I've helped subs into a variety of fun and kinky costumes, but my favorite, by far, was one of my own creation, the backwards blowup doll. One year I saw someone wearing a crappy blowup doll costume that was just a skin colored bodysuit with blowup doll written around the belly button. I liked the concept, it was especially fitting for a sub, but the costume itself was so bad that I couldn't help but think of ways to improve it. Regular blowup dolls just aren't big enough to fit someone in, but the plastic look is unmistakable. To make sure I had enough material I got two identical female, "life size" blowup dolls. (Any cheap blowup doll
should work.) I cut one in half above the waste to make pants, and one below the waste to make a top. This ensures there will be some overlap and makes it a bit taller. This still isn't wide enough for a person to wear, so I cut along the seam and super glued in strips of material from the spare halves so it would fit my sub. I also super glued a couple Velcro strips to the pants and shirt so they wouldn't come apart. I cut off the feet so I could just tape them to my sub's shoes, and I removed the face and attached two elastic strings to it so it could be worn like a mask. This is when I noticed two things. First, the holes in the mask for eyes, nose, and mouth, weren't going to align with anyone's face. Second, the blowup doll pants didn't leave enough room for both the sub and penetrable pockets. And what I had really wanted was a fuckable blowup doll.After a couple days of moping, inspiration struck me. I would put the costume on backwards. To clean him up and make sure he wouldn't have to take a dump after being dress, I started out with a simple enema. Next, I got him naked, and hard. I inserted a dildo in his ass as a placeholder, and while holding his ass cheeks apart best I could, I cling wrapped him a pair of underwear with his cock and balls sticking out front, and dildo sticking out the back. I had him put on the blowup doll pants with the front facing backwards, and as we pulled it up I filled it out where it wasn't tight so that it had that smooth balloon look. I don't remember what stuffing I used, just something random
from the craft store. When we got up to ass level, I removed the dildo and exposed a direct line of sight to his asshole. I lubed up the backside of the pussy and worked it into his ass with a dildo. Basically pressing the fake vaginal opening in from the outside of the costume. Now the blowup doll had a reasonably fuckable pussy! I tried to position the hole for the doll's ass so I could poke at his cock and balls, but it was only an afterthought. To do the top of the doll the process was similar to the bottom, again with the front facing backwards. I had to have him lay down so the stuffing wouldn't fall out during packing, and everything pretty much stayed in place. To make them feel similar to the breasts on the blowup doll, I used two large balloons but only inflated them enough to fill up the boobs. My sub had some black shoes so I had him put those on so they wouldn't be too visible. I stuffed the cut off doll feet, sealed them up good, and attached them to the back of the shoes and pants so the feet pointed in the right direction as well. For the face, I took the head from the second doll, which had no holes cut in it and attached the elastic strings. I then put the mask on the back of his head. (Yes the strings went over his face.) This looked great because it was round just like a blowup doll and didn't have the shape of a human face. I put a black wig on him, also backwards, with the hair covering his face. It was a cheap wig so there wasn't enough hair to entirely block his vision, but it did a good enough job of hiding his face. To complete the effect I told him not to bend his arms or knees as he walked, and I had him walk backwards. From the back, he looked like a blowup doll facing forward.I made sure to tell everyone the blowup doll's vagina went in, and was 100% fuckable. I expected everyone to squeeze the breasts, which is why I went through the trouble of filling them with balloons, so they'd feel like blowup doll boobs. But I didn't think anyone would really want to touch his "pussy." To my pleasant surprise a lot of people actually wanted to feel it or even stick a finger in! I was more than happy to let anyone who wanted to poke around to do so. Someone even volunteered to test it out for us at the end of the night. How awesome is that? The "vagina" is air tight (or else a blowup doll wouldn't hold any air), but I made sure the guy used a condom as not to make a mess of the costume. I sure felt proud. To adapt the costume for general public throw a bra and panties on your sub once he's in his blowup doll costume. I suppose you could even throw on a short skirt to make it more "safe" for the public depending on where you're going. The only real problem is getting your sub to walk backwards without stumbling over everything. I would either just tell him when to step up or down, or just hold his hand and would pull it up or down so he'd know to step. It was probably the funnest Halloween costume I've ever played with.
