Lucy's Revenge Ch. 06

Story Info
Cynthia is the Bachelor party's entertainment.
10.2k words
4.46
155.8k
59
0

Part 6 of the 6 part series

Updated 10/27/2022
Created 07/20/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Cynthia_D
Cynthia_D
607 Followers

Final Chapter

It was Friday night after a very long week of being humiliated. I had a couple of cocktails to calm down after my latest forced outdoor adventure - being exposed to numerous people while crossdressed. The phone had rung and I made the mistake of answering it thinking it was my wife who was due home that weekend. But the caller wasn't my wife it was Lucy.

Lucy continued the conversation "I'll pick you up at 10:00 tomorrow morning as we've got a lot to do to get you ready for your stripping debut."

"What do you mean a lot to do?" I hesitantly asked.

"Well I wasn't going to spoil the surprise but I'm sure you want to fantasize all night long about going to the spa and then the beauty salon tomorrow. After all you do want to look as feminine as you can don't you? "

This wasn't a fantasy this was a nightmare! But I had to answer "yes" immediately to anything Lucy asked or be punished. Damn being blackmailed sucked! So I said "Yes Mistress."

"Yes Mistress, what?" Lucy asked so I'd have to embarrass myself by telling her I wanted to do something that she knew damn well I didn't.

"Yes Mistress, I want to look as feminine as possible for tomorrow night when I perform a striptease at the bachelor party."

I couldn't believe she followed that up with "And why is that slut? Is it so all the real men will find you irresistible and want you to suck their cocks? Well is it?"

I'm straight and I didn't want to suck on any cocks but Lucy was enjoying humiliating me by making me say I did.

"Yes Mistress, I want all the men to find me irresistible so they allow me to suck their cocks."

"You are the perfect little slut! I'm going to miss blackmailing you into submission and humiliating the hell out of you after tomorrow. So let's make tomorrow special. I'll give it my best shot to get you to refuse to do something I order you to. If I succeed, I'll abandon you handcuffed in the bathroom at the truck stop for the night. Only this time I will not come back to release you. I remember how much fun you had last time."

I also remembered when Lucy abandoned me at the truck stop. What a painful experience it was and I swore to myself I'd do any degrading and humiliating thing Lucy dreamt up to prevent being handcuffed in the truck stop's bathroom and allowing the truckers to use me sexually over and over again.

She continued "Sleep tight and I'll see you in the morning." Lucy was laughing hard when she hung up the phone.

I didn't sleep well and was nervously waiting for Lucy when she showed up the next morning. I let her into my house and she told me to strip naked and put on what she brought me to wear. It consisted of red bike shorts with a 2 inch inseam, a matching red sports bra and red 4 inch heels.

I got dressed and she told me to go outside and stand on the front porch till she went through all my feminine attire to choose what I'd be wearing that evening. As soon as I stepped outside Lucy locked the front door behind me ensuring I had no place to escape to and hide. I prayed none of my neighbors walked by.

If I was a woman and wearing tennis shoes instead of the red heels I might have looked ready to work out at the gym but I knew I looked ridiculous which is what Lucy wanted. Needless to say my face matched the red in my outfit.

After what seemed like an hour but I'm sure was closer to thirty minutes, Lucy came out with a couple of big bags but I couldn't tell what was in them. She put them in the trunk of her car then unlocked the car doors so we could get in. Before she backed out of the driveway and drove us to the spa she put the top down on her convertible car ensuring a very exposed and embarrassing ride for me.

It turned out to be an exclusive women only spa but Lucy had made prior arrangements to get me in the back door and for me to receive the "full" treatment.

There were two absolutely drop dead gorgeous employees there to take care of me. I don't know what it cost me since Lucy was using my credit card but I'm sure it was plenty extra because they were both naked! My cock was straining to get hard but the chastity device did its job.

I knew Lucy was doing this to make sure I would be horny as hell with a severe case of blue balls for the bachelor party. But as sexy as these two naked women looked, I didn't care if I got blue balls. They had me strip naked other than the chastity device then spent the next few hours giving me a full spa treatment.

