tagTransgender & CrossdressersMy One True Love Ch. 03

My One True Love Ch. 03


Third installment of My One True Love. I apologize for the late posting, been going through some rough times recently. Things are looking up though, if anyone cares.

Seeing as I have so few readers now with this series this may be the last entry in the series. Yeah the last one got good ratings but almost no one bothered to read it.

I want to reemphasize my last posting 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.

Please right comments, I was reading a story the other day and the author seemed pretty displeased as to why his/her story wasn't well received. They mentioned how people don't comment on why they didn't like it, so if you don't like my story (or maybe my writing style) then let me know what's wrong. I want to try and put the best product out there and if I don't get feedback then I don't know what I'm doing wrong.

For those of you still reading this far, I hope you enjoy this next installment!


Part 3

Chapter 10

After our first day of making love, we didn't the rest of the week because Lindsay's mother had the week off and was home for the week so we couldn't really get any privacy. I was still battling my thoughts about having sex with her, which I think was another reason why we didn't do it. Lindsay tried to convince me to come over but I politely declined, knowing she wouldn't be able to control herself and her voice. She pouted but I reassured her that we would when there were more appropriate chances.

I wouldn't say I necessarily avoided her, but for the rest of break I kept my distance; always bringing up an excuse not to come over. The few times I did go over we talked a bit and played some video games, which I now knew why she enjoyed them so much. I also ended up chatting with Lindsay and her mother. I learned a lot about Lindsay's childhood and how tough it was for her to grow up in the wrong body, let alone losing her father at the age of six. I also learned that her past boyfriends beat her once they found out what she had between her legs. It was very emotional for her to retell her past and I comforted her as best I could, telling her I'd never do anything to hurt her. I also found out that she was mostly natural, her breasts were a half-fake/half-natural B-cup but her hips were entirely hormone made. She also had facial restructuring surgery. She told me she already had feminine features and the surgery helped complete her look. Along with that she had her Adam's apple shaved in addition to getting laser hair removal, so in all essence she was in fact a girl. I also asked her why her penis and balls were so big, I had thought that taking the hormones would shrink them or at least halt their growth. She told me because of her mild doses the effects of the drugs weren't as strong in her. She also added on that it varies from person to person and also what types they took. She still told me though it was a nuisance, she didn't like her cock, especially with how big it was.

I later looked up on the internet about transsexuals and found a lot of porn, which I admittedly visited, though not often, but most of what I was looking for was information on the subject. Seeing some photos of other transsexuals and Lindsay blew these other girls out of the water, some looked like guys with make-up and girls' clothes; others were closer but not quite there. There were only a few that were more like Lindsay; you couldn't tell unless you saw what they had between their legs. I was as supportive as I could be, but I was still fighting with myself over my sexuality. So that was mainly the final week of winter break.

School finally started back up, I was glad to be back in school, because the year was half over. My classes got moved around (as we're supposed to have with each semester), and Lindsay and I didn't have any classes together, though we still had the same lunch. On the Monday we got back, I asked Lindsay out on another date. Quite often I'd ask her out on Friday's or Saturday's for a date as it gave us private time out of school and the house. By then we had known each other for quite some time but I still found it fun, I hope she did too.

The week ended and I picked up Lindsay from her house at 6:30 for reservations at 7. We had a good dinner and chatted about the week.

We had dessert and had a good time. Now, by this point in our relationship -- especially after we first had sex -- Lindsay made very little attempt to hide her arousal around me and that night was no different. It's kinda weird; it almost felt like I was dating a completely new girl because how much sex opened everything up.

