You know I have my honor and ethics."

"I know, I'm not crying because you hurt me..." she sniffled, "I'm crying because you care so much about me..."

"I know baby, I love you. Lindsay, I love you." I hugged her and let her cry on my shoulder until she calmed down. The mood of the afternoon quickly died after that and we let it rest for that day.

Chapter 9

We spent Christmas apart; I actually don't celebrate it as I've hated how it's become such a materialized holiday. I was with my family while Lindsay was with hers, I did end up getting her a present, it was a cheesy little teddy bear, but she seemed to like it, having seen all her stuffed animals in her room. She got me an action shot of one of my throws from our first come-from-behind victory. It was pretty cool, she had it framed and looked really professional.

Seeing as Christmas and New Years were so close we weren't able to see each other then. After New Years we had one more week off before school started back up. I was at her place again. We were cuddled up on her living room sofa again watching another movie when she said, "I think I'm ready."

"Ready for what babe?" I asked, not even realizing what she meant.

"You know..." she smiled up at me and that's when I knew.

"Oh, okay. But are you sure? I can still wait."

"Yes. You've been the utmost gentleman and I think I trust and love you enough not to hurt me, so yes. I'm ready! Plus, I don't know if I can wait any longer!" she giggled and smiled and took my hand. She led me up to her bedroom and sat me down on her bed. It always killed me to see all her stuffed animals. I saw the stuffed teddy I had given her for Christmas right next to her pillow and smiled.

We sat there holding hands for a moment before she swung her legs across my lap and wrapped her arms around my neck as we kissed passionately, exploring each others' mouths before Lindsay broke off. She smiled at me and I smiled back.

"I love you," she said.

"I love you too Lindsay. More than anything."

"I know you do and I want to show you how much I love you..." she trailed off there at the end.

"But... something's the matter. What is it?"

"But... you see, I'm not like other girls."

"I know you're not, and that's why I love you."

"No you don't understand. There's something different about me from other girls."

"I know, you respect me and care for me for who I am."

"No, that's not it either... I don't know how to say it. I know you're an open minded person."

"Yes, very open minded," I added.

"I know, but I don't know how open minded."

"I don't know what you're getting at Lindsay," I said confusedly, "what's going on?" I saw tears begin to well up and somehow I knew they weren't tears of joy. She swung her legs around and let go of me. She stood up and faced me. I smiled to her to try and reassure her and also because she was standing in front of me with her cute tank top and tight fitting jeans. But seeing that she didn't smile back I looked into her eyes. I saw fear and betrayal within her watery eyes and knew that she'd gone through some tough times with past boyfriends. My smile soon faded as I realized how serious she was being.

"Come on baby, you know you can tell me anything. I promise I won't judge."

"That's what the last boyfriend said..." she began to well up again. I saw tears cascading down her pretty cheeks. I couldn't let this happen so I stood up and embraced her in a caring hug. "It's okay baby, I'm here for you. Forever and ever. If you can't tell me, then that's okay. I know this must be hard." I tried my best to console her and she seemed to calm down a bit.

"Okay, I'll tell you, but sit down." She pressed me down so I was sitting on her bed again. She started undressing, which I thought was odd. She started with her tank top and let that fall to the ground, and then her pink bra. Her blonde hair was lose and rest past her shoulders while I locked my eyes on hers barely paying attention to what she was taking off now. For the first time I noticed she had a very cute piercing on her naval as she grabbed her tight fitting jeans and unbuttoned them and then zipped them down. She shimmied her jeans off her legs and kicked them away. She stood there now just in her pink panties and she looked as gorgeous as can be. I loved the piercing she had on her belly button. It was just a simple jewel of some sort but looked really sexy dangling there. "Baby, what's wrong?" I asked utterly confused, "You look amazing. I know I can't really compare this to anyone but I think you could be a model." She smiled through her tears but that didn't last long as she spoke up, "you love me, no matter what?"

"Yes Lindsay, I love you no matter what."

"You wouldn't hurt me?"

"No, of course not. I could never hurt a girl, let alone you."

"Okay..." she sighed, "only a few people know this about me..."

"Okay..." my curiosity really kicked in now.

There was another pause before she spoke up, "I... I... ihaveapenis..." she mumbled.

"I didn't catch that, it almost sounded like you said, 'I have a penis'." She teared up again and I was shocked that that was in fact what she said. I must have sat there open mouthed for a good minute or so before she spoke up again through sobs, "so..."

"I don't believe you, you're the most gorgeous girl at school."

"But it's true..." she bowed her head and began to bawl now. I sat on the bed thinking.

"So does that mean you're a boy?" I asked dumbly.

"NO!!" she shouted. I was taken aback by her resounding defense. "I was born a boy, but always felt like a girl." I didn't know what to do. My first girlfriend dropped the biggest bombshell I had ever heard. I really couldn't believe what she was saying was true so I said, "I really don't believe you... can you show me?" I was even surprised I asked that last bit. She looked up with the reddest eyes I had seen and she nodded. Her nose was running now and I could hear her try to sniff up her mucus. She put her fingers in the thin waistband of her panties and started to pull them down when she stopped suddenly, "You won't hurt me will you?"

I reassured her, "No, like I said, I would never hurt you. Even if you do have a... a... penis." She tried to stay strong and choke back more tears but she couldn't as she began pulling her cute panties down. She bent all the way down and kicked her underwear away. She stood there completely naked now, but all I could see was a smooth shaven, or waxed, mound between her legs. Next is what shocked me, she parted her legs slightly and out swung a cock and balls. She stood there crying as I looked over our situation. Her balls hung quite low and were massive. It looked like she was holding two golf balls inside her scrotum. I next looked at her cock; it was flaccid and looked to be about 4 or 5 maybe 6 inches soft. I sat there starring at her genitals and realized I called her a her. Is she really a her?

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