October of 2016 was the first time I actually took dick.
Before that I'd done anal, being a top, with a few guys, but I consider this time my best, and really when I fully developed myself in terms of sexuality.
I was nineteen, shorter than I am now, and lived with this girl I'd known for a while. In highschool, we were both familiar with each other from being in the same Phys Ed class. I guess we were relatively good friends before moving in, because she comforted me after I was outed my Junior year.
She dated a guy I didn't know, but liked, because he was tall and muscular, as muscular as you could get as a teenager, and one of the only black kids in our predominantly white school.
We were in the same AP classes, and he was always the kid to answer questions without having raised his hand. Teachers liked him. The soccer coach liked him. I went over to his house with my friend, his girlfriend, one time after school, and was greeted by his wheel-chair-bound mother, who adored him and praised him for having multiple friends on top of all the extracurriculars he engaged in.
We went into his room upstairs, he had two cats asleep on his bed, and although messy he apologized and turned on this large old school stereo system connected to his MacBook.
This was the first time I really began to culminate my crush on him, because despite expecting to hear any semi-alternative rapper blast through the old speakers, and one I could enjoy to an extent, and preliminarily with the both of them, I heard none other than Kate Bush, and this wave of excitement rolled over me, as if I was experiencing something completely out-of-body.
It continued to fluctuate—my crush on him. Every day, I would wake up, and before doing anything else, check my phone. I just wanted to hear something from him. I assume that's how most crushes go. And, although I knew he was, or thought he was, straight, I always loved to imagine.
It was late October, just before Halloween, I got a text from my friend asking if I wanted to come over. She said a few other people, including him, would be there too.
Of course I obliged. Even though I expected them to want to go out to some party somewhere downtown, I wanted to spend as much time as I could with this guy who barely knew who I was.
I showered and asked her if anyone was dressing up—dumb question, as I see it now, but she told me her friend was going as a "sexy mummy". I decided that was her way of telling me what a dumbass I was for asking, so I showed up in shorts and timbs.
I wasn't good at driving, and didn't like driving, but despite wanting to beg her to pick me up, I decided to drive myself—this is important, because I was, at the time, the only kid who owned a car not co-owned by my parents. I knew they'd want me to drive them to wherever they were planning on going to.
Somewhere around seven I left, locked my door and called my dad to tell him about my prosperous endeavors.
Her house was in Hawthorne, a little less than three miles away.
She was standing in her driveway, a few feet from the garage door. Fresh-faced Indigo—not his real name, but the color of his room—stood, looming over my friend like protecting her from the rest of the planet.
I got out and immediately shivered, cradling myself like a child as I looked both ways through hazy, streetlight-lit darkness of what had to be millions of cars lining the road. I'm not a parallel parker myself, but found it justifiable to park close enough to her dad's car that it was out of the way of any threat traffic could bring, but blocked him from getting to work if I was still there in the morning.
"No wonder you're freezing. Are you wearing shorts? It's like sixteen out tonight."
I shook my head. "Eighteen", I smiled and jingled my keys.
"We going somewhere?"
"Were," my friend sighed, and I then saw one of our mutual friends sitting idle in her parent's driveway.
"Don't wake her," my friend gestured to the medical band on her wrist. Something about her stomach being pumped.
"She's good though?" Indigo lifted her by her shoulders, and my friend lifted her legs to take her upstairs.
"Yeah, passed out like five, ten minutes ago." I nodded and got in front of Indigo to help lead him into the house as he had his back to the door.
I watched them move her sleeping body into a bedroom while my friend half-heartedly explained that it was actually from raw crawfish and indeed not alcohol.
Indigo pointed to my legs.
"You're not freezing?"
"I'm alright," I gulped when his hand lightly grazed over my right arm.
We had to stay inside the whole night, because my friend wanted, of course, to watch over the kid passed out in her parent's bedroom. Our other mutual and his brother decided not to show after Indigo explained to them the situation.
"We should watch a romcom. We're practically stuck in one now." Indigo shook his head.
"She literally always wants to watch a romcom."
"It's the best type of movie. And if not now, when?"
