I dressed in a matching purple bra and thong, remembering his comment that he had a preference for thongs. I think it felt like a permanent wedgie, but at least there wouldn’t be a panty line.
I painted my nails with mother of pearl, and a holo top coat, and took the time to do both my fingers and toes. Hadn’t redone my toes in months, so it was really time.
Checking my hair, applying a little make-up, I am not the best at this, but did manage some foundation, concealer to hide a zit, a little colour on the cheeks, and mascara.
I put on a blue sundress with small white dots, and checked myself in the mirror again. I think I looked good, and more adult than I felt, 18 years of age, and going on a real date for the first time. And not just any date, a Tinder date, and I was quite sure he was expecting for something to happen. I wondered again if I should tell him I was a virgin, but looking at myself in the mirror, standing only 1.50 tall, weighing in at 60 kg, I wanted to be more mature than I looked. At least I was still staying in shape, but my gymnast body was gone, I’d never weighed as much before, but my new butt was what had gotten his attention. Still small boobs though, maybe it was just not in my genes. At least my now long ash blonde hair, identified me as a girl, if not my butt, my face was still a bit boyish, with a wide nose. Wished I was better a make-up! I took one last look, put on my footies, and my clunky black Dr. martens boots, and left my dorm room.
As I walked towards the café where we’d meet, I thought about the absurdity of what I was doing. I remembered going on Tinder, and beginning to swipe through the pictures, I couldn’t help, but check every profile for what they’d written, when I came across his profile. His picture was a bit better than most of them, good looking, but angles and filters do a lot. His profile though, “I’m a butt man pure an simple, I only swipe right on a good butt, so no butt picture, and we won’t match. I’m here for sex, especially anal sex, if that isn’t you swipe left.” I couldn’t believe the audacity of it, and after reading it I was first going to swipe left, but decided to swipe right, simply because I had to talk to this dude and find out if he was for real.
I spent almost an hour taking pictures of my butt before I finally got couple that I thought was good, and added them to my profile, hoping he hadn’t seen it yet. He matched me later that day, and from the beginning he made it very clear he found my butt to be “Extra fine!” and me to be “Delightfully thick!”. I really hadn’t meant for anything, but figuring him out, but the constant flattery, began wearing me down. Quickly the talk fell on sex, and not wanting to reveal my inexperience, I thought it was safe to tell I never had anal when he asked. He explained in great detail, that it was the ultimate pleasure for both women and men, and how he’d introduce me, and make it my preferred way of sex if I’d let him.
Might have been the attention, might be the weed I’d bought from another girl in the dorm, but I finally agreed to a meet.
I arrived at the café, where I quickly spotted him waiting at an outdoor table, he saw me at the same time, a smile splitting his face. He looked very much like his picture, handsome with light brown hair, and grey piercing eyes. He was wearing a blue band t-shirt and khaki shorts, even sitting down I could see he was tall, and sorta lanky.
As I got there, in his haste to get up, he knocked a coaster of the table and it landed on the ground rolling past me. I turned, bending down to pick it up, and it hit me that it might not be so accidental as I presumed. I looked back and saw him admiring my backside, and the look on his face made my body tingle, it was a look of lust and hunger, something I’d never seen before.
Standing up, I turned putting the coaster on the table. “Get a good look, or you want to see more?” His eyes were glazed over a bit, before he smiled looked me in the eyes, and answered “Definitely want to see more, could look at that for hours.” That was it, though our date went on for sometime, I knew I’d go home with him.
After some tapas, and some happy hour drinks, we were on his bed, him on his back me on top kissing slowly and deeply. He tasted like margaritas and garlic, I was a bit giddy, and had a stupid grin on my face I couldn’t quite get rid off.
After a while I noticed his hands on my thighs, gently kneading first, then slowly stroking touching higher and higher, raising the hem of my dress. I caught myself moaning lightly into his mouth, he broke of shortly smiling looking me in the eyes, “Is this ok?”, at the same time I felt his fingers stroking my inner thigh, my whole body shuddered, and I had to fight to get out a throaty “Fuck yes!”, “Ok, say no if it goes past your limit alright?”, I nodded “Uhhuh!” and began swallowing his mouth again in response.
He had a sweet scent to him I noticed, and briefly wondered what it was before his fingers again began to move, and making me focus solely on them.
