“So, right, a little anatomy. These are the outer labia. On us, the same little patch of skin fuses together pretty early in development, forming the scrotum. Reach down and feel the ridge along the center of your balls. Found it? That’s the seam.” I peek, to see most guys were, in fact, gently playing with their balls, or playfully recruiting a lab partner & checking his. “On trans guys though, gonad tissue stays inside instead of migrating down to form the balls. So the skin of the outer labia is a little thicker, the lips themselves plumper, than a ballsack.” He demonstrates, pinching each of my labia between a thumb and forefinger, rolling the smooth, shaved skin between his fingers, gently tugging them apart to show off my inner folds.
“Now, his cock, like I said, grew pinned against his body at an angle. He’s had his released, and had some of the inner labia moved to close together underneath. In guys that haven’t, you’d see the ‘legs’ of his cock or clit—whatever he calls it—extend down to form the inner labia, the thinner lips around the hole. Instead, they stitched the remaining bits together to extend this perineum down to his pussy, so he’s a little tighter than most.” A finger traces ever so lightly over each of these landmarks in turn, slick now and frictionless as a hocky rink.
“Above the pussy hole we have the urethra. Differences in sounding are more of a graduate-level class, and most of the time you actually want to go easy on this part. The piss hole is sensitive, sometimes uncomfortably hypersensitive or easily inflamed. So while you might stroke his cock upppp”—he pulls me to my full length, out away from my body—”and downnnn”—sliding his fingers down the shaft until they press into the base of my cock, then continuing his path down. As they left my shaft, though, he let his thumb and forefinger separate again to each trace out along the edge, along the inner fold of my lips—”you might want to go arouuuuund the urethra before you end the movement insiiiiiide him—”he finished, as he plunges his index finger inside me.
He repeates the movement one more time in silence, pulling out of my thoroughly-teased pussy and up the shaft of my cock till he’d brought it back to it’s apex, then repeating the downstroke while adding a second finger inside me.
He withdrew both fingers and shifted his body so he was facing me enough to fill my hole without straining his wrist. He flashes me a smile before turning halfway out to keep addressing the crowd over his shoulder, working my pussy in long, slow strokes with his hand.
“Look how fucking wet he’s getting. That’s one of my favorite parts. The more he wants you, the more his body gets that hole ready for you. I love reaching down to find he’s already fucking ready to slide my cock into. It’s kind of romantic to not even pause to lube up, you know? Just stay in the moment and enter him whenever you choose. And I love how easy it is to make him come hands-free. In fact, I think he’s going to be a good boy for me and show you in just a moment, aren’t you baby?”
I’d been so lost in my own sensation that I barely caught my line. It felt like a k-hole made of lust. I moan ‘Yes sir’ a moment later than made sense, as he transitioned to not touching my cock at all, just plowing his soaking wet fingers slowly and firmly into my hole.
“Now, there’s a lot of debate about whether the G-spot is a real thing anatomically, if it works on everyone with a vagina, etc etc. My favorite theory is that it’s a little intersection of nerves derived from the same tissue that becomes a prostate in us. It’s in about the same spot, and while it’s a little less reliable than the p-spot person to person, Andy here likes it when you stroke his. On his back like this, you just reach in with your palm up, and curl your fingers to make a ‘come here’ gesture inside him.”
I moan and squirm some more. My arms were getting tired from holding the table legs over my head, so I instinctively start to reach for my cock. But Daddy tut-tutted, so I put them at my sides, gripping the edge of the narrow table instead, and using the leverage to rock my hips and push his fingers in deeper.
Something about Daddy’s soothing instructions, always delivered with just a little wry smirk, really does it for me. He turned back towards me and shifted from the professorial tone he used to address the room to a more intimate baby talk meant just for me: “Yeah that’s a good boy. Show Daddy how much you appreciate it when he fills your pussy. Good boy. Uh-huh. Come here. Come for Daddy. Help Daddy show all the nice men how much you love being fucked. I’m gonna let a bunch of them fuck your pussy later. And you’re gonna be a good boy and come just like this on their cocks, come nice and hard just from getting filled up—”
I lose it. My whole body begins convulsing. Daddy matched my passion, uncurling his fingers from the more subtle play on my g-spot in favor of simply pumping his hand in and out of me, hard and fast. I can hear the wet smacking each time the rest of his fist makes contact with my body, the messy squelching as he pulls out. My first orgasm had been delicious, born of teasing and careful ministrations. This was more feral. I thrashed and bounced against his penetrating hand as hard as I could. My back arched off the table as though I were being electrocuted. Daddy rolled with it easily, tracking the tilt of my pelvis so he never let up. He kept up the patter of praise, but in the hushed, almost scared tone he might use on a cornered animal “Good boy. Good boy. Come hard. Squeeze my fingers. It’s ok. Daddy wants you to come hard for him. Good boy, good boy, come when you get fucked.”
It seemed to stretch on for minutes. I couldn’t say for sure, but I heard him working to keep up a string of dirty talk as I kept coming and coming. He looped around and repeated many of the same bits, so it must’ve lasted for quite a while. I didn’t care.
Eventually I collapse. My arching back fell onto the table, and I pulled my body up and away so his fingers left my drenched pussy. At the same time I gave him three quick little taps on the forearm, our signal to tap out. At that, he knew I couldn’t take any more, and aborted any attempt to track and re-enter my hole.
Daddy held up his hand. “Look how juicy he gets! It starts with arousal but an orgasm or two really gets his hole in prime condition. I strongly recommend a warm-up orgasm with all your trans boy bottoms. They generally don’t have a refractory period like we do, once you get ’em going they can be really insatiable little piggies. Then, by the time you do fuck them, everything will be nice and wet. Just look at this”
He spread me back open. His speech was becoming faster and more passionate. I can tell he’s having as much fun as I am with his little private sex ed seminar.
“His little cock is hard as fuck, it’s almost doubled in size from when he’s soft. And while I was fingering him, I made sure to spread his natural lube all over the outside of his pussy too, so there’s no chance of friction later. I’ll be able to just aim my cock in the general direction and thrust into him, it basically funnels you in. You can probably see his juices glistening everywhere, from his cock down to where they’re dripping onto his ass. And the great thing is the taste—sweet and salty, a little funky. Those of you who’ve been with cis women will sort of recognize it, but testosterone gives him a muskier, more masculine flavor, closer to ball sweat than girl-come. You can have all kinds of fun fucking him. Having him suck his juices off your cock. In a threesome you can spit roast him and switch holes with your co-top any time you want. Of course, usually there’s STI risk if you don’t use a condom, but you don’t have to worry about enterics or fecal matter. So you can really go to town. There’s only one real limit: front to back is fine—taking a toy, finger, cock, whatever out of his dripping wet pussy & pushing it into his ass—but never go back to front. The natural flora aren’t compatible & he can get a mild but unpleasant infection from getting butt stuff in his pussy. In a group sex situation, if you’re gonna go from fucking ass to fucking puss, switch out condoms or take a breather & go wash up.”