An Anal Journey

Author's note: Thank you for reading my first story! I already had this one ready to go when I was working out the mechanics of this site, so here is the next installment of the story of Mikey and Jason.

Please be aware that language like 'clit' and 'pussy' is used for a trans-masc character.

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Things with Jason are going... Well, they're just still going - and it's better than I ever dreamed it could be.

I woke up the following morning being spooned by him in his bed where we then had sex again. I was sore from the night before having not been used to taking a man of his size, so he was incredibly careful with me. He may have warned that he likes to be rough and dominating but on that morning he wasn't. I will never forget how sweetly he kissed me as he slowly rocked into me, being mindful not to put any unnecessary weight on my tender body.

Returning to work was interesting, especially bumping into him in the corridor when we both had other co-workers with us. I definitely blushed but he kept his cool. He seems to be able to take most things in his stride which is good because for me it is the opposite. I'm an overthinker, but he thankfully has the ability to put me at ease even though that isn't exactly what he signed up for. We aren't boyfriends. He said he didn't want that kind of relationship which I understand, but friends with benefits doesn't really work either because we were nothing but distant colleagues when we first hooked up. I don't really know how to label what we are other than lovers, I suppose.

I honestly thought that he would discard me after that first night together which turned into a weekend. But he didn't. The following weekend I was back in his bed, catching my breath, sprawled across him with his arms wrapped tightly around my slim torso. "I know you said before that you wanted to try anal." He said lethargically. "But I wanted to... talk about that first but whenever I see you, I immediately want to jump on you and fuck you silly."

"Even at work?"

"Hm... let's just say I'm glad I have a private office with blinds I can shut." I dreamt about him pounding one out with his fist in his office that night, with me interrupting him to finish him off with my mouth.

Work has become a little complicated after we found out in a large, company-wide online meeting that our departments are merging. Jason isn't my line manager nor is he ever going to be, but he's still my senior in more ways than one so when I learned this news, I felt deflated. I was convinced that things wouldn't be able to continue between us... but he turned up on my doorstep that night and showed me otherwise. It was innocent enough involving takeout food and a movie, but then I found myself dragging him into my shower where I lowered to my knees to take him in my mouth. I love the weight of him on my tongue and I'm getting better at squeezing him down my throat without gagging (too much).

We were hardly dry when Jason carried me to my bed and tossed me down on it. He kissed me like he meant it with his hands caressing any patch of skin he could touch. I was panting heavily when his lips separated from mine and with his hand heading south towards a region of my body I really wanted to be touched, all I could think about was one particular hole I wanted to feel him. "Are you going to fuck my ass?" I asked him breathlessly and watched an inquisitive look pass his face.

Jason brought a hand to my face and delicately rested it against my soft skin, rubbing my cheekbone lightly with his thumb. "You really want that huh..." He didn't say this to make me feel small or needy, but with wonder in his voice that I'm not sure where it originates from.

I have never really felt before that it is okay to be vulnerable when underneath someone waiting to be fucked, but Jason makes it seem okay to be vulnerable. He doesn't judge me, and he sees me for who I am as opposed to what others believe I should be. "I guess I want to know what's it like to be a gay man who doesn't have a vagina and is a bottom." I admitted with a wavering tone. "I know it isn't the same. It's not like I have a prostrate to stimulate... but I want to try."

He smiled at this before dipping his head to kiss me again, but much more gently this time. It was like he was thanking me for my honesty. He kissed my lips, then the corner of my mouth, and then my cheek, and the cuteness of the interaction was quite the juxtaposition to his following instructions. "Lie on your front." I embarrassingly giggled as I obeyed.

I was so ready for him to take me there and then but instead his hands swept down my back as he started to give me a somewhat harmless massage. I almost protested but Jason has magic hands, and I did have quite a stressful day with all the merger talks, wondering what this meant for our relationship. He expertly kneaded the knots from my shoulder blades gradually moving further down in no kind of rush. I knew that when he eventually got to the cheeks of my ass which he playfully felt that I was probably already glistening wet. Then again, my juices had been dribbling down my thighs since my shower.

