Don't Ever Get Caught

by: Cissykay

 

Chapter 2

I had a very uneasy night. As much as I tried, I couldn't sleep as I kept replaying all that had happened to me in the last twelve hours. I knew that everything I had worked for since college was now gone. Cheryl would most certainly file for a divorce first thing Monday morning. I awoke at 6:00 AM and laid in bed trying to get my thoughts together. I had two days to convince her that I would change my ways, and never be unfaithful to her again. After all, I did love her very much, and I didn't want to lose her. I resigned myself to do whatever it would take to give me one more chance. I finally got myself out of bed, and went to the closet to get the maid's outfit.

I struggled to get into my new uniform. After a few minutes I had the zipper up and looked at myself in the mirror. Although my wig was all a mass of tangles, and my makeup had faded, I still looked damn good for a man dressed as a maid. I walked back into the closet to get thecollar, and noticed a small piece of paper taped to it. It instructed me to put on a fresh coat of lipstick, brush my hair, and do nothing else. I fastened the collar around my neck, and locked it in place. I did as instructed in the note, and was ready to go downstairs to prepare breakfast for Cheryl and Barbara.

As I tried to walk down the stairs I immediately realized that my feet were killing me from having had these heels on since yesterday. I managed to hold on to the railing, and get myselk to the bottom without falling. When I reached the bottom and began to walk, I noticed that I had to take very small steps because of the pain. I almost had to walk on my tiptoes so the heels wouldn't take my full weight, and make me wince in pain. I finally made it to the kitchen and went directly to the refridgerator. There was a note taped to it also. "My darling Kendra, this will be your last opportunity to leave. I realize that you can find something to cut through all the leather that is locked to various parts of your body. If you choose to do that, I will proceed with everything that I threatened yesterday. If you choose to stay, you will be required to show me that you are truly sorry for breaking my heart. I do love you, but you have forced me to punish you for your transgressions. I know there have been many more than just Barbara. If you wish to stay as my husband, then I am going to make sure that you never cheat on me again. On the diningroom table, you will find a pair of steel handcuffs. Lock them on your wrists, and then begin to make breakfast for the three of us. I know we will all be quite ravished after yesterday, so make plenty. There is a list of what we would like on the diningroom table. Now be a good little slut and get to work."

Cheryl was right. I could get out of what I was wearing, and remove all the makeup. I could leave now, and take my chances in court. I am a damn good attorney, but with the film and Barbara as a witness, I knew I wasn't that good. Perry Mason couldn't win this one. I decided that my only hope was to placate Cheryl until she calmed down, and then I could talk some sense to her. I went to the diningroom and locked the steel cuffs on my wrists. Then I read the breakfast note and knew I could take care of their requests. Bacon, eggs, juice, toast, and coffee. Just thinking about it made my stomach rumble. I prepared a huge breakfast by the time I heard the sound of slippers sliding into the kitchen. "Good morning Kendra. I am so glad that for once you have decided to think with the head on your shoulders instead of the one between your legs. Is breakfast ready?" "Yes Cheryl, breakfast is ready, and I'm not really sure that I like the name Kendra. My name is Ken." "Well that just too bad. From now on until I'm sure that you have changed your ways, you will be addressed as Kendra by me and my friends. What's more, you will address me as Mistress Cheryl at all times, and any other female that you talk to in private as Mistress. If that isn't acceptable to you, we can always make it sissy Kendra, and you will be required to address all women as Mistress at all times. Which will it be?" I knew that this wasn't the time to test her resolve, so I agreed to her terms.

"Now, be a dear and set up breakfast in the diningroom. Mistress Barbara will be down shortly." I set up everything that was needed in the diningroom, and sat down to eat. "What the fuck do you think you're doing. The maid always stands and waits for her Mistresses to be seated before she serves them." I jumped to my feet and stood at attention until both ladies were seated, and then served them before I went back to my breakfast. When we were through eating, and the ladies were finishing their coffee, the talk was mostly woman stuff, and it was like I wasn't even there. "Kendra, please remove the dirty dishes and return as soon as you are through. There are a few things we need to address. On your way back, get a pad and pen from the study, and bring them with you." I did as I was ordered. I had a feeling that I didn't want to piss her off. Especially after reading in the note that she still loved me. I returned with pad and pen in hand. My wrists were beginning to feel the effects of the manacles by this time. I sat back at the table and waited silently until Cheryl and Barbara were ready to try to humiliate me further.

