Sensual Surprises with J

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Trans man and a cis man have sex for the first time.
2.1k words
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Author's note: This story builds off of previous tales involving the same characters: a cis man, a trans guy, and the trans guy's cis wife. This can be read independently. This is a slow burning story, so I hope you enjoy it. Language in here to refer to the narrator's genitalia is "feminine" in nature, so just a heads up on that. I'd love to know your thoughts!

----

J's placement into our lives was natural, and although we only intended our relationship to be a casual threesome, my wife and I found ourselves meeting up with him more often than not. Only a couple of months after our first encounter, J was staying at our place regularly, spending the night, and we would even sometimes do things that didn't involve ravenous fucking. The sex was incredible --- while he had finger-fucked me a few times, he was still incredibly mindful of boundaries; watching J fucking my wife was a life-changing vision that I never grew tired of. The sex was generally rough, needy, sweaty, never approaching the sensual hunger some sex becomes.

Well, that is...until it did.

J slid into the bed next to me, coming "home" after working an overnight shift at his factory job. It had to be about 7 in the morning; I could hear my wife getting ready for her work day: the coffee cup hitting the counter, the open-close of the fridge, the whir of the blowdryer. I was in that half-awake, half-asleep state, relaxing back into the sheets with the knowledge that I didn't have anywhere to be today. J's warm radiated in the bed and I nestled into his body, smiling sleepily when he shifted, moving so his hand rested innocently on the side of my thigh.

My attraction to J was still strange to me. Now close to a decade into my transition, my sexual draw to men wasn't necessarily new, but this was definitely the first time it had remained as consistent and as overwhelming as this. I pressed into him more, loving the way the warmth of his chest radiated through my back, my thigh tingling from the heat of his hand, which was lazily stroking me, still innocently.

T rushed into the bedroom then, quickly kissing us both on the cheek. "Running late for work, boys." She grabbed her shoes and almost ran out of the door. "Y'all behave," she said, a small laugh in her voice.

About half an hour passed and I shifted awake, laying still in the bed as I listened to J's deep breaths, still wrapped close enough in him to feel the rise and fall of his chest. I slipped away from him and tiptoed to the bathroom, jumping in the shower. When I heard the shower curtain move, I jumped, almost swinging out of instinct, but it was only J.

"Well, good morning," he smiled, gently guiding to the side so we could both stand under the shower head.

"Dude, you know you have to announce yourself," I grinned up at him, playfully reaching around and grabbing his ass cheek. "Surprised you're awake. You just got home."

He nodded, yawned, reaching for the washcloth and bodywash. "I know you're off today so I thought we could hang out." He said it almost shyly, staring up at the ceiling as he began scrubbing the nightshift off of him.

Butterflies raced through me and I kissed his chest, stepping back to get out of the water, aware of the way his eyes followed me, the way he licked his lips unconsciously when his eyes moved across my groin, my testosterone-enhanced clit, though soft, on display. "I'd love that. Finish up in here and I'll make us some breakfast."

---

The morning was relaxed: J lounged around on the couch in gym shorts and a t-shirt and I matched him. We watched some tv, caught up on our days. Nothing special. Around 10am, I looked over and saw him fighting sleep, his eyes closing and fluttering open in a desperate attempt to stay up. "Hey, sleepy boy." I stood up and tugged at him. "Let's get you in the bed for a bit." He groaned, but didn't fight it, shuffling to the bedroom.

"Join me." He crawled into the bed, flopping on his back and patting the space beside him.

I surveyed the scene, thought "Fuck it," and pounced on the space next to him, but threw a leg over him, nuzzling my face into his neck, kissing him gently, moving up to his jawline as he shifted, giving me access. I moved to be entirely on top of him, shivering when I felt his hands come to rest on my lower back, snaking into the waist band of my shorts. I met his mouth and sucked at his bottom lip, tugging at it quickly. "Mm. I'll let you sleep, then." I whispered against his cheek and acted to move off of him.

"Like hell you will." He quickly moved his hands from my lower back to my waist, moving his knee to between my legs and his mouth to mine, hungrily kissing me, one hand moving to my face, cupping my jaw as our tongues traced the other, as our pulses quickened.

This was new. J and my wife had certainly fucked without me, and J and I had some steamy make out sessions, but something felt...different now, more vulnerable, more emotionally invested. I couldn't think too much about it, though: J deftly sat up and brought me with him, spinning our bodies to be on top of me, one knee still between my legs. I pressed against him, reaching for his shirt hem to pull it off, desperate to feel the warmth of him against me.

His hands roamed my body as we found our rhythm in the making out. He danced along the waist band of my gym shorts, fingers threatening to pull them away but never following through, causing me to squirm each time in anticipation. I snaked my leg out from beneath him, now with him fully between my legs. My pussy throbbed, and I knew I was already dripping wet. He pushed against me, his cock hard and insistent, one hand moving to my hipbone, squeezing me, causing me to arch against him.

