Converting the Homophobes - Chapter 2: Jeff

Everyone is 18.

Chapter 2: Jeff

I left Jack and Nick’s house the next morning with a sense of easiness and pride. I had finally taken the leap, and it paid off amazingly. Jack had even asked me for one more blowie while I was in the shower. I was on my knees quickly and he humped my mouth for about twenty-five seconds before giving me another load. Discovering his little brother (age 18), Nick’s naughty side and potentially an underground gay hookup scene was an unexpected bonus part of the night. On my short walk home, I thought about the next guy on my list. I was ready for more dick, and I had friends who needed open-mindedness training with my body. All my friends were horny, but moving forward I would have to be more careful than how I had handled my sloppy introduction with Jack. He was an easy mark, but Jeff, by my estimation the second horniest friend in our group, was going to require a gentler approach.

Jeff was not the kind of guy you’d expect to say yes to anything remotely outside his comfort zone. He wore socks with sandals and still used “bro” as a full sentence. He once said the phrase “no homo” while hugging someone at a graduation. Classic Jeff. But maybe that’s why I was curious. The more someone overcompensated, the more I figured there was something underneath worth poking at. Metaphorically. For now.

One thing that was notable about Jeff was his obsession with a girl’s backside. His face lit up every time a girl with a fat ass in tight pants walked by. He couldn’t hide it at all. The guys would laugh at him when his eyes opened wide and his mouth dropped. I always had a thick posterior myself, even on my thin frame, and he would poke fun at me regularly. That meant he was aware of my ass. That was something I could work with. 

He lived across the street, in the blue house with the broken basketball hoop and that weird metal sculpture his mom made during her “found object” phase. I waited until the afternoon, and even though my ass and throat were still sore, I went for a run, took a nice hot shower and texted him:

Me: yo u home

Jeff: ya, bored af

Me: come thru

I put on a slightly shorter than average pair of gym shorts that I had outgrown a couple years prior. I needed a tight fit to show off some ass. I hid a bottle of baby oil from my bathroom in the couch cushion in case it would come in handy. Five minutes later, he showed up in gym shorts and a tank top that said “Keg Stand Survivor.” His hair was still wet from a shower, or possibly from sticking his head under the sink — I didn’t ask.

“Yo,” he said, flopping on the couch like it owed him money. “What are we watching?”

“Nothing yet,” I said. “I was gonna ask you something.”

His eyes narrowed, suspicious. “Like what?”

I hesitated for a second, then decided to just go for it. “You ever wonder what it’d be like… if a dude did stuff with you?”

He choked on his LaCroix. “What kind of stuff?”

“You know,” I said casually. “Like what girls do. But a guy instead. Just to try it.”

He blinked. “Like—stuff stuff?”

I nodded. “Yeah. Not all of it. Just the first level.”

Jeff leaned back, looking at the ceiling like he was scanning an invisible FAQ. “Huh.”

There was a long pause.

Then: “So wait, are you offering?”

“I mean,” I shrugged. “Only if you’re curious.”

Another pause. A longer one. Then, with a tone of someone testing the waters but also already halfway into the pool:

“…You’d be the one doing it?”

I nodded again.

He stared at the blank TV screen like it was going to give him a sign. Then he slowly set his LaCroix on the coffee table, leaned back, and said, “I mean… I’ve always been curious about getting with a trans girl, and you wouldn’t be that different. You can try if you want. But like, if it’s weird, I’m just gonna say so.”

“Deal,” I said, my heart pounding out of my chest. I could not believe he said that thing about trans girls. If he’s ok with them having a dick, then there would be even more wiggle room than I thought.

Since we had the house to ourselves, I threw some big butt bimbo porn onto the living room TV, which instantly drew his attention and made him adjust his crotch. He sat comfortably, and we didn’t talk much more about it, I just sat next to him, with my own hardness obvious, but I refused to touch it, making it all about Jeff for now. The big living room window was open, giving anyone out on the sidewalk a direct view of us. If Jeff didn’t care about any potential spies, neither did I.

When the girl on the screen suddenly had a dick poking her big butt cheeks, I knew Jeff was ready. I reached over and carefully put a hand on his bare thigh. He flinched only slightly, and didn’t look down. Keeping my own eyes on the screen, attempting casualness, I moved my hand up his thigh, through the leg of his shorts, feeling the light hairs get more sparse as I approached his ball sack, until the tops of my fingers grazed his hairless nuts. His body was braced somewhat tight, but his firm pole pressing tight against his shorts told me he was ready for it. I reached for the base of his swelled rod, and it was torture trying to keep my eyes on the screen while I moved toward giving my buddy a gentle bro-job. I gave him a gentle squeeze on his shaft, and felt his cock pulse like a heartbeat, forcefully resisting the pressure of my palm as the blood pumped firmly and pressed back. With my first stroke to the tip, he let out a long sigh, eyes focused on the big butts on the screen.

I pulled my hand out of the leg of his shorts, and reached for his waistband. He just lifted his ass off the couch and let me pull them down. I got them to his ankles and returned back to his exposed cock. It was thickest at the base, and it throbbed against his abs. His balls were big and round. He suddenly looked a little shy about being exposed, so I sat back next to him again and removed my own shorts as well. Still looking at the TV, he nodded in a light appreciation of my camaraderie with him. I admired that he was willing to go this far already, but we weren’t done yet. 

I reached back down to his cock and started stroking him. I thought back to Jack and Nick abusing my hole the night before. Even though it hurt, I craved that sensation of getting my button pushed from deep inside my body. Jeff’s cock was different, just as long as Jack’s but thicker at the base. He would make me squirm.

