My First Anal Sex Experience

My First Anal Sex Experience

Distinguishing between pleasure, pressure, and pain

Image for postPhoto by Dainis Graveris on Unsplash

I?m fairly sure I opened my mouth so wide that I looked like a terrified person watching a car accident in slow motion the first time I felt a penis slide into my anus. Ever see that painting The Scream by Edvard Munch?

Yes, just think of that. Something tells me it wasn?t my most flattering moment. The preparation and sex itself were a long and arduous process getting everything exactly right meaning I?m sure I made that not-so-sexy face a lot.

At first, I winced in pain feeling myself stretch. It felt like my skin was being peeled back and torn off. But quickly this feeling subsided and I felt a bit more comfortable taking the first half-inch of him.

Bent over on the edge of a couch and my knees were on the carpet and I braced myself and prepared for what came next. I know what you?re thinking, how romantic.

Taking my hand and placing it on his hip I pushed backward to start to guide his entry. I put my hand right on the hip bone to give myself a good leverage in case I needed to push him outward. No, I wasn?t some skilled porn star breaking out all the tricks, I was just inexperienced and wanted to save myself from what my nervous mind interpreted as the severe damage to come.

?My poor butt!? I thought to myself, but there I was, and I was determined to get this right. If things went really wrong, I could always just tell him to stop and we could have regular sex, I figured. Fortunately for me, nothing of the destructive sort took place.

Then I bent my elbow and retracted my hand toward my own back so he could ease in and suddenly the pain was replaced with immense pressure. I felt like I couldn?t speak. My belly felt so full. The air escaped my lungs as I exhaled heavily.

It was the oddest feeling as I felt myself stretch out to accommodate him. For the men out there who can?t quite relate, if you?ve ever stretched a piercing with a gauge, it feels a lot like that, a little bit of sting and a whole lot of pressure.

Your nervous system sends all the signals to your brain, something doesn?t feel quite right, but without the horrible pain you were expecting, you don?t know why.

I was confused. I wondered to myself, ?Is this really what anal sex is like? Is this how it?s supposed to be? The women in porn make it look so much more enjoyable than this??

I didn?t know what to make of it but little did I know at the time, it would be the hardest it would ever get. Controlling his depth with my own hand was a must and probably saved my ass that day (literally) from serious pain.

Pro-tip for all those out there looking for ideas on how to make it more comfortable, you want to be in control of the depth and speed yourself. We kept this up for a few minutes and then I just opted to help him reach orgasm with my mouth instead. He didn?t last long so the first time was anticlimactic in every sense of the term.

Another pro-tip: if you experience this unusual feeling the first time, relax, it?s perfectly normal and it gets better from here. If you?re really uncomfortable and don?t like the feeling, you can always ask your partner to stop and that should be respected.

Anal sex is an extremely tight fit no matter what. I guess that?s why men love it so much, right? There?s no denying that the first time will be pretty uncomfortable. None of the other women I know have reported having a great time their first time. The same is usually true of vaginal sex for most women.

But the second time was so much easier. I was a little more lubed up and by ?lubed? I mean ?liquored? as I had three or four drinks beforehand. For lube, the guy just used saliva which was surprisingly sufficient. I was more turned on, more excited, and with a much more experienced partner. Coincidentally, we ended up on a similar couch, this time with a hardwood floor (his poor knees!) and I bent myself over before him so he could enter me.

I think it was his experience and self-control that made it great. He slipped into me and it was a breeze compared to the first time. I should also note, the first guy had a lot of girth and this guy was more of an average size. I was extremely turned on.

I couldn?t help myself and began to shake with horniness as my veins filled with adrenaline and desire. I felt hot. I felt really hot. I felt like I was doing something naughty, using my body in a different way that was pleasurable and off-limits.

I wanted to climax but even this second time wasn?t sending me into mind-blowing orgasms or anything. It just felt really good, it rubbed up against a part of me that I?d never played with or experienced before. It was so new and different. I liked it but I wasn?t sent over the moon.

It was extremely intimate, so I liked that part. I rubbed myself and tried to get off, but that was a no go. Sometimes when I drink, the alcohol makes it extremely hard for me to achieve orgasm.

He kept going and made sure to take care of me asking me how I was. He was so sweet. When he finally climaxed, I didn?t even know what had happened. I just heard him exhale. ?Are you finished?? I asked. ?Oh yeah,? he said back to me. I couldn?t believe it, for the first time, someone used my ass to get off. I felt proud!

I was surprised because usually when you?re with a guy and he climaxes inside of you, you can feel him pulse and shake and shudder, you can feel his penis basically do jumping jacks inside of you, and it?s really hot. But this time I felt nothing. Not with anal sex. The only cues I had were audible.

He left and I went to bed. Later that night I masturbated to the idea of it. The thought kept replaying in my head over and over again. It was really a hot experience and he was such an amazing person. All of it just turned me on and I got myself off a few times, rolled over, and went to sleep.

From here on out, it got a little easier with each time until it was an enjoyable experience and I was literally asking for it because it would give me a different kind of orgasm. I know all bodies are built differently and this might make anal sex more pleasurable for some than others, but I also think a lot of people are scared off by this first uncomfortable experience, especially if they had an inexperienced partner. I?m here to let you know, it gets easier with time. Sometimes it gets easier really fast, too. It?s not for everybody but it?s definitely for me.

A lot of women simply don?t want anal sex and don?t want to enjoy it and like Bobby Brown said, that?s their prerogative. It should be a personal choice. In my experience, it got a whole lot better with time and became an amazing thing that I enjoy as a part of my routine sex life. Just remember to?

  • control the speed yourself
  • control the depth yourself
  • don?t expect magic the first time around
  • stop or don?t even start if you aren?t comfortable
  • maintain honest communication and discuss how you?re feeling
  • come back to it if you?re not feeling it the first time
  • distinguish between pressure and pain
  • do what feels right

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