The first time she took my monster up the ass

I remember the first girl who took me in the ass. It had been years since I lost my virginity, and it was at all times hard enough getting girls to take me all the way up their pussy without the pressure and weight of it being too overwhelming. So anal was a no go, no way, no how. I at all times wanted to know what it would be like to fuck a tight ass with my cock, which I by now knew to be monstrous, but I was basically resigned to it never happening.
This all changed when I was introduced to Jen, a slender and lanky blonde with a pretty, Spanish looking face, and very pert features (both her tits and her ass were so juicy they looked practically bolted on, although they were evidently real!). It was the years after school, and the atmosphere in our social group was rife with experimentation. I forget how the message was first passed, but it came to light that Jen had something of a degradation fetish – in fact, she could only get off when sex scared or hurt her. Far be it from me to psychoanalyze her, but I think that’s what she needed to conquer her own inhibition and ride the waves of intensity toward sexual pleasure and expression.
Anyway, Jen saw a couple photos of my cock that were going around the friend group (yep), and another mutual friend of ours essentially brokered an anal sex romp. I had never been in a girl’s ass before, and I was so excited in the days prior to our meeting that my heart was literally palpitating. I don’t know what she was going through. But on the appointed day and time of our meeting, the doorbell to my apartment rang, and sure enough, there she was. She wore a blue little tank top that flashed a nice amount of cleavage, and pink hot pants that were very hard for me to take my eyes off of. She wasn’t a big talker, more of a doer, but she noticed my obvious interest in her body. With the apartment door safely shut, she bent down on her knees and wiggled her tight shorts at me.
“I want you to be my master. And I want to be your anal whore, daddy.”
This practically knocked the wind out of me, but I tried my best to keep my cool. My cock was stiffening considerably now, pushing hard against my pants. She sat her bubble butt down onto her feet, having kicked off her shoes revealing cute socks. She gave me a nod of encouragement and I began to play with her ass cheeks, kneading them and spanking them a little. I pulled her hair back a little bit and kissed her hard on the mouth. At that very moment I grabbed her politely but firmly by the neck in a way I wondered she would like, and stood her up. As she moaned and writhed, standing against the wall, I buried my face in her ass which was still being hugged tightly by those little hot pants. She giggled, squirmed and moaned against my lips. Quickly, her shorts slid down exposing a set of sheer pink hip hugging underwear. Her ass looked even more ridiculously amazing, and I felt like a god, or at least as lucky as one. I began to kiss around the hem of her underwear, sometimes moving beneath it, kissing her asshole (it was clean, fresh and delicious!) and occasionally darting my tongue downward toward her pussy, which would make her flinch and moan.
I couldn’t withstand but to keep smacking her ass. “Smack it harder,” she whispered, biting her lip. I smacked it harder. “Harder, master.” I felt self conscious about going too hard, and I was still adjusting to my natural dom sexual personality. But I kept smacking her ass cheeks harder, reddening them, as she moaned. I noticed her eyes tearing a little bit, but she kept them mostly shut and seemed to be in some sort of ecstasy. At that moment I took control.
“Crawl toward me, whore.”
Obediently, without missing a beat, she began to crawl across the apartment floor towards me.
“Wiggle that ass while you crawl toward your master.” She did so, following me to the living room couch, which she obediently hopped onto and thrust her perky little ass in my face again. I kept smacking it and kissing it. I was in heaven. Just wheN I wondered things couldn’t get any better, she began to fiddle with my pants. She could feel my monster bulging out of them, and it was certainly interesting her. I took the opportunity to tear down her underwear, and exposed her gorgeous ass and pussy for all the angels to see. I began to stroke her clit and finger her pussy. She stopped what she was doing and moaned. While she was stopping, I licked my pointer finger, coating it thickly in saliva and began to work it into her little asshole.
By now, she was hungrily unzipping my pants. My cock popped out with a sproing, as it at all times does. She gaped at it wide-eyed. “It’s bigger than it looked in the pictures,” she gulped. I giggled, flattered as ever. And, as at all times happens, she immediately put her mouth on it, checking its dimensions for herself in the most tactile way imaginable. I reclined in absolute ecstasy, lightly fingering her asshole while she sucked on my cock, which was getting harder and harder. She was stroking it with both of her hands too while she sucked it, and the feeling of her satiny blonde hair cascading down on it and my thighs was almost too much to handle. I pushed head down as far as she could go, which was only about half way before she choked. But was a good choke. We both felt it. I kept playing with her ass and pussy as she sucked me expertly. Too turned on to restrain myself, I held her hair and began to thrust upward into her mouth and throat. She gagged, burbled and moaned, and the sounds of her glorious struggle were delicious feeling on my cock.
I kept on throat fucking her for a little while. When she couldn’t take any more, she gently pushed my hips down and sucked just the head of my cock for a while, very lovingly. This was one of the best moments. So simple, so pleasurable, so rare. I could see her glossy red lipstick as her lips were stretched to their capacity just taking in my cock head. What a sight; if I could distribute it with you-
“Master, I can’t suck you anymore. I need to feel your monster cock inside me.”
