Anal With My Best Friend’s Girl

Big Tits

Why was my best friend telling me this? God, why couldn’t he keep his mouth shut?

I sat back against the hood of his car and sipped on a beer. On Javier’s front lawn was a grill and flames were shooting up from the charcoal we’d just lit. We were both nineteen. I don’t remember how the topic got started, but the sentence I’ve committed to memory was:

“She really wants me to fuck her in the ass. Last night was like the hundredth time she’d asked me. She’s been bugging me a lot about it lately.” Javier said, acting as if he had a problem on his hands. He opened up his can of beer and gulped it down.

Javier had been dating Danitza for three years. He’d lost his virginity to her back in high school, as she was his first real, serious girlfriend. I’d always thought of her as a shy girl, reserved and very quiet when we went on double dates. Thinking back on it now, I know it was because she wasn’t comfortable around me, or any of Javier’s friends. She wasn’t comfortable with anyone who wasn’t from a rich family. But that didn’t stop her from liking Javier, and reveling in the excitement that he brought her with his gang lifestyle.

“Why don’t you do it? You’re an idiot.” I said.

“Cause…it’s gross, don’t you think? She shits out that hole–how am I going to stick my finger up there, or my dick? She’s tripping. Men aren’t supposed to put it up a girl’s butt, that’s what a pussy is for. Only gay people do it.” He stopped speaking for a moment and looked at me, I could tell by his face that this conversation bothered him. “Have you ever fucked Ivonne up the ass?”

“No. She won’t let me.” This was true, at the time she’d denied me, but even if we were having anal sex, I wouldn’t have told him. My sex life was private for a reason–for a reason like what was running through my mind about his girl at the moment.

“But you would do it if she let you?”

“I would, and you’re stupid for not doing it with Danitza. Just try it. It’ll probably hurt her and she won’t ask anymore.”

“Hell no, I won’t. I hate that she asks over and over. I fuck her good, and when I’m drunk I eat her out, but I won’t touch her ass.”

So now I knew that my best friend’s girl wanted it up the ass and wasn’t getting it—that wasn’t good. At that time in my life(maybe still), my ultimate goal was that rare, and magnificent chance to have anal sex with a woman; any woman. And until then, I’d yet to meet a willing female who wanted it in the ass.

The last thing I wanted was to be fantasizing about my friend’s girl. Her image came to mind as I drank that beer on his driveway. Danitza had long straight hair, brown in color. She wore neatly cut bangs always. Her eyes were brown, almost black, and were gigantic on her narrow face. Her nose was a too pointy for her face, it was prominent when you looked at her, but it didn’t hinder her looks, in fact it spiced her up.

She was Spanish, not Mexican like most everyone in our circle of friends. There is a very, very big difference between Mexicans and Spaniards. The Spanish are white people…Europeans, and more often than not think they are superior to any Latino. She’d moved from Madrid to the United States with her family six years ago. There’s not very many Spaniards you meet in California’s Bay Area, so it made her very exotic like.

Danitza didn’t have much of a body either…in my regards at least. Remember, I like thick women. And Danitza never caught my eye in the least bit—not till Javier ruined it. Danitza had skinny, toned legs, and a somewhat curvy butt (compared to her body) that you could probably make disappear in the palm in your hand. Her breasts were tiny things–she was petite, that’s the word. Javier liked his girls like that, real athletic like and fragile. Her body looked breakable almost, she was like a china doll; all pointy elbowed and bird boned.

“I think you should do it. It’s supposed to feel good, for the guy.”

“Have you done it with any girl?”

“No. Not yet, but one day I will.” This was a lie. At that time I’d fucked two girls in the ass. The most recent was my girlfriend’s younger cousin Bianca, who I couldn’t admit to anybody about, (not that I would) because I didn’t want to embarrass Ivonne, who’d been part of the threesome. The other woman was, Lorry, the mother of one of our friend’s(see: A First For Everyone). Lorry was the biggest secret. Ivonne didn’t even know about her at the time.

The thing about those two women was that they hadn’t wanted it in the ass. Bianca had been barely willing, Lorry less so–but to think that Danitza wanted to try it; wanted to be fucked in her ass…it just drove me crazy.

From that day on, I couldn’t help but become aroused whenever Danitza was around. I found myself studying her face, her puffy pink lips, her slender hips and skinny toned thighs. I felt bad about these feelings. I knew it wasn’t right to be lusting after a friend’s girl, so I buried these feelings deep, like any man in my situation should do.

