My Loving and Caring Girlfriend

Hi! This is my first story and I hope you all enjoy. This feature a man and woman, both 18+, who are madly in love and shares their love each other through the sacred art of sex. This story contains the following: anal, male on dickgirl (man penetrating a trans woman), and a balljob. Sending love and good vibes your way!

*****

I met Alice during the end of my junior year of high school. She was a transfer from a rival school, but came here because her family had to move here for work. Usually, our class makes a big deal about a new student (technically two students since her brother was also transferring), but nope, not this time.

Everyone just carried on with their lives, like she didn't even exist.

My friend group immediately realized her brother, Brandon, existed so why not her?

My friends apparently met her when they met Brandon and from what they said, she was awkward. She couldn't keep up a conversation and her eye contact was too drawn out and it creeped them out, and she would do this weird breathing thing sometimes when she got excited.

They outed her out of the group indirectly and only Brandon joined us on our adventures. It would be us and Brandon, and when I'd ask about Alice, he tell me that she's just at home, which made me feel horrible.

Some days, I would just feel bad for her. She was always alone: either walking to class, to lunch, and even some days, walking home. Most days, of course, because she and her brother would walk home together. But weirdly, I didn't meet her from walking home with them.

I actually met her at the graduation rehearsal for the graduating class before we graduated. For those who are unaware, at our school, the top 12 students in the class were junior honor guides, thus the people who would help escort the graduates to their seats during graduation.

I was number #12 and she was #2. Her gown was decked out with models, and a completely different color: silver, while mines was red and bland. Even to this day, I remember our first conversation. She came up to me, sat next to me, and started talking to me. We talked, which was not like how my friends perceived her as a shy, inept girl.

We talked about anime, and video games, and I realized just how wrong this guys were wrong about her. She was just a shy girl, and maybe she just had trouble getting her point across. It was clear she was more comfortable talking about the things she liked than about interpersonal things. I started to like her a lot...

...but only as a friend at first.

It's funny because when I had first met her, I didn't see her as romantic material. She was just a quiet girl. She was a slender girl with caramel skin, raven-colored unkempt hair, and she had hazel eyes. And she always wore these thick black glasses, because her vision was bad. I mean, sure, she was also very nice and polite to me, but nothing in her personality stood out, which made her a lot like me.

But as time went on, the numbers of time we walked home together increased, the times she would start to touch me got more consistent, and how well me and her got along and how she genuinely liked being around me, what happened next was inevitable.

I started to fall in love with her. We were both 18 at the time of my feelings emerging.

But then, our graduation came.

We both graduated in the top 10 of our class, and seeing her walk up on stage made me so proud and at the same time, so sad. I was sad because this was it. This was the last time we'd see each other, because I wasn't staying here for college. I was leaving our state.

I was so shy, but I masked it by being overtly positive with others. I didn't have the guts to tell her that I liked her. I didn't have the guts to even ask for her number.

So I just ... let it happen.

We went our ways for a year, to our respective colleges, and life spiraled out of control for me. I got depressed and everyday became a struggle. Wanting to live was a daily chore. I wanted it all to end, and it wasn't even about her. I just hated myself because I was lonely and had no direction in life — I didn't connect with anyone there either, which made things worst.

After freshman year of college, I got a hold of her number from a friend, and I wasn't gonna make the same mistake twice. We grew over time via text, conversations grew longer, and talks got more personal. We were only able to hang out a few times in the summer but those were a lot of fun. She told me about her hardships and I felt so happy knowing she trusted me with that information.

Some time before I started the next year of college started , I finally did it. I confessed that I liked her. And —

She rejected me.

It was so unexpected because I thought we would be together. I was still so sure it would happen. She told me that it wasn't me but she didn't like anyone that way.

I kept talking to her and it was painful. I tried to see the best of the situation, that she's still in my life and that I should be glad with just that. But I couldn't — well, i could, but it was hard. I wanted her as more but I just couldn't let go.

But I'm glad I didn't.

A year passed. We're both 20 now. She helped me through my depression, and words can't describe how much that meant to me. A lot changed for me. I beat depression, I was more confident and upfront, and I was on my way to be a better person. I tried to lose weight but failed, but I ultimately got a way better mindset, that counts more, right?

