Claire: A failed vaginal entry

So we drink and talk. He's naked, and I'm still dressed. My high-beam headlights are on for him. He runs a finger along my arm then down to trace the outline of my nipple poking through the shirt. It feels great. "Show me your tits, girl. You've been teasing me with those all night."

I wonder briefly if Mark has forgotten my name. I know I am just a statistic to him, a notch on his ladder if I let him have his way.

"Well I do have amazing breasts," I say. They are my best feature besides my eyes, especially since I still have some gut I need to burn off, and I want to impress him. I pull off the top and reach back to unhook the bra. My tits spill out. They look phenomenal. He reaches out and cups them, lifts them, then leans down and kisses a nipple while his thumb brushes the other one. I close my eyes and exhale as I feel the electric charge course through me from my breasts to my loins.

His cock is starting to swell. "These are fucking perfect," he moans. I really love this praise. "Why don't you put out? You deserve some pleasure."

"I do, just not on the first date as a general rule," I say with a grin. I don't want to admit I'm a virgin. I'm worried he will mock me or be turned off. Mark is older and surely been with lots of women.

"Well, you give head like a pro. I'm grateful. Well done." He raises his glass and toasts.

"Thanks, I pride myself on at least that," I reply.

He finishes his drink in one large sip. I can see the **** is affecting him, but at least he's not slurring words yet. But the drink will make him less predictable and more aggressive. And how the hell is he getting home? He isn't worried at all it seems. I worry too much. I will myself to relax and just have fun.

"I want to eat your pussy. Let me make you come. I owe you."

He has a point.

We're facing each other sideways on the couch. He leans over, hooks the waist of my jeans and panties, and tugs to sneak a peak at my pussy. "Let me return the favor."

I scoff and waffle. I'm very nervous getting naked with this guy. I fake the confidence. "Finally. I was starting to think you're selfish." I take a deep breath, then say, "Okay. Show me what you can do."

"Bedroom?"

"Okay."

And that's how I end up naked on the bed with a guy I had no intention of doing this with. My body is clearly in charge tonight. I take my jeans off myself, then I start trembling when he removes my panties. This is way more **** than having just him be naked with his cock in my mouth. But I'm curious. And I like the idea of him servicing me. But I'm very insecure about my genitals. I recently started shaving, and I love how my pussy feels bare. But it accentuates the size of my large lips. And I've seen all the Internet memes making fun of this look, the roast beef analogy, the implication that I am a slut with a loose, used pussy somehow due to the size of my labia. Not true! I've never stuck anything bigger than one finger in my pussy.

"Damn, girl, look at those big MILF flaps," he jokes. I scoff, then he adds, "Shaved clean, I like it."

And we move on as he spreads my thighs. I'm not sure if he was making fun or not. I guess I don't care.

He's drunk now for sure. He eats my pussy erratically. It feels really good just having his lips anywhere on my erogenous zones. But I know he's not good at this, even though I've never had it done to me. I have a large clitoral hood to go with those lips, and the whole vulvar area is larger since I'm tall. My clit is a very easy target, yet Mark is unable to find it.

Minutes go by. I get off easily with solo play, and Mark should have delivered the big O already. I pinch a nipple, a trick I do help reach orgasm. Nothing. I reach down and hold his head like he did when I was going down on him. I steer him to my clit, but it doesn't help. I groan in frustration.

He stops, and I look down to meet his eyes. "Are you giving up?" I whine. "I got close a few times."

"My head's spinning from that last drink. Need a break. Let's kiss."

Mark climbs up my body. I foolishly let him, leaving my legs spread wide. He settles his weight, mashing my breasts under his chest. I'm a few inches taller and have been working out with heavy weights. I feel like a boss lady since I can handle his weight on me easily. He moves up on me further to kiss, and I let him. As his weight settles again, I feel his bulge, his thick penis, right against my pussy!

He doesn't feel hard yet, but he has definitely swelled up since I made him come. He's just grinding it against me as he moves his hips reflexively in a circular pattern. At least I'm finally getting some clitoral stimulation, so it feels unfairly good. My legs wrap around him without my permission. "Mark," I playfully accost him. "No penetration. Be careful with that thing."

"Come on, baby, let's fuck. I'll make you come, it will feel great."

He's slurring his words now. "That's not going to happen," I say with a nervous laugh, but his tongue pushes back into my mouth to shut me up, and I suck his tongue and run my hands along his back, enjoying the sensations. It's fun, so I put my feet back on the bed and begin to undulate beneath him, and I lower my long arms until I cup his cute little butt cheeks. Instead of stopping him, I encourage him, pulling him into his grind, moving and angling my own hips to hit my clit. It feels really good against my pussy, and I like having a man on me like this. I'm curious and horny and safe when he's flaccid. A few minutes go by, and I ignore the red flag that he's getting harder.

Then one push hits me perfectly. The now-thick head parts my swollen lips, and his grind pushes the tip in, filling the vestibule, and I feel the stretch as he tries to squeeze into the tight canal. My eyes go wide, and luckily he's angled slightly to the side with just enough softness in the shaft to not push in and pop my cherry. The head slips out.