Now for some fun ideas that take less work. The first is the obvious drag queen costume. Tell your sub not to shave that morning, or for a couple days depending on how fast his facial hair grows. If he just can't get that manly stubble then you can draw it in. Any pen or fine marker will work, just draw in a bunch of little lines. If you're going to a kink friendly party you can get away with something a little more lingerie like, either way, go as slutty as you can safely get away with. Your local super store or discount clothing store are a good place for finding this type of clothing without paying too much. The idea with this one is to be obvious, so overdo it with the makeup. Powder his face too much or go heavy with foundation, put on a bit too much blush, and way too much eyeliner. Throw some overly bright red or pink lipstick into the mix, and finish up the package with a blond, or even pink wig. High heel shoes aren't necessary for the "obvious" look, just have him wear shoes that contrast sharply, such as tennis shoes. Don't do anything half way, chose either obviously male, or overly female.
Female masked costumes are great but often overlooked for men, but these can be fun as well since it can be difficult to tell if it's a man or a woman in the costume. Your sub may even get hit on by guys, which is something I always enjoy seeing. This set of costumes includes the Disney princesses, but the grownup versions of these costumes don't usually come with a mask. Sometimes you can find a child's mask that will fit an adult, or an adult mask that's generically female enough to pass as a princess, but a celebrity mask can also make a good costume. Sarah Palin masks are pretty easy to get right now and could make a sexy costume since she wears skirts. You could probably get away with a Condolisa Rice or Hillary Clinton costume as well, but those don't strike me as being as much fun. Since the mask makes this costume, find a mask first and then build the costume around it. If you can only find a generic female face then I suggest getting a Cinderellas costume, as that's most recognizable. A wig and high heels are necessary, so don't overlook those. You may have to go to a big and tall store for the heels but I think it's really worth it. To keep it fun and sexy I wouldn't suggest using a dress that fully covers the legs unless your sub has very manly legs, or the dress itself really completes the costume, like a frilly blue Cinderella dress. In cases where you end up with a longer dress I'd suggest leaving off the panties to keep things sexy. If legs are shown I also recommend your sub shave his legs as not to give away his gender.
The other option is of course a sexy costume meant for a woman. The french maid outfit is often overdone on Halloween, but great nonetheless. Any sexy costume
will work and can be a lot of fun, but when choosing this type of costume, keep in mind that it can really be a lot of work. You have to go full out feminine as with the the previous suggestion. This includes a wig, high heels, and shaved legs, but you also have to make a good attempt at makeup.
Greasepaint can hide stubble on the face. And don't feel bad about having your pet shave his legs for a Halloween costume; whenever the sub sees, feels, or even thinks about his shaved legs this will not only remind him sub of his place, but of the fun you two had. This can make him (more?) horny even when you aren't around to tease him. Keep in mind that if your sub doesn't normally shave his legs because it would cause too many questions, or is unacceptable for one reason or another, having the excuse of "it was for a Halloween costume" often suffices. That said, opaque hosiery will generally hide leg hair. The darker the hair, the darker or more opaque you need it to be.
Halloween is also a great time to pick up a wig or two. Many stores carry them around this time of the year, so you can have your sub try them on to see how they look and to make sure they fit well. It's also a great time to pick up fun costumes for your sub if he's into humiliation or feminization, for example, french maid attire is desired by many subs. If there's no urgent need for an extra wig or costume I suggest you wait until the day after Halloween to buy them, as most every place marks them down to clear them out. Wigs and costumes such as the french maid can be rather costly the rest of the year, but if you go after Halloween you can get them for a great price.
Halloween is not only a great excuse for cross dressing, but a great excuse for all kinds of fun. It sparks the imagination, and if nothing else, is a great excuse to try just about anything. Want an excuse to try pegging? Dress up your pet as a woman. Want an excuse to try rimming? Dress up as a cheerleader and tell your sub his tongue is only worthy of your ass. Hell, the excuse doesn't even have to make sense. If you want to play with a chastity device tell your pet that in order to properly fill the role of his costume - and any costume will work as an excuse - you're going to keep him locked up all day and only let him out to tease him from time to time. Whatever you do, have a fun and happy Halloween.
