My first boyfriend 5

sex stories

Wow. I stopped writing a moment and looked back. I’ve written well over twenty pages already and I still haven’t even gotten to the part where I get fucked. It’s just that I remember that day so vividly in my mind. And the strange thing is, as I sit here, I’m trying to remember any other time in my life that I such a clear memory of. But none come to mind, except for other days and nights I spent with Sam. Things I always figured I’d never forget are becoming hazy. I can barely remember my high-school graduation, and while I do have a more recollections of graduating from college, even those are starting to fog over. The first day on my job has blurred with almost every other day I spent there. Yet I can still remember that day, nearly thirty years ago now, as though it had happened only yesterday.
I remember lying on top of Sam, my step-brother and new boyfriend, end to end, his cock in my mouth and my hard dick pressing against his chest, while he played with my butt. I was wearing a bra (although the socks that had been stuffing the cups had fallen-out at some point, much like the long, brunette wig I’d had on earlier) and a pair of fishnet stockings being held-up by a garter-belt, with smeared make-up all over my face. But none of that mattered at that moment. While I’ll admit that Sam’s fingers did feel great as he poked, pinched and prodded at my butt, all my focus was on the long, thick, uncut cock in my mouth. All I could think about was making my boyfriend feel good, and doing whatever came to my mind to achieve that goal. I sucked and nibbled his cock, then I did the same to his balls (he really seemed to like it when I pulled one or the other of his egg-sized nuts all the way into my mouth and slathered my tongue all over the fuzzy skin while gently sucking on it), I licked right below his balls, then all the way up to his cockhead. I pulled his foreskin up tight and shoved my tongue in through the little puckered nub, feeling his flared cockhead with my tongue (he really seemed to like that too). I hesitated a moment, when I felt him start actually pushing one of his fingers into my butthole. It hurt, but not so bad that I couldn’t deal with it. And as his finger slowly got deeper inside me, his cock seemed to get even harder and it throbbed. I nursed the head, playing with his foreskin with my tongue, as I felt Sam’s long finger slip inside the hole, which until that point, things had only ever come out of.
And the whole time, I could hear him muttering things like, “Oh yeah, suck my cock, slut,” and “Fuck, that’s one hot, tight little pussy.” And for some reason every time he called me something like a girl, or a cock-slut, or a whore, I started sucking his cock even more fervently, bound and determined to let him know that if it was true, if I was a cock-slut, I was his cock-slut and I was going to try with everything I had to be the best I could be. And after a bit I knew my efforts were paying off. Sam’s finger was buried deep in my butt and I could feel him wiggling it around inside me. I had to lift my body off his, the friction of my cock on his chest and upper-belly was getting to be too much, along with feeling a finger in my butt for the first time, and I could feel the tingles which always preceded my orgasms. And when I raised my body, I found that his cock was at a much better angle for me to suck it. It was easier to get it in the back of my mouth, and… I tried not to gag, and actually did a good job of preventing it. I felt his cock push my throat muscles open and slide through them. I left it there for only a second, before pulling off and swallowing a couple times to keep from retching. Then I went back down on him, this time taking his cockhead a bit deeper down my throat and leaving it there a bit longer. It didn’t take long for me to feel his cock starting to get even bigger and I could hear his breathing becoming a bit harder and faster.
“Holy fuck,” I heard him huff, as he pulled his finger from my butt (which seemed to hurt even more than when he’d put it in), “You are a little cock-slut, aren’t you, Tammy?”
He’d asked me a question, so I pulled my mouth off his cock and said, “Yes, Sam, I love your cock.”
“I about popped when you got it down your throat,” he said, his hands now rubbing over my butt cheeks, and I could feel wetness from one of his fingers, and realized it was the one he’d had inside me. you learn to do that?”
“Just now,” I said. Both my hands were on his cock, one down by his balls and the other up by the head, and both were slowly rubbing him.
“You ain’t never sucked a cock before, have you?”
“Not a real cock, like yours,” I responded.
“What does that mean?” and I felt his hands grip my cheeks tightly.
I wondered how best to word my confession, “When I was a little boy, me and another boy, well…”
“So you’ve sucked a little boy-dick, but never a man’s cock.”
I responded, “I never even seen a big cock like yours.”
