Double Jeopardy

Editor's note: this story contains scenes of incest or incest content.

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Author's note: This is a relatively new story I wrote. While editing it I thought about breaking it up into different chapters but figure most people just like being able to enjoy a story that is completely published. I would also like to dedicate this story to my friend Niki. Enjoy.

Chapter 1 - The First One

I have always had a thing for my mother in law. I've seen pictures of when she was younger and she was quite the looker. Now that she is older she is still very good looking, and in fact I think she is even more striking. So when my wife asked me to go over to her parents' house and help out her mom I readily agreed.

I walked in my mother in law and saw she was laying on the couch with a wash cloth over her eyes. I asked her if she was okay, and she replied that she had spent a lot of time on her feet and that she was tired. My mother in law, Linda is a classy lady and always wears either a dress or skirt and pantyhose or nylons with a garter belt. I know this because I have pawed my way through her delicates drawer.

I also know that she still wears some very racy thongs and since she no longer gets her period she does not have a single pair of cotton panties. So, knowing all this, I offered to give her feet a massage. I figured what better way to not only touch her hose covered feet, but also possibly see a peek up her skirt and catch a glimpse of a sexy thong and what it holds.

She said sure if I didn't mind touching her sweaty feet. I just laughed it off, but was hoping that she hadn't had her heels off for too long so I could enjoy that heavenly aroma. As I sat down she lifted her legs in order to put her feet in my lap I caught a quick flash of red. As I rubbed her feet she continued to lay there with the wash cloth over her eyes so I figured it wouldn't hurt to lean down and inhale that wonderful scent from her feet.

What I didn't realize was that when I did that I shifted and since I did it several times Linda shifted the wash cloth so she could see what was going on and watched as I inhaled deeply. Thinking she would have some fun and see how much of a pervert I was she shifted, spreading her legs allowing me to see her nylon covered mound.

With that view distracting me she shifted the foot that I was not massaging into my groin and began to lightly rub it up and down against my hard on that was desperately trying to burst out of my pants. Had I not had so many sensory overloads I probably would have been okay, but without thinking I reached down and pushed her foot against my hard on so that it would rub even more.

At this point Linda sat up and asked if I was enjoying myself. With my one hand holding her foot against my crotch, the other one holding her foot close to my nose and my mind and eyes stuck on her crotch I knew I was caught and just stared at her with my mouth agape. She moved the foot that I was rubbing to my open mouth and told me to suck on her toes.

Obediently I began to suck her toes while she continued to rub my crotch with her other foot. As I sat there she merely laid back and enjoyed the attention. When she felt I was done with her right foot she removed it from my mouth and put her left foot in my mouth and told me to suck on those toes. She then took her wet right foot and began to rub it all over my chest and try to pinch my nipples with her toes.

After removing her left foot from my mouth she got up and headed to her bedroom and told me to follow her. Needless to say I had no idea where this was going, but was extremely hopeful.

As she entered her room she reached behind her and unzipped her skirt and let it fall to the floor, revealing a garter belt and nylons and her red thong. She then climbed up on her bed, spread her legs and told me to show her how good I was at eating pussy.

I approached and she told me to remove all my clothes so she could have something to look at while I ate her out. I quickly removed all my clothes and crawled between her legs. I stared at her nylon covered pussy and realized I could not see much pubic hair. Reaching up to remove her thong she lifted her hips putting her mound very close to my face and based on the scent coming from her pussy I could tell that she was very excited.

I peeled away the nylon and got quite a surprise. Instead of a hairy snatch as I was expecting Linda was completely shaved smooth. As I stared at her hairless pussy with my mouth agape she just smiled at me and told me to get busy. I leaned in and I could see that her lips were glistening and couldn't wait to taste her juice.

I started out by gently licking the outer edges of her lips, slowly working my way closer and closer to her slit. As I did I could feel her trying to thrust up and get me to slip my tongue inside her, but I resisted and continued to tease her. The longer I did the more she seemed to leak fluid.

