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Arianna Sinn

In my first story about Allie, I broke her cherry. This story is about the time I took her ass virginity.

After we had been having sex for a couple months, Allie and I had gotten really good at it. We knew what each other liked and had no problems giving each other mind-bending orgasms. Of course, it was easy for her to get me off with her tight cunt and mouth. Getting her off was different a bit for me. I found that she would have a couple different types of orgasms….slow and soft when I fingered her clit, intense and fast when I fucked her and hard and violent when I licked her pussy. Sometimes, she would almost pass out when I licked her . I came to realize the reason she came so hard and nearly lost consciousness when I licked her was that I usually was fingering her asshole and it really got her off.

We were in my bedroom one afternoon on a summer day. My parents were at work and we usually fucked at my house a couple times a week. We quickly stripped each other and got into my bed. We had recently tried a 69 and both loved it, so we had been starting with it lately. She slammed her mouth down onto my cock as I stuck my tongue up into her hot, tight slit. As we licked and sucked on each other, both of us responded to each other’s actions with more intensity of our own. Quickly, we had each other on the brink of orgasm…the first of what was usually 7 or 8 for her.

I could see her cunt start to twitch and shake. When she was like this, she’d pull off my cock and throw her head back to scream when she came. As she shoved her pussy and asshole into my face as she came, I stuck a finger into her ass, knowing she loved it. She hit her orgasm hard…..and squirted a gusher onto my face. Her contractions were felt by my finger up her ass and mirrored by the tremors in her pussy. Moaning and hollering for me to bury my finger, I pounded her little butthole with my digit.

I rolled her off of me as her orgasm ebbed and got behind her. She loved doggy style and grabbed for my cock to guide me into her hot, steamy snatch. I loved when she did this and let her. She pressed me up to her opening and I shoved hard.

“UUUNNNGGHHHHH!!!” she moaned as I ripped into her over and over. As her pink, perfect asshole looked up at me, I breathed in the aroma of her. I loved how her pussy and ass smelled when we fucked. It was some sort of body chemistry thing and it made me crazy. I grabbed her hips and tried to split her open with my pounding thrusts. I got a look at her face in my mirror and her face was a sheet of ecstasy…eyes rolled back, jaw open and her breath coming in short pants. She was getting close to coming again and I wanted to come together. I felt her pussy grab me and start that wonderful spasming.

I tried to wait for her but I started to come first and let go inside her. Wave after wave of hot sperm crashed inside her cunt. Her orgasm started about then, joining mine in both intensity and pleasure. She shook and rocked her pelvis, trying to milk every ounce of pleasure from both of us. She did a great job and we both collapsed gaziantep escort in each other’s arms.

“God, that was good. I love how you make me come so easily. You really know how to push my buttons.” she sighed as we kissed softly in the afterglow.

“Do you notice how different your orgasms are when we do it different way?” I asked.

“Yeah, but I enjoy all of it. You can do whatever you want when you’re getting me off.”

“You like my finger in your butt, huh?” I asked.

“Yeah,” she said shyly, “it feels really good. It’s a whole different feeling and I can really zero in on it when you do it. There’s something almost more intimate and trusting about it. I never even thought about that until you did it our first time.” she admitted. That was the opening I was looking for.

“Well, what if I stuck this up there?” and took her hand and placed it on my cock.

“Ummm…..I don’t know about that. Your finger is smaller and I’m scared it will hurt too much.” she said. “But if you want to try it, I guess it’s okay. You’d have to stop if I asked you too. And you’d have to use Vaseline or something…I don’t want to do this dry.”

I reached into my nightstand and took a new tube of K-Y out. I had bought it that week in anticipation of this moment and wanted to be ready. She looked at it and gulped. Then she looked at my cock and into my eyes after.

“O-okay. I trust you and I love you. Please be gentle.”

“Let me prep you for this. Relax…I’ll make you ready for me. I love you too.” I told her. I scooted down between her legs and rolled her legs back, exposing her little butthole to me. I had rimmed her before and it dove her crazy and knew I should start with something she loved. I flicked that balloon-knot and teased it with my tongue, gently moistening her and arousing her. She was enjoying what I was doing and settled into a nice rhythm with her hips. She was rolling them to the motion of my mouth on her and whimpering slightly. It was time to prep her.

I uncapped the lube and squirted a long bead onto my index finger. I figured she’d need a bunch but wanted to drive her mad and apply it 2 or 3 different times before I fucked her. Sliding my finger in her ass, I worked the lube around, coating her sphincter well. I withdrew and re-beaded my finger. This time, I slid two fingers into her and worked the lube in. She was moaning now and pinching her nipples in delight. I went all the way in with my fingers and started to wiggle them. She liked when I did this and I felt her grab my fingers with her ass muscles.

Once again, I coated my fingers and lubed her inside her asshole. She was incredibly turned on and panting hard. Her pussy was soaked again, with her juices dripping down her onto my fingers inside her and onto my bed below her ass. Over and over she was saying, “Oh God, oh yeah, oh God, oh yeah, feels so good.” I figured this was as good a time as any to go for it. I sat up and squirted a glob of lube on my rigid cock and smeared it all over.

“Do you want me on top of you or behind you for this?” I asked.

“Get….behind….me….please….go….slow…..I’m….scared…but….want….you….in….my….asshole.” she stammered.