Jason brought a flexed finger to my tight hold and lightly brushed over it making me shiver. "Have you ever inserted anything back here before?" His Midwest accent seemed thicker than usual, and I had a feeling that he was doing everything in his power to control himself.

"A finger once or twice, but nothing bigger than that." He couldn't see my blush when I admitted this, but he most likely knew it was there because he already appeared to know me so well.

"And you have slender fingers." His hinting about the stretch of anything other than my fingers made a whine leave my throat, and he lightly slapped my ass suggestively just so I would whine again. Jason chuckled and climbed back up the mattress so he could kiss me on my cheek. "I want to wreck your hole, Mikey." He obscenely whispered only a few inches from my face so I could feel the heat from his breath. "But I also don't want to hurt you. So we will have to take things slow." He states and then he was moving back down near my butt to continue what he had barely begun.

I wasn't quite sure what he was doing when he spread my legs a little so he could settle between them. I thought that perhaps he was going to eat out my pussy from this angle but then he was pulling my ass-cheeks apart. "Not everyone enjoys this, so tell me to stop if it isn't for you."

"What are you- oh." Oh, was about right. I wasn't expecting to feel a gentle, wet glide of his tongue over my virgin rosebud as his hands fondled the globe of my ass. I froze initially, analysing the alien feeling but it didn't take long for me to relax. Turns out there are a lot of nerve endings back there and Jason definitely has the skill to satisfy each and every one of them. I moaned into the mattress and pushed back against his mouth, my eyes rolling back into my skull at the mixture of sensations. His teasing tongue... the brush of his chapped lips... the scratch of his stubble against my skin. It was close to being overstimulating, but I loved it. I started to question how I got from nervously messaging my co-worker on Grindr to a month later being rimmed by him on my sheets, but my brain couldn't think about it for long. I lost any thoughts that vaguely made sense.

I started to moan like a man possessed but that just spurred Jason on. He wrapped an arm around my torso, so I was no longer flat on the bed, to pull me to my hands and knees with my ass in the air for him to get easier access to. He moved his mouth away just long another to grab hold of my meaty thighs as support and to demand, "Rub your dick until you cum." It was difficult to hold my body weight up with one arm, but it was worth it. I massaged my engorged clit in tight circles. I came so hard that I strained my throat from the sounds I made as I did.

But one orgasm wasn't enough. Jason wasn't done. He flipped me onto my back and when he kissed me roughly, I hissed because of a cold liquid being poured clumsily onto my hole. I couldn't tell you at what point he managed to fish the bottle of lube from the drawer to my nightstand, but he did, and he generously spread it over two of his fingers. His mouth feasted on my pussy with so much urgency yet his fingers probing at my asshole were so delicate. He may have never said that this isn't his first time getting someone into anal, but he has sure been showing his experience surrounding the subject. He knows just what to do and I can't put into words how good it felt to thrash on top of the sheets with his tongue in my pussy and his fingers playing with my ass, slowly spreading me open. "I have a feeling that you're going to love being fucked in the ass." Jason mumbled into my hair after my second orgasm, as he held me close to him with nothing but affection. He certainly has a skill at saying something completely filthy whilst doing something so loving.

Taking things slow has been frustrating at times but mainly a lot of fun. Last week I arrived at his with a bag of groceries to cook him dinner, but he also had something for me. He passed the cardboard box over to me so casually as if it didn't contain a bunch of new toys he ordered. There were three different sizes of butt plugs, a small vibe, and something else I didn't recognize. I held up the packaging, but Jason was quick to explain. "It's a vibrating pussy plug." My brow dipped at this confusing explanation. It is not like I needed to train that particular hole to take large objects, he has very much proven that. "I thought about what you said and not having a prostate. Anal might not be as stimulating as you hoped, thought this may help." I'm ashamed about how touched I was about this.

