Crossing a Line

Author's note: Hello! This is my first story on here. I hope you like it! Comments very much welcome.

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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I've seen him around the office. He's in a more senior position than me but in a different department so it wouldn't be weird, meeting him like this. This is what I've been trying to persuade myself as I stare at his Grindr profile. I had no idea he was gay, or at least not straight. He's always come across as the straightest guy in the room but perhaps it is unfair to stereotype. I hardly fit the standard profile of a gay guy on this stupid app. It is one of the reasons why I have never got very far with it. Amongst all the anger and the thoughts of dysphoria, I understand why most people don't want to go very far with me. It sucks though.

Being a gay transgender man has more downs than ups, especially when it comes to dating or something a lot less cute. A lot of trans guys find their luck with queer women who are sensitive and sympathetic enough to understand the difficulties that come along with being trans. I tried to ignore the lack of attraction to women for so long because of this, but then I realized that I much preferred being friends with these people than anything else.

One of them who I have kept in touch with, suggested I'd try Grindr. "There are all sorts on there." She said as a persuader, and I downloaded the app that same night. That was two weeks ago, but I'm yet to meet up with anyone. There have been plenty of failed conversations, but now I'm here, staring at the profile of someone who is a co-worker. It is a risk.

I don't think I've ever conversed with Jason before. We may have been in the room together when he has spoken or when I have spoken, but those words were never directed at each other. All I really know about him is that he must be good with numbers being a data analyst, he must be from the Midwest from the slight twang in his accent, and he must have a thing for younger guys as I'm almost twenty years his junior, and both of our profiles reflect our honest age.

His profile doesn't give much away.

Name -- Jason

Age -- 45

Height -- 182 cm

Weight -- 170 lbs

Ethnicity -- White

Body Type -- Average

Position -- Switch

I am -- Single

Gender -- Cis male

It doesn't say what he is looking for. His bio just says: 'Come on, let's chat.' The thing that really grabs my attention though is the fact that he is online and only two kilometres away. It would be hypocritical to mock his profile though when mine isn't much more helpful.

Name -- M

Age -- 27

Height -- 160 cm

Weight -- 120 lbs

Ethnicity -- White

Body Type -- Slim

Position -- Bottom

I am -- Single

Looking for -- Not really sure yet

And the photograph I've used barely looks like me. Maybe I'm scared of putting myself out there, and I prefer anonymity. The thought of anyone I know finding my profile is terrifying to me.

Almost as terrifying as sending an opening message.

I take a swig of my bottle of beer whilst checking out the time at the top of my phone screen. It is still early. I was at the office less than two hours ago, in the same building as this guy. There is still time to meet. I'm not usually so brazen but I'm also a bit of a lightweight and this is the second drink of the evening already, the first was in an Irish bar around the corner from work with a bunch of people from my department. I was naturally one of the first to leave, especially when Karen suggested karaoke.

Screw it. He could just not reply.

*M: Hi there. How's your evening going?*

Way to sound lame Mikey. Way to sound lame... but he reads the message and starts typing almost immediately.

*J: Hi there yourself.

My evening is a bit of a bust, so heading out to a bar near mine. Joey's. Do you know it?*

It means nothing to me, but thankfully Google Maps exists, and it says it is an option for tonight. Not too far. Could walk if I dared, but also a taxi wouldn't be too expensive. Am I really going to do this?

*M: Never been... Would you like some company this evening?

J: That would be nice. I will be there by 8. Probably sitting at the bar.*

Okay, so this is happening.

I'm not someone who needs ages to get ready to go out, but suddenly half an hour doesn't seem long enough. I discard my half-drunk bottle of beer on the coffee table and practically leap to my feet as my limbs shake with excitement. The contents of my closet stare back at me and I huff at myself because I'm getting all up in my head like I always do. Growing up people would call me frigid but behind closed doors, I love the feeling of bringing myself to orgasm. It's just finding someone else to give me that feeling which I find nearly impossible.