The wax job they gave me to remove all my body hair hurt like hell but everything else they did was almost orgasmic – especially all the fondling of my balls and nipples. I knew the only reason they were paying extra attention to my balls and nipples was the large tip they were going to get from my credit card but damn it felt good and I was horny.

When they were done with my facial and total body wrap my body, I smelled like a woman and was soft to the touch. The bikini wax they gave me would make any stripper proud but the waxed eyebrows had me very concerned. How long before they grew back? When could I go out in public without wearing sunglasses to hide my very feminine look?

Lucy gave me a pair of red lacy boy short panties, a red lacy bra and red heels to put on. Once I had them on she handed me my 40DD breast forms to put in the bra. To cover what I was wearing when we left the spa she allowed a very short white robe that barely covered my ass.

Only this time it wasn't the back door for me. No, she had me leave through the front door. Unfortunately the lobby had several women in there waiting for their spa treatments. They immediately stopped reading their magazines or conversations to stare at me. It was obvious I was a man dressed in heels and had fake tits under the robe. My face turned the color of the lingerie I was wearing as I walked out of the spa.

Once outside I had no choice but to wait for Lucy who had gone out the back to get her car to drive around and pick me up. Lucy took her sweet time to make sure there was plenty of time for a lot of women to go in and out of the spa and see me.

Eventually Lucy drove up and let me in her car. She actually apologized for taking so long but said she had an important phone call she had to make before she could pick me up. I knew she was lying but what could I say? She has taken her time to humiliate me further!

Lucy drove me to the beauty salon next. I knew the beauty salon was located at one end of a strip mall because Lucy pointed it out as she drove past it. Lucy parked at the opposite end of the strip mall and as far out in the parking lot as she could. She ordered me out of her car and she got out also. She came around to my side of the car and removed the belt from my robe. She told me to turn around and put my hands behind my back so she could tie them. I was determined to do whatever she ordered so I did.

She tied my hands tightly so there was no escaping then told me to turn around and face her. Once I turned around she opened my robe and pulled the sides far apart so my red lacy stuffed bra and boy short panties were totally exposed.

Lucy smiled when she said "You are now going to walk to the beauty salon but there will be no hiding on your part. You should be proud of how you look in your bra, panties and heels and I know you want to show them off. So you're going to walk to this end of the building before you get on the sidewalk. Then you're going to walk the entire length of the strip mall to the beauty salon on the sidewalk where everyone can see you. You really want to do this, don't you slut?" She couldn't help herself from laughing at me.

I told myself I could survive anything she ordered me to today to end this and said "Yes Mistress, I want to do this."

"I just knew you did. And remember if you try to hide or step off the sidewalk for any reason I'm going to abandon you at the truck stop. Have a fun walk slut."

I hesitantly walked through the parking lot hiding behind cars till I reached the end of the sidewalk. This is where my truly exposed walk would begin. The robe was wide open and I had no way of closing it with my hands tied behind my back. The heels were obviously going to be visible no matter what, but now my bra stuffed with the breast forms were on display as well as the lacy boy short panties. At least I was covered decently enough the police could only hassle me but not arrest me for indecent exposure.

However, once I stepped onto the sidewalk I didn't really care about the police. I knew I was going to walk past at least twenty people if not fifty before I made it to the beauty salon! There was no way I could cover up and everyone one of them would know I was a man dressed in lingerie. And if someone wasn't already looking at me, I knew the clicking of my heels on the sidewalk would attract their attention. What man doesn't turn to look when they hear heels? They're always hoping for a hot babe in a mini-skirt. However, these men were in for a real surprise when they'd see me. It was a very long walk and I was seen by a lot of people. Most people just stared but some said rude comments while still others made very suggestive remarks. Thank God I didn't see anyone I knew or it would have been that much worse.

When I arrived at the beauty salon Lucy was standing out front holding the door open for me so I could enter. I know she wasn't doing it out of the kindness of her heart. She wanted to make sure I didn't try to hide behind a pole or step off the sidewalk to avoid being seen.

Once in the beauty salon I was led to a private room so none of the other customers would be offended by what happened next. Lucy untied my hands and told me to strip off everything other than the damn chastity device that I couldn't take off anyway.

