"What Does She See in Him?"

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For some reason that just turned me on even more.

But for Laura, on the other hand, this was all preliminary action and I hadn't even gotten five inches into my mouth before she pulled back, stroking the back of my head with her hand, "That's enough of the warm-up Andy. You ever had anal before?"

I shook my head, wiping up a bit of stray precum and drool that had run from the corner of my lips and down my chin. As I opened my eyes and saw the size of Laura, I realized I might need to think that particular thing through before I agreed to anything. I'm certainly no slouch in the genital department, but compared to a healthy seven inches, Laura's looked like a meat bat, with a flared head and open tip that just drooled precum continuously.

"Do you want to try give it a shot?" My expression must've betrayed my apprehension to her and she immediately added, "Don't worry, I have lube and I won't like... powerfuck you or anything..."

"Promise?" Those were the first words out of my mouth since I'd started sucking on her. My own cock twitched, almost painfully erect, in my slacks and I undid my belt.

"Promise."

I sat up and unbuttoned my slacks while Laura leaned over to kiss my forehead then run her tongue down my nose until finally kissing me. Kissing my mouth while it was still full of her precum. She slipped her tongue between my lips forcefully and scooped my spit into her mouth while her hands lifted my shirt up. I was so caught up in the intensity of the moment I could barely raise my hips and slide down my pants, but Laura eventually broke the kiss and helped me get them down to my ankles.

She opened her mouth and licked my bare stomach and chest, then slipped my boxers down to join all my other clothes on the floor. If my cock was a disappointment to her, she hid the fact very well, letting it flop upwards and sling precum on chest and neck without complaint. Honey-brown eyes, glazed with lust, let me know she was still in the market for fucking me and I reached over to my bag. It was awkward to stretch across the couch while my girlfriend tongued down my belly, but I felt amazing to have her lick and suck on my skin there.

I snagged my condoms and pulled one of them out, bringing the wrapper to my lips and tearing it with my teeth.

"Uh Andy?"

I was just spitting out the torn corner, "Hmm?"

"Is it cool if..." she exhaled slowly and took a deep breath, "Is it cool if I bareback you for your first time? Condoms make lube dry up really fast and kill the feeling so it'd probably be better for both of us if I went bare."

I didn't even pretend to consider saying no. "Sure!" Her smile returned in all its brilliance and she rewarded me by taking my cock between her lips and sucking until her cheeks went in, filling her mouth with my precum and making a big show of swallowing.

"You're the best, Andy! Just scoot your butt to the edge of the couch."

I nodded and did as she asked, then spread my legs while she reached into the couch's side storage, pulling a packet of lube out. I didn't even know lube came in packets then, but apparently she not just knew more about this whole anal thing, she practiced it regularly: there was more than one packet in there and at least two that had been emptied.

The sudden feeling of being exposed and vulnerable came over me as she tore the packet open and applied the first half to her cock, stroking it in with a schlck-schlck-schlck and looking back up into my eyes, "Do you ever play with your butt?"

"What?"

Laura bit her lip and reconsidered, "You know? Finger your ass a little? Stuff like that."

"No..."

Her head gave a small nod and she squeezed tight along her girth, lip quivering as the excess of lube built up on her hand. While she did that, her other hand poured the remainder of the packet's contents between my crack. It was cold, too cold and I shivered while feeling the greasy liquid travel down to my pucker before she pushed a finger, slick with wetness, right inside me. I thought I was tight, but Laura had tiny fingers and didn't actually encounter much resistance. What I encountered was a weird sort of full feeling, more like being tickled than anything particularly erotic. But she kept right on, eventually getting her finger as deep as it could go before pulling back and adding a second finger.

Whoa. Now we're cooking with gas.

