Having been an extreme fan of anal my entire adult life - breaking the friend barrier with my best friend of over 13 years was nothing short of heaven. For years I had masturbated at the idea of having sex with her. I even took candid photos of her fat ass in leggings, and stole a few pairs of panties from her dirty hamper. After years of appreciating her from afar, I took a risk and attempted to break the friend barrier.
I spent the first 21 years of my life in a large apartment building complex and much of my childhood was spent with the other kids around my age in the building. We grew up together and summers consisted of hanging out in the back-yard basketball court, pool, and in each other’s apartments.
My best friend from the group was a girl named Eva. She’s two years older than me and we met when we were little. She’s always been a beautiful girl; purely Irish with blonde hair and a thicker, but not fat, build. She was also always the troublemaker of the group – the first to come up with a stupid idea like borrowing her mom’s car without a license, wandering off around town without telling our parents, and doing all sorts of things that got me in trouble.
As we grew older and entered high school, our two-year age divide started to show itself. She started getting into drinking and smoking with her friends, wearing tight leggings and dating guys. We started to drift away in closeness but always remained friendly. I remember coming to school freshman year and seeing how wild she was – she had a reputation for being a slut, had a fat ass and liked to show it off in really tight leggings with tee shirts (so everyone could see her ass), and she sold pot.
It wasn’t until my senior year of high school, and her sophomore year in college, that we started hanging out again almost every day. By then, I myself had started getting into drinking and smoking so we’d link up every night to blaze in the back of my building with many people from our original building group as well as other new friends. It was at this age that I started to appreciate just how sexy Eva was. She had dyed her hair red, had such a thick ass and thighs that she always stuffed into leggings that were a size smaller than she needed, and had a fun personality.
I had always wanted to bust a move on her, but she always saw me as so much younger and was into guys with tattoos and beards, so I lacked confidence. I settled for the next best thing I could at the time – pictures. Whenever we’d hang out, I’d try snap a few shots of her ass in leggings for jerk off material at night. I eventually compiled hundreds of these photos – and would secretly appreciate her beauty without her knowledge.
Eventually, since I spent a lot of time at her house just hanging out, I had many opportunities to steal her thongs and finally mustered up the courage to take one. On three occasions, she had briefly stepped out of her apartment and I was able to grab a thong buried in her dirty clothes hamper while I waited for her to come back. One day she even took a shower while I was at her house, and I actually stole a pair of her leggings by putting them on under my jeans. Let’s just say that those nights were spent with my nose glued to her croch strings. Her thongs were all g strings – tiny little vagina and asshole strings that absolutely reeked of her musk – especially by the little dental floss by her asshole. For at least a year, the scent of her pussy and asshole, plus the pictures, kept me as content as I’d be actually fucking her.
As time moved on, we remained close – spending a lot of time together during the summers. We continued studying and dating other people. The musk eventually faded from her thongs and leggings and they were no longer giving me the daily satisfaction they once had. For years I had been trying to find an opportunity to make a move on her, and that opportunity finally presented itself during my junior year of college.
We both were in relationships at the time – Eva had been in one with some rocker guy for practically 2 years and I was with some other girl for like 6 months. Eva started posting statuses on facebook questioning some of the fucked up things he did to her such as screenshots of him flipping out on her through text, and it was clear that they were breaking up. I took the initiative to talk to her about the statuses that she posted and to comfort her. She told me that they had broken up and that she was in a rough place, and I just told her that I found her so sexy, intelligent and fun and that she’ll have no problem finding a better man. She kind of had a twinkle in her eye as she looked at me after I said that, and she gave me a hug. I returned the hug but put my hands way lower than usual, wrapped around her lower back right above her ass and gave her a solid squeeze. I felt the slight dampness of her sweat through her shirt as we hugged for a few seconds in silence. After the hug it felt like I should have kissed her, but I just took a step back and we parted ways.