“Okay, whore. Straddle me.”
She did, with wide legs, and lowered herself down on my cock which was now at full gargantuan power, standing in wait to feel inside of her. She lowered herself down onto me. My mushroom head caught her pussy lips and didn’t fit in at first at all – but she moved her hips expertly, applied some awfully sexually persuasion and her pussy lips began to part or me. Within another fifteen seconds, my head had popped inside her. She yelped, moaned, wide eyed. She put her hands on my thighs to steady herself and prevent it from going too deep too fast. As I sensed her obvious trepidation, I began to wonder – does this whore really need it in the ass?
But she was a good whore, and eager to work for it, and she moved up and down me over and over again, taking me a little more each time. The sight of her tight pussy lips swallowing my cock tighter than any condom I’d ever tried to fit on made it hard not to bust immediately. Finally, like the good whore she was, she basically bottomed out. She let out a combination of a yell and a moan. I’d been to this point with other women, and seen them tap out. To my surprise, Jen started to bounce up and down on me quickly, pushing through the pain, pushing through the difficulty. It was so intense. She made fierce eye contact with me and continued to bounce up and down on my monster cock, her legs still straddling me widely. After a second, she had to slow down, and took me all the way a few strokes, but slowly and softly. At that point I noticed my dick was covered in her white pussy cream. I slapped her ass, grabbed it and made her bounce more quickly again. We were both moaning and gasping.
She had to get off for a second and reorient herself in a slightly less acrobatic standard cowgirl. Once I was inside her, she put her hands on my chest and started to ride me hard. The fit was so tight. I could tell it hurt her. But I could also tell she loved it. “Fuck me, master,” she whined sexily at me. It occurred to me that she was still doing most of the fucking. But that was just fine with me, watching her tight little creamy pussy bounce up and down on my endowment. I kept smacking her ass, and started thrusting back upwards, hard. It became so intense for her she had to bury her face in the couch, whining and crying out as I impaled her little pussy. It was so wet, so creamy, I could tell she was enjoying every inch of painful intensity.
“Keep riding me, whore!”
“Yes, master,” she quavered, but this time she wasn’t as good as her word. She got off me for a second, looked me in the eye with an expression that said “FUCK!”, and sat there on the couch, rocking back and forth and catching her breath. I took the opportunity to stand and present my cock to her again, which she took and began obediently sucking, this time just the head and a little more. That wasn’t enough for me, and I pushed her down again to her limit, which seemed to be about halfway. I could tell it was a struggle for her, but that’s what she had wanted. And when I let go my hands, she kept sucking and stroking me hungrily, making desperately sexy eye contact with me as she did so. I stroked her hair and kept pushing her soft lips onto my cock.
When I couldn’t wait anymore, I bent her over the couch so I could take her, standing from behind. I slapped her ass a couple more times. I could feel her quivering nerves. It was time to cut the shit, and do what we came here to do. A novice, I angled my throbbing pulsating cock toward her perfect little anus. She looked me in the eye with a combination of fear, respect and lust. And I went for it. Pouring a nice dollop of lube on, I slid the head of my cock in. In all my furtive anal explorations, that was as far as I had ever gotten, and it had at all times ended before it began. This time, I was determined to complete what I had started. I pushed the head in and her entire body stiffened and she stood up straight and yelped in pain.
“Yes. You’re such a good whore for your master.”
She moaned and whined some more, but she didn’t stop me. I pulled her hair a little and worked the head of my cock around in a tiny circle. She groaned deeply. Then I began to fuck her ass. She wasn’t an anal virgin, but it was clear she had never taken anything like me in there before. She shut her eyes, like she could barely engage with the reality of what was happening. As I started to fuck her, at first gently and then increasing in intensity, she couldn’t stop herself from pushing me back a few times. I wondered this might be coming to an end, like the other times. Then I heard a noise that surprised me more than anything else:
“Yes, master…”
Her eyes were closed, like she was on some far away plane, and she appeared to be loving the absolute reaming my monster cock was giving her little ass. Encouraged, I started to fuck her a little harder, pinching her ass cheeks as I did so. Then I was pulling her hair with one hand and pushing down on her back with the other as I continued to slide it in and out. Her moans rose to a scream, and she began to spread her ass cheeks for me with her pretty little fingers, even rubbing her pussy a little bit. This was too much for me to bear, and I started fucking her for real for real. She was fully keeling on the couch and I was standing, and about half my monster cock was buried up her ass sliding in and out while she moaned, whined and cried out feebly. Every time I wondered she was about to make me stop, she’d fuck me back a little bit, or pull my hips toward her. Time stood still in that moment. It was one of the most outrageous sexual experiences of my life.
It was time for me to take over once and for all now, and I pushed her head down onto the couch and started putting more of myself in…maybe three quarters now. I kept holding her hips, fucking her. Somehow, as much as she whined in protest and even seemed to sob sometimes, she kept fucking me back, that unyielding primordial hip movement that says “Fuck me master, fuck me, fuck me, fuck me.”
