Tokyo - The Challenge - 30th September

Background

Messages were exchanging back and forth with a friend on Stumbleupon and I mentioned that I’d love a challenge; something to do that might be difficult and fun, here in Tokyo. He thought about it and came up with something.

The Challenge

The challenge sounded simple but, as you know, simple things can get complicated so easily. I was to find a young virgin guy (of legal age, of course) and convince him to give his virginity to me. Now, as I said, it sounds simple.

What Happened

The plan

Tokyo is a big city, heavily populated and divided into sections in a loose kinda way. Somewhere in this city I had to find a virgin guy, take him somewhere private, or not, and have sex with him. Now, I talked to a friend, Kishi, and she talked to a few other friends, guys and girls, to try and find the most likely place to fulfill this challenge.

Kishi’s circle of friends is mostly from the more ‘interesting’ side of life and not one of the guys she knows is a virgin. It took a while but finally they came up with Akihabara. It was a place I’d thought might be likely when talking to my SU friend and it was confirmed by Kishi and her friends.

Why Akihabara? It’s Tokyo’s geek paradise. A lot of guys go there to ‘maid cafes’ to be served by waitresses dressed in the costume of their favourite Anime character. Most of the guys live in a kind of fantasy world of their own, obsessed by ‘characters’ rather than real women. It couldn’t be hard to find a virgin among that lot although I was warned that some might be scared off by an ‘actual’ woman. Worth a try.

My friends managed to secure a place nearby for a ‘tryst’ and found a costume I could wear that would serve the fantasy element. In the end I emerged from my friend’s car dressed in a French maid’s outfit, complete with hat, white stockings and razor sharp, and tall, stiletto heels. I even had a tiny purse and a feather duster. Red, red lipstick and pale makeup finished off the look.

On the town

Once on the street, eyes fixed on me and I have to admit I was a little embarrassed. Yes, me embarrassed. Can you imagine walking down a street at night in London dressed like this? Anyway, I tottered along for a bit then stood, looking into the window of a store. A small group of guys gathered near me, some smiling, some serious, and some digging each other in the ribs and sniggering. None came within ten feet of me though. It was like a show but I wasn’t there for a show so I turned around and smiled at the boys. Now, I don’t speak Japanese and they didn’t speak English so it was ‘difficult’.

They just gawked and none would approach me. They just stared. If this continued I wasn’t going to get anywhere and I had a party to get to in just over an hour. Kishi had given me a few words to try, like virgin boy, and when I said them most of the boys walked away, a few backed off looking nervous, and a few stayed and kept gawking. It wasn’t really working though. You know how you just know when something is going well? So I walked a little further down the street and came near a café where a bunch of guys were hanging out, exchanging what appeared to be colourful cards of some sort. I just strolled along and one by one, my little entourage dropped away.

I was nearing the corner of the street when a small voice said “Excuse”. From beside me a guy, he must have been around twenty, stood. He was kinda moving from foot to foot like someone who really needs to go to the bathroom. His hair was a little messy, his clothes non-descript, a stereotypical geek. I almost laughed, more from surprise than anything. Anime fanboys are like that I guess. Anyway, his English was broken but I could understand most of it. Roughly what he said was “boy..virgin..fuck..ok?”

Time was getting shorter and he was nice enough so I took his hand and led him to the little place my friends had found. I took the guy inside the barely lit room with its bed and basin. He took out some money and I waved it away. Jesus, he thought I was a whore. No way was I taking money for this.

I started to undo my skirt and he stopped me. “Like this” he said and pointed to my costume. He wanted the whole fantasy thing it seemed so I just slipped out of my panties and handed them to him. He put them to his face and took a long breath in. “For you.” I told him, and he laid them out carefully on the side of the basin.
His cock was pressing hard against his pants and I unzipped him and slipped it out. Not a bad length. Already there was a bead of cum seeping from the eye and when I took it in my mouth I could feel it was ready to burst. At that point I couldn’t really think what taking a guy’s virginity would mean. I guessed it was putting it inside a pussy so I took my mouth away and rolled a condom onto his dick. I walked over to the bed, laid down and spreading my legs and he took my lead. Just before I guided him into me I said “slow”.

The rubber helped a little to desensitize him and he did go quite slowly but within not more than thirty seconds he tensed, made a gasping guttural sound and collapsed onto me. Well, I’d completed my challenge but there was no way I was going to let this guy go without having a little more fun, and now I was horny too. He apologized over and over and I put him at ease with repeated oks. I guided his mouth down to my pussy and moved his head a little to show him how I liked to be licked. Credit to him, he wasn’t bad for a first timer. It took a while but he was determined and after ten minutes or so I came. When I started to cum he pulled away and stared but I grabbed him and shoved his mouth back onto my cunt. If I didn’t finish cumming I’d be cranky all night and no way was I letting that happen.

After I came I handed him another condom which he slipped on, and I guided his cock into me again. This time he lasted a little longer and I was still sensitive from my orgasm so I came again which made him cum. He fucked me hard as he came and that just took me over the top into another one.

We both cleaned up and I showed him out the door, reminding him to take my panties. He was smiling as he left.

A few minutes later I phoned my friend who brought a bag with my party clothes inside and I changed out of the maid’s costume, then walked out into the street, recalling, to her, what happened. We jumped in the car and off to the party.