Claire: our night out, and a dildo to ruin me

A month of Ramya’s coaching and I’m a different girl. She’s relentless with wardrobe audits, makeup lessons, technical learning, and networking assignments. My clothes get tighter, my posture straighter, my smiles confident.

She's never too busy for me, even as she kills it at her new job as an executive. She tunes my online dating profiles, and we debrief every date over wine at my place: what worked, what I learned about the man, what made me wet.

She never pushes, but the message is clear: lose the virginity, safely, soon.

On one of the dates, I give my second blow job. This time I'm mentally prepared and swallow the ejaculate with no issues. It's a weird taste, but I know I will enjoy it the more I practice.

One random Friday she texts: Dinner at mine after CrossFit?

No dates lined up for either of us, so we cook, drink, laugh, and at 10 p.m. decide the night’s too young to end.

She transforms me in her bathroom mirror: Light brown hair styled with some body, tasteful makeup, a top that plunges low enough to turn my large breasts into weapons.

"Holy shit, I'm hot," I whisper in the mirror. "It doesn't feel like me."

Ramya stands behind me, hands cupping my breasts through the fabric, lifting and jiggling them with a wicked grin. “No, this is you. You have no idea how sexy you are, Claire. Own it.”

"Okay. Hell yes. Let's go," I say. Ramya is ahead of me on the wine tonight, so I drive. I owe her from last time.

We want to leave our inhibitions behind, so the bar we pick isn't close. Western theme, line dancing, chaos. We are not in Western-themed outfits, and it doesn't matter. Men swarm, this time to both of us.

I'm more in my element here. I'm from the country. This is my crowd. Or more accurately, this is a bunch of city folk pretending to be my crowd.

I make out with a cute cowboy on the dance floor, drunk on attention more than ****. I can feel his erection against me through his pants, poking under the oversized belt buckle. I have to pull his hand off my ass twice, but I'm not about to kick him out of the saddle.

Ramya’s wrapped around a gorgeous tall and muscular black guy in a cowboy hat, but she keeps a protective eye on me.

When my cowboy invites me home, I hesitate. Ramya appears at my side, thigh pressing mine, a possessive arm around me. She's drunk off her ass, probably for the first time in ages. I'm so happy to give her a good night out. "Oh he's cute." she says, and my cowboy tips his hat at her.

“He wants to take me home,” I tell her.

"You're wasting your time," she shouts over the loud music. "She's still a virgin."

I'm horrified. Ramya's mentoring is the only thing that keeps me from crawling into a hole. My cowboy's eyes go wide, and Ramya is pulling my arm, leading me away. "Wait, let me say goodbye," I say and pull my arm free. I come back up to the cowboy and get in close. "I have to take her home anyway. It wasn't going to happen for us tonight. Let me text you my number."

He stares at my tits as he gives me his number. While I type, he asks with his voice in a thick southern drawl (he might be the only real cowboy here), "You ain't been fucked yet? A pretty little thing like you?"

I chuckle. My pussy tingles at the thought. There's a condom burning a hole in the back of my cell phone case if I want the cowboy to pop me.

"She's right about that. But she's wrong about me being a waste of your time. Call me." I lean up to kiss him as Ramya drags me away.

She steers me to the exit. "Ramya, I'm super horny," I whine. "What the hell was that?" I'm laughing, because I love her so much. But that wasn't cool!

"I'm not sharing you tonight," she says, suddenly sounding a lot more sober.

"Okay. Well, I wasn't going to leave you here to catch an Uber all the way home," I say. I really like her endearing, possessive attitude towards me. "But I could have led him on a little longer. What about that hot black guy you were just hanging on? Damn, Ramya, that is literally my biggest fantasy right in your lap."

"I gave him my number. I'll hookup with him another night," she says matter-of-factly.

"You're such a slut," I tease. "An absolutely horrible influence."

I drive us home. "Your place," Ramya says as I lean out the window to punch in the code to open the gate. "I want to talk more about your virginity. You're keeping secrets."

"Uh oh," I laugh. But I've grown to trust her so much, I'll talk about sex with her all night long if she wants. I wish she'd tell me more about her own escapades. I invite her in and pour drinks. It's after midnight.

"You're Baptist, so it's not too surprising. Tell me more," she demands.

She listens while I spill: the weight, the loneliness with no steady boyfriend, the fear no one will want the late-blooming virgin. She asks if I'm waiting for marriage.

"I thought it was. I don't know. It's easy when the men aren't trying to get down your pants. But now I'm older, I'm more comfortable with my body, I'm in a new town. I think I'm ready."

