29. Jake
Chapter 29
Jake
S urely, I didn’t hear him right. I pull back, searching those blue eyes I love so much and I see him fighting to not look away from me.
“I’m not asking you to change, Dylan.” Do I want to sink into his tight ass? Hell, fucking, yes, I do. But not at the cost of extreme inner turmoil or an existential identity crisis.
“I know, but I’m trying to embrace some personal growth,” he jokes.
“And you think having my cock in your ass is the best route to take for that growth?”
“Are you trying to talk me out of it? Because if you don’t want—”
I cover his mouth with my palm, holding him to me with my other hand. “Don’t even finish that fucking sentence. Of course, I want to experience this with you, but there’s a lot going on in our lives right now. Do you really want to add processing losing your ass virginity to the mix?”
This gets a laugh from him.
“Let’s continue this conversation in the car. It’s getting cold and I think we should count our blessings that we haven’t been caught out here yet.”
“It’s just a big step,” I explain, clicking my seatbelt back into place.
He gives me the side eye. “I know how anal sex works, Jake.”
“Correction. You know how topping during anal sex works, Dylan. Bottoming…well, enjoying bottoming, takes a level of knowledge and comfort with yourself that I’m not sure you have. Not to mention, a level of comfort with me that I’m not sure one blow job — regardless of how good it was — has achieved.”
I’m trying to be honest, not discouraging, but I can tell he’s in his head, so I try again.
“Look, I want nothing more than to take this step with you and if you’re sure you’re ready, then I’m all in. I just don’t want it to be something you regret. This is a lot of first steps in one night.”
He chews on his bottom lip as he stares at the road, only visible in the beams of the headlights. His speed is controlled, well within the speed limit. His shoulders are relaxed, but his eyes are alight with excitement, like he’s a kid on Christmas Eve.
“I want to do this. I want to do this with you . And I want to do it tonight.”
“What’s the rush, baby? I’m not going anywhere.” I rub my hand back and forth across his thigh for reassurance of my presence.
“The rush is because I’m ready. My body craves you… I crave you…in a way I’ve never felt before. Back there, just now, I loved having you inside my mouth. Bringing you pleasure like that was a heady feeling. And now I want to try this.”
I pull my hand back to rub along my jaw, while my other adjusts my growing cock in my pants. The prospect of sinking deep inside him is overwhelming. I didn’t last long with just his mouth wrapped around me…I can’t imagine—
A low groan escapes my parted lips without my permission.
Dylan looks over and sees my hand trying to tamp down this erection. Getting hard again after just coming so violently is actually painful.
“Your cock seems on board with my plan,” he says, not trying to hide his haughty smirk.
“Yeah, well, my cock has an invested interest since your plan directly affects him.”
“You said you’d give me whatever I want,” he says seriously.
“And I meant it.”
“Well…I want this. So much is changing in my life and in some ways, it feels like I’m losing everything I know. I need to feel like I can control some of that change and I need to feel like I’m gaining something too.”
“And my cock buried in your ass will give you that control?” At this point, I know it will, but I keep asking questions to make sure his line of reasoning is sound. He’s fighting a lot of demons and there’s no better weapon to do that with than the truth. Breaking through cultural norms and schemas you’ve believed your whole life is no easy feat.
“Yes. While I was on my knees, I realized I’ve had it all wrong, or rather, the beliefs that were ingrained in me from a man I respected were wrong. Being the receiver doesn’t make you powerless. It makes you the greatest source of pleasure for the person you love and that is power ful. ”
I understand what he means all too well and I’m so damn proud of him for arriving at this conclusion, so blowing out a deep breath, I commit to fulfilling his request.
Doing this with him tonight is a really big fucking deal and my mind is in overdrive working through a few details.
On our way back toward his house, we pass a drugstore.
“Can you pull in here?” I ask almost too late. It’s a little after nine, but their light is on and their hours say they’re open until eleven. He pulls into a space and my door is already open. “Wait here, I’ll be back in a minute.”
“Why can’t I come in?” he argues.
“Do you trust me?”
He purses his lips at me and cocks his head to the side, clearly meaning duh .
And while that look might not mean shit for a lot of people, it makes Dylan’s point perfectly. I lean over the console to kiss him.
