Double Jeopardy

She told her she had confronted me about it and that I admitted it to her in confidence and begged her to help me make my fantasies come true. I started to object, but Linda saw it coming and slapped my face so hard it caused me to sit back down and just stare at her. She then went on to tell me that she could see that her daughter was unhappy, that I wasn't satisfying her and so she devised a plan to turn me into a sissy sex slave so I could satisfy them both in a more subservient way.

She told me that I was to become Gwen's hand maid and that I would be under her, Linda's, control and that if I disobeyed her I would be sorry. She then handed me a small duffle and told me to change into these clothes and go and show my wife her sissy husband. As I opened the bag I saw my maid's outfit along with all the lingerie, heels and some make up. I quickly changed and applied some make up and went to talk to my wife.

As I knocked at our bedroom door I heard her crying and asked if I could come in. Not hearing a reply I slowly opened the door and walked in. Hearing the door Gwen lifted her head and saw me walking like a woman wearing a maid's uniform and make-up. As I walked in I went to comfort her, but Gwen backed away from me and told me that if this is what I wanted she would support me. I wanted to tell her otherwise, but I heard a noise behind me and saw Linda standing there and told my wife I appreciated her support.

She then stood up and told me to help her get ready for her date. I just about fell over when I heard her say date and was going to protest, when Linda came in gave me a stern glare and told me to go and run a hot bath for my mistress. I quickly hurried away, and heard Linda talking quietly to her daughter.

Gwen came in and stood as I undressed her, I wanted to touch her and comfort her, but I could tell she was still upset. She stepped in the tub and as she lay there Linda told me to grab the scrubby and begin washing her. I started with her hands and arms and as I got near her tits I could feel my penis start to swell, but Linda was sitting behind me and had her heel pressing on the butt plug and so I don't know what was actually stimulating me.

I finished with her upper body and moved to her feet and worked my way up to her pussy. When I got to her mound Linda told me to make sure I cleaned it nice and good so that it would smell nice for her date. Linda then instructed me to shave my wife's mound so that it would be nice and smooth, when Gwen looked up questioningly Linda told her that all men love a shaved pussy. Gwen blushed at her mother's language, but spread her legs so I could shave her.

Once I was done, she stood up, had me rinse her off and as she stepped out of the tub, dry her off. I then followed her back into the bedroom and just stared dumbly at the clothes my mother in law had laid out for my wife's date. There on the bed was a very short, low cut dress, a garter belt, some nylons and a pair of CFM pumps. As I looked around for the bra and panties, my mother in law told me that Gwen needed easy access for her date. I helped her put on the garter, rolled up the nylons, buckled the heels on and helped her slip on the dress.

I then had her sit down at the vanity and applied her make-up. With the colors Linda had picked out, Gwen was looking very sexy and slutty. As I longing stared at my dolled up wife I couldn't believe that I had actually helped her get ready for a date and yet, there I stood wearing a maid's outfit, lingerie and make-up. As I stared at Gwen, I could see she was no longer troubled and figured that her mother must be right about me, especially upon seeing at how well I could apply her make-up.

Just then the doorbell rang and Linda told me to go and answer the door and invite my wife's date in. I hesitated for a moment before I saw the look of evil in her eyes and quickly went down stairs to answer the door. With my head down, I meekly opened the door and told the man standing there to come in.

He didn't hear me and so he grabbed my face and told me that I was to look at him when I spoke and to address him as 'Sir'. What I saw sent a shiver down my spine, there in the doorway stood a rather large black man who looked like he could crush me without even trying. I visibly swallowed and replied, "Yes Sir". He then pushed past me, sat on the couch and told me to bring him a vodka gimlet.

I had no idea how to make it and was about to say so, when my wife and mother in law came down the stairs. Her date saw her, whistled and said he couldn't wait to get her out on the dance floor. He then got up off the couch and told me to forget about the drink. He then wrapped his arms around my wife and gave her a long, hard kiss, which she seemed to resist at first, but then seemed to enjoy it and responded.

