Claire: virginity inspection and a dildo for Ramya's ass

I wanted so bad to give the weak trans girl a gigantic bitch-slap for being so careless. That small-dick gelding didn't deserve to be anywhere near Ramya's virgin pussy. But even as I think that, my pussy throbs with filthy arousal at the thought that I might have just seen my mentor finally pop her cherry.

"Everything is going to be okay," I reassure her. "Come on, let me check."

Ramya rolls over to her back, and I see the speck of blood on the pillow. She draws her knees back and spreads her own lips for me in that practiced, **** way I love so much.

I lean in close enough to smell her aroused scent and let her feel my hot breath on her damp, freshly used pussy.

I breathe a sigh of relief. "You didn't pop your cherry."

"But-"

"You're bleeding a little on the bottom of your opening. I think it was from her jamming it in at the wrong angle. You're inflamed and red, but the hymen is intact. I've seen it a bunch of times, Ramya, I can tell for sure. You're still marriageable."

I can tell she's relieved, at least not enough to call me out for that last jab. Ramya might be ready to lose her virginity, but we can agree Erin wasn't worthy. I lean in, settling between her thighs, and peck her lips. "It was a huge turn-on watching you perform. It would have been hot as hell for me if she had gotten it all the way in."

Ramya grins. "Maybe I'll let you watch when it finally happens."

"I'll be right back."

I take the harness into the bathroom and put the small dildo in the sink. When I come back, Ramya is relaxing on the bed and doesn't notice me attach the Outlaw dildo to the harness and put it back on. It looks obscene — thick, veiny, and way bigger than the lighter-skinned amateur one I wore earlier.

"Oh my God!" Ramya cries when she sees me. "You look sexy as hell with that thing, Claire. But... I'm sore already."

“I know, baby. I’m going to lube it up good and work it in real slow for you.”

I settle between her legs, the dildo impatiently poking her inner thigh as I kiss her. I gradually dial up the intensity, my tongue exploring her mouth. Ramya moans and starts undulating her thighs beneath me like she does any time I grind on top of her.

She desperately wants to come again. All that pent-up sexual tension from getting fucked in the ass by Erin, and now me grinding on her, familiar and safe with the hot threat of being impaled by the dildo.

I kneel upright and lubricate the dildo while she nervously watches.

"Claire, I don't know..." she weakly protests.

"Shh, trust me, Ramya," I coo as I press the head against her tiny slit. "The head is wider than your entire slit top to bottom," I laugh. "Girl, you're going to have to stretch a lot."

"Yeah, and it... scares... woah," she moans as I tease out her clit and dampen it with the slick head, then slide the dildo down and wiggle it at the bottom of her crease.

"I'm going to put the tip in. Tell me when you feel it start to stretch," I coach. Ramya exhales deep but doesn't object, and I ease in, watching in amazement as her tiny inner lips appear, then begin to slide across the fat head.

"Woah," she groans. "I feel it stretching. It's huge. Claire, there's no way."

The amount of trust my mentor is putting in me right now is one of the hottest moments of my life. Nothing is preventing me from driving the dildo home and claiming her virginity.

"This part might have to hurt a little," I tease.

"It does already," she says. "The opening is just raw after earlier. I guess I can try a little more. I trust you, Claire."

I give a sly grin. "Beg me. Beg for it. I know you want me to fuck you."

Ramya’s voice is shaky but full of need. “I want it to be you, Claire. Please…”

I smile and pull the dildo away from her pussy. “Good girl. But you’re already sore down here. I want this to feel amazing for you, so we’ll deflower this pretty virgin pussy later. Tonight I’m claiming your tight ass instead.”

Ramya scoffs. "You bitch. You played me."

"And you loved it."

Her butthole is still shiny with lube from Erin. I push, a little harder than I should, and the head of the outlaw pops into her tight ass.

"Oww! Arggh. Fuck, Claire, that hurts."

I grin, and Ramya giggles. Her ass burns, but it's a welcome release of nervous energy from me sparing her pussy. She's got this no problem.

"Take that big cock," I tease as I slide in the first few inches.

"Ooof. Geez, Claire. Go easy, you know I don't fuck black guys. I've never had one that big."

"Stop whining," I tease. "You good? Do I need to pull it out?"

Ramya rolls her eyes then shakes her head. "Go slow."

I push the massive dildo halfway in, watching her face the entire time. Then I slowly pull it almost all the way out, leaving just the head inside her. I lean down and kiss her deeply, our tongues sliding together as I very slowly push more and more thick inches back inside. I feed the last two inches very slowly over a minute, and she takes it all. My hips press against her ass, and the entire Outlaw is buried to the hilt. That's 8.5 inches of thick black cock buried in my mentor's tight ass.

"You are such a fucking slut," I whisper against her lips, amazed. "I can't believe the whole thing fit."

"Barely," she groans. "I'm so stuffed. You found my limit."

Ramya breathes deep and slow, continuing to relax and adapt to the huge dildo.

I keep the thick dildo fully sheathed, savoring the moment while Ramya trembles. The intense stretch feels surprisingly good despite the burn, awakening a deep submissive thrill in her. She's being opened wider by the woman she mentors than any guy that fucked her. The trust and intimacy of it all has her dangerously close.

“Can you orgasm from anal?” I ask between kisses.

“Yes if I rub my clit,” she breathes.

“Then do it for me.” I slide the dildo out half an inch to give her room.

Ramya’s hand slides between us. She rubs her clit in fast, **** circles with the huge dildo buried deep in her ass. It doesn’t take long. Her body suddenly tenses, her back arches, and she cums hard with the entire Outlaw stretching her ass, moaning my name into my mouth.

I pull out slowly, leaning up so I can watch her well-fucked asshole. For a few beautiful seconds it stays gaped and open. Ramya’s strong ring then begins to wink and slowly contract, pulling itself closed in tired, fluttering pulses. Even after it seals, her once-tight little starfish looks thoroughly ravaged: puffy, reddened, and slightly agape at the center, the delicate wrinkles loosened and shiny with lube.

I did that.

Easily one of the hottest moments of my life, one I will cherish forever. I kiss my mentor again, remind her how sexy she is and how much I love her, then roll off her to go clean up the dildos.