"Mark, wait," I say. I wrap my long, strong legs around his torso and squeeze just enough to stop him from finding the hole and pushing in again. Except that now, after having him at my entrance and sparking my curiosity, I kind of want him there.

"What, baby? Let's do this, I know you want it, too," he says with a cocky, drunken grin.

I scoff. His tongue finds my mouth again. My own head spins now, too, and I start to admit the truth to myself. Mark, is offering exactly what I've needed for a while now, a stiff cock to quench my horny desires once and for all!

I have no future with this man. I know it's a one-night stand. I begin to justify in my mind what my body wants: I can lose my virginity now so when the right guy comes along, he won't think I'm some inexperienced little girl he has to teach about sex. It would be so embarrassing to be in pain or bleed when it matters. Most guys don't want to deal with a 22 year-old virgin girl. They want a woman that knows what she is doing. Letting Mark take my virginity is an investment in myself. I will be more desirable to other men and be a better lover.

"Mark?" I say louder. His cock pokes lower now, at my perineum. There's hardness in the shaft this time. He's ready. "Shit." I waffle. "Mark, stop."

And he does. He looks up at me and grins, waits.

"I wasn't going to do this." I scoff, and I roll my eyes. I can't believe the next words that come out of my mouth. "Fine. I'll let you put it in. Do you have protection?"

His grin grows. "No, baby, it's okay. Nobody uses those anymore. I pull out."

He's kissing me again, a wet, sloppy distraction as he pumps his cock below, into my perineum, both my pussy and my anus in danger. I'm not sure if he's aware he's not in me yet.

"Wait," I say, and he looks at me expectantly, and I surrender. I'm super horny, and it's definitely affecting my judgement. I relax my legs' grip on his torso, spread them, and bend back at the knees. I reach around, under my thighs, and I clasp his dick. "You better pull out. We can risk it, I guess. Promise me you'll pull out!"

"Okay, geez. I will."

"You're off target, a little low. " I look into his eyes as I make the adjustment, lifting his unit. I seat him at my entrance, and the tip slips inside my wet pussy. "Ooh! Yep," I laugh, "You're in me now. Go slow, please." He pushes and immediately begins to penetrate. The head fills in and dilates my opening, and I feel all the skin around it stretching. An intense stretch and the beginning of a burn. My eyes squinch up, and I almost bite his tongue. I'm too tight for him. He can't get it in.

I don't know for sure what awaits him, what barrier he might need to breach. My pussy muscles contract, guarding my virtue, objecting to the intrusion even though I want him inside to get the hard part over with.

The pressure subsides with the natural rhythm of his hips. His next push is angled lower, into my perineum area. My skin presses in with his push, and my opening moves down a little as my vulva is imploded, seeking the coupling. "You slipped out," I chuckle. "Hold on, let me."

I reach down again to guide his cock to my pussy.

Be a boss girl. You got this.

“I’ve never had one this big,” I say with a grin. Not a lie.

I will myself to relax, to accept him into my body. I try to lower my defenses. The muscles inside open as I exhale deeply. I **** a grin, reach down and slap his butt affectionately, and pull him into me. “Come on, push,” I command.

I’ve opened space for him. The resistance isn’t clenched muscles as much as it’s the tissues themselves, that tight ring at my entrance that’s never been stretched like this before. The blunt head nudges in, spreads my lips, and I feel everything give a little, flexing inward to let him through without breaking.

The ridge pops past, and suddenly the head is fully inside me. It hurts immediately, a burning pressure as the ring is pushed deeper into the canal, still intact, still holding.

“Oooof,” I moan.

He’s really, really fucking big. The stretch is intense, like I’m being opened for the first time, but something’s still stubbornly holding him from going deeper.

He pauses, lets me adjust, then drives forward, and one more inch, then two slides inside. The thicker part behind the head dilates my opening, passes, and I'm beginning to accept him. The burn turns white-hot. The tip passes through whatever’s holding him back, stretching and thinning it as it slides up to the crown, but it will have to tear to pass the whole head at its widest point. My pussy clamps down like a vault, trying to push him out to protect my virtue even as I want more.

My cheeks puff out as I muffle a scream.

I inhale deeply as he pulls back, the head retreating until it’s just holding my entrance open, that tight ring intact, battered but not fighting.

I'm not sure if I'm still a virgin, if I've crossed that line. But I still need to be deflowered.

“What’s wrong?” He’s looking into my eyes now, concern mixing with lust.

“Hurts a lot,” I whine, voice small. “You’ve got a big dick.”

Does my cherry still need to pop? I sense that I won't yield more ground without a lot more pain and trauma, and I'm just not willing to endure that with Mark. He's not the one. My body resists, clenched muscles stop him earlier this time, and the head plops out as my drunk, frustrated lover fails to complete the deflowering.

I shake my head no. "Mark, sorry, but this isn't going to work. I'm really worried about getting pregnant." He pushes anyway, but this time he's off target, and I've positioned my hand to block him anyway.

He doesn't complain or call me out on the lie. I think I had a moment of clarity as he was about to pop me, where I realized maybe losing my virginity for a one-night stand might be a bad idea, and that I should respect myself more. Not sure.

"Can you take it in the ass? You said I could fuck you, and I promise you won't get pregnant!"

Mark's bought girth-to-length ratio and why he won't fit :)