Claire: fucking the trans girl in the ass

I get to tap this:

I look through the cracked door to see Ramya and Erin peck on the lips in greeting. That's a good sign. Erin has styled her hair well and cleaned up after the beach. She's in a loose skirt that comes above her knees and a tight top that hugs her small breasts.

Ramya wastes no time once the door is locked. She unties her robe, exposing her shaved pussy to Erin's gaze. "Oops," she says with a grin.

Erin comes in closer. "May I?" she asks. Ramya nods, and Erin parts the robe more, enough to see my tall mentor's breasts. She cups one of the heavy hangers and lifts it.

I come out of the bathroom now, naked with the strap-on dangling between my legs. Erin laughs. "Ooh, is that for me?"

I ignore the question and say, "Your turn. Show us."

Erin lifts the front of her skirt. She's not wearing any panties, and her tiny cock is there in full glory, little more than a nub, a shriveled noodle atop a deflated sac. "I don't have to tuck anything in this skirt, it's great."

We pull her onto the bed and start kissing. She is timid but eager, melting between our taller, stronger bodies. Her breasts are small but sensitive and enhanced through hormone therapy.

I laugh as Ramya sucks Erin's tiny, limp, uncircumcised noodle of a cock. She's patient, but I can tell she's getting annoyed that she can't get Erin hard. Ramya, the self-proclaimed fellatio expert, has just met her biggest challenge: a trans girl with a penis and no balls. She tries everything: first taking all of her cock into her mouth and sucking, then leaving it out and flicking her tongue across the sensitive underside. She even brings her large, sagging breasts into play rubbing her cock, but that's challenging with the small penis. Ramya reaches down several times to tickle or cup her balls, then remembers there's nothing there but a deflated scrotum. Our castrated lover has zero potency.

"My turn," I say, and I slide my hand in place of Ramya's. Erin reaches down and pushes me lower, guiding me to her anus as she draws her knees back.

"The boner pill will kick in. You don't have to wait for that to fuck me."

I grab the lube and start fingering her ass. Our guest struggles even to get used to one finger. We coach her gently: “Relax… bear down like you’re pushing me out… that’s it.” It takes a long time before I can comfortably add a second finger. By then Erin is whimpering but taking it. When I can pull the fingers out and insert them again without feeling her clench and resist, I know she's ready for cock.

I stroke her hair and smile. "I'm going to fuck you now, okay. We'll go slow. You can stop any time." She nods.

“Deep breath,” I coach. “Push out as I go in.”

The dildo isn't a big jump from two fingers, but Erin fights it. On the fourth attempt, the head finally pops past the tight ring. Erin whines immediately. “Wait— take it out, please…”

“No, baby. Just wait. Don’t clench. It will pass,” I murmur. She winces and gasps, but once the head is in, I know she's conquered. I ease a few more inches into her incredible tightness.

"Ow, fuck," she complains.

"Relax, you did it. Stop fighting it," I coach. I glance at Ramya. Erin's fragility is exhausting. Ramya and I have both taken bigger cocks in our assholes and would never struggle like this.

Erin exhales deeply, and another two inches slide into her ass with me barely pushing. Our eyes meet. "Good girl," I praise her.

She lights up at the words, clearly loving the gender affirmation. “It’s… better than last night,” she whispers.

I start thrusting gently, going deeper until I am riding the full length of the dildo into her. Ramya watches intently lying next to her and stroking her hair. She has her legs parted and is lazily masturbating. When I glance again at her, she slides a single finger into her own virgin pussy and winks at me, and I swear if I could touch my own clit now, I'd come in seconds.

Erin's tightness continues to fade, her sphincter relaxes, and pleasure climbs as I fuck her harder. Her tiny breasts and penis jiggle from my movements. "It's good. I like it. Thank you so much." She's grinning, and her tiny penis has come out of hiding, a solid three inches of shaft showing with a shiny drop of something oozing out the tip.

I grab her cock with my thumb and first finger and massage it while I fuck her, and Erin grows more until she tops out at almost five inches with a bit more than an inch in diameter maybe. Smallest one I've seen, adorable and perfect on her frame and fitting perfectly with her new submissive lifestyle.

I keep fucking her for a few more minutes. I want to make sure she's broken in really well and gains the confidence and skill she'll need. When I can pull the dildo out all the way and see an impressive gape that lingers, I know I'm done.

"You did it, Erin. Good job, girl," I say. "I have a bigger dildo if you want me to break you in more. Or you can take a turn on me now that you're hard."

"I want to fuck you now if that's cool, she says breathlessly.

Hard and ready for us: