The Girlfriend Who Wrecked My Ass

My girlfriend of three weeks, Lillian (who goes by Lily), had been overwhelmingly drawn to my butt since the night we met.

It didn't strike me as odd, not at first. I'm an ass guy. I'd take a girl with a great ass over one with big boobs every day. I figured Lily was like me, but in female form. An "ass girl"--if that's even a thing.

What's more, Lily isn't the first woman to dig my backside. I have a nice butt for a man, I realize. I've been told that before. Plus, I shave down there to keep things sanitary. Good hygiene wins over the ladies, always. Lily smiled when she first noticed. She said how much she appreciated it when a guy keeps a smooth butt.

Was Lily more into my rear end than other women I've been with?

Maybe.

OK, definitely.

She'd place her hands on my butt when we'd kiss. The deeper we'd kiss, the more she'd sink her nails into my cheeks.

Every time I was over at her place or she was at mine, right after I'd step out of the shower, Lily would steal the towel from my waist, roll it into a burrito, and slap my butt with it roommate-style.

If I cracked a joke Lily didn't like, she'd pinch my butt cheek hard, leaving a mark, staring me down angrily.

So, yeah, there was something there.

I never gave it much thought, really. I just saw it as Lily's thing.

Then, one day, she took ass play to the extreme.

I was on the couch at Lily's with closed eyes and fingers sunk into my hair as she was sucking me off.

Just when I was about to plaster her face with cum, Lily put her palm to my butt and forced her manicured little finger straight into my hole--my virgin hole!

Until then, my ass was a sacred space. I had never let any woman anywhere near it. Lily went right in without asking.

I leaped from the cushion in protest, but before I could say a word, Lily inserted a second finger in, took my full cock in her mouth, and--with her gaze fixed on mine--curled her fingers against a spot in my ass I didn't even know existed.

That spot, dude... That spot.

I get goosebumps just thinking about it.

So, Lily's assaulting my prostate as I'm twitching and twisting and spasming and squealing in her hands like a little girl. Warm waves of pleasure are making my skin tingle and leaving my limbs numb. I swear--I almost blanked out there on the couch. She kept tracing the tips of her fingers against that spot over, and over, and over again... it felt magical.

Lily spat and slurped and sucked and gargled and bobbed her head up and down my prick until I could no longer hold the cum in. I growled out like a caveman and shot my load. I must have spurted seven or eight wads of cum straight into Lily's mouth. There was so much of it that it flowed right out. She jerked out every last drop, leaving no drop behind, then climbed on top of me and started grinding her wet pussy against my throbbing cock.

We kissed.

Cum gushed out of her mouth into mine. I had never tried my own cum before. It tasted like chlorinated water, but salty and sticky. Lily got so turned on by it that we went for a second round and fucked like animals.

I had a heart-to-heart with Lily that night. She told me how obsessed she was with the male butt, and how all her previous boyfriends hadn't let her play with their asses. But when she saw me, she said, she could tell straight away I would agree.

"How could you have possibly known?" I asked.

"Babe. You can't have an ass this gorgeous and not let me play with it."

Lily asked if I had ever tried anal before. Not if I was the one taking it, I replied.

Not until I met her.

We saw each other two days later at the movies. Some stupid western.

Before the ads were done playing, Lily undid my zipper and yanked the semi-erect cock out of my shorts. She kissed me, then spat on my cock and began pumping it like a shotgun.

Thwap! Thwap! Thwap! We turned heads in the theater. Lilly had only been stroking me for under a minute and I was already on the verge of blowing my load. Since we were in the movie theater, I figured I'd just shoot it in her hand. However, she had something else in store.

Lily edged me to the point where I was begging her to cum. When I begged so loudly that the people in the seats nearby stared at us, Lily clasped her fist around my rod and finished me off with five hard, long strokes. But instead of catching my cum with her hand like I thought she would, Lily angled my prick straight at my face!

I came all over myself.

"What the hell, Lily?" I protested as discreetly as I could.

"What?" she asked, as if nothing had happened.

"What do you mean 'what'? There's cum on my face!" I objected.

"Mmm-hmm," Lily reacted, leaning in. She licked a trickle of semen from my cheek. "Look at you go!" She whispered in my ear, "You made such a mess!"

I didn't watch the movie.

I fumed about the trick Lily pulled on me the whole time. There was cum even on the popcorn. She didn't seem to mind.

I drove Lily home after, even though I was kind of mad at her. She said she had bought us something special and she really wanted me to see it, and invited me in.

"Are you still upset about what happened at the theater, silly?"

"Lily! You made me shoot my load all over myself!"

"Babe, quiet: You should be thanking me. That T-shirt was boring. Now it's not."

There was a gift box on the coffee table. A big one. More on the long side, actually--like 18--19 inches.

