Jess and Jessica

"I see you're taking a liking to what a bought for you." my wife says sneaking up behind me.

"I guess, hun," I replied.

"Please don't call me hun, you are hardly a husband to me anymore, call me by my first name," she said.

"Sorry hun, I mean Jessica," lowering my head in shame.

"Also, you better appreciate the things I bought you. Because you're responsible for keeping up with your cosmetic needs from now on," she says with a smirk.

"But with what money? You made me quit my job," I ask baffeled.

She cracks an evil grin, "Well that's part of your surprise!" she says, as if I was supposed to be excited.

She walks over to the trunk and pulls out a key from her bra, and unlocks it.

I can't see what's in there from where I'm sitting, but she pulls out a box from the top of what looks like a bunch of surprises waiting for me.

She closes the trunk and calls me over to the bed.

"Sit on the bed, lay back and close your eyes," she tells me.

As I lay back with my eyes closed, I feel her unzip my snug fitting designer jeans. She pulls my panties down exposing my flaccid excuse for a penis.

She tells me, "No peeking."

I obliged.

I couldn't figure out what she was doing to my cock, but it was the first time she's touched it in almost a year. I started to get excited.

"Down girl," she says, "You know the rules, you're a girl now, and that means we have to train you."

She finishes what she was doing and tells me to look. She had locked me in a chastity cage. It started to hurt, as it was restricting my pathetic excuse of an erection.

"This is to stay on at all times, even when you shower," she demanded.

She zipped me back up. It felt a little uncomfortable, but she reassured that I'll get used to it.

"Now, I have another surprise for you. Your new source of income," she says while gesturing to my laptop.

I looked at her with a bewildered expression.

"A girl with a body and face like yours shouldn't waste it. I've set you up to perform live web-cam shows daily. You're schedule will during the day, while John and I are at the office, leaving some time to finish your chores. We're off today, and your first show is in an hour, so I can walk you through it," she explains.

My heart raced. "A show with what? What am I doing?"

"Well," she says, "Beings you are no longer a man in most peoples eyes, we're going to have to train your ass, or might I say, pussy."

"My ass?!?" I ask frantically.

"No Jess, your pussy. I want you to perform shows for people. In order to keep them happy, you better to be able to complete requests or else."

I didn't bother to ask about the consequences.

Jessica, my loving wife starts to pull items out of the trunk at the foot of the bed.

My eyes widen.

All sorts of dildos, vibrators, and butt plugs, all different colors, and different sizes. Some of the items I didn't even recognize. She gave me some time to get acquainted. Meanwhile Jessica is tinkering with my laptop, and she sets the web-cam up to face the bed.

"You know what? We can get started now," as she pulls me over to the bed. She has a website open with some sort of control panel active.

"And action!" ahe says before I can even grab a hold of what's going on.

What I see on the screen is a chat room and two video boxes, one of which is me. I assume the other is for any one-on-one private shows. The chat room quickly fills up, and my heat races. Jessica is to the side, out of the scene. The chat room lights up with action.

"Hey beautiful. Let me see that sissy clit."

"Wow I would marry you."

"U wanna get fucked?"

"I wanna see that pretty ass."

The list goes on...

All typical, degrading pickup lines from anonymous people from who knows where.

"Give them a peek," Jessica whispers from an area outside the camera view.

I'm scared beyond belief.

"Do it!" she demands.

I get on my knees and slowly unzip my jeans. Showing a tease of my silver panties.

More degrading text on the screen as I look at Jessica.

She nods.

I lay on my back and kick my legs up to remove my skin tight jeans.

"Are you sure you're not a real woman?" one person types.

A wiggle my legs and the leans come off. I threw them to the side, and got back on my knees for the room to see my flat tummy and ultra tight panties.

There was about a hundred people in the room.

A notification pops up in the corner.

"'StudDaddy' would like to start a private chat with you. Click yes to start the show."

I knew what I was required to do. My wife smiled with approval.

A face pops up on the blank video screen. All it showed was a video feed of a decent sized cock.

"Hi there," came from my speakers. "Now let's finished what you started. Take that top off."

On my knees, I reached down, crossed my arms, and pulled my top off in a sensual manner. Leaving me exposed wearing only my matching bra and panties.