I learned a lot about Alice too. One day, while texting each other, I asked about her sexuality, which led to her telling me about how she DIDN'T reject me. I asked her to go in depth and she told me that when she rejected me, she was unsure of herself. She knew she was into men but she just never wanted to date. She told me that she doesn't know herself.

I decided to shot my shot one last time with her then as a final closure, I asked if she would ever date me.

She said she can see us dating, but she's still trying to figure herself out. This made me happy, because I knew it was gonna happen now. I could feel it with my newfound confidence.

This leads us to the present. One faithful hangout.

*

"Hey Alice, are you free today?", I shot to her via text.

"Yes.", she says back.

"Wanna hang out? We haven't finished Bleach."

"Sounds good, be over in a hour."

As I read, I sit back and sigh.This is it, I thought.

I have the house to myself — my dad was at his house and my mom was visiting my aunt in the city, and she wouldn't be back until Saturday (it was a Tuesday during the summer). We haven't hung out in nearly a year. I wonder if she looks the same. Maybe she put on some weight, I don't know.

As I sat, the realization she was coming over here set in, knowing the house was a complete mess. I brushed my teeth, fixed up our living room, and after all of that, I looked at the clock. I had about seven minutes left.

I ran to the bathroom, to give myself a pep talk.

"Okay, Cody, you got this. You're gonna show your macho and she'll basic —— no that's so cringy and bad."

The doorbell rang.

"Fuck." My heart starts to beat so much faster, my palms became hotter and sweaty, and my hand-eye coordination went to shit.

"You got this, dude. We made a plan for today, follow the plan and it won't get awkward, I swear."

I go to the door and opened it.

And there she stood, beautiful as I remembered.

She smiled and I let her in.

The time goes by fast. We have a lot of fun. We made brownies, we finished our anime (finally), and it was good to know I could still make her laugh. It was around noon when we started, and now it was about 6PM.

We go out to my patio with a swing, and sit there as we finish arguing about something. The beautiful sky — purple and orange highlights, surrounding the pink sky. The sky almost like from the Black Panther but a bit brighter. Despite all of the beauty, there was something I had to settle with Alice.

"Ichigo is the strongest, hands down!" I shout.

"Ew, no." she says disgusted.

"Then who?"

"Not him."

I stared at her. She starts.

"Okay fine, I think it's Soi Fon."

"Really how?"

"I mean, she has a dagger that if she stabs twice in the same spot, you die no matter what. Arancar, Quincy, anyone."

She takes her index finger and pokes me in the chest twice, mimicking her ability, but stops at the second on my chest. She looks at her finger and places her palm on my chest. She then stares at my chest then into my eyes.

"Do you have a heart condition?"

"No. Why?"

"Then why is your heart beating so fast?"

"I —"

"I know why, don't worry. I guess it is something we have to talk about in person sooner or later. I mean, it was bound to happen." She shifts a bit closer to me and begins.

"I have something to tell you."

"And what's that?"

She sighs, "I — I really like you." But as she says that, tears start to form in her eyes. "I've been thinking lately and I really want this now. I'm sorry it took me so long and I even rejected you, but I want to be with you."

Though those words warm my heart, I had to ask.

"Why are you crying?"

"Because there are things about me that I know you won't accept."

"Then try me, what is it?"

She stops moving and I see her sigh again. "I wasn't born a female."

I was shocked because she was so beautiful. She didn't look like a man. But more importantly, my feelings were still intact.

"I still like you, that doesn't change how I feel about you."

She smiled and then it suddenly dropped back to the empty face from before. "I still have it, if you know what I mean."

I know what she meant but still, my feelings were still as strong as ever.

"And that's fine. You're still a beautiful girl to me.", I said while holding her hand.

She exhaled sharply and then looked at me, and we embraced for a big hug. She was clenching me tight like she didn't want to let go.

Then she pulled back and kissed me. Words couldn't describe that kiss. How bad I wanted that kiss. A kiss I had long for for five years. It felt like sparks were firing in my mind, a burning sensation in the right side of my brain, as her tongue explored my mouth. It lasted for a few seconds until she pulled back, bothered.

She looks down and back up, readjusting her shirt. She slouches back on the swing.

"Damnit." she says quietly.

"What?" Then she points down to her dress.

"Oh."

"Yeah."

