My [NB] First Time With a Guy [M] and He Asked For Anal

I was starting my first relationship with a guy and we were ready to jump into bed. We’re on the same college campus, and we go back to his room as soon as possible that evening. The lights are low. We press together. I’m all over him. He’s a good few years older than me and pretty, with whatever the 24-year-old version of a dad bod is. He’s bi, and has plenty of experience with girls and guys. I love that. I’m nervous, but so ready to get fucked. He breaks off as I’m kissing down his collar, and asks, ‘Would it be ok if we did anal?’.

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So. I had no interest in anal at all. I figured it would probably hurt. I’d had my hands on his penis before and while I’d learn it wasn’t especially big, it *was* sort of imposing at the time… So naturally I flash him a huge smile, look him dead in the eyes, and say, ‘Of course, anything you want!’.

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He grabs a condom from the desk draw and we laugh and kiss as we strip and put it on. He adds some lube on top of that. He moves to the bed, holds my hands, and lays down, pulling me on top. I’m tall and thin, but back then I was positively skinny. He just handled me on top. I leant down close to him. I kept my hair super long back then and I loved how it spilled over his chest and shoulders in a dark mess. He guided my hips over his penis. He had such a pretty dick!

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I could not get it in my ass. I struggled to get the angle right, I was tense, tight too, of course… I think I hurt him a little trying to just force it in. I tried leaning forwards, sitting upright… Somehow I managed to split the condom.

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I apologised and went to blow him to make up for the inconvenience, but he smiled, rolled me over onto my back, grabbed and donned another condom, and knelt back on the bed between my legs, which I’ve got spread and raised for him.

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He looks me dead in the eyes as he presses the fingers of one hand either side of my ass and *gently* works the head of his dick in. His other hand is holding my ankle up. Fuck me, it hurt. I wanted to take it, though, and loved every moment of the intimacy. He gave this low growl as he forced into me. I kept eye contact when I wasn’t rolling my head back on the pillow. I took a little more, then a little more… Once the head was in he asked if I was ok. I think I said ‘Yeah’, but I might have just squeaked. He pushed a little more, then back, then slowly worked into a rhythm until he was almost all the way in.

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I was not expecting to feel so, like, *filled*. I figured I’d moan and whimper ‘cause my instinct when I’m masturbating is to be loud. I was not expecting to, like, have to breathe around his thrusts too. At some point I managed to say, ‘Fuck me’, and felt him twitch inside me mid-thrust. My arms are crossed up by my head, my hair is brushed back from my body, and I’m just *open* for him. I love how he looks between my legs. I’ve got, like, zero bust to get in the way of the view. I’m just in awe of how gorgeous he looks. And getting stuffed, obviously. I’m angled too low to see down to my ass but I can see the base of his dick. He’s a little flushed. I want to stroke his tummy, or his chin, but I’m just lost watching how worked up he’s getting. He’s smiling, and I know he’s holding back for me. Half the time I have to look away from his body and just arc my head back to the pillow to be able to take him.

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We fuck like that for ages. He mutters about how it’s cute how tight I am, bless him. Eventually I can feel him pick up the pace again; either he can’t wait, or he thinks I can take it now. He’s right. It still hurts, and I’m still panting and moaning around his movements, but it feels really, really good. Out of nowhere he stops, and I can’t stand it. I beg for him to keep going. He says the condom broke and starts very gently pulling out. I prop myself up on my elbows and tell him just to get back in me without a condom. He says something like, ‘I hoped you’d say that’, pulls out, whips off the band of the condom, sticks on some more lube, and thrusts back inside me.

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Oh my god. Safe sex is important y’all, but nothing feels as good as raw dick. He pushes all the way in for the first time and I’m seeing stars. It *really* turns me on feeling his hips against my backside, my thighs… I want to wrap my legs around him, but I can’t not keep them up and wide. He’s red in the face and panting. I’m absolutely mewling. We’re covered in sweat. I *feel* like I came, but it’s all a blur. I couldn’t tell you how long we went like that, but eventually he gasps that he doesn’t want to come yet and slows down, then pulls out. He tells me, ‘Get on your hands and knees’.

