tagTransgender & CrossdressersMy One True Love Ch. 04

My One True Love Ch. 04


Hello all!

Sorry for missing last month's installment of MOTL, I had to put it on pause for a month. Thanks for the feedback! It's greatly, really it is, appreciated!

I'm happy to say I've gotten back into writing after taking a few months off. These next few chapters just flew out of me, I don't know why. Also a few more story ideas have popped into my head and have already started other stories, can't wait to get them out!

Just a reminder, I realize my story may not be entirely realistic 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. Especially in these next set of chapters, the way things unfold may seem unrealistic.

Without further ado enjoy!


Part 4

Chapter 15

A week passed, Barbie and I had a share of sex, which was great of course. But things started to change. It was the middle of the week, Wednesday or Thursday, I didn't quite remember. I was in the library doing some research for a class project. I had already said goodbye to Barbie as she had a doctor's appointment that afternoon.

I leaned back to take a mini break. Looking around I saw the stacks of books and no other students, at least in my vicinity. I wasn't surprised, high school wasn't really known for students studying. I took a walk, just to see what was up; some students were here and there. I meandered my way back to my little spot and plopped myself down. I dug back into my books.

Maybe half an hour passed before I heard some rustling in the room I was in. I was too engrossed in my books to see who had come in. Whoever it was sat down not too far from me and did whatever they came to do.

I minded my own business as did they until they sat right across from me not too much later. I again didn't look up, but was soon interrupted by the clearing of their throat, the rustling of papers, and what not. I glanced up because the person wasn't at all quiet. I know knew why they were so noisy.

It was one of Lindsay's best friends, Hailey. She was a cute little thing, and I mean little, not more than 5 feet 1 inches and I didn't know if she even exceeded 100 pounds. I said I glanced, but it was more like a double-take, because of who it was. She sat there smiling at me and what I thought fluttering of her eye lashes. We didn't say anything for the longest time; it was kinda awkward to be honest.

I finally spoke up wondering what was up, "So... what's up?"

"Oh nothing..." was all she said, still smiling.

I wasn't buying it, "No, really, what's up? We haven't talked since I broke up with Lindsay."

"I knew it!" she nearly shouted.


"I knew you'd mention Lindsay first!"

"Well yeah, you are her best friend; I assumed that's why you're here..." I stated matter-of-factly.

"Well I guess you do have a point," she said. There was another pause.

"So..." I asked.

There wasn't an answer so I decided to initiate it, "So how's Lindsay been?"

"She's great! Never been better!" Her over enthusiasm concerned me.


"Yeah, she's great!"

"Okay, so then why are you here? Just to gloat in my face or something?"

"No, that's not why..." she looked down, as if ashamed. "You see... the real reason is..." It looked like Hailey was having a really hard time coming out with it. "Lindsay isn't doing so good..."

"Yeah I gathered that from your acting skills."

"That obvious?"

"Yeah..." I nodded, "So what's wrong with Lindsay. She seemed fine at the assembly the other week. I thought I even saw happiness when we locked eyes at one point."

"She was faking it..." that felt like Hailey had driven a dagger right through my heart, it physically hurt.

"Why? And don't tell me because she was just trying to not look miserable."

"Well that's why," Hailey said, "She told me not to tell you this... but I really want to..." she began.

"It's up to you."

"She really misses you," Hailey looked back down, apparently guilty of what she wasn't supposed to say to me. I'm glad that she told me though; it felt like the dagger lessened its pierce, a little. I felt really bad for Lindsay, how could I have done this to her? How could I have done this to myself, after all I did love her.

"So, why'd you come here again?"

"Lindsay doesn't know I'm doing this... I really want you two to be together again."

"I know, but I've got a girlfriend now."

"Do you love her?" I knew she was referring to me and Barbie. That was a hard question. Even though we labeled ourselves as boyfriend and girlfriend, neither of us had said 'I love you' to the other. We both knew that our relationship wasn't going anywhere. I glanced back up to see Hailey waiting patiently. "No," was all I could say. Hailey smiled meekly, trying to hide her little victory.

"So you love Lindsay?"

I couldn't help myself as I smiled and said, "Yes." Even just hearing her name (from another person) brought a smile to me.

