Her First Anal Stories

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Her First Anal Stories
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Leanna Commins
I'm Lee, a news writer and a millennial who doesn't like avocado toast — but don't congratulate me yet, because I still spend half of my paycheck on regular toast.


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WARNING: This is not for the weak of stomach.
Anal sex can be a pleasurable experience for both parties if there's honest communication and the right amount of preparation beforehand. But anal sex can also beget awkward mishaps and downright horrifying moments that you'll (hopefully) laugh about later. From uncontrollable bowel movements to using lube that is certainly not meant for down there (#NoJudgment), you may want to think twice about venturing into the world of anal sex unprepared.
Twelve brave souls offer their most cringeworthy anal sex stories that'll make you want to take it nice and slooooooow.
1. “My then-boyfriend (now husband) and I decided to try having anal sex in the shower. We made the very stupid mistake of using shampoo for lube . It was terrible and embarrassing! I jumped out of the shower, called my sister, and asked what the hell to do because it burned so badly. She laughed at me. I had to kick him out of the shower and let the water run on it for a while. It took a couple days for the hurt to finally go away. I don't suggest trying this ever.” — Julia, 21
2. “ I broke my boyfriend's tailbone with a misdirected thrust.” — Matt, 20
3. “I was having anal sex with my boyfriend at his parents' place while they were gone and we decided to do it on the couch. When he pulled out, I pooped all over the couch , and we tried to clean it up but it was a white couch, and it wouldn't come out, so we just blamed it on the dog.” — Katie, 21
4. “I was hooking up with this guy and we got super stoned before having sex. While we were doing it doggy style, I told him 'Let's do anal.' He put it in all the way! It was my first time. I hit my head on the headboard from going forward because of the pain and passed out . I woke up a few minutes later and he was sitting next to me concerned with water [for me]. Sweet guy. Never doing anal again. For now.” — Genevieve, 19
5. “The guy I was dating at the time and I had done anal before, but this time was significantly more uncomfortable than before. He finished and got up to get dressed. I rolled over and noticed a tub of hair gel sitting on the table next to his bed . When he reached next to his bed for what he thought was lube, he accidentally grabbed the hair gel and used it as lube.” — Paige, 22
6. “It was our first time. He wasn't a particularly well-endowed man but he was a pretty good lover. Until we got to anal sex — now, mind you, I'm a bigger girl with a big butt — and he couldn't reach. We tried all sorts of positions and he was too small to get in there . I was mortified and I'm sure he was just as embarrassed. We put back on our clothes and sat awkwardly apart all night.” — Liz, 20
7 . “My boyfriend and I wanted to try anal sex for the first time. As we were doing it, he was super nervous I was going to shit on him, making the experience awkward and nerve-wracking. When I get nervous, I get gassy, so although that never happened, I let out a huge fart as he pulled out and he jumped back, thinking I had shit on him. And then tumbled off the bed. Really weird. Never did it again.” — Emily, 23
8. “He didn't use a condom. I ended up with a really bad yeast infectio n and a trip to university health services. It wouldn't have been so bad if it wasn't my nurse's first pelvic exam. Not only was it painful, but her supervisor decided to quiz her on vaginal infections and STIs. I couldn't get out of there quick enough!” — Jessica, 22
9. “My then-boyfriend (now husband) and I were just starting to experiment with butt play. I was bent over and he had a vibrator on my butt hole while we were having sex. At some point, he decided to actually put it in my butt. Well, it was a small bullet vibrator with no cord or anything on it, and it got fully stuck in my butt hole . I was so embarrassed, I spent the rest of the night in the bathroom trying to get the still vibrating vibrator out of my butt! Luckily, I got it out. I couldn't imagine going to the hospital with that problem!” — Jacqueline, 29
10. “My boyfriend and I had anal sex for the first time one night. It was great! The next day we went to an amusement park — I didn't realize that your bowel movements were not going to be as 'solid' as they normally are after that. Needless to say it all came out on a roller coaster!” — Taylor, 24
11. “My boyfriend and I decided we wanted to try anal sex, so we started doing our research to make sure we did everything right and made it a good first time. We knew we need to have lots of lube so we bought some, but what we didn't know was that w e accidentally bought warming lube . The more we did it the more it burned, it was awful ... never again.” — Brooklyn, 24
12. “My boyfriend and I were having sex for the first time. I'm a gay man, so I knew beforehand what was in store. I had a glass of wine or two or four to help ease my nerves. He was very slow about everything, gently making his way down. When he finally stuck his penis in, I completely freaked out and kicked him in his chest with both of my feet . It happened so fast, he just flew back! We went on to date for another three months. And my friends haven't let me live it down since!” — Kaleb, 20
Butt Stuff PSA: Trying a new sex activity should never be a surprise for either partner! If you want to see if anal sex is something you might enjoy, check out these foreplay tips to ease you into it slowly and *~safely~*.

