Two Lovers First Anal

(This is my first attempt at a Literotica story. Please take note that this is a true story, but like movies and similar stories some events are exaggerated for added effect.)

A quick background on Alanna and I, we met while playing a game over the internet. Quickly we found huge interest in each other, and within a week of flirting, we were off to dating.

Alanna lived in Tennessee, and I lived in California. From city to city, we lived approximately two thousand miles away from each other. But, we were undeterred.

Fast forward a year and a half into our relationship, it was early June and I was embarking on my second trip to go visit the love of my life.

"I'm getting on the plane, I love you so much baby," I texted her before I got on the plane.

"I love you too Devy."

Ten hours of layovers, flight times, and traversing huge airports, I finally arrived at my destination.

The smell of clean air entered my nose, how nice it is to not breathe in the smoggy, filthy air of my birthplace. After disembarking from the plane, I headed to go see the one that I called baby.

There she was, the most beautiful thing I had ever set my eyes on. At a height of 4'9", a weight of 110 and curves to die for, she was a sight like no other. Moving toward her as swiftly as possible without making my steps seem awkward, I embraced her lovingly.

"I've missed you so much," I said.

"I've missed you so much more,Devy."

I could smell the conditioner she used in her hair, it was a beautiful fragrance that mixed perfectly with the perfume she was wearing. The sight of her was almost too much to bear, and it didn't go unnoticed.

"Really Devon?" She asked smiling.

"Sorry, I can't help it!" I replied.

She giggled, and we walked hand-in-hand to go pick up my luggage.

We drove to her house, where she lives with her family. As we were exiting the car, I could not help but stare at her perfectly round ass as it swayed in front of my awe-stricken eyes. I had to avert my eyes from this delicious eye candy before I embarrassed myself in front of her family.

She led me to her brothers' room, where I would be sleeping for the duration of my stay.

I set my luggage near the door, and followed her into her bedroom. It was clean, except for her desk where she spends most of her time playing online games with me. Soon after settling in, we got right to work. I sat on the bed, and we began almost immediately making out.

"It's been so long," she moaned sexily into my mouth.

"I know baby, this time, you can have it all."

This statement acted like a catalyst and our kissing became more intense. She detached from our making out, and sat on my lap cowgirl style and bounced up and down on my clothed, erect cock.

God damn, she's such a tease, I thought.

"I've only been here for five minutes and you're already all over me," I said laughingly, "don't you think we should wait a little before we get down to business?"

"Hell no! I've waited a year to have this. I'm not going to waste my time."

After a couple more minutes of being the stereotypical horndog teenagers we were, we had to stop before some of her family entered the room.

I couldn't wait to have it. A virgin, short, hot girl, all to myself.

Alanna is a very small girl, her hair color varies almost monthly, but at the time it was a beautiful dark purple-ish brown. Her hair is long, and soft. It's the kind of hair that actresses and celebrities spend thousands of dollars on yearly just to have a fake version of. She has a lean frame, with sexy curves. She has perky breasts at about 34B in size. You might not think that's big, but put that on a girl who is 4'9" in height and it's more than enough. Her legs are to die for, her sexy thighs, well-toned from her countless hours of jogging and exercise. And leading from her sexy legs is her most appealing physical trait, her perfectly-sized, round ass. It's the kind of ass that makes you turn your head 90 degrees just to get a good look at it's perfection. It didn't just look good in pants, either. She has the most beautiful pair of green eyes I have ever seen, and occasionally yellow rings will be circling her pupils.

A little about myself, I am not in her league whatsoever. I was a peasant to a queen. I am a bit overweight, but not obese. I have long, blonde hair that goes down past the collar of my shirt. I have a mediocre face, but no acne or blemishes thanks to good hygiene and good genes. I would like to think of myself as well-endowed, with a little over 6.5 inches in length and five inches in girth. Enough to please the sexy little girl that yearned for it.

As night began to descend, and every one started heading for bed, we made our move. We entered her brothers' room quietly. We began as usual by making out, kissing passionately and swirling each others' tongues in one anothers' mouth. I sat on the edge of the bed, my rock hard cock straining against the fabric of my pants.

"Daddy want his dick sucked?" She asked with a sexy grin.

God damn, I love it when she calls me that.

"Please... " I moaned in reply.

She began unbuttoning my pants, until they were completely off. My erect cock sticking straight out of the hole in my boxers. She wasted no time getting to work.

"Mmm, I love daddy's big cock," she said as she placed one of her little hands on the base of my dick.

She began stroking my dick slowly, making sure her daddy was completely hard before she used her hot, wet mouth on my thick cock.

She opened her mouth and put the head in her mouth.

The sensation was unimaginable, it had been too long since I've had this sexy girl sucking my fully erect cock. She began to suck deeper into her mouth, and swirl her tongue around the head of my dick all the while.

"Mmm, god damn, baby, you are too good," I quietly said, making sure no one heard.

She giggled while my cock was still in her hot mouth, it sent shivers down my spine.

Unfortunately, and fortunately, I am not an easy person to get off. But that is no problem for me, with her, the orgasm isn't all that matters. The journey is equal to the pleasure of the climax.

"Now it's your turn," I said, switching positions with her.

There I was, between the sexy legs of the love of my life, unzipping her pants and undressing her from the waist down. After her pants were off, all that was blocking me from her delicious pink pussy was a cute pair of panties. I slid her panties down her legs, and marveled at the sight before me. A small, hot pink, virgin pussy, just for me, right before my eyes.

