2nd hookup turns into (m)y (f)irst time doing anal

I had seen this guy once before but we hadn’t met up in over a month. This is how our text conversation went.

Me “wanna fuck?” Him “when?” Me “now”

He says he needs an hour to get home from school but he’ll meet me then. Hearing that was exactly what I wanted. I went to the mall to kill some time and then texted him that I was on my way there. He says yeah come now. I drive to his place and park and he then tells me “PS I’m not perfectly groomed right now.” Like that matters at this point, I’m horny and really want to fuck him.

Some description of this guy, 26 years old, has scruffy facial hair, a very hairy chest which I love, he’s fit, cut, and the thickest person I have been with so far (my sample size is only 4 though lol). He is the hottest guy I have slept with and the one I have had the best sex with so far.

Probably some of you have read my stories before, but for those of you who haven’t.

My appearance: 5’4’’, 115lbs, 32DD, pretty fit, some definition on my abs, brown wavy hair that’s past my shoulders. And I’m 19.

Okay so I get there, and he meets me in the parking lot. We briefly exchange some words as we walk down the hallway to his place. I drop my stuff at the door and realize I’m wearing the same shirt I was wearing the first time I saw him. I mention what are the odds I’m wearing the same shirt I was the first time I was here, he laughs and says he wouldn’t have noticed. We sit down on the couch a few feet apart and begin to talk about school. Eventually I got tired of waiting and moved to sit right next to him.

He looked at me funny and said “well if I don’t make the first move I guess you are going to” And I replied “Yeah well I came here for a reason…” Then he says “Well if you came here for a reason…”

He quickly peels his shirt off revealing his hot body and slides both his pants and boxers off. We haven’t even touched, and he’s semi hard. I’ve only been in his place for like 2 minutes. That was super hot to see. So he jumps on the couch and straddles me putting his dick right in my face. I start to suck and lick him but because I’m basically pinned to the couch, I can’t do a very good job. I tell him if he backs up a little I can do it better. He eagerly moved back a little so that I was actually able to move my head. He is reaching around behind him and rubbing my pussy over my jeans. I was already wet.

I tell him to get on his back and then I straddle him and take my own shirt off. We start kissing and he unclasps my bra. Then he takes my one nipple into his mouth and licks, sucks, lightly bites and I don’t even know what else but it felt good. He tells me to take off my pants and I do (this part is always funny to me because at this point its pretty heated and then I have to struggle to get skinny jeans off). I left my underwear on, which were violet and had a lace front. He tells me those can come off too you know. But I leave them on and straddle him again and resume making out with him. He is grabbing my ass and boobs but not touching my pussy yet.

Me “Feel how wet I am” Him “Already?”

And he touches me initially outside of my underwear and then slips his fingers inside where he really gets to feel how wet I am. I think he was pretty happy (most guys would be getting a girl that wet so fast). So then he starts going to finger me, and I don’t want him to ruin my underwear or stretch them out or something. That’s when I take them off.

I ask “are we going to do this here/the couch or should we move to your room?” Him “It doesn’t matter” Me “Well you’ll have to go get a condom eventually” Him “Yeah I know”

Since I’m straddling him still, he lifts me up (which by the way is one of my favourite moves), and I thought he was going to carry me to his room. But he sets me down on my back on the couch and walks away to get a condom. I later learned he grabbed two. I’ll get to that part eventually.

He returns and pulls me to the edge of the couch. He starts entering me and his face was insanely hot. And I was gasping for air. He must have been standing, because his thrusts were too strong for him to be on his knees. He kept saying fuck every once in a while and that was hot, but if I could film his face it would be priceless. This guy lasted really long the first time I was with him, so when he kept uttering fuck, it had me a little nervous he was going to blow his load fast.

He is thrusting and bottoming out hard in me, which I don’t really understand because he’s not that lengthy. I do like the feeling of bottoming out a little hard but on a scale of 1-100, with him it’s pretty close to 100. I tell him that it’s getting way too intense for me and I want to be on top for a bit. I don’t think he liked hearing that, but follows my request anyways. When I’m straddling him he is pulling my hips hard forward and pushing them back. Eventually he figures out the angle to move me to hit my gspot which is one of the things I remembered the most from the first time I was with him. He continues and says he wants to make me squirt. I kinda laugh and tell him a guy hasn’t been able to make me do that yet, so if he does I would be shocked. I also tell him he might have better luck with his fingers, since that’s the way I have got myself to (the handful of times I have). He tells me to get up on the soles of my feet, and I do, then comment that he’s going to make me work now. A few minutes later, I go back onto my knees and he resumes grabbing my hips making me grind on him hard. After all the gspot contact, I was feeling pretty good. My legs were starting to be shaky but I didn’t really know that until he got me to stand.