I began to distance bahis firmaları myself from Danitza, declining invitations to go out if she’d be around, so I wouldn’t see her. But, all situations couldn’t be avoided, and I knew I had to man up and push these evil thoughts from my mind, and it worked. But the seed had been planted in the soil of my mind and soon the seed grew like an uncontrollable weed.

Ivonne, my girlfriend, decided to go wine tasting in Napa with a few female friends. Naturally, Ivonne and Danitza had become friends because Javier and I hung out so often. Danitza had been invited, along with Bianca, Ivonne’s cousin, and another friend named Susie. The group of girls all had fake I.D’s, so tasting wine at nineteen wasn’t a problem.

I’d dropped them off early on an autumn Saturday morning. We picked up Danitza first at her parent’s large house and as soon as she stepped out of the door my dick began to stir. She was wearing a small black dress and her bare legs were blindingly white.

The ride up there was uneventful. I tried my best to not look at Danitza in the rearview mirror, but it was hard. It was easy to disappear as driver with a group of girls laughing and talking and I found myself secretly glancing back in the mirror to her position seated behind the passenger. Each glimpse of her seductive face and pouty pink lips only tortured me more. I’d been cursed with this stupid knowledge, and now I’d be forever uncomfortable in the vicinity of this Spanish beauty.

A couple of times Danitza caught me looking at her and I embarrassingly looked away each time our eyes caught in the rearview mirror. For her it was probably nothing to catch eyes like this, but for me, I felt an electric pang in my stomach, a static jumpstart to my penis.

Half of my excitement, I’m sure, was the guilt I felt, secretly checking out my best friend’s beloved girlfriend right in front of my girl’s nose; the other half was my secret knowledge that Danitza craved a cock up her ass–not her pussy–but her ass. And sadly, I wanted it to be my dick in her asshole. I wanted to be the one to violate her tiny, sweet rosebud, and to plow unmercifully through her fertile virgin ass. I wanted to be the one to stretch her little hole out to the width of my cock, repeatedly and repeatedly, filling her bowels with my manhood. What could be so wrong with wanting to listen to her squirm and moan when I pushed in her backside for the first, and third, and hundredth time? What could be so wrong with wanting to rest my balls against her wet pussy lips while my cock was buried full length up her hot, oven like rectum?

It was only a fantasy, right? What was wrong with a fantasy? Nothing.

Yes, I could fantasize all I wanted, I told myself, people do it all the time.

How would she be in bed I wondered? She was so reserved and quiet…did she moan loud during sex? Was she silent? How did she look sucking cock? I wondered if she swallowed cum. How did her small breasts look naked. What kind of noise would she make the first moment she felt a cock enter her ass and stretch her and fill her. Would she take it in silence?

Thinking all of this on the hour long ride to St. Helena’s made my dick painfully hard.

She looked stunning sitting there in the back seat looking out of the window at the passing vineyards. Her white skin was sharply contrasted by her black almond like eyes and red lipstick. Her bangs were hanging curtain like over her forehead, cut right above her eyebrows. She sat there silent most of the time, smiling every now and then, but not speaking much. Ivonne could be very loud around her friends, and this difference in socializing intrigued me. You could tell Danitza was always full of thoughts. She remained aloof of conversations, and mysterious in her soft seldom spoken words.

I dropped them off and watched as they walked away. It was hard not to look right at Ivonne’s massive behind wiggling with each step, she wore tight cotton pants that didn’t hide a thing. Bianca too, looked lovely in a short pleaded skirt and knee high stockings. The other girl Susie was fat and easy to avoid with the eyes. I forced myself to watch Danitza, and her small firm behind caught the dress only slightly. But by the way it hung, I thought I could detect a thong. I grabbed my cock as I watched them walking away into the beautiful winery.

I’d managed to fuck two of the girls walking there; Ivonne and Bianca, and now I wanted Danitza—geez, I was crazy. I shook my head at my horny, irrational self. I was lucky enough to have gotten Bianca, but now my dick was pushing things too far. How could I expect to fuck Danitza, who wouldn’t look twice at me, and had spoken maybe fifty words to me in over three years.

I was just a guy fantasizing, nothing more.

I drove home, and when I arrived I masturbated about Danitza. My cock had been hard for too long and I needed relief. Once I’d come, my lust vanished and I felt guilty. I spent the day watching the Giant’s game and kaçak iddaa smoking weed. Finally, some five hours later, I received a phone call from a very, slurring and drunk Ivonne: they were ready to be picked up.

