Her First Anal Story

Her First Anal Story

Top Books

Top Audiobooks

Tim Finally Gets Jane's Ass: A First Anal Sex Erotica Story (Unabridged)
Arthur Takes the Virgin's Ass: A Barely Legal First Anal Sex Erotica Story (If I Can't Have Your Virginity, I'm Taking Your Ass) (Unabridged)
Bent Over and Giving It Up: Five First Anal Sex Erotica Stories (Unabridged)
The Anal Sex Collection: Twenty Backdoor Sex Erotica Stories (Unabridged)
Bent Over and Butt F--ked While On the Phone: First Anal Sex While on the Phone (Unabridged)
Bent Over While My Best Friend Watched: A Rough First Anal Sex Short (Unabridged)

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Murray isn't letting Liz out of the deal. It was simple. He goes to her cousin's stupid wedding and she gives him first anal sex. Now, though, she's nervous as hell about her first anal sex encounter, and not knowing what to do, she calls her friend Mandy. Of course, Mandy knows you don't make a sex deal and back out, so she shows up in short order to help her friend get used to the idea with some lesbian sex and a nice sex toy to get her used to a stuffed rear! Liz and Mandy never expected Murray to show up right then, and Liz's first anal sex just turned into her first anal MFF threesome! Warning: This audiobook contains very graphic depictions of sexual activity during a first anal sex MFF threesome. It includes oral sex, lesbian sex, sex toys, butt play, and anal sex. It is intended for mature listeners who will not be offended by explicit descriptions of sex acts between consenting adults.

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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~*.