As the week went on, we continued talking a lot through text and I’d throw in some subtle flirtations like “feel better beautiful” to see if she’d flirt back – to confirm whether or not I should make a more formal move on her. Surely enough, she did – she told me how my girlfriend was so lucky to have me and that she’s jealous she can never find a man like me. After she told me how lonely she was feeling I went in for the move and sent a “I’d be more than happy to spend time with you this weekend so you’re not lonely anymore” with a winking face. The second I hit send, my heart absolutely fell to the bottom of my chest and I had the butterflies feeling you get when you ride a roller coaster. All of those years of watching from the sideline and never making a move, appreciating her figure in the pictures I took of her, and smelling her thong and imagining it was the real thing – led up to this moment. I didn’t know whether to regret it or be excited for her response.
Minutes went by and still no response – I started to get really worried that I fucked everything up. Maybe she just put her phone down for a shower. Did I freak her out? Did she not know how to respond? All of these thoughts consumed my mind as I nervously awaited the response to the move I’ve been waiting to make for years.
Finally, she responded by asking me what I meant by that. Not the worst response. I told her that if she was feeling lonely, I’d be willing to come over and make her happy, and less lonely, with another wink. She replied, “Oh … how would Christine (my girlfriend at the time) feel about that?” I explained that we were on the verge of breaking up too and that I’d be willing to end it for some kinky sex. She told me she was shocked that I’ve never expressed interest in sex (to her knowledge) for all those years, and that she’d think about it (with a smile face).
For the next couple of days, we kept texting and kept flirting until I finally asked whether I should end my current relationship. She asked what I meant by “kinky sex.” I gave her a one-word answer. “Anal.” I had talked with one of her ex-boyfriends at a party one night and he was telling me how she loved anal sex and ass play (which was, and still is, my biggest fantasy and fetish) – so I knew that might trigger a positive response from her. While I only said anal, I actually meant a whole lot more – like eating out and gaping that asshole and squirting loads of cum into it. I knew that if she accepted the idea of anal she’d be down for any other ass play.
She almost instantly texted back “LOL” in all caps and proceeded to tell me that she’s down. I couldn’t resist beating one off in excitement the second she responded – my sexual fantasies becoming reality after all that time. Shortly after that I let my girlfriend go, and eagerly waited until time came for me to take the trip downstairs to her apartment to merge my tongue with her holes.
We didn’t talk to each other for days after that, until one Friday night when she asked me if I wanted to come over to get fucked up, just the two of us. I texted back “hell yeah,” got some whiskey and a gram of some buddha.
When I got to her house it was a tad bit awkward, giving her a hug hello as we did when we were only friends - the same night we planned to break the friend barrier and hit a massive sex session. She looked beautiful as all hell that night – she straightened her hair, wore tight black leggings with a t-shirt (not hiding her ass whatsoever), and smelled like lavender. At first things were really business as usual: we got really stoned, started taking shots, got more stoned, more shots, but no talk of sex whatsoever.
About 7 shots and all our weed later, she finally asked if we were going to do this or not. I was so nervous that I didn’t want to make a move and put it off for so long that she had to take the initiative. Slightly embarrassed I smiled and asked her to come closer to me. I was on a beanbag chair in her room and, smiling, she came and sat down cuddled next to me. I held her in my arms and we shared our first kiss together. Her tongue was pierced. It was the most passionate make out session of my life – it was as if our tongues were wrestling each other in a desperate attempt to penetrate the other’s throat. I used my tongue to stimulate her piercing. Even at this early stage, her experience as a lover really showed and I could tell that she was an absolute freak when getting fucked.
I ran my hands along her body as she did mine, feeling her everywhere I could. As we kissed her skin was so soft to the touch. I worked my hand inside her shirt and felt up her bosom through her bra as she reached into my pants and grabbed my already rock solid, pre-cum oozing, cock. She even laughed and asked “a little wet already, huh?” As she started to masterfully play with my dick things got more intense. I started rubbing her clit through her leggings, the kissing become more passionate, moans of pleasure were being released, and I could just tell that she was dying to have my cock in her.