The drive out was fantastic. The winery was past St. Helena and in majestic northern California wine country. Rolling yellow hills dotted with oak trees were on either side of the road. All of the vineyards and fancy houses were inspiring, and romantic to say the least. There were many bicyclists and motorcyclist out enjoying the day.

As I rolled up to the parking lot of the vineyard they’d shuttled to, I spotted the group of girls sitting along a stone fountain. There was only three of them, Susie the big one, was missing. They saw me, well, Ivonne saw me and immediately jumped up and frantically waved at me. I saw her tugging at Bianca, who was asleep.

“Help us.” Ivonne shouted, too loud.

I parked and put the hazard lights on. Danitza was standing there looking very embarrassed, but she was drunk too, as she kept laughing louder than normal at Ivonne’s attempts to lift her sexy little cousin.

I walked over to them and Ivonne kissed me passionately. I could taste the wine on her.

“I’m drunk.” She said.

“I can see.” I looked to Danitza. “And so are you.”

She smiled and laughed. “A little.”

“Where’s Susie?” I asked.

“She found a man. He’s gonna drive her home.” Danitza said.

I picked up Bianca and walked her to the car, sitting her in the back seat and buckling her up. Her skirt had ridden up and I saw the tops of her nylon leggings. I quickly pulled the skirt down over her thick brown legs.

There were many wine tasters out that afternoon and I had to stop and slow for them to pass the parking lot. As I stopped for another group of women drinkers walking nonchalantly through the lot, a gust of wind shot through them and lifted up a woman’s dress exposing her black panties. She was an older woman, but did have ass.

“Oh, watch your skirt lady. Woot, woot!” Ivonne yelled out the window.

The woman shot our car a dirty look and Ivonne laughed.

“You liked that, don’t lie.” Ivonne asked me.

I didn’t answer.

“I know you did. You’re such an ass man.” She turned to Danitza in the backseat and said, “He loves a girl’s ass.” She giggled. I saw Danitza smirk and she looked at me through the rearview mirror, this time I didn’t look away and we both exchanged a smile. Her eyes seemed full of emotion as if she were trying to convey something to me through their steady gaze.

It was a moment, our first moment, I thought. Always she dismissed me and ignored me. Was she smiling because of drunken Ivonne? Or because Ivonne said I loved ass on a girl. Or was she just drunk?

Either way, the moment pleased me, and her eyes seemed to stay on me in the mirror afterwards. Every time I looked back her eyes were on me, and she glanced away, but not after a secret holding of the eyes. Our eye contact was lasting too long and it gave me butterflies in my belly. This was wrong, I thought, but I couldn’t help but look back at her and see if I was imagining this or if she’d give me a long stare again.

There were a lot of people out on the road, and after a few minutes of blasting music, Ivonne was snoring beside me. I looked in the rearview mirror and saw Bianca asleep as well, only Danitza was awake, staring out the window. I saw I needed gas, so I pulled over at a small gas station in St. Helena.

When I got out the car to go to the pump, I saw Danitza get out too. She began walking to the store, but halfway there, stopped and turned and looked at me. She saw me staring at her, and I looked away. Danitza came slowly to me, I had the feeling she was hesitant in approaching me.

“Want something from the store?” She asked. Her voice was a bit deeper than most girls I knew, full of tone and body, yet still feminine.

“No, I’m fine.”

“I’m going to get some smokes.” She said, turning around and walking off.

I followed her with my eyes, watching her tiny butt pop out slyly from under the black dress. I noticed a man leaving the store couldn’t keep his eyes off of her, and he turned his head to follow her with his eyes. Suddenly she flashed her face back at me and saw me gawking at her. She held my eyes and gave me the sexiest smile I’d ever received from a woman at that point in my life. Her smile hit my soul, and when her gaze turned away, the world didn’t seem as bright as before; like when a cloud passes in front of the sun, the world had dulled after her smile.

I finished pumping and she returned.

“I didn’t know you smoked.” I said.

“I don’t really, only when I’m buzzing.”

“Do you want me to drive to a park so you can smoke? You can’t smoke here, obviously. No smoking in my car, except for weed.” I said.

“Yeah, a park would be good. Thanks.”

She climbed back into the car and shut the door. I finished pumping and drove off. I knew there kaçak bahis was a park coming up just down the road. But there was so much traffic in that small little town because of the stop lights, that it took forever. While driving I looked in the rearview mirror and sure enough, I caught Danitza looking at me again.