When they were through with their conversation, Barbara got this evil look on her face. "Mistress Cheryl has told me that I am not the first woman that you have had an affair with. Did you tell all of them that you were divorced, or just me? You don't have to answer that. I really don't care." I was in shock. Not because of the question, but because Cheryl knew that I had played games with other women beside Barbara. "Before we begin, Barbara has brought something from her playroom that I would love to see on you. It will give you something to think about instead of trying to lie your way out of what you have done." Barbara then went behind me and took something out of a bag that was on the floor. I had no idea what it could be, and since I couldn't see behind me, I had no way of getting a look. "Open wide honey, NOW. I just did as I was told. Barbara then inserted a vile looking gag in my mouth. I could feel some sort of fairly hard rubber inside my mouth. When I lowered my eyes, I saw what had to be an eight inch black rubber penis protruding out the front. The big black prick had a small hole in the head, just like a real penis. She tightened the strap as far as she could, and then buckled it. I heard a click and knew at once that it was locked on, and not coming off without the key.

"Oh that looks so delicious Barbara. I just love it. It's too bad though that the penis in her mouth is so small though. I would like it even more if she could experience what it's like for us girls, when we have to make men happy while we get no pleasure." "Not to worry Cheryl, I think I may have the soloution for that little problem." Barbara than walked in front of me, and inserted a small metal tube in the hole. It was attached to a tube and a bulb. When Barbara started to squeeze the bulb, I could feel the penis inside my mouth expand. The more she squeezed, the more it filled my mouth. My cheeks couldn't expand because of the strap on the gag. It wasn't long before my mouth was totally full and it became very uncomfortable. Barbara kept pumping until I began to gag on the gag. "Oh, look at her eyes. I believe they are going to pop right out of her head." Finally Barbara removed the pin, and I began to struggle with the gag to rip it off, but it was useless. "Be a good girl Kendra, or we'll leave it on all day." I removed my hands from the gag and just sat there in pain.

Cherly finally stopped laughing at my plight, and then dropped her first bomb on me. "I want you to sit there and write down the name of every woman that you have fucked, sucked, or fondled since we were married. Don't be so foolish as to think you can omit any because I already know of some, and if I ever find out that you weren't honest, I'll have your balls removed." I was in tears. It was partially because of the discomfort of the gag, nut mostly because of what I was ordered to do. I didn't want Cheryl to know how many women I had slept with, but I also knew that she was dead serious about what she said. I started to write down all the names of the women. I found it strange that I had to really think of some of the women, because they were one night stands. I was very grateful that I had never slept with a prostitute because I would have never remembered their names if they had told me. After about fifteen minutes, I thought I had them all, so I slid the list to Cheryl.

Cheryl read the list very carefully and then broke out in a fit of laughter. "Thirteen names on the list Kendra. I guess what they say it true. Thirteen is a very unlucky number. You are going to find that out before I'm through with you. I guess I didn't satisfy you in bed if you had to go sleep with all of these other women." I shook my head from side to side violently to tell Cheryl that it wasn't the reason I cheated on her, but it was no use. I knew that there was nothing I could say right now to extinguish the fire in her eyes. "Go to the kitchen and wash and dry the breakfast dishes while Barbara and I figure out what to do with you." I almost ran to the kitchen so I wouldn't have to look at her distain. I did the dishes as quickly as I could. As I was putting the last plate in the cupboard, the front doorbell rang. "Kendra, answer the door and see who's there." My heart stopped beating. I couldn't go to the front door dressed as a maid with my wrists chained together, and this huge penis sticking out from my mouth. "NOW, you dumb bitch." Cheryl was in the kitchen in a flash and grabbed a hendful of my gag and started to drag me to the front door. I had to run in my heels to keep up with her. We got to the front door and she scowled, "open the door now, or I'll chain your ass to a post in the cellar and leave you there until until you learn some manners." I had no choice but to do as I was told. As soon as I opened the door I was blinded by the flash of a camera. "Smile for me honey. I want some nice photos of you for me series on the male transvestite."