Then I felt a slap on my butt and Sam started moving under me. “Alright then. I don’t give a shit about some little boys, so long as my girlfriend ain’t never been touched by another man…” Then he flipped me over, so that he was lying on top of me and we were face to face. He was holding both my wrists over my head, so that the bra pulled high up my chest and my nipples were exposed below it. The fingers of his other hands were moving over my face and I could feel his cock pressing at the skin of my belly and at the garter-belt I wore. He was looking me right in the eye and I was feeling a mixture of fear and excitement. I knew what he had planned, what he wanted from me. That thought scared the hell out of me. But at the same time, all I wanted to do was please my boyfriend.
Sam was looking down at my face and his expression changed, he suddenly looked mean. “You look like shit that make-up smeared all over your face. You really are a whore.” And as I looked up at him, I almost told him that he had make-up smeared all over his face too, from all the kissing we’d done. But with that look in his eyes, I didn’t dare say anything. I could feel his fingertips on my face, smearing the make-up even more. “Hot little slut,” he cooed, and then kissed me. And after a moment, he pulled his tongue from my mouth and looked at me again, the mischievous grin bright on his face.
“Now I’m gonna pop your tight, little cherry, you faggot-ass pussy,” his words were full of lust. “I’m gonna make you mine, like a fucking dog, I’m gonna make you my bitch.”
Sam got off me and got me on my hands and knees, with my butt right at the edge of the bed. I heard him spit, then a warm, wet glob landed in the crack of my butt. Within seconds, I felt his finger digging inside me again, slick with his spit. And even though I was terrified knowing what was about to happen, my dick was bone-hard and bouncing up against my belly. My step-brother slowly slid his finger in and out of my butthole and it actually felt really good. And at one point he touched something inside me, something that sent an electric shock through me, and I thought I was either going to pee or come. I moaned.
“Oh fuck yeah,” I heard Sam hiss, “You like getting finger-fucked, don’t you, cunt?”
“Mmm yeah,” I groaned as he pushed the tip of his finger right at that spot and I felt my whole body clench.
it slut,” he said, moving his finger inside me with more effort, as his other hand slapped my butt-cheek sharply. “Tighten-up that pussy on my finger.” I did as he said and clenched my body again. “Oh fuck yeah,” he pushed his finger in me hard and deep and slapped my butt again. “I just gotta get my cock in that tight little pussy and pop that fucking cherry.”
He pulled his finger out of me and I heard him moving around. I was still up on my knees, though as he’d played with my butt I’d lowered my chest to the bed and was supporting myself on my elbows and forearms, instead of my hands, with my face was flat against the sheet. A moment later, I felt Sam back by my butt and he was rubbing something cold on my hole. I looked over my shoulder and saw him standing there, the jar of vaseline in one hand, digging one of the fingers of his other hand inside the jar. Then his finger went to my butt and I felt him putting it back inside me. It went in a lot easier than it had before, and I felt myself opening up down there. I was itching to feel even more of my boyfriend inside me and at the same time, I was terrified too.
I didn’t have to wait too long at all. After poking one of his fingers in and out of my butthole a couple times, he pulled it all the way out. And when he went to put it back in, it felt bigger, thicker, and it even hurt a bit.
“Oh yeah,” he said and as though he could read my mind he informed me, two fingers up that tight, wet pussy.” He fucked me with two fingers for a few minutes, slapping my butt a couple times, so that I’d squeeze my butthole around them. And when I did, he told me how good of a girl I was, what a slut I was, and how great it was going to make him feel when he started fucking my pussy. Only a moment after he’d gotten four of his fingers through my greasy hole, which was feeling more stretched-out than it ever had, Sam slapped my ass as hard as he ever had and said, ready.”
His fingers were yanked from my hole and as I looked back, over my shoulder, I could see the slimy fingers that had just been inside me rubbing the goo all over his hard, red and angry-looking cock. He had a glazed expression on his face, a bit of a grin, but more, well, hungry-looking than I’d seen before.
“Get on your back, slut,” he said when he realized I was looking at him. “I wanna see your face when you’re feeling my big cock pop your fucking cherry.”
I did as he said, flipping over on my back so that my legs dangled off the bed at my knees. They didn’t stay that way long, Sam stepped-up and, as I stared at his glistening, slimy hard cock bobbing there, he grabbed my legs and shoved them up to my chest. The hand that had been greasing my hole and his cock left a big, gooey spot on my leg and all over the fishnets stockings. He pulled his hands away, and my legs started moving down again. He roughly shoved them back to my chest and told me to hold them there.
