DP Me, Baby: My Anal Stretching Diary

I used to hate putting things up my butt—specifically, my partner’s penis—because it hurt. We had anal about every two years, seriously, because I found it so uncomfortable and unrewarding. But after I became a sex toy reviewer, I realized I was limiting my options by using only my vagina.

It started when I reviewed the Sportsheets Sedeux Flare. Such a nicely shaped dildo, but one that did so little for my vag because of its smaller size and lack of texture. It didn’t take long for me to decide that the toy simply had to go up my ass too. For a couple weeks, the Flare sat around my dildo shelves, lonely and unused, before I worked up the resolve to try it anally. The experience was a struggle, but eventually my partner and I managed to get the Flare past my sphincters. And having it in my ass wasn’t bad; it was kinda fun. Really, I guess it was so exciting because we’d never used any dildo anally, ever before; it was a novelty.

Afterward, though, my butt hurt. I made another decision: to go through an anal training journey. One day, I hoped, I could take my partner’s penis without discomfort. Along the way, I’ve written out the the full, blow-by-blow story—how I got through many minor aches and learned to take both a cock and a dildo (or just one of these). Plus, after lots of experimentation, I feel qualified to write out some pointers about how to make any anal stretching journey more successful.

The Early Days

Day 1: He managed to get the Flare into me, finally, with much work. Some finger play, and lots of twisting, and pop! at least the Flare’s rounded head got pulled inside. Then, after a minute, I told him to start thrusting, sloooowly. (“Slowly” is always the key word when it comes to anal exploration, especially for us newbies.)

It was a new sensation, the Flare’s slickness. I can’t say I loved the feeling by itself; it was new and exciting, but really a bit overwhelming. After another minute, I told him to stop fiddling with the Flare and get his dick into my vagina. And wow, did I feel full. Just after that, I pulled the dil out and told him to continue as normal. My butthole ached and throbbed as he continued pounding me; it was distracting.

Day 2: My rectum hurts a little. It’s not an overwhelming pain; I didn’t tear anything. Still, I realize that starting with even a small-ish dildo like the Flare was too much for me, personally. I resolve to go smaller and then to work up to an average-sized dildo, maybe even to thrusting with a penis-sized silicone toy before I give him free rein in my ass.

Day 4: Peepshow Toys asks if I wanna review a butt plug, given my experience with the Flare. I think for a while. Do I really want to do butt plug reviews? 

Maybe I am limiting myself by sticking to dildos so much. After all, silicone lover that I am, I should be interested in all forms of platinum-cure silicone sex toys, right? I write back and say that sure, I’ll review a b-Vibe Snug Plug, but I’m gonna need the small size!

Day 7: Peepshow Toys mentions to me in another e-mail that Hurricane Irma has delayed a shipment of Snug Plugs, so they only have the second-smallest size in stock. That’s fine, I’m in no rush; I’ll wait for the small. They suggest sending me a Tantus Perfect Plug Kit in the meantime. I blithely agree, not knowing how much trouble this beginner’s kit will present me with.

Day 14: The Perfect Plug Kit arrives! (Actually, when I opened the box, I was hoping it was a dildo I’d agreed to review, but no dice.) Anyway, I pull out the two purple plugs and arrange the following “bouquet of cocks,” as Tantus’ graphic designer calls it:

Afterward, I sanitize the plugs by boiling ’em, like any body-safe toy user should.1 Then I’m excited to lube the smaller plug up and test it out.

I steal into the bathroom, because my kids are home already. Wow, is the Perfect Plug pointy. I guess this is a good thing (maybe?), since my butt can’t take broader heads. Poke, poke…I wiggle and turn, and the sharp head is finally in. My ass feels invaded, honestly. I want to poop the plug out, but I persevere. I don’t hurt—I know to never push through pain with anal play, because that’s how you seriously damage yourself. But I’m not at ease.