Cheryl was in hyterics and I was in shock. "Don't you think you should let our guest in the house Kendra?" I stepped aside and the young woman I had met last night jumped into the house and walked right past me. "Get our guest a cup of coffee Kendra, and then join us in the dining area." I was now totally beaten, so I just hung my head and went to get her coffee. When I returned with the coffee, Barbara introduced the young girl as Donna. "Donna is a cub reporter for the newspaper. I was very instrumental in getting her the job. She will be taking photos of you from time to time. Nothing has been sent in to be printed as of yet, but it can and will be done if you decide to rebel. Also, the two policewoman you met last night are friends, and the ticket you got hasn't been filed with the court." For the first time since yesterday, I now had a reason to be happy. The life that I had worked so hard to attain was still intact.

After Barbara's speech, and a warning as to how Donna was to be addressed at all times, I was told that it was time to begin my first full day of repentance. Cheryl gave me my instructions. "I want you to go upstairs to the guest bedroom. There you will find everything you need to remove the breasts and fingernails. You will also find a bottle of makeup remover. Get everything off and take a shower. On the bed is a new set of lingerie for you to put on when you are through. I don't want you to use any of your male deoderant. There is a bottle of perfume on the dressing table also. Just put a little on your chest and neck. Put your dirty undies in the hamper and your breastforms and heels on a shelf in the closet. Now hurry off like a good little girl. You have twenty minutes."

Barbara then unlocked the cuffs from my wrists so I could undress. I removed my heels at the foot of the stairs and went to the guest bedroom. The first thing I noticed was what was on the bed. It was a pair of fire engine red crotchless panties, a matching bra and corset with eight garter straps, and a pair of sheer red silk stockings. I removed all of the effects of the previous night and jumped into the shower. It was the most soothing shower I had ever experienced. I noticed in the vanity mirror that the water was not penetrating my gag. The leather must have been treated.

When I was finished, I dressed as quickly as a man could considering I was trying to squeeze into woman's underwear. I finally cinched the corset, and after what seemed like forever got the silk stockings attached to the garters. I spritzed the perfume on the places that Cheryl had told me to, and I was ready to return to the diningroom. As I reached the three ladies, Donna took three or four more pictures.

This time it was of a man not wearing anything but woman's lingerie. No makeup, and no way to hide my identity. Not to mention the black rubber prick sticking out of my mouth. Try to explain that to a judge. "Oh you look so cute Kendra, and you did everything just as you were instructed to. If I cut you some slack this morning, will you promise to do exactly as you're told without a word?" I nodded yes. Anything had to be better than aprading around like this all day. Cheryl then deflated and unlocked my gag and I could move my jaw again. The relief was fantastic.

"I'm going to leave your collar locked on so you'll remember who is in charge at all times, but we've decided that you might be more comfortable wearing your own slacks and sweater. I've brought down the clothes for you. You're taste in clothes is so appalling that I thought I would match the outfits for you from now on. Now please put on the sweater I've laid out for you." It was my favorite white cotton turtleneck. I pulled it over my head and when I made an adjustment to the top, it hid my leather collar completely. Next came a pair of red slacks that almost matched my underwear. I hadn't worn them in quite some time."Hurry up Kendra, you take all day getting dressed. I have things to do." I got the slacks on as fast as I could and started to buckle my leather belt. "Stop right there Kendra. I'm not sure that this is the look that I want here." Cheryl walked up in front of me and knelt to inspect my pants. I had no idea why. She pulled the fly all the way down and then asked Mistress Donna to hand her the steel cuffs. All at once she looped the chain around the base of my penis behind my testicles and inserted a very small lock on the chain. The cuffs were now left dangling from my balls. She pulled the slacks up slightly and ordered me to put my hands in my pockets. To me surprise, the pockets had been cut out. When my hands went in Cheryl attached a cuff to each wrist and locked them. Next she pulled the slacks up, zipped the zipper, and buckled my belt.

I was now a prisoner in my own pants.

