Nick - "On My Way"

I’m not in the closet, but I still keep my Grindr profile to a single torso pic so guys can see my abs, but not my face. Only because I’ve seen too many people I work with that I would never hook up with, and it’s less awkward to just block them than it is for them to know I blocked them. I have my stats filled out: 5’10”, 145 lbs, white, and I put “slim” because I am on the skinny side, but I exercise at the gym, so my torso pic lets them know I’m more of a fit twink than anything. I keep the rest of my info pretty light. It’s not that I don’t want guys to know what I’m into as much as “what I’m into” changes from day to day. 

I used to mark myself as “versitle” but that was just sugar water for bottoms and for some reason that got me a ton of asshole pics. Also, when I say I’m vers, I don’t mean that I want to flip-fuck; it means some days I want to top, some days I want to bottom. Rather than explain that, I just leave that section blank as well. I did make sure to put in when I was last tested, that I’m negative, and use condoms. 

All of this is to say that my Grindr experience is hit or miss because I flip-flop on what I’m into way too often. I usually get blocked by guys who don’t get what they want right away, and others will block me or stop responding after a few back-and-forth messages.

I moved in with my parents after graduating from college in the spring of 2013 and immediately got a job for the summer in the heart of Cincinnati, Ohio. We live on the outskirts of the city and since I’m a horny 22 year old, with student loans, I refuse to pay for Grindr, which means my grid is always clogged up with the same dozen profiles when I’m at home. Not that it matters because most guys in my neighborhood can’t host, and neither can I.

A few weeks ago, I was hit up by a somewhat older guy in his mid-thirties. He’s black, on the muscular side, slightly hairy torso, but keeps it trimmed, 6’ even, 200 lbs, and he clearly hits the gym pretty regularly. He has longer, chunky braids almost down to his shoulders, with a short, trimmed, scruffy beard. He hit me up and we started chatting during my lunch break at work. We shared pics, his dick is a massive 9” beast with a cut head that thankfully is narrow like a cone rather than a fat blunt tip. I usually shy away from anything bigger than 6 inches, but he was fun to chat with and got me pretty turned on while eating my turkey sandwich. I thought the conversation would end when he asked, “Are you looking for right now?”

Me: No, I’m at work.

GoodTime: When do you get out of work? You’re close by.

Me: Umm, I’m out at 6, but I already told some coworkers I’d go with them to a bar trivia night they do. Since I’m the new guy, I can’t bail.

GoodTime: Cool, hit me up when you’re done.

I went to the trivia night and got shitfaced, completely forgetting about GoodTime and went home to sleep.

I woke up Saturday with a hangover and checked my Instagram, then Facebook, then Twitter, and my texts to make sure I didn’t drunkenly message someone. I have a bad history of doing exactly that and having to apologize in the morning. With no drunk messages, I opened Grindr to make sure I didn’t make any promises to hang out today, while nursing a glass of water and some Advil.

GoodTime: Are you still out?

Fuck, I completely forgot about him.

Me: Damn, sorry, I had a little too much fun last night and never logged back in to Grindr 😕

I didn’t expect to hear from him again. I took a long, hot shower in an attempt to shake my hangover.

Out of the shower, I had a new message.

GoodTime: No worries, you free now?

Me: I am, but I’m recovering.

GoodTime: Oh, did you get fucked last night?

Me: lol, I wish, no, just drank too much.

GoodTime: Been there.

GoodTime: Do you still want to get fucked? I didn’t jerk off last night, so I’m bricked up.

Not really in the mood to do anything, but also still horny from yestereday and having fallen asleep without jerking off either. My dick was responding, though, pulsing along with my headache.

Me: Want to? Yes. Able to? Probably not.

GoodTime: I see. How about tomorrow?

Me: Maybe. I’ll be honest, I’m not always in the mood to get fucked, it’s kinda hit or miss.

GoodTime: I understand. I only ever top, so I’m always in the mood to fuck a tight hole. I have bottomed, but only a few times, and only when all the stars align.

Me: I am about 50/50.

GoodTime: Don’t worry, when you’re with me, you’ll be bottoming.

Me: You’ll have to wait for me to be in the mood then 🫣

GoodTime: Let’s see how you feel tomorrow when you’re not hungover. [sends dick pic]

Me: damn, that looks big.

GoodTime: It is 😈

Me: I think the biggest I’ve taken is maybe 7”

GoodTime: That’s ok, I’ll open you up one inch at a time. I ooze precum, so it helps to lube you up.

Me: Oh, I only play safe.

There was a long pause.

GoodTime: I can wear condoms, but it’s not as good for either of us.

Me: lol, yeah, but I’m not trying to catch anything.

GoodTime: Which is good, I don’t have anything to catch. 😇

Me: Still, better safe than sorry.

GoodTime: Hit me up tomorrow and let me know how you feel.

I ended up not hitting him up for a week. I went out for drinks again with my coworkers and started up my Grindr while in the bathroom, taking a piss, just to see who was on that I might want to hook up with. Getting a bunch of new messages pushed my conversation with GoodTime down further and further, so I didn’t even notice if he was online.