Anyways... so after dessert Lindsay was getting really frisky around me, and I didn't want to make a scene at the restaurant so I quickly paid the bill and we drove away. I found a spot not too far away that I thought was romantic. It was a hill that overlooked a nice natural valley with no hint of civilization. I drove us there and I was lucky that it was a rather clear night. The moon was out, only a waning gibbous, but it still looked nice. We held hands in the car looking out the windshield. I always had a fascination with the stars and space so was taken by surprise when Lindsay kissed me on the cheek. I turned my head and kissed her back. As always she looked gorgeous and that night was no different. She dressed to impress, she wore her hair back in a ponytail, nice deep red lipstick, a modest dark blue top showing a bit of cleavage, a short black mini skirt, and to top it all off, 3 inch spiked heels; she looked ravishing, though I was still a little disturbed by what was between her legs. I pushed that to the back of my mind though.

I didn't know what she had on underneath but somehow I knew I'd know sooner or later. We started making out now and were starting to get a bit hot and heavy. She pushed my seat back and straddled me. It was a little cramped in the car but we made do. I could feel her growing arousal under her skirt and smirked. She didn't really notice my smirk because she came right at my face and attacked my mouth. We were moaning into each others' mouths as I fumbled with her blouse. I had it off showing her black bra and perfect boobs. I fondled her playful mounds as we continued to make out.

Before I knew it I felt her full erection under her skirt. From the way it felt, it felt like it was straining to get out. She maneuvered over me and I felt her cock flop out as she slid her panties to the side. I chuckled during our kiss as I saw her skirt tent out and the head of her cock peek out below. "Boy, you sure are frisky tonight."

"Oh god! I need you ssssoooo much! I need your cock inside me!!!!" Lindsay lifted herself off me and unbuttoned my jeans and quickly got my cock out. I was sporting my erection and she straddled me again. I could feel her perfect ass on my cock and groaned in anticipation. I still had my shirt on, as did Lindsay mostly, and she liked missionary, I had no complaints. There wasn't much room on the driver seat so we mashed our way to the back seats. Lindsay lay down lengthwise and I knelt in between her legs. There still wasn't much room but we somehow managed. Lindsay's left leg was down by the leg area so I propped her smooth legs up to present me her cute bum. She left her skirt on, which I thought was hot, and flipped it up to reveal her ragging hard-on. In her purse she handed me some lube and I applied a generous amount to my cock, lathering it up nice and good.

Before I started I looked to Lindsay, she had a huge smile on her face and her cock was leaking precum all over her skirt and exposed belly. She left her bra on, which I actually found rather hot too, but had her blouse open. "Ready?"

"Oh god yes!" she moaned, with that she grabbed the back of her legs and slid onto her back completely so she could give me better access. I laughed to myself quietly seeing her puckering hole. It was really cute and I guided my cock into her. Seeing as this was only the second time she'd had sex it was still tough for her to let me in. As I mentioned before, I'm only 5.5 inches long but about as big as a soda can around. I looked into Lindsay's eyes as I pressed my cock to her winking hole. She grimaced and whimpered a little and gasped loudly as the head of my uncut uncircumcised cock broke through her anal ring. She tried to pull away again, but did her best to resist that. I gently pushed into her ever so slowly, making sure I wasn't hurting her too much. The look on her face told it all though, she did her best to mask the pain, but I could tell she was struggling. She groaned and huffed until I was all the way in. Tears were in her eyes like last time, but she was able to take me more quickly, I was proud of her.

She tried to smile through her tear soaked eyes, but looked really strained, "It's okay baby, if you want me to pull out please let me know."

"No it's okay, it's just... you're sssssssoooooo big!" she groaned, "uuuuuggggghhhhhh!" Her smile faded but she was still happy, I knew because her cock was throbbing with her heartbeat and it was leaking a lot of precum. I stayed deep inside her and watched as she grabbed her aching cock. She used her precum to lube herself and gently stroke her long cock.

I rested inside her for a while and she increased the pace of her strokes and I was wondering if she wanted me to start. Her eyes were closed and she was biting her bottom lip as she stroked faster and faster. I waited though, but knew I got the signal once she started bouncing on my cock. She slowly slid her body on the car seat trying to get me to move in and out but with little success. I couldn't wait much longer so slowly I started to thrust inside Lindsay. Her face lit up instantly and quiet moans escaped her perfect mouth.

