Lucy's Revenge

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Former employee blackmails me into gay sex.
8.2k words
4.52
313.1k
163
4

Part 1 of the 6 part series

Updated 10/27/2022
Created 07/20/2006
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Cynthia_D
Cynthia_D
607 Followers

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. Why are you going to set this up? And not that I'm complaining just curious."

"Let's just say that at the bachelor party I was referring to, I suspected Cynthia had sex with my husband and I want some revenge."

"What?" I wanted to scream but couldn't. I never attended a bachelor party as Cynthia and definitely never had sex with her husband – I've never had any sex with any man!!!

"The price for me setting this up is I get to attend your party with a large strap-on and fuck Cynthia's ass. Don't worry I won't stay too long and prevent you from having fun. I just want a little payback and I know you guys with all your lesbian fantasies would love to see me fuck her ass." Lucy smiled at me when she said this and I knew then this had to do with me demoting her a couple of years ago and she was finally going to pay me back in spades. There's nothing like a woman scorned!

OK, let me say at this point I was totally humiliated and embarrassed although no one but Lucy would have known or suspected what was going through my mind. But the worse part was I had an erection! How could that be?

Thinking back now I think for the first time someone was able to duplicate the humiliation my sister put me through when I was 10 and I was turned on. I knew then I'd do whatever Lucy ordered going forward no matter how embarrassing or humiliating to keep this "sexual feeling". This doesn't mean I'd ever let her know. In fact I was determined to say "no" every time she told me to do something and force her to order me to "do it or else." The "or else" threat I knew she would be good for and she probably wanted to do anyway so I thought the more I said "No" and fought her orders the more she'd push my limits! Man, was I right!

The next day Lucy called me at work. How she got my number I don't know since I recently changed employers and she never called me there before. When I answered the phone she sweetly asked for Cynthia. I pretended I didn't know who Lucy was even though the caller ID gave it away and told her she must have the wrong number.

Unfazed she said "I don't think so and I'm just calling to confirm my lunch date with Cynthia for tomorrow at noon at Scopazis restaurant." I didn't say a word. After about a minute of dead silence where you definitely hear a pin drop from a mile away Lucy said "Cynthia better be there or the entire tape, not the edited version, with about 50 copies will show up at work and also with your family and friends. Would you like that?"

Again I was speechless. What could I do? What could I say" "If Cynthia's not at the restaurant at noon the tape will be distributed. It's your choice." I finally spoke and agreed to meet her for lunch but said I couldn't dress as Cynthia at work and would therefore have to come dressed in my male clothes. She laughed then said "I agree so here's what you're going to do. You will call in sick tomorrow. You will dress as Cynthia and you will meet me at Mt Diablo state park at 11:00AM at the picnic grounds." I now knew she'd already given this plenty of thought and I was being played by someone better than me at this. So much for me trying to control the situation.

The next day I woke up early without the need for my alarm clock. As you could expect, I was very nervous, had lost that "sexual feeling" and tried for the umpteen time to think of a way out of meeting Lucy but couldn't. I called in sick with the flu – a lot's been going around so no one at work would think anything of it.

I finally gave in to the inevitable and got in the shower and shaved my entire body extra close including my cock and balls but left a little landing strip just like a woman would do. I even shaved my face twice but left the hair on my head. After drying off I rubbed some of my wife's body lotion all over. My cock immediately got rock hard and I wondered whether if it was the lotion or was it because I finally had someone forcing me to dress as a woman and do who knows what and I wouldn't have a choice! I was totally humiliated and turned-on at the same time. I wanted to stroke myself and knew it wouldn't take much to make me cum. But I knew if I did I'd lose the horny feeling and anything Lucy made me do would be that much more difficult mentally to do so I didn't.

Then I dressed as "Cynthia" but not knowing what Lucy expected and being the middle of the day in a state park I decided to dress casual and for outdoors. I put on beige thigh-high stockings, a lacy white thong that had enough material to keep my cock and balls tucked back between my legs but showed off my landing strip. I put on a lacy white racer-back bra stuffed with my 40DD breast forms and a white racer-back t-shirt, a blue jean mini-skirt and women's white with pink accent tennis shoes. The outfit wasn't overly feminine but would never be mistaken for men's clothing.