As I would lick up from the bottom to the top I occasionally got a taste. Finally when I had had enough, I parted her lips with my tongue and licked her the length of her slit. She immediately grabbed my head and pulled me in close and ground her groin onto my face. I felt her shiver, and I just continue to lap up her juices. I then focused on her clit and began to suck, nibble and rub it.

That seemed to hit the spot, because it wasn't long before she clamped my head between her thighs and had a very intense orgasm. Needless to say, during this entire ordeal I was rock hard and very eager for release. As I sat between her legs enjoying her cum covering my face she got up, turned around on all fours and presented her backside to me.

I took that as an invitation and easily slipped my raging hard on into her well lubricated pussy. I was so excited, it only took a couple of strokes before I was blowing my load inside of her. When I finished, she told me to lay down on the bed and proceeded to climb on top of my chest and place her freshly fucked pussy at my mouth. She then told me to clean her up while she explained how things were going to be from now on.

As much as I was enjoying this, I was a little apprehensive at that comment. As I lay there licking my cum out of her pussy, she explained that her daughter Gwen, had been complaining to her about my lack of abilities in the bedroom. I started to object, but she just forced more of her pussy into my mouth and told me I was merely to listen.

She went on to say that Gwen thought I did an excellent job of eating pussy but that due to my small penis I just wasn't hitting her g spot and therefore, not bringing her to orgasm that way. As I listened to this, it all made sense why Gwen always wanted to 69. Upon hearing that I could eat pussy Linda wanted to find out for herself and so she arranged to have me come over today.

Upon hearing that I had been set up was not nearly as upsetting as hearing that my wife shared our love life with her mother. As she continued to grind her pussy into my face and bring herself to another orgasm she explained that since I wasn't man enough to take care of her daughter she felt that I should learn to serve woman.

I wondered what she meant, but didn't have long as she explained that she got her daughter to agree to have me come over to her house on a regular basis and do things around the home for her. Gwen obviously thought that I was merely going to help her mom out with things as her dad was extremely busy with work and not home much.

In reality Linda told me that I was to spend time learning my place. As she climbed off me, she told me to be back at her house tomorrow right after work and that we would start my training. As I made to wipe my face she told me that I should be grateful for her gift and that I had to leave it on my face and that once I pulled into my drive way I was to rub it into my pores.

She must have known I was thinking about just wiping it off once I got in my car, because she came up to me, grabbed my balls, squeezed them and told me that I had better obey her or things would not turn out well for me.

I visibly swallowed and said, "Yes Ma'am", she merely smiled and said that I was learning. I then quickly got dressed and headed home with today's events rolling around in my mind.

Thankfully Gwen was not home when I got home so I was able to rub my mother in laws juices into my face without my wife wondering what I was doing. Afraid that she would know something was up, I went inside and took a shower. All night I kept wondering what my mother in law had in store and did not sleep very well.

The next day, I could not wait for work to be over so I could see what Linda had in store. As I entered the house I heard her call me from her bedroom to come back and join her. I walked in to her room, half hoping, half expecting her to be scantily clad and waiting for me, but that was not the case. Instead she was wearing what looked like old workout clothes, an old pair of shorts, an old t-shirt and socks and sneakers.

I honestly didn't realize she had these clothes, but I did notice that she was also wearing a pair of pantyhose underneath her shorts and it did not look like she was wearing a bra. At the sight of her pantyhose clad legs, I immediately began to get hard. She told me to strip, which I thought was odd, but remembering her threat yesterday, I quickly did as I was told.

Standing there fully undressed I naturally covered my groin with my hands, especially since I was still sporting a semi hard on. Linda then told me to follow her into the bathroom. To say her bathroom was huge would be an understatement. Not only did she have two sinks, but a walk in shower that could easily hold 3 people and a Jacuzzi tub in the corner.

