A work conference connection leads to a rough threesome with trans husband and his wife (f, ftm, m)

Thanks to work, I’ve fallen behind on my gwstories postings. And, apparently, this sub has now become riddled with bad AI-written stories and clear OF marketing ploys? So let me do my part to return it to its true stories roots and try to help our hardworking mods.

This story took place a few years ago. I was at a conference for work, You know the drill. Get suited up. Make small talk. Enjoy the company per diem without doing any actual work. Living the dream, I know.

So quick about me. I’m 6’ tall. Work out regularly. Good looking. But, above all, I’m charming AF. Trust me, dear reader, I’m a completely unbiased source on this. 

Anyway, here I am, at the conference, happily making LinkedIn connections that I’ll probably never actually interact with again, when I met Chris and Teena. They were a husband and wife team in their 40s, and we legitimately hit it off. A similar, sardonic sense of humor and a mutual love of basketball will do that. And it didn’t hurt that Teena had massive breasts that were as tastefully covered as massive breasts can be. But we were there for business, so we swapped LinkedIns (of course), and parted ways professionally. 

The night was winding down and I headed back to my hotel. And, because we’re in the digital age of hooking up, I fired up a dating app. Tonight’s selection was Feeld, def the kinkiest of all the dating apps. You might remember it as Threender, the threesome app before Tinder sued them for a trademark violation (ah, the battle of the sex apps), and it had evolved into an app that was still about threesomes, but now also catered to people who enjoyed all kinds of non-vanilla sex. And, if you’ve read my prior stories, you know that I’m definitely a non-vanilla kind of guy.

So I fired up Feeld. Scrolled through the various offerings. Until I caught an ad that immediately set off an alarm bell. It was one for a couple, a husband and wife, and although they blacked out their faces (as I also did)…it looked just like Chris and Teena. I immediately recognized Teena’s stacked body. She was thicker, probably 5’8” and 220 lbs, but so much of that was in her tits and ass. Easily DDDs with a 40” ass that had me salivating. And, to my surprise, Chris was listed as a transexual man (ftm). They were looking for a man to share. Yeah, it was an immediate swipe right for me.

After 15 min, I got a notification that we’d matched. I quickly sent over a message, “I think I may know you” along with my unblocked face. Three dots appeared on the screen…and then Chris and Teena’s lovely faces were sent back with a simple “yup. We hoped we’d find you on here.” That was all I needed.

Ten minutes later, I was in their room. Sharing a drink and a few laughs as we worked past the awkwardness of the three of us sitting on their bed, planning to fuck each others’ brains out at a work conference. And then the lull in the conversation, that delicious tension when we all knew exactly what’s going to happen.

I reached a hand over to Teena’s face and gently stroked her cheek. Leaned in for a kiss. Her tongue thrusting into my mouth. She gently helped me take my shirt off. Pushed me back onto the bed. Moved her mouth down to my chest, tongue running over my nipples.

And then I felt a second head nuzzling on my abs. Chris. Kissing his way to my jeans. Unbuckling them. Sliding them down, my cock tenting my underwear, the pre-cum leaking through the thin fabric. 

Teena brought her head down as well. And then, together, they pulled my underwear down, releasing my aching cock. Fully erect. Precum leaking from my engorged mushroom head. 

I heard a sharply indrawn moan from Chris. And then his tongue along the shaft, sliding up to the head, wet lips kissing my cock. Teena joining him. The two of them sharing my cock until I felt Teena’s mouth greedily swallow it down. Deep throating it as Chris tongued my balls, going low to rim me. Switching off. Back and forth as I arched my back, moaning in pleasure, struggling to keep my head straight. But, amidst the bliss, I had one thought raring through my mind. I want more.

I gently sat up. My hand running through Teena’s hair as I gently pulled her off my cock. Chris looking up from my balls as he felt the movement.

