I Bought My First Sexy Halloween Costume

I even posted a photo of myself in it

Every year, I follow the mini debates that come up about sexy Halloween costumes.

I’ve heard the criticisms my whole life, and I totally get it and endorse a lot of them.

I know that women are oversexualized to the point of being objectified. I know that men’s costumes are undersexualized (seriously, guys, bring the sexy once in a while).

I know women are expected to perform sexiness, even when they’re dressed as crayons.

I never take part in those debates, though, because I’m always busy having another one. Every year, I debate myself on whether or not I should buy a sexy Halloween costume.

I want one. I really, really want one. I see other women dress up in sexy, cute, revealing outfits and I’m envious of their confidence.

I love everything sexy and naughty, but sometimes I just don’t feel like it’s for me. I feel like what’s expected of women who look like me, who have chubby bodies like mine, is to tone down the sexiness, not lean into it.

I never felt sexy — still don’t — so I figured wearing a sexy costume would just make me feel silly. I got the message loud and clear that those costumes are for other girls, girls with other kinds of bodies.

Still, I can’t remember an October going by when I didn’t spend time window shopping online for sexy costumes.

I don’t plan to ever wear them out. I never go to parties and I don’t dress up to take my kids trick or treating. I want them for the same reason I want half the things I buy: for sex.

I wanted to wear something cute for my husband. I wanted to be able to surprise him and get flirty in some kind of crazy get-up. And I wanted it for me, too. I wanted to feel as sexy in my costume as other women looked in theirs.

Even though I’d only be wearing it behind closed doors, I could never bring myself to do it. I could never see those costumes as being right for me. I’d just have to stick to fucking in my socks.

I’ll Do (Almost) Anything for Content

This year, I finally did it. I bought a costume to fuck in.

Not gonna lie, though, I did it for the content. I was trying to think of a fun Halloween-themed blog post to write, and this is the one that I kept coming up with.

I figured, either way, it would be a winning idea. Either I’d wear it, feel sexy, have great sex, and write an empowering article about it, or I’d feel stupid, have an awkward night, and write something that hopefully makes people laugh.

There’s really no losing when you put your life on display for a living. So, for the first time, I turned window shopping into regular shopping.

I wanted something modest that didn’t show too much skin. I’m dipping my toe, not jumping in with both feet, so I’m not going to buy a Slave Princess Leia costume or anything like that (I don’t like Star Wars anyway — don’t @ me!)

I narrowed it down to a few options that were cute and looked comfortable. I finally settled on an Alice in Wonderland costume. Or, rather, a copyright-friendly Miss Wonder costume. It was cute, with a bit of a frilly skirt. The thigh-high socks and black hair bow didn’t hurt.

I placed the order and tried not to get cold feet before the package even got to my doorstep. I had enough confidence to put some cold hard cash down, but I wasn’t sure I’d have the confidence to actually pull off the whole costumed sex thing. There was still a good chance I’d put it on, take one look at myself in the mirror, and never let the costume see the light of day again.

Mrs. Dressup

When I finally got the costume, it looked cute — on the model pictured on the package.

On me, not so much.

I tried it on alone. I stood in front of my mirror and felt dumb. I felt embarrassed and humiliated — done in by an outfit.

I did look a bit like Alice. But also kind of like a maid. And also a little like the Tooth Fairy. And not the sexy version of any of those.

I felt ridiculous having done myself up and worn a costume like this. I started questioning what I was even doing. I never roleplay during sex. I never play out scenarios or pretend I’m someone else. Even when Mr. Austin was in grad school and teaching classes, I never once asked him to pretend he was a professor who needed to help me “study” (huge missed opportunity, tbh!)

We just fuck, talk dirty, and have a good time.

And here I was, dressing like I was going to steal his teeth in exchange for sex.

But I was determined to go as far as I could. So what if I look like the Tooth Fairy? Tooth Fairy’s gotta fuck, too, right?

I decided to take a bold step. I took a photo. Actually, I took like twenty. I wanted to see if I could get a good shot for Instagram.

I really didn’t think I would, but I eventually narrowed it down to one that I thought looked alright, even though I still felt silly looking at it. I grit my teeth and posted the photo for all my 50-ish followers to maybe see. (I know that’s a small step, but it’s a big one for me!)

Photo from author’s Instagram

After I shared a photo, all that was left was to actually put the costume to use. And I’m really glad I did. Getting in the costume was intimidating. Putting it on made me feel stupid. Having sex in it, though, was really fucking fun.

Falling Down the (Sexy) Rabbit Hole

On the big night, I told Mr. Austin to light some candles and wait for me in bed.