I then took the time to make sure my make-up was perfect as I knew in a couple of hours I was going to have to try to pass for a woman. My pink lipstick matched my pink eye shadow which was the same shade of pink as my long fake fingernails I had glued on. My wig was a deep auburn color that came just to my shoulders and had a lot of loose curls. To finish off my outfit I put on a gold necklace, dangling clip on earrings (my ears aren't pierced) and a women's ring on each hand. It might not have been needed but not knowing what Lucy expected, I sprayed on some of my wife's Obsession perfume. I had no place for my wallet so I grabbed a small pink purse I bought one time on a whim and because it was on sale. I put my driver's license, a credit card, the $8.00 dollars in cash I had and my cell phone into my purse and at 10:30 got into my car in the garage, opened the garage door and drove off to the state park. I prayed none of the neighbors saw me as I never go out during the day as "Cynthia" and would die of embarrassment if I was caught by someone I knew and would see everyday going forward.

The drive to the park was nerve racking but also a turn-on. The only way to the park was to drive the entire way on 4 lane roads with lots of stoplights. Every time I came to a stop I didn't want anyone stopping next to me and looking over and seeing I was a man dressed as a woman. On the other hand, every time I stopped for a red light I wanted a truck to pull up along side me and have the driver check out my stocking covered legs, my miniskirt and my 40DD breasts with nipples that clearly showed. My little head started thinking for my big head and the fantasies started coming and I got as hard as my tucked cock could.

My fantasies and hard-on came crashing down when I had to stop and pay the entrance fee at the park's gate. The ranger looked hard at me and I knew he knew I was a man dressed as a woman. I paid the $5.00 entrance fee and didn't say a word as my voice would have confirmed I was a man.

As I was about to drive off he smiled and said "Lucy wanted me to tell you she has moved your lunch from the picnic grounds to campsite #13 and you're to meet her there. I'll see you later."

Uh oh! I now knew I was in deeper trouble than I could ever have imagined. I thought all Lucy would have me do was get out of the car and force me to walk around the picnic area all dressed up as a woman so I'd be seen by other picnickers to humiliate me. I never guessed she would involve someone else, much less a ranger!

I looked at the map the Ranger had given me and drove to campsite #13. Not that I'm superstitious, but in the back of my mind I hoped it wasn't an unlucky #13.

When I arrived I found Lucy already there. She was sitting at the campsite's picnic table with an evil grin and indicated I was to get out of my car and walk over to her. I hesitated as long as I dared then slowly got out of the car and walked over to her.

Other than my wife this was the first time anyone I knew was seeing me dressed as a woman. I was totally humiliated and it would have been bad enough if it was a friend or neighbor that caught me by accident. But this was a woman that had a grudge against me and I had no option but to do anything she wanted.

When I finally stood in front of her she smiled and told me to turn around slowly in a circle so she could see all of me. When I was back facing her she smiled her evil grin again and said "I'm glad to see you can follow orders Cynthia because that's what you're going to be doing all afternoon and then anytime in the future I choose to give them. Do you understand?"

"Not entirely. I know you have a tape of me dressed and doing things I'd rather not let anyone see, but I'm assuming you've ordered me here today to embarrass and humiliate me for some revenge you perceive you need to get. I'm reluctantly complying with your demands today and will do anything you order me to do to satisfy your need to humiliate me. But then it's over and I want my tape back and we never need to speak to each other again."

I was being eloquent, logical but delusional and Lucy saw it different. "You demoted me two years ago and I've had to face my family, friends and business acquaintances everyday since then with embarrassment and now you're going to pay. However, you're not worth two years of my time so here's the deal. I'm going to condense your humiliation into two days. You will do anything and everything I want today and then again one night in the near future. Then I'll give you back your tape and all the copies I've made. Do you agree or should I distribute the copies I made of your tape tomorrow?"

"How do I know you'll keep up your end of the bargain if I do whatever you say?"

"You won't know for sure, but in all the years I worked for you or we've known each other, have you ever known me to lie?"

"No, you've never lied that I've known about, so I guess I have no option but to trust you. So do your worst and let's get this over with. No, no, no, I'm just kidding; please, please do not do your worst!" Damn I hate it when my turned on cock makes me say things that will get me into trouble!

Cynthia_D
Cynthia_D
607 Followers