She walked into the shower and after I entered began rubbing a foul smelling cream all over my body. At first it felt nice to have her rubbing my body, but after a while the cream began to burn and I began to dance around. Reaching down she grabbed my package and told me that if I didn't hold still that she would rub this cream on my groin area. As it was she had me turn around, bend over and spread my ass cheeks so she could apply it back there.

Once she was done, she exited the shower and closed the door. As I stood there wondering how long I was going to have to endure this pain she told me to go ahead and rinse off. I quickly turned the shower on and ducked under the cold water. I closed my eyes and just stood there enjoying the relief the water brought and didn't realize that the water was washing away all of my body hair.

Linda told me to make sure I got all the cream off or else I would continue to feel it burn. So, I opened my eyes and as I rubbed my body I quickly realized that I was now hairless from the neck down, except for my pubic hair. I finished and quickly got out, drying off with a pink, fluffy towel that Linda had given me.

I began to object about not having hair, but she just put a finger on my lips and ran her finger nails up my thigh toward my groin while shushing me. I don't know if it was her proximity to my cock or her shear animal magnetism, but I ceased my objections. She then told me to spread my legs and put my hands on the top of my head. Which I readily did.

She then knelt down in front of me and grabbed my cock. This immediately took me from having a semi to a full blown erection. I was hoping that she was going to give me a blow job, but instead I felt her use electric clippers and shave my pubic hair off. Once she was done with the trimmer, she applied some shaving cream and picked up a razor. I started to move, but she had a firm hold on my cock and told me that if I wanted to keep all my parts I would be very still.

I swallowed hard and did as she commanded. She then very adeptly shaved my groin area so that I was completely smooth. She then washed the area with a warm wash cloth, but what happened next I was not prepared for. She then took a bag of ice and held it to my groin. I jumped at the change in temperature and was rewarded with a slap on the head of my penis.

I immediately took a step back and allowed her to finish what she had started. I couldn't really see past her to what she was doing so I just stared at the ceiling hoping this would end soon and that I would get to have sex with her again.

Once she was done making my member very cold and very small she slide a chastity cage on me. It wasn't until I heard the click of the lock that I realized something was not right. As she stood up, she told me that since I was not well endowed downstairs that she felt I could best be used as a sex slave to both her and her daughter and that she was going to train me on how to improve my pussy eating skills along with some other things.

I must have looked crestfallen, as she told me not to worry, that as the sole key holder she would make sure that I got relief on a regular basis. I asked her what I was supposed to tell Gwen, and she said she had already worked it out with her. I wasn't sure how I felt about my mother in law and my wife deciding my love life, but it didn't look like I had much choice.

She then told me to follow her and we went into their guest bedroom. She then proceeded to tell me that everything I would need was in this room and opened the top drawer of the dresser and removed a red thong. She held it out and told me to step into it. I merely just stood there in a daze gawking at her until she reached out and grabbed my caged package and began twisting.

Once she saw she had my attention she told me that I was going to dress as a woman so that way I wouldn't detract from her pleasure and that if I continued to disobey her she would take even more drastic measures to ensure I was controllable. I couldn't think of anything more drastic than the situation I was already in and didn't want to find out what she was referring to and so I meekly lifted my feet one at a time and stepped into the thong. With the chastity device on, the thin material up front was able to hold everything and she made sure the thong part was well nestled between my now hairless cheeks.

Next came a garter belt and nylons which she helped me roll up my legs, but informed me that she expected me to become adept at dressing myself within the next week. She then rubbed some cream on my chest and then put what she called a training bra on me. She said once I started to develop she would make sure I had the right size bra. I wasn't entirely sure of what she was talking about, but was way too distracted with wearing all this lingerie to really pay attention.