Nevertheless, I decide that this is just part of the process. I stick the larger Perfect Plug (the Plus) into my vag, to create my first DP experience, ever. (I know, I’m remarkably sheltered for a sex blogger.) I’m afraid the Perfect Plug Plus might fall out of my vag, so I take it out for now and proceed to cook dinner for the fam. A few minutes later, hubby comes home (don’t we seem like the stereotypical 1950s nuclear family from this picture? I promise it’s not always like this.). I text him the picture I’d tweeted an hour before, along with the words, “Guess what I’m wearing?”

He races into the pantry, where I’m trying to find the spaghetti. “What do you mean??” he says, a note of alarm in his voice. (It’s not until the next day that I realized he’d immediately homed in on the largest toy in the sex toy bouquet, the Tantus Echo, and he’s thinking I’m wearing that around the house.)

“It’s a plug, you know,” I respond. “A butt plug. That you wear in your butt.”

“Oh, OK,” he says, relieved. “Hmm…” He still seems concerned.

It’s getting late, and so I finish up dinner still plugged. The Perfect Plug is really small, but I still feel stretched; I’m just not used to wearing anything in my butt. Every now and then I feel the urge to push it out, but I manage to just squeeze around it instead.

After the organized chaos of feeding and cleaning up after two small children, I send their father off to bathe them, and I have a couple minutes alone. I gingerly remove the Perfect Plug. Oooh! It’s a relief, in one way, but I do kinda miss the fullness. Cleaning the plug is a (forgive the expression) pain in the ass compared to cleaning a toy I’ve used vaginally; I’m concerned about getting traces of shit in the sink.

I’ll just have to learn to be less anal, I think. (Har, har.)

Day 16: I try wearing the Perfect Plug again. It’s a little easier to get it in, and I don’t feel the need to push it out quite as much. Still, I’m not comfortable with the full length. I wear it for about an hour and am glad to take it out afterward.

Day 21: It’s been a few days, so I put my mind to testing out the Perfect Plug again. I’m supposed to be reviewing the kit, and I’m usually very prompt in writing my reviews. (With a few exceptions.) Anyway, I still think it’s too pointy; maybe I always will. I determine that maybe being plugged will be more fun if I wear the Perfect Plug Plus in my vag again.

After taking the photos for my Echo Super Soft review—which consumes way too much of my time—I stick both Perfect Plugs in. I’m still having a hard time with the two bulbs on the small one (in my ass), but I don’t mind the even larger bulbs on the big one (because they’re in my vag). I almost manage to get off on the vibrations while I’m editing my photos, but I need a little more movement. Plus it’s lunchtime and I’m starving; orgasms will have to wait an hour.Tantus Perfect Plug Kit purple

Day 28: I’ve been slack with testing the Perfect Plugs again; the small one just isn’t doing a whole hell of a lot for me, and the large one seems like an impossible dream (or nightmare?). I’m not sure in what universe these are considered beginner’s toys. (I guess my asshole is just tight?)

Then, the B-Vibe Snug Plug 1 (the smallest out of four possible sizes) arrives. Based on my experience the past few weeks, I’m not too hot to stick it up my ass, but I carefully remove the plug from the packaging to check out the silicone. It’s nice! Maybe I can handle this.

It seems like the sex gods have aligned the stars for me, because on the same day Fuze Silicone sends me a huge collection of their minor flops so that I can test out the squish for my Silicone Dildo Firmness Guide:

Since the smaller Fuze Ten dildos (the flesh-toned ones above) are so tapered and smaller than pretty much all the toys I use vaginally, I figure they’ll be great to use in my anal journey.

Day 29: I’m enthusiastic enough about the Snug Plug 1’s silicone (and the weighted ball inside) that I take it with me into the shower. Like I’ll soon discuss in my review, getting the not-especially-tapered head in takes a little maneuvering. But once it’s in, it’s sucked up and away! I can’t sit on it at first because it’s a bit long, so I leave the thin stem hanging out between my ass checks. Later I take it out and actually miss the weights.BVibe Snug Plug 1 wood

Day 30: I try the Snug Plug again and am able to comfortably sit on it and wear it around for hours, no problem. This is my first fully OK anal experience!

