Another Halloween was approaching and again I had the urge to dress as a woman to trick unsuspecting men into letting me suck their cocks. Something about tricking them really did it for me.
I'd only ever sucked on two other occasions and without some serious trickery I would never be passable. My hands were too big and my shoulders were too wide.
But the feelings were welling up inside me and I knew it was an itch I would have to scratch.
However, I also really wanted to go to the street festival this year. Could I think up a costume that would work out on the streets? And could I lure guys into doing something?
I started searching the internet for ideas and after hours of looking at costumes I figured it out.
You see, I saw this costume where some guy put a large box over himself which had cutouts in the front for girls to put their boobs into. His sign read, "Free Breast Enlargement."
I'm sure over the course of a night of partying a few girls would have taken him up on it - either because they were adventurous, or because they were dared to do it.
Now...suppose, I made a box with a lower hole which read, "Free Dick Enlargement?"
Answering my own question I decided it would be an invitation for small cocks only.
How about "Free Penis Massage"? Hmm, that one might sound too little like a joke and attract the attention of police.
Maybe, "Free Testicular Exams"? Yea, that could work. I'd paint it to look medical and have some testicular cancer brochures on the side.
Furthermore, if someone peeked through the hole, I'd be dressed like a girl in the dark interior of the box.
Then I had second thoughts and went back to the "Enlargement" idea. I could draw some illustrations showing dicks getting very large. Who doesn't want just one more inch?
I sure hoped some guys would be bold enough to insert their cocks through my hole, right there in the street. Maybe at least one out of all the guys at a whole festival would do it, right?
I made my box strong enough to withstand some serious pounding, just in case some guy got carried away or the crowds pushed me around.
I added blinders or wings so the rube would be standing in a little alcove, partially blocked from view.
On the big day I was nervous. Nervous it wouldn't work, nervous I'd get arrested.
Underneath I wore girls' jeans, girls' pink canvas shoes, a colorful ploofy blouse, and a wig. The shoes could be seen as I walked, so from far away anyone would think they saw a girl.
I didn't need to, since no one would see them, but I wore girls' panties under the jeans.
It was loud on the street. Crowds were streaming this way and that, moving from carnival games to tasty treats. Inside the big box I could barely manage to get from one place to another but I had a great time eyeing my marks.
Lots of folks laughed when they read my sign, realizing that the hole was meant for guys to put their dicks through.
Unfortunately, to me it seemed like every guy was with a girl and would never accept.
I bought a churro, passing money through a sliding door. I watched street performers through the screened eyeholes. And I tried to place myself in front of guys who looked like they might be crazy enough to do it.
By midnight only two guys had pressed their pants up to the glory hole. I felt them up, but neither would let me unzip them. Well, I heard them laughing as they went to tell their buddies about the "hot" girl in the box. Funny how guys exaggerate.
A long hour later I'd had three beers and two hot dogs but, sadly, no 'dick dogs'.
Feeling like my night had been a waste of time I turned down a less populated street and sat down. The stilts on the box let my little bench inside support me perfectly.
I had thought guys would be less inhibited than girls. I now wished I'd worn a breast enlarging box instead. I've seen the videos of girls gone wild. I felt dejected.
But a few minutes later some bloke stumbled past me and took a piss on the wall about ten feet away. Apparently he used my box to shield his activity from the distant crowd's view.
He came back, resting one arm on my box, and lit up a joint. I would've asked for a hit, or asked him to leave, but I couldn't speak or he would hear my male voice. Moreover, none of my prerecorded messages said, "Go away."
After a few minutes he noticed my box, as if for the first time. Bending low he spoke into the hole, "Is someone in there?"
I pushed a little button to answer, "Beep, beep."
The guy jumped back, startled, "I'll be!" He looked closer, "Shit! There's a girl in there. What you doing way over here? All the fun's over there."
I turned the dial which displayed a few preprinted messages, "Try it out."
He read the message slowly. Then stopped to look over the whole box. "You don't say? But people would see."
I wanted to shout, "You just took a piss right back there." But had no message for that. Instead I pushed the R2D2 button on an app on my phone playing encouraging squeaks and bleeps.