I throw on an ensemble of dark skinny jeans, and a plain black tea with an open red, plaid shirt over the top. It doesn't look right, I look too young, so I button it up and then throw my oversized leather jacket over the top. This looks better but I'm still not one hundred percent happy with the outfit however it will have to do because I don't want to be late. Being late on a first meet is a big no-no in the dating/hooking up world and although I know it is probably going to be a massive no as soon as Jason spots who I am, I don't want to give him any ammunition. So I grab my phone, wallet, and keys before heading out into the busy city, immediately in search of a bright, yellow taxi.

My heart is pounding as I walk into the unknown bar. I'm a person who likes routine and familiarity, especially in a world that threatens people like me. For a second, I have to remind myself how to breathe as I stare at the backs of the heads of various fellas sitting at the bar, trying to visualize what the back of Jason's head could look like. He's got dark hair with a few smatterings of greys so that rules out the blondie in the middle of the row. I'm going to have to be brave, is what I tell myself as I approach the edge of the bar, and just as luck would have it, the man I'm seeking is sitting on the end seat with an empty space beside him.

Jason is wearing a pressed navy shirt which would seem too smart for this kind of establishment if it weren't for the faded black jeans. The beginning of a grey beard decorates his face, and he looks relaxed as he gazes into his glass of what was probably whiskey. I am psyching myself up to say something when he finally looks up, his soft brown eyes wide when he spots me, standing awkwardly a few meters away. "Michael?" He questions with shock in his tone.

"It's Mikey." I correct with a blush. The last thing I want right now is to hear my professional name. "Is it alright if I sit down?"

"Yeah, of course." He's checking me out, it is obvious by the sweeping glance from my head down to my toes. It makes me glad that I decided to wear the pants my ass looks good in. "Do you want a drink?"

"Yeah, a beer please."

Jason smoothly and calmly waves over the bartender as I take a seat beside him, trying to mask how nervous I am but it almost becomes abundantly clear when I struggle to get on the stool. I think I manage to keep enough of my cool for him not to notice. By the time I have settled, his glass has been refilled and a green bottle has been put down on the bar in front of me. It takes every ounce of restraint to not start to anxiously pick at the label that is peeling away from the glass thanks to condensation. "I like your jacket." He breaks the quiet between us. "I used to wear stuff like that when I was your age. It looks good." I am ready to be disheartened by the age comment, for a second believing that he wouldn't be into this but then another comment quickly comes. "You look good." He compliments and I know my blush must be shining from my cheeks.

"Thank you." I send him a smile but can't keep eye contact for long. My compliment in reply is directed at a chip in the bar's wood. "You do, too."

Jason takes matters into his own hands and picks up my bottle of beer before he pushes it in my eyeline, encouraging me to drink it. A bit of Dutch courage. I smile at him again but this time it is much more relaxed, and I chuckle a little as I take the drink from his grasp. I knock a quarter of it back, increasing the fuzziness I'm experiencing in my head. "I didn't think this would be how I would be spendin' my night." He shakes his head at himself with a light laugh that doesn't at all feel targeted, it just feels warm. "Your profile said you didn't know what you're looking for?"

"I'm trying to figure things out. I want... something though." I reveal, continuing to keep things vague but that probably stems from years of insecurities building up. "Your profile didn't have any information about what you want either."

"Sex. Companionship. Just none of the messy stuff that you get in relationships." He honestly states, not at all skirting around the subject. Him being so upfront and just saying 'sex' almost has me choking on my drink. "I've been married twice. Divorced twice. Heck, I've got kids. I don't think I'm bad at relationships, but my history isn't great." He admits and even though he's keeping things casual, I perceive a hint of hurt behind his deep, brown eyes. But he's quick to brush the intrusive thoughts off. "The anonymity of your profile intrigued me."

"Would you have come, if you knew it were me?"

"I don't know." He says and taps the edge of the whiskey glass a couple of times. "The rational part of my brain is screamin' that this is a bad idea. What is it they say? Don't shit where you eat."

"We don't work that closely together. No one else has to know." It comes out of my mouth so quickly and I am instantly mortified by the tone of it. "Sorry, that sounded needy."