“My turn,” I told them with a smile. And I wanted Teena first. I pushed her onto the bed. Threw on a condom and slowly entered her pussy missionary style. Chris tenderly cradling her head as I worked my cock in deep, feeling her getting wetter. Slowly thrusting my hips. Making sure I enjoyed every part of her vagina. And then faster. Harder. My hand around her neck. Slamming my hips against hers until I felt that familiar tightening in her pussy and heard her moans contort into a primal scream. I slowed down some, helping her come back down. But I wasn’t done yet.

Pulling my dripping cock out, I rolled her over. Spanked her ass and she moved into standing doggy. Good girl. Her heavy tits rested on the mattress as I finally grabbed those wide as fuck hips, sliding my cock into her pussy as she moaned in pleasure. 

I pointed to Chris, “I’m not forgetting about you. Behind me, tongue in my ass.” And, like a good boy, he complied, tongue rimming my asshole as I fucked his wife doggystyle. Harder. Deeper. Until she began squirming her hips, trying to get away, trying to avoid the orgasm. I shoved her into the bed. Held her down with my body. Worked my cock in, over and over without mercy until she started screaming, her entire body convulsing as she came a second time.

I slowly pulled my cock out. The condom soaked in her juices. She needed a break. But I have annoyingly long stamina. And I needed more. I turned to Chris with a smile. “Your turn.”

Chris looked a bit like Chaz Bono in that he had short, close-cropped hair and was a bit overweight. But, unlike Chaz, he had shockingly large breasts that he usually pinned. Easily a DDD himself. And his front hole (vagina) was almost as wet as wife’s. I pushed him onto the bed and bent in for a kiss, my cock gently thrusting in his front hole. And then, to my surprise, I felt Teena’s tongue on my ass. But, unlike her husband, she wanted to go deep. She spread my cheeks with her hands, her tongue pushing deep into my ass. I could feel my whole body tightening in pleasure, my thrusts starting to go faster. I dropped a hand onto Chris’s throat. And began to fuck him harder. Faster. Fucking the life out of him, his face contorting in ecstasy as I felt him cumming on me. 

I turned back to Teena. Pulled her to her feet, leaning down to kiss her. My fingers moving down to finger her pussy, ensuring it was wet enough to fuck. Because I wanted her again. I was so fucking attracted to this thick, amazingly dirty woman. I moved her into doggystyle, sliding my cock into her pussy, telling her to eat out her husband as I fucked her. My thumb on her ass, resting on her asshole as I thrusted. And then she looked back and told me the most magical words of the night.

“I love anal, you know?” It was all I needed to hear. My thumb was in my mouth, getting nice and wet, before I was working it in her asshole. My thumb feeling my cock inside her as I thrusted. Her head arching back, ignoring her poor husband as I fucked both her holes. 

I slowly pulled out my thumb. Replaced it with my cock. Lubed with her and her husband’s juices. And slowly worked my throbbing mushroom head into her ass. Leaving it there for a minute while Chris made out with her. And then as she relaxed, I plunged my cock in deeper. Down to the balls. Feeling her ass tighten on my cock with that wonderful pressure you can only get from anal.

Started thrusting. Slowly at first. Feeling her ass clamping on my cock. And then loosening. Allowing me to truly fuck her. To own her ass. Slamming my cock into her. Over and over, hearing her screaming in ecstasy as her whole body shook from an anal orgasm.

And it was too much for me. I pulled out. Told them to get on their knees. Tearing off the condom. My balls tightened, the pressure building.

I turned to Teena. “Open wide”. The first ropes into her mouth for letting me take her ass. The rest into Chris’s mouth. Eight full, heavy loads of cum. My calling card, an unusually massive amount of cum that has amazed every single sexual partner of mine.

Teena and Chris turned to each other and moved into a sloppy make out session, my cum leaking down the corner of their mouths as I collapsed onto the bed. Spent for the moment. And then I felt them joining me, snuggling into me, our hands finding each other’s as we held on in that post-orgasmic bliss.

And no, I didn’t endorse them for threesomes on LinkedIn.