Author's Note: This story is based on lived experience. Publishing permission was granted so long as I changed the names and a couple identifying details.
Alex was my best friend's older brother. He was a senior and I was a sophomore. We were both in marching band, both played percussion. I never hung out with him before college, but I remember being flirty to him the few times I was over at his house. Now that I was in the varsity band with him, we started sitting next to each other on bus rides. He kissed me on the way home from our second away game. It was a 30 minute bus ride but I don't remember anything except kissing him.
When we got back to the school, he made a point of saying he was going to shower. Some of the guys did when we had home games but away games meant not getting back to school before 11. Nobody stuck around for long when it was that late. However, I wanted to spend more time with him so I was willing to stay here all night if I had to.
---
I let him go off to the locker room first while I helped put equipment away. Once enough people left, I snuck away and headed for the showers. The lights were on, the water was running, and I saw my first glimpse of him. He was burly but hot in all the best ways. He saw that I had come in and smiled.
"I was hoping you'd try and spy on me."
"It's not spying if I'm not sneaking."
"Do you want to come in?"
"No but I'll gladly towel you off."
He turned off the water and walked out of the shower room. He grabbed his towel and tossed it to me. I worked every inch of him like I was waxing a car. I "accidentally" grabbed his dick more than once, causing him to moan softly.
Once he was dry, I kissed him again and said goodnight.
"I'll join you next time, promise."
He slapped my ass as I walked away. I was harder than glass and spent most of the weekend jerking off to just his image.
--
After that first shower together, we found ourselves running off for makeouts and gropes whenever we could. I started showering with him after practices, but we waited until people left before fooling around.
One evening, we were under the shower head. I was leaning back into him, feeling his cock slip between my cheeks. I wasn't ready for sex yet, but I was getting there. His dick was so much bigger than mine. At least 7 inches. Mine barely topped out at 4 but looked more like 2 and a half.
"Do you think my dick is small?"
"No. Why?"
"Sometimes I worry about it being too small."
"Can I tell you something without you getting upset?"
"Maybe?"
He ran his hands down my tummy but stopped short of my cock.
"I think it's kind of cute. A bit girly, but in a good way."
I'm not trans. I'm 100% happy as a man. Today I still identify as a man. But, in that moment, for a brief second, I wanted to be cute for him. I wanted to be girly for him.
"Is that what you want? A girly boyfriend?"
"Maybe. But I think whatever you are to me, I think I want to be your boyfriend."
My limp dick suddenly stood at attention. I turned around and kissed him. Dwarfed by his thick package, my cock might as well have been a clit.
"Yes. Please be my boyfriend."
I gripped his cock and mine in the same hand and jerked them slowly. He reached up and ran a finger over my nipple. I moved my hand faster and looked up at him. Then, burying my face in his chest hair, I squeaked and came.
"Dont fucking stop."
He gripped my hair as I kept my hand moving. I moved my head over a bit and nipped his pec with my teeth. That was enough for him. I couldn't tell how much I came but I know his load was bigger.
I caught my breath and looked up at him.
"We should go get dried off."
---
We could only fool around at school. Neither of us were out to our parents and we were very interested in keeping it that way. Things would change in college but that was a year from now. We held hands around school on the bus and in the safety of the band hall. I sat on his lap once but we agreed that would lead to something we couldn't stop.
After about 3 weeks of "shower time", the weather started to snap cold. It was late October when he asked if I wanted to come over after the game Friday night. It was a home game so we would be done with everything by 10. I accepted and let him kiss me deeper than we had before.
After the game, we both skipped showering at school. Just packed up our gear and fled quickly. He practically pulled me along as we raced for his truck.
Once we were at his house, he told me his parents were gone for the weekend so we had everything to ourselves. He sat down on the couch and I straddled him.
"I have you, I don't need anything else."
We made out harder than we ever did at school. It wasn't long before both our shirts were off and we were running our fingers across the others skin. Mine pale, his tan. My body skinny, his muscley. My boyfriend was a man. I still couldn't figure out what I wanted to be.
With our shirts gone, I decided to get my pants off. When I dismounted him he took my by surprise and picked me up, carried me into his bedroom. He was quick to get me undressed and wouldn't stop running his hands over me. I was warm all over. I started to unbutton his pants but he stopped me. He finished undressing himself and then laid down on the bed. I assumed the same position we were in before, only now much closer.
I spent a few minutes licking his neck and chest, gently nipping where I wanted to. At some point he reached into his side table and pulled out some KY.
Sensing his impatience, I sat back up and looked him over some more. I was about to give him my virginity and I couldn't be happier about it. Like that moment in the shower weeks ago, I felt his cock slide between my cheeks and his tip grazed my hole. I closed my eyes and felt my dick bounce. I was so ready for this.
I leaned forward to continue kissing him as he grabbed me by the hips. I grabbed the lube and squirted it in my hand. I stroked him while spreading it over him and my hole. He moved his hands down to my ass and spread my cheeks while I slowly slid him into me.
Despite how tight I must have been, it was like I was a glove to his hand. He stopped frequently for me to adjust but there was very little pain. I almost came when he bottomed out in me, both from physical pleasure and mental bliss. My head was back and my eyes were closed. He dragged his nails down my chest and lightly pinched my nipples. I was breathing heavy and moaning. He sat up and I felt his tongue and mouth against my nipple. I grunted, gasped, and came harder than I ever had before.
He was grinning like an idiot when I opened my eyes again. There was a little bit of cum on his chest and face. Sure it was the biggest load I had ever shot, but it was nothing compared to his smallest.
Without saying anything, he pushed me back onto the bed and started pounding me. I wrapped my legs around him and pulled him tight. I wanted to feel every inch inside me and every drop that came out. My moaning progressed back to squeaking, his turned to growling. Predator and prey.
When he came, he practically roared. His cumshot was like nothing I had ever felt before. It was as if it reached all the way up into my stomach. My legs stayed wrapped around him while his cock continued to convulse inside me. We looked at each other and started giggling again. This is what love felt like. I fell asleep with his chest hair against my face, his arms around me, and his cum dribbling out of my ass
The next morning, he was already awake when I rolled over. He kissed my forehead and I felt my heart flutter.
"I've never felt like this with anyone before." I was blushing furiously.
"You look like a princess this morning."
We were back on the topic of my femininity.
"Is that what you want me to be, your princess?"
