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It had taken 15 minutes of cooperative efforts between Mae and myself to embed my long fat cock into her tiny young Japanese pussy.

Mae was a very willing participant. She was really pissed at her older boyfriend for having lost heavily at the weekly card game, and mostly for adding her to the pot when he ran out of money and other credits.

I had won the pot ... and 24 hours with Mae.

I had insisted that a bet was a bet, and that he had to pay up. Having sex with her was not part of my thoughts until she offered her body. Before she made that offer we had already had hours of fun - she was surprised what fun that a petite 18 year old girl and a 55 year old guy could get up to together.

We were resting after a few hours in the fun parlor, having a cold drink back in my apartment when she said to me “Would you like to fuck me?”

I was gobsmacked.

“You’re a nice guy ... and I’ve enjoyed myself” she started to explain. “I thought that I would hate this but I’ve been very surprised and I’m loving your company”.

She then went on to explain that sex between her and her boyfriend was a totally unfulfilling experience - all over within minutes. She had heard that western men, and older ones in particular were particularly good lovers.

So that is how I came to be naked on my bed with this petite Japanese girl who had a child-like body - slim with subtle curves, and just little bumps for breasts - but with the hardest of little nipples. Her pussy was what concerned me - it was totally bare, but it was so tiny looking.

What Mae didn’t plan on was my cock size. I’m blessed (or cursed) with a cock that is right off the size scale (at the upper end) - measuring in at 10.5 inches. She was fascinated by it - its length, its fatness, its hardness and the heat that it emitted.

Before I’d even tried to penetrate her I had teased her pussy with over an hour of tongue and finger attentions. She had cum gangbusters every time, with each cum getting wetter and wetter. I found some lube, giving my cock a liberal coating before I nudged the head between her tightly closed pussy lips.

“It’s not going to fit” I exclaimed with some exasperation.

“Hey ... take it slow and it will” Mae reassured me.

“Why ... how do you know?” I asked her.

She didn’t answer for a moment, then she meekly responded with “I’ve had a big fake cock in me. So I know that your cock will fit”.

Now there is a story that I will need to explore ... later.

With my cock poised at the entrance to her tight canal, I pushed firmly against the tightness. It probably took 10 to 15 seconds of constant pressure before I felt my cockhead slowly enter.

“Fuck that’s tight ... insanely tight” I commented.

“Keep going ... keep going” she urged me. Progress was slow but steady, and that’s why it took 15 minutes for me to impale her with my cock.

I rested and enjoyed the sensations of my cock trapped in this velvety smooth vice.

“I love it ... so full and stretched” she moaned.

I lifted her legs by ankles and looped them over my shoulders, putting my arms around her trim thighs and pulling her hard against me. Just a couple more millimeters of my cock slid into her. I started a bump and grind fuck with very small subtle movements in and out, and round and round.

“Yes ... yes ... fuck me” she wailed, eyes closed with her hands cupping and squeezing her tiny breasts.

I closed my eyes and focused my attentions to the feelings running along the length of my cockshaft. Her pussy felt like a second skin in my cock - she was wrapped so tight against my shaft.

I have never been inside a pussy so tight, and she was my first young Japanese girl. I’d had some so-so sessions in a local Asian brothel with some disinterested young girls but this was a full-in encounter with a very willing participant.

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Kalie was already pissed at David, they had argued earlier in the day about coming out tonight. The two had been dating since their sophomore year of high school and had been nearly inseparable since. It was now the start of their second semester at college, they had gone to the same school in Colorado. The two were from Nebraska and the school had been a compromise, Kalie wanted to get out away from home but David wanted to be near his parents. Now they were a short drive away but at least...

Innocence and a Bet

Cherry was the perfect name for ripe innocence, at 18 and her last year in high school had taken a bet from several of the other girls. She had always done wild and crazy things and had always won every bet she had ever taken. Thinking this latest one would be no different! The bet was that she had to go to the Rusty Dyke a notorious lesbian bar that had a reputation for catering to the meanest Bull Dyke's that one could imagine. She was to act like she was a young lesbian bottom and kiss...

Jessies Fantasy Chapter 1 Losing a Bet

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was on my way to meet my usual group of friends. The eight of us had been friends since high school, and we...

Crossdressing

The Bet

The Bet by Laura Brooks I can pinpoint the day this all started. It was a chilly, Sunday afternoon in early December. A light rain was falling outside and Carol (my wife) and I had built a cozy fire in the fireplace. She was sitting on one of the couch, her legs curled up beneath her reading and sipping a glass of wine and I was sitting at the other watching the Giants begin to give away a 21 point lead to the Eagles. Carol stood up and stretched, heading toward the...

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