Progressing, Slowly

Day 35: Life’s gotten busy, and worse, I’ve gotten sick—like my-kid-brought-home-the-plague sick. I don’t have much strength, but my husband is home sick, and we’ve sent the kids to daycare. We almost never have the house alone, so this is a rare and elusive opportunity. After slogging through the “dissertation” from hell, I stop my editing work and decide to put the Snug Plug up my butt. It’s comfortable to get in now, so much that I’m starting to wish I had the second size in the series.

I come on to my husband, and we take our clothes off and get down to it. He’s intrigued by the butt plug at first, and possibly a little turned on. I think he’s jealous, too, because he wants his dick in my ass instead. I tell him to hold his horses; there’s no way I’m ready.

Having the Snug Plug in my butt while he’s thrusting in and out is overwhelming. I feel so much, maybe too much. This is why I don’t like vibrators during PIV, I think. I’m too fucking sensitive.

We keep going for a couple minutes, and maybe it’s the cold/sinus infection, or maybe the stimulation is too much—I can’t orgasm. Plus, the front of the T-bar base is hitting the back of the mouth of my vag when he thrusts deep, and it’s distracting. (I later find out this is a common issue for T-bar-based plugs.) I pull out the Snug Plug and we proceed as usual. It’s not the greatest sex because, again, illness, but it’s new and interesting.

Day 39: We’re having sex again, and he wants to “just put [his] tip in” my butt. No, sirree—his cock isn’t tapered; it’s widest at the coronal ridge, and there’s no way it’s not going to hurt. I tell him he’s too impatient, and he backs off.

Later, I take out my Fuze Pleasure Plug 2 and start considering it. It’s beautiful, actually; a sparkly, deep blue. I stack it up against my Tantus Perfect Plug Plus and realize that they’re about the same max. diameter, but the Fuze plug is nicely tapered. I know I can work up to this.

Day 40: I ask him if he wants to help me get the Pleasure Plug in. He goes nice and slow, just like I’ve asked. He stops when I say that it’s too much pressure. I can get at least an inch diameter in, but that last widest part isn’t working for me quite yet.

Day 41: I twist and turn the Pleasure Plug 2; I slowly thrust it in and out, I still can’t quite get that maximum width in without pain. I’m short on time too; the kids are home.

Day 42: I manage to get the widest point of the Fuze plug in! Wow, it’s stretching. It’s a little uncomfortable; I can’t take the stem and the plug seems eager to slip out. I don’t want to force it deeper, so I walk around the house with two inches sticking out my butt. (I wonder if anyone will notice that it looks like I have a stick up my ass. Nope.) I sit at the computer and write for an hour, with the whole plug stem still protruding. I just can’t seem to get the whole thing in. Maybe in a couple days—gotta see how that T-bar base feels between my cheeks.

Day 44: I put out my Snug Plug review; I’m surprised at how comfortable I am with this little, weighted plug. My next goal is to take the whole Fuze Pleasure Plug 2, and then to use the smallest of the softer Fuze dildos to see if I can stand some thrusting too. My sphincter hurts a little as I just think about that kind of movement. Maybe I’m being paranoid.

Day 48I haven’t stuck anything in my ass for several days because my vag has been particularly demanding. Plus, my man has come down with the sinus infection from hell and spends most of the time complaining about how awful he feels—so he’s definitely not helping me out here. Anyway, I decide to get back in the anal-stretching saddle myself. I stick almost all of the Pleasure Plug 2 in, but I feel more resistance than before. No more five-day breaks! I think. (Boy, am I wrong about how that’s going to turn out.)

Day 49: Maybe today will be the day I fit that gosh-darn Fuze plug in. I lube it up…and I can get the widest part in! But the stem doesn’t want to go. Hmm. I thrust it in and out a little and then decide I’ll wear it while I’m putting up the dishes.