“Then wait here.”
He doesn’t need to see the lube, the Gatorade, or the butt plug I’m about to purchase.
I’m back in the car in under ten minutes and he eyes the bags now resting on the floorboard between my feet.
“You gonna tell me what’s in there?”
It’s my turn to smirk. “Nope.”
He pulls back onto the road and follows the signs for the highway. “I thought we’d better head uptown to your place for this…for obvious reasons,” he says, looking over his shoulder as he merges into light traffic.
“I was actually thinking we should grab a hotel room.”
He looks over at me with furrowed brows. “Really? Why?”
The need to touch him constantly has become my norm. I rub my hand along his biceps, down to his forearm, and back up again, craving the feel of his inked skin under my hands.
“Because I don’t want to do this in my space. I want to do this on neutral ground. Some place neither of us has memories of someone else. A place where there’s no possibility of someone stopping by to interrupt us. A place where we can truly shut the world out and focus solely on each other.”
He nods his head and licks his lips. “Yeah. Okay.”
I fire off a text to Charlie, letting him know Dylan and I are safe, but won’t be back until the morning and then I make a reservation at the Hacienda Gótico, an upscale hotel I’ve passed several times, but have never had a reason to stay since it’s local. With an average of four-point-eight stars out of seven thousand reviews, I feel pretty confident it’s a good choice.
The architecture reminds me of the older buildings in a small town called Puebla, Mexico. A place I visited several years ago with a group of friends in undergrad. The pictures online show that the rooms are done with a light Mexican gothic theme and they remind me of Dylan’s tattoo.
Most hotels these days have a chat box feature that connects you to the front desk. Since my requests are specific and on such short notice, I begin typing.
Guest: Good evening. My boyfriend and I are in need of a hotel room at the last minute. I’m searching for a garden-view room, preferably on the end or corner.
On a random Wednesday in September, I don’t expect to have much trouble and am relieved when the message comes through.
Hacienda Gótico: Hello! Thank you for reaching out to us. I am pleased to inform you that we can accommodate your request. If the room selection below is satisfactory, please click the link to proceed and complete your booking.
I click the link for the Corner Suite with Garden View and Balcony and fill out the form. There are add-ons on the last page. I select a bottle of Dom Perignon and the room-service breakfast. I’m tempted to click all the damn buttons, but Dylan isn’t really a roses on the bedspread kind of guy.
I check out and give him directions to our new destination.
Check-in at the hotel is easy and since this is totally impromptu, we have no bags except for the ones from the drugstore. I chuckle because it’s pretty obvious what we’ve come here to do, but the staff is nothing but professional, welcoming us with smiles.
A lot of older buildings in Mexico aren’t much higher than five stories, and true to its heritage, this building only has four. It’s open in the center to a courtyard that houses the tables and chairs of the restaurant. Hanging baskets, fountains, and small pools create an authentic, intimate feel. The cast iron railings of the balconies facing the courtyard are visible from the lobby and I feel good about my choice of an exterior facing room.
We’re riding the elevator up to the fourth floor when Dylan realizes, “Shit, I don’t even have toothpaste.”
I smile and hold up the heaviest of the bags in my hands.
He smiles at me from across the elevator. “I love a man of action.”
Since my hands are full, he unlocks the door for us and stops just over the threshold, causing me to run into his back.
“Is everything okay?” Concern laces my voice.
He doesn’t answer, but continues to walk forward ever so slowly. I set the bags down on the small bench and crowd into the room behind him, finally seeing what he sees.
It’s better than I could have imagined. A deep red — almost black— patterned wallpaper gives the room a sensual feel. A cream-colored duvet is on the king-sized bed and matching cream curtains frame the doors leading to the balcony, but what’s caught his attention, immediately has mine as well.
On the far wall, facing us as we enter, is an incredible print of a face painted for Dia de Los Muertos. The person in the picture is a man, but I feel his connection to it nonetheless. A popular aspect of Mexican culture, the aesthetic surrounding it is embodied well by this hotel, and this room. Roses matching the color of the wallpaper are in a black vase on a shelf above the T.V. There are two chairs with a small table between them and my mind conjures up an image of Dylan sitting on my lap, sinking down onto me. The height of the chair would allow him to keep his feet on the floor which means more control for his speed and my depth.