When I got home, I was pretty tipsy and took a shower. Climbing into bed naked with the intention to jerk off. I turned on my TV to mask the sounds of me stroking or any noises that would be interpreted as me stroking and started looking for some hot porn to watch on mute on my laptop. I started stroking to one video, which rolled into another, and another. When a video with a black guy fucking a white guy popped up, I couldn’t help but think of GoodTime and reached for my phone. It was almost 1:30 am, but he had a green dot next to his name.

Me: Still up?

GoodTime: Yeah, you looking?

Me: Kinda.

GoodTime: Looks like you’re pretty far now.

Me: Yeah, I’m at home, just took a shower and was lying in bed, thinking of you…touching myself.

GoodTime: That cute little ass is hungry, huh?

Me: It definitely needs a snack.

GoodTime: Let me wiggle the tip in, that’ll be enough dick to satisfy those cravings.

Me: Mmm…the tip would feel so good.

I started stroking my dick faster.

GoodTime: I’d love to tease and grind on your hole, get you ready for me to push in.

I looked at his profile again, his sexy torso pics, then I scrolled up in our chat to see his huge dick. I dropped a finger down to my hole to tease my pucker while I messaged him back.

Me: That’s so hot, I’m so horny, I’d love to feel you push in a little.

GoodTime: Not yet, I want to eat your ass first, get you nice and wet, loose enough to take more than the head.

I spread my legs wide and took a pick of my asshole and sent it to him.

GoodTime: Mmm, yeah, I’d eat that hole until you beg me to put my dick in. It looks hairless, is it natural or shaved?

Me: There’s hair, it’s not a lot, but there’s hair, I’ve never shaved it.

GoodTime: Mmm, love a natural hole. Tasting you before I slide my tip in.

Me: That’s hot, I can’t remember the last time I had my ass eaten.

GoodTime: Come over and I’ll take care of you. My tongue knows how to work over a tight little hole like yours.

This guy had me dripping precum.

Me: Fuck, I’m so horny.

I kept stroking my dick, spreading my legs as I imagined him eating me out.

GoodTime: You need my cock?

Me: Yeah

GoodTime: Mmm, yeah, I’d spit on the tip and wiggle it on your hole. Let your pucker suck on my head and try to eat my cock.

Me: That’s so hot, I need to feel you in me.

GoodTime: I would push a few inches into you, not too deep, just enough to let you feel it.

I never go bareback, but the fantasy of him fucking me bare was getting me really turned on.

Me: Mmm, yeah, just a few inches, I can handle a few inches.

I started stroking furiously, imagining how good his thick dick would feel.

GoodTime: Once I feel your hole open up, I’m going to start digging you out until I can get balls deep in you.

Me: Oh God, that’s hot.

GoodTime: Don’t bitch out on me, open up that ass and give me full access.

I was getting close to blowing my load.

Me: I won’t bitch out, I promise, just be gentle.

GoodTime: Good, now take this big dick like a man. I want to feel my balls slap against your ass.

Me: I want that too.

I was so close to the point of no return.

GoodTime: Once you feel me in your guts, that’s when I’ll start giving you the full pipe. Hold you tight and give it to you nice and slow so you feel all 9 inches. In and out. In and out.

That did it for me. A few more strokes and I was spurting all over my abs.

GoodTime: Then when you’re ready, I’m going to dump my load in you.

I read that as I squeezed out the last few drops of cum. The horny fog leaving my brain, and just that quickly the idea of a stranger dumping his load inside me went from being hot to being gross. I felt the need to remind him I don’t bareback.

Me: That’s hot, but if we fuck for real, you’ll wear a condom, right?

GoodTime: When* we fuck for real, I’ll wear a condom if you want.

GoodTime: Are you free tomorrow?

I cleaned up my mess and didn’t get back to my phone until he had already messaged again.

GoodTime: Let me know when you’re free, sexy.

We repeated this sexting session for the better part of two months. Once a week, he would indulge my fantasies and let me jerk off to his pictures. Every time, it was a variation of the exact same fantasy. I basically had his routine memorized, but since it was just fantasy, I let him continue with the details about fucking me raw and he would pitch a different way to cum in me every time. Afterward, I would remind him that it was just fantasy and that that particular part wouldn't happen in real life. He seemed to take that as a challenge. As if he could come up with the right scenario that I'd let him do it in real life if I didn't tell him no in writing. 

One time our conversation got so hot that he blew his load before I did and he floated that into our fantasy, telling me, “Your ass is so tight, I tried to pull out in time but blew my load in you.” It had me cumming real quick for some horny reason.

Me: And this is why I don't let you get “a few strokes in” before making you put on a condom lol.

GoodTime: 🤷🏿‍♂️ It was an accident. 

Me: I'm sure it was. 

GoodTime: Don't worry, I have really good control, I've never accidentally popped off inside a guy. 

Me: and yet here we are, and now I'm pregnant 😆

GoodTime: lol, I promise I will only cum in you if you want it. 

