The Loophole

My friend Kyle is super hot and super religious. I enjoy the former thing about him and do my best to ignore the latter. We met at work and we get along well; we lift together and get dinner afterward.

I could tell something was up with him that day. He seemed distracted. We were doing squats and when it was time to switch he would be staring off into space.

“Kyle!” I said at one point, waving my hand in front of his face. He was staring up at the video monitor where some sexy pop star was gyrating.

“Wha - oh, sorry,” he said, and went to rack his weights.

I brought it up at dinner. At first he acted like he didn’t know what I was talking about, but then he got into it: he’d been having some issues with Delilah, his fiancé.

“We’re waiting for marriage, of course,” he said, a wince flashing over his face. “She’s just as devout as me. But lately, well, she’s been wearing these outfits…nothing scandalous but they just take my brain to this place that I’m having trouble getting out of,” he said, absent-mindedly grabbing at his crotch. “So I’m really struggling with these, you know, sexual thoughts around her. And even when I’m not around her, now,” he said.

“Do you masturbate?” I said. The word seemed to startle him.

“No, no,” he immediately said. I nodded. I guessed that was a sin.

“That’s rough,” I said, somewhat at a loss, as I usually am when Kyle’s religious-based worldview comes to the fore.

“Yeah,” he said. He took a deep breath then gave me this level look. “My pastor…he’s pretty progressive,” he said, and stopped.

“Yeah?” I said. Kyle looked like he was unsure about going on.

“He told me about something that might help,” he said. Weirdly, I felt my cock stir. “A way to relieve the pressure of waiting till marriage. Like a safety valve. A loophole, he called it.”

“Interesting,” I said.

“Well, what he said was, I could lie back and he would get on top and sort of…manipulate me, like inside of himself,” he said, his voice getting quieter. “Until I get some relief,” he finished, and looked at me. I did my best not to react.

“So, like, in his…butt?” I said, careful to use words he’d approve of.

“Exactly,” Kyle said. “He’s said it’s like a cheat code - something that isn’t sex or masturbation, but would help take me out of that dark and lustful place I get when I’m with my fiancé.”

“Interesting,” I said again.

“Yeah,” he said. “Except I can’t imagine having him help me with that. He isn’t…” Kyle paused, unable to say what I assumed was the word “attractive.”

“He’s my pastor,” he finally said. “I think of him like a mentor, you know?”

“Sure,” I said.

“That’s why I was kind of wondering if you would be open to helping me out,” he said.

My cock shot right up. “Oh,” I said.

“I know it’s a lot to ask,” he said. “You can say no and I would totally understand.”

I shrugged. I didn’t want to seem too eager. And it all was pretty odd.

“I could explain it how he explained it to me; take you through it step by step,” he said. “I don’t think it would take super long. And, I mean, the way he described it - I think it would really help me out,” he said.

“Let me think about it,” I said, even though my cock had already decided.

“Yeah, absolutely,” he said, and I could sense some disappointment. “Like I said, I know it’s a lot to ask.”

Maybe it was, but Kyle was hot as fuck with his sandy-haired movie-star looks and muscular build. So after our next workout I told him I was willing to give it a shot. He got really excited.

“Oh, man, you don’t know how much I appreciate this,” he said. “Delilah was even saying last night - I’ve been snapping at her, just totally on edge. I definitely need to do something and I really think this is gonna help.”

He suggested we do it that night, after we went home and showered and stuff. I was honestly nervous - I hadn’t bottomed in forever, and I had a feeling Kyle’s cock was a big one.

He greeted me at the door of his apartment in his cut-off shirt and shorts.

“I can’t thank you enough for being willing to try this out for me,” he said, sounding even more nervous and excited than I was. He looked good, though - clean-cut and toned. “Do you want a drink?” he asked. It seemed like he’d had at least one before I got there, and I had one with him while he described the process as it had been explained to him by his pastor.

“So I’ll go into my bedroom and, you know, remove my clothes. You’ll have to do the same - I hope that’s okay,” he said.

“I assumed I would,” I said.

“Good,” he said. “I’ll try not to look…”

“It’s okay,” I said.