“How’d you find this place?” he whispers, eyes still glued to the framed picture.
“I’ve passed it several times. Always wanted to stop in, but never had a reason to.” I wrap my arms around his waist and kiss his neck. “Until now.”
A horrible thought suddenly occurs to me.
“Oh, fucking hell. Did I mess this all up?”
Perhaps since his heritage and cultural expectations are the particular demons he’s trying to overcome, choosing this place wasn’t the smartest idea. Like, here baby, since you’ve never allowed a man to fuck you because your Mexican grandfather was ashamed of you and convinced you only weak men take it in the ass, let me bring you to a place that shoves it right in your face.
Jesus Christ, what is wrong with me?
I’m ready to yank him from the room when he spins in my arms and runs his hands along my back. “This is so fucking thoughtful. I love it and I don’t want to run from it anymore. It’ll be a good reminder that who I am is a Mexican American man with an incredible boyfriend who I love and trust and one of the ways I show that love and trust is by opening myself up to him. So, no, you didn’t mess anything up. This is perfect.”
Relief floods my veins as I remind myself this is supposed to be about him .
I nod, kissing his lips before issuing instructions. “Here’s what I want you to do. I rummage through the bags of items I bought and hand him the bottle of lube before going over all the unsexy things I want him to do to himself in the shower in the next however-long-it-takes. “The more comfortable you are the better the whole experience will be.”
“Doesn’t this kind of kill the mood?” he asks, hesitantly reaching for the bottle of lube.
I push him backwards so hard he falls onto the bed. While he’s getting his bearings after the abrupt shove, I climb on after him, stripping my shirt over my head. Tucking my legs like a frog beneath me, I place one hand lightly around his throat, one hand on his pec, and rut my hips into his until I feel him getting hard in his jeans. Through his shirt, I tweak his nipple with the hand over his pec and smile when I feel his hips push up into mine.
Using both hands, I slide his shirt up his torso until he takes over and pulls it off, allowing me to lean down so our bare chests are flush against each other and fuck does he feel good.
It’s hard not to lose my mind when I’m on him like this, especially when his hands grip my ass, encouraging the rhythm and pressure he wants on his dick. But coming in our pants isn’t the end goal tonight. I tease him by hovering my mouth half an inch from his, backing away when he sits up to kiss me.
“Damn it, Jake,” he pants, fully turned on.
“Are you satisfied that I can get the mood back once you’re done in the shower?”
His head drops back on the bed and his erection is still grinding against me. “Oh, you asshole.”
I slide off of him, chuckling. “Go do as I said because I plan to fuck your ass so well, you’ll be begging me to do it all night. I can guarantee you’ve never come as hard as you’re about to.”
Thirty-two minutes later, I’m leaning on the railing of the balcony on my forearms, my hands hanging loosely over the edge, looking down into the quiet, urban garden, when I hear the bathroom door open inside. It’s a nice evening, fall’s cooler temperatures have really settled in since the moon has been out for a while.
I turn to go inside and find Dylan in just a towel. Small beads of water are still trickling down his chest in a slow cascade like they’re hesitant to leave his body.
“God damn, ” I breathe when seeing him. He’s a work of fucking art. “Come here.” I hold my hand out for him as I walk toward him, wanting to take my time, but feeling the sense of urgency growing within me.
I grab his wrist and he allows me to pull him to my chest, but as soon as we collide, I walk him backwards until he’s flush with the wall.
He glances over my shoulder at the bed and I see the worried expression on his face at the towel I’ve laid out. “It’s for all the lube I’ll be using,” I reassure him, already knowing where his mind has gone. “It stains and while I’m happy to pay the cleaning fee, it’s also easily avoidable with the towel.”
“Okay,” is all he says at first, but then he adds, “Why are you still dressed?” The question comes out annoyed more than playful and I pull back to look at him.
