Filming a Monster's Tail

I moped around my apartment for a few days trying to think of a way to get Jim to hire me back again. I told myself the money was just too good but a part of me wanted to dress up again and a bigger part of me wanted to do more with Pete and his wonderful cock. Of course I wouldn't admit that to anyone for a fear of being labeled as gay.

I was going crazy thinking about it too much so I decided to go for a walk. Before long I found myself on the main boulevard. It was busy as usual. Everyone seemed to be in a hurry to get somewhere and almost everyone seemed to be lost in their own world. It's really sad when you think about it.

Anyway, I started walking back to my apartment. I was only about a quarter the way home when a black dodge pick-up pulled up beside me. I looked at the driver. It was Pete.

I went up to the passenger window as he rolled it down.

"I thought that was you Mr Todd. Can I offer you a lift?"

Emotions flooded me. I didn't expect this. I felt happy to see him but also shy I guess. Why would I feel shy around Pete, the only man to take me as his for the night. The only guy to ever make me feel like a woman or a gay sissy, whatever.

I smiled as I got in. "Hey Pete, just the guy I wanted to talk to."

"Oh, what do you want to talk about, I hope it's not about the job. Mr Jim was very clear. He doesn't want you around anymore." He said.

"Yeah I know. I really could use the work though, you know. The yard work. That sort of work." I beat around the bushes a bit not wanting him to know I wanted him to take me again.

"The yard work? Is that all the work you want? Because I know people who are always looking for a good man like you Mr Todd.

I kinda half smiled and laughed at the same time. "Yeah, you know. Good old fashioned labor. That's the kind of work I'm looking for. I'm not sure if I was trying to convince him or me as I said this.

"You know Mr Todd, I don't think you are being honest with me. I think you want to look beautiful like you did for Mr Jim's movie. Am I right?

Being called out like that kinda sucked because he was one hundred percent correct.

"Okay, let me be honest. I still don't know how the whole thing worked so well on me. I mean, I didn't think I was gay or anything but what you did to me made me open my eyes and that's all I've been able to think of ever since. Jim is never gonna hire me again because of what I said about him and Stella but I know I'm right.

"You are right but it's not for you or anyone to question them. It's their lives, not yours. Like I said, I know other people that would hire you if you want to do something similar with someone else." Pete told me.

I looked down at my feet as he drove. I do like dressing up and I know Pete. But to work with someone else both scared the crap out of me and excited the hell out of me.

"How about I take you to see someone I know, right now. I will introduce you and you can think about it but I doubt you will think for very long. Sound good to you Mr Todd? Pete asks.

"Okay Pete. Let's do this." I said.

My thoughts went wild as he drove. Would this guy treat me the same way Jim did? Would the clothes be as nice? Would someone be there to do my make-up, hair and nails? What else haven't I tried as a crossdresser? So many questions flooded my head.

Eventually we came to a stop at a huge mansion. The huge double rot iron gate with lion heads on each side opened as Pete drove up as if they expected him or something.

The grounds were extremely well kept. I bet there wasn't a single blade of grass out of place.

We drove up the windy road until we parked between the front double doors and a massive water fountain with a beautiful mermaid spitting water into the pool. Pete got out and a valet man opened my door for me.

"Thank you." I smiled as I got out.

I followed Pete inside.

"Okay, you wait here for a few minutes while I go talk to her. Then I'll introduce you." Pete said then walked away.

I looked around as I stood there. Holy crap was this place huge. There was a massive statue of a Roman soldier or something holding a sword and a shield. This thing must have been 40 ft high. Art adorned the walls and huge five foot by five foot tiles covered the floors.

Whoever owned this place had some serious money.

Ture to Pete's word. He came and got me after about ten minutes.

"Mr Todd. She's looking forward to seeing you now. I'll take you to her." He told me.

We walked through a few rooms. I don't even know how to describe these rooms other than to say WOW. The rich really do have more money than brains.

"Mrs Taylor Maron, this is Mr Todd." Pete introduced us.

Oh my god. Mrs Taylor was a movie star, I recognized her immediately. But I couldn't remember for the life of me what movie I saw her in.

"Pete here tells me you look great in lingerie? Is that true Mr Todd?

I blushed as she asked her question.

"Please, call me Todd." I say. "Well I guess that's a matter of opinion."

