Give Me A Squeeze

Author's note: Hello! This is my first story in a little while. Just a warning it does contain references to a past physical assault and transphobia.

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 can see that he's hurting. Hurting because I'm hurting. I wish I could make it stop but I just can't forget easily. Three weeks ago, Jason and I went to a gay bar together. I remember being so excited because I had wanted to do that for ages, but I didn't think it would be his bag. He only did it for me, I know that, but we did have fun... mostly.

I went outside for a smoke. I'm not a big smoker, but there is something about a bar that gives me an itch to have a puff or two. It was easy to commandeer a cigarette and a lighter from a couple who complimented my shirt before suggesting that I should go home with them. I politely declined of course. I am into a lot of kinky shit, but I am all for monogamy, and Jason is the only fella for me.

He stayed inside because he needed to relieve himself, but when he came out to check on me, I was being pushed against the wall of the bar with a big guy's hands around my neck. It wasn't a naughty encounter, it was a bigoted attack. Someone was pressed that I, a transgender man, would even consider frequenting a gay bar. He spat in my face. Told me that I was catfishing because I have a pussy. I was so scared.

Jason pulled him off me and punched him square in the jaw. The guy spluttered, but we weren't going to hang around for the retaliation. Jason grabbed my hand, and we ran. All the way to the subway. I apologised but he was horrified and told me it wasn't my fault. But it was because I took him there. He didn't want to go in the first place.

I will get over it. I know I will. But it is getting in the way of our sex life. I know this should be the least of my worries, but I hate that Jason is holding back because of me. "Do you want a drink?" I tear my gaze from staring into space to my partner who is hovering in the doorway with a bottle of soda in one hand and a bottle of beer in the other. He looks worried. He seems to always look worried now.

"I want you to stop looking at me like I'm a wounded animal." I don't expect it to come out, but it does. "It was not the first transphobic attack I've been a victim of, and it won't be the last."

He looks down at the striped socks his son got him for Father's Day and sighs before he looks back at me. "It's not that." I cock my head at this. "Well, it's not just that." He clarifies before sighing again but this time with his shoulders slumped. "You were frightened of me." Oh.

I buried my feelings for a few days after the incident, pretended like it never happened, and it hadn't affected me. That resulted in me freaking out when we were next fucking. Jason is a Dom, and I have loved his hands around my neck, squeezing lightly (and sometimes tightly) ever since we first hooked up. But him doing it that night stopped me from breathing because of panic. It is like he's been scared to touch me ever since and maybe that's valid. "I'm not scared of you. I could never." He doesn't look like he believes me. "It just... took me by surprise."

Jason sighs yet again but he does move towards me, putting down the bottles on the coffee table as he passes it. "Mikey..." He starts by saying before taking a seat beside me on the couch, so close that his right knee bumps against my left. "What happened at that bar, happened. You shouldn't be numb to transphobic attacks, that's wrong. You were assaulted."

"You're right, but not by you." My tone is pleading. "I shouldn't have screwed things up."

"Mikey." He sternly states. "This isn't your fault."

"Maybe, but how we were in bed together, scared you. That was wrong." And it is hard for him to disagree. "Jason, I want to be touched by you. Squeezed by you." I will beg if I have to. "Please let me prove that."

Jason doesn't answer verbally. His initial response is a timid nod, but then he hooks his fingers in the waistband of my basketball shorts and pulls them down roughly with no hint of pre-amble. As usual when I'm lounging about the house, I'm not wearing any underwear, so my boy pussy is exposed to the elements. "Sit on my face." He instructs and immediately I'm feeling weak at the knees. He hasn't touched me down there in a fortnight and it has been impossibly long.

It is clumsy. Me standing up and kicking off my shorts whilst he reclines on the leather couch. It is cold in the winter, but at least it is easy to wipe down if we do ever have fun in this very spot. The first time I straddled his face here, I was nervous about hurting him in some way but now we are experts at finding the right position, to get us both comfortable. "You smell divine." He announces before blowing cool air over my pussy lips and my T dick. It is almost unfair teasing, but he is quick to put me out of my misery.