“Okay” he said, letting out his breath. “So you’ll come in, remove your clothes, and then I may need your help with, um, getting excited enough so that we can get started. He gave me a couple suggestions for that,” Kyle said, sheepishly. “So, should we get started?”

“Let’s do it,” I said.

“Great. Give me just a minute,” he said, and headed off into his bedroom. I finished off my drink and took a swig from the bottle for good measure as Kyle prepared.

“Okay, ready!” I heard him say from the bedroom. My heart was pounding as I headed down the hall and turned the corner to his open bedroom door.

Kyle was propped up against his headboard. He had kept the lights off but had lit some candles, and in the dim light he looked incredible, his lithe and muscular body on display. He had a smattering of chair across his broad chest, hair that spread across his tight abs and down to the bush above his cock. His legs were splayed, and just as toned as the rest of him. And in between them stood his cock, just as thick as I’d imagined it to be, not to mention hairy, and hard as nails. Clearly him “getting excited enough” wasn’t going to be a problem, intrigued though I was by the prospect of helping him with that part. His cock was practically vibrating in its need for attention. Below his cock was a healthy set of shaved balls that sat like a wet teabag, the bottom of his sack flat where it rest on the bed.

We didn’t say much as I undressed. Kyle, true to his word, kept his eyes downward, but sometimes I could feel him glance at me, especially when I shucked off my briefs and bent down to slide them off my ankles. I turned to approach him. His eyes went to my erection, but he didn’t comment on it.

“Okay,” he said, sounding rather unsure of himself. “He said we would need something to help get it, um, inside, so there’s some olive oil there on the bedside table. You’ll just apply it to yourself and then to me. And then you’ll sit astride me and begin to, um…well, we’ll get to that, I guess.”

“Okay,” I said, going for the olive oil and drizzling some on my fingers. Kyle glanced at me again as I spread the oil on my hole and pushed some inside. When he saw me noticing him, he quickly glanced away.

I assumed condoms were out of the question given that were weren’t, supposedly, “having sex.” Not that I cared. The idea of taking Kyle raw and possibly taking his load was pretty exciting.

“So now I put some on you?” I said, drizzling more oil into my palm.

“Yeah,” Kyle said, shifting a little as I leaned over him on the bed. His eyes followed my hand as I reached for his cock and took hold of it. I spread the oil along his shaft, starting at the top and moving downward.

“Ah…yeah, that’s good. Maybe a little more,” Kyle said, his voice shaking as I stroked the oil onto his rod. “He said it’s pretty important to use enough of it - for your comfort,” he said. “That’s why I put the towel down.”

“Okay,” I said, pouring more oil on his rod and slathering it on. I kept it quick because it felt like it would have been all over if I’d stroked for too long, which made me wonder: did Kyle really never masturbate? It seemed insane to me, but so much about this scenario was insane anyway.

“So you can get on the bed and sort of straddle my legs,” Kyle said.

“Should I face you?”

“Yes, exactly,” Kyle said, and I got in what I suppose was the pastor-approved position. “So go ahead and take hold of my erection, then you’re going to place it against yourself and bear down until it starts to go inside. He said this is the most difficult part so you should take your time.”

The surreality of it all paled to how turned-on I was as I lined up Kyle’s ragingly-hard cock tip with my asshole and began to sit on it. It took some shifting around at first, but finally I lodged the head of him inside me.

“Is that good?” I said, my ass adjusting to the tip.

 “Yeah,” Kyle said, sounding out of breath. “That’s good,” he added. “When you’re ready you can try to take some more.”

“Okay,” I said, and began to tease the head of him as I adjusted, working my hips in a bobbing motion and taking his thick cock inside my asshole, bit by bit.

“Oh my gosh,” Kyle said when I’d gotten him in about halfway.

“It’s okay?” I said.

“Yeah it’s good,” Kyle said quickly. “I think it should work.”

“Good,” I said. “Oh Go—gosh,” I said, because I’d started taking the fat root of his cock inside me, and it was really stretching me out. “I think it’s all the way in,” I said, reaching down to feel his balls pressed against my ass. Kyle flinched when I did that - I guess hands were off-limits in certain circumstances, so I took my hand away.