All of my toys were on display, laid across the bed.

I stayed locked in this position not knowing what to do.

"Take your panties off," the screen says.

I inch my panties down, terrified of the reaction I'll get when I expose my caged clit.

"Keep going, I'm paying you by the minute," he encourages.

"Here we go," I thought.

I pull my panties down to my knees, exposing my locking device.

"Wow, a trained sissy," he says. "Turn around and show me your ass."

I turn and get on my hands and knees, raising my ass in the air, and give it a little wiggle to play the part.

"Spread your cheeks, I want to see your pussy."

I reach around and use both of my hands to spread for him. Leaving my face buried in the bed sheets.

I hear him moaning, and pleasuring himself.

I must say, I was starting to enjoy the fact I was turning him on so much.

After a few minutes I heard him say, "See the black one, use it on yourself."

I reach over and grab it, still facing my ass towards the camera. It was huge. At least ten inches long, and two inches thick. I peek over my shoulder to Jessica. Her eyes widened as if she was threatening me to proceed. She points to the lube.

I reach over to grab the lube, and coated the huge toy cock, whatever was left on my hand was rubbed into my exposed pussy.

"Go ahead baby," encouraged the stranger.

I put the tip of the cock to my ass, and push a little. The pain took over my body.

"Relax," I heard whispered from the corner. It was Jessica, who was now joined by John. His arms around her, claiming her.

I relax my body, and pushed deeper. Before I knew it I had half of the cock inside of me. The feeling was an intense mix of pain and pleasure I've never felt before.

"Deeper," my laptop continued to moan.

I thrust the fallace deep until the artificial balls rubbed against the cage that wrapped around mine.

In medical school, ones of our classes covered the prostate, otherwise known as the male g-spot. We were told that enough stimulation to this area would trigger an orgasm in some people. Today I was experiencing something that reminded me of that class.

I started to gyrate my hips as I pushed the toy in and out.

Another groan from the speakers.

Faster and faster I rammed what was once a tight little hole. My feet started to go numb. My legs followed.

I peek out of the corner of my eye to see my wife Jessica, and John with evil grins on their faces.

"I'm cumming baby!" screamed the man enjoying my show for him.

At the very same time I felt an explosion inside of me. This wasn't an ordinary orgasm. Usually when I cum it's from external stimulation.

I squirt from my tiny clit, and stain my bed sheet. My entire body numb and tingling. I look over at my laptop to see that my audience member had disconnected. He was apparently satisfied.

"Well that was a success!" said my wife. "I'm a little worked up after that. Clean this mess up and get back in front of that camera. You have three and a half more hours until you're done. If you don't stick to your schedule, your rating could go down, and I'll be upset with you."

She takes John with her as she leaves.

I quickly and shamefully clean my mess up. Meanwhile, I hear John in the next room satisfying my wife in a fashion I was unable to.

I out my clothes on and sat on the bed in front of the camera to finish my duties. About fifteen minutes go by chatting and responding to lackluster pickup lines and compliments.

""Hardcore2269" would like to start a private chat with you. Click yes to start the show."

The black dildo was a popular choice that day.

After my four-hour show, and many private shows, my body was exhausted. It takes a lot of energy to force yourself to have multiple orgasms in such a short time. I take off my sweaty clothes, slide out of my bra and panties, and hop into the shower. I never knew how refreshing women's hygiene products were. That helped relax me. Sitting in front of my vanity wrapped in a towel, I blow dry my hair and use my new hair straightener.

"How ya feeling?" my wife asks. I didn't hear her walk in.

"I feel better after my shower," I responded.

"Good, because you're making dinner tonight. This is pretty much going to be your new daily routine. I hope you can get used to it. Or else you'll be out of here, with no job, and no friends."

She was right, the only people I socialized with were coworkers from the hospital. After my resignation letter, I'm sure I won't want to socialize with them any time soon.

"Get dressed, you're going shopping. Also, we're having a special guest tonight."

"Who?" I asked.

"You left his card in the car."

"Bruce!?!"

"Yes... Bruce. I took the liberty of calling him to set up a date. I told him on the phone that you're shy, and you can't stop talking about him. But you didn't have the guts to call him. And it just so happens that tonight is good for him"

"But he doesn't know about me!" I pleaded.

