My Girly Side

I am Ethan, currently a 19 year old guy. Or well, that's what i am biologically at least. I have never been really masculine in my life, to be honest. Ever since high school, I never really conformed to the idea of traditional masculinity. To be fair though, I have always had an androgynous face, a slim and delicate body, a plump behind, a very small penis and a soft and slim body. Obviously, I always tried to make myself more masculine by going to the gym, but that just resulted in me having more toned legs and a plumper behind, causing me to be the object of several curious gazes, especially during senior year.

However, everything changed in Freshman year of college. It was the second week, i barely knew anyone and was attending classes here and there, both for the credits and to meet new people. Not that I didn't know anyone. My best friend, Mia, was in my same English Writing class and another friend of mine, Pete, was in the college football team. Both of them knew damn well that, despite my desperate attempts, i was a girl at heart and liked men, but especially Mia was always supportive towards me, even encouraging me to grow my silky blonde hair out and style it, which boosted my self esteem quite a lot.

Mia was also my roommate. In fact, she hosted me at her gorgeous house, owned by her dad, since dorms were too expensive for me.

Anyways, on a fateful afternoon of that second week of college, while I was sitting on the couch, scrolling on my phone, Mia came out of the bathroom with a mischievous grin. I couldn't help but furrow my brow. She was usually very kind and polite to me. But when she sat down, I noticed that it wasn't a malevolent grin: it was an excited one. Quickly, she whipped out her phone and showed me some texts from Pete. One of them said "I'd fuck him if he was a girl lol," another one said "his ass is kinda nice tbh." I blushed. And I mean, BLUSHED. Mia started giggling, as i scrolled down the whole chat. It was him constantly asking what I liked, if i liked boys and whether i identified as a girl or a boy.

"Isn't he so sweet?" Mia said, looking at my surprised face.

"I-I mean kinda," i replied, my voice a bit shaky "but like... um... we never really talk and um..." but Mia stopped me on my tracks.

"Babe, we both know damn well that you like him. And I know that you wanna be a girl soooo bad," she said, pointing at my outfit. I was wearing a white crop hoodie, some tight jeans that highlighted my ass and some fuzzy slippers, while my hair was tied up in a messy bun. I did look like a girl.

"Yeah, I guess you're right..." I admitted, sighing.

"I know I am. And I have a plan for you." Mia said proudly, before heading to her bedroom.

She came back around 5 minutes later with a full bag. From what i could see, it was full of clothes and accessories. Without saying a word, she handed it to me and I headed to the bedroom. In it where some lingerie sets, loungewear, a cute dress and some shoes. I opted for the more sexy side of things and grabbed the white lace lingerie set, a dark, clingy and short dress and some heeled sandals. I then carefully applied some nail polish from Mia's collection, watched a few makeup tutorials and managed to turn my feminine face into the one of a goddess.

After having practiced my girl walk for about 5 minutes, i came out, the heels clicking on the floor, but when i saw who was in the living room, I almost fainted. It was Pete.

"MIA!" I exclaimed, blushing hard and on the verge of tears. Mia looked at me with a satisfied smile and winked.

"Hey, you read it yourself, he wanted to see you like this. Plus, you look gorgeous!" she said, proudly. I wiped my eyes and looked at her, furiously, but when i saw Pete, i almost melted. His dark hair, absolutely chaotic yet majestic, made his chiseled face an object of beauty. Before i could say anything else, Mia got up and patted my shoulder. "Well, i gotta go out for a bit, you two behave," she said, before walking out with a proud smile.

Pete and I sat there, a bit confused, a bit aroused. I could clearly notice his gaze drifting towards my plump thighs and painted toenails, and I gotta say, I didn't hate the attention. After a few more awkward minutes, I looked at him.

"You like me, don't you?" I asked, blushing a bit but keeping my gaze on his face.

"Well, I'd be lying if I said i don't..." he replied, trailing off as if there was a continuation to his phrase. I nodded understandingly. After all, neither of us thought we would find ourselves in this situation, so instead of whining about it I thought that maybe we could make something out of it.

"Have you ever... had a relationship with a boy... like me?" I asked, looking down to avoid his gaze.