His tongue glides over my slit and it feels incredible after a couple of weeks of abstinence. We are very sexually active, both massive horn dogs to be honest, so it has been nearly impossible. He hums as if I'm a tasty meal, and I know now is the time to prepare myself for the throws of my pleasure. I grip the back of the couch with my left hand whilst the palm of my right presses against the arm of the chair. He gives me barely a second to settle before his tongue begins to work its magic.

I remember the first time I experienced oral sex. I couldn't believe how something so wet and sloppy could be so good. A person's fingers are nothing compared to a warm, wet, soft tongue on my boy pussy. Some of my more recent partners have been surprised that I don't find the experience dysphoric as a trans man, but how can I when it feels this fucking good?

Jason is also an expert at it. We hadn't been together long when I realized how completely in tune he was with my body. He knows what order to touch me, what areas to give more attention to, and the ultimate pressures to get me over the line. He treats my clit like a tiny dick and does his best to give it a blow job but with his tongue leaving it intermittently to return to my slick, vaginal opening.

The noises that fill the living room are obscene. The sounds of sucking, lapping, and my moans are almost musical if not a bit desperate. I don't even care that someone may see us across the road through the open blinds. In fact, that thought has the ability to turn me on even more. I don't know how that's even possible -- I'm already incredibly riled up.

It has been so long since we've done this that it doesn't take me long to finish. I grip onto the back of the couch, so I don't crush him as my release spurts out of me and all over my lover's face below. My moaning pants turn into a cracked squeal as I cum and with his tongue continuing to lap at me, my orgasm seems to be everlasting. My muscles keep tensing and then relaxing, my breath stutters in my chest and I feel sweat drip from my skin.

Eventually, he relinquishes when I hiss at him wrapping his lips around my little dick. This is not the position to be in when being overstimulated and I can barely hold myself up at this point. He taps my naked thigh twice, signalling me to hop off. His face glistens with my juices when I shakily climb off him so instead, I'm sitting on the edge of the couch. I can barely breathe but in a good way. My clothed chest heaves and he watches this with a smirk on his face. Nothing boosts Jason's confidence more than making me cum. "How was that for touching you?"

"It was... It was..." I just chuckle under my breath, and he smiles at me knowingly. He felt how I convulsed, and heard how I moaned, he knows just how it was -- but it wasn't quite what I was expecting. "There wasn't much squeezing though."

"Baby steps. I just wanted you to relax before we go back there." He then sits up and helps pull the t-shirt from my sweaty body, leaving me completely naked whilst he is still fully dressed. It almost feels unfair, but I know it won't be for long. I can see his hardness is outlined by his jeans, and his willpower will only take him so far. "Now how about we take this to the bedroom?" I don't need to be asked twice.

I am so... euphoric from my release that briefly I can forget about the incident a few weeks ago and what got us here. When we're up off the couch, and his hand leads me to the bedroom by pressing at the base of my back, I feel supported. I meant what I said to him. I'm not scared of him. I could never fear him.

His hand shifts from my back so he can take my own and guide me carefully to sit down on the pristinely made bed. It is one of many of his sexy qualities, how house-proud he is. Before we started hooking up, before we fell in love, most days I couldn't be bothered to make my bed. There was no one to see it and I lived alone, and the art of casual sex seemed difficult as a trans guy. Perhaps that shows our age difference. He has a maturity that I don't.

The sheets are navy. We've joked many times that perhaps we need a different colour as this one shows signs of our lovemaking. Jason once said that he doesn't care because it is the artwork of our passion. I called him out for being cheesy, but it actually made my insides flutter. "Which hole do you want me in?"

"Are you going to put your hands around my neck?" I ask a question to his question, making him raise his brow.

"That's the idea."

"Asshole." I tell him, but the quizzical look doesn't change. "Acts as more of a distraction." It is more difficult to take him there thanks to his large size, so maybe if I'm so focused on not being ripped apart, I won't fluster at his hands being wrapped around me.

Jason nods, like he understands, and pulls open the drawer to his nightstand. I watch him silently (apart from my heavy breaths) when he retrieves some winds of black rope, a large bottle of lube and my trusty vibrating pussy plug. A shiver ripples down my spine. "Seems like you have a plan then." It is meant to come out playful, but it turns kind of nervy.

