Anal Sex Adventures

Anal sex is in, and to be blunt – most guys want to fuck a girl in her ass at some point in his life!

It’s the hard (pun intended) truth. It can become a pressure between partners when one person definitively wants to try anal sex and one doesn’t even have anal sex on their sexy-time radar. The truth though, is that anal sex and ass play in general can be some of the most intense and enjoyable sexual experiences when done properly.

When it comes to anal sex, some of us girls are success stories with positive first experiences. Other girls, however, have horror stories or fears that make us never want a guy going back there under any circumstance. Some of us lucky ones were converted, only to become addicted to the pleasure of ass play and anal sex, with the hope of introducing it to new partners of our own.

Is Anal Sex “Vanilla” or “Taboo”?

Depending on who you ask, anal sex and ass play can get shockingly different reactions. Of my group of best friends, only two of us girls admit to enjoying anal sex and three have tried it but say it’s not for them. The remaining three of the eight of us have an absolute hell-to-the-no response any time the topic comes up.

I became sexually active at a young age. It was my freshman year in high school when my then boyfriend first mentioned the prospect of anal sex to me. To generations older than my own, the idea of sex at that age, not to mention anal sex, might already be surprising. Yet, those people must remember, my generation is hyper-sexualized. I mean, all teens are obsessed with sex and have raging hormones, regardless of what decade their adolescence took place in. However, my generation is one groomed off of Internet porn and other forms of entertainment that pushes sexual limits. Things that might have been taboo to our parents’ generation has become matter-of-fact or even “vanilla” to us.

Regardless of age or gender, though, sexual fetishes are subjective. What’s the norm and expected sexual play to one person might be deviant and offensive to another. It’s anal sex, though, that is one of those fetishes that falls within the mainstream that is still met with shock and whispers when discussed in social circles.

I’ve known girls who claimed to give blow jobs before they ever had their first kiss. I’ve known other girls who had anal sex because they didn’t consider that as giving up their virginity (eye roll). Other girls of course were harassed into it by boyfriends, while some had a very clear “no enter” policy on ass play of any kind. Sex acts like oral sex, vaginal sex, and YES, even anal sex are the norms for most average teens in a world where SnapChat and secret texting apps that our parents don’t know about are the main form of communication among friends and classmates.

Once, during my sophomore year of high school, a boy from one of my classes who might never have had the nerve to speak to me in school had all the courage in the world talking over direct message. Alone in his room one night, he got horny; having seen some pictures I added to Instagram, his self control was tested and he became so confident that he felt the need to text me. He wrote something to the effect of, “I want you to wrap those sexy lips around my cock so bad.” As a young woman, I feel flattered by this compliment, while at the same time questioning the nerve to be so bold to a girl he’d never had a real conversation with in person.

As you can imagine, if propositions like this come from mere acquaintances, when it comes to someone you’re already sexually active with, the limits are tested and pushed constantly. From requests of naughty SnapChats to acting out fantasies your boyfriend or friend saw in a porn the night before, this tends to be how many girls my age come around to trying anal sex for the first time. Just like “regular” sex, once anal sex is practiced within your circle of friends, it becomes more normalized, less taboo, and just another way to switch things up in the bedroom (or in the car or wherever the hell you can get it in before you have to be home for dinner). 

Ease Into Anal Sex with Ass Play

From early on in my sexual experiences I enjoyed having a guy lick me all over, which includes finding his tongue exploring around my tight little asshole. Feeling a finger press against that spot as I got my pussy licked, would make me quiver all over. Eventually, having that very first finger start to press against that tightness, I was introduced to a world that made my orgasms more intense and my sexual appetite even more exaggerated than it already was. I have amazing memories back to my early sexual experiences when my boyfriend would go down on me literally every single day after school. He’d always in some way explore my perfect little tight asshole, telling me he dreams about the day that I finally let him fuck me there.

Due to his desire to take things to the next level, my boyfriend showed me an anal sex video of a girl hardcore fucked in the ass. In his own misguided youth, he chose a video that was particularly rough and hard and turned me OFF rather than ON to the whole idea of it. I still wanted ass play with his tongue and finger, but gave a strong “no” on anything more. One day he even “accidentally” slipped back there as he was fucking me, and the excruciating pain made me scream and cry and tell him that the whole idea of him, me, and anal sex just isn’t going to happen.