I made dinner that night with the smallest plug snug in my ass. He was pleasantly surprised by my suggestion and before I could blink, I was bent over his knee as he sat on the couch, having the toy slowly worked into me helped by a lot of lube. It wasn't uncomfortable, not after him fingerfucking me back there a few times, but it did feel strange having this thing inside me as I cooked at the stove. He pounded into my pussy so hard after we ate that I could barely see afterward. I suggested that I take the rest of the toys home to get myself ready for him, but he insisted that we are in this together. "It's a marathon. Not a sprint. I'm in no rush when there's plenty of other things we can do together."

The second size of toy was more difficult to take. Jason's mouth had just brought me to orgasm, so my legs were shaky as he encouraged me to get on my hands and knees in the middle of the bed. He prepared me with two fingers and so much lube that he squeezed straight into my small, gaping asshole. I flinched at the coldness of the liquid, and he stroked a hand over my back in an attempt to soothe me. On paper, the difference in the size of the butt plugs didn't seem that huge, but when he was edging the toy into me it felt ginormous. "Good boy..." He praised which did help me relax the ring of muscles slightly. "There we go... In it goes..." It was only an inch longer and a third of an inch thicker, but it was like it was splitting me open. I couldn't imagine being able to take a bigger one never mind his monster cock.

It took time and a lot of patience from us both to get the third one in me just a few days ago. "How big is this?" I asked in a strangled tone that sounded like I was suffocating from an elephant sitting on my chest. My face was pressed into the back of my left arm whilst my right hand was prising one of my ass-cheeks away from my hole. Jason was pulling at the other one as his opposite hand was pushing the plastic object into the gap it was creating.

"Like four-and-a-half inches in length and a girth of nearly five." Smaller than him. I may have not taken a tape measure to his impressive dick, but it looks to be eight inches in length with a girth of six when hard. It isn't exactly easy to take it in my pussy, and as he struggled to get the plug fully in me, I thought that getting his dick there would be impossible... I'm now feeling a bit more optimistic three days into using the plug.

I can feel the stretch now as I try to go about my Friday but knowing what tonight will bring is making it difficult to concentrate. I head to the vending machines out of the main area of offices near the elevators in search of a drink to pass some of the time, but a quick glance at my watch tells me I still have an hour to go of the workday and several until my scheduled meet with Jason. He's insisting on taking me out for dinner, but I negotiated a reasonably early time of half past six, just so we can have more time to play. "Looking at the clock ain't going to make the time pass faster." I hear him tease as he joins me by the machine looking all dashing in his perfectly pressed suit and important by him clutching a couple of files.

"You don't need to tell me that. I've only been checking it all day." I confess, but I direct this at the drinks machine just in case anyone passes by and gets suspicious... but it looks like we're alone.

Jason double-checks this by looking down both directions of the corridor before he leans in a little. "Is it still...?" He says in a hushed tone. He doesn't need to finish what he is getting at because I know.

"Snug."

"How long for?"

"About six hours." I reveal and his eyes darken at this. If only neither of us cared about our jobs and reputations, so he could fuck me right here for anyone to see. "I am so going to be ready for you."

"Yes, you are baby boy. Yes, you are." He growls but then he's walking off back in the direction of his office, not even peering backwards as he does.

Dinner is one of the most difficult things I have ever had to get through. Jason said when we sat down that we had to order at least two courses to fill us up, so we decided on the main course and dessert... but we never got to dessert. He catches me pressing my weight down onto the chair to try and get some pressure on the toy wedged in my ass, and he snaps. "Looks like we're going to have a different kind of dessert." He announces as he waves over the waiter to pay the bill.

He's kissing me forcefully as soon as the door is shut to his apartment whilst pushing the dinner jacket away from my shoulders, so it crumples onto the floor beneath us. "You're such a bad boy." He scolds with clear naughtiness in his tone before he's nipping at my bottom lip making my mouth open so he can assault my tongue with his own. We're hurriedly unbuttoning each other's shirts and then unbuckling each other's belts, as we make the messy journey to his bedroom. All that can be heard is the sound of clothes being shed and our mixed moans, both incredibly needy.