Her smirk told me she believes Pete. "Well Pete has told me a bit about you, why don't you tell me the rest!"

"Okay well I'm 23 years old. Stand 5"5 and weigh 130 pounds. I have..." she cut me off.

"What I meant is tell me how you became a crossdresser that's hungry for cock?" She looked me right in the eyes as she asked.

I was stunned to say the least. I wasn't sure how to answer really.

"I um. Well by accident, kinda. Maybe. I don't know." I stumbled trying to think of the right words.

"Would you look at that Pete? I flabbergasted him and I asked just one question! He's so adorable. Isn't he.? Taylor teased saying.

"Yes Ma'am Mrs Taylor. That's not the first time I've seen his turn red."

"Oh you must tell me about it sometime Pete, you know I love a good story. Especially when someone is outed so deliciously well.

"So Todd, 130 pounds you say? I don't think so. 125 maybe but not 130. Have you eaten today?"

"Yes ma'am. I have."

"Call me Amy, that's my real name."

"Nice to meet you Amy."

"Come and sit with me for a while so I can get to know the real you."

We talked about everything you can imagine. I found it very easy to open up to her about pretty much everything. Even some things I thought were too personal. It was getting late and so I told her I'd like to come back and talk again soon.

"How about I hire you to do something similar as you did with Pete, only a bit more risque." Amy asks.

"Risque? What do you have in mind?" I ask.

"Let me come up with something and I'll get back to you soon. I think you're gonna love it though."

I gave her my name, address and phone number and she had her chauffeur take me to my apartment.

About a week had gone by without a word. I was starting to get worried that maybe she changed her mind. I was so happy when she called. Well her assistant called asking me to be at her place Saturday afternoon at one pm. I was told to make sure I was hairless from the nose down and I needed to moisturize as much as possible.

It was Tuesday so I had lots of time.

I went to the drug store to buy a few things I would need to comply with Amy's requests.

A six pack of razors and some shaving cream but I had never used lotion.

They seemed to have a lotion for everything and all of them said for softer skin or smoother more flexible skin.

A clerk saw me standing there so she approached me.

"Can I help you sir?" She asked with a smile.

I smiled back at her. "Yeah I need some lotion to make my skin softer."

"Are you talking about your hands or elbows?" she asks as she scans my hands.

"Um, no. Not just those. I need something for everywhere." I realized that ment my junk as the words slipped from my mouth.

She inquisitively smiled. "Everywhere? Well we do have a lot of choices. Do you want scented or unscented?

I hadn't thought of that but now I was. Do I want someone I'm shooting a scream with to smell a scent like summer breeze or fresh autumn slenderness? Oh hell no.

"Unscented please." I answered.

"Well this one I think would be better for those nether regions and if by chance you had a problem there, it would help to get rid of it if it wasn't too serious."

"Oh I um don't have anything, I just need to er, want to be um smooth. That's all." I sounded a lot more embarrassed, then ashamed I think.

She kept smiling, "I'm just kidding with you. Lotions don't do much other than moisturize and make your skin look better. Here, this one is the one I use." She handed me a big bottle of lotion.

I looked at it for a moment.

She put her hand in mine, "see how smooth my fingers are. I use it every day."

Her fingers were slightly cool but very smooth and soft.

I looked into her eyes, "thank you. They feel perfect. I mean soft and smooth perfect."

I paid for the items and went home.

I regularly shave because I competitively swim so shaving is rather easy. I only needed two razors to finish the job. Moisturizing on the other hand I had never done. The bottle said apply as needed and smooth over with a hand. But it didn't say how often so as soon as I was out of the shower I applied some all over my body. I did this five or six times a day.

By Friday I was slipping out of the cotton sheets of my bed with ease. My skin looks great.

I stayed up late Friday night purposely so I would sleep in on Saturday. I woke up at eleven twenty am.

Oh shit. I jumped in the shower quickly and ran the razor over my body one more time and got out. I moisturized the hell out of myself and headed out the door at five after twelve. The walk to her place took me just over an hour. Thank god it wasn't overly hot but the forecast said it would warm up big time in the afternoon. I pressed the buzzer on the gate and a moment later it opened.

"Please wait there, I'll be right there to pick you up sir." A voice on the speaker said.

Sure enough a side by side drove up to me. The chauffeur driver was driving it. I got in and we drove up to the mansion without a word spoken.