My sphincter isn’t on board with this plan, though. It feels so full, and it wants to push the plug out. I adjust a couple times, through my shorts, while I’m putting up the plates. I then realize what an incredibly unhygenic idea this was. I bend over again, and now I can really feel the wide part of the plug struggling to escape. I hastily set down a couple glasses and go to the bathroom to remove the plug and wash, wash, wash.

Day 50: I was so close to fitting the Pleasure Plug 2 in yesterday that I resolve that it will happen. I will wear this thing around.

Firm resolution made, I pull out the plug in question and—gasp!—actually get the widest part in my ass. The plug’s stem still sticks out a little. I have more laundry to do (kids create so much fucking laundry), so I finish that and then go into the living room to be with the fam. I’ve changed from my skimpy pink shorts into thicker navy ones in hopes that my parents, who are visiting for a couple days, don’t notice that I have a plug stem slightly protruding from my anus.

I’ve had the plug in for about 40 minutes and am sitting (gingerly) on the floor when my kid lunges into my arms—pushing me down all the way onto the plug. Ouch. I’m not sure I was ready for the full length of the plug, but it’s in all the way now, no turning back.

I feel so stretched. Again, it doesn’t really hurt, but it’s uncomfortable. I wish I had a Snug Plug 2 instead, because I crave that weight—so much more fun than just solid silicone.

After a few minutes, I excuse myself and go to the bathroom to remove the plug. I realize that I’m wet; I certainly didn’t feel aroused, but I guess all the butt stimulation did something to my brain.

When I first pull the plug out, it’s a great relief. My butthole aches. But a couple minutes later, I realize that the aching has become a pleasurable kind of pain. Now I’m definitely aroused and aware of it, too. For the next few hours, whenever I think about the plug, my butt still throbs, but now it’s a turn-on. Hmm, new discoveries! I dream about having my partner finally use the Fuze Ace on me, because I know I can take the width now, and I know I like it when I move my plugs in and out.

Maybe my butt can finally learn to enjoy thrusting like my vag enjoys it!

Day…Oh, Who the Hell Knows, I Got Some Kind of Contagion: My anal journey has gone off the rails. I got a really terrible, lasting virus (maybe the flu?), and a sinus infection, and butt play is the last thing on my mind.

So I’m not counting by days anymore. I’ve just about given up on my goal of ever having painless anal sex, in fact. I haven’t even gotten around to using that Fuze dildo in my butt, even though its taper makes it look very manageable.

But one day, I’m feeling slightly better, and I decide I have to get the Perfect Plug Plus in—because I still haven’t finished that review. So I wiggle, and twist…and you know what? It’s not that bad. I was afraid my butt would’ve tightened back up since I hadn’t put anything in it for weeks.

After we have PIV one afternoon (he’s taken the day off work for once), I decide that it’s now or never. I have to test out these vibrations! And, much to my surprise, I end up really liking the vibrating Perfect Plug. Maybe we’ll finally get around to thrusting that dildo in my ass soon.

But I have a new toy to challenge me: the b-Vibe Rimming Plug Petite. I agreed to test the small version (about 1.4″ max. diameter and not too long), but I was apprehensive when I got it. So much so that I decided to use it vaginally first! And I loved it.

But, you know, the toy is called a butt plug for a reason. I test it vaginally for weeks—my partner and I still mostly use it this way—but I have to feel the “rimming” sensation in my ass too.

We enlist the help of the smaller, softer Fuze Ace to loosen me up a little. The Rimming Plug‘s tapered head feels wide and firm. I’m anxious. But he goes slow, and still it only takes a minute or two. The Rimming Plug’s rotating beads are something else. I don’t come multiple times with the plug in my butt, like I do with it in my vag, but the sensation is definitely something to write home about. He rubs around my clit while controlling the plug; I tell him to not use the high vibration settings because it’s so much. I’m incredibly turned on, and I come hard after a minute. Then I want the Rimming Plug, as exciting as it is, out of me. B-Vibe Rimming Plug PetiteAfter another trial run, I’m able to finish my gushing Rimming Plug review (let me say it again: AAAAHHHHH rotating beads *shrieks*).