The full feeling was still there, but impressively amplified. I couldn't describe it at the time, but it was like... almost like you know something is going to happen, but you don't know what? That bit of anticipation and mild offering of fear? That emotion passed through me while my girlfriend used two fingers to play with my ass. And while the rest of me might have been confused, my cock was certainly unequivocal in its approval, throbbing harder than I could ever recall while pumping out precum by the bead.

"That's it... loosen up for me Andy... I'm going to take you to cloud nine and leave you there."

She added a third finger and I finally moaned, feeling my ring stretch but not in a bad way. I just wanted to let her know whatever she was doing, I was definitely on-board with it. Laura gave me another smile and licked my balls, then started pumping her fingers faster and deeper. Then, just like that, I was empty my whole body jerking at the sensation of being suddenly denied with a longing whimper to match.

"Don't worry Andy, just a few seconds and I'll show you how to take it." Her voice practically dripped lust, "I bet you'll love it."

As she spoke, her hand on her cock lined her up with my pucker, rolling the tip in a slow circle around my ring, which sent lightning bolts of pleasure through my spine. My precum was coming out in a solid stream now and I did my best to relax, hoping against hope she'd remember her promise not to pound my virgin ass. The old joke about guys saying, "Just the tip" and ramming it all in once they were there bounced around my head and I shuddered at the idea of taking all eight or nine of her inches at once.

She took a deep breath, mouthed the word "relax" and started pushing. Almost immediately, I started to have second thoughts, feeling my outer ring stretch around her girth. It was incredible in every sense of the word and I hissed. As I tried to loosen up and mostly succeeded, the movie's soundtrack filled my ears, with one of the characters screaming "WITNESS ME" at the exact moment Laura pumped her girlmeat up my ass.

I'm not going to lie: I screamed.

But the initial penetration was nowhere near as bad as I'd been dreading and my cry died away. Laura had stopped right after getting the crown of her cock inside and was looking at me, "Are you OK?"

"Y-yeah... I'm fine."

"Good," she started backing out and pushing in, "Because your ass is the best and tightest I've ever felt.. holy shit, I'm surprised I'm the first... if any of the others had known, they would have been all over you like..." Her voice trailed off.

"Like nerds on Star Wars merch? Like –" I didn't complete the phrase, as Laura grunted and pumped two or three inches in me. You never think two or three inches is much, but when it's up your ass, it is suddenly a lot more than you've been led to believe. And Laura's was thick, so it was especially straining.

But once she got those inches in, she let go of the rest of her cock and looked down, "I'm gonna make you cum Andy. I'm gonna make you cum from having anal... I bet you'll love it."

Her hands took up my ankles and raised my legs even higher as my girlfriend pushed them back, spreading me even wider while her hips worked back and forth. It wasn't the jerky, spasmodic sort of thrusting usually associated with desperate virgins in the throes of casting off their virginity. No, this was the slow, thorough driving that made my hole quiver in a mix of pain and pleasure. It certainly burned a bit but as her plump shaft rolled over my prostate, I really did see stars, incredible stars, all over my vision. Even better was when she pulled back and the flared head of her cock caught against my ring, stretching it out just a bare few millimeters, all that was needed to make my insides sing her praises.

"Fuck, fuck, fuck.. so tight."

She didn't pick up the pace, but she did bite down on her lip and close her eyes as her cock worked in and out of my stretched, recently unused hole. My cock was twitching like mad now, completely drenched in precum that was being milked out by her thick shaft squeezing at my prostate. I had the overwhelming sensation of being a huge slut.

It felt really good.

"Can I cum inside you?"

My eyes popped open and I looked at Laura. Her head was thrown back and she was drooling and hissing, clearly in the throes of ecstasy as she fucked me. Barebacking was one thing, but actually taking a cumshot? That seemed somehow... more taboo.

"Go ahead."

"Gonna breed your tight ass Andy... gonna spunk you so good... you're gonna be dripping with me all night long..."

She let go of my ankles and grabbed my hips, holding me tight as she finally broke her promise not to powerfuck me, "So fuckin' good... god I love buttfucking boys... so tight... fuck... I can feel your prostate. Are you gonna cum for me Andy?"