We had some miscommunication about where he wanted me to go, he said over there or something and I thought he meant to his room, but he really wanted something else (I’m not sure what). He follows me into his room and tells me he now has a different idea. He gets me to bend over the couch, his place is open concept so the back of the couch is where a wall would be between the two rooms. He wants me to keep my legs pretty close together and I think the height would’ve been better for him if I was a bit taller. He tells me to keep my legs straight. But as he starts thrusting into me, my legs are shaking a lot. I tell him I can’t keep my legs straight, lol. I’m super sweaty at this point and my hair is sticking to my face. I really do appreciate a guy with that much stamina, but damn he can fuck forever. He fucks me hard bent over and slaps my ass hard once. It stings and I’m breathing hard.

Eventually I convince him that it would be easier for both of us if we were laying down. And that’s when he starts focusing on trying to make me cum. He starts thrusting gentler, but not gentle by any means and is rubbing my clit. I’ve never had my legs go like a vice grip before, but they did around him. I can tell he does like making a girl cum because his face just lights up. It’s kind of cute.

I’m shaking and breathing hard and he keeps going and I’m scared I’m getting too loud (sorry whoever lives next to him). He didn’t say anything, but a couple of times I thought to myself that I should be quieter. I couldn’t help it though. He tells me how hot it is making me cum. During this time my legs are either on his shoulders, at his sides, or spread eagle. He was always grabbing and repositioning my legs. Sometimes he would lean closer to me and take my nipples in his mouth or kiss me, both of which I love while having sex.

His face is just centimeters away from mine and I can tell by the way he is moving that he’s getting really close.

Me “are you gonna cum?” Him “Yeah sorry. I am really close.”

I think he was apologizing because this didn’t last as long as the first time I was with him. But I was still happy with it, it wasn’t short by any means. I can’t give an exact amount of time but I was at his place for 2 hours in total and there wasn’t a lot of talking, mainly sex.

He starts groaning and stays deep in me and then thrusts really slow as he cums. He gets up and tosses the condom in the garbage. I move over on the bed and he collapses on the bed next to me. We both just relax for a bit. He is super sweaty and breathing hard still and I’m a little sweaty too. As we are laying there he starts asking me about the best ways to make me cum. He got me to once, but probably had me on the edge 5 or 6 other times. Once he cools off a bit, he stretches out his arm and I rest my head on it and I lay with my back against his side.

Anyways I’m feeling like I should go get dressed soon as we are both just laying there and not talking. But he tells me we don’t have to get dressed. He wants to make me cum more. He tells me to do whatever I want to him, which I don’t like. And then we get into this dom/sub discussion. I tell him I like a guy who tells me what to do more, and he says he gets tired of always leading. He wants me to do whatever I want to him and be direct about what I want too. I tell him I did miss his amazing oral. He replies that I should’ve told him that before. Anyways he can be more dominant as I soon find out.

So I’m laying now facing him with my arm over his chest and running my fingertips over his chest hair. We are just chatting but eventually I slide my hand down to his balls (realizing I hadn’t touched them yet). At this point he is back completely soft but not for long. I fondle his balls in my hand and he starts getting hard (who knew that could happen). Not like hard hard, but semi hard. And then I feel bad because we haven’t really discussed if this is it for the night or if we are going to do more. I don’t want to get him hard and then just get up and walk out. I stop touching him.

Him “You didn’t have to do that” Me “Well I don’t want to get you hard and horny again if we aren’t going to do anything else. And do you have other plans for tonight?” Him “I’m perfectly happy here with this, couldn’t you tell?”

I return to grabbing and stroking his dick and even when he’s not fully hard he is thick. I never noticed before because every damn time he takes his pants off, he’s already hard for me. I sit up beside him.

Him “Have you ever gagged before?” Me “Yes” Him “I want you to”

I briefly tell him about the time I let a guy facefuck me and force my head down on his dick to the point where I couldn’t breathe. And we hadn’t discussed a way for me to signal to him that I needed air. I ask if he likes that (facefucking, forcing a girl’s head down), he replies that he does too.

I make myself gag but not really hard and keep jerking him off with my spit coating his dick. Then the next time I put my mouth on his dick he forcefully pushes my head down farther than I had ever taken anyone before. When I jerk my head back to get a breath, he tells me he knows I can take more. My eyes are watering and he notices.