Suddenly our mouths parted ways, she gave me a playful glance, pushed me back so I was leaned back in the seat, got onto her knees and ripped off my shorts and underwear. She gave my dick a quick inspection then licked it from the base of my balls to the head with her pierced tongue. While making direct eye-contact, and without blinking an eye, she opened her mouth and engulfed the entirety of my eight-inch dick into her seemingly bottomless throat. She was a master at giving head – still haven’t encountered better to this day over 5 years later. She masterfully utilized her tongue, lips and hands to give an absolutely mind-numbing cock sucking experience. Saliva was dripping all over my balls and the beanbag chair as I laid back, closed my eyes and enjoyed the moment. She must’ve sucked an ounce of pre-cum from my brutally hard shaft.
After a single minute I knew I’d cum if she didn’t stop so I mustered the courage to stop her in her tracks and told her that it was my turn to taste her. Drunk, high and filled with pure lust living out my sexual fantasies, I entered a trance – unable to stop until each and every one of my sexual desires were satisfied. Too kinky or too weird meant absolutely nothing to me at this point; if she didn’t verbally stop me, I wasn’t stopping. With my throbbing cock out of her mouth, I stood up, picked her up and through her onto the bed, meeting her mouth with a kiss as I mounted her. Dry humping her, I got out of my shirt and helped her out of hers and began to squeeze her plump breasts, caressing her nipples as we continued to embrace. As I kissed her neck and held her tight I inhaled the scent of her hair and her lavender perfume, I felt my love for her flow through my body in a wave of warmth. As I gave her ear a playful nibble I told her to stop me if she felt uncomfortable and she agreed.
With that I got up from on top of her, straddled her on my knees, and flipped her to her stomach. I told her to stay like that; face down, body flat, exposing that fat ass in tight black leggings. For a second, I had to just sit there and take in the fact that I was staring directly at the ass I’ve been silently appreciating for years – ready for me to make it mine.
I started with her feet, sliding all the way to the edge of the bed so her feet were right in my face. I rubbed them as I stared up towards her thighs and ass which looked like big black bubbly mountains from the angle I was at. After massaging her feet and sucking her toes I moved up her legs, massaging her ankles and strong calves. Rubbing the black leggings that I’ve seen her wrapped for years, even at her calves and ankles, had my cock standing straight up in excitement. They were soft and thin and were glued to her legs as if they were a second skin. At this point I couldn’t stand teasing myself any longer and her massive ass cheeks became my target – I was about to give her booty a complete inspection and service.
I crawled onto her body and could immediately tell that she was a veteran at getting her ass worshipped – not surprisingly since I couldn’t fathom how any man wouldn’t want to embed themselves in such a plump ass. The moment I mounted her she curled her feet into a hole so I could fuck her feet as I played with her cheeks. She laughed as my cock shot out a hefty stream of pre-cum onto her feet when I squeezed the shit out of her massive butt cheeks for the first time. After grope massaging her thick things and ass I plunged my face right between her cheeks, spread them wide, put my nose right to her ass and inhaled deeply. To my dismay (as I’m a freaky guy and hoped to inhale her true musk scent), her butthole smelled like nothing through her leggings despite at least a few hours passing since she showered in anticipation for sex. Eva moaned in satisfaction as I vigorously pushed my face into her croch and pumped my cock through her feet.
I pulled off her leggings to uncover her bare, silk-smooth, pale legs and fat ass cheeks with a black g-string wedged between them. I spent a good thirty seconds feeling her soft skin as I massaged the entirety of her freshly revealed lower body. I pumped her feet with my cock as I moved my face within inches of her ass. With a firm grip on both of her cheeks I spread them as hard as I could to reveal her pink butthole skin piercing through her tiny black g string that barely even covered the asshole. Shaved and clean as a whistle, her asshole called my name and my ballsack was dying to give it the semen it deserved. I took a deep whiff and she moaned intensely as I started to kiss and lick her thighs, ass cheeks and butthole through her g string.