Not too much longer I saw Lindsay open her eyes. She raised her head and watched her cock. I did too and saw that her golf ball sized balls tighten. "Ooooooohhhhhhhh!!!!!!" she moaned. I knew what was about to happen and wasn't sure how I felt about her finishing so quickly. She groaned and grimaced with pleasure as I pulled out and pushed back into her. Her lips parted slightly and a soft sensuous moan escaped her lips as she slowed her fisting.

Her grimace didn't last long at all as she quickly switched to her smile as she looked up at me seemingly innocently. She raised her arms to my back and beckoned me to come in close. I hesitated for a split second, knowing I'd be closer to her cock, but leaned down and gave her a soft kiss. She didn't seem to notice my hesitation which I was glad. After our kiss she moaned huskily, "Oh god I fucking love you!... now fuck me like the stud you are!"

I wasn't really thinking about what Lindsay had between her legs, I was inside her and it felt great so I began full long strokes of her love canal and she groaned and moaned under me. Hearing her squeal under me as I picked up the pace was quite erotic. Within a few minutes I was starting to really give it to her. I felt a tingle inside my loins and knew there wasn't much time left. I think Lindsay sensed this and grabbed her aching cock again. She matched my pace quickly and we were soon in rhythm. Her hand jerked down as I entered her and she jerked back up as I pulled out.

"I'm close," I moaned.

"Me too!" she chirped. I gazed into her beautiful blue eyes and she into mine. Like our first time, I bent over so I could place my head to hers as we got closer and closer to the finish. Our sweat and bodies became one as we were just mere inches from each others' faces.

I thrusted my hips into her and I watched as she closed her eyes and bit her bottom lip. She looked absolutely gorgeous like that and soon she arched her back. Her eyes shot open and I looked down her slender body. Her hand furiously fisted her womanhood and I watched as a thick stream of pearly white goo exploded from the tip. She screamed in ecstasy as I too exploded. My cock throbbed inside her, filling her with my own white creamy goo.

I was amazed to see her launch seven massive reams from her cock before her cock slowly dribbled out a few more white loads. I couldn't count how many I shot into her as I was so transfixed on her orgasm. We laid there panting after having sex. I stayed inside her, still semi-hard, and we kissed madly, our tongues embracing in our mouths.

I felt my cock shrink inside Lindsay so I pulled out of her. She gasped and pouted cutely, "I'll miss your friend..." she smiled.

"I know babe, don't worry," I said, "we'll have a lot of time together." She smiled and pecked me on the lips again before she went through her purse. I was puzzled at first but then looked to her stomach and saw the aftermath of what she'd done. I chuckled, though slightly disturbed again by what I had done, as she dabbed her belly, she left some over and coated her fingers in it before licking her fingers clean, "Mmmm! Yummy!" I just smiled and watched her.

Soon enough we got dressed and I took Lindsay back home, "Night babe."

"Night Jay, see you next week at school. I'll miss you!"

"I'll miss you too Lindsay, have fun!"

"I will!" she smiled. We kissed as I left, she was going to her grandparents for the weekend so we'd be apart, but I was okay with that. I'd get to see her once the weekend was over.

Chapter 11

Over the weekend I had time to think about our relationship. The more and more I thought about it the more I felt wrong about it. I couldn't believe what came into my mind soon after. I knew I loved Lindsay, but I just really couldn't get past her genitals. I had to break up with her... it was tearing me up inside. I hated myself for it, for not being able to be okay with Lindsay's extra bits.

Having never been through a breakup I didn't really know proper etiquette so I did it at school, on the Monday after she had visited her grandparents. I guess I was fortunate that we didn't have any more classes together, or it might've been even more awkward than it already was.

After classes we met up like we usually did, but today I took her to the library, not really knowing where I should do it. I did my best acting and didn't show Lindsay what I was up to. It was difficult to say the least considering I knew this wouldn't end well. I tried to reason with myself that I was doing this to help her as well. She shouldn't be with someone who couldn't cope with her specialness, and unfortunately I was that someone. Once we sat down I think she had a hint that there was some bad news coming her way because her smile quickly faded.