Fast forward a couple of years, after my aforementioned anal-dreaming boyfriend and I broke up. I got into a relationship with a man who was much older than me and very married (oops). He loved my youth, energy, and sexual appetite. I loved his experience, gentleness, and sexually explorative nature. He told me there wasn’t anything he wouldn’t want to do with me, and this naturally opened the topic of anal sex.

He told me he’d done it before, but never with his wife. She never wanted to try it and once she said she didn’t have that interest, anal sex and ass play of any kind was shut down completely. Hearing him talk about his experience of fucking girls in the ass in his past and loving it, but being cut off from ever having the chance to experience that again made me think about my own sexual choices.

I never wanted nor do I ever want to be that woman who says “never.” I knew I didn’t want to go that far with my ex-boyfriend and do anal a couple years prior, but now… I was intrigued. I had this experienced, sexy, mature older man who knew what he was doing. Furthermore, the extent to which he would get hard when we would talk about it would turn me on so fucking much.

So one brave night, I took solace in the distance of not being with him at the time and texted him a selfie of me with my ass up in the air behind me. The accompanying message read, “I want you to fuck me so bad, and I want you to put it in my ass next time.” So the following Friday after school, when my parents thought I was going to my best friend’s house and staying the night, I showed up at the hotel to meet up with him. I was nervous and excited. He came equipped with lube and was already hard, but fully expecting me to tell him to stop as soon as he got started. He took his time with me. He ate me out, warmed my little ass up by licking it and fingering it, and telling me how fucking hot I am and he can’t wait to feel that tight butt wrapped around his cock.

I’ll never forget the feeling of the head of his cock pressing against my ass for the first time. His cock was so wet, and it took a really long time for him to even be able to fit the head inside of me, which was the most painful part. He was patient, gentle, and sweet. He constantly asked me if I was okay and wanted more. I could only keep expressing a breathy “yes” as he tried to fit it in. Eventually, he got the head in, and started to slowly push in further, never being rough or getting too carried away.

If I could ever give a man advice about turning a girl on to anal sex, it would be to use this patient and gentle approach. The “oops, I slipped” and rough anal sex porn approach of my previous boyfriend got him nowhere with my ass at that time. However, this sensual, slow, and conscientious technique not only turned me on to anal sex, but eventually got me begging for him to fuck me in my ass nearly every time we would hook up after that.

Like most things, this affair came to an end. He’s still with his wife, but it makes me smile every time I think about being able to make his teen anal sex fantasies come true. It makes me smile even more, though, that he turned me on to something that I otherwise would have potentially cut myself off from trying simply because it was, with my ex-boyfriend, the wrong person at the wrong time.

Guy’s who call me on NiteFlirt for phone sex fun know that I’m an “anything goes” phone-fuck teen who loves it in my mouth, my pussy, and my ass. I like it slow and sensual and I like it hard and wild. Anal sex is always on the menu for my insanely sexy NiteFlirt boyfriends, but when it comes to real life I’ve only given my ass up to one other guy after my first anal sex partner.

The one other person was that ex-boyfriend who turned me off to it in the first place. For a very brief 3-month period, we got back together our last year of high school, and I never told him at the time that I had anal with someone else before him. I did, however, walk him through the slower, more sensual approach and it was amazing. It confirmed, if nothing else, that it wasn’t just a fluke; I’m a fan of anal sex! Things not long after got contentious between my boyfriend and I again. One day, in a cruel moment of too much honesty, I admitted to him that he was NOT the first guy to fuck me in my ass. Part of me took pleasure in this due to some of the ways he had previously treated me. However, there was that little part of me that felt guilty since he and I had so many other “firsts” together throughout our relationship.

I’m still waiting though, for that next guy in REAL LIFE who is going to get my ass. I love anal play and anal sex and can’t wait to meet another partner who goes above and beyond to worship my hot ass, do everything in his power to make it feel good, and who will cum harder than ever when he knows he’s in an elite club of guys I’d ever let slide into my ass and spread me open in such an intimate and exhilarating way. Until then though, where are my anal sex phone sex partners? I am craving a good anal fuck right now!