So there I was, on my back with my legs pulled so tight against my torso that my knees were touching my chin. I watched Sam dig another big glob from the jar of lubricating jelly and rub it all over his long, hard cock. Then he put the hand on my butt, and sticking a finger or two back in my hole, he deposited the rest of the goo there. When he took his fingers out and I saw him grab his cock again, and as I saw him bend-down a bit, aiming the greasy rod at my butt, I let my head relax, took a deep breath and closed my eyes.
I could feel him rubbing the fleshy head of his cock up and down my crack and each time he rubbed it across my hole, I felt one of his fingertips poke in a little bit. “Open your eyes, cunt,” he hissed, pushing the head of his cock a bit more firmly against my butt. “I wanna see ‘em roll back in your head when I bust into your tight pussy.” I did as he said. Again, his expression was a bit scary. It almost reminded me of a zombie, or a possessed person from one of those horror movies. He was panting and sweat was dripping over his body. His cockhead and fingers were moving with more focus at my hole, pushing tighter and tighter against me.
“You ready to get fucked?” He asked in a harsh voice.
I nodded. Then I felt a finger or two push quickly and deeply into my butt and when he repeated his question, his voice was deeper and even scarier.
“Are you ready to get fucked, bitch?” he demanded of me, pushing his fingers roughly, as deep inside me as he could. “You ready for that cherry to be popped. You wanna get fucked?”
I managed to utter softly.
“Tell me what you want, bitch,” he demanded.
I uttered.
“Yeah, you want my big cock?” he pushed his fingers in even deeper and I could feel the head of his cock pushing in a bit too.
I nodded. He pushed his fingers in harder. “Beg me for it. I wanna hear how bad my little cock-slut wants to get fucked.”
I can’t explain it. It was like a switch was flipped somewhere inside me and all the sudden I heard myself, like it really wasn’t me. “Fuck me Sam,” I yelled. “Fuck my pussy. Pop my cherry. I got to have that big cock inside me. Give it to me, please Sam, give me your cock. I want to be your cock-slut. Fuck me, Sam! Please fuck me!”
“Shit yeah,” he said, pulling his fingers from my hole. “My little slut girlfriend want’s my cock.” And with that, he gave it to me.
Sam told me later that my eyes did roll back in my head when he shoved it in. He said that my mouth opened and I let out a sound like he’d never heard before. He wasn’t gentle about it. He gave me every single inch of his cock with one powerful thrust. One moment my butt was empty and the next, it was stuffed full. The pain was excruciating. I couldn’t imagine anything that would hurt worse. I thought I was going to die, right then and there, with my cock buried deep in my guts.
But his cock didn’t stay deep inside me for very long. He left it there only a second before he drew back. The pain eased a bit, though my hole still felt like it would snap like a rubber-band stretched too the limit. He didn’t pull his cock all the way out of me. When its flared head was caught by my tight ring of muscle, he slammed it back in again.
Now I must admit that as vivid as that memory is in my mind, that first time Sam fucked me is a bit hazy. I can remember the pain (is there a man alive who’s been butt-fucked, who doesn’t remember the pain of that first time?). It hurt like hell. And not just the first violent thrust. Though the pain did ease a bit, each time he rammed his long cock inside me, it felt like he was punching something deep in my belly. He told me that every time he thrust into me, I let out a grunt like he’d been pounding on my chest. Sam fucked me hard and rough. I have no idea how long it lasted. The whole time, he leaned over me and stared down at my face, telling me how good it felt to fuck my pussy, or what a great girlfriend I was going to be for him, or how much of a cock-slut and whore I was. And every time I closed my eyes, trying to focus on anything but the pain of my first fuck, Sam would slap me and order me to open them again.
It wasn’t until he was really pounding in and out of me, sweat dripping off his body all over me, and it felt like his cock was getting even bigger and harder inside me, that I realized I kept closing my eyes on purpose. I realized that every time he slapped my face, or chest, or shoulder, and he commanded me to open my eyes again, my whole body would clench. And when I felt my butthole cinch around his cock, well, even though it did hurt, it also felt incredible.