"There's nothing wrong with being a bit needy." He flirts and suddenly I am very aware of my loins being on fire and my wetness making a mess of my boxer shorts. My lips part with obvious arousal and Jason, that mother fucker, has the audacity to grin. He takes a sip of the amber liquid in his glass before he leans in close to me so that I can smell his musky cologne and the drink on his tongue, and whispers in a low, sensual voice. "I do love it when boys whine underneath me as they take my dick." His hand resting on my clothed thigh seems to have the ability to scorch the skin underneath the fabric.

His hand remains where it is when he pulls back. It is positioned in a spot that won't draw attention to us in the busy bar but still sets every part of me on fire. Oh how I would love for him to move it higher and more in-seam. I gulp down nothing and focus on my breathing. I feel like I could completely melt simply from his wanting gaze. This is not the same man I see around the office. He's a completely different animal.

He gives my thigh a squeeze before removing his hand and something changes his expression. He blinks away the lustful look in his eyes and turns serious, which is almost like a bucket of ice-cold water has been thrown over me. Have I blown it already? "Mikey, I have to warn you. I'm very dominant in bed. Especially with bottoms like yourself." Oh I haven't blown it, he's just warning me, and I feel the tips of my ears turn pink as the room suddenly gets even warmer. "Oh." He mutters with glee as his whole face lights up. "Do you want to be dominated in bed?"

"I haven't got a huge amount of experience of being dominated." More like any... "But my body is saying yes right now." I reveal, ignoring the screaming voice that usually holds me back. I can't let this opportunity go to waste. I need to know what he looks like when he's naked and what it feels like when he's pumping into me -- but there is something to establish first. "W-What is your sexuality, anyway? Are you like... fully gay or-"

"Mikey, I know you're transgender." He interrupts, clearly having worked out the source of my nervous stuttering.

"You do?"

"It is pretty common knowledge in the office." This makes my being deflate which must be obvious because he is quick to backtrack. "Not because you don't pass or anything. You are a guy. Just someone made it public knowledge. I had no idea until that point." This works at picking me back up. "To answer your question though, I'm bisexual. Can I ask if you've transitioned at all?"

"Hormones and top surgery, yes. Bottom surgery, no. I-it's why I asked. A lot of gay men aren't into fucking a man with a pussy."

Jason lays a hand on my forearm with affection that surprises me but is very much welcome and asks considerately. "Are you okay with the word 'pussy'? I wouldn't want to use any language which would make you uncomfortable."

"Language for... parts, anything really goes. Just no calling me a good girl or anything similar."

"How about, good boy?" He asks and the sudden spurt of slick that exits my center almost makes me light-headed, and he smirks because he's spotted this written all over my face. "Oh you like that." He growls under his breath and possessively tightens his grip on my arm. It is crazy how much I want his touch to bruise me, mark me. But then he loosens his hold and turns soft once again. "My apartment is just round the corner if you want to take this somewhere quieter. If you don't then that's okay too. Or if you'd rather we go to yours..." At this moment in time, I can't imagine this man being dominant in the bedroom. He seems so soft, and lovely, and kind.

"Shouldn't we finish our drinks first?"

"I can think of something else I'd rather drink." He may be soft, lovely, and kind, but he also has a hot streak that I cannot wait to explore.

Jason pays the bill and soon we're walking out of Joey's together so close that our arms bump together as we walk. No one gives us a second look; they obviously cannot see or feel the sexual tension that is bubbling between us which somehow makes the situation even hotter. He presses a hand to the small of my back after opening the door to his apartment building, guiding me to the elevator before he presses the button for the sixth floor. God I want to kiss him so bad, but I wait for his first move. I thought that maybe it would come when the elevator door closes or after he's shut the door behind us to his apartment, but he continues to keep things lowkey and casual.

He takes my jacket from me with a smile as I toe off my sneakers, leaving them near the three pairs he has near the door. His apartment is neat and tidy, with dark walls and lovely wooden furniture. It is cozy but undeniably a bachelor's pad. This should probably be unsurprising after being divorced twice. I explore his living room whilst he disappears to who knows where and when he returns, I'm inspecting a photo frame that is on a side table next to a reading lamp. It's full of pictures of who I assume are his children. A boy and a girl, both who look to be under ten years old.