Me: 🙄 and inside a condom. 

GoodTime: whatever you want, all I want is to get you off and see you blessed out from my dick. 

Me: I'll subscribe to that.

On Wednesday this week, he saw me active on the app.

GoodTime: You should come over after work Friday.

Me: Maybe.

GoodTime: I’m starting to think you’re bitching out on me.

Me: No, it’s not that…honestly, I’m just nervous about hooking up.

GoodTime: Why?

Me: I don’t know. Your dick is a bit intimidating. 

GoodTime: I promise I’ll be gentle 😇 I am all about your pleasure, it gets me off to get you off.

Me: You promise you’ll go easy on me? I haven’t been fucked in months and your dick would be the biggest I’ve ever tried to take.

GoodTime: Of course. You gotta trust me, though. I know how to work it into a tight hole, but you gotta trust me and let me in.

Me: The other thing is condoms. When we’re just talking dirty on here it’s hot to think about you fucking me raw and breeding me, but I really do only play safe.

GoodTime: Lol, I know. I’ve got plenty of Magnums with your name on them.

Me: What is your name btw?

GoodTime: I’m Caleb

Me: I’m Nick

GoodTime: Look forward to meeting you in person, Nick.

I went to sleep after a quick jerk sesh. I didn’t really think about Caleb at all on Thursday, but on Friday, when I was getting dressed for work, it did cross my mind that I might be in the mood tonight and dressed a little sexier than usual. Some tight chinos that show off my ass, a pair of black briefs, a button up shirt that shows off my tight torso. I told myself it was just in case since I wasn’t planning to do anything.

While at work, I resisted going on Grindr. A part of me was worried that if Caleb were active, he would talk me into going to his place, or worse, I’d have to lie to him about why I wasn’t able to go, and he might block me. 

As the day closed at 6:00 p.m., I lost the battle and opened the app. Caleb was the last person I chatted with, so it wasn’t hard to see he was not active. A part of me was disappointed, and a part of me was relieved.

After work, I went with my coworkers for a drink and some finger food. I drank three Bud Lights in three hours. I was having a great time, but when I went to the bathroom, there was a line. Of course, I took that opportunity to log into Grindr. Sure enough, Caleb messaged me.

GoodTime: You coming over?

It had been more than an hour since he messaged me, so I didn’t expect him to be waiting for my response.

Me: I’m out with some friends having a drink.

I peed and then headed back to our table. The bar was filling up, so I scooted into the corner seat so I could check my phone if I found the opportunity. After a few more sips of my beer, one of my coworkers launched into a work story from before my time, and I got bored, so I pulled out my phone.

GoodTime: It looks like you’re close by, you should come over. [Location sent]

I looked at it on the map, sure enough, he’s only about eight blocks away.

Me: I don’t know how much longer I’ll be here, but I want to.

As soon as I hit send, I started getting that nervous rush.  Questioning if I wanted to go over or not. If I go, I feel like I'm committed to bottoming no matter what mood I'm in. That made me start questioning whether or not I'm prepared enough to bottom, but I know my body well and am confident I'd be good on that front. I started scrolling back through our conversations, reading only the messages he sent, and I was getting turned on.

“Nick, do you want another beer?” my coworker asked.

“Umm, no, I think I’m going to head out,” I told him, nervous that he could read my mind and knew I was leaving to go get fucked by a stranger. 

“Oh really?” He asked again, a disapproving look on his face.

“Yeah, I’m pretty tired, I didn’t get a good night's sleep,” I stretched, trying to sell it.

He rolled his eyes, “Alright.”

I gave him cash for my drinks, told him to leave the rest as a tip, and practically ran out of the bar.

I pulled up Grindr and went to our messages.

Me: On my way.

GoodTime: I’ll be waiting.

Caleb buzzed me in. He is on the first floor, so he opened his door to the hallway right away, and I walked into a warm apartment. He looked sexy as hell. He wasn’t wearing a shirt, and his shoulder-length chunky braids were loose and flaring out like a lion's mane. His basketball shorts showed a bulge that I expected, but his boxer briefs were doing their best to conceal what he had underneath, and it still looked intimidating.

He brought me to the bedroom, which was even warmer and had a distinct scent, a cross between sandalwood and weed. I sat on the edge of his bed. He grabbed a bong off the dresser—it was already packed—and set it on the trunk at the foot of the bed. He took a hit and then offered it to me. I quickly took a big hit to hopefully calm my nerves.

Caleb set the bong back on the dresser and walked over to me, running his big hands through my hair and massaging my head. He smelled clean like soap. His hands cupped the sides of my head, tilted it back, and leaned in to kiss me. He tasted like he had just brushed. It was gentle, sensual, and teasing at times, but very relaxing and sexy to have someone touch me the way two people who love each other would.

He reached down and pulled at the hem of my shirt. I raised my arms and let him pull it off, and then he immediately went back to kissing me. His tongue parted my lips to explore my mouth. It felt so right, almost like he read the book on how to kiss me. I was melting into him from the way his hands explored my body, which was incredibly sensual. It wasn't the aggressive, rushed experience I've come to expect from a Grindr hookup. 

