Looking after Him

Author's note: This is a shorter installment in this series but still hopefully hot.

Please note that this story contains the words 'pussy' and 'clit' being used for a transgender man. If this triggers you in any way, I wouldn't advise reading on.

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The past couple of weeks have felt almost impossible.

I've been chasing a promotion which has meant more work to show willingness to improve blah blah and my dad has been giving me the run-around about meeting up. He keeps canceling. I don't know why I bother giving him any time when he's been discarding me like I'm worth nothing since I was a pre-teen. He doesn't respect me, and he's still not completely okay with me being trans. It's just a lot to deal with.

I am exhausted. Jason has been doing all he can without interfering too much like cooking us dinner and running me a bath when I need to simmer down at the point my head feels like it is going to explode. I know it has been killing him, to not get involved with my work stuff, because he probably could help, but that would be one step too far. We need boundaries with our work, otherwise, we may have to face the risks of us having any sort of relationship that isn't platonic.

I still don't know how to label our relationship. We're two people fucking who kind of like each other but both have our reservations about commitment. To me commitment is scary and well, he said when we first hooked up that he didn't want that kind of relationship. So I try not to think about it too much because if I did I might realize that I'm starting to become dissatisfied about just screwing around. Maybe I want something more. "Hey, Mikey." I hear him walk up behind me now in my kitchen as I work tiredly at the table. It may be a Friday night but here I am staring at a bunch of spreadsheets until my eyes go blurry. Jason's hands go to rest on my shoulders where he starts to massage some of the knots out of the muscles there from when I've been too tensed up. "I've ordered some pizza. Thought we could have a quiet one and snuggle up on the couch. It should be here in a minute."

Is this the actions of a man who just wants to screw around? I've never felt so taken care of before, and it hurts a little that it is by a man who doesn't want to commit. I run my fingers through my disheveled hair, shrugging off his touch in the process, and wonder if tonight is the night that I will be brave enough to have an honest conversation. "Alright." I simply say as my tummy begins to grumble. I am hungry and I'm hardly going to get all this extra work done on an empty stomach.

Jason sighs and wanders around to the other side of the table so he can study my expression. I pretend I don't see him for a second and instead focus on the figures that are looking back at me on my laptop screen, but his following statement is too much of a distraction to continue. "I'm worried about you."

"As my co-worker or as a guy who fucks me sometimes?" It just comes out and I feel my cheeks heat up from embarrassment.

"Ah." Jason mutters and pulls the chair nearest to him away from the table so he can sit down. "I was wondering when this would come up." He rests his clasped hand on the tabletop, and I watch him think for a few seconds, as the fingers on one of them drum against the back of his hand. "Mikey, I like you, a lot and I care a great deal about you..."

"But...?" I interrupt, ready to get my heart broken on this already shit week.

There's a flicker of something in Jason's eyes that I haven't seen before. Regret? Anxiety? Sadness? I can't tell for definite, all I do know is I have never witnessed him being so unsure before. He takes a deep breath and wets his bottom lip with his tongue, and all I can do is impatiently tap my foot on top of the floor tiles. "I've thought about this a lot and even though I want it to work I don't see how it can." I almost choke at this revelation.

This man who told me explicitly that he was looking for a fuck, for companionship, and not a relationship is currently making it seem that maybe he does want the latter which is totally unexpected. "Wait, you want this to work?" I blink at him in disbelief.

"Of course." He says like this was obvious and if I wasn't so stunned right now, I would be annoyed at his blasé attitude.

"Like... us being boyfriends?" I check and he smiles as soon as I say the 'B' word.

"Yes, but..." He sighs, evidently remorseful. "We couldn't be open about it. Not with us working together."

"I know that." I tell him and his brow darts up towards his hairline. "That doesn't mean I don't want us to be boyfriends."

Jason awkwardly chuckles at this and unclasps his hands just so he can scratch the back of his neck nervously. "Well now I feel silly." He admits and it is like there are butterflies fluttering in my stomach, threatening to escape. The buzzer to my apartment then rings, stopping the interaction sooner than I would like but I'm feeling positive. "That will be the pizza. Grab a couple of beers and I will join you on the couch."

I'm smiling as he gets up, and that smile grows when he presses a kiss to the top of my hair as he passes me by.