How old you were, with who it was. How it was, did you enjoy it?
Girls, at wich age you had your first anal sex?
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25. It was my very first sexual encounter, and I was so nervous that I went numb down there. I didn't even feel anything, even though his dick was 8" with a girth that I had trouble blowing him. It was disturbing that I couldn't feel a thing. The only thing I felt was when he went limp inside me.
Maybe he did it slowly and careful, or your ass is wide. It doesn't have to hurt" I think
It should've hurt, or at least I should've felt something. Because when I finger myself or played with a dildo in my ass, it sometimes hurts. And the dildo was not as thick as him. Also, I was really numb as I could't feel anything. Not even when he was fingering my vagina. It was so bizarre
I was 20 I actually did enjoy it, we switched to anal because vaginal penetration was too painful.
18 and I didn't enjoy it because it was surprise anal
Not sure if I would say lol after that question.
20. I enjoyed it but for some reasons his penis kept slipping out from my butt.
'In' and 'Out' action is REALLY amazing!! My GF was 'teasing' me, just dipping in and out with a little ribbed toy, and she made me cum so hard I had to tell her to stop!!!
I was 18 and it was my bf, and it was different, but not uncomfortable, because I gave him cues on when to go and when to stop.
i have never had anal sex. i've heard mixed reviews about it
19, a guy I'd been sleeping with. I've done it over a dozen times with 3-4 guys and never grown to like it.
Never, and never will. If guys want to do that then go be with a another man!
22 and it did not hurt but I didn't like it either

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It felt like I was taking a giant shit except it hurt really bad and I could feel him ripping me. It hurt like a bitch, and I started crying, and I couldn't move for a little bit because it hurt so bad. The next time, we did our research and used a lot of foreplay, a lot of lube, and butt plugs, but it still felt terrible. It hurt at first, but then the pain went away. Then I just felt like I was pooping the whole time and it was super gross and weird. It didn't feel good at all. I had goosebumps and I legit felt like I was coming down with the flu. I've tried and tried because my boyfriend is really into it, but even when it stops hurting and I feel fine, anal just isn't for me. I don't get any pleasure from it. It just makes me feel sick.
Well i tried it for the first time about a week ago and stupidly enough my bf just went along shoved the whole thing in there (he did have lube) and i just screamed and it took about a minute for me to not feel like i was dying of pain but i still wanted to carry on i just made him put little bits in at a time and it was fine i enjoyed it and i liked how i just surprised my bf by saying lets do anal
Well, I'm probably different from the other females. Because I love anal sex lol. The First Time I tried it I actually suggested to my ex. He was a little iffy but I got him to want To try. But I already would play with my ass when I masturbate so when we did it it wasn't that Foreign. And yeah It did hurt at first because he was pretty big but eventually once I got adjusted it felt really good. I was more enthusiac about anal sex than when I lost my virginity. So I support anal sex xD.
All I'm gonna say is it hurt like hell. Worse than when I gave my virginity up. It's not my favorite way to do things.
I've tried it a few times but will never do it again. Sexually it did nothing for me and it hurts like hell.
It was uncomfortable and made me have to take s dump afterwards. Not worth it to me.
Painful as ****. NEVER doing it again
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Secret Solitary
By Thomas Bartlett Whitaker


Ketamine
By Bria Adimora Godley


from Beyond the Somber Station
By Liliana Ponce, translated by Michael Martin Shea


rising to the earth’s height
By Raquel Salas Rivera, translated from the Spanish by Carla Canseco

