Lucy's Revenge
Keywords: Lucy's, Revenge,
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First of all, you need to understand I'm not gay. I've never had a gay experience in my life but have had a few fantasies over the last few years. I'm guessing that's because my sex life with my wife has faded over the years and I'm looking for alternative stimulation.
Just a little background. When I was about 10 years old my older sister forced me into her open bottom girdle and then picked me up and put me over her shoulder and carried me outside the house and into the front yard. I had pissed her off for some silly reason that I don't remember and this was her revenge. She wanted to embarrass and humiliate me in front of the neighbors and all my boyhood friends. So she carried me across the street and put me down in the yard where by buddies were playing ball. I had nothing on but the open bottom girdle and died of embarrassment as I ran home while my friends laughed at me.
Little did she know that would lead to me crossdressing today. It turned me on so much (not that I knew what "turned-on" was then) but it gave me both a mental and physical rush that I can still remember it to this day. I've tried unsuccessfully over the years to recreate the same rush by dressing up in women's clothes – specifically lingerie and going outdoors but haven't duplicated the feeling.
My wife knows about my crossdressing and tolerates it but doesn't endorse it nor does she participate. Therefore, I only dress up when she's gone for a weekend to visit one of her girlfriends or on a business trip.
In the past I tried to get her to dominate me and order me outside dressed in lingerie and she did a few times but she wasn't really into it and I stopped asking for it. Since I still craved to be dominated I finally posted a profile on ALT.com.
I had a lot of BS responses but after about two months a serious response came from a man living in a different state. We traded e-mails for awhile then got on Instant Messenger. He pried all my fantasies out of me, called me his slut and I called him Master.
One night he decided I was going to perform a striptease for him via webcam. Well I didn't have a webcam so he ordered me to purchase one and the next night my wife was out of town I would be giving him a performance.
My wife was going out of town in two weeks so I purchased the webcam and told my wife we could use it when we talked with out of town relatives. She was OK with that explanation. I also went on the internet and downloaded a few striptease videos to give me an idea of how to do a striptease.
For the next two weeks I practiced my striptease in front of a mirror whenever my wife was out of the house. If I say so myself, I got pretty good and was looking forward to stripping for my Master. He already had a few pictures of me he ordered me to send him but this going to take it to another level.
On the big night I needed liquid courage and drank a couple of Martinis. Since I knew this was going to be a once in a lifetime experience I also set up my video camera behind and above the webcam so I could capture the entire evening on film and relive it whenever I had the urge.
I gave the performance a professional would have been proud of. My outfit was sexy, my make-up was perfect and with my wig you couldn't tell I was a man - at least until the very end. I had music going in the background and stripped down to my garterbelt, stockings, lacy thong and matching lacy bra stuffed with my 40DD breast forms. I then pulled out an 8 inch realistic dildo and proceeded to give it head while looking into the cameras.
I licked it from tip to base to tip and then tried my hardest to deep throat it. Although I couldn't take it all I was able to get most of it in my mouth. I was trying to show my Master how I would treat his cock if I ever had the opportunity. I then turned around and got on my hands and knees.
This wasn't part of my planned striptease but the Martinis had loosened my inhibitions and I wanted my Master to get hard and horny watching me. I then reached behind me and pulled the thong to one side and proceeded to work the dildo up my ass. With only my saliva as lubricant it was difficult but I was horny and succeeded.
I fucked my ass silly then turned around so I was facing the cameras and pulled down my thong to show my Master how hard I was and to thank him for allowing me to perform. My Master rarely allows me to cum but I guess my show did the trick as he told me to stroke myself till I came while he watched.
It didn't take much effort for me to cum then my Master signed off and I went to bed totally satisfied and exhausted.
The next morning I was awakened by my wife coming home early from her trip and opening the garage door. Fortunately, a neighbor was outside and she talked with her for fifteen minutes which gave me the opportunity to do a quick clean-up.
I quickly put the video camera away, hid my lingerie, put on shorts and a t-shirt, made sure I had no leftover make-up then went downstairs and greeted my wife. All was well and I escaped being caught by my wife crossdressing.