I fall to his mattress as soon as I feel the backs of my legs touch the edge of his bed. He helps me down with two firm hands on my shoulders. The sudden connection with the furniture makes a jolt of pleasure hit me because of the prod of the plug and I bite down on my bottom lip so hard that I break through the skin. "I should punish you for being a bad boy." Jason considers but he's pushing down his pants and underwear making his rock-hard cock spring free, before he kicks the items of clothing to the floor. "But shit Mikey, I wanna fuck your ass so bad."

"Please... Sir..." I beg as he steps into my space, separating my legs by planting his between them. With his thumb and his index finger, he tilts up my chin so I'm looking up at him and it hits me how truly vulnerable I am right now. Like this. Yet I feel safe with him. "I-I need it so bad."

Jason grins and leans down to capture my lips with his, being sweet at first but quickly making it filthy. He picks up my legs just so he can swivel me to lay down with my head against one of his soft pillows and then he is tugging at his already hard cock most likely to relieve some pressure. He doesn't need to retrieve his big bottle of lube from his drawer because it is already sitting on his nightstand next to his lamp, a bottle of water, and a couple of additional sex toys. He's been prepared since he left for work this morning.

So he joins me on the bed and sits on the backs of his legs with his dick standing ready but he first has to work at getting the plug out of me. He bends my legs at the knees, so my feet are flat on top of the mattress and then wordlessly takes hold of the handle by the tips of his fingers and begins to carefully pull. "You gotta relax for me Mikey." He gently instructs and I focus on breathing out as his other hand starts to stroke my gut, helping me along.

It isn't easy to get the plug out because of how long it has been in there. The lube dried up many hours ago. But the slight sting is worth it because I am left with a wide, gaping asshole ready to make it even wider. "Is it okay?" I nervously ask even with the content smile on his face.

"It's more than okay. It's beautiful." He compliments and my skin flushes from my face, down my neck, and across my scarred chest. "I should probably clean you out."

"I did that this morning." I reveal and he raises his eyebrows from being happily surprised. "I'm ready for you to ruin me with your dick, Sir." And how his eyes darken is just like they did earlier next to the vending machines.

Jason sneaks a hand around the back of my head and pulls me in for a firm kiss. "I love being able to look into your gorgeous eyes when I fuck you, but I think you will be more comfortable if I take you from behind." He mumbles next to my lips, but I don't have the chance to respond because he's already maneuvering me on the bed like I weigh absolutely nothing.

We're not new to doggy style. He's pounded into my pussy from behind on more than one occasion with my hands turning white from gripping the headboard, but it usually is in the heat of the moment. There's a lot more care being taken as he positions me on my hands and knees in the middle of the bed with his lips littering kisses down my back until they finish on my right ass cheek.

I needily moan when he sucks the skin there between his teeth to mark me. I love it when he marks me -- it's just disappointing that he can only mark me where no one else can see.

My arms are shaking but I think it is from the anticipation more than anything. I hiss when he squeezes a generous dollop of lube directly into my asshole, and then he's shoving two fingers inside making a squelch sound, spreading the liquid around along with his fingers. "This is going to be great." He mumbles potentially to himself before I hear the sound of the bottle being squeezed again but no coolness comes. Instead, the next thing I feel is the head of his dick being pressed against my well-lubed hole. "Are you ready baby?"

"Definitely. Please... fuck me." I whimper and I have barely uttered the last syllable when I feel the pressure of him pushing forward.

Even with all the preparation, just the head breaching my ring feels like too much. He's girthier than the biggest plug and he creates a stretch that makes me gasp towards the headboard. Shit. He's so big. "You've got this..." He encourages but a tiny yelp escapes me when he abruptly sinks a couple of inches inside. "Shh... It's okay sweetheart." He strokes down my back with one hand whilst his other guides his hardness into me, slowly, inch by inch. "Breathe through the pain." I release a long exhale, loosening my muscles so he can push deeper, past the point any of the toys we were trying can reach. "Be a good boy for me."

The hand that is stroking my back adds some nails to the mix which scrape down my delicate skin in a way that has me moaning loudly. "There we go... Almost there." It is disappointing when his hand disappears, but the disappointment doesn't last because the sound of a vibrator starting up fills my ears. One press of it against my swollen clit helps him ease the final inch of his cock into my ass, so he is balls-deep inside me.