He chuckled and looked at me, lifting my chin, and I can't deny that such a small gesture made my cock twitch.

"Like you? You mean a trans girl?" he asked, with a genuine tone in his voice that would make me exclude any bad intention of his.

"I mean... I don't know if I'm trans... I just mean..." I trailed off, feeling a lump in my throat. But he didn't need any more words. And just like that, i felt his warm lips on mine. I deepened the kiss, a stray tear falling down my cheek as he rubbed my soft back.

"Shhh... don't worry, I don't care what you are or what you like... I just know that you're fucking gorgeous" he said. And god, did that make my heart skip a beat. I smiled at him as i pulled back. My teary eyes made me look cuter, apparently, because he scooped me up and brought me upstairs bridal style, while i started giggling in a feminine way.

When we reached the bedroom he closed the door and dropped me on the bed, before leaning in for another kiss. Instinctively, I reached out and took his shirt off, revealing his god-like physique. My hands started trailing down his chiseled body, when i finally reached his sweatpants' waistband. I could clearly see the outline of his large cock, and without hesitation pulled down his pants and his underwear.

Before me now stood a naked, very well endowed college freshman. His cock was large, maybe 10 inches long and 3 inches thick, with an uncut and drippy tip which made my mouth salivate. My right hand wrapped around his shaft, while my left hand cupped his balls. When I started stroking, a low groan filled the room.

"Mhhh... fuck yeah... ah SHIT," he groaned even louder, enjoying my attention. To make things more interesting, I got on my knees and kissed his tip, savoring the salty drop of precum that coated his glans.

"Sorry for crying earlier," I said shyly "had i known that you had such a cock I would have led you here even before Mia left." I added, making him chuckle.

After a bit of foreplay, I finally went down on that cock, wrapping my lips around his tip and feeling the whole shaft twitch in my hand. Then, i slowly started moving forward, inch by inch, making sure my virgin mouth could withstand such an intrusion. At the 6 inch mark i had to stop, since going deeper would have caused too much discomfort for a first timer like me. I started moaning and bobbing my head back and forth, leaving a trail of saliva on his thick meat.

"Fuck babygirl... oh shit baby yeah... suck my dick, just like that," he said. Being called babygirl made my cock stir and harden in my panties, so, without interrupting my blowjob, i reached down and pulled up my tight dress and freed my 5 inch cock from my underwear. Prior to now, i never reached such a length, even though it is shorter than average, but for a small-dicked guy like me this was a huge advancement.

As i started stroking my cock, i kept sucking his, flicking my tongue on his sensitive underside. That seemed to do the trick, because around 10 minutes later he gently grabbed the back of my head, holding my hair tightly, and tensed up.

"F-fuck! Babygirl, I'm CUMMING!" he said, gritting his teeth and closing his eyes. Suddenly, his cock got engorged and what followed was a huge, sticky and tangy flow of semen straight into my mouth. I gagged a bit, but swallowed every drop before pulling it out. My mascara was now ruined, with streaks painting my cheeks, while my lipstick was smeared on his cock. I got up, a bit shakingly, but thank god he helped me sit down.

"That was amazing baby," he said, giving me a soft kiss on the lips.

"Yeah..." i replied, breathlessly, "but can you bring me some water, please?" I asked.

He nodded and brought me a nice and cold glass of water, which i chugged down.

After a bit, we started cleaning ourselves up: Pete wiped his cock with some wet wipes, while i hopped in the shower to get all the sweat and extra makeup off of me. When i had removed the last few layers of makeup in front of the mirror, i grabbed a pair of simple black panties and an oversized shirt, using them as a temporary outfit, and put my hair in a messy bun. But when i came out of the bathroom, Pete was gone. I checked my phone, to see if he left any voicemail or texts, and sure enough, he texted me while i was in the shower.

"Had a great time lol. Sorry for not staying, had to go. Let's do this again."

I smiled. At least he cared enough to text me.

With this in mind, i texted Mia goodnight and crashed on my bed, tired, happy and, most importantly, finally comfortable with my new me.

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I hope you all enjoyed. Please tell me if you want a part 2 to this and, if so, if you have any particular suggestions for what happens next.