At this point, the girls on the TV were getting anally stuffed by some frat boys with giant cocks. I was slowly rubbing Jeff’s cock, careful not to let him explode just yet. He was loving the treatment, alternating closing his eyes with his hands behind his head, and occasionally looking down at his cock getting a handy from his friend.

“So,” I started my query, “would you ever actually do a girl in her ass?”

“Abso-fuckin-lutely,” he said between breaths.

“You wanna watch her squirm while she takes your big, thick cock, bro?” I asked, giving him some dirty talk and buttering him up, literally.

“Yeah, dude, wouldn’t that be awesome?” He replied.

“Yeah, but I think it’d be cool to take it too.”

“You wanna take it up your ass?” He asked, curious, not even realizing what I was hinting at.

I quickly stood up, pressed my legs together, and bent over, showing him the thick ass I carried around under my thin waist.

“Bro, I can take it.”

“Bro!” He said, starting to laugh, “I didn’t expect that.”

“You know I’ve always had a thick ass dude,” I said.

“I guess yeah. Isn’t that kinda crazy though?” He asked. I looked back at him as my ass was aimed right at his face. He hadn’t said no, only asked more questions, as his throbbing and wet cock levitated above his abs. “Not to me.”

He started “I mean, if you want–” and before he finished his sentence, I reached behind him and grabbed the baby oil from the couch, popping the top open and slowly dripping a generous amount onto his meat pole. He chuckled as the cold lube coated him, before I reached down and warmed it up as I spread up and down. His face turned red–it was already feeling better than he expected. I turned away from him and bent over my coffee table, giving him a perfect view of my ass as well as the porn on the TV. I didn’t push him any further, just waited for him to find his way into me.

“I haven’t even fucked a girl yet,” he said, as I heard the wet sloshing sound of him beginning to stroke himself.

“I’ve heard that before,” I said, my mind flashing back to the two stuffing me the night before.

“From who??” he instantly demanded.

“Couldn’t possibly say,” I said as I stayed in position, leaning on my elbows on the coffee table, “and I’ll never tell anyone about this either.”

“Perfect answer,” he said, confidence returning to his voice. I heard him shift off the couch, and felt his pole press between my cheeks. As he pressed forward, putting his hand on the table next to my body and releasing a long breath, I felt both out bodies tingle at the contact. His dick found my hole more easily than the others had, and his hands caressed my back seductively. He gripped handfuls of my cheeks and really took advantage of my body. I felt notably wanted, even cared for. It was better than the simple, filling pleasure of having a dick in my ass again.

When he started to push deep, fully stretching out my hole, it struck me what was different about Jeff. He wasn’t just being tentative, he was actually gentle. He took care as he was using his body. He had already started fucking me, but even with the obsessive drive of a teen male trying to cum, he cared about me the whole time. It didn’t even hurt the entire time he fucked me, and he was the thickest of the three dicks so far.

I looked back and watched his body as he picked up the pace. His own perky ass bounced in the air as he pistoned his teen shaft into me, making a lubed up and tight, repetitive squishing sound. He started to get close to cumming, then pause. His cock throbbed inside me as he waited to come back from the brink of orgasm. Then he would return to a rapid sawing, uttering mild sex talk under his breath, like “good ass”, “cum slut”, and “fucking tight”. The line was obviously blurred whether he was referring to his porn ladies on the screen or the tight, male teen ass in front of him, and I loved the ambiguity of the situation. There was plausible deniability, even in the gayest of times. His short brown hair got sweaty and began to stick to his forehead, and he finally said it. “I’m gonna–”

But he froze, and I felt his thick rod, balls deep inside me, begin to unload in bursts. He released some involuntary throaty sounds as his legs trembled from holding the position, and finally his body released. He slowly pulled out of my ass with a wet pop, and I felt cum run down my legs. I wondered whether my hole would ever learn to not leak after sex. I hated the feeling of being empty after an especially heightened sexual experience, and turned around to face him as he plopped back onto the couch, naked and still hard. I didn’t say anything, just started jerking my cock, while probing my ass with two fingers. I looked at his cock and started to get myself to the edge quickly, but, to my surprise, he stopped me. 

Wordlessly, he sank to his knees off the couch, and pressed his hard dick back inside me. He pushed my hands away and jerked my cock with a tight grip, focusing on my entire length and pumping rapidly, his strong hand becoming a blur on me. I felt my hole tense on his thickness as I quickly unloaded my white goo onto my tummy. 

“Good girl,” he said, for some reason, as he pulled out yet again and grabbed his underwear, pulling them up over his ass and tucking his junk away. 

Then we shared a long moment of silent eye contact, that actually didn’t feel weird at all.

Jeff muttered, “That was not what I expected.”

“How so?” I asked, trying to sound chill.

“It was kinda awesome,” he said, furrowing his brow. “Just… huh.”

Another pause.

“I wanna do it again when you’re ready,” he said, still looking up at the ceiling, as a random streaming TV show was playing in the background.

We did it twice more that day, and the third time he actually lasted several minutes. With his gentle, caring nature, I wasn’t as sore as I thought I would be. When he finally left, the sun was just about to set. He gave me a knowing smirk, said goodbye with minimal words, and headed across the street to his house.

Three down. A couple more to go. And each one left me a little more sure: this wasn’t just about me experimenting. It was about showing them — and maybe myself — that whatever we were all scared of? It wasn’t actually that scary. Maybe the all-boys school hadn’t ruined us after all.

Next on the list? Tommy. And he had… opinions. This was gonna be fun.