Seeing right through me Lindsay spoke first, "Is something wrong?"

"Yeah," I sighed.

"What is it?" I gently held her hand and looked into her eyes, before gazing away.

"It's me..." is all I started.

"What's wrong with you?" she asked, I thought she was trying to evade what was coming next.

"I can't deal with this..."

"With what?" she asked, tears started to form in her eyes.

By this point we both knew what I was going to say next. "I love you Lindsay, with all my heart, but... I feel absolutely terrible about this... I don't think I can get past your specialness. I think it's only right to you to find someone who can, because you are a great girl, and I'm really not just saying that. I feel so terrible that that is what's holding me back..." I began to tear up, Lindsay already was. As I trailed off there at the end Lindsay pulled her hands away from mine.

That really hurt.

Lindsay looked at me, soaked and with bloodshot eyes. She opened her mouth but then stopped herself.

She began crying now, but tried to compose herself. In a flash she got up and ran out crying in her hands, never speaking another word to me. I felt just absolutely horrible. I sat there alone, fortunately we were in a secluded spot so no one was staring or glaring at me, I didn't need to deal with that now. I felt like I had ripped my own heart out, not to mention hers.

After making myself presentable I left and went straight home. That night was another restless night; I still couldn't believe that Lindsay and I weren't together anymore. I also vowed not to tell anyone of Lindsay's secret, it was for her to decide who to tell, not me. I had no ill intentions to our breakup, like I said, I still loved her, but her anatomy was something I couldn't deal with now. I know we had had sex, twice, but after each time it just felt wrong... but also right. My mind wandered that night, 'did I make a mistake?' I really couldn't sleep and maybe got 3 hours of sleep before the next school day.

The next school day was glum to say the least. I didn't see Lindsay, for all I knew she might've seen me and ran away, I had hoped not. All throughout classes Lindsay was on my mind. I felt so guilty about what I did and felt sick to my stomach.

By now in the school year I had some good friends, Tom and John. Neither played football or were in the bands, I met them separately in some classes. I hung out with them during the week of our breakup. They knew about us and were shocked when I told them I broke it off with her. They did their best to cheer me up, but it didn't work for me.


Despite now having a girlfriend under my belt, I was still intensely shy around girls. So when a girl came up to me about a week after our breakup I was surprised. She was a cute girl, I didn't know who she was but she seemed to know me, calling me by my name.

I learned that we had had a few classes together, I had no idea. Barbie was her name and she told me I came recommended. I was a little puzzled by that comment, "What do you mean recommended?" I asked.

"Lindsay said you were a great guy," she said. I had to stop and think for a moment. After what I had said to Lindsay she, or at least it seemed, wasn't upset at me, I thought she would've been. The girl standing before me was quite pretty, a petite brunette girl, smiling at me waiting patiently. I was torn between what I should do. I really didn't want to get myself in another relationship, especially just for the sake of it, but I didn't know if it would've been wise to pass up an opportunity like this considering my demeanor.

I noticed her smile fading, still waiting for my reply, "Uh thanks... I guess..."

She smiled again, "I know this might be too soon, but I thought we could be friends," she said.

"Uh, yeah, sure," I didn't think I could get any more awkward with girls than I had with Lindsay, but this was proving to be even more so. The next few minutes were just little snippets back and forth between us. I wasn't trying to be standoffish, but Barbie seemed to lose confidence as our 'conversation' continued.

Thankfully Barbie had somewhere to be that afternoon, not because I didn't like her, I actually did, but because the conversation was too forced. We parted ways and I headed home. Like I said earlier in the story I usually had no clue when a girl was interested, but after having been with Lindsay I picked up on some of the hints. Barbie kept laughing at some of the things I said, despite not trying to be funny, and she kept touching my arm and shoulder. So for the second time this year, for some reason, another girl seemed to have an interest in me.

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byf1dude_lotus© 12 comments/ 25869 views/ 18 favorites

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