I started off with slow, flat licks on her clitoris. Making sure not to go too fast. After a couple minutes of warming her up, I began to sharpen my tongue, and eat her out faster and faster. Her taste is astonishing, her being my only girl friend, I had no idea it was going to be so delicious. I began licking furiously, enjoying every drop of pussy juice that was offered to my wanting tongue. I spread her pussy lips apart with my fingers, and shoved my tongue as deep as I could inside her opening. The taste of her nectar washed over my tongue, I began to feel intoxicated by her scent.

"Ohhh goddd Devon, it feels so good!" She exclaimed.

I know her every spot. I know just how to get her going. Her climax was approaching fast, and I wanted nothing more to bring her the greatest orgasm she had yet to experience. I could see her hands clenching the sheets, almost in preparation for the coming orgasm.

"Ohhh goddd, Devonnn!" She almost screamed.

She began bucking her hips wildly, but that only acted as an aphrodisiac to me, and I licked and sucked relentless at her clitoris, until it was too much for her, and she ordered me to stop. She laid there, breathing heavily, whimpering, shaking from her earth shattering orgasm.

I bent over her and kissed her passionately, letting her enjoy the pussy juice that was still on my tongue, her tongue swirled around mine and she enjoyed it just as much as I did. Both satisfied with our encounter, we said our good nights and departed, only ten feet away from each other in separate rooms.

The next night I was offered sex by my young, virgin lover. But not the sex that you would think.

You see, her mother is very over-protective, and we are not allowed to make love. Alanna was not on birth control, nor did we have condoms that we could use with out making it completely obvious to her mother that I had defiled her daughter in her own home.

Her offer was unexpected, but welcome. Instead of risking pregnancy, she offered me anal sex.

How could I refuse? It was always something of my fantasies, albeit a bit odd that I was going to experience anal sex before vaginal. However, I didn't care. All I knew was it was going to feel amazing.

Later that night, Alanna snuck into my room with some make-shift lubricant, vaseline.

"Are you sure you want to do this? I don't want to hurt you, Alanna," I said softly.

"Yes, Devon, I want this," she said in reply.

We started off as usual, making out intensely, feeling each others body's through our clothes.

However, we decided to skip oral sex just to make sure no one would suspect Alanna was missing from her bedroom.

I was shaking in anticipation, fear, anxiety, love, and so many other emotions.

"What's wrong , Devy? Are you sure you want to do this? You don't have to," she said with a worried tone.

"I want this, Alanna, I want it so bad," I said through chattering teeth.

I manned up, and I bent her over the bed. I pulled down her pajamas, along with her cute panties and was delighted to see her beautifully-shaped ass awaiting my entry. The room was dimly lit with christmas lights that her brother had put up in his room.

I started by putting a dab of lubricant on my index fingering and inserting it into her tight, virgin ass.

"Ohhh," she moaned pleasantly.

Being inexperienced, that's all I did before I started lubing up my fully erect cock. I put the head of my cock at the entrance of ass and pushed very slowly. I could feel the head begin to enter her extremely tight ass. I heard her take in a deep breath of air, and slowed my pace. The last thing I wanted to do was hurt my little angel. I waited for her ass to stretch to accommodate my thick cock, and began to push further into her ass. Inch by inch, my cock began disappearing into her ass. Eventually, I had bottomed out inside her, and I was literally balls-deep into my baby girl's sweet ass.

"Mmm," she moaned as I began to slowly thrust in and out of her ass.

The feeling of her tight, virgin ass around my thick cock was unbelievable. Thankfully, her ass was well-lubricated and ready for a pounding from her daddy. After ten minutes of letting her get used to the rhythm of my cock sliding in and out of her ass, I began to pick up the pace.

"Fuck me harder," she said unexpectedly.

It turned me on dramatically to hear my sexy girl tell me dirty things like that. I began to thrust harder, and deeper into her ass. Her hips acted as a perfect handle for me to hold on to, and I plowed into her relentlessly.

I couldn't believe it, she was actually enjoying taking a cock in her ass. God damn, I am the luckiest guy on Earth, I thought.

I felt my climax soon approaching, I couldn't hold out much longer.

"Can I cum inside you?" I asked, panting, all the while not losing my rhythm.

"Yes, cum in your baby girl's ass, daddy."

The feeling of her ass around my cock, mixed with her dirty talk pushed me over the edge.

"I'm cummingggg," I moaned loudly.

"Hold me, daddy, hold me while you cum!" she said to me.

I bent over her tiny body and held her. I could feel every rope of cum spurting inside of her, I never came so hard in my entire life. I filled her up with my hot, sticky cum fast. After my mind-boggling orgasm, I slowly slid my still-erect cock out of her ass. The moment I took my dick out of her ass, streams of cum were dripping from her gaping asshole.

"Oh, god, we're going to make a mess!" She exclaimed frantically.

Did I care? Not really, I just had experienced anal sex for the first time, and I was still mind blown from my orgasm.

She ran out of the room to the bathroom, still naked, just down the hall.

A couple minutes later of cleaning up, and letting the cum ooze from her freshly-fucked asshole, she came back in the room.

"That was amazing," she said, walking up to me.

She placed her hands on my cheeks and kissed me deeply.

"I love you," she whispered.

"I love you too baby girl."