Jason had ordered my favorite pizza amatriciana which is topped with tomatoes, caramelized onions, pancetta, pecorino cheese, and basil. It's from the place that costs more to be delivered but apparently that's how much he cares. He opens the box and takes one of the bottles of beer from me. "So, tell me what's on your mind." It turns out it is actually quite nice to vent. He listens patiently, doesn't give unwanted advice, but simply shares comforting words every so often.

Pizza, beer, and talking about what is on my mind is exactly what I needed. When the box is empty, I don't stand up to go back to work but reach for the TV remote to find something to watch, as background noise really. A re-run of a sitcom comes on and I settle next to Jason and lay into his side.

I quickly realize that although his eyes may be trained on the TV set, his mind and well, hand, is somewhere else. His hand which at first was innocently resting on my upper thigh, comfortingly stroking, is edging closer and closer to my core that is already dripping with want.

We've not done anything sexual for almost a fortnight which is easiest the longest time we've ever gone, and that's on me. I hadn't realized how much I had been longing for it until I felt his touch creeping under the leg of my oversized basketball shorts. It's so... teasing, that I have to put my hand on top of his to tell him that I've felt it.

Jason freezes and looks over at me with a pinkish hue painting his cheeks. He starts to pull away, but I press down my hand firmly to keep his in place. "Keep going." He nods with a sign of a smile ghosting his lips before he easily shifts me from a sitting position to lying down on the couch. It's only small but we've had enough practice now, so he knows how to fit between my legs perfectly.

He tugs down the shorts and beams on finding me completely naked underneath. "Easy access, just for me?"

"For comfort." I claim but it is obvious by how he rolls his eyes that he doesn't believe it. "Perhaps I hoped that you would offer some kind of stress relief tonight."

"Oh like a hot, bubbly bath with scented candles kind of stress relief?" He teases but his fingers do find my clit which he starts to rub to get the fire started. "Or a different kind of stress relief?"

"I think you know."

"Well, I can certainly feel it." He appreciates, his fingers leaving my clit for a second to stroke at my folds, telling me just how wet I already am. He always knows how to push my buttons. "What do you want?"

"You're asking me what I want?" I ask in reply, my jaw almost dropping at how sweet he's being. "What happened to that dominating fella I fell into bed with that time?"

"Maybe tonight he's feeling gentle." He softly says and the butterflies return, they're only chased away by the jolt of electricity of his fingers brushing over my little dick again. "But still dirty of course."

"Can I sit in your lap?"

"Is that all you want?"

"If you keep using those strong hands of yours..." I flirt and he hums in agreement before he's pushing his legs together and patting his thigh. I can feel my grin as I clumsily get up so I can sit in his lap, facing the TV. My legs hang in the air on either side of his thighs as I settle against his hard chest. Being small has always been an insecurity of mine as a trans guy, but I like feeling small compared to him because of how he looks after me. "I hope I'm not crushing you." I joke and Jason squeezes my hip before peppering kisses down my neck, knowing everything about my insecurities.

He doesn't reply with words, but his left hand finds my wet opening where he spreads some of my natural lubricant to get me ready. "Relax for me baby. You really need it." Two of his fingers dip into me easily and my head falls back onto his shoulder from the sensations, but that just gives him the opportunity to sweetly kiss my cheek as his fingers work me up perfectly. I chuckle warmly at the combination of his actions, instantly feeling so much better.

There have been times during the stresses of the last couple of weeks whilst wondering where this relationship was going, that the age difference between us played heavily on my mind. Eighteen years is a big gap, and I can only imagine the reaction of my friends and family if they found out, but in times like this, with him taking care of me so well, I don't care that he's older than me. He's not taking advantage of me. I trust that I genuinely matter. I smile at this thought but then I'm gasping because of Jason curving his fingers to brush the special spot inside me, like he's perfectly attuned to my body and what it needs.

My toes curl and I hiss as he suddenly adds a third finger, stretching me beautifully. It's impossible not to react to his thrusts and I moan desperately, with a hand gripping his left forearm and squeezing. Jason's right-hand joins in by reaching my clit, which he goes back to rubbing in tight circles, agonizingly slowly. "So responsive." He whispers in a gruff, low tone. "I love to imagine what it would be like seeing you spread wide on my fist. Bet you could take my whole hand like the good boy you are." His ministrations become quicker and rougher, trying to make me cum. The actions along with his dirty talk get me closer to the edge. "Would you like that, Mikey? Would you want to be stretched around my hand?"

