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So back when I (F24) was in my senior year of school, I started to get the urge to liberate myself sexually. I was by no means a virgin, but my boyfriend of 2 years was pretty vanilla in bed. Missionary, occasionally doggystyle, but little else. I would wear sexy lingerie, greet him after class naked with a butt plug inserted…I feel like I tried everything! I loved him but I wanted more. I wanted to get my ass fucked! I begged him to stick it in my butt and he just seemed grossed out by the idea. I consider myself pretty hot, and others have commented as much: 5’7″, 34c tits, a slender waste and a nice, perky little ass. I keep it all waxed and squeaky clean down there but he was not interested. I get it: Anal is not for everyone, but he was just not satisfying me anymore so I decided to move on.

Not long after we broke it off I hit up Tinder for the first time in my life. Using a somewhat risque photo as my account pic and a tag line of “Seeking new adventures,” it only took a few hours of swiping before I had a ridiculous amount of messages to sort through. I was forward and a bit naughty in my messages to guys but holy shit I was not expecting so many unsolicited dick pics! I wasn’t offended just…surprised. I wanted hot, kinky dirty sex, and though feeling sexually liberated I was still a bit shy. I arranged a couple of coffee meets and the third was a winner. We’ll call him…Mark. He was 6’1′, a tan complexion and a hypnotizing smile. Mark was flirty and a bit touchy feeling, but not in a weird sort of way. I returned his advances and we developed a chemistry very quickly. We agreed to meet again, this time for dinner at his place.

Mark had a tidy little flat in a famous part of town. He was a few years older than me with a career and some type of sporty car. Neither of us were much good at cooking so we agreed on takeout. I honestly can not remember what we ordered as it was the rest of the evening that I will never forget. I could tell that Mark was quite a bit more experienced than me by his Tinder account and some of the comments he had made about past lovers. That was fine with me as there were things I wanted to learn and I wasn’t interested in trying my luck at the frat parties or school bars. And no, I did not directly ask him if he was down for anal, lol but I could tell he was adventurous. His sly little smile made me flutter and I was starting to get wet before dinner was done.

I was shy, but horny as fuck, and I was ready to get down. Mark started to clean up our takeout and as he was washing dishes in the sink I came up from behind and wrapped my arms around him, feeling up and down his chest. I could feel the pace of his heartbeat quicken. I put my hands up his shirt and noticed his hard, muscular abs and a bit of hair around his naval. I continued up to his pecs as he spun around and wrapped his arms around my back. Our lips met and tongues engaged, and he grabbed my ass, kneading my cheeks through the thin cover of my yoga pants. Now I was really wet! I could feel Mark getting hard through his jeans, his cock bulging and trying to break free. I undid his belt and the buckle of his jeans and helped him pull down his jeans to finally free his now bulging 8″ cock. I grabbed his member and gave a squeeze, and noticed a bit of pre-cum emerging from the tip. I slowly went down and found his shaft with my mouth. I stroked as I took as much of him as I could down my throat. He let out a little laugh as I gagged and he held the back of my head as he gently thrusted.

Mark moaned as he used my mouth and then gently grabbed me under the arms to bring me back up as we continued to make out, still in his kitchen. He put his hands down the back of my leggings, squeezing my ass and exploring with his fingers. He asked if we wanted to take this party into the bedroom, and I grabbed him by the hand and led him away, then realizing I actually had no idea which of the closed doors in his apartment led to his room. “Over here,” he motioned as he led me into a sparse room, his pants still around his ankles. We stopped at the foot of his bed as I unbottoned the buttons of his shirt and he stepped out of his pants and briefs. I lifted my shirt over my head and Mark adeptly unclasped my bra before bending down to suck on my nipples. I wiggled my ass as he pulled down my pants, leaving me standing there in the sexy little thong I had chosen specifically for this occasion: Black, transparent lace that just screamed “Come fuck me!”

I pushed him down onto his bed and crawled over him to again stick my tongue into his mouth. His rock hard cock writhing against the thin lace of my thong. He squeezed my ass and then helped me out of this last bit of clothing. I was soaking wet by this time and mounted him, taking him inside of me. I screamed and moaned as I took more and more of his cock, riding him until I had the first orgasm of the evening. We then rolled over together, him on top of me. He pounded my pussy and made me cum again! I pushed him up and off so I could roll over and take it from behind. On my elbows and knees, this allowed him to reach new depths. He fucked me at a pace I have never experienced before, slapping my ass while his balls bounced against my body. “I’m going to cum!” he said. With that, I quickly flopped around so I could take all of his cum in my mouth. He let go of his load in five gushing streams, cum making it mostly into my mouth but some finding my face and tits. I swallowed his load as we collapsed onto the bed. We lay there a while, whispering and eventually made our way naked back out his kitchen for another glass of wine.

We laughed and got a little tipsy but the night was still young. He asked if I would stay or if I wanted a ride home, and I responded by sitting on his lap and we started making out again. We fondled and felt each other up, and Mark’s cock was once again hard, obviously ready for round 2. I led him back to the bedroom, this time knowing exactly where it was and what I was gonna do. We made our way back onto the bed, and I wanted to make my move. I wanted him to fuck my ass, but as I’ve mentioned I am (or was) a bit shy and I didn’t want him to think I was a whore asking for anal on the first date.