Finally she had me step into a black and white maid's uniform. And lastly she applied some simple make up, all the while telling me that I would be practicing these techniques so I could do this myself. Once I was ready she then led me around the house telling me all the things she wanted me to do while I was here. They included cleaning, vacuuming, dusting and of course laundry.

he instructed me that I needed to hand wash her delicates and then hang everything outside to dry. I was extremely nervous about this as even though I was dressed like a woman, I did not have long hair and so if anyone saw me they would know I was not a woman. When I started to protest she merely grabbed my ear and dragged me over to the couch where she proceeded to put me over her lap, raise my skirt and spank my bare ass until I was crying like a baby and kicking my feet.

Through my sobs I told her that I would do what she said. She then dropped me onto the floor and told me to get started. I worked the rest of the afternoon and after only a couple of hours my feet and legs were really beginning to hurt from the heels. Linda saw me rubbing my calves and told me that I would get used to it.

When I had finished for the day she told me that I should return tomorrow so I could practice getting ready. She then had me remove all my new clothes except for my thong and patted my ass as I left her house.

Chapter 2 - Deeper I Go

That night I quickly changed into my pj's before my wife saw the red thong I was wearing and got in bed before she even got to our room. She seemed distracted, but I figured it had to do with work and didn't bother to ask her. The next day after work, I headed to my in laws house and upon entering Linda told me to go into my special room and try to get dressed and apply my make-up.

She said she would be in shortly. I headed to their guest bedroom and began undressing. I figured since I had leaked some in my thong from yesterday I would change it, so I peeled off the red one and pulled a pink one on. I then struggled through getting the garter belt on correctly, but eventually got it and proceeded to work on putting on my nylons. I ended up putting a run in two pairs, but got it on my next try.

As I rolled the nylons up my legs my cock kept twitching, but couldn't go anywhere with it being in the cage. Little did I know, but Linda was filming me the entire time, making sure to capture my excitement at wearing women's clothing. I put on the same heels as yesterday and then stepped into the maid's outfit and got it zipped up and had just sat down at the vanity when Linda walked in.

She told me to stand so she could inspect my work. She had me lift my dress in the front so she could check to make sure the thong was holding everything in place. Her touch on my caged cock only caused it to pulse even more. She then had me turn around, lift the back of my dress and bend over. She then pulled my thong aside and applied some kind of cream or something. It actually felt pretty nice, until she started to insert her finger.

I squeaked and started to stand up, but she quickly reached between my legs, grabbed my cage and pulled and told me to stay in this position. I leaned back down and she continue to work several fingers into my backside. When she removed them I thought I was done, until I felt something rather cold at my sphincter. She told me to take a deep breath, let it out and relax.

As I did she pushed a butt plug into my ass. As I worked through the widest part I thought I was going to cry, but eventually it slide in and my ass closed around the neck of it and I felt relief. Linda then put my thong back in place and told me to stand up and walk around the room.

Having the butt plug in was very different and at first it felt weird but as the pain subsided it started to feel good and without thinking about it I started to sway my hips. Linda told me that a woman walks by putting one foot in front of the other and that I needed to practice that for the next 2 hrs.

I couldn't believe my ears, but didn't want to be punished today and so I walked around the house for the next two hours. By the end I was exhausted, but had trained my body to walk that way and it actually made it easier. As I got undressed, Linda told me to keep the butt plug in so I could get used to it. I went home and that night once again was in bed well before my wife.

The rest of the week I worked on applying my make-up, walking in heels and doing chores in a lady like manner. On Thursday Linda informed me that she would be over at my house Friday afternoon. I was a bit worried about this, but didn't have much choice.

Friday afternoon arrived and as I walked in my house Linda was already there talking with my wife. She was showing her some videos on her phone and telling her that this would be for the best. When I walked in and greeted them, Gwen looked up with tears in her eyes and just ran out of the room. Not sure of what was going on I looked to my mother in law for an explanation.

She told me to have a seat and proceeded to show me the different videos she had taken of me this past week. Every one of them showed how excited I was, you could see how much I was enjoying it. Linda then informed me that she had told Gwen that I was a closet cross dresser and that she had caught me wearing some of her clothes and prancing around the house when I thought I was alone.