I was completely heartbroken seeing all this and couldn't figure out how I had ended up where I was. Gwen and her date, Jerome left and as the door closed Linda came over to where I was standing and told me that this was for the best, since I was unable to satisfy Gwen as a man, it is only natural for her to find someone who can and that as her sissy sex slave I should be happy for her that she is getting her needs met. Linda then told me that she had a fun night planned for us and told me to make her a gin and tonic.

As I returned with Linda's drink I found her reclined on our couch with her legs spread and her skirt riding up so that I could see she was wearing a garter belt and nylons and a very, very skimpy string bikini. The sight of her succulent mound made my penis stir, but due to my cock cage I was not able to get hard.

Linda told me to hand her, her drink and bury my face between her legs. As I got down between her beautifully tanned thighs I could smell that she was excited and that her lips were already glistening with wetness. I pulled aside the patch and began to insert my tongue when she smacked me on the top of my head and told me to tease her and get her more excited.

I didn't really know what she meant, so she spent the next hour instructing me how to properly satisfy her. First she had me lick gingerly around the outer lips, barely putting any pressure on them. As I did this her lower half seemed to quiver. Next she had me work my way closer to her slit, using more and more pressure until I was licking directly on her slit with the width of my tongue.

She kept me doing that for what seemed like an hour. Finally I was able to gently lick with just the tip inside her pussy. As my tongue split her lips a deep moan escaped her mouth. Again I slowly worked more and more of my tongue inside of her until my nose was rubbing against her clit. She then told me to suck on her clit and make her cum. She told me the faster I made her cum the gentler she would be.

I was puzzled by her comment, but didn't want to incur her wrath and so I attacked her clit with gusto. Within a matter of minutes she was thrashing about telling me to "suck it hard, bitch", I did so eagerly and was rewarded with several body racking orgasms. As I continued to lick, suck and savor, she stroked my head and told me that she knew I would do a good job at being her sissy sex slave.

She then told me to make her another drink and meet her upstairs in our spare bedroom. As I entered the room I saw her sitting on the edge of the bed. She had removed her blouse, bra and skirt and was sitting there in her garter belt, nylons and heels and had a rather large dildo sticking out from between her legs. She told me that as part of my training I needed to be able to handle a cock properly so I could get my treat straight from the source and not always second hand.

She told me to kneel down between her legs and she would teach me how to properly worship a cock and how to get it ready. So we spent the next hour with her instructing me how to suck cock. She had me start by freshening up my lipstick, she told me that all guys love to see lipstick marks on their cocks as it shows them how far a woman can take his monster.

I started out by kissing her "cock" all over and then slowly licking it from base to tip. She told me to make sure I pay extra attention to the underside as guys love that. Next she had me place just the tip in my mouth and swirl my tongue around, making sure I played with the pee hole. Then she told me to breathe through my nose, relax my throat and take more and more of her cock.

I only got about a third of it in my mouth before I started to gag. She grabbed me by my ear and told me to relax and just get used to having a cock in my mouth. As I sat there with her cock in my mouth I just couldn't believe this was all happening. How was it I was learning to give blow jobs instead of getting them? Once I calmed down I was able to go a little deeper and so Linda told me to slide back and forth, sucking as I went.

After doing that for nearly half an hour she told me to get on all fours on the bed. Figuring I knew what was coming next I dallied a bit too much and received several smacks on my bare ass which elicited a yelp from me, I then quickly got into position.

As Linda stood behind me stroking her cock she told me that since I brought her to several orgasms earlier in such a short period of time she was going to use lube, but since I still had some defiance in me she decided not to. I looked back with pleading eyes and begged her to be gentle, but she merely place the tip of her cock against my sphincter and told me to prepare to be deflowered.

With a sharp thrust she pushed her cock past my ring causing me to cry out in pain and kept pushing until her nylon covered thighs were pressed against mine. As she stood there catching her breathe I took the opportunity to try and relax so I could endure the rest of this. She then pulled the dildo out until it was almost all the way out, leaving only the tip inside me and then slammed it home again. She did this several times, until the pain finally subsided and it actually started to feel good.