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I, shakily, roll over onto my front and present myself like I’ve been told. I’m clutching the pillow tight as he holds my hips and just presses the length of his penis over my ass. He guides himself in and starts a good rhythm again. He pulls my hair into a ponytail as he fucks deep. He releases my hair, plays with it for a bit, then moves it over my shoulder so he can, as he said, ‘See your whole back’. He moves his hands back to my hips, a little quickly.

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It was at that point I lost it completely and discovered something new about myself. I was a moaning wreck just dedicated to taking him and I *loved* how it felt to have his palm slap against my hip. I reached back, grabbed his wrist, and just flailed his loose hand against my backside. I couldn’t ask him to spank me between mewls, but fuck I needed it. He was genuinely confused and stopped thrusting. I actually let out a ‘No!’ when he stopped. I twisted, propped up on one hand, looked back, and said, ‘Fuck me, slap my ass’. He did – fucking me hard but spanking me gently. I told him I loved him, I loved how he felt, but I wanted it harder. I started slapping my own backside *hard*. Maybe not my proudest moment. I could have been playing with myself, but no, spanking it was. It took some of the pain away from anal, so I was left with more of the pleasure, and *fuck* I liked being slapped. I had my ass up for him and at some point I’d arched my back and buried my face in the pillow. I was moaning and gasping and occasionally panting out that I loved him. He was moaning louder, and told me he loved me back. I was completely lost in a blaze of orgasms, or just rolling pleasure as good as orgasms. I heard him give that sexy, elongated ‘Ughhh ughhhh ughhhhhh’ noise guys make when they come. I can’t remember if he came inside me or pulled out and came over my back; he did plenty of both in the future when he wasn’t blowing over my face or in my mouth.

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We collapsed and cuddled. He made sure I was ok with what had happened. We were exhausted. We checked the time. It was like 3AM; we’d been fucking for hours. He had an en-suite shower so we cleaned up together. He was sat in the shower. I was sat in his lap. Well, sorta. I rested my thighs on his legs so my backside wasn’t directly on anything. Like I said, I’m tall, so I slumped around his shoulders. I cried – I was so tired, and so sore, and had such a good time. He asked if I was ok. I reached down to his penis, which looked sore too, and asked if would be ok to go for round two. He laughed and said ‘No’; in retrospect, I’m really glad. I couldn’t have taken it then. I stayed the night. Single bed, but I didn’t take up much space in it.

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The next morning, though, I blew him like I did most every day we were together, then went to class. I was a little wobbly and sore, but *I* thought I hid it well. I was an A* student and didn’t miss a class or question; I didn’t exactly hide in the back. Some of our study time was in the library and I heard some of my classmates, all guys, speaking with my then-boyfriend. They said they could tell he’d had fun with me ‘cause I couldn’t walk straight. He said something like, ‘Yeah, [Hydralt] loves it in the ass, and took it for hours. They’re such a slut in bed’. I was mortified. It didn’t take long for the details to spread to everyone. Most of my girl friends had heard I got dicked before I could tell them. And there was the small matter of the rooms next-door having heard…

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We were kinda, like, addicted to anal. Almost as much as *I* was addicted to blowing him. Probably 75-80% of our time fucking was him fucking my ass. You’ll be glad to hear that I learned how to properly ride like that. He’s the only guy I did more than blow, though, and I’m now happily married to a woman who teases me about when I was an absolute mewling wreck for anal, and occasionally threatens to fuck my ass with our dildos when we get sassy.

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I tend to lurk rather than post, so apologies if this isn’t right or isn’t what you expected to read when you clicked! <3

Source: reddit.com/r/gonewildstories/comments/wxljdg/my_nb_first_time_with_a_guy_m_and_he_asked_for