His expression which was one of intent softens when I say this. "We don't have to use it if you don't want to." He would never push me further than my limits -- unless asked to of course.

"I want to." And that's enough to get things going again.

How he binds my arms and legs isn't very tight. With rope at my wrists tied to the headboard and at my ankles, making me spreadeagle as they're fastened to posts at the foot of the double bed. It is one of the reasons why Jason picked this bed, he told me the fourth time we slept together. It is incredibly hot, and although we aren't regular users of rope, it always adds a bit more spice to the situation. I know I am free to move a bit, but the restraints give the impression that I can't, it is a mental thing more than anything, but I can't deny that the sensation of the rope rubbing against my skin is making my whole body hot with want. My boy pussy is already back to leaking.

Jason may be acting all cool from the outside but in reality, he is very turned on. He palms himself through the fabric of his jeans for a few seconds, to relieve some of the strain, and I appreciate what he's going through to hold off. The mattress dips as he joins me on the bed and he's straightaway turning on the small vibrator. A breath hitches in my throat. "You good?" He double checks and I nod enthusiastically. "Good." He states and then he is roughly plunging the toy into my soaking pussy.

My back arches on the bed and I pull at the restraints making him lightly laugh, clearly proud of himself. The vibrating pussy plug is probably one of his best purchases. It makes the anal experience out of this world. I close my eyes and focus on the sensations it gives me as it presses over my special spot. It isn't long before my eyes snap open though with a hiss as cold lube is poured over my asshole. "You would have thought you would be used to the feeling by now." Jason teases and I try to scowl at him, but I cannot muster it because of the tip of his finger against my ring, to test the resistance.

It has been a couple of months since we've last gone back there so I'm tight. This is basically proven when Jason inserts the finger and he is met with a lot of defiance and I tense, preventing him from going any further. Jason takes his free hand and gently trails his fingertips up the inside of my thigh a few times to get me to relax, allowing the finger in my hole to sink deeper. He rocks it in and out, first watching the digit disappear me and then peeking at my face, to see it beautifully twisted with need. He removes his hand from my thigh to find the lube bottle near my knee and squirts a lot of it on another finger which then joins the first making a strangled moan leave me which transforms higher in pitch as Jason scissors his fingers. "Fuck." I curse at the ceiling, and I cannot help but think about what this would be like on the outside.

Once happy that I'm prepared, he removes his fingers with a squelch and begins to awkwardly get off the bed earning a cry of displeasure from me. "One second baby boy." On other days he would probably be more dominating, and more demanding, but he's being careful with me because of the circumstances that have got us here. I don't mind having to be patient though, because Jason then quickly strips before my eyes and I'm thrumming with so much want that I may vibrate off the bed even with the rope retraining me. Subconsciously, my tongue darts out to wet my bottom lip from the anticipation.

It is amazing that even after all this time, the sight of Jason's cock makes me drool. The thickness, the length, the veins bulging from the raging member. Watching him pump it a few times as he goes to grab a cushion from the small chair in the corner of the bedroom is entrancing. He signals for me to lift my hips which I manage to, slightly, as he slips it under my hips to ensure a more comfortable angle for us both.

Jason is sure to grab the bottle of lube from the nightstand before clambering back onto the bed. He generously slathers some onto his hard dick and adds another dollop to my hole before he presses the head of his cock against my entrance. Even with all the preparation, it is a tight squeeze as he pushes inside. I gasp at the intrusion. "Remember to breathe." He reminds me whilst stroking my torso.

With the loving actions and the vibrating plug inside my boy pussy, my ring of muscles does loosen, allowing for more and more of him to slide inside of me. Like usual, once he starts, he almost can't stop, and he is bottoming out, filling me up with eight inches of goodness, and it is difficult to remember how to breathe, even with Jason's instructions. I can feel everything. How he throbs, the veins, how I stretch to accommodate him. Momentarily, he stays still and the only noise in the room is our heavy breathing which has synched. "Color?" Jason eventually questions and I raise an eyebrow at him. "Yes, we are doing this today."

