Much gratitude goes out to the various people who encouraged me to post some of the stories I have written for personal reasons. I would also like to thank Lisa for the ideas that turned a dry narrative into a conversation, and SpreadLegsWetLips for editing and review.
I walked into the diner where I was meeting a friend for lunch and saw the he was already there. He looked like he was daydreaming.
"Hey Ron, what's up?" I said while I was sliding into the booth.
"Just thinking about that game last night. That was some nail-biting finish huh?"
"I didn't really get a chance to watch it. I hooked up with Sasha last night."
"So you were fucking stupid enough to go through with it? Dumb... give me all the details."
"Okay, okay. I know what you are thinking. Yes, I contacted an escort off the Internet. Yes, I actually followed through with it and met her. I know, you think that was a very stupid thing to do. Yes, I will never do it again... at least not until Sasha comes back through town anyways. Now, if you will stop rolling your eyes at me I promised you the details."
"Whatever. How did you find this chick on the Internet again?"
"I was planning that Vegas trip for next month and cruising through web sites on bordellos in Nevada when I hit a site advertising escorts right here in town. It must have been a missed click that hit a banner or something, but I was bored so I went ahead and scanned through the ads."
"Well that was your first mistake."
"Yeah, yeah. Do want me to finish the story?"
"Okay. Sasha's ad and picture both jumped out at me, and it was the only ad I saw that did not have a phone number. In her ad she described herself as very aggressive, and there was a link to her site. From the pictures Sasha appeared to be a beautiful Asian woman with a classic hourglass figure. Her shiny straight black hair fell to just below her shoulder blades, and from her long chiseled legs it looks like she must work out regularly. I'm still not exactly sure why I did it, but on a whim I filled out the contact form on her site and sent it off. It was only after sending the form that it dawned on me that the site was called Palm Springs Fetish, and Palm Springs was just over 1000 miles away!"
"Needless to say I was pleasantly surprised when I got an email the following day. It turned out that Sasha was going to be here in town for a few days the next week, so after a couple dozen emails or so we setup a four hour dinner date."
"We met at a local steak house and spent over an hour just getting to know each other. We talked about a little of everything from sports and music to personal goals and current events. We also spent quite a lot of time talking about sex, even getting around to discussing various kinky fantasies."
"Wait. You met with an escort and wasted your time with her going out to eat?"
"Of course. You know how much I hate going out to eat alone."
"Gentlemen, we have found mistake number two. Please continue."
"We went back to her suite and started kissing and cuddling on the love seat..."
"Seriously?" Ron interrupted again. "You just went to some random hotel with someone you just met? Are you that fucking stupid that you WANT to get robbed?"
"Hey, between the emails and talking over dinner I thought I knew her pretty well!"
"Unbelievable, I never thought you were THAT naive. We officially have your third mistake. Please continue, I want to know just how far this little rabbit hole goes."
"While we were making out Sasha helped me out of my clothes while I only managed to get her dress off. At this point she was still wearing black thigh-high stockings with a lacy black panty and bra set that did wonders for my cock's posture. Soon she pulled me up off the couch and started moving me toward the bed. Next thing I know I am flat on my back in some kind of wrestling hold."
"I was shocked. I never expected her to be so aggressive in bed, even though I did see it in the ad. Even more important is that since I am a 'leg man' I find that I am incredibly turned on. Having her nylon-wrapped legs all over me, holding me, controlling me, squeezing me while we continue stroking, kissing, and nibbling on the fun parts is a fantasy that I will be dreaming about for years to come. While I was paying attention to her legs wrapped around me, pinning one arm to my chest she managed to tie down my right hand. It happened so fast she had to have planned this and setup the ropes and shit in advance."
"She then used all her body weight to pin my left hand while she tied it to the other corner of the bed. Without my hands free I was pretty ineffective at stopping her and soon she had my feet tied down as well. She took a minute to walk around and pull everything tight. I am now tightly spread-eagled on the bed. I'm helpless, barely able to move, and in her complete control as she tells me I am now her personal toy and sex experiment."
