Claire: Ramya stretches my pussy for the party

I promised to include her. And it's an experience I want to share with her anyway.

I shower before she arrives and give my pussy a fresh shave. But hair and make-up will have to wait.

I really like what I see in the mirror. Heavy, perfect breasts, my best feature. Shapely buttocks from the heavy lifting. A defined waist and other signs that enough fat has melted off through my hard work, leaving great curves. Combine that with my social confidence from Ramya's tutoring, and I feel sexy and powerful.

I don't know what the night will bring. But my gut says it could happen tonight. And I remember the last time I tried. Mark couldn't get it in. It was awkward, and it hurt. Tonight I might actually lose it with a guy I want to date, and I deserve to have a pain-free first time. I'm not a teenager. I'm 22, and I don't need the baggage of the physical evidence of my virginity holding me back.

I hear Ramya climbing the stairs. I throw on a robe and meet her at the door and close it quickly behind her.

A quick hug, and I feel her breasts lower than normal against me. She's braless under her coat. I take the initiative and peck her lips. "Thanks for coming," I say in a low voice. She's super excited and energetic, but I need calm.

"I'd be so annoyed if you didn't call me," she says and takes her coat off. She's in a plain T-shirt and leggings, hair in a ponytail and no makeup, her pendulous tits swaying underneath. She's stunning and incredibly sexy with zero effort.

I take the robe off for dramatic effect. Her eyes take in my entire form, lingering on my shaved pussy with the big lips showing. I clasp her hand. "Let's do it in the bedroom."

I've got pillows propped up in all the right places and soft mood music playing. My blinds are closed, dimming the afternoon light through the windows. The vaginal dilators are unpacked, cleaned, and staged in ascending order, and at the end is "The Outlaw," a Big Black Cock as my reward if I can make it that far.

"Virgin friendly" with great reviews, I have what I need to open my pussy:

I lay back on the bed and grin. "I think if I come first, it will be easier. Are you patient enough to wait?" I tease.

"Of course. I want to watch."

I grin and start masturbating while my mentor sits on the bed and watches. It's later when I'm running it back in my mind, I realize this single act was probably about the least inhibited thing I've done and most symbolic of my confidence transformation. She's close and occasionally lightly touches my leg, but content to be a spectator.

I use my normal techniques at first. Light rubbing against my clit, legs clenching tight. I lock eyes with my mentor, and as I get used to her and realize how much she loves watching, her gaze turns me on. I feel my breathing change and go with it, starting to moan. I don't exaggerate for my guest. Everything is real. My pussy gets wet fast, space opens inside, the hole relaxes.

"Can I see your breasts?" I ask. "It will turn me on."

She scoffs but likes my praise. "I guess if it will help." Ramya pulls the T-shirt over her head, and those giant, sexy saggers are there to help me come.

"Thank you." I spread my legs and slide in a finger. I work it in and out, waking up the hole, getting it ready. "Can I see your pussy too?"

"Absolutely not," Ramya replies with a grin.

I scoff, annoyed. But I can tell she likes me asking. I slip the finger out, close my legs and attack my clit again harder.

I pinch my nipples, rub them, helping the waves peak in my own practiced way. Ramya is amused, looking in close, tucks a strand of hair out of my face.

"Coming," I breath. "Uh! Uh! Uh!" I groan as it hits. It's a small one, a warm-up I rushed with no edging. My thighs tremble, my tits jiggle, and I'm left panting and ready for more.

"Good girl. Are you ready?" Ramya grins and grabs the lube. I draw back my knees and give her space on the bed in front of me. "Can I touch you down there?" she asks.

"Kind of have to," I grin.

"I love these big lips," she muses as her fingers trace them, then tug to spread me open. She's looking, inspecting. "Checking your hymen. I can see it better this time. You have the crescent-type hymen, intact around most of the opening."

"You seem to know a lot about this," I say.

"Indian in-laws are obsessed with intact hymens. Virginity is important in my culture. It can set your worth on the marital bed. You'd made a great bride."

"Not for long," I laugh.

"What you're doing is smart. If you're aroused and work up in size slowly, it might stretch enough and not even tear with intercourse." Ramya squirts lubricating gel and works it onto her fingers, then rubs it into my lips and wiggles the finger tips at my opening. Cool gel warms quickly. "First time with two?"

I nod.

"Some pressure. Relax," she coaches as I feel the stretch, a little uncomfortable, as her digits slide inside.

"Oof. Woah," I moan.

"Good job," she coaches as the fingers flow in and out slowly. "You're very tight. Grip my fingers and then relax more. Good."

Ramya looks so cool between my legs, serving me like this. I love it. I hand her the first dilator. She grins, and it goes in no problem. "That was easy," I say and hand her the second. Also easy. The third is a challenge, but her fingers are about the same size.

"Try number five," I say and hand it over.