Clearly visible was a bulge but from where I was sitting, I can't tell how big she is. At one point, It looked like it was about to rip through her panties, through her dress, and give way to a giant erection, but from some angles, it looked unnoticeable. However, she was clearly uncomforable nevertheless

"I can take care of that!" I say proudly.

"Cody, I appreciate it but you don't have to do this. I can just —"

I kissed her, shutting her up temporarily. "I want you, Alice, all of you."

She looks away, and then turns back, smiling helplessly. "Okay, thank you."

I hold her hand and into my house we went. Up the mag phony stairs, past the oak wood dressers in the hallway, and into the marble lined bathroom. As we get there, she goes a bit ahead of me and stops.

"I'm a bit afraid, Cody."

"Why?"

"I've never done this before. I never even be naked in front of anyone before, I mean, besides family when I was little."

"I see. It's okay to feel that way."

"I've never even been with anyone much or less done anything sexual with someone else."

I looked away. "If it makes you feel better, I haven't either."

She looked in complete shock. "You're lying, right!"

"Nope, never had a girlfriend."

She smiled but like before, it faded. "I'm actually flattered to be the first. That kinda makes me happy. But uh, what are we gonna do?"

"Oh right, well, so first, I think we should both get naked. It make the experience more calmer for both of us and more intimate."

"Yeah, you're right. Okay. But I want it to be a surprise."

"Yeah, definitely. So we'll both turn our backs, and on the count of 3, we'll be turn around. Deal?"

She smiles and nods. She takes off her thick ass glasses to reveal a very beautiful face, her natural beauty practically glowing before me. She turns around and I start to see her pull down her skirt. I almsot forgot that I need to turn around to, and proceed to do so myself.

I'm getting naked with my crush right now., I thought to myself. My member grows uncontrollably hard, realizing that I'm about to live out a fantasy I had for years on end. A minute passed and I heard the sounds behind me stop.

"You ready?"

"Yeah..." she says sheepishly.

"It's gonna be okay... Okay?"

"I know."

"1...

...2...

...3!"

I turned to meet the beauty of Alice. Upon seeing her, her face grows red and she begins to cover herself but stops when she sees me. She had small breasts, a slender belly, and a nice ass. I guess I never saw it because she always wore dresses.

She was so sexy but a part felt very emasculating for me.

As much as I found Alice to be sexy, there was no denying that she was bigger than me in that apartment. Her dick grew hard when she saw my body, and it was easily clearly mine. It was much bigger in fact. She had a bit hairy down there but she was still so feminine. Her dick was just so beautiful. I never thought I'd say that but yeah.

She was long and thick, with hairless and smooth, jumbo chicken egg sized balls. Her sack was so smooth looking, almost like her breasts. Her shaft was a slight darker color compared to the rest of her body, which gave me clear indication that she masturbates often.

She was embarrassed, standing there in the open, with her womanhood twitching uncontrollably towards me.

"You're beautiful."

She stares me and my glory. "You are too, so pretty."

"Oh, so I'm pretty?" I tease.

"Yes." she replies completely unaware and not getting my sarcasm, which makes me like her more because of her innocence.

We go to each other and lock lips. Our bodies start to grind against each other, smelling her scent and embracing her hump and grind she gave. Her dick was above my bellybutton, and with me being nearly 6 inches taller than her, I pulled back. I just need to know.

"Hey, Alice, I'm curious."

She stops sucking my nipple and looks up at me, lost in thought. "Hmm?"

"Can I ... can I measure us?"

"Oh, yeah... Go ahead!"

I pull out a tape measured from under the sink from when we did rennovations on the bathroom a few weeks ago.

I measure myself first. She steps forward to see my length.

"5.7 inches..." I say out quietly.

"Ooh!" she says supportively.

"Now, your turn."

She steps forward, smiling. Her dick, unknowing to her, skids across my stomach and thigh, and the intimate touch sent an electrical shook through my body. I gasp and my cock flexes hard.

"Are you okay?" she says with concern, touching my arm.

"Oh, hehehe. I'm fine, your dick felt good when it went across my body."

"Oh!" she says innocently shocked.

"I'm gonna measure you now, try to make your cock as non-twitching as possible."

"Gotchu!" she says enthusiastically.

I measure her and stop at her length.