"Your new loafers are on the side over there. Step into them and let's see what you look like." These were leather woman's loafers with a one inch heel. Anyone who saw them would surely recognize that I was a man wearing woman's flats. "Let me take a look at you sweetheart. Yes, I think that is just what I wanted for a full day of shopping." I began to protest, but as soon as I got the first word out Donna slapped my face very hard. "Be quiet you sissy. My daddy would never yell at my mother like you were going to do. You still need to be taught how to act like a lady." Donna then looked at Cheryl. "Well, I think I have all that I need here. I'm off to the lab to do some developing. Have a good day ladies, and I'll see you tonight at the party. Oops, did I let the cat out of the bag?" "Don't worry dear, it's perfectly all right." "Your two options Kendra are to come shopping with me or I'll put you in the yard and you can wait for me to return. What will it be?" I knew I had no choice, so I opted for the shopping. "Good, it'll be so much fun. Just us two. We will shop till we drop." Barbara said her goodbyes, and left. I was excorted to my convertble, and Cheryl opened the passenger's door for me. "See, isn't it fun to be treated like a lady, even though you are nothing but a whoring little slut?" I didn't say a word as we drove away.

After driving for about thirty minutes, Cheryl told me that we were on our way to the "Unique Boutique" that Barbara had told her about. "Not to worry sweetheart, nobody there will recoginize you. Some may glance at your very swanky loafers though." She gave out with a hearty laugh. It was another fifteen minutes before we reached our destination. As we pulled into the parking lot, I noticed that this was not a very busy area. The small group of stores consisted of the boutique, a video rental store, and a full service beauty salon. There was nothing else in the general area. Cheryl opened my door and I stwpped out of the car. "Well, here we are sweetie. This little boutique caters to a special kind of clientel, and according to Barbara, it has some very special services that I'd like to try. If you are a good little whore, I may be very kind, and take you to lunch when we're through." As we started toward the store, I noticed some very bizzare leatherwear in the window. Somehow, I knew I wasn't going to like this one bit.

Inside the boutique there were racks and racks of leather skirts, dresses, vests, pants, and just about everything else one could imagine.

The was also a section of lingerie. It all looked extremely sexy with lots of lace. There was a shoe department, and a makeup counter. We were greeted by a clerk as soon as we were inside. "May I help you with anything this morning?" Cheryl immediately told the girl that she had an appointment with Miss Monique, but she was a bit early. "I'll tellher that her appointment is here, and you may feel free to browse if you'd like. She should be available in about thirty minutes. There is fresh coffee on the table at the back of the shop. Fell free to help yourself." I felt a little awkward standing there with my hands in my pockets, but the clerk didn't even set eyes on me while she spoke to Cheryl. It was as if I wasn't there. Cheryl went directly to the woman's undies. She looked at every style. She would occasionally hold a pair up and ask what I thought. I don't think she really wanted my opinion. Cheryl finally selected at least two dozen pair of panties. Most were lacy in all different colors, but I couldn't help but notice tha some were crotchless. Next she went to the stockings. About a dozen pair of those were soon in her cart. Fishnets, seamed, sheer. She had them all covered. "Barbara was right. This is a great place."

We then went to the lingerie section. Cheryl picked out about six nighties in all different colors, and all with lace trim. The more I trailed behind her, the more uncomfortable I became. I was starting to think that everyone around knew that my hands were chained to by balls. Cheryl then went to the racks that contained the leather skirts and dresses. She rumaged through the entire inventory and chose about three skirts, three dresses, and a couple of pairs of leather slacks. "I can't remember when I've had so much fun shopping dear. Can You?" I was about to tell her that this entire morning was a load od shit, but in my present state, I thought better of it and just nodded. "Good girl. You have already learned not to open your cute little mouth without permission." I was turning beat red, both in frustration and anger. The clerk reappeared just as Cheryl was through in the leatherwear isle. "Did you know madam that we have some very nice accessories to go with some of you selections?" "I didn't, but I'd like to see them when I'm through talking to Miss Monique. Thank you." "We also have a very special new type of leather dress that has just come in. Judging by your taste for tight fitting leather, you may be interested in this item. It is quite expensive, but worth every penny, I assure you." "I'll look at that also when I have a free moment." Just then Cheryl was told that Monique was ready for her.