I wanted to make her whore for me a little more so I roughly pulled her up, knelt her on the ground and fed her my cock some more. This time I was really throat fucking her, and she was gagging and tearing, but this was what we were both here for. I felt like an animal, and she was my animal. When she looked into my eyes, I could have sworn I saw love.
As if to give me everything, she finally stood up and pulled off her tank top, revealing her braless tits, which were essentially perfect, mid sized but full, with beautifully placed erect areoles. I laid her down, this time on the table and spread her legs wide. Taking her hand, I placed it between her legs. Understanding me, she began to stroke her clit, and I eased my cock back into her asshole, this time from the front.I fucked her unyieldingly this time, and I could see the skin around her anus bending against the pressure of my monster. This time, she wanted to see, and she raised her head and watched me pound her, her face a mask of pain, pleasure, fear, excitement and just plain overwhelmed. She yelped and gritted her teeth. I kept fucking her, and began to suck her toes which made their way to my lips. “Ah fuck!” She screamed. “Yes master, fuck me! Punish my asshole!” What could I do but do as she asked? I moaned and fucked her with my entire length now, disappearing inside her in a way I did not know was feasible. The pleasure in her moans seemed to increase as she rubbed her pussy rhythmically. I had to pull out for a second cause I was so close to coming. But once I caught my breath I shoved it right back in, bending her knees together to give me full, cruel easy access.
“Oh fuck, master,” she yelled in pain, as I fucked her little ass with all of me. It was like nothing I had ever felt before. And the power of the moment? We were both suspended in the electricity of our Dom-sub arrangement. I could have pounded that ass forever in that position, and her mouth gaped wide, screaming and howling with the pain and pleasure of the moment. “Is it good?” I asked. “Oh, yes master,” she gasped out between wails. I kept fucking and fucking and fucking. My balls were slapping her ass cheeks now – it was the deepest I had been. But all things must pass, and it was time to move again.
We laid on the couch in a spooning position, and I worked myself back into her ass. This time I let her do most of the moving as I kneaded her gorgeous tits and kissed her body up and down. She was wailing and moaning and her pleasure was unbelievable. She grabbed one of my hands and placed it on her pussy while she kept fucking my rod with her ass. She turned her pretty little face to kiss me. And at that moment, I felt her cum, her entire body convulsing in shakes and her screams rising to a fever pitch. With the sensitivity of the orgasm, she kept trying to move my fingers away from her pussy now, but I was unrelenting and kept rubbing and pinching, kept fucking that little ass. Her screams must have been audible 5 apartments away.
She put a willowy arm around my neck, kissed mea again and continued to bounce her ass on my giant cock. This was really something else. I was squeezing her tits, pulling her hair and choking her gorgeous lithe neck and she was howling now. I guess she’d had enough, because she suddenly popped onto the floor and began sucking my cock again. By now I could barely take the lead – I was so close to busting. I had to close my eyes to disorient myself from the situation. How did I even get here?
Finally, she climbed back on me one more time, her back to me, my cock up her ass, riding me in reverse cowgirl. “Fuck me, master,” she whined again. I held her hands forcefully, preventing them from moving, holding her in place as she bounced her gorgeous ass on my cock. By now most of the pain seemed to have transitioned, and she kept saying “Yes, yes, yes!” I held her in place in the air, controlling her whole body, and began to ream her myself, thrusting up and down. But she was implacable and wouldn’t stop bouncing too. We were locked in a gorgeous, intense, fearsome tandem, bouncing and rocking, my 10 inch cock filling her entire asshole. I began to swell the way I do when I’m gonna come – it becomes almost scarily big. I could tell she was feeling that, because her cries were becoming higher pitched and more desperate. Still she rode me, and still I fucked her back.
She needed yet another break, and it was back to sucking. I was happy to let her worship my cock. She knew what it was now, she knew what it could do, and she knew what she was worshiping. Once she had sucked for a minute she crawled up me, looked into my eyes hungrily and kissed me deeply on the mouth with tongue. At the same time, she eased herself back onto me, facing me again now, and angled my cock for her pussy again. I guess her ass had had enough. I wasn’t complaining, because her pussy was so tight and wonderful. She put her hands on my shoulders and started riding me aggressively. I could feel every inch of her insides.
“Yes! Aw yes, master,” she continued to scream. I don’t know how long this went on for. It felt like forever and also like an instant. We hadn’t discussed birth control in all our impetuousness, and I could feel the moment getting very close for me. I was getting harder and harder and taking control over her entire body as it rode me, doll-like. Her tits were bouncing in my mouth and I had never been harder. Her cries got louder and louder.
“I’m gonna cum!” I suddenly yelled. As if on cue, she hopped off me, dropped to her knees and began sucking and stroking my cock, which by now was in absolutely massive condition. The sights of her naughty, pretty eye contact and her lips on my mushroom head were simply too much to bear, and I shot a load all over her lovely lips, down her chin and even into her hair. I came and came and came. Holy shit.
“Was I a good whore, master?” She asked.
“You were a good whore. Now crawl out of here.”
Giggling, she did as she was told. Jen and I met up many more times over the years. But nothing could really beat the shock and awe of that first encounter.

NSFW: yes


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