"Well then, improvise. He's looking forward to meeting you, I wouldn't want to hurt his feelings by canceling," she says leaving me no time to respond.

I finish my hair and go through the closet for something to wear to the supermarket. I pick out a pair of tight black yoga style pants, with a long tan, almost dress-like sweater. A black thong, to avoid panty lines would be a wise choice with-as always-a matching bra. I finish the outfit with matching high heeled boots lined with fur. I should thank my wife for these, as she supplied much of her own clothing, in which she stopped wearing. Anything she felt she wouldn't wear anymore would end up in my closet.

I walk out to the car, purse in hand-compliments of my wife-and I see the neighbor out front washing his car. I started to panic as he looked over at me. He gestured a friendly wave, and went back to what he was doing.

The drive to the supermarket seem to be the longest trip of my life. As I finally pull into the parking lot, I keep my eye open for a spot closer to the front. No luck. It seemed like the whole town was there. I ended up parking near the end if the lot. I turned the car off, took a deep breath, stepped out of the car, and took my first steps as full-time Jessica in a public setting. As I walked into the store, I was greeted by a young clerk going though puberty. He stammered as greeted me and asked if need help with anything.

"No thank you," I said as I put a little sexy into my step. I felt him staring at me as I passed.

As I walk though the store, the only sound I noticed was the tapping of my heeled boots on the polished concrete floors. I notice men with their wives scoping me out as their significant others read over their shopping lists. One gentleman actually turned around after he passed me as if he forgot something I that aisle. I quickly stopped, and bent down seductively, as if I was looking for something on the bottom row. I felt his eye burn a hole though my tight-fitting pants as he passed.

I was enjoying this too much. The attention was exciting me beyond belief.

I walked out of the supermarket feeling like a different person, or woman, might I say.

As I pull into my driveway, I notice that my wife and John are not home. They must have gone to the office to review some case they were working on. Dinner was in a few hours. There was a note on the counter.

"Change into something a little more appropriate for dinner tonight. I don't want Bruce to be disappointed. I set out a nice outfit for you."

I walk into my room to find a black cocktail dress laid across my bed. I get undressed and try it on. It was extremely tight around my upper body, and flared out around my thighs. It was very short. The spaghetti straps gave me the idea of wearing my strapless bra, which had a little padding to give me the illusion of small breasts. I threw on my sexy strap stilettos and went back to my cooking duties.

As I was finishing dinner, my wife arrived home with John right behind her.

"Great, dinners almost done," she says, "Let's get the table set up before your date arrives."

Just as we finish the table setting, the doorbell rings. Jessica hurries to the door to answer.

"Oh hi Bruce!" I hear her say as I'm setting out the food.

"Please, come in! Welcome to our home. This is my husband John," Bruce shakes his and and greets him with a warm smile.

"My wife just introduced another man as her husband," I thought, as every last bit of dignity I had was flushed down the toilet.

"And I'm sure you remember my cousin, Jessica," as she points my way.

I just smile. With my tail further between my legs. Well... Actually my cock, if you wanted to be literal.

Bruce walks over to give me a hug. As he holds me, I see my wife giving me the thumbs up in approval.

"Wait, you both share the same name? That must be confusing," says Bruce, trying to be social.

My wife interjects, "Sometimes it can be, but everyone usually calls me Jess, and calls her Jessica," as she points my way. "She's always been more ladylike than me. So Jessica suits her better."

"I can deal with that," Bruce says, "So, Jessica, what's on the menu tonight?"

As we sat and ate dinner, Jess started to explain the story of how I moved from L.A. after graduating nursing school to keep her company, and help out after her grandmother passed away. All if which was a lie. I just played along and validated her story with subtle nods. This was how most of the dinner conversation went. As we finished, Jess and John excused themselves, and retreated to the bedroom.

"Give him a tour, our home is his home," she said as her and John disappeared into her bedroom.

"They seem like a really nice couple," Bruce said, as he helped me clean up.

After I give Bruce a quick tour of the house we end up in my room.

"Nothing too exciting," I say as I flatten the wrinkles in my bed sheets. My back turned to Bruce.

