My First Time: Anal Sex

my tickle trunk first time anal sex buzzfeed chart

This is not the tale of how someone fucked my ass. It’s the long story of how I got there, because for some of us, it is a long journey. But spoiler alert: I get my butt fucked.

I sometimes forget that in the sexual scope of things, I’m relatively new to anal play. With the exception of an experiment using the tip of a broomstick once as a teenager, my first real encounter with assplay came from my current relationship, less than 2 years ago, on a night when we went and bought His & Her’s butt plugs. Seriously. His was purple, mine was black (this was so long ago that I still thought black was a “cool & unique” sex toy colour)

We tried it once before, and we tried it like we were 16 – without warm-up. A quick kiss and a hug and “OH FUCK NO STOP” after approximately 1/16th of an inch of dick was entering me and the blinding pain of anal tears washed over me.

After that we waited (and waited and waited and waited, if you ask him) so that I could work my way up, because here is a strangely under-discussed factor in anal sex – girth. Yes, thick dick is great, and I’m blessed to have a boyfriend with a great sized cock, but up until this year I only owned a butt plug – one little butt plug. To go from a finger or two to a full sized dick is a big jump, and it’s okay to take that time.

I used that to time to enjoy myself. The more anal-friendly toys I got, the more I was able to experiment enthusiastically and work myself up in stages to find that I liked working at my own pace. I don’t know about you, but my biggest appeal in anal play is the challenge of it; once I’m enjoying one toy, I want to move up to more. I want to take more and more, so that I know that I can take his cock one day.

my tickle trunk first time anal sex buzzfeed chart

The Decision

Last week was my gateway. Through a brand new porn membership to Dorcel Club, I found myself obsessed with DP gangbangs and wanted so much to live out this fantasy to the best of my ability. Being alone, my imagination ran wild and I was able to relax and take as long as I wanted, and before I knew it, I was sexting my man, asking him to guess which toy I had in my bum. This guessing game turned into video proof and as the toy size grew from Tsunami to Uncut #1 (!!!), I knew I was ready. Watching the videos of me fucking myself with these giant dildos kept me hot and eager as I waited for him to come over that week, fantasizing of what it might look like if that were his cock.

The Preparing Of Butts

Look, your butt is a pretty integral part of your body, and it’s there for a reason that normally isn’t dick storage. Because of this, it’s pretty rare that you can have unprepared butt sex. Here are a few factors we took into consideration.

  • Food: On this night, we were running late for a show, and had to figure out a quick dinner. I offered to whip up a nice alfredo pasta, but my feeling stuffy with his mild gluten intolerance didn’t bode well. Stay light – you can always eat afterwards. Stay away from spice, coffee, and don’t stuff yourself (it has to go somewhere after all). We went with a good old wrap – grilled chicken with veggies & hummus (and then had a McChicken later on, because reward)
  • Anal Douching: It was an experience that left me with a feeling much like that of my first Pap smear; weird, sort of violated, and confused in the genitals. I used the Cal Exotics Anal Douche, squirted in water, jumped around in the bathtub, and clenched for dear life to hop over to the toilet. I did this twice because I’m not sure if there’s a way to tell you’ve done it right. Either way, it feels sickly to eject pure water.
  • Toys & Planning: I’m actually quite glad we did this, but at the time it was tremendously weird and sexy/unsexy. I laid out all the toys that were butt-friendly and we decided in which order we were each going to use them, weighing the pros and cons of each. Here was my selection:

Anal Toys:



my tickle trunk first time anal sex

The Warm Up

After douching, I applied a small blob of the anal relaxant. I’ve said it in my review before, and I’ll say it again – GET THIS. I think it’s a spray now, but I can’t imagine my anal play life without it.
It’s not for everyone, but we did some foreplay in the form of bondage – I guess to let my ass know from the outside that it was about to be invaded. During this time I was teased with my rather strong We-Vibe Rave, bent over the bed, and slapped & whipped into delicious submission.

The entire warm-up process was an exercise in mutual masturbation, starting with a few minutes of clitoral stimulation from my Lovehoney clit vibe. It’s old news that being relaxed is an integral part of anal, so get relaxed by being turned on as fuck. K?

Bring in the butts! I started by squirting some Sliquid Sassy on my Romeo, the harmless little guy; the small little beads slide in and out so easily that even an anal virgin can pump away to get the sphincter used to penetrating sensations.

