“How does this shit always happen to me?” I wondered as I lay on the bed, face down, ass up. I couldn’t even appreciate my tailor-made shit/ass pun, because I was too nervous about what I was getting myself into, or, er — what was about to get into me.
I had said yes to #buttstuff, and now? Well, I was fucked, or about to be. In the, uh, butt.
By now, you probably think I’m a total slut. I mean, I’ve written about getting caught having public sex, my ill-fated threesome, and, of course, the time I tried Fifty Shades of Grey sex. The thing is, I’m a firm believer of not knocking something until I’ve tried it — sex stuff included. You never know what you will and won’t like, and I’m not about to limit myself on the pleasure front. Besides, as the ultimate slut, T-Swift once said, “haters gonna hate, and they give shitty BJs” or something like that.
Anyway, my butt journey started the same way all butt-related stuff does. I was young, dumb, and in love. That’s how the guys do it. As soon as you fall in love, they start asking to put it in the butt. It’s like a sixth sense they have. When they gaze into your eyes and tell you that they love you, what they really mean is, “I’d love to put my penis in your pooper.”
So here I am, just a butt virgin in love. I had been dating my boyfriend for a year and we were having regular sex, after I awkwardly took his virginity months before. We had gotten pretty used to this vaginal intercourse thing. I knew how to ride his (slightly below average-sized) penis in a way that would get me off in minutes flat, and he knew how to, well, thrust. It wasn’t the best sex I’d ever had, but hey, we were just two kids breaking the law of the Lord. Then the topic of the “red sea” came up. You know — pounding while aunt flow is in town? Getting down with the crimson tide? Period sex, guys.
Back then, it wasn’t happening. I’m not sure if I was embarrassed or if he was grossed out, but either way, P in the V during the bloody M week wasn’t a thing in our relationship. So, after months of not getting any while I was on the rag, my boyfriend uttered the words no girl ever wants to hear:
“Can we try anal?”
Butt Stuff Tip 1: Just Say No
Seriously.
I said yes. Next thing I know, I was sitting in the “naughty” section of Barnes & Noble trying to figure out how to insert a penis in my butt hole. Just what all parents dream for their little girl, amirite? Needless to say, I was not prepared. It sounded complicated. You needed lube, but not too much lube. You needed to be loose, but not too loose. You most likely wouldn’t shit on his dick, but it wasn’t impossible. Basically, you needed to be a fucking wizard to make this happen, and a mere muggle such as myself had no hope. (Butt stuff and Harry Potter? Talk about a winning combo.)
Butt Stuff Tip 2: Do Your Research
And by that, I mean find a delightful European country to move to, pack your bags, and flee from your home to avoid ever being a part of this. Or just google “how to have anal sex.” Personally, I’d say go with the first option.
Basically, it sounded awful. I honestly just hoped that my boyfriend would forget the whole thing. I mean, he forgot our anniversary, the fact that he wasn’t supposed to kiss other girls, and my middle name, so, like, maybe he would forget this, too.
Butt Stuff Tip 3: He Won’t Forget
As soon as you give any indication that you would even consider butt stuff, he won’t let the idea go. Ever. Crush his spirit as soon as you can to avoid a forever of saying, “Not tonight, I’m constipated.”
Unfortunately, because life isn’t fair, he didn’t forget. We just got back to his place after a night out with friends. We were kind of tipsy, giddy for each other’s company, and in the beautiful drunk/horny stage that occurs before the drunk/crying stage. But, since I was bleeding out of my vagina, I figured we’d just have a little over-the-pants action and call it a night. I was wrong. As we were kissing, he pulled back to gaze deeply into my eyes. I felt my heart pound and the blood flood my face. This was it. He was going to say something beautiful about how much he loves me. What if he proposes? OMG, HE’S GOING TO SAY HE WANTS TO MARRY ME.
“Hey baby. Do you think — will you — I mean. We…”
Butt Stuff Tip 4: Expect The Unexpected
He’ll pounce when you least expect it.
“Do you think we can try anal?” he asked.
WHAT THE FUCK? I scrambled to make a decision. Say “yes” and be the coolest girlfriend ever or say “no” and keep my butt hole intact? I wished I could be the role model girl in the situation. You know, the one who took a good, hard look at herself and said, “No, I don’t think this is for me.” Unfortunately, I’m not that girl. Thanks to the clouded judgement of young love — and Bacardi Dragon Berry — I took off my clothes and got down on the bed. I wanted to seem like I knew what I was doing, so I bent over, ass cheeks spread, and said, “Put it in.”
