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Old 08-09-2017
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a9127 a9127 is offline
Senior Ladyboy Lover
Join Date: Jun 2013
Location: Zionsville, IN USA
Posts: 2,106
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Default Pretty Woman 2017

Not having much luck getting laid this summer, I decided to try the site “” to meet someone in Zionsville. There were over 40 profiles. The girl I finally decided on went by the name “SluttyCindy97.” She described herself as 20, 5’11”, slender build, long legs, blue eyes, long blonde hair, and large cock. She said she could be a top or bottom and was willing to try anything once.

I texted her and we agreed to meet downtown at the Dairy Queen next to the Bentley dealership. Very beautiful, she seemed friendly and we chatted over a “Guardians of The Galaxy” Blizzard. She had noticed the car I was driving and said “That’s really awesome, what do you do?” I told her I owned my own company in Zionsville and also taught at one of the local universities. She told me she was going back to Indiana University this fall and wanted to become a journalist. “You’re really cute. I bet I know some of your students. You’d be surprised. I can fix you up if you want.”

We chat for a while and you say, “I usually meet my ‘dates’ in the building where the antique store is. I’ve got my own place up there. It’s very private. Why don’t you walk over there with me? You saw on the website how much it is. I’ll leave the ‘tip’ up to you. Oh yeah, you can just call me ‘Cindy’ if you want.”

When we get to Cindy’s loft she kisses me then says "just leave it over there on the dresser." We continue making out and she says “You want me on my knees or you want to get on yours?” Already on my knees she giggles and says “well I guess that answers that…” She has already removed her top revealing a gorgeous tan body with small natural breasts. I can see the outline of her cock through her tight white cutoff shorts. It looks huge. Unzipping her shorts I slide them down her legs kissing her thighs and teasing her cock with my tongue.

Finally I start to suck her off. I don’t think I’ve ever been with anybody who had such a large cock before. She stands, legs far apart, bracing herself against a wall as I slowly bring her to orgasm. As I do I work a finger into her and massage her prostate. “Fucking Christ, that feels awesome baby. I might give you a freebie” you laugh. I do my best to take all of her in my mouth but I start to gag and she says “Don’t worry about it. Just keep doing whatever you were doing…”

After several minutes, she finally explodes in my mouth and I swallow most of her cum with the rest making a mess on the floor. She collapses to the ground sitting against the wall with her legs up. I’m on my hands and knees facing her. We both smile at each other. “You’ve still got another two hours coming baby. What would you like to do next? I can do anything you’ve ever dreamed of. You wanna get on the bed?”

We climb on and she lays there looking at me. “You’ve done this before haven’t you? Wow that was something else. I’ve never had a blow job like that before. Maybe I should pay you?”

I’m in no hurry so we both lay there and talk. You tell me a little more about yourself. You just turned 20 and it turns out you also live in Zionsville. You knew you were a “girl” when you were very young and had always been popular in school. One day you were looking at porn on your computer and realized there were a lot of guys who would love to spend a night with you. So…

“I bet I make more than I ever would with a college degree. Someday I will meet the right guy and settle down. Until then this is fun. And nobody knows.”

You lean over and kiss me again. Your mouth is open and the kiss is very lingering and sensual. “Just so you know, I don’t usually do that with a ‘client.’ So what would you like to do next?”

“Umm… what do YOU think?” I say as I kiss her and touch her breasts, running my hands all over her body.

“OK” you say smiling. “But I have to insist on ‘protection.’ Sorry, I believe you’re 100% clean but, well, you know…”

“Sure no problem.” Putting on a condom, I kiss you very hard then instantly we’re all over each other. I can tell you aren’t ‘faking’ it either. Our lovemaking is raw and aggressive. You are very strong and it’s almost like wrestling. Except that we are laughing and giggling. I was expecting someone cute who just laid there while I fucked her or she sucked my cock and took the money. This is way more than I ever expected.

Pausing you say “I always use this stuff, baby.” I gently insert my fingers and go to work on you. I can tell you are really turned on. Lying back on the bed you pull your legs up as I enter you. You let out a gasp once I’m inside then as I begin to fuck you, you moan and writhe while you grab onto the bars at the head of your bed. “God, that is fucking awesome… Christ…” You take your hands off the bars and stretch your arms out wide. Seeing the opportunity, I take hold of your wrists gently but firmly. You look me in the eyes and smile. Held tightly, your body squirms beneath mine, you say “Fuck me baby. Goddamn it... Ohhhhhh… Shit!” When I come it’s in the fucking rubber. To me it feels a little weird. I’ve almost always had unprotected sex with my partners but it still feels awesome with you. Your cum spurts onto your tummy and breasts. After I pull out I lick it off.

Both totally exhausted we lie there together. You say “God. I would have loved to let you shoot your load into me.”

You sit up and look at me. Touching my face you say “You know you can stay here as long as you want.”

We smile at each other. Then it’s time to go.

“What’s your name baby?”


“That was amazing Andy. Do you think we’ll ever see each other again?”

“Maybe. Do you like movies and long walks?”


After I finish getting dressed we kiss for a very long time.

“You know how to get ahold of me Cindy.”

As I walk out the door I leave twice what you had asked for on the dresser.

Copyright 2017 AMS

Last edited by a9127; 08-09-2017 at 09:09 PM.
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