After a few minutes with that guy, simultaneously using my clit vibe, I moved on to the Ripple. This one, while with similar beads as the Romeo, is much larger and with much more significant progressions in size. Using the top two beads to work the anus and ensure that it’s ready, I slowly inserted the 3rd, feeling full for the first time. (due to sheer length I’m unable to fit the fourth bead, but if you can, I suggest doing so for an extra little stretch)

3-5 minutes of playing with that had my ass starting to feel the burn, the stretching of the skin; it’s not painful, just kind of a point that you have to get past. I added more anal relaxant, and next up was probably one of my favourites for relaxing anal play – my glass double dildo. Smooth glass (or metal) is a great choice for anal since there’s such little drag and you can pump to your heart’s desire. It’s especially good as a nice break in between toys because both of those materials absorb temperature and can hold a nice, soothing chill while you warm up. I used this for about 5 minutes, him watching me, and my writhing in ecstasy against my same Lovehoney vibe. I was definitely getting ready.

Soon it was last call, and there was just one left – the one that had surprised me with its anal capability during my solo runs – the Tsunami. Lube lube lube. I slowwwwwly slid it into me, feeling the coolness of the lube slide against my skin and its curved tip entered me, continuing to expand as I pushed the widening dildo inside. He watched intently, marveling at all my hard work and knowing that if I could take as much as I had, I was ready.

The Sex

Half an hour of warm-up later, it was time. The extent of my intention was to simply have him inside me, mayyyybe some slow thrusting, but full-on sex wasn’t something I was counting on. This is a good expectation to go in with, because I’m pretty sure you’ll both feel content with whatever level of dick-in-the-ass you achieve.

Piling on a bunch of lube (and yet another blob of anal relaxant), I lay on my side, positioned him behind me, and brought my legs about halfway to my chest. This nicely opens up the cheeks and makes it a bit easier to find, but this also allows you to sort of back up onto him, while giving you a spare arm to guide him in with. He found his position and lightly pushed into me, while I reached back and used a firm hand to captain the dick in slowly. Control is key here, both his and yours.

It’s in. I gasp – mainly from surprise – and there’s the perfect amount of lube to keep going all the way.

my tickle trunk first time anal sex buzzfeed chart

It started out closer to “meh ok” – I could feel my anus was taking some time to adjust to the new sensation. – not unpleasant, but I could feel a sort of warm irritation that wasn’t painful, just odd. I thought, “okay, in a minute we’ll stop and take a break” and that’s the last thing I remember thinking before my brain turned into a dirty slut and all I wanted was more ass-fucking.

The slow, steady movements felt awesome, and he was considerate of letting me control that direction, but after only a minute or two of getting used to that new tingle, it dissipated, and I knew I was ready for more. I told him to fuck my ass. “Say it again” he groaned into my ear, still thrusting slowly. I do loved to be spurred on, so I did, and I said it a lot more that night.

my tickle trunk first time anal sex buzzfeed chart

Once I’d gotten comfortable in that position, we moved onto my stomach. I had actually asked him to film what it looked like to fuck my ass so we could revisit it later, much like my solo sessions, but obviously technical difficulty intervened. I laid with the vibrator pressed between my hand and my thighs, pinned to the bed, 100% relaxed (knowing that this is one time in bed where doing nothing will favour me) as I grunted and groaned, telling him to fuck my ass, telling him how much I loved the feeling of cock.

So… anal sex turns me into my raunchiest whore self. I mean I get pretty explicit here and there, but it was every porn-induced, slutty phrase I’d ever wanted to utter just thrown out there. It just felt so different and new and like this was the sexual mecca that I was meant to reach.

“I think we skipped sex and went to full-on ass-fucking”

Right after we both came, I wanted it again. However we waited a little too long and all the hard work from warm-up had worn off, so we were back to “Nope, get it out” – let that be a lesson. If you want an ass-fucking, ass-fuck now!

For the sake of describing this experience, I have borrowed some visual aids from Buzzfeed’s 11 Charts Only People Who Have Had Anal Sex Will Understand because I am now one of them, and it is fact.

Other Posts You May Like...


  1. Jessi says:

    Anal is The Thing my guy wants most. We’ve tried for years. Ten years. Sometimes we’ve worked up to it’s not terrible, but never passed that. It’s like no amount of relaxation is enough relaxation, as I tend to develop fissures that hurt forever. Recently we’ve made more progress, and my subby tendencies get a feeling of accomplishment from finally progressing.

    • mytickletrunk says:

      The feeling of accomplishment is definitely my driving factor. The anal relaxant I used it perfect, and I’m even prone to fissures without anal sex, so it can be done. I can’t stress for how long the warm-up took, and I wanted to trust toys before I trusted him.

Leave a Reply