"Yes!" It's an easy reply that mixes with an urgent moan. It probably wouldn't be difficult to get his entire fist in there when he's already got me accustomed to large objects. "Need... more. Need to cum." I sound almost drunk because of how slurred my words are, combined with my needy moans. I clench around him, needing that release but struggling to quite get there.

"Another night." He grunts and temporarily stops the rubbing of my tiny dick to pull me closer to his groin. Despite his cock being contained, he roughly rocks his hips against me, seeking his own release, not caring that it will be inside his pants.

But I care. "Stop." I choke out and he halts what he's doing so quickly, including removing both his hands from me which he extends in front of him as if he's been doing something wrong. "Sorry." I immediately apologize -- I didn't mean to freak him out. "I just need you to fuck me. I need your cum to fill me, Sir." I hear Jason's relieved sigh as he puts his hand on my thighs.

As soon as I shakily climb off his lap, he's hurriedly pushing down his pants and underwear that he kicks to the floor, with his shirt still done up but creased. Perhaps it is only fair as I'm still wearing a plain white tee. We are too desperate for each other to even consider shedding any more layers. "How do you want me?" He questions, his Midwestern drawl thick with desire.

"Hard and fast. From behind." I tell him and I'm already positioning myself that way on my knees, leaning on my elbows on the cramped couch. I want this right now too much to move to the bedroom. "I need to feel you for days."

I feel the head of his large cock brush over my opening a few times to gather my slick before Jason's strong arms wrap around my torso as he enters me. There's something so fiery yet doting how he leans almost the entirety of his weight on me by laying on my back, keeping me close with his arms holding me tight. A strangled moan leaves my lips as he fills me so well, giving me every inch of the eight he owns. "Fuck." He curses, his hot breath near my ear. "Always so tight for me, but my good boy takes me so well."

His praise has me gushing around him, but I don't have the opportunity to reply, because he pulls out apart from the tip before his hips snap forward in a brutal thrust. The pace he then sets is ruthlessly rough with his balls slapping my skin and his animalistic groans showing just how raring he also is to cum. It's not just me who has gone without sex over the past couple of weeks. The severity of thrusts has me collapsing with my face burying into one of the couch cushions, muffling my moans yet they're still incredibly loud. His hold loosens on me just so he can resume rubbing my clit, with his other hand near my head to keep his balance.

It's almost too much. I can feel my high coming, every ounce of me is becoming overstimulated because that's how close I am, but I am struggling to quite crash over the edge. It's difficult and frustrating, especially because of how much I need it. "Come on baby boy. You can cum for me. I know you can do it, my good boy. Cum all over my cock."

There are tears in my eyes as I finally cum. My legs painfully tense and my pussy hugs his cock as his name in the form of a scream gets ripped from my throat. He fucks me through it, not relinquishing his movements but he does shift some of his weight off me so he can watch me shake beneath me. The digging of his fingers into my hips keeps my orgasm going, my body feeling ridiculously sensitive to his touch. "J-Jason... Sir..." I moan with my core almost burning from the overstimulation. "Please cum inside. Fill me up. I need to feel you leaking out of me."

Jason groans with faltering movements and I feel his hot cum spurt inside me, filling me up just like I wanted. I can feel the pulsing of his cock as he continues his shallow thrusts with more and more cum being pushed deep inside me. The sensations and his delicious noises are almost enough to make me orgasm again, but he pulls out before he gets there, going back to sit on the couch.

I can't move straight away. My chest heaves as I breathe, face first, into the couch. I focus on the feeling of his seed leaking from my hole as I carefully lower my ass from the air. I jolt a little at his fingers going back to probe at my pussy. "Wanna taste?" He offers, catching some of our combined releases on the end of his fingers.

"Finger it back inside." I request and he groans again.

"Shit Mikey, are you trying to make me hard again?" He questions but then he does shove his fingers all the way inside, pushing the cum in as deep as possible. I purposely clench, to draw it deeper, before he pulls his fingers out with a satisfying squelch. "Alright baby. How about I run that bubble bath now with scented candles? To keep you all relaxed."

"As long as you join me..."

"I thought that was very much implied."