"... 9.2 inches." I say out loud, a bit monotone.

I felt a bit sad. Here I was, with the love of my life, and yet her dick is just so big. She should be the top, not me.

She continues to smile until she realizes that I'm a bit off. Though context, she realizes why and tells me, first by holding my arm.

"Cody, so what if I'm a lot bigger than you? It doesn't change that I'm a woman and you're a man. And to be very honest, I love your size, and I really like you. I know you probably felt like you chose me but I chose you too."

She's right. I shouldn't be sad about this.

I smile and hug her, our dicks hugging, mines much more down her shaft.

She smiles. "So ... sex right?"

"Oh right, hehehe, so um... How do you get off? Top, bottom vers?"

"I'm just a bottom, if that helps." she shrugs.

I was in shock. "Really?"

"Yeah, I've never really had much of an interest in penetrating guys. I mean, booty looks so good. Like yours! But I don't know about putting my dick in it. Even in nice booty. Besides, when I'm masturbating, I usually get off with anal beads and stuff like that."

"Oh, okay, that's pretty hot!"

She giggles.

"So off we go!"

I take her by the hand and we quickly run to my room. There's my bed in the corner with a TV and fireplace in the other corner.

"Oh, that's fancy." she says

"I know right!"

We sit on my bed for a while, talking about our preferences. I tell her that I want to try doggy and she's all for it. I asked if she wants to try anything of her own, but she doesn't really have anything come to mind.

I would be lying if I said I wasn't looking at her beautiful body the whole time we were talking. Eye contact became so hard and half way, through the talk, she leaned on my bed, revealing her dick, still completely erect against her stomach. Words cannot describe how hard it was not to ounce in her right then and there.

"So time for business!" I say excitedly.

"Yup."

"Hey, have you ever gotten head before?"

"No." she says sadly.

I realized how dumb I sounded "I mean, yeah, it's just with a dick like that, I wouldn't be surprised if you could suck yourself off."

She looks away, a bit embarassed. "I mean, I can but only the tip. I'm flexible enough."

"Then let me do it for you."

"Okay!" she says, immediately laying down on her back in my bed.

"Oh." she says

"Hmm?" I say, getting into position between her legs.

"I should have showered. I can smell myself."

I immediately sniff her cock.

"Hey, don't do that. That's dirty."

Her cock smelled so wonderful. I could smell her musk. Strong and full of pheromones, I couldn't help but get harder. My dick became instantly agonizing.

"Okay, here I go."

"Fine. Be careful." she says with concern, which made me choke from laughing with her cock in my mouth because she knew her dick was a lethal weapon but she was still an caring angel.

But I went to work. I had never sucked a cock, but damn, I gave it my best and she was loving it. Her moans and grunts made me know she was genuinely enjoying my barrage of slurps. Her taste was out of this world.

But as much as I sucked her, she never came. She just really enjoyed it. Even when her moans grew very loud, she still wasn't get close. Her endurance was godly, mine wasn't. In fact, me giving her head actually made ME cum. Her musky aroma and the sight of her in heat, wanting me, sent me overbroad. I ended up coming on her right leg and her balls.

I pull back, with an audible pop from my mouth from suck I g her dick. Her dick was still at attention. She got a bit and kissed me.

"I'm glad you enjoy it. I never would have thought you came to that." she giggled.

"Yeah, I just wished I could have made you cum."

"It's okay, really. Also, we need to get you up again. Because I'm really horny right now. So I have a treat for you. Lay down."

I laid down, slick from my nut still on my dick tip. Alice got up and got situated between my legs. Was she about to return the favor?

"Well, Cody, I would give you head but I just got a root canal and I need to get the second one out soon, so I don't if it's the best idea."

"Try me."

"Okay."

She puts my dick in her mouth and in the back, I was met with one crooked teeth. Was it it the second teeth? Was it in the middle of her mouth? Because it hurt like hell.

"Ahh, Ou- AHH!" I screamed.

She pulls my dick out her mouth, embracing me for a big hug. I'm praying in my back and she's on top of me, her dick sliding between my checks.

"I'M SO SORRY. I don't mean to hurt you. I just wanted to see if it was possible but not until I get that one out. I do have something else in mind though." she says smiling. I see her dick grab her and starts to slap her dick against the base of my taint, slowly sliding up.