However, that same morning my boss called and told me she needed me on the east coast the next day for an emergency meeting. I quickly packed and caught a flight to Florida that afternoon.
This is where this story begins...
While I was on my trip to Florida my wife unbeknownst to me loaned the video camera to her very good friend Lucy so she could film one of nieces in a school play. Lucy used to work for me and we were once friends. But she now dislikes me from when I had to demote her. Lucy and my wife remain good friends while Lucy will not even talk to me.
A couple of weeks later Lucy invited my wife and I to a BBQ at her house. As there were going to be a houseful of friends and relatives I didn't feel I would be obligated to make nice with Lucy and agreed to go.
The BBQ was good and it being a very hot day, I like everyone else drank too much beer. As things were winding down Lucy called us all inside the house to watch a couple of home videos. Almost all of us moaned but felt obligated to watch after enjoying the BBQ.
Lucy showed us her niece's play and all the men complained. So she offered to show us a video of a stripper that she took at a recent party. All the guys including myself cheered and she pressed play.
Within 10 seconds I thought I was going to die of embarrassment. The stripper was me and it was the video I took when performing for my Master. How in the hell did she get a hold of it? I still didn't know my wife had loaned Lucy our camera with the video I made still in it!
The guys were enjoying the show and I wanted to crawl away. Then I realized with my make-up and wig no one knew it was me and they even thought it was a woman. They went nuts when I sucked then fucked the dildo. Looking around I saw a few tents in the front of their pants and even a couple of guys were rubbing their hard-ons. Those sick individuals, didn't they realize they were watching a man strip and suck and fuck the dildo?
I knew what was coming at the end of the video when I pulled down my thong and jerked-off for my Master and was waiting for the group's reaction. It never came as the video ended before then and everyone thought I was still a woman and my identity was safe.
The guys wanted more details about the stripper and Lucy exclaimed "Her name is Cynthia and she claims she strips at parties to earn extra income but I suspect she does it because she's a slut and an exhibitionist." How did Lucy know my feminine name was Cynthia? Had my wife shared some of my secrets???
Mark, one of the single guys at the BBQ, announced he wanted to hire Cynthia to strip at a bachelor party he'd be throwing in a few weeks. Lucy with a big smile at me offers to set it up.
"Does Cynthia do more than strip?" asked Mark
"What do you mean?"
"Does she do more than strip and play with a dildo?"
"Like what?"
"You know"
"No I don't know, you need to spell it out."
"OK, S E X"
"I guess we could ask her right now" with an evil smile at me.
"What are you going to do, give her a call right now?
"No, I'll just ask..." long pause with that evil grin "you to think about what you specifically might want like. Usually men want blowjobs and to fuck tight little asses – is that what you want me to ask Cynthia if she'll do?"
"Hell yes, and how much?"
"OK, I'll do it." as Lucy smiled at me. "I know Cynthia charges a flat fee for an evening's entertainment and will perform any and all sex acts. So if you hire her she will arrive at the specified time and not leave till everyone is totally satisfied." "How do you know this?" asked Mark. "Because my husband once hired her for a bachelor party and I understand she didn't leave until no guy could get it up anymore." I wanted to run and hide! But what could I say or do? I just sat there looking at Lucy while she kept digging a deeper hole for me.
My only thought that kept me from running was that no one would ever see Cynthia again. I made up my mind right then and there that I would never dress up again. Cynthia would just disappear from the face of the earth. At least that's what I thought till Mark asked Lucy if she really thought she could get Cynthia to perform for him and his friends?
Lucy said with a shit eatin grin "I can guarantee it!" And then it hit me, Lucy has the entire original tape where I filmed myself from start to finish transforming myself from a nude man with a hard-on to the woman everyone just saw doing the striptease and then sucking and fucking the dildo. She was the one that edited out the parts that would give away my identity. I knew then Lucy had me over a barrel and I'd be forced to do everything she ordered or she'd share my secret.
"So my recommendation is you invite as many friends as you can think of to your party and charge them a nominal fee to cover Cynthia's fee. That way you and your friends can get all the sex you can handle for almost free."
"Wow, that's pretty sweet of you Lucy! We've known each other for years but have never been close friends.
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Keywords: Lucy's, Revenge,