"I got you some water." He announces his arrival in the room, and I take the cold glass from him before he directs me to sit on the couch. I would rather have another beer or something to keep the buzz going, but it is obvious that he's trying to look after me, so I have a few sips and then place it down on the coffee table next to this morning's newspaper. "Just some housekeeping bits before we begin." He says with his knee touching mine due to our proximity. "I don't plan to be too rough with you tonight, so I don't think we need a safe word or need to establish the traffic light system, but I do sometimes get carried away, but only with guys that really catch my eye... If you do need to stop though you must say something."

"I will. I promise." This is really happening.

"Good, good." He smiles warmly and his hand returns to my thigh like it was in the bar, but this time it edges higher. "So, where do you like to be fucked?" The vulgarity of the question makes my cheeks turn a deeper shade of pink, and that's before the hand slides down the crotch area of my pants. "Your pussy or your ass?" He's touching each of these body parts in turn and I restrain myself from grinding into his hand.

"Oh, I've never actually been fucked in my ass before." This is enough to answer his question.

"Okay, another time then." He hints and I think I'm grinning because he's saying that this won't be a one-time thing. "I assume then you haven't been rimmed?" I shake my head. "But you like to be eaten out?" I nod, not trusting coherent words to leave my mouth. "Let's start there then. But first..."

He slides his hand back to my thigh whilst his opposite arm snakes around my waist, pulling me closer to him. Our lips crash together as he kisses me deeply and sensually with an obvious desire. I can taste the whiskey in his mouth as our tongues mix together as well as a hint of spearmint the deeper I explore. Soon I'm moaning from the intensity of his kiss, moving perfectly in time with him. I whine when he pulls away, but the moans return because he starts to litter kisses along my jaw and down my neck, sucking the skin there hard enough to spark arousal but not hard enough to leave any lasting marks. He's doing the smart thing, but I would actually love it if he left bruises for all the world to see.

There is a burn to my skin because of his short, well-trimmed grey beard that is turning me red, but it is the kind of burn that I can get behind. "Fuck..." I groan and it makes my chest rumble. It's evidently a noise that urges Jason on because his hands fly to the buttons on my shirt so he can begin to undo them. I mirror his actions, wanting to get his blue shirt off as soon as possible. I need to feel his chest and rake my fingers through his hair there. Before today I had never thought about Jason in this way. I had never passed him at work and wanted him to fuck me whilst bent over his desk, but now I need to have him like my life depends on it.

We both lose our shirts and I just about have time to take in his soft yet sculpted physique before he is yanking the black t-shirt up over my head. He pushes me down to lie with my head against the arm of the couch with his lips on mine again, kissing with such force that I'm sure I will start to swell. "You're fucking gorgeous." He groans and then his mouth is travelling downwards so he can take one of my nipples in his mouth.

I used to find any kind of breast play quite dysphoric, but since my top surgery, I have enjoyed my nipples being pulled into the mouths of my sexual partners. I love it when they're sucked and drawn between teeth causing a brief twinge of pain that swiftly turns into pleasure, especially when my nipple is then tongued to soothe it. Jason is expertly giving one of my tits attention with his mouth whilst the other he plays with his hand and I writhe underneath him, desperate for more. "Jason... please..." I beg, but he doesn't change what he is doing. "S-sir..."

This makes him freeze and for a second, I think that maybe I've crossed a line (like screwing a co-worker isn't crossing a line!!). "Say that again." He instructs as he leans back from my chest, and I realize I haven't. He likes this. His eyes have gone dark from his pupils blowing with lust.

"Please, Sir. I need more."

He grins. And then he's giving my left tit a light slap and then the right, each tiny slap makes a needy moan crawl from my throat, but my moans turn into anticipating gasps when he begins to roughly tug my pants and boxers from around my waist in one move. "Fuck I can smell you. You smell delicious." He almost knocks the glass of water off the coffee table when he tosses my clothes to one side, and I'm left completely naked apart from my socks. He's too eager to get going that he leaves them on. "Mikey, do you definitely want to do this?"