He shook his head again, but flipped over to Netflix and began sorting.
"Do you really listen to Kate Bush?" It was a really out-of-place question, but genuine, and my friend looked at me from behind her boyfriend with a dumb expression.
"Uh, as much as anyone else, why?"
I shook my head.
"Do you listen to Kate Bush?" He turned away from the TV to look at me.
"Yeah." I nodded.
"My mom used to really like her. When she was in the hospital we would listen to her together, because she sang me this one song by her when I was a baby. I don't remember it, but she likes to think it calmed me, which I guess it did, but only because it calmed her more."
He turned off the TV after speaking.
I nodded and explained to him vaguely about my fascination for her wording and childlike interface in her lyrics.
I loved the dynamic between him, this tall, frat-like, athletic runner, and the sweet, sometimes startling yet charming vocal patterns of Kate Bush.
My friend had left, and gone into her parent's room with the door shut. I didn't suspect our other friend to be awake yet.
The TV wasn't on. It was just Indigo and I talking. As far as relationships go, he seemed very laid back. I knew his mom dated a woman at one point, because my friend mentioned it to me, I guess it was in college though, because she married, got pregnant with Indigo, and divorced immediately after.
He told me he loved his mother more than anyone when I asked him about his relationships. He told me he believed in everything she says, because he trusted her more than anyone.
I told him the relationship he had with his mother was sweet, and desirable as many people have to ask for their parent's affection. I asked if we should check in on our friend. He shook his head and instead wanted to go on a walk with me.
It was very cold outside, I'll admit, and he understood without me having to say anything. He took off his jacket and put it over my shoulders like a couple in a fifties movie.
Talking more, and side-by-side, it was a lot easier to establish how down to earth he really was.
He easily could have impressed me with vocabulary, or knowledge over the literature he'd read, but instead wanted to talk to me about relationships and, more specifically, friendships.
At one point, he asked me what I thought it meant when two guys, guys specifically, feel comfortable enough with each other to do things with each other that they'd typically only do with girls.
I didn't look at him when I asked what he meant. He bumped my bicep with his, and got me to look him in the eye.
"You know I'm bi, right?"
I nodded. I didn't.
"___ and I aren't doing well." I looked at him, and stopped walking. We were walking back to her house at this point.
"What do you mean,"
"She keeps insinuating shit-"
"That's not what I meant,"
"Yeah, well," he shook his head and looked at me.
"I'm just curious."
"You think it's a good idea for us to, whatever?"
He stopped looking at me, and we kept walking in silence.
"I think it's a good idea for me to, for you to, experiment. I'm comfortable with you, I just want to feel something different."
I knew he was referring to something emotionally different, but it got me hard, what he said.
We went behind the house instead of inside it.
He didn't kiss me. He took my hand and told me to turn around to face the back of the house. I did, and could feel my boner press against the brick chimney.
He told me to spread my legs, I did, and he touched along my thigh, then up my ass slowly, on my right side.
"She's not coming back," he whispered in my ear, and then lightly kissed my cheek.
"What-What did you tell her?" He hushed me, and touched down the back of my right thigh. I was loving it, not having ever gotten any attention on my ass before.
"I said we went for a walk."
I moved my hand behind me to touch his stomach. He reached around and gently felt my bulge.
"That exciting, huh?"
"Don't flatter yourself."
He slowly rubbed my bulge through short basketball shorts, before peeling off his jacket and dropping it next to me in the grass.
"You've never done anything with a guy?" I softly asked when I knew he was very close to me, because I felt his breath against my neck.
"I've kissed men before." He said that before turning me around, holding me against the wall, and kissing me.
"You wanna get undressed?" He looked me in the eye, holding the collar of my t-shirt, and about four inches from my face.
"It's really cold,"
He shook his head before taking my shirt and pulling it off my body, then pulling me closer to him in an almost hug, but stuck my hands under his sleeves.
I told him he had pretty eyes as he unfolded our arms and kissed down my stomach, hands under the drawstring of my shorts the whole time.
"You're really—pretty." He spoke into the waistband of my precum-stained boxers and I shivered.