I followed him inside and he led me straight to Amy.

"Ah yes Todd. It's so good to see you." She said as she held my hands and gave me a kiss on the cheek. "Oh my, your hands are soft. Whatever you're using, please keep using it. It's working wonders." She commented.

"Please sit while I get my notes."

I smiled as I sat on the loveseat.

She scanned her notes as I curiously watched.

"Yes I think I have just the character for you to play. Would you like me to tell you all about it or would you rather it be a surprise, you know what. I think it's better to be surprised, don't you?" She asks.

"Surprises can be a lot more fun!" I explained with a smile.

"Surprise it is. This is going to be so fun. Oh I should ask. Do you have any inhibitions?

The confusion on my face told her more than I wanted to say.

"What I mean is, is there anything you don't or won't do? Sexually, of Course." a devilish grin crept across her face.

The look on her face had me convinced she was up to no good but she still looked so innocent so I told her no.

"Perfect. Now you do remember I said it was going to be something similar to what you did for Jim?"

"Yes, I remember." I said.

"Good. My maid will help you with everything you will need." Just then a young lady appeared dressed in a black and white maids uniform.

My cheeks felt like they spontaneously combusted.

"Oh my, do you know my beautiful maid? Amy asks.

"Mistress, if I may. I helped him pick out the lotion at the drug store I work at." The maid explained.

Amy looked at her.

"Do I not pay you enough young lady? You have to moonlight. Amy asked, sounding a bit upset.

"Yes mistress, you compensate me well. I just do it after I'm done working here so I can save up and go to university in the fall." The maid said.

Amy smiled at her.

"Were you planning on quitting working for me when you went to university Sabrina or do you have a clone to take your place here? Amy didn't sound too happy all of a sudden.

"I planned to give you two full weeks' notice, mistress."

"A maid as good as you are is not easily replaced, Sabrina. I would have you know that.

"Yes mistress." Is all she said as she looked down.

"What were you planning on studying in university, Sabrina?" Amy asked.

"Business and film management. Mistress." Sabrina told her.

"Film management, well I can help you with that and it won't cost you a fortune in tuition fees. Would you be interested, Sabrina?"

Sabrina's eyes lit up. "I would, mistress, I definitely would be interested in learning from a legend like you, mistress."

"I of course would need something in return." Amy scoffed.

"Anything, mistress. Anything at all. Just name it my lady." Sabrina sounded extremely excited.

"I'll keep that in mind but for now, I need you in the position you are in now. Okay?" Amy said.

Sabrina curtsied. "Yes, mistress."

"Okay, take our star upstairs and help him get dressed for the opening scene." Amy ordered.

I got up and followed Sabrina up the huge spiral staircase and into a huge room similar to Jim's dressing room but way bigger and much fancier.

"Okay so I need you to get undressed." Sabrina says.

I stripped everything off except my boxers.

She watched but when the boxers stayed on she motioned for them to follow suit.

I slid them down my smooth legs and caught her smirk as she saw how small my penis is.

"It's kinda cool in here, isn't it?" I asked.

"No sir, it's quite warm. I assure you."

"Do you have much experience in putting on lingerie?" Sabrina asked.

Clearing my throat a bit I say, "um yes I do. Not a lot mind you but there was this one time..."

She cut me off. "Good, we don't have a lot of time. Mrs Amy is waiting and sometimes she can be quite impatient so if you can please put these on." She handed me a pair of black sheer stockings.

She stood there watching me as I slipped my feet into each one and pulled them up my freshly shaved ever so smooth legs.

The goosebumps covered my entire body as I slowly closed my legs together. The sheer felt incredible on the inside of my thighs.

I opened my eyes to see her reaction. She watched with intense interest.

"Very good now put this on." She handed me a black garter belt with pink roses.

I put it on and attached the clasps to the stockings.

"And now the bra." She handed it to me as she smiled.

I put the bra on and fastened it behind me then looked at her and smiled. The empty cups were large.

"I'll need a lot of help filling these." I said smiling.

"Yes you will but for now, please put these on." She said as she handed me a pair of black satin panties.

The feel as I slid them up my legs just about sent me over the edge even though I didn't have a hard on yet. I felt incredibly aroused. The panties hid any possibility of a bump magically to my surprise.