"I need to feel you," I gasped into him and in what felt like one fluid motion, he yanked my shorts off, as well as his own, quickly reassuming his place in between my legs. He kissed along my jawline, thrusting softly against me as I looped my arms around him. The shaft of his dick slipped along the length of my pussy: my wet mixed with his precum to create an effortless glide. I squirmed each time his cockhead hit my clit, so close to cumming I couldn't even fathom it. Still, J was slow, sensual and didn't assume what was happening --- which was great, because I didn't know exactly what was happening, either. I just knew he felt incredible between my legs and I wanted to sink into all of him, give into the way he manipulated my flesh in a way that set me on fire.

"J...I..." I stammered, pushing at him to look at his face. He looked wild-eyed, concern flashing across his face.

"Are you okay?" He pushed himself up, causing his cock to shift, the tip pressing intently at my clit. I throbbed.

"I want you inside of me." I whispered, staring into his eyes, unsure of what he would do, unsure of what I would do.

He studied my face for a moment before simply sinking back on top of me, his mouth meeting mine wholly, grinding against me gently still. "Are you sure?" He whispered into my mouth, sliding one hand between our bodies to touch my pussy.

I shivered and whimpered when his hand met my throbbing desire, arched against him when he plunged his middle finger into me, first fast, and then slow, sliding my wetness across my entirety before slipping another finger into me. I gasped, still so tight and unused to penetration this way; I almost changed my mind. J was huge, after all, and I knew it would hurt. But as he fingered me, he tapped against my g-spot and I flooded with need. "Please." I brought my legs up, spreading them as much as I could. "Now."

J moved deftly to his knees, pulling me to him so the backs of my thighs rested against the front of his. Because we did so much grinding, and because I was so fucking wet, I knew I was ready for him, but he still took his time. "Let me know if you want me to stop." With that, he gripped his cock and guided it to my hungry pussy, pressing against my hole in full for the first time. I tensed, and he pulled away. "Relax, baby boy."

I did, and he pushed again. This time, watching him watch himself enter me, his swollen tip pushed past the resistance and I gasped out, the pain ripping through me before quickly becoming a sign of more need. "Do. Not. Stop." I gritted my teeth and arched up, signalling him to enter me still.

More than J's length, I had to get used to his width. Up to this point, only his fingers had entered me, and only smaller sex toys had penetrated me at all. Nothing like J. He stayed where he was before pulling back a bit, pushing forward, a little deeper each time. I dug my fingers into his thighs as he penetrated me; before long, he bottomed out and as he did, he growled, almost subconsciously; I felt him shudder with desire as his groin crashed into me fully. "You...feel...so...good," he whispered into my mouth, licking my lips to punctuate each word.

I was scared to talk, breathless, feeling my insides adjust to this new feeling, this fullness, this need. In response, I just kissed him and raised my hips to his, trying to show how badly I needed him. He understood and began pulling out, pushing in, gently, slowly, sensually.

We found a rhythm and I gave into it -- so many years spent trying to avoid this space, trying to ignore what might feel good, and yet, here I was, letting this man fill me in ways I could not consider even weeks before. J was entering me in ways different than he did my wife; he wasn't fucking me as much as he was becoming one with me, and me with him. "Let me take over," he said, knowing how prone I was to control; I nodded, letting him bring both of my arms over my head, hold them there at my wrists as he pumped into me, steady in his pace, each thrust bringing us closer to the edge.

Before too long, he positioned himself to be supported by one arm, looking at me deeply. "Will you cum for me?" He didn't break eye contact as he spoke to me, no longer thrusting, just resting his entire length inside of me. I tightened my pussy around him in response.

"If you cum in me."

The response surprised both of us, and he smiled. "Yes."

I brought one hand to my clit, spreading my legs wider as he pumped, gasping as he lifted me a bit, now feeling the head of his cock hit my spot each time he pumped. I rubbed at my clit, shivering at the way my length rubbed against his shaft as he thrusted into me. My toes curled and my breathing quickened; J's pace did, too, but only slightly. "I'm close." I managed to gasp out, speeding up my circling on my clit, feeling him swell inside of my pussy.

"I'm...I'm..." He couldn't get the rest out, but he lurched forward, roughly pulling me to him as his balls crashed into me, a stillness overtaking him as he came deep inside of me.

Feeling him fill me was enough and I lost it with him, crying out and letting my orgasm overtake me, arching, gasping, wrapping my legs around J to keep him inside.

"Oh...My...God." I whimpered, the waves of my orgasm still crashing over me; I felt the walls of my pussy continue to pulse around J, milking him hungrily.

He collapsed onto me breathlessly. I opened my eyes, coming to my senses just a bit as J slowly pulled out of me, trembling as he did. I gasped, suddenly empty inside, my nerves on fire from the sex.

"Well, damn." My wife's voice broke the silence. J and I stared, slackjawed, my legs still spread wide open as she approached the bed. My pussy, full of J's cum, throbbed and I felt the evidence of our sex drip out of me.

I could only watch as my wife reached out, scooped up the cum dripping from my cunt, and fed it to J. She moved to unbutton her pants as J swallowed hard, tasting the mix of our cum.

"Time to clean up, boys."

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AnonymousAnonymous3 months ago

beautiful story. eveything was detailed perfectly!

AnonymousAnonymousalmost 2 years ago

really really hot. you write sexual tension/flirtation perfectly

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