His fingers moved higher and higher, dancing over my skin tickling me, giving me goosebumps all over, and raising my dress up above my ass. When he got to my ass his one hand went from light touches to grabbing and kneading my right cheek, while the other hands fingers kept dancing and quickly finding my crack. When he hit the top, and the string of the thong, he broke into a wide grin, “I really love thongs”, “I remember, ahh!” I replied with a small surprise at the end, as he slowly pulled the string from between my cheeks. I was sure it was sweaty from my crack, but it felt heavenly as the wedgie disappeared, I was slightly disappointed as he released it, pulling out on both cheeks to let it fall back in.
His one hand kept kneading an pulling on my cheek while the other went exploring between, finding the string burrowed there. At this point I couldn’t concentrate on kissing him anymore, and let my head fall to the pillow besides his ear. He bit my earlobe, and whispered “You’re really enjoying this.”, I could only moan out a “Yeeesss!” as my whole body was overloaded with signals. Being able to focus again, his fingers was now moving back and forth along the string of the thong, finally resting right on my anus, gently putting pressure while he wiggled his fingers.
It felt like there was butterflies in my butt, trying to get out, and I couldn’t help, but push back against the fingers. “Eager there aren’t you? Well, I won’t be the one to deny you.”
Again he pulled out the string, this time he slid it to the side, so it caught under my cheek and stayed there. His fingers quickly came back between the cheeks, finding my little tight hole, and gently massaged it.
Again I could help, but moan directly into his ear, a brief thought that I should be mortified to be enjoying it this much, quickly banished by a wave of pleasure as his breath warmed my ear, and one of his fingers placed itself right on my sphincter.
Instead of pressing in as I expected, he removed his fingers, and he reached out to the side of the bed, and scooped something from a jar. “Coconut oil.” He answered to my unasked question.
His fingers moved to my butt again, and began spreading the oil between my cheeks, quickly focusing on my sphincter.
The oil, with the massage of his fingers loosened my sphincter, and his finger easily slid inside me, it felt weird. He began moving it in and out slowly, with each movement getting a little deeper. I kept expecting him to have his entire finger in there, but it kept going deeper and deeper.
When he finally got as far in as it could, it felt as if it was half way to my stomach.
“How does that feel?” He asked me, I waited a little with answering, feeling everything, as he kept slowly moving it in and out, slowly rotating it stretching my hole as he did it. It felt weird to be honest, a bit like pooping, but it also tingled my butt. I also felt just how warm and wet I was, and something I hadn’t noticed before, something hard pressing against me through my dress and his pants. I sent a small wave of happiness through me, and I purred into his ear “I feels wonderful, so wonderful.” and began kissing and biting his earlobe, licking his ear slowly.
“Ready for a finger more?”, a finger more, could I take that? A thought flittered by, but my mouth moaned “Oh yes!”
He pulled out his finger, and two fingers was pressing against my anus, my whole butt crack swimming in oil. He pressed in, this time there was a bit of pressure as my sphincter was stretched around his fingers, a slight discomfort, but the tingling drowned it.
I was wholly focused on my breathing, his fingers, and the twitches of what I assumed was his hard cock pressing against me.
Slowly again he moved the fingers in an out, deeper and deeper, rotating and stretching, the pressured loosened, and only pleasure remained. I was so caught up in it, didn’t even notice how long it was, before he asked “And a third?”, “Huh, oh! Yes.” I got out, fully concentrated on the feeling of his fingers.
As the third finger was added, the discomfort and pressure came back, but still the tingling overwhelmed it, and as he slowly worked them in and out the discomfort loosened again.
“I think you’re ready soon, you want to feel a real cock up your ass?” Just the thought of it made me shudder. “Yes, I’m ready.”
His tone grew more firm, but still with a smirk in his voice “Look me in the eyes, and tell me what you’re ready for.”
I pulled up, looked him in his eyes, started, then blushed a bit, but got my voice. Looked him right in his eyes, and said “I’m ready to feel your hard cock up my ass.”, I almost burst out giggling at that, had I really said that? Lying here on top of a man I met a couple of hours ago, with three fingers up my ass, begging him to fuck my ass.
“Let’s get out of some of this clothes then.” He said, pulling his fingers from me, I couldn’t help, but gasp and felt a bit of disappointment in suddenly being empty.
I sat up and removed my dress, as he saw my bra, a small smile cross his lips, and his hand briefly touched the one cup. He sat up a bit and removed his t-shirt, and then had me help pull down his shorts. Apparently he went commando, and as I pulled them down, his cock stood upright hard as a doornail.
This was the first cock I’d ever seen in real life, and it seemed really much larger than I anticipated, and got a bit nervous about it going into me.
I let my fingers lightly touch it, it was so soft and smooth.