In an eruption of horniness, I wrapped my arms around his neck and tried to pull him down on top of me, but he was rock solid in being bent over me, holding himself from falling onto the bed with me and maintaining his control.

He pulled me up and started kissing my neck; his scruff was scratching my skin, but it was a perfect balance to the pleasure he was giving me with his lips. I couldn’t help but let out soft panting moans. His hands worked over my back, pulling me tight into him, my bare chest against his. His chest hair was also scratching my hairless chest, I was quickly getting lost in the heat of the moment as his hands massaged my back muscles up to my shoulders and then down to my ass, it all felt so good. Everywhere his hands went I found myself leaning into his touch, arching my back so he could cup my ass, spreading my legs in the hopes he’d touch me even deeper. He let his hands roam everywhere and seemed to be memorizing the touch of my body, specifically where my erogenous zones are and what kind of touch got the most significant sexual reaction from me. I’ve never been so turned on by gentle caresses and hot kisses.

He went back to kissing my lips as his hands made their way into the back of my pants and underwear to give my ass cheeks a gentle but firm squeeze, forcing a moan out of my mouth and into his. I could feel his lips denying himself a smile so he could concentrate on working over my mouth with his tongue as his hands continued to grope my ass, an occasional finger tracing over my hole and I instinctively sucked in air in anticipation of the finger entering me. It didn’t, though. I could tell from the sounds he was making and the way he would hold me tightly and restrain his animal instincts to just make me his that he was getting off on teasing me, letting me know that he isn’t just another Grindr hookup.

Satisfied with his hands-on inspection of my ass, he pulled his hands out of my pants and his lips went back to my neck, the other side this time, sucking and nibbling on the sensitive skin as his fingers worked the button and zipper on my Chinos. Pushing them to my thighs, exposing my briefs and the rock hard cock they were barely containing. 

He didn’t go straight to stroking my cock, though. His hands went back around to my ass, rubbing and squeezing my glutes. Letting his fingers trace the elastic along the leg holes until my thighs prevented both hands from going further. That’s when he would grope my ass and pull, pulling me up to my tippy-toes and pulling my ass cheeks apart enough that I felt my hole being tugged a little. Another breathy moan escaped my lips.

His left hand started going down to the small of my back, and his right hand traced up my abs to my neck, where his massive paw gently wrapped around my throat and gave it a subtle squeeze. He broke our kiss as he looked into my eyes to see if this was okay. When I didn’t respond negatively and leaned into it, he grinned, and his tongue lapped at my lips before reentering my mouth, and we both moaned.

I tried to reach for his basketball shorts to touch his bulge, but he denied me. I had barely hooked a finger in the waistband before his hips leaned away, and the elastic snapped back against his taught waist. 

With his hand still on my throat, he broke our kiss and gently pushed me back to the bed. His left hand guided me as he lowered me down. He kissed his way down my chest and abs once he had me flat on my back. His hands traveled down with him to the waistband of my briefs, not skipping a beat as he clamped his fingers on and swiftly pulled them down and off, freeing my cock and legs for him to spread wide.

He stood admiring my naked body, already g grated up and turned on for him, just waiting for him to give me more. He slipped his thumbs into the waistband of his shorts and stretched them out slightly before deciding to drop them to the floor and show off his red Reebok boxer briefs. Then he put a knee on the mattress, lifting my legs high and wide as he dove head first right into my hole.

“Mmmfff, fuck that feels good,” I squirmed under his massive tongue lapping at my hole, clenching his blankets in my fists to keep my arms from flailing like a puppet from the intensity of instant pleasure. His braids tickled my legs in the best possible way, and all I could do was spread my legs as wide as possible to get as much of this pleasure as possible. 

I’ve had guys eat my ass before, but Caleb seemed to have invented it. Licking my pucker, pushing in, licking my inner walls, licking around the ring, rhythmically teaching my hole to open to his touch. “Mmm, holy shit,” I groaned, reaching for my 6” cut dick and slowly stroking myself with my right hand as my left continued to fist the blankets. Not trying to jerk myself to orgasm, I just wanted to add to the pleasure he’s giving me. I know if I cum this early on it’s all over, and after weeks of fantasizing and teasing Caleb, I owe him at least a few minutes of anal before I cum.

He pulled his face from my ass, pulling a basket from under his bed. He had a new bottle of poppers and an open bottle of lube. He ripped the plastic seal off the bottle of poppers with his teeth in one experienced try. Shaking it first, he opened it and took a hit under both sides before passing me the bottle.

In our sexting, he only once brought up using poppers, and I told him I had only ever used them once before, but it gave me a headache, so I didn't try it again, but he insisted his poppers wouldn't do that. So I sat up on my elbows, taking a hit from the fresh bottle as his tongue went back to my crack, licking and drooling. The rush was from the poppers was intense on it’s own but combined with the pleasure of his tongue going into my ass had me arching my ass up to his mouth and leaking precum onto his blankets. 