“Okay, great,” Kyle said, his voice strained. “Now whenever you’re ready, he said you just kind of move up and down - bounce on it, like you’re sitting on a yoga ball.”

“Like this?” I said, and began to fuck myself on it, starting shallow but taking a little more of his cock in and out of me with each motion of my hips.

“Yeah, that’s good,” Kyle said, looking up at me. “Oh, wow. Yeah I think it’s working.”

We were mostly silent as I got a rhythm going, riding my tight ass up and down the thick length of Kyle’s raw cock. He kept his hands at his sides and let me work. Mostly he kept his eyes closed but sometimes he would open them and our eyes would catch on each other. Each time that happened I could sense his orgasm creeping closer.

“This is working really well,” he said at one point. I wanted to stroke myself so badly, but I sensed it would bring things too much in the realm of “sex” for Kyle, rather than a “technique” to relief his tension. But finally I couldn’t resist; I wrapped my hand around my cock and began to pump. Kyle’s eyes shot right to it, but he didn’t say anything.

We went like that for a while, with just the quiet sounds of his house and the soft suction of his cock plunging in and out of my ass as I took him inside me again and again. A couple times I sensed he was getting close, and I slowed down. I could tell he liked that. Then I was getting close, and I started to speed up.

 “Wait,” he said.

“Is it working okay?” I said.

“Yeah, but I’m just wondering if it would work even better standing up? My pastor said it might be worth trying some different positions to get a better effect,” Kyle said.

“Yeah?” I said, lifting myself off of his cock. “So, like, both of us standing?”

Kyle got off the bed. “Yeah,” he said, positioning himself against his wall. “Get in front of me. Bend over,” he said, with a demanding tone that made my cock throb. I backed up into him, holding his cock and sliding my ass back onto it.

Kyle moaned when I took it deep, but then made it sound like he was just clearing his throat. I had to stifle a laugh at that one.

“There we go,” Kyle said as I began to bounce on his cock again. In this position I was basically letting Kyle fuck me from behind, but of course I was doing all the work, backing up on his dick as he braced himself against the wall. It felt really good.

“Oh, yeah,” Kyle said, an unmistakeable edge of lust in his voice. “This will definitely work. Keep going. Yeah…yeah…” he said, his voice getting higher-pitched with each thrust of my ass onto his cock.

“It’s working, it’s working, oh my gosh,” he said. Suddenly I felt his cock swell and pulse, then felt the unmistakeable sensation of him blasting his load into me. Was it the first time he’d ever fucked someone? Was I taking Kyle’s virginity? I guess it was all up to interpretation. But his shaft enlarged with each shot of his cum, and I just kept working it.

“Yeah, yeah,” Kyle panted. I was so close, all I needed to do was give my cock a couple of strokes and I was ready to blast. I cupped my hand and held it out in front of my rod to catch it.

“Holy—!” Kyle said when he felt my ass squeeze around his rod with my first shot of cum. He seemed to hold his breath as I came, my asshole tightening around his spasming cock with each shot of my load. I kept it up until we were both spent.

“Oh, wow,” he said when I detached myself from him.

“It worked?” I said.

“Yeah,” Kyle said. His big, dripping cock was hanging between his thick thighs, slick with cum. “Even better than I thought it would,” he said, wiping his brow. I had a handful of cum and was doing all I could not to spill it. Kyle noticed. “Oh, did you get some relief too?”

“Yeah,” I said as I dashed into his bathroom to wash it down the sink. “Is that okay?”

“My pastor didn’t really mention that,” he said.

Kyle was already half-dressed when I came out of the bathroom.

“Man, I appreciate this so much,” he said.

“It’s no problem,” I said, slipping on my underwear. “Maybe we could make it a regular thing. Until you get married, I mean.”

“Seriously?” Kyle said. Like the thought hadn’t occurred to him. He scratched his head, his bicep flexing and hairy pit on display as he regarded me. “Are you doing anything tomorrow?” he said.