I couldn’t control my cock from thrusting her feet and knew that I’d cum if I kept up ass worship for much longer, so I finally decided that it was time for dinner and penetration. I removed my dick from her foot hole, dismounted her, and took a second to appreciate Eva’s 99% naked body laying ready for me after all those years of fantasy. My solid-steel cock pulsed and jumped with excitement as I gracefully removed the dental floss thong from her woman parts. I kept her on her stomach but spread her legs wide and laid down directly behind her ass. With another firm grab of both butt cheeks, and a bird’s eye view of her croch, I spread booty even stronger than before and witnessed the perfection of her bare, pink, clean shaven vagina and asshole. Her holes were perfect; a soft, delicately layered bright pink pussy with a beautiful pearl clitoris, and a flawless dark pink butthole with a tiny birthmark right by the opening.
I had no idea where to start pleasuring her, so I decided to hit both at once. Moving super slowly, I sloppily ran my tongue from her clitoris all the way up to the top of her asshole and Eva let out an intense moan of pleasure. My willingness to be a slave to her holes must’ve made her lose it. She was so clean that her holes tasted like nothing but skin; even the entirety of her dripping wet pussy was practically tasteless. I made her squirm in pleasure by systematically licking her clit, lips and asshole; alternating between massaging her holes counterclockwise to clockwise. As I made her cum she reached back and pulled my head deeper into her croch, gasping for breath in sheer pleasure.
With that, Eva commanded me to fuck her hard as I could – an easy request to oblige since my cock could no longer wait to expand her holes. I got to my knees as I watched her get onto hers, arching her back low, sticking her beautiful ass high in the air for me to enjoy. I got into position, applied some saliva to lubricate my rod, and with a hard smack on the ass I slowly stuck my head into her soaking wet pussy. My cock was instantly met with the tight grip of her warm, slippery pussy hole as she moaned in pleasure. I wanted to give it to her slowly at first and work my way up to a faster tempo, but I lost control, instinct took over, and I started absolutely pounding her delicate kitty. I spread that ass wide and watched the entirety of my cock go in and out of her doggystle pussy and rubbed her asshole with my thumb. My cock was so rock solid and pulsing that it felt as though I was sticking a metal bat into her tight, wet pleasure-hole. For the next few minutes I kept pounding away, grunting like a monkey with each pump, sucking away at her g-string’s vagina cover while staring into her asshole between her spread doggystyle asscheeks.
After a few minutes of ravaging her pussy in doggy-style, we began to change positions. For minutes I enjoyed deep pumps of her missionary vagina, inhaling the scent of her hair as I sucked her gauged earlobes. Her tight love canal pulled my cock back each time I rammed it all the way inside, like a suction cup. With the passing of each minute, I’d stick my cock entirely inside her and sit still to avoid prematurely dumping a load; and with my solid cock shoved entirely into her, I felt her vagina secreting lubrication as it pulsed around my meat. After a few minutes of missionary, she rode the shit out of my cock in cowgirl and reverse cowgirl. What a sight it was to stare at her asshole as she squatted up and down on my rod while spreading her cheeks for me. After about 10 minutes total of enjoying her vagina, I knew I couldn’t last longer and would need to blow my load soon, so I decided that it was time to enjoy some asshole.
As squatted down one last time my cock, I told her to get back to her knees. She slowly slid off my cock, pushing the air out of her pussy as new air rushed to fill the hole my cock left in her. I asked her where the lube was, and she laughed as she got to her knees and stuck her ass in the air directly towards me. I grabbed the lube, applied a good pump to my pointer and middle finger, and immediately began lathering it on her asshole. Spreading her cheeks wide for me, I began rubbing in circular patterns at first – eventually sticking my pointer finger inside her warm and tight butthole chasm. She let out an intense “ahhh fffuckk” as the entirety of my pointer finger slowly went in and out of her asshole. With a little more lube, I added my middle finger to her asshole, continuing to pump in and out of her hole, getting it nice and ready for my now diamond hard cock.