I took a hit on the other side, and I felt the rush washing over me and relaxed flat on my back as his tongue easily entered my hole, even deeper than before. “Mmm, fuck, Caleb, that feels so good,” I moaned, putting my heels on the mattress and lifting my ass some more for him to get even better access. Rocking my hole on his tongue like my own personal sex toy.

He eventually pulled his tongue from my hole. “You like that?” He asked, crossing the room to where his bong was. I took the opportunity to stare are his semi hard dick stretching the fabric of his underwear. I felt my hole twitch, knowing it's only halfway hard. 

I huffed, “Oh yeah, I can tell this isn’t your first time,” I joked.

He ripped the bong, then handed it to me. I took a big hit and passed it back. He placed it on the dresser, then picked his shorts up off the floor and dug into the pocket to pull out Magnum. 

Knowing he had the condom in his pocket made me feel more relaxed. Then he dropped his boxer briefs to the floor, his semi hard cock flopping out and dangling like a snake in the air. My hole instantly closed back up, undoing all of his hard work as my nerves kicked back into overdrive. He was going to try to fuck me with that thing?

He pushed me to the center of the mattress, my head falling on the pillow which smelled like him, as he set the condom and lube next to me. “Roll over,” said.

I quickly rolled onto my stomach, my heart started pounding, and my nerves kicked into high gear. He spread my legs and started tapping his cock on my hole. The warmth and spongy feeling of his meat felt good against my hole. He slid his cock like a hotdog into my buns, the length of his dick going across my hole and I let out a breathy hum. He repeated it a few times, just teasing my hole. Then he grabbed the poppers and took another hit before passing them back to me.

I took a deep hit, and then another, trying to calm my nerves and reopen my hole for him. I felt him spit on my pucker and his cock head started to circle it as he spread my ass cheeks to really rub it in. I started to relax a little as the rush from the poppers washed over me. He added more spit and rocked his hips, his tip pushing on my pucker until my tight hole won the battle and his cock slipped off my ring and slid up my crack. His balls resting on my balls as he rocked his dick back and forth over my hole a few more times.

His hands held onto my hips, pushing me into the mattress as he started frotting, grinding against my ass, rubbing himself hard against me and panting. It was almost like getting a full body massage but we were both naked and he was contorting my body to use me to rub his dick on. It felt so good I couldn’t help but pant with him and push back against his hot cock. He let his head catch on my hole again and pushed until it slipped off again. Repeating the movement a few times, my hole dialating ever so slightly with each attempt, and fuck it was turning me on. I was nervous about him penetrating me before coming over, but all this teasing had me desperate to feel him inside me.

He didn’t push in, though. He slid his hands up my back, leaning over me as he rocked his dick between my ass cheeks with the full weight of his body. He lay on my back, all 200 lbs of him pressing me into the mattress as he continued his frotting, and I instinctively pushed my ass back against his cock to get as much pleasure out of it as possible. He slid his dick up and down my crack. Every frew slides up and down he’d lift his ass so the head of his dick would point directly at my hole and he’d gently push on my sphincter, it felt so good I found myself trying to open my hole to let him in but he would only let it go as far as parting my ring before he’d let it slide out and over my crack, both of us groaning in horniness but far from satisfied.

His big arms wrapped around my chest and he dug his tongue into my ear, making me squirm and then I’d feel his cock slide over my hole again and my body didn’t know which hole to protect, my ear or my ass and I moaned like a little bitch. Feeling a little embarrased by my high pitched moan I tried to regain my composure, the next time his cock pressed on my hole I let out a more masculine moan. That urged him to push the helmet into my pucker, wrapping my tight hole around his tip, shooting pleasure into my body I moaned out an “Oh fuck.” Unsure if he was trying to push in or if I let him in, my brain was too shattered with pleasure and teasing to connect one dot to the next and form a proper thought. 

When he pushed himself back down my body and landed his mouth right back on my hole I nearly jizzed on his blankets. His tongue went right into my hole like the key to a lock. “Mmm fuck, that feels…nhg…good,” I moaned, once again fisting the blankets under me and arching my ass up to his mouth.

He started aggressively eating my ass as I moaned and squirmed under his invading toungue. Scooping his arms under my legs to pull my ass up onto his tongue as he pushed it in as far as it would go. I did my part to relax and let him, just absorbing all the pleasure I could. I can’t believe I waited so long to let this guy play with my ass. I can’t even comprehend why I would have, it feels so damn good.

He pulled his mouth off of my ass and adjusted himself between my wide spread legs so his cock could tap on my wet hole some more. The heavy thump of his cock reverberated into my ass, teasing all the parts of my body that like to get fucked, drawing a breathy moan from my body. He slid his cock over my hole a few more times, thrusting gently across and back enough to drive me insane with anticipation. I arched my ass up and he spit on my hole, then wiggled the tip of his cock into my pucker. This time, I could feel my hole open enough that only the gentlest of pressure was enough to allow his head to slide into me. He could tell how primed my hole was and he pushed the tip in gently, one milimeter at a time, just watching my ass pulse around the helmet. He didn’t try to push in further, just teasing my hole for a minute before adjusting his angle so a little more pressure pushed against the ring until the head sprang free and slid up my crack again.