Like I said, I have no clue how long he went at me. It could have been hours, though if I had to guess, I’d say it probably didn’t last any longer than five minutes or so. Sam had lowered his body on mine, crushing me against the mattress, as his hips drove his cock in and out. Then he grabbed me and pulled me tight, thrusting his hips hard and I felt his cock punch whatever it was inside me even harder than it had before. His face was right over mine and I heard him hiss, “It’s a good thing you can’t fucking get knocked-up, cause I’m about to fill your cunt with all my little fucking babies.”
I thought I’d been getting fucked rough and hard. I had no clue. Sam grabbed my hair and twisted my head up so that he could kiss me. As soon as I felt his tongue pushing into my mouth, I felt his cock thrusting inside me again. I’d gotten used to the pain, but as he gave me his last effort, it all came back. He was grunting and growling right into my mouth as he fucked my butt with everything he had. Then he pushed himself deeper than he had been in my guts and let out a howl. His cock felt like a tree-trunk inside me and my whole body seized. It was bigger and harder and hotter and deeper inside me than it ever had been. And I could feel even more heat spreading inside me, then it was like my innards were being coated by molten-lava.
Sam let out an incoherent stream of curses and called me a bunch of names, as his body quaked and trembled over me, causing more of his sweat to rain down upon my skin, and he kept trying to shove his cock even deeper inside me. He pulled my hair and mauled my face with his mouth. He kissed my mouth, nose, eyes and ears, and at one point he even took a big mouthful of my hair, as he shot his wad up my butt. And as I said, it hurt like hell. But at the same time, I knew I’d never felt anything like it. Again, he could have been pumping me full of cum for an hour, though I highly doubt it. Time didn’t matter. So when I felt that log up my butt pumping with a bit less strength, and the quakes of Sam’s body slowed to mere quivers, and Sam’s kisses became a bit tender, I threw my arms around his back and tried to pull him as tight against me as possible, kissing him back as we both caught our breath.
We stayed like that for a while. Sam on top of me with his still-hard, but no longer throbbing cock in my butt, gently kissing and cooing to each other, both of us spent for the moment. When he finally did pull back a bit to look down at me, it was like he was ripping his body off me. Like something had glued our torsos together. He looked down between us and his face changed. I felt his cock surge, stretching my butthole some.
“You fucking little slut,” he hissed. “I never told you to shoot your load!”
I was shocked. I hadn’t touched my dick. I couldn’t have… But as I looked down, there was no denying the evidence. Both our chests and bellies were coated with goo, and considering all of Sam’s cum was churning around up my butt, and with his cock still lodged up there, it wasn’t going anywhere. It had to be my cum sticking us together.
“I can’t fucking believe you popped just from getting fucked. You are a little slut, aren’t you?”
I didn’t recognize what he’d said as a question until after he slapped my face.
you?” he demanded.
“Yes, I am,” I said softly, bewildered that I hadn’t realized the incredible sensations wracking my body a moment earlier for the orgasm that it was.
“And who’s little cock-slut are you?”
“I’m your slut, Sam,” I said with a bit more voice, and having a feeling as to what he wanted to hear, I continued. “I’m your girlfriend, Tammy. And you just popped my cherry. I’m not a virgin anymore,” and I squeezed my battered hole around the cock still in my butt. “You fucked me, Sam. You fucked my pussy and I can feel all your sperms swimming around inside me. And I’m such a slut and I loved it so much, I shot my cum too.” An evil look flashed across his face as I said that and I gave his cock another squeeze, clenching my butthole tightly around it. “I’m sorry, Sam. I didn’t mean to shoot. I didn’t even know it happened. It felt so good, that big cock of yours squirting up there. I couldn’t help it.” I squeezed the whole center of my body and I could feel his cock, which was still quite hard, twitch inside me.
His hands were all over my torso, rubbing my own cum into my skin. Then I felt more than a twitch inside me, it was a throb. ok baby,” he said and lowered himself again to kiss me. And as he did, I felt his hips moving, and he slowly started pushing his big, still-fairly-hard cock deeper inside me. “I guess I can’t complain that my hot, slutty girlfriend got-off from being fucked by a man for the first time.” As he talked, he started moving faster and with a bit more intent. “I’m gonna fuck you again, right here and now, with my own spunk making your tight pussy all wet. Is that what you want, baby? Do you want to get fucked again?”

story by: Verytas

Tags: fiction virginity cum swallowing transvestite boy teen oral sex authoritarian ass to mouth sex story

Author: Verytas

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