Lily gestured toward it like a quiz show host and urged, "Go on, unwrap it."

"What is it?"

"You'll have to find out," she said with a wink.

"Ugh, Lily... Is that what I think it is?"

"A strap-on?"

"Strap-on?! No. Better--it's double the fun."

"Wait. Oh. It's a double dildo."

"Mmm-hmm," Lily nodded a few times.

"Is it for you?"

"It's called a double dildo for a reason, silly. It's for both of us."

"For both of us?"

"It's something I've always wanted to try with a guy," Lily added, biting her lip. "Trust me, we're going to have so much fun!"

"I trust you, Lily... And that's nice of you," I said, keeping my voice steady, "but we really need to talk about this before going any further."

"Talk about what?"

"You bought us a double dildo!"

"What's wrong with it?"

"What's wrong with it? I can kill someone with it!" I removed the dildo from its box and jiggled it left and right. It was heavier and more flexible than I expected.

"I know," her eyes lit up. "Look at it jiggle. Isn't it fabulous?"

"Come on, Lily," I said. "I'm straight."

Fingering my ass was one thing, but a double dildo? I wasn't sure if this kink was for me.

"What are you talking about? Men have such fragile egos. It's just a toy, babe. It's not a real dick."

"Ugh, that's not something I agree with--at all."

Lily moved closer to me. She caressed my neck and murmured softly, "Babe, you came so hard when I put my fingers in your ass." She licked her middle finger, slipped it under my boxers, and ran it along my butt crack, widening the space between the cheeks. "I know what turns you on," she teased. "We match up so well."

"We're breaking up."

"No, we're not."

She bit my ear, grabbed my butt, and shoved her middle finger into my hole controllingly. My dick, solid as steel by then, twitched in her other hand.

"You're not going anywhere--look at that boner."

Lily pulled off my shorts and began jerking me off.

"We both know you like it when I take charge. Don't fight it, babe."

Lily let go of me, snatched the dildo, and wrapped it around my neck like a snake. She nibbled on my ear, turning me on even more, and we made out.

I stripped off my T-shirt, played with Lily's pussy through the fabric of her jeans, then slipped my hand past the waistband, pulling her soaked G-string to the side.

Tumbling Lily to the couch as the dildo fell off my neck, I slid off her jeans and panties and gave her pussy an eager lick.

Lily groaned.

She clutched the back of my hair and started bucking her hips, using my mouth to fuck herself. It was wild--at times my face was buried deep so in her cunt that I couldn't breathe. I had pussy cream on my nose, cheeks, and chin as Lily purred and mewled and moaned to the action.

Her pulsating clit told me that she was close to cumming. She pushed me to stop, leaped to her feet from the couch, and took the dildo with her, walking us to the bedroom. We let ourselves fall on the bed--arms and legs intertwined--kissing and fondling our naked bodies. Lily arched and turned so her pussy was now on my face. I buried my face between her soft inner thighs and, as she circled my cock's head with her tongue, we began 69-ing.

Grrrh!

I can't even begin to tell you how good Lily tastes down there. Like vanilla-flavored soft serve, but laced with pussy-juice aphrodisiac. The second my tongue touches Lily's sweet little pussy, it's over. I turn into a cunt licker who can't get enough.

Lily kept lapping at my shaft as I was eating her out. She interrupted me to stick three fingers in my mouth, gagging me forcefully until the fingers glistened with throaty white spit. Then Lily smacked my butt and shoved the fingers past my sphincter. Having so many fingers in my ass hurt. But the pain also felt so good.

Lily reached for something--a bottle of lube. She squirted it on my hole and smeared it around my anal ring, spreading it in circle and a pushing some of it in.

Hey, I'm not dumb.

I can see what you're thinking.

The more I share of the story, the more you're scratching your head, wondering why I didn't say a word and went along with everything Lily wanted. The honest answer is, I don't know. It was like she snapped her fingers and took away my agency without even asking.

Granted, Lily's a bombshell. Men stop to stare at her when she walks the street. Some women look at her too. They want to lick her pussy. However, I've been with a dozen girls--and I've never had any of them call the shots over me like that. So there's got to be something more there. There's no way it's Lily's looks.

It could be her gaze, though. She has this predatory way of looking at you. It's like she wants to fuck you and eat you alive at the same time.

Like I told you--I don't know.

The way she squeezes my butt and sticks in her fingers so casually... Dude... It's like, she's got me under her thumb or something. It turns me on in the most depraved way.

So there I was, on top of her in the bed, ass high in the air and cock on Lily's face, when she grabbed the giant dildo with both hands and positioned it right against my ass.

In case you haven't figured it out by now, my hole's tiny. In contrast, that silicone dick was huge. The more she pressed it into my ass, the more overwhelmed I felt. The pain became unbearable.