I rolled her over onto her hands and knees again and got behind that tight ass. God, she looked great, bent over and glistening with lube and pussy juice.

“Allie, finger your pussy for me. I want to see you play with yourself for me.” I told her. She immediately stuck two fingers into her cunt and began to frig herself. I slowly stroked my cock while she did that, never taking my eyes off her asshole. She moaned and whimpered and her cunt was making nice slurping, sucking sounds around her fingers.

“Fuck my ass now. I want you inside me. Oh God….FUCK ME!!!”

The tone of her voice almost made me come right there as I had never heard it before. It was deep, throaty and husky…kind of like Demi Moore would sound when taking one up the ass. I waited a second to make sure I was okay and pressed the head of my cock against her browneye. She shuddered and grabbed both her ass cheeks and pulled them apart, inviting me into her virgin ass.

Her asshole was obviously tight and I went slow working the head in. The lube made it possible to get that far as she was nervous-tight still. I told her to relax and trust me. She did a bit and I managed to get the head in at last. She gasped and went rigid, tightening every inch of her body. I pushed a bit and felt her open up for me. She let a loud yelp of pain go and slapped at the mattress, trying to bear the pain. Slowly I pushed, about halfway in by now. She wasn’t asking me to stop or resisting, but was still nervous-tight.

“Do you want to stop or try another position?”

“What..other…OUCH….position…can…we…OHHHHHH” she got out before I felt her asshole finally relax and I slid all the way into her, balls deep. I gasped as I wasn’t prepared for how an asshole felt. It was incredibly tight and felt almost grainy, but it was amazing. I slid out about halfway and went back in.

“OOOOOOOOHHHHH!!!! OH, GO SLOW!!! OH GOD, FUCK MY ASSHOLE. OOOOOOOHHHHH!!!!” she moaned in ecstasy. I went very slowly in and out, making her grunt and produce sounds I had no idea a woman could make. They were gutteral and almost like an animal’s. She wasn’t making words now, just word fragments and sounds.


I was in a nice rhythm now, sliding in and out nice and easy, feeling her tight asshole grip me with each stroke, the lube really sealing me inside her and her butthole making these nice queef-type sounds with the in-thrusts. Suddenly, she tensed up and I thought she was having a spasm of pain and was going to ask me to stop. I wasn’t sure if maybe she had had enough and was done. Instead, she let loose with a scream and let an orgasm rip that I’m sure registered on the Richter scale. She threw her head up and down and side to side, slammed her ass back onto my cock and was shaking the headboard so hard I thought she’d rip it off the moorings.

“OH JESUS FUCK I’M COMING OH MY ASS IS THROBBING OH SO GOOD OH MY GOD FUCK ME HARD NOW FUCK MY ASS HARD NOW OH PLEASE POUND MY DIRTY SHITHOLE!!!” she shrieked as she came. It was amazing feeling her ass contractions abuse my hard cock. I gave her what she wanted and began to pummel her shit-pipe as hard as I thought she could take it. Hard, but not as hard as I could. I didn’t want to hurt her.

“I SAID FUCK MY HARD MOTHERFUCKER NOW FUCK ME DON’T TICKLE ME POUND MY ASS!!” she yelled in a voice overtaken with passion and emotion.

As I began to go balls-deep, every stroke, with as much force as I could muster, I watched her jam two fingers into her pussy again and grind on her clit. I wanted to pull out and lick her, but knew I had to finish what I was doing. I felt ready to come, but was almost afraid to, since she was coming so hard being fucked like this. I wanted to pleasure her until she begged me to stop, but knew that wasn’t going to happen.

She had collapsed onto the bed with my cock still embedded in her asshole. I dropped on top of her and kept pounding away inside her. She was just shaking and shaking, not coming anymore, but having some sort of seizure I thought. I turned her head over and looked in her eyes…she was gone. Just….gone. She was in there somewhere, but somebody else was driving the bus. I pulled out and rolled her over and plowed right back into her ass.

She shuddered and locked eyes with me. I asked her if she was enjoying this and she nodded, but couldn’t do more than grunt. I knew I was close and told her I was going to come inside her asshole. I went rigid as my seed exploded from my cock and scalded her insides. She gasped and grabbed me tight as I spurted over and over into her. As I finished, I fell on top of her, exhausted. We both must have fallen asleep immediately.

When I came to, she was still curled up next to me asleep. I got up to take a leak and as I pissed, I noticed my cock was covered with smears of lube and ass-mess. I cleaned up and went back to her with a wet cloth. She was awake and let me gently clean her. She was a mess….the cum had leaked out and had dried on her ass, she had lube and ass-mess on her as well. Her butthole was bright red from the pounding. I asked her if she was okay.

“Y-y-yeah. What happened? I don’t remember much after it was over.”

“We passed out. I think you liked it.” I teased.

“I did, but my butt feels like it’s on fire. We can’t do that again for a while, but we ARE doing it again.” she promised. We fucked once more that night, nice and slow and gentle and caring. We both had nothing left to give but were ready to express ourselves once more that night.

Anal was a nice part of our sex life until we split up. Her favorite way ended up being with her on top of me, riding me with my cock up her ass. I liked it too because she could squirt cum really easily when she did that and I loved having it splatter my chest and face. I still dream about that tight little teen asshole and wonder if she still dreams about me.

Coming soon…I find Allie on Facebook.

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