I went to the bathroom to get ready. I put on the dress, patted the hair bow in place, and pulled the socks up to my thighs. I still felt stupid, but also kind of turned on. Putting on the costume had set things in motion and the anticipation was having an effect on me.

I took one last look in the mirror (didn’t help) and then it was go time.

I walked into the room. It wasn’t as dark as I hoped it would be, but at least I could clearly see my Mr. Austin waiting for me in his donut-print underwear (“Alice likes cakes, right?” he asked earlier that day, “I feel like that’s a thing”).

Mr. Austin looked me up and down and made me laugh by saying, “Well, well, well… Look who fell down my rabbit hole.”

He had set pillows at the head of the bed and told me to lay down and make myself comfortable. He thought it would be really fun to flip my skirt up and go down on me for a long time, and that sounded really good to me, too.

As promised, he laid between my legs and went to work on me, occasionally gripping my socked knees to push my legs up. He teased me with his tongue and his lips. He took his time and explored me very thoroughly. He basically gave me a pussy massage with his mouth.

He promised to go for half an hour, but I couldn’t take all the teasing. About twenty minutes in, I begged him to make me come. And he did, with three fingers inside me (I’ll let you guess where) and his tongue circling my clit.

Well, after all that, I really wanted to repay the favor. I pulled off his colorful boxer briefs and kneeled over him and started kissing his cock.

Mr. Austin later told me that something about the cute hair bow and maid-like outfit made for a very nice visual while I was servicing him. And I have to say, I like what the costume was doing, too. Being on my knees with a skirt only half-covering my bare ass felt really good. As shy as I am, I love being exposed, and somehow the skirt almost made me feel more exposed than being naked.

The costume dictated everything we did after that. I rode him cowgirl because I loved the way the skirt just fell over us. My tits in the outfit made nipple play tricky, so Mr. Austin gripped my ribs instead while he pumped into me. There was so much energy in his thrusts. The costume seemed to excite him, and I got to enjoy the benefits of his enthusiasm.

There were two more positions we wanted to try in the costume. He had mentioned missionary to me earlier — something, again, about liking the idea of flipping my skirt up. And I told him, “With a skirt like this, we just have to do doggystyle.”

We don’t do doggystyle too often. It’s a hard position for me (I suspect it’s the curve of Mr. Austin’s cock, but the height of our bed frame might not help). But I really wanted to have a go at it. We had the usual difficulties of getting in the right positions and getting the angle right, but it was nice once we did.

The costume changed our dynamic a little. I think it made Mr. Austin see me as slightly more submissive, or just inspired him to take a more dominant role. I noticed it especially during doggystyle, when he told me to put my face down and my ass up instead of resting on my hands or elbows like I normally do. I complied, and I’m glad I did because I got some really satisfying dick from it.

We ended in our typical way, but I worked the costume into my dirty talk this time. “Why don’t you come on Alice’s ass?” I asked as I got into position with my vibrator.

He made himself come sooner than he normally does, which I suppose is confirmation that this costume was some hot stuff. I may have felt silly putting it on, but Mr. Austin clearly felt like I managed to bring the sexiness.

Well, I’m Sold

After a night like that, there’s no turning back. I’m sold. I’m going to wear this costume again.

I loved feeling exposed without being completely naked. That was a very nice element, and I didn’t feel any less sexy even though I was hiding more skin.

I also liked how tight and snug it was. It felt cozy and accentuated my curves, which is one of my features I don’t mind emphasizing.

This was so different for me. I’ve never had anything special to wear for sex. I don’t have lingerie. I don’t have any outfits I pull out when I want to show Mr. Austin it’s time to get down. The underwear I get in my MyUndies subscription is the closest I’ve come to dressing up for sex.

And it felt really nice to be able to dress up for sex. There was a satisfying ritual to it. And I appreciated being able to do something special for Mr. Austin, and for me, too.

Miss Wonder is hanging in the closet now, but she won’t be forever. She’ll see the light of day again. And she won’t be alone. At least once a year (if I can wait that long), I’m going to add a new outfit to my collection of sex costumes.

Not wanting to dress sexy is fine. But if you’d like to do it, I’m in full support of doing it your way. Find what sexy is to you and jump in with both feet.

You don’t have to go skimpy if you don’t want to. You don’t have to go with black lace and fishnets. You can wear something comfortable that still helps you get playful. For me, that was a Halloween costume with a short skirt and ample bosom space. For you, it might be a classic like a sexy nurse or an opportunity to fulfill your partner’s vampire sex fantasy.

And if any of you think you’re not the type who can pull off a sexy costume, just remember that I somehow managed to have amazing sex while dressed like the Tooth Fairy pulling a double shift cleaning hotels in Wonderland.