"So why'd you break up with her then if you still love her?" I dreaded this question, what was I supposed to say? 'Oh yeah, I broke up with Lindsay because she's got a cock.' Fortunately I prepared for this question, it wasn't a great answer, but I guess it'd have to do, "Her mother didn't really approve of me. She really didn't like me and even threatened to have Lindsay moved from school unless I stopped dating her." I wasn't proud of my answer by any means, I mean, what if Hailey actually knew why I broke up with Lindsay. As far as I knew no one besides me, her mother, and a few of her past boyfriends knew about her cock. I took the chance that she probably didn't know about Lindsay. I guess my lie was believable enough, "Oh wow, I had no idea!" she seemed genuinely stunned.

"Yeah, it kinda sucked how it ended like that."

"So what are you going to do now?" she asked.

"I don't know, maybe I'll try talking with her mother first to see if I can convince her I'm not as bad a person as she thinks I am."

"I guess that's a good start, maybe I could help you."

"Oh no, that's fine, I think I should do it alone, to prove my worth to Lindsay and her mother. I wouldn't tell Lindsay though; I'd want it to be a surprise if it works out. And if it doesn't then she wouldn't need to know what I tried to do."

"Aw, that's so sweet!" she smiled, "Okay, I promise I won't tell Lindsay." Again, I didn't really believe her, considering she already went against her word with Lindsay.

The two of us chatted for a little while, I'd never actually hung out with Lindsay's friends without her being there, it was kinda cool. As Hailey left I realized that I was getting more and more comfortable talking with girls, I didn't really even miss a beat with Hailey. She wished me luck and I thanked her. It brought a smile to me as I thought about getting back together with Lindsay, I really hopped she'd take me back though, especially with the way I treated her. I figured my chances were decent considering Hailey's testimony.

Chapter 16

I didn't dwell on my lie to Hailey too much. I'm sure if Lindsay heard it she'd understand why I made it up. With this interesting revelation I was thinking more and more about Lindsay.

I really did miss her.

For fear of seeming too eager, I waited until the next week before I did anything. Barbie and I kept at it like rabbits, me feeling guiltier as the time passed.

I gathered my courage for Thursday, I didn't know why though, but I felt unbelievably nervous. And all I was planning to do was text Lindsay a simple 'hi.'

Yeah, I never deleted her number.

I waited until lunch time, because I knew she'd have time to respond if she wanted and sent her a text.

'Hi.' That's all I said, from here it was just a waiting game. I had hoped she didn't delete my number, I thought the worst answer I could get now was, 'who's this?'

I waited and waited; I gave up lunch just to wait for a reply but never got one. Maybe she blocked me on her phone, it was a scary thought, but that certainly ran through my mind.

Defeated I went to my next class as lunch ended. It felt almost as bad as when Hailey said that Lindsay was faking her smile, like the other cheerleaders. I moped about the day, occasionally checking my phone. I received a few texts from Barbie, in which I replied, but none from Lindsay.

Barbie was mostly asking for a booty call. Honestly I wasn't really feeling the mood, depressed from my rejection, but I went to her house anyway. I picked her up and we headed to the mall. She did her shopping while I was her mule, still glancing at my phone for Lindsay's reply.

The afternoon went by and we eventually went to her house to drop off her shopping, fortunately she didn't make me pay for it all. I thought the night would be finished but she wanted to go out some more, I agreed and we decided on a movie.

We went to the theater and found that it was mostly empty by the time the movie rolled around. It wasn't really late, but it was a Thursday night so I guessed people didn't want to stay out too late. We chose the back where we were alone, save for a couple more couples towards the front. Barbie kept giggling like she usually did as her hands roamed my body and mine hers.

Without paying attention to the movie Barbie rose and led me by the hand out of the theater. Like I said earlier, there really was nobody here, it was kinda eerie. Except for the ticket teller there was no one else nearby as far as we could tell. Barbie led me down the hall and to a closet. She couldn't possibly want it here. Apparently she did because once in, she locked it by putting the lone chair against the door, like they do in the movies. There was a workbench opposite the door and Barbie planted her hands exposing her tight jean ass to me. She was frantic in her motions, unzipping her jeans and pulling her panties down in a flash. She spread her legs as far as they could go with her jeans still around her ankles and stuck her butt out at me. We'd never done doggy-style or anything close to it before, but here she was bent over a bench and waiting for me.

