Claire: pegging the male virgin

All women who don't marry their high school sweethearts encounter this eventually. That moment when your level of experience surpasses that of your date.

It's Tuesday after the holiday party, and I'm on a first date with Tyler. Picture the name and you’ve basically got him: extremely handsome, smooth shaved face, great hair, and a slim, effeminate build. He’s also three inches shorter than me (another guy who lies about height on his dating profile). I can squat more than this boy.

Most of my dates are older, but Tyler is a year younger than me at 21, unless he's lying about that, too. He could pass for a high school senior. I'm relieved when he gets carded and convinces the bartender.

I'm a horny mess after Ramya's fingers and the Deion and Tanner threesome temptation. But Tyler has exactly zero chance of getting the pussy tonight. Any man that can convince me to spread my legs and let him skip the line in front of Tanner will be much more masculine and have serious game. I don't feel bad about that. Tyler needs dating experience. I'm doing him a favor while exploring a new type of lover: younger and inexperienced.

I’m much better at reading men after the recent flurry of dating and Ramya's mentoring, but Tyler is a mystery. I’m definitely getting gay vibes, but he also checks out my rack several times. He’s decent at conversation for an engineer (nice career = a plus) and has a good brain on his shoulders. But he's very unsure of himself.

I'm shocked when he tries to convince me to go home with him. I guess all men just expect to get laid on first dates now. I'm mildly offended he would think himself worthy.

The words slip out before I can stop myself. "You're still a virgin, aren't you?"

His face instantly flushes. He looks around nervously, and before I can apologize for being so blunt, he admits it. "Maybe. Yeah."

My clit throbs, my legs squirm together. His answer is not a surprise. My reaction to it definitely is. An idea forms.

I lean in, lower my voice, and double down. "Have you been with a man?"

Now he's beet red. This guy is as white as me, and his complexion betrays his emotions. He's not answering, and now I'm more curious.

"It's between us, I promise," I say.

"I fooled around in college a few times, nothing serious."

"Have you done anal? As the recipient."

"No," he says, putting his finger in front of my lips begging me to keep my voice down.

I laugh, put my hand gently on his, and say, "Tyler, I'm a virgin too. I mean, mostly. I've been to third base as you call it quite a few times. I won't give you my virginity just to help you find yourself. But I do have an interesting proposal for you..."

Tyler agrees to come to my apartment and indulge my request. In exchange, I agree to suck his dick and let him see me naked.

We make out on my couch, and he's a decent kisser. I take my top and bra off and let him fondle my breasts. If any small part of him likes women, he'll love my perfect tits. Sure enough, his cock is already rock-hard when he undresses. It' cute. Small, slim, and completely shaved — non-threatening and kind of adorable.

After taking off my pants and letting him ogle my fully nude body, I say, "I should go first. It will be more fun for you if we do it before you come."

I disappear to don the strap-on harness and "The Outlaw" big black cock dildo. The slimmer dilators fit with the harness, but I want to break him in properly.

When I step back into the living room, his eyes go wide. "That's huge!" he shouts. "Really?"

A wicked smile spreads across my face as I sway my hips, letting the massive black dildo swing like a weapon. The heavy weight pulls deliciously at the harness, and something primal wakes up inside me. The shy church girl is fading. In her place is someone hungry and predatory. I'm going to ruin this boy and enjoy every second of it.

"You’re not scared, are you?” I tease, stepping closer. “I’ve taken this in my ass before,” I purr. “It feels amazing. Now be a good boy and go to my bed. Hands and knees.”

Tyler is good at following orders. With his knees on the foot of my bed, I'm at the perfect height standing behind him. I squirt lube onto my fingers.

His butthole is immaculately shaved just like his front. I work a finger in. He's tight but clenches only for a second, then we're good. He knows what he's doing. I chuckle and work quickly up to two fingers.

"Your bum is trained for this. You lied to me. You've been fucked already, haven't you?"

"No, I swear." His denial and shame are cute. "I've explored by myself is all. Nothing that big."

After a minute of listening to him whimper fake objections while his back arches and he pushes back against my hand anyway, I’m confident he’s ready.

“I'm going to insert the dildo now,” I say. "It might hurt a little at first, but trust me, you're going to love it." Using the same line a guy would use before popping my cherry is super hot for me. I line it up, push, and his hole dimples inward under the pressure, but no penetration.

“A little higher,” Tyler says, his voice shaky.

I adjust gently. “Like that?” I chuckle as he gasps, his butt muscles clench in surprise, and he moves his hips forward to escape.

"Ow," he whines.

"Come on, the head wasn't even in yet," I tease.

He wags his butt playfully and returns to position. He wants it now. I push again.

“Yep, that’s… Oof!” he moans as the head pops in. “Fuck!”

"Good boy," I purr as I slide in a few more inches. Once the sphincter pops open, the rest can fit easily except about two inches at the base. I've found his depth. "Stop squirming. You've got this."

I love how his haunches tremble and flex in surprise, his pale white cheeks spreading wide around the thick black shaft. The harness grinds against my big clit and oversized pussy lips with each tiny shift, sending sparks through me. I'm obsessed with this new power, watching his hard cock leak pre-cum untouched onto my sheets.

I start thrusting — slow and deep at first, then building a steady rhythm. I wish I had a mirror. I love my hard-earned muscles flexing as I dominate this man. The soft curve of my large breasts above the sight of his ass swallowing the thick cock.

I feel him relax and loosen around the dildo as my steady thrusts eat away at his nerves and tightness, awakening him to his new purpose. It takes him a minute, but he turns the corner from pain to pleasure. He grips the sheets white-knuckled, but his body betrays him, pushing back for more as whimpers turn to needy groans. “That’s it, open up for me.”

We're both edging close to a climax. If I replaced the harness with my fingers against my clit, I'd come in seconds. Tyler has kept his erection, leaking precum, and I could reach around and stroke him to orgasm if I wanted. But I'm not ready to let him come. I pull back and rest the dildo with just the head inside. A few seconds go by, then he impatiently wiggles his butt and pushes back, but the head slips out. "Beg for it," I command.

"Fuck me," he moans. "Please. Fill me up with that big dick."

With a triumphant groan, I drive forward and fuck him harder. He's not only stretching wider, I'm rearranging things deep inside him, opening up space deeper. Only an inch of the long dildo remains outside during my relentless cock-stabs. I keep going until he’s a moaning mess, begging me to go harder. Every thrust makes me feel stronger, like the thick cock is a part of me. I love using it. Finally, I pull out slow, watching his stretched hole gape, then clench at the emptiness until it finally closes most of the way, perhaps stretched permanently.

"The boy has officially become a man," I tease. Fucked senseless by a virgin girl with a big black strap-on.

I slap his ass playfully, and he collapses onto the bed, panting, his cute little cock still hard and twitching.

“Claire, that was insane,” he gasps, rolling over with a dazed grin. “Can I fuck you now? Please?”