And now I know I’m finally getting close to my goal: comfortable anal sex with a man. (Plus maybe trying out double penetration.) Onto the last phase!

Will I Reach My Goal(s)?

It’s almost Christmas, and no one in his office is working. He comes home early. He’s stressed about some special kind of ongoing bullshit at work. But we’re alone, so you can guess what’s next.

He asks if I’ve put anything up my butt lately. It’s been a while since the Rimming Plug test. I say I haven’t. He’s incredibly eager to finally put his dick in my ass, so I tell him to be patient. Then I go and dig out the designated anal dildo and the oil-based lube.

As before, it’s not difficult to get in, but the thrusting is whoaSoon he takes the toy out and positions himself over me, ready to take its place. I feel my sphincters stretch a little more as he fits his head into my greased-up butt. I’d thought that I’d have to tell him to stop almost immediately, but he slides most of his length in right away.

I beg him to not thrust too hard, and he reassures me that he’ll take it slow. My face gets pressed down into a couple pillows, because he’s always more at ease with flat doggy style, but I don’t care enough to ask to stop and reposition. I try to rub myself while he’s pressing his weight into my ass (we really haven’t thought this positioning out).

Obviously he loves the tightness, because even with slow, shallow strokes, he gets off in two minutes or less. I wipe all the grease off, and then I realize that the stimulation has made me need to take a shit. (Again, not much preplanning here!) But overall, he’s very pleased, and I’m not displeased. I’m glad that it wasn’t painful, and yes, it was very filling. We need more practice.

Our second attempt at penis-in-anus sex is still kinda awkward. We’ve had PIV first, and I’m still turned on and ready to go; I have lube (duh) and a trusty bullet vibe ready. We use the warm-up dildo again, and then he tries to enter me. For some reason (the wetness of the Sliquid Silk?), his penis keeps sliding forward. I stick my ass farther up in the air and tell him to be careful, because I don’t want anal bacteria around my vag. His head slips forward once more; he keeps angling sideways too. (We’re so anally inexperienced.) But after a minute he succeeds, and we’re good to go.

It’s better this time. I wish I hadn’t gotten lube all over the Charged Vooom, though, because as good as the vibe is, I’m having a hard time adjusting the speed because of the small button. (I’m wishing I’d invested in the longer, more flexible FemmeFunn Bullet.) The lubed Vooom’s plastic is so slippery. Fuck it, though, I think I have it on the second steady setting, and that works.

His thrusting is a little deeper, but still not hard, and I’m having fun with my vibe. I come, and he’s right behind me. (In time and in space.) When we’re done, we decide that anal probably won’t be an all-the-time thing for us, but it’s a good change of pace. Then, I wipe the bullet off and keep playing with it, while he goes to shower. I’m happy to not feel any discomfort, just a dull throbbing.

A week later, we find the time to finally try out my end goal: What’s DP like? Well…awkward. We don’t have a harness (that’ll hold a dildo and have a hole/room for his penis), so positioning is incredibly awkward. There’s just no way we’re going to pull the act off in flat doggy (his usual favorite), and even in normal doggy style, it’s really uncomfortable for him to attempt to hang onto the dildo while thrusting himself into my vag. Finally we settle on missionary with pillows under my butt. The Sedeux Flare is resting in my rectum, and he’s moving in and out above it. He complains that his balls are hitting the circular base.

As for me, I’m wondering what I’ve gotten myself into. It’s kinda hot…but kinda not. Three minutes in, I decide that WTF, I either like (1) pure vaginal sex or (2) anal sex while my clit is being indirectly vibrated/circled.

Maybe, in the end, DP just isn’t for me. There are a good number of vagina owners who find that having something in their butt during vaginal sex makes it more stimulating, more exciting, easier to get off. I just happen to be in the camp that finds DP distracting. Since I finished writing this diary, we’ve occasionally tried DP again, like in testing the T.O.M. suction cup dildo mount, but I personally don’t feel called to it. It’s just not something I actively seek out. I honestly think my vagina takes up too much space (witness my large dildo category) in my pelvic floor for me to really enjoy average-sized anal toys.