She then settled into a rhythm and continued to pound my virgin ass until finally I felt her shudder as an orgasm rippled through her body. Oddly enough I started to enjoy being filled by the dildo and when she pulled it out of my ass I felt empty. That feeling didn't last long as she quickly inserted a butt plug back in.

She then had me turn around and clean the dildo off with my mouth. She said a good sissy sex slave always makes sure that her Master or Mistress is cleaned up after they've had their fun. Once done, she had me change into a silky peignoir set and crawl into bed. She told me that Gwen would probably be home late and that I should make sure I have coffee and toast ready for her in the morning as she will probably be very hungry. As I lay there I heard her lock the door to the bedroom and then leave the house. I had completely forgotten about the date my wife was on and began to wonder what all she was doing as I drifted off to sleep.

Chapter 3 - The Next Phase

The next morning I was awakened by hearing the key unlock my bedroom door. It was Gwen and she looked very tired, but also very satisfied. She informed me that she wanted me to make her some breakfast. I grabbed the matching robe, slipped on my fluffy mules and headed downstairs.

As I prepared Gwen her favorite breakfast, dippy eggs, crispy bacon and sourdough bread I couldn't help wondering where we were going to go from here. As I place the plate of food in front of her she asked me to sit so we could talk. As I took a seat I winced due to being sore from my mother in law's ass pounding, if Gwen noticed, she didn't say anything. While she ate she asked me if I still loved her and if I would be willing to do whatever was needed to make our marriage last.

When I readily told her I did still love her and would do anything she asked, she told me to get on the floor, get between her legs and clean her up. At first I figured she just wanted me to go down on her, but once between her legs, I could smell a different scent and when I began eating her out I tasted a different taste and realized that Jerome had fucked my wife.

At first I got upset and was going to stop, but decided that I would put on a happy face and do what she asked. What I didn't realize was that if I had refused once I realized Jerome had fucked her she would have released me from my chastity device and stopped everything her mother was doing, but because I merely accepted my position she figured that what he mother had been telling her was correct and that I wanted all the changes.

As she enjoyed my tongue she thought about the fun time she had last night and how Jerome made her feel special and how hot he had gotten her. She couldn't believe her husband had not heard them. She couldn't wait to ride Jerome's monster cock again and again. As I finished up cleaning out her pussy, she scooted forward and told me to clean out her backside as well.

I couldn't believe my ears. In all the time we had been married, she had never let me near her asshole to even lick or kiss it let alone fuck her there. And yet after one date Jerome had fucked her in both holes. I was crushed and didn't know what I needed to do, so I just dove into my task with gusto.

I probed her ass with my tongue and she reached down and began to rub herself. As her orgasm rippled through her body, she squeezed a large amount of cum from her ass into my mouth. I obediently swallowed it all. Once done, she told me that I could wear a skirt and blouse today while I cleaned up the house, washed her sheets and remade her bed. Crestfallen, I reply, "Yes, Mistress" and headed upstairs.

The next month continued with me doing all the house work at both my mother in law's house and my house, always dressed up in my maid's outfit. I was actually getting quite good at walking around in high heels. One thing I did notice was that my nipples seemed be getting tender and whenever something brushed against them it caused a stirring in my groin.

I didn't think much of it and figured it was the lingerie was I wearing, not realizing that the cream Linda kept rubbing into my chest was actually breast enlargement cream. Also, every Friday and Saturday night Gwen would go out with Jerome and I would always help her get ready. It wasn't too bad until this last weekend.

Friday as Gwen is soaking in the tub, the doorbell rings and Linda tells me to go ahead and answer the door and see to Gwen's guest. As I answer the door, there stands Jerome with a big grin on his face. As I ask him in, he grabs my ass and tells me to make him 'his' drink. I quickly leave and return with his vodka gimlet and was going to head upstairs when he tells me to come back. Reluctantly I return to stand in front of the man who is regularly fucking my wife.

He says that he wants to get to know me better and tells me to remove my uniform. As I stare at him in disbelief, he tells me that I had better obey him before Linda finds out about my disobedience. At the mention of my mother in law's name, I quickly begin to undress. As I take off my bra Jerome can see the slight swell of my breasts and tells me to come closer.