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Welcome to Great Moments in Drunken Hookup Failure, where we showcase four heartwarming true stories of drunken love gone horribly awry. Off we go.
In college several years ago, there was a girl that I was seeing for a few weeks. We hadn't yet consummated our relationship, but I had a feeling it was coming soon. One night after a night of moderately heavy drinking, we go back to my room and sexy time begins. After about a half hour of making out, heavy petting, etc..., she decides that tonight is the night. I put on a condom and surprisingly, she wants it doggy style. However, between the booze, the darkness and my excitement, my aim was off by about two inches to the north. It wouldn't have been that bad if I had stuck just my tip in, but due to my excitement, I went, ahem, balls deep in her ass. She made a sound not dissimilar to what a dog sounds like when you step on its tail, a high-pitched yelp. Nothing kills sexy time more quickly than accidental sodomy. We dated for a weeks after that, but I never sealed the deal. The next time I was with a girl, some soft mood lighting made all the difference.
Yeah, women never think that's an accident either.
First week of my last semester of senior year of college. I end up at a party hooking up with a friend of mine, Liz, that I'd known since freshman orientation. Our mutual friends had been trying for years to get us together. Apparently regular sized people can't stand the thought of two tall people (I'm 6'6, she's 5'11) being in the same vicinity of one another without being in a relationship. I always resisted because I happened to be into other people whenever the suggestion was made and besides, no one likes to be told who the fuck they should or shouldn't be with.
So back to the party. I run into her and we end up talking. After a few drinks the cobwebs in by brain clear and I realize I'd be a complete moron if I didn't at least try to see if this beautiful, awesome, height-appropriate chick isn't into me. I lay it all on the line and tell her how I feel. She feels the same way. Sweet. We start making out and things move quickly. I think because we had known each other so well it brought a comfort level to everything that got things moving faster than they would have normally; like we were making up for lost time. I ask her if she wants to go back to my room. She does, and we leave together.
I lived in a six person suite; three bedrooms (each with its own bathroom and shower) and a common room. Only problem was there were five of us who signed up to live together, so one of us ended up having to get a randomly assigned roommate. I knew my roommate (one of the five friends) wouldn't be back for another day, and when we got back to the suite I yelled out to see if anyone else was there and got no response. So I thought we had the whole place to ourselves.
Back in my room, we began going at it. Clothes come off, foreplay commences. After going down on one another she asks if I have a condom. I get up to go to my desk to get it, put in on and crawl back into my bed where she's waiting for me. I'm beginning to slowly ease inside her when all of a sudden we hear a deep, guttural, moan coming from the other side of my paper thin wall. It's Lou, the rando added to our suite that lived in the room over from me. Jerking off. And talking to himself. Loudly. He must have thought he was alone, too. Apparently repeatedly assuring himself how large his penis was and how badly it could destroy any woman that got in its path really got him off. And the greatest part was he doing all this while talking in a voice not unlike Christian Bale's Batman. We ended up spending the next ten minutes trying our best to stifle our laughter until Lou finished, which he did while proclaiming loudly "GAHHH FUCK TAKE THE DRAGON! THAT"S WHAT THE FUCK I'M TALKING ABOUT!" After that, we both knew nothing was going to happen. So we just ended up making out a little bit more and spent the rest of the night laughing quietly about what just happened until we went to sleep.
It all actually ended up working out great for me. Liz and I are coming up on three years together in January. As for Lou, I never spoke to him or tried to contact him in any way after we graduated; so for all I know he's still out there looking for someone to take the dragon.
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I lost my virginity at the end of freshman year of college. Fast forward through summer, and its the second week of sophomore year and I had just moved into a fraternity and we were throwing lots of "beginning of the year let's get as many freshman girls into the house as possible" parties. After one of these parties where I didn't land a woman yet again I challenged my roommate to a shot taking contest. Mind you this is the end of the night not the beginning. After 5 shots we decide that we would rather smoke bongs. After about 3 rips a girl I had met earlier in the night comes stumbling into the room. She clearly wanted to get it on. So I kick my roommate out and show this girl how to climb the ladder into my lofted style bed. Before you know it she's blowing me. After a few minutes I sit up to put a condom on and get on top of her. And that's when I felt it all spinning. Instantly I knew I was going to barf, and it would be really really hard to clean up barf in a loft. So what did I do? I leaned over and barfed onto my coffee table from 6.5 feet in the air. Then I rolled over and passed out. I woke up to find out the girl left, barf all over the table and floor, a 5 inch gash on my leg and a condom on my dick.
Two days later (Monday) I talked to the girl and shockingly she invited me over to her dorm room the next day to finish what we started. The next day? Tuesday, September 11th 2001.
I live in an apt in San Francisco and I was drinking some beers and taking some shots with my roommate, as we prepared to head out for the evening. My third roommate and a group of about 10 guys and girls were already at the bar, so we were trying to play catch up and get out of the house. Shortly before we were about to leave, my roommate got a call from a mutual friend of ours, who was in the neighborhood with two girls. He came over, the girls were decently cute, though one had a boyfriend, and we proceeded to get even more hammered. We head out the bar and I'm doing pretty well with the other girl who was single. We consume god knows how many more drinks at the bar and I guess we left. I remember walking out of the bar with her, into the cold, but that's it. At this point, my memory is 100% gone.
The roommate that I was out with, wasn't in quite as bad of shape as me, and so he had some vague recollections and told me that we got back to the house without incident and also that I began to make out with the girl in the hallway and then walk down to my bedroom. I woke up the next day with most of my clothes on, so I was reasonably sure we didn't have sex, but slightly confused as to why it didn't go further. I figured it was no matter though, I had a great time, got hammered and made out with a cute girl in my bed. Good enough, right?
So, the next day, I talk to the mutual friend that had brought the girls over and he had a sordid tale for me. Apparently, my roommate was correct in his description: we did indeed start kissing in the hallway and then moved it down to my room. It gets a little weirder though. Apparently, things were going fine, when I said I had to go pee real quick. Rather than walk out of my bedroom door and into the bathroom, which is about 3 feet away, for some reason, I decided to stand in my doorway and piss out onto the kitchen floor. After I was done, I sopped it up with a t-shirt from my dirty clothes pile and put it at the bottom of the pile. All while this girl is looking on, horrified. Again, I don't remember any of this, but the girl certainly did. Anyway, she immediately left, went to sleep on the living room floor near her friend and they left at like 8am, well before I was conscious. The worst part is, I didn't know about this until way later in the next day, so not long after I woke up, I sent her a friend request on Facebook. Needless to say, that was not accepted.

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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 m
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Her First Anal Story

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