The real revelation for me is that having something just in my butt makes external clit stim a lot more interesting. I’m glad I started on this journey, because there are so many butt plugs to explore. And, most of all, my husband likes the change of pace (and the tightness) that anal can provide. The experience was good enough for him that we’re now exploring putting things up his butt!2

Overall Thoughts: What I’d Tell Anal Noobs

If you’re like me, butt stuff can seem overwhelming at first. Or maybe you’re not like me, and you’re raring to stick things up your rectum. Either way, it’s important to not go too far, too fast. Here are my tips:3

  1. There’s some debate over how to clean yourself out beforehand: Is douching necessary, and is it a good thing (or can it introduce more bad bacteria)? If you’re advanced and are going really deep, maybe. For beginners, I’d say to just make sure you’ve had a good bowel movement an hour or two before you begin. Then, clean the anus itself (the outside) as well as you can, with a shower or some baby wipes.
  2. Pick yer lube. Water-based lube is OK but is absorbed very quickly. Hybrid lube (like Sliquid Silk) is better. Silicone lube (assuming you’re not using silicone toys4) is even better than that. Oil-based lubes, like The Butters or virgin coconut oil, are probably the best, in my experience, but they are hardest to clean up—lots of staying power. Also know that you can’t used oil-based lubes with latex condoms; they’ll tear.
  3. Make sure you get lube into your butthole, not just around it. You can use a clean finger (and wash very well afterward). Or put loads of lube on the top of your toy.
  4. Obviously, start small and work up. An inch diameter is the max. you’ll want in a sex toy, maybe even .75″ diameter if your butt is tight like mine. Don’t jump up much more than a quarter inch diameter (an inch circumference or probably less) between toys.
  5. At the very beginning, you may want to use fingers (with nails trimmed as far as you can get them without cutting into the nail bed) instead of sex toys. Consider buying a pack of latex gloves for easier clean-up. (Though it’s harder to find someone else’s prostate with gloved fingers, I later found out.)
  6. Once you feel really stretched to the max, stop. You may want to wait two or three days for your butt to recover after an intense session. Remember that anal (or vaginal) pain is how your body tells you that something is wrong.
  7. Long-term wear may be difficult at first. Don’t go for more than an hour or two.
  8. Thrusting is harder on the butt than just wearing a plug. Be gentle!

Good luck in your own explorations! Feel free to share your story with me in the comments, or say if anything in my stretching diary spoke to you.

  1. You never know what the packing and shipping conditions are like, especially for cheaper toys (not as much for Tantus). Never hurts to be safe, though! Also use soap and water to wash before an after boiling.
  2. And he loves prostate stim now. I guess I need to write a prostate exploration post next, lol.
  3. Also check out my article on sizing up with sex toys.
  4. Or if you’re sure your silicone toys are compatible with silicone lube, like quality silicone (think Tantus or Fun Factory dildos) almost always are. Do a patch test on the toy’s base if you’re unsure. If that dab of lube doesn’t change the surface of the silicone, it’s safe to use on the toy.


Editor, writer, introvert, hedonist, and lover of all the finer things in life—including lots of high-quality sex toys.

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One thought on “DP Me, Baby: My Anal Stretching Diary

  1. Chris Myno

    February 21, 2018 at 6:03am

    Lovely story and I really appreciate the detail and honesty! I think you are a great sport for committing to seeing if it can develop into something you enjoy. I’ve noticed that pain anxiety is far easier to work with than those who simply find everything butt-related to be icky. I mean, you need to find butt play sexy at least in theory to want to work with it.

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    • Author


      February 21, 2018 at 9:51pm

      Thank you! I honestly like the idea of playing with other people’s butts more than having something in my own, haha. You’re totally right, working through the fear was the biggest hurdle for me.

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