We entered a small room at the rear of the store next to the dressing rooms. The room had a table, and some chains hanging from the ceiling, and a chair next to the wall. "Be a dear, and go sit for a few minutes while Miss Monique talk privately." I was starting to get a little tired, so I took the opportunity to take a load off my loafers. By this time, I didn't care if Monique saw that I was wearing red stockings, and woman's shoes. I had the feeling that she had seen it many times before. The two women talked for a few minutes. It appeared that Cheryl was doing most of the listening as MOnique was explaining something to her. When they were through, both women walked up to me. Cheryl took me by the arm and lifted me to my feet. She then walked with me, arm in arm, to the rear of the room. As I stood there facing the door, Monique came, and walked behind me. I heard her do something with one of the chains, and before I could jump away, she had locked the middle chain to the back of my collar. "Your wife said that you may not be as receptive to this as we would like, so I suggested that you be slightly restrained." Now I was standing straight up with my neck attached to a chain hanging from the ceiling, and my wrists shackled inside my pants. Cheryl then reminded me of what would happen if I said a word, and she started to undo my belt. She lowered my slacks, and unlocked one of my wrists. Miss Monique took hold of it and attached a leather cuff. She then locked it to one of the other two chains hanging down. The process was repeated on the other wrist, and I was now standing with my arms straigt out at my sides.

"There, that should hold her until we're through. You will have to remove the chain from the balls though, and take off the slacks. But please, leave that pretty underwear on her. She looks darling in it. I get so turned on when I see sexy undies on a man." I immediately got a raging hardon. "Oooh, and so well endowed too. I think I'm in love." Miss Monique was a strikingly beautiful woman. My mind immediately began to fantasize about her wrapping her lips around it to relieve the stress. "If your wife wasn't here, I swear I'd be all over that gun, cowboy. Have you ever got a real good blowjob?" I stood there in total shock. '"You may answer Monique. I'd like to know too." My head just dropped, and I knew thay knew the answer. Monique looked at me with a form of delight I had never seen. She walked directly in front of me and giggled. "Have you ever goteen one from another man?" I looked at her face, and she had an adam's apple. I fought violently against the chains, but to no avail. "Don't worry Kendra. I've told Miss Monique that you are strictly heterosexual. She is just trying to get you all worked up."

Monique than pulled a measuring tape and a ruler from a drawer in the table. "This tape is to take your measurements, and this ruler is for bad little girls that can't control themselves." Monique then laid the ruler right on the head of my erect penis. I squeeled and looked down at what she had done. The erection was gone. "See, it works every time." Monique then measured my waist and thighs. "O.K. that didn't hurt a bit now did it? Just one or two more and I'm through. Think about that nasty ruler." Monique then measured by scrotum and my flacid penis."It's time to wake that big boy up again. Tickle, tickle." Monique began to play with my balls, and as hard as I tried to fight it, I had another erection. She measured my shaft again, and declared that she was done. "I suggest that we leave Kendra here just the way she is until I am completely through. I don't think she'll be as willing to be chained up the next time." Cheryl agreed, and I was stuck until Miss Monique was through with whatever she was doing. Monique told Cheryl that it would take four to five hours to be ready for a fitting. Cheryl asked if she was needed any longer. "Not until I've completed the job." "Well in that case, I think I'll look at some of the things that the sales clerkj told me about, and then I'll grab a bite a a local restaurant." "Are you sure you want to leave me alone with this cowboy here all chained up and helpless?" Cheryl got a mean look in her eye and began to scold Monique. "I brought my husband here because I was told your reputation was the best. Now you threaten to exploit my husband while I'm away? If I see that she's been sexually abused by you when I return, I will not pay this quite expensive fee you are charging. In fact, I will make you take at least two dollars off the bill if you do that. Ta Ta sweets." With that she was gone and Monique was roaring, and rubbing her hands together.

"Don't worry honey. I'm not going to turn you gay while she's away. You can start breathing again. So, your wife tells me that you've been a bad little boy, and have been sticking your dick where it doesn't belong. Don't you men understand what can happen when you piss a woman off? I have a feeling you're going to find out." With that comment, Monique left the room and I was left there looking like I was trying to fly. It seemed like forever before Cheryl returned. She brought a sandwich and a drink back with her. "Seems like you'll have a bit of trouble eating lunch in your present state, so I guess I'll just have to feed you myself." She then unwrapped the sandwich and held it up to my mouth. It was difficult to get a bite since my neck was chained to the ceiling, and I had very little slack to move. We finally got through with lunch, and Cheryl said that she had some more shopping to do out front. Again, I was left alone. At about 3:00, Monique came back in and called to my wife. "It's time honey. Would you like to watch?" Cheryl ran back into the room telling Monique that she wouldn't miss this for the world.