"Harder."

Laura smiled and went harder, easily working five out of her nine inches in and out with every thrust, her flared head penetrating me deep and touching spots I never knew I had, tits swinging back and forth over me. She was so big, it was like having a battering ram through my insides and only the feeling of pleasure that passed over me in waves kept me in the game, so to speak. And it was good. Real good. Good enough that I was actually having mini-orgasms every time she bottomed out, my own cock dribbling a bit on my belly when her balls clapped against me.

Not gonna lie: feeling like a slut was amazing. I don't even know how girls go through life denying they enjoy getting fucked, because – for me – getting fucked was seventh heaven. It took basically every lusty, hedonistic fantasy I'd conjured up in my head, neatly packed it into a box, then used that box to bend me over and fuck me. Imagining what my pucker must looked like stretched around Laura's girth was what filled my head and fueled my fantasies now, along with the realization that this would be happening a lot.

"Andy... I'm close..."

"Uh-huh!"

"I'm gonna cum inside you..."

"Uh-huh! Do it!" This went well beyond the naughty act of barebacking – she was going to blow her load right up my ass. I don't know how I'd keep a straight face when my friends asked what happened over the weekend, but that was a fuzzy concern somewhere on the periphery of my mind. What was first and foremost was squeezing her shaft, milking it as tight as I could.

There was a sudden and deep strain to her voice and I felt her cock throb inside me. "Alright slut, here it comes!"

Then I felt her climax. It was hot, sticky and sinful, pouring inside me like honey, washing over my prostate and mixing with the lube to fill every bit of my guts. I came right along with her, hard and would have sprayed my own face, but Laura – sodomite-angel that she was – knew I was close and pulled my cock up towards her as I dug my fingers into the couch and cried out. My own load rocketed up and blasted her in the chin before the second rope adorned the underside of her huge tits.

It was the sort of deep, soul-wrenching orgasm that made my balls feel like they'd been turned inside out and continued on even as the little orbs were empty, my cock twitching almost violently while my vision blurred and a ringing sounded in both ears. In and of itself, it would have been the climax of climaxes for me, but Laura's incredible cock had one last surprise in store. As she withdrew, slowly, the slight upturn on the head of her ladystick stroked my prostate at the exact right angle to trigger another orgasm. I jerked up and I sang her praises as nothing but runny precum bubbled out of my cock, dribbling down my shaft and letting her no, without a doubt that I'd enjoyed bottoming for her.

"I've never seen a guy cum that hard from being fucked before," she said with a slight note of exasperation in her voice, "Most just pop real quick and that's it. Is that how you long you normally cum for or what?"

"No... never like that," I nearly gasped.

Her smiled spread across her face, mischievous and sincere, "So you're saying that this," she pointed to her cummy breasts and belly, "Was all me?"

"All you Laura... holy shit it was all you..."

"That's good to know," she flipped her hair back with a toss of her head and lifted my thighs once more, "Because we have plenty more to go before I'm all done."

And with that, she bent down to kiss me softly, while sliding her cock back deep inside my creamed in ass.

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45 Comments
1Martiniman1Martiniman3 months ago

This story was fantastic! The sex scenes were hot, the premise was fun and that little bit of mystery was intoxicating…who is Laura and who are the “others” she briefly mentioned?

A must read! I’m ready for the next part.

AnonymousAnonymous3 months ago

WOW!!!!!

AnonymousAnonymous4 months ago

Great. Made me extremely horny

Yankee0717Yankee07175 months ago

That was incredible!! At 65 i doubt that will ever happen to me, but a guy can dream 🤫😁

Blackbear7Blackbear76 months ago

I would love to have a fling with a teen femboi. Experience and explore our secrets and deep dark fantasy come to life. Might be start to a long drawn out saga. Needsomeloving1968@yahoo.com is waiting.

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