I rolled over so we could spoon, and I wiggled my ass up against his rock hard cock. He grabbed and squeezed my tits as his shaft worked slowly up and down the crack of my ass. I pushed back hard against him, allowing my body to send the signals that I was too nervous to express with my words. I moved my ass in a way that on the down stroke, the tip of his cock would brush against my sphincter. I squeezed his cock with my cheeks as we moved steadily together. I could again feel the pre-cum starting to flow from his cock and I was once again getting wet. More and more, his cock would move over and catch upon my asshole, probing but not quite entering in. Was he interpreting my signals correctly?

I reached back and grabbed my left ass cheek to slightly pull aside and make a more welcoming path for his tool. He continued to grind and during one of his long strokes his cock snagged and then pushed against my hole almost going inside. He apologized, but I am pretty sure it was intentional. “That’s okay,” I said, “but if you’re going to keep doing that I think we might need some lube.” I turned to see him smiling slyly, and he responded by gently biting my neck. He rolled me fully onto my belly and worked his way down my back with his lips and tongue. His muscular hands grabbed an ass cheek each, squeezed and pulled my ass aside as his tongue found my crack. He nudged me upwards so my ass was extended in the air, giving his tongue full access to my grateful ass hole. I let out a loud “Ahhhh!”, in complete ecstasy that this was finally gonna happen!

He probed and worked my hole with his tongue as I moaned. I stroked my clit and noticed that my pussy was sopping wet, maybe wetter than it had ever been. His tongue was just magic and if that was the extent of my pleasure that evening I would have been totally fine with. I had dreamed of having my ass eaten for so long and this was something that my previous BF would have NEVER given me. Mark continued with his tongue and began mixing in his fingers, giving my hole more attention than it had ever received. He gradually started inserting a finger, just a little at first and gradually working deeper. I gasped as his middle finger worked all the way in and wiggled around gently inside of my ass. He worked it in and out and he had me in a puddle, both figuratively and literally as he introduced another finger. He checked in that I was okay and I said, “Oh fuck yeah, I want you in my ass!”

He was able to enter me with both fingers, again working them to properly stretch me out for what was to come. He spread me cheeks aside and said, “Good girl,” as my ass, pointed high in the air, remained a bit gaped each time he pulled his fingers out. He stepped away briefly and returned with a bottle of lube. As he drizzled lube down my crack and used his fingers to push the gel into my hole, I was excited but started to get a bit nervous. I wanted this, I knew I did, but Mark’s cock was significantly longer and girthier than anything I had ever had in my ass. I had fucked around with butt plugs and small dildos for the last couple of years and had even started an anal training regimen recently but I wasn’t sure if I would be able to take Mark’s enormous cock: A cock bigger than I had ever had, in any hole.

Mark slathered a generous amount of thick lube onto his shaft and suggested that we lay on our sides while we warmed up. He had totally done this before! He lined himself up with my waiting asshole. He spread my ass open and slid up and down my crack a couple of times and then his tip found my entrance and stopped. I remembered just in time to take the deep breaths recommended for anal sex as Mark gently pushed against my sphincter. He had apparently done a great job loosening me up, or maybe it was all the recent training, but it did not take much effort for him to slip inside. The sensations of pleasure, and yes, a little pain, shot up my spine as I let out a deep breath and a moan. He stopped momentarily, squeezed his body close to mine and nibbled at my neck. He checked in that I was okay and probably noticed my rapid heartbeat and probably the bit of sweat forming on my forehead. The stubble of his chin grazed the back of my neck, and he held me as he pushed a bit deeper.

I moaned loudly with each slow thrust forward, as he was gradually able to go deeper inside of my ass. The presence of pain had subsided completely within a few minutes, and my body began more readily accepting his girth. Eventually, he was all the way in and I started to work my ass back and forth in rhythm to his motion. The pace increased and I screamed as I experienced my first anal orgasm! I wasn’t stopping there though: My ass was now fully warmed up, stretched and I was ready for a full night of hot, dirty anal!

I had Mark lay on his back and I mounted him, grabbing his lubed shaft and lining it up with my hole. I was able to take all of it immediately, sliding all the way down to the base. He grunted as I slid up and down his pole, and he grabbed and squeezed my ass cheeks. Another orgasm later, I slid off and turned around so I could take him reverse cowgirl. “How many times have you done this?” he asked. He was more than surprised and perhaps didn’t believe me when I told him that he was taking my anal virginity. Turns out I was a natural butt slut, taking it in the ass like a professional on our first date.

Mark slid me off his cock and placed me on my hands and knees. He fucked my ass from behind, reaching even further inside into the depths of my body. He started pounding me vigorously now, and slapping my ass hard. “Fuck yeah, Fuck my ass!” I screamed as he pushed further, pulling fully out and re-entering. This was so dirty. So nasty and kinky. So…right! After an hour of full on butt fucking I had orgasmed multiple times and he was ready to explode. He pushed deep one last time and held, planting his seed deep inside of my bowels. I could feel the pulsing of his cock and a warmth in my belly as he gushed into my ass. We fell into a pile on his bed and he remained inside me as he gently kissed my face and neck.

Mark and I hooked up a few more times that spring before I graduated school and moved on to another city. We are still friends and still meet up very occasionally when we are in the same city. We are not “together” and I have no desire to be “together” with anyone at this point in my life. Over the last few years I have had lots more kinky anal sex. I am on a constant quest for everything butt and it has become one of my main motivators in life. I am currently anal only and no longer even bother luring men with the promise of pussy. Opinion and DM me if you like anal too (both girls and guys), want to flirt or if you’re lucky and close by maybe we can hook up. I look forward to you telling me all the dirty, nasty things you want to do to me and maybe I’ll distribute more of my experiences in the future.

-Frills

NSFW: yes

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