“Because as soon as I’m naked I’m going to want to be inside you and we’ve got a few bridges to cross first. It’s better if he stays caged for now.” Dylan’s shoulders relax. He thought I was changing my mind. Deciding it will be better to prove my intentions with actions instead of words, I rip the towel open and let it fall to the floor. I run my hands down his chest and over the ridges of his abs. “You have to talk to me, Dylan. You have to tell me if it’s too much or if you want me to stop.”
“I will,” he agrees, panting against my lips.
“Did you follow all my instructions?” I ask slowly.
He nods.
“Words, baby.”
He rolls his eyes and grits his teeth. “ Yes .”
I smile, realizing his nervousness is shortening his temper. I can tell he wants to get right to it, but that isn’t how this is going to work. I plan to have him so turned on and so ready for me, he’ll wonder what all the fuss about the pain was.
“Good.” Without warning, I rip him off the wall, pushing him toward the bed with my free hand on his shoulder blade.
I’ve never been someone’s first top before. I was a little afraid my dislike of calling the shots in the bedroom would make this difficult, but the opposite seems to be happening. His need for this is making my ability to control the situation clear and confident. Knowing he’s traditionally thought of the bottom as the weaker partner, I’m rough with him now to prove he’s just as strong as he’s always been, regardless of whether he’s taking cock or giving it.
He lands on the bed, already short-tempered from his nerves and spins on me, pushing back against my shoulders.
“You could’ve just asked me to get on the bed,” he seethes.
I give him a cocky smile. “I’ll be gentle when the time comes, but right now isn’t it.” I flip him onto his stomach, straddling his thighs and smack him across his ass before rubbing my palms along the skin to soothe the sting.
He bucks under me, pushing up on his hands, trying to twist so he can face me. I bear down on his legs, but his extra mass wins and he knocks me off to the side. Thankfully this bed is big enough for these games.
He rolls with me, pinning me to the mattress, with my hands trapped between my legs underneath his body.
Just like I wanted.
He’s now straddling me and if I flex my wrist, my middle fingertip will hit its mark. Physiologically, the fight or flight response elicits the same reaction in the body as being turned on. I want him to fight me so his elevated heart rate pumps increased testosterone through his veins, adding to his lust, dulling his nerves and numbing any pain.
“Kiss me,” I whisper. Come on, Dylan. Lean forward. Open yourself up for me.
He only hesitates for a second before leaning forward and sealing our mouths together as his hands dive into my hair. He groans and I move my finger into place, applying pressure on the outside of his hole.
He jerks, but doesn’t pull away.
“That’s it, baby, relax into it.”
“Are you topping me from the bottom?” he asks against my mouth, making my smile widen.
“How about we forget about labels and roles and norms and expectations, and we just fuck like two guys in love?” I ask, all the while, rubbing small circles along his puckered flesh to get him comfortable with sensation.
By the time he agrees, he’s pushing back onto my finger a little.
Knowing he’s enjoying it thus far, I wrap my legs around his torso and roll us — gently this time — so I’m back on top. I quickly scramble off his legs so I can spread them and push them in the air while I lay down on my stomach.
One swipe of my tongue across his asshole and I know I’m done for.
“What the fuck are you doing?” he barks, trying to pull out of my grip. He’s not successful though, because the short fight pumped my own muscles up and now that I know what he tastes like, no fucking way is he getting away from me this time.
“I’m eating your ass. What the fuck does it look like I’m doing?”
I wrap my hands around his quads, locking him to my face as I continue my assault while he tires himself out. Once he realizes he’s lost the fight, I loosen my grip on his legs and spread his cheeks wider.
“Jake…I don’t think… ohhh shit …I’ve never… fuck …are you sure you…oh wow…that feels…”
While he keeps rambling, I gather spit in my mouth and aim it right at his asshole. Maybe I should keep it PG but goddamn he makes me feel dirty in the best way possible and I want him there with me.
“ Did you just…” he starts.
I spit again and bury my tongue inside him this time.
“ OH FUCK! Oh, goddamnit. Jake…” Finally, he gives in the way I need him to. “Fuck it. Give me more.”
I cut my laugh off before it can leave my mouth because this position is already vulnerable enough. It would be way worse if the person whose face was buried in your ass started laughing. I listen with rapt attention as his words go from panicked to resigned to enjoyment, as is the normal progression of ass play in my humble opinion.