I see tenderness in her eyes. "I sympathize. Indian culture values female virginity for marriage. I'm sorry for pushing you to do it without asking you these questions."

"I wouldn't change a thing with you," I assure her.

"Are you horny? Do you want to get laid?" Ramya asks with a laugh, lightening the mood.

"Oh hell yes," I say. "I masturbate... often." I put my hand over my mouth, embarrassed, but my mentor just laughs.

"Let me see what I'm working with. Take your clothes off."

"What?" I stammer. "Wait, really?"

"You've seen me."

"Just your boobs," I scoff. An eye roll, then, "Fuck it," I stand, peel off the top, unclasp the bra. My breasts spill free: heavy, perfect shape and perky, nipples already swollen from nerves and wine. I can barely fit into a D-cup bra, and that's after the weight loss.

I turn, push down the jeans down. I pause long enough for Ramya to complement my ass in the thong she made me buy, then I push down my last piece of clothing and turn, completely exposed.

I spread my legs just a little, letting her see everything: the smooth skin, the thick, prominent lips that hang longer than most girls’, dark pink and glistening. My biggest insecurity, right in my mentor's face.

Ramya’s breath catches. “Jesus, Claire,” she whispers, eyes fixed between my thighs. “Those lips are gorgeous. Full and just made to be kissed and suckled and spread wide. You are blessed. The shaved look really brings them out. I love it."

Heat floods my face, but I don’t cover up. Her praise feels real, and I like her hungry look. She has no idea how good she just made me feel. I almost cry, and the best I can do is eek out a "Thanks."

"Your tits are perfect, of course. I'm not surprised at all," Ramya says. "Claire, you're sexy. That is a killer body. You've worked so hard for it."

"Thanks. And I have a confession,” I say, voice shaky. “I sort of tried sex once, right before I met you. Hurt too much.”

"Oh." Ramya’s eyebrows shoot up with genuine surprise. "Did he at least break you in for the next guy? Were you penetrated?”

I shake my head, cheeks burning. “Well, yes, partially. I don't know. Then he couldn't go deeper before I made him stop."

She leans back, studying me with that mentor smile. "You poor thing. You didn't pop your cherry yourself to be ready?"

"No. But..." I bite my lip. The silence stretches. She’s waiting, curious now. "I can't believe I'm going to talk to talk to you about this."

She takes the bait. "Tell me right now, Claire. What is it?"

"I'll be ready next time. I bought a dildo."

Ramya is delighted and laughs softly. “You did? How did that go?”

"I... haven't tried it yet."

"You're scared," she teases.

"No. I got this. But what's the rush?" I counter.

"Show me. I know you want to."

I bite my lower lip, enjoying the flirting. "I'll be right back."

I disappear into the bedroom, heart racing, and return with the big black dildo hidden behind my back.

Ramya waits, eyes curious.

“Don’t laugh,” I say, grinning despite the flush on my cheeks. I hand it to her. Her fingers brush mine as she takes it, and her eyes widen.

"Holy big black cock! Claire, you dark horse!” She looks up from the dildo. “Black guy fantasy?”

I just nod.

Ramya scoffs. "Well that will definitely get you ready. It's been a while since I've taken a real one this big. You'll love it if you can manage to get it in."

"The guy who couldn't fit was white but pretty big. I'm not taking any chances."

Ramya's gaze shifts from the dildo to my crotch, lingering like she’s already imagining it inside me. She drags the thick tip along her lower lip. “Claire... Sweetheart... I want to be the one who opens you,” she says, voice low and rough.

My breath catches. “What?” I tremble, pussy throbbing, lips already swollen under her gaze.

“I want to push this inside you myself,” she murmurs, eyes dark. “Feel you fight it… then give in… then beg for more.”

I close my eyes as a fresh gush of wetness coats my thighs. “Ramya… are we gay if we do this?”

She laughs, soft and wicked. “No. But spaghetti’s straight until it gets wet. I won't tell if you won't.”

"Hmm," I say. I slip my middle finger into my hole, then pull it out, the digit shiny with my arousal. "Can confirm. Wet already." I'm suddenly awash with confidence, feeling sexier than ever.

She steps closer, breath hot on my face, and reaches around to grab my ass, hard and possessive. The squeeze spreads my cheek, tugs my swollen lips open, and a jolt shoots straight to my clit.

“Claire,” she whispers, “I’m so horny right now I can’t stand it. You trust me with everything else. Let me break you in. Bleed for me.”