"That's much better Mr Todd. Nobody wants to see such a little embarrassment now do we?" Sabrina said confidentiality.

"Um, I guess not." I said feeling rather let down. Sabrina is a really good looking girl. I was kinda hoping we were gonna hook up but by what she just said. I realized that probably wouldn't happen.

"Don't worry. We will be taking good care of you." She told me.

She handed me a large breast form and I slipped it into place then she handed me the other one and I slipped that one into place too.

Next came the hollow out cage and the dress.

She tightened the laces in the back to pull my ribcage in and then she played a set of high heels on my feet as I'm sure I couldn't bend over to save my life.

The dress made me look like a sophisticated woman from the 1800s. The dress covered everything except a patch of skin on my chest.

She sat me down and applied make-up and curled my hair. She tied a bow in my hair as well. Then lightly dusted me in a perfume.

She handed me a small clutch with some lipstick and told me I was ready.

She led the way down the stairs and outside to a large wooden deck.

"Oh my, I must say Todd, you look perfect. My compliments Sabrina on a Job well done." Amy said, sounding pleased.

"Excuse me Amy but if possible. I'd like to be called Lisa while I'm dressed in ladies wear, if that's okay." I asked.

"If it's okay, oh definitely Lisa. Excuse me everyone, may I present Mrs Lisa. Our star performer."

Everyone clapped their hands and said yes ma'am.

When I say everyone, I mean the four cameramen, the four or five men holding long poles with the microphones on them. A whole bunch of people running around doing various jobs. Hell there must have been a good fourty or fifty people just within sight of me. I suddenly felt much more exposed even though I was fully covered.

"Okay, Lisa. We will be shooting you in a few different scenes so we don't have to undress and redress you again later. These scenes you will be fully clothed.

The first scene had me sitting on a park bench reading a book as people walked by. I didn't interact with anyone. Easy scene.

The next scene showed me walking in the same park and acknowledging the men as they graciously tipped their hats to me.

The third showed me eating dinner alone in a home setting.

The fourth showed me going up to a bedroom alone.

These scenes were all very easy and I felt more and more confident as the day went on.

"Beautiful people, cut. Lisa, please go change and we will see you back here in the bedroom when you are done. Sabrina, please accompany her." Amy directed.

As soon as we were back in the changing room. Sabrina untied the back of the dress and I stripped naked reluctantly. The stocking felt so good I didn't want to take them off.

Sabrina went through a few things gathering my next outfit.

"Lisa, are you familiar with one of these?" She was holding a very small flat chastity cage.

"Yeah. I am but do I really need it? I mean isn't it small enough?"

"Small is one thing. Out of sight is another so if you please. I need you to put it on." Sabrina tells me.

"To be honest, I've never actually put one on before." I confessed.

She took a deep breath and exhaled.

"Well I guess I'll have to put it on you then. Please sit down and spread your legs wide."

I did as she directed and she unlocked it and split it into three pieces.

"This works better if you're hard so do what you have to to get it hard please." Sabrina says, sounding a bit nervous.

"You mean in front of you?" I ask.

"I can turn my back if that would help." She suggests.

"No I mean. I can't just will it to be hard. I'm gonna need a stimulant of some sort."

"I can get you a magazine."

Seeing her squirm a bit gave me an idea.

"No. I'll need to see the real thing." I suggest.

Her eyes got a bit bigger as she realized I wanted to see her.

"Oh I'm not exactly, well that is um..."

I cut her off saying, "well you can always go tell Amy you couldn't get me into the cage."

She stared straight in the eyes. I held my gaze not flinching one bit.

It was as if I hypnotized her or something. She just pulled her top down exposing her bare breasts.

My god they were perfect in every way. They looked to be a full D cup and stood up on her young chest nice and tight. Her nipples hardened as my gaze flashed back and forth between them. My little cock reacted almost immediately. Her eyes dropped to my cock as she waited.

As soon as I was hard enough she approached and got between my legs. I sat back and closed my eyes hoping to feel her soft lips on my cock but instead a drop of lube covered the small head and her slightly cool hand cradles my balls.

The three or four inch tube slid into the head of my soon to be locked away dick, then the back ring snapped around my whole package and the flat tube pushed my dick into my body. A nut screwed on to hold the tube straight and a tube lock slid into place, I was done.