Claire: Self-Deflowering Tease

I don't know what the night will bring. But I want to get laid. And I'm haunted by the only other time I tried, when my date's penis wouldn't fit. It was awkward, it hurt, and it left me an unpopped virgin. 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'm going to stretch my tight little pussy myself now to be ready to be filled with hard cock. There is nobody I trust to deflower me more than myself. The thought alone has me aching in anticipation.

I really like what I see in the mirror after a shower and a fresh shave down there. 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.

My nipples harden under my gaze, begging for a tweak. I trail my hands down my curves, cupping my heavy breasts, imagining a man's rough palms there instead. Heat pools between my thighs as I spread my legs and part the big lips with a finger, finding them already gleaming with arousal.

I stretch out on my bed and begin masturbating. 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.

The lube's cool slickness coats my finger as I tease my entrance, circling the sensitive folds before slipping inside. God, the warmth of my walls gripping me with tight, velvet heat. I curl it deeper, hitting that spot that makes my toes curl, while my thumb grinds against my swollen clit. My breaths come in gasps, building to a shatter: "Oh fuck, yes!" I scream, my body arching as the orgasm rips through me. This isn't overweight, quiet Claire version 1.0 masturbating in a dorm room.

I relax for a few minutes in afterglow. There is no rush.

Time for two fingers. This is an escalation, a new challenge for my pussy. Lubed, they slide in easily. I've prepared myself well. The tightness is there, and I feel the tension as my walls clamp down. Mild discomfort. I grip the digits with my muscles, then relax, then repeat, each time loosening more around them. I can feel the ring of my hymen taut around two fingers, distinct from the muscle tone as I gain awareness from the added stretch the second finger brings.

This feels really good. I'm ready for more.

I edge close to another orgasm and am now ready to begin pussy dilation. Seven phallic objects with increasing size, "virgin friendly" according to reviews, and I should easily conquer half of them after using two fingers.

With lube, the first three slide in easy. The fourth goes in without pain, but the stretch has definitely begun. It's thinner than two of my fingers, but its round cross-section makes it more filling, and it goes in deeper than my fingers can reach. Easy peasy.

With unearned bravado, I skip number five and pick up number six. This one presents serious risk to my V-card. I might have to pop my cherry to get it in, which is a sacrifice I am willing to make, and it's even kind of the whole point to this. But I'm not nervous. I can go at my pace. I can stop if needed.

The tip nestles between my large lips. I push, harder this time to squeeze it in, and oh shit! I gasp, and it stings, that sharp stretch pulling at my virginal barrier as it slides through. But it's good pain, the kind that promises more. I breathe through it, inching it deeper, feeling my pussy yield, hugging the intruder like it was made for this. Deeper still, filling me to six inches, brushing places no one's touched. I moan, low and throaty and slowly fuck myself with it. My clit throbs under my thumb in a coordinated attack, and a thrilling orgasm overtakes me soon, and finally, I can clench around something substantial when I come, my pussy fluttering and milking it, pulling it in deeper. The orgasm hits different, a rolling climax coming from the inside out. The toy slips out. It served its purpose. Also, the apartment below probably knows I'm masturbating.

The Outlaw dildo waits on the nightstand until I have the courage to submit. I eye it warily. Each bigger dilator has felt better. My pussy craves more girth and the promise of even bigger orgasms.

Two fingers again. My pussy is elastic, more relaxed from the medium dilator and the orgasms. I feel looser than I have ever been. I could work my way up the larger dilators, but I'm impatient for what's next. I wipe my fingers on the sheets, searching for evidence of a deflowering, but finding no blood.

My thoughts drift to Tanner, the guy I met at church, the guy I also work with. My crush. He will be at the party, and I want him.

The dildo is shaped like a penis with an actual head and helps the fantasy, although the color is "wrong." Tanner is a tall ex-military guy and probably has a big dick like this. I lube it generously and bring it to my meaty lips.

I angle it down to the hole and am amazed at how big it feels just with the tip in. It's enough girth to prepare me for any-sized guy. This will be a legit, full deflowering. If I take this, I’m doing it to myself. No romance, no sweet boyfriend, just me on my bed deciding I’m ready to stop being afraid, ready to stop being ashamed of pleasuring myself, ready to be a modern woman.

This is going to hurt.

I should have had a few drinks first, but then I'd have to worry about driving to the party.

I pull the phallus and feel the head widen my opening, stretching me until the ridge catches on the ring of flesh that guards my opening and defines me as a virgin. I will have to stretch more than I did with Mark to completely engulf the head. If I still need to pop the traditional way, the ceremonial tearing of the hymen, the dildo is going to do that for me.

I'm on my reliable basketball team fantasy now, triggered by the dildo's size and, ahem, color. That picture fades, and now I see Tanner’s face. His kind eyes going dark when he realizes I’m trusting him to be the first. I picture him sliding in slow, whispering my name like a prayer while I claw his back. I push, enough to feel it start to hurt but not enough to breach. That pain is laced with fire, and just the mere presence of the big toy pushing my boundaries, threatening to deflower me, puts me suddenly over the edge. I'm already in the throes of orgasm when I rub my clit and ride the waves.

I put the dildo down. I want to finish the deflowering, but this is not the right time. Maybe I think I have the right guy and want to give him the old-fashioned honor of making me bleed. Maybe I just realized taking the dildo would leave me bloody and raw for the party. Either way, I'm going to the holiday party super horny and possibly still with an intact hymen.

I know how to dress sexy after Ramya's coaching. I try on several outfits that show cleavage and cling to my hips. These clothes will still be tame for a holiday party filled with young women. Then I take them off and put on a conservative top and a skirt. My large, natural breasts are downplayed, the waist and curve of my toned buttocks are muffled in fabric, and my long legs are hidden above the knee. The guy I want already likes me (I think) for the conservative version he met. If it's meant to be, he will overlook the sluttier women and find me.

But underneath the skirt, I am bare, my exposed wet pussy a secret reminder of how ready I am to get fucked. I'll feel every breeze wafting up the skirt and every brush of the fabric against my meaty pussy lips, keeping me on edge for Tanner.

Is a small stretch enough?