Monique whispered something in Cheryls ear, and they both started to giggle. "I think that is a wonderful idea, Monique. Please go right ahead. Monique the went to the other room and retuened with a leather blindfold. She placded it over my eyes, and fastened the buckle. I was now in total darkness. "I've found it easier to do my job, when my client is unable to see." She then began to take my crotchless panties off. Next she lifted my left foot and put it back on the floor. The same thing with my right. "If you try to step out of this, I'll be forced to chain your legs to the floor." I stood motionless. I felt something cold sliding up my silk stockings. "Cheryl, could you please assist me for a moment? I want you to hold this up so I can complete the next step." I couldn't figure out what was going on. Cheryl held whatever it was and then I felt something very cold on my balls and penis. "Just a little something to cool you off. You look so hot in red." She held it there for about two minutes. I knew right away that it was ice. "O.K., that should do it. I now you told me that he was an extra bad boy, so I contoured the tube to be extra tight." I then felt something like tweezers on the head of my penis. It was being stretched out as far as it could go. Something cold completely covered it. It was some kind of tube. The head was released, and Monique took what Cheryl was holding and brought it up to my waiste. Next she grabbed the tube and inserted it into something and I heard a click. A band went around my waiste and another click.

"Thats all there is to it Cheryl. Doesn't it look nice on her, all shiny and new?" Cheryl was squeeling with delight. "Now I'll remove the blindfold and Kendra can see my handywork." When I looked down I couldn't believe my eyes. I was in a chastity belt. "Let me explain the features of this belt. First it is totally inescapable. It is made of stainless steel with a neoprene liner. The manufacturer offers $5,000.00 to anyone who can free himself from it. The closest anyone has come was to cut halfway through the waistband. He also cut himself to shreads in the process. I hope you don't need the money that bad, because he just can't get out of it without the key. Next. it is designed to let the wearer go to the bathroom at will. Of course, he won't be able to stand and pee, so he'll have to sit, just like a woman. No more toilet seats having to be lowered when you want to go Cheryl. It also has the lockable bar in the back that can be inserted into the slot on the belt. This will hold any of the buttplugs you've ordered in place with no chance of escape either." My eyes nearly jumped right out of my head. There are only two keys in the world that will open the locks. If you lose them, the only way you can get a new one is to contact the manufacturer with the serial number on the belt, and the password that you requested. Although it can be worn for extended periods, I recommend that you remove it once a month at least for cleaning of the belt and the area it's designed to protect, if you know what I mean. That's about it. Shall I let her down now?" "No, not quite yet. Let's leave her there for a bit longer. I want to try on all the leather I bought for her today. I don't want to have to return anything." My heart sunk. All the money she spent today was on female clothes for me.

Cheryl spent the next hour trying on all sorts of strange leather, rubber, and vinyl outfits and very high heeled shoes on me. Finally she put a pair of form fittinf leather pants on me and forced the waisteband to close. "That should do it. Let me throw away these silly slacks, and we'll be on our way." She released me and told me not to forget my flats. Now, everyone who saw me would know I was wearing woman's clothing. "Just one word out of you slut, and you'll be walking home like this with no money and no identification. How long do you think it will be before you get picked up?" I was cooked. I had to go along with what she told me to do. I put on my shoes, and we went to the front. "I have to cash out before we leave. I have already bought some specialty items and put them in the trunk. You'll get to see them at a later time." We went to the cashier and it took her forever to check everything out. "That will be four thousand and twent one dollars please." "Kendra, did you bring your credit card with you sweets? Of course you didn't. Where would you put it. Luckily for you, I took it out of your wallet. Now, be a good girl and sign the receipt." I signed it and loaded the Mercedes with the bags. The sales clerk gave me my first call as I left. As I finished Cheryl asked if I minded if we stopped in at the salon for just a minute or two. I didn't have much choice, so I followed. When we got inside, Cheryl handed a girl a bag a snapped at me to sit in one of the beauty chairs. More ice and fifteen minutes later, I left the salon with three gold hoops in each ear. The ride home was going to be fun.

 

 

 

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