As I finish my sentence I feel two hands grab my hips, and slide around to my tummy. Bruce hugs me tight from behind.

"We can change that if you like," as he starts to kiss the back of my neck.

He turns me around and plants his lips on mine. He caresses my face as we interlock our tongues in each others mouths.

I slide my hand up his shirt to feel his rock hard body. Soon both of my hands were exploring his upper torso.

He then picked me up and wrapped my legs around him, and he kissed me with more intensity. His hands exploring my body. Luckily he still had his pants on, so he couldn't feel my clit cage pressing against him.

He laid me back onto the bed while still holding and kissing me. He worked his way to my neck, then my chest. As he started kissing my belly through my dress, I felt his hand run up my leg. In a moment of panic I stopped him.

"What?" he asked. "Am I coming on too strong? I'm sorry, the last thing I want to do is make you feel uncomfortable."

"No. You're not," I said, as I thought quickly. "If we're going to do this, I want to do it my way."

"What did you have in mind?" he asked.

I pushed him off of me. He laid back with his head on my pillow.

I go to the trunk at the foot of the bed. Bruce raises his head.

"No peeking," I said, as I grab a pair of handcuffs Jess was generous enough to add to my collection of toys.

I stand in front of him, and hang the cuffs from my index finger trying to be as sexy as possible.

"Wow, Jessica, I thought your cousin said that you were the proper one," he says. Clearly excited for what's to follow.

"There's a lot of things people don't know about me," I said with a smile.

I straddle him and pull his hands to the bars in my headboard. I pass the cuffs through, and lock them around his wrists so he is unable use them.

"Wait here," I said. "I have a surprise for you."

His smile grew.

I go over to my walk-in closet, and grab the pieces I needed for a school girl outfit. I stripped down to my bra and panties, and throw my dress in the corner. The white dress shirt was very snug around my waist, but left enough slack to tie the bottom, revealing my belly. The skirt was unnecessarily short, but fit perfect, as always. The white socks went just above the knee, and the black Mary Jane heels made my legs look longer than they actually were. Putting my hair in pigtails with two hair ties from my accessory bag was the cherry on top. I squeeze some lube into my hand and pull my thong to the side to spread some around generously into my pussy.

I walked back in the room into his sight.

"You look amazing!" he says.

I just smirk, light the candles on my end tables, and walk over to turn the lights off. The lighting was perfect.

I seductively trot over to the bed and stand in front of Bruce. I reach up into the sides of my skirt while letting the front of it cover my little secret, and pull my thong down, letting them fall down my legs.

I step out of them onto the bed, and throw my legs over my lover, making sure my skirt is still concealing my cage.

I unbuckle his belt and pull his pants down, then his underwear. I throw them on the floor.

His cock was huge, almost an exact replica of the toy made famous by my web-cam shows.

I reposition my self so that his shaft is resting against my pussy, and started to kiss him again. I gyrated my hips and moved my pussy up and down his rock hard member to help cover it in lube.

"You're so wet already," he says between kisses.

As I rub my pussy up and down his shaft, I pull my ass all the way up to the tip of his cock. I slowly press it against my wet hole.

He lets out a moan.

I push him deeper into me with my own weight. And before I knew it, he was completely inside of me.

He trusts in and out of me, impaling me with his huge rod. I couldn't help not to moan with intense pleasure.

My tiny cock was shrinking even more. Which was strange, because this was one of the most erotic experiences of my life.

We fucked in this position for a good twenty minutes before I turned around and faced the other way. I placed my feet down and used my legs to bounce up and down on his cock.

I felt the fire inside of me begin to flair. His cock hit my spot perfectly every time I slammed down, bringing me closer to eruption.

I didn't want to cum and squirt on him. I had my identity to protect.

"I want you to taste me," he said between moans.

I quickly jump off, turn around, and take him into my mouth. I struggled at first, but after a few minutes I was easily taking most of his nine inches orally. I always had a knack for sticking large things in my mouth. Looks like that talents paying off. I pleasured him for a while, occasionally stopping to lick his balls and shaft. He started to fuck my face violently and let out a long moan.

"I'm going to cum. Get back on top of me," he grunts.

I quickly hop up on top of him, jam his cock inside of me, and ride him as fast and as hard as I could to try and make him cum before I did.