Knowing it’s getting close to time for me to sink something other than my tongue in him, I hop off the bed and shimmy out of my clothes. Not wanting to give him a single second to let his thoughts get away from him, I lay back down and dive back in, trying to keep the pleasure train rolling.
This time, I sit my own ass back on my heels to create a small amount of space between my chest and the mattress while I keep assaulting Dylan with my tongue. I flip the cap to the lube open one handed, pass the bottle to myself under my chest and pour a healthy dollop on my fingers.
Then, pulling my head back ever so slightly, I make room for one finger to penetrate him, making sure a good amount coats both he and I. I run my finger around the outside so he knows it’s coming. His breathing is so loud and heavy, I know he’s turned on as hell.
Sitting up a little straighter, I grab his cock in my left hand and begin slow pulls as my right middle finger finally breaches him.
And oh my fuck. I should’ve made myself come while he was in the shower because no fucking way I’m going to last more than twelve seconds inside him. My dick is drenched in pre-cum just from the way he’s gripping my finger.
“D…Dyl…Dylan.” It takes me three tries to get his full name to fall from my lips. “You have to relax baby, or this is gonna end before it starts.”
“It feels so…” I wait with baited breath for him to finish the sentence. “…so fucking good. ”
My heart soars. I’m doing it. I’m making this scary leap good for him.
“That’s it, just keep talking to me,” I tell him, before adding more lube and another finger. “How’re you doing?”
“I’m okay,” he replies, relaxing even further. He’s keeping his eyes closed and although I wish I could see those blue irises staring back at me, I want him to stay however he’s most comfortable. I repeat the process and work him up to the plug I bought which is slightly thinner than me, but since actual skin and spongy tissue compress more easily, I figure my own girth will feel similar inside him.
Keeping my movements slow and steady, I work him over until he no longer seems in control of his hips as his own weeping cock seeks friction. Every push of the plug against his prostate has him moaning and writhing beneath me, giving in to the pleasure and forgetting about the bullshit.
Meaning it’s go-time.
I squirt a literal fuck-ton of lube onto my shaft and give myself a couple easy strokes to ease the pressure, careful not to blow my load and ruin the last forty minutes of prep work.
“Last chance, to change your mind baby, because once I start, I’m going to plant a flag so deep in your ass, you’ll never fucking forget who was here first.”
“Yes… please. ” He moans, finally opening his eyes, almost paralyzing me with that shock of blue against his sweat coated face.
Nudging the head of my cock against his entrance, I feel him tense in anticipation before he exhales and allows me to come home. However, as a natural result of being invaded, his ass clamps down on my dick to halt my progress. Stopping my forward thrust so I don’t hurt him is the hardest thing I’ve ever done — literally.
“Are you okay?” I ask again, fighting tooth and nail to not give in to the pleasure being inside him brings. I inch my way forward by millimeters singing the alphabet in my head so I don’t come on the spot.
“I think so,” he answers. His wince almost makes me stop again, but that would be cruel seeing as I’m now at the widest part of myself.
“Take a deep breath for me,” I instruct, knowing once we get past this, his body will no longer rebel against me, but rather pull me into him. On his exhale, I place a comforting hand on his lower abdomen and nudge my hips forward ever so slightly, feeling him take me in.
He throws his head back on the pillows behind him, his eyes screwing shut again. “Ay dios mío,” he mutters, moving his arms around in the sheets like he’s not sure where to put them.
I grab his right hand and lead him to his own dick. Eventually, I’ll do this part for him, but it’s taking all my concentration to support his legs, help him stay relaxed, and control my thrusts.
“Eres jodidamente enorme.”
“I love when you speak Spanish, but I don’t understand a word you’re saying, so if you’re telling me you need a minute, or that my cock is too small and you can’t feel anything, I need you to switch back to English.”
“I said you’re fucking huge .”
I grin down at him. “Well, that’s not anything you didn’t already know,” I tease, starting to work my hips forward and back in a short range of motion. The smile he gives me in return runs the serious risk of stopping my heart in my chest.
“True, but it’s different when I’m taking it up the ass,” he grunts, starting to tense up.
