This is a story of the best Halloween costume I’ve ever worn.  It’s a simple story with no danger and no sex, but it was a fun experience and I wanted to share it.  It also involves cross-dressing since I’m a guy that likes to be bound while I’m dressed in women’s clothes.  In fact, I spend about as much time describing my outfit as I do my eventual serious bondage.  You’ve been warned now though, so if that kind of thing doesn’t interest you you might as well read something else.

Anyway, this all took place about eight years ago, when I was still single and living in the city.  The only person who knew my secret was my friend, Lisa.  She used to come and “play” with me about once a month.  This one time in early October, when she had tied me to a chair in my ubiquitous long-sleeved leotard and L’eggs pantyhose, we got to talking about Halloween costumes.

“Have you ever thought about dressing as a woman for Halloween?” she asked.  “There’s a party I’ve been invited to and I’d really like to bring you.”

“I’ve thought about it,” I said, as I worked on the ropes, “but I don’t think I could do it.  I’d either have to look like most guys who do drag for Halloween with the balloons for breasts and the thrift store dress or I’d have to impersonate a celebrity, like Marilyn Monroe.  I like dressing up but I can’t do the clown look and I don’t think I could pull off anyone famous.”

“You know we could make you look almost real.  You’ve got those wigs and I could do your makeup…”

“Yeah, but I could never be dressed like this at a party with people I know.” I continued as I unwound the ropes holding me to the chair.  “I’d die of embarrassment if any of my friends saw me getting aroused.  Do you know how long it took me to get up the nerve to tell you about this?”

“But you don’t know these people!” she said eagerly.  “And we can come up with an outfit that would hide your erection.”

“Maybe,” I said, still unconvinced.  “The thing is, I never get dressed up unless I’m going to be tied up.  I don’t know if I’d want to be cross-dressed at a party without some kind of bondage and I’ve never come up with anything that might work.”

I had finished freeing my body from the chair and was just about to start in on the ropes around my knees and ankles when she grabbed my hands.  “If I could come up with an outfit and a way to tie you just enough to be interesting but still let you enjoy the party would you come with me?” she asked.

“I don’t know…”

“I’ll make you a deal.”  She had a dangerous twinkle in her eyes.  “Let me tie you to the chair again.  If you can escape within 30 minutes you win and you don’t have to go.  But if you can’t, if there’s still any rope holding you down, then I win and you have to go with me.  I’ll even tie your hands in front and let you win if your legs are still tied.  Come on, you know you like a challenge.”

I thought about it for a few seconds.  Lisa had gotten better at tying me up in the couple of years she had been playing with me.  I couldn’t always get out the way I used to.  But I was just a little bit curious, and highly aroused, and that was always a dangerous combination.  And she was right – I did like a challenge.  I agreed, and let her tie me to the chair again.  She put my hands in front of me, like she said she would, but there was so much rope pinning them to my lap that I couldn’t move them.  My arms and body were tightly secured the chair back.  My legs looked like some crazy spider had spun a web over them with the rope going every which way (including between my hands and arms).  Forget my hands – I couldn’t move anything.  She had used at least 100 feet of rope, if not more.  I should never have agreed to the bet but I struggled anyway, because I had to.  After 30 minutes I hadn’t even begun to make a dent in the ropes around my wrists.  Lisa smiled broadly and let me loose, all the while telling me how much fun I’d have without telling me what she had in mind.

So there I was on the day of the party, sitting naked at my kitchen table having just showered and shaved (including my legs, as per Lisa’s instructions).  She wanted to make me look like she did, with the same wig and makeup.  We started with my nails, putting false ones on and painting them a deep burgundy.  She did my lips next, in the same color, and added some lip gloss to make them shiny.  Slightly smoky eyes with just a hint of silver completed the look, along with black eyeliner and mascara, some foundation and blush.  We even tried shaping my eyebrows but had to settle for highlighting them.  I had never had such a full makeup job done on me and it looked good with my wig of shoulder-length, straight black hair with the slightly spiked bangs in front.  When my nails had dried and we were both satisfied with my face and hair we moved on to the bedroom to get dressed.