He asked me if I'd ever taken dick and I told him I hadn't. He said it was alright, and asked if I had lube. I had lotion in my car.
He kissed my mouth before I gave him my keys and watched him jog around to the front of the house.
He tasted how he smelled; clean, a bit sweet I assume from the pears his girlfriend cut up for us.
I felt like a dick, to be honest, though I thought he was content with his decision to break things off with her. I was completely taking advantage, I mean, of her. She was stuck inside with our hurting friend, her boyfriend left her, and is now hooking up with her soon-to-be best friend.
He came back with a bottle of this aveeno baby lotion.
He laughed as he squirted some onto his hands and gently pressed some on the top of my ass, before slowly pulling my pants down to reveal my hole.
"Did you talk to her already?"
"What?" He seemed occupied. I wanted to forget about it but it was growing more difficult as he got closer and closer to me.
"Indigo—I don't want to hurt ___."
"You're not," he sounded a bit annoyed, but kissed the side of my neck anyway.
"You cut things off with her?"
I believed him. That didn't stop me from feeling relatively bad through the foreplay, though.
I told him it felt better at a certain angle when he was eating me out, and he told me he liked it when I pushed his head deeper into my ass. He had this great laugh—and smile, that sent shivers down my back. He would giggle when he came up, kissing my lower stomach, around my balls, and up to my chest. He didn't suck my dick, but I was more than happy to move down to his bulge peaking through pretty-tight jeans.
I undid the button pretty quickly considering how dark it was, and kissed around his—heavily moist—underwear. His thighs were muscular and hairy in all the right ways. His shins were hairier than his thighs, and he had this thick, black bush that cradled his heavy, dragging balls beautifully. He wasn't afraid to make noise, either. I kissed around his balls and felt his left leg begin to shiver and wobble and his voice gently tremble.
Then came the cute giggling on his end, telling me it tickled. He apologized, saying again that it was his first time with a guy. He was pretty thick, around the same length as me; I could go down on him and let him touch the back of my throat relatively well. I gagged a bit, which in reflux made him grasp the back of my head. He would ask if I was alright, if it was too much, and I would shake my head and take him in all the way again.
When he picked me up, he kissed around my shoulders before pressing my chest against the chimney, pulled my dick out right beneath my ass, and rubbed some lotion over it for me. My hole had already been well-lubed, so he just slid his dick against my crack, moving his hand along the front of my torso as he did.
He asked if I was ready, and I told him I had been waiting forever. I was pretty tight, he told me; whispered it in my ear, and quickly, as if he were about to explode. He asked me if I could take him, and to tell him if I needed to stop.
Of course, it hurt for about two minutes. I was pretty confident that I was a bottom. I was hard as a rock, after all.
He kept up this steady speed for only about four minutes before telling me he was close. He kept pressing his long fingers into my stomach, and pushing my down doggy, then standing me up and kissing my shoulders and upper back.
He pulled out when he came, then told me to cum for him. He helped stroke me, and kept watching my face, through the dark, as I made myself cum for him. I hadn't cum in a while, so my load was a decent size; not as big as his.
Afterward—I pulled on my shorts and shirt pretty quickly— he told me he'd gone in and used his girlfriend's home phone to call his friend to come pick him up. I thought that was awful, and then reminded me that I had just totally disregarded my friend in this short little endeavor.
I asked what he was going to do, and he told me he would talk to her tonight, as they always did. I told him we shouldn't have done this, and he just shook his head. He knew, I knew, we weren't going to make this a second or third time thing.
After that, I went back inside for a few minutes. My friend was talking with our other friend. She was awake and fine, at that point. She asked how our walk was with a weird expression, but I knew she meant nothing of it and was simply teasing me as she knew I had a bit of a crush on our friend's boyfriend.
I left pretty quickly afterward, my excuse being that my dad was home now; he got home usually around ten or eleven on Sundays, which was today.
Still think about it. I don't think about Indigo that often because I still see him as a mutual on the TL. He's studying abroad in Taiwan right now, which is interesting because his father is Taiwanese. He's also dating—planning on marrying a woman. How time can break a man.