Next Lucy told me I was to submit to whatever the two beauticians had in store for me. I knew my credit card was taking a serious hit when these two beauties got naked. They were just as gorgeous as the two from the spa and I wasn't going to complain. Other than I couldn't get hard or off – damn I hated Lucy!

One beautician painted my toenails a bright red and then glued very long fingernails on me. The other beautician weaved long hair into mine then worked her magic with make-up on my face. In between the coats of nail polish or make-up these two gorgeous women played with my balls and sucked on my nipples. They offered me their nipples to suck on but then kept them out of reach to tease me. They were driving me nuts and Lucy just stood off to the side watching me squirm and laughing at me.

Lucy finally asked "Slut, are you willing to do everything I can dream up for me to take off your chastity device and allow you to cum?"

I was desperate "Yes Mistress! I'll do anything you want. Just free my cock so I can cum. Please, please, please!!!"

"I might, but not yet. I still want you horny for tonight so you'll do anything. Why don't you tell us what you're going to do tonight?"

I know it's hard to believe but I'd gotten over my embarrassment of the beauticians seeing me naked and feminizing me. But now I blushed bright red. There was no reason not to tell them other the utter humiliation of admitting what I was going to do. And besides, if I didn't tell them, Lucy would and I'd be punished.

"I'm going to perform a striptease at a bachelor party."

"And?" demanded Lucy.

I bowed my head in shame as I said "I'm to be the party's entertainment and make sure everyone is satisfied before they go home."

"And how are you going to do that?" asked one of the beauticians in a very sexy voice as she pinched and twisted my nipples.

"I'm going to suck every cock dry unless of course the guy chooses to fuck my ass."

Both beauticians giggled and asked Lucy if they could come to the party watch me. After all they were feminizing me for the party and also assuming their boyfriends didn't mind.

Lucy told them that they should attend especially after making me so pretty. "In fact, you should bring your boyfriends with you. Cynthia here wants as big as audience for his show as he can get. And who knows, maybe your boyfriends might even want to join in and get blowjobs. Unless of course you're worried a crossdressing slut like this sucking their cocks while you watch will take them away from you."

One beautician spoke for both "No, we're not worried Cynthia will take away our boyfriends. But to tell the truth, sometimes after too much drinking our boyfriends do like rough sex and it might be fun to have them have it with Cynthia while we watch and so we won't have to satisfy them later."

What was Lucy trying to do me? I didn't want a bigger audience! And I sure as hell didn't want any more cocks to blow or fuck. The obvious answer was Lucy was trying and succeeding in making tonight as humiliating as possible.

When the beauticians were done, Lucy gave me back my red lacy boy shorts, bra and heels to put on. When I was dressed she had me put my breast forms in the bra and then look in a full length mirror. I was shocked. It's amazing what professional beauticians can do. My make-up was perfect; my hair was long and in a very feminine style. Having the wax job to remove all my hair and all the lotions rubbed into my skin made me look more like a woman than I ever had in my life.

Not to be egotistical but I looked hot and if I didn't know I was a man I may not have suspected it. But I did know I was a man and still had concerns about passing as a woman.

Lucy told me to put my hands behind my back and she tied them tightly. "OK slut, time for you to walk back to the car so we can head to the party."

I looked in the mirror and realized something was terribly wrong. I wasn't wearing the short white robe. Not that it covered much but it gave me some feeling of decency.

"But Mistress, what about the robe?"

Lucy laughed and said "I want everyone to have a totally unobstructed view of you in your lingerie and your bouncing tits. I bet you don't know how far away someone can see those massive 40DDs on your chest and how much they bounce when you walk in heels."

"Now, the same as before. You will walk on the sidewalk to the other end of the mall without hiding or stepping off the sidewalk. You know what will happen if you do. If anyone engages you in a conversation you will stop and talk with them till they walk away. You will not break off a conversation and walk away; only they are allowed to."

"Think of the excitement you're going to give every man that sees you. Every man will be staring at you in just your lingerie. Then think of the sexual offers you'll receive from them. And when you respond you'll give it away that you're a man. I just can't imagine the humiliation you'll feel."

"But before you walk back to the car lets see if we can make this more difficult for you." And with that Lucy knelt down and proceeded to tie a very thin but strong piece of string around my ankles leaving a piece about eight inches between them. I was very effectively hobbled.