"Lily," I cried out, "I-- I can't do this."

"Shhhhh," she shushed, licking the tip of my cock's head to distract and console me. "I lubed you up. Just relax."

"Lily, I--"

"Babe!!! Get a hold of yourself and take it like a man!"

She smacked my ass, gripped the dildo until her knuckles went white, and pushed it in as hard as she could. I buried my face between her legs and inhaled the dampness above her pussy.

The dildo's tip popped in. It literally tore my ass open. I had never experienced pain this brutal my entire life. Soft silicone dildo, my ass! The more my butt tightened, the more solid this thing felt. She thrust it in again, now a few inches inside me.

I clenched my hands into fists and wrinkled the bedsheets. Fuck. Fuck, fuck, fuck, fuck... This cycling of pain, then pleasure, then pain, then pleasure again was driving me mad.

I wanted it to stop so bad, yet I couldn't get enough of it. The sorer my ass became, the more I wanted Lily to wreck it. Was that why men fuck with men? Aargh! Why was I picturing it?! I tried hard to erase the picture from my mind. I focused on licking Lily's cunt again.

"That's the way, baby!" Lily hooted. "You half of the dildo's almost all the way in!"

My attempt at focusing on Lily's cunt failed. All I could think about was the eight or nine-inch silicone cock in my ass.

It felt wrong. But it also felt so right.

I wanted to push the fucking thing out. Yet I wanted so bad to hold it in.

I was supposed to be the one giving it to Lily. It felt so liberating that Lily was giving it to me.

Fuck.

Fuck, fuck, fuck. Fuck me.

Lily rolled me to my back and sat on my face. I felt her feet around my head.

"Eat my ass," she commanded.

She rested her palms on my chest and arched her back, throwing her hair to the side and tilting her head back in anticipation. Like a goddess: back and shoulders so sexy from below, tanned and lean.

Watery precum spurted out from the stiff tip of my cock. It made my ass contract and quiver around the dildo. I moistened my tongue with spit, stuck it out, and touched the small hole in Lily's ass, sticking my tongue in as far as it would go. Her ass tasted differently than her pussy. It was earthier.

Lily gasped.

She held me by the back of my hair and backed into me with the force of a bulldozer.

My cock stiffened again, and my ass twitched. It made me push out a few inches of the dildo. Lily noticed and leaned in to shove it right back where it came from.

"Now I'm ready." she announced.

"For what?" I looked up with puzzled eyes.

"You'll see."

Moving to the bed's end, Lily wrapped her hands around my ankles and gradually lifted my legs back and over my head. I had boned so many women in the seashell position--but never before had a woman folded me into it.

A grin spread across Lily's face. "God, babe," Lily announced between gritted teeth, "I've wanted to try this for so long."

Lily lubed up her butt and smeared some lube on the half of the dildo that wasn't in my ass. She held the dildo steady in the middle, resting her fist on the crack of my ass, and then eased it into her butt slowly, inch by inch.

When Lily's cunt met the tip of my cock, she lined them up and slipped my boner inside. Her pussy gripped my shaft with a tight seal. The swollen head of my cock filled her cream-coated velvety walls like a glove.

"OH, FUCK YES!!!" roared with the zeal of a lioness.

The double dildo now stuffed both of our asses. My cock was buried deep in her cunt.

Lily held my feet by the ankles, spread them wide apart, and began fucking herself rhythmically on the two cocks like an Amazon.

We panted and groaned and moaned and screamed and cried as our butts smacked together again and again and again. The more Lily bounced on my cock and the double dildo, the more overwhelming the pleasure became. It felt surreal. Unreal. Intense. Words don't do it justice. I was simultaneously fucking Lily and getting fucked by her. Oh wow.

Lily's movements grew more and more frantic. Each and every rocking of her hips and twist of her body made the dildo bend, wiggle, and poke my insides. The silicone veins protruding from the shaft kept hitting some spot on my prostate that made my dick rock-hard. It thrust me over the edge. I locked my eyes on Lily's, grabbed the back of her neck, and pulled her in for a hard sloppy kiss.

"OH FUCK! GOD! I'M CUMMING! OOOOOH FFFUUUCK..." Lily began screaming as I pumped stream after stream of cum into her wet orgasming cunt. The 18-inch double dildo coasted back and forth between our spasming asses, as my contracting core hurled it toward her, only for Lily's butt to thrust it back harder and deeper into me--a non-stop grind of mutual ass-pounding. I came so much. She squirted.

The bedsheets were a mess. We let the dildo plop out of our sore holes and lay next to each other, gasping for air and staring blissfully at the ceiling.

"Wow, babe!" Lily exclaimed.

"That was wild."

She threw me a crazy look and proposed, "Wanna try that again?"

That's when it dawned on me: sex with Lillian would never be the same.