“Mmmm, fuck,” I groaned in dissapointment and need.

I heard the cap on the lube pop open as he squeezed some out, the cool liquid poured directly onto my hole and then a generous amount onto his cock. He stroked the whole length of his dick to spread the lube and I thought this was it. So I grabbed the poppers and took another deep hit. His cock head went to my hole, smearing the glob of lube right into my pucker. I took another hit on the other side and as soon as I capped the poppers I felt the head push into my hole, just about an inch before we both felt my ass resisting and he stopped.

The rush of the poppers washed over me, and my hole unclenched enough to let him push in a little more. He only pushed in a half inch more and held it there for a brief moment before pulling out and letting his cock slide between my cheeks again. Now coated in lube, it felt even better as it slid over my hole. He lay back on top of me and started frotting with even more intensity, helping me relax as I let the weight of his sexy body press me into the mattress and hump against me for his pleasure and mine.

He kissed my neck and rocked his hips, pushing the length of his cock against my ass hard each time. It felt so good, like he was imagining being deep inside me, I felt his precum smearing on my lower back as his mouth made it’s way back to my neck, kissing and sucking as his hips rocked a few more times into my ass. “Ungh,” I moaned in heat, pushing back against him. He was grinding small circles with his hips for a minute before resuming his thrusting. I’ve never been so turned on by frotting in my life, but Caleb was enjoying it so much, his enthusiasm was intoxicating.

A few more minutes of humping against me and his arms came up under mine, planking himself on his elbows as I reached around to pull him tighter into me. He grabbed the poppers and took a hit, then another, his hips still grinding small circles into me and I could feel how much harder his dick was now than when we first started. He held the poppers under my nose, pinching off a nostril so I could take a deep hit. “Hold it,” He whispered as his hips arched back and I felt his cock slid down my crack, below my balls. Then I blew it out, he gave me one long stroke, his cock over my hole and then quickly pinched off my other nostril, and I took another deep hit. “Hold it,” he insisted again. His hips started sliding down again, and his helmet caught on my hole. He held it for a second, but as the poppers rushed through my system, my hole relaxed around his head, and I felt him inch a good amount of cock into me. Far more than the head, probably four inches, gently stopping as I groaned and my hole tightened around his girth. We both moaned as he continued holding the poppers under my nose while I tried to take a deep breath to relax around his cock.

He held them under my nose and I took another hit on each side, my head spinning as his cock twitched a few inches deep inside me. “That’s it, Nick, let me in, baby,” he whispered in my ear as I felt a fifth and sixth inch pushing into me.

“Oh fuck,” I groaned, his girth stretching my hole. His bare skin slid easily into my own, the lack of friction turning me on even more. I squirmed under him, feeling that pang of being penetrated, but the pleasure was so good I couldn’t help but want more. I was going to have to remind him to wrap his cock up before he started fucking me. He didn’t push deeper though, he retracted a little and then only pushed in as deep as my ass would let him, both of us moaning as he hit resistance and restrained himself from pushing deeper. Then retracted a little more and pushed in to that same spot, no deeper. “Mmmm, Jesus,” I groaned, letting my horniness takeover and my need to get fucked cranked up another notch. I clenched my hole around his bare cock, savoring the feeling of his skin slick against mine, my heart pounding as I tried to find my voice and tell him to put a condom on.

I spread my arms under the pillow in front of me, pulling my face tight into it as I tried to breathe through the pangs of being stretched wider than I’ve ever been stretched. Caleb started kissing my neck and holding my body tight like he had while we were frotting. I couldn’t help but lift my head to give him better access to my neck which naturally arched my ass up a little onto his cock as the next gentle thrust pushed him the tiniest bit deeper into my hole. “Ngh…oh fuck,” I panted in pleasure. My head flopping down onto the pillow, I inhaled his scent from the soft, silky fabric. He rocked his hips again, this time a solid seven of his thick inches pushed into my hole, hitting as deep as any man has ever gone, and the pressure had me hiss and wince in discomfort.

“Just relax, baby, just relax, I won’t go any deeper until you’re ready,” he whispered in my ear, holding me tight and making small circles with his hips, his cock stirring my insides like a paint mixer.

“Mmm,” His movement inside me quickly took away that sting. Gently massaging my insides, even though I wasn’t ready for more inches, the ones in me had me feeling like a king. “Fuck, you’re so big,” I huffed.

He rocked his hips out, most of his inches pulling from my ass and I expected him to push back in but then his tip popped out of my hole and his cock slipped between my ass cheeks again, sliding all of his inches across the rim of my hole and we both let out a sigh of relief.