Lisa wouldn’t let me see what was in the suitcase she had brought over.  I had to put on each piece of clothing as she handed them to me.  We were going to wear similar outfits, she had said, but her costume would be different in some not so subtle ways.  The first item was a white lace, long-line bra, with lots of boning and about a million hooks up the back.  Okay, obviously there weren't a million hooks, but there were a lot and it took a while to put on. When it was in place, the cups stuffed with my rolled up sock "breasts", she handed me a pair of fine mesh black fishnet pantyhose. I wondered what was next as I put them on, making sure to keep the back seams straight.

I had an idea where this was going when I saw the next piece of clothing.  It was a white cotton bodysuit and the part above the waist was a long-sleeve tuxedo shirt.  I had seen bodysuits like this before but they were usually just regular button-down dress shirt styles for women who wanted to look like their shirts were always tucked in.  The snaps on the bottom allowed the wearer to go to the bathroom without having to remove the whole thing.  It fit perfectly (after a little adjusting of my dick and balls) and was surprisingly comfortable.  When we finished putting in the studs and cufflinks I noticed that the whole thing had burgundy accents to match our lips and nails.  I didn’t expect the tap pants, though.  They were actually black satin dance shorts and short they were.  Even with the elastic waist they were just baggy enough to help hide my raging erection, at least a little.

"It was the best I could come up with short of putting you in sweat pants," she said as she checked me out. "They aren't perfect but they'll do."

"I like them." I said, smiling.

"Good." She smiled back at me as she handed me a pair of knee-high black boots.  They were a leather-like material but they hugged my ankles and calves like no leather boots had before, and had four-inch heels and a half inch platform. I was used to walking around in three-inch heels so these weren't a problem for me.  The final touches were bow ties and cummerbunds (also in burgundy to match our lipstick) and black vests. When we were done we looked like a couple of old fashioned magicians assistants.

Which is exactly what we were – sort of.  Lisa wouldn't tell me what I was supposed to be yet, saying only that I'd have to wait, but I'd like it.  First, I had to splatter fake blood on her while she stood in my shower.  She had a bag with some sleight-of-hand tricks that she was going to pull out at the party.  (She was good with them, too.)  She was going as the assistant who had killed the magician because he wouldn't teach her more tricks.  When the blood was dry and she looked nice and gory she had me stand in the middle of the room and close my eyes.

I could hear chains.  I didn't think it was possible for my dick to become even harder than it was, but it did.  The thought of being bound in chains had long been a fantasy of mine.  Just the idea of being trapped in that cold, hard metal was almost enough to make me cum right there, but I restrained myself (pardon the pun).  She started by pulling my arms out in front of me and locking a pair of handcuffs on them.  They were just loose enough for me to move my wrists without being able to pull my hands out.  Once they were double locked she dropped my hands and placed leg irons on my ankles.

"The chain on the leg irons is only six inches long," she said as she tightened and double locked them.  "That will allow you to take very short steps but won't be long enough to get caught in your heels."  Finally, she took a short length of chain and wrapped it twice around my arms and body, just above my elbows and under my breasts.  She pulled this one very tight before locking it with a small padlock.  When she was satisfied she told me to open my eyes and look in the mirror.

"I love it," I said.  I really did, too.  "But what am I supposed to be?"

"You're the World's Worst Escape Artist!" she said, with a flourish.

"Oh. My. God." I said.  "What a perfect idea!"  I was actually going to a Halloween party while dressed and bound.  I walked around a little to get used to the leg irons, then, when I was ready, we got in her car and drove over.

We were a hit from the moment we walked in.  The party was being thrown by a bunch of graduate students from the nearby art institute.  I went in as Michelle, speaking in a higher pitched voice all night.  It was pretty obvious right from the start that I was a guy but they weren’t surprised and didn’t treat me like a freak.  They all decided that I was making some kind of artistic statement or doing a performance art piece and I did nothing to challenge that belief.  Even my erection was seen as a part of the performance.  Since I couldn’t walk very well I spent most of the time sitting down in the kitchen, letting various people bring me food and drinks.  The few times I had to use the bathroom I did have to walk around to find Lisa because she had the keys but that effort just added to my arousal.  She would only remove my arm chain, however.  She said I had to suffer for my art.  I stuck my tongue out at her and did the best I could.