After getting her dunghole lubricated and ready to go, I asked her to relax her asshole muscles for me and to gape as best she could. That’s when I could tell this girl was experienced with asshole pleasure. Without a moment’s notice, while I spread her cheeks wide, her tight little lubricated pink asshole popped open with the suction cup sound of her asshole’s pressure being released. My cock shot precum as her spread pink hole morphed to reveal a black hole the size of a penny. I entered autopilot; pouring lube straight from the bottle into her penny-sized gaping hole, applying plenty to my diamond cutter cock, and getting right into position to ram asshole.
With a hard smack of her ass, I spread her cheeks wide, stared directly into her gape, and slowly slid my rock penis into the deepest depths of her shithole. We simultaneously let out deep moans of pleasure as my ballsack pressed directly against her vagina. I stood still for a few seconds as the entirety of my pulsing cock was embedded into that asshole – taking in the tightness of her hole, the amazing texture of her asshole skin, and the soul-pleasing sight of my cock balls deep in her asshole, her pink booty skin and tiny birthmark surrounding my cock like a ring. I slowly pulled my cock out in its entirety, spreading her asscheeks as wide as I could to see that gape. *puluup* Removing my cock from her asshole sounded like removing a plunger from a wall as her hole gaped wide – about the size of a quarter after my cock stretched it out.
Instinct took over, and I began to grunt like a monkey as I stuck my cock back into her gaping asshole and began pounding away. I wasn’t able to fuck slow anymore, after seeing her asshole gape I was stuck at 100%. Pound after pound, my cock went from tip to ballsack at the rate of an olypmic athlete of asshole pounding. I’d only stop pounding once per 30 seconds to get a quick glance of her gape before stuffing it right back in and continuing the asshole pounding. The sound of “Ohh yahhh, fuck my asshole” was burned into my brain as it was all I could hear for what seemed to be an eternity. In reality, only three minutes had passed before I felt the nutsack getting ready to blow its load. With one final gape, I squirted the last of the lube into her blackhole the size of my cock’s diameter, guided my tip into the event horizon, and pounded as fast as I could while giving her the gorilla grunts (what she likes to call my asshole fucking moans).
It was pure bliss as I pumped my gigantic nut into her asshole and felt the natural lubrication of my warm semen fill her tight hole with each throb of my cock. I let out a stronger “ahhh” than an explorer drinking Poland Spring after being stranded for three days in the Sahara. I couldn’t know for sure as I didn’t watch her squirt the cum from her asshole’s depths, but it must’ve been two or three fluid ounces of semen that my balls poured into her shitter. I smacked her ass one last time as I pulled my still solid, recently emptied cock from her used hole. *pppuuup* The suction cup sound was even stronger with an asshole filled with a full ballsack’s supply of sperm cells.
I immediately plopped down to the bed, breathing heavily, still amazed that I just ate and pounded the pussy and asshole of my long-time fantasy. I heard her farting out the cum into the toilet before she took another shower and rejoined me in her bed. Shortly after rejoining me, it was time for round two – followed of course, by a round three (only in the vagina those times). After hours of sex, we finally called it a night and passed out some time in the early morning. The following day we expressed how great a time we both had exploring each other’s genitals, and that it had to happen again.
Since then, we’ve had plenty, and I mean plenty of sex. Her asshole and pussy have become very familiar territory for my cock and we’ve done all types of wild sex. Plenty of interesting sex stories to share involving her. It’s been years since our first fuck, and we have had periods of time where we’d hang out plenty and have no sex at all, then one day decide to fuck like monkeys. We’ve had our own relationships, and always kept in touch, but every now and then I find my cock back up her asshole.