He really must be worried, but there are too many feelings going on right now to be touched by this. "Green," I reply with a strained voice.

At first he is slow, mindful not to hurt me, stretching me out wonderfully and watching his cock vanish inside whilst biting his bottom lip. Each thrust gets deeper and the sound of sex fills space. Skin against skin, tasty moans. It doesn't take him long to pick up the pace like it has suddenly hit him that it has been a while since they've been like this. His breathing loudens as do my moans. "You feel fucking amazing my good boy." Jason praises and I feel my blush.

I spot something change in his eyes. Like he is thinking as his hips thrust rhythmically. I know what he's thinking when he brings a hand to my neck. My heart, which was already beating quickly and loudly, somehow gets faster and louder. It is like I can hear it, and that's before he even makes contact. It is gentle at first, a vast juxtaposition to the speed and intensity of his thrusts, but after a brief inspection of my features, as if he is checking in, he squeezes me... but suddenly I am back outside that bar.

My eyes go wide and everything about me tenses, making me tighten around Jason's dick. "Yellow." I mutter with panic and immediately he pulls his hand away and stills, the only thing that doesn't stop is the buzzing from the plug inside my pussy. Jason even raises his arms to show that he isn't a threat. He doesn't need to do that; I know he wouldn't hurt me.

"Do you need me to pull out?" He asks carefully and in a reassuring manner, pushing back the loose strands of hair that have matted against my forehead with sweat.

"No, no." I repeat to persuade that I am being honest. "I want to keep going. It feels good."

"Just good?" He teases, a smirk ghosting his lips.

"Alright, it feels incredible." I confess and he manages to chuckle lightly -- but this may be from nerves. "The neck thing too I think."

"We will try it again and if it is too much say yellow, and we can finish without me touching you there or red for us to stop entirely. Okay?"

"Yes... green." Jason falters for a second. "I swear I am fine. Now fuck me so hard that I can't walk tomorrow I beg."

"I would love to hear you beg." He flirts and seductively runs his index finger from my temple and down along my cheekbone before settling against my lips. "But not tonight." He adds, before starting to move again.

Jason doesn't press any weight on my neck straightaway. He just continues his heated movements, but he switches the angle, so the jerk of his hips makes the tip of his cock brush the vibrating walls of my pussy but from inside my hole. The whine that leaves my throat when he does this has his eyes darkening with lust. He loves it when I am at his mercy like this. He loves me as his sub. So I continue to allow myself to groan loudly as I see nothing but stars. "Look at you. You take me so well." He praises me, knowing that this is something that turns me on. "You love taking cock up your ass, don't you?"

"Y-yes."

"Yes, what?"

"Yes sir." And now Jason can't hold back a loud, guttural, moan. He then goes for my neck again with a surprising surety, as his fingers wrap so tightly around the hot skin that there is probably a chance of leaving a mark. This time my reaction isn't me tensing up, but I feel myself let go further and Jason spots how my pussy starts to leak copious amounts of fluid. It feels so good.

With one hand around my neck, the other finds my plump clit, and he is stroking it in time with his thrusts, my hips lift a little from the cushion to meet the movements needily. Jason is leaning back on his legs now, not wanting to risk collapsing on top of me yet showing his athleticism despite being in his forties. He continues to impress me. I will have to tell him that when I have my breath back. "Harder." I plead and Jason blinks a few times but does try to piston into me more forcefully. "No." I correct. "Squeeze me harder."

Somehow in the scorching heat of the moment, Jason raises his brow, forming a sort of question, double checking that it is okay. I do nod amongst the fevered movements, something that my partner manages to perceive before he squeezes my neck harder. "My good boy." The pressure on my windpipe builds and my lips stay parted as moan after moan tumbles out freely. I don't need to tell him how close I am, we've been sexual partners long enough for him to know the signs.

The increase in my moans, in both volume and intensity, to the point that any breaths I can take are shallow, almost like gasps. My juices are also slicking up his fingers that continue to rub at my tiny dick, encouraging him to chase down his own orgasm by speeding up his thrusts with any energy he has left. They become disordered, with messy movements and a chorus of grunts and moans, but it is bliss.