Her ass looked so inviting, I couldn't resist, despite being in public. In a jiffy my cock was out and hard as a rock. Barbie handed me a condom and I wrapped it around my aching member. Next, Barbie did one of the sexiest things I'd seen a girl do. She grabbed her butt cheeks and spread herself for me. Her puckered hole was so inviting but I knew she wanted it in her pussy. She was already gaping and dripping with anticipation.

I stood behind Barbie gently letting my cock glide along her butt crack. She moaned to me, "Oh god, fuck me now!" With a bit of resistance I entered Barbie's tight pussy. She groaned at my sudden intrusion. She inadvertently tried to pull away but stopped herself as she realized what she was doing. Before long I was deeply inside Barbie. She groaned in discomfort and even winced and hissed. I began to pull out but she came back, "no wait..." so I did.

I waited before Barbie made the first move. She pulled herself out, moaning the entire way before plunging back into me. Slow deep thrusts were just the beginning. As we picked up speed, I grabbed onto her hips and plowed into her. I was shocked as to how into it Barbie was. As we progressed she kept leaning forward further and further until she was as far away from the bench as she could possibly be while still holding on. She was parallel with the floor and ramming her pussy back into me with just as much force as I was.

She was loud! Moaning and squirming until she shuddered in which she screamed almost silently. Her body shook like she had cold shivers. I wasn't too far off either as I plunged into her dripping cunt one final time and unloaded my cream. I collapsed onto her back and we both panted as we rested. Her butt and legs were all sweaty, like mine, but her top hid any evidence of her upper body's exertion.

Gently lying on top of Barbie I played with her breasts from the outside of her shirt. She purred quietly. We only did this for as long as my cock was semi hard. I soon slipped from her pussy and threw away the condom. I patted her naked butt, to which she laughed and we got dressed. We headed out of the closet and to the screen where our movie was showing. Satisfied, we sat hand-in-hand finishing the movie.

I took Barbie home and kissed her goodnight. On my way back to my car I checked my phone for the time. The first thing I saw was a text, it was from Lindsay!


I nearly jumped for joy, but I soon calmed down, wondering if it was a good message or a bad one. Not able to wait any longer I opened the message, 'hi,' it just said. I was glad that it didn't say anything like, 'who's this?' or 'don't text me,' or 'I hate you...' I'll take 'hi.' I checked the time the message was sent, and my heart fell. She texted it just about the time Barbie and I were having sex. I felt weird, at the time I wasn't even thinking about her, just Barbie, but now it felt wrong in some way.

'How are you doing?' I texted. I wasn't expecting a reply back so soon, but I heard my phone chirp.

'I'm okay, how about you?'

'I'm good.' I paused, thinking about what I might say next. I wanted to talk to her, face to face, but I didn't know if she wanted to. I decided to take the chance, 'can we talk?' there wasn't a response right away, I took it as her thinking whether or not to talk or not.

'Um...' was her reply a few minutes later.

'Please,' I hoped it didn't sound like begging.

'Just give me another chance,' I quickly added.

'...' was her reply, I took that as her thinking. I was sitting in my car, still at Barbie's and about to start the car when my phone chirped again, 'Okay.' I fist pumped my joy!

'Can we meet at lunch tomorrow?'

'Sure, by the art?'

'Sounds great, see you then.' I knew what she meant; there was a corner where very few students ate lunch. There was this creepy looking art that scared everyone away. And now my chance to win Lindsay back was in place, all I had to do was not screw it up!



The next day I was giddy with excitement, and dread, and anger, and nervousness. All these emotions were killing me in the early class periods but somehow I managed to get through them and on to lunch. I got to our designated meeting place before Lindsay and waited patiently. I didn't have to wait long before the most gorgeous girl in school came by and sat across from me.

"Hi," I meekly smiled.

"Hi," she replied, also smiling shyly. Lindsay looked even better than last week at the assembly. I usually didn't like girls with dyed hair but Lindsay really pulled it off. She had this hot pink dye in just a small bunch of hair along the length on her middle-left side. She had her hair in a pony tail, which I always liked and her earrings dangling just off her mousy cute ears. She tried hiding her smile but I was able to tell that she was, at least, moderately excited to see me too. Maybe Hailey was right, maybe Lindsay wanted me back as much as I wanted her back.