Him “I’m making you cry” Me “That tends to happen when you are gagging hard….I’m not sure if you’ve experienced that before”

After being forced hard down a couple of times, I realized I can take him farther myself. Maybe I’m getting close to learning how to deepthroat. One time when he is completely in my mouth he starts thrusting up and maybe gets 3 thrusts before I pull my head back and gag really hard. So then I take a break.

Me “Tell me what you want” (AKA are we gonna fuck again tonight or?) Him “I want my dick in your mouth” Me “Well I want your tongue on me”

I straddle him and he helps me move so that I’m in a good position for him because this is only my second time 69ing ever. I love the feeling of a tongue on me, it is amazing. I’m taking him only a small amount in my mouth and bobbing up and down. He starts off with one finger in me as he’s eating me. And then two. When he does things I like, I move more on him sort of as a non-verbal “thank you, that feels really good”.

When he gets into a really good rhythm I slide off him and am laying beside him but my head is towards his groin still. He is fingering me and rubbing my clit and it feels awesome. He starts doing the weird slap thing (as a guy described it to me, when you use your hand to kind of slap the clit as you thrust your fingers in). I would never have said it is one of my favourite things but it feels amazing and I’m starting to shake and grab his legs in desperation. He is intently watching me which is hot. And continues to watch as he makes me cum.

I start feeling sore already from his thick dick and the amount of time he has been fingering me, and tell him to cut back on the fingers if he wants to fuck again tonight.

Me “If we fuck again, you’re going to have to be way more gentle” Him “What do you mean by gentle?” I laugh and say “Imagine it’s your wife on your anniversary and you’re having really slow sex in missionary” Him “I can’t promise that, I do like it rough and hard”

Which I do too, but I know I probably won’t be able to handle it. This is the first time I am ever having a second round (and it’s only been like a 15 minute break). To add to that, I’m not used to his thickness and remind him that we will have to be gentler. He gets up to grab the second condom (he must have been able to tell instinctively we were going to fuck twice). I tell him I haven’t done this before (the two rounds in one night), so be nice. And I smirk.

We start off in missionary and he is being gentle but even when he’s not bottoming out the sensation is crazy. I don’t know it it’s the fact that I had just cum or that it was so much sex, or a different reason. He’s licking and sucking my nipples as he slowly moves his hips. I can tell it’s driving him insane not being able to move hard and fast. When he does start bottoming out I’m letting out “ah ah ah” every time. He tells me he’s not even in that far. I’m like I know.

He says he really wants to stick it in my ass. Here’s where I’m a little in disbelief still.

Me “You know I’ve never done it and I’m scared it will hurt” Him “ Well you’re already in some pain now anyways…” Me “What if it’s gross?” Him “It usually isn’t and if it is I am wearing a condom anyways” Me “You’re not going ass to vagina just so you know”

We are both looking directly at each other and he’s waiting for the go ahead.

Him “I’ll just start with the tip” Me “I’d be more likely to say yes if you had lube” Him “I have lots of spit”

I give him the go ahead not entirely sure what I’ve just agreed to. He puts a ton of spit on my ass and starts to push into me. I tell him I don’t think I can do this, it hurts. He pulls back and can tell I’m not really feeling it. He informs me it will hurt, but it does feel better once it’s in. I’m a little reluctant, but give him the chance to try once more. I try to relax, but as his head pushes into me it does hurt a lot. Once it’s in though it feels better.

He doesn’t move at all in the beginning so I definitely appreciated that. I don’t even know how much of him was in, but yeah. Also when I got home, I learned missionary maybe isn’t the best position to be in when you take it in the ass for the first time, but yeah it happened. He thrusts really softly and starts rubbing my clit and fingering me again. Now I’ll admit, I’m a little excited to try a DP someday. He maybe fucks my ass for 5 minutes. At one point he takes his hand and places it on my neck. Not hard, like not actually trying to choke me. But more of I am in control of this situation. Having him in my ass feels good, not amazing and I’m not sure how much more I can handle. I tell him he might have to stop before he cums. Haha what guy wants to hear that? He says he is close, I don’t know how he could be…he is barely moving. I guess maybe just the novelty and excitement of anal. He thrusts a little more and then does cum in the condom in me. I ask what the normal procedure is after this, and he doesn’t give good advice or tell me anything specific to do.

I go to the bathroom and my ass is super slippery from my own wetness and his spit. I clean up a little and go back to lay with him for a bit. Eventually get dressed, he puts boxers on and we both get on our phones and start talking about life again. He walks me to the door, kisses me goodbye and says see you. And that’s how my first time having 2 rounds in one night and first time doing anal went. Hope you liked the story!

Source: reddit.com/r/gonewildstories/comments/54hef6/2nd_hookup_turns_into_my_first_time_doing_anal