I step between his legs and he reaches up and begins to grab my sensitive breasts. As I squirm and fidget he reaches up with his other hand and grabs my ass and begins to squeeze it, he makes sure his fingers brush against the butt plug, which only heightens my arousal and squirming. He then reaches up with both hands, grabs both my nipples and pulls down forcing me onto my knees in-between his legs.

He then tells me to undo his pants and pull them down so that I can take care of the hard on I have given him. As I hesitate he pinches my nipples harder and I quickly reach up and undo his pants. He lifts his hips so that I can pull them down around his ankles revealing a pair of boxers that are being tented by a rather large cock.

He then tells me to remove his boxers. As I reach up and hook his waist band, he again lifts his ass off the couch and as I pull his boxers down this causes his giant cock to spring forward and hit me on the forehead.

I am a bit taken aback by this and my mouth opens is surprise and that is when Gwen walks into the room. So there I am kneeling between the legs of her lover with his giant cock out and my mouth open. Gwen can't hardly believe what she is seeing, but tells me to continue. Dejected I reach up and grasp Jerome's cock. It is so big around that I can hardly wrap my fingers around it and have to use both hands. I then apply the skills that Linda had me practice.

I start by kissing the tip and then working my way down the shaft until I reach his balls. Once there he tells me to make sure I worship his nuts good, so I spend several minutes licking and sucking on them. I then work my way back up his shaft and take just the tip in my mouth. As I swirl my tongue around the head of his monster cock Gwen comes to kneel beside me.

I don't want to upset her so I try to smile with Jerome's cock head in my mouth, instead of making her happy this only seems to cause her to make a decision and proceeds to tell me to loosen my throat so that I can take Jerome's cock down it.

She tells me that it will take some getting used to, but with practice I should be able to handle it all in no time. She then places her hand on the back of my head and helps push my mouth farther and farther down his cock. As I begin to gag she lets up somewhat and allows me to catch my breath.

I am only able to handle about a third of his cock and can't even imagine being able to take all of this monster down my throat when Gwen tells me to get him off. I pull back, until only the tip is in my mouth and feel Gwen push my head back down. We slowly get into a rhythm until eventually Gwen doesn't even have to help and I am going to town on Jerome's cock.

As his climax builds he grabs my head and holds it as he fills me with his load of cum. Gwen tells me that I had better start swallowing if I don't want to drown in an ocean of cum. I begin gulping down as much as I can, but some still leaks out of the corner of my mouth. As Jerome finishes, he continues to hold my head in place until he is only semi hard. He then tells me to remove my mouth as Gwen stands up and straddles his semi hard cock.

Next Jerome tells me to help guide his cock into my wife's pussy. As I hold onto his cock, Gwen lowers herself onto his tool and I can see that she is already wet and ready for him. I watch his monster cock bury itself into my wife's pussy and I can't believe she is able to take it all in. I then hear Gwen's voice tell me, in a condescending voice, that since it looked like I enjoyed sucking his cock that I should suck on his balls while he fills and satisfies her.

I am crestfallen by her comment and tone, but obediently obey her. To further show her disappointment in me Gwen makes sure she bounces just a little bit extra so that her ass pushes on my head. I must have zoned out at one point, because I am not paying attention and when Gwen's ass hits my head it causes me to bite down on Jerome's nuts. He immediately squeezes his knees together trapping my head and cries out in pain. Gwen stops what she is doing and asks him what is wrong. He tells her that her pussy whipped sissy of a husband just bit him, at hearing this she gets off Jerome and stares at me in shock.

Once she is off him, Jerome reaches down, grabs my hair and yanks me up over his lap. He then proceeds to lift my skirt and give me the worse spanking of my life. After only a few swats of his giant hands and I am blubbering and begging him to stop.

When he finally does stop my ass is on fire and I am a hot mess. He dumps me on the floor and tells me that if I ever bite him again he will punish me even worse. I try to apologize, but through my sobbing and tears you can't tell anything. Gwen then grabs me by my ear and tells me to apologize so everyone can hear and to kiss his sack until she tells me to stop.