I have to admit, I had a great time.  The people were interesting and they didn't treat me like a freak.  When Lisa came to take me home and told me it was 1:30 in the morning I was shocked.  We had arrived at 8:30.  I couldn’t believe I had just spent the last five hours cross-dressed and bound in public!  And not just in public, but having interesting conversations with strangers.  This was an experience I didn't want to end.  It had to, though, so we said our goodbyes and headed back to my place.

“It sounds like you had a really good time,” Lisa said as she parked the car.

“Oh, I did.  I’m sorry.  Was I babbling?”

“Just a little.  But it’s okay.  I’m glad you enjoyed yourself.  And you seem really comfortable in that outfit and those chains.”

“Oh shit.  I completely forgot about it, it all feels so natural.”

“Would you like to stay like that all night?  I could leave the keys on your dresser.”

“Could you… make it better?  I mean, don’t get me wrong.  I really appreciate that you came up with this idea and got this outfit for me and you know I’ll clean it before I give it back to you…”

“You can keep it.  It’s yours.”

“Seriously?”  I was shocked.  “Holy shit!  Thank you!”

“So if you like the outfit what did you mean by ‘make it better’?  Did you want to be more tied up?”

By that time we were up in my apartment, sitting on my bed.  I didn’t know what to say so I just looked at the floor and nodded yes.  I was a little embarrassed to ask that of her after what she just told me but I could be insensitive sometimes when it came to indulging in my desires.  I would have been fine just the way I was, but I wanted more.

“Okay,” she said.  “I can do that but you’ll have to let me do what I want.”

I wondered what she meant but looked at her and said, “Okay.”

Lisa removed all my bonds then so I could have one last bathroom break and touch up my makeup.  When I was back in the bedroom she cuffed my hands behind my back and had me press my lips tightly together so she could place an X of duct tape over my mouth.  I was a little surprised when she checked my wig to make sure it was secure before tightly wrapping more tape over my mouth and around my head five or six times.  It covered my face from my nose down to my chin.  I was even more surprised when she told me to close my eyes.  I did, though, and felt her taping large gauze pads over my eyes and eyebrows before wrapping more duct tape around the upper part of my head another five or six times.  When she was done I was more securely gagged and blindfolded than I had ever been.

She put the arm chain back on next, right where it was before.  I thought I’d be able to easily squeeze out of it but didn’t want to try yet.  I would have been wrong.  Her next step was to hook a padlock to the handcuff chain and attach the end of a longer chain that I didn’t know she had.  She pulled this one up and over one shoulder, pulling my wrists up to the small of my back in the process, then pulled it down and under the arm chain, back up and over the other shoulder and down my back, hooking it to the padlock.  I thought that would be it but she had enough to wrap it tightly around my waist, twice, finally locking the other end with the lock that started it all.  I couldn’t move my arms at all.

She led me over to my bed and helped me sit down.  I thought she would reattach the leg irons but again, I was wrong.  She started wrapping yet another chain around my ankles, moving it down to pass it around my feet then back up to my ankles.  When this one was locked off my feet moved as one.  If I could have I would have laughed when she said, “I’ve run out of chain so I’ll have to use rope on your knees.”  She did, too, expertly tying my knees together with a short piece of rope that was cinched off between my legs.  I wasn’t going anywhere and oh boy, was my dick hard.  She helped me get comfortable on the bed.  With a quick caress on my cheek she said, “I’ll leave the keys by the front door so you can escape when you’re ready.”  She laughed.  “I’ve got to go meet a guy but I’ll call you tomorrow around four to check on you.  That’s only about 12 hours from now.  You should be able to get out by then.”  She left, laughing.

I rolled around on the bed for a bit, thinking about trying to escape right then, but I was tired.  Not too tired, though, because it only took a few seconds of struggling before I came, releasing the orgasm that had been building up all night.