© 2004-2022 Guernica . All Rights Reserved.
Photograph via Flickr by Michele Molinari
My mother stands ironing in the kitchen. There is barely room to squeeze between the kitchen counter and her bottom. I am about twelve; she is five foot two. It would be unnatural to turn to face the cupboards as I slip past. I am wearing loose-fitting pants. She is in a skirt. As I brushed quickly by she bends to iron and presses her bottom against me. My penis swells with joy. I will remember this for many years to come, in unexpected situations, soothing, erotic, violent, or clumsy.
It also reminded me of an earlier time, in third grade, when Tawny Collie—that was really her name—the sexiest girl at Elbow Elementary bent over to pick up a red rubber ball during recess and a couple of my friends pushed me onto her behind and she turned around and said, “Clancy, that’s not nice!” I protested, and my friends laughed. In first grade Tawny had had a crush on me and had invited me over to her house at lunch for fish sticks, which I couldn’t eat. But by third grade I was well established as one of the unpopular kids, and flying below everyone’s sexual radar. Still, or for that reason, Tawny should have known better.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) .
Last night our little brother, as my stepsister Teryn told the story the following morning, had come downstairs while the rest of us were out and Teryn was alone watching television in the family room and asked her to “pull on my thing.” The thing was on full display, Teryn claims, out of the pajamas. “It was hard and he was rubbing it.” The little brother was age nine or ten. It is widely known or at least agreed in my family that Teryn is a liar and will lie in particular about this little brother, because she was the baby until we arrived, and then he became the baby, and my mother has never liked Teryn, and often accused her of sexual deviance and promiscuity from a surprisingly young age. So there’s no guessing whether or not the story Teryn tells me is true, though later in life my mother will similarly tell me that she saw the same little brother (now age sixteen) out mowing the lawn with his shirt off in the low, modest Calgary summer sun and pronounced fiery claw marks down his back. Why my mother told me this story also remains mysterious to me, though she once told me that “he got the looks, he could have been a model,” and another time she told me how much he resembled my father, who had no appeal for my mother other than as a sex object. He was a terrible husband, my dad. But the old man had gigantic sexual charisma. I’d seen him, in years past and in many different cities, pick up waitresses right there in the restaurant, before we’d even paid the check.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) . The process was slow and often seemed hopeless: I think it took an hour or more. I could still hear the movie in the background. I imagined my penis as a straw and a girl from school sucking on the straw. When I orgasmed it was qualitatively different than any orgasm I have had since. They say that, the first time you smoke heroin, it is called “riding the dragon,” and after that you are always only approximating that birth into a new world of pleasure and disappointment.
You can French kiss yourself. Take your tongue, fold it back upon itself, and now roll the tip of your tongue back and forth across the middle of the muscle. I learned this after French kissing Denise at the seventh grade dance. We had those at Rideau Junior High: every five or six dances the teachers would play a slow song, turn the lights down low, and we would have a kiss dance, during which, with luck, you would French kiss the entire time. I passed Denise’s house wearing my canvas bag of rolled and rubber-banded Calgary Heralds and tossed one on her porch, while French kissing myself. It is mildly titillating, but seems filthier, somehow, than masturbation.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not.
Age five and I am inspecting statues of nudes in a large museum book my parents keep in my stepfather’s study. The book is fascinating and I take it back to my bedroom and climb on the top bunk—my bunk—to look at the pictures more closely. The fact that the most interesting statues—the ones with breasts—have no penises puzzles me. In the bathroom I stand naked on the toilet so that I can see myself in the mirror and tuck my penis and balls between my legs and press my legs tightly together to achieve the desired effect. Ah yes, that must be what is happening in those pictures, I conclude. Then my mother enters the bathroom—there are two doors into it, one from the hallway and the other from my parent’s bedroom, and I’ve forgotten to lock their door—and begins to shriek. “Never do that again! That’s very bad!” Etc. To be fair to my mother, she has always been hysterical and repressed on the subject of sex (I don’t particularly like the topic either), and my father claimed that this was a main cause of their divorce. It’s true that she avoided physical contact with us for years. She had been abused as a child, though I don’t know in what fashion. On her wedding night there were some problems in bed with my father, and he left their hotel room, returned a few hours later, and threw a pair of woman’s panties at her.
After my mother married my stepfather there are some sexual experiences between age five and age fifteen that I do not recall well and may be inventing that took place between myself and one or more of my angry older stepbrothers behind the furnace in our basement. I was terrified of that small black hot space.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not; Kierkegaard might have been gay; it is possible that Friedrich Nietzsche’s first sexual experience was with a man, a kind of wandering prophet, a forester who walked with a stick and professed to be a wise man, and preyed on school boys; Oscar Wilde was gay; Marcel Proust was gay (I’m told that stuff about the rats and the hookers is invented); Jean Genet was gay; Burroughs was gay (William—Augusten is too, but, capable writer though he is, he’s not a hero of mine, and anyway hadn’t made the scene yet when I was in graduate school, or who knows, perhaps he might have been, I was in the hero-forming business in those days); was Levinas gay?; Plato was gay. My best friend at the time, Robert Ramirez, was gay, and wanted me to be gay too
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