Put it in? Are you insane? I was acting like this was a cheesy, low-budget porn film. You can’t just put it in! You have to prep. You have to loosen, lube, and limber up. But no. All of my research immediately went out the window. Tight little butt-holed me wanted to seem with it, so I waited while my boyfriend unbuckled his pants and asked “Are you sure?”
Butt Stuff Tip 5: Take The “Out”
If he asks, “Are you sure?” the answer is “no.” Immediately clamp your ass cheeks together.
“Yeah, totally,” I slurred seductively from my downward dog position. I felt my entire body tense up as he knelt behind me. I kept thinking, “I got this, I got this. Just a thing in another thing. Body part in body hole. Anal sex is perfectly natural. Maybe I’ll like it. Some people like it, right?”
Butt Stuff Tip 6: No, People Don’t Like It
They’re just liars. Or, at least, making the rest of us look bad. Don’t trust them.
I could feel the tip of his penis touch the entrance of my anal region. Just a little poke and I knew I was in trouble. It was like someone was trying to jam a hot dog up my butt. You can’t just shove a giant piece of meat up a teeny, tiny hole. That goes against science. Fortunately, I wasn’t the only person who realized this. I could feel the awkwardness fall over him as he rubbed his penis on the opening of my butt. I wasn’t quite sure how, exactly, he was planning to get himself in there. It seemed like an attempt to penetrate me via osmosis.
“Maybe I should…spit on it?” he mumbled.
Spit on it? As in spit on my asshole? This was going from awkward to humiliating. Sure, spit is a great resource during sex, but not spitting in someone’s butt. Is that even safe? Did he have to…put his mouth on it? I felt the color drain from my face. Doesn’t that violate a safety code or something? Shit. We didn’t have any lube, and there was no way that sausage was getting in my buns without a little slippery help. I figured it was now or never. Time to take life by the anal passage.
Butt Stuff Tip 7: Don’t Spit On It
For your first time, spend $5 and buy a bottle of lube for God’s sake. You have to splurge before you splooge.
“Yeah, spit allll up on it.”
Ew. Who was I? I felt a cold, snotty liquid slide down in between my cheeks. Luckily, he didn’t put his mouth on my asshole, but the fact that saliva was slipping into my ass was alarming enough. Imagine a slug in your pants. It was like that, except worse, because I knew what was following that slug. A big, erect…
“OWWW!” I screamed.
What the actual FUCK just happened? I felt like someone stabbed me in the ass. Apparently he thought shoving his dick into my shitter was the best way to “slowly make butt love.” No warning. No, countdown. No fucking numbing cream.
“Are you okay? Did that hurt?” he asked, while still balls-deep in my back door.
“No. Yes. I mean, it’s fine. Just keep going.” I said, through tears.
TEARS. Literally tears were coming out of my eyes. I wanted to say this was a fucking mistake, but I felt like I should give it a chance. All I could hear were his grunts as he slid his pain stick in and out of my ass cavity. Apparently someone was having a good time. UGH. “I got this, I got this. Pain is sexy. Pain feels good. Deep breaths. Be one with the thrust.” And it actually started to work. Sort of. The initial shock of the activity passed and then? Well, then it felt — good? Different? Full? Just as I was getting into it, he made a loud, animalistic groan and I knew what that meant.
Butt Stuff Tip 8: Take Your Time
Both getting it in and doing the act. This isn’t a race. This isn’t all about the dick. The butt should be having a good time, too.
“I just came so hard,” he grunted as he fell down onto the floor.
The end, folks. Take your final bows. After about three minutes of intense pain and thirty seconds of mediocre pleasure, that was the end. That was fucking anal sex. I turned to him and prayed that things weren’t too…messy. Fortunately, his penis looked normal and skin-colored, and he looked happier than I’d ever seen him. So, naturally, I decided that we could no longer be together. Maybe I’m the black widow of sex, and as soon as I do something weird with a guy, I have to dump him. Maybe it was the fact that he had felt a little too much of me. Or in me. Whatever it was, I excused myself to go to the restroom, tried to close my asshole back up, and walked into the room to dump him.
My relationship with him, and with butt stuff, ended that day. Sure, there’s been the occasional “that’s not the right hole” situation since then, but never have I ever had actual anal after that. Not because I didn’t like it, but because, well yeah — because I didn’t like it. I did, however, switch over to period sex. Something about having a hot dog-shaped object get shoved up my ass made a little blood not seem like a big deal. My advice? Skip the anal and go back to vaginal sex. Or, better yet, order yourself a pizza and have a date with your vibrator. It never steals the best slice, and I promise, it won’t ask for ass play. Not even “just the tip.”
Butt Stuff Tip 9: You Shouldn’t Knock It ‘Til You Try It
Except anal. You can totally knock it before you try it..
Loading ...This column was originally published on March 9, 2015.
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