I felt like the first thing I should do was tell her no one knows about her specialness, "I would never want to hurt you Lindsay, even if things never did or will work out between us." Lindsay began blushing, because of my forwardness to her uniqueness? I didn't know. "Oh yeah, Hailey came by and talked to me last week."

This perked Lindsay right up, "Really? What'd she say?"

"She really wanted for us to be together again."

"Really? She came by and talked to you about us?"

"Yeah," I said, "And she really got me thinking," I lied. I had already been thinking before Hailey came along, "That I don't love Barbie and she doesn't love me. But I do..."

"Love me?" asked Lindsay sheepishly smiling while butting in.

"Yeah," I sighed, "I love you Lindsay!"

"Oh Jay! I love you too!" We were too far away to kiss or hug or anything so we sat there smiling to one another, unabashed now. I felt happy, something I hadn't felt since I was with Lindsay. Barbie was great and all, but I was getting bored with the loveless sex. Don't get me wrong, it was great sex but there was definitely something missing.

Unfortunately lunch came to a close all too soon. I stood to get up and leave, I wanted to at least hug Lindsay, but she refused. "What's wrong?" I asked.

"Uh... let's just say I'm just a little excited... well a lot," she was blushing beat-red. It took me a moment to appreciate what she meant and went wide-eyed at her predicament. "Oh wow, really?"

"Yeah," she smiled coyly.

"But why?"

"I've been thinking about you almost every day now, and now that we're talking again, it's got me all hot thinking about what we could be doing again soon," Lindsay was blushing even more now and I couldn't help but chuckle. "Plus," she began again, "I need some!" she giggled this time. My god it was so cute how she giggled and blushed there in her seat, unable to get up.

I didn't want to be late for class, so she understood when I said I had to go. I hugged her from behind, at least, since she still couldn't get up. I made my way out, but then turned right around. I couldn't just leave like that. Lindsay was still just sitting there, trying to think unsexy thoughts. I knew I wasn't helping her when I turned her head and planted a soft sensual kiss on her lips. She parted her lips and our tongues danced in one another's mouths. How I missed those lips...

The second bell rang and we were both late for class, we didn't care, none of that mattered. We broke away and smiled to each other. "Okay, I really have to go now..."

"I know," she said, "but you've got me all worked up again... thanks..."

I laughed, "Sorry Lindsay I just couldn't leave it like I did. I'd offer to wait with you, but I'm afraid we may never leave."

"Yeah I know, it's okay. Don't miss class because of me, I'll be okay."

"Are you sure?" I had to ask.

"Yeah, now go, or I'll be here forever!" I smiled and gave her a peck on the cheek before I finally left. I was so happy about how everything turned out, it couldn't have gone better. The only thing left was to break up with Barbie.


The end of the school day couldn't come sooner, but it eventually did. I met up with Barbie, as per her request. We walked back to her place, me trying to think of a way to end our relationship. I soon found that we were alone again in her house. Without a moment's notice we were upstairs in her large room. She sat down on her bed, very cutely I might add, and I stood there in front of her. She was smiling at me but I wasn't as forthcoming with mine.

Barbie saw my seriousness, she almost looked afraid. "Okay, I have to say this..." I started, "and I don't know how to say this. Firstly, I don't want to be taking advantage of you by telling you after we had done anything so I'll say it before anything even happens..." I dropped my head, thinking how I should bring all this up.

"You want to get back with Lindsay?" she said. I raised my head in shock.

"Uh, well... yeah..."

"It's okay, I saw how you two looked at each other at the assembly. It was only a matter of time before you two'd be together again. And honestly, I only really wanted you for your cock." I blushed by Barbie's last statement.


"Well yeah, I mean, you're hot and all, but I talked to Lindsay before we met and she said how huge you were. I just had to see for myself! Well, and feel!"

"So you're okay with breaking up?"

"Yeah, it's okay," Barbie said, though she sounded a little rejected.

"You don't sound that okay with it."

"Well, yeah... I mean I'm gonna miss the sex..." she trailed off.

There was an awkward pause until I spoke up, "So, is this it then?"

"Uh..." Barbie sat there, fiddling with her hands in her lap, "Could we... go... one last time?" she asked meekly.

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