“Uhh, that tickles! Want to lube it up?” He held out the jar of coconut oil, it took me a while, but I scooped up a glob of the cream, and began applying it to his stiff cock. It quickly turned to oil, as I slowly rubbed it up and down, I couldn’t help notice that my fingers couldn’t reach all the way around it.
It sounded like it felt good, he was moaning lightly, he interrupted with “Pull back the foreskin, and lube the head too.” It took me a while, but finally figured out what he meant, and gently tucked downwards on the skin, with my other hand, getting the head to reveal itself. Using both hands, and a little more oil, I finally thought it was lubed up and ready.
“Ready? So how do you want me?” Trying not to sound too green, “First time it’s best you’re in control, so straddle it, with your back to me, and slowly insert it. Once I’m fully in, you can lean back into me.” he explained.
It took a little coaching, but I finally understood, and turned around squatting over his cock, one hand on his stomach, the other holding his cock, trying to push it against my slippery asshole.
He was holding my steady, and holding my thong to the side, which I hadn’t removed, had a feeling he wanted me to keep it on.
First it slipped up, then down, and would likely have gone in my pussy if it wasn’t for the thong. Third time he told me “Push out, like when you habe to poop, it’ll open you up.”, so I did, and suddenly the head popped in. I was so surprised, that I sat a little more down, getting maybe a couple of centimetres more in before I got control. It felt so weird, and his cock felt humongous, much much larger than his fingers. The discomfort and pressure was there instantly, but still it was countered by some pleasure, though not as much, so I was holding very still breathing.
“You ok?”, “Yes, yes…, just give me a minute.”, “Take all the time you need, your ass feel insanely good, and it looks amazing stretched around my cock.”
That comment made me want to see, but there was no way to see my ass from this angle, so I reached back, and felt his cock stabbing into my body, and my sphincter stretched with no wrinkles around his humongous cock. Something about it made me want more, and keeping my hand there, I slowly began moving a bit up and down his cock, and slowly it got further into me.
It began feeling like it was way into me, but feeling I could feel that there was more than a hand left outside, it felt quite daunting. It felt like I couldn’t get it further in, and that’s when it struck me, here I was trying to get a cock as far as possible into my ass, still being a virgin, couldn’t help, but let out a giggle.
“You seem to be enjoying ourself.” He moaned, I looked back as I moved up and down his gaze was transfixed to my ass. “Yeah, this feels pretty good.” And I realised as I said it, it actually did. “I’m not sure I can get it further in though.”, he looked and me and smiled, reaching up and holding my sides. “Take your bra off, and lean back towards me, you’ll see why I had you like this.” I took off my bra, and did as he asked, slowly leaning back till I was lying on his chest.
He moved me a little to the side, so I was lying mostly on his left shoulder, his cock stayed in me all the way down, my feet planted on each side of him. He tilted his head down and kissed me, and we began kissing again, slowly while kissing, he began moving his hips, thrusting into me.
It felt wild, my senses slowly getting overwhelmed again, his one hand grabbing my left boob, squeezing my nipple between two fingers while doing so. The other moved over my skin down over my stomach and into the thong, and began rubbing the outside over my clit. I exploded immediately, I let out a “Fuck!” and then my whole body just seized up, I could feel myself clamping down hard on his cock, and everything was just too much. It was the best and longest orgasm of my life, so far, and I spent maybe a minute clenching and unclenching. After I finally regained control, I couldn’t say anything again, but “Fuck.” Though more softly this time.
“Don’t mind if I do.” He replied, and slowly started thrusting again, I could feel him going deeper now, I couldn’t really focus as my whole body felt like butter, and his thrusting just felt good, and mellow.
I noticed he picked up speed, and as I regained focus, his kisses became more intense before he suddenly announced “I’m cumming!”, and grunted as he began filling my bowels with semen. I could actually feel it, felt like hot water being spurted into me.
We stayed like this for a couple of minutes, me on top with his cock in my ass, we kissed a little, but mostly he just hugged me.
“So was anal as good as vaginal?” He asked into my ear kissing me.
I blushed a little, and answered “I was pretty good, but I’ve never had vaginal so I don’t know.”
He was quite a bit, then said “Well that crosses of an item from my bucket list, which also means I swear never to fuck your pussy.”
“You don’t have to fuck it, not as long as it feel this good to have my ass fucked.”
“Well anytime you want your ass fucked, just ask, and I’ll be there.” he replied.
“What about now?” I smirked at him.
“Well, aren’t you insatiable, let me go pee, then we can go again.”
Source: reddit.com/r/Erotica/comments/v5q35y/fm_first_time_ever_anal_anal