"Holy shit, you have got to be making this crap up!"
"I know. It sounds like something out of a bad porno right?"
"So this is when the sexy bad lady robs you and leaves you to be found by the maid," said Ron while he was half laughing at me.
"No, she started kissing me and playing with my cock and balls. I was so turned on I was ready to shoot in under a minute, but she stopped me by grabbing my nuts and pulling. She proved to be a genius about knowing when I'm about to cum, and also about preventing it. She never ignored me, but she kept me balanced on the edge of orgasm against my will."
"Seriously? Against your will?"
"Seriously! If I tried to ignore her, she teased and stroked me relentlessly; not allowing my interest to flag... and when I tried to cum she wouldn't let me. She was also an expert at applying just enough pain to stop my oncoming explosion without being cruel. Of course, I couldn't exactly prevent her from touching me, cuddling, kissing me, or using any part of her body to excite me. I also could not stop her when she toyed with me for her pleasure, but she never allowed me to cum."
"The best I could do was to return an occasional kiss, or sometimes lick and nibble her a little when she put something close enough to my mouth. I did get to suck her tits a little, she seemed to enjoy that. She also seemed to enjoy having me lick and suck on her toes. I actually did quite a bit of that. Never got to taste any pussy though..."
"Anyways, this seemed to go on forever! Finally when I felt that I would go insane with lust if I couldn't cum she relented. She squeezed me while licking my balls and pushed me off that cliff. Then She continued pushing me, working my shaft and balls while avoiding the head of my dick. She fucking milked me for all I was worth, giving me the longest orgasm and one of the greatest cums I think have ever had."
"When the orgasm finally ended I had the thought that I didn't really know her."
Ron started laughing so hard he almost sent the coke he was drinking out through his nose! "So now brain-dead boy finally stops thinking with his dick."
"Yeah, so what?" I said chuckling a little and turning 3 shades of red. "It's not like I had much choice."
"Shall we review your mistakes thus far, or will you simply continue with your little fantasy here?"
"I swear I'm not making this up! Anyways, now that lust was no longer making me an idiot, and stop with the eye rolling already, I realized I was crazy to let her make me helpless. A cold shaft of fear strikes through my gut. She began to tickle me, playing with the head of my cock. What felt so very good a moment ago is now pure sweet torture. The pleasure is simply too much for me to handle as I scream, buck, squirm, yank, and do everything possible in an adrenalin-fueled panic to break free and make it stop by brute force. It is an epic failure. In the next minute I spend an eternity in heaven and hell at the same time, but then something really strange happened."
"No fucking way. You sound like an infomercial saying 'But wait, there's more!'"
"I'm only telling the truth, but if you don't want to hear the best part..."
"No, no, no... What happened next?"
"While I was screaming to make it stop I suddenly realize that I'm quickly approaching that cliff again. Slowly as lust starts to take over my brain I notice that my hips have started bucking into that sensation instead of trying to pull away. My screams changed their note as well, and they are now an expression of my mounting pleasure. That's when I felt her spreading lube into my bum hole. A single finger pushed up my ass and reached inside to tickle my prostate. The prostate massage was the last straw as I immediately began blowing my load again in an honest to God male multiple orgasm."
"That's not possible. Even if you came twice it's still not a multiple."
"Then what would you call it when you cum twice in as many minuets"
"After it was over she cuddled with me, holding me and comforting me with pillow talk half-whispered in my ear as we both came down from the sexual high. Eventually she went to clean up, and then she cleaned me up before returning for more cuddling and pillow talk. We fell asleep like that with me still tied up. After a short nap she finally let me go."
"What pile of bullshit! You had to have made up that whole fucking story."
"Sorry, that's my story and I'm sticking to it."
"If that was for real then I only have one question."
"Yeah? What's that?"
"What was the name of that web site again?"