“Okay, joke’s over. I need you to relax again. You feel so fucking good, baby.” One more push and I’m seated inside him all the way to my balls. My dick jerks in response to the depth and Dylan shudders.
“That feels amazing.”
“Are you okay if I move a little faster?” As soon as he gives his consent, I add more lube, making sure everything stays coated in the thick gel. I place his calf on my shoulder, freeing up a hand so I can jerk him off while burying myself inside him.
“Oh, holy shit, Jake. There’s pressure everywhere,” he pants between breaths.
“Let it build,” I tell him, gripping his thigh with my other hand for leverage as I pull myself into him. “Don’t fight it.”
Every time I talk, I feel the small adjustments his body makes at the sound of my voice. His shoulders relax, he takes a deeper breath, his hips rise to meet mine. Wanting to test a theory, I dig really deeply and try to climb a little further out of my own shell by saying all the shit I’m thinking out loud while still pulling on his shaft.
“You take my cock so well, Dylan. Fuck, it’s like your ass was made just for me. I’ve never felt this way in my life. You’re fucking perfect. All smooth, hard muscle, bronze skin, and the strength to take me head-on. I’m going to fill your sweet ass full of cum.”
His breathing increases and I’m barely holding back anymore as I piston in and out of him. My climax is rapidly approaching, but so is his and if I back off, I’m afraid his will too.
“Shit, Dylan, I’m close. Too close. This tight ass has me barely holding on.”
“Then let go.”
I thought I had maybe another minute in me until he raises his head, locks his eyes on mine and says, “Fill me up, Jake. Mark my ass like you promised. It’s yours.”
I feel the head of my dick swell just before my balls release inside him. With every spasm of my dick, I pull harder on his cock until he cries, “Oh fuck, I’m coming too.”
His abs contract, bringing him toward me. With every wave of his pleasure, he bears down on my sensitive cock inside him, leaving me panting and gasping for breath until his own spasms subside and my hand and his stomach are covered in cum.
We lay in silence for a beat, my dick taking longer to soften than usual.
“I didn’t think I’d actually be able to feel you come, but I definitely did,” Dylan says, processing out loud.
“Did you like it?” I ask hesitantly. I know it’s a loaded question and probably not fair to ask until he’s had a chance to really sit with it for a minute, but the insecurity in me needs an answer.
“Yeah, I really did, but I think that has more to do with the fact that it was you inside me and wasn’t just because it felt good. But, damn…it felt good.”
I smile and start to pull out of him.
“Don’t move,” I tell him, repeating the same words he spoke to me the first time we ever had sex.
A sleepy smile passes his lips. “I couldn’t even if I wanted to.”
I wipe us both up as best I can, but even still, “It’s probably best we hop back in the shower.”
Dylan doesn’t protest as he makes his way to the bathroom on jelly legs. The shower’s already hot since I started it when I came in for the extra washcloths and he stands, letting the water run over his glorious body.
His eyes are scrunched tightly again like he’s trying to block out internal voices and my heart falters. I know he said it felt good, but to expect him to just suddenly be okay with switching roles is immature and unfair.
“Dylan, look at me.”
He opens his eyes and the creases at the corners, the furrow in his brow, and the way his jaw is clenched speaks to the shame he feels and I hate it.
“You’re still the same man you were.” I grab his hands and place them on my chest over my heart. “You’ve given me everything by trusting me with that. I’ll never use it against you.”
I’m not sure why I chose those words instead of telling him I love him and that that was the best sex of my life, but it seems to do the trick and pull him out of his own head a little. His fingers curl into my pecs and he drops his forehead to mine.
“I’m glad it was you.”
I don’t push for more. Instead, I lather up my hands using the body wash dispenser on the wall and begin to knead his muscles. I work my way down his entire body until I’m on the floor of the shower, pulling his foot into my lap and rubbing soap into his arches.
“Jake, you don’t have to…but damn, that feels so fucking good.”
I smile and think to myself, that’s not the first time you’ve said that tonight.
Dylan chuckles above me. “I know what you’re thinking.”
“Do you now?” I ask, pulling his other foot into my hands.
“And you’re right. It isn’t the first time I’ve said that tonight.”
My smile grows in tandem with my heart.