He sat up on my legs, tapping his cock on my hole, he added more lube and then reached up by my face, grabbing the gold wrapped condom, and it really sank in that he had been in me raw up to this point. All of that delicious pleasure was his bare cock sliding into me. I knew it while he was in me, but seeing the condom made it real. I sat up on my elbows to watch him tear open the wrapper and roll the condom down his shaft, adding lube to him and me, continuously stroking himself to stay hard.

I grabbed the poppers and took a big hit. Knowing he has the condom on I know I’m about to get fucked for real. I took another deep hit and he lined his cock up with my hole and started to push in gently. Slowly sinking one inch, two, three, until he was right back to that spot of resistance. “Mmmm,” I hummed as he spread me open, the tip trying to push a little deeper but not with enough pressure to actually get in. He leaned on his arms at either side of my shoulders and started stirring his cock inside me again. The condom straining to stretch to his girth as much as my asshole was, the feeling inside me not as great but knowing he was wrapped up made me feel better mentally.

He thrust into me a few times, just those seven inches, not pushing deeper until he could tell I was no longer straining to take him. He hooked his arms under my shoulders again, resting his torso on my back and took a hit of the poppers, then gave me a hit, stirring his cock in me the entire time. Another hit on the other side, and then he started kissing my neck as his legs adjusted around my hips, and he pulled my shoulders as he slowly hunched those last two inches into my inner ring.

“Ungh…fuu–ck,” I groaned and panted. My inner ring was virginal until now and holy fuck does that sting. 

“Just breathe,” He held himself there, kissing my neck. I turned my head so he could kiss me as my body adjusted to having a thick cock in my guts. He didn’t pull his cock back but he did grind it deeper into me, trying to tease my inner ring open the same way he did my hole. “Fuck, ungh,” I whimpered as he dug even deeper into me. I felt my heart pounding out of my chest. 

“You’re so tight,” he said, kissing my neck. “Mmm,” he grind deeper, “it feels so good,” he circled his hips, his pubes tickling my ass like the rest of the hair on his body and face. 

He kissed my neck some more as his hands worked down to my hips and pushed my waist down into the mattress so he could grind into me the way he was frotting against me earlier. Fulfilling his fantasy of being deep inside my tight hole as I moaned and squirmed under his cock, spearing me deep and grinding into my guts. A feeling I’ve never experienced before, but now it’s radiating pleasure into my intestines and, “Mmm…fuck,” I can’t help but moan each time that last inch rocks into me.

He started rocking his hips to get bigger thrusts, testing the water at first to make sure it didn’t hurt me, and once he heard me moan in pleasure, he started picking up the pace. His cock making love to my hole wiht gentle but firm thrusts. Half of his cock pulled out and then he’d thrust deep into me and hunch those last two inches deep into me, eliciting a higher pitched moan each time. “Fuck that feels so good,” I whimpered. The thickness of his cock had my body weak and wanting to just receive the next thrust. 

I was exhausted after a ten-minute stretch of constant thrusting in and out. My toes curled every time those last two inches broke into my inner ring, and I’d let out that higher-pitched moan that made me feel more vulnerable than ever as precum dripped from my semi-hard cock. Trying to absorb as much of his cock with each thrust, I’d curl my legs up and hook myheels on his ass cheeks, pushing him deeper into me and groaning when he hit that spot. “That feels…mmmm…so good,” I cried in pleasure.

When he felt he had sufficiently dug me out in this position, he flipped me back over onto my back and pushed all nine inches into me. Folding me in half so he could get those last two inches into me with minimal resistance, and only pleasure for me. He kissed me and we made out as he fucked me with passion. His hips slamming gently into my ass, the smacking noise bouncing off the walls, his fucking slowly swinging towards a focus on his orgasm.

He rolled back onto his back, and I was on top of him. I was pretty worn out at this point but I tried my best to ride his dick, his hips meeting my ass on the down stroke so I didn’t pull off when his head hit my inner ring. This position definitely hit different, and I felt myself getting close to blowing my load. “Oh shit,” I groaned, riding him with more grinding and less up and down. “Oh fuck that feels good,” I moaned.

I tucked my knees in just above his hips and started riding him more aggressively, rocking my hips and grinding harder against him. Feeling his dick deep in my guts having now stretched my inner ring enough that it didn’t sting anymore, “Mmm, ahhh,” I moaned, biting my lower lip and throwing my head back. He pulled my hand off my dick and started bucking up into me so I fell forward a little, bracing myself on his chest as his hips started slamming into my ass. The loud pat, pat, pat, echoing through the room loud enough to make me self-conscious, but my groaning to the onslaught was equally audible. “Ahhhh shiiiiiit,” I moaned for a long stretch of him slamming into my hole from below. I tried to slow him down by riding him, but he ended up bucking me up and letting me slide back down his shaft enough to do it over and over again in rapid succession. “Fuuuuuuck….unghhhh,” I growled as he held my hip and ground up into me, the intensity was draining my soul out as he hit a new depth in my bowels, pounding my prostate with each thrust. I collapsed onto him and let him really go for it, focusing on his orgasm instead of my own. 