Finally we reached the park and I pulled over along the road. I shook Ivonne and she opened her eyes, man they were bloodshot. “Are we there?” She asked.

“No. Do you wanna smoke? We’re stopping to smoke?” I asked.

“What? No. Wake me when you get there, God I’m sleepy, I drank too much.” She said. Bianca didn’t respond at all when we asked her. So, it looked like it was going to be just me and Danitza sharing a cigarette.

I wasn’t sure if this was a good thing or a bad thing.

I don’t smoke, but I was thinking with my cock, so I exited and walked with Danitza under the tall oak trees that shaded the green grass of the park. Most of the leaves were turning yellow and orange and there was a sea of dead leaves on the park floor. There was a wooden bench up a ways on the path, slightly hidden by a grove of oaks.

“Wanna sit there?” I asked.


We walked in silence, side by side. I could feel her presence next to me like a source of heat. Her sexuality latently oozed from her and smashed against my senses, I felt out of my league beside her. She was in a different class of sexiness. Ivonne, my girlfriend, was all physical. It was her model like looks, and thick butt and breasts and the skimpy clothes she wore, the way she spoke and touched and looked at you; that was Ivonne, and it was sexy as hell, but Danitza’s sexiness was different.

It’s hard to put to words how Danitza works. It’s magic like, and it lies deep within her silent personality, and European way. Maybe it was because she wasn’t mine, and I could never have her, but walking beside her, I had the feeling she was the center of the world, and everything and one, moved around her.

Even walking with her alone felt wrong. I felt as if I’d committed some sort of crime and that I’d somehow betrayed my friend and Ivonne, but at the same it was exciting.

The wind picked up a little and her silky brown hair turned like a curtain caught in the breeze. She swept her delicate fingers through her hair and I could smell her perfume lift from her by the wind. The silence between us was awkward, but I felt that if I spoke I would ruin everything and she would become distant and dismissive of me as she usually was.

We sat down together and she opened up the pack and pulled out a cigarette for me. I saw that her hands were tiny, and her nails a simple maroon red to match her lipstick. She put her cigarette to her mouth and tried to light the tip, but it was too windy, and I could see she was having trouble.

“May I?” I asked, leaning in and covering her smoke with my hands. A wisp of her hair touched my outstretched palm. She lit it and inhaled deeply. I lit my smoke.

“So did you have fun wine tasting?”

“Yes, I love wine.” She finished as if she had nothing else to say or hear from me, so I shut up.

The silence resumed and it killed me. And then out of nowhere she spoke.

“What did Ivonne mean when she said you were an ass man?” She asked, not smiling, but genuinely serious. Wow, Danitza is all business, I thought.

I chuckled, meanwhile my stomach turned. It means I’d take great pleasure in putting my penis in your butt, I answered in my head.

“Ah, she was drunk.” I said. “It’s just because…well, I don’t know how to say this, it’s kind of personal—”

“What?” She smiled.

“I feel weird telling you.”


“Because…I don’t know. You really want to know? Promise you won’t tell anyone then.”


“Don’t laugh at me, but when we’re having sex, me and Ivonne, sometimes I ask if she’ll let know, put it in her ass. I feel weird talking to you about sex, you know, you’re my friend’s girl and all.” I looked away embarrassed.

Truly, I don’t think Ivonne meant to imply anal sex when she said I was an ass man, I think she meant that I like girl’s with big butts. But this was an opportunity that I couldn’t pass up. It was a perfect chance to breach the exotic subject.

She fondled her cigarette for a while and hit it. What was she thinking I wondered? She looked very sexy sitting there with her glowing white legs crossed and the wind blowing in her hair, a cigarette dangling perilously from the tips of her fingers.

“She doesn’t allow you to do it?” I smelled wine on her breathe as she spoke.

“No. Sadly no.”

“That’s funny you say that.”


“Oh, no. I could never say.” She smiled secretly to herself.

“You can’t tell me? I just admitted something personal to you.” I said in a joking tone.

“I can’t tell you because I’m a girl for one, and for two, I’m your best friend’s girlfriend. You’ll look at me different if I tell you.”

“I won’t. Do you see me differently after I told you about my wanting anal sex with Ivonne?”

She looked me up and down in a glance, “Yes.”

“You do? You’re supposed to say no. What’s different then?”

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