"Now we're talking," Ramya says. "You're in 'small penis' territory now. You might pop," she warns.

"I think that's the point," I say.

"Well alright!" Ramya lubes it, inserts it slowly, looking into my eyes often to check in.

"Fuck, it hurts a little," I whine.

"It's okay, you got this," she says.

I know I need this, I know it will help. The dilator is thinner than Mark's penis, but it's in me deeper than he made it, and I can feel it through whatever resistance I have, whatever was blocking Mark from truly being "inside" me even with the head in. The dilator is doing its job, stretching my hymen, loosening my opening, preparing me for real sex.

I'm used to number five now, she knows it, pulls it out, lubes up number six. Thicker, longer, it passes into me. Conquered.

"Is that okay?" she asks.

"Yeah, that one doesn't hurt really," I say, even though I feel the expansion, the additional stretch on top of number five.

Ramya leaves it in all the way, as she did with earlier numbers. "Grip it, clench your muscles, then relax. Do that a few times, it helps. We're training your muscles to open more, not just stretching the hymen."

"Okay." I take full breaths and clamp down on it a few times. She leaves it in another minute, letting me adapt inside.

She leans in before taking it out, kisses me. "Thanks for letting me help. I'm really enjoying doing this for you. I'm so turned on."

"I'm glad I asked," I say as her hard nipples brush my shoulder.

She slides the dilator out and hold up number seven, adds more lube. "Last one. You're doing great. Are you ready?"

"Do it." This one is 1.6 inches of diameter and 6.5 inches of length. That's a little bigger than the average penis, and it's very intimidating. But with my mentor here, I'm not scared.

Deep breath. Relax. Ramya pushes.

I grimace. Pain, but bearable. She doesn't stop, and I feel it slide inside, more, all the way.

"It's in you."

I shake my head no, but my training takes over right away, lessons from smaller dilators. Relax inside, let the tissues stretch. I grin stupidly, the pain lessening already, and I know I can do it now.

"Are you good now?" she asks.

"Yeah. It's definitely stretching me. And it feels really deep."

I feel the dilator sliding out, slowly, then she pushes back in. Then she does it again, then again. Ramya is fucking me! "Um, Ramya..."

"I'm just getting you used to the motion of being stroked. Slow and steady."

Ramya slides the dildo in and out for another minute, and it starts to feel good. "It's starting to feel really good. Better take it out soon or we're lesbians," I joke.

She chuckles and removes the toy. I feel her tug my lips apart again to inspect. "There's a little bit of blood, but I'm not sure where it's from. Your hymen has thinned out a lot, but I don't see any tears. Your opening looks a lot bigger."

Ramya's prep complete:

We both look at the Outlaw at the same time. Am I ready for Big Black Cock?

"As much as I would love to see you try, I wouldn't do that one," she says. "It will definitely stretch your pussy more and help from that perspective. But you're more likely to tear, and that will leave you sore and raw. So if you have sex tonight, it might actually hurt more."

I pout. "Okay, I guess."

"Plus your pussy will be stretched so much, normal men will feel loose. You might not be able to make them come.”

"Oh my God," I laugh.

"I'll put that one in you later if you don't have sex tonight. I kind of insist actually. Speaking of that, you're taking a chance, you know. You're violating my rule for dating at work."

I almost never see Tanner at work, most of our interaction is at church. Ramya knows that's where I met him. "I think it's worth the risk. And I don't even know if he's into me that way."

She asks me for more details. I talk about his time in the Marines, I tell her what department he works in. Ramya asks for his name, then her eyes go wide. Tanner started there a little before she left the company, and she obviously knows him. I connect the dots quickly.

"You had sex with him," I say. "Just tell me, it's okay."

She holds back, I think she doesn't want to say anything, but then she can't resist an opportunity for a good joke. She reaches for dilator number six, not even the biggest one, and holds it up. "You could have stopped at this one."

"Oh my God, Ramya!" My face turns red, and she laughs.

She says. "We just went out a couple times before he worked there. We didn't have sex. I can tell you more after tonight, I don't want to influence your decisions. But I will say that I think he's a good man. Claire, your mentor approves."

"Thank you. Do you want to help me get dressed?"

Ramya shoots down my first two outfit selections. They hide my bust and don't show off my body nearly enough for her tastes. I object that the man I'm after will find me in the crowd. She lectures me on my mistakes, and I know she's right. We settle on a red dress she made me buy that clings to my hips and shows a tasteful amount of cleavage for this type of party. Then she helps with hair and makeup, and by the time she finishes, I am worried if I have the confidence to handle all the heads I will definitely be turning. I'm oozing sex appeal.

"Wow," I say in the mirror.

"My work here is done," Ramya says. "Make him chase you a little, okay. If you want to get laid tonight, you're going to get laid. Just one more thing." Ramya slides her hand up my leg, under the dress, tugs my panties down. "You don't need these."