She stood up and smiled saying "That will ensure you only take short mincing steps all the way back to the car."

I already couldn't walk very fast in 4 inch heels, but this guaranteed I'd be walking at a snail's pace. And the outfit I was wearing? It was designed for maximum attraction without getting me busted for indecent exposure.

"And here," Lucy said stuffing some business cards down the front of my panties "you are to offer every man that talks to you one of these cards. You will tell them the card has the address where you'll be performing your striptease later tonight as well as a coupon good for a free blowjob from you. It's a shame you can't hand them a card yourself since your hands are tied behind your back. I guess they will just have to reach into your panties and get the card themselves. That should be fun, huh slut?"

"Just to make sure you humiliate the hell out of yourself on the walk back to the car, I'm going to walk five feet behind you and if you deviate from anything I've told you to do, you're going to be abandoned at the truck stop after the bachelor party. I'm especially looking forward to listening in on your conversations with the men. And you had better convince more than half of the men to take a card out of your panties and show up tonight for a blowjob or it's to the truck stop."

And I thought the walk to the beauty parlor was long. This took me at least four times as long. Lucy had guaranteed it by hobbling my ankles but then every man that saw me either thought I was a damsel in distress or a hot slut ready to be fucked and they were going to be the man to do it. Every fucking man (and a few women) stopped to talk with me.

As Lucy predicted, as soon as I responded to them my voice gave me away and most were turned off but there were a few sick men still interested in me. But only a few men weren't good enough for Lucy. No, she required me to convince more than half the men to reach into my panties and take a business card.

This forced me to flirt with every man. Or if that didn't work, beg them to reach inside my panties to take a card. Can you even imagine the things I had to say and promise to do to get some of the straight men to reach into my panties??? I promised to perform every sexual act imaginable. And trust me more than a few of the activities the men wanted were in my mind sick and disgusting but I had no choice.

Lucy listened to every word said and the promises I made. She handed each of these men a different business card from what they'd taken from my panties as they were walking away.

When we eventually got to her car she explained that the cards she handed out contained my real name, home address and both my work and home phone numbers.

Lucy laughingly told me this was just in case they couldn't make tonight's party. She wanted them to still have the opportunity to get a blowjob when it was more convenient for them. How could Lucy do this to me???

Lucy finally let me in her car without untying my hands and put the seatbelt on me. I couldn't free myself nor could I cover up. Of course she put the top down on the convertible then drove me to a hall that was rented for the bachelor party. She drove slow and stayed on multi-lane surface streets with lots of stoplights. I swear she hit every light red on purpose so cars would pull up along side us and let and let the driver and/or passengers get a good look at me till the light turned green.

To add to my humiliation she ordered me to face whoever was looking at me and smile. It was so embarrassing but I did as ordered. Most of the men rolled down their windows and made sexual comment that made me blush even more. I couldn't believe Lucy could make this more humiliating but she managed to.

She pulled over to the curb and stopped the car. Next she reached into my panties and pulled my cock that (that had been tucked and hidden) from between my legs and now to the front of my panties so I had this large lump. Obviously it wasn't all my cock since I had the chastity device on but it was an impressive lump that no one looking would ever mistake me for a woman. Then Lucy pulled my bra straps off my shoulders and partially down my arms. It exposed the top of my breast forms but I knew if it was a real woman looking like this she would be hot!

"From now on slut," Lucy said before pulling back into traffic "I want you to look at everyone that sees you and smile then lick your lips in a very suggestive way. You are to sell yourself for the slut you are with just that or I'm abandoning you at the truck stop. Do you understand slut?"

"Yes Mistress" I said.

"Now for practice I want you to smile at me and run your tongue over your lips. And it better convince me what a complete and total slut you are."

Oh God, how can I do this? Sure I wanted to fuck Lucy because she was hot, but I absolutely hated her for what she had put me through and was still going to tonight. As humiliating as it was, which was Lucy's intent, I turned to her, smiled and licked my lips. Of course my fantasy was my lips were coated with Lucy's pussy juice which definitely helped me smile.

Cynthia_D
Cynthia_D
607 Followers