He noticed my transition to focus on getting him off and rolled us back over, folding me in half, my ankles up by my head, he started kissing me deep as he burried his cock deeper into me. A slow, long stroking where he pulled out until all but the tip was out and then gave me all of his inches until his hips slammed into my ass. Not fast, just powerful thrusts that felt so good. I was a rag doll at this point. My orgasm was both on the edge and nowhere in sight because I was so overstimulated from his vigor. He could see that I was fucked out and gave me a few more deep thrusts, grinding with each one and then kissed me sensually before pulling out.

“You good?” He asked, concerned.

I let out a breathy chuckle and nodded, “Oh yeah.”

He stayed between my legs, pulling off the condom, and started stroking himself. I followed his lead and started jerking myself off. I took a bit for me to get my erection back; his pounding really took a lot out of me, even though it felt so good. He scooted back up between my legs, put his cock head on my hole and started jerking himself just inside the ring. The slight pressure felt good, really good. The heat of his cock soothed my stretched asshole. He spit right down on his cock and used the tip to push the saliva into my hole and his teasing felt even better than before.

I stretched my legs around his waist and pulled myself onto him just an inch, and that was all I needed. I rocked my hips up and down gently on his bare tip, and it pushed me over the edge. My balls tightened and my abs clenched, my hole clamped down on his cock head and spurt after spurt of cum landed on my torso. I was spent.

He grabbed the rag he used to wipe his hands earlier and wiped my cum off, setting it aside. Then he flipped me over onto my stomach and started grinding his cock against me again, frotting like before but with the goal to get himself off now. He lay flat on my back and humped harder against my ass, faster, then grinding tight against me like he did when he was deep inside me and I weakly arched my ass up to meet his thrusts instinctively.

He was groaning and panting in my ear, then I heard him wipe saliva onto his palm and reach down to lube up his cock, and pointed it at my hole, sliding it up and down my crack again. He took a dramatic pause, then added more saliva, getting his cock nice and slick. He started arching his ass high so his tip dragged across my hole, catching easily now on my hole, and then sank an inch into me. The sting of that inch catching my hole by surprise sent a dull pang into my guts.

“Ahhh, fuck,” I winced and clenched. I reached for the bottle of poppers taking a big hit to kill that sting, then another to dull the burn of his cock entering my hole post orgasm. He reached under me, grabbing my shoulders, and pulled himself deeper into me. I could tell by how easily he slipped in that he hadn’t put the condom back on and was balls deep in me, raw, stretching me to the limits. “Oh fuck, ungh,” I groaned as he pulled himself most of the way into me. Then he pulled out a bit and then hunched up into me again. “Ungh, fuck, Caleb,” I groaned. Then he pulled himself deeper into me, those last two inches punching into my inner hole and I yelped, “Oh fuck, nghhh.” I was fucked out and exhausted, and getting caught up in the heat of the moment as his thrusting was no longer for my pleasure but to get him a long overdue orgasm.

He panted in my ear, thrusting again and again. Each time he pushed those last two inches into my inner hole, it hurt like hell, but felt so good at the same time. He thrust again and hunched even quicker, then again even faster, and one more thrust that came with a heavy grunt and I felt his cock twitching inside me as he held himself deep in my guts. The heat of his cum shooting into my stomach was undeniably hot, the swelling of his cock stretching both my holes to the max as he pulsed inside me and pumped shot after shot of jizz into me had me moaning in pleasure. I clenched the blankets in my fists as I felt a trembling inside me, almost like I could feel his pleasure through osmosis. He grinds his hips harder into me, hunching up into me to a new depth. His body shudders, and his orgasm finished with a grunt. His entire body relaxed on mine with a groan of pleasure.

“Fuck,” I sighed, catching my breath now that his cock wasn’t swelling to twice it’s natural size and stretching my guts to the limits.

“Shit,” He agreed, slowly pulling his spent cock out of my hole and rolling off of me, breathing heavily.

I lay there, completely destroyed in all the best ways. Fucked to my core, with his cum deep inside my guts. I panted and slowly rolled over onto my back. He rolled onto his side and cuddled me, rolling me onto my side so his soft cock was against my ass. The warmth was comforting. 

My brain started going into a complete panic having just let a guy I technically just met fuck me raw and cum inside me. I tried to rationalize it since it felt so good, and I had been talking with him for weeks. I felt like I could trust him. It just felt right as we lay there letting our bodies recover and our breathing return to normal. After a few minutes of quiet, calm bliss, I dozed off.

I woke up to his alarm going off. He got up, showered, and then made breakfast.

“I’m going to the gym,” he said, with a tone that implied I needed to leave too.

“Oh, right,” I said, sitting up. My legs are wobbly from last night, but I manage to dress quickly.

When I got home, I had to suffer the embarrassment of seeing my parents making breakfast as I did the walk of shame. My mother played like she didn’t know why I was up so early and insisted she make breakfast for me too, “since you’re up.”

Thankfully, after breakfast, my parents went out to run errands, and I went to bed and passed out.