He complained, "No really. This is too open." After a pause, "Let's go down to the end of the alley."
I didn't feel safe all the way down there. So staying near the entrance to the alley, I just turned my box to at least face away from the main street.
He walked around, thinking out loud, "Hmmm, this might work... How much?"
I turned the dial, "It's free." Then, "It'll make you larger." Naturally any soft cock would get larger when it grew hard.
He pressed his pants to the hole just like the others. I massaged his unit through his jeans then when I started to unzip him, he reluctantly let me.
Pulling the fly to the side, the second obstacle was his underpants. I fished through the fly in his tighty whities, but it's kinda hard to pull a dick other than one's own through one of those.
When it was finally free it felt nicely thick and was longer soft than my lightly closed fist. Though, by this point I no longer cared if it were big, any cock would do.
I massaged and stroked it in the dark box, I fondled and caressed it too. I circled my fingers around it, pulling and tugging to get it to its full rigidity. Even from my place inside I could tell he was leaning the full weight of his arms on top of my box.
I imagined the hard dick pointing straight at my mouth. It had been two years since I had sucked, let alone touched a stiff one, and I was relishing the moment.
Outside my box he noticed I wasn't doing any more manipulation of his organ, "Aww, is that it? You can't stop now."
I had the urge to play with his emotions a little so I turned the dial, "Congratulations! It has been enlarged."
"Wait! You can't stop now. I'll pay you."
I cranked it again, "It's free." He didn't know I had every intention of sucking him.
"But I need more. Please! Please!" He begged. "Just kiss the tip. I won't put it in."
I guessed he'd used that line on girls before. Of course, if I didn't want to suck it there was no way he could make me from the safety of my box.
I kissed the tip softly, eliciting a low moan. "That's right, Baby. I love it."
Now I was flying high. He really thought I was a girl. That's what I loved! I imagined his desperation and his lust fueled fires. I could make him do anything.
My mischievous side got the best of me, I wanted to see how far I could push him. Thinking creatively, and ignoring my previous statements about it being free, I took out my phone and typed: "Drop in a twenty." Then had my phone say it out loud.
I felt his dick jerk as he fumbled in his pockets like a mad man. When the bill popped in I sucked on just the tip for the briefest of moments, then typed, "Now call a friend and have a casual conversation as if nothing is happening." Could I really make him do it?
Upon hearing my instruction he faltered for a second, but I slurped crazily on the end then dropped his lonely bouncing cock to hang free - ignored.
"OK, OK, I'll do it. Just keep sucking. Please!"
My phone played, "Bloop bleep bloop bloop." And I kept sucking.
On his phone I could hear only his side of the conversation, "Ted, it's Joey, where are you guys?" Then, "I went down the alley by Papa John's to take a wizz." After another pause he went on, "Where'd they go?" and "Yea that's too girly." and "So it's just you guys?"
He was humping at my mouth steadily and I returned the favor by sucking just as steadily.
The next thing he said into the phone thrilled me, "You should come on over. You'll never guess what I found." followed by "Just come here. You won't be sorry."
He hung up. "Whoever you are in there. You give better head than my girlfriend. Not that she does it often."
I felt pretty good hearing that, and I made a point of sucking especially hard and going down especially far to let him know I liked what he said.
"Oh yea," he muttered drunkenly, "you keep that up and I'll come right down your pretty little throat."
I milked the base of his cock as if to say, "Give it to me. Come down my throat."
I heard a voice coming closer, "Hey Joey, what's so big we gotta come down here. All the action is by the Ferris Wheel. There's a magician with a real hot assistant. And every time his cash box gets fuller she takes off more clothing."
Joey knocked on the plywood on top of my box, "You know what this is?"
Ted waited a sec, presumably looking over the back of my box, "It's a chest Joey. I've never seen it here before. Is this what you wanted to show me? Because...magician's assistant...getting more naked all the time."
Joey admonished him, "Teddy, Teddy, this